# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_liangdd_1027
_database_code_depnum_ccdc_archive 'CCDC 2048401'
loop_
_audit_author_name
_audit_author_address
'Ming-Hui Xu'
;lanzhou university
China
;
_audit_update_record             
;
2020-12-05 deposited with the CCDC.	2021-04-14 downloaded from the CCDC.
;
_audit_creation_date             2020-11-02
_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         'C25 H24 O5'
_chemical_formula_sum            'C25 H24 O5'
_chemical_formula_weight         404.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.1221(4)
_cell_length_b                   16.6749(15)
_cell_length_c                   21.0774(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2151.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3780
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      58.2310
_cell_measurement_theta_min      4.1820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11429
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         4.195
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     58.00 110.00   1.00    2.50    --  108.00-111.00 150.00   52
  2  ω     67.00 130.00   1.00    2.50    --  108.00 -50.00 -30.00   63
  3  ω     75.00 174.00   1.00    2.50    --  108.00  25.00 150.00   99
  4  ω    110.00 174.00   1.00    2.50    --  108.00 111.00 -30.00   64
  5  ω     28.00  80.00   1.00    2.00    --   54.00 -77.00 -90.00   52
  6  ω     30.00 126.00   1.00    2.00    --   54.00  38.00  60.00   96
  7  ω     20.00  59.00   1.00    1.00    --    0.00  57.00 -90.00   39
  8  ω     12.00  37.00   1.00    1.00    --    0.00  57.00-120.00   25
  9  ω    -18.00   7.00   1.00    1.00    --    0.00  57.00-120.00   25
 10  ω    -14.00  18.00   1.00    2.00    --   54.00 -57.00 -90.00   32
 11  ω    -14.00  13.00   1.00    2.00    --   54.00 -77.00 -90.00   27
 12  ω    -53.00 -28.00   1.00    1.00    --    0.00 136.00  39.00   25
 13  ω     17.00  68.00   1.00    2.00    --   54.00 -57.00 -30.00   51
 14  ω    111.00 137.00   1.00    4.00    --  108.00 178.00  30.00   26
 15  ω     49.00 114.00   1.00    4.00    --  108.00 -38.00  60.00   65
 16  ω     40.00  66.00   1.00    4.00    --  108.00-111.00  60.00   26
 17  ω     78.00 106.00   1.00    4.00    --  108.00-111.00  60.00   28
 18  ω     57.00  95.00   1.00    4.00    --  108.00 178.00  30.00   38
 19  ω     54.00  85.00   1.00    4.00    --  108.00 -63.00 120.00   31
 20  ω    -70.00  30.00   1.00    1.00    --    0.00 -77.00 150.00  100
 21  ω    -69.00  21.00   1.00    1.00    --    0.00 -57.00-120.00   90
 22  ω     33.00 123.00   1.00    2.00    --   54.00  57.00 -60.00   90
 23  ω     24.00 124.00   1.00    2.00    --   54.00  77.00 120.00  100
 24  ω    -16.00  73.00   1.00    2.00    --   54.00 -77.00  90.00   89
 25  ω     33.00 123.00   1.00    2.00    --   54.00  57.00-150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011648000
_diffrn_orient_matrix_UB_12      0.0117305000
_diffrn_orient_matrix_UB_13      0.0724500000
_diffrn_orient_matrix_UB_21      -0.0052966000
_diffrn_orient_matrix_UB_22      -0.0917040000
_diffrn_orient_matrix_UB_23      0.0092830000
_diffrn_orient_matrix_UB_31      0.2515278000
_diffrn_orient_matrix_UB_32      -0.0019487000
_diffrn_orient_matrix_UB_33      0.0005299000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3070
_reflns_number_total             3799
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.127
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.024
_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)+(0.0584P)²+0.0627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1157
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6AA(H6AA), C3(H3), C4AA(H4AA)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20),
 C3AA(H3AA), C2(H2), C0AA(H0AA), C1AA(H1AA), C2AA(H2AA), C8AA(H8AA)
2.d Idealised Me refined as rotating group:
 C5AA(H5AA,H5AB,H5AC), C9AA(H9AA,H9AB,H9AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.9795(3) -0.22950(13) -0.20609(10) 0.0508(5) Uani 1 1 d . . . . .
C6AA C -0.7100(5) -0.34613(17) -0.33302(14) 0.0482(7) Uani 1 1 d . . . . .
H6AA H -0.566529 -0.350817 -0.312725 0.058 Uiso 1 1 calc R U . . .
C3 C -0.8806(5) -0.33532(18) -0.27987(14) 0.0488(7) Uani 1 1 d . . . . .
H3 H -1.019596 -0.320447 -0.299724 0.059 Uiso 1 1 calc R U . . .
C4 C -0.7017(5) -0.27390(18) -0.37691(13) 0.0454(7) Uani 1 1 d . . . . .
C5 C -0.8794(6) -0.25437(19) -0.41486(14) 0.0532(8) Uani 1 1 d . . . . .
H5 H -1.006391 -0.284762 -0.412029 0.064 Uiso 1 1 calc R U . . .
O6 O -1.2088(5) -0.11949(18) -0.12668(16) 0.0943(10) Uani 1 1 d . . . . .
C7 C -0.8807(5) -0.17514(19) -0.16567(15) 0.0539(8) Uani 1 1 d . . . . .
C8 C -0.5969(5) -0.49993(18) -0.46713(15) 0.0499(7) Uani 1 1 d . . . . .
C9 C -0.8144(5) -0.2685(2) -0.23666(14) 0.0497(7) Uani 1 1 d . . . . .
O10 O -0.4295(4) -0.54700(13) -0.48170(10) 0.0567(6) Uani 1 1 d . . . . .
C11 C -0.9168(5) -0.4125(2) -0.24271(15) 0.0544(8) Uani 1 1 d . . . . .
C12 C -0.7500(7) -0.4447(3) -0.20627(19) 0.0796(12) Uani 1 1 d . . . . .
H12 H -0.619752 -0.416605 -0.201626 0.096 Uiso 1 1 calc R U . . .
O13 O -0.7608(4) -0.49221(16) -0.49718(12) 0.0756(7) Uani 1 1 d . . . . .
O14 O -0.3677(4) -0.43458(18) -0.39273(12) 0.0786(8) Uani 1 1 d . . . . .
C15 C -1.1102(7) -0.4540(2) -0.24670(18) 0.0686(10) Uani 1 1 d . . . . .
H15 H -1.224798 -0.432839 -0.270382 0.082 Uiso 1 1 calc R U . . .
C16 C -0.5089(7) -0.1626(2) -0.42457(16) 0.0630(9) Uani 1 1 d . . . . .
H16 H -0.382640 -0.131899 -0.427739 0.076 Uiso 1 1 calc R U . . .
C17 C -0.6862(7) -0.1446(2) -0.46150(16) 0.0621(9) Uani 1 1 d . . . . .
H17 H -0.681087 -0.101560 -0.489512 0.075 Uiso 1 1 calc R U . . .
C18 C -0.6649(6) -0.1806(2) -0.17043(17) 0.0663(10) Uani 1 1 d . . . . .
H18 H -0.562455 -0.150869 -0.147892 0.080 Uiso 1 1 calc R U . . .
C19 C -0.7476(5) -0.42284(18) -0.37143(16) 0.0554(8) Uani 1 1 d . . . . .
H19A H -0.792651 -0.465200 -0.342727 0.066 Uiso 1 1 calc R U . . .
H19B H -0.866348 -0.413676 -0.401034 0.066 Uiso 1 1 calc R U . . .
C20 C -0.5166(5) -0.2270(2) -0.38217(15) 0.0563(8) Uani 1 1 d . . . . .
H20 H -0.395437 -0.238340 -0.357128 0.068 Uiso 1 1 calc R U . . .
C3AA C -0.8711(7) -0.1904(2) -0.45690(15) 0.0617(9) Uani 1 1 d . . . . .
H3AA H -0.991704 -0.178638 -0.482066 0.074 Uiso 1 1 calc R U . . .
C2 C -0.6208(5) -0.2399(2) -0.21597(17) 0.0680(10) Uani 1 1 d . . . . .
H2 H -0.483303 -0.256441 -0.229432 0.082 Uiso 1 1 calc R U . . .
C4AA C -0.4444(7) -0.5935(2) -0.54076(17) 0.0715(11) Uani 1 1 d . . . . .
H4AA H -0.525385 -0.562614 -0.572582 0.086 Uiso 1 1 calc R U . . .
C0AA C -0.7751(10) -0.5179(3) -0.1768(2) 0.1070(17) Uani 1 1 d . . . . .
H0AA H -0.659973 -0.539805 -0.153875 0.128 Uiso 1 1 calc R U . . .
C1AA C -0.9689(12) -0.5586(3) -0.1813(2) 0.1045(18) Uani 1 1 d . . . . .
H1AA H -0.986271 -0.607567 -0.160809 0.125 Uiso 1 1 calc R U . . .
C2AA C -1.1372(9) -0.5266(3) -0.2160(2) 0.0912(14) Uani 1 1 d . . . . .
H2AA H -1.269391 -0.553799 -0.218981 0.109 Uiso 1 1 calc R U . . .
C5AA C -0.5640(10) -0.6700(3) -0.5267(3) 0.126(2) Uani 1 1 d . . . . .
H5AA H -0.487157 -0.699316 -0.494525 0.189 Uiso 1 1 calc R U . . .
H5AB H -0.572729 -0.701810 -0.564598 0.189 Uiso 1 1 calc R U . . .
H5AC H -0.708747 -0.657763 -0.512093 0.189 Uiso 1 1 calc R U . . .
C7AA C -0.5523(6) -0.45051(19) -0.40756(14) 0.0499(7) Uani 1 1 d . . . . .
C8AA C -1.0135(7) -0.1222(2) -0.12795(19) 0.0679(10) Uani 1 1 d . . . . .
H8AA H -0.939730 -0.086417 -0.101788 0.081 Uiso 1 1 calc R U . . .
C9AA C -0.2158(8) -0.6059(3) -0.5628(2) 0.1096(17) Uani 1 1 d . . . . .
H9AA H -0.148023 -0.554767 -0.570168 0.164 Uiso 1 1 calc R U . . .
H9AB H -0.216583 -0.636225 -0.601511 0.164 Uiso 1 1 calc R U . . .
H9AC H -0.135273 -0.634549 -0.530996 0.164 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.383(4) . ?
O1 C9 1.364(4) . ?
C6AA H6AA 0.9800 . ?
C6AA C3 1.543(4) . ?
C6AA C4 1.519(4) . ?
C6AA C19 1.531(4) . ?
C3 H3 0.9800 . ?
C3 C9 1.495(4) . ?
C3 C11 1.523(4) . ?
C4 C5 1.389(4) . ?
C4 C20 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C3AA 1.387(4) . ?
O6 C8AA 1.197(4) . ?
C7 C18 1.328(5) . ?
C7 C8AA 1.439(5) . ?
C8 O10 1.327(4) . ?
C8 O13 1.193(4) . ?
C8 C7AA 1.526(4) . ?
C9 C2 1.350(4) . ?
O10 C4AA 1.469(4) . ?
C11 C12 1.386(5) . ?
C11 C15 1.373(5) . ?
C12 H12 0.9300 . ?
C12 C0AA 1.378(6) . ?
O14 C7AA 1.202(4) . ?
C15 H15 0.9300 . ?
C15 C2AA 1.383(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(5) . ?
C16 C20 1.397(5) . ?
C17 H17 0.9300 . ?
C17 C3AA 1.369(5) . ?
C18 H18 0.9300 . ?
C18 C2 1.404(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C7AA 1.491(4) . ?
C20 H20 0.9300 . ?
C3AA H3AA 0.9300 . ?
C2 H2 0.9300 . ?
C4AA H4AA 0.9800 . ?
C4AA C5AA 1.500(7) . ?
C4AA C9AA 1.490(6) . ?
C0AA H0AA 0.9300 . ?
C0AA C1AA 1.369(7) . ?
C1AA H1AA 0.9300 . ?
C1AA C2AA 1.372(7) . ?
C2AA H2AA 0.9300 . ?
C5AA H5AA 0.9600 . ?
C5AA H5AB 0.9600 . ?
C5AA H5AC 0.9600 . ?
C8AA H8AA 0.9300 . ?
C9AA H9AA 0.9600 . ?
C9AA H9AB 0.9600 . ?
C9AA H9AC 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
_geom_angle_publ_flag
C9 O1 C7 106.3(2) . . ?
C3 C6AA H6AA 107.4 . . ?
C4 C6AA H6AA 107.4 . . ?
C4 C6AA C3 111.8(2) . . ?
C4 C6AA C19 110.2(2) . . ?
C19 C6AA H6AA 107.4 . . ?
C19 C6AA C3 112.3(2) . . ?
C6AA C3 H3 107.9 . . ?
C9 C3 C6AA 110.2(2) . . ?
C9 C3 H3 107.9 . . ?
C9 C3 C11 110.9(2) . . ?
C11 C3 C6AA 111.9(2) . . ?
C11 C3 H3 107.9 . . ?
C5 C4 C6AA 120.7(3) . . ?
C20 C4 C6AA 121.7(3) . . ?
C20 C4 C5 117.6(3) . . ?
C4 C5 H5 119.3 . . ?
C3AA C5 C4 121.3(3) . . ?
C3AA C5 H5 119.3 . . ?
O1 C7 C8AA 119.7(3) . . ?
C18 C7 O1 110.1(3) . . ?
C18 C7 C8AA 130.2(3) . . ?
O10 C8 C7AA 111.8(3) . . ?
O13 C8 O10 126.2(3) . . ?
O13 C8 C7AA 121.9(3) . . ?
O1 C9 C3 116.2(3) . . ?
C2 C9 O1 109.2(3) . . ?
C2 C9 C3 134.3(3) . . ?
C8 O10 C4AA 117.4(3) . . ?
C12 C11 C3 120.3(3) . . ?
C15 C11 C3 121.3(3) . . ?
C15 C11 C12 118.3(3) . . ?
C11 C12 H12 119.7 . . ?
C0AA C12 C11 120.7(4) . . ?
C0AA C12 H12 119.7 . . ?
C11 C15 H15 119.5 . . ?
C11 C15 C2AA 121.0(4) . . ?
C2AA C15 H15 119.5 . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C20 120.4(3) . . ?
C20 C16 H16 119.8 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C3AA 119.5(3) . . ?
C3AA C17 H17 120.2 . . ?
C7 C18 H18 126.5 . . ?
C7 C18 C2 106.9(3) . . ?
C2 C18 H18 126.5 . . ?
C6AA C19 H19A 108.7 . . ?
C6AA C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C7AA C19 C6AA 114.1(3) . . ?
C7AA C19 H19A 108.7 . . ?
C7AA C19 H19B 108.7 . . ?
C4 C20 C16 120.9(3) . . ?
C4 C20 H20 119.5 . . ?
C16 C20 H20 119.5 . . ?
C5 C3AA H3AA 119.9 . . ?
C17 C3AA C5 120.3(3) . . ?
C17 C3AA H3AA 119.9 . . ?
C9 C2 C18 107.5(3) . . ?
C9 C2 H2 126.2 . . ?
C18 C2 H2 126.2 . . ?
O10 C4AA H4AA 109.5 . . ?
O10 C4AA C5AA 108.2(4) . . ?
O10 C4AA C9AA 106.2(3) . . ?
C5AA C4AA H4AA 109.5 . . ?
C9AA C4AA H4AA 109.5 . . ?
C9AA C4AA C5AA 113.7(4) . . ?
C12 C0AA H0AA 119.8 . . ?
C1AA C0AA C12 120.3(5) . . ?
C1AA C0AA H0AA 119.8 . . ?
C0AA C1AA H1AA 120.2 . . ?
C0AA C1AA C2AA 119.6(4) . . ?
C2AA C1AA H1AA 120.2 . . ?
C15 C2AA H2AA 120.0 . . ?
C1AA C2AA C15 120.0(5) . . ?
C1AA C2AA H2AA 120.0 . . ?
C4AA C5AA H5AA 109.5 . . ?
C4AA C5AA H5AB 109.5 . . ?
C4AA C5AA H5AC 109.5 . . ?
H5AA C5AA H5AB 109.5 . . ?
H5AA C5AA H5AC 109.5 . . ?
H5AB C5AA H5AC 109.5 . . ?
O14 C7AA C8 120.1(3) . . ?
O14 C7AA C19 123.6(3) . . ?
C19 C7AA C8 116.3(3) . . ?
O6 C8AA C7 126.9(4) . . ?
O6 C8AA H8AA 116.6 . . ?
C7 C8AA H8AA 116.6 . . ?
C4AA C9AA H9AA 109.5 . . ?
C4AA C9AA H9AB 109.5 . . ?
C4AA C9AA H9AC 109.5 . . ?
H9AA C9AA H9AB 109.5 . . ?
H9AA C9AA H9AC 109.5 . . ?
H9AB C9AA H9AC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C18 C2 0.7(4) . . . . ?
O1 C7 C8AA O6 0.6(6) . . . . ?
O1 C9 C2 C18 0.2(4) . . . . ?
C6AA C3 C9 O1 152.7(3) . . . . ?
C6AA C3 C9 C2 -33.5(5) . . . . ?
C6AA C3 C11 C12 65.6(4) . . . . ?
C6AA C3 C11 C15 -111.2(3) . . . . ?
C6AA C4 C5 C3AA -177.5(3) . . . . ?
C6AA C4 C20 C16 177.5(3) . . . . ?
C6AA C19 C7AA C8 -153.4(3) . . . . ?
C6AA C19 C7AA O14 25.1(5) . . . . ?
C3 C6AA C4 C5 -65.6(3) . . . . ?
C3 C6AA C4 C20 116.5(3) . . . . ?
C3 C6AA C19 C7AA -160.4(3) . . . . ?
C3 C9 C2 C18 -174.0(3) . . . . ?
C3 C11 C12 C0AA -174.5(4) . . . . ?
C3 C11 C15 C2AA 175.9(3) . . . . ?
C4 C6AA C3 C9 -65.8(3) . . . . ?
C4 C6AA C3 C11 170.4(2) . . . . ?
C4 C6AA C19 C7AA 74.2(3) . . . . ?
C4 C5 C3AA C17 -0.4(5) . . . . ?
C5 C4 C20 C16 -0.5(5) . . . . ?
C7 O1 C9 C3 175.6(3) . . . . ?
C7 O1 C9 C2 0.2(3) . . . . ?
C7 C18 C2 C9 -0.5(4) . . . . ?
C8 O10 C4AA C5AA -85.7(4) . . . . ?
C8 O10 C4AA C9AA 151.9(4) . . . . ?
C9 O1 C7 C18 -0.6(4) . . . . ?
C9 O1 C7 C8AA 177.8(3) . . . . ?
C9 C3 C11 C12 -57.9(4) . . . . ?
C9 C3 C11 C15 125.3(3) . . . . ?
O10 C8 C7AA O14 26.1(4) . . . . ?
O10 C8 C7AA C19 -155.3(3) . . . . ?
C11 C3 C9 O1 -82.8(3) . . . . ?
C11 C3 C9 C2 91.0(5) . . . . ?
C11 C12 C0AA C1AA -2.5(7) . . . . ?
C11 C15 C2AA C1AA -0.4(6) . . . . ?
C12 C11 C15 C2AA -1.0(6) . . . . ?
C12 C0AA C1AA C2AA 1.0(8) . . . . ?
O13 C8 O10 C4AA 0.9(5) . . . . ?
O13 C8 C7AA O14 -150.5(4) . . . . ?
O13 C8 C7AA C19 28.1(4) . . . . ?
C15 C11 C12 C0AA 2.5(6) . . . . ?
C16 C17 C3AA C5 0.4(5) . . . . ?
C17 C16 C20 C4 0.5(5) . . . . ?
C18 C7 C8AA O6 178.6(5) . . . . ?
C19 C6AA C3 C9 169.7(3) . . . . ?
C19 C6AA C3 C11 45.8(3) . . . . ?
C19 C6AA C4 C5 60.1(4) . . . . ?
C19 C6AA C4 C20 -117.8(3) . . . . ?
C20 C4 C5 C3AA 0.5(5) . . . . ?
C20 C16 C17 C3AA -0.4(5) . . . . ?
C0AA C1AA C2AA C15 0.4(7) . . . . ?
C7AA C8 O10 C4AA -175.6(3) . . . . ?
C8AA C7 C18 C2 -177.5(3) . . . . ?

_olex2_date_sample_data_collection 2020-10-27
_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 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.656
####################################################################### 
# 
# 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_xumh_0110
_database_code_depnum_ccdc_archive 'CCDC 2048402'
loop_
_audit_author_name
_audit_author_address
'Ming-Hui Xu'
;lanzhou university
China
;
_audit_update_record             
;
2020-12-05 deposited with the CCDC.	2021-04-14 downloaded from the CCDC.
;
_audit_creation_date             2020-04-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H27 F6 N3 O2 S'
_chemical_formula_sum            'C22 H27 F6 N3 O2 S'
_chemical_formula_weight         511.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.8909(2)
_cell_length_b                   12.4974(3)
_cell_length_c                   22.9357(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2548.46(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2733
_cell_measurement_temperature    293.58(10)
_cell_measurement_theta_max      67.8990
_cell_measurement_theta_min      10.4000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8895
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.588
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_min         4.028
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.58(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  23.00   1.00    1.00    --    0.00  57.00  60.00   41
  2  ω     10.00  62.00   1.00    1.00    --    0.00  57.00 -60.00   52
  3  ω    -11.00  91.00   1.00    1.50    --   54.00   0.00 -60.00  102
  4  ω     86.00 119.00   1.00    1.50    --  108.00  63.00 -60.00   33
  5  ω    123.00 177.00   1.00    1.50    --  108.00  38.00 -60.00   54
  6  ω    109.00 166.00   1.00    1.50    --  108.00 111.00 -60.00   57
  7  ω    102.00 164.00   1.00    1.50    --  108.00 111.00 -30.00   62
  8  ω    100.00 176.00   1.00    1.50    --  108.00  50.00  60.00   76
  9  ω     89.00 115.00   1.00    1.50    --  108.00  38.00 -60.00   26
 10  ω     54.00  98.00   1.00    1.50    --  108.00 -50.00-120.00   44
 11  ω     77.00 146.00   1.00    1.50    --  108.00 -91.00 -60.00   69
 12  ω     38.00 107.00   1.00    1.50    --  108.00-111.00 120.00   69
 13  ω     11.00  80.00   1.00    1.50    --   54.00 -99.00 -90.00   69
 14  ω      3.00  69.00   1.00    1.50    --   54.00 -57.00 -60.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0023724000
_diffrn_orient_matrix_UB_12      -0.0102045000
_diffrn_orient_matrix_UB_13      -0.0669114000
_diffrn_orient_matrix_UB_21      0.0012580000
_diffrn_orient_matrix_UB_22      -0.1228555000
_diffrn_orient_matrix_UB_23      0.0056291000
_diffrn_orient_matrix_UB_31      -0.1732776000
_diffrn_orient_matrix_UB_32      -0.0009772000
_diffrn_orient_matrix_UB_33      -0.0008275000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3802
_reflns_number_total             4515
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.108
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1353 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.0733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0998
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F10(0.85) F23(0.85) F25(0.85) F1(0.85) F2(0.85) F4(0.85) F3(0.15)
 F7(0.15) F9(0.15) F1AA(0.15) F0AA(0.15) F2AA(0.15)
3.a Ternary CH refined with riding coordinates:
 C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B), C21(H21A,H21B), C24(H24A,H24B), C26(H26A,
 H26B), C29(H29A,H29B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), C9(H9), C12(H12), C17(H17)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C30(H30A,H30B,H30C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.14752(9) -0.30380(7) -0.06753(4) 0.0611(2) Uani 1 1 d . . . . .
N2 N 0.0988(3) -0.3367(2) -0.00282(12) 0.0584(7) Uani 1 1 d . . . . .
H2 H 0.178325 -0.308929 0.012246 0.070 Uiso 1 1 calc R U . . .
N3 N 0.1520(3) -0.2548(2) -0.17220(12) 0.0605(7) Uani 1 1 d . . . . .
O4 O 0.3662(3) -0.2343(2) -0.11856(12) 0.0716(7) Uani 1 1 d . . . . .
N5 N 0.1010(3) -0.1873(2) -0.05704(11) 0.0541(6) Uani 1 1 d . . . . .
H5 H 0.183568 -0.175161 -0.038641 0.065 Uiso 1 1 calc R U . . .
O6 O 0.2997(3) -0.3947(2) -0.15809(12) 0.0738(7) Uani 1 1 d . . . . .
C7 C 0.0250(4) -0.2743(3) -0.04187(13) 0.0494(7) Uani 1 1 d . . . . .
C8 C 0.2816(4) -0.2900(3) -0.14734(15) 0.0600(8) Uani 1 1 d . . . . .
C9 C 0.0986(4) -0.4666(3) 0.07334(14) 0.0554(8) Uani 1 1 d . . . . .
H9 H 0.138355 -0.415335 0.098366 0.067 Uiso 1 1 calc R U . . .
F10 F 0.1083(11) -0.5195(5) 0.1900(2) 0.118(3) Uani 0.85 1 d . . P A 1
C11 C 0.0635(4) -0.4399(3) 0.01629(14) 0.0526(7) Uani 1 1 d . . . . .
C12 C 0.0049(4) -0.5173(3) -0.02044(16) 0.0626(9) Uani 1 1 d . . . . .
H12 H -0.014941 -0.500854 -0.059238 0.075 Uiso 1 1 calc R U . . .
C13 C 0.0743(4) -0.5699(3) 0.09290(15) 0.0598(8) Uani 1 1 d . . . . .
C14 C 0.0589(4) -0.1108(3) -0.10144(15) 0.0587(8) Uani 1 1 d . . . . .
H14 H -0.049305 -0.096867 -0.098349 0.070 Uiso 1 1 calc R U . . .
C15 C 0.0958(4) -0.1445(3) -0.16598(15) 0.0624(9) Uani 1 1 d . . . . .
C16 C -0.0511(5) -0.1492(4) -0.20202(19) 0.0885(13) Uani 1 1 d . . . . .
H16A H -0.136800 -0.161299 -0.176686 0.106 Uiso 1 1 calc R U . . .
H16B H -0.066351 -0.082645 -0.222925 0.106 Uiso 1 1 calc R U . . .
C17 C 0.0117(4) -0.6464(3) 0.05695(18) 0.0683(10) Uani 1 1 d . . . . .
H17 H -0.005969 -0.715319 0.070564 0.082 Uiso 1 1 calc R U . . .
C18 C -0.0240(4) -0.6187(3) 0.00044(17) 0.0667(9) Uani 1 1 d . . . . .
C19 C -0.0336(6) -0.2389(4) -0.2433(2) 0.1048(17) Uani 1 1 d . . . . .
H19A H 0.018641 -0.215844 -0.278230 0.126 Uiso 1 1 calc R U . . .
H19B H -0.130791 -0.267838 -0.254225 0.126 Uiso 1 1 calc R U . . .
C20 C 0.5711(5) -0.4049(5) -0.1684(2) 0.1019(17) Uani 1 1 d . . . . .
H20A H 0.557145 -0.407109 -0.209894 0.153 Uiso 1 1 calc R U . . .
H20B H 0.658688 -0.445740 -0.158132 0.153 Uiso 1 1 calc R U . . .
H20C H 0.584275 -0.332077 -0.156138 0.153 Uiso 1 1 calc R U . . .
C21 C 0.0578(4) -0.3209(4) -0.21057(16) 0.0734(11) Uani 1 1 d . . . . .
H21A H -0.006484 -0.368223 -0.188146 0.088 Uiso 1 1 calc R U . . .
H21B H 0.118788 -0.363204 -0.236963 0.088 Uiso 1 1 calc R U . . .
F23 F 0.2660(7) -0.6227(10) 0.1550(2) 0.148(2) Uani 0.85 1 d . . P A 1
C24 C 0.1439(6) -0.0053(3) -0.09190(19) 0.0850(13) Uani 1 1 d . . . . .
H24A H 0.086346 0.042881 -0.067373 0.102 Uiso 1 1 calc R U . . .
H24B H 0.240840 -0.018198 -0.073797 0.102 Uiso 1 1 calc R U . . .
F25 F 0.0449(14) -0.6767(7) 0.1758(4) 0.160(5) Uani 0.85 1 d . . P A 1
C26 C 0.1628(6) 0.0400(3) -0.1515(2) 0.0936(14) Uani 1 1 d . . . . .
H26A H 0.242612 0.092890 -0.152462 0.112 Uiso 1 1 calc R U . . .
H26B H 0.070285 0.072381 -0.165300 0.112 Uiso 1 1 calc R U . . .
C27 C 0.1224(6) -0.5985(4) 0.15319(19) 0.0819(12) Uani 1 1 d . . . . .
C29 C 0.2038(6) -0.0584(4) -0.1874(2) 0.0942(15) Uani 1 1 d . . . . .
H29A H 0.189823 -0.044986 -0.228686 0.113 Uiso 1 1 calc R U . . .
H29B H 0.307376 -0.079302 -0.180601 0.113 Uiso 1 1 calc R U . . .
C30 C 0.4491(6) -0.4489(4) -0.07294(18) 0.1012(16) Uani 1 1 d . . . . .
H30A H 0.464786 -0.376600 -0.060220 0.152 Uiso 1 1 calc R U . . .
H30B H 0.532590 -0.492387 -0.060937 0.152 Uiso 1 1 calc R U . . .
H30C H 0.358211 -0.476224 -0.055948 0.152 Uiso 1 1 calc R U . . .
C31 C 0.4361(5) -0.4514(4) -0.13890(18) 0.0795(12) Uani 1 1 d . . . . .
F1 F -0.1173(15) -0.7926(4) -0.0177(3) 0.141(2) Uani 0.85 1 d . . P B 1
F2 F -0.2200(12) -0.6670(5) -0.0620(5) 0.177(4) Uani 0.85 1 d . . P B 1
C0AA C -0.0908(8) -0.6996(4) -0.0399(3) 0.1063(18) Uani 1 1 d . . . . .
F4 F 0.0021(14) -0.7192(10) -0.0847(3) 0.196(5) Uani 0.85 1 d . . P B 1
C1 C 0.4052(7) -0.5651(4) -0.1602(2) 0.1152(19) Uani 1 1 d . . . . .
H1A H 0.316432 -0.592201 -0.141502 0.173 Uiso 1 1 calc R U . . .
H1B H 0.489274 -0.610096 -0.150860 0.173 Uiso 1 1 calc R U . . .
H1C H 0.390380 -0.564390 -0.201673 0.173 Uiso 1 1 calc R U . . .
F3 F -0.220(5) -0.733(5) -0.012(3) 0.21(2) Uani 0.15 1 d . . P B 2
F7 F -0.104(5) -0.662(2) -0.0880(13) 0.116(9) Uani 0.15 1 d . . P B 2
F9 F -0.014(6) -0.779(4) -0.040(4) 0.21(3) Uani 0.15 1 d . . P B 2
F1AA F 0.174(6) -0.700(2) 0.1553(9) 0.101(9) Uani 0.15 1 d . . P A 2
F0AA F 0.007(4) -0.622(6) 0.1879(16) 0.16(3) Uani 0.15 1 d . . P A 2
F2AA F 0.204(8) -0.535(4) 0.181(2) 0.17(3) Uani 0.15 1 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
S1 C7 1.684(3) . ?
N2 H2 0.8600 . ?
N2 C7 1.357(4) . ?
N2 C11 1.398(4) . ?
N3 C8 1.358(4) . ?
N3 C15 1.473(4) . ?
N3 C21 1.469(4) . ?
O4 C8 1.220(4) . ?
N5 H5 0.8600 . ?
N5 C7 1.327(4) . ?
N5 C14 1.446(4) . ?
O6 C8 1.342(4) . ?
O6 C31 1.472(4) . ?
C9 H9 0.9300 . ?
C9 C11 1.386(5) . ?
C9 C13 1.384(5) . ?
F10 C27 1.306(7) . ?
C11 C12 1.384(5) . ?
C12 H12 0.9300 . ?
C12 C18 1.379(5) . ?
C13 C17 1.379(5) . ?
C13 C27 1.491(5) . ?
C14 H14 0.9800 . ?
C14 C15 1.574(5) . ?
C14 C24 1.535(5) . ?
C15 C16 1.547(5) . ?
C15 C29 1.522(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C19 1.475(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(5) . ?
C18 C0AA 1.494(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C21 1.507(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C31 1.496(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
F23 C27 1.313(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C26 1.489(6) . ?
F25 C27 1.302(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C29 1.525(7) . ?
C27 F1AA 1.34(2) . ?
C27 F0AA 1.33(3) . ?
C27 F2AA 1.25(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C30 C31 1.518(6) . ?
C31 C1 1.527(6) . ?
F1 C0AA 1.291(8) . ?
F2 C0AA 1.320(9) . ?
C0AA F4 1.341(11) . ?
C0AA F3 1.38(4) . ?
C0AA F7 1.20(3) . ?
C0AA F9 1.21(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
_geom_angle_publ_flag
C7 N2 H2 115.5 . . ?
C7 N2 C11 129.0(3) . . ?
C11 N2 H2 115.5 . . ?
C8 N3 C15 123.4(3) . . ?
C8 N3 C21 123.5(3) . . ?
C21 N3 C15 113.0(3) . . ?
C7 N5 H5 116.8 . . ?
C7 N5 C14 126.5(3) . . ?
C14 N5 H5 116.8 . . ?
C8 O6 C31 120.9(3) . . ?
N2 C7 S1 123.0(2) . . ?
N5 C7 S1 123.5(2) . . ?
N5 C7 N2 113.4(3) . . ?
O4 C8 N3 124.4(3) . . ?
O4 C8 O6 125.6(3) . . ?
O6 C8 N3 109.9(3) . . ?
C11 C9 H9 120.1 . . ?
C13 C9 H9 120.1 . . ?
C13 C9 C11 119.7(3) . . ?
C9 C11 N2 117.9(3) . . ?
C12 C11 N2 122.6(3) . . ?
C12 C11 C9 119.4(3) . . ?
C11 C12 H12 120.0 . . ?
C18 C12 C11 120.0(3) . . ?
C18 C12 H12 120.0 . . ?
C9 C13 C27 118.7(3) . . ?
C17 C13 C9 121.0(3) . . ?
C17 C13 C27 120.3(3) . . ?
N5 C14 H14 108.7 . . ?
N5 C14 C15 115.6(3) . . ?
N5 C14 C24 109.8(3) . . ?
C15 C14 H14 108.7 . . ?
C24 C14 H14 108.7 . . ?
C24 C14 C15 105.1(3) . . ?
N3 C15 C14 114.4(3) . . ?
N3 C15 C16 101.5(3) . . ?
N3 C15 C29 114.6(3) . . ?
C16 C15 C14 109.7(3) . . ?
C29 C15 C14 104.2(3) . . ?
C29 C15 C16 112.8(4) . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C19 C16 C15 106.4(4) . . ?
C19 C16 H16A 110.4 . . ?
C19 C16 H16B 110.4 . . ?
C13 C17 H17 120.6 . . ?
C18 C17 C13 118.8(3) . . ?
C18 C17 H17 120.6 . . ?
C12 C18 C0AA 118.7(4) . . ?
C17 C18 C12 121.0(3) . . ?
C17 C18 C0AA 120.3(4) . . ?
C16 C19 H19A 110.8 . . ?
C16 C19 H19B 110.8 . . ?
C16 C19 C21 104.7(3) . . ?
H19A C19 H19B 108.9 . . ?
C21 C19 H19A 110.8 . . ?
C21 C19 H19B 110.8 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C31 C20 H20A 109.5 . . ?
C31 C20 H20B 109.5 . . ?
C31 C20 H20C 109.5 . . ?
N3 C21 C19 102.9(3) . . ?
N3 C21 H21A 111.2 . . ?
N3 C21 H21B 111.2 . . ?
C19 C21 H21A 111.2 . . ?
C19 C21 H21B 111.2 . . ?
H21A C21 H21B 109.1 . . ?
C14 C24 H24A 110.8 . . ?
C14 C24 H24B 110.8 . . ?
H24A C24 H24B 108.9 . . ?
C26 C24 C14 104.5(3) . . ?
C26 C24 H24A 110.8 . . ?
C26 C24 H24B 110.8 . . ?
C24 C26 H26A 111.3 . . ?
C24 C26 H26B 111.3 . . ?
C24 C26 C29 102.5(3) . . ?
H26A C26 H26B 109.2 . . ?
C29 C26 H26A 111.3 . . ?
C29 C26 H26B 111.3 . . ?
F10 C27 C13 113.0(4) . . ?
F10 C27 F23 104.3(5) . . ?
F23 C27 C13 111.3(4) . . ?
F25 C27 F10 105.1(6) . . ?
F25 C27 C13 113.4(5) . . ?
F25 C27 F23 109.2(6) . . ?
F1AA C27 C13 110.9(10) . . ?
F0AA C27 C13 112.8(17) . . ?
F0AA C27 F1AA 92(2) . . ?
F2AA C27 C13 119.5(13) . . ?
F2AA C27 F1AA 112(3) . . ?
F2AA C27 F0AA 106(3) . . ?
C15 C29 C26 104.2(4) . . ?
C15 C29 H29A 110.9 . . ?
C15 C29 H29B 110.9 . . ?
C26 C29 H29A 110.9 . . ?
C26 C29 H29B 110.9 . . ?
H29A C29 H29B 108.9 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C31 C30 H30C 109.5 . . ?
O6 C31 C20 109.8(4) . . ?
O6 C31 C30 110.6(4) . . ?
O6 C31 C1 101.7(4) . . ?
C20 C31 C30 112.5(4) . . ?
C20 C31 C1 111.2(4) . . ?
C30 C31 C1 110.6(4) . . ?
F1 C0AA C18 116.0(5) . . ?
F1 C0AA F2 105.7(7) . . ?
F1 C0AA F4 104.4(7) . . ?
F2 C0AA C18 112.0(5) . . ?
F2 C0AA F4 107.3(9) . . ?
F4 C0AA C18 110.7(6) . . ?
F3 C0AA C18 104.0(16) . . ?
F7 C0AA C18 110.2(12) . . ?
F7 C0AA F3 118(3) . . ?
F7 C0AA F9 112(4) . . ?
F9 C0AA C18 109(2) . . ?
F9 C0AA F3 103(3) . . ?
C31 C1 H1A 109.5 . . ?
C31 C1 H1B 109.5 . . ?
C31 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C11 C12 C18 178.2(3) . . . . ?
N3 C15 C16 C19 -23.0(5) . . . . ?
N3 C15 C29 C26 -153.1(3) . . . . ?
N5 C14 C15 N3 6.8(5) . . . . ?
N5 C14 C15 C16 120.0(3) . . . . ?
N5 C14 C15 C29 -119.0(4) . . . . ?
N5 C14 C24 C26 149.4(4) . . . . ?
C7 N2 C11 C9 -147.0(3) . . . . ?
C7 N2 C11 C12 37.4(5) . . . . ?
C7 N5 C14 C15 -80.3(4) . . . . ?
C7 N5 C14 C24 161.0(3) . . . . ?
C8 N3 C15 C14 -61.9(5) . . . . ?
C8 N3 C15 C16 -179.9(3) . . . . ?
C8 N3 C15 C29 58.3(5) . . . . ?
C8 N3 C21 C19 -159.8(4) . . . . ?
C8 O6 C31 C20 -62.4(5) . . . . ?
C8 O6 C31 C30 62.2(5) . . . . ?
C8 O6 C31 C1 179.7(4) . . . . ?
C9 C11 C12 C18 2.7(5) . . . . ?
C9 C13 C17 C18 1.1(6) . . . . ?
C9 C13 C27 F10 34.1(7) . . . . ?
C9 C13 C27 F23 -82.9(8) . . . . ?
C9 C13 C27 F25 153.5(8) . . . . ?
C9 C13 C27 F1AA -144(2) . . . . ?
C9 C13 C27 F0AA 114(4) . . . . ?
C9 C13 C27 F2AA -11(5) . . . . ?
C11 N2 C7 S1 10.9(5) . . . . ?
C11 N2 C7 N5 -170.0(3) . . . . ?
C11 C9 C13 C17 -1.7(5) . . . . ?
C11 C9 C13 C27 176.0(4) . . . . ?
C11 C12 C18 C17 -3.4(6) . . . . ?
C11 C12 C18 C0AA 178.5(4) . . . . ?
C12 C18 C0AA F1 -179.1(8) . . . . ?
C12 C18 C0AA F2 -57.6(11) . . . . ?
C12 C18 C0AA F4 62.1(10) . . . . ?
C12 C18 C0AA F3 -124(4) . . . . ?
C12 C18 C0AA F7 3(3) . . . . ?
C12 C18 C0AA F9 126(5) . . . . ?
C13 C9 C11 N2 -175.9(3) . . . . ?
C13 C9 C11 C12 -0.2(5) . . . . ?
C13 C17 C18 C12 1.4(6) . . . . ?
C13 C17 C18 C0AA 179.5(5) . . . . ?
C14 N5 C7 S1 -7.1(4) . . . . ?
C14 N5 C7 N2 173.9(3) . . . . ?
C14 C15 C16 C19 -144.3(4) . . . . ?
C14 C15 C29 C26 -27.4(4) . . . . ?
C14 C24 C26 C29 -41.6(5) . . . . ?
C15 N3 C8 O4 -1.7(6) . . . . ?
C15 N3 C8 O6 176.9(3) . . . . ?
C15 N3 C21 C19 17.1(4) . . . . ?
C15 C14 C24 C26 24.4(4) . . . . ?
C15 C16 C19 C21 34.3(5) . . . . ?
C16 C15 C29 C26 91.5(4) . . . . ?
C16 C19 C21 N3 -31.0(5) . . . . ?
C17 C13 C27 F10 -148.2(6) . . . . ?
C17 C13 C27 F23 94.9(8) . . . . ?
C17 C13 C27 F25 -28.8(9) . . . . ?
C17 C13 C27 F1AA 34(3) . . . . ?
C17 C13 C27 F0AA -68(4) . . . . ?
C17 C13 C27 F2AA 167(5) . . . . ?
C17 C18 C0AA F1 2.8(11) . . . . ?
C17 C18 C0AA F2 124.2(9) . . . . ?
C17 C18 C0AA F4 -116.0(9) . . . . ?
C17 C18 C0AA F3 58(4) . . . . ?
C17 C18 C0AA F7 -175(3) . . . . ?
C17 C18 C0AA F9 -52(5) . . . . ?
C21 N3 C8 O4 174.9(4) . . . . ?
C21 N3 C8 O6 -6.5(5) . . . . ?
C21 N3 C15 C14 121.1(4) . . . . ?
C21 N3 C15 C16 3.2(4) . . . . ?
C21 N3 C15 C29 -118.6(4) . . . . ?
C24 C14 C15 N3 128.1(3) . . . . ?
C24 C14 C15 C16 -118.7(4) . . . . ?
C24 C14 C15 C29 2.2(4) . . . . ?
C24 C26 C29 C15 43.3(5) . . . . ?
C27 C13 C17 C18 -176.6(4) . . . . ?
C29 C15 C16 C19 100.0(5) . . . . ?
C31 O6 C8 N3 176.3(3) . . . . ?
C31 O6 C8 O4 -5.1(6) . . . . ?

_olex2_date_sample_data_collection 2020-01-13
_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 1.416
_oxdiff_exptl_absorpt_empirical_full_min 0.557
####################################################################### 
# 
# 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_yuanyh_0924
_database_code_depnum_ccdc_archive 'CCDC 2048404'
loop_
_audit_author_name
_audit_author_address
'Ming-Hui Xu'
;lanzhou university
China
;
_audit_update_record             
;
2020-12-05 deposited with the CCDC.	2021-04-14 downloaded from the CCDC.
;
_audit_creation_date             2020-12-04
_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         'C17 H17 F6 N3'
_chemical_formula_sum            'C17 H17 F6 N3'
_chemical_formula_weight         377.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   12.0427(3)
_cell_length_b                   12.0427(3)
_cell_length_c                   22.0973(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2775.36(17)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1447
_cell_measurement_temperature    294.03(15)
_cell_measurement_theta_max      65.1680
_cell_measurement_theta_min      7.3200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1170
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6679
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.829
_diffrn_reflns_theta_min         4.239
_diffrn_ambient_temperature      294.03(15)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -26.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   77.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
  2 omega   62.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega   41.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega  106.00  168.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 62

#__ type_ start__ end____ width___ exp.time_
  5 omega   87.00  169.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
  6 omega   84.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 87

#__ type_ start__ end____ width___ exp.time_
  7 omega  131.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
  8 omega  100.00  169.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
  9 omega   80.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0444384000
_diffrn_orient_matrix_UB_12      -0.0474600000
_diffrn_orient_matrix_UB_13      -0.0650270000
_diffrn_orient_matrix_UB_21      -0.1388356000
_diffrn_orient_matrix_UB_22      -0.0825852000
_diffrn_orient_matrix_UB_23      0.0226775000
_diffrn_orient_matrix_UB_31      -0.0236307000
_diffrn_orient_matrix_UB_32      0.1129573000
_diffrn_orient_matrix_UB_33      -0.0107723000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.829
_reflns_number_gt                2431
_reflns_number_total             3199
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.28(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3199
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.103
_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)+(0.0600P)²+0.0577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1292
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3AA) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2AA) \\sim Ueq, Uanis(F13)
\\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F17) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C4AA) \\sim Ueq, Uanis(C2AA) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C9AA)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C7AA) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6AA)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F4(0.5) F9(0.5) F12(0.5) F14(0.5) F17(0.5) F2AA(0.5) H3Aa(0.5)
 H3Ab(0.5) H3Ac(0.5) H3Ad(0.5) H5Ac(0.5) H5Ad(0.5) H5Aa(0.5) H5Ab(0.5) F1(0.5)
 F0AA(0.5) F1AA(0.5) F2(0.5) F13(0.5) F3AA(0.5) C2AA(0.5) H2Aa(0.5) H2Ab(0.5)
 C2(0.5) H2a(0.5) H2b(0.5) C4AA(0.5) H4Aa(0.5) H4Ab(0.5) C9AA(0.5) H9Aa(0.5)
 H9Ab(0.5) C7AA(0.5) H7Aa(0.5) H7Ab(0.5) C6AA(0.5) H6Aa(0.5) H6Ab(0.5) C4(0.5)
 H4a(0.5) H4b(0.5) C5(0.5) H5a(0.5) H5b(0.5)
4.a Ternary CH refined with riding coordinates:
 C0AA(H0AA)
4.b Secondary CH2 refined with riding coordinates:
 C3AA(H3Aa,H3Ab), C3AA(H3Ac,H3Ad), C5AA(H5Ac,H5Ad), C5AA(H5Aa,H5Ab), C2AA(H2Aa,
 H2Ab), C2(H2a,H2b), C4AA(H4Aa,H4Ab), C9AA(H9Aa,H9Ab), C7AA(H7Aa,H7Ab),
 C6AA(H6Aa,H6Ab), C4(H4a,H4b), C5(H5a,H5b)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), N6(H6), C15(H15), C1AA(H1AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2821(3) -0.2290(3) -0.47118(16) 0.0550(7) Uani 1 1 d . . . . .
N2 N -0.2032(3) -0.1683(3) -0.51463(14) 0.0634(7) Uani 1 1 d . . . . .
C3 C 0.0204(3) -0.0097(4) -0.51705(16) 0.0630(8) Uani 1 1 d . . . . .
H3 H -0.002532 0.053156 -0.520780 0.076 Uiso 1 1 calc R . . . .
F4 F 0.2327(15) 0.2288(11) -0.4892(7) 0.147(6) Uani 0.5 1 d . . P A 1
N5 N -0.4091(3) -0.2614(3) -0.47498(15) 0.0661(8) Uani 1 1 d . . . . .
N6 N -0.2607(3) -0.2657(3) -0.41713(14) 0.0684(8) Uani 1 1 d . . . . .
H6 H -0.186284 -0.250139 -0.405230 0.082 Uiso 1 1 calc R . . . .
C7 C -0.0752(3) -0.1383(4) -0.51086(16) 0.0586(7) Uani 1 1 d . . . . .
C8 C 0.2461(4) 0.1624(5) -0.5264(3) 0.0946(15) Uani 1 1 d . . . . .
F9 F 0.3612(12) 0.1765(17) -0.5095(14) 0.206(12) Uani 0.5 1 d . . P A 1
C10 C 0.1480(4) 0.0249(4) -0.51766(19) 0.0712(10) Uani 1 1 d . . . . .
C11 C 0.0906(5) -0.1935(5) -0.5082(2) 0.0862(13) Uani 1 1 d . . . . .
F12 F 0.099(3) -0.362(2) -0.4631(12) 0.214(9) Uani 0.5 1 d . U P B 1
C13 C -0.4814(4) -0.3422(5) -0.4230(2) 0.0859(13) Uani 1 1 d . . . . .
F14 F 0.257(2) 0.1993(18) -0.5811(9) 0.164(9) Uani 0.5 1 d . . P A 1
C15 C 0.1836(4) -0.0665(5) -0.5134(2) 0.0871(13) Uani 1 1 d . . . . .
H15 H 0.269891 -0.042874 -0.513957 0.104 Uiso 1 1 calc R . . . .
F17 F 0.0352(12) -0.4110(12) -0.5052(10) 0.150(4) Uani 0.5 1 d . U P B 2
C0AA C -0.3762(4) -0.3345(5) -0.38078(19) 0.0823(12) Uani 1 1 d . . . . .
H0AA H -0.392117 -0.420224 -0.370067 0.099 Uiso 1 1 calc R . . . .
C1AA C -0.0379(4) -0.2300(4) -0.5072(2) 0.0731(10) Uani 1 1 d . . . . .
H1AA H -0.099552 -0.316267 -0.504049 0.088 Uiso 1 1 calc R . . . .
F2AA F 0.2522(18) -0.248(2) -0.5102(10) 0.192(8) Uani 0.5 1 d . U P B 1
C3AA C -0.4808(4) -0.3205(5) -0.5306(2) 0.0929(15) Uani 1 1 d . . . . .
H3AA H -0.507183 -0.265073 -0.549899 0.111 Uiso 0.5 1 calc R . P C 1
H3AB H -0.428452 -0.336238 -0.558772 0.111 Uiso 0.5 1 calc R . P C 1
H3AC H -0.423651 -0.298850 -0.565000 0.111 Uiso 0.5 1 calc R . P D 2
H3AD H -0.543005 -0.293629 -0.538777 0.111 Uiso 0.5 1 calc R . P D 2
C5AA C -0.3754(6) -0.2607(8) -0.3250(2) 0.119(2) Uani 1 1 d . . . . .
H5AC H -0.290827 -0.218288 -0.306725 0.143 Uiso 0.5 1 calc R . P E 2
H5AD H -0.436280 -0.318832 -0.295411 0.143 Uiso 0.5 1 calc R . P E 2
H5AA H -0.412655 -0.316626 -0.290267 0.143 Uiso 0.5 1 calc R . P F 1
H5AB H -0.289555 -0.192793 -0.314986 0.143 Uiso 0.5 1 calc R . P F 1
C8AA C 0.1286(8) -0.2936(9) -0.5052(5) 0.136(3) Uani 1 1 d . . . . .
F1 F 0.1991(12) 0.2480(10) -0.5237(8) 0.142(6) Uani 0.5 1 d . . P A 2
F0AA F 0.3015(18) 0.188(2) -0.5767(9) 0.139(9) Uani 0.5 1 d . . P A 2
F1AA F 0.3415(18) 0.2129(16) -0.4900(8) 0.166(9) Uani 0.5 1 d . . P A 2
F2 F 0.2166(19) -0.2784(19) -0.5441(8) 0.164(6) Uani 0.5 1 d . U P B 2
F13 F 0.1741(18) -0.2887(17) -0.4422(8) 0.176(6) Uani 0.5 1 d . U P B 2
F3AA F 0.071(3) -0.380(2) -0.5550(11) 0.224(8) Uani 0.5 1 d . U P B 1
C2AA C -0.5925(16) -0.4409(17) -0.5123(10) 0.104(4) Uani 0.5 1 d . U P G 1
H2AA H -0.616613 -0.504071 -0.544304 0.125 Uiso 0.5 1 calc R . P G 1
H2AB H -0.664395 -0.427979 -0.504352 0.125 Uiso 0.5 1 calc R . P G 1
C2 C -0.5877(16) -0.4546(17) -0.4465(9) 0.101(5) Uani 0.5 1 d . U P G 2
H2A H -0.664378 -0.447283 -0.445675 0.121 Uiso 0.5 1 calc R . P G 2
H2B H -0.603269 -0.529180 -0.423138 0.121 Uiso 0.5 1 calc R . P G 2
C4AA C -0.5482(17) -0.4660(15) -0.5167(9) 0.111(5) Uani 0.5 1 d . U P G 2
H4AA H -0.490131 -0.499782 -0.519005 0.133 Uiso 0.5 1 calc R . P G 2
H4AB H -0.622373 -0.515889 -0.542221 0.133 Uiso 0.5 1 calc R . P G 2
C9AA C -0.5576(17) -0.4866(16) -0.4561(9) 0.097(5) Uani 0.5 1 d . U P G 1
H9AA H -0.501346 -0.520912 -0.464215 0.116 Uiso 0.5 1 calc R . P G 1
H9AB H -0.632089 -0.548239 -0.433454 0.116 Uiso 0.5 1 calc R . P G 1
C7AA C -0.555(2) -0.3090(18) -0.3885(10) 0.105(5) Uani 0.5 1 d . U P G 1
H7AA H -0.620669 -0.382185 -0.366701 0.126 Uiso 0.5 1 calc R . P G 1
H7AB H -0.593895 -0.270918 -0.412800 0.126 Uiso 0.5 1 calc R . P G 1
C6AA C -0.4137(19) -0.157(2) -0.3451(10) 0.109(5) Uani 0.5 1 d . U P G 2
H6AA H -0.438494 -0.123296 -0.311109 0.131 Uiso 0.5 1 calc R . P G 2
H6AB H -0.346709 -0.087485 -0.368278 0.131 Uiso 0.5 1 calc R . P G 2
C4 C -0.5305(17) -0.2501(17) -0.3850(9) 0.098(4) Uani 0.5 1 d . U P G 2
H4A H -0.552475 -0.202337 -0.413240 0.117 Uiso 0.5 1 calc R . P G 2
H4B H -0.604691 -0.303220 -0.360059 0.117 Uiso 0.5 1 calc R . P G 2
C5 C -0.454(2) -0.2109(19) -0.3454(12) 0.133(7) Uani 0.5 1 d . U P G 1
H5A H -0.401968 -0.130132 -0.366195 0.160 Uiso 0.5 1 calc R . P G 1
H5B H -0.495338 -0.196069 -0.311244 0.160 Uiso 0.5 1 calc R . P G 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.290(5) . ?
C1 N5 1.379(4) . ?
C1 N6 1.343(4) . ?
N2 C7 1.399(5) . ?
C3 C7 1.401(5) . ?
C3 C10 1.376(5) . ?
F4 C8 1.212(11) . ?
N5 C13 1.475(5) . ?
N5 C3AA 1.466(5) . ?
N6 C0AA 1.454(5) . ?
C7 C1AA 1.387(5) . ?
C8 F9 1.361(19) . ?
C8 C10 1.490(6) . ?
C8 F14 1.27(2) . ?
C8 F1 1.403(13) . ?
C8 F0AA 1.253(16) . ?
C8 F1AA 1.279(12) . ?
C10 C15 1.369(7) . ?
C11 C15 1.377(8) . ?
C11 C1AA 1.382(6) . ?
C11 C8AA 1.489(8) . ?
F12 C8AA 1.171(19) . ?
C13 C0AA 1.539(6) . ?
C13 C2 1.417(18) . ?
C13 C9AA 1.675(17) . ?
C13 C7AA 1.37(2) . ?
C13 C4 1.715(19) . ?
F17 C8AA 1.294(15) . ?
C0AA C5AA 1.518(8) . ?
F2AA C8AA 1.310(19) . ?
C3AA C2AA 1.457(19) . ?
C3AA C4AA 1.549(17) . ?
C5AA C6AA 1.59(2) . ?
C5AA C5 1.42(3) . ?
C8AA F2 1.305(17) . ?
C8AA F13 1.486(19) . ?
C8AA F3AA 1.43(2) . ?
C2AA C9AA 1.50(3) . ?
C2 C4AA 1.65(3) . ?
C7AA C5 1.53(3) . ?
C6AA C4 1.56(3) . ?

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
N2 C1 N5 120.9(3) . . ?
N2 C1 N6 129.8(3) . . ?
N6 C1 N5 109.2(3) . . ?
C1 N2 C7 120.4(3) . . ?
C10 C3 C7 120.8(4) . . ?
C1 N5 C13 110.1(3) . . ?
C1 N5 C3AA 119.3(4) . . ?
C3AA N5 C13 108.8(3) . . ?
C1 N6 C0AA 113.1(3) . . ?
N2 C7 C3 118.0(3) . . ?
C1AA C7 N2 123.5(4) . . ?
C1AA C7 C3 118.1(3) . . ?
F4 C8 F9 101.2(13) . . ?
F4 C8 C10 110.6(7) . . ?
F4 C8 F14 116.1(14) . . ?
F9 C8 C10 107.1(10) . . ?
F14 C8 F9 107.1(13) . . ?
F14 C8 C10 113.5(11) . . ?
F1 C8 C10 115.1(6) . . ?
F0AA C8 C10 114.7(10) . . ?
F0AA C8 F1 102.4(12) . . ?
F0AA C8 F1AA 101.5(14) . . ?
F1AA C8 C10 118.1(9) . . ?
F1AA C8 F1 102.7(12) . . ?
C3 C10 C8 118.8(4) . . ?
C15 C10 C3 120.5(4) . . ?
C15 C10 C8 120.6(4) . . ?
C15 C11 C1AA 120.9(4) . . ?
C15 C11 C8AA 119.7(5) . . ?
C1AA C11 C8AA 119.4(6) . . ?
N5 C13 C0AA 103.7(3) . . ?
N5 C13 C9AA 100.5(7) . . ?
N5 C13 C4 103.6(7) . . ?
C0AA C13 C9AA 109.5(8) . . ?
C0AA C13 C4 101.8(8) . . ?
C2 C13 N5 107.4(8) . . ?
C2 C13 C0AA 127.1(10) . . ?
C2 C13 C4 110.9(11) . . ?
C7AA C13 N5 119.7(9) . . ?
C7AA C13 C0AA 106.0(10) . . ?
C7AA C13 C9AA 116.7(11) . . ?
C10 C15 C11 119.4(4) . . ?
N6 C0AA C13 102.9(3) . . ?
N6 C0AA C5AA 113.0(4) . . ?
C5AA C0AA C13 107.0(5) . . ?
C11 C1AA C7 120.2(4) . . ?
N5 C3AA C4AA 103.4(7) . . ?
C2AA C3AA N5 106.1(9) . . ?
C0AA C5AA C6AA 108.2(8) . . ?
C5 C5AA C0AA 100.3(10) . . ?
F12 C8AA C11 119.4(12) . . ?
F12 C8AA F2AA 104.2(17) . . ?
F12 C8AA F3AA 103.5(17) . . ?
F17 C8AA C11 115.7(7) . . ?
F17 C8AA F2 110.8(14) . . ?
F17 C8AA F13 98.4(13) . . ?
F2AA C8AA C11 113.9(12) . . ?
F2AA C8AA F3AA 106.0(15) . . ?
F2 C8AA C11 114.4(9) . . ?
F2 C8AA F13 110.7(12) . . ?
F13 C8AA C11 105.4(10) . . ?
F3AA C8AA C11 108.7(9) . . ?
C3AA C2AA C9AA 107.8(12) . . ?
C13 C2 C4AA 105.3(11) . . ?
C3AA C4AA C2 95.8(12) . . ?
C2AA C9AA C13 95.1(12) . . ?
C13 C7AA C5 101.2(16) . . ?
C4 C6AA C5AA 96.1(13) . . ?
C6AA C4 C13 105.2(13) . . ?
C5AA C5 C7AA 108.1(16) . . ?

_olex2_date_sample_data_collection 2019-09-25
_olex2_submission_special_instructions 'No special instructions were received'
