# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_tazeen
_database_code_depnum_ccdc_archive 'CCDC 2113872'
loop_
_audit_author_name
_audit_author_address
aaaaa
;FJIRSM
China
;
_audit_update_record             
;
2021-10-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_audit_creation_date             2020-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H21 F5 O4'
_chemical_formula_sum            'C22 H21 F5 O4'
_chemical_formula_weight         444.39
_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 0.0147 0.0070 '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'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z+2/3'
3 '-x+y, -x, z+1/3'

_cell_length_a                   17.8769(9)
_cell_length_b                   17.8769(9)
_cell_length_c                   5.8193(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1610.58(19)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    15302
_cell_measurement_temperature    109.85(16)
_cell_measurement_theta_max      60.5600
_cell_measurement_theta_min      2.4590
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             690
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            21941
_diffrn_reflns_theta_full        60.49
_diffrn_reflns_theta_max         60.49
_diffrn_reflns_theta_min         2.48
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.85(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  26.00   0.50    0.05    --   72.03 -19.00 -30.00   56
  2  ω      6.00  33.00   0.50    0.05    --   72.03 -38.00   0.00   54
  3  ω     -3.00  24.00   0.50    0.05    --   72.03 -19.00  60.00   54
  4  ω     30.00  65.00   0.50    0.05    --   72.03 -57.00 150.00   70
  5  ω     -2.00  23.00   0.50    0.05    --   72.03 -38.00 150.00   50
  6  ω     -2.00  25.00   0.50    0.05    --   72.03 -19.00 120.00   54
  7  ω     90.00 136.00   0.50    0.05    --   72.03 101.00  76.00   92
  8  ω    -43.00  -3.00   0.50    0.05    --  -75.46  77.00  60.00   80
  9  ω    -98.00 -59.00   0.50    0.05    --  -75.46  77.00  60.00   78
 10  ω    -96.00 -65.00   0.50    0.05    --  -75.46  77.00 -60.00   62
 11  ω    -51.00  -3.00   0.50    0.05    --  -75.46  77.00 -60.00   96
 12  ω    -80.00  -2.00   0.50    0.05    --  -75.46  77.00-120.00  156
 13  ω    -66.00 -18.00   0.50    0.05    --  -75.46  57.00 -60.00   96
 14  ω    -60.00 -16.00   0.50    0.05    --  -75.46  57.00  60.00   88
 15  ω    -43.00 -18.00   0.50    0.05    --  -75.46  38.00 120.00   50
 16  ω    -25.00   0.00   0.50    0.05    --  -75.46  19.00 120.00   50
 17  ω    -38.00  -3.00   0.50    0.05    --  -75.46  38.00   0.00   70
 18  ω     29.00  61.00   0.50    0.05    --   -1.72  38.00  60.00   64
 19  ω    -13.00  71.00   0.50    0.05    --   -1.72  57.00 -90.00  168
 20  ω    -26.00  -1.00   0.50    0.05    --  -75.46  19.00-180.00   50
 21  ω    -25.00   0.00   0.50    0.05    --  -75.46  19.00-150.00   50
 22  ω    -25.00   0.00   0.50    0.05    --  -75.46  19.00-120.00   50
 23  ω    -26.00  -1.00   0.50    0.05    --  -75.46  19.00  90.00   50
 24  ω   -110.00 -45.00   0.50    0.05    --  -75.46 125.00  60.00  130
 25  ω    -78.00 -53.00   0.50    0.05    --  -75.46 101.00  76.00   50
 26  ω   -135.00 -91.00   0.50    0.05    --  -75.46-101.00 -28.00   88
 27  ω   -134.00 -96.00   0.50    0.05    --  -75.46 -99.00  60.00   76
 28  ω    -74.00  -5.00   0.50    0.05    --   -1.72 -19.00 120.00  138
 29  ω      3.00  28.00   0.50    0.05    --   72.03 -99.00 -90.00   50
 30  ω     63.00 101.00   0.50    0.05    --   72.03-101.00 -28.00   76
 31  ω     62.00 104.00   0.50    0.05    --   72.03 -99.00 -90.00   84
 32  ω     21.00 107.00   0.50    0.05    --   72.03-125.00-180.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0689454000
_diffrn_orient_matrix_UB_12      -0.0753220000
_diffrn_orient_matrix_UB_13      0.0603668000
_diffrn_orient_matrix_UB_21      0.0511980000
_diffrn_orient_matrix_UB_22      -0.0337906000
_diffrn_orient_matrix_UB_23      0.0346569000
_diffrn_orient_matrix_UB_31      0.0108464000
_diffrn_orient_matrix_UB_32      0.0260289000
_diffrn_orient_matrix_UB_33      0.2196101000
_diffrn_oxdiff_digest_frames     
;
01809d0d6f8f6f889c34eb1954e3cf2d0400039238f
;
_diffrn_oxdiff_digest_hkl        
;
011884ab70ca1e11b76d9135260a00e8ad4b80
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34050
_diffrn_source                   'micro-focus metaljet'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3577
_reflns_number_total             3736
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_coef       0.0031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3736
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.057
_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)+(0.0388P)²+0.1460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0713
_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. 
;
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C31(H31), C27(H27), C29(H29), C30(H30), C28(H28)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C9 C -0.63475(9) -0.72325(8) -0.7229(2) 0.0174(3) Uani 1 d . . .
H9 H -0.6393 -0.7183 -0.8894 0.021 Uiso 1 calc . . R
C31 C -0.50926(9) -0.68976(10) -0.4555(3) 0.0224(3) Uani 1 d . . .
H31 H -0.5469 -0.7345 -0.3596 0.027 Uiso 1 calc . . R
C20 C -0.68873(10) -0.69655(9) -0.3414(2) 0.0215(3) Uani 1 d . . .
H20A H -0.6984 -0.7519 -0.2913 0.032 Uiso 1 calc . . GR
H20B H -0.7317 -0.6858 -0.2751 0.032 Uiso 1 calc . . GR
H20C H -0.6324 -0.6524 -0.2933 0.032 Uiso 1 calc . . GR
C2 C -0.79149(10) -0.57569(10) -0.7369(3) 0.0243(3) Uani 1 d . . .
C11 C -0.66173(9) -0.86245(9) -0.8337(3) 0.0211(3) Uani 1 d . . .
C27 C -0.48311(9) -0.60498(10) -0.7988(3) 0.0224(3) Uani 1 d . . .
H27 H -0.5032 -0.5930 -0.9333 0.027 Uiso 1 calc . . R
C15 C -0.78845(9) -0.75900(9) -0.6743(3) 0.0207(3) Uani 1 d . . .
C1 C -0.72161(9) -0.56620(9) -0.6097(2) 0.0202(3) Uani 1 d . . .
C7 C -0.66727(9) -0.60409(9) -0.6923(3) 0.0196(3) Uani 1 d . . .
H7A H -0.6079 -0.5655 -0.6470 0.024 Uiso 1 calc . . R
H7B H -0.6689 -0.6058 -0.8589 0.024 Uiso 1 calc . . R
C6 C -0.70218(10) -0.51629(10) -0.4133(3) 0.0242(3) Uani 1 d . . .
F22 F -0.90716(7) -0.55008(7) -0.8027(2) 0.0476(3) Uani 1 d . . .
O14 O -0.63089(7) -0.83465(7) -1.01944(19) 0.0274(2) Uani 1 d . . .
F24 F -0.72897(8) -0.43053(7) -0.15250(19) 0.0440(3) Uani 1 d . . .
C17 C -0.87795(10) -0.84222(12) -0.9883(3) 0.0346(4) Uani 1 d . . .
H17A H -0.8909 -0.8179 -1.1212 0.041 Uiso 1 calc . . R
H17B H -0.9227 -0.8566 -0.8742 0.041 Uiso 1 calc . . R
F21 F -0.81284(6) -0.62175(7) -0.93314(17) 0.0343(2) Uani 1 d . . .
C4 C -0.81878(11) -0.48978(11) -0.4765(3) 0.0327(4) Uani 1 d . . .
O10 O -0.66878(6) -0.81364(6) -0.66623(17) 0.0214(2) Uani 1 d . . .
F23 F -0.63438(6) -0.50172(6) -0.28252(17) 0.0332(2) Uani 1 d . . .
O19 O -0.84929(7) -0.78436(10) -0.5486(2) 0.0432(3) Uani 1 d . . .
O16 O -0.79403(7) -0.77994(8) -0.89421(19) 0.0315(3) Uani 1 d . . .
F25 F -0.86629(8) -0.45460(7) -0.4114(2) 0.0504(3) Uani 1 d . . .
C29 C -0.36567(10) -0.57423(10) -0.5416(3) 0.0284(3) Uani 1 d . . .
H29 H -0.3076 -0.5416 -0.5024 0.034 Uiso 1 calc . . R
C5 C -0.74992(11) -0.47827(10) -0.3454(3) 0.0291(3) Uani 1 d . . .
C8 C -0.69467(9) -0.69592(9) -0.6024(2) 0.0183(3) Uani 1 d . . .
C3 C -0.83971(11) -0.53843(11) -0.6734(3) 0.0311(4) Uani 1 d . . .
C26 C -0.54030(9) -0.67150(9) -0.6559(3) 0.0188(3) Uani 1 d . . .
C30 C -0.42230(10) -0.64116(11) -0.3998(3) 0.0263(3) Uani 1 d . . .
H30 H -0.4018 -0.6535 -0.2666 0.032 Uiso 1 calc . . R
C28 C -0.39568(10) -0.55605(10) -0.7415(3) 0.0276(3) Uani 1 d . . .
H28 H -0.3578 -0.5114 -0.8372 0.033 Uiso 1 calc . . R
C12 C -0.69561(13) -0.95404(10) -0.7550(3) 0.0332(4) Uani 1 d . . .
H12A H -0.7511 -0.9746 -0.6807 0.040 Uiso 1 calc . . R
H12B H -0.6562 -0.9552 -0.6423 0.040 Uiso 1 calc . . R
C13 C -0.70595(16) -1.01395(11) -0.9509(4) 0.0469(5) Uani 1 d . . .
H13A H -0.7449 -1.0130 -1.0630 0.070 Uiso 1 calc . . GR
H13B H -0.7288 -1.0716 -0.8932 0.070 Uiso 1 calc . . GR
H13C H -0.6508 -0.9953 -1.0209 0.070 Uiso 1 calc . . GR
C18 C -0.87508(15) -0.92153(13) -1.0561(6) 0.0641(7) Uani 1 d . . .
H18A H -0.8279 -0.9060 -1.1602 0.096 Uiso 1 calc . . GR
H18B H -0.9283 -0.9616 -1.1301 0.096 Uiso 1 calc . . GR
H18C H -0.8672 -0.9479 -0.9216 0.096 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C9 H9 0.9800 . ?
C9 O10 1.4516(15) . ?
C9 C8 1.5496(18) . ?
C9 C26 1.5156(19) . ?
C31 H31 0.9300 . ?
C31 C26 1.398(2) . ?
C31 C30 1.388(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C8 1.5233(19) . ?
C2 C1 1.387(2) . ?
C2 F21 1.3468(18) . ?
C2 C3 1.377(2) . ?
C11 O14 1.2024(19) . ?
C11 O10 1.3552(17) . ?
C11 C12 1.505(2) . ?
C27 H27 0.9300 . ?
C27 C26 1.391(2) . ?
C27 C28 1.397(2) . ?
C15 O19 1.1959(19) . ?
C15 O16 1.3233(18) . ?
C15 C8 1.5383(19) . ?
C1 C7 1.5137(19) . ?
C1 C6 1.383(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5504(18) . ?
C6 F23 1.3416(18) . ?
C6 C5 1.388(2) . ?
F22 C3 1.346(2) . ?
F24 C5 1.3449(19) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 O16 1.4560(18) . ?
C17 C18 1.497(3) . ?
C4 F25 1.3398(18) . ?
C4 C5 1.374(3) . ?
C4 C3 1.372(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.388(2) . ?
C29 C28 1.386(2) . ?
C30 H30 0.9300 . ?
C28 H28 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.511(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
O10 C9 H9 108.5 . . ?
O10 C9 C8 106.09(10) . . ?
O10 C9 C26 109.87(11) . . ?
C8 C9 H9 108.5 . . ?
C26 C9 H9 108.5 . . ?
C26 C9 C8 115.21(11) . . ?
C26 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C26 119.98(14) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 C20 H20A 109.5 . . ?
C8 C20 H20B 109.5 . . ?
C8 C20 H20C 109.5 . . ?
F21 C2 C1 119.32(13) . . ?
F21 C2 C3 117.92(14) . . ?
C3 C2 C1 122.75(15) . . ?
O14 C11 O10 123.46(13) . . ?
O14 C11 C12 125.11(14) . . ?
O10 C11 C12 111.42(13) . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.43(14) . . ?
C28 C27 H27 119.8 . . ?
O19 C15 O16 123.96(14) . . ?
O19 C15 C8 124.26(14) . . ?
O16 C15 C8 111.75(12) . . ?
C2 C1 C7 121.07(13) . . ?
C6 C1 C2 116.10(13) . . ?
C6 C1 C7 122.72(13) . . ?
C1 C7 H7A 108.4 . . ?
C1 C7 H7B 108.4 . . ?
C1 C7 C8 115.66(11) . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C1 C6 C5 122.23(15) . . ?
F23 C6 C1 120.33(13) . . ?
F23 C6 C5 117.42(14) . . ?
H17A C17 H17B 108.4 . . ?
O16 C17 H17A 110.0 . . ?
O16 C17 H17B 110.0 . . ?
O16 C17 C18 108.26(15) . . ?
C18 C17 H17A 110.0 . . ?
C18 C17 H17B 110.0 . . ?
F25 C4 C5 120.23(16) . . ?
F25 C4 C3 119.85(16) . . ?
C3 C4 C5 119.92(14) . . ?
C11 O10 C9 115.55(11) . . ?
C15 O16 C17 118.90(12) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.00(14) . . ?
F24 C5 C6 120.25(16) . . ?
F24 C5 C4 120.22(15) . . ?
C4 C5 C6 119.53(15) . . ?
C9 C8 C7 106.20(11) . . ?
C20 C8 C9 112.77(11) . . ?
C20 C8 C15 108.66(11) . . ?
C20 C8 C7 110.97(11) . . ?
C15 C8 C9 108.53(11) . . ?
C15 C8 C7 109.64(11) . . ?
F22 C3 C2 120.27(16) . . ?
F22 C3 C4 120.26(15) . . ?
C4 C3 C2 119.47(15) . . ?
C31 C26 C9 121.55(13) . . ?
C27 C26 C9 119.08(13) . . ?
C27 C26 C31 119.36(13) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 C31 120.45(14) . . ?
C29 C30 H30 119.8 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.76(15) . . ?
C29 C28 H28 120.1 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C11 C12 C13 112.42(14) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C2 C1 C7 C8 -92.86(16) . . . . ?
C2 C1 C6 F23 -178.33(13) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C1 C2 C3 F22 -179.69(15) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 C7 C8 C9 175.91(12) . . . . ?
C1 C7 C8 C20 -61.20(16) . . . . ?
C1 C7 C8 C15 58.84(15) . . . . ?
C1 C6 C5 F24 179.71(14) . . . . ?
C1 C6 C5 C4 -0.2(2) . . . . ?
C7 C1 C6 F23 -2.1(2) . . . . ?
C7 C1 C6 C5 176.68(14) . . . . ?
C6 C1 C7 C8 91.10(17) . . . . ?
O14 C11 O10 C9 -1.1(2) . . . . ?
O14 C11 C12 C13 -13.1(3) . . . . ?
F21 C2 C1 C7 2.2(2) . . . . ?
F21 C2 C1 C6 178.45(13) . . . . ?
F21 C2 C3 F22 1.6(2) . . . . ?
F21 C2 C3 C4 -178.86(15) . . . . ?
O10 C9 C8 C20 66.72(14) . . . . ?
O10 C9 C8 C15 -53.72(14) . . . . ?
O10 C9 C8 C7 -171.54(10) . . . . ?
O10 C9 C26 C31 -37.85(17) . . . . ?
O10 C9 C26 C27 141.38(13) . . . . ?
O10 C11 C12 C13 168.01(16) . . . . ?
F23 C6 C5 F24 -1.5(2) . . . . ?
F23 C6 C5 C4 178.58(14) . . . . ?
O19 C15 O16 C17 -4.5(2) . . . . ?
O19 C15 C8 C9 142.20(16) . . . . ?
O19 C15 C8 C20 19.2(2) . . . . ?
O19 C15 C8 C7 -102.20(18) . . . . ?
O16 C15 C8 C9 -39.63(16) . . . . ?
O16 C15 C8 C20 -162.59(12) . . . . ?
O16 C15 C8 C7 75.97(15) . . . . ?
F25 C4 C5 C6 178.97(14) . . . . ?
F25 C4 C5 F24 -1.0(2) . . . . ?
F25 C4 C3 C2 -178.80(15) . . . . ?
F25 C4 C3 F22 0.8(2) . . . . ?
C5 C4 C3 C2 0.3(2) . . . . ?
C5 C4 C3 F22 179.93(15) . . . . ?
C8 C9 O10 C11 145.02(12) . . . . ?
C8 C9 C26 C31 81.88(16) . . . . ?
C8 C9 C26 C27 -98.90(15) . . . . ?
C8 C15 O16 C17 177.33(13) . . . . ?
C3 C2 C1 C7 -176.58(14) . . . . ?
C3 C2 C1 C6 -0.3(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C3 C4 C5 F24 179.87(15) . . . . ?
C26 C9 O10 C11 -89.84(14) . . . . ?
C26 C9 C8 C20 -55.07(15) . . . . ?
C26 C9 C8 C15 -175.51(12) . . . . ?
C26 C9 C8 C7 66.68(15) . . . . ?
C26 C31 C30 C29 0.1(2) . . . . ?
C26 C27 C28 C29 0.3(2) . . . . ?
C30 C31 C26 C9 179.83(13) . . . . ?
C30 C31 C26 C27 0.6(2) . . . . ?
C30 C29 C28 C27 0.4(2) . . . . ?
C28 C27 C26 C9 179.92(13) . . . . ?
C28 C27 C26 C31 -0.8(2) . . . . ?
C28 C29 C30 C31 -0.6(2) . . . . ?
C12 C11 O10 C9 177.79(12) . . . . ?
C18 C17 O16 C15 -113.99(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.091
_oxdiff_exptl_absorpt_empirical_full_min 0.530
####################################################################### 
# 
# 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_1721
_database_code_depnum_ccdc_archive 'CCDC 2113873'
loop_
_audit_author_name
_audit_author_address
bbb
;FJIRSM
China
;
_audit_update_record             
;
2021-10-05 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-03-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_chemical_formula_moiety         'C12 H12 F O3'
_chemical_formula_sum            'C12 H12 F O3'
_chemical_formula_weight         223.226
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'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'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'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 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'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 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   10.0078(5)
_cell_length_b                   5.8787(2)
_cell_length_c                   19.4922(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.878(5)
_cell_angle_gamma                90
_cell_volume                     1144.15(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3182
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.0760
_cell_measurement_theta_min      4.8310
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       plate
_exptl_crystal_F_000             469.802
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_Laue_measured_fraction_full 0.9877
_diffrn_reflns_Laue_measured_fraction_max 0.9161
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9609
_diffrn_reflns_point_group_measured_fraction_full 0.9719
_diffrn_reflns_point_group_measured_fraction_max 0.8807
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         78.33
_diffrn_reflns_theta_min         4.43
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9877
_diffrn_measured_fraction_theta_max 0.9161
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -30.00   0.50    0.50    --    0.00 -77.00-180.00   52
  2  ω    -85.00 -15.00   0.50    0.50    --    0.00 -19.00  90.00  140
  3  ω    -87.00 -54.00   0.50    0.50    --    0.00 -19.00 -30.00   66
  4  ω    -14.00  14.00   0.50    0.50    --    0.00 -19.00  90.00   56
  5  ω    -13.00  27.00   0.50    0.50    --    0.00 -77.00-180.00   80
  6  ω    -15.00  14.00   0.50    0.50    --    0.00 -19.00 -30.00   58
  7  ω      6.00 125.00   0.50    4.50    --   95.20 -77.00-120.00  238
  8  ω     78.00 143.00   0.50    4.50    --   95.20  45.00 120.00  130
  9  ω     79.00 183.00   0.50    4.50    --   95.20  30.00  90.00  208
 10  ω     18.00  70.00   0.50    4.50    --   95.20 -61.00 150.00  104
 11  ω     84.00 120.00   0.50    4.50    --   95.20  30.00  30.00   72
 12  ω     11.00  94.00   0.50    4.50    --   95.20 -61.00 -60.00  166
 13  ω     16.00  43.00   0.50    4.50    --   95.20 -77.00 120.00   54
 14  ω     96.00 123.00   0.50    4.50    --   95.20 -77.00 120.00   54
 15  ω     89.00 116.00   0.50    4.50    --   95.20  30.00 -60.00   54
 16  ω    126.00 167.00   0.50    4.50    --   95.20  30.00 150.00   82
 17  ω     17.00 100.00   0.50    4.50    --   95.20 -61.00-120.00  166
 18  ω     78.00 152.00   0.50    4.50    --   95.20  61.00 150.00  148
 19  ω     79.00 183.00   0.50    4.50    --   95.20  45.00 -60.00  208
 20  ω     81.00 183.00   0.50    4.50    --   95.20  30.00 -90.00  204
 21  ω     72.00  97.00   0.50    4.50    --   95.20  15.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1468105000
_diffrn_orient_matrix_UB_12      -0.0738155000
_diffrn_orient_matrix_UB_13      -0.0153808000
_diffrn_orient_matrix_UB_21      -0.0474921000
_diffrn_orient_matrix_UB_22      0.2104440000
_diffrn_orient_matrix_UB_23      0.0386784000
_diffrn_orient_matrix_UB_31      -0.0061165000
_diffrn_orient_matrix_UB_32      0.1376152000
_diffrn_orient_matrix_UB_33      -0.0673288000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.838
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              24
_reflns_limit_l_min              -24
_reflns_number_gt                3612
_reflns_number_total             4335
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.5553
_refine_diff_density_min         -0.3511
_refine_diff_density_rms         0.1001
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_d_res_high            0.7872
_refine_ls_d_res_low             9.9849
_refine_ls_goodness_of_fit_ref   1.0358
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4335
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0821
_refine_ls_restrained_S_all      1.0358
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1382P)²+1.2768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2301
_refine_ls_wR_factor_ref         0.2373
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00a,H00b), C00L(H00d,H00e)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U), C1(H1)
2.d X=CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003), O007(H007)
;
_atom_sites_solution_primary     dual
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
F001 F 0.5496(3) -0.0430(4) 0.26086(14) 0.0347(6) Uani 1.000000 .
F002 F 0.0358(3) 1.0152(4) 0.25619(14) 0.0344(6) Uani 1.000000 .
O003 O -0.1982(3) 0.7810(6) 0.18537(18) 0.0328(7) Uani 1.000000 .
H003 H -0.210(2) 0.889(7) 0.211(2) 0.0492(11) Uiso 1.000000 GR
O004 O 0.7428(3) 0.2228(6) 0.22267(19) 0.0363(8) Uani 1.000000 .
O005 O 0.2435(3) 0.7443(6) 0.2896(2) 0.0386(8) Uani 1.000000 .
O006 O 0.6022(3) 0.5188(6) 0.20808(19) 0.0376(8) Uani 1.000000 .
O007 O 0.3144(3) 0.1889(6) 0.3112(2) 0.0404(9) Uani 1.000000 .
H007 H 0.2574(12) 0.2892(14) 0.311(4) 0.0606(13) Uiso 1.000000 GR
O008 O 0.1060(4) 0.4446(6) 0.2943(2) 0.0422(9) Uani 1.000000 .
C009 C 0.4421(4) 0.2883(8) 0.3010(3) 0.0306(10) Uani 1.000000 .
H009 H 0.4260(4) 0.4476(8) 0.2881(3) 0.0367(12) Uiso 1.000000 R
C00A C 0.6326(5) 0.3053(8) 0.2230(2) 0.0298(10) Uani 1.000000 .
C00B C 0.1300(5) 0.6592(8) 0.2846(3) 0.0311(10) Uani 1.000000 .
C00C C -0.0662(5) 0.6973(8) 0.1976(3) 0.0338(10) Uani 1.000000 .
H00C H -0.0730(5) 0.5318(8) 0.2024(3) 0.0406(12) Uiso 1.000000 R
C00D C 0.5068(4) 0.1735(8) 0.2405(3) 0.0300(10) Uani 1.000000 .
C00E C 0.0195(5) 0.7421(8) 0.1373(3) 0.0353(11) Uani 1.000000 .
C00F C 0.0032(4) 0.7884(8) 0.2658(2) 0.0287(9) Uani 1.000000 .
C00G C 0.5318(5) 0.2888(9) 0.3669(3) 0.0332(10) Uani 1.000000 .
C00H C 0.4126(5) 0.1495(10) 0.1762(3) 0.0395(12) Uani 1.000000 .
H00a H 0.3377(5) 0.0533(10) 0.1865(3) 0.0474(14) Uiso 1.000000 R
H00b H 0.3772(5) 0.2981(10) 0.1631(3) 0.0474(14) Uiso 1.000000 R
C00I C 0.1823(6) 0.8271(11) 0.0290(3) 0.0465(14) Uani 1.000000 .
H00I H 0.2347(6) 0.8550(11) -0.0078(3) 0.0558(16) Uiso 1.000000 R
C00J C 0.6092(5) 0.4774(10) 0.3842(3) 0.0381(11) Uani 1.000000 .
H00J H 0.6069(5) 0.6015(10) 0.3545(3) 0.0457(13) Uiso 1.000000 R
C00K C -0.0215(6) 0.8360(11) 0.3925(3) 0.0480(14) Uani 1.000000 .
H00K H 0.0283(6) 0.7235(11) 0.4160(3) 0.0576(17) Uiso 1.000000 R
C00L C -0.0902(5) 0.7761(9) 0.3247(3) 0.0375(11) Uani 1.000000 .
H00d H -0.1648(5) 0.8793(9) 0.3151(3) 0.0450(13) Uiso 1.000000 R
H00e H -0.1260(5) 0.6233(9) 0.3271(3) 0.0450(13) Uiso 1.000000 R
C00M C 0.1115(6) 0.5798(10) 0.1192(3) 0.0417(12) Uani 1.000000 .
H00M H 0.1180(6) 0.4423(10) 0.1428(3) 0.0501(15) Uiso 1.000000 R
C00N C 0.5355(6) 0.1033(9) 0.4117(3) 0.0421(13) Uani 1.000000 .
H00N H 0.4856(6) -0.0262(9) 0.4000(3) 0.0505(15) Uiso 1.000000 R
C00O C 0.0113(6) 0.9496(10) 0.1013(3) 0.0415(12) Uani 1.000000 .
H00O H -0.0484(6) 1.0613(10) 0.1136(3) 0.0498(15) Uiso 1.000000 R
C00P C 0.0919(6) 0.9868(10) 0.0479(3) 0.0460(13) Uani 1.000000 .
H00P H 0.0848(6) 1.1237(10) 0.0240(3) 0.0552(15) Uiso 1.000000 R
C00Q C 0.6115(6) 0.1103(11) 0.4722(3) 0.0471(14) Uani 1.000000 .
H00Q H 0.6107(6) -0.0126(11) 0.5022(3) 0.0565(16) Uiso 1.000000 R
C00R C 0.6906(6) 0.4859(11) 0.4451(3) 0.0485(13) Uani 1.000000 .
H00R H 0.7437(6) 0.6126(11) 0.4558(3) 0.0582(16) Uiso 1.000000 R
C00S C 0.6906(6) 0.2992(12) 0.4899(3) 0.0506(14) Uani 1.000000 .
H00S H 0.7431(6) 0.3014(12) 0.5311(3) 0.0607(17) Uiso 1.000000 R
C00U C 0.1953(6) 0.6219(11) 0.0652(3) 0.0493(14) Uani 1.000000 .
H00U H 0.2584(6) 0.5146(11) 0.0539(3) 0.0592(17) Uiso 1.000000 R
C1 C 0.4806(6) 0.0497(13) 0.1173(3) 0.0525(15) Uani 1.000000 .
H1 H 0.4933(6) -0.1070(13) 0.1174(3) 0.0631(18) Uiso 1.000000 R
C2 C -0.0268(8) 1.0379(14) 0.4212(4) 0.069(2) Uani 1.000000 .
C3 C 0.5228(8) 0.1615(18) 0.0670(4) 0.075(2) Uani 1.000000 .
H2a H -0.0758(8) 1.1540(14) 0.3990(4) 0.082(2) Uiso 1.000000 R
H2b H 0.0184(8) 1.0646(14) 0.4637(4) 0.082(2) Uiso 1.000000 R
H3a H 0.5121(8) 0.3186(18) 0.0650(4) 0.089(3) Uiso 1.000000 R
H3b H 0.5642(8) 0.0859(18) 0.0323(4) 0.089(3) Uiso 1.000000 R


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
F001 C00D 1.392(5) . ?
F002 C00F 1.388(5) . ?
O003 H003 0.8200 . ?
O003 C00C 1.415(6) . ?
O004 C00A 1.205(6) . ?
O005 C00B 1.239(6) . ?
O006 C00A 1.319(6) . ?
O007 H007 0.8200 . ?
O007 C009 1.432(5) . ?
O008 C00B 1.301(6) . ?
C009 H009 0.9800 . ?
C009 C00D 1.539(6) . ?
C009 C00G 1.517(7) . ?
C00A C00D 1.536(6) . ?
C00B C00F 1.503(6) . ?
C00C H00C 0.9800 . ?
C00C C00E 1.524(7) . ?
C00C C00F 1.553(7) . ?
C00D C00H 1.524(7) . ?
C00E C00M 1.388(7) . ?
C00E C00O 1.407(7) . ?
C00F C00L 1.531(7) . ?
C00G C00J 1.381(7) . ?
C00G C00N 1.395(8) . ?
C00H H00a 0.9700 . ?
C00H H00b 0.9700 . ?
C00H C1 1.494(8) . ?
C00I H00I 0.9300 . ?
C00I C00P 1.371(9) . ?
C00I C00U 1.400(9) . ?
C00J H00J 0.9300 . ?
C00J C00R 1.395(8) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.490(8) . ?
C00K C2 1.314(10) . ?
C00L H00d 0.9700 . ?
C00L H00e 0.9700 . ?
C00M H00M 0.9300 . ?
C00M C00U 1.411(8) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.360(8) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.378(8) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00S 1.393(9) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.403(9) . ?
C00S H00S 0.9300 . ?
C00U H00U 0.9300 . ?
C1 H1 0.9300 . ?
C1 C3 1.277(10) . ?
C2 H2a 0.9300 . ?
C2 H2b 0.9300 . ?
C3 H3a 0.9300 . ?
C3 H3b 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
C00C O003 H003 109.5 . . ?
C009 O007 H007 109.5 . . ?
H009 C009 O007 107.0(2) . . ?
C00D C009 O007 110.7(4) . . ?
C00D C009 H009 107.0(2) . . ?
C00G C009 O007 111.4(4) . . ?
C00G C009 H009 107.0(3) . . ?
C00G C009 C00D 113.2(4) . . ?
O006 C00A O004 125.4(5) . . ?
C00D C00A O004 124.2(4) . . ?
C00D C00A O006 110.4(4) . . ?
O008 C00B O005 123.9(5) . . ?
C00F C00B O005 124.7(4) . . ?
C00F C00B O008 111.4(4) . . ?
H00C C00C O003 106.9(2) . . ?
C00E C00C O003 112.2(4) . . ?
C00E C00C H00C 106.9(3) . . ?
C00F C00C O003 112.5(4) . . ?
C00F C00C H00C 106.9(2) . . ?
C00F C00C C00E 111.0(4) . . ?
C009 C00D F001 108.7(4) . . ?
C00A C00D F001 106.5(4) . . ?
C00A C00D C009 110.1(4) . . ?
C00H C00D F001 108.1(4) . . ?
C00H C00D C009 113.7(4) . . ?
C00H C00D C00A 109.5(4) . . ?
C00M C00E C00C 119.7(4) . . ?
C00O C00E C00C 121.2(5) . . ?
C00O C00E C00M 119.1(5) . . ?
C00B C00F F002 108.4(4) . . ?
C00C C00F F002 108.2(4) . . ?
C00C C00F C00B 110.8(4) . . ?
C00L C00F F002 107.9(4) . . ?
C00L C00F C00B 110.0(4) . . ?
C00L C00F C00C 111.4(4) . . ?
C00J C00G C009 119.8(5) . . ?
C00N C00G C009 121.1(5) . . ?
C00N C00G C00J 119.0(5) . . ?
H00a C00H C00D 109.1(3) . . ?
H00b C00H C00D 109.1(3) . . ?
H00b C00H H00a 107.9 . . ?
C1 C00H C00D 112.3(4) . . ?
C1 C00H H00a 109.1(3) . . ?
C1 C00H H00b 109.1(4) . . ?
C00P C00I H00I 120.2(4) . . ?
C00U C00I H00I 120.2(4) . . ?
C00U C00I C00P 119.6(5) . . ?
H00J C00J C00G 119.3(3) . . ?
C00R C00J C00G 121.4(5) . . ?
C00R C00J H00J 119.3(4) . . ?
C00L C00K H00K 117.9(3) . . ?
C2 C00K H00K 117.9(5) . . ?
C2 C00K C00L 124.1(6) . . ?
C00K C00L C00F 112.7(4) . . ?
H00d C00L C00F 109.1(3) . . ?
H00d C00L C00K 109.1(3) . . ?
H00e C00L C00F 109.1(3) . . ?
H00e C00L C00K 109.1(3) . . ?
H00e C00L H00d 107.8 . . ?
H00M C00M C00E 119.8(3) . . ?
C00U C00M C00E 120.4(5) . . ?
C00U C00M H00M 119.8(4) . . ?
H00N C00N C00G 119.8(3) . . ?
C00Q C00N C00G 120.5(5) . . ?
C00Q C00N H00N 119.8(4) . . ?
H00O C00O C00E 120.1(3) . . ?
C00P C00O C00E 119.8(5) . . ?
C00P C00O H00O 120.1(4) . . ?
C00O C00P C00I 121.7(6) . . ?
H00P C00P C00I 119.2(4) . . ?
H00P C00P C00O 119.2(4) . . ?
H00Q C00Q C00N 119.5(4) . . ?
C00S C00Q C00N 121.0(6) . . ?
C00S C00Q H00Q 119.5(4) . . ?
H00R C00R C00J 120.7(4) . . ?
C00S C00R C00J 118.5(6) . . ?
C00S C00R H00R 120.7(4) . . ?
C00R C00S C00Q 119.5(5) . . ?
H00S C00S C00Q 120.2(4) . . ?
H00S C00S C00R 120.2(4) . . ?
C00M C00U C00I 119.2(6) . . ?
H00U C00U C00I 120.4(4) . . ?
H00U C00U C00M 120.4(4) . . ?
H1 C1 C00H 117.3(4) . . ?
C3 C1 C00H 125.5(8) . . ?
C3 C1 H1 117.3(6) . . ?
H2a C2 C00K 120.0 . . ?
H2b C2 C00K 120.0 . . ?
H2b C2 H2a 120.0 . . ?
H3a C3 C1 120.0 . . ?
H3b C3 C1 120.0 . . ?
H3b C3 H3a 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C00D C009 O007 -72.5(4) . . . . ?
F001 C00D C009 C00G 53.4(4) . . . . ?
F001 C00D C00A O004 5.1(5) . . . . ?
F001 C00D C00A O006 -175.3(4) . . . . ?
F001 C00D C00H C1 -62.5(5) . . . . ?
F002 C00F C00B O005 -0.6(5) . . . . ?
F002 C00F C00B O008 180.0(4) . . . . ?
F002 C00F C00C O003 -73.4(4) . . . . ?
F002 C00F C00C C00E 53.2(4) . . . . ?
F002 C00F C00L C00K -68.3(4) . . . . ?
O003 C00C C00E C00M -142.3(4) . . . . ?
O003 C00C C00E C00O 40.4(5) . . . . ?
O003 C00C C00F C00B 167.9(4) . . . . ?
O003 C00C C00F C00L 45.0(4) . . . . ?
O004 C00A C00D C009 122.7(5) . . . . ?
O004 C00A C00D C00H -111.6(5) . . . . ?
O005 C00B C00F C00C 117.9(5) . . . . ?
O005 C00B C00F C00L -118.4(5) . . . . ?
O006 C00A C00D C009 -57.6(4) . . . . ?
O006 C00A C00D C00H 68.0(4) . . . . ?
O007 C009 C00D C00A 171.2(4) . . . . ?
O007 C009 C00D C00H 47.9(5) . . . . ?
O007 C009 C00G C00J -138.3(4) . . . . ?
O007 C009 C00G C00N 40.1(5) . . . . ?
O008 C00B C00F C00C -61.5(5) . . . . ?
O008 C00B C00F C00L 62.2(5) . . . . ?
C009 C00D C00H C1 176.7(5) . . . . ?
C009 C00G C00J C00R 178.6(4) . . . . ?
C009 C00G C00N C00Q -176.8(5) . . . . ?
C00A C00D C00H C1 53.1(5) . . . . ?
C00B C00F C00C C00E -65.5(4) . . . . ?
C00B C00F C00L C00K 49.8(5) . . . . ?
C00C C00E C00M C00U -177.6(5) . . . . ?
C00C C00E C00O C00P 178.8(5) . . . . ?
C00C C00F C00L C00K 173.1(4) . . . . ?
C00D C00H C1 C3 -101.2(6) . . . . ?
C00E C00M C00U C00I -1.6(6) . . . . ?
C00E C00O C00P C00I -0.9(6) . . . . ?
C00F C00L C00K C2 97.9(6) . . . . ?
C00G C00J C00R C00S -1.3(6) . . . . ?
C00G C00N C00Q C00S -2.1(7) . . . . ?
C00J C00R C00S C00Q 0.9(6) . . . . ?
C00N C00Q C00S C00R 0.8(7) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.957
_oxdiff_exptl_absorpt_empirical_full_min 0.543
