# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_234
_database_code_depnum_ccdc_archive 'CCDC 1830098'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-06-08 downloaded from the CCDC.
;
_audit_creation_date             2018-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C25 H19 N3 O)'
_chemical_formula_sum            'C50 H38 N6 O2'
_chemical_formula_weight         754.86
_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'
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                   8.2339(2)
_cell_length_b                   14.7918(4)
_cell_length_c                   17.1794(5)
_cell_angle_alpha                101.330(2)
_cell_angle_beta                 95.203(2)
_cell_angle_gamma                106.126(2)
_cell_volume                     1947.28(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11984
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.1900
_cell_measurement_theta_min      4.6090
_shelx_estimated_absorpt_T_max   0.813
_shelx_estimated_absorpt_T_min   0.764
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19522
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.608
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00  89.00   1.00    1.00    --    0.00  57.00  30.00   40
  2  ω     33.00  88.00   1.00    1.00    --    0.00  38.00-150.00   55
  3  ω     10.00  83.00   1.00    1.00    --    0.00  77.00-120.00   73
  4  ω    -23.00  32.00   1.00    1.00    --    0.00  57.00  30.00   55
  5  ω    -89.00 -14.00   1.00    1.00    --    0.00 -77.00-180.00   75
  6  ω      6.00  59.00   1.00    1.00    --   95.80 -82.00-150.00   53
  7  ω     72.00 182.00   1.00    1.00    --   95.80  15.00 -60.00  110
  8  ω     10.00 127.00   1.00    1.00    --   95.80 -82.00  90.00  117
  9  ω     38.00  63.00   1.00    1.00    --   95.80 -82.00 150.00   25
 10  ω     53.00  79.00   1.00    1.00    --   95.80 -61.00  30.00   26
 11  ω     56.00 127.00   1.00    1.00    --   95.80 -82.00 -30.00   71
 12  ω      7.00 101.00   1.00    1.00    --   95.80 -30.00  90.00   94
 13  ω     47.00 103.00   1.00    1.00    --   95.80 -61.00 -30.00   56
 14  ω      8.00  41.00   1.00    1.00    --   95.80 -61.00  30.00   33
 15  ω     48.00 120.00   1.00    1.00    --   95.80 -61.00-150.00   72
 16  ω      9.00  42.00   1.00    1.00    --   95.80 -61.00-150.00   33
 17  ω      7.00  53.00   1.00    1.00    --   95.80 -15.00 -60.00   46
 18  ω     58.00 122.00   1.00    1.00    --   95.80 -15.00 -60.00   64
 19  ω     93.00 127.00   1.00    1.00    --   95.80 -82.00  30.00   34
 20  ω     67.00 122.00   1.00    1.00    --   95.80 -82.00-150.00   55
 21  ω     48.00 102.00   1.00    1.00    --   95.80 -30.00-180.00   54
 22  ω     94.00 119.00   1.00    1.00    --   95.80 -82.00 150.00   25
 23  ω     94.00 120.00   1.00    1.00    --   95.80 -82.00  60.00   26
 24  ω     85.00 110.00   1.00    1.00    --   95.80 -82.00 120.00   25
 25  ω     34.00 108.00   1.00    1.00    --   95.80 -30.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0761891000
_diffrn_orient_matrix_UB_12      -0.1106795000
_diffrn_orient_matrix_UB_13      -0.0287547000
_diffrn_orient_matrix_UB_21      0.0419539000
_diffrn_orient_matrix_UB_22      -0.0106629000
_diffrn_orient_matrix_UB_23      0.0863356000
_diffrn_orient_matrix_UB_31      -0.1768944000
_diffrn_orient_matrix_UB_32      0.0075501000
_diffrn_orient_matrix_UB_33      0.0169552000
_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                6266
_reflns_number_total             6920
_reflns_odcompleteness_completeness 99.71
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.382
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         6920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.030
_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)+(0.0350P)²+1.0360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C34(H34A,H34B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29),
  C30(H30), C31(H31), C40(H40), C41(H41), C42(H42), C43(H43), C46(H46),
 C47(H47), C48(H48), C49(H49), C50(H50)
;
_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
O1 O 0.48559(15) 0.55796(8) 0.67432(8) 0.0354(3) Uani 1 1 d . . . . .
N1 N 0.15533(18) 0.57139(10) 0.77216(9) 0.0306(3) Uani 1 1 d . . . . .
N2 N 0.28047(16) 0.73857(9) 0.66039(7) 0.0207(3) Uani 1 1 d . . . . .
N3 N 0.19490(18) 0.87544(9) 0.73251(8) 0.0264(3) Uani 1 1 d . . . . .
H3 H 0.203373 0.919268 0.705497 0.032 Uiso 1 1 calc R . . . .
C1 C 0.14374(19) 0.77321(11) 0.69733(9) 0.0226(3) Uani 1 1 d . . . . .
H1 H 0.038995 0.754083 0.658195 0.027 Uiso 1 1 calc R . . . .
C2 C 0.22873(18) 0.89410(11) 0.81552(9) 0.0214(3) Uani 1 1 d . . . . .
C3 C 0.29360(19) 0.98285(11) 0.87036(9) 0.0241(3) Uani 1 1 d . . . . .
H3A H 0.327511 1.040026 0.853026 0.029 Uiso 1 1 calc R . . . .
C4 C 0.30655(19) 0.98401(12) 0.95187(9) 0.0261(3) Uani 1 1 d . . . . .
H4 H 0.348647 1.042899 0.989351 0.031 Uiso 1 1 calc R . . . .
C5 C 0.2579(2) 0.89909(12) 0.97832(10) 0.0285(3) Uani 1 1 d . . . . .
H5 H 0.267553 0.901384 1.033084 0.034 Uiso 1 1 calc R . . . .
C6 C 0.19454(19) 0.81028(12) 0.92287(9) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.161839 0.753080 0.940260 0.031 Uiso 1 1 calc R . . . .
C7 C 0.18087(18) 0.80825(11) 0.84154(9) 0.0213(3) Uani 1 1 d . . . . .
C8 C 0.11144(19) 0.72414(11) 0.76921(9) 0.0228(3) Uani 1 1 d . . . . .
C9 C -0.0632(2) 0.65253(11) 0.77206(11) 0.0298(4) Uani 1 1 d . . . . .
H9A H -0.124396 0.681813 0.810203 0.036 Uiso 1 1 calc R . . . .
H9B H -0.133610 0.629676 0.719555 0.036 Uiso 1 1 calc R . . . .
C10 C -0.0117(2) 0.57007(12) 0.79954(12) 0.0352(4) Uani 1 1 d . . . . .
H10A H -0.000224 0.580329 0.857559 0.042 Uiso 1 1 calc R . . . .
H10B H -0.097332 0.508385 0.775733 0.042 Uiso 1 1 calc R . . . .
C11 C 0.21611(19) 0.65388(10) 0.75794(9) 0.0217(3) Uani 1 1 d . . . . .
C12 C 0.36304(19) 0.69058(10) 0.71424(9) 0.0216(3) Uani 1 1 d . . . . .
C13 C 0.39558(19) 0.60582(11) 0.65572(10) 0.0256(3) Uani 1 1 d . . . . .
C14 C 0.3023(2) 0.59870(11) 0.57760(10) 0.0259(3) Uani 1 1 d . . . . .
C15 C 0.2750(2) 0.53053(12) 0.50492(11) 0.0345(4) Uani 1 1 d . . . . .
H15 H 0.321438 0.479525 0.500978 0.041 Uiso 1 1 calc R . . . .
C16 C 0.1781(2) 0.54038(13) 0.43935(11) 0.0383(4) Uani 1 1 d . . . . .
H16 H 0.158068 0.495586 0.390559 0.046 Uiso 1 1 calc R . . . .
C17 C 0.1097(2) 0.61762(13) 0.44599(11) 0.0355(4) Uani 1 1 d . . . . .
H17 H 0.044247 0.623070 0.401105 0.043 Uiso 1 1 calc R . . . .
C18 C 0.1362(2) 0.68611(12) 0.51703(10) 0.0287(3) Uani 1 1 d . . . . .
H18 H 0.089792 0.737075 0.520393 0.034 Uiso 1 1 calc R . . . .
C19 C 0.23489(19) 0.67653(10) 0.58365(9) 0.0225(3) Uani 1 1 d . . . . .
C20 C 0.52199(19) 0.75834(11) 0.77028(9) 0.0228(3) Uani 1 1 d . . . . .
C21 C 0.6202(2) 0.84107(11) 0.75091(10) 0.0278(3) Uani 1 1 d . . . . .
H21 H 0.587359 0.856734 0.703305 0.033 Uiso 1 1 calc R . . . .
C22 C 0.7672(2) 0.90066(12) 0.80208(12) 0.0348(4) Uani 1 1 d . . . . .
H22 H 0.833506 0.955347 0.788121 0.042 Uiso 1 1 calc R . . . .
C23 C 0.8156(2) 0.87905(14) 0.87393(11) 0.0377(4) Uani 1 1 d . . . . .
H23 H 0.913908 0.919156 0.908303 0.045 Uiso 1 1 calc R . . . .
C24 C 0.7165(2) 0.79735(14) 0.89411(11) 0.0374(4) Uani 1 1 d . . . . .
H24 H 0.747397 0.783122 0.942661 0.045 Uiso 1 1 calc R . . . .
C25 C 0.5715(2) 0.73658(13) 0.84237(10) 0.0293(4) Uani 1 1 d . . . . .
H25 H 0.506927 0.681053 0.855829 0.035 Uiso 1 1 calc R . . . .
O2 O -0.02239(14) 0.07374(8) 0.64521(7) 0.0299(3) Uani 1 1 d . . . . .
N004 N 0.33352(15) 0.28330(9) 0.66234(7) 0.0202(3) Uani 1 1 d . . . . .
N4 N 0.58654(18) 0.41007(10) 0.74411(8) 0.0294(3) Uani 1 1 d . . . . .
N5 N 0.38848(18) 0.07712(10) 0.70619(8) 0.0290(3) Uani 1 1 d . . . . .
C26 C 0.52360(19) 0.31587(11) 0.69050(9) 0.0241(3) Uani 1 1 d . . . . .
H26 H 0.586059 0.312796 0.644616 0.029 Uiso 1 1 calc R . . . .
C27 C 0.59982(19) 0.40052(12) 0.82349(10) 0.0262(3) Uani 1 1 d . . . . .
C28 C 0.6313(2) 0.47219(13) 0.89314(11) 0.0342(4) Uani 1 1 d . . . . .
H28 H 0.643155 0.536066 0.891220 0.041 Uiso 1 1 calc R . . . .
C29 C 0.6445(2) 0.44535(14) 0.96626(11) 0.0377(4) Uani 1 1 d . . . . .
H29 H 0.666048 0.492322 1.013867 0.045 Uiso 1 1 calc R . . . .
C30 C 0.6262(2) 0.35025(15) 0.96963(10) 0.0359(4) Uani 1 1 d . . . . .
H30 H 0.633708 0.333929 1.019135 0.043 Uiso 1 1 calc R . . . .
C31 C 0.5964(2) 0.27894(13) 0.89896(10) 0.0296(4) Uani 1 1 d . . . . .
H31 H 0.584902 0.215085 0.900821 0.036 Uiso 1 1 calc R . . . .
C32 C 0.58438(18) 0.30490(11) 0.82612(9) 0.0234(3) Uani 1 1 d . . . . .
C33 C 0.55345(19) 0.24432(11) 0.74115(9) 0.0237(3) Uani 1 1 d . . . . .
C34 C 0.6776(2) 0.18499(13) 0.72048(10) 0.0308(4) Uani 1 1 d . . . . .
H34A H 0.709895 0.188266 0.667950 0.037 Uiso 1 1 calc R . . . .
H34B H 0.780115 0.207692 0.760326 0.037 Uiso 1 1 calc R . . . .
C35 C 0.5723(2) 0.08181(13) 0.72147(11) 0.0351(4) Uani 1 1 d . . . . .
H35A H 0.597440 0.034994 0.680089 0.042 Uiso 1 1 calc R . . . .
H35B H 0.598876 0.067902 0.773178 0.042 Uiso 1 1 calc R . . . .
C36 C 0.38512(19) 0.16398(11) 0.71915(9) 0.0219(3) Uani 1 1 d . . . . .
C37 C 0.24143(18) 0.20639(10) 0.70150(9) 0.0204(3) Uani 1 1 d . . . . .
C38 C 0.09689(19) 0.13679(10) 0.63422(9) 0.0216(3) Uani 1 1 d . . . . .
C39 C 0.13736(19) 0.16591(10) 0.55999(9) 0.0217(3) Uani 1 1 d . . . . .
C40 C 0.0660(2) 0.12029(11) 0.48018(9) 0.0251(3) Uani 1 1 d . . . . .
H40 H -0.028680 0.065263 0.467795 0.030 Uiso 1 1 calc R . . . .
C41 C 0.1395(2) 0.15886(12) 0.41993(10) 0.0277(3) Uani 1 1 d . . . . .
H41 H 0.097587 0.128259 0.366287 0.033 Uiso 1 1 calc R . . . .
C42 C 0.2771(2) 0.24411(12) 0.44016(10) 0.0305(4) Uani 1 1 d . . . . .
H42 H 0.322606 0.270547 0.399125 0.037 Uiso 1 1 calc R . . . .
C43 C 0.3480(2) 0.29048(12) 0.51892(10) 0.0271(3) Uani 1 1 d . . . . .
H43 H 0.439506 0.347078 0.531154 0.033 Uiso 1 1 calc R . . . .
C44 C 0.27743(19) 0.24946(11) 0.57944(9) 0.0220(3) Uani 1 1 d . . . . .
C45 C 0.17116(18) 0.24298(11) 0.77544(9) 0.0202(3) Uani 1 1 d . . . . .
C46 C 0.1555(2) 0.33575(11) 0.79369(10) 0.0253(3) Uani 1 1 d . . . . .
H46 H 0.190621 0.377774 0.760478 0.030 Uiso 1 1 calc R . . . .
C47 C 0.0875(2) 0.36530(13) 0.86161(10) 0.0327(4) Uani 1 1 d . . . . .
H47 H 0.076312 0.427184 0.873592 0.039 Uiso 1 1 calc R . . . .
C48 C 0.0360(2) 0.30374(14) 0.91169(10) 0.0345(4) Uani 1 1 d . . . . .
H48 H -0.007679 0.324585 0.957638 0.041 Uiso 1 1 calc R . . . .
C49 C 0.0495(2) 0.21097(13) 0.89335(10) 0.0321(4) Uani 1 1 d . . . . .
H49 H 0.014127 0.169265 0.926768 0.038 Uiso 1 1 calc R . . . .
C50 C 0.11589(19) 0.18023(12) 0.82518(9) 0.0257(3) Uani 1 1 d . . . . .
H50 H 0.123576 0.117617 0.812568 0.031 Uiso 1 1 calc R . . . .
H4A H 0.553(3) 0.4573(15) 0.7303(12) 0.040(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
O1 C13 1.2206(19) . ?
N1 C10 1.489(2) . ?
N1 C11 1.265(2) . ?
N2 C1 1.5017(19) . ?
N2 C12 1.4945(18) . ?
N2 C19 1.4017(19) . ?
N3 H3 0.8600 . ?
N3 C1 1.4387(19) . ?
N3 C2 1.385(2) . ?
C1 H1 0.9800 . ?
C1 C8 1.558(2) . ?
C2 C3 1.389(2) . ?
C2 C7 1.394(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.391(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(2) . ?
C7 C8 1.512(2) . ?
C8 C9 1.542(2) . ?
C8 C11 1.519(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.539(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.511(2) . ?
C12 C13 1.548(2) . ?
C12 C20 1.519(2) . ?
C13 C14 1.454(2) . ?
C14 C15 1.398(2) . ?
C14 C19 1.401(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.398(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.396(2) . ?
C20 C21 1.386(2) . ?
C20 C25 1.393(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.386(3) . ?
C25 H25 0.9300 . ?
O2 C38 1.2099(18) . ?
N004 C26 1.5060(19) . ?
N004 C37 1.4953(17) . ?
N004 C44 1.4017(19) . ?
N4 C26 1.438(2) . ?
N4 C27 1.396(2) . ?
N4 H4A 0.88(2) . ?
N5 C35 1.492(2) . ?
N5 C36 1.269(2) . ?
C26 H26 0.9800 . ?
C26 C33 1.551(2) . ?
C27 C28 1.384(2) . ?
C27 C32 1.395(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.394(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.386(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.395(2) . ?
C31 H31 0.9300 . ?
C31 C32 1.382(2) . ?
C32 C33 1.513(2) . ?
C33 C34 1.544(2) . ?
C33 C36 1.513(2) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.536(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.519(2) . ?
C37 C38 1.554(2) . ?
C37 C45 1.509(2) . ?
C38 C39 1.461(2) . ?
C39 C40 1.397(2) . ?
C39 C44 1.395(2) . ?
C40 H40 0.9300 . ?
C40 C41 1.385(2) . ?
C41 H41 0.9300 . ?
C41 C42 1.399(2) . ?
C42 H42 0.9300 . ?
C42 C43 1.382(2) . ?
C43 H43 0.9300 . ?
C43 C44 1.396(2) . ?
C45 C46 1.391(2) . ?
C45 C50 1.395(2) . ?
C46 H46 0.9300 . ?
C46 C47 1.386(2) . ?
C47 H47 0.9300 . ?
C47 C48 1.381(3) . ?
C48 H48 0.9300 . ?
C48 C49 1.384(3) . ?
C49 H49 0.9300 . ?
C49 C50 1.386(2) . ?
C50 H50 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C10 106.14(13) . . ?
C12 N2 C1 111.16(11) . . ?
C19 N2 C1 117.86(12) . . ?
C19 N2 C12 107.46(11) . . ?
C1 N3 H3 124.4 . . ?
C2 N3 H3 124.4 . . ?
C2 N3 C1 111.22(12) . . ?
N2 C1 H1 110.6 . . ?
N2 C1 C8 105.60(11) . . ?
N3 C1 N2 114.19(12) . . ?
N3 C1 H1 110.6 . . ?
N3 C1 C8 104.99(12) . . ?
C8 C1 H1 110.6 . . ?
N3 C2 C3 128.61(14) . . ?
N3 C2 C7 110.52(13) . . ?
C3 C2 C7 120.82(14) . . ?
C2 C3 H3A 120.8 . . ?
C2 C3 C4 118.31(14) . . ?
C4 C3 H3A 120.8 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.28(15) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.02(15) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.19(15) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C8 109.10(13) . . ?
C6 C7 C2 120.37(14) . . ?
C6 C7 C8 130.48(14) . . ?
C7 C8 C1 102.94(12) . . ?
C7 C8 C9 115.60(13) . . ?
C7 C8 C11 114.69(12) . . ?
C9 C8 C1 121.90(13) . . ?
C11 C8 C1 102.35(12) . . ?
C11 C8 C9 99.05(12) . . ?
C8 C9 H9A 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C10 C9 C8 102.48(13) . . ?
C10 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
N1 C10 C9 106.36(13) . . ?
N1 C10 H10A 110.5 . . ?
N1 C10 H10B 110.5 . . ?
C9 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.6 . . ?
N1 C11 C8 118.36(13) . . ?
N1 C11 C12 130.19(14) . . ?
C12 C11 C8 110.14(12) . . ?
N2 C12 C11 99.69(11) . . ?
N2 C12 C13 103.98(12) . . ?
N2 C12 C20 113.92(12) . . ?
C11 C12 C13 110.80(12) . . ?
C11 C12 C20 113.07(13) . . ?
C20 C12 C13 114.14(12) . . ?
O1 C13 C12 124.66(15) . . ?
O1 C13 C14 129.14(15) . . ?
C14 C13 C12 106.19(12) . . ?
C15 C14 C13 130.75(15) . . ?
C15 C14 C19 120.94(16) . . ?
C19 C14 C13 108.31(14) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.71(16) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.07(16) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122.13(17) . . ?
C18 C17 H17 118.9 . . ?
C17 C18 H18 121.0 . . ?
C17 C18 C19 117.98(16) . . ?
C19 C18 H18 121.0 . . ?
C14 C19 N2 112.54(14) . . ?
C18 C19 N2 127.30(14) . . ?
C18 C19 C14 120.16(15) . . ?
C21 C20 C12 121.42(14) . . ?
C21 C20 C25 119.12(15) . . ?
C25 C20 C12 119.46(14) . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.43(16) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.30(17) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.48(16) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.38(17) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.27(16) . . ?
C24 C25 H25 119.9 . . ?
C37 N004 C26 111.66(11) . . ?
C44 N004 C26 117.32(12) . . ?
C44 N004 C37 106.97(11) . . ?
C26 N4 H4A 117.7(13) . . ?
C27 N4 C26 109.59(13) . . ?
C27 N4 H4A 121.4(13) . . ?
C36 N5 C35 106.35(14) . . ?
N004 C26 H26 110.7 . . ?
N004 C26 C33 105.06(11) . . ?
N4 C26 N004 113.98(13) . . ?
N4 C26 H26 110.7 . . ?
N4 C26 C33 105.53(12) . . ?
C33 C26 H26 110.7 . . ?
C28 C27 N4 128.16(16) . . ?
C28 C27 C32 121.32(15) . . ?
C32 C27 N4 110.46(14) . . ?
C27 C28 H28 121.1 . . ?
C27 C28 C29 117.72(17) . . ?
C29 C28 H28 121.1 . . ?
C28 C29 H29 119.3 . . ?
C30 C29 C28 121.48(16) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 H30 119.9 . . ?
C29 C30 C31 120.18(16) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 120.6 . . ?
C32 C31 C30 118.81(16) . . ?
C32 C31 H31 120.6 . . ?
C27 C32 C33 109.05(13) . . ?
C31 C32 C27 120.46(15) . . ?
C31 C32 C33 130.48(15) . . ?
C32 C33 C26 102.19(12) . . ?
C32 C33 C34 116.69(13) . . ?
C34 C33 C26 121.05(13) . . ?
C36 C33 C26 102.41(12) . . ?
C36 C33 C32 114.26(12) . . ?
C36 C33 C34 99.81(13) . . ?
C33 C34 H34A 111.2 . . ?
C33 C34 H34B 111.2 . . ?
H34A C34 H34B 109.1 . . ?
C35 C34 C33 103.05(13) . . ?
C35 C34 H34A 111.2 . . ?
C35 C34 H34B 111.2 . . ?
N5 C35 C34 106.71(13) . . ?
N5 C35 H35A 110.4 . . ?
N5 C35 H35B 110.4 . . ?
C34 C35 H35A 110.4 . . ?
C34 C35 H35B 110.4 . . ?
H35A C35 H35B 108.6 . . ?
N5 C36 C33 118.39(14) . . ?
N5 C36 C37 131.24(14) . . ?
C33 C36 C37 109.23(12) . . ?
N004 C37 C36 99.16(11) . . ?
N004 C37 C38 104.30(11) . . ?
N004 C37 C45 114.72(12) . . ?
C36 C37 C38 112.57(12) . . ?
C45 C37 C36 113.49(12) . . ?
C45 C37 C38 111.70(12) . . ?
O2 C38 C37 124.52(14) . . ?
O2 C38 C39 129.93(14) . . ?
C39 C38 C37 105.55(12) . . ?
C40 C39 C38 130.11(14) . . ?
C44 C39 C38 108.39(13) . . ?
C44 C39 C40 121.35(14) . . ?
C39 C40 H40 120.8 . . ?
C41 C40 C39 118.47(15) . . ?
C41 C40 H40 120.8 . . ?
C40 C41 H41 120.2 . . ?
C40 C41 C42 119.67(15) . . ?
C42 C41 H41 120.2 . . ?
C41 C42 H42 118.8 . . ?
C43 C42 C41 122.40(15) . . ?
C43 C42 H42 118.8 . . ?
C42 C43 H43 121.1 . . ?
C42 C43 C44 117.75(15) . . ?
C44 C43 H43 121.1 . . ?
C39 C44 N004 113.08(13) . . ?
C39 C44 C43 120.31(14) . . ?
C43 C44 N004 126.61(14) . . ?
C46 C45 C37 121.94(13) . . ?
C46 C45 C50 119.56(14) . . ?
C50 C45 C37 118.47(13) . . ?
C45 C46 H46 120.2 . . ?
C47 C46 C45 119.69(15) . . ?
C47 C46 H46 120.2 . . ?
C46 C47 H47 119.7 . . ?
C48 C47 C46 120.67(16) . . ?
C48 C47 H47 119.7 . . ?
C47 C48 H48 120.1 . . ?
C47 C48 C49 119.87(16) . . ?
C49 C48 H48 120.1 . . ?
C48 C49 H49 120.0 . . ?
C48 C49 C50 120.02(15) . . ?
C50 C49 H49 120.0 . . ?
C45 C50 H50 119.9 . . ?
C49 C50 C45 120.16(15) . . ?
C49 C50 H50 119.9 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.000 0.500 111.1 44.9 ?

_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 2.524
_oxdiff_exptl_absorpt_empirical_full_min 0.486
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1830573'
_audit_update_record             
;
2018-03-17 deposited with the CCDC.
2018-06-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H16 F3 N3 O2'
_chemical_formula_sum            'C25 H16 F3 N3 O2'
_chemical_formula_weight         447.41
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_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                   19.5242(3)
_cell_length_b                   8.44750(10)
_cell_length_c                   25.5820(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.178(2)
_cell_angle_gamma                90
_cell_volume                     4031.04(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    19854
_cell_measurement_temperature    100(10)
_cell_measurement_theta_max      74.2440
_cell_measurement_theta_min      5.5160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.968
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_transmission_factor_max   0.824
_exptl_transmission_factor_min   0.785
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            43726
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.361
_diffrn_reflns_theta_min         3.692
_diffrn_ambient_temperature      100(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7388
_reflns_number_total             8222
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         8129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1456
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C18(H18A,H18B), C44(H44A,H44B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C39(H39), C35(H35), C28(H28), C50(H50), C10(H10), C3(H3), C27(H27), C5(H5),
 C25(H25), C24(H24), C14(H14), C47(H47), C23(H23), C22(H22), C4(H4), C29(H29),
 C2(H2), C38(H38), C11(H11), C30(H30), C13(H13), C49(H49), C36(H36), C48(H48)
;
_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
F5 F 0.19075(5) 0.24156(10) 0.11384(4) 0.0223(2) Uani 1 1 d . . . . .
F4 F 0.12426(5) 0.04404(10) 0.12157(4) 0.0213(2) Uani 1 1 d . . . . .
O3 O 0.12591(6) -0.25388(12) -0.04730(4) 0.0208(2) Uani 1 1 d . . . . .
F2 F 0.20632(6) 0.62966(11) 0.31294(4) 0.0314(2) Uani 1 1 d . . . . .
O1 O 0.09949(6) 0.01279(12) 0.24012(4) 0.0205(2) Uani 1 1 d . . . . .
F3 F 0.47817(6) 0.46270(16) 0.28026(5) 0.0421(3) Uani 1 1 d . . . . .
F1 F 0.13148(6) 0.50392(12) 0.34542(4) 0.0315(2) Uani 1 1 d . . . . .
N2 N 0.20205(7) 0.23251(15) 0.39407(5) 0.0188(3) Uani 1 1 d . . . . .
N3 N 0.34814(7) 0.08356(16) 0.39370(5) 0.0227(3) Uani 1 1 d . . . . .
F6 F 0.46761(6) 0.29657(15) 0.07927(5) 0.0408(3) Uani 1 1 d . . . . .
N1 N 0.15548(7) 0.25647(14) 0.25632(5) 0.0160(3) Uani 1 1 d . . . . .
N4 N 0.16139(7) -0.03581(14) 0.00853(5) 0.0154(3) Uani 1 1 d . . . . .
C39 C 0.32955(9) 0.08515(18) 0.11808(6) 0.0209(3) Uani 1 1 d . . . . .
H39 H 0.3221 0.0372 0.1487 0.025 Uiso 1 1 calc R . . . .
C31 C 0.09787(8) 0.16287(17) 0.03419(6) 0.0166(3) Uani 1 1 d . . . . .
C9 C 0.27775(8) 0.37712(17) 0.29524(6) 0.0183(3) Uani 1 1 d . . . . .
N5 N 0.20128(7) -0.23266(14) 0.12667(5) 0.0182(3) Uani 1 1 d . . . . .
C15 C 0.21064(8) 0.22171(16) 0.34716(6) 0.0157(3) Uani 1 1 d . . . . .
C40 C 0.21602(8) -0.16674(16) 0.08702(6) 0.0152(3) Uani 1 1 d . . . . .
C20 C 0.27165(8) -0.00481(17) 0.30627(6) 0.0170(3) Uani 1 1 d . . . . .
C26 C 0.10201(8) 0.06760(16) -0.00922(6) 0.0160(3) Uani 1 1 d . . . . .
C45 C 0.29567(8) -0.26312(16) 0.02758(6) 0.0180(3) Uani 1 1 d . . . . .
C35 C 0.28576(9) 0.15685(17) 0.02274(6) 0.0192(3) Uani 1 1 d . . . . .
H35 H 0.2492 0.1568 -0.0102 0.023 Uiso 1 1 calc R . . . .
C34 C 0.27522(8) 0.08361(16) 0.06842(6) 0.0159(3) Uani 1 1 d . . . . .
C42 C 0.16450(8) -0.19253(17) -0.00624(6) 0.0161(3) Uani 1 1 d . . . . .
C17 C 0.14626(8) 0.09753(17) 0.26730(6) 0.0167(3) Uani 1 1 d . . . . .
C19 C 0.18399(9) -0.04310(18) 0.36332(6) 0.0193(3) Uani 1 1 d . . . . .
H19A H 0.2141 -0.1364 0.3729 0.023 Uiso 1 1 calc R . . . .
H19B H 0.1343 -0.0759 0.3497 0.023 Uiso 1 1 calc R . . . .
C1 C 0.10143(8) 0.35825(17) 0.22450(6) 0.0177(3) Uani 1 1 d . . . . .
C28 C -0.00248(9) 0.18856(19) -0.06682(7) 0.0226(3) Uani 1 1 d . . . . .
H28 H -0.0374 0.1974 -0.1005 0.027 Uiso 1 1 calc R . . . .
C50 C 0.29902(9) -0.22430(18) -0.02465(7) 0.0213(3) Uani 1 1 d . . . . .
H50 H 0.2572 -0.1970 -0.0517 0.026 Uiso 1 1 calc R . . . .
C10 C 0.29065(9) 0.35573(18) 0.24516(6) 0.0205(3) Uani 1 1 d . . . . .
H10 H 0.2539 0.3214 0.2151 0.025 Uiso 1 1 calc R . . . .
C18 C 0.19570(9) 0.06903(18) 0.41311(6) 0.0208(3) Uani 1 1 d . . . . .
H18A H 0.1555 0.0617 0.4280 0.025 Uiso 1 1 calc R . . . .
H18B H 0.2390 0.0398 0.4415 0.025 Uiso 1 1 calc R . . . .
C3 C 0.00217(9) 0.4471(2) 0.15243(6) 0.0229(3) Uani 1 1 d . . . . .
H3 H -0.0331 0.4294 0.1194 0.027 Uiso 1 1 calc R . . . .
N6 N 0.35702(8) -0.3342(2) 0.12141(6) 0.0316(3) Uani 1 1 d . . . . .
C27 C 0.05215(8) 0.07716(18) -0.06054(6) 0.0195(3) Uani 1 1 d . . . . .
H27 H 0.0550 0.0127 -0.0893 0.023 Uiso 1 1 calc R . . . .
C6 C 0.10584(8) 0.50560(17) 0.24962(6) 0.0194(3) Uani 1 1 d . . . . .
C33 C 0.20459(8) 0.00164(16) 0.06575(6) 0.0144(3) Uani 1 1 d . . . . .
C5 C 0.05809(9) 0.62602(18) 0.22662(7) 0.0233(3) Uani 1 1 d . . . . .
H5 H 0.0608 0.7241 0.2436 0.028 Uiso 1 1 calc R . . . .
C25 C 0.26332(9) -0.08585(17) 0.25724(6) 0.0191(3) Uani 1 1 d . . . . .
H25 H 0.2178 -0.0978 0.2327 0.023 Uiso 1 1 calc R . . . .
C24 C 0.32251(9) -0.14909(19) 0.24477(6) 0.0229(3) Uani 1 1 d . . . . .
H24 H 0.3158 -0.2052 0.2124 0.027 Uiso 1 1 calc R . . . .
C12 C 0.41173(9) 0.4351(2) 0.28532(8) 0.0283(4) Uani 1 1 d . . . . .
C14 C 0.33326(9) 0.42752(19) 0.34037(6) 0.0235(3) Uani 1 1 d . . . . .
H14 H 0.3246 0.4415 0.3739 0.028 Uiso 1 1 calc R . . . .
C21 C 0.34144(8) 0.00931(17) 0.34207(6) 0.0194(3) Uani 1 1 d . . . . .
C47 C 0.42605(10) -0.2979(2) 0.05521(8) 0.0316(4) Uani 1 1 d . . . . .
H47 H 0.4684 -0.3211 0.0824 0.038 Uiso 1 1 calc R . . . .
C23 C 0.39135(9) -0.1296(2) 0.27995(7) 0.0252(3) Uani 1 1 d . . . . .
H23 H 0.4305 -0.1705 0.2708 0.030 Uiso 1 1 calc R . . . .
C22 C 0.40125(9) -0.0495(2) 0.32853(7) 0.0236(3) Uani 1 1 d . . . . .
H22 H 0.4472 -0.0344 0.3521 0.028 Uiso 1 1 calc R . . . .
C37 C 0.40339(9) 0.2277(2) 0.07595(7) 0.0256(3) Uani 1 1 d . . . . .
C4 C 0.00622(9) 0.5952(2) 0.17746(7) 0.0257(3) Uani 1 1 d . . . . .
H4 H -0.0262 0.6740 0.1610 0.031 Uiso 1 1 calc R . . . .
C29 C -0.00615(9) 0.28674(18) -0.02406(7) 0.0241(3) Uani 1 1 d . . . . .
H29 H -0.0425 0.3617 -0.0299 0.029 Uiso 1 1 calc R . . . .
C2 C 0.04943(8) 0.32512(19) 0.17553(6) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.0463 0.2263 0.1590 0.024 Uiso 1 1 calc R . . . .
C44 C 0.20487(8) -0.43533(17) 0.05897(6) 0.0189(3) Uani 1 1 d . . . . .
H44A H 0.2414 -0.5128 0.0586 0.023 Uiso 1 1 calc R . . . .
H44B H 0.1590 -0.4721 0.0356 0.023 Uiso 1 1 calc R . . . .
C38 C 0.39466(9) 0.1576(2) 0.12219(7) 0.0256(3) Uani 1 1 d . . . . .
H38 H 0.4313 0.1589 0.1551 0.031 Uiso 1 1 calc R . . . .
C46 C 0.36077(9) -0.29857(19) 0.06725(7) 0.0238(3) Uani 1 1 d . . . . .
C7 C 0.16224(9) 0.50124(17) 0.30386(6) 0.0200(3) Uani 1 1 d . . . . .
C11 C 0.35846(10) 0.3854(2) 0.23981(7) 0.0272(4) Uani 1 1 d . . . . .
H11 H 0.3675 0.3721 0.2064 0.033 Uiso 1 1 calc R . . . .
C43 C 0.20180(9) -0.40574(17) 0.11831(6) 0.0207(3) Uani 1 1 d . . . . .
H43A H 0.1589 -0.4530 0.1233 0.025 Uiso 1 1 calc R . . . .
H43B H 0.2432 -0.4528 0.1445 0.025 Uiso 1 1 calc R . . . .
C30 C 0.04370(9) 0.27437(18) 0.02718(7) 0.0212(3) Uani 1 1 d . . . . .
H30 H 0.0409 0.3388 0.0560 0.025 Uiso 1 1 calc R . . . .
C13 C 0.40106(10) 0.4569(2) 0.33577(7) 0.0286(4) Uani 1 1 d . . . . .
H13 H 0.4382 0.4903 0.3657 0.034 Uiso 1 1 calc R . . . .
C49 C 0.36372(10) -0.2258(2) -0.03692(7) 0.0279(4) Uani 1 1 d . . . . .
H49 H 0.3644 -0.2018 -0.0722 0.033 Uiso 1 1 calc R . . . .
C36 C 0.35083(10) 0.23027(19) 0.02620(7) 0.0252(3) Uani 1 1 d . . . . .
H36 H 0.3586 0.2795 -0.0041 0.030 Uiso 1 1 calc R . . . .
C48 C 0.42749(10) -0.2627(2) 0.00278(8) 0.0331(4) Uani 1 1 d . . . . .
H48 H 0.4706 -0.2637 -0.0058 0.040 Uiso 1 1 calc R . . . .
C41 C 0.22382(8) -0.27100(16) 0.04021(6) 0.0153(3) Uani 1 1 d . . . . .
C16 C 0.20555(8) 0.05835(17) 0.32054(6) 0.0157(3) Uani 1 1 d . . . . .
C8 C 0.20452(8) 0.34449(17) 0.30309(6) 0.0168(3) Uani 1 1 d . . . . .
C32 C 0.15392(8) 0.11499(16) 0.08552(6) 0.0167(3) Uani 1 1 d . . . . .
O2 O 0.40950(6) 0.10069(16) 0.42352(5) 0.0306(3) Uani 1 1 d . . . . .
O4 O 0.41428(8) -0.3617(2) 0.15539(6) 0.0527(5) 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
F5 C32 1.3701(16) . ?
F4 C32 1.3641(16) . ?
O3 C42 1.2135(18) . ?
F2 C7 1.3613(18) . ?
O1 C17 1.2060(18) . ?
F3 C12 1.3612(19) . ?
F1 C7 1.3671(17) . ?
N2 C15 1.2629(19) . ?
N2 C18 1.4817(19) . ?
N3 C21 1.4327(19) . ?
N3 O2 1.2241(18) . ?
F6 C37 1.3622(19) . ?
N1 C17 1.3942(18) . ?
N1 C1 1.4171(19) . ?
N1 C8 1.4917(18) . ?
N4 C26 1.4150(18) . ?
N4 C42 1.3830(18) . ?
N4 C33 1.4916(17) . ?
C39 H39 0.9300 . ?
C39 C34 1.394(2) . ?
C39 C38 1.387(2) . ?
C31 C26 1.393(2) . ?
C31 C30 1.388(2) . ?
C31 C32 1.496(2) . ?
C9 C10 1.388(2) . ?
C9 C14 1.396(2) . ?
C9 C8 1.526(2) . ?
N5 C40 1.2625(19) . ?
N5 C43 1.4781(18) . ?
C15 C16 1.5292(19) . ?
C15 C8 1.5104(19) . ?
C40 C33 1.5157(19) . ?
C40 C41 1.5299(19) . ?
C20 C25 1.396(2) . ?
C20 C21 1.404(2) . ?
C20 C16 1.537(2) . ?
C26 C27 1.387(2) . ?
C45 C50 1.396(2) . ?
C45 C46 1.405(2) . ?
C45 C41 1.531(2) . ?
C35 H35 0.9300 . ?
C35 C34 1.390(2) . ?
C35 C36 1.393(2) . ?
C34 C33 1.5266(19) . ?
C42 C41 1.543(2) . ?
C17 C16 1.541(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.549(2) . ?
C19 C16 1.5433(19) . ?
C1 C6 1.392(2) . ?
C1 C2 1.388(2) . ?
C28 H28 0.9300 . ?
C28 C27 1.396(2) . ?
C28 C29 1.391(2) . ?
C50 H50 0.9300 . ?
C50 C49 1.389(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.397(2) . ?
C3 C2 1.393(2) . ?
N6 C46 1.441(2) . ?
N6 O4 1.219(2) . ?
C27 H27 0.9300 . ?
C6 C5 1.388(2) . ?
C6 C7 1.496(2) . ?
C33 C32 1.5642(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.387(2) . ?
C25 H25 0.9300 . ?
C25 C24 1.393(2) . ?
C24 H24 0.9300 . ?
C24 C23 1.389(2) . ?
C12 C11 1.378(2) . ?
C12 C13 1.379(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.386(2) . ?
C21 C22 1.403(2) . ?
C47 H47 0.9300 . ?
C47 C46 1.397(2) . ?
C47 C48 1.382(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.378(2) . ?
C22 H22 0.9300 . ?
C37 C38 1.378(2) . ?
C37 C36 1.379(2) . ?
C4 H4 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.387(2) . ?
C2 H2 0.9300 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C44 C43 1.557(2) . ?
C44 C41 1.5488(19) . ?
C38 H38 0.9300 . ?
C7 C8 1.564(2) . ?
C11 H11 0.9300 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C30 H30 0.9300 . ?
C13 H13 0.9300 . ?
C49 H49 0.9300 . ?
C49 C48 1.390(3) . ?
C36 H36 0.9300 . ?
C48 H48 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N2 C18 107.01(12) . . ?
O2 N3 C21 115.63(13) . . ?
C17 N1 C1 125.55(13) . . ?
C17 N1 C8 114.14(11) . . ?
C1 N1 C8 110.55(11) . . ?
C26 N4 C33 110.87(11) . . ?
C42 N4 C26 126.96(12) . . ?
C42 N4 C33 114.42(11) . . ?
C34 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C38 C39 C34 120.46(14) . . ?
C26 C31 C32 110.12(12) . . ?
C30 C31 C26 120.70(14) . . ?
C30 C31 C32 128.98(13) . . ?
C10 C9 C14 119.64(14) . . ?
C10 C9 C8 122.02(14) . . ?
C14 C9 C8 118.33(13) . . ?
C40 N5 C43 107.88(12) . . ?
N2 C15 C16 118.62(13) . . ?
N2 C15 C8 131.00(13) . . ?
C8 C15 C16 107.86(11) . . ?
N5 C40 C33 131.15(13) . . ?
N5 C40 C41 118.29(12) . . ?
C33 C40 C41 107.30(11) . . ?
C25 C20 C21 117.44(14) . . ?
C25 C20 C16 120.04(13) . . ?
C21 C20 C16 122.45(13) . . ?
C31 C26 N4 109.62(13) . . ?
C27 C26 N4 128.27(13) . . ?
C27 C26 C31 122.09(14) . . ?
C50 C45 C46 116.96(14) . . ?
C50 C45 C41 121.13(14) . . ?
C46 C45 C41 121.88(13) . . ?
C34 C35 H35 119.9 . . ?
C34 C35 C36 120.23(14) . . ?
C36 C35 H35 119.9 . . ?
C39 C34 C33 118.63(13) . . ?
C35 C34 C39 120.02(14) . . ?
C35 C34 C33 121.35(13) . . ?
O3 C42 N4 125.40(14) . . ?
O3 C42 C41 128.05(13) . . ?
N4 C42 C41 106.53(12) . . ?
O1 C17 N1 125.19(14) . . ?
O1 C17 C16 128.71(13) . . ?
N1 C17 C16 106.08(12) . . ?
H19A C19 H19B 109.0 . . ?
C18 C19 H19A 111.0 . . ?
C18 C19 H19B 111.0 . . ?
C16 C19 H19A 111.0 . . ?
C16 C19 H19B 111.0 . . ?
C16 C19 C18 103.81(11) . . ?
C6 C1 N1 110.08(13) . . ?
C2 C1 N1 128.18(13) . . ?
C2 C1 C6 121.74(14) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 H28 119.1 . . ?
C29 C28 C27 121.77(15) . . ?
C45 C50 H50 119.4 . . ?
C49 C50 C45 121.13(16) . . ?
C49 C50 H50 119.4 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.25(15) . . ?
C11 C10 H10 119.9 . . ?
N2 C18 C19 107.81(12) . . ?
N2 C18 H18A 110.1 . . ?
N2 C18 H18B 110.1 . . ?
C19 C18 H18A 110.1 . . ?
C19 C18 H18B 110.1 . . ?
H18A C18 H18B 108.5 . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.83(15) . . ?
O4 N6 C46 115.43(15) . . ?
C26 C27 C28 116.57(14) . . ?
C26 C27 H27 121.7 . . ?
C28 C27 H27 121.7 . . ?
C1 C6 C7 109.54(13) . . ?
C5 C6 C1 121.16(15) . . ?
C5 C6 C7 129.04(14) . . ?
N4 C33 C40 97.70(10) . . ?
N4 C33 C34 112.43(11) . . ?
N4 C33 C32 102.64(11) . . ?
C40 C33 C34 111.98(12) . . ?
C40 C33 C32 119.90(12) . . ?
C34 C33 C32 110.92(11) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 C6 117.78(15) . . ?
C4 C5 H5 121.1 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.64(15) . . ?
C24 C25 H25 119.7 . . ?
C25 C24 H24 119.5 . . ?
C23 C24 C25 121.05(15) . . ?
C23 C24 H24 119.5 . . ?
F3 C12 C11 118.34(15) . . ?
F3 C12 C13 118.54(16) . . ?
C11 C12 C13 123.12(16) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.80(15) . . ?
C13 C14 H14 119.6 . . ?
C20 C21 N3 116.44(13) . . ?
C22 C21 N3 121.75(14) . . ?
C22 C21 C20 121.79(14) . . ?
C46 C47 H47 120.1 . . ?
C48 C47 H47 120.1 . . ?
C48 C47 C46 119.74(17) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 C24 119.58(15) . . ?
C22 C23 H23 120.2 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.42(15) . . ?
C23 C22 H22 120.3 . . ?
F6 C37 C38 118.36(15) . . ?
F6 C37 C36 118.11(15) . . ?
C38 C37 C36 123.53(15) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.74(15) . . ?
C5 C4 H4 119.6 . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.90(14) . . ?
C30 C29 H29 119.6 . . ?
C1 C2 C3 116.74(14) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
H44A C44 H44B 109.0 . . ?
C43 C44 H44A 111.0 . . ?
C43 C44 H44B 111.0 . . ?
C41 C44 H44A 111.0 . . ?
C41 C44 H44B 111.0 . . ?
C41 C44 C43 103.87(11) . . ?
C39 C38 H38 121.1 . . ?
C37 C38 C39 117.89(15) . . ?
C37 C38 H38 121.1 . . ?
C45 C46 N6 116.57(14) . . ?
C47 C46 C45 122.00(15) . . ?
C47 C46 N6 121.44(15) . . ?
F2 C7 F1 104.77(12) . . ?
F2 C7 C6 113.19(13) . . ?
F2 C7 C8 111.57(13) . . ?
F1 C7 C6 110.41(13) . . ?
F1 C7 C8 112.25(12) . . ?
C6 C7 C8 104.84(12) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.29(15) . . ?
C12 C11 H11 120.9 . . ?
N5 C43 C44 107.69(11) . . ?
N5 C43 H43A 110.2 . . ?
N5 C43 H43B 110.2 . . ?
C44 C43 H43A 110.2 . . ?
C44 C43 H43B 110.2 . . ?
H43A C43 H43B 108.5 . . ?
C31 C30 H30 121.0 . . ?
C29 C30 C31 117.95(14) . . ?
C29 C30 H30 121.0 . . ?
C12 C13 C14 117.89(16) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C50 C49 H49 119.5 . . ?
C48 C49 C50 121.02(16) . . ?
C48 C49 H49 119.5 . . ?
C35 C36 H36 121.1 . . ?
C37 C36 C35 117.88(15) . . ?
C37 C36 H36 121.1 . . ?
C47 C48 C49 119.12(16) . . ?
C47 C48 H48 120.4 . . ?
C49 C48 H48 120.4 . . ?
C40 C41 C45 116.70(12) . . ?
C40 C41 C42 97.46(11) . . ?
C40 C41 C44 100.68(11) . . ?
C45 C41 C42 110.18(12) . . ?
C45 C41 C44 114.96(12) . . ?
C42 C41 C44 115.47(12) . . ?
C15 C16 C20 118.07(12) . . ?
C15 C16 C17 97.64(11) . . ?
C15 C16 C19 100.41(11) . . ?
C20 C16 C17 109.22(11) . . ?
C20 C16 C19 113.57(12) . . ?
C17 C16 C19 117.07(12) . . ?
N1 C8 C9 112.87(11) . . ?
N1 C8 C15 98.45(11) . . ?
N1 C8 C7 102.48(11) . . ?
C9 C8 C7 111.54(12) . . ?
C15 C8 C9 110.59(12) . . ?
C15 C8 C7 119.86(12) . . ?
F5 C32 C31 112.76(12) . . ?
F5 C32 C33 111.44(12) . . ?
F4 C32 F5 104.28(11) . . ?
F4 C32 C31 111.45(12) . . ?
F4 C32 C33 112.64(11) . . ?
C31 C32 C33 104.49(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C42 C41 C40 -148.19(15) . . . . ?
O3 C42 C41 C45 89.74(17) . . . . ?
O3 C42 C41 C44 -42.6(2) . . . . ?
F2 C7 C8 N1 -138.34(12) . . . . ?
F2 C7 C8 C9 -17.32(17) . . . . ?
F2 C7 C8 C15 114.17(15) . . . . ?
O1 C17 C16 C15 -146.89(15) . . . . ?
O1 C17 C16 C20 89.78(17) . . . . ?
O1 C17 C16 C19 -41.0(2) . . . . ?
F3 C12 C11 C10 179.39(15) . . . . ?
F3 C12 C13 C14 -179.65(16) . . . . ?
F1 C7 C8 N1 104.42(13) . . . . ?
F1 C7 C8 C9 -134.57(13) . . . . ?
F1 C7 C8 C15 -3.08(19) . . . . ?
N2 C15 C16 C20 -119.53(15) . . . . ?
N2 C15 C16 C17 123.86(14) . . . . ?
N2 C15 C16 C19 4.43(18) . . . . ?
N2 C15 C8 N1 -128.81(17) . . . . ?
N2 C15 C8 C9 112.79(18) . . . . ?
N2 C15 C8 C7 -19.1(2) . . . . ?
N3 C21 C22 C23 175.49(15) . . . . ?
F6 C37 C38 C39 -178.79(15) . . . . ?
F6 C37 C36 C35 178.73(15) . . . . ?
N1 C17 C16 C15 31.57(13) . . . . ?
N1 C17 C16 C20 -91.76(13) . . . . ?
N1 C17 C16 C19 137.43(13) . . . . ?
N1 C1 C6 C5 -179.39(13) . . . . ?
N1 C1 C6 C7 -4.68(17) . . . . ?
N1 C1 C2 C3 179.90(14) . . . . ?
N4 C26 C27 C28 178.68(14) . . . . ?
N4 C42 C41 C40 29.85(13) . . . . ?
N4 C42 C41 C45 -92.22(13) . . . . ?
N4 C42 C41 C44 135.48(12) . . . . ?
N4 C33 C32 F5 -136.67(11) . . . . ?
N4 C33 C32 F4 106.52(13) . . . . ?
N4 C33 C32 C31 -14.62(13) . . . . ?
C39 C34 C33 N4 -161.87(12) . . . . ?
C39 C34 C33 C40 -53.03(17) . . . . ?
C39 C34 C33 C32 83.85(16) . . . . ?
C31 C26 C27 C28 0.5(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C9 C14 C13 C12 0.1(3) . . . . ?
N5 C40 C33 N4 -123.30(17) . . . . ?
N5 C40 C33 C34 118.68(17) . . . . ?
N5 C40 C33 C32 -13.9(2) . . . . ?
N5 C40 C41 C45 -121.94(15) . . . . ?
N5 C40 C41 C42 120.98(14) . . . . ?
N5 C40 C41 C44 3.20(17) . . . . ?
C15 N2 C18 C19 -13.29(17) . . . . ?
C40 N5 C43 C44 -11.26(17) . . . . ?
C40 C33 C32 F5 116.63(14) . . . . ?
C40 C33 C32 F4 -0.18(18) . . . . ?
C40 C33 C32 C31 -121.31(13) . . . . ?
C20 C25 C24 C23 -1.8(2) . . . . ?
C20 C21 C22 C23 -3.0(2) . . . . ?
C26 N4 C42 O3 22.3(2) . . . . ?
C26 N4 C42 C41 -155.84(13) . . . . ?
C26 N4 C33 C40 136.05(12) . . . . ?
C26 N4 C33 C34 -106.28(13) . . . . ?
C26 N4 C33 C32 12.96(14) . . . . ?
C26 C31 C30 C29 0.5(2) . . . . ?
C26 C31 C32 F5 133.34(13) . . . . ?
C26 C31 C32 F4 -109.76(13) . . . . ?
C26 C31 C32 C33 12.16(15) . . . . ?
C45 C50 C49 C48 -1.4(2) . . . . ?
C35 C34 C33 N4 18.66(18) . . . . ?
C35 C34 C33 C40 127.49(14) . . . . ?
C35 C34 C33 C32 -95.63(15) . . . . ?
C34 C39 C38 C37 0.3(2) . . . . ?
C34 C35 C36 C37 -0.1(2) . . . . ?
C34 C33 C32 F5 -16.38(16) . . . . ?
C34 C33 C32 F4 -133.19(12) . . . . ?
C34 C33 C32 C31 105.67(13) . . . . ?
C42 N4 C26 C31 141.19(14) . . . . ?
C42 N4 C26 C27 -37.1(2) . . . . ?
C42 N4 C33 C40 -15.56(15) . . . . ?
C42 N4 C33 C34 102.11(14) . . . . ?
C42 N4 C33 C32 -138.64(12) . . . . ?
C17 N1 C1 C6 137.41(14) . . . . ?
C17 N1 C1 C2 -42.0(2) . . . . ?
C17 N1 C8 C9 105.40(14) . . . . ?
C17 N1 C8 C15 -11.26(15) . . . . ?
C17 N1 C8 C7 -134.51(12) . . . . ?
C1 N1 C17 O1 22.4(2) . . . . ?
C1 N1 C17 C16 -156.12(13) . . . . ?
C1 N1 C8 C9 -106.56(13) . . . . ?
C1 N1 C8 C15 136.79(12) . . . . ?
C1 N1 C8 C7 13.53(14) . . . . ?
C1 C6 C5 C4 -0.6(2) . . . . ?
C1 C6 C7 F2 134.72(13) . . . . ?
C1 C6 C7 F1 -108.20(14) . . . . ?
C1 C6 C7 C8 12.90(16) . . . . ?
C28 C29 C30 C31 1.0(2) . . . . ?
C50 C45 C46 N6 178.33(14) . . . . ?
C50 C45 C46 C47 -1.0(2) . . . . ?
C50 C45 C41 C40 -123.79(15) . . . . ?
C50 C45 C41 C42 -13.92(18) . . . . ?
C50 C45 C41 C44 118.64(15) . . . . ?
C50 C49 C48 C47 -0.2(3) . . . . ?
C10 C9 C14 C13 0.2(2) . . . . ?
C10 C9 C8 N1 12.49(19) . . . . ?
C10 C9 C8 C15 121.69(15) . . . . ?
C10 C9 C8 C7 -102.26(16) . . . . ?
C18 N2 C15 C16 5.52(19) . . . . ?
C18 N2 C15 C8 165.17(15) . . . . ?
C18 C19 C16 C15 -11.62(15) . . . . ?
C18 C19 C16 C20 115.40(13) . . . . ?
C18 C19 C16 C17 -115.83(14) . . . . ?
C27 C28 C29 C30 -1.7(2) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C6 C5 C4 C3 0.5(2) . . . . ?
C6 C7 C8 N1 -15.46(14) . . . . ?
C6 C7 C8 C9 105.55(13) . . . . ?
C6 C7 C8 C15 -122.96(14) . . . . ?
C33 N4 C26 C31 -5.99(16) . . . . ?
C33 N4 C26 C27 175.66(14) . . . . ?
C33 N4 C42 O3 168.49(13) . . . . ?
C33 N4 C42 C41 -9.62(15) . . . . ?
C33 C40 C41 C45 76.21(15) . . . . ?
C33 C40 C41 C42 -40.87(13) . . . . ?
C33 C40 C41 C44 -158.65(12) . . . . ?
C5 C6 C7 F2 -51.1(2) . . . . ?
C5 C6 C7 F1 66.0(2) . . . . ?
C5 C6 C7 C8 -172.93(15) . . . . ?
C25 C20 C21 N3 -175.94(13) . . . . ?
C25 C20 C21 C22 2.6(2) . . . . ?
C25 C20 C16 C15 -139.69(14) . . . . ?
C25 C20 C16 C17 -29.48(17) . . . . ?
C25 C20 C16 C19 103.19(15) . . . . ?
C25 C24 C23 C22 1.4(2) . . . . ?
C24 C23 C22 C21 0.9(2) . . . . ?
C14 C9 C10 C11 -0.5(2) . . . . ?
C14 C9 C8 N1 -166.46(13) . . . . ?
C14 C9 C8 C15 -57.26(17) . . . . ?
C14 C9 C8 C7 78.80(17) . . . . ?
C21 C20 C25 C24 -0.3(2) . . . . ?
C21 C20 C16 C15 43.23(19) . . . . ?
C21 C20 C16 C17 153.44(13) . . . . ?
C21 C20 C16 C19 -73.90(17) . . . . ?
C4 C3 C2 C1 -0.6(2) . . . . ?
C29 C28 C27 C26 1.0(2) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C1 C6 C7 174.78(13) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C38 C39 C34 C35 -0.9(2) . . . . ?
C38 C39 C34 C33 179.66(14) . . . . ?
C38 C37 C36 C35 -0.5(3) . . . . ?
C46 C45 C50 C49 2.0(2) . . . . ?
C46 C45 C41 C40 58.00(18) . . . . ?
C46 C45 C41 C42 167.86(13) . . . . ?
C46 C45 C41 C44 -59.58(18) . . . . ?
C46 C47 C48 C49 1.1(3) . . . . ?
C7 C6 C5 C4 -174.19(15) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C43 N5 C40 C33 161.81(15) . . . . ?
C43 N5 C40 C41 5.07(18) . . . . ?
C43 C44 C41 C40 -9.35(14) . . . . ?
C43 C44 C41 C45 116.96(13) . . . . ?
C43 C44 C41 C42 -113.02(13) . . . . ?
C30 C31 C26 N4 -179.74(13) . . . . ?
C30 C31 C26 C27 -1.3(2) . . . . ?
C30 C31 C32 F5 -51.7(2) . . . . ?
C30 C31 C32 F4 65.15(19) . . . . ?
C30 C31 C32 C33 -172.93(14) . . . . ?
C13 C12 C11 C10 -0.1(3) . . . . ?
C36 C35 C34 C39 0.8(2) . . . . ?
C36 C35 C34 C33 -179.74(14) . . . . ?
C36 C37 C38 C39 0.4(3) . . . . ?
C48 C47 C46 C45 -0.5(3) . . . . ?
C48 C47 C46 N6 -179.81(17) . . . . ?
C41 C40 C33 N4 35.33(13) . . . . ?
C41 C40 C33 C34 -82.68(14) . . . . ?
C41 C40 C33 C32 144.75(13) . . . . ?
C41 C45 C50 C49 -176.34(14) . . . . ?
C41 C45 C46 N6 -3.4(2) . . . . ?
C41 C45 C46 C47 177.26(15) . . . . ?
C41 C44 C43 N5 12.80(16) . . . . ?
C16 C15 C8 N1 32.48(14) . . . . ?
C16 C15 C8 C9 -85.92(14) . . . . ?
C16 C15 C8 C7 142.18(13) . . . . ?
C16 C20 C25 C24 -177.48(13) . . . . ?
C16 C20 C21 N3 1.2(2) . . . . ?
C16 C20 C21 C22 179.78(14) . . . . ?
C16 C19 C18 N2 15.59(16) . . . . ?
C8 N1 C17 O1 164.89(14) . . . . ?
C8 N1 C17 C16 -13.64(16) . . . . ?
C8 N1 C1 C6 -6.17(16) . . . . ?
C8 N1 C1 C2 174.41(14) . . . . ?
C8 C9 C10 C11 -179.40(14) . . . . ?
C8 C9 C14 C13 179.16(15) . . . . ?
C8 C15 C16 C20 76.47(15) . . . . ?
C8 C15 C16 C17 -40.13(14) . . . . ?
C8 C15 C16 C19 -159.57(12) . . . . ?
C32 C31 C26 N4 -4.34(16) . . . . ?
C32 C31 C26 C27 174.13(13) . . . . ?
C32 C31 C30 C29 -173.94(14) . . . . ?
O2 N3 C21 C20 -177.18(14) . . . . ?
O2 N3 C21 C22 4.2(2) . . . . ?
O4 N6 C46 C45 -178.69(17) . . . . ?
O4 N6 C46 C47 0.7(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_229
_database_code_depnum_ccdc_archive 'CCDC 1830099'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-06-08 downloaded from the CCDC.
;
_audit_creation_date             2018-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 F2 N3'
_chemical_formula_sum            'C26 H21 F2 N3'
_chemical_formula_weight         413.46
_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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   18.76710(10)
_cell_length_b                   18.76710(10)
_cell_length_c                   24.2076(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8526.01(14)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    20897
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0100
_cell_measurement_theta_min      4.6630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3456
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            44385
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.058
_diffrn_reflns_theta_max         67.058
_diffrn_reflns_theta_min         4.713
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  11.00   1.00    3.00    --    0.00  82.00  60.00   41
  2  ω    -82.00 -57.00   1.00    3.00    --    0.00 -57.00 -30.00   25
  3  ω    -18.00   8.00   1.00    3.00    --    0.00 -57.00 -30.00   26
  4  ω    -18.00  26.00   1.00    3.00    --    0.00  38.00-180.00   44
  5  ω     29.00  88.00   1.00    3.00    --    0.00  38.00-180.00   59
  6  ω    -21.00  16.00   1.00    3.00    --    0.00  57.00  60.00   37
  7  ω     19.00  89.00   1.00    3.00    --    0.00  82.00  60.00   70
  8  ω    -38.00   8.00   1.00    3.00    --    0.00 -38.00-150.00   46
  9  ω    -86.00 -49.00   1.00    3.00    --    0.00 -38.00-150.00   37
 10  ω     79.00 105.00   1.00    7.00    --   95.80  45.00 -90.00   26
 11  ω     89.00 115.00   1.00    7.00    --   95.80 -82.00 -30.00   26
 12  ω     65.00 115.00   1.00    7.00    --   95.80 -30.00  30.00   50
 13  ω     58.00 116.00   1.00    7.00    --   95.80 -45.00-150.00   58
 14  ω     60.00  88.00   1.00    7.00    --   95.80 -82.00 150.00   28
 15  ω      8.00 127.00   1.00    7.00    --   95.80 -82.00 -60.00  119
 16  ω     12.00  42.00   1.00    7.00    --   95.80 -61.00 -60.00   30
 17  ω     89.00 127.00   1.00    7.00    --   95.80 -82.00  90.00   38
 18  ω     53.00  79.00   1.00    7.00    --   95.80 -82.00-150.00   26
 19  ω     47.00 127.00   1.00    7.00    --   95.80 -82.00  30.00   80
 20  ω     49.00  75.00   1.00    7.00    --   95.80 -82.00  90.00   26
 21  ω     86.00 121.00   1.00    7.00    --   95.80 -82.00-150.00   35
 22  ω     10.00  36.00   1.00    7.00    --   95.80 -30.00  30.00   26
 23  ω     15.00  85.00   1.00    7.00    --   95.80 -45.00  60.00   70
 24  ω    142.00 171.00   1.00    7.00    --   95.80  15.00  30.00   29
 25  ω     68.00 137.00   1.00    7.00    --   95.80  15.00  30.00   69
 26  ω      6.00 122.00   1.00    7.00    --   95.80 -15.00 120.00  116
 27  ω     96.00 125.00   1.00    7.00    --   95.80 -82.00 150.00   29
 28  ω     55.00 115.00   1.00    7.00    --   95.80 -61.00 -60.00   60
 29  ω     33.00  97.00   1.00    7.00    --   95.80 -82.00-180.00   64
 30  ω     92.00 118.00   1.00    7.00    --   95.80 -82.00  60.00   26
 31  ω     32.00 115.00   1.00    7.00    --   95.80 -15.00 -30.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0598176000
_diffrn_orient_matrix_UB_12      -0.0555947000
_diffrn_orient_matrix_UB_13      0.0065172000
_diffrn_orient_matrix_UB_21      0.0511940000
_diffrn_orient_matrix_UB_22      -0.0589788000
_diffrn_orient_matrix_UB_23      -0.0195319000
_diffrn_orient_matrix_UB_31      0.0231104000
_diffrn_orient_matrix_UB_32      -0.0131494000
_diffrn_orient_matrix_UB_33      0.0602256000
_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                3491
_reflns_number_total             3816
_reflns_odcompleteness_completeness 99.95
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.274
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.041
_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     281
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.041
_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)+(0.0420P)²+8.3800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_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.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 0.88215(4) 0.42697(5) 0.54171(3) 0.0299(2) Uani 1 1 d . . . . .
F2 F 0.86927(5) 0.51363(4) 0.59996(4) 0.0295(2) Uani 1 1 d . . . . .
N1 N 0.62753(6) 0.38707(7) 0.67136(5) 0.0255(3) Uani 1 1 d . . . . .
H1 H 0.617537 0.394822 0.705506 0.031 Uiso 1 1 calc R . . . .
N2 N 0.75548(6) 0.40898(6) 0.65103(5) 0.0205(3) Uani 1 1 d . . . . .
N3 N 0.76863(7) 0.33590(6) 0.51999(5) 0.0254(3) Uani 1 1 d . . . . .
C1 C 0.58216(8) 0.40154(8) 0.62764(6) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.51609(8) 0.43537(8) 0.62832(7) 0.0320(4) Uani 1 1 d . . . . .
H2 H 0.496950 0.452882 0.661047 0.038 Uiso 1 1 calc R . . . .
C3 C 0.47967(9) 0.44216(10) 0.57867(8) 0.0399(4) Uani 1 1 d . . . . .
H3 H 0.435382 0.464387 0.578426 0.048 Uiso 1 1 calc R . . . .
C4 C 0.50752(9) 0.41671(10) 0.52951(8) 0.0416(4) Uani 1 1 d . . . . .
H4 H 0.482309 0.422382 0.496731 0.050 Uiso 1 1 calc R . . . .
C5 C 0.57357(9) 0.38253(9) 0.52932(7) 0.0337(4) Uani 1 1 d . . . . .
H5 H 0.592749 0.365278 0.496523 0.040 Uiso 1 1 calc R . . . .
C6 C 0.60996(8) 0.37469(8) 0.57833(6) 0.0242(3) Uani 1 1 d . . . . .
C7 C 0.69370(7) 0.35729(7) 0.65195(6) 0.0212(3) Uani 1 1 d . . . . .
H7 H 0.706091 0.314620 0.673218 0.025 Uiso 1 1 calc R . . . .
C8 C 0.68003(7) 0.33783(7) 0.59056(6) 0.0214(3) Uani 1 1 d . . . . .
C9 C 0.68516(8) 0.26068(7) 0.56928(6) 0.0254(3) Uani 1 1 d . . . . .
H9A H 0.638279 0.240213 0.563572 0.030 Uiso 1 1 calc R . . . .
H9B H 0.711782 0.230839 0.594669 0.030 Uiso 1 1 calc R . . . .
C10 C 0.72528(8) 0.27001(8) 0.51399(6) 0.0276(3) Uani 1 1 d . . . . .
H10A H 0.755715 0.229253 0.506900 0.033 Uiso 1 1 calc R . . . .
H10B H 0.691830 0.274816 0.483667 0.033 Uiso 1 1 calc R . . . .
C11 C 0.74348(7) 0.36970(7) 0.56081(6) 0.0213(3) Uani 1 1 d . . . . .
C12 C 0.77029(8) 0.43345(7) 0.59285(6) 0.0223(3) Uani 1 1 d . . . . .
C13 C 0.85237(8) 0.44249(7) 0.59191(6) 0.0243(3) Uani 1 1 d . . . . .
C14 C 0.87878(7) 0.39892(7) 0.63848(6) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.94764(8) 0.37932(8) 0.65285(6) 0.0259(3) Uani 1 1 d . . . . .
H15 H 0.985824 0.389470 0.629659 0.031 Uiso 1 1 calc R . . . .
C16 C 0.95812(8) 0.34430(8) 0.70252(6) 0.0268(3) Uani 1 1 d . . . . .
H16 H 1.003914 0.330716 0.712750 0.032 Uiso 1 1 calc R . . . .
C17 C 0.90069(8) 0.32902(7) 0.73762(6) 0.0239(3) Uani 1 1 d . . . . .
C18 C 0.83153(7) 0.34743(7) 0.72188(6) 0.0219(3) Uani 1 1 d . . . . .
H18 H 0.793020 0.336244 0.744452 0.026 Uiso 1 1 calc R . . . .
C19 C 0.82097(7) 0.38265(7) 0.67214(6) 0.0204(3) Uani 1 1 d . . . . .
C20 C 0.91272(8) 0.29358(9) 0.79274(7) 0.0307(4) Uani 1 1 d . . . . .
H20A H 0.910985 0.242784 0.788283 0.046 Uiso 1 1 calc GR . . . .
H20B H 0.876281 0.308286 0.818138 0.046 Uiso 1 1 calc GR . . . .
H20C H 0.958539 0.307124 0.806902 0.046 Uiso 1 1 calc GR . . . .
C21 C 0.72920(8) 0.52033(8) 0.52127(7) 0.0284(3) Uani 1 1 d . . . . .
H21 H 0.753292 0.492818 0.495349 0.034 Uiso 1 1 calc R . . . .
C22 C 0.69250(9) 0.58054(9) 0.50451(7) 0.0340(4) Uani 1 1 d . . . . .
H22 H 0.691983 0.593418 0.467412 0.041 Uiso 1 1 calc R . . . .
C23 C 0.65652(9) 0.62162(9) 0.54308(8) 0.0393(4) Uani 1 1 d . . . . .
H23 H 0.631339 0.661744 0.531815 0.047 Uiso 1 1 calc R . . . .
C24 C 0.65811(11) 0.60287(9) 0.59834(8) 0.0447(5) Uani 1 1 d . . . . .
H24 H 0.634334 0.630723 0.624225 0.054 Uiso 1 1 calc R . . . .
C25 C 0.69510(10) 0.54261(8) 0.61530(7) 0.0356(4) Uani 1 1 d . . . . .
H25 H 0.696330 0.530297 0.652496 0.043 Uiso 1 1 calc R . . . .
C26 C 0.73024(8) 0.50077(8) 0.57660(6) 0.0251(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
F1 C13 1.3688(17) . ?
F2 C13 1.3860(16) . ?
N1 H1 0.8600 . ?
N1 C1 1.3852(19) . ?
N1 C7 1.4406(18) . ?
N2 C7 1.5119(17) . ?
N2 C12 1.5072(18) . ?
N2 C19 1.4199(17) . ?
N3 C10 1.4873(18) . ?
N3 C11 1.2656(19) . ?
C1 C2 1.393(2) . ?
C1 C6 1.397(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.396(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(2) . ?
C6 C8 1.5150(19) . ?
C7 H7 0.9800 . ?
C7 C8 1.552(2) . ?
C8 C9 1.5398(19) . ?
C8 C11 1.5147(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.546(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.5120(19) . ?
C12 C13 1.550(2) . ?
C12 C26 1.522(2) . ?
C13 C14 1.478(2) . ?
C14 C15 1.388(2) . ?
C14 C19 1.391(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.402(2) . ?
C17 C18 1.396(2) . ?
C17 C20 1.508(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9300 . ?
C21 C22 1.384(2) . ?
C21 C26 1.389(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.389(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.389(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
C1 N1 H1 124.6 . . ?
C1 N1 C7 110.90(12) . . ?
C7 N1 H1 124.6 . . ?
C12 N2 C7 110.52(10) . . ?
C19 N2 C7 115.80(11) . . ?
C19 N2 C12 106.41(11) . . ?
C11 N3 C10 106.79(12) . . ?
N1 C1 C2 128.86(14) . . ?
N1 C1 C6 110.65(13) . . ?
C2 C1 C6 120.46(14) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.02(15) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.76(15) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.77(16) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.14(16) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C8 108.77(12) . . ?
C5 C6 C1 120.84(14) . . ?
C5 C6 C8 130.37(14) . . ?
N1 C7 N2 114.64(11) . . ?
N1 C7 H7 110.5 . . ?
N1 C7 C8 105.13(11) . . ?
N2 C7 H7 110.5 . . ?
N2 C7 C8 105.30(11) . . ?
C8 C7 H7 110.5 . . ?
C6 C8 C7 102.90(11) . . ?
C6 C8 C9 114.73(12) . . ?
C9 C8 C7 122.09(12) . . ?
C11 C8 C6 114.15(11) . . ?
C11 C8 C7 103.43(11) . . ?
C11 C8 C9 99.38(11) . . ?
C8 C9 H9A 111.3 . . ?
C8 C9 H9B 111.3 . . ?
C8 C9 C10 102.34(11) . . ?
H9A C9 H9B 109.2 . . ?
C10 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
N3 C10 C9 106.02(11) . . ?
N3 C10 H10A 110.5 . . ?
N3 C10 H10B 110.5 . . ?
C9 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
N3 C11 C8 117.81(12) . . ?
N3 C11 C12 132.30(13) . . ?
C12 C11 C8 109.28(12) . . ?
N2 C12 C11 100.19(10) . . ?
N2 C12 C13 103.33(11) . . ?
N2 C12 C26 113.79(12) . . ?
C11 C12 C13 114.19(12) . . ?
C11 C12 C26 111.10(12) . . ?
C26 C12 C13 113.34(11) . . ?
F1 C13 F2 103.67(10) . . ?
F1 C13 C12 113.31(12) . . ?
F1 C13 C14 114.99(12) . . ?
F2 C13 C12 109.32(11) . . ?
F2 C13 C14 110.41(11) . . ?
C14 C13 C12 105.15(11) . . ?
C15 C14 C13 130.53(13) . . ?
C15 C14 C19 121.42(13) . . ?
C19 C14 C13 107.87(12) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.41(13) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 120.94(13) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C20 120.76(13) . . ?
C18 C17 C16 119.91(13) . . ?
C18 C17 C20 119.32(13) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.16(13) . . ?
C19 C18 H18 120.4 . . ?
C14 C19 N2 112.83(12) . . ?
C18 C19 N2 126.98(12) . . ?
C18 C19 C14 120.11(13) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 H21 119.8 . . ?
C22 C21 C26 120.37(15) . . ?
C26 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 119.92(15) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 119.96(15) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.23(17) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.89(16) . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C12 118.40(13) . . ?
C25 C26 C12 121.97(14) . . ?
C25 C26 C21 119.63(14) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.250 0.125 192.5 46.6 ?
2 0.000 0.750 0.875 192.5 46.6 ?
3 0.500 0.250 0.375 192.5 46.6 ?
4 0.500 0.750 0.625 192.5 46.6 ?

_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 6.636
_oxdiff_exptl_absorpt_empirical_full_min 0.186
