# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_prapd203a_2
_database_code_depnum_ccdc_archive 'CCDC 2173723'
loop_
_audit_author_name
_audit_author_address
'KAKOLI MAJI'
;INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA
India
;
_audit_update_record             
;
2022-05-19 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F N2 O, C3 H7'
_chemical_formula_sum            'C26 H26 F N2 O'
_chemical_formula_weight         401.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.1117(2)
_cell_length_b                   20.3860(3)
_cell_length_c                   9.62050(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.152(2)
_cell_angle_gamma                90
_cell_volume                     2082.34(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10887
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.1240
_cell_measurement_theta_min      4.1550
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0948
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15565
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.278
_diffrn_reflns_theta_min         4.164
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 109.00   0.50    0.29    --   41.33  43.00  30.00  168
  2  ω     70.00 165.00   0.50    1.15    --   96.67  77.00 -38.00  190
  3  ω     80.00 163.00   0.50    1.15    --   96.67  42.00 -60.00  166
  4  ω     83.00 164.00   0.50    1.15    --   96.67  33.00 -90.00  162
  5  ω     15.00 110.00   0.50    0.29    --   41.33  77.00 -38.00  190
  6  ω    -68.00  27.00   0.50    0.29    --  -41.33  77.00 -38.00  190
  7  ω    -24.00  35.00   0.50    0.29    --  -41.33  11.00-180.00  118
  8  ω    -28.00  30.00   0.50    0.29    --  -41.33  21.00 120.00  116
  9  ω     18.00  80.00   0.50    0.29    --   41.33-104.00  90.00  124
 10  ω     30.00 109.00   0.50    1.15    --   96.67-117.00 120.00  158
 11  ω     30.00 109.00   0.50    1.15    --   96.67-117.00  90.00  158
 12  ω     27.00 127.00   0.50    1.15    --   96.67 -87.00-180.00  200
 13  ω     28.00 105.00   0.50    1.15    --   96.67 -77.00-164.00  154
 14  ω     29.00  68.00   0.50    1.15    --   96.67 -59.00-120.00   78
 15  ω     29.00  83.00   0.50    1.15    --   96.67 -68.00 -60.00  108
 16  ω     30.00  57.00   0.50    1.15    --   96.67 -50.00 -90.00   54
 17  ω     30.00  57.00   0.50    1.15    --   96.67 -50.00-150.00   54
 18  ω     29.00  54.00   0.50    1.15    --   96.67 -59.00 -30.00   50
 19  ω     28.00 105.00   0.50    1.15    --   96.67 -77.00  90.00  154
 20  ω     29.00  68.00   0.50    1.15    --   96.67 -59.00 120.00   78
 21  ω   -110.00 -14.00   0.50    0.29    --  -41.33 -77.00-164.00  192
 22  ω   -149.00 -78.00   0.50    1.15    --  -82.50-117.00 -90.00  142
 23  ω   -151.00 -55.00   0.50    1.15    --  -82.50 -77.00-164.00  192
 24  ω    -47.00 -15.00   0.50    1.15    --  -82.50  42.00-150.00   64
 25  ω   -105.00 -14.00   0.50    1.15    --  -82.50  77.00 -38.00  182
 26  ω    -47.00 -15.00   0.50    1.15    --  -82.50  42.00 -30.00   64
 27  ω     81.00 164.00   0.50    1.15    --   96.67 145.00 -90.00  166
 28  ω     99.00 164.00   0.50    1.15    --   96.67 117.00 150.00  130
 29  ω    -30.00  28.00   0.50    0.29    --   41.33 -21.00   0.00  116
 30  ω    -27.00  68.00   0.50    0.29    --   41.33 -77.00-164.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3355
_reflns_number_total             3735
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.056
_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)+(0.0697P)²+0.6029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1278
_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:
 C14(H14), C17(H17), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C26(H26a,H26b), C25(H25a,H25b)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C12(H12), C2(H2), C9(H9), C20(H20), C3(H3), C19(H19), C22(H22),
 C23(H23), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C24(H24a,H24b,H24c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.10604(9) 0.16948(5) 0.69741(11) 0.0402(3) Uani 1 1 d . . . . .
O1 O 0.65243(11) 0.51775(5) 0.31402(11) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.67575(11) 0.54647(6) 0.60745(13) 0.0225(3) Uani 1 1 d . . . . .
N2 N 0.67158(13) 0.43937(6) 0.65255(13) 0.0270(3) Uani 1 1 d . . . . .
C15 C 0.60519(12) 0.34933(7) 0.40063(15) 0.0188(3) Uani 1 1 d . . . . .
H15 H 0.605859 0.348573 0.499588 0.023 Uiso 1 1 calc R U . . .
C6 C 0.62359(13) 0.40435(7) 0.33350(14) 0.0197(3) Uani 1 1 d . . . . .
C8 C 0.50057(14) 0.35982(7) 0.09703(15) 0.0218(3) Uani 1 1 d . . . . .
C13 C 0.47798(13) 0.30356(7) 0.16864(15) 0.0211(3) Uani 1 1 d . . . . .
C4 C 0.66297(13) 0.48427(7) 0.54951(15) 0.0209(3) Uani 1 1 d . . . . .
C18 C 0.81465(13) 0.25119(7) 0.37184(15) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.64638(13) 0.47180(7) 0.39382(15) 0.0202(3) Uani 1 1 d . . . . .
C14 C 0.58329(13) 0.28858(7) 0.30647(15) 0.0199(3) Uani 1 1 d . . . . .
H14 H 0.564375 0.249257 0.358561 0.024 Uiso 1 1 calc R U . . .
C17 C 0.70402(13) 0.27813(7) 0.25329(15) 0.0206(3) Uani 1 1 d . . . . .
H17 H 0.681487 0.244694 0.173745 0.025 Uiso 1 1 calc R U . . .
C12 C 0.37011(14) 0.26649(8) 0.11044(16) 0.0256(3) Uani 1 1 d . . . . .
H12 H 0.354535 0.228425 0.159432 0.031 Uiso 1 1 calc R U . . .
C2 C 0.69297(14) 0.53959(8) 0.75254(16) 0.0270(3) Uani 1 1 d . . . . .
H2 H 0.704649 0.573783 0.822353 0.032 Uiso 1 1 calc R U . . .
C7 C 0.62271(13) 0.39351(7) 0.17678(15) 0.0211(3) Uani 1 1 d . . . . .
H7 H 0.634827 0.435369 0.128387 0.025 Uiso 1 1 calc R U . . .
C16 C 0.73058(14) 0.34329(7) 0.18459(15) 0.0215(3) Uani 1 1 d . . . . .
H16A H 0.736538 0.334826 0.085503 0.026 Uiso 1 1 calc R U . . .
H16B H 0.811954 0.361742 0.243858 0.026 Uiso 1 1 calc R U . . .
C9 C 0.41650(15) 0.37875(8) -0.03445(16) 0.0266(3) Uani 1 1 d . . . . .
H9 H 0.432476 0.416496 -0.084171 0.032 Uiso 1 1 calc R U . . .
C20 C 0.94772(14) 0.15801(8) 0.47317(17) 0.0283(4) Uani 1 1 d . . . . .
H20 H 0.970870 0.113468 0.467305 0.034 Uiso 1 1 calc R U . . .
C3 C 0.69016(16) 0.47381(8) 0.77811(16) 0.0303(4) Uani 1 1 d . . . . .
H3 H 0.699854 0.454740 0.870874 0.036 Uiso 1 1 calc R U . . .
C19 C 0.84918(14) 0.18560(7) 0.36519(16) 0.0232(3) Uani 1 1 d . . . . .
H19 H 0.804226 0.159383 0.285051 0.028 Uiso 1 1 calc R U . . .
C1 C 0.67066(14) 0.60972(7) 0.53422(17) 0.0263(3) Uani 1 1 d . . . . .
H1A H 0.745196 0.614624 0.500434 0.039 Uiso 1 1 calc R U . . .
H1B H 0.668792 0.645165 0.602365 0.039 Uiso 1 1 calc R U . . .
H1C H 0.594579 0.611753 0.450794 0.039 Uiso 1 1 calc R U . . .
C22 C 0.98182(14) 0.26174(8) 0.59970(17) 0.0283(4) Uani 1 1 d . . . . .
H22 H 1.027865 0.287591 0.679947 0.034 Uiso 1 1 calc R U . . .
C21 C 1.01128(14) 0.19660(8) 0.58907(17) 0.0286(4) Uani 1 1 d . . . . .
C23 C 0.88342(14) 0.28861(8) 0.49053(16) 0.0258(3) Uani 1 1 d . . . . .
H23 H 0.862228 0.333457 0.496474 0.031 Uiso 1 1 calc R U . . .
C10 C 0.30789(15) 0.34131(8) -0.09247(16) 0.0305(4) Uani 1 1 d . . . . .
H10 H 0.249158 0.353991 -0.181958 0.037 Uiso 1 1 calc R U . . .
C11 C 0.28499(15) 0.28585(8) -0.02075(17) 0.0296(4) Uani 1 1 d . . . . .
H11 H 0.210727 0.260885 -0.061384 0.036 Uiso 1 1 calc R U . . .
C26 C 0.98453(16) 0.48569(8) 0.42400(18) 0.0317(4) Uani 1 1 d . . . . .
H26A H 0.912186 0.455391 0.409058 0.038 Uiso 1 1 calc R U . . .
H26B H 1.057487 0.459771 0.415848 0.038 Uiso 1 1 calc R U . . .
C25 C 0.95259(17) 0.53735(9) 0.30455(19) 0.0359(4) Uani 1 1 d . . . . .
H25A H 1.026967 0.565825 0.315353 0.043 Uiso 1 1 calc R U . . .
H25B H 0.883338 0.565201 0.316560 0.043 Uiso 1 1 calc R U . . .
C24 C 0.91288(19) 0.50778(9) 0.1508(2) 0.0430(5) Uani 1 1 d . . . . .
H24A H 0.885034 0.542911 0.078984 0.064 Uiso 1 1 calc R U . . .
H24B H 0.843653 0.476738 0.141852 0.064 Uiso 1 1 calc R U . . .
H24C H 0.984643 0.484809 0.133600 0.064 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 C21 1.3614(17) . ?
O1 C5 1.2254(18) . ?
N1 C4 1.3756(18) . ?
N1 C2 1.359(2) . ?
N1 C1 1.4623(19) . ?
N2 C4 1.3318(19) . ?
N2 C3 1.359(2) . ?
C15 H15 0.9500 . ?
C15 C6 1.340(2) . ?
C15 C14 1.5112(19) . ?
C6 C5 1.485(2) . ?
C6 C7 1.5210(19) . ?
C8 C13 1.398(2) . ?
C8 C7 1.513(2) . ?
C8 C9 1.387(2) . ?
C13 C14 1.5185(19) . ?
C13 C12 1.388(2) . ?
C4 C5 1.4762(19) . ?
C18 C17 1.512(2) . ?
C18 C19 1.398(2) . ?
C18 C23 1.398(2) . ?
C14 H14 1.0000 . ?
C14 C17 1.5847(19) . ?
C17 H17 1.0000 . ?
C17 C16 1.5503(19) . ?
C12 H12 0.9500 . ?
C12 C11 1.392(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.365(2) . ?
C7 H7 1.0000 . ?
C7 C16 1.5612(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C10 1.398(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.387(2) . ?
C20 C21 1.377(2) . ?
C3 H3 0.9500 . ?
C19 H19 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C21 1.379(2) . ?
C22 C23 1.386(2) . ?
C23 H23 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C26 C26 1.517(3) 3_766 ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C25 1.522(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C24 1.536(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C4 N1 C1 129.27(12) . . ?
C2 N1 C4 106.70(12) . . ?
C2 N1 C1 124.02(12) . . ?
C4 N2 C3 105.38(13) . . ?
C6 C15 H15 122.7 . . ?
C6 C15 C14 114.69(12) . . ?
C14 C15 H15 122.7 . . ?
C15 C6 C5 128.28(12) . . ?
C15 C6 C7 113.51(12) . . ?
C5 C6 C7 118.20(12) . . ?
C13 C8 C7 112.78(12) . . ?
C9 C8 C13 120.46(14) . . ?
C9 C8 C7 126.75(14) . . ?
C8 C13 C14 113.03(12) . . ?
C12 C13 C8 120.47(13) . . ?
C12 C13 C14 126.47(13) . . ?
N1 C4 C5 122.47(13) . . ?
N2 C4 N1 110.84(12) . . ?
N2 C4 C5 126.65(13) . . ?
C19 C18 C17 119.08(13) . . ?
C19 C18 C23 117.91(14) . . ?
C23 C18 C17 123.00(13) . . ?
O1 C5 C6 119.84(12) . . ?
O1 C5 C4 119.37(13) . . ?
C4 C5 C6 120.79(12) . . ?
C15 C14 C13 107.76(11) . . ?
C15 C14 H14 112.2 . . ?
C15 C14 C17 107.56(11) . . ?
C13 C14 H14 112.2 . . ?
C13 C14 C17 104.65(11) . . ?
C17 C14 H14 112.2 . . ?
C18 C17 C14 112.49(11) . . ?
C18 C17 H17 107.1 . . ?
C18 C17 C16 114.72(12) . . ?
C14 C17 H17 107.1 . . ?
C16 C17 C14 107.95(11) . . ?
C16 C17 H17 107.1 . . ?
C13 C12 H12 120.4 . . ?
C13 C12 C11 119.11(15) . . ?
C11 C12 H12 120.4 . . ?
N1 C2 H2 126.8 . . ?
N1 C2 C3 106.42(13) . . ?
C3 C2 H2 126.8 . . ?
C6 C7 H7 112.0 . . ?
C6 C7 C16 105.50(11) . . ?
C8 C7 C6 108.14(11) . . ?
C8 C7 H7 112.0 . . ?
C8 C7 C16 106.73(11) . . ?
C16 C7 H7 112.0 . . ?
C17 C16 C7 110.02(11) . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C7 C16 H16A 109.7 . . ?
C7 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.83(15) . . ?
C10 C9 H9 120.6 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C21 C20 C19 118.54(14) . . ?
N2 C3 C2 110.66(14) . . ?
N2 C3 H3 124.7 . . ?
C2 C3 H3 124.7 . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.36(14) . . ?
C20 C19 H19 119.3 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C21 C22 H22 120.8 . . ?
C21 C22 C23 118.42(15) . . ?
C23 C22 H22 120.8 . . ?
F1 C21 C20 118.95(15) . . ?
F1 C21 C22 118.77(15) . . ?
C20 C21 C22 122.28(14) . . ?
C18 C23 H23 119.3 . . ?
C22 C23 C18 121.48(14) . . ?
C22 C23 H23 119.3 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.67(14) . . ?
C11 C10 H10 119.7 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.45(15) . . ?
C10 C11 H11 119.8 . . ?
C26 C26 H26A 108.9 3_766 . ?
C26 C26 H26B 108.9 3_766 . ?
C26 C26 C25 113.44(17) 3_766 . ?
H26A C26 H26B 107.7 . . ?
C25 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C26 C25 C24 113.08(15) . . ?
H25A C25 H25B 107.8 . . ?
C24 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
N1 C4 C5 O1 5.0(2) . . . . ?
N1 C4 C5 C6 -175.51(12) . . . . ?
N1 C2 C3 N2 -0.01(19) . . . . ?
N2 C4 C5 O1 -172.82(14) . . . . ?
N2 C4 C5 C6 6.7(2) . . . . ?
C15 C6 C5 O1 -174.76(14) . . . . ?
C15 C6 C5 C4 5.8(2) . . . . ?
C15 C6 C7 C8 54.87(15) . . . . ?
C15 C6 C7 C16 -59.03(15) . . . . ?
C15 C14 C17 C18 75.46(14) . . . . ?
C15 C14 C17 C16 -52.12(14) . . . . ?
C6 C15 C14 C13 -52.32(15) . . . . ?
C6 C15 C14 C17 60.00(15) . . . . ?
C6 C7 C16 C17 60.69(14) . . . . ?
C8 C13 C14 C15 53.87(15) . . . . ?
C8 C13 C14 C17 -60.40(14) . . . . ?
C8 C13 C12 C11 0.4(2) . . . . ?
C8 C7 C16 C17 -54.19(14) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C13 C8 C7 C6 -51.94(15) . . . . ?
C13 C8 C7 C16 61.14(14) . . . . ?
C13 C8 C9 C10 1.2(2) . . . . ?
C13 C14 C17 C18 -170.13(11) . . . . ?
C13 C14 C17 C16 62.29(13) . . . . ?
C13 C12 C11 C10 0.2(2) . . . . ?
C4 N1 C2 C3 0.01(16) . . . . ?
C4 N2 C3 C2 0.01(18) . . . . ?
C18 C17 C16 C7 -132.19(12) . . . . ?
C5 C6 C7 C8 -126.29(13) . . . . ?
C5 C6 C7 C16 119.81(13) . . . . ?
C14 C15 C6 C5 179.43(13) . . . . ?
C14 C15 C6 C7 -1.87(17) . . . . ?
C14 C13 C12 C11 -177.34(13) . . . . ?
C14 C17 C16 C7 -5.90(15) . . . . ?
C17 C18 C19 C20 -178.23(13) . . . . ?
C17 C18 C23 C22 177.90(13) . . . . ?
C12 C13 C14 C15 -128.25(14) . . . . ?
C12 C13 C14 C17 117.48(15) . . . . ?
C2 N1 C4 N2 -0.01(16) . . . . ?
C2 N1 C4 C5 -178.14(13) . . . . ?
C7 C6 C5 O1 6.59(19) . . . . ?
C7 C6 C5 C4 -172.89(12) . . . . ?
C7 C8 C13 C14 -1.86(16) . . . . ?
C7 C8 C13 C12 -179.88(12) . . . . ?
C7 C8 C9 C10 179.79(13) . . . . ?
C9 C8 C13 C14 176.93(12) . . . . ?
C9 C8 C13 C12 -1.1(2) . . . . ?
C9 C8 C7 C6 129.36(14) . . . . ?
C9 C8 C7 C16 -117.56(15) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C3 N2 C4 N1 0.00(17) . . . . ?
C3 N2 C4 C5 178.04(14) . . . . ?
C19 C18 C17 C14 106.35(14) . . . . ?
C19 C18 C17 C16 -129.74(13) . . . . ?
C19 C18 C23 C22 -0.8(2) . . . . ?
C19 C20 C21 F1 178.35(13) . . . . ?
C19 C20 C21 C22 -1.3(2) . . . . ?
C1 N1 C4 N2 -178.99(13) . . . . ?
C1 N1 C4 C5 2.9(2) . . . . ?
C1 N1 C2 C3 179.06(14) . . . . ?
C21 C20 C19 C18 0.5(2) . . . . ?
C21 C22 C23 C18 0.1(2) . . . . ?
C23 C18 C17 C14 -72.38(17) . . . . ?
C23 C18 C17 C16 51.53(18) . . . . ?
C23 C18 C19 C20 0.6(2) . . . . ?
C23 C22 C21 F1 -178.62(13) . . . . ?
C23 C22 C21 C20 1.0(2) . . . . ?
C26 C26 C25 C24 -176.19(18) 3_766 . . . ?


_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
;
####################################################################### 
# 
# 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_prapd208_2
_database_code_depnum_ccdc_archive 'CCDC 2173728'
loop_
_audit_author_name
_audit_author_address
'KAKOLI MAJI'
;INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA
India
;
_audit_update_record             
;
2022-05-19 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 F O'
_chemical_formula_sum            'C20 H17 F O'
_chemical_formula_weight         292.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   38.8063(6)
_cell_length_b                   15.6732(3)
_cell_length_c                   9.8717(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6004.15(19)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    4784
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.0230
_cell_measurement_theta_min      4.5460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5410
_diffrn_reflns_point_group_measured_fraction_full 0.795
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.162
_diffrn_reflns_theta_min         4.558
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 106.00   0.50    3.03    --   40.33  39.00  24.00  162
  2  ω    117.00 155.00   0.50   11.00    --   96.67  39.00  24.00   76
  3  ω    111.00 163.00   0.50   11.00    --   96.67 117.00 -90.00  104
  4  ω    138.00 166.00   0.50   11.00    --   96.67  88.00-142.00   56
  5  ω    100.00 131.00   0.50   11.00    --   96.67  88.00-142.00   62
  6  ω     85.00 115.00   0.50   11.00    --   96.67  39.00  24.00   60
  7  ω     43.00  69.00   0.50   11.00    --   96.67 -68.00   0.00   52
  8  ω     34.00  77.00   0.50   11.00    --   96.67-108.00  14.00   86
  9  ω     52.00  88.00   0.50   11.00    --   96.67 -88.00 101.00   72
 10  ω     31.00  58.00   0.50    3.03    --   40.33-108.00  14.00   54
 11  ω     19.00  46.00   0.50    3.03    --   40.33 -88.00 101.00   54
 12  ω     32.00  57.00   0.50   11.00    --   96.67 -50.00  30.00   50
 13  ω     30.00  57.00   0.50   11.00    --   96.67 -50.00   0.00   54
 14  ω     30.00  55.00   0.50   11.00    --   96.67 -50.00 -30.00   50
 15  ω     29.00  67.00   0.50   11.00    --   96.67 -59.00-120.00   76
 16  ω     32.00  57.00   0.50   11.00    --   96.67 -50.00-180.00   50
 17  ω    -33.00  21.00   0.50    3.03    --   40.33 -12.00-180.00  108
 18  ω    -71.00  30.00   0.50    3.03    --  -40.33  88.00-142.00  202
 19  ω    -44.00  26.00   0.50    3.03    --  -40.33  39.00  24.00  140
 20  ω    -44.00 -19.00   0.50   11.00    --  -82.50  39.00  24.00   50
 21  ω    -72.00 -47.00   0.50   11.00    --  -82.50 108.00 111.00   50
 22  ω    -81.00   1.00   0.50    3.03    --  -40.33 108.00 111.00  164
 23  ω    -35.00   6.00   0.50    3.03    --   40.33 -12.00  90.00   82
 24  ω    -17.00  12.00   0.50    3.03    --   40.33 -88.00 101.00   58
 25  ω     30.00  55.00   0.50   11.00    --   96.67 -50.00 150.00   50
 26  ω     29.00  64.00   0.50   11.00    --   96.67 -59.00  90.00   70
 27  ω   -106.00 -25.00   0.50    3.03    --  -40.33 -39.00-129.00  162
 28  ω   -119.00 -92.00   0.50   11.00    --  -82.50 -39.00-129.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.547
_reflns_Friedel_fraction_full    0.601
_reflns_Friedel_fraction_max     0.597
_reflns_number_gt                2111
_reflns_number_total             2167
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 738 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2167
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+6.0426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1014
_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:
 C11(H11), C4(H4), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C20(H20), C6(H6), C7(H7), C16(H16), C8(H8), C19(H19),
 C17(H17)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.24083(4) 0.36150(11) 0.03882(17) 0.0344(4) Uani 1 1 d . . . . .
O2 O 0.35878(5) 0.48434(16) 0.9612(2) 0.0400(5) Uani 1 1 d . . . . .
C10 C 0.33332(6) 0.30324(17) 0.5677(3) 0.0217(5) Uani 1 1 d . . . . .
C5 C 0.31563(6) 0.32205(17) 0.6885(3) 0.0218(5) Uani 1 1 d . . . . .
C11 C 0.35240(6) 0.37910(16) 0.5109(3) 0.0230(5) Uani 1 1 d . . . . .
H11 H 0.365660 0.364358 0.427226 0.028 Uiso 1 1 calc R U . . .
C18 C 0.26053(7) 0.38415(18) 0.1479(3) 0.0272(6) Uani 1 1 d . . . . .
C4 C 0.32078(6) 0.41307(17) 0.7342(3) 0.0231(5) Uani 1 1 d . . . . .
H4 H 0.309441 0.424447 0.823409 0.028 Uiso 1 1 calc R U . . .
C14 C 0.32466(6) 0.45182(17) 0.4842(3) 0.0245(6) Uani 1 1 d . . . . .
H14 H 0.337458 0.504454 0.456834 0.029 Uiso 1 1 calc R U . . .
C3 C 0.35924(6) 0.43129(17) 0.7385(3) 0.0241(6) Uani 1 1 d . . . . .
C9 C 0.33121(6) 0.22266(18) 0.5109(3) 0.0250(6) Uani 1 1 d . . . . .
H9 H 0.343440 0.209674 0.430139 0.030 Uiso 1 1 calc R U . . .
C12 C 0.37531(6) 0.41389(16) 0.6215(3) 0.0243(6) Uani 1 1 d . . . . .
H12 H 0.399322 0.422782 0.609075 0.029 Uiso 1 1 calc R U . . .
C13 C 0.30620(6) 0.47135(18) 0.6198(3) 0.0256(6) Uani 1 1 d . . . . .
H13A H 0.281139 0.461338 0.609678 0.031 Uiso 1 1 calc R U . . .
H13B H 0.309704 0.532002 0.644140 0.031 Uiso 1 1 calc R U . . .
C20 C 0.30954(7) 0.45411(17) 0.2376(3) 0.0252(6) Uani 1 1 d . . . . .
H20 H 0.329623 0.487718 0.224227 0.030 Uiso 1 1 calc R U . . .
C15 C 0.30103(6) 0.42787(17) 0.3679(3) 0.0241(6) Uani 1 1 d . . . . .
C6 C 0.29497(6) 0.26099(18) 0.7484(3) 0.0239(6) Uani 1 1 d . . . . .
H6 H 0.282401 0.274180 0.828228 0.029 Uiso 1 1 calc R U . . .
C7 C 0.29267(6) 0.17996(18) 0.6910(3) 0.0283(6) Uani 1 1 d . . . . .
H7 H 0.278606 0.137669 0.732188 0.034 Uiso 1 1 calc R U . . .
C16 C 0.27130(7) 0.37893(18) 0.3844(3) 0.0287(6) Uani 1 1 d . . . . .
H16 H 0.265094 0.360117 0.472605 0.034 Uiso 1 1 calc R U . . .
C8 C 0.31095(7) 0.16086(19) 0.5735(3) 0.0284(6) Uani 1 1 d . . . . .
H8 H 0.309593 0.105211 0.535725 0.034 Uiso 1 1 calc R U . . .
C2 C 0.37560(7) 0.47010(18) 0.8593(3) 0.0274(6) Uani 1 1 d . . . . .
C19 C 0.28933(7) 0.43232(18) 0.1262(3) 0.0275(6) Uani 1 1 d . . . . .
H19 H 0.295414 0.450480 0.037516 0.033 Uiso 1 1 calc R U . . .
C1 C 0.41327(7) 0.4923(2) 0.8526(3) 0.0340(7) Uani 1 1 d . . . . .
H1A H 0.420936 0.513295 0.941177 0.051 Uiso 1 1 calc R U . . .
H1B H 0.416880 0.536687 0.784182 0.051 Uiso 1 1 calc R U . . .
H1C H 0.426550 0.441383 0.828227 0.051 Uiso 1 1 calc R U . . .
C17 C 0.25064(7) 0.35713(17) 0.2757(3) 0.0298(6) Uani 1 1 d . . . . .
H17 H 0.230249 0.324550 0.288242 0.036 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 C18 1.368(3) . ?
O2 C2 1.219(3) . ?
C10 C5 1.407(4) . ?
C10 C11 1.509(4) . ?
C10 C9 1.384(4) . ?
C5 C4 1.510(4) . ?
C5 C6 1.381(4) . ?
C11 H11 1.0000 . ?
C11 C14 1.590(3) . ?
C11 C12 1.510(4) . ?
C18 C19 1.366(4) . ?
C18 C17 1.385(4) . ?
C4 H4 1.0000 . ?
C4 C3 1.520(3) . ?
C4 C13 1.559(4) . ?
C14 H14 1.0000 . ?
C14 C13 1.549(4) . ?
C14 C15 1.517(4) . ?
C3 C12 1.341(4) . ?
C3 C2 1.482(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.392(4) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C20 H20 0.9500 . ?
C20 C15 1.390(4) . ?
C20 C19 1.394(4) . ?
C15 C16 1.395(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(4) . ?
C8 H8 0.9500 . ?
C2 C1 1.504(4) . ?
C19 H19 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C17 H17 0.9500 . ?

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
C5 C10 C11 112.9(2) . . ?
C9 C10 C5 120.4(2) . . ?
C9 C10 C11 126.7(2) . . ?
C10 C5 C4 112.8(2) . . ?
C6 C5 C10 120.0(2) . . ?
C6 C5 C4 127.1(2) . . ?
C10 C11 H11 112.2 . . ?
C10 C11 C14 107.1(2) . . ?
C10 C11 C12 107.7(2) . . ?
C14 C11 H11 112.2 . . ?
C12 C11 H11 112.2 . . ?
C12 C11 C14 105.0(2) . . ?
F1 C18 C17 118.9(2) . . ?
C19 C18 F1 118.5(3) . . ?
C19 C18 C17 122.6(3) . . ?
C5 C4 H4 112.0 . . ?
C5 C4 C3 108.4(2) . . ?
C5 C4 C13 106.8(2) . . ?
C3 C4 H4 112.0 . . ?
C3 C4 C13 105.4(2) . . ?
C13 C4 H4 112.0 . . ?
C11 C14 H14 107.5 . . ?
C13 C14 C11 108.2(2) . . ?
C13 C14 H14 107.5 . . ?
C15 C14 C11 110.9(2) . . ?
C15 C14 H14 107.5 . . ?
C15 C14 C13 115.0(2) . . ?
C12 C3 C4 113.2(2) . . ?
C12 C3 C2 125.3(2) . . ?
C2 C3 C4 121.4(2) . . ?
C10 C9 H9 120.4 . . ?
C10 C9 C8 119.3(3) . . ?
C8 C9 H9 120.4 . . ?
C11 C12 H12 122.5 . . ?
C3 C12 C11 115.0(2) . . ?
C3 C12 H12 122.5 . . ?
C4 C13 H13A 109.7 . . ?
C4 C13 H13B 109.7 . . ?
C14 C13 C4 110.0(2) . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C15 C20 H20 119.2 . . ?
C15 C20 C19 121.6(2) . . ?
C19 C20 H20 119.2 . . ?
C20 C15 C14 118.9(2) . . ?
C20 C15 C16 117.9(3) . . ?
C16 C15 C14 123.2(2) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
O2 C2 C3 120.6(2) . . ?
O2 C2 C1 120.9(3) . . ?
C3 C2 C1 118.4(2) . . ?
C18 C19 C20 118.1(3) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C18 C17 H17 121.0 . . ?
C16 C17 C18 118.1(2) . . ?
C16 C17 H17 121.0 . . ?

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
F1 C18 C19 C20 -179.1(2) . . . . ?
F1 C18 C17 C16 178.5(2) . . . . ?
C10 C5 C4 C3 -52.0(3) . . . . ?
C10 C5 C4 C13 61.1(2) . . . . ?
C10 C5 C6 C7 2.1(3) . . . . ?
C10 C11 C14 C13 57.8(3) . . . . ?
C10 C11 C14 C15 -69.3(3) . . . . ?
C10 C11 C12 C3 -53.2(3) . . . . ?
C10 C9 C8 C7 0.7(4) . . . . ?
C5 C10 C11 C14 -58.9(3) . . . . ?
C5 C10 C11 C12 53.7(3) . . . . ?
C5 C10 C9 C8 1.0(4) . . . . ?
C5 C4 C3 C12 54.0(3) . . . . ?
C5 C4 C3 C2 -130.0(3) . . . . ?
C5 C4 C13 C14 -57.5(3) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C11 C10 C5 C4 -1.5(3) . . . . ?
C11 C10 C5 C6 175.6(2) . . . . ?
C11 C10 C9 C8 -176.7(2) . . . . ?
C11 C14 C13 C4 -0.5(3) . . . . ?
C11 C14 C15 C20 -92.2(3) . . . . ?
C11 C14 C15 C16 86.4(3) . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C4 C3 C12 C11 -0.7(3) . . . . ?
C4 C3 C2 O2 3.8(4) . . . . ?
C4 C3 C2 C1 -175.5(3) . . . . ?
C14 C11 C12 C3 60.8(3) . . . . ?
C14 C15 C16 C17 -178.9(2) . . . . ?
C3 C4 C13 C14 57.7(3) . . . . ?
C9 C10 C5 C4 -179.6(2) . . . . ?
C9 C10 C5 C6 -2.5(3) . . . . ?
C9 C10 C11 C14 119.0(3) . . . . ?
C9 C10 C11 C12 -128.5(3) . . . . ?
C12 C11 C14 C13 -56.6(3) . . . . ?
C12 C11 C14 C15 176.3(2) . . . . ?
C12 C3 C2 O2 179.3(3) . . . . ?
C12 C3 C2 C1 0.0(4) . . . . ?
C13 C4 C3 C12 -60.1(3) . . . . ?
C13 C4 C3 C2 115.9(3) . . . . ?
C13 C14 C15 C20 144.6(2) . . . . ?
C13 C14 C15 C16 -36.8(4) . . . . ?
C20 C15 C16 C17 -0.3(4) . . . . ?
C15 C14 C13 C4 124.2(2) . . . . ?
C15 C20 C19 C18 0.2(4) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C6 C5 C4 C3 131.1(3) . . . . ?
C6 C5 C4 C13 -115.7(3) . . . . ?
C6 C7 C8 C9 -1.1(4) . . . . ?
C2 C3 C12 C11 -176.6(2) . . . . ?
C19 C18 C17 C16 -1.2(4) . . . . ?
C19 C20 C15 C14 178.4(2) . . . . ?
C19 C20 C15 C16 -0.3(4) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_prapd205b_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2173850'
loop_
_audit_author_name
_audit_author_address
'KAKOLI MAJI'
;INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA
India
;
_audit_update_record             
;
2022-05-20 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F N2 O'
_chemical_formula_sum            'C23 H19 F N2 O'
_chemical_formula_weight         358.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   12.6548(4)
_cell_length_b                   7.2987(2)
_cell_length_c                   20.6049(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.6430(10)
_cell_angle_gamma                90
_cell_volume                     1881.53(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0920 before and 0.0629 after correction. The Ratio of minimum to maximum transmission is 0.9485. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47061
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.999
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2305
_reflns_number_total             3308
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.108
_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)+(0.0632P)²+0.0436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.094) H3(0.087) H5(0.068) H6A(0.077) H6B(0.077) H7(0.064)
 H11(0.088) H12(0.089) H13(0.078) H14(0.063) H15(0.066) H18(0.098) H19(0.137)
 H20(0.132) H21(0.1) H22(0.086) H23A(0.127) H23B(0.127) H23C(0.127)
 Fixed X: H2(0.948142) H3(0.809817) H5(0.636085) H6A(0.63234) H6B(0.535054)
 H7(0.554952) H11(0.442838) H12(0.894745) H13(0.75834) H14(0.625211)
 H15(0.778248) H18(0.708154) H19(0.887914) H20(1.002209) H21(0.939459)
 H22(0.299015) H23A(0.235143) H23B(0.320614) H23C(0.235688)
 Fixed Y: H2(1.002918) H3(0.948924) H5(0.558766) H6A(0.925695) H6B(0.789744)
 H7(0.927048) H11(0.061432) H12(0.518979) H13(0.463741) H14(0.388741)
 H15(0.466661) H18(1.113524) H19(1.133254) H20(0.900536) H21(0.640379)
 H22(0.227237) H23A(0.549407) H23B(0.697526) H23C(0.634682)
 Fixed Z: H2(0.896472) H3(0.811599) H5(0.801176) H6A(0.779381) H6B(0.768177)
 H7(0.664282) H11(0.534175) H12(0.974858) H13(0.889443) H14(0.663289)
 H15(0.739593) H18(0.6297) H19(0.623056) H20(0.659451) H21(0.706259)
 H22(0.467281) H23A(0.455853) H23B(0.482249) H23C(0.525732)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 1.01472(9) 0.79624(16) 0.99193(6) 0.1072(4) Uani 1 1 d . . . . .
O1 O 0.40504(9) 0.75956(15) 0.60372(6) 0.0815(4) Uani 1 1 d . . . . .
N1 N 0.48488(11) 0.29934(16) 0.58221(7) 0.0613(4) Uani 1 1 d . . . . .
N2 N 0.35195(10) 0.45116(17) 0.52280(6) 0.0575(4) Uani 1 1 d . . . . .
C1 C 0.93225(14) 0.7647(3) 0.94199(9) 0.0732(5) Uani 1 1 d . . . . .
C2 C 0.90930(15) 0.8944(3) 0.89483(9) 0.0780(5) Uani 1 1 d . . . . .
H2 H 0.948142 1.002918 0.896472 0.094 Uiso 1 1 calc R . . . .
C3 C 0.82661(15) 0.8611(2) 0.84421(8) 0.0726(5) Uani 1 1 d . . . . .
H3 H 0.809817 0.948924 0.811599 0.087 Uiso 1 1 calc R . . . .
C4 C 0.76842(12) 0.7004(2) 0.84097(7) 0.0572(4) Uani 1 1 d . . . . .
C5 C 0.68076(12) 0.6533(2) 0.78518(7) 0.0567(4) Uani 1 1 d . . . . .
H5 H 0.636085 0.558766 0.801176 0.068 Uiso 1 1 calc R . . . .
C6 C 0.60653(13) 0.8120(2) 0.75832(8) 0.0645(4) Uani 1 1 d . . . . .
H6A H 0.632340 0.925695 0.779381 0.077 Uiso 1 1 calc R . . . .
H6B H 0.535054 0.789744 0.768177 0.077 Uiso 1 1 calc R . . . .
C7 C 0.60310(13) 0.82901(18) 0.68292(7) 0.0532(4) Uani 1 1 d . . . . .
H7 H 0.554952 0.927048 0.664282 0.064 Uiso 1 1 calc R . . . .
C8 C 0.56877(11) 0.64386(17) 0.65397(7) 0.0477(4) Uani 1 1 d . . . . .
C9 C 0.46640(12) 0.62899(18) 0.60959(7) 0.0515(4) Uani 1 1 d . . . . .
C10 C 0.43699(11) 0.46150(18) 0.57217(7) 0.0491(4) Uani 1 1 d . . . . .
C11 C 0.42829(16) 0.1854(2) 0.53828(9) 0.0730(5) Uani 1 1 d . . . . .
H11 H 0.442838 0.061432 0.534175 0.088 Uiso 1 1 calc R . . . .
C12 C 0.87762(14) 0.6049(3) 0.94162(9) 0.0738(5) Uani 1 1 d . . . . .
H12 H 0.894745 0.518979 0.974858 0.089 Uiso 1 1 calc R . . . .
C13 C 0.79600(13) 0.5734(2) 0.89060(8) 0.0647(4) Uani 1 1 d . . . . .
H13 H 0.758340 0.463741 0.889443 0.078 Uiso 1 1 calc R . . . .
C14 C 0.63580(12) 0.50983(18) 0.67676(7) 0.0521(4) Uani 1 1 d . . . . .
H14 H 0.625211 0.388741 0.663289 0.063 Uiso 1 1 calc R . . . .
C15 C 0.72972(12) 0.56874(19) 0.72582(7) 0.0552(4) Uani 1 1 d . . . . .
H15 H 0.778248 0.466661 0.739593 0.066 Uiso 1 1 calc R . . . .
C16 C 0.78519(12) 0.7224(2) 0.69539(7) 0.0570(4) Uani 1 1 d . . . . .
C17 C 0.71591(13) 0.8628(2) 0.67229(7) 0.0560(4) Uani 1 1 d . . . . .
C18 C 0.75413(18) 1.0184(2) 0.64502(9) 0.0817(6) Uani 1 1 d . . . . .
H18 H 0.708154 1.113524 0.629700 0.098 Uiso 1 1 calc R . . . .
C19 C 0.8614(2) 1.0292(4) 0.64110(12) 0.1146(9) Uani 1 1 d . . . . .
H19 H 0.887914 1.133254 0.623056 0.137 Uiso 1 1 calc R . . . .
C20 C 0.93009(19) 0.8904(4) 0.66313(12) 0.1103(8) Uani 1 1 d . . . . .
H20 H 1.002209 0.900536 0.659451 0.132 Uiso 1 1 calc R . . . .
C21 C 0.89290(16) 0.7347(3) 0.69093(10) 0.0833(6) Uani 1 1 d . . . . .
H21 H 0.939459 0.640379 0.706259 0.100 Uiso 1 1 calc R . . . .
C22 C 0.34780(16) 0.2759(3) 0.50115(9) 0.0720(5) Uani 1 1 d . . . . .
H22 H 0.299015 0.227237 0.467281 0.086 Uiso 1 1 calc R . . . .
C23 C 0.27966(15) 0.5956(3) 0.49421(9) 0.0847(6) Uani 1 1 d . . . . .
H23A H 0.235143 0.549407 0.455853 0.127 Uiso 1 1 calc GR . . . .
H23B H 0.320614 0.697526 0.482249 0.127 Uiso 1 1 calc GR . . . .
H23C H 0.235688 0.634682 0.525732 0.127 Uiso 1 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
F1 C1 1.3704(19) . ?
O1 C9 1.2237(17) . ?
N1 C10 1.3317(17) . ?
N1 C11 1.352(2) . ?
N2 C10 1.3673(18) . ?
N2 C22 1.353(2) . ?
N2 C23 1.460(2) . ?
C1 C2 1.356(3) . ?
C1 C12 1.355(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(2) . ?
C4 C5 1.512(2) . ?
C4 C13 1.385(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.541(2) . ?
C5 C15 1.578(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.553(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.5141(19) . ?
C7 C17 1.497(2) . ?
C8 C9 1.473(2) . ?
C8 C14 1.3332(18) . ?
C9 C10 1.463(2) . ?
C11 H11 0.9300 . ?
C11 C22 1.351(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.503(2) . ?
C15 H15 0.9800 . ?
C15 C16 1.509(2) . ?
C16 C17 1.386(2) . ?
C16 C21 1.383(2) . ?
C17 C18 1.386(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.367(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C10 N1 C11 105.05(14) . . ?
C10 N2 C23 129.46(14) . . ?
C22 N2 C10 106.55(13) . . ?
C22 N2 C23 123.93(15) . . ?
C2 C1 F1 118.54(17) . . ?
C12 C1 F1 118.61(18) . . ?
C12 C1 C2 122.85(16) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.27(17) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.55(17) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 123.69(14) . . ?
C3 C4 C13 117.33(15) . . ?
C13 C4 C5 118.93(14) . . ?
C4 C5 H5 107.4 . . ?
C4 C5 C6 116.12(13) . . ?
C4 C5 C15 110.46(12) . . ?
C6 C5 H5 107.4 . . ?
C6 C5 C15 107.75(12) . . ?
C15 C5 H5 107.4 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C5 C6 C7 110.08(12) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7 111.9 . . ?
C8 C7 C6 106.62(12) . . ?
C8 C7 H7 111.9 . . ?
C17 C7 C6 106.00(12) . . ?
C17 C7 H7 111.9 . . ?
C17 C7 C8 108.24(12) . . ?
C9 C8 C7 118.93(12) . . ?
C14 C8 C7 112.73(13) . . ?
C14 C8 C9 128.18(13) . . ?
O1 C9 C8 119.32(13) . . ?
O1 C9 C10 119.41(14) . . ?
C10 C9 C8 121.26(12) . . ?
N1 C10 N2 110.82(12) . . ?
N1 C10 C9 125.94(14) . . ?
N2 C10 C9 123.20(13) . . ?
N1 C11 H11 124.5 . . ?
C22 C11 N1 110.91(15) . . ?
C22 C11 H11 124.5 . . ?
C1 C12 H12 120.9 . . ?
C1 C12 C13 118.11(17) . . ?
C13 C12 H12 120.9 . . ?
C4 C13 H13 119.1 . . ?
C12 C13 C4 121.89(17) . . ?
C12 C13 H13 119.1 . . ?
C8 C14 H14 122.5 . . ?
C8 C14 C15 115.09(12) . . ?
C15 C14 H14 122.5 . . ?
C5 C15 H15 112.0 . . ?
C14 C15 C5 105.69(12) . . ?
C14 C15 H15 112.0 . . ?
C14 C15 C16 107.67(12) . . ?
C16 C15 C5 107.03(11) . . ?
C16 C15 H15 112.0 . . ?
C17 C16 C15 112.50(14) . . ?
C21 C16 C15 126.91(16) . . ?
C21 C16 C17 120.57(16) . . ?
C16 C17 C7 113.32(13) . . ?
C16 C17 C18 120.25(17) . . ?
C18 C17 C7 126.38(16) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.6(2) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.5(2) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 118.7(2) . . ?
C16 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
N2 C22 H22 126.7 . . ?
C11 C22 N2 106.66(15) . . ?
C11 C22 H22 126.7 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 C1 C2 C3 179.41(16) . . . . ?
F1 C1 C12 C13 -178.96(15) . . . . ?
O1 C9 C10 N1 -166.75(15) . . . . ?
O1 C9 C10 N2 10.7(2) . . . . ?
N1 C11 C22 N2 -1.2(2) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C12 C13 C4 -0.7(3) . . . . ?
C2 C1 C12 C13 0.6(3) . . . . ?
C2 C3 C4 C5 -177.08(15) . . . . ?
C2 C3 C4 C13 0.1(3) . . . . ?
C3 C4 C5 C6 -39.9(2) . . . . ?
C3 C4 C5 C15 83.16(19) . . . . ?
C3 C4 C13 C12 0.4(2) . . . . ?
C4 C5 C6 C7 126.22(14) . . . . ?
C4 C5 C15 C14 174.28(12) . . . . ?
C4 C5 C15 C16 -71.16(15) . . . . ?
C5 C4 C13 C12 177.68(15) . . . . ?
C5 C6 C7 C8 55.92(17) . . . . ?
C5 C6 C7 C17 -59.26(15) . . . . ?
C5 C15 C16 C17 -60.34(15) . . . . ?
C5 C15 C16 C21 117.78(17) . . . . ?
C6 C5 C15 C14 -57.93(15) . . . . ?
C6 C5 C15 C16 56.64(16) . . . . ?
C6 C7 C8 C9 115.92(14) . . . . ?
C6 C7 C8 C14 -59.97(16) . . . . ?
C6 C7 C17 C16 60.62(15) . . . . ?
C6 C7 C17 C18 -116.77(17) . . . . ?
C7 C8 C9 O1 -9.4(2) . . . . ?
C7 C8 C9 C10 170.24(13) . . . . ?
C7 C8 C14 C15 0.24(18) . . . . ?
C7 C17 C18 C19 177.67(17) . . . . ?
C8 C7 C17 C16 -53.45(16) . . . . ?
C8 C7 C17 C18 129.16(16) . . . . ?
C8 C9 C10 N1 13.6(2) . . . . ?
C8 C9 C10 N2 -168.99(13) . . . . ?
C8 C14 C15 C5 60.30(16) . . . . ?
C8 C14 C15 C16 -53.82(16) . . . . ?
C9 C8 C14 C15 -175.19(14) . . . . ?
C10 N1 C11 C22 0.83(19) . . . . ?
C10 N2 C22 C11 1.01(17) . . . . ?
C11 N1 C10 N2 -0.17(17) . . . . ?
C11 N1 C10 C9 177.54(15) . . . . ?
C12 C1 C2 C3 -0.2(3) . . . . ?
C13 C4 C5 C6 142.98(15) . . . . ?
C13 C4 C5 C15 -93.97(16) . . . . ?
C14 C8 C9 O1 165.75(16) . . . . ?
C14 C8 C9 C10 -14.6(2) . . . . ?
C14 C15 C16 C17 52.88(15) . . . . ?
C14 C15 C16 C21 -129.00(16) . . . . ?
C15 C5 C6 C7 1.77(17) . . . . ?
C15 C16 C17 C7 -0.01(17) . . . . ?
C15 C16 C17 C18 177.56(14) . . . . ?
C15 C16 C21 C20 -177.75(17) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C7 C8 C9 -130.41(14) . . . . ?
C17 C7 C8 C14 53.69(16) . . . . ?
C17 C16 C21 C20 0.2(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C19 C20 C21 C16 0.5(3) . . . . ?
C21 C16 C17 C7 -178.27(14) . . . . ?
C21 C16 C17 C18 -0.7(2) . . . . ?
C22 N2 C10 N1 -0.53(16) . . . . ?
C22 N2 C10 C9 -178.31(14) . . . . ?
C23 N2 C10 N1 -177.73(15) . . . . ?
C23 N2 C10 C9 4.5(2) . . . . ?
C23 N2 C22 C11 178.40(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kmcke212_2
_database_code_depnum_ccdc_archive 'CCDC 2173729'
loop_
_audit_author_name
_audit_author_address
'KAKOLI MAJI'
;INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA
India
;
_audit_update_record             
;
2022-05-19 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 Cl O'
_chemical_formula_sum            'C20 H17 Cl O'
_chemical_formula_weight         308.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   9.4028(2)
_cell_length_b                   19.5701(2)
_cell_length_c                   9.3681(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.798(2)
_cell_angle_gamma                90
_cell_volume                     1552.05(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7636
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.9920
_cell_measurement_theta_min      2.2490
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.814
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.885
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8978
_diffrn_reflns_point_group_measured_fraction_full 0.885
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.103
_diffrn_reflns_theta_min         4.519
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.885
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     78.00 163.00   0.50    0.46    --   96.67  50.00 -91.00  170
  2  ω     99.00 164.00   0.50    0.46    --   96.67 117.00-150.00  130
  3  ω    105.00 170.00   0.50    0.46    --   96.67  96.00 120.00  130
  4  ω    106.00 171.00   0.50    0.46    --   96.67  97.00 131.00  130
  5  ω    -22.00  69.00   0.50    0.20    --   40.33 -81.00 -86.00  182
  6  ω     40.00  65.00   0.50    0.46    --   96.67 -97.00  23.00   50
  7  ω     -7.00  75.00   0.50    0.20    --   40.33 -97.00  23.00  164
  8  ω     28.00 125.00   0.50    0.46    --   96.67 -81.00 -86.00  194
  9  ω     29.00  83.00   0.50    0.46    --   96.67 -68.00-180.00  108
 10  ω     30.00  57.00   0.50    0.46    --   96.67 -50.00   0.00   54
 11  ω     30.00  57.00   0.50    0.46    --   96.67 -50.00  30.00   54
 12  ω     30.00  57.00   0.50    0.46    --   96.67 -50.00  60.00   54
 13  ω     30.00  57.00   0.50    0.46    --   96.67 -50.00  90.00   54
 14  ω     30.00  57.00   0.50    0.46    --   96.67 -50.00 122.00   54
 15  ω     29.00  83.00   0.50    0.46    --   96.67 -68.00  90.00  108
 16  ω    -26.00  57.00   0.50    0.20    --   40.33 -50.00 122.00  166
 17  ω    -30.00  31.00   0.50    0.20    --   40.33 -25.00   0.00  122
 18  ω    -74.00  29.00   0.50    0.20    --  -40.33  97.00 131.00  206
 19  ω    -81.00  -8.00   0.50    0.46    --  -82.50  97.00 131.00  146
 20  ω    -68.00  29.00   0.50    0.20    --  -40.33  81.00  36.00  194
 21  ω    -57.00  26.00   0.50    0.20    --  -40.33  50.00 -91.00  166
 22  ω    -57.00 -16.00   0.50    0.46    --  -82.50  50.00 -91.00   82
 23  ω   -106.00 -25.00   0.50    0.20    --  -40.33 -38.00-150.00  162
 24  ω   -152.00 -78.00   0.50    0.46    --  -82.50 -81.00 -86.00  148
 25  ω   -156.00 -84.00   0.50    0.46    --  -82.50 -97.00  23.00  144
 26  ω   -149.00 -63.00   0.50    0.46    --  -82.50 -50.00 122.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2441
_reflns_number_total             2500
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2500
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.087
_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)+(0.0384P)²+1.5930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1053
_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:
 C4(H4), C14(H14), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C16(H16), C12(H12), C17(H17), C20(H20), C19(H19), C8(H8),
 C7(H7)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.03676(5) 0.52712(3) 0.22123(6) 0.02410(17) Uani 1 1 d . . . . .
O1 O 1.03742(18) 0.28732(8) 1.0348(2) 0.0352(4) Uani 1 1 d . . . . .
C5 C 0.6020(2) 0.36561(10) 0.9362(2) 0.0180(4) Uani 1 1 d . . . . .
C15 C 0.3786(2) 0.39047(10) 0.5128(2) 0.0197(4) Uani 1 1 d . . . . .
C10 C 0.4675(2) 0.32773(10) 0.8410(2) 0.0182(4) Uani 1 1 d . . . . .
C9 C 0.3338(2) 0.32974(10) 0.8673(2) 0.0194(4) Uani 1 1 d . . . . .
H9 H 0.243546 0.303302 0.803753 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7347(2) 0.35741(10) 0.8874(2) 0.0191(4) Uani 1 1 d . . . . .
H4 H 0.832711 0.381755 0.961273 0.023 Uiso 1 1 calc R U . . .
C3 C 0.7635(2) 0.28176(10) 0.8765(2) 0.0198(4) Uani 1 1 d . . . . .
C6 C 0.5991(2) 0.40834(10) 1.0531(2) 0.0208(4) Uani 1 1 d . . . . .
H6 H 0.688354 0.435641 1.115058 0.025 Uiso 1 1 calc R U . . .
C16 C 0.3341(2) 0.44425(10) 0.5839(3) 0.0212(4) Uani 1 1 d . . . . .
H16 H 0.392548 0.452491 0.694222 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6329(2) 0.24735(10) 0.7828(2) 0.0200(4) Uani 1 1 d . . . . .
H12 H 0.633530 0.199637 0.764396 0.024 Uiso 1 1 calc R U . . .
C17 C 0.2057(2) 0.48561(10) 0.4952(3) 0.0218(5) Uani 1 1 d . . . . .
H17 H 0.176156 0.521757 0.544555 0.026 Uiso 1 1 calc R U . . .
C20 C 0.2886(2) 0.37896(11) 0.3522(3) 0.0225(5) Uani 1 1 d . . . . .
H20 H 0.314904 0.341909 0.302605 0.027 Uiso 1 1 calc R U . . .
C18 C 0.1214(2) 0.47365(10) 0.3347(3) 0.0208(4) Uani 1 1 d . . . . .
C19 C 0.1605(2) 0.42044(11) 0.2618(3) 0.0233(5) Uani 1 1 d . . . . .
H19 H 0.100897 0.412224 0.151613 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3331(2) 0.37091(10) 0.9878(3) 0.0222(5) Uani 1 1 d . . . . .
H8 H 0.242701 0.371813 1.008267 0.027 Uiso 1 1 calc R U . . .
C7 C 0.4636(3) 0.41075(10) 1.0785(3) 0.0227(5) Uani 1 1 d . . . . .
H7 H 0.460621 0.439814 1.158409 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6710(2) 0.38521(11) 0.7151(3) 0.0220(5) Uani 1 1 d . . . . .
H13A H 0.645928 0.434413 0.713620 0.026 Uiso 1 1 calc R U . . .
H13B H 0.752883 0.380072 0.676223 0.026 Uiso 1 1 calc R U . . .
C14 C 0.5200(2) 0.34524(11) 0.6050(2) 0.0204(4) Uani 1 1 d . . . . .
H14 H 0.545167 0.320064 0.525986 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4847(2) 0.28985(10) 0.7087(2) 0.0188(4) Uani 1 1 d . . . . .
H11 H 0.389550 0.261658 0.644167 0.023 Uiso 1 1 calc R U . . .
C2 C 0.9235(2) 0.25184(11) 0.9565(3) 0.0232(5) Uani 1 1 d . . . . .
C1 C 0.9436(3) 0.17658(12) 0.9390(3) 0.0332(6) Uani 1 1 d . . . . .
H1A H 1.055311 0.164326 0.997865 0.050 Uiso 1 1 calc R U . . .
H1B H 0.907772 0.165501 0.826646 0.050 Uiso 1 1 calc R U . . .
H1C H 0.880880 0.150853 0.981198 0.050 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
Cl1 C18 1.749(2) . ?
O1 C2 1.218(3) . ?
C5 C10 1.401(3) . ?
C5 C4 1.513(3) . ?
C5 C6 1.387(3) . ?
C15 C16 1.404(3) . ?
C15 C20 1.387(3) . ?
C15 C14 1.516(3) . ?
C10 C9 1.383(3) . ?
C10 C11 1.512(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.389(3) . ?
C4 H4 1.0000 . ?
C4 C3 1.517(3) . ?
C4 C13 1.555(3) . ?
C3 C12 1.339(3) . ?
C3 C2 1.479(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.507(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.392(3) . ?
C18 C19 1.380(3) . ?
C19 H19 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.389(3) . ?
C7 H7 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.555(3) . ?
C14 H14 1.0000 . ?
C14 C11 1.583(3) . ?
C11 H11 1.0000 . ?
C2 C1 1.503(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
C10 C5 C4 112.72(18) . . ?
C6 C5 C10 119.97(18) . . ?
C6 C5 C4 127.17(19) . . ?
C16 C15 C14 122.43(18) . . ?
C20 C15 C16 117.98(19) . . ?
C20 C15 C14 119.59(18) . . ?
C5 C10 C11 113.09(17) . . ?
C9 C10 C5 120.67(19) . . ?
C9 C10 C11 126.17(19) . . ?
C10 C9 H9 120.4 . . ?
C10 C9 C8 119.16(19) . . ?
C8 C9 H9 120.4 . . ?
C5 C4 H4 112.0 . . ?
C5 C4 C3 108.60(16) . . ?
C5 C4 C13 106.30(16) . . ?
C3 C4 H4 112.0 . . ?
C3 C4 C13 105.71(17) . . ?
C13 C4 H4 112.0 . . ?
C12 C3 C4 113.29(18) . . ?
C12 C3 C2 125.01(19) . . ?
C2 C3 C4 121.63(18) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.21(19) . . ?
C7 C6 H6 120.4 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.98(19) . . ?
C17 C16 H16 119.5 . . ?
C3 C12 H12 122.4 . . ?
C3 C12 C11 115.11(18) . . ?
C11 C12 H12 122.4 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.32(19) . . ?
C18 C17 H17 120.3 . . ?
C15 C20 H20 119.2 . . ?
C15 C20 C19 121.53(19) . . ?
C19 C20 H20 119.2 . . ?
C17 C18 Cl1 119.58(16) . . ?
C19 C18 Cl1 119.33(17) . . ?
C19 C18 C17 121.09(19) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 C20 119.1(2) . . ?
C18 C19 H19 120.5 . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.54(19) . . ?
C7 C8 H8 119.7 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C4 C13 H13A 109.7 . . ?
C4 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 C4 109.91(16) . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C15 C14 C13 113.92(17) . . ?
C15 C14 H14 107.3 . . ?
C15 C14 C11 112.58(16) . . ?
C13 C14 H14 107.3 . . ?
C13 C14 C11 108.19(16) . . ?
C11 C14 H14 107.3 . . ?
C10 C11 C14 107.02(16) . . ?
C10 C11 H11 112.2 . . ?
C12 C11 C10 107.46(17) . . ?
C12 C11 C14 105.21(16) . . ?
C12 C11 H11 112.2 . . ?
C14 C11 H11 112.2 . . ?
O1 C2 C3 120.91(19) . . ?
O1 C2 C1 120.3(2) . . ?
C3 C2 C1 118.75(19) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C18 C19 C20 178.64(16) . . . . ?
C5 C10 C9 C8 1.2(3) . . . . ?
C5 C10 C11 C12 54.0(2) . . . . ?
C5 C10 C11 C14 -58.6(2) . . . . ?
C5 C4 C3 C12 53.6(2) . . . . ?
C5 C4 C3 C2 -129.5(2) . . . . ?
C5 C4 C13 C14 -58.1(2) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C15 C20 C19 C18 -0.9(3) . . . . ?
C15 C14 C11 C10 -69.3(2) . . . . ?
C15 C14 C11 C12 176.55(16) . . . . ?
C10 C5 C4 C3 -51.5(2) . . . . ?
C10 C5 C4 C13 61.9(2) . . . . ?
C10 C5 C6 C7 2.7(3) . . . . ?
C10 C9 C8 C7 1.4(3) . . . . ?
C9 C10 C11 C12 -129.1(2) . . . . ?
C9 C10 C11 C14 118.3(2) . . . . ?
C9 C8 C7 C6 -2.0(3) . . . . ?
C4 C5 C10 C9 -179.24(18) . . . . ?
C4 C5 C10 C11 -2.1(2) . . . . ?
C4 C5 C6 C7 178.00(19) . . . . ?
C4 C3 C12 C11 -0.5(3) . . . . ?
C4 C3 C2 O1 0.4(3) . . . . ?
C4 C3 C2 C1 -179.3(2) . . . . ?
C4 C13 C14 C15 125.91(18) . . . . ?
C4 C13 C14 C11 -0.1(2) . . . . ?
C3 C4 C13 C14 57.2(2) . . . . ?
C3 C12 C11 C10 -53.3(2) . . . . ?
C3 C12 C11 C14 60.5(2) . . . . ?
C6 C5 C10 C9 -3.3(3) . . . . ?
C6 C5 C10 C11 173.81(18) . . . . ?
C6 C5 C4 C3 132.9(2) . . . . ?
C6 C5 C4 C13 -113.7(2) . . . . ?
C16 C15 C20 C19 2.0(3) . . . . ?
C16 C15 C14 C13 -46.2(3) . . . . ?
C16 C15 C14 C11 77.5(2) . . . . ?
C16 C17 C18 Cl1 -178.09(15) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C12 C3 C2 O1 177.0(2) . . . . ?
C12 C3 C2 C1 -2.7(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C20 C15 C16 C17 -1.4(3) . . . . ?
C20 C15 C14 C13 133.9(2) . . . . ?
C20 C15 C14 C11 -102.4(2) . . . . ?
C13 C4 C3 C12 -60.1(2) . . . . ?
C13 C4 C3 C2 116.8(2) . . . . ?
C13 C14 C11 C10 57.4(2) . . . . ?
C13 C14 C11 C12 -56.7(2) . . . . ?
C14 C15 C16 C17 178.72(18) . . . . ?
C14 C15 C20 C19 -178.14(19) . . . . ?
C11 C10 C9 C8 -175.48(19) . . . . ?
C2 C3 C12 C11 -177.27(19) . . . . ?

# end Validation Reply Form
_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
;
# start Validation Reply Form
_vrf_PLAT029_kmcke212_2          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.885 Why?  
RESPONSE: The diffraction peaks were found to be weak at the higher 
2theta resolution due to poor crystalline nature of the compound.
However, this is best possible data that obtained so far.
;
_vrf_PLAT911_kmcke212_2          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        322 Report
RESPONSE: This alert is due to beamstop. So, some low angle refelections
are probably missed.
;
####################################################################### 
# 
# 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_kmc-ke257_2_auto_2
_database_code_depnum_ccdc_archive 'CCDC 2190337'
loop_
_audit_author_name
_audit_author_address
'KAKOLI MAJI'
;INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA
India
;
_audit_update_record             
;
2022-07-14 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_audit_creation_date             2022-07-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 F O3'
_chemical_formula_sum            'C22 H19 F O3'
_chemical_formula_weight         350.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     100K
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/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                   13.8641(2)
_cell_length_b                   10.52260(10)
_cell_length_c                   12.11710(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.0290(10)
_cell_angle_gamma                90
_cell_volume                     1722.21(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12932
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      68.0110
_cell_measurement_theta_min      3.2310
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         3.272
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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    0.23    --  -40.33 108.00 126.00  164
  2  ω     21.00  81.00   0.50    0.23    --   40.33-108.00  29.00  120
  3  ω   -152.00 -82.00   0.50    1.01    --  -82.50-108.00  29.00  140
  4  ω    -83.00 -13.00   0.50    1.01    --  -82.50 108.00 126.00  140
  5  ω    103.00 166.00   0.50    1.01    --   96.67 108.00 126.00  126
  6  ω     27.00 108.00   0.50    1.01    --   96.67-108.00  29.00  162
  7  ω    -24.00  35.00   0.50    0.23    --  -40.33  12.00  30.00  118
  8  ω    -43.00  26.00   0.50    0.23    --  -40.33  38.00 150.00  138
  9  ω    -31.00  30.00   0.50    0.23    --  -40.33  25.00  30.00  122
 10  ω   -108.00 -17.00   0.50    0.23    --  -40.33 -64.00  30.00  182
 11  ω     25.00 111.00   0.50    0.23    --   40.33  25.00 150.00  172
 12  ω    -30.00  31.00   0.50    0.23    --   40.33 -25.00  30.00  122
 13  ω    -27.00  64.00   0.50    0.23    --   40.33 -64.00 -90.00  182
 14  ω    -47.00 -15.00   0.50    1.01    --  -82.50  42.00 -90.00   64
 15  ω    -47.00 -15.00   0.50    1.01    --  -82.50  42.00  60.00   64
 16  ω   -150.00 -69.00   0.50    1.01    --  -82.50 -33.00  60.00  162
 17  ω     83.00 164.00   0.50    1.01    --   96.67  33.00-180.00  162
 18  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00  90.00   54
 19  ω     82.00 167.00   0.50    1.01    --   96.67  25.00  30.00  170
 20  ω     29.00  68.00   0.50    1.01    --   96.67 -59.00  30.00   78
 21  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00   0.00   54
 22  ω     80.00 163.00   0.50    1.01    --   96.67  42.00  60.00  166
 23  ω     27.00 127.00   0.50    1.01    --   96.67 -87.00  30.00  200
 24  ω     82.00 167.00   0.50    1.01    --   96.67  25.00 -60.00  170
 25  ω     29.00  83.00   0.50    1.01    --   96.67 -68.00  60.00  108
 26  ω     30.00 109.00   0.50    1.01    --   96.67-117.00 120.00  158
 27  ω     81.00 164.00   0.50    1.01    --   96.67 145.00 -90.00  166
 28  ω     29.00  68.00   0.50    1.01    --   96.67 -59.00-150.00   78
 29  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00  60.00   54
 30  ω     29.00  68.00   0.50    1.01    --   96.67 -59.00  90.00   78
 31  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00-180.00   54
 32  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00 150.00   54
 33  ω   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00 -60.00  192
 34  ω    -78.00   4.00   0.50    0.23    --  -40.33 104.00 -90.00  164
 35  ω   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00   0.00  192
 36  ω   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00-120.00  192
 37  ω    -31.00  30.00   0.50    0.23    --  -40.33  25.00  90.00  122
 38  ω   -108.00 -17.00   0.50    0.23    --  -40.33 -64.00 120.00  182
 39  ω   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00  90.00  192
 40  ω     21.00 107.00   0.50    0.23    --   40.33  50.00-120.00  172
 41  ω     14.00 109.00   0.50    0.23    --   40.33  77.00-120.00  190
 42  ω     17.00 108.00   0.50    0.23    --   40.33  64.00 -30.00  182
 43  ω     22.00 106.00   0.50    1.01    --   96.67 -96.00-150.00  168
 44  ω     78.00 163.00   0.50    1.01    --   96.67  50.00 120.00  170
 45  ω     83.00 164.00   0.50    1.01    --   96.67  33.00-120.00  162
 46  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00-120.00   54
 47  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00 -90.00   54
 48  ω     75.00 148.00   0.50    1.01    --   96.67  59.00 -30.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1032743000
_diffrn_orient_matrix_UB_12      0.0289310000
_diffrn_orient_matrix_UB_13      0.0211058000
_diffrn_orient_matrix_UB_21      0.0095339000
_diffrn_orient_matrix_UB_22      0.1391859000
_diffrn_orient_matrix_UB_23      -0.0354439000
_diffrn_orient_matrix_UB_31      -0.0474714000
_diffrn_orient_matrix_UB_32      -0.0349621000
_diffrn_orient_matrix_UB_33      -0.1238168000
_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                2862
_reflns_number_total             3149
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.065
_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)+(0.0517P)²+0.6784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1086
_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:
 C13(H13), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C8(H8), C22(H22), C10(H10), C9(H9), C18(H18), C19(H19),
 C21(H21)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C1(H1A,H1B,H1C)
;
_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 0.49734(7) 0.81032(10) 0.64546(8) 0.0391(3) Uani 1 1 d . . . . .
O2 O 0.71444(7) 0.45587(9) 0.11975(8) 0.0236(2) Uani 1 1 d . . . . .
O3 O 0.86712(8) 0.45555(10) 0.08264(8) 0.0297(3) Uani 1 1 d . . . . .
O1 O 0.78639(9) 0.20488(10) 0.14912(9) 0.0342(3) Uani 1 1 d . . . . .
C7 C 0.79801(10) 0.59302(13) 0.27643(11) 0.0211(3) Uani 1 1 d . . . . .
C12 C 0.83273(10) 0.60213(13) 0.39396(11) 0.0216(3) Uani 1 1 d . . . . .
C17 C 0.64387(10) 0.55617(14) 0.48120(12) 0.0232(3) Uani 1 1 d . . . . .
C5 C 0.77878(11) 0.45082(13) 0.05032(12) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.75380(10) 0.46379(13) 0.23996(11) 0.0214(3) Uani 1 1 d . . . . .
C3 C 0.82715(10) 0.35959(13) 0.29246(12) 0.0226(3) Uani 1 1 d . . . . .
C11 C 0.87432(10) 0.71420(14) 0.44263(12) 0.0235(3) Uani 1 1 d . . . . .
H11 H 0.899614 0.719357 0.522178 0.028 Uiso 1 1 calc R . . . .
C15 C 0.66345(10) 0.44913(14) 0.29485(12) 0.0228(3) Uani 1 1 d . . . . .
H15A H 0.631399 0.365764 0.274046 0.027 Uiso 1 1 calc R . . . .
H15B H 0.614341 0.516587 0.266483 0.027 Uiso 1 1 calc R . . . .
C13 C 0.81429(10) 0.48362(13) 0.45546(11) 0.0225(3) Uani 1 1 d . . . . .
H13 H 0.841500 0.490577 0.538996 0.027 Uiso 1 1 calc R . . . .
C14 C 0.85780(10) 0.37287(13) 0.40507(12) 0.0229(3) Uani 1 1 d . . . . .
H14 H 0.903855 0.316159 0.449902 0.028 Uiso 1 1 calc R . . . .
C8 C 0.79820(10) 0.69908(14) 0.20882(12) 0.0236(3) Uani 1 1 d . . . . .
H8 H 0.771040 0.694823 0.129586 0.028 Uiso 1 1 calc R . . . .
C22 C 0.62256(11) 0.52623(14) 0.58528(12) 0.0257(3) Uani 1 1 d . . . . .
H22 H 0.641914 0.445844 0.618703 0.031 Uiso 1 1 calc R . . . .
C2 C 0.84545(11) 0.24169(14) 0.23343(12) 0.0249(3) Uani 1 1 d . . . . .
C16 C 0.69840(10) 0.45903(13) 0.42575(11) 0.0226(3) Uani 1 1 d . . . . .
H16 H 0.687233 0.374070 0.457680 0.027 Uiso 1 1 calc R . . . .
C10 C 0.87876(11) 0.81897(14) 0.37433(13) 0.0265(3) Uani 1 1 d . . . . .
H10 H 0.909151 0.895314 0.406742 0.032 Uiso 1 1 calc R . . . .
C9 C 0.83875(11) 0.81213(14) 0.25854(12) 0.0266(3) Uani 1 1 d . . . . .
H9 H 0.839039 0.885357 0.212755 0.032 Uiso 1 1 calc R . . . .
C18 C 0.61468(11) 0.67490(14) 0.43388(12) 0.0275(3) Uani 1 1 d . . . . .
H18 H 0.629333 0.697468 0.363518 0.033 Uiso 1 1 calc R . . . .
C20 C 0.54577(11) 0.72615(16) 0.59094(13) 0.0293(3) Uani 1 1 d . . . . .
C19 C 0.56444(11) 0.76085(15) 0.48807(13) 0.0302(3) Uani 1 1 d . . . . .
H19 H 0.543668 0.841023 0.455098 0.036 Uiso 1 1 calc R . . . .
C21 C 0.57380(11) 0.61118(16) 0.64090(12) 0.0287(3) Uani 1 1 d . . . . .
H21 H 0.560107 0.590212 0.712084 0.034 Uiso 1 1 calc R . . . .
C6 C 0.72237(12) 0.43965(15) -0.07025(12) 0.0283(3) Uani 1 1 d . . . . .
H6A H 0.673022 0.371792 -0.076400 0.042 Uiso 1 1 calc GR . . . .
H6B H 0.768243 0.419549 -0.118594 0.042 Uiso 1 1 calc GR . . . .
H6C H 0.688936 0.520290 -0.094621 0.042 Uiso 1 1 calc GR . . . .
C1 C 0.93735(12) 0.16685(15) 0.28156(14) 0.0318(4) Uani 1 1 d . . . . .
H1A H 0.938142 0.143187 0.359985 0.048 Uiso 1 1 calc GR . . . .
H1B H 0.995748 0.218616 0.279825 0.048 Uiso 1 1 calc GR . . . .
H1C H 0.938219 0.089822 0.236330 0.048 Uiso 1 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
F1 C20 1.3680(17) . ?
O2 C5 1.3582(17) . ?
O2 C4 1.4381(16) . ?
O3 C5 1.1999(18) . ?
O1 C2 1.2195(18) . ?
C7 C12 1.4000(19) . ?
C7 C4 1.5159(19) . ?
C7 C8 1.385(2) . ?
C12 C11 1.385(2) . ?
C12 C13 1.5038(19) . ?
C17 C22 1.395(2) . ?
C17 C16 1.516(2) . ?
C17 C18 1.396(2) . ?
C5 C6 1.498(2) . ?
C4 C3 1.533(2) . ?
C4 C15 1.5526(19) . ?
C3 C14 1.342(2) . ?
C3 C2 1.482(2) . ?
C11 C10 1.388(2) . ?
C15 C16 1.5539(18) . ?
C13 C14 1.5037(19) . ?
C13 C16 1.587(2) . ?
C8 C9 1.393(2) . ?
C22 C21 1.384(2) . ?
C2 C1 1.500(2) . ?
C10 C9 1.389(2) . ?
C18 C19 1.393(2) . ?
C20 C19 1.378(2) . ?
C20 C21 1.369(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 C4 118.52(11) . . ?
C12 C7 C4 112.43(12) . . ?
C8 C7 C12 120.04(13) . . ?
C8 C7 C4 127.23(12) . . ?
C7 C12 C13 112.92(12) . . ?
C11 C12 C7 120.41(13) . . ?
C11 C12 C13 126.59(12) . . ?
C22 C17 C16 118.50(13) . . ?
C22 C17 C18 118.21(13) . . ?
C18 C17 C16 123.29(12) . . ?
O2 C5 C6 109.61(12) . . ?
O3 C5 O2 124.12(13) . . ?
O3 C5 C6 126.27(13) . . ?
O2 C4 C7 112.54(11) . . ?
O2 C4 C3 116.34(11) . . ?
O2 C4 C15 105.64(10) . . ?
C7 C4 C3 109.50(11) . . ?
C7 C4 C15 106.05(11) . . ?
C3 C4 C15 105.96(11) . . ?
C14 C3 C4 112.08(12) . . ?
C14 C3 C2 121.90(13) . . ?
C2 C3 C4 124.63(12) . . ?
C12 C11 C10 119.51(13) . . ?
C4 C15 C16 109.55(11) . . ?
C12 C13 C16 107.42(11) . . ?
C14 C13 C12 108.23(11) . . ?
C14 C13 C16 105.06(11) . . ?
C3 C14 C13 115.44(13) . . ?
C7 C8 C9 119.12(13) . . ?
C21 C22 C17 121.38(14) . . ?
O1 C2 C3 120.96(14) . . ?
O1 C2 C1 120.68(13) . . ?
C3 C2 C1 118.35(12) . . ?
C17 C16 C15 115.20(12) . . ?
C17 C16 C13 111.73(11) . . ?
C15 C16 C13 108.02(11) . . ?
C11 C10 C9 119.98(13) . . ?
C10 C9 C8 120.74(13) . . ?
C19 C18 C17 121.12(14) . . ?
F1 C20 C19 118.55(14) . . ?
F1 C20 C21 118.67(13) . . ?
C21 C20 C19 122.78(14) . . ?
C20 C19 C18 118.05(14) . . ?
C20 C21 C22 118.45(14) . . ?

_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.850
