# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_exp_15643
_database_code_depnum_ccdc_archive 'CCDC 1917274'
_audit_update_record             
;
2019-05-20 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;
_audit_creation_date             2019-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H15 F5 N2 O)'
_chemical_formula_sum            'C44 H30 F10 N4 O2'
_chemical_formula_weight         836.72
_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 0.0181 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      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                   14.0842(5)
_cell_length_b                   6.3205(2)
_cell_length_c                   42.4385(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.560(3)
_cell_angle_gamma                90
_cell_volume                     3774.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.3570
_cell_measurement_theta_min      3.8250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            35658
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.945
_diffrn_reflns_theta_min         3.692
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  65.00   1.00    6.91    --   37.91 -77.00-150.00   95
  2  ω     21.00 105.00   1.00    6.91    --   37.91  57.00 -60.00   84
  3  ω    -30.00  65.00   1.00    6.91    --   37.91 -77.00 -90.00   95
  4  ω    -31.00  57.00   1.00    6.91    --   37.91 -37.00 -60.00   88
  5  ω    -29.00  55.00   1.00    6.91    --   37.91 -57.00-150.00   84
  6  ω    -30.00  65.00   1.00    6.91    --   37.91 -77.00   0.00   95
  7  ω     91.00 176.00   1.00   27.65    --  108.00  45.00 -60.00   85
  8  ω     39.00 109.00   1.00   27.65    --  108.00 -94.00 120.00   70
  9  ω     38.00 129.00   1.00   27.65    --  108.00 -30.00-150.00   91
 10  ω     41.00 126.00   1.00   27.65    --  108.00 -61.00  30.00   85
 11  ω     38.00 129.00   1.00   27.65    --  108.00 -30.00 120.00   91
 12  ω    100.00 178.00   1.00   27.65    --  108.00 111.00-120.00   78
 13  ω     38.00 116.00   1.00   27.65    --  108.00-111.00-150.00   78
 14  ω     39.00 109.00   1.00   27.65    --  108.00 -94.00-120.00   70
 15  ω     11.00 105.00   1.00    6.91    --   37.91  77.00-180.00   94
 16  ω     21.00 105.00   1.00    6.91    --   37.91  57.00 120.00   84
 17  ω     11.00 105.00   1.00    6.91    --   37.91  77.00  30.00   94
 18  ω     21.00 105.00   1.00    6.91    --   37.91  57.00   0.00   84
 19  ω     11.00 105.00   1.00    6.91    --   37.91  77.00-150.00   94
 20  ω    -30.00  65.00   1.00    6.91    --   37.91 -77.00  90.00   95
 21  ω     90.00 175.00   1.00   27.65    --  108.00  61.00-180.00   85
 22  ω     91.00 176.00   1.00   27.65    --  108.00  45.00-120.00   85
 23  ω     39.00 109.00   1.00   27.65    --  108.00 -94.00   0.00   70
 24  ω     70.00 178.00   1.00   27.65    --  108.00  15.00 150.00  108
 25  ω     70.00 178.00   1.00   27.65    --  108.00  15.00  60.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1040722000
_diffrn_orient_matrix_UB_12      0.0243403000
_diffrn_orient_matrix_UB_13      0.0122212000
_diffrn_orient_matrix_UB_21      0.0315333000
_diffrn_orient_matrix_UB_22      0.0175284000
_diffrn_orient_matrix_UB_23      -0.0341855000
_diffrn_orient_matrix_UB_31      -0.0126845000
_diffrn_orient_matrix_UB_32      0.2419934000
_diffrn_orient_matrix_UB_33      0.0012389000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5491
_reflns_number_total             7320
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         7320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.012
_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)+(0.0617P)²+1.0971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1410
_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:
 C27(H27), C37(H37)
2.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C53(H53A,H53B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15), C17(H17), C24(H24), C29(H29), C43(H43), C49(H49), C55(H55),
 C59(H59), C18(H18), C41(H41), C42(H42), C46(H46), C52(H52), C54(H54), C56(H56),
  C57(H57), C60(H60)
2.d Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C58(H58A,H58B,H58C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.43188(9) 0.7784(2) 0.23667(3) 0.0833(4) Uani 1 1 d . . . . .
N2 N 0.39281(11) 1.4077(3) 0.17516(4) 0.0592(4) Uani 1 1 d . . . . .
C3 C 0.27799(13) 1.6803(3) 0.15989(5) 0.0563(4) Uani 1 1 d . . . . .
H3 H 0.239508 1.638224 0.175996 0.068 Uiso 1 1 calc R . . . .
C5 C 0.36138(12) 1.5709(3) 0.15493(4) 0.0522(4) Uani 1 1 d . . . . .
C6 C 0.30145(14) 1.0048(3) 0.22420(4) 0.0563(5) Uani 1 1 d . . . . .
F7 F 0.16014(9) 1.2036(3) 0.21567(4) 0.0934(5) Uani 1 1 d . . . . .
N8 N 0.32754(11) 1.3203(3) 0.19438(4) 0.0598(4) Uani 1 1 d . . . . .
O9 O 0.28936(13) 2.0856(3) 0.09749(4) 0.0860(5) Uani 1 1 d . . . . .
F10 F 0.32789(12) 0.5115(3) 0.26799(4) 0.1003(5) Uani 1 1 d . . . . .
C11 C 0.33948(15) 0.8237(4) 0.23854(5) 0.0633(5) Uani 1 1 d . . . . .
C12 C 0.56605(13) 1.3422(3) 0.16776(4) 0.0530(4) Uani 1 1 d . . . . .
C13 C 0.35756(13) 1.1381(3) 0.20386(4) 0.0548(4) Uani 1 1 d . . . . .
C15 C 0.59330(15) 1.5204(4) 0.18422(6) 0.0672(5) Uani 1 1 d . . . . .
H15 H 0.549245 1.592866 0.195829 0.081 Uiso 1 1 calc R . . . .
C17 C 0.25143(14) 1.8511(3) 0.14118(5) 0.0613(5) Uani 1 1 d . . . . .
H17 H 0.195752 1.924087 0.144985 0.074 Uiso 1 1 calc R . . . .
C19 C 0.30694(15) 1.9143(3) 0.11688(5) 0.0614(5) Uani 1 1 d . . . . .
F21 F 0.05918(10) 0.9371(3) 0.24832(4) 0.1108(6) Uani 1 1 d . . . . .
F22 F 0.14030(12) 0.5878(3) 0.27514(4) 0.1167(6) Uani 1 1 d . . . . .
C24 C 0.41500(14) 1.6314(3) 0.12961(5) 0.0602(5) Uani 1 1 d . . . . .
H24 H 0.469618 1.556135 0.125256 0.072 Uiso 1 1 calc R . . . .
C27 C 0.46623(13) 1.2543(3) 0.16684(5) 0.0546(4) Uani 1 1 d . . . . .
H27 H 0.450639 1.197843 0.145735 0.065 Uiso 1 1 calc R . . . .
C29 C 0.38802(15) 1.8017(4) 0.11093(5) 0.0648(5) Uani 1 1 d . . . . .
H29 H 0.424773 1.840711 0.094216 0.078 Uiso 1 1 calc R . . . .
C30 C 0.20521(15) 1.0373(4) 0.22864(5) 0.0668(5) Uani 1 1 d . . . . .
C33 C 0.28650(18) 0.6840(4) 0.25520(5) 0.0734(6) Uani 1 1 d . . . . .
C38 C 0.15159(16) 0.8999(5) 0.24556(5) 0.0779(7) Uani 1 1 d . . . . .
C39 C 0.45225(13) 1.0798(3) 0.19137(5) 0.0609(5) Uani 1 1 d . . . . .
H39A H 0.450423 0.940763 0.181674 0.073 Uiso 1 1 calc R . . . .
H39B H 0.502083 1.082900 0.207896 0.073 Uiso 1 1 calc R . . . .
C43 C 0.68609(18) 1.5935(4) 0.18368(6) 0.0819(7) Uani 1 1 d . . . . .
H43 H 0.703912 1.715482 0.194682 0.098 Uiso 1 1 calc R . . . .
C49 C 0.63324(16) 1.2359(4) 0.15147(6) 0.0795(7) Uani 1 1 d . . . . .
H49 H 0.616121 1.113683 0.140404 0.095 Uiso 1 1 calc R . . . .
C50 C 0.19215(18) 0.7219(5) 0.25885(5) 0.0801(7) Uani 1 1 d . . . . .
C51 C 0.21445(19) 2.2217(4) 0.10500(7) 0.0883(8) Uani 1 1 d . . . . .
H51A H 0.215019 2.344274 0.091664 0.132 Uiso 1 1 calc GR . . . .
H51B H 0.222321 2.264502 0.126666 0.132 Uiso 1 1 calc GR . . . .
H51C H 0.154970 2.148907 0.101802 0.132 Uiso 1 1 calc GR . . . .
C55 C 0.75140(18) 1.4856(5) 0.16691(7) 0.0892(8) Uani 1 1 d . . . . .
H55 H 0.813488 1.534995 0.166276 0.107 Uiso 1 1 calc R . . . .
C59 C 0.72528(18) 1.3069(6) 0.15126(7) 0.0996(9) Uani 1 1 d . . . . .
H59 H 0.769977 1.231732 0.140291 0.120 Uiso 1 1 calc R . . . .
F4 F 0.05335(11) 0.2797(2) 0.01227(3) 0.0874(4) Uani 1 1 d . . . . .
N14 N -0.01058(14) 0.0053(3) 0.05317(4) 0.0689(5) Uani 1 1 d . . . . .
C16 C 0.06563(17) -0.1026(4) 0.04929(5) 0.0660(5) Uani 1 1 d . . . . .
C18 C -0.19688(16) 0.1418(4) 0.05924(5) 0.0670(5) Uani 1 1 d . . . . .
H18 H -0.153893 0.231255 0.049907 0.080 Uiso 1 1 calc R . . . .
C20 C 0.14344(17) -0.0147(4) 0.03175(5) 0.0680(6) Uani 1 1 d . . . . .
N23 N -0.06950(15) -0.1062(3) 0.07156(5) 0.0781(5) Uani 1 1 d . . . . .
C25 C -0.02148(15) -0.3454(3) 0.11598(5) 0.0617(5) Uani 1 1 d . . . . .
F26 F 0.24750(11) -0.2961(3) 0.04612(4) 0.0996(5) Uani 1 1 d . . . . .
C28 C -0.16519(17) -0.0478(4) 0.07228(5) 0.0673(5) Uani 1 1 d . . . . .
C31 C 0.23268(19) -0.1089(5) 0.03146(5) 0.0797(7) Uani 1 1 d . . . . .
O32 O -0.45035(13) 0.1116(4) 0.07564(5) 0.1006(6) Uani 1 1 d . . . . .
C34 C 0.13605(19) 0.1757(4) 0.01513(5) 0.0732(6) Uani 1 1 d . . . . .
F35 F 0.19960(15) 0.4497(3) -0.01456(4) 0.1138(6) Uani 1 1 d . . . . .
C36 C -0.35567(17) 0.0683(4) 0.07372(6) 0.0764(6) Uani 1 1 d . . . . .
C37 C -0.03168(19) -0.3148(4) 0.08063(5) 0.0735(6) Uani 1 1 d . . . . .
H37 H -0.071961 -0.426432 0.071159 0.088 Uiso 1 1 calc R . . . .
C40 C 0.2114(2) 0.2662(5) 0.00079(6) 0.0863(7) Uani 1 1 d . . . . .
C41 C -0.32399(19) -0.1201(4) 0.08699(6) 0.0834(7) Uani 1 1 d . . . . .
H41 H -0.366970 -0.209160 0.096423 0.100 Uiso 1 1 calc R . . . .
C42 C -0.23028(19) -0.1777(4) 0.08647(6) 0.0793(7) Uani 1 1 d . . . . .
H42 H -0.210188 -0.304427 0.095681 0.095 Uiso 1 1 calc R . . . .
F44 F 0.37268(14) 0.2580(4) -0.01130(4) 0.1312(7) Uani 1 1 d . . . . .
C45 C 0.30922(19) -0.0204(6) 0.01727(6) 0.0927(9) Uani 1 1 d . . . . .
C46 C -0.29113(17) 0.1999(4) 0.05988(5) 0.0735(6) Uani 1 1 d . . . . .
H46 H -0.311278 0.327641 0.050999 0.088 Uiso 1 1 calc R . . . .
C47 C 0.2985(2) 0.1699(6) 0.00219(6) 0.0957(9) Uani 1 1 d . . . . .
F48 F 0.39226(13) -0.1216(4) 0.01855(4) 0.1282(7) Uani 1 1 d . . . . .
C52 C 0.01649(18) -0.4185(5) 0.17950(7) 0.0883(8) Uani 1 1 d . . . . .
H52 H 0.030945 -0.443249 0.200777 0.106 Uiso 1 1 calc R . . . .
C53 C 0.0657(2) -0.3133(4) 0.06541(6) 0.0877(8) Uani 1 1 d . . . . .
H53A H 0.117377 -0.323844 0.081242 0.105 Uiso 1 1 calc R . . . .
H53B H 0.070804 -0.427986 0.050397 0.105 Uiso 1 1 calc R . . . .
C54 C -0.02331(18) -0.1809(4) 0.13701(6) 0.0782(6) Uani 1 1 d . . . . .
H54 H -0.037002 -0.044613 0.129900 0.094 Uiso 1 1 calc R . . . .
C56 C -0.00320(18) -0.5459(4) 0.12740(6) 0.0786(6) Uani 1 1 d . . . . .
H56 H -0.004118 -0.659824 0.113520 0.094 Uiso 1 1 calc R . . . .
C57 C 0.0163(2) -0.5801(5) 0.15888(7) 0.0945(8) Uani 1 1 d . . . . .
H57 H 0.029555 -0.716347 0.166078 0.113 Uiso 1 1 calc R . . . .
C58 C -0.4863(2) 0.2985(6) 0.06133(8) 0.1037(9) Uani 1 1 d . . . . .
H58A H -0.475236 0.295323 0.039178 0.156 Uiso 1 1 calc GR . . . .
H58B H -0.454675 0.418866 0.070780 0.156 Uiso 1 1 calc GR . . . .
H58C H -0.553278 0.308374 0.064313 0.156 Uiso 1 1 calc GR . . . .
C60 C -0.00446(19) -0.2186(5) 0.16931(6) 0.0883(8) Uani 1 1 d . . . . .
H60 H -0.006259 -0.107670 0.183679 0.106 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.338(2) . ?
N2 C5 1.401(2) . ?
N2 N8 1.372(2) . ?
N2 C27 1.472(2) . ?
C3 C5 1.387(3) . ?
C3 C17 1.382(3) . ?
C5 C24 1.394(3) . ?
C6 C11 1.392(3) . ?
C6 C13 1.463(3) . ?
C6 C30 1.392(3) . ?
F7 C30 1.334(3) . ?
N8 C13 1.285(3) . ?
O9 C19 1.376(3) . ?
O9 C51 1.408(3) . ?
F10 C33 1.340(3) . ?
C11 C33 1.372(3) . ?
C12 C15 1.371(3) . ?
C12 C27 1.511(3) . ?
C12 C49 1.372(3) . ?
C13 C39 1.503(3) . ?
C15 C43 1.387(3) . ?
C17 C19 1.381(3) . ?
C19 C29 1.378(3) . ?
F21 C38 1.333(3) . ?
F22 C50 1.332(3) . ?
C24 C29 1.380(3) . ?
C27 C39 1.535(3) . ?
C30 C38 1.374(3) . ?
C33 C50 1.366(4) . ?
C38 C50 1.372(4) . ?
C43 C55 1.370(4) . ?
C49 C59 1.372(3) . ?
C55 C59 1.353(4) . ?
F4 C34 1.338(3) . ?
N14 C16 1.288(3) . ?
N14 N23 1.361(3) . ?
C16 C20 1.462(3) . ?
C16 C53 1.497(3) . ?
C18 C28 1.386(3) . ?
C18 C46 1.379(3) . ?
C20 C31 1.391(3) . ?
C20 C34 1.396(3) . ?
N23 C28 1.399(3) . ?
N23 C37 1.467(3) . ?
C25 C37 1.513(3) . ?
C25 C54 1.371(3) . ?
C25 C56 1.377(3) . ?
F26 C31 1.348(3) . ?
C28 C42 1.388(3) . ?
C31 C45 1.377(4) . ?
O32 C36 1.367(3) . ?
O32 C58 1.412(4) . ?
C34 C40 1.372(4) . ?
F35 C40 1.337(3) . ?
C36 C41 1.383(4) . ?
C36 C46 1.382(3) . ?
C37 C53 1.542(4) . ?
C40 C47 1.369(4) . ?
C41 C42 1.370(4) . ?
F44 C47 1.335(3) . ?
C45 C47 1.367(4) . ?
C45 F48 1.332(3) . ?
C52 C57 1.344(4) . ?
C52 C60 1.364(4) . ?
C54 C60 1.405(4) . ?
C56 C57 1.369(4) . ?

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
C5 N2 C27 122.97(16) . . ?
N8 N2 C5 117.32(15) . . ?
N8 N2 C27 111.95(15) . . ?
C17 C3 C5 120.78(19) . . ?
C3 C5 N2 121.37(18) . . ?
C3 C5 C24 118.13(18) . . ?
C24 C5 N2 120.48(17) . . ?
C11 C6 C13 121.61(18) . . ?
C30 C6 C11 114.84(19) . . ?
C30 C6 C13 123.34(19) . . ?
C13 N8 N2 109.09(16) . . ?
C19 O9 C51 117.5(2) . . ?
F1 C11 C6 120.39(18) . . ?
F1 C11 C33 116.5(2) . . ?
C33 C11 C6 123.1(2) . . ?
C15 C12 C27 123.67(18) . . ?
C15 C12 C49 118.4(2) . . ?
C49 C12 C27 117.95(18) . . ?
C6 C13 C39 125.29(18) . . ?
N8 C13 C6 121.46(18) . . ?
N8 C13 C39 113.23(17) . . ?
C12 C15 C43 120.5(2) . . ?
C19 C17 C3 120.48(19) . . ?
O9 C19 C17 125.6(2) . . ?
O9 C19 C29 115.2(2) . . ?
C29 C19 C17 119.28(19) . . ?
C29 C24 C5 120.80(19) . . ?
N2 C27 C12 114.49(16) . . ?
N2 C27 C39 101.42(15) . . ?
C12 C27 C39 113.22(16) . . ?
C19 C29 C24 120.4(2) . . ?
F7 C30 C6 120.6(2) . . ?
F7 C30 C38 116.8(2) . . ?
C38 C30 C6 122.6(2) . . ?
F10 C33 C11 119.7(2) . . ?
F10 C33 C50 120.3(2) . . ?
C50 C33 C11 120.0(2) . . ?
F21 C38 C30 119.7(3) . . ?
F21 C38 C50 119.9(2) . . ?
C50 C38 C30 120.3(2) . . ?
C13 C39 C27 101.85(16) . . ?
C55 C43 C15 119.8(2) . . ?
C59 C49 C12 121.0(2) . . ?
F22 C50 C33 120.4(3) . . ?
F22 C50 C38 120.5(2) . . ?
C33 C50 C38 119.1(2) . . ?
C59 C55 C43 119.8(2) . . ?
C55 C59 C49 120.4(3) . . ?
C16 N14 N23 109.37(19) . . ?
N14 C16 C20 120.8(2) . . ?
N14 C16 C53 113.3(2) . . ?
C20 C16 C53 125.8(2) . . ?
C46 C18 C28 121.1(2) . . ?
C31 C20 C16 122.7(2) . . ?
C31 C20 C34 114.3(2) . . ?
C34 C20 C16 123.0(2) . . ?
N14 N23 C28 119.24(18) . . ?
N14 N23 C37 113.11(19) . . ?
C28 N23 C37 124.8(2) . . ?
C54 C25 C37 123.0(2) . . ?
C54 C25 C56 118.5(2) . . ?
C56 C25 C37 118.3(2) . . ?
C18 C28 N23 120.9(2) . . ?
C18 C28 C42 118.5(2) . . ?
C42 C28 N23 120.6(2) . . ?
F26 C31 C20 119.5(2) . . ?
F26 C31 C45 116.8(3) . . ?
C45 C31 C20 123.7(3) . . ?
C36 O32 C58 118.2(2) . . ?
F4 C34 C20 120.9(2) . . ?
F4 C34 C40 116.3(2) . . ?
C40 C34 C20 122.8(3) . . ?
O32 C36 C41 116.5(2) . . ?
O32 C36 C46 124.5(2) . . ?
C46 C36 C41 119.0(2) . . ?
N23 C37 C25 113.08(19) . . ?
N23 C37 C53 101.76(19) . . ?
C25 C37 C53 111.7(2) . . ?
F35 C40 C34 119.7(3) . . ?
F35 C40 C47 119.9(3) . . ?
C47 C40 C34 120.3(3) . . ?
C42 C41 C36 121.0(2) . . ?
C41 C42 C28 120.4(2) . . ?
C47 C45 C31 119.3(3) . . ?
F48 C45 C31 119.4(3) . . ?
F48 C45 C47 121.3(3) . . ?
C18 C46 C36 120.0(2) . . ?
F44 C47 C40 120.8(3) . . ?
F44 C47 C45 119.7(3) . . ?
C45 C47 C40 119.4(3) . . ?
C57 C52 C60 120.2(3) . . ?
C16 C53 C37 102.4(2) . . ?
C25 C54 C60 119.9(2) . . ?
C57 C56 C25 121.0(3) . . ?
C52 C57 C56 120.6(3) . . ?
C52 C60 C54 119.7(3) . . ?

_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 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.663
####################################################################### 
# 
# 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_exp_15560
_database_code_depnum_ccdc_archive 'CCDC 1917276'
_audit_update_record             
;
2019-05-20 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;
_audit_creation_date             2019-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 F5 N3'
_chemical_formula_sum            'C25 H22 F5 N3'
_chemical_formula_weight         459.45
_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 0.0181 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'

_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                   19.5027(9)
_cell_length_b                   5.9539(3)
_cell_length_c                   20.2366(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.013(5)
_cell_angle_gamma                90
_cell_volume                     2193.54(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5153
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1180
_cell_measurement_theta_min      3.9230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20846
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.872
_diffrn_reflns_theta_min         3.930
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  77.00   1.00    5.25    --   37.78 -99.00 -60.00   81
  2  ω    -29.00  55.00   1.00    5.25    --   37.78 -57.00-120.00   84
  3  ω    -30.00  65.00   1.00    5.25    --   37.78 -77.00 150.00   95
  4  ω     -4.00  77.00   1.00    5.25    --   37.78 -99.00  30.00   81
  5  ω     11.00 105.00   1.00    5.25    --   37.78  77.00 -90.00   94
  6  ω    -29.00  55.00   1.00    5.25    --   37.78 -57.00  30.00   84
  7  ω     21.00 105.00   1.00    5.25    --   37.78  57.00   0.00   84
  8  ω     40.00 125.00   1.00   21.00    --  108.00 -45.00-150.00   85
  9  ω     41.00 126.00   1.00   21.00    --  108.00 -61.00 120.00   85
 10  ω     39.00 109.00   1.00   21.00    --  108.00 -94.00  90.00   70
 11  ω     70.00 178.00   1.00   21.00    --  108.00  15.00 -60.00  108
 12  ω     38.00 116.00   1.00   21.00    --  108.00-111.00-120.00   78
 13  ω     37.00 146.00   1.00   21.00    --  108.00 -15.00  90.00  109
 14  ω    -34.00  67.00   1.00    5.25    --   37.78 -19.00 -90.00  101
 15  ω     21.00 105.00   1.00    5.25    --   37.78  57.00  30.00   84
 16  ω     11.00 105.00   1.00    5.25    --   37.78  77.00 150.00   94
 17  ω     11.00 105.00   1.00    5.25    --   37.78  77.00  90.00   94
 18  ω     21.00 105.00   1.00    5.25    --   37.78  57.00-120.00   84
 19  ω     21.00 105.00   1.00    5.25    --   37.78  57.00  90.00   84
 20  ω     91.00 176.00   1.00   21.00    --  108.00  45.00-180.00   85
 21  ω     81.00 172.00   1.00   21.00    --  108.00  77.00 120.00   91
 22  ω     81.00 176.00   1.00   21.00    --  108.00  77.00-150.00   95
 23  ω     70.00 178.00   1.00   21.00    --  108.00  15.00  30.00  108
 24  ω     41.00 126.00   1.00   21.00    --  108.00 -61.00 -30.00   85
 25  ω     87.00 178.00   1.00   21.00    --  108.00  30.00 120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0842448000
_diffrn_orient_matrix_UB_12      0.0166173000
_diffrn_orient_matrix_UB_13      0.0238500000
_diffrn_orient_matrix_UB_21      0.0053752000
_diffrn_orient_matrix_UB_22      0.0216306000
_diffrn_orient_matrix_UB_23      0.0775771000
_diffrn_orient_matrix_UB_31      0.0058849000
_diffrn_orient_matrix_UB_32      -0.2572623000
_diffrn_orient_matrix_UB_33      0.0080403000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2869
_reflns_number_total             4257
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.920
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      1.054
_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)+(0.1611P)²+0.4132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2284
_refine_ls_wR_factor_ref         0.2659
_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:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C9BA(H9BA,H9BB), C2CA(H2CA,H2CB), C6CA(H6CA,H6CB)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C21(H21), C22(H22), C24(H24), C20(H20), C26(H26),
 C28(H28), C25(H25)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.18865(12) 0.8929(4) 0.10585(10) 0.1030(7) Uani 1 1 d . . . . .
F7 F 0.20187(12) 0.7760(4) 0.23569(9) 0.1125(8) Uani 1 1 d . . . . .
F11 F 0.05006(10) 0.2340(3) 0.01850(9) 0.0897(6) Uani 1 1 d . . . . .
C3 C 0.12027(12) 0.5673(5) 0.05483(13) 0.0661(7) Uani 1 1 d . . . . .
N9 N 0.08354(12) 0.4968(5) -0.06954(11) 0.0766(7) Uani 1 1 d . . . . .
F13 F 0.14153(11) 0.3862(4) 0.25990(9) 0.1062(7) Uani 1 1 d . . . . .
F19 F 0.06456(12) 0.1247(4) 0.14854(11) 0.1074(7) Uani 1 1 d . . . . .
C5 C 0.11676(13) 0.6270(5) -0.01629(13) 0.0689(7) Uani 1 1 d . . . . .
C4 C 0.16486(15) 0.6394(6) 0.18165(14) 0.0807(8) Uani 1 1 d . . . . .
C8 C 0.13424(15) 0.4462(6) 0.19404(14) 0.0807(9) Uani 1 1 d . . . . .
C2 C 0.15750(15) 0.6997(5) 0.11364(14) 0.0737(7) Uani 1 1 d . . . . .
C6 C 0.08908(14) 0.3742(5) 0.06982(13) 0.0706(7) Uani 1 1 d . . . . .
C17 C 0.05114(13) 0.4891(6) -0.19509(13) 0.0728(8) Uani 1 1 d . . . . .
C12 C 0.09563(16) 0.3128(6) 0.13789(15) 0.0784(8) Uani 1 1 d . . . . .
C18 C 0.20195(14) 0.7596(5) -0.13343(12) 0.0688(7) Uani 1 1 d . . . . .
N14 N 0.08897(14) 0.5872(6) -0.12912(12) 0.0901(8) Uani 1 1 d . . . . .
C19 C 0.01245(14) 0.2920(6) -0.19992(14) 0.0759(8) Uani 1 1 d . . . . .
H19 H 0.011760 0.222859 -0.158949 0.091 Uiso 1 1 calc R . . . .
C27 C -0.02688(15) 0.2962(7) -0.32827(14) 0.0843(9) Uani 1 1 d . . . . .
C23 C -0.02526(16) 0.1965(6) -0.26506(15) 0.0831(8) Uani 1 1 d . . . . .
H23 H -0.050287 0.062226 -0.267003 0.100 Uiso 1 1 calc R . . . .
C21 C 0.24239(18) 0.5653(6) -0.11463(16) 0.0854(9) Uani 1 1 d . . . . .
H21 H 0.226586 0.450984 -0.092197 0.103 Uiso 1 1 calc R . . . .
C22 C 0.22618(18) 0.9271(6) -0.16693(16) 0.0874(9) Uani 1 1 d . . . . .
H22 H 0.199048 1.058699 -0.180522 0.105 Uiso 1 1 calc R . . . .
C24 C 0.01137(16) 0.4936(7) -0.32202(15) 0.0905(10) Uani 1 1 d . . . . .
H24 H 0.010789 0.566299 -0.362886 0.109 Uiso 1 1 calc R . . . .
C15 C 0.13359(17) 0.7906(5) -0.11703(15) 0.0785(8) Uani 1 1 d . . . . .
H15 H 0.104398 0.913892 -0.145565 0.094 Uiso 1 1 calc R . . . .
N29 N -0.06361(19) 0.1939(7) -0.39355(14) 0.1126(11) Uani 1 1 d . . . . .
C9BA C 0.14792(19) 0.8339(6) -0.03755(17) 0.0876(9) Uani 1 1 d . . . . .
H9BA H 0.200028 0.848623 -0.010535 0.105 Uiso 1 1 calc R . . . .
H9BB H 0.122783 0.968151 -0.031211 0.105 Uiso 1 1 calc R . . . .
C20 C 0.05060(16) 0.5874(7) -0.25715(15) 0.0901(10) Uani 1 1 d . . . . .
H20 H 0.077078 0.718808 -0.255121 0.108 Uiso 1 1 calc R . . . .
C26 C 0.2903(2) 0.9013(8) -0.1805(2) 0.1044(12) Uani 1 1 d . . . . .
H26 H 0.306680 1.015685 -0.202410 0.125 Uiso 1 1 calc R . . . .
C2CA C -0.0678(4) 0.2976(13) -0.4583(2) 0.166(3) Uani 1 1 d . . . . .
H2CA H -0.022131 0.376245 -0.451136 0.199 Uiso 1 1 calc R . . . .
H2CB H -0.073178 0.181861 -0.493590 0.199 Uiso 1 1 calc R . . . .
C28 C 0.3298(2) 0.7054(9) -0.1613(2) 0.1056(13) Uani 1 1 d . . . . .
H28 H 0.372792 0.687524 -0.170630 0.127 Uiso 1 1 calc R . . . .
C25 C 0.30668(19) 0.5375(8) -0.12873(19) 0.0999(11) Uani 1 1 d . . . . .
H25 H 0.333592 0.405223 -0.116017 0.120 Uiso 1 1 calc R . . . .
C32 C -0.1844(4) 0.082(2) -0.3959(3) 0.282(7) Uani 1 1 d . . . . .
H32A H -0.176929 0.139859 -0.349543 0.424 Uiso 1 1 calc GR . . . .
H32B H -0.215652 -0.047891 -0.404593 0.424 Uiso 1 1 calc GR . . . .
H32C H -0.207111 0.194780 -0.430703 0.424 Uiso 1 1 calc GR . . . .
C6CA C -0.1116(4) 0.0171(11) -0.4002(2) 0.167(3) Uani 1 1 d . . . . .
H6CA H -0.088297 -0.091639 -0.363270 0.200 Uiso 1 1 calc R . . . .
H6CB H -0.120435 -0.056092 -0.445333 0.200 Uiso 1 1 calc R . . . .
C1 C -0.1249(9) 0.446(2) -0.4837(6) 0.395(11) Uani 1 1 d . . . . .
H1A H -0.151963 0.449467 -0.452357 0.592 Uiso 1 1 calc GR . . . .
H1B H -0.156676 0.399359 -0.529919 0.592 Uiso 1 1 calc GR . . . .
H1C H -0.105952 0.593060 -0.486487 0.592 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.337(4) . ?
F7 C4 1.346(3) . ?
F11 C6 1.337(3) . ?
C3 C5 1.460(4) . ?
C3 C2 1.395(4) . ?
C3 C6 1.384(4) . ?
N9 C5 1.297(4) . ?
N9 N14 1.359(3) . ?
F13 C8 1.337(3) . ?
F19 C12 1.327(4) . ?
C5 C9BA 1.503(4) . ?
C4 C8 1.361(5) . ?
C4 C2 1.379(4) . ?
C8 C12 1.370(4) . ?
C6 C12 1.386(4) . ?
C17 N14 1.400(4) . ?
C17 C19 1.380(4) . ?
C17 C20 1.382(4) . ?
C18 C21 1.375(4) . ?
C18 C22 1.381(4) . ?
C18 C15 1.496(4) . ?
N14 C15 1.460(4) . ?
C19 C23 1.381(4) . ?
C27 C23 1.400(5) . ?
C27 C24 1.373(5) . ?
C27 N29 1.397(4) . ?
C21 C25 1.392(5) . ?
C22 C26 1.382(5) . ?
C24 C20 1.379(4) . ?
C15 C9BA 1.552(4) . ?
N29 C2CA 1.425(6) . ?
N29 C6CA 1.383(7) . ?
C26 C28 1.374(6) . ?
C2CA C1 1.368(13) . ?
C28 C25 1.360(6) . ?
C32 C6CA 1.503(9) . ?

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 C3 C5 122.0(3) . . ?
C6 C3 C5 123.3(2) . . ?
C6 C3 C2 114.7(2) . . ?
C5 N9 N14 109.0(3) . . ?
C3 C5 C9BA 126.9(2) . . ?
N9 C5 C3 120.4(3) . . ?
N9 C5 C9BA 112.6(2) . . ?
F7 C4 C8 120.3(3) . . ?
F7 C4 C2 119.2(3) . . ?
C8 C4 C2 120.6(3) . . ?
F13 C8 C4 120.9(3) . . ?
F13 C8 C12 120.2(3) . . ?
C4 C8 C12 119.0(3) . . ?
F1 C2 C3 120.4(3) . . ?
F1 C2 C4 116.9(3) . . ?
C4 C2 C3 122.7(3) . . ?
F11 C6 C3 121.4(2) . . ?
F11 C6 C12 115.6(3) . . ?
C3 C6 C12 123.1(3) . . ?
C19 C17 N14 120.7(3) . . ?
C19 C17 C20 118.0(3) . . ?
C20 C17 N14 121.3(3) . . ?
F19 C12 C8 120.1(3) . . ?
F19 C12 C6 119.9(3) . . ?
C8 C12 C6 119.9(3) . . ?
C21 C18 C22 118.7(3) . . ?
C21 C18 C15 120.7(3) . . ?
C22 C18 C15 120.6(3) . . ?
N9 N14 C17 119.9(3) . . ?
N9 N14 C15 114.3(2) . . ?
C17 N14 C15 125.8(2) . . ?
C17 C19 C23 120.6(3) . . ?
C24 C27 C23 116.4(3) . . ?
C24 C27 N29 122.5(3) . . ?
N29 C27 C23 121.0(4) . . ?
C19 C23 C27 121.8(3) . . ?
C18 C21 C25 120.9(3) . . ?
C18 C22 C26 120.7(4) . . ?
C27 C24 C20 122.2(3) . . ?
C18 C15 C9BA 114.0(2) . . ?
N14 C15 C18 112.7(3) . . ?
N14 C15 C9BA 100.7(2) . . ?
C27 N29 C2CA 121.5(4) . . ?
C6CA N29 C27 121.6(3) . . ?
C6CA N29 C2CA 115.3(4) . . ?
C5 C9BA C15 102.7(2) . . ?
C24 C20 C17 120.9(3) . . ?
C28 C26 C22 119.6(4) . . ?
C1 C2CA N29 113.3(8) . . ?
C25 C28 C26 120.8(3) . . ?
C28 C25 C21 119.4(4) . . ?
N29 C6CA C32 114.8(7) . . ?

_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 1.327
_oxdiff_exptl_absorpt_empirical_full_min 0.544
####################################################################### 
# 
# 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_exp_15640
_database_code_depnum_ccdc_archive 'CCDC 1917277'
_audit_update_record             
;
2019-05-20 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;
_audit_creation_date             2019-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H15 F5 N2)'
_chemical_formula_sum            'C44 H30 F10 N4'
_chemical_formula_weight         804.72
_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 0.0181 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'

_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                   11.1225(4)
_cell_length_b                   12.8307(5)
_cell_length_c                   13.8928(5)
_cell_angle_alpha                100.865(3)
_cell_angle_beta                 91.711(3)
_cell_angle_gamma                103.357(3)
_cell_volume                     1888.83(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12472
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.7230
_cell_measurement_theta_min      4.0900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.022
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34588
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.740
_diffrn_reflns_theta_min         4.097
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00 107.00   1.00    1.00    --   35.91  19.00 -60.00  100
  2  ω     -4.00  75.00   1.00    1.00    --   35.91 -99.00 -30.00   79
  3  ω      9.00 103.00   1.00    1.00    --   35.91  77.00 -90.00   94
  4  ω     56.00 108.00   1.00    1.00    --   35.91 179.00-120.00   52
  5  ω    -35.00  65.00   1.00    1.00    --   35.91 -19.00  90.00  100
  6  ω     53.00 108.00   1.00    1.00    --   35.91-179.00 -60.00   55
  7  ω     -4.00  75.00   1.00    1.00    --   35.91 -99.00 150.00   79
  8  ω    -31.00  53.00   1.00    1.00    --   35.91 -57.00-120.00   84
  9  ω     -4.00  75.00   1.00    1.00    --   35.91 -99.00 120.00   79
 10  ω     56.00 108.00   1.00    1.00    --   35.91 179.00  60.00   52
 11  ω    -31.00  53.00   1.00    1.00    --   35.91 -57.00   0.00   84
 12  ω     87.00 178.00   1.00    1.00    --  108.00  30.00   0.00   91
 13  ω     41.00 125.00   1.00    1.00    --  108.00 -59.00-150.00   84
 14  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00-180.00   70
 15  ω     40.00 125.00   1.00    1.00    --  108.00 -45.00 120.00   85
 16  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00   0.00   70
 17  ω     40.00 125.00   1.00    1.00    --  108.00 -45.00 -30.00   85
 18  ω     40.00 125.00   1.00    1.00    --  108.00 -45.00-150.00   85
 19  ω     90.00 175.00   1.00    1.00    --  108.00  61.00 150.00   85
 20  ω     38.00 116.00   1.00    1.00    --  108.00-111.00 120.00   78
 21  ω     40.00 125.00   1.00    1.00    --  108.00 -45.00  30.00   85
 22  ω     38.00 116.00   1.00    1.00    --  108.00-111.00 -60.00   78
 23  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00 120.00   70
 24  ω     39.00 177.00   1.00    1.00    --  108.00   0.00 -30.00  138
 25  ω     19.00 103.00   1.00    1.00    --   35.91  57.00-120.00   84
 26  ω      7.00 107.00   1.00    1.00    --   35.91  19.00-180.00  100
 27  ω      9.00 103.00   1.00    1.00    --   35.91  77.00 120.00   94
 28  ω     19.00 103.00   1.00    1.00    --   35.91  57.00  90.00   84
 29  ω      9.00 103.00   1.00    1.00    --   35.91  77.00  30.00   94
 30  ω      9.00 103.00   1.00    1.00    --   35.91  77.00-180.00   94
 31  ω     19.00 103.00   1.00    1.00    --   35.91  57.00  30.00   84
 32  ω     19.00 103.00   1.00    1.00    --   35.91  57.00 -30.00   84
 33  ω      9.00 103.00   1.00    1.00    --   35.91  77.00 -30.00   94
 34  ω     -4.00  75.00   1.00    1.00    --   35.91 -99.00-150.00   79
 35  ω     91.00 176.00   1.00    1.00    --  108.00  45.00 120.00   85
 36  ω     91.00 176.00   1.00    1.00    --  108.00  45.00  30.00   85
 37  ω     87.00 178.00   1.00    1.00    --  108.00  30.00-150.00   91
 38  ω     81.00 176.00   1.00    1.00    --  108.00  77.00 -90.00   95
 39  ω     87.00 178.00   1.00    1.00    --  108.00  30.00  90.00   91
 40  ω     81.00 176.00   1.00    1.00    --  108.00  77.00  30.00   95
 41  ω     81.00 176.00   1.00    1.00    --  108.00  77.00 -60.00   95
 42  ω     81.00 176.00   1.00    1.00    --  108.00  77.00-120.00   95
 43  ω     81.00 176.00   1.00    1.00    --  108.00  77.00 120.00   95
 44  ω     81.00 176.00   1.00    1.00    --  108.00  77.00-150.00   95
 45  ω      9.00 103.00   1.00    1.00    --   35.91  77.00  60.00   94
 46  ω     17.00 105.00   1.00    1.00    --   35.91  37.00 -30.00   88
 47  ω     19.00 103.00   1.00    1.00    --   35.91  57.00 -60.00   84
 48  ω     17.00 105.00   1.00    1.00    --   35.91  37.00-150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0471714000
_diffrn_orient_matrix_UB_12      0.1007823000
_diffrn_orient_matrix_UB_13      -0.0127745000
_diffrn_orient_matrix_UB_21      -0.0927513000
_diffrn_orient_matrix_UB_22      -0.0216866000
_diffrn_orient_matrix_UB_23      0.0782955000
_diffrn_orient_matrix_UB_31      0.0977681000
_diffrn_orient_matrix_UB_32      0.0724043000
_diffrn_orient_matrix_UB_33      0.0808193000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5870
_reflns_number_total             7310
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         7310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      1.045
_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)+(0.0983P)²+0.4424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1672
_refine_ls_wR_factor_ref         0.1799
_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:
 C12(H12), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C16(H16), C17(H17), C24(H24), C25(H25), C29(H29),
 C32(H32), C34(H34), C36(H36), C39(H39), C40(H40), C42(H42), C47(H47), C48(H48),
  C56(H56), C57(H57), C58(H58)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C54(H54A,H54B,H54C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.29264(11) 0.35770(10) 0.11747(11) 0.0713(4) Uani 1 1 d . . . . .
F2 F -0.14211(11) 0.27051(10) 0.13689(11) 0.0741(4) Uani 1 1 d . . . . .
N3 N -0.01352(14) 0.12481(11) 0.15671(11) 0.0485(4) Uani 1 1 d . . . . .
N4 N 0.01465(14) 0.02570(11) 0.15711(12) 0.0488(4) Uani 1 1 d . . . . .
F5 F 0.28692(14) 0.55982(11) 0.10953(15) 0.1018(6) Uani 1 1 d . . . . .
C6 C -0.08748(16) -0.06504(13) 0.14828(13) 0.0444(4) Uani 1 1 d . . . . .
F7 F -0.14401(14) 0.47427(12) 0.13119(15) 0.0971(5) Uani 1 1 d . . . . .
C8 C 0.07585(18) 0.30341(14) 0.12910(13) 0.0484(4) Uani 1 1 d . . . . .
C9 C 0.21091(16) -0.03792(14) 0.15836(14) 0.0490(4) Uani 1 1 d . . . . .
C10 C -0.03334(19) 0.33872(15) 0.13163(16) 0.0553(5) Uani 1 1 d . . . . .
C11 C -0.20671(18) -0.05127(15) 0.16025(15) 0.0531(4) Uani 1 1 d . . . . .
H11 H -0.219991 0.018801 0.173922 0.064 Uiso 1 1 calc R . . . .
C12 C 0.13083(16) 0.01975(14) 0.10968(13) 0.0458(4) Uani 1 1 d . . . . .
H12 H 0.110324 -0.017640 0.040835 0.055 Uiso 1 1 calc R . . . .
C13 C 0.18235(19) 0.38256(16) 0.12091(15) 0.0554(5) Uani 1 1 d . . . . .
C14 C 0.08064(16) 0.19058(13) 0.13229(13) 0.0452(4) Uani 1 1 d . . . . .
C15 C -0.17151(18) -0.25927(15) 0.12148(15) 0.0538(5) Uani 1 1 d . . . . .
H15 H -0.158522 -0.329467 0.108946 0.065 Uiso 1 1 calc R . . . .
C16 C -0.30546(18) -0.14076(16) 0.15200(16) 0.0574(5) Uani 1 1 d . . . . .
H16 H -0.384578 -0.129667 0.160038 0.069 Uiso 1 1 calc R . . . .
C17 C -0.07051(17) -0.17100(14) 0.12880(15) 0.0516(4) Uani 1 1 d . . . . .
H17 H 0.008471 -0.182427 0.120734 0.062 Uiso 1 1 calc R . . . .
F18 F 0.06940(16) 0.62303(11) 0.11742(16) 0.1086(6) Uani 1 1 d . . . . .
C19 C 0.18986(17) 0.14138(14) 0.11348(15) 0.0493(4) Uani 1 1 d . . . . .
H19A H 0.254793 0.170631 0.166340 0.059 Uiso 1 1 calc R . . . .
H19B H 0.223433 0.153203 0.051712 0.059 Uiso 1 1 calc R . . . .
C20 C -0.29048(18) -0.24701(15) 0.13206(15) 0.0529(4) Uani 1 1 d . . . . .
C21 C 0.1811(2) 0.48834(16) 0.11679(18) 0.0671(6) Uani 1 1 d . . . . .
N22 N -0.4820(2) -0.42017(17) 0.36452(15) 0.0732(5) Uani 1 1 d . . . . .
C23 C 0.0718(2) 0.51987(17) 0.1209(2) 0.0730(6) Uani 1 1 d . . . . .
C24 C -0.7112(2) -0.67271(19) 0.37166(16) 0.0638(5) Uani 1 1 d . . . . .
H24 H -0.661008 -0.721675 0.370318 0.077 Uiso 1 1 calc R . . . .
C25 C 0.26288(19) -0.11454(17) 0.10071(19) 0.0631(5) Uani 1 1 d . . . . .
H25 H 0.249224 -0.127804 0.032649 0.076 Uiso 1 1 calc R . . . .
C26 C -0.3996(2) -0.34480(18) 0.1209(2) 0.0729(6) Uani 1 1 d . . . . .
H26A H -0.443134 -0.356561 0.057635 0.109 Uiso 1 1 calc GR . . . .
H26B H -0.454466 -0.331581 0.171433 0.109 Uiso 1 1 calc GR . . . .
H26C H -0.370539 -0.408393 0.126710 0.109 Uiso 1 1 calc GR . . . .
N27 N -0.53246(18) -0.52950(16) 0.35428(15) 0.0710(5) Uani 1 1 d . . . . .
C28 C -0.0355(2) 0.44482(17) 0.12837(19) 0.0668(6) Uani 1 1 d . . . . .
C29 C 0.2342(2) -0.0178(2) 0.25829(18) 0.0701(6) Uani 1 1 d . . . . .
H29 H 0.201864 0.034259 0.298142 0.084 Uiso 1 1 calc R . . . .
C30 C -0.44590(19) -0.69038(18) 0.29202(17) 0.0633(5) Uani 1 1 d . . . . .
C31 C -0.3629(2) -0.4026(2) 0.37503(16) 0.0721(6) Uani 1 1 d . . . . .
C32 C -0.8372(2) -0.7073(2) 0.38083(16) 0.0698(6) Uani 1 1 d . . . . .
H32 H -0.870023 -0.779501 0.385647 0.084 Uiso 1 1 calc R . . . .
C33 C -0.6594(2) -0.56498(19) 0.36445(15) 0.0618(5) Uani 1 1 d . . . . .
C34 C -0.4630(2) -0.6873(2) 0.19438(18) 0.0748(6) Uani 1 1 d . . . . .
H34 H -0.472437 -0.623523 0.175825 0.090 Uiso 1 1 calc R . . . .
F35 F -0.4496(2) -0.20494(15) 0.42259(16) 0.1224(7) Uani 1 1 d . . . . .
C36 C -0.7379(2) -0.4942(2) 0.36588(18) 0.0733(6) Uani 1 1 d . . . . .
H36 H -0.705935 -0.422050 0.360538 0.088 Uiso 1 1 calc R . . . .
F37 F -0.1044(2) -0.3569(2) 0.35188(19) 0.1413(9) Uani 1 1 d . . . . .
C38 C -0.4388(2) -0.5910(2) 0.37045(17) 0.0673(6) Uani 1 1 d . . . . .
H38 H -0.447296 -0.612325 0.434496 0.081 Uiso 1 1 calc R . . . .
C39 C 0.3546(2) -0.1524(3) 0.2409(3) 0.0956(10) Uani 1 1 d . . . . .
H39 H 0.401589 -0.191790 0.268928 0.115 Uiso 1 1 calc R . . . .
C40 C 0.3067(3) -0.0759(3) 0.3003(2) 0.0951(9) Uani 1 1 d . . . . .
H40 H 0.322565 -0.062682 0.368203 0.114 Uiso 1 1 calc R . . . .
C41 C -0.3177(2) -0.5032(2) 0.37415(19) 0.0778(7) Uani 1 1 d . . . . .
H41A H -0.265103 -0.496401 0.433055 0.093 Uiso 1 1 calc R . . . .
H41B H -0.272344 -0.519338 0.316888 0.093 Uiso 1 1 calc R . . . .
C42 C 0.3340(2) -0.1709(2) 0.1427(3) 0.0845(8) Uani 1 1 d . . . . .
H42 H 0.367979 -0.221863 0.103113 0.101 Uiso 1 1 calc R . . . .
F43 F -0.3051(4) -0.0081(2) 0.43226(19) 0.1798(13) Uani 1 1 d . . . . .
C44 C -0.1568(4) -0.2736(3) 0.3724(2) 0.1052(12) Uani 1 1 d . . . . .
C45 C -0.2532(6) -0.0952(3) 0.4133(3) 0.1287(16) Uani 1 1 d . . . . .
C46 C -0.9154(2) -0.6378(2) 0.38302(17) 0.0765(7) Uani 1 1 d . . . . .
C47 C -0.8630(3) -0.5314(2) 0.37525(18) 0.0808(7) Uani 1 1 d . . . . .
H47 H -0.913773 -0.482976 0.376354 0.097 Uiso 1 1 calc R . . . .
C48 C -0.4313(3) -0.8761(3) 0.2458(4) 0.1150(12) Uani 1 1 d . . . . .
H48 H -0.420013 -0.939583 0.263838 0.138 Uiso 1 1 calc R . . . .
C49 C -0.2849(3) -0.2919(3) 0.38451(18) 0.0859(8) Uani 1 1 d . . . . .
C50 C -0.3280(4) -0.1985(3) 0.4056(2) 0.1025(11) Uani 1 1 d . . . . .
F51 F -0.0585(3) 0.0195(2) 0.40651(18) 0.1956(16) Uani 1 1 d . . . . .
C52 C -0.1284(6) -0.0816(4) 0.3999(3) 0.140(2) Uani 1 1 d . . . . .
C53 C -0.0825(4) -0.1708(5) 0.3817(3) 0.1335(18) Uani 1 1 d . . . . .
C54 C -1.0526(3) -0.6773(3) 0.3928(3) 0.1090(11) Uani 1 1 d . . . . .
H54A H -1.087420 -0.737787 0.339961 0.164 Uiso 1 1 calc GR . . . .
H54B H -1.092536 -0.618951 0.390294 0.164 Uiso 1 1 calc GR . . . .
H54C H -1.064871 -0.700166 0.454474 0.164 Uiso 1 1 calc GR . . . .
F55 F 0.0371(2) -0.1569(3) 0.3698(2) 0.1922(15) Uani 1 1 d . . . . .
C56 C -0.4484(3) -0.8734(3) 0.1513(4) 0.1126(13) Uani 1 1 d . . . . .
H56 H -0.448504 -0.934966 0.103647 0.135 Uiso 1 1 calc R . . . .
C57 C -0.4303(3) -0.7863(3) 0.3166(3) 0.0937(9) Uani 1 1 d . . . . .
H57 H -0.418910 -0.789639 0.382404 0.112 Uiso 1 1 calc R . . . .
C58 C -0.4659(3) -0.7803(3) 0.1236(2) 0.0988(10) Uani 1 1 d . . . . .
H58 H -0.479740 -0.779523 0.057386 0.119 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.337(2) . ?
F2 C10 1.332(2) . ?
N3 N4 1.3791(19) . ?
N3 C14 1.282(2) . ?
N4 C6 1.410(2) . ?
N4 C12 1.479(2) . ?
F5 C21 1.334(3) . ?
C6 C11 1.388(2) . ?
C6 C17 1.393(2) . ?
F7 C28 1.345(3) . ?
C8 C10 1.390(3) . ?
C8 C13 1.394(3) . ?
C8 C14 1.470(2) . ?
C9 C12 1.502(2) . ?
C9 C25 1.391(3) . ?
C9 C29 1.369(3) . ?
C10 C28 1.376(3) . ?
C11 C16 1.378(3) . ?
C12 C19 1.537(2) . ?
C13 C21 1.373(3) . ?
C14 C19 1.501(2) . ?
C15 C17 1.385(3) . ?
C15 C20 1.377(3) . ?
C16 C20 1.389(3) . ?
F18 C23 1.340(2) . ?
C20 C26 1.511(3) . ?
C21 C23 1.367(3) . ?
N22 N27 1.363(3) . ?
N22 C31 1.291(3) . ?
C23 C28 1.370(3) . ?
C24 C32 1.387(3) . ?
C24 C33 1.393(3) . ?
C25 C42 1.372(3) . ?
N27 C33 1.400(3) . ?
N27 C38 1.480(3) . ?
C29 C40 1.401(3) . ?
C30 C34 1.373(3) . ?
C30 C38 1.498(3) . ?
C30 C57 1.384(3) . ?
C31 C41 1.487(4) . ?
C31 C49 1.463(4) . ?
C32 C46 1.379(4) . ?
C33 C36 1.395(3) . ?
C34 C58 1.389(4) . ?
F35 C50 1.367(4) . ?
C36 C47 1.381(4) . ?
F37 C44 1.321(5) . ?
C38 C41 1.536(3) . ?
C39 C40 1.375(5) . ?
C39 C42 1.343(4) . ?
F43 C45 1.360(6) . ?
C44 C49 1.410(5) . ?
C44 C53 1.365(5) . ?
C45 C50 1.375(5) . ?
C45 C52 1.382(7) . ?
C46 C47 1.381(4) . ?
C46 C54 1.512(4) . ?
C48 C56 1.329(5) . ?
C48 C57 1.363(5) . ?
C49 C50 1.377(5) . ?
F51 C52 1.334(4) . ?
C52 C53 1.343(7) . ?
C53 F55 1.321(5) . ?
C56 C58 1.376(5) . ?

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
C14 N3 N4 109.13(14) . . ?
N3 N4 C6 115.85(14) . . ?
N3 N4 C12 111.01(13) . . ?
C6 N4 C12 122.97(14) . . ?
C11 C6 N4 121.11(15) . . ?
C11 C6 C17 118.40(16) . . ?
C17 C6 N4 120.49(16) . . ?
C10 C8 C13 115.16(16) . . ?
C10 C8 C14 123.36(17) . . ?
C13 C8 C14 121.46(17) . . ?
C25 C9 C12 119.37(18) . . ?
C29 C9 C12 121.95(18) . . ?
C29 C9 C25 118.67(19) . . ?
F2 C10 C8 121.22(16) . . ?
F2 C10 C28 116.50(18) . . ?
C28 C10 C8 122.29(19) . . ?
C16 C11 C6 120.41(17) . . ?
N4 C12 C9 114.12(14) . . ?
N4 C12 C19 101.31(13) . . ?
C9 C12 C19 114.28(15) . . ?
F1 C13 C8 120.37(17) . . ?
F1 C13 C21 116.62(18) . . ?
C21 C13 C8 123.0(2) . . ?
N3 C14 C8 119.97(16) . . ?
N3 C14 C19 113.43(14) . . ?
C8 C14 C19 126.55(16) . . ?
C20 C15 C17 122.46(17) . . ?
C11 C16 C20 122.02(18) . . ?
C15 C17 C6 119.83(17) . . ?
C14 C19 C12 101.43(14) . . ?
C15 C20 C16 116.86(17) . . ?
C15 C20 C26 121.43(18) . . ?
C16 C20 C26 121.70(19) . . ?
F5 C21 C13 119.6(2) . . ?
F5 C21 C23 120.52(19) . . ?
C23 C21 C13 119.8(2) . . ?
C31 N22 N27 108.9(2) . . ?
F18 C23 C21 120.4(2) . . ?
F18 C23 C28 120.3(2) . . ?
C21 C23 C28 119.30(18) . . ?
C32 C24 C33 120.3(2) . . ?
C42 C25 C9 121.0(2) . . ?
N22 N27 C33 118.66(19) . . ?
N22 N27 C38 112.50(19) . . ?
C33 N27 C38 124.8(2) . . ?
F7 C28 C10 119.6(2) . . ?
F7 C28 C23 119.98(18) . . ?
C23 C28 C10 120.4(2) . . ?
C9 C29 C40 119.8(2) . . ?
C34 C30 C38 121.0(2) . . ?
C34 C30 C57 118.5(2) . . ?
C57 C30 C38 120.4(2) . . ?
N22 C31 C41 113.8(2) . . ?
N22 C31 C49 120.4(3) . . ?
C49 C31 C41 125.7(2) . . ?
C46 C32 C24 122.0(2) . . ?
C24 C33 N27 120.8(2) . . ?
C24 C33 C36 118.1(2) . . ?
C36 C33 N27 121.1(2) . . ?
C30 C34 C58 119.4(3) . . ?
C47 C36 C33 120.0(3) . . ?
N27 C38 C30 113.90(19) . . ?
N27 C38 C41 101.39(19) . . ?
C30 C38 C41 112.86(19) . . ?
C42 C39 C40 120.6(2) . . ?
C39 C40 C29 119.8(3) . . ?
C31 C41 C38 102.5(2) . . ?
C39 C42 C25 120.1(3) . . ?
F37 C44 C49 120.3(3) . . ?
F37 C44 C53 117.7(4) . . ?
C53 C44 C49 122.0(5) . . ?
F43 C45 C50 118.7(5) . . ?
F43 C45 C52 121.2(4) . . ?
C50 C45 C52 120.0(5) . . ?
C32 C46 C47 117.1(2) . . ?
C32 C46 C54 121.1(3) . . ?
C47 C46 C54 121.8(3) . . ?
C46 C47 C36 122.4(2) . . ?
C56 C48 C57 120.5(3) . . ?
C44 C49 C31 121.3(3) . . ?
C50 C49 C31 124.1(3) . . ?
C50 C49 C44 114.6(3) . . ?
F35 C50 C45 116.5(4) . . ?
F35 C50 C49 120.3(3) . . ?
C45 C50 C49 123.2(4) . . ?
F51 C52 C45 118.6(6) . . ?
F51 C52 C53 122.9(6) . . ?
C53 C52 C45 118.4(4) . . ?
C52 C53 C44 121.7(5) . . ?
F55 C53 C44 120.3(6) . . ?
F55 C53 C52 117.9(5) . . ?
C48 C56 C58 120.4(3) . . ?
C48 C57 C30 121.1(3) . . ?
C56 C58 C34 120.0(3) . . ?

_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 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.673
