# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_hpd119b
_database_code_depnum_ccdc_archive 'CCDC 2009993'
loop_
_audit_author_name
_audit_author_address
haifeng
;The Cambridge Crystallographic Data Centre 
China
;
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_audit_creation_date             2020-06-15
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H23 F O5'
_chemical_formula_sum            'C29 H23 F O5'
_chemical_formula_weight         470.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     HF-0610
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9631(3)
_cell_length_b                   9.1494(2)
_cell_length_c                   13.3605(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.001(3)
_cell_angle_gamma                90
_cell_volume                     1191.28(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6038
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.3640
_cell_measurement_theta_min      4.5230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -1 -8 0.0820
0 -6 -1 0.0527
-2 1 8 0.0344
0 6 0 0.0504
6 0 2 0.0131
-3 -1 8 0.0450
-6 0 -2 0.0075

_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.021
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.4417 -1.2390 -8.3326 0.0994 0.4065 0.9082
0.0917 -5.9034 -0.9309 0.2320 0.9658 -0.1154
-2.4631 1.0512 8.3845 -0.0925 -0.3778 -0.9212
0.3045 5.9291 -0.3974 -0.2247 -0.9367 0.2686
5.9270 -0.1935 1.7243 0.9723 -0.2337 -0.0089
-3.0366 -1.2930 8.1111 -0.0890 0.0232 -0.9958
-5.9270 0.1935 -1.7243 -0.9723 0.2337 0.0089

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14112
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.406
_diffrn_reflns_theta_min         3.382
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00  -1.00   0.50    0.38    --  -46.62 109.00 122.00  160
  2  ω    -51.00 -16.00   0.50    1.52    --  -88.50  45.00  60.00   70
  3  ω    -51.00 -16.00   0.50    1.52    --  -88.50  45.00  90.00   70
  4  ω    -82.00 -15.00   0.50    1.52    --  -88.50 109.00 122.00  134
  5  ω    -51.00 -16.00   0.50    1.52    --  -88.50  45.00 -30.00   70
  6  ω    -51.00 -16.00   0.50    1.52    --  -88.50  45.00 -60.00   70
  7  ω   -119.00 -83.00   0.50    0.38    --  -46.62 -57.00-150.00   72
  8  ω   -120.00 -48.00   0.50    0.38    --  -46.62 -37.00-120.00  144
  9  ω   -119.00 -87.00   0.50    0.38    --  -46.62-125.00-120.00   64
 10  ω   -119.00 -83.00   0.50    0.38    --  -46.62 -57.00   0.00   72
 11  ω   -120.00 -32.00   0.50    0.38    --  -46.62 -37.00   0.00  176
 12  ω     22.00  87.00   0.50    0.38    --   46.62-109.00  26.00  130
 13  ω     34.00 108.00   0.50    1.52    --  106.69-109.00  26.00  148
 14  ω     34.00 111.00   0.50    1.52    --  106.69-125.00   0.00  154
 15  ω     34.00 101.00   0.50    1.52    --  106.69 -77.00   0.00  134
 16  ω     34.00  71.00   0.50    1.52    --  106.69 -61.00 120.00   74
 17  ω     34.00 101.00   0.50    1.52    --  106.69 -77.00  60.00  134
 18  ω     34.00  71.00   0.50    1.52    --  106.69 -61.00   0.00   74
 19  ω     83.00 120.00   0.50    0.38    --   46.62  57.00-150.00   74
 20  ω     83.00 120.00   0.50    0.38    --   46.62  57.00-180.00   74
 21  ω     83.00 120.00   0.50    0.38    --   46.62  57.00 -90.00   74
 22  ω     95.00 178.00   0.50    1.52    --  106.69 125.00-150.00  166
 23  ω    104.00 178.00   0.50    1.52    --  106.69 109.00 122.00  148
 24  ω     34.00 101.00   0.50    1.52    --  106.69 -77.00-180.00  134
 25  ω     34.00  71.00   0.50    1.52    --  106.69 -61.00-180.00   74
 26  ω   -119.00 -87.00   0.50    0.38    --  -46.62-125.00  60.00   64
 27  ω   -120.00 -32.00   0.50    0.38    --  -46.62 -37.00  90.00  176
 28  ω   -160.00 -82.00   0.50    1.52    --  -88.50-109.00  26.00  156
 29  ω   -160.00-100.00   0.50    1.52    --  -88.50 -94.00  60.00  120
 30  ω   -160.00-101.00   0.50    1.52    --  -88.50 -77.00  90.00  118
 31  ω   -160.00-101.00   0.50    1.52    --  -88.50 -77.00  60.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1513375000
_diffrn_orient_matrix_UB_12      -0.0430721000
_diffrn_orient_matrix_UB_13      0.0388238000
_diffrn_orient_matrix_UB_21      -0.0343531000
_diffrn_orient_matrix_UB_22      -0.1585794000
_diffrn_orient_matrix_UB_23      -0.0352750000
_diffrn_orient_matrix_UB_31      0.0303977000
_diffrn_orient_matrix_UB_32      0.0366671000
_diffrn_orient_matrix_UB_33      -0.1055404000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.792
_reflns_number_gt                3887
_reflns_number_total             4208
_reflns_odcompleteness_completeness 100.00
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.022
_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)+(0.0500P)²+0.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7(3)
 0.3(3)
2. 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, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C28(H28), C5(H5), C27(H27), C15(H15), C19(H19), C8(H8), C25(H25),
 C7(H7), C24(H24), C17(H17), C16(H16), C18(H18)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3438(2) 0.0513(2) 0.45385(16) 0.0364(5) Uani 1 1 d . . . . .
O1 O 0.4387(3) 0.3133(3) 0.94540(17) 0.0300(6) Uani 1 1 d . . . . .
H1 H 0.517339 0.281758 0.960852 0.045 Uiso 1 1 calc R U . . .
O5 O 0.6546(3) 0.2076(3) 0.92387(17) 0.0337(6) Uani 1 1 d . . . . .
O3 O 0.3045(3) 0.8279(3) 0.84249(19) 0.0344(6) Uani 1 1 d . . . . .
O4 O 0.4692(3) 0.8573(3) 0.7523(2) 0.0353(6) Uani 1 1 d . . . . .
O2 O 0.0765(3) 0.5978(4) 0.6645(2) 0.0436(7) Uani 1 1 d . . . . .
C22 C 0.6204(4) 0.2285(4) 0.8248(3) 0.0282(8) Uani 1 1 d . . . . .
C14 C 0.0068(4) 0.6239(4) 0.8211(3) 0.0266(7) Uani 1 1 d . . . . .
C20 C 0.3860(4) 0.7808(4) 0.7808(3) 0.0282(8) Uani 1 1 d . . . . .
C3 C 0.2569(4) 0.5486(4) 0.8074(3) 0.0255(7) Uani 1 1 d . . . . .
H3 H 0.276046 0.581299 0.878834 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4202(4) 0.1687(4) 0.6113(3) 0.0261(7) Uani 1 1 d . . . . .
H10 H 0.446629 0.078867 0.641558 0.031 Uiso 1 1 calc R U . . .
C1 C 0.4026(4) 0.3247(4) 0.8468(2) 0.0261(7) Uani 1 1 d . . . . .
C9 C 0.3640(4) 0.1784(4) 0.5084(3) 0.0287(7) Uani 1 1 d . . . . .
C12 C 0.4911(4) 0.2870(4) 0.7816(3) 0.0263(7) Uani 1 1 d . . . . .
C28 C 0.7508(4) 0.2667(4) 0.6849(3) 0.0293(8) Uani 1 1 d . . . . .
H28 H 0.695865 0.347187 0.662101 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4368(3) 0.2978(4) 0.6696(2) 0.0242(7) Uani 1 1 d . . . . .
C4 C 0.3563(4) 0.6239(4) 0.7524(3) 0.0261(7) Uani 1 1 d . . . . .
C13 C 0.1099(4) 0.5931(4) 0.7574(3) 0.0280(7) Uani 1 1 d . . . . .
C6 C 0.3958(3) 0.4322(4) 0.6213(3) 0.0258(7) Uani 1 1 d . . . . .
C5 C 0.4093(4) 0.5749(4) 0.6748(3) 0.0267(7) Uani 1 1 d . . . . .
H5 H 0.464257 0.642172 0.649926 0.032 Uiso 1 1 calc R U . . .
C23 C 0.7258(4) 0.1851(4) 0.7678(3) 0.0281(7) Uani 1 1 d . . . . .
C27 C 0.8551(4) 0.2298(5) 0.6369(3) 0.0345(8) Uani 1 1 d . . . . .
H27 H 0.872563 0.288696 0.584355 0.041 Uiso 1 1 calc R U . . .
C15 C -0.1306(4) 0.6146(4) 0.7749(3) 0.0335(8) Uani 1 1 d . . . . .
H15 H -0.155466 0.583784 0.707286 0.040 Uiso 1 1 calc R U . . .
C19 C 0.0439(4) 0.6674(5) 0.9235(3) 0.0367(9) Uani 1 1 d . . . . .
H19 H 0.135888 0.671582 0.956099 0.044 Uiso 1 1 calc R U . . .
C2 C 0.2601(4) 0.3797(4) 0.8059(3) 0.0264(7) Uani 1 1 d . . . . .
H2A H 0.198635 0.341501 0.847074 0.032 Uiso 1 1 calc R U . . .
H2B H 0.228623 0.345204 0.736264 0.032 Uiso 1 1 calc R U . . .
C8 C 0.3268(4) 0.3081(4) 0.4584(3) 0.0312(8) Uani 1 1 d . . . . .
H8 H 0.290979 0.310505 0.388346 0.037 Uiso 1 1 calc R U . . .
C25 C 0.9109(4) 0.0238(4) 0.7483(3) 0.0368(9) Uani 1 1 d . . . . .
H25 H 0.964183 -0.058386 0.769573 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9356(4) 0.1054(4) 0.6654(3) 0.0348(9) Uani 1 1 d . . . . .
C7 C 0.3443(4) 0.4342(4) 0.5158(3) 0.0308(8) Uani 1 1 d . . . . .
H7 H 0.321207 0.523318 0.483306 0.037 Uiso 1 1 calc R U . . .
C24 C 0.8091(4) 0.0629(4) 0.7992(3) 0.0326(8) Uani 1 1 d . . . . .
H24 H 0.795523 0.007745 0.854777 0.039 Uiso 1 1 calc R U . . .
C17 C -0.1946(4) 0.6957(5) 0.9284(3) 0.0404(10) Uani 1 1 d . . . . .
H17 H -0.261956 0.720433 0.964241 0.049 Uiso 1 1 calc R U . . .
C16 C -0.2315(4) 0.6504(5) 0.8275(3) 0.0416(10) Uani 1 1 d . . . . .
H16 H -0.323559 0.644128 0.795359 0.050 Uiso 1 1 calc R U . . .
C18 C -0.0572(4) 0.7040(6) 0.9757(3) 0.0432(10) Uani 1 1 d . . . . .
H18 H -0.032786 0.734655 1.043465 0.052 Uiso 1 1 calc R U . . .
C21 C 0.3212(5) 0.9794(4) 0.8732(3) 0.0399(9) Uani 1 1 d . . . . .
H21A H 0.293786 1.040858 0.814230 0.060 Uiso 1 1 calc R U . . .
H21B H 0.415709 0.997696 0.903740 0.060 Uiso 1 1 calc R U . . .
H21C H 0.265234 1.000136 0.921858 0.060 Uiso 1 1 calc R U . . .
C29 C 1.0431(4) 0.0596(6) 0.6081(4) 0.0481(11) Uani 1 1 d . . . . .
H29A H 1.000196 0.036338 0.538754 0.072 Uiso 1 1 calc R U . . .
H29B H 1.090524 -0.024889 0.640331 0.072 Uiso 1 1 calc R U . . .
H29C H 1.107249 0.137955 0.608530 0.072 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
F1 C9 1.365(4) . ?
O1 H1 0.8200 . ?
O1 C1 1.296(4) . ?
O5 C22 1.311(4) . ?
O3 C20 1.342(4) . ?
O3 C21 1.445(5) . ?
O4 C20 1.205(4) . ?
O2 C13 1.218(4) . ?
C22 C12 1.404(5) . ?
C22 C23 1.474(5) . ?
C14 C13 1.490(5) . ?
C14 C15 1.382(5) . ?
C14 C19 1.399(5) . ?
C20 C4 1.499(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.517(5) . ?
C3 C13 1.533(5) . ?
C3 C2 1.546(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.375(5) . ?
C10 C11 1.406(5) . ?
C1 C12 1.406(5) . ?
C1 C2 1.497(5) . ?
C9 C8 1.374(5) . ?
C12 C11 1.484(5) . ?
C28 H28 0.9300 . ?
C28 C23 1.400(5) . ?
C28 C27 1.372(5) . ?
C11 C6 1.409(5) . ?
C4 C5 1.334(5) . ?
C6 C5 1.482(5) . ?
C6 C7 1.397(5) . ?
C5 H5 0.9300 . ?
C23 C24 1.404(5) . ?
C27 H27 0.9300 . ?
C27 C26 1.399(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(6) . ?
C19 H19 0.9300 . ?
C19 C18 1.381(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C7 1.376(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.399(6) . ?
C25 C24 1.381(6) . ?
C26 C29 1.500(5) . ?
C7 H7 0.9300 . ?
C24 H24 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.385(6) . ?
C17 C18 1.386(6) . ?
C16 H16 0.9300 . ?
C18 H18 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C1 O1 H1 109.5 . . ?
C20 O3 C21 115.7(3) . . ?
O5 C22 C12 119.6(3) . . ?
O5 C22 C23 114.8(3) . . ?
C12 C22 C23 125.6(3) . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 C19 119.3(3) . . ?
C19 C14 C13 122.6(3) . . ?
O3 C20 C4 110.5(3) . . ?
O4 C20 O3 123.4(3) . . ?
O4 C20 C4 126.0(3) . . ?
C4 C3 H3 108.6 . . ?
C4 C3 C13 109.2(3) . . ?
C4 C3 C2 115.5(3) . . ?
C13 C3 H3 108.6 . . ?
C13 C3 C2 106.3(3) . . ?
C2 C3 H3 108.6 . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.5(3) . . ?
C11 C10 H10 120.8 . . ?
O1 C1 C12 122.2(3) . . ?
O1 C1 C2 116.1(3) . . ?
C12 C1 C2 121.7(3) . . ?
F1 C9 C10 117.6(3) . . ?
F1 C9 C8 118.8(3) . . ?
C8 C9 C10 123.7(3) . . ?
C22 C12 C1 118.7(3) . . ?
C22 C12 C11 123.4(3) . . ?
C1 C12 C11 117.7(3) . . ?
C23 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C27 C28 C23 121.0(3) . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 C6 119.3(3) . . ?
C6 C11 C12 122.0(3) . . ?
C20 C4 C3 115.2(3) . . ?
C5 C4 C20 115.5(3) . . ?
C5 C4 C3 128.9(3) . . ?
O2 C13 C14 120.0(3) . . ?
O2 C13 C3 119.2(3) . . ?
C14 C13 C3 120.7(3) . . ?
C11 C6 C5 124.0(3) . . ?
C7 C6 C11 119.0(3) . . ?
C7 C6 C5 116.9(3) . . ?
C4 C5 C6 131.3(3) . . ?
C4 C5 H5 114.3 . . ?
C6 C5 H5 114.3 . . ?
C28 C23 C22 121.8(3) . . ?
C28 C23 C24 118.1(3) . . ?
C24 C23 C22 120.0(3) . . ?
C28 C27 H27 119.3 . . ?
C28 C27 C26 121.4(4) . . ?
C26 C27 H27 119.3 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(4) . . ?
C16 C15 H15 119.4 . . ?
C14 C19 H19 120.3 . . ?
C18 C19 C14 119.4(4) . . ?
C18 C19 H19 120.3 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 C3 110.6(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C9 C8 H8 121.2 . . ?
C9 C8 C7 117.6(3) . . ?
C7 C8 H8 121.2 . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.3(4) . . ?
C27 C26 C29 121.2(4) . . ?
C25 C26 C27 117.7(3) . . ?
C25 C26 C29 121.1(4) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 H7 119.0 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.5(4) . . ?
C25 C24 H24 119.7 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C15 C16 C17 119.5(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
F1 C9 C8 C7 178.1(3) . . . . ?
O1 C1 C12 C22 3.1(5) . . . . ?
O1 C1 C12 C11 177.2(3) . . . . ?
O1 C1 C2 C3 84.2(4) . . . . ?
O5 C22 C12 C1 1.4(5) . . . . ?
O5 C22 C12 C11 -172.4(3) . . . . ?
O5 C22 C23 C28 -141.5(4) . . . . ?
O5 C22 C23 C24 35.4(5) . . . . ?
O3 C20 C4 C3 -7.0(4) . . . . ?
O3 C20 C4 C5 166.2(3) . . . . ?
O4 C20 C4 C3 174.0(3) . . . . ?
O4 C20 C4 C5 -12.8(5) . . . . ?
C22 C12 C11 C10 60.2(5) . . . . ?
C22 C12 C11 C6 -122.8(4) . . . . ?
C22 C23 C24 C25 -178.0(4) . . . . ?
C14 C15 C16 C17 -0.3(6) . . . . ?
C14 C19 C18 C17 1.1(7) . . . . ?
C20 C4 C5 C6 -175.8(3) . . . . ?
C3 C4 C5 C6 -3.7(6) . . . . ?
C10 C9 C8 C7 -1.5(6) . . . . ?
C10 C11 C6 C5 -179.5(3) . . . . ?
C10 C11 C6 C7 -2.4(5) . . . . ?
C1 C12 C11 C10 -113.6(4) . . . . ?
C1 C12 C11 C6 63.4(4) . . . . ?
C9 C10 C11 C12 177.1(3) . . . . ?
C9 C10 C11 C6 0.0(5) . . . . ?
C9 C8 C7 C6 -1.1(5) . . . . ?
C12 C22 C23 C28 39.0(6) . . . . ?
C12 C22 C23 C24 -144.1(4) . . . . ?
C12 C1 C2 C3 -96.3(4) . . . . ?
C12 C11 C6 C5 3.5(5) . . . . ?
C12 C11 C6 C7 -179.4(3) . . . . ?
C28 C23 C24 C25 -1.0(5) . . . . ?
C28 C27 C26 C25 -3.3(6) . . . . ?
C28 C27 C26 C29 175.7(4) . . . . ?
C11 C10 C9 F1 -177.5(3) . . . . ?
C11 C10 C9 C8 2.1(5) . . . . ?
C11 C6 C5 C4 -60.3(5) . . . . ?
C11 C6 C7 C8 3.0(5) . . . . ?
C4 C3 C13 O2 43.0(4) . . . . ?
C4 C3 C13 C14 -139.8(3) . . . . ?
C4 C3 C2 C1 54.9(4) . . . . ?
C13 C14 C15 C16 -176.0(4) . . . . ?
C13 C14 C19 C18 175.4(4) . . . . ?
C13 C3 C4 C20 78.9(4) . . . . ?
C13 C3 C4 C5 -93.1(4) . . . . ?
C13 C3 C2 C1 176.1(3) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C23 C22 C12 C1 -179.2(3) . . . . ?
C23 C22 C12 C11 7.1(6) . . . . ?
C23 C28 C27 C26 3.3(6) . . . . ?
C27 C28 C23 C22 175.9(3) . . . . ?
C27 C28 C23 C24 -1.1(5) . . . . ?
C15 C14 C13 O2 18.7(5) . . . . ?
C15 C14 C13 C3 -158.5(3) . . . . ?
C15 C14 C19 C18 -1.7(6) . . . . ?
C19 C14 C13 O2 -158.5(4) . . . . ?
C19 C14 C13 C3 24.3(5) . . . . ?
C19 C14 C15 C16 1.3(6) . . . . ?
C2 C3 C4 C20 -161.4(3) . . . . ?
C2 C3 C4 C5 26.5(5) . . . . ?
C2 C3 C13 O2 -82.2(4) . . . . ?
C2 C3 C13 C14 95.0(4) . . . . ?
C2 C1 C12 C22 -176.4(3) . . . . ?
C2 C1 C12 C11 -2.3(5) . . . . ?
C26 C25 C24 C23 1.0(6) . . . . ?
C7 C6 C5 C4 122.5(4) . . . . ?
C24 C25 C26 C27 1.1(6) . . . . ?
C24 C25 C26 C29 -177.8(4) . . . . ?
C16 C17 C18 C19 -0.1(7) . . . . ?
C18 C17 C16 C15 -0.3(7) . . . . ?
C21 O3 C20 O4 0.5(5) . . . . ?
C21 O3 C20 C4 -178.5(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.654
_oxdiff_exptl_absorpt_empirical_full_min 0.732
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7(3)
2 0.3(3)
####################################################################### 
# 
# 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_hpd207
_database_code_depnum_ccdc_archive 'CCDC 2024481'
loop_
_audit_author_name
_audit_author_address
haifeng
;The Cambridge Crystallographic Data Centre 
United States of America
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_audit_creation_date             2020-08-20
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 F O2'
_chemical_formula_sum            'C15 H15 F O2'
_chemical_formula_weight         246.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O F Si'
_chemical_oxdiff_usercomment     HF_08_17
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3867(2)
_cell_length_b                   19.0785(5)
_cell_length_c                   9.3357(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.972(3)
_cell_angle_gamma                90
_cell_volume                     1220.09(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6160
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7310
_cell_measurement_theta_min      2.4110
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 6 3 0.0268
0 2 -6 0.1152
4 -7 -3 0.0418
1 -3 5 0.0553
1 11 1 0.0142
4 2 -4 0.0509
-1 -11 -2 0.0645
-4 0 5 0.0268

_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.072
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.9525 6.4742 3.0870 0.1014 0.4150 0.9042
-0.0337 1.7927 -5.5432 0.1953 0.8165 -0.5434
3.9682 -6.5546 -2.9237 -0.1079 -0.4422 -0.8904
0.6191 -2.7670 5.1351 -0.2121 -0.8851 0.4143
1.1592 11.2372 1.3894 0.8969 -0.2164 0.3857
4.2532 2.1259 -4.4206 0.5652 -0.1344 -0.8139
-0.6995 -11.2103 -1.9165 -0.8500 0.2053 -0.4852
-4.1285 0.0694 4.8101 -0.3999 0.0945 0.9117

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13853
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.263
_diffrn_reflns_theta_min         4.635
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00  26.00   0.50    0.11    --  -46.62  93.00-110.00  208
  2  ω    -13.00  78.00   0.50    0.11    --   46.62 -93.00 137.00  182
  3  ω    -80.00 -15.00   0.50    0.44    --  -88.50  93.00-110.00  130
  4  ω     34.00 105.00   0.50    0.44    --  106.69 -93.00 137.00  142
  5  ω    104.00 178.00   0.50    0.44    --  106.69  93.00-110.00  148
  6  ω   -119.00 -87.00   0.50    0.11    --  -46.62-125.00 -60.00   64
  7  ω   -119.00 -83.00   0.50    0.11    --  -46.62 -57.00-180.00   72
  8  ω   -119.00 -83.00   0.50    0.11    --  -46.62 -57.00-120.00   72
  9  ω   -119.00 -83.00   0.50    0.11    --  -46.62 -57.00 150.00   72
 10  ω   -119.00 -87.00   0.50    0.11    --  -46.62-125.00-150.00   64
 11  ω     83.00 120.00   0.50    0.11    --   46.62  57.00  30.00   74
 12  ω    -51.00 -16.00   0.50    0.44    --  -88.50  45.00-180.00   70
 13  ω    -71.00 -15.00   0.50    0.44    --  -88.50  61.00  30.00  112
 14  ω    -51.00 -16.00   0.50    0.44    --  -88.50  45.00-120.00   70
 15  ω    -51.00 -16.00   0.50    0.44    --  -88.50  45.00 -60.00   70
 16  ω   -160.00-101.00   0.50    0.44    --  -88.50 -77.00 -90.00  118
 17  ω    -51.00 -16.00   0.50    0.44    --  -88.50  45.00  90.00   70
 18  ω   -160.00 -83.00   0.50    0.44    --  -88.50 -93.00 137.00  154
 19  ω     34.00 101.00   0.50    0.44    --  106.69 -77.00-180.00  134
 20  ω     34.00  71.00   0.50    0.44    --  106.69 -61.00 -90.00   74
 21  ω     34.00  71.00   0.50    0.44    --  106.69 -61.00-180.00   74
 22  ω    101.00 178.00   0.50    0.44    --  106.69  77.00 -60.00  154
 23  ω     34.00  71.00   0.50    0.44    --  106.69 -61.00-150.00   74
 24  ω     34.00  71.00   0.50    0.44    --  106.69 -61.00 -30.00   74
 25  ω     34.00 105.00   0.50    0.44    --  106.69 -94.00  30.00  142
 26  ω   -120.00 -32.00   0.50    0.11    --  -46.62 -37.00 -90.00  176
 27  ω   -120.00 -32.00   0.50    0.11    --  -46.62 -37.00-180.00  176
 28  ω   -120.00 -32.00   0.50    0.11    --  -46.62 -37.00  90.00  176
 29  ω   -120.00 -32.00   0.50    0.11    --  -46.62 -37.00   0.00  176
 30  ω   -120.00 -52.00   0.50    0.11    --  -46.62 -37.00-150.00  136
 31  ω     83.00 120.00   0.50    0.11    --   46.62  57.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0838337000
_diffrn_orient_matrix_UB_12      0.0726802000
_diffrn_orient_matrix_UB_13      -0.0122402000
_diffrn_orient_matrix_UB_21      -0.1863442000
_diffrn_orient_matrix_UB_22      0.0173456000
_diffrn_orient_matrix_UB_23      -0.1405486000
_diffrn_orient_matrix_UB_31      -0.0939081000
_diffrn_orient_matrix_UB_32      0.0305977000
_diffrn_orient_matrix_UB_33      0.1084869000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2122
_reflns_number_total             2429
_reflns_odcompleteness_completeness 99.96
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.091
_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)+(0.0550P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1096
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C8(H8), C15(H15)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.66202(11) 0.34646(4) 0.92199(8) 0.0291(2) Uani 1 1 d . . . . .
O1 O -0.04657(14) 0.43209(5) 0.16331(9) 0.0264(2) Uani 1 1 d . . . . .
H1 H -0.054882 0.388308 0.153584 0.040 Uiso 1 1 calc R U . . .
O2 O 0.03381(14) 0.30394(5) 0.23589(10) 0.0300(3) Uani 1 1 d . . . . .
C9 C 0.32092(17) 0.41689(6) 0.56024(13) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.08159(18) 0.44842(7) 0.30463(13) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.55470(19) 0.39354(7) 0.81352(14) 0.0228(3) Uani 1 1 d . . . . .
C4 C 0.34071(17) 0.48933(7) 0.59719(13) 0.0203(3) Uani 1 1 d . . . . .
C6 C 0.57667(18) 0.46428(7) 0.85404(14) 0.0232(3) Uani 1 1 d . . . . .
H6 H 0.662591 0.479116 0.953377 0.028 Uiso 1 1 calc R U . . .
C10 C 0.18532(18) 0.39645(6) 0.40934(13) 0.0204(3) Uani 1 1 d . . . . .
C5 C 0.46915(18) 0.51154(7) 0.74461(14) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.481240 0.560156 0.768359 0.027 Uiso 1 1 calc R U . . .
C2 C 0.10371(18) 0.52125(7) 0.34087(14) 0.0207(3) Uani 1 1 d . . . . .
C11 C -0.01323(19) 0.57341(7) 0.21979(14) 0.0226(3) Uani 1 1 d . . . . .
H11A H -0.153475 0.561979 0.188774 0.027 Uiso 1 1 calc R U . . .
H11B H 0.020942 0.567600 0.127556 0.027 Uiso 1 1 calc R U . . .
C3 C 0.23041(18) 0.53919(6) 0.48478(14) 0.0213(3) Uani 1 1 d . . . . .
H3 H 0.246014 0.587467 0.511553 0.026 Uiso 1 1 calc R U . . .
C8 C 0.43414(18) 0.36850(7) 0.67353(14) 0.0216(3) Uani 1 1 d . . . . .
H8 H 0.426198 0.319648 0.652369 0.026 Uiso 1 1 calc R U . . .
C12 C 0.01651(19) 0.65008(7) 0.26929(14) 0.0239(3) Uani 1 1 d . . . . .
H12A H -0.018133 0.656489 0.361155 0.029 Uiso 1 1 calc R U . . .
H12B H 0.156188 0.662193 0.299298 0.029 Uiso 1 1 calc R U . . .
C15 C 0.14921(19) 0.32391(7) 0.36365(14) 0.0247(3) Uani 1 1 d . . . . .
H15 H 0.218576 0.289177 0.436409 0.030 Uiso 1 1 calc R U . . .
C13 C -0.1058(2) 0.69988(7) 0.14242(16) 0.0311(3) Uani 1 1 d . . . . .
H13A H -0.061091 0.697494 0.054903 0.037 Uiso 1 1 calc R U . . .
H13B H -0.243963 0.684772 0.104343 0.037 Uiso 1 1 calc R U . . .
C14 C -0.0911(3) 0.77508(8) 0.1993(2) 0.0420(4) Uani 1 1 d . . . . .
H14A H -0.166002 0.805760 0.113319 0.063 Uiso 1 1 calc R U . . .
H14B H 0.046034 0.789721 0.240154 0.063 Uiso 1 1 calc R U . . .
H14C H -0.143858 0.778263 0.281006 0.063 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
F1 C7 1.3639(14) . ?
O1 H1 0.8400 . ?
O1 C1 1.3414(14) . ?
O2 C15 1.2384(15) . ?
C9 C4 1.4187(17) . ?
C9 C10 1.4436(16) . ?
C9 C8 1.4172(17) . ?
C1 C10 1.4019(17) . ?
C1 C2 1.4250(18) . ?
C7 C6 1.3946(19) . ?
C7 C8 1.3632(17) . ?
C4 C5 1.4131(17) . ?
C4 C3 1.4249(17) . ?
C6 H6 0.9500 . ?
C6 C5 1.3713(18) . ?
C10 C15 1.4434(18) . ?
C5 H5 0.9500 . ?
C2 C11 1.5112(17) . ?
C2 C3 1.3628(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5249(18) . ?
C3 H3 0.9500 . ?
C8 H8 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5234(17) . ?
C15 H15 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.520(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C4 C9 C10 118.11(11) . . ?
C8 C9 C4 118.34(11) . . ?
C8 C9 C10 123.54(11) . . ?
O1 C1 C10 121.47(11) . . ?
O1 C1 C2 115.85(11) . . ?
C10 C1 C2 122.68(11) . . ?
F1 C7 C6 117.36(11) . . ?
C8 C7 F1 118.08(12) . . ?
C8 C7 C6 124.56(12) . . ?
C9 C4 C3 119.52(11) . . ?
C5 C4 C9 119.97(11) . . ?
C5 C4 C3 120.50(12) . . ?
C7 C6 H6 121.4 . . ?
C5 C6 C7 117.26(11) . . ?
C5 C6 H6 121.4 . . ?
C1 C10 C9 119.21(11) . . ?
C1 C10 C15 118.67(11) . . ?
C15 C10 C9 122.10(11) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.27(12) . . ?
C6 C5 H5 119.4 . . ?
C1 C2 C11 118.81(11) . . ?
C3 C2 C1 117.03(11) . . ?
C3 C2 C11 124.16(12) . . ?
C2 C11 H11A 108.4 . . ?
C2 C11 H11B 108.4 . . ?
C2 C11 C12 115.33(10) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C4 C3 H3 118.3 . . ?
C2 C3 C4 123.43(12) . . ?
C2 C3 H3 118.3 . . ?
C9 C8 H8 120.7 . . ?
C7 C8 C9 118.60(12) . . ?
C7 C8 H8 120.7 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 112.72(11) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
O2 C15 C10 124.34(12) . . ?
O2 C15 H15 117.8 . . ?
C10 C15 H15 117.8 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 111.91(12) . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
F1 C7 C6 C5 179.77(11) . . . . ?
F1 C7 C8 C9 179.59(10) . . . . ?
O1 C1 C10 C9 -179.74(11) . . . . ?
O1 C1 C10 C15 -1.21(18) . . . . ?
O1 C1 C2 C11 -0.96(17) . . . . ?
O1 C1 C2 C3 178.83(11) . . . . ?
C9 C4 C5 C6 0.12(19) . . . . ?
C9 C4 C3 C2 0.23(19) . . . . ?
C9 C10 C15 O2 179.69(12) . . . . ?
C1 C10 C15 O2 1.2(2) . . . . ?
C1 C2 C11 C12 178.91(11) . . . . ?
C1 C2 C3 C4 0.73(19) . . . . ?
C7 C6 C5 C4 0.32(19) . . . . ?
C4 C9 C10 C1 1.13(17) . . . . ?
C4 C9 C10 C15 -177.34(11) . . . . ?
C4 C9 C8 C7 0.95(18) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C10 C9 C4 C5 178.85(11) . . . . ?
C10 C9 C4 C3 -1.16(17) . . . . ?
C10 C9 C8 C7 -178.63(11) . . . . ?
C10 C1 C2 C11 179.46(11) . . . . ?
C10 C1 C2 C3 -0.75(19) . . . . ?
C5 C4 C3 C2 -179.78(12) . . . . ?
C2 C1 C10 C9 -0.18(19) . . . . ?
C2 C1 C10 C15 178.35(11) . . . . ?
C2 C11 C12 C13 -179.82(11) . . . . ?
C11 C2 C3 C4 -179.50(12) . . . . ?
C11 C12 C13 C14 173.81(12) . . . . ?
C3 C4 C5 C6 -179.87(12) . . . . ?
C3 C2 C11 C12 -0.87(19) . . . . ?
C8 C9 C4 C5 -0.76(18) . . . . ?
C8 C9 C4 C3 179.24(11) . . . . ?
C8 C9 C10 C1 -179.29(11) . . . . ?
C8 C9 C10 C15 2.24(19) . . . . ?
C8 C7 C6 C5 -0.1(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.789
####################################################################### 
# 
# 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_hpd195
_database_code_depnum_ccdc_archive 'CCDC 2024482'
loop_
_audit_author_name
_audit_author_address
haifeng
;The Cambridge Crystallographic Data Centre 
United States of America
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_audit_creation_date             2020-08-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H20 F N O4'
_chemical_formula_sum            'C28 H20 F N O4'
_chemical_formula_weight         453.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     hf-08-07
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.28538(14)
_cell_length_b                   20.3181(2)
_cell_length_c                   8.91344(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.0372(11)
_cell_angle_gamma                90
_cell_volume                     2197.31(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11498
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.0240
_cell_measurement_theta_min      3.6450
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.756
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.437
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             944
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -6 -5 0.0532
2 11 2 0.0735
0 -8 5 0.1053
-8 -1 0 0.0462
-2 10 4 0.0879
8 2 0 0.0042

_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.058
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.1932 -6.1946 -4.8396 0.0905 -0.3119 0.9458
1.5576 11.4141 2.4647 0.0714 -0.2352 -0.9693
-0.4332 -7.7801 4.6468 -0.2822 0.9544 -0.0976
-7.8244 -1.1410 -0.0988 -0.8963 -0.2645 0.3560
-1.7681 9.7538 3.8401 -0.3792 -0.1139 -0.9183
7.6626 2.0246 0.4467 0.8617 0.2541 -0.4392

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21382
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.713
_diffrn_reflns_theta_min         3.643
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00 120.00   0.50    0.05    --   46.87  58.00 -18.00  178
  2  ω     90.00 178.00   0.50    0.14    --  106.69  58.00 -18.00  176
  3  ω    101.00 178.00   0.50    0.14    --  106.69  77.00  30.00  154
  4  ω     95.00 178.00   0.50    0.14    --  106.69 125.00 150.00  166
  5  ω     96.00 177.00   0.50    0.14    --  106.69  61.00  60.00  162
  6  ω     56.00  87.00   0.50    0.14    --  106.69 -77.00-180.00   62
  7  ω     34.00  67.00   0.50    0.14    --  106.69 -58.00-159.00   66
  8  ω     40.00  65.00   0.50    0.14    --  106.69 -61.00 -90.00   50
  9  ω     34.00  71.00   0.50    0.14    --  106.69 -61.00 -30.00   74
 10  ω     46.00  95.00   0.50    0.14    --  106.69 -94.00   0.00   98
 11  ω     43.00  71.00   0.50    0.14    --  106.69 -61.00  60.00   56
 12  ω     45.00  71.00   0.50    0.14    --  106.69 -61.00  90.00   52
 13  ω     34.00  71.00   0.50    0.14    --  106.69 -61.00  30.00   74
 14  ω     35.00  62.00   0.50    0.14    --  106.69 -61.00   0.00   54
 15  ω     34.00 105.00   0.50    0.14    --  106.69 -94.00 -60.00  142
 16  ω    -25.00  63.00   0.50    0.05    --   46.87 -58.00-159.00  176
 17  ω    -63.00  26.00   0.50    0.05    --  -46.87  58.00 -18.00  178
 18  ω    -51.00 -16.00   0.50    0.14    --  -88.50  45.00 150.00   70
 19  ω    -51.00 -16.00   0.50    0.14    --  -88.50  45.00 120.00   70
 20  ω    -67.00 -15.00   0.50    0.14    --  -88.50  58.00 -18.00  104
 21  ω    -51.00 -16.00   0.50    0.14    --  -88.50  45.00 -90.00   70
 22  ω    -51.00 -16.00   0.50    0.14    --  -88.50  45.00-180.00   70
 23  ω   -120.00 -30.00   0.50    0.05    --  -46.87 -58.00-159.00  180
 24  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00  30.00   66
 25  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 -30.00   66
 26  ω   -160.00 -72.00   0.50    0.14    --  -88.50 -58.00-159.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1150120000
_diffrn_orient_matrix_UB_12      0.0009997000
_diffrn_orient_matrix_UB_13      -0.0483264000
_diffrn_orient_matrix_UB_21      0.0398951000
_diffrn_orient_matrix_UB_22      -0.0522985000
_diffrn_orient_matrix_UB_23      0.1215419000
_diffrn_orient_matrix_UB_31      -0.0360271000
_diffrn_orient_matrix_UB_32      -0.0548960000
_diffrn_orient_matrix_UB_33      -0.1162831000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4040
_reflns_number_total             4485
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.057
_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)+(0.0467P)²+0.6233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0947
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C12(H12), C24(H24), C5(H5), C25(H25), C16(H16), C13(H13),
 C19(H19), C26(H26), C27(H27), C28(H28), C11(H11), C18(H18)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.92234(7) 0.14659(4) 0.03859(9) 0.02137(19) Uani 1 1 d . . . . .
O3 O 0.86109(7) 0.18642(4) -0.19491(9) 0.02209(19) Uani 1 1 d . . . . .
F1 F 1.49686(6) -0.00150(4) -0.21268(9) 0.03269(19) Uani 1 1 d . . . . .
O4 O 0.91109(7) 0.16793(4) -0.53062(9) 0.0256(2) Uani 1 1 d . . . . .
N1 N 1.20726(8) 0.29177(5) -0.19998(12) 0.0224(2) Uani 1 1 d . . . . .
C7 C 1.04784(9) 0.14167(6) -0.31658(12) 0.0183(2) Uani 1 1 d . . . . .
H7 H 1.102872 0.108517 -0.340250 0.022 Uiso 1 1 calc R U . . .
C20 C 0.93035(9) 0.15778(5) -0.10724(12) 0.0173(2) Uani 1 1 d . . . . .
C6 C 1.03360(9) 0.13096(5) -0.15197(12) 0.0173(2) Uani 1 1 d . . . . .
C22 C 0.94161(10) 0.12961(6) -0.42797(13) 0.0197(2) Uani 1 1 d . . . . .
C8 C 1.09435(10) 0.20993(6) -0.34534(13) 0.0218(2) Uani 1 1 d . . . . .
H8A H 1.116203 0.210405 -0.447614 0.026 Uiso 1 1 calc R U . . .
H8B H 1.035569 0.243197 -0.344436 0.026 Uiso 1 1 calc R U . . .
C9 C 1.19183(9) 0.22893(6) -0.23034(13) 0.0191(2) Uani 1 1 d . . . . .
C15 C 1.50692(10) 0.28380(6) 0.09313(14) 0.0226(2) Uani 1 1 d . . . . .
H15 H 1.488819 0.323958 0.040493 0.027 Uiso 1 1 calc R U . . .
C14 C 1.60130(10) 0.27996(6) 0.20107(14) 0.0247(3) Uani 1 1 d . . . . .
H14 H 1.647627 0.317365 0.221705 0.030 Uiso 1 1 calc R U . . .
C12 C 1.55892(10) 0.16755(6) 0.25011(14) 0.0249(3) Uani 1 1 d . . . . .
H12 H 1.576566 0.127836 0.304793 0.030 Uiso 1 1 calc R U . . .
C23 C 0.87807(10) 0.06799(6) -0.41121(12) 0.0206(2) Uani 1 1 d . . . . .
C1 C 1.34043(9) 0.23363(6) -0.05658(13) 0.0195(2) Uani 1 1 d . . . . .
C10 C 1.43815(9) 0.22895(6) 0.06120(13) 0.0198(2) Uani 1 1 d . . . . .
C24 C 0.76421(11) 0.06964(6) -0.45651(15) 0.0271(3) Uani 1 1 d . . . . .
H24 H 0.729579 0.109293 -0.495102 0.033 Uiso 1 1 calc R U . . .
C5 C 1.10846(9) 0.10013(5) -0.05144(13) 0.0183(2) Uani 1 1 d . . . . .
H5 H 1.093246 0.094367 0.048992 0.022 Uiso 1 1 calc R U . . .
C2 C 1.27480(9) 0.18919(6) -0.14317(13) 0.0184(2) Uani 1 1 d . . . . .
C25 C 0.70129(12) 0.01381(7) -0.44558(17) 0.0350(3) Uani 1 1 d . . . . .
H25 H 0.623467 0.015613 -0.473396 0.042 Uiso 1 1 calc R U . . .
C16 C 1.38579(10) 0.09026(6) -0.18366(13) 0.0215(2) Uani 1 1 d . . . . .
H16 H 1.437482 0.117893 -0.221868 0.026 Uiso 1 1 calc R U . . .
C13 C 1.62814(10) 0.22159(6) 0.27890(14) 0.0249(3) Uani 1 1 d . . . . .
H13 H 1.693457 0.218635 0.351422 0.030 Uiso 1 1 calc R U . . .
C17 C 1.40421(10) 0.02380(6) -0.16844(15) 0.0242(3) Uani 1 1 d . . . . .
C19 C 1.23827(10) 0.00768(6) -0.06913(15) 0.0242(3) Uani 1 1 d . . . . .
H19 H 1.188720 -0.020377 -0.027712 0.029 Uiso 1 1 calc R U . . .
C26 C 0.75210(12) -0.04492(7) -0.39385(16) 0.0339(3) Uani 1 1 d . . . . .
H26 H 0.709041 -0.083410 -0.388133 0.041 Uiso 1 1 calc R U . . .
C27 C 0.86533(12) -0.04736(6) -0.35070(14) 0.0283(3) Uani 1 1 d . . . . .
H27 H 0.899964 -0.087729 -0.317343 0.034 Uiso 1 1 calc R U . . .
C28 C 0.92850(11) 0.00919(6) -0.35607(13) 0.0232(3) Uani 1 1 d . . . . .
H28 H 1.005762 0.007873 -0.322344 0.028 Uiso 1 1 calc R U . . .
O1 O 1.30243(7) 0.29539(4) -0.08900(10) 0.02319(19) Uani 1 1 d . . . . .
C11 C 1.46418(10) 0.17076(6) 0.14238(14) 0.0224(2) Uani 1 1 d . . . . .
H11 H 1.417256 0.133507 0.123999 0.027 Uiso 1 1 calc R U . . .
C21 C 0.82613(10) 0.17479(6) 0.08963(14) 0.0235(3) Uani 1 1 d . . . . .
H21A H 0.759376 0.158862 0.025037 0.035 Uiso 1 1 calc R U . . .
H21B H 0.829381 0.222887 0.083266 0.035 Uiso 1 1 calc R U . . .
H21C H 0.824578 0.161699 0.195091 0.035 Uiso 1 1 calc R U . . .
C18 C 1.33389(11) -0.01854(6) -0.10975(16) 0.0276(3) Uani 1 1 d . . . . .
H18 H 1.350307 -0.064093 -0.097516 0.033 Uiso 1 1 calc R U . . .
C3 C 1.28963(9) 0.11669(6) -0.14201(12) 0.0183(2) Uani 1 1 d . . . . .
C4 C 1.21366(9) 0.07452(6) -0.08808(12) 0.0189(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C20 1.3383(14) . ?
O2 C21 1.4496(13) . ?
O3 C20 1.2101(14) . ?
F1 C17 1.3625(13) . ?
O4 C22 1.2149(14) . ?
N1 C9 1.3128(16) . ?
N1 O1 1.4098(13) . ?
C7 H7 1.0000 . ?
C7 C6 1.5204(15) . ?
C7 C22 1.5303(15) . ?
C7 C8 1.5369(16) . ?
C20 C6 1.4913(15) . ?
C6 C5 1.3350(16) . ?
C22 C23 1.4953(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.4994(16) . ?
C9 C2 1.4303(16) . ?
C15 H15 0.9500 . ?
C15 C14 1.3877(17) . ?
C15 C10 1.4006(17) . ?
C14 H14 0.9500 . ?
C14 C13 1.3872(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.3878(18) . ?
C12 C11 1.3892(17) . ?
C23 C24 1.3941(17) . ?
C23 C28 1.3989(17) . ?
C1 C10 1.4685(16) . ?
C1 C2 1.3658(16) . ?
C1 O1 1.3542(14) . ?
C10 C11 1.3967(17) . ?
C24 H24 0.9500 . ?
C24 C25 1.3846(19) . ?
C5 H5 0.9500 . ?
C5 C4 1.4766(15) . ?
C2 C3 1.4841(16) . ?
C25 H25 0.9500 . ?
C25 C26 1.391(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3723(17) . ?
C16 C3 1.3998(16) . ?
C13 H13 0.9500 . ?
C17 C18 1.3791(18) . ?
C19 H19 0.9500 . ?
C19 C18 1.3886(17) . ?
C19 C4 1.3957(17) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.3916(18) . ?
C28 H28 0.9500 . ?
C11 H11 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C18 H18 0.9500 . ?
C3 C4 1.4063(16) . ?

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
C20 O2 C21 115.19(9) . . ?
C9 N1 O1 105.81(9) . . ?
C6 C7 H7 106.9 . . ?
C6 C7 C22 112.80(9) . . ?
C6 C7 C8 113.10(9) . . ?
C22 C7 H7 106.9 . . ?
C22 C7 C8 109.74(9) . . ?
C8 C7 H7 106.9 . . ?
O2 C20 C6 113.14(9) . . ?
O3 C20 O2 123.88(10) . . ?
O3 C20 C6 122.98(10) . . ?
C20 C6 C7 115.94(9) . . ?
C5 C6 C7 122.91(10) . . ?
C5 C6 C20 121.15(10) . . ?
O4 C22 C7 121.12(11) . . ?
O4 C22 C23 120.51(10) . . ?
C23 C22 C7 118.33(10) . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 C7 113.34(9) . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
N1 C9 C8 117.73(10) . . ?
N1 C9 C2 111.68(10) . . ?
C2 C9 C8 130.59(11) . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C10 120.52(11) . . ?
C10 C15 H15 119.7 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.13(12) . . ?
C13 C14 H14 119.9 . . ?
C13 C12 H12 119.6 . . ?
C13 C12 C11 120.87(12) . . ?
C11 C12 H12 119.6 . . ?
C24 C23 C22 117.83(11) . . ?
C24 C23 C28 119.41(11) . . ?
C28 C23 C22 122.74(11) . . ?
C2 C1 C10 134.82(11) . . ?
O1 C1 C10 115.36(10) . . ?
O1 C1 C2 109.81(10) . . ?
C15 C10 C1 119.54(11) . . ?
C11 C10 C15 119.12(11) . . ?
C11 C10 C1 121.34(11) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.39(12) . . ?
C25 C24 H24 119.8 . . ?
C6 C5 H5 118.3 . . ?
C6 C5 C4 123.47(10) . . ?
C4 C5 H5 118.3 . . ?
C9 C2 C3 129.81(10) . . ?
C1 C2 C9 103.94(10) . . ?
C1 C2 C3 126.25(10) . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 119.97(13) . . ?
C26 C25 H25 120.0 . . ?
C17 C16 H16 120.5 . . ?
C17 C16 C3 118.96(11) . . ?
C3 C16 H16 120.5 . . ?
C14 C13 C12 119.56(11) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
F1 C17 C16 118.35(11) . . ?
F1 C17 C18 118.43(11) . . ?
C16 C17 C18 123.22(11) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C4 121.18(11) . . ?
C4 C19 H19 119.4 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.10(12) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.15(12) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 H28 120.0 . . ?
C27 C28 C23 119.91(12) . . ?
C27 C28 H28 120.0 . . ?
C1 O1 N1 108.76(8) . . ?
C12 C11 C10 119.78(11) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C18 C19 117.75(11) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C16 C3 C2 119.13(10) . . ?
C16 C3 C4 119.33(10) . . ?
C4 C3 C2 121.32(10) . . ?
C19 C4 C5 119.78(10) . . ?
C19 C4 C3 119.44(10) . . ?
C3 C4 C5 120.78(10) . . ?

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
O2 C20 C6 C7 179.73(9) . . . . ?
O2 C20 C6 C5 -0.90(15) . . . . ?
O3 C20 C6 C7 0.05(16) . . . . ?
O3 C20 C6 C5 179.42(11) . . . . ?
F1 C17 C18 C19 -178.23(11) . . . . ?
O4 C22 C23 C24 -31.83(16) . . . . ?
O4 C22 C23 C28 146.53(12) . . . . ?
N1 C9 C2 C1 0.75(13) . . . . ?
N1 C9 C2 C3 -179.54(11) . . . . ?
C7 C6 C5 C4 1.37(18) . . . . ?
C7 C22 C23 C24 150.46(11) . . . . ?
C7 C22 C23 C28 -31.18(16) . . . . ?
C7 C8 C9 N1 -150.09(11) . . . . ?
C7 C8 C9 C2 29.66(17) . . . . ?
C20 C6 C5 C4 -177.96(10) . . . . ?
C6 C7 C22 O4 134.13(11) . . . . ?
C6 C7 C22 C23 -48.17(13) . . . . ?
C6 C7 C8 C9 46.84(13) . . . . ?
C6 C5 C4 C19 -121.39(13) . . . . ?
C6 C5 C4 C3 58.60(16) . . . . ?
C22 C7 C6 C20 -42.41(13) . . . . ?
C22 C7 C6 C5 138.24(11) . . . . ?
C22 C7 C8 C9 173.75(9) . . . . ?
C22 C23 C24 C25 179.11(12) . . . . ?
C22 C23 C28 C27 -176.63(11) . . . . ?
C8 C7 C6 C20 82.87(12) . . . . ?
C8 C7 C6 C5 -96.49(13) . . . . ?
C8 C7 C22 O4 7.05(15) . . . . ?
C8 C7 C22 C23 -175.25(10) . . . . ?
C8 C9 C2 C1 -179.02(11) . . . . ?
C8 C9 C2 C3 0.7(2) . . . . ?
C9 N1 O1 C1 -0.21(12) . . . . ?
C9 C2 C3 C16 118.48(13) . . . . ?
C9 C2 C3 C4 -66.86(16) . . . . ?
C15 C14 C13 C12 -1.21(18) . . . . ?
C15 C10 C11 C12 -1.73(17) . . . . ?
C14 C15 C10 C1 -178.25(10) . . . . ?
C14 C15 C10 C11 1.72(17) . . . . ?
C23 C24 C25 C26 -2.1(2) . . . . ?
C1 C10 C11 C12 178.24(11) . . . . ?
C1 C2 C3 C16 -61.87(16) . . . . ?
C1 C2 C3 C4 112.79(13) . . . . ?
C10 C15 C14 C13 -0.25(17) . . . . ?
C10 C1 C2 C9 177.86(12) . . . . ?
C10 C1 C2 C3 -1.9(2) . . . . ?
C10 C1 O1 N1 -178.30(9) . . . . ?
C24 C23 C28 C27 1.71(17) . . . . ?
C24 C25 C26 C27 1.2(2) . . . . ?
C2 C1 C10 C15 159.25(13) . . . . ?
C2 C1 C10 C11 -20.7(2) . . . . ?
C2 C1 O1 N1 0.70(12) . . . . ?
C2 C3 C4 C5 8.87(16) . . . . ?
C2 C3 C4 C19 -171.14(10) . . . . ?
C25 C26 C27 C28 1.3(2) . . . . ?
C16 C17 C18 C19 2.2(2) . . . . ?
C16 C3 C4 C5 -176.48(10) . . . . ?
C16 C3 C4 C19 3.51(16) . . . . ?
C13 C12 C11 C10 0.29(18) . . . . ?
C17 C16 C3 C2 173.75(11) . . . . ?
C17 C16 C3 C4 -1.01(17) . . . . ?
C26 C27 C28 C23 -2.68(18) . . . . ?
C28 C23 C24 C25 0.69(19) . . . . ?
O1 N1 C9 C8 179.46(9) . . . . ?
O1 N1 C9 C2 -0.34(12) . . . . ?
O1 C1 C10 C15 -22.08(15) . . . . ?
O1 C1 C10 C11 157.95(10) . . . . ?
O1 C1 C2 C9 -0.86(12) . . . . ?
O1 C1 C2 C3 179.42(10) . . . . ?
C11 C12 C13 C14 1.19(18) . . . . ?
C21 O2 C20 O3 -3.46(16) . . . . ?
C21 O2 C20 C6 176.86(9) . . . . ?
C18 C19 C4 C5 176.72(11) . . . . ?
C18 C19 C4 C3 -3.26(18) . . . . ?
C3 C16 C17 F1 178.51(10) . . . . ?
C3 C16 C17 C18 -1.89(19) . . . . ?
C4 C19 C18 C17 0.47(19) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.852
