# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_852
_database_code_depnum_ccdc_archive 'CCDC 2154342'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-07-24 downloaded from the CCDC.
;
_audit_creation_date             2020-09-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H25 N O5'
_chemical_formula_sum            'C32 H25 N O5'
_chemical_formula_weight         503.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.4214(10)
_cell_length_b                   12.2255(9)
_cell_length_c                   14.5032(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.431(7)
_cell_angle_gamma                90
_cell_volume                     2545.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2796
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.3950
_cell_measurement_theta_min      3.8290
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16553
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.971
_diffrn_reflns_theta_min         3.620
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     66.00  92.00   1.00   50.00    --   22.36-144.00  41.00   26
  2  ω    -48.00  48.00   1.00   50.00    --   22.36 -23.00  65.00   96
  3  ω    -96.00 -39.00   1.00   50.00    --  -24.08-178.00 -90.00   57
  4  ω     33.00  59.00   1.00   50.00    --   21.89 -23.00  64.00   26
  5  ω     46.00  97.00   1.00   50.00    --   21.89 178.00  30.00   51
  6  ω    -90.00 -38.00   1.00   50.00    --  -23.61 -57.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047413000
_diffrn_orient_matrix_UB_12      -0.0520225000
_diffrn_orient_matrix_UB_13      -0.0216840000
_diffrn_orient_matrix_UB_21      -0.0393527000
_diffrn_orient_matrix_UB_22      0.0191323000
_diffrn_orient_matrix_UB_23      -0.0283920000
_diffrn_orient_matrix_UB_31      0.0294405000
_diffrn_orient_matrix_UB_32      0.0173172000
_diffrn_orient_matrix_UB_33      -0.0336971000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3480
_reflns_number_total             6968
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6968
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.005
_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)+(0.1000P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.2183
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C8(H8), C7(H7), C21(H21), C19(H19), C18(H18), C17(H17),
 C27(H27), C20(H20), C33(H33), C32(H32), C31(H31), C26(H26), C29(H29), C23(H23),
  C24(H24), C30(H30), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.29469(10) 0.70418(12) 0.23668(10) 0.0530(4) Uani 1 1 d . . . . .
O4 O 0.06080(12) 1.09787(14) 0.08893(12) 0.0615(4) Uani 1 1 d . . . . .
O3 O 0.03766(11) 0.75183(14) 0.03804(11) 0.0600(4) Uani 1 1 d . . . . .
C4 C 0.20319(13) 0.84285(17) 0.09220(14) 0.0415(5) Uani 1 1 d . . . . .
N1 N 0.05552(12) 0.74524(15) 0.12147(13) 0.0480(4) Uani 1 1 d . . . . .
O5 O 0.13217(12) 1.07920(14) -0.06151(11) 0.0651(5) Uani 1 1 d . . . . .
C2 C 0.20337(14) 0.67761(18) 0.19544(15) 0.0460(5) Uani 1 1 d . . . . .
C10 C 0.34209(14) 0.79097(17) 0.20310(14) 0.0453(5) Uani 1 1 d . . . . .
O2 O 0.00336(11) 0.70539(17) 0.17332(12) 0.0719(5) Uani 1 1 d . . . . .
C14 C 0.15490(13) 0.94746(17) 0.05657(13) 0.0433(5) Uani 1 1 d . . . . .
C5 C 0.30231(13) 0.86265(17) 0.13572(13) 0.0422(5) Uani 1 1 d . . . . .
C12 C 0.07715(17) 0.9628(2) 0.20498(16) 0.0522(5) Uani 1 1 d . . . . .
C3 C 0.15077(13) 0.78439(17) 0.16502(13) 0.0435(5) Uani 1 1 d . . . . .
C15 C 0.16249(15) 0.98529(19) -0.03586(15) 0.0493(5) Uani 1 1 d . . . . .
C13 C 0.10159(15) 1.00452(18) 0.11345(15) 0.0482(5) Uani 1 1 d . . . . .
C6 C 0.35592(14) 0.95042(19) 0.11188(15) 0.0504(5) Uani 1 1 d . . . . .
H6 H 0.330815 0.999310 0.067150 0.060 Uiso 1 1 calc R U . . .
C16 C 0.20492(15) 0.91761(19) -0.10698(14) 0.0495(5) Uani 1 1 d . . . . .
C11 C 0.13534(15) 0.86577(19) 0.24457(14) 0.0471(5) Uani 1 1 d . . . . .
C28 C 0.20699(17) 0.59515(18) 0.11780(15) 0.0522(5) Uani 1 1 d . . . . .
C9 C 0.43148(16) 0.8068(2) 0.24386(18) 0.0580(6) Uani 1 1 d . . . . .
H9 H 0.457237 0.757920 0.288317 0.070 Uiso 1 1 calc R U . . .
C22 C 0.10242(18) 0.8192(2) 0.33295(15) 0.0570(6) Uani 1 1 d . . . . .
C8 C 0.48220(16) 0.8950(2) 0.21837(19) 0.0678(7) Uani 1 1 d . . . . .
H8 H 0.542315 0.906030 0.246058 0.081 Uiso 1 1 calc R U . . .
C7 C 0.44467(16) 0.9678(2) 0.15189(18) 0.0619(6) Uani 1 1 d . . . . .
H7 H 0.479086 1.027427 0.134616 0.074 Uiso 1 1 calc R U . . .
C21 C 0.17209(18) 0.8141(2) -0.13103(18) 0.0689(7) Uani 1 1 d . . . . .
H21 H 0.123308 0.784250 -0.101717 0.083 Uiso 1 1 calc R U . . .
C19 C 0.28342(18) 0.7963(3) -0.24177(17) 0.0695(7) Uani 1 1 d . . . . .
H19 H 0.309176 0.756085 -0.287452 0.083 Uiso 1 1 calc R U . . .
C18 C 0.3170(2) 0.8976(3) -0.2171(2) 0.0829(9) Uani 1 1 d . . . . .
H18 H 0.366922 0.925964 -0.245599 0.100 Uiso 1 1 calc R U . . .
C17 C 0.27840(19) 0.9581(3) -0.15115(18) 0.0737(8) Uani 1 1 d . . . . .
H17 H 0.301906 1.027291 -0.135899 0.088 Uiso 1 1 calc R U . . .
C27 C 0.1683(2) 0.7748(2) 0.39857(16) 0.0692(7) Uani 1 1 d . . . . .
H27 H 0.230586 0.772113 0.386853 0.083 Uiso 1 1 calc R U . . .
C20 C 0.2114(2) 0.7552(3) -0.19807(19) 0.0805(9) Uani 1 1 d . . . . .
H20 H 0.188331 0.685983 -0.213939 0.097 Uiso 1 1 calc R U . . .
C33 C 0.1341(2) 0.5219(2) 0.1016(2) 0.0762(8) Uani 1 1 d . . . . .
H33 H 0.086777 0.520740 0.140936 0.091 Uiso 1 1 calc R U . . .
C32 C 0.1309(3) 0.4511(3) 0.0281(3) 0.1124(14) Uani 1 1 d . . . . .
H32 H 0.081426 0.402402 0.017653 0.135 Uiso 1 1 calc R U . . .
C31 C 0.1995(5) 0.4520(3) -0.0294(3) 0.132(2) Uani 1 1 d . . . . .
H31 H 0.195908 0.405669 -0.080476 0.158 Uiso 1 1 calc R U . . .
C26 C 0.1415(3) 0.7342(3) 0.4818(2) 0.0941(11) Uani 1 1 d . . . . .
H26 H 0.186021 0.704854 0.525497 0.113 Uiso 1 1 calc R U . . .
C29 C 0.2784(2) 0.5930(2) 0.0610(2) 0.0792(9) Uani 1 1 d . . . . .
H29 H 0.328897 0.639957 0.072366 0.095 Uiso 1 1 calc R U . . .
C23 C 0.0102(2) 0.8212(3) 0.3523(2) 0.0826(9) Uani 1 1 d . . . . .
H23 H -0.035009 0.850786 0.309453 0.099 Uiso 1 1 calc R U . . .
C24 C -0.0153(3) 0.7796(3) 0.4353(3) 0.1129(13) Uani 1 1 d . . . . .
H24 H -0.077603 0.780517 0.447014 0.135 Uiso 1 1 calc R U . . .
C30 C 0.2752(4) 0.5215(3) -0.0125(2) 0.1150(15) Uani 1 1 d . . . . .
H30 H 0.323484 0.519892 -0.050678 0.138 Uiso 1 1 calc R U . . .
C25 C 0.0498(4) 0.7373(3) 0.4997(3) 0.1169(15) Uani 1 1 d . . . . .
H25 H 0.032182 0.710717 0.555485 0.140 Uiso 1 1 calc R U . . .
H2 H 0.1725(14) 0.6438(17) 0.2476(14) 0.046(5) Uiso 1 1 d . . . . .
H4A H 0.2073(14) 0.7944(17) 0.0402(14) 0.043(5) Uiso 1 1 d . . . . .
H11 H 0.1957(14) 0.8937(17) 0.2604(13) 0.039(5) Uiso 1 1 d . . . . .
H12A H 0.0803(16) 1.022(2) 0.2508(17) 0.064(7) Uiso 1 1 d . . . . .
H12B H 0.0103(18) 0.939(2) 0.1970(15) 0.064(7) Uiso 1 1 d . . . . .
H4 H 0.083(2) 1.111(3) 0.017(2) 0.114(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.431(3) . ?
O1 C10 1.376(3) . ?
O4 C13 1.317(3) . ?
O4 H4 1.13(4) . ?
O3 N1 1.216(2) . ?
C4 C14 1.523(3) . ?
C4 C5 1.526(3) . ?
C4 C3 1.533(3) . ?
C4 H4A 0.97(2) . ?
N1 O2 1.215(2) . ?
N1 C3 1.533(3) . ?
O5 C15 1.272(3) . ?
O5 H4 1.45(4) . ?
C2 C3 1.553(3) . ?
C2 C28 1.516(3) . ?
C2 H2 1.00(2) . ?
C10 C5 1.395(3) . ?
C10 C9 1.380(3) . ?
C14 C15 1.432(3) . ?
C14 C13 1.370(3) . ?
C5 C6 1.385(3) . ?
C12 C13 1.495(3) . ?
C12 C11 1.533(3) . ?
C12 H12A 0.98(3) . ?
C12 H12B 1.00(3) . ?
C3 C11 1.555(3) . ?
C15 C16 1.497(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(3) . ?
C16 C21 1.385(3) . ?
C16 C17 1.381(3) . ?
C11 C22 1.519(3) . ?
C11 H11 0.94(2) . ?
C28 C33 1.384(3) . ?
C28 C29 1.379(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.374(3) . ?
C22 C27 1.390(4) . ?
C22 C23 1.386(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.383(4) . ?
C7 H7 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.374(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.366(4) . ?
C19 C20 1.363(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.369(4) . ?
C17 H17 0.9300 . ?
C27 H27 0.9300 . ?
C27 C26 1.393(4) . ?
C20 H20 0.9300 . ?
C33 H33 0.9300 . ?
C33 C32 1.371(4) . ?
C32 H32 0.9300 . ?
C32 C31 1.353(6) . ?
C31 H31 0.9300 . ?
C31 C30 1.387(7) . ?
C26 H26 0.9300 . ?
C26 C25 1.372(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.375(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.387(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.362(6) . ?
C30 H30 0.9300 . ?
C25 H25 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
C10 O1 C2 119.69(16) . . ?
C13 O4 H4 102.3(17) . . ?
C14 C4 C5 112.79(17) . . ?
C14 C4 C3 112.70(16) . . ?
C14 C4 H4A 108.1(12) . . ?
C5 C4 C3 107.02(16) . . ?
C5 C4 H4A 107.2(12) . . ?
C3 C4 H4A 108.9(12) . . ?
O3 N1 C3 119.11(16) . . ?
O2 N1 O3 123.87(18) . . ?
O2 N1 C3 116.96(17) . . ?
C15 O5 H4 100.9(13) . . ?
O1 C2 C3 109.47(16) . . ?
O1 C2 C28 111.49(17) . . ?
O1 C2 H2 103.6(12) . . ?
C3 C2 H2 108.7(12) . . ?
C28 C2 C3 113.47(17) . . ?
C28 C2 H2 109.6(12) . . ?
O1 C10 C5 123.18(18) . . ?
O1 C10 C9 115.56(19) . . ?
C9 C10 C5 121.2(2) . . ?
C15 C14 C4 121.05(18) . . ?
C13 C14 C4 119.19(18) . . ?
C13 C14 C15 119.7(2) . . ?
C10 C5 C4 119.81(18) . . ?
C6 C5 C4 122.86(19) . . ?
C6 C5 C10 117.33(19) . . ?
C13 C12 C11 115.46(18) . . ?
C13 C12 H12A 110.5(14) . . ?
C13 C12 H12B 107.5(13) . . ?
C11 C12 H12A 109.2(14) . . ?
C11 C12 H12B 107.8(14) . . ?
H12A C12 H12B 105.9(19) . . ?
C4 C3 N1 110.05(16) . . ?
C4 C3 C2 109.17(16) . . ?
C4 C3 C11 109.11(17) . . ?
N1 C3 C2 104.42(16) . . ?
N1 C3 C11 108.65(16) . . ?
C2 C3 C11 115.30(17) . . ?
O5 C15 C14 120.7(2) . . ?
O5 C15 C16 116.69(19) . . ?
C14 C15 C16 122.6(2) . . ?
O4 C13 C14 122.7(2) . . ?
O4 C13 C12 113.48(19) . . ?
C14 C13 C12 123.6(2) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.3(2) . . ?
C7 C6 H6 118.8 . . ?
C21 C16 C15 121.8(2) . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 C21 118.0(2) . . ?
C12 C11 C3 109.20(17) . . ?
C12 C11 H11 105.7(12) . . ?
C3 C11 H11 102.6(12) . . ?
C22 C11 C12 113.74(19) . . ?
C22 C11 C3 117.65(19) . . ?
C22 C11 H11 106.6(11) . . ?
C33 C28 C2 118.5(2) . . ?
C29 C28 C2 122.5(2) . . ?
C29 C28 C33 119.0(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C27 C22 C11 118.4(2) . . ?
C23 C22 C11 123.2(2) . . ?
C23 C22 C27 118.4(2) . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C6 C7 C8 118.9(2) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C20 C19 C18 118.7(3) . . ?
C19 C18 H18 119.5 . . ?
C19 C18 C17 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C22 C27 H27 119.9 . . ?
C22 C27 C26 120.3(3) . . ?
C26 C27 H27 119.9 . . ?
C21 C20 H20 119.4 . . ?
C19 C20 C21 121.3(3) . . ?
C19 C20 H20 119.4 . . ?
C28 C33 H33 119.7 . . ?
C32 C33 C28 120.7(3) . . ?
C32 C33 H33 119.7 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 C33 120.1(4) . . ?
C31 C32 H32 120.0 . . ?
C32 C31 H31 119.8 . . ?
C32 C31 C30 120.4(3) . . ?
C30 C31 H31 119.8 . . ?
C27 C26 H26 119.8 . . ?
C25 C26 C27 120.3(4) . . ?
C25 C26 H26 119.8 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.5(3) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(4) . . ?
C25 C24 H24 119.6 . . ?
C31 C30 H30 120.2 . . ?
C29 C30 C31 119.6(4) . . ?
C29 C30 H30 120.2 . . ?
C26 C25 H25 120.1 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 61.7(2) . . . . ?
O1 C2 C3 N1 179.39(15) . . . . ?
O1 C2 C3 C11 -61.5(2) . . . . ?
O1 C2 C28 C33 148.5(2) . . . . ?
O1 C2 C28 C29 -33.8(3) . . . . ?
O1 C10 C5 C4 -3.2(3) . . . . ?
O1 C10 C5 C6 176.33(19) . . . . ?
O1 C10 C9 C8 -176.4(2) . . . . ?
O3 N1 C3 C4 8.5(3) . . . . ?
O3 N1 C3 C2 -108.5(2) . . . . ?
O3 N1 C3 C11 127.9(2) . . . . ?
C4 C14 C15 O5 -171.04(19) . . . . ?
C4 C14 C15 C16 9.6(3) . . . . ?
C4 C14 C13 O4 177.19(19) . . . . ?
C4 C14 C13 C12 -8.4(3) . . . . ?
C4 C5 C6 C7 179.6(2) . . . . ?
C4 C3 C11 C12 60.6(2) . . . . ?
C4 C3 C11 C22 -167.85(19) . . . . ?
N1 C3 C11 C12 -59.4(2) . . . . ?
N1 C3 C11 C22 72.1(2) . . . . ?
O5 C15 C16 C21 -123.2(3) . . . . ?
O5 C15 C16 C17 56.4(3) . . . . ?
C2 O1 C10 C5 6.5(3) . . . . ?
C2 O1 C10 C9 -176.66(19) . . . . ?
C2 C3 C11 C12 -176.19(17) . . . . ?
C2 C3 C11 C22 -44.6(3) . . . . ?
C2 C28 C33 C32 175.3(3) . . . . ?
C2 C28 C29 C30 -175.5(3) . . . . ?
C10 O1 C2 C3 -35.3(2) . . . . ?
C10 O1 C2 C28 91.1(2) . . . . ?
C10 C5 C6 C7 0.1(3) . . . . ?
C10 C9 C8 C7 -0.4(4) . . . . ?
O2 N1 C3 C4 -174.10(18) . . . . ?
O2 N1 C3 C2 68.8(2) . . . . ?
O2 N1 C3 C11 -54.7(2) . . . . ?
C14 C4 C5 C10 153.70(18) . . . . ?
C14 C4 C5 C6 -25.8(3) . . . . ?
C14 C4 C3 N1 64.5(2) . . . . ?
C14 C4 C3 C2 178.56(16) . . . . ?
C14 C4 C3 C11 -54.6(2) . . . . ?
C14 C15 C16 C21 56.3(3) . . . . ?
C14 C15 C16 C17 -124.2(3) . . . . ?
C5 C4 C14 C15 88.9(2) . . . . ?
C5 C4 C14 C13 -92.7(2) . . . . ?
C5 C4 C3 N1 -170.93(16) . . . . ?
C5 C4 C3 C2 -56.9(2) . . . . ?
C5 C4 C3 C11 69.9(2) . . . . ?
C5 C10 C9 C8 0.5(4) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C12 C11 C22 C27 -147.8(2) . . . . ?
C12 C11 C22 C23 30.5(3) . . . . ?
C3 C4 C14 C15 -149.79(19) . . . . ?
C3 C4 C14 C13 28.6(3) . . . . ?
C3 C4 C5 C10 29.2(2) . . . . ?
C3 C4 C5 C6 -150.30(19) . . . . ?
C3 C2 C28 C33 -87.3(3) . . . . ?
C3 C2 C28 C29 90.4(3) . . . . ?
C3 C11 C22 C27 82.7(3) . . . . ?
C3 C11 C22 C23 -99.0(3) . . . . ?
C15 C14 C13 O4 -4.4(3) . . . . ?
C15 C14 C13 C12 170.0(2) . . . . ?
C15 C16 C21 C20 178.6(2) . . . . ?
C15 C16 C17 C18 -179.2(3) . . . . ?
C13 C14 C15 O5 10.6(3) . . . . ?
C13 C14 C15 C16 -168.84(19) . . . . ?
C13 C12 C11 C3 -40.9(3) . . . . ?
C13 C12 C11 C22 -174.6(2) . . . . ?
C16 C21 C20 C19 0.5(5) . . . . ?
C11 C12 C13 O4 -169.75(19) . . . . ?
C11 C12 C13 C14 15.4(3) . . . . ?
C11 C22 C27 C26 178.0(2) . . . . ?
C11 C22 C23 C24 -178.5(3) . . . . ?
C28 C2 C3 C4 -63.5(2) . . . . ?
C28 C2 C3 N1 54.1(2) . . . . ?
C28 C2 C3 C11 173.28(18) . . . . ?
C28 C33 C32 C31 0.2(5) . . . . ?
C28 C29 C30 C31 0.3(5) . . . . ?
C9 C10 C5 C4 -179.9(2) . . . . ?
C9 C10 C5 C6 -0.4(3) . . . . ?
C9 C8 C7 C6 0.1(4) . . . . ?
C22 C27 C26 C25 0.2(5) . . . . ?
C22 C23 C24 C25 0.9(6) . . . . ?
C21 C16 C17 C18 0.4(4) . . . . ?
C19 C18 C17 C16 0.7(5) . . . . ?
C18 C19 C20 C21 0.6(5) . . . . ?
C17 C16 C21 C20 -1.0(4) . . . . ?
C27 C22 C23 C24 -0.2(4) . . . . ?
C27 C26 C25 C24 0.5(6) . . . . ?
C20 C19 C18 C17 -1.2(5) . . . . ?
C33 C28 C29 C30 2.2(4) . . . . ?
C33 C32 C31 C30 2.3(6) . . . . ?
C32 C31 C30 C29 -2.6(6) . . . . ?
C29 C28 C33 C32 -2.5(4) . . . . ?
C23 C22 C27 C26 -0.4(4) . . . . ?
C23 C24 C25 C26 -1.1(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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.904
####################################################################### 
# 
# 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_1137
_database_code_depnum_ccdc_archive 'CCDC 2154344'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-07-24 downloaded from the CCDC.
;
_audit_creation_date             2021-03-02
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C33 H23 F3 O3'
_chemical_formula_sum            'C33 H23 F3 O3'
_chemical_formula_weight         524.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   11.9059(6)
_cell_length_b                   13.1467(9)
_cell_length_c                   16.8474(12)
_cell_angle_alpha                95.452(6)
_cell_angle_beta                 94.131(5)
_cell_angle_gamma                97.412(5)
_cell_volume                     2593.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2614
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.8180
_cell_measurement_theta_min      2.0930
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20412
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         1.57
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9872
_diffrn_measured_fraction_theta_max 0.9346
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -97.00  -48.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362 -178.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   21.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362  178.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
  4 omega    2.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362   57.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  5 omega  -10.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362   19.0000    0.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0011451000
_diffrn_orient_matrix_UB_12      0.0358241000
_diffrn_orient_matrix_UB_13      0.0340828000
_diffrn_orient_matrix_UB_21      -0.0194978000
_diffrn_orient_matrix_UB_22      -0.0410011000
_diffrn_orient_matrix_UB_23      0.0222165000
_diffrn_orient_matrix_UB_31      0.0570468000
_diffrn_orient_matrix_UB_32      -0.0053822000
_diffrn_orient_matrix_UB_33      0.0121082000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5830
_reflns_number_total             13600
_reflns_odcompleteness_completeness 98.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     767
_refine_ls_number_reflns         13600
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1758
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0792P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.2033
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.64985(14) -0.16423(13) 0.31219(14) 0.0624(6) Uani 1 1 d . . .
F3 F 0.13868(16) 0.13116(13) 0.31438(12) 0.0859(6) Uani 1 1 d . . .
O2A O 0.85253(15) 0.31860(13) 0.37506(13) 0.0609(5) Uani 1 1 d . . .
F3A F 0.49889(16) -0.24106(13) 0.40868(12) 0.0871(6) Uani 1 1 d . . .
O1 O 0.13899(17) 0.33831(14) 0.30993(13) 0.0727(6) Uani 1 1 d . . .
O3A O 0.71717(15) 0.31833(13) 0.25929(13) 0.0579(5) Uani 1 1 d . . .
F2A F 0.45987(17) -0.09241(15) 0.45000(12) 0.0911(6) Uani 1 1 d . . .
F1A F 0.62883(18) -0.12513(17) 0.46781(13) 0.1021(7) Uani 1 1 d . . .
O3 O 0.48358(18) 0.57022(16) 0.08795(14) 0.0691(6) Uani 1 1 d . . .
O2 O 0.60592(15) 0.58483(15) 0.21092(14) 0.0698(6) Uani 1 1 d . . .
F1 F 0.2931(2) 0.22653(18) 0.35919(15) 0.1165(8) Uani 1 1 d . . .
F2 F 0.28535(18) 0.13406(15) 0.24803(14) 0.1013(7) Uani 1 1 d . . .
C4A C 0.70147(18) 0.05295(17) 0.31938(15) 0.0398(6) Uani 1 1 d . . .
C5A C 0.77497(18) -0.01587(18) 0.28126(15) 0.0388(6) Uani 1 1 d . . .
C10A C 0.74397(19) -0.12215(18) 0.27769(16) 0.0437(6) Uani 1 1 d . . .
C4 C 0.32366(19) 0.44098(18) 0.23898(16) 0.0441(6) Uani 1 1 d . . .
C18A C 0.73420(19) 0.16698(17) 0.32242(16) 0.0417(6) Uani 1 1 d . . .
C17A C 0.82049(19) 0.22340(19) 0.37938(16) 0.0446(6) Uani 1 1 d . . .
C5 C 0.25591(19) 0.49811(18) 0.29174(15) 0.0422(6) Uani 1 1 d . . .
C16A C 0.8782(2) 0.17730(19) 0.44493(16) 0.0453(6) Uani 1 1 d . . .
C2A C 0.5641(2) -0.10311(18) 0.33490(17) 0.0483(7) Uani 1 1 d . . .
C10 C 0.1642(2) 0.44405(18) 0.32392(16) 0.0463(6) Uani 1 1 d . . .
C3A C 0.6050(2) 0.01121(19) 0.34450(18) 0.0479(7) Uani 1 1 d . . .
C2 C 0.1897(2) 0.28141(18) 0.24904(18) 0.0523(7) Uani 1 1 d . . .
C19A C 0.6866(2) 0.21923(19) 0.26292(17) 0.0461(6) Uani 1 1 d . . .
C18 C 0.4212(2) 0.49674(19) 0.20235(17) 0.0467(6) Uani 1 1 d . . .
C3 C 0.2924(2) 0.3408(2) 0.22003(18) 0.0528(7) Uani 1 1 d . . .
C6A C 0.8731(2) 0.0197(2) 0.24701(17) 0.0491(7) Uani 1 1 d . . .
C28 C 0.1012(2) 0.24103(19) 0.17948(18) 0.0526(7) Uani 1 1 d . . .
C33A C 0.4598(2) -0.12816(19) 0.27385(18) 0.0515(7) Uani 1 1 d . . .
C20A C 0.6021(2) 0.1684(2) 0.20026(18) 0.0520(7) Uani 1 1 d . . .
C22A C 0.4675(2) 0.1742(2) 0.08025(17) 0.0520(7) Uani 1 1 d . . .
C19 C 0.4027(2) 0.5191(2) 0.12343(18) 0.0533(7) Uani 1 1 d . . .
C9 C 0.0954(2) 0.4928(2) 0.37252(19) 0.0558(7) Uani 1 1 d . . .
C9A C 0.8074(2) -0.1914(2) 0.24190(18) 0.0514(7) Uani 1 1 d . . .
C21A C 0.5523(2) 0.2182(2) 0.14536(18) 0.0533(7) Uani 1 1 d . . .
C17 C 0.5301(2) 0.53051(19) 0.24485(18) 0.0523(7) Uani 1 1 d . . .
C8A C 0.9050(2) -0.1535(2) 0.20873(19) 0.0579(8) Uani 1 1 d . . .
C11A C 0.9939(2) 0.2082(2) 0.46366(19) 0.0587(8) Uani 1 1 d . . .
H11A H 1.0332 0.2545 0.4336 0.070 Uiso 1 1 calc R . .
C16 C 0.5651(2) 0.5069(2) 0.32658(19) 0.0564(7) Uani 1 1 d . . .
C6 C 0.2751(2) 0.6045(2) 0.31054(19) 0.0543(7) Uani 1 1 d . . .
C15A C 0.8215(2) 0.1102(2) 0.49165(18) 0.0579(7) Uani 1 1 d . . .
H15A H 0.7439 0.0892 0.4803 0.069 Uiso 1 1 calc R . .
C20 C 0.2957(3) 0.4882(2) 0.0752(2) 0.0555(7) Uani 1 1 d . . .
C7A C 0.9380(2) -0.0489(2) 0.2109(2) 0.0588(8) Uani 1 1 d . . .
C1A C 0.5378(3) -0.1406(2) 0.4153(2) 0.0636(8) Uani 1 1 d . . .
C7 C 0.2061(3) 0.6530(3) 0.3592(2) 0.0688(9) Uani 1 1 d . . .
C21 C 0.2812(3) 0.4995(2) -0.0023(2) 0.0614(8) Uani 1 1 d . . .
C22 C 0.1789(3) 0.4675(2) -0.05577(19) 0.0598(8) Uani 1 1 d . . .
C8 C 0.1168(3) 0.5978(2) 0.3903(2) 0.0643(8) Uani 1 1 d . . .
C27 C 0.0825(3) 0.4107(2) -0.0327(2) 0.0729(9) Uani 1 1 d . . .
H27 H 0.0823 0.3907 0.0187 0.087 Uiso 1 1 calc R . .
C28A C 0.3614(3) -0.0866(2) 0.2873(2) 0.0780(10) Uani 1 1 d . . .
H28A H 0.3577 -0.0429 0.3336 0.094 Uiso 1 1 calc R . .
C29 C 0.1292(3) 0.1807(2) 0.1141(2) 0.0717(9) Uani 1 1 d . . .
H29 H 0.2027 0.1642 0.1126 0.086 Uiso 1 1 calc R . .
C23A C 0.4288(2) 0.2388(3) 0.02621(19) 0.0670(8) Uani 1 1 d . . .
H23A H 0.4571 0.3086 0.0327 0.080 Uiso 1 1 calc R . .
C27A C 0.4226(2) 0.0702(2) 0.0695(2) 0.0663(8) Uani 1 1 d . . .
H27A H 0.4450 0.0261 0.1058 0.080 Uiso 1 1 calc R . .
C1 C 0.2264(3) 0.1927(2) 0.2927(2) 0.0690(9) Uani 1 1 d . . .
C25 C -0.0129(4) 0.4118(3) -0.1627(3) 0.0960(14) Uani 1 1 d . . .
H25 H -0.0770 0.3935 -0.1986 0.115 Uiso 1 1 calc R . .
C15 C 0.5258(3) 0.4179(3) 0.3580(2) 0.0788(10) Uani 1 1 d . . .
H15 H 0.4704 0.3701 0.3284 0.095 Uiso 1 1 calc R . .
C25A C 0.3090(3) 0.0975(3) -0.0474(2) 0.0821(11) Uani 1 1 d . . .
H25A H 0.2569 0.0715 -0.0906 0.099 Uiso 1 1 calc R . .
C30A C 0.2736(4) -0.1719(3) 0.1626(3) 0.1006(14) Uani 1 1 d . . .
H30A H 0.2111 -0.1864 0.1249 0.121 Uiso 1 1 calc R . .
C32A C 0.4641(3) -0.1906(2) 0.2046(2) 0.0705(9) Uani 1 1 d . . .
H32A H 0.5301 -0.2188 0.1949 0.085 Uiso 1 1 calc R . .
C23 C 0.1764(3) 0.4939(3) -0.1336(2) 0.0813(10) Uani 1 1 d . . .
H23 H 0.2405 0.5311 -0.1506 0.098 Uiso 1 1 calc R . .
C33 C -0.0072(3) 0.2672(2) 0.1792(2) 0.0731(9) Uani 1 1 d . . .
H33 H -0.0269 0.3090 0.2223 0.088 Uiso 1 1 calc R . .
C12A C 1.0504(3) 0.1712(3) 0.5261(2) 0.0742(10) Uani 1 1 d . . .
H12A H 1.1281 0.1915 0.5374 0.089 Uiso 1 1 calc R . .
C32 C -0.0863(3) 0.2323(3) 0.1161(3) 0.0951(13) Uani 1 1 d . . .
H32 H -0.1594 0.2502 0.1167 0.114 Uiso 1 1 calc R . .
C26 C -0.0135(3) 0.3836(3) -0.0857(3) 0.0894(12) Uani 1 1 d . . .
H26 H -0.0782 0.3464 -0.0696 0.107 Uiso 1 1 calc R . .
C14A C 0.8789(3) 0.0740(3) 0.55502(19) 0.0721(9) Uani 1 1 d . . .
H14A H 0.8399 0.0291 0.5862 0.087 Uiso 1 1 calc R . .
C26A C 0.3452(3) 0.0321(3) 0.0054(2) 0.0785(10) Uani 1 1 d . . .
H26A H 0.3173 -0.0378 -0.0023 0.094 Uiso 1 1 calc R . .
C13A C 0.9934(3) 0.1044(3) 0.5719(2) 0.0775(10) Uani 1 1 d . . .
H13A H 1.0323 0.0797 0.6143 0.093 Uiso 1 1 calc R . .
C29A C 0.2683(3) -0.1103(3) 0.2318(3) 0.1017(14) Uani 1 1 d . . .
H29A H 0.2012 -0.0840 0.2417 0.122 Uiso 1 1 calc R . .
C24A C 0.3499(3) 0.2008(3) -0.0362(2) 0.0825(10) Uani 1 1 d . . .
H24A H 0.3239 0.2451 -0.0711 0.099 Uiso 1 1 calc R . .
C30 C 0.0495(3) 0.1448(3) 0.0512(2) 0.0976(12) Uani 1 1 d . . .
H30 H 0.0683 0.1028 0.0080 0.117 Uiso 1 1 calc R . .
C31 C -0.0583(3) 0.1718(4) 0.0530(3) 0.1035(14) Uani 1 1 d . . .
H31 H -0.1124 0.1483 0.0104 0.124 Uiso 1 1 calc R . .
C31A C 0.3713(4) -0.2119(3) 0.1491(2) 0.0911(11) Uani 1 1 d . . .
H31A H 0.3754 -0.2539 0.1020 0.109 Uiso 1 1 calc R . .
C24 C 0.0819(4) 0.4663(3) -0.1857(3) 0.0996(13) Uani 1 1 d . . .
H24 H 0.0823 0.4851 -0.2375 0.120 Uiso 1 1 calc R . .
C14 C 0.5669(3) 0.3981(4) 0.4326(3) 0.0977(13) Uani 1 1 d . . .
H14 H 0.5391 0.3374 0.4529 0.117 Uiso 1 1 calc R . .
C11 C 0.6481(3) 0.5748(3) 0.3719(3) 0.0931(12) Uani 1 1 d . . .
H11 H 0.6768 0.6355 0.3519 0.112 Uiso 1 1 calc R . .
C12 C 0.6893(4) 0.5546(4) 0.4461(3) 0.1227(17) Uani 1 1 d . . .
H12 H 0.7458 0.6013 0.4756 0.147 Uiso 1 1 calc R . .
C13 C 0.6481(4) 0.4669(4) 0.4766(3) 0.1070(14) Uani 1 1 d . . .
H13 H 0.6751 0.4540 0.5273 0.128 Uiso 1 1 calc R . .
H21A H 0.580(2) 0.297(2) 0.1498(17) 0.069(8) Uiso 1 1 d . . .
H20A H 0.587(2) 0.100(2) 0.1985(16) 0.055(8) Uiso 1 1 d . . .
H20 H 0.233(2) 0.462(2) 0.0990(19) 0.076(10) Uiso 1 1 d . . .
H2A H 0.785(3) 0.348(3) 0.318(3) 0.124(13) Uiso 1 1 d . . .
H8A H 0.948(2) -0.204(2) 0.1824(17) 0.062(8) Uiso 1 1 d . . .
H8 H 0.063(2) 0.623(2) 0.4252(19) 0.075(9) Uiso 1 1 d . . .
H6A H 0.8973(19) 0.097(2) 0.2498(15) 0.054(7) Uiso 1 1 d . . .
H9 H 0.034(2) 0.453(2) 0.3927(17) 0.061(8) Uiso 1 1 d . . .
H7A H 1.002(2) -0.025(2) 0.1881(17) 0.060(8) Uiso 1 1 d . . .
H9A H 0.780(2) -0.267(2) 0.2433(17) 0.074(9) Uiso 1 1 d . . .
H7 H 0.216(3) 0.714(2) 0.370(2) 0.080(11) Uiso 1 1 d . . .
H3AA H 0.5555(18) 0.0532(17) 0.3674(14) 0.041(7) Uiso 1 1 d . . .
H3A H 0.3328(19) 0.3080(18) 0.1824(15) 0.047(7) Uiso 1 1 d . . .
H6 H 0.337(2) 0.640(2) 0.2868(19) 0.076(10) Uiso 1 1 d . . .
H21 H 0.345(2) 0.534(2) -0.0291(19) 0.079(10) Uiso 1 1 d . . .
H3 H 0.553(3) 0.580(3) 0.134(3) 0.111(13) 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
O1A C10A 1.376(3) . ?
O1A C2A 1.430(3) . ?
F3 C1 1.331(3) . ?
O2A C17A 1.271(3) . ?
O2A H2A 1.33(4) . ?
F3A C1A 1.333(3) . ?
O1 C10 1.378(3) . ?
O1 C2 1.427(3) . ?
O3A C19A 1.315(3) . ?
O3A H2A 1.23(4) . ?
F2A C1A 1.328(3) . ?
F1A C1A 1.330(3) . ?
O3 C19 1.314(3) . ?
O3 H3 1.07(4) . ?
O2 C17 1.280(3) . ?
O2 H3 1.40(4) . ?
F1 C1 1.330(4) . ?
F2 C1 1.326(4) . ?
C4A C5A 1.474(3) . ?
C4A C18A 1.495(3) . ?
C4A C3A 1.323(3) . ?
C5A C10A 1.393(3) . ?
C5A C6A 1.387(3) . ?
C10A C9A 1.379(3) . ?
C4 C5 1.462(3) . ?
C4 C18 1.496(3) . ?
C4 C3 1.324(3) . ?
C18A C17A 1.433(3) . ?
C18A C19A 1.395(3) . ?
C17A C16A 1.478(4) . ?
C5 C10 1.397(3) . ?
C5 C6 1.390(3) . ?
C16A C11A 1.389(3) . ?
C16A C15A 1.381(4) . ?
C2A C3A 1.509(3) . ?
C2A C33A 1.534(4) . ?
C2A C1A 1.525(4) . ?
C10 C9 1.373(4) . ?
C3A H3AA 0.94(2) . ?
C2 C3 1.502(4) . ?
C2 C28 1.525(4) . ?
C2 C1 1.529(4) . ?
C19A C20A 1.454(4) . ?
C18 C19 1.397(4) . ?
C18 C17 1.430(3) . ?
C3 H3A 0.93(2) . ?
C6A C7A 1.388(4) . ?
C6A H6A 1.01(3) . ?
C28 C29 1.382(4) . ?
C28 C33 1.377(4) . ?
C33A C28A 1.380(4) . ?
C33A C32A 1.369(4) . ?
C20A C21A 1.332(4) . ?
C20A H20A 0.89(3) . ?
C22A C21A 1.459(4) . ?
C22A C23A 1.396(4) . ?
C22A C27A 1.392(4) . ?
C19 C20 1.450(4) . ?
C9 C8 1.371(4) . ?
C9 H9 0.95(3) . ?
C9A C8A 1.380(4) . ?
C9A H9A 1.01(3) . ?
C21A H21A 1.04(3) . ?
C17 C16 1.483(4) . ?
C8A C7A 1.377(4) . ?
C8A H8A 0.97(3) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.370(4) . ?
C16 C15 1.372(4) . ?
C16 C11 1.374(4) . ?
C6 C7 1.374(4) . ?
C6 H6 0.95(3) . ?
C15A H15A 0.9300 . ?
C15A C14A 1.382(4) . ?
C20 C21 1.330(4) . ?
C20 H20 0.92(3) . ?
C7A H7A 0.91(3) . ?
C7 C8 1.373(4) . ?
C7 H7 0.80(3) . ?
C21 C22 1.452(4) . ?
C21 H21 0.99(3) . ?
C22 C27 1.387(4) . ?
C22 C23 1.386(4) . ?
C8 H8 0.97(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.385(4) . ?
C28A H28A 0.9300 . ?
C28A C29A 1.381(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.374(5) . ?
C23A H23A 0.9300 . ?
C23A C24A 1.370(4) . ?
C27A H27A 0.9300 . ?
C27A C26A 1.379(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.383(6) . ?
C25 C24 1.358(6) . ?
C15 H15 0.9300 . ?
C15 C14 1.375(5) . ?
C25A H25A 0.9300 . ?
C25A C26A 1.378(5) . ?
C25A C24A 1.374(5) . ?
C30A H30A 0.9300 . ?
C30A C29A 1.366(6) . ?
C30A C31A 1.362(5) . ?
C32A H32A 0.9300 . ?
C32A C31A 1.376(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.365(5) . ?
C33 H33 0.9300 . ?
C33 C32 1.371(5) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.371(5) . ?
C32 H32 0.9300 . ?
C32 C31 1.354(6) . ?
C26 H26 0.9300 . ?
C14A H14A 0.9300 . ?
C14A C13A 1.372(4) . ?
C26A H26A 0.9300 . ?
C13A H13A 0.9300 . ?
C29A H29A 0.9300 . ?
C24A H24A 0.9300 . ?
C30 H30 0.9300 . ?
C30 C31 1.377(5) . ?
C31 H31 0.9300 . ?
C31A H31A 0.9300 . ?
C24 H24 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.358(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.355(6) . ?
C13 H13 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
C10A O1A C2A 121.04(18) . . ?
C17A O2A H2A 107.3(16) . . ?
C10 O1 C2 121.1(2) . . ?
C19A O3A H2A 106.1(17) . . ?
C19 O3 H3 101(2) . . ?
C17 O2 H3 101.0(15) . . ?
C5A C4A C18A 118.8(2) . . ?
C3A C4A C5A 118.5(2) . . ?
C3A C4A C18A 122.6(2) . . ?
C10A C5A C4A 118.9(2) . . ?
C6A C5A C4A 123.3(2) . . ?
C6A C5A C10A 117.8(2) . . ?
O1A C10A C5A 121.7(2) . . ?
O1A C10A C9A 116.0(2) . . ?
C9A C10A C5A 122.2(2) . . ?
C5 C4 C18 120.2(2) . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 C18 120.8(2) . . ?
C17A C18A C4A 122.6(2) . . ?
C19A C18A C4A 118.7(2) . . ?
C19A C18A C17A 118.4(2) . . ?
O2A C17A C18A 120.3(2) . . ?
O2A C17A C16A 115.9(2) . . ?
C18A C17A C16A 123.8(2) . . ?
C10 C5 C4 118.8(2) . . ?
C6 C5 C4 123.9(2) . . ?
C6 C5 C10 117.3(2) . . ?
C11A C16A C17A 118.2(2) . . ?
C15A C16A C17A 123.2(2) . . ?
C15A C16A C11A 118.5(3) . . ?
O1A C2A C3A 113.2(2) . . ?
O1A C2A C33A 109.8(2) . . ?
O1A C2A C1A 101.4(2) . . ?
C3A C2A C33A 110.3(2) . . ?
C3A C2A C1A 110.7(2) . . ?
C1A C2A C33A 111.1(2) . . ?
O1 C10 C5 121.8(2) . . ?
C9 C10 O1 116.2(2) . . ?
C9 C10 C5 122.0(2) . . ?
C4A C3A C2A 123.9(2) . . ?
C4A C3A H3AA 120.3(14) . . ?
C2A C3A H3AA 115.7(14) . . ?
O1 C2 C3 113.8(2) . . ?
O1 C2 C28 109.9(2) . . ?
O1 C2 C1 102.0(2) . . ?
C3 C2 C28 110.8(2) . . ?
C3 C2 C1 109.1(2) . . ?
C28 C2 C1 110.9(2) . . ?
O3A C19A C18A 121.7(2) . . ?
O3A C19A C20A 115.5(2) . . ?
C18A C19A C20A 122.8(2) . . ?
C19 C18 C4 117.6(2) . . ?
C19 C18 C17 119.1(2) . . ?
C17 C18 C4 123.3(2) . . ?
C4 C3 C2 123.7(2) . . ?
C4 C3 H3A 116.8(15) . . ?
C2 C3 H3A 119.2(15) . . ?
C5A C6A C7A 120.7(3) . . ?
C5A C6A H6A 118.7(14) . . ?
C7A C6A H6A 120.5(14) . . ?
C29 C28 C2 120.7(2) . . ?
C33 C28 C2 120.6(3) . . ?
C33 C28 C29 118.6(3) . . ?
C28A C33A C2A 120.4(3) . . ?
C32A C33A C2A 120.4(3) . . ?
C32A C33A C28A 119.2(3) . . ?
C19A C20A H20A 116.3(17) . . ?
C21A C20A C19A 123.3(3) . . ?
C21A C20A H20A 120.3(17) . . ?
C23A C22A C21A 118.9(3) . . ?
C27A C22A C21A 122.9(3) . . ?
C27A C22A C23A 118.2(3) . . ?
O3 C19 C18 121.0(2) . . ?
O3 C19 C20 115.6(3) . . ?
C18 C19 C20 123.3(3) . . ?
C10 C9 H9 119.4(16) . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 121.2(16) . . ?
C10A C9A C8A 118.5(3) . . ?
C10A C9A H9A 117.1(15) . . ?
C8A C9A H9A 124.3(15) . . ?
C20A C21A C22A 127.4(3) . . ?
C20A C21A H21A 114.5(15) . . ?
C22A C21A H21A 118.1(15) . . ?
O2 C17 C18 119.1(3) . . ?
O2 C17 C16 115.5(2) . . ?
C18 C17 C16 125.4(3) . . ?
C9A C8A H8A 117.4(16) . . ?
C7A C8A C9A 120.8(3) . . ?
C7A C8A H8A 121.7(16) . . ?
C16A C11A H11A 119.7 . . ?
C12A C11A C16A 120.5(3) . . ?
C12A C11A H11A 119.7 . . ?
C15 C16 C17 124.1(3) . . ?
C15 C16 C11 117.5(3) . . ?
C11 C16 C17 118.2(3) . . ?
C5 C6 H6 115.6(18) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 123.9(18) . . ?
C16A C15A H15A 119.7 . . ?
C16A C15A C14A 120.7(3) . . ?
C14A C15A H15A 119.7 . . ?
C19 C20 H20 119(2) . . ?
C21 C20 C19 123.6(3) . . ?
C21 C20 H20 117(2) . . ?
C6A C7A H7A 120.3(17) . . ?
C8A C7A C6A 119.8(3) . . ?
C8A C7A H7A 119.9(17) . . ?
F3A C1A C2A 112.2(3) . . ?
F2A C1A F3A 106.4(2) . . ?
F2A C1A F1A 105.6(3) . . ?
F2A C1A C2A 112.8(3) . . ?
F1A C1A F3A 107.1(3) . . ?
F1A C1A C2A 112.1(2) . . ?
C6 C7 H7 121(2) . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 118(2) . . ?
C20 C21 C22 127.5(3) . . ?
C20 C21 H21 119.5(18) . . ?
C22 C21 H21 113.1(18) . . ?
C27 C22 C21 122.8(3) . . ?
C23 C22 C21 119.3(3) . . ?
C23 C22 C27 117.8(3) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 111.7(17) . . ?
C7 C8 H8 128.4(17) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 C22 120.6(4) . . ?
C26 C27 H27 119.7 . . ?
C33A C28A H28A 120.2 . . ?
C33A C28A C29A 119.6(3) . . ?
C29A C28A H28A 120.2 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.7(3) . . ?
C30 C29 H29 119.7 . . ?
C22A C23A H23A 119.5 . . ?
C24A C23A C22A 121.0(3) . . ?
C24A C23A H23A 119.5 . . ?
C22A C27A H27A 119.8 . . ?
C26A C27A C22A 120.5(3) . . ?
C26A C27A H27A 119.8 . . ?
F3 C1 C2 112.7(3) . . ?
F1 C1 F3 106.5(3) . . ?
F1 C1 C2 112.0(3) . . ?
F2 C1 F3 107.1(3) . . ?
F2 C1 F1 106.1(3) . . ?
F2 C1 C2 112.0(3) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C24 C25 C26 119.6(4) . . ?
C16 C15 H15 119.5 . . ?
C16 C15 C14 121.1(4) . . ?
C14 C15 H15 119.5 . . ?
C26A C25A H25A 120.0 . . ?
C24A C25A H25A 120.0 . . ?
C24A C25A C26A 120.1(3) . . ?
C29A C30A H30A 120.3 . . ?
C31A C30A H30A 120.3 . . ?
C31A C30A C29A 119.4(4) . . ?
C33A C32A H32A 119.7 . . ?
C33A C32A C31A 120.5(3) . . ?
C31A C32A H32A 119.7 . . ?
C22 C23 H23 119.3 . . ?
C24 C23 C22 121.3(4) . . ?
C24 C23 H23 119.3 . . ?
C28 C33 H33 119.7 . . ?
C32 C33 C28 120.6(3) . . ?
C32 C33 H33 119.7 . . ?
C11A C12A H12A 119.7 . . ?
C11A C12A C13A 120.6(3) . . ?
C13A C12A H12A 119.7 . . ?
C33 C32 H32 119.9 . . ?
C31 C32 C33 120.1(4) . . ?
C31 C32 H32 119.9 . . ?
C27 C26 H26 120.1 . . ?
C25 C26 C27 119.9(4) . . ?
C25 C26 H26 120.1 . . ?
C15A C14A H14A 120.0 . . ?
C13A C14A C15A 120.0(3) . . ?
C13A C14A H14A 120.0 . . ?
C27A C26A H26A 119.9 . . ?
C25A C26A C27A 120.1(3) . . ?
C25A C26A H26A 119.9 . . ?
C12A C13A C14A 119.8(3) . . ?
C12A C13A H13A 120.1 . . ?
C14A C13A H13A 120.1 . . ?
C28A C29A H29A 119.6 . . ?
C30A C29A C28A 120.8(4) . . ?
C30A C29A H29A 119.6 . . ?
C23A C24A C25A 120.1(3) . . ?
C23A C24A H24A 120.0 . . ?
C25A C24A H24A 120.0 . . ?
C29 C30 H30 120.4 . . ?
C29 C30 C31 119.3(4) . . ?
C31 C30 H30 120.4 . . ?
C32 C31 C30 120.6(4) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C30A C31A C32A 120.5(4) . . ?
C30A C31A H31A 119.8 . . ?
C32A C31A H31A 119.8 . . ?
C25 C24 C23 120.7(4) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14 119.9 . . ?
C16 C11 H11 119.4 . . ?
C12 C11 C16 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(4) . . ?
C13 C12 H12 119.8 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C10A C9A C8A -177.8(3) . . . . ?
O1A C2A C3A C4A 13.0(4) . . . . ?
O1A C2A C33A C28A 173.3(3) . . . . ?
O1A C2A C33A C32A -7.9(4) . . . . ?
O1A C2A C1A F3A -61.0(3) . . . . ?
O1A C2A C1A F2A 178.8(2) . . . . ?
O1A C2A C1A F1A 59.6(3) . . . . ?
O2A C17A C16A C11A -38.4(3) . . . . ?
O2A C17A C16A C15A 137.3(3) . . . . ?
O1 C10 C9 C8 178.7(3) . . . . ?
O1 C2 C3 C4 -10.2(4) . . . . ?
O1 C2 C28 C29 -178.0(3) . . . . ?
O1 C2 C28 C33 4.5(3) . . . . ?
O1 C2 C1 F3 64.6(3) . . . . ?
O1 C2 C1 F1 -55.5(3) . . . . ?
O1 C2 C1 F2 -174.5(2) . . . . ?
O3A C19A C20A C21A -4.3(4) . . . . ?
O3 C19 C20 C21 7.0(4) . . . . ?
O2 C17 C16 C15 -147.9(3) . . . . ?
O2 C17 C16 C11 27.4(4) . . . . ?
C4A C5A C10A O1A -3.2(4) . . . . ?
C4A C5A C10A C9A 179.0(2) . . . . ?
C4A C5A C6A C7A -179.0(2) . . . . ?
C4A C18A C17A O2A 173.6(2) . . . . ?
C4A C18A C17A C16A -5.7(4) . . . . ?
C4A C18A C19A O3A -175.7(2) . . . . ?
C4A C18A C19A C20A 3.2(4) . . . . ?
C5A C4A C18A C17A -78.5(3) . . . . ?
C5A C4A C18A C19A 95.4(3) . . . . ?
C5A C4A C3A C2A -1.4(4) . . . . ?
C5A C10A C9A C8A 0.1(4) . . . . ?
C5A C6A C7A C8A 0.1(4) . . . . ?
C10A O1A C2A C3A -20.1(4) . . . . ?
C10A O1A C2A C33A 103.7(3) . . . . ?
C10A O1A C2A C1A -138.7(2) . . . . ?
C10A C5A C6A C7A -0.3(4) . . . . ?
C10A C9A C8A C7A -0.3(4) . . . . ?
C4 C5 C10 O1 2.7(4) . . . . ?
C4 C5 C10 C9 -178.6(3) . . . . ?
C4 C5 C6 C7 178.5(3) . . . . ?
C4 C18 C19 O3 178.3(2) . . . . ?
C4 C18 C19 C20 -2.1(4) . . . . ?
C4 C18 C17 O2 -174.5(2) . . . . ?
C4 C18 C17 C16 6.3(4) . . . . ?
C18A C4A C5A C10A -179.4(2) . . . . ?
C18A C4A C5A C6A -0.7(4) . . . . ?
C18A C4A C3A C2A 173.8(2) . . . . ?
C18A C17A C16A C11A 141.0(3) . . . . ?
C18A C17A C16A C15A -43.3(4) . . . . ?
C18A C19A C20A C21A 176.8(3) . . . . ?
C17A C18A C19A O3A -1.6(4) . . . . ?
C17A C18A C19A C20A 177.3(2) . . . . ?
C17A C16A C11A C12A 177.2(3) . . . . ?
C17A C16A C15A C14A -176.3(3) . . . . ?
C5 C4 C18 C19 -99.1(3) . . . . ?
C5 C4 C18 C17 78.8(3) . . . . ?
C5 C4 C3 C2 0.6(4) . . . . ?
C5 C10 C9 C8 0.0(5) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C16A C11A C12A C13A -1.1(5) . . . . ?
C16A C15A C14A C13A -0.2(5) . . . . ?
C2A O1A C10A C5A 16.3(4) . . . . ?
C2A O1A C10A C9A -165.8(2) . . . . ?
C2A C33A C28A C29A -179.8(3) . . . . ?
C2A C33A C32A C31A -179.0(3) . . . . ?
C10 O1 C2 C3 16.2(4) . . . . ?
C10 O1 C2 C28 -108.7(3) . . . . ?
C10 O1 C2 C1 133.6(3) . . . . ?
C10 C5 C6 C7 0.4(4) . . . . ?
C10 C9 C8 C7 0.3(5) . . . . ?
C3A C4A C5A C10A -4.1(4) . . . . ?
C3A C4A C5A C6A 174.6(3) . . . . ?
C3A C4A C18A C17A 106.4(3) . . . . ?
C3A C4A C18A C19A -79.7(3) . . . . ?
C3A C2A C33A C28A -61.3(3) . . . . ?
C3A C2A C33A C32A 117.6(3) . . . . ?
C3A C2A C1A F3A 178.6(2) . . . . ?
C3A C2A C1A F2A 58.3(3) . . . . ?
C3A C2A C1A F1A -60.8(3) . . . . ?
C2 O1 C10 C5 -13.3(4) . . . . ?
C2 O1 C10 C9 167.9(3) . . . . ?
C2 C28 C29 C30 -179.6(3) . . . . ?
C2 C28 C33 C32 179.0(3) . . . . ?
C19A C18A C17A O2A -0.2(4) . . . . ?
C19A C18A C17A C16A -179.6(2) . . . . ?
C19A C20A C21A C22A 179.7(2) . . . . ?
C18 C4 C5 C10 178.9(2) . . . . ?
C18 C4 C5 C6 0.8(4) . . . . ?
C18 C4 C3 C2 -174.8(3) . . . . ?
C18 C19 C20 C21 -172.6(3) . . . . ?
C18 C17 C16 C15 31.3(4) . . . . ?
C18 C17 C16 C11 -153.4(3) . . . . ?
C3 C4 C5 C10 3.5(4) . . . . ?
C3 C4 C5 C6 -174.7(3) . . . . ?
C3 C4 C18 C19 76.2(3) . . . . ?
C3 C4 C18 C17 -105.8(3) . . . . ?
C3 C2 C28 C29 55.3(3) . . . . ?
C3 C2 C28 C33 -122.2(3) . . . . ?
C3 C2 C1 F3 -174.7(3) . . . . ?
C3 C2 C1 F1 65.3(3) . . . . ?
C3 C2 C1 F2 -53.8(3) . . . . ?
C6A C5A C10A O1A 178.0(2) . . . . ?
C6A C5A C10A C9A 0.2(4) . . . . ?
C28 C2 C3 C4 114.3(3) . . . . ?
C28 C2 C1 F3 -52.4(3) . . . . ?
C28 C2 C1 F1 -172.5(2) . . . . ?
C28 C2 C1 F2 68.5(3) . . . . ?
C28 C29 C30 C31 1.7(5) . . . . ?
C28 C33 C32 C31 -0.3(5) . . . . ?
C33A C2A C3A C4A -110.5(3) . . . . ?
C33A C2A C1A F3A 55.7(3) . . . . ?
C33A C2A C1A F2A -64.6(3) . . . . ?
C33A C2A C1A F1A 176.3(2) . . . . ?
C33A C28A C29A C30A -2.0(6) . . . . ?
C33A C32A C31A C30A -0.5(5) . . . . ?
C22A C23A C24A C25A -1.3(5) . . . . ?
C22A C27A C26A C25A -1.9(5) . . . . ?
C19 C18 C17 O2 3.4(4) . . . . ?
C19 C18 C17 C16 -175.7(2) . . . . ?
C19 C20 C21 C22 177.6(3) . . . . ?
C9A C8A C7A C6A 0.2(5) . . . . ?
C21A C22A C23A C24A 179.5(3) . . . . ?
C21A C22A C27A C26A -177.9(3) . . . . ?
C17 C18 C19 O3 0.2(4) . . . . ?
C17 C18 C19 C20 179.8(2) . . . . ?
C17 C16 C15 C14 176.1(3) . . . . ?
C17 C16 C11 C12 -176.1(4) . . . . ?
C11A C16A C15A C14A -0.7(4) . . . . ?
C11A C12A C13A C14A 0.2(5) . . . . ?
C16 C15 C14 C13 -0.2(6) . . . . ?
C16 C11 C12 C13 -0.5(7) . . . . ?
C6 C5 C10 O1 -179.0(3) . . . . ?
C6 C5 C10 C9 -0.3(4) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C15A C16A C11A C12A 1.3(4) . . . . ?
C15A C14A C13A C12A 0.5(5) . . . . ?
C20 C21 C22 C27 -5.9(5) . . . . ?
C20 C21 C22 C23 174.4(3) . . . . ?
C1A C2A C3A C4A 126.1(3) . . . . ?
C1A C2A C33A C28A 61.9(3) . . . . ?
C1A C2A C33A C32A -119.3(3) . . . . ?
C21 C22 C27 C26 179.0(3) . . . . ?
C21 C22 C23 C24 -179.4(3) . . . . ?
C22 C27 C26 C25 1.1(5) . . . . ?
C22 C23 C24 C25 -0.1(6) . . . . ?
C27 C22 C23 C24 0.9(5) . . . . ?
C28A C33A C32A C31A -0.1(5) . . . . ?
C29 C28 C33 C32 1.4(5) . . . . ?
C29 C30 C31 C32 -0.6(6) . . . . ?
C23A C22A C21A C20A -177.1(3) . . . . ?
C23A C22A C27A C26A 2.3(4) . . . . ?
C27A C22A C21A C20A 3.1(4) . . . . ?
C27A C22A C23A C24A -0.7(4) . . . . ?
C1 C2 C3 C4 -123.4(3) . . . . ?
C1 C2 C28 C29 -66.0(3) . . . . ?
C1 C2 C28 C33 116.5(3) . . . . ?
C15 C16 C11 C12 -0.5(6) . . . . ?
C15 C14 C13 C12 -0.8(7) . . . . ?
C32A C33A C28A C29A 1.4(5) . . . . ?
C23 C22 C27 C26 -1.4(4) . . . . ?
C33 C28 C29 C30 -2.1(5) . . . . ?
C33 C32 C31 C30 -0.1(6) . . . . ?
C26 C25 C24 C23 -0.2(6) . . . . ?
C26A C25A C24A C23A 1.7(5) . . . . ?
C29A C30A C31A C32A 0.0(6) . . . . ?
C24A C25A C26A C27A -0.1(5) . . . . ?
C31A C30A C29A C28A 1.3(6) . . . . ?
C24 C25 C26 C27 -0.3(6) . . . . ?
C11 C16 C15 C14 0.8(5) . . . . ?
C11 C12 C13 C14 1.2(8) . . . . ?

####################################################################### 
# 
# 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_875
_database_code_depnum_ccdc_archive 'CCDC 2154343'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-07-24 downloaded from the CCDC.
;
_audit_creation_date             2020-09-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 F3 N O5'
_chemical_formula_sum            'C27 H20 F3 N O5'
_chemical_formula_weight         495.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.7920(6)
_cell_length_b                   12.2767(8)
_cell_length_c                   19.2845(12)
_cell_angle_alpha                87.355(5)
_cell_angle_beta                 85.247(5)
_cell_angle_gamma                88.238(5)
_cell_volume                     2307.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.7300
_cell_measurement_theta_min      3.6530
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22870
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.762
_diffrn_reflns_theta_min         3.526
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  63.00   1.00   60.00    --   22.21-101.00 161.00   73
  2  ω    -67.00  23.00   1.00   60.00    --  -23.92 101.00 -95.00   90
  3  ω      1.00  91.00   1.00   60.00    --   22.21  57.00 150.00   90
  4  ω     -2.00  92.00   1.00   60.00    --   22.21  38.00 -90.00   94
  5  ω    -92.00   4.00   1.00   60.00    --  -23.92 -77.00   0.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0334647000
_diffrn_orient_matrix_UB_12      0.0194106000
_diffrn_orient_matrix_UB_13      -0.0295764000
_diffrn_orient_matrix_UB_21      0.0645052000
_diffrn_orient_matrix_UB_22      0.0061857000
_diffrn_orient_matrix_UB_23      -0.0191739000
_diffrn_orient_matrix_UB_31      -0.0025259000
_diffrn_orient_matrix_UB_32      -0.0541537000
_diffrn_orient_matrix_UB_33      -0.0110635000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5586
_reflns_number_total             12399
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     724
_refine_ls_number_reflns         12399
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1528
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.004
_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)+(0.0670P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1968
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F1B-C1A
 1.34 with sigma of 0.02
 C1A-F3B
 1.34 with sigma of 0.02
 C1A-F3A
 1.34 with sigma of 0.02
 C1A-F1A
 1.34 with sigma of 0.02
 C1A-F2A
 1.34 with sigma of 0.02
 C1A-F2B
 1.34 with sigma of 0.02
3. Others
 Fixed Sof: F1A(0.7) F3A(0.7) F2A(0.7) F3B(0.3) F1B(0.3) F2B(0.3)
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C7(H7), C23(H23), C27(H27), C8(H8), C26(H26), C24(H24),
 C17(H17), C19(H19), C25(H25), C20(H20), C18(H18), C21(H21), C6A(H6A),
 C23A(H23A), C27A(H27A), C9A(H9A), C17A(H17A), C21A(H21A), C26A(H26A), C8A(H8A),
  C7A(H7A), C20A(H20A), C25A(H25A), C24A(H24A), C18A(H18A), C19A(H19A)
;
_atom_sites_solution_hydrogens   mixed
_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
F3 F 0.45206(18) 0.71211(14) 0.23389(10) 0.0787(6) Uani 1 1 d . . . . .
F2 F 0.5181(2) 0.62479(19) 0.32297(11) 0.1038(8) Uani 1 1 d . . . . .
F1 F 0.5891(2) 0.57649(16) 0.22280(15) 0.1164(9) Uani 1 1 d . . . . .
O1 O 0.63920(18) 0.82459(13) 0.30311(8) 0.0459(4) Uani 1 1 d . . . . .
O4 O 1.18547(19) 0.61170(16) 0.36549(11) 0.0602(5) Uani 1 1 d . . . . .
O5 O 1.0711(2) 0.45235(16) 0.42774(10) 0.0629(5) Uani 1 1 d . . . . .
O3 O 0.8618(3) 0.63161(17) 0.16070(10) 0.0789(7) Uani 1 1 d . . . . .
O2 O 0.8758(3) 0.50816(17) 0.24143(11) 0.0846(8) Uani 1 1 d . . . . .
N1 N 0.8557(2) 0.60143(18) 0.22189(11) 0.0484(5) Uani 1 1 d . . . . .
C3 C 0.8192(3) 0.68822(18) 0.27494(12) 0.0379(5) Uani 1 1 d . . . . .
C4 C 0.8101(3) 0.63845(19) 0.34960(12) 0.0386(5) Uani 1 1 d . . . . .
C11 C 0.9349(3) 0.77437(19) 0.26814(13) 0.0387(5) Uani 1 1 d . . . . .
C5 C 0.7539(3) 0.72936(19) 0.39676(12) 0.0402(6) Uani 1 1 d . . . . .
C10 C 0.6731(3) 0.81563(19) 0.37200(12) 0.0410(6) Uani 1 1 d . . . . .
C6 C 0.7872(3) 0.7334(2) 0.46607(13) 0.0479(6) Uani 1 1 d . . . . .
H6 H 0.840729 0.677376 0.484795 0.057 Uiso 1 1 calc R U . . .
C13 C 1.0689(3) 0.6396(2) 0.34413(13) 0.0439(6) Uani 1 1 d . . . . .
C2 C 0.6794(3) 0.7397(2) 0.25789(14) 0.0425(6) Uani 1 1 d . . . . .
C12 C 1.0714(3) 0.7185(2) 0.28257(15) 0.0472(6) Uani 1 1 d . . . . .
C15 C 0.9550(3) 0.4905(2) 0.40843(13) 0.0465(6) Uani 1 1 d . . . . .
C22 C 0.9469(3) 0.8520(2) 0.20435(12) 0.0421(6) Uani 1 1 d . . . . .
C9 C 0.6298(3) 0.9018(2) 0.41213(15) 0.0523(7) Uani 1 1 d . . . . .
H9 H 0.577558 0.958790 0.393596 0.063 Uiso 1 1 calc R U . . .
C14 C 0.9462(3) 0.59053(19) 0.37064(12) 0.0410(6) Uani 1 1 d . . . . .
C16 C 0.8384(3) 0.4157(2) 0.42172(14) 0.0492(7) Uani 1 1 d . . . . .
C7 C 0.7420(3) 0.8187(2) 0.50689(14) 0.0562(7) Uani 1 1 d . . . . .
H7 H 0.764140 0.819237 0.552849 0.067 Uiso 1 1 calc R U . . .
C23 C 1.0409(3) 0.8354(2) 0.14762(13) 0.0552(7) Uani 1 1 d . . . . .
H23 H 1.092781 0.770660 0.145740 0.066 Uiso 1 1 calc R U . . .
C27 C 0.8694(3) 0.9496(2) 0.20467(14) 0.0527(7) Uani 1 1 d . . . . .
H27 H 0.804388 0.962373 0.241553 0.063 Uiso 1 1 calc R U . . .
C1 C 0.5596(3) 0.6626(2) 0.25955(16) 0.0561(7) Uani 1 1 d . . . . .
C8 C 0.6640(3) 0.9032(2) 0.47958(15) 0.0571(7) Uani 1 1 d . . . . .
H8 H 0.634591 0.961139 0.506955 0.069 Uiso 1 1 calc R U . . .
C26 C 0.8883(4) 1.0273(2) 0.15071(16) 0.0640(8) Uani 1 1 d . . . . .
H26 H 0.835989 1.091814 0.151642 0.077 Uiso 1 1 calc R U . . .
C24 C 1.0588(4) 0.9135(3) 0.09386(15) 0.0686(9) Uani 1 1 d . . . . .
H24 H 1.121827 0.900776 0.056140 0.082 Uiso 1 1 calc R U . . .
C17 C 0.7225(4) 0.4396(3) 0.46396(17) 0.0709(9) Uani 1 1 d . . . . .
H17 H 0.715025 0.505480 0.486149 0.085 Uiso 1 1 calc R U . . .
C19 C 0.6259(5) 0.2703(3) 0.4413(2) 0.0882(12) Uani 1 1 d . . . . .
H19 H 0.555441 0.220912 0.448292 0.106 Uiso 1 1 calc R U . . .
C25 C 0.9834(4) 1.0099(3) 0.09602(16) 0.0724(10) Uani 1 1 d . . . . .
H25 H 0.997113 1.063092 0.060397 0.087 Uiso 1 1 calc R U . . .
C20 C 0.7394(5) 0.2467(3) 0.3983(3) 0.1094(15) Uani 1 1 d . . . . .
H20 H 0.744525 0.182083 0.374731 0.131 Uiso 1 1 calc R U . . .
C18 C 0.6160(4) 0.3665(3) 0.47396(19) 0.0839(11) Uani 1 1 d . . . . .
H18 H 0.538228 0.383333 0.502928 0.101 Uiso 1 1 calc R U . . .
C21 C 0.8466(4) 0.3175(3) 0.3893(2) 0.0863(11) Uani 1 1 d . . . . .
H21 H 0.924919 0.299057 0.361207 0.104 Uiso 1 1 calc R U . . .
O4A O 0.5554(2) 0.92346(14) 0.10146(10) 0.0558(5) Uani 1 1 d . . . . .
O5A O 0.6627(2) 1.06413(15) 0.02067(9) 0.0579(5) Uani 1 1 d . . . . .
O1A O 0.1422(2) 1.26439(15) 0.21806(10) 0.0638(6) Uani 1 1 d . . . . .
O3A O 0.4552(2) 1.13360(17) 0.32930(10) 0.0677(6) Uani 1 1 d . . . . .
C14A C 0.4961(3) 1.11079(19) 0.10967(12) 0.0405(6) Uani 1 1 d . . . . .
C4A C 0.4046(3) 1.19583(19) 0.14626(12) 0.0403(6) Uani 1 1 d . . . . .
C13A C 0.4830(3) 1.00099(19) 0.13097(13) 0.0438(6) Uani 1 1 d . . . . .
C11A C 0.2908(3) 1.04924(19) 0.22550(13) 0.0403(6) Uani 1 1 d . . . . .
C16A C 0.6294(3) 1.2532(2) 0.03137(14) 0.0450(6) Uani 1 1 d . . . . .
C3A C 0.3595(3) 1.16281(19) 0.22205(12) 0.0410(6) Uani 1 1 d . . . . .
C22A C 0.2213(3) 1.00883(19) 0.29534(13) 0.0429(6) Uani 1 1 d . . . . .
C5A C 0.2766(3) 1.22775(19) 0.10933(13) 0.0431(6) Uani 1 1 d . . . . .
N1A N 0.4811(3) 1.15106(19) 0.26713(12) 0.0549(6) Uani 1 1 d . . . . .
C15A C 0.5952(3) 1.1386(2) 0.05514(13) 0.0449(6) Uani 1 1 d . . . . .
C6A C 0.2744(3) 1.2240(2) 0.03736(14) 0.0495(7) Uani 1 1 d . . . . .
H6A H 0.350957 1.196610 0.011326 0.059 Uiso 1 1 calc R U . . .
C12A C 0.3931(3) 0.9640(2) 0.19364(15) 0.0485(7) Uani 1 1 d . . . . .
C23A C 0.0879(3) 1.0426(2) 0.31532(15) 0.0548(7) Uani 1 1 d . . . . .
H23A H 0.042650 1.092677 0.286983 0.066 Uiso 1 1 calc R U . . .
F1A F 0.3540(9) 1.4136(5) 0.2001(3) 0.0829(17) Uani 0.7 1 d D . P A 1
C27A C 0.2852(3) 0.9346(2) 0.33971(13) 0.0525(7) Uani 1 1 d . . . . .
H27A H 0.374797 0.910870 0.327786 0.063 Uiso 1 1 calc R U . . .
C9A C 0.0442(3) 1.3032(2) 0.11228(19) 0.0698(9) Uani 1 1 d . . . . .
H9A H -0.033143 1.330150 0.137868 0.084 Uiso 1 1 calc R U . . .
C17A C 0.6279(3) 1.2824(2) -0.03870(15) 0.0619(8) Uani 1 1 d . . . . .
H17A H 0.604440 1.231320 -0.069545 0.074 Uiso 1 1 calc R U . . .
C10A C 0.1579(3) 1.2654(2) 0.14573(15) 0.0530(7) Uani 1 1 d . . . . .
C21A C 0.6666(3) 1.3290(2) 0.07668(15) 0.0573(7) Uani 1 1 d . . . . .
H21A H 0.668520 1.310485 0.123898 0.069 Uiso 1 1 calc R U . . .
O2A O 0.5965(3) 1.1569(3) 0.23953(12) 0.1018(10) Uani 1 1 d . . . . .
C26A C 0.2178(4) 0.8954(3) 0.40119(15) 0.0661(9) Uani 1 1 d . . . . .
H26A H 0.262282 0.845635 0.430035 0.079 Uiso 1 1 calc R U . . .
C2A C 0.2618(3) 1.2512(2) 0.25404(16) 0.0554(8) Uani 1 1 d . . . . .
C8A C 0.0471(4) 1.3002(3) 0.0411(2) 0.0739(10) Uani 1 1 d . . . . .
H8A H -0.028403 1.325665 0.018261 0.089 Uiso 1 1 calc R U . . .
C7A C 0.1606(3) 1.2601(2) 0.00359(17) 0.0648(8) Uani 1 1 d . . . . .
H7A H 0.161561 1.257022 -0.044542 0.078 Uiso 1 1 calc R U . . .
C20A C 0.7010(4) 1.4330(3) 0.05124(19) 0.0727(10) Uani 1 1 d . . . . .
H20A H 0.727846 1.483740 0.081461 0.087 Uiso 1 1 calc R U . . .
F3A F 0.2149(6) 1.4293(3) 0.2866(3) 0.1272(17) Uani 0.7 1 d D . P A 1
C25A C 0.0859(4) 0.9293(3) 0.41990(16) 0.0731(10) Uani 1 1 d . . . . .
H25A H 0.040746 0.902956 0.461317 0.088 Uiso 1 1 calc R U . . .
C24A C 0.0212(4) 1.0026(3) 0.37699(17) 0.0700(9) Uani 1 1 d . . . . .
H24A H -0.068436 1.025661 0.389415 0.084 Uiso 1 1 calc R U . . .
C18A C 0.6607(4) 1.3864(3) -0.06333(19) 0.0786(10) Uani 1 1 d . . . . .
H18A H 0.659043 1.405200 -0.110521 0.094 Uiso 1 1 calc R U . . .
C19A C 0.6958(4) 1.4618(3) -0.0183(2) 0.0796(10) Uani 1 1 d . . . . .
H19A H 0.716009 1.532337 -0.034727 0.095 Uiso 1 1 calc R U . . .
F2A F 0.4207(10) 1.3650(4) 0.2969(4) 0.142(4) Uani 0.7 1 d D . P A 1
C1A C 0.3228(5) 1.3639(3) 0.2603(2) 0.0814(12) Uani 1 1 d D . . . .
H4AA H 0.458(3) 1.260(2) 0.1471(12) 0.043(7) Uiso 1 1 d . . . . .
H4B H 0.743(2) 0.5770(18) 0.3519(11) 0.033(6) Uiso 1 1 d . . . . .
H2A H 0.233(2) 1.2291(18) 0.3011(13) 0.040(6) Uiso 1 1 d . . . . .
H2 H 0.688(3) 0.774(2) 0.2101(14) 0.050(7) Uiso 1 1 d . . . . .
H12C H 1.108(3) 0.676(2) 0.2455(14) 0.060(9) Uiso 1 1 d . . . . .
H11A H 0.221(3) 1.0574(19) 0.1914(12) 0.042(7) Uiso 1 1 d . . . . .
H11 H 0.912(2) 0.8220(18) 0.3054(12) 0.034(6) Uiso 1 1 d . . . . .
H12A H 0.341(3) 0.897(3) 0.1807(14) 0.074(9) Uiso 1 1 d . . . . .
H12D H 1.140(3) 0.774(2) 0.2876(14) 0.062(8) Uiso 1 1 d . . . . .
H12B H 0.451(4) 0.939(3) 0.2302(17) 0.093(12) Uiso 1 1 d . . . . .
H4A H 0.620(4) 0.973(3) 0.055(2) 0.120(13) Uiso 1 1 d . . . . .
F3B F 0.4697(13) 1.3491(10) 0.2614(7) 0.109(5) Uani 0.3 1 d D . P A 2
H4 H 1.155(5) 0.522(4) 0.397(2) 0.154(17) Uiso 1 1 d . . . . .
F1B F 0.3158(18) 1.4010(12) 0.3256(6) 0.139(6) Uani 0.3 1 d D . P A 2
F2B F 0.316(3) 1.4336(15) 0.2100(11) 0.170(11) Uani 0.3 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 C1 1.320(3) . ?
F2 C1 1.324(3) . ?
F1 C1 1.311(4) . ?
O1 C10 1.394(3) . ?
O1 C2 1.415(3) . ?
O4 C13 1.278(3) . ?
O4 H4 1.26(5) . ?
O5 C15 1.293(3) . ?
O5 H4 1.30(5) . ?
O3 N1 1.218(3) . ?
O2 N1 1.204(3) . ?
N1 C3 1.525(3) . ?
C3 C4 1.535(3) . ?
C3 C11 1.567(3) . ?
C3 C2 1.544(3) . ?
C4 C5 1.533(3) . ?
C4 C14 1.518(3) . ?
C4 H4B 1.02(2) . ?
C11 C12 1.524(4) . ?
C11 C22 1.520(3) . ?
C11 H11 0.95(2) . ?
C5 C10 1.393(3) . ?
C5 C6 1.405(3) . ?
C10 C9 1.375(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(4) . ?
C13 C12 1.496(3) . ?
C13 C14 1.408(3) . ?
C2 C1 1.528(4) . ?
C2 H2 0.99(2) . ?
C12 H12C 0.94(3) . ?
C12 H12D 0.99(3) . ?
C15 C14 1.403(3) . ?
C15 C16 1.486(4) . ?
C22 C23 1.389(4) . ?
C22 C27 1.398(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.371(4) . ?
C16 C17 1.374(4) . ?
C16 C21 1.380(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(4) . ?
C27 H27 0.9300 . ?
C27 C26 1.384(4) . ?
C8 H8 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.368(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.376(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.393(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.362(6) . ?
C19 C18 1.361(5) . ?
C25 H25 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.379(5) . ?
C18 H18 0.9300 . ?
C21 H21 0.9300 . ?
O4A C13A 1.294(3) . ?
O4A H4A 1.20(4) . ?
O5A C15A 1.288(3) . ?
O5A H4A 1.34(4) . ?
O1A C10A 1.390(3) . ?
O1A C2A 1.411(4) . ?
O3A N1A 1.215(3) . ?
C14A C4A 1.516(3) . ?
C14A C13A 1.398(3) . ?
C14A C15A 1.408(3) . ?
C4A C3A 1.531(3) . ?
C4A C5A 1.524(3) . ?
C4A H4AA 0.95(2) . ?
C13A C12A 1.496(4) . ?
C11A C3A 1.563(3) . ?
C11A C22A 1.526(3) . ?
C11A C12A 1.539(4) . ?
C11A H11A 0.99(2) . ?
C16A C15A 1.499(3) . ?
C16A C17A 1.383(4) . ?
C16A C21A 1.383(4) . ?
C3A N1A 1.531(3) . ?
C3A C2A 1.541(4) . ?
C22A C23A 1.388(4) . ?
C22A C27A 1.391(4) . ?
C5A C6A 1.393(4) . ?
C5A C10A 1.386(4) . ?
N1A O2A 1.211(3) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.388(4) . ?
C12A H12A 1.03(3) . ?
C12A H12B 0.97(3) . ?
C23A H23A 0.9300 . ?
C23A C24A 1.385(4) . ?
F1A C1A 1.305(6) . ?
C27A H27A 0.9300 . ?
C27A C26A 1.382(4) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.389(4) . ?
C9A C8A 1.374(5) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.380(4) . ?
C21A H21A 0.9300 . ?
C21A C20A 1.388(4) . ?
C26A H26A 0.9300 . ?
C26A C25A 1.369(5) . ?
C2A C1A 1.537(4) . ?
C2A H2A 0.96(2) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.365(5) . ?
C7A H7A 0.9300 . ?
C20A H20A 0.9300 . ?
C20A C19A 1.376(5) . ?
F3A C1A 1.384(6) . ?
C25A H25A 0.9300 . ?
C25A C24A 1.370(5) . ?
C24A H24A 0.9300 . ?
C18A H18A 0.9300 . ?
C18A C19A 1.368(5) . ?
C19A H19A 0.9300 . ?
F2A C1A 1.237(8) . ?
C1A F3B 1.445(14) . ?
C1A F1B 1.353(11) . ?
C1A F2B 1.268(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C2 119.30(19) . . ?
C13 O4 H4 99(2) . . ?
C15 O5 H4 101(2) . . ?
O3 N1 C3 116.8(2) . . ?
O2 N1 O3 123.3(2) . . ?
O2 N1 C3 119.9(2) . . ?
N1 C3 C4 111.27(19) . . ?
N1 C3 C11 108.44(19) . . ?
N1 C3 C2 106.86(19) . . ?
C4 C3 C11 108.17(19) . . ?
C4 C3 C2 110.3(2) . . ?
C2 C3 C11 111.76(19) . . ?
C3 C4 H4B 107.5(12) . . ?
C5 C4 C3 106.29(19) . . ?
C5 C4 H4B 109.9(13) . . ?
C14 C4 C3 112.9(2) . . ?
C14 C4 C5 112.4(2) . . ?
C14 C4 H4B 107.7(13) . . ?
C3 C11 H11 105.1(13) . . ?
C12 C11 C3 109.6(2) . . ?
C12 C11 H11 106.3(14) . . ?
C22 C11 C3 119.1(2) . . ?
C22 C11 C12 112.4(2) . . ?
C22 C11 H11 103.1(13) . . ?
C10 C5 C4 121.7(2) . . ?
C10 C5 C6 116.4(2) . . ?
C6 C5 C4 121.9(2) . . ?
C5 C10 O1 122.1(2) . . ?
C9 C10 O1 115.3(2) . . ?
C9 C10 C5 122.4(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
O4 C13 C12 115.9(2) . . ?
O4 C13 C14 122.8(2) . . ?
C14 C13 C12 120.9(2) . . ?
O1 C2 C3 110.93(19) . . ?
O1 C2 C1 107.4(2) . . ?
O1 C2 H2 106.5(15) . . ?
C3 C2 H2 109.1(16) . . ?
C1 C2 C3 116.6(2) . . ?
C1 C2 H2 105.7(15) . . ?
C11 C12 H12C 112.7(18) . . ?
C11 C12 H12D 109.5(17) . . ?
C13 C12 C11 116.1(2) . . ?
C13 C12 H12C 103.2(16) . . ?
C13 C12 H12D 109.2(16) . . ?
H12C C12 H12D 105(2) . . ?
O5 C15 C14 121.1(2) . . ?
O5 C15 C16 115.3(2) . . ?
C14 C15 C16 123.3(2) . . ?
C23 C22 C11 122.8(2) . . ?
C23 C22 C27 117.7(2) . . ?
C27 C22 C11 119.2(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.1 . . ?
C13 C14 C4 119.4(2) . . ?
C15 C14 C4 121.8(2) . . ?
C15 C14 C13 118.2(2) . . ?
C17 C16 C15 123.4(3) . . ?
C17 C16 C21 118.4(3) . . ?
C21 C16 C15 118.2(3) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.5 . . ?
C22 C27 H27 119.6 . . ?
C26 C27 C22 120.7(3) . . ?
C26 C27 H27 119.6 . . ?
F3 C1 F2 106.5(3) . . ?
F3 C1 C2 110.9(2) . . ?
F2 C1 C2 113.6(2) . . ?
F1 C1 F3 106.9(2) . . ?
F1 C1 F2 105.9(3) . . ?
F1 C1 C2 112.6(3) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C27 C26 H26 119.8 . . ?
C25 C26 C27 120.5(3) . . ?
C25 C26 H26 119.8 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.8(3) . . ?
C26 C25 C24 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.7(4) . . ?
C21 C20 H20 119.6 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.1 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.4(4) . . ?
C20 C21 H21 119.8 . . ?
C13A O4A H4A 102(2) . . ?
C15A O5A H4A 102.0(18) . . ?
C10A O1A C2A 117.5(2) . . ?
C13A C14A C4A 119.1(2) . . ?
C13A C14A C15A 118.6(2) . . ?
C15A C14A C4A 122.3(2) . . ?
C14A C4A C3A 113.4(2) . . ?
C14A C4A C5A 113.9(2) . . ?
C14A C4A H4AA 106.7(15) . . ?
C3A C4A H4AA 106.9(14) . . ?
C5A C4A C3A 108.0(2) . . ?
C5A C4A H4AA 107.5(15) . . ?
O4A C13A C14A 122.8(2) . . ?
O4A C13A C12A 114.2(2) . . ?
C14A C13A C12A 122.8(2) . . ?
C3A C11A H11A 104.3(13) . . ?
C22A C11A C3A 117.8(2) . . ?
C22A C11A C12A 112.2(2) . . ?
C22A C11A H11A 108.5(14) . . ?
C12A C11A C3A 109.4(2) . . ?
C12A C11A H11A 103.4(15) . . ?
C17A C16A C15A 118.5(2) . . ?
C21A C16A C15A 122.2(2) . . ?
C21A C16A C17A 119.2(2) . . ?
C4A C3A C11A 109.71(19) . . ?
C4A C3A C2A 109.9(2) . . ?
N1A C3A C4A 112.0(2) . . ?
N1A C3A C11A 106.73(19) . . ?
N1A C3A C2A 106.9(2) . . ?
C2A C3A C11A 111.6(2) . . ?
C23A C22A C11A 120.1(2) . . ?
C23A C22A C27A 117.5(3) . . ?
C27A C22A C11A 122.3(3) . . ?
C6A C5A C4A 121.9(2) . . ?
C10A C5A C4A 121.4(2) . . ?
C10A C5A C6A 116.7(3) . . ?
O3A N1A C3A 117.1(2) . . ?
O2A N1A O3A 123.7(3) . . ?
O2A N1A C3A 119.2(2) . . ?
O5A C15A C14A 120.9(2) . . ?
O5A C15A C16A 114.7(2) . . ?
C14A C15A C16A 124.4(2) . . ?
C5A C6A H6A 119.2 . . ?
C7A C6A C5A 121.5(3) . . ?
C7A C6A H6A 119.2 . . ?
C13A C12A C11A 116.7(2) . . ?
C13A C12A H12A 108.0(16) . . ?
C13A C12A H12B 109(2) . . ?
C11A C12A H12A 109.5(18) . . ?
C11A C12A H12B 107(2) . . ?
H12A C12A H12B 107(2) . . ?
C22A C23A H23A 119.6 . . ?
C24A C23A C22A 120.8(3) . . ?
C24A C23A H23A 119.6 . . ?
C22A C27A H27A 119.4 . . ?
C26A C27A C22A 121.2(3) . . ?
C26A C27A H27A 119.4 . . ?
C10A C9A H9A 120.3 . . ?
C8A C9A H9A 120.3 . . ?
C8A C9A C10A 119.4(3) . . ?
C16A C17A H17A 119.6 . . ?
C18A C17A C16A 120.7(3) . . ?
C18A C17A H17A 119.6 . . ?
C5A C10A O1A 122.5(3) . . ?
C5A C10A C9A 122.1(3) . . ?
C9A C10A O1A 115.4(3) . . ?
C16A C21A H21A 120.2 . . ?
C16A C21A C20A 119.6(3) . . ?
C20A C21A H21A 120.2 . . ?
C27A C26A H26A 119.8 . . ?
C25A C26A C27A 120.4(3) . . ?
C25A C26A H26A 119.8 . . ?
O1A C2A C3A 111.3(2) . . ?
O1A C2A C1A 108.8(3) . . ?
O1A C2A H2A 107.0(15) . . ?
C3A C2A H2A 109.1(15) . . ?
C1A C2A C3A 116.3(3) . . ?
C1A C2A H2A 103.8(14) . . ?
C9A C8A H8A 119.9 . . ?
C7A C8A C9A 120.2(3) . . ?
C7A C8A H8A 119.9 . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A C6A 120.0(3) . . ?
C8A C7A H7A 120.0 . . ?
C21A C20A H20A 119.7 . . ?
C19A C20A C21A 120.5(3) . . ?
C19A C20A H20A 119.7 . . ?
C26A C25A H25A 120.3 . . ?
C26A C25A C24A 119.3(3) . . ?
C24A C25A H25A 120.3 . . ?
C23A C24A H24A 119.6 . . ?
C25A C24A C23A 120.8(3) . . ?
C25A C24A H24A 119.6 . . ?
C17A C18A H18A 120.0 . . ?
C19A C18A C17A 120.0(3) . . ?
C19A C18A H18A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C18A C19A C20A 119.9(3) . . ?
C18A C19A H19A 120.0 . . ?
F1A C1A C2A 113.0(4) . . ?
F1A C1A F3A 101.1(5) . . ?
F3A C1A C2A 105.3(4) . . ?
F2A C1A F1A 110.2(7) . . ?
F2A C1A C2A 115.2(4) . . ?
F2A C1A F3A 111.0(5) . . ?
F3B C1A C2A 108.0(5) . . ?
F1B C1A C2A 115.3(6) . . ?
F1B C1A F3B 89.9(9) . . ?
F2B C1A C2A 118.6(13) . . ?
F2B C1A F3B 100.6(14) . . ?
F2B C1A F1B 117.8(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C9 C8 -176.7(2) . . . . ?
O1 C2 C1 F3 64.6(3) . . . . ?
O1 C2 C1 F2 -55.4(3) . . . . ?
O1 C2 C1 F1 -175.7(2) . . . . ?
O4 C13 C12 C11 -164.9(2) . . . . ?
O4 C13 C14 C4 171.8(2) . . . . ?
O4 C13 C14 C15 -16.3(4) . . . . ?
O5 C15 C14 C4 -177.9(2) . . . . ?
O5 C15 C14 C13 10.5(4) . . . . ?
O5 C15 C16 C17 119.1(3) . . . . ?
O5 C15 C16 C21 -61.6(4) . . . . ?
O3 N1 C3 C4 178.0(2) . . . . ?
O3 N1 C3 C11 -63.2(3) . . . . ?
O3 N1 C3 C2 57.4(3) . . . . ?
O2 N1 C3 C4 -1.4(3) . . . . ?
O2 N1 C3 C11 117.5(3) . . . . ?
O2 N1 C3 C2 -121.9(3) . . . . ?
N1 C3 C4 C5 -172.33(19) . . . . ?
N1 C3 C4 C14 64.0(3) . . . . ?
N1 C3 C11 C12 -60.2(3) . . . . ?
N1 C3 C11 C22 71.3(3) . . . . ?
N1 C3 C2 O1 -177.81(18) . . . . ?
N1 C3 C2 C1 58.9(3) . . . . ?
C3 C4 C5 C10 25.7(3) . . . . ?
C3 C4 C5 C6 -150.8(2) . . . . ?
C3 C4 C14 C13 33.4(3) . . . . ?
C3 C4 C14 C15 -138.1(2) . . . . ?
C3 C11 C12 C13 -44.6(3) . . . . ?
C3 C11 C22 C23 -99.2(3) . . . . ?
C3 C11 C22 C27 86.8(3) . . . . ?
C3 C2 C1 F3 -170.3(2) . . . . ?
C3 C2 C1 F2 69.8(3) . . . . ?
C3 C2 C1 F1 -50.6(3) . . . . ?
C4 C3 C11 C12 60.6(3) . . . . ?
C4 C3 C11 C22 -167.9(2) . . . . ?
C4 C3 C2 O1 61.1(2) . . . . ?
C4 C3 C2 C1 -62.3(3) . . . . ?
C4 C5 C10 O1 -0.3(4) . . . . ?
C4 C5 C10 C9 -175.3(2) . . . . ?
C4 C5 C6 C7 176.5(2) . . . . ?
C11 C3 C4 C5 68.6(2) . . . . ?
C11 C3 C4 C14 -55.1(3) . . . . ?
C11 C3 C2 O1 -59.3(3) . . . . ?
C11 C3 C2 C1 177.3(2) . . . . ?
C11 C22 C23 C24 -173.1(3) . . . . ?
C11 C22 C27 C26 173.2(2) . . . . ?
C5 C4 C14 C13 -86.9(3) . . . . ?
C5 C4 C14 C15 101.6(3) . . . . ?
C5 C10 C9 C8 -1.4(4) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C10 O1 C2 C3 -34.5(3) . . . . ?
C10 O1 C2 C1 94.0(2) . . . . ?
C10 C5 C6 C7 -0.2(4) . . . . ?
C10 C9 C8 C7 0.3(4) . . . . ?
C6 C5 C10 O1 176.4(2) . . . . ?
C6 C5 C10 C9 1.3(4) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C2 O1 C10 C5 4.7(3) . . . . ?
C2 O1 C10 C9 -179.9(2) . . . . ?
C2 C3 C4 C5 -53.9(2) . . . . ?
C2 C3 C4 C14 -177.60(18) . . . . ?
C2 C3 C11 C12 -177.7(2) . . . . ?
C2 C3 C11 C22 -46.3(3) . . . . ?
C12 C11 C22 C23 31.0(3) . . . . ?
C12 C11 C22 C27 -143.1(3) . . . . ?
C12 C13 C14 C4 -16.0(4) . . . . ?
C12 C13 C14 C15 155.8(3) . . . . ?
C15 C16 C17 C18 179.5(3) . . . . ?
C15 C16 C21 C20 -178.1(3) . . . . ?
C22 C11 C12 C13 -179.4(2) . . . . ?
C22 C23 C24 C25 0.4(5) . . . . ?
C22 C27 C26 C25 0.0(4) . . . . ?
C14 C4 C5 C10 149.7(2) . . . . ?
C14 C4 C5 C6 -26.8(3) . . . . ?
C14 C13 C12 C11 22.4(4) . . . . ?
C14 C15 C16 C17 -68.0(4) . . . . ?
C14 C15 C16 C21 111.3(3) . . . . ?
C16 C15 C14 C4 9.5(4) . . . . ?
C16 C15 C14 C13 -162.1(3) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C23 C22 C27 C26 -1.2(4) . . . . ?
C23 C24 C25 C26 -1.6(5) . . . . ?
C27 C22 C23 C24 1.0(4) . . . . ?
C27 C26 C25 C24 1.4(5) . . . . ?
C17 C16 C21 C20 1.3(5) . . . . ?
C19 C20 C21 C16 -2.5(7) . . . . ?
C20 C19 C18 C17 -0.8(6) . . . . ?
C18 C19 C20 C21 2.2(7) . . . . ?
C21 C16 C17 C18 0.2(5) . . . . ?
O4A C13A C12A C11A -172.3(2) . . . . ?
O1A C2A C1A F1A -59.0(6) . . . . ?
O1A C2A C1A F3A 50.5(5) . . . . ?
O1A C2A C1A F2A 173.1(6) . . . . ?
O1A C2A C1A F3B -149.9(7) . . . . ?
O1A C2A C1A F1B 111.4(11) . . . . ?
O1A C2A C1A F2B -36.5(14) . . . . ?
C14A C4A C3A C11A -54.3(3) . . . . ?
C14A C4A C3A N1A 64.0(3) . . . . ?
C14A C4A C3A C2A -177.4(2) . . . . ?
C14A C4A C5A C6A -29.5(3) . . . . ?
C14A C4A C5A C10A 152.7(2) . . . . ?
C14A C13A C12A C11A 12.8(4) . . . . ?
C4A C14A C13A O4A 178.6(2) . . . . ?
C4A C14A C13A C12A -7.0(4) . . . . ?
C4A C14A C15A O5A -173.5(2) . . . . ?
C4A C14A C15A C16A 5.3(4) . . . . ?
C4A C3A N1A O3A 174.3(2) . . . . ?
C4A C3A N1A O2A -7.4(4) . . . . ?
C4A C3A C2A O1A 61.2(3) . . . . ?
C4A C3A C2A C1A -64.0(3) . . . . ?
C4A C5A C6A C7A -175.6(2) . . . . ?
C4A C5A C10A O1A -7.8(4) . . . . ?
C4A C5A C10A C9A 174.7(2) . . . . ?
C13A C14A C4A C3A 28.4(3) . . . . ?
C13A C14A C4A C5A -95.8(3) . . . . ?
C13A C14A C15A O5A 7.1(4) . . . . ?
C13A C14A C15A C16A -174.1(2) . . . . ?
C11A C3A N1A O3A -65.7(3) . . . . ?
C11A C3A N1A O2A 112.6(3) . . . . ?
C11A C3A C2A O1A -60.7(3) . . . . ?
C11A C3A C2A C1A 174.0(3) . . . . ?
C11A C22A C23A C24A 176.9(2) . . . . ?
C11A C22A C27A C26A -177.0(2) . . . . ?
C16A C17A C18A C19A 0.2(5) . . . . ?
C16A C21A C20A C19A 1.3(5) . . . . ?
C3A C4A C5A C6A -156.5(2) . . . . ?
C3A C4A C5A C10A 25.6(3) . . . . ?
C3A C11A C22A C23A 83.6(3) . . . . ?
C3A C11A C22A C27A -99.1(3) . . . . ?
C3A C11A C12A C13A -38.1(3) . . . . ?
C3A C2A C1A F1A 67.5(6) . . . . ?
C3A C2A C1A F3A 177.0(4) . . . . ?
C3A C2A C1A F2A -60.4(7) . . . . ?
C3A C2A C1A F3B -23.4(7) . . . . ?
C3A C2A C1A F1B -122.1(11) . . . . ?
C3A C2A C1A F2B 90.0(14) . . . . ?
C22A C11A C3A C4A -171.8(2) . . . . ?
C22A C11A C3A N1A 66.6(3) . . . . ?
C22A C11A C3A C2A -49.8(3) . . . . ?
C22A C11A C12A C13A -170.7(2) . . . . ?
C22A C23A C24A C25A 0.5(4) . . . . ?
C22A C27A C26A C25A -0.2(4) . . . . ?
C5A C4A C3A C11A 73.0(2) . . . . ?
C5A C4A C3A N1A -168.70(19) . . . . ?
C5A C4A C3A C2A -50.1(3) . . . . ?
C5A C6A C7A C8A -0.2(4) . . . . ?
N1A C3A C2A O1A -177.0(2) . . . . ?
N1A C3A C2A C1A 57.7(3) . . . . ?
C15A C14A C4A C3A -151.1(2) . . . . ?
C15A C14A C4A C5A 84.8(3) . . . . ?
C15A C14A C13A O4A -1.9(4) . . . . ?
C15A C14A C13A C12A 172.5(2) . . . . ?
C15A C16A C17A C18A -179.0(3) . . . . ?
C15A C16A C21A C20A 178.1(3) . . . . ?
C6A C5A C10A O1A 174.3(2) . . . . ?
C6A C5A C10A C9A -3.3(4) . . . . ?
C12A C11A C3A C4A 58.5(3) . . . . ?
C12A C11A C3A N1A -63.0(3) . . . . ?
C12A C11A C3A C2A -179.4(2) . . . . ?
C12A C11A C22A C23A -148.1(3) . . . . ?
C12A C11A C22A C27A 29.3(3) . . . . ?
C23A C22A C27A C26A 0.4(4) . . . . ?
C27A C22A C23A C24A -0.6(4) . . . . ?
C27A C26A C25A C24A 0.1(5) . . . . ?
C9A C8A C7A C6A -1.2(5) . . . . ?
C17A C16A C15A O5A 50.9(4) . . . . ?
C17A C16A C15A C14A -128.0(3) . . . . ?
C17A C16A C21A C20A 0.3(4) . . . . ?
C17A C18A C19A C20A 1.4(6) . . . . ?
C10A O1A C2A C3A -42.8(3) . . . . ?
C10A O1A C2A C1A 86.5(3) . . . . ?
C10A C5A C6A C7A 2.4(4) . . . . ?
C10A C9A C8A C7A 0.3(5) . . . . ?
C21A C16A C15A O5A -127.0(3) . . . . ?
C21A C16A C15A C14A 54.2(4) . . . . ?
C21A C16A C17A C18A -1.1(5) . . . . ?
C21A C20A C19A C18A -2.2(6) . . . . ?
C26A C25A C24A C23A -0.2(5) . . . . ?
C2A O1A C10A C5A 16.5(4) . . . . ?
C2A O1A C10A C9A -165.8(2) . . . . ?
C2A C3A N1A O3A 53.9(3) . . . . ?
C2A C3A N1A O2A -127.9(3) . . . . ?
C8A C9A C10A O1A -175.7(3) . . . . ?
C8A C9A C10A C5A 2.0(4) . . . . ?

_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 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.771
####################################################################### 
# 
# 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_1204
_database_code_depnum_ccdc_archive 'CCDC 2154345'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-07-24 downloaded from the CCDC.
;
_audit_creation_date             2021-05-12
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_formula_moiety         'C31 H25 Cl F3 N O9, C7 H8'
_chemical_formula_sum            'C38 H33 Cl F3 N O9'
_chemical_formula_weight         740.13
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.9834(10)
_cell_length_b                   11.4504(11)
_cell_length_c                   19.4781(18)
_cell_angle_alpha                73.898(8)
_cell_angle_beta                 86.642(8)
_cell_angle_gamma                83.762(8)
_cell_volume                     1912.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.2150
_cell_measurement_theta_min      2.4240
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2850
_exptl_crystal_description       block
_exptl_crystal_F_000             768.8016
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.1106
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13790
_diffrn_reflns_theta_full        26.000000
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         1.86
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9879
_diffrn_measured_fraction_theta_max 0.8398
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  43.00   1.00  100.00    --   17.44 -77.00 -30.00   82
  2  ω    -25.00  34.00   1.00  100.00    --   17.44 -57.00  60.00   59
  3  ω     -9.00  32.00   1.00  100.00    --   17.44  77.00  60.00   41
  4  ω     -7.00  39.00   1.00  100.00    --   17.44  77.00-180.00   46
  5  ω    -50.00  33.00   1.00  100.00    --   17.44 -57.00-150.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0312072000
_diffrn_orient_matrix_UB_12      -0.0325444000
_diffrn_orient_matrix_UB_13      -0.0208854000
_diffrn_orient_matrix_UB_21      -0.0050037000
_diffrn_orient_matrix_UB_22      -0.0505097000
_diffrn_orient_matrix_UB_23      0.0306026000
_diffrn_orient_matrix_UB_31      -0.0729064000
_diffrn_orient_matrix_UB_32      0.0241996000
_diffrn_orient_matrix_UB_33      0.0080703000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                3589
_reflns_number_total             8637
_reflns_odcompleteness_completeness 98.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.572067
_refine_diff_density_min         -0.685039
_refine_diff_density_rms         0.123057
_refine_ls_d_res_high            0.730259
_refine_ls_d_res_low             8.926233
_refine_ls_goodness_of_fit_ref   1.043143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     491
_refine_ls_number_reflns         8637
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.177662
_refine_ls_R_factor_gt           0.073808
_refine_ls_restrained_S_all      1.040845
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0843P)²+0.0222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.225982
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Cl1 Cl 0.60642(17) 1.12893(14) 0.01270(7) 0.1030(5) Uani 1.000000 .
O2 O 0.1253(3) 0.7298(2) 0.20926(13) 0.0492(7) Uani 1.000000 .
F3 F 0.1985(4) 1.3126(3) 0.34074(16) 0.1256(14) Uani 1.000000 .
O3 O 0.0486(3) 1.0767(2) 0.08062(13) 0.0573(7) Uani 1.000000 .
O1 O 0.3933(3) 1.1237(2) 0.30412(13) 0.0504(7) Uani 1.000000 .
F1 F 0.1960(3) 1.3067(2) 0.23356(14) 0.0814(8) Uani 1.000000 .
O8 O 0.6101(3) 0.8501(3) 0.52651(14) 0.0670(8) Uani 1.000000 .
O9 O 0.3991(5) 0.7619(3) 0.62404(15) 0.0798(11) Uani 1.000000 .
O6 O 0.1854(3) 0.3839(3) 0.03967(17) 0.0758(9) Uani 1.000000 .
O4 O -0.0807(3) 1.0029(3) 0.28481(18) 0.0867(11) Uani 1.000000 .
O5 O -0.0091(3) 1.0133(3) 0.38672(16) 0.0732(9) Uani 1.000000 .
O7 O -0.0668(4) 0.3040(3) 0.10620(19) 0.0757(10) Uani 1.000000 .
N1 N 0.0144(4) 1.0119(3) 0.32428(19) 0.0543(8) Uani 1.000000 .
F2 F 0.0123(4) 1.2503(3) 0.30257(18) 0.1100(11) Uani 1.000000 .
C7 C 0.5398(5) 1.1271(4) 0.0988(2) 0.0654(12) Uani 1.000000 .
C14 C 0.1480(4) 0.9436(3) 0.18714(18) 0.0382(8) Uani 1.000000 .
C13 C 0.1577(4) 0.8284(3) 0.22907(19) 0.0430(9) Uani 1.000000 .
C22 C 0.1065(4) 0.4579(4) 0.0766(2) 0.0498(10) Uani 1.000000 .
C27 C 0.3683(5) 0.7907(4) 0.55305(19) 0.0535(10) Uani 1.000000 .
C11 C 0.2670(4) 0.8915(3) 0.32848(18) 0.0418(9) Uani 1.000000 .
C21 C -0.0234(4) 0.4136(4) 0.1103(2) 0.0518(10) Uani 1.000000 .
C4 C 0.1871(4) 1.0495(3) 0.21407(17) 0.0374(8) Uani 1.000000 .
C15 C 0.0732(4) 0.9725(3) 0.11850(19) 0.0439(9) Uani 1.000000 .
C3 C 0.1780(4) 1.0184(3) 0.29639(18) 0.0391(8) Uani 1.000000 .
C18 C 0.0626(4) 0.6320(3) 0.1229(2) 0.0485(10) Uani 1.000000 .
C26 C 0.4750(4) 0.8391(3) 0.5006(2) 0.0497(10) Uani 1.000000 .
C5 C 0.3425(4) 1.0892(3) 0.18912(19) 0.0422(9) Uani 1.000000 .
C29 C 0.1968(4) 0.8029(4) 0.46110(19) 0.0534(10) Uani 1.000000 .
C24 C 0.2991(4) 0.8550(3) 0.40850(18) 0.0446(9) Uani 1.000000 .
C25 C 0.4402(4) 0.8708(3) 0.42961(19) 0.0452(9) Uani 1.000000 .
C17 C 0.1139(5) 0.7482(3) 0.1323(2) 0.0501(10) Uani 1.000000 .
C23 C 0.1495(4) 0.5672(3) 0.0830(2) 0.0505(10) Uani 1.000000 .
C10 C 0.4353(4) 1.1239(3) 0.2338(2) 0.0457(9) Uani 1.000000 .
C19 C -0.0663(5) 0.5875(4) 0.1572(2) 0.0609(11) Uani 1.000000 .
C20 C -0.1100(5) 0.4776(4) 0.1507(2) 0.0651(12) Uani 1.000000 .
C12 C 0.1966(5) 0.7914(3) 0.30587(19) 0.0519(10) Uani 1.000000 .
C2 C 0.2391(4) 1.1172(4) 0.3230(2) 0.0474(10) Uani 1.000000 .
C6 C 0.3979(4) 1.0928(3) 0.1202(2) 0.0513(10) Uani 1.000000 .
C16 C 0.0185(5) 0.8644(3) 0.1003(2) 0.0540(11) Uani 1.000000 .
C28 C 0.2315(5) 0.7726(4) 0.5325(2) 0.0598(11) Uani 1.000000 .
C9 C 0.5774(4) 1.1585(4) 0.2123(2) 0.0615(11) Uani 1.000000 .
C1 C 0.1595(6) 1.2467(4) 0.2997(2) 0.0632(12) Uani 1.000000 .
C8 C 0.6301(5) 1.1599(4) 0.1442(3) 0.0720(13) Uani 1.000000 .
C31 C 0.7307(5) 0.8844(5) 0.4765(2) 0.0752(14) Uani 1.000000 .
C30 C 0.3251(6) 0.4166(5) 0.0080(3) 0.0964(17) Uani 1.000000 .
C6S C 0.5362(7) 0.7055(8) 0.1788(4) 0.125(2) Uani 1.000000 .
C1S C 0.5312(7) 0.6060(6) 0.2359(4) 0.110(2) Uani 1.000000 .
C2S C 0.5871(10) 0.6040(9) 0.3017(5) 0.161(3) Uani 1.000000 .
C5S C 0.5996(10) 0.8029(9) 0.1787(6) 0.162(3) Uani 1.000000 .
C3S C 0.6551(11) 0.7140(11) 0.3009(5) 0.171(3) Uani 1.000000 .
C4S C 0.6535(9) 0.8064(8) 0.2405(6) 0.140(3) Uani 1.000000 .
C7S C 0.4598(9) 0.5006(8) 0.2294(6) 0.206(4) Uani 1.000000 .
H2 H 0.234(3) 1.093(3) 0.3760(17) 0.032(8) Uiso 1.000000 .
H17 H 0.220(5) 0.763(3) 0.112(2) 0.068(12) Uiso 1.000000 .
H11 H 0.367(3) 0.900(3) 0.2997(15) 0.031(8) Uiso 1.000000 .
H25 H 0.5115(4) 0.9033(3) 0.39504(19) 0.0542(11) Uiso 1.000000 R
H28 H 0.1607(5) 0.7394(4) 0.5672(2) 0.0718(13) Uiso 1.000000 R
H29 H 0.1040(4) 0.7882(4) 0.44827(19) 0.0641(12) Uiso 1.000000 R
H19 H -0.1244(5) 0.6306(4) 0.1849(2) 0.0731(14) Uiso 1.000000 R
H20 H -0.1974(5) 0.4479(4) 0.1737(2) 0.0781(14) Uiso 1.000000 R
H23 H 0.2372(4) 0.5966(3) 0.0601(2) 0.0606(12) Uiso 1.000000 R
H8 H 0.7254(5) 1.1827(4) 0.1290(3) 0.0864(15) Uiso 1.000000 R
H9a H 0.6365(4) 1.1806(4) 0.2434(2) 0.0738(14) Uiso 1.000000 R
H6 H 0.3390(4) 1.0720(3) 0.0885(2) 0.0615(12) Uiso 1.000000 R
H30a H 0.3124(8) 0.4962(15) -0.0252(15) 0.145(3) Uiso 1.000000 G
H30b H 0.3920(14) 0.418(3) 0.0445(4) 0.145(3) Uiso 1.000000 G
H30c H 0.366(2) 0.3582(19) -0.0167(17) 0.145(3) Uiso 1.000000 G
H31a H 0.7028(13) 0.9624(13) 0.4438(10) 0.113(2) Uiso 1.000000 G
H31b H 0.8176(11) 0.889(3) 0.5016(3) 0.113(2) Uiso 1.000000 G
H31c H 0.753(2) 0.8243(14) 0.4504(11) 0.113(2) Uiso 1.000000 G
H6S H 0.4917(7) 0.7043(8) 0.1371(4) 0.150(3) Uiso 1.000000 R
H5S H 0.6069(10) 0.8670(9) 0.1375(6) 0.195(4) Uiso 1.000000 R
H4S H 0.6926(9) 0.8776(8) 0.2419(6) 0.168(3) Uiso 1.000000 R
H3S H 0.6992(11) 0.7204(11) 0.3415(5) 0.206(4) Uiso 1.000000 R
H2S H 0.5814(10) 0.5384(9) 0.3422(5) 0.194(4) Uiso 1.000000 R
H7Sa H 0.3531(10) 0.520(3) 0.228(4) 0.309(6) Uiso 1.000000 G
H7Sb H 0.495(7) 0.481(5) 0.186(2) 0.309(6) Uiso 1.000000 G
H7Sc H 0.485(7) 0.432(2) 0.270(2) 0.309(6) Uiso 1.000000 G
H12a H 0.1067(5) 0.7714(3) 0.33498(19) 0.0623(12) Uiso 1.000000 R
H12b H 0.2664(5) 0.7183(3) 0.31500(19) 0.0623(12) Uiso 1.000000 R
H16a H -0.0841(5) 0.8557(3) 0.1180(2) 0.0648(13) Uiso 1.000000 R
H16b H 0.0196(5) 0.8793(3) 0.0488(2) 0.0648(13) Uiso 1.000000 R
H4 H 0.1136(4) 1.1194(3) 0.19544(17) 0.0449(10) Uiso 1.000000 R
H7 H 0.007(5) 0.269(4) 0.086(2) 0.074(16) Uiso 1.000000 .
H9 H 0.480(6) 0.778(5) 0.625(3) 0.10(2) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C7 1.742(4) .
O2 C13 1.354(4) .
O2 C17 1.464(4) .
F3 C1 1.325(5) .
O3 C15 1.221(4) .
O1 C10 1.399(4) .
O1 C2 1.416(4) .
F1 C1 1.322(5) .
O8 C26 1.372(4) .
O8 C31 1.427(5) .
O9 C27 1.367(5) .
O9 H9 0.77(5) .
O6 C22 1.372(4) .
O6 C30 1.407(5) .
O4 N1 1.213(4) .
O5 N1 1.226(4) .
O7 C21 1.378(5) .
O7 H7 0.86(4) .
N1 C3 1.539(4) .
F2 C1 1.317(5) .
C7 C6 1.381(5) .
C7 C8 1.385(6) .
C14 C13 1.342(5) .
C14 C4 1.529(5) .
C14 C15 1.470(5) .
C13 C12 1.489(5) .
C22 C21 1.379(5) .
C22 C23 1.389(5) .
C27 C26 1.398(5) .
C27 C28 1.368(5) .
C11 C3 1.563(5) .
C11 C24 1.533(5) .
C11 C12 1.543(5) .
C11 H11 1.03(3) .
C21 C20 1.374(5) .
C4 C3 1.542(4) .
C4 C5 1.526(5) .
C4 H4 0.9800 .
C15 C16 1.515(5) .
C3 C2 1.531(5) .
C18 C17 1.514(5) .
C18 C23 1.375(5) .
C18 C19 1.377(5) .
C26 C25 1.375(5) .
C5 C10 1.399(5) .
C5 C6 1.395(5) .
C29 C24 1.385(5) .
C29 C28 1.383(5) .
C29 H29 0.9300 .
C24 C25 1.400(5) .
C25 H25 0.9300 .
C17 C16 1.498(5) .
C17 H17 1.02(4) .
C23 H23 0.9300 .
C10 C9 1.385(5) .
C19 C20 1.399(5) .
C19 H19 0.9300 .
C20 H20 0.9300 .
C12 H12a 0.9700 .
C12 H12b 0.9700 .
C2 C1 1.533(5) .
C2 H2 0.99(3) .
C6 H6 0.9300 .
C16 H16a 0.9700 .
C16 H16b 0.9700 .
C28 H28 0.9300 .
C9 C8 1.377(5) .
C9 H9a 0.9300 .
C8 H8 0.9300 .
C31 H31a 0.9600 .
C31 H31b 0.9600 .
C31 H31c 0.9600 .
C30 H30a 0.9600 .
C30 H30b 0.9600 .
C30 H30c 0.9600 .
C6S C1S 1.356(8) .
C6S C5S 1.306(10) .
C6S H6S 0.9300 .
C1S C2S 1.397(10) .
C1S C7S 1.465(9) .
C2S C3S 1.454(12) .
C2S H2S 0.9300 .
C5S C4S 1.336(10) .
C5S H5S 0.9300 .
C3S C4S 1.346(11) .
C3S H3S 0.9300 .
C4S H4S 0.9300 .
C7S H7Sa 0.9600 .
C7S H7Sb 0.9600 .
C7S H7Sc 0.9600 .

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
C17 O2 C13 115.5(3) . .
C2 O1 C10 116.5(3) . .
C31 O8 C26 118.2(3) . .
H9 O9 C27 105(4) . .
C30 O6 C22 118.5(3) . .
H7 O7 C21 107(3) . .
O5 N1 O4 124.6(3) . .
C3 N1 O4 119.1(3) . .
C3 N1 O5 116.3(3) . .
C6 C7 Cl1 119.2(3) . .
C8 C7 Cl1 119.4(3) . .
C8 C7 C6 121.4(4) . .
C4 C14 C13 121.7(3) . .
C15 C14 C13 119.2(3) . .
C15 C14 C4 118.2(3) . .
C14 C13 O2 125.3(3) . .
C12 C13 O2 109.9(3) . .
C12 C13 C14 124.7(3) . .
C21 C22 O6 114.3(3) . .
C23 C22 O6 125.4(4) . .
C23 C22 C21 120.3(3) . .
C26 C27 O9 120.9(4) . .
C28 C27 O9 120.0(4) . .
C28 C27 C26 119.1(3) . .
C24 C11 C3 117.7(3) . .
C12 C11 C3 109.9(3) . .
C12 C11 C24 112.5(3) . .
H11 C11 C3 102.4(16) . .
H11 C11 C24 108.9(16) . .
H11 C11 C12 104.2(16) . .
C22 C21 O7 121.5(4) . .
C20 C21 O7 118.6(4) . .
C20 C21 C22 119.9(4) . .
C3 C4 C14 111.8(3) . .
C5 C4 C14 113.3(3) . .
C5 C4 C3 108.1(3) . .
H4 C4 C14 107.83(18) . .
H4 C4 C3 107.83(18) . .
H4 C4 C5 107.83(18) . .
C14 C15 O3 122.7(3) . .
C16 C15 O3 122.0(3) . .
C16 C15 C14 115.1(3) . .
C11 C3 N1 108.5(3) . .
C4 C3 N1 110.9(3) . .
C4 C3 C11 109.4(3) . .
C2 C3 N1 106.4(3) . .
C2 C3 C11 110.4(3) . .
C2 C3 C4 111.2(3) . .
C23 C18 C17 119.7(4) . .
C19 C18 C17 120.4(3) . .
C19 C18 C23 119.8(3) . .
C27 C26 O8 114.7(3) . .
C25 C26 O8 125.4(3) . .
C25 C26 C27 119.9(3) . .
C10 C5 C4 121.8(3) . .
C6 C5 C4 121.1(3) . .
C6 C5 C10 117.1(3) . .
C28 C29 C24 120.6(4) . .
H29 C29 C24 119.7(2) . .
H29 C29 C28 119.7(2) . .
C29 C24 C11 123.2(3) . .
C25 C24 C11 118.7(3) . .
C25 C24 C29 118.1(3) . .
C24 C25 C26 121.1(3) . .
H25 C25 C26 119.5(2) . .
H25 C25 C24 119.5(2) . .
C18 C17 O2 106.5(3) . .
C16 C17 O2 110.2(3) . .
C16 C17 C18 116.6(3) . .
H17 C17 O2 105(2) . .
H17 C17 C18 113(2) . .
H17 C17 C16 106(2) . .
C18 C23 C22 120.1(4) . .
H23 C23 C22 119.9(2) . .
H23 C23 C18 119.9(2) . .
C5 C10 O1 122.7(3) . .
C9 C10 O1 114.7(3) . .
C9 C10 C5 122.5(3) . .
C20 C19 C18 120.2(4) . .
H19 C19 C18 119.9(2) . .
H19 C19 C20 119.9(2) . .
C19 C20 C21 119.8(4) . .
H20 C20 C21 120.1(2) . .
H20 C20 C19 120.1(2) . .
C11 C12 C13 113.0(3) . .
H12a C12 C13 109.0(2) . .
H12a C12 C11 109.0(2) . .
H12b C12 C13 109.0(2) . .
H12b C12 C11 109.0(2) . .
H12b C12 H12a 107.8 . .
C3 C2 O1 110.4(3) . .
C1 C2 O1 108.1(3) . .
C1 C2 C3 117.5(3) . .
H2 C2 O1 105.3(17) . .
H2 C2 C3 108.9(18) . .
H2 C2 C1 105.9(16) . .
C5 C6 C7 120.4(4) . .
H6 C6 C7 119.8(2) . .
H6 C6 C5 119.8(2) . .
C17 C16 C15 111.8(3) . .
H16a C16 C15 109.3(2) . .
H16a C16 C17 109.3(2) . .
H16b C16 C15 109.3(2) . .
H16b C16 C17 109.3(2) . .
H16b C16 H16a 107.9 . .
C29 C28 C27 121.1(4) . .
H28 C28 C27 119.5(2) . .
H28 C28 C29 119.5(2) . .
C8 C9 C10 119.2(4) . .
H9a C9 C10 120.4(2) . .
H9a C9 C8 120.4(2) . .
F1 C1 F3 105.6(4) . .
F2 C1 F3 107.8(4) . .
F2 C1 F1 105.9(4) . .
C2 C1 F3 110.0(4) . .
C2 C1 F1 113.2(3) . .
C2 C1 F2 113.8(4) . .
C9 C8 C7 119.4(4) . .
H8 C8 C7 120.3(3) . .
H8 C8 C9 120.3(2) . .
H31a C31 O8 109.5 . .
H31b C31 O8 109.5 . .
H31b C31 H31a 109.5 . .
H31c C31 O8 109.5 . .
H31c C31 H31a 109.5 . .
H31c C31 H31b 109.5 . .
H30a C30 O6 109.5 . .
H30b C30 O6 109.5 . .
H30b C30 H30a 109.5 . .
H30c C30 O6 109.5 . .
H30c C30 H30a 109.5 . .
H30c C30 H30b 109.5 . .
C5S C6S C1S 124.0(9) . .
H6S C6S C1S 118.0(5) . .
H6S C6S C5S 118.0(6) . .
C2S C1S C6S 121.3(8) . .
C7S C1S C6S 119.3(9) . .
C7S C1S C2S 119.3(8) . .
C3S C2S C1S 113.7(9) . .
H2S C2S C1S 123.1(5) . .
H2S C2S C3S 123.1(6) . .
C4S C5S C6S 117.0(10) . .
H5S C5S C6S 121.5(6) . .
H5S C5S C4S 121.5(7) . .
C4S C3S C2S 119.2(9) . .
H3S C3S C2S 120.4(6) . .
H3S C3S C4S 120.4(7) . .
C3S C4S C5S 124.5(10) . .
H4S C4S C5S 117.7(6) . .
H4S C4S C3S 117.7(7) . .
H7Sa C7S C1S 109.5 . .
H7Sb C7S C1S 109.5 . .
H7Sb C7S H7Sa 109.5 . .
H7Sc C7S C1S 109.5 . .
H7Sc C7S H7Sa 109.5 . .
H7Sc C7S H7Sb 109.5 . .

_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 -0.314 0.500 0.500 236.9 80.0 ?
2 0.261 0.168 0.966 13.1 0.9 ?
3 0.739 0.832 0.034 13.1 0.9 ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.060
_oxdiff_exptl_absorpt_empirical_full_min 0.958
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C6S 0.0100
C1S 0.0100
C2S 0.0100
C5S 0.0100
C3S 0.0100
C4S 0.0100

####################################################################### 
# 
# 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_1002
_database_code_depnum_ccdc_archive 'CCDC 2154346'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-07-24 downloaded from the CCDC.
;
_audit_creation_date             2021-06-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H22 Cl2 F3 N3 O3'
_chemical_formula_sum            'C33 H22 Cl2 F3 N3 O3'
_chemical_formula_weight         636.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.4663(7)
_cell_length_b                   12.6932(12)
_cell_length_c                   13.8600(13)
_cell_angle_alpha                79.867(8)
_cell_angle_beta                 78.202(7)
_cell_angle_gamma                85.035(7)
_cell_volume                     1433.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1972
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.9310
_cell_measurement_theta_min      3.5780
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0961
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13615
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.915
_diffrn_reflns_theta_min         3.479
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     51.00  77.00   1.00   30.00    --   22.52-138.00   1.00   26
  2  ω     18.00  43.00   1.00   30.00    --   22.52-132.00 177.00   25
  3  ω    -86.00 -20.00   1.00   30.00    --  -23.92 132.00-113.00   66
  4  ω    -89.00 -58.00   1.00   30.00    --  -23.92 138.00  63.00   31
  5  ω     -3.00  92.00   1.00   30.00    --   22.52  38.00-180.00   95
  6  ω      1.00  91.00   1.00   30.00    --   22.52  57.00 -90.00   90
  7  ω    -46.00  48.00   1.00   30.00    --   22.52 -38.00   0.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0282104000
_diffrn_orient_matrix_UB_12      -0.0354731000
_diffrn_orient_matrix_UB_13      0.0446660000
_diffrn_orient_matrix_UB_21      0.0144006000
_diffrn_orient_matrix_UB_22      0.0381890000
_diffrn_orient_matrix_UB_23      0.0284953000
_diffrn_orient_matrix_UB_31      -0.0796386000
_diffrn_orient_matrix_UB_32      0.0226825000
_diffrn_orient_matrix_UB_33      0.0003330000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3497
_reflns_number_total             7704
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0046(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         7704
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.020
_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)+(0.0581P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1880
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
 C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.05658(11) 0.99621(9) 0.29727(7) 0.0757(3) Uani 1 1 d . . . . .
Cl2 Cl 0.45335(13) 0.97779(9) 0.85392(7) 0.0766(3) Uani 1 1 d . . . . .
F1 F 0.3021(2) 0.50403(19) 0.05723(15) 0.0737(6) Uani 1 1 d . . . . .
F2 F 0.1977(2) 0.54072(18) 0.20165(14) 0.0708(6) Uani 1 1 d . . . . .
F3 F 0.4009(3) 0.42808(19) 0.18358(18) 0.0839(7) Uani 1 1 d . . . . .
O1 O 0.3796(2) 0.70241(19) 0.07199(14) 0.0495(6) Uani 1 1 d . . . . .
O2 O 0.7071(3) 0.4899(2) 0.20433(19) 0.0721(7) Uani 1 1 d . . . . .
O3 O 0.5443(3) 0.4957(2) 0.34411(18) 0.0742(8) Uani 1 1 d . . . . .
N1 N 0.5095(3) 0.7750(2) 0.49471(17) 0.0469(7) Uani 1 1 d . . . . .
N2 N 0.6498(3) 0.7834(2) 0.42501(18) 0.0537(7) Uani 1 1 d . . . . .
N3 N 0.5962(3) 0.5325(2) 0.2576(2) 0.0505(7) Uani 1 1 d . . . . .
C1 C 0.3377(4) 0.5202(3) 0.1424(2) 0.0534(8) Uani 1 1 d . . . . .
C2 C 0.4541(3) 0.6107(3) 0.1213(2) 0.0451(7) Uani 1 1 d . . . . .
C3 C 0.5183(3) 0.6367(2) 0.2098(2) 0.0398(7) Uani 1 1 d . . . . .
C4 C 0.6498(3) 0.7233(3) 0.1713(2) 0.0457(7) Uani 1 1 d . . . . .
C5 C 0.7370(4) 0.7358(4) 0.2549(3) 0.0557(9) Uani 1 1 d . . . . .
C6 C 0.6166(3) 0.7473(3) 0.3473(2) 0.0475(8) Uani 1 1 d . . . . .
C7 C 0.4552(3) 0.7193(3) 0.3645(2) 0.0417(7) Uani 1 1 d . . . . .
C8 C 0.3819(3) 0.6787(3) 0.2876(2) 0.0389(7) Uani 1 1 d . . . . .
C9 C 0.2768(3) 0.7622(3) 0.2323(2) 0.0390(7) Uani 1 1 d . . . . .
C10 C 0.1707(3) 0.8344(3) 0.2823(2) 0.0437(7) Uani 1 1 d . . . . .
C11 C 0.0760(3) 0.9095(3) 0.2323(2) 0.0502(8) Uani 1 1 d . . . . .
C12 C 0.0843(4) 0.9164(3) 0.1308(3) 0.0581(9) Uani 1 1 d . . . . .
C13 C 0.1849(4) 0.8450(3) 0.0804(2) 0.0537(9) Uani 1 1 d . . . . .
C14 C 0.2798(3) 0.7688(3) 0.1312(2) 0.0431(7) Uani 1 1 d . . . . .
C15 C 0.3884(3) 0.7361(3) 0.4602(2) 0.0415(7) Uani 1 1 d . . . . .
C16 C 0.2250(3) 0.7165(3) 0.5180(2) 0.0449(7) Uani 1 1 d . . . . .
C17 C 0.1683(4) 0.6144(3) 0.5351(2) 0.0591(9) Uani 1 1 d . . . . .
H17 H 0.236049 0.558222 0.513046 0.071 Uiso 1 1 calc R U . . .
C18 C 0.0119(5) 0.5953(4) 0.5846(3) 0.0802(13) Uani 1 1 d . . . . .
H18 H -0.024737 0.526328 0.597319 0.096 Uiso 1 1 calc R U . . .
C19 C -0.0905(5) 0.6798(5) 0.6153(3) 0.0872(15) Uani 1 1 d . . . . .
H19 H -0.196824 0.667548 0.646943 0.105 Uiso 1 1 calc R U . . .
C20 C -0.0359(4) 0.7805(4) 0.5993(3) 0.0765(13) Uani 1 1 d . . . . .
H20 H -0.104487 0.836414 0.621110 0.092 Uiso 1 1 calc R U . . .
C21 C 0.1202(4) 0.7998(3) 0.5511(2) 0.0570(9) Uani 1 1 d . . . . .
H21 H 0.156459 0.868784 0.540435 0.068 Uiso 1 1 calc R U . . .
C22 C 0.5006(3) 0.8187(3) 0.5837(2) 0.0433(7) Uani 1 1 d . . . . .
C23 C 0.4156(4) 0.7716(3) 0.6747(2) 0.0520(8) Uani 1 1 d . . . . .
H23 H 0.367230 0.707270 0.679841 0.062 Uiso 1 1 calc R U . . .
C24 C 0.4022(4) 0.8197(3) 0.7577(2) 0.0530(8) Uani 1 1 d . . . . .
H24 H 0.343053 0.788758 0.818747 0.064 Uiso 1 1 calc R U . . .
C25 C 0.4769(4) 0.9140(3) 0.7499(2) 0.0514(8) Uani 1 1 d . . . . .
C26 C 0.5676(4) 0.9595(3) 0.6614(2) 0.0577(9) Uani 1 1 d . . . . .
H26 H 0.619874 1.022007 0.657487 0.069 Uiso 1 1 calc R U . . .
C27 C 0.5809(4) 0.9112(3) 0.5775(2) 0.0537(8) Uani 1 1 d . . . . .
H27 H 0.643525 0.940772 0.517094 0.064 Uiso 1 1 calc R U . . .
C28 C 0.7622(3) 0.7173(3) 0.0712(2) 0.0468(8) Uani 1 1 d . . . . .
C29 C 0.7259(4) 0.7838(3) -0.0131(2) 0.0624(10) Uani 1 1 d . . . . .
H29 H 0.633365 0.829131 -0.006895 0.075 Uiso 1 1 calc R U . . .
C30 C 0.8243(4) 0.7841(4) -0.1062(3) 0.0752(12) Uani 1 1 d . . . . .
H30 H 0.797682 0.828932 -0.161909 0.090 Uiso 1 1 calc R U . . .
C31 C 0.9618(4) 0.7176(4) -0.1156(3) 0.0714(12) Uani 1 1 d . . . . .
H31 H 1.028259 0.716961 -0.177882 0.086 Uiso 1 1 calc R U . . .
C32 C 1.0006(4) 0.6524(4) -0.0335(3) 0.0651(11) Uani 1 1 d . . . . .
H32 H 1.093256 0.607210 -0.040180 0.078 Uiso 1 1 calc R U . . .
C33 C 0.9036(3) 0.6531(3) 0.0591(2) 0.0560(9) Uani 1 1 d . . . . .
H33 H 0.933378 0.609696 0.114557 0.067 Uiso 1 1 calc R U . . .
H2 H 0.544(3) 0.589(3) 0.074(2) 0.053(9) Uiso 1 1 d . . . . .
H4 H 0.578(3) 0.788(2) 0.1585(18) 0.036(7) Uiso 1 1 d . . . . .
H8 H 0.316(3) 0.621(2) 0.3193(19) 0.038(8) Uiso 1 1 d . . . . .
H10 H 0.166(3) 0.831(2) 0.351(2) 0.040(8) Uiso 1 1 d . . . . .
H13 H 0.186(3) 0.846(3) 0.010(2) 0.060(9) Uiso 1 1 d . . . . .
H5A H 0.811(4) 0.674(3) 0.263(2) 0.072(11) Uiso 1 1 d . . . . .
H12 H 0.020(3) 0.965(3) 0.095(2) 0.055(9) Uiso 1 1 d . . . . .
H5B H 0.805(4) 0.797(3) 0.232(2) 0.061(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.733(3) . ?
Cl2 C25 1.743(3) . ?
F1 C1 1.329(3) . ?
F2 C1 1.331(3) . ?
F3 C1 1.327(4) . ?
O1 C2 1.411(4) . ?
O1 C14 1.391(3) . ?
O2 N3 1.220(3) . ?
O3 N3 1.213(3) . ?
N1 N2 1.368(3) . ?
N1 C15 1.377(3) . ?
N1 C22 1.424(3) . ?
N2 C6 1.330(3) . ?
N3 C3 1.530(4) . ?
C1 C2 1.528(5) . ?
C2 C3 1.535(4) . ?
C2 H2 0.95(3) . ?
C3 C4 1.580(4) . ?
C3 C8 1.538(4) . ?
C4 C5 1.532(4) . ?
C4 C28 1.523(4) . ?
C4 H4 1.00(3) . ?
C5 C6 1.485(4) . ?
C5 H5A 0.96(4) . ?
C5 H5B 0.97(4) . ?
C6 C7 1.404(4) . ?
C7 C8 1.519(4) . ?
C7 C15 1.377(4) . ?
C8 C9 1.527(4) . ?
C8 H8 0.95(3) . ?
C9 C10 1.397(4) . ?
C9 C14 1.385(4) . ?
C10 C11 1.376(4) . ?
C10 H10 0.94(3) . ?
C11 C12 1.383(4) . ?
C12 C13 1.371(5) . ?
C12 H12 0.93(3) . ?
C13 C14 1.391(4) . ?
C13 H13 0.98(3) . ?
C15 C16 1.467(4) . ?
C16 C17 1.385(5) . ?
C16 C21 1.399(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.363(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(4) . ?
C22 C27 1.388(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.375(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(5) . ?
C25 C26 1.367(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.389(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.388(4) . ?
C28 C33 1.386(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.386(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.375(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.364(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.376(4) . ?
C33 H33 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
C14 O1 C2 117.4(2) . . ?
N2 N1 C15 112.1(2) . . ?
N2 N1 C22 118.2(2) . . ?
C15 N1 C22 129.1(2) . . ?
C6 N2 N1 104.6(2) . . ?
O2 N3 C3 116.8(3) . . ?
O3 N3 O2 123.6(3) . . ?
O3 N3 C3 119.6(2) . . ?
F1 C1 F2 106.4(2) . . ?
F1 C1 C2 109.7(3) . . ?
F2 C1 C2 113.7(3) . . ?
F3 C1 F1 107.0(3) . . ?
F3 C1 F2 107.4(3) . . ?
F3 C1 C2 112.3(3) . . ?
O1 C2 C1 107.7(2) . . ?
O1 C2 C3 111.2(2) . . ?
O1 C2 H2 106.4(18) . . ?
C1 C2 C3 117.5(3) . . ?
C1 C2 H2 105.2(19) . . ?
C3 C2 H2 108.2(16) . . ?
N3 C3 C2 106.9(2) . . ?
N3 C3 C4 109.5(2) . . ?
N3 C3 C8 109.6(2) . . ?
C2 C3 C4 109.8(2) . . ?
C2 C3 C8 111.7(2) . . ?
C8 C3 C4 109.3(2) . . ?
C3 C4 H4 99.4(15) . . ?
C5 C4 C3 110.7(3) . . ?
C5 C4 H4 108.8(15) . . ?
C28 C4 C3 117.7(2) . . ?
C28 C4 C5 113.9(2) . . ?
C28 C4 H4 104.8(15) . . ?
C4 C5 H5A 107(2) . . ?
C4 C5 H5B 108.4(19) . . ?
C6 C5 C4 109.7(2) . . ?
C6 C5 H5A 113(2) . . ?
C6 C5 H5B 112.7(19) . . ?
H5A C5 H5B 105(3) . . ?
N2 C6 C5 124.0(3) . . ?
N2 C6 C7 111.6(2) . . ?
C7 C6 C5 124.4(3) . . ?
C6 C7 C8 123.3(2) . . ?
C15 C7 C6 106.0(2) . . ?
C15 C7 C8 130.7(2) . . ?
C3 C8 H8 107.8(16) . . ?
C7 C8 C3 109.2(2) . . ?
C7 C8 C9 114.6(3) . . ?
C7 C8 H8 109.6(16) . . ?
C9 C8 C3 108.2(2) . . ?
C9 C8 H8 107.3(15) . . ?
C10 C9 C8 121.2(2) . . ?
C14 C9 C8 121.8(3) . . ?
C14 C9 C10 116.9(3) . . ?
C9 C10 H10 118.6(17) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 120.2(17) . . ?
C10 C11 Cl1 119.8(2) . . ?
C10 C11 C12 120.9(3) . . ?
C12 C11 Cl1 119.3(3) . . ?
C11 C12 H12 122.8(19) . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 118.0(19) . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.0(19) . . ?
C14 C13 H13 120.0(19) . . ?
C9 C14 O1 123.2(3) . . ?
C9 C14 C13 122.0(3) . . ?
C13 C14 O1 114.8(3) . . ?
N1 C15 C7 105.6(2) . . ?
N1 C15 C16 125.0(2) . . ?
C7 C15 C16 129.4(2) . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 C21 118.6(3) . . ?
C21 C16 C15 121.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(4) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.7(4) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.3(4) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.3(4) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.5(4) . . ?
C20 C21 H21 119.7 . . ?
C23 C22 N1 121.9(3) . . ?
C23 C22 C27 119.7(3) . . ?
C27 C22 N1 118.3(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.6(3) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 Cl2 119.7(3) . . ?
C26 C25 Cl2 119.2(3) . . ?
C26 C25 C24 121.1(3) . . ?
C25 C26 H26 120.4 . . ?
C25 C26 C27 119.3(3) . . ?
C27 C26 H26 120.4 . . ?
C22 C27 C26 120.0(3) . . ?
C22 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C4 118.4(3) . . ?
C33 C28 C4 124.3(3) . . ?
C33 C28 C29 117.3(3) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 C28 121.6(3) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 H30 120.3 . . ?
C31 C30 C29 119.4(4) . . ?
C31 C30 H30 120.3 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0(3) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C33 120.5(3) . . ?
C33 C32 H32 119.8 . . ?
C28 C33 H33 119.4 . . ?
C32 C33 C28 121.2(3) . . ?
C32 C33 H33 119.4 . . ?

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
Cl1 C11 C12 C13 -177.6(3) . . . . ?
Cl2 C25 C26 C27 -177.3(2) . . . . ?
F1 C1 C2 O1 57.4(3) . . . . ?
F1 C1 C2 C3 -176.2(3) . . . . ?
F2 C1 C2 O1 -61.5(3) . . . . ?
F2 C1 C2 C3 64.9(4) . . . . ?
F3 C1 C2 O1 176.3(2) . . . . ?
F3 C1 C2 C3 -57.3(3) . . . . ?
O1 C2 C3 N3 -180.0(2) . . . . ?
O1 C2 C3 C4 -61.2(3) . . . . ?
O1 C2 C3 C8 60.2(3) . . . . ?
O2 N3 C3 C2 58.9(3) . . . . ?
O2 N3 C3 C4 -60.1(3) . . . . ?
O2 N3 C3 C8 -179.9(2) . . . . ?
O3 N3 C3 C2 -119.7(3) . . . . ?
O3 N3 C3 C4 121.4(3) . . . . ?
O3 N3 C3 C8 1.5(4) . . . . ?
N1 N2 C6 C5 -176.6(3) . . . . ?
N1 N2 C6 C7 2.1(4) . . . . ?
N1 C15 C16 C17 -121.0(4) . . . . ?
N1 C15 C16 C21 63.3(4) . . . . ?
N1 C22 C23 C24 -176.2(3) . . . . ?
N1 C22 C27 C26 176.4(3) . . . . ?
N2 N1 C15 C7 0.0(4) . . . . ?
N2 N1 C15 C16 178.9(3) . . . . ?
N2 N1 C22 C23 -145.2(3) . . . . ?
N2 N1 C22 C27 34.6(4) . . . . ?
N2 C6 C7 C8 178.2(3) . . . . ?
N2 C6 C7 C15 -2.2(4) . . . . ?
N3 C3 C4 C5 -52.7(3) . . . . ?
N3 C3 C4 C28 80.7(3) . . . . ?
N3 C3 C8 C7 70.5(3) . . . . ?
N3 C3 C8 C9 -164.1(2) . . . . ?
C1 C2 C3 N3 55.4(3) . . . . ?
C1 C2 C3 C4 174.1(3) . . . . ?
C1 C2 C3 C8 -64.5(3) . . . . ?
C2 O1 C14 C9 14.0(4) . . . . ?
C2 O1 C14 C13 -167.7(3) . . . . ?
C2 C3 C4 C5 -169.9(3) . . . . ?
C2 C3 C4 C28 -36.5(4) . . . . ?
C2 C3 C8 C7 -171.2(3) . . . . ?
C2 C3 C8 C9 -45.8(3) . . . . ?
C3 C4 C5 C6 -48.0(4) . . . . ?
C3 C4 C28 C29 98.1(4) . . . . ?
C3 C4 C28 C33 -85.0(4) . . . . ?
C3 C8 C9 C10 -162.9(3) . . . . ?
C3 C8 C9 C14 18.4(4) . . . . ?
C4 C3 C8 C7 -49.5(3) . . . . ?
C4 C3 C8 C9 75.9(3) . . . . ?
C4 C5 C6 N2 -164.0(3) . . . . ?
C4 C5 C6 C7 17.5(5) . . . . ?
C4 C28 C29 C30 178.8(3) . . . . ?
C4 C28 C33 C32 -179.3(3) . . . . ?
C5 C4 C28 C29 -130.0(4) . . . . ?
C5 C4 C28 C33 46.9(5) . . . . ?
C5 C6 C7 C8 -3.2(6) . . . . ?
C5 C6 C7 C15 176.5(3) . . . . ?
C6 C7 C8 C3 19.8(4) . . . . ?
C6 C7 C8 C9 -101.7(3) . . . . ?
C6 C7 C15 N1 1.3(3) . . . . ?
C6 C7 C15 C16 -177.6(3) . . . . ?
C7 C8 C9 C10 -40.8(4) . . . . ?
C7 C8 C9 C14 140.4(3) . . . . ?
C7 C15 C16 C17 57.6(5) . . . . ?
C7 C15 C16 C21 -118.1(4) . . . . ?
C8 C3 C4 C5 67.3(3) . . . . ?
C8 C3 C4 C28 -159.3(3) . . . . ?
C8 C7 C15 N1 -179.1(3) . . . . ?
C8 C7 C15 C16 2.0(6) . . . . ?
C8 C9 C10 C11 -179.9(3) . . . . ?
C8 C9 C14 O1 -1.4(4) . . . . ?
C8 C9 C14 C13 -179.7(3) . . . . ?
C9 C10 C11 Cl1 179.0(2) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C10 C9 C14 O1 179.8(3) . . . . ?
C10 C9 C14 C13 1.6(4) . . . . ?
C10 C11 C12 C13 2.0(5) . . . . ?
C11 C12 C13 C14 -1.6(6) . . . . ?
C12 C13 C14 O1 -178.6(3) . . . . ?
C12 C13 C14 C9 -0.2(5) . . . . ?
C14 O1 C2 C1 87.6(3) . . . . ?
C14 O1 C2 C3 -42.5(3) . . . . ?
C14 C9 C10 C11 -1.2(4) . . . . ?
C15 N1 N2 C6 -1.3(4) . . . . ?
C15 N1 C22 C23 44.3(5) . . . . ?
C15 N1 C22 C27 -135.9(3) . . . . ?
C15 C7 C8 C3 -159.7(3) . . . . ?
C15 C7 C8 C9 78.7(4) . . . . ?
C15 C16 C17 C18 -176.4(3) . . . . ?
C15 C16 C21 C20 175.6(3) . . . . ?
C16 C17 C18 C19 1.6(5) . . . . ?
C17 C16 C21 C20 -0.2(5) . . . . ?
C17 C18 C19 C20 -1.9(6) . . . . ?
C18 C19 C20 C21 1.1(6) . . . . ?
C19 C20 C21 C16 -0.1(5) . . . . ?
C21 C16 C17 C18 -0.6(5) . . . . ?
C22 N1 N2 C6 -173.3(3) . . . . ?
C22 N1 C15 C7 170.9(3) . . . . ?
C22 N1 C15 C16 -10.2(5) . . . . ?
C22 C23 C24 C25 -1.3(5) . . . . ?
C23 C22 C27 C26 -3.8(5) . . . . ?
C23 C24 C25 Cl2 177.5(2) . . . . ?
C23 C24 C25 C26 -1.6(5) . . . . ?
C24 C25 C26 C27 1.8(5) . . . . ?
C25 C26 C27 C22 0.9(5) . . . . ?
C27 C22 C23 C24 4.0(5) . . . . ?
C28 C4 C5 C6 176.7(3) . . . . ?
C28 C29 C30 C31 -0.3(6) . . . . ?
C29 C28 C33 C32 -2.4(5) . . . . ?
C29 C30 C31 C32 -0.3(6) . . . . ?
C30 C31 C32 C33 -0.4(6) . . . . ?
C31 C32 C33 C28 1.8(6) . . . . ?
C33 C28 C29 C30 1.7(5) . . . . ?


_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 1.191
_oxdiff_exptl_absorpt_empirical_full_min 0.850
