# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_dkr117_0m
_database_code_depnum_ccdc_archive 'CCDC 2247084'
loop_
_audit_author_name
_audit_author_address
'Dineshchakravarthy Senthurpandi'
;Indian Institute of Science, Bangalore, Karnataka
India
;
_audit_update_record             
;
2023-03-08 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 F2 O2 S'
_chemical_formula_sum            'C22 H22 F2 O2 S'
_chemical_formula_weight         388.45

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1488(5)
_cell_length_b                   13.7389(7)
_cell_length_c                   15.2173(8)
_cell_angle_alpha                68.135(2)
_cell_angle_beta                 83.265(2)
_cell_angle_gamma                86.091(2)
_cell_volume                     1954.89(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9799
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.132
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7118
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode x-ray tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            96899
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.449
_diffrn_reflns_theta_max         30.137
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11514
_reflns_number_gt                9278
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.5748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11514
_refine_ls_number_parameters     663
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1_1 S 0.71903(3) 0.60416(2) 0.00226(2) 0.01461(6) Uani 1 1 d . . . . .
F1_1 F 0.68300(7) 0.87374(5) -0.01825(5) 0.02091(15) Uani 1 1 d . . . . .
F2_1 F 0.85950(7) 0.84963(6) 0.05864(5) 0.02320(16) Uani 1 1 d . . . . .
O1_1 O 0.48245(9) 0.71796(7) -0.04989(6) 0.02219(19) Uani 1 1 d . . . . .
O2_1 O 0.42182(8) 0.75858(6) 0.08050(6) 0.01614(16) Uani 1 1 d . . . . .
C1_1 C 0.60942(11) 0.64823(8) 0.08729(7) 0.01247(19) Uani 1 1 d . . . . .
C2_1 C 0.69332(11) 0.71097(8) 0.12315(8) 0.0137(2) Uani 1 1 d . . . . .
H2_1 H 0.7646(14) 0.6696(11) 0.1565(10) 0.017(3) Uiso 1 1 d . . . . .
C3_1 C 0.73121(11) 0.82182(9) 0.06667(8) 0.0161(2) Uani 1 1 d . . . . .
C4_1 C 0.64595(11) 0.80009(9) 0.15463(8) 0.0147(2) Uani 1 1 d . . . . .
C5_1 C 0.57439(12) 0.83323(10) 0.21611(9) 0.0192(2) Uani 1 1 d . . . . .
H5A_1 H 0.5704(15) 0.9073(13) 0.2086(11) 0.028(4) Uiso 1 1 d . . . . .
H5B_1 H 0.5238(16) 0.7852(12) 0.2703(11) 0.027(4) Uiso 1 1 d . . . . .
C6_1 C 0.49839(11) 0.71359(8) 0.02847(8) 0.0149(2) Uani 1 1 d . . . . .
C7_1 C 0.30128(11) 0.82173(9) 0.04614(9) 0.0189(2) Uani 1 1 d . . . . .
C8_1 C 0.20164(14) 0.75067(11) 0.03541(12) 0.0302(3) Uani 1 1 d . . . . .
H8A_1 H 0.1158(18) 0.7895(13) 0.0217(12) 0.039(5) Uiso 1 1 d . . . . .
H8B_1 H 0.2309(16) 0.7317(13) -0.0216(12) 0.029(4) Uiso 1 1 d . . . . .
H8C_1 H 0.1908(18) 0.6866(15) 0.0954(13) 0.047(5) Uiso 1 1 d . . . . .
C9_1 C 0.33796(14) 0.91391(10) -0.04506(10) 0.0229(3) Uani 1 1 d . . . . .
H9A_1 H 0.2589(16) 0.9588(12) -0.0585(11) 0.028(4) Uiso 1 1 d . . . . .
H9B_1 H 0.4114(17) 0.9485(14) -0.0348(12) 0.036(5) Uiso 1 1 d . . . . .
H9C_1 H 0.3654(17) 0.8915(13) -0.0962(13) 0.038(5) Uiso 1 1 d . . . . .
C10_1 C 0.25292(14) 0.85869(11) 0.12726(10) 0.0271(3) Uani 1 1 d . . . . .
H10A_1 H 0.1684(18) 0.8985(14) 0.1134(12) 0.041(5) Uiso 1 1 d . . . . .
H10B_1 H 0.2371(16) 0.7974(13) 0.1871(12) 0.036(4) Uiso 1 1 d . . . . .
H10C_1 H 0.3206(17) 0.9067(13) 0.1344(12) 0.034(4) Uiso 1 1 d . . . . .
C11_1 C 0.83034(11) 0.51802(9) 0.07950(8) 0.0150(2) Uani 1 1 d . . . . .
C12_1 C 0.95152(12) 0.55339(9) 0.08864(8) 0.0178(2) Uani 1 1 d . . . . .
H12_1 H 0.9721(15) 0.6258(12) 0.0539(11) 0.025(4) Uiso 1 1 d . . . . .
C13_1 C 1.04097(13) 0.48407(10) 0.14544(9) 0.0212(2) Uani 1 1 d . . . . .
H13_1 H 1.1250(16) 0.5068(13) 0.1525(11) 0.029(4) Uiso 1 1 d . . . . .
C14_1 C 1.01058(13) 0.37921(10) 0.19202(9) 0.0248(3) Uani 1 1 d . . . . .
H14_1 H 1.0709(16) 0.3334(13) 0.2314(11) 0.031(4) Uiso 1 1 d . . . . .
C15_1 C 0.89072(14) 0.34343(10) 0.18192(10) 0.0265(3) Uani 1 1 d . . . . .
H15_1 H 0.8689(17) 0.2692(14) 0.2131(12) 0.039(5) Uiso 1 1 d . . . . .
C16_1 C 0.80017(12) 0.41222(9) 0.12598(9) 0.0212(2) Uani 1 1 d . . . . .
H16_1 H 0.7145(17) 0.3871(13) 0.1191(11) 0.032(4) Uiso 1 1 d . . . . .
C17_1 C 0.54290(11) 0.55662(8) 0.16860(8) 0.0133(2) Uani 1 1 d . . . . .
C18_1 C 0.46915(11) 0.48765(9) 0.14712(8) 0.0173(2) Uani 1 1 d . . . . .
H18_1 H 0.4611(15) 0.4997(12) 0.0812(11) 0.023(4) Uiso 1 1 d . . . . .
C19_1 C 0.40621(12) 0.40415(10) 0.21912(9) 0.0207(2) Uani 1 1 d . . . . .
H19_1 H 0.3570(17) 0.3586(13) 0.2040(12) 0.033(4) Uiso 1 1 d . . . . .
C20_1 C 0.41497(13) 0.38861(10) 0.31390(9) 0.0233(3) Uani 1 1 d . . . . .
H20_1 H 0.3703(16) 0.3307(13) 0.3631(12) 0.031(4) Uiso 1 1 d . . . . .
C21_1 C 0.48657(13) 0.45762(10) 0.33562(9) 0.0229(3) Uani 1 1 d . . . . .
H21_1 H 0.4911(16) 0.4484(12) 0.4010(12) 0.029(4) Uiso 1 1 d . . . . .
C22_1 C 0.55076(12) 0.54121(9) 0.26360(8) 0.0176(2) Uani 1 1 d . . . . .
H22_1 H 0.5974(15) 0.5860(12) 0.2807(11) 0.024(4) Uiso 1 1 d . . . . .
S1_2 S 0.25225(3) 0.09867(2) 0.50709(2) 0.01621(7) Uani 1 1 d . . . . .
F1_2 F 0.34719(7) 0.36911(6) 0.56598(5) 0.02369(16) Uani 1 1 d . . . . .
F2_2 F 0.17928(7) 0.38842(6) 0.48218(5) 0.02182(15) Uani 1 1 d . . . . .
O1_2 O 0.04744(9) 0.22868(7) 0.42439(6) 0.02330(19) Uani 1 1 d . . . . .
O2_2 O -0.07096(8) 0.24965(6) 0.55204(6) 0.01784(17) Uani 1 1 d . . . . .
C1_2 C 0.12849(11) 0.15078(8) 0.57994(8) 0.0138(2) Uani 1 1 d . . . . .
C2_2 C 0.20034(11) 0.21901(9) 0.61732(8) 0.0151(2) Uani 1 1 d . . . . .
H2_2 H 0.2737(14) 0.1827(11) 0.6509(10) 0.016(3) Uiso 1 1 d . . . . .
C3_2 C 0.22457(12) 0.33382(9) 0.56738(8) 0.0173(2) Uani 1 1 d . . . . .
C4_2 C 0.13514(11) 0.29994(9) 0.65388(8) 0.0157(2) Uani 1 1 d . . . . .
C5_2 C 0.05158(13) 0.32198(10) 0.71706(9) 0.0214(2) Uani 1 1 d . . . . .
H5A_2 H 0.0348(16) 0.3937(13) 0.7136(11) 0.030(4) Uiso 1 1 d . . . . .
H5B_2 H 0.0034(16) 0.2663(12) 0.7684(11) 0.027(4) Uiso 1 1 d . . . . .
C6_2 C 0.03106(11) 0.21501(8) 0.50778(8) 0.0157(2) Uani 1 1 d . . . . .
C7_2 C -0.18236(12) 0.31024(10) 0.49893(9) 0.0210(2) Uani 1 1 d . . . . .
C8_2 C -0.13318(14) 0.41440(10) 0.42743(10) 0.0233(3) Uani 1 1 d . . . . .
H8A_2 H -0.2078(17) 0.4554(13) 0.3992(12) 0.037(5) Uiso 1 1 d . . . . .
H8B_2 H -0.0880(18) 0.4504(14) 0.4597(13) 0.040(5) Uiso 1 1 d . . . . .
H8C_2 H -0.0699(16) 0.4044(12) 0.3787(12) 0.031(4) Uiso 1 1 d . . . . .
C9_2 C -0.27762(15) 0.32468(14) 0.57785(11) 0.0346(3) Uani 1 1 d . . . . .
H9A_2 H -0.3576(18) 0.3650(14) 0.5497(13) 0.045(5) Uiso 1 1 d . . . . .
H9B_2 H -0.3029(17) 0.2557(14) 0.6267(13) 0.042(5) Uiso 1 1 d . . . . .
H9C_2 H -0.2383(15) 0.3625(12) 0.6106(11) 0.023(4) Uiso 1 1 d . . . . .
C10_2 C -0.24243(15) 0.24566(11) 0.45178(11) 0.0292(3) Uani 1 1 d . . . . .
H10A_2 H -0.3255(18) 0.2791(14) 0.4284(12) 0.040(5) Uiso 1 1 d . . . . .
H10B_2 H -0.1804(18) 0.2433(14) 0.3935(13) 0.046(5) Uiso 1 1 d . . . . .
H10C_2 H -0.2593(16) 0.1708(14) 0.4978(12) 0.036(5) Uiso 1 1 d . . . . .
C11_2 C 0.05634(11) 0.06237(8) 0.66040(8) 0.0139(2) Uani 1 1 d . . . . .
C12_2 C 0.07113(12) 0.04093(9) 0.75569(8) 0.0165(2) Uani 1 1 d . . . . .
H12_2 H 0.1264(14) 0.0825(11) 0.7735(10) 0.020(4) Uiso 1 1 d . . . . .
C13_2 C 0.00567(12) -0.04283(9) 0.82700(9) 0.0198(2) Uani 1 1 d . . . . .
H13_2 H 0.0159(15) -0.0576(12) 0.8928(11) 0.024(4) Uiso 1 1 d . . . . .
C14_2 C -0.07445(12) -0.10561(9) 0.80399(9) 0.0198(2) Uani 1 1 d . . . . .
H14_2 H -0.1174(16) -0.1629(13) 0.8527(12) 0.028(4) Uiso 1 1 d . . . . .
C15_2 C -0.08971(12) -0.08476(9) 0.70896(9) 0.0186(2) Uani 1 1 d . . . . .
H15_2 H -0.1449(16) -0.1261(13) 0.6927(11) 0.028(4) Uiso 1 1 d . . . . .
C16_2 C -0.02526(11) -0.00122(9) 0.63797(8) 0.0166(2) Uani 1 1 d . . . . .
H16_2 H -0.0376(14) 0.0147(11) 0.5719(11) 0.019(4) Uiso 1 1 d . . . . .
C17_2 C 0.35930(11) 0.02374(9) 0.59394(8) 0.0162(2) Uani 1 1 d . . . . .
C18_2 C 0.48227(12) 0.06349(10) 0.59390(9) 0.0197(2) Uani 1 1 d . . . . .
H18_2 H 0.5055(15) 0.1313(12) 0.5475(11) 0.025(4) Uiso 1 1 d . . . . .
C19_2 C 0.57097(12) 0.00388(10) 0.65754(10) 0.0234(3) Uani 1 1 d . . . . .
H19_2 H 0.6558(17) 0.0306(13) 0.6568(12) 0.037(5) Uiso 1 1 d . . . . .
C20_2 C 0.53759(13) -0.09536(11) 0.72168(10) 0.0257(3) Uani 1 1 d . . . . .
H20_2 H 0.5984(17) -0.1341(13) 0.7640(12) 0.035(4) Uiso 1 1 d . . . . .
C21_2 C 0.41604(13) -0.13543(10) 0.72176(10) 0.0260(3) Uani 1 1 d . . . . .
H21_2 H 0.3933(17) -0.2060(14) 0.7676(12) 0.038(5) Uiso 1 1 d . . . . .
C22_2 C 0.32709(13) -0.07654(9) 0.65802(9) 0.0209(2) Uani 1 1 d . . . . .
H22_2 H 0.2428(16) -0.1040(12) 0.6582(11) 0.026(4) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1_1 C11_1 1.7753(11) . ?
S1_1 C1_1 1.8527(11) . ?
F1_1 C3_1 1.3536(13) . ?
F2_1 C3_1 1.3608(13) . ?
O1_1 C6_1 1.2009(14) . ?
O2_1 C6_1 1.3294(13) . ?
O2_1 C7_1 1.4799(13) . ?
C1_1 C2_1 1.5249(15) . ?
C1_1 C17_1 1.5267(15) . ?
C1_1 C6_1 1.5418(15) . ?
C2_1 C3_1 1.4944(15) . ?
C2_1 C4_1 1.5042(15) . ?
C2_1 H2_1 0.959(14) . ?
C3_1 C4_1 1.4476(15) . ?
C4_1 C5_1 1.3125(16) . ?
C5_1 H5A_1 0.979(16) . ?
C5_1 H5B_1 0.959(16) . ?
C7_1 C8_1 1.5147(18) . ?
C7_1 C9_1 1.5174(17) . ?
C7_1 C10_1 1.5209(18) . ?
C8_1 H8A_1 0.992(18) . ?
C8_1 H8B_1 1.002(17) . ?
C8_1 H8C_1 1.006(19) . ?
C9_1 H9A_1 0.971(16) . ?
C9_1 H9B_1 0.968(18) . ?
C9_1 H9C_1 0.946(18) . ?
C10_1 H10A_1 0.986(18) . ?
C10_1 H10B_1 0.988(17) . ?
C10_1 H10C_1 1.025(17) . ?
C11_1 C12_1 1.3928(16) . ?
C11_1 C16_1 1.3968(16) . ?
C12_1 C13_1 1.3897(17) . ?
C12_1 H12_1 0.962(15) . ?
C13_1 C14_1 1.3862(18) . ?
C13_1 H13_1 0.959(16) . ?
C14_1 C15_1 1.388(2) . ?
C14_1 H14_1 0.939(16) . ?
C15_1 C16_1 1.3886(18) . ?
C15_1 H15_1 0.980(17) . ?
C16_1 H16_1 0.987(16) . ?
C17_1 C22_1 1.3921(15) . ?
C17_1 C18_1 1.3962(15) . ?
C18_1 C19_1 1.3871(17) . ?
C18_1 H18_1 0.967(15) . ?
C19_1 C20_1 1.3900(18) . ?
C19_1 H19_1 0.933(17) . ?
C20_1 C21_1 1.3857(19) . ?
C20_1 H20_1 0.961(17) . ?
C21_1 C22_1 1.3934(17) . ?
C21_1 H21_1 0.961(16) . ?
C22_1 H22_1 0.926(16) . ?
S1_2 C17_2 1.7770(12) . ?
S1_2 C1_2 1.8603(11) . ?
F1_2 C3_2 1.3610(13) . ?
F2_2 C3_2 1.3503(13) . ?
O1_2 C6_2 1.2045(14) . ?
O2_2 C6_2 1.3267(14) . ?
O2_2 C7_2 1.4864(14) . ?
C1_2 C11_2 1.5211(15) . ?
C1_2 C2_2 1.5238(15) . ?
C1_2 C6_2 1.5415(15) . ?
C2_2 C3_2 1.4974(16) . ?
C2_2 C4_2 1.5026(15) . ?
C2_2 H2_2 0.956(14) . ?
C3_2 C4_2 1.4471(16) . ?
C4_2 C5_2 1.3136(16) . ?
C5_2 H5A_2 0.971(16) . ?
C5_2 H5B_2 0.975(16) . ?
C7_2 C8_2 1.5136(18) . ?
C7_2 C9_2 1.5151(19) . ?
C7_2 C10_2 1.5246(19) . ?
C8_2 H8A_2 0.956(17) . ?
C8_2 H8B_2 0.980(18) . ?
C8_2 H8C_2 0.967(17) . ?
C9_2 H9A_2 0.996(18) . ?
C9_2 H9B_2 0.990(18) . ?
C9_2 H9C_2 0.972(16) . ?
C10_2 H10A_2 0.972(18) . ?
C10_2 H10B_2 1.035(19) . ?
C10_2 H10C_2 1.019(17) . ?
C11_2 C12_2 1.3925(15) . ?
C11_2 C16_2 1.3974(16) . ?
C12_2 C13_2 1.3957(17) . ?
C12_2 H12_2 0.954(15) . ?
C13_2 C14_2 1.3838(18) . ?
C13_2 H13_2 0.962(15) . ?
C14_2 C15_2 1.3912(17) . ?
C14_2 H14_2 0.946(16) . ?
C15_2 C16_2 1.3875(16) . ?
C15_2 H15_2 0.936(16) . ?
C16_2 H16_2 0.968(15) . ?
C17_2 C22_2 1.3935(16) . ?
C17_2 C18_2 1.3958(17) . ?
C18_2 C19_2 1.3900(18) . ?
C18_2 H18_2 0.961(15) . ?
C19_2 C20_2 1.3859(19) . ?
C19_2 H19_2 0.956(17) . ?
C20_2 C21_2 1.385(2) . ?
C20_2 H20_2 0.933(17) . ?
C21_2 C22_2 1.3897(18) . ?
C21_2 H21_2 0.984(17) . ?
C22_2 H22_2 0.957(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11_1 S1_1 C1_1 100.56(5) . . ?
C6_1 O2_1 C7_1 122.09(9) . . ?
C2_1 C1_1 C17_1 112.10(9) . . ?
C2_1 C1_1 C6_1 113.95(9) . . ?
C17_1 C1_1 C6_1 106.82(9) . . ?
C2_1 C1_1 S1_1 107.44(7) . . ?
C17_1 C1_1 S1_1 112.14(7) . . ?
C6_1 C1_1 S1_1 104.20(7) . . ?
C3_1 C2_1 C4_1 57.73(7) . . ?
C3_1 C2_1 C1_1 123.41(9) . . ?
C4_1 C2_1 C1_1 126.67(9) . . ?
C3_1 C2_1 H2_1 112.3(8) . . ?
C4_1 C2_1 H2_1 113.7(8) . . ?
C1_1 C2_1 H2_1 112.4(8) . . ?
F1_1 C3_1 F2_1 107.79(9) . . ?
F1_1 C3_1 C4_1 120.61(10) . . ?
F2_1 C3_1 C4_1 121.61(10) . . ?
F1_1 C3_1 C2_1 119.84(9) . . ?
F2_1 C3_1 C2_1 119.60(10) . . ?
C4_1 C3_1 C2_1 61.47(7) . . ?
C5_1 C4_1 C3_1 150.07(11) . . ?
C5_1 C4_1 C2_1 149.08(11) . . ?
C3_1 C4_1 C2_1 60.80(7) . . ?
C4_1 C5_1 H5A_1 121.6(9) . . ?
C4_1 C5_1 H5B_1 120.8(10) . . ?
H5A_1 C5_1 H5B_1 117.6(13) . . ?
O1_1 C6_1 O2_1 126.71(10) . . ?
O1_1 C6_1 C1_1 124.35(10) . . ?
O2_1 C6_1 C1_1 108.86(9) . . ?
O2_1 C7_1 C8_1 108.73(9) . . ?
O2_1 C7_1 C9_1 109.96(10) . . ?
C8_1 C7_1 C9_1 113.41(11) . . ?
O2_1 C7_1 C10_1 102.24(9) . . ?
C8_1 C7_1 C10_1 110.85(12) . . ?
C9_1 C7_1 C10_1 111.04(11) . . ?
C7_1 C8_1 H8A_1 109.5(10) . . ?
C7_1 C8_1 H8B_1 110.1(9) . . ?
H8A_1 C8_1 H8B_1 105.2(13) . . ?
C7_1 C8_1 H8C_1 109.3(11) . . ?
H8A_1 C8_1 H8C_1 110.9(14) . . ?
H8B_1 C8_1 H8C_1 111.7(14) . . ?
C7_1 C9_1 H9A_1 106.5(9) . . ?
C7_1 C9_1 H9B_1 108.0(10) . . ?
H9A_1 C9_1 H9B_1 112.8(14) . . ?
C7_1 C9_1 H9C_1 111.4(10) . . ?
H9A_1 C9_1 H9C_1 110.0(14) . . ?
H9B_1 C9_1 H9C_1 108.1(15) . . ?
C7_1 C10_1 H10A_1 109.0(10) . . ?
C7_1 C10_1 H10B_1 109.7(10) . . ?
H10A_1 C10_1 H10B_1 108.4(14) . . ?
C7_1 C10_1 H10C_1 110.7(9) . . ?
H10A_1 C10_1 H10C_1 108.6(14) . . ?
H10B_1 C10_1 H10C_1 110.4(13) . . ?
C12_1 C11_1 C16_1 119.80(11) . . ?
C12_1 C11_1 S1_1 120.51(9) . . ?
C16_1 C11_1 S1_1 119.52(9) . . ?
C13_1 C12_1 C11_1 120.10(11) . . ?
C13_1 C12_1 H12_1 121.4(9) . . ?
C11_1 C12_1 H12_1 118.5(9) . . ?
C14_1 C13_1 C12_1 120.05(12) . . ?
C14_1 C13_1 H13_1 118.5(10) . . ?
C12_1 C13_1 H13_1 121.4(10) . . ?
C13_1 C14_1 C15_1 119.98(12) . . ?
C13_1 C14_1 H14_1 119.3(10) . . ?
C15_1 C14_1 H14_1 120.7(10) . . ?
C14_1 C15_1 C16_1 120.43(12) . . ?
C14_1 C15_1 H15_1 120.9(10) . . ?
C16_1 C15_1 H15_1 118.7(10) . . ?
C15_1 C16_1 C11_1 119.63(12) . . ?
C15_1 C16_1 H16_1 120.6(9) . . ?
C11_1 C16_1 H16_1 119.7(9) . . ?
C22_1 C17_1 C18_1 118.94(10) . . ?
C22_1 C17_1 C1_1 121.99(10) . . ?
C18_1 C17_1 C1_1 119.05(10) . . ?
C19_1 C18_1 C17_1 120.68(11) . . ?
C19_1 C18_1 H18_1 120.3(9) . . ?
C17_1 C18_1 H18_1 119.0(9) . . ?
C18_1 C19_1 C20_1 120.23(12) . . ?
C18_1 C19_1 H19_1 120.0(10) . . ?
C20_1 C19_1 H19_1 119.8(10) . . ?
C21_1 C20_1 C19_1 119.33(11) . . ?
C21_1 C20_1 H20_1 121.3(10) . . ?
C19_1 C20_1 H20_1 119.4(10) . . ?
C20_1 C21_1 C22_1 120.69(12) . . ?
C20_1 C21_1 H21_1 119.7(10) . . ?
C22_1 C21_1 H21_1 119.6(10) . . ?
C17_1 C22_1 C21_1 120.13(11) . . ?
C17_1 C22_1 H22_1 121.5(10) . . ?
C21_1 C22_1 H22_1 118.4(9) . . ?
C17_2 S1_2 C1_2 100.83(5) . . ?
C6_2 O2_2 C7_2 120.51(9) . . ?
C11_2 C1_2 C2_2 111.71(9) . . ?
C11_2 C1_2 C6_2 110.03(9) . . ?
C2_2 C1_2 C6_2 112.37(9) . . ?
C11_2 C1_2 S1_2 111.24(7) . . ?
C2_2 C1_2 S1_2 108.32(7) . . ?
C6_2 C1_2 S1_2 102.84(7) . . ?
C3_2 C2_2 C4_2 57.68(7) . . ?
C3_2 C2_2 C1_2 125.97(10) . . ?
C4_2 C2_2 C1_2 125.29(10) . . ?
C3_2 C2_2 H2_2 111.7(8) . . ?
C4_2 C2_2 H2_2 113.2(8) . . ?
C1_2 C2_2 H2_2 112.5(8) . . ?
F2_2 C3_2 F1_2 107.76(9) . . ?
F2_2 C3_2 C4_2 121.15(10) . . ?
F1_2 C3_2 C4_2 121.08(10) . . ?
F2_2 C3_2 C2_2 121.23(10) . . ?
F1_2 C3_2 C2_2 118.35(10) . . ?
C4_2 C3_2 C2_2 61.34(8) . . ?
C5_2 C4_2 C3_2 150.28(12) . . ?
C5_2 C4_2 C2_2 148.65(12) . . ?
C3_2 C4_2 C2_2 60.98(8) . . ?
C4_2 C5_2 H5A_2 121.4(10) . . ?
C4_2 C5_2 H5B_2 120.4(9) . . ?
H5A_2 C5_2 H5B_2 118.2(13) . . ?
O1_2 C6_2 O2_2 126.74(11) . . ?
O1_2 C6_2 C1_2 123.47(10) . . ?
O2_2 C6_2 C1_2 109.77(9) . . ?
O2_2 C7_2 C8_2 109.56(10) . . ?
O2_2 C7_2 C9_2 101.84(10) . . ?
C8_2 C7_2 C9_2 111.48(12) . . ?
O2_2 C7_2 C10_2 109.65(10) . . ?
C8_2 C7_2 C10_2 112.15(11) . . ?
C9_2 C7_2 C10_2 111.66(12) . . ?
C7_2 C8_2 H8A_2 108.3(10) . . ?
C7_2 C8_2 H8B_2 109.5(11) . . ?
H8A_2 C8_2 H8B_2 110.7(14) . . ?
C7_2 C8_2 H8C_2 111.0(9) . . ?
H8A_2 C8_2 H8C_2 109.8(14) . . ?
H8B_2 C8_2 H8C_2 107.5(14) . . ?
C7_2 C9_2 H9A_2 108.7(11) . . ?
C7_2 C9_2 H9B_2 110.4(10) . . ?
H9A_2 C9_2 H9B_2 110.6(14) . . ?
C7_2 C9_2 H9C_2 112.2(9) . . ?
H9A_2 C9_2 H9C_2 108.7(14) . . ?
H9B_2 C9_2 H9C_2 106.3(14) . . ?
C7_2 C10_2 H10A_2 109.1(10) . . ?
C7_2 C10_2 H10B_2 110.6(10) . . ?
H10A_2 C10_2 H10B_2 107.0(14) . . ?
C7_2 C10_2 H10C_2 111.7(10) . . ?
H10A_2 C10_2 H10C_2 109.4(14) . . ?
H10B_2 C10_2 H10C_2 108.8(14) . . ?
C12_2 C11_2 C16_2 118.73(10) . . ?
C12_2 C11_2 C1_2 122.32(10) . . ?
C16_2 C11_2 C1_2 118.94(10) . . ?
C11_2 C12_2 C13_2 120.29(11) . . ?
C11_2 C12_2 H12_2 120.9(9) . . ?
C13_2 C12_2 H12_2 118.8(9) . . ?
C14_2 C13_2 C12_2 120.52(11) . . ?
C14_2 C13_2 H13_2 119.2(9) . . ?
C12_2 C13_2 H13_2 120.3(9) . . ?
C13_2 C14_2 C15_2 119.57(11) . . ?
C13_2 C14_2 H14_2 120.0(10) . . ?
C15_2 C14_2 H14_2 120.5(10) . . ?
C16_2 C15_2 C14_2 120.02(11) . . ?
C16_2 C15_2 H15_2 119.7(10) . . ?
C14_2 C15_2 H15_2 120.2(10) . . ?
C15_2 C16_2 C11_2 120.88(11) . . ?
C15_2 C16_2 H16_2 120.3(9) . . ?
C11_2 C16_2 H16_2 118.8(9) . . ?
C22_2 C17_2 C18_2 119.20(11) . . ?
C22_2 C17_2 S1_2 121.52(9) . . ?
C18_2 C17_2 S1_2 119.15(9) . . ?
C19_2 C18_2 C17_2 120.28(12) . . ?
C19_2 C18_2 H18_2 121.0(9) . . ?
C17_2 C18_2 H18_2 118.7(9) . . ?
C20_2 C19_2 C18_2 120.14(12) . . ?
C20_2 C19_2 H19_2 119.6(10) . . ?
C18_2 C19_2 H19_2 120.3(10) . . ?
C21_2 C20_2 C19_2 119.85(12) . . ?
C21_2 C20_2 H20_2 121.3(10) . . ?
C19_2 C20_2 H20_2 118.9(10) . . ?
C20_2 C21_2 C22_2 120.35(12) . . ?
C20_2 C21_2 H21_2 119.2(10) . . ?
C22_2 C21_2 H21_2 120.4(10) . . ?
C21_2 C22_2 C17_2 120.17(12) . . ?
C21_2 C22_2 H22_2 120.5(9) . . ?
C17_2 C22_2 H22_2 119.4(9) . . ?

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
C11_1 S1_1 C1_1 C2_1 65.42(8) . . . . ?
C11_1 S1_1 C1_1 C17_1 -58.19(8) . . . . ?
C11_1 S1_1 C1_1 C6_1 -173.36(7) . . . . ?
C17_1 C1_1 C2_1 C3_1 -158.50(10) . . . . ?
C6_1 C1_1 C2_1 C3_1 -37.04(14) . . . . ?
S1_1 C1_1 C2_1 C3_1 77.86(11) . . . . ?
C17_1 C1_1 C2_1 C4_1 -86.33(13) . . . . ?
C6_1 C1_1 C2_1 C4_1 35.13(15) . . . . ?
S1_1 C1_1 C2_1 C4_1 150.03(9) . . . . ?
C4_1 C2_1 C3_1 F1_1 -110.88(11) . . . . ?
C1_1 C2_1 C3_1 F1_1 4.57(16) . . . . ?
C4_1 C2_1 C3_1 F2_1 112.17(11) . . . . ?
C1_1 C2_1 C3_1 F2_1 -132.38(11) . . . . ?
C1_1 C2_1 C3_1 C4_1 115.45(11) . . . . ?
F1_1 C3_1 C4_1 C5_1 -67.6(3) . . . . ?
F2_1 C3_1 C4_1 C5_1 73.7(3) . . . . ?
C2_1 C3_1 C4_1 C5_1 -177.3(2) . . . . ?
F1_1 C3_1 C4_1 C2_1 109.66(11) . . . . ?
F2_1 C3_1 C4_1 C2_1 -109.00(12) . . . . ?
C3_1 C2_1 C4_1 C5_1 177.3(2) . . . . ?
C1_1 C2_1 C4_1 C5_1 67.4(2) . . . . ?
C1_1 C2_1 C4_1 C3_1 -109.98(12) . . . . ?
C7_1 O2_1 C6_1 O1_1 0.55(17) . . . . ?
C7_1 O2_1 C6_1 C1_1 -176.31(9) . . . . ?
C2_1 C1_1 C6_1 O1_1 126.57(12) . . . . ?
C17_1 C1_1 C6_1 O1_1 -109.08(12) . . . . ?
S1_1 C1_1 C6_1 O1_1 9.78(14) . . . . ?
C2_1 C1_1 C6_1 O2_1 -56.48(12) . . . . ?
C17_1 C1_1 C6_1 O2_1 67.87(11) . . . . ?
S1_1 C1_1 C6_1 O2_1 -173.27(7) . . . . ?
C6_1 O2_1 C7_1 C8_1 64.89(14) . . . . ?
C6_1 O2_1 C7_1 C9_1 -59.83(13) . . . . ?
C6_1 O2_1 C7_1 C10_1 -177.84(10) . . . . ?
C1_1 S1_1 C11_1 C12_1 -95.40(10) . . . . ?
C1_1 S1_1 C11_1 C16_1 89.29(10) . . . . ?
C16_1 C11_1 C12_1 C13_1 -1.35(17) . . . . ?
S1_1 C11_1 C12_1 C13_1 -176.65(9) . . . . ?
C11_1 C12_1 C13_1 C14_1 0.95(18) . . . . ?
C12_1 C13_1 C14_1 C15_1 -0.01(19) . . . . ?
C13_1 C14_1 C15_1 C16_1 -0.5(2) . . . . ?
C14_1 C15_1 C16_1 C11_1 0.1(2) . . . . ?
C12_1 C11_1 C16_1 C15_1 0.80(18) . . . . ?
S1_1 C11_1 C16_1 C15_1 176.15(10) . . . . ?
C2_1 C1_1 C17_1 C22_1 5.55(14) . . . . ?
C6_1 C1_1 C17_1 C22_1 -119.92(11) . . . . ?
S1_1 C1_1 C17_1 C22_1 126.52(10) . . . . ?
C2_1 C1_1 C17_1 C18_1 -176.09(9) . . . . ?
C6_1 C1_1 C17_1 C18_1 58.44(12) . . . . ?
S1_1 C1_1 C17_1 C18_1 -55.12(12) . . . . ?
C22_1 C17_1 C18_1 C19_1 -0.94(17) . . . . ?
C1_1 C17_1 C18_1 C19_1 -179.35(10) . . . . ?
C17_1 C18_1 C19_1 C20_1 0.54(18) . . . . ?
C18_1 C19_1 C20_1 C21_1 0.31(19) . . . . ?
C19_1 C20_1 C21_1 C22_1 -0.76(19) . . . . ?
C18_1 C17_1 C22_1 C21_1 0.49(17) . . . . ?
C1_1 C17_1 C22_1 C21_1 178.85(11) . . . . ?
C20_1 C21_1 C22_1 C17_1 0.36(19) . . . . ?
C17_2 S1_2 C1_2 C11_2 -61.16(9) . . . . ?
C17_2 S1_2 C1_2 C2_2 61.98(8) . . . . ?
C17_2 S1_2 C1_2 C6_2 -178.90(7) . . . . ?
C11_2 C1_2 C2_2 C3_2 -148.94(11) . . . . ?
C6_2 C1_2 C2_2 C3_2 -24.72(15) . . . . ?
S1_2 C1_2 C2_2 C3_2 88.21(12) . . . . ?
C11_2 C1_2 C2_2 C4_2 -76.14(13) . . . . ?
C6_2 C1_2 C2_2 C4_2 48.09(14) . . . . ?
S1_2 C1_2 C2_2 C4_2 161.01(9) . . . . ?
C4_2 C2_2 C3_2 F2_2 -110.98(12) . . . . ?
C1_2 C2_2 C3_2 F2_2 1.70(17) . . . . ?
C4_2 C2_2 C3_2 F1_2 111.94(11) . . . . ?
C1_2 C2_2 C3_2 F1_2 -135.38(11) . . . . ?
C1_2 C2_2 C3_2 C4_2 112.67(12) . . . . ?
F2_2 C3_2 C4_2 C5_2 -65.3(3) . . . . ?
F1_2 C3_2 C4_2 C5_2 76.0(3) . . . . ?
C2_2 C3_2 C4_2 C5_2 -176.4(2) . . . . ?
F2_2 C3_2 C4_2 C2_2 111.10(12) . . . . ?
F1_2 C3_2 C4_2 C2_2 -107.59(12) . . . . ?
C3_2 C2_2 C4_2 C5_2 176.6(2) . . . . ?
C1_2 C2_2 C4_2 C5_2 62.8(3) . . . . ?
C1_2 C2_2 C4_2 C3_2 -113.81(12) . . . . ?
C7_2 O2_2 C6_2 O1_2 1.49(18) . . . . ?
C7_2 O2_2 C6_2 C1_2 -177.42(9) . . . . ?
C11_2 C1_2 C6_2 O1_2 -123.29(12) . . . . ?
C2_2 C1_2 C6_2 O1_2 111.56(12) . . . . ?
S1_2 C1_2 C6_2 O1_2 -4.70(13) . . . . ?
C11_2 C1_2 C6_2 O2_2 55.67(11) . . . . ?
C2_2 C1_2 C6_2 O2_2 -69.48(12) . . . . ?
S1_2 C1_2 C6_2 O2_2 174.26(7) . . . . ?
C6_2 O2_2 C7_2 C8_2 -66.22(14) . . . . ?
C6_2 O2_2 C7_2 C9_2 175.64(11) . . . . ?
C6_2 O2_2 C7_2 C10_2 57.26(14) . . . . ?
C2_2 C1_2 C11_2 C12_2 -7.79(14) . . . . ?
C6_2 C1_2 C11_2 C12_2 -133.31(11) . . . . ?
S1_2 C1_2 C11_2 C12_2 113.39(10) . . . . ?
C2_2 C1_2 C11_2 C16_2 173.75(10) . . . . ?
C6_2 C1_2 C11_2 C16_2 48.23(13) . . . . ?
S1_2 C1_2 C11_2 C16_2 -65.07(12) . . . . ?
C16_2 C11_2 C12_2 C13_2 0.20(16) . . . . ?
C1_2 C11_2 C12_2 C13_2 -178.26(10) . . . . ?
C11_2 C12_2 C13_2 C14_2 0.09(17) . . . . ?
C12_2 C13_2 C14_2 C15_2 -0.05(18) . . . . ?
C13_2 C14_2 C15_2 C16_2 -0.27(18) . . . . ?
C14_2 C15_2 C16_2 C11_2 0.57(17) . . . . ?
C12_2 C11_2 C16_2 C15_2 -0.53(16) . . . . ?
C1_2 C11_2 C16_2 C15_2 177.99(10) . . . . ?
C1_2 S1_2 C17_2 C22_2 80.27(10) . . . . ?
C1_2 S1_2 C17_2 C18_2 -103.97(10) . . . . ?
C22_2 C17_2 C18_2 C19_2 -0.44(18) . . . . ?
S1_2 C17_2 C18_2 C19_2 -176.30(9) . . . . ?
C17_2 C18_2 C19_2 C20_2 -0.21(19) . . . . ?
C18_2 C19_2 C20_2 C21_2 0.5(2) . . . . ?
C19_2 C20_2 C21_2 C22_2 -0.2(2) . . . . ?
C20_2 C21_2 C22_2 C17_2 -0.5(2) . . . . ?
C18_2 C17_2 C22_2 C21_2 0.78(18) . . . . ?
S1_2 C17_2 C22_2 C21_2 176.54(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8_1 H8B_1 O1_1 1.002(17) 2.545(16) 3.0661(18) 112.1(11) . yes
C9_1 H9C_1 O1_1 0.946(18) 2.480(17) 2.9978(15) 114.4(13) . yes
C8_2 H8C_2 O1_2 0.967(17) 2.506(16) 3.0501(16) 115.5(11) . yes
C10_2 H10B_2 O1_2 1.035(19) 2.394(18) 2.9282(18) 111.0(12) . yes

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.053



####################################################################### 
# 
# 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_reduced1
_database_code_depnum_ccdc_archive 'CCDC 2250643'
loop_
_audit_author_name
_audit_author_address
'Dineshchakravarthy Senthurpandi'
;Indian Institute of Science, Bangalore, Karnataka
India
;
_audit_update_record             
;
2023-03-22 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;

_vrf_PLAT430_reduced1            
;
PROBLEM: Short Inter D...A Contact  O1       ..O1       .       2.82 Ang.
RESPONSE: This inter-molecular short contact is between the same 
centrosymmetrically related oxygens and not due to missed hydrogen bonds.

d(O1-C1) = 1.410A
d(O1-C7) = 1.349A
angle(C1-O1-C7) = 118.39deg

d(O1 ... O1#) = 2.823A
d(O1 ... C1#) = 3.164A
# = 1-x, 1-y, 1-z
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 F2 O2 Se'
_chemical_formula_sum            'C20 H18 F2 O2 Se'
_chemical_formula_weight         407.30

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'
O O 0.0106 0.0060 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8764(10)
_cell_length_b                   12.9635(12)
_cell_length_c                   12.9906(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.134(4)
_cell_angle_gamma                90
_cell_volume                     1830.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    9694
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      29.58

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    2.080
_shelx_estimated_absorpt_T_min   0.505
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6517
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS-2016/2
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            92660
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.143
_diffrn_reflns_theta_max         29.590
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5120
_reflns_number_gt                4759
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)²+1.6095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5120
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
Se1 Se 0.60687(2) 0.79007(2) 0.43188(2) 0.02218(5) Uani 1 1 d . . . . .
C1 C 0.47997(14) 0.52814(12) 0.64994(11) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.36615(15) 0.57145(13) 0.66917(13) 0.0265(3) Uani 1 1 d . . . . .
C3 C 0.29421(17) 0.52039(14) 0.73998(15) 0.0342(4) Uani 1 1 d . . . . .
H3 H 0.215986 0.547659 0.755551 0.041 Uiso 1 1 calc R U . . .
C4 C 0.33493(18) 0.43096(14) 0.78769(14) 0.0352(4) Uani 1 1 d . . . . .
H4 H 0.284410 0.397042 0.835261 0.042 Uiso 1 1 calc R U . . .
C5 C 0.44887(17) 0.39046(13) 0.76663(13) 0.0304(3) Uani 1 1 d . . . . .
H5 H 0.475944 0.328877 0.799999 0.036 Uiso 1 1 calc R U . . .
C6 C 0.52467(15) 0.43895(12) 0.69690(12) 0.0240(3) Uani 1 1 d . . . . .
C7 C 0.63033(12) 0.64761(11) 0.59758(11) 0.0182(2) Uani 1 1 d . . . . .
C8 C 0.69991(13) 0.67871(11) 0.50389(11) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.703029 0.617935 0.456655 0.024 Uiso 1 1 calc R U . . .
C9 C 0.82976(14) 0.70952(12) 0.53354(12) 0.0228(3) Uani 1 1 d . . . . .
H9 H 0.839767 0.771017 0.579562 0.027 Uiso 1 1 calc R U . . .
C10 C 0.92981(15) 0.69151(14) 0.45866(14) 0.0283(3) Uani 1 1 d . . . . .
C11 C 0.92399(14) 0.62534(13) 0.54805(14) 0.0279(3) Uani 1 1 d . . . . .
C12 C 0.32048(18) 0.66849(15) 0.61717(17) 0.0382(4) Uani 1 1 d . . . . .
H12A H 0.301971 0.720155 0.669443 0.057 Uiso 1 1 calc R U . . .
H12B H 0.245759 0.653276 0.575440 0.057 Uiso 1 1 calc R U . . .
H12C H 0.383948 0.695305 0.572716 0.057 Uiso 1 1 calc R U . . .
C13 C 0.64823(16) 0.39486(14) 0.67332(14) 0.0320(4) Uani 1 1 d . . . . .
H13A H 0.648165 0.373754 0.600879 0.048 Uiso 1 1 calc R U . . .
H13B H 0.665208 0.334833 0.717446 0.048 Uiso 1 1 calc R U . . .
H13C H 0.711914 0.447242 0.686253 0.048 Uiso 1 1 calc R U . . .
C14 C 0.63222(14) 0.89854(12) 0.53058(12) 0.0227(3) Uani 1 1 d . . . . .
C15 C 0.73392(16) 0.96344(13) 0.52515(13) 0.0292(3) Uani 1 1 d . . . . .
H15 H 0.793944 0.951457 0.475222 0.035 Uiso 1 1 calc R U . . .
C16 C 0.74708(18) 1.04597(14) 0.59333(15) 0.0356(4) Uani 1 1 d . . . . .
H16 H 0.816439 1.090226 0.590044 0.043 Uiso 1 1 calc R U . . .
C17 C 0.65951(18) 1.06372(14) 0.66578(14) 0.0339(4) Uani 1 1 d . . . . .
H17 H 0.668211 1.120845 0.711269 0.041 Uiso 1 1 calc R U . . .
C18 C 0.55935(16) 0.99866(14) 0.67229(13) 0.0307(3) Uani 1 1 d . . . . .
H18 H 0.500312 1.010291 0.723113 0.037 Uiso 1 1 calc R U . . .
C19 C 0.54508(15) 0.91636(13) 0.60455(12) 0.0258(3) Uani 1 1 d . . . . .
H19 H 0.475815 0.872103 0.608613 0.031 Uiso 1 1 calc R U . . .
C20 C 0.98407(19) 0.71933(18) 0.37472(15) 0.0403(4) Uani 1 1 d . . . . .
H20A H 1.056141 0.684450 0.354603 0.048 Uiso 1 1 calc R U . . .
H20B H 0.951351 0.774386 0.333950 0.048 Uiso 1 1 calc R U . . .
F1 F 1.00944(9) 0.63227(9) 0.62614(9) 0.0379(3) Uani 1 1 d . . . . .
F2 F 0.88661(9) 0.52602(8) 0.54066(10) 0.0367(2) Uani 1 1 d . . . . .
O1 O 0.55008(10) 0.57170(9) 0.57179(8) 0.0241(2) Uani 1 1 d . . . . .
O2 O 0.64285(10) 0.68374(9) 0.68223(8) 0.0231(2) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C14 1.9159(15) . ?
Se1 C8 1.9780(15) . ?
C1 C6 1.387(2) . ?
C1 C2 1.390(2) . ?
C1 O1 1.4102(17) . ?
C2 C3 1.396(2) . ?
C2 C12 1.504(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(2) . ?
C5 H5 0.9500 . ?
C6 C13 1.502(2) . ?
C7 O2 1.1983(18) . ?
C7 O1 1.3494(17) . ?
C7 C8 1.512(2) . ?
C8 C9 1.504(2) . ?
C8 H8 1.0000 . ?
C9 C11 1.504(2) . ?
C9 C10 1.505(2) . ?
C9 H9 1.0000 . ?
C10 C20 1.310(2) . ?
C10 C11 1.447(2) . ?
C11 F2 1.352(2) . ?
C11 F1 1.353(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.394(2) . ?
C14 C19 1.394(2) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9500 . ?
C20 H20B 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
C14 Se1 C8 99.25(6) . . ?
C6 C1 C2 123.88(14) . . ?
C6 C1 O1 117.41(13) . . ?
C2 C1 O1 118.47(14) . . ?
C1 C2 C3 116.84(16) . . ?
C1 C2 C12 122.58(15) . . ?
C3 C2 C12 120.58(16) . . ?
C4 C3 C2 121.05(17) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.35(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.83(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.05(15) . . ?
C1 C6 C13 121.94(14) . . ?
C5 C6 C13 121.00(16) . . ?
O2 C7 O1 124.28(13) . . ?
O2 C7 C8 126.26(13) . . ?
O1 C7 C8 109.46(12) . . ?
C9 C8 C7 110.98(12) . . ?
C9 C8 Se1 112.73(10) . . ?
C7 C8 Se1 108.23(9) . . ?
C9 C8 H8 108.3 . . ?
C7 C8 H8 108.3 . . ?
Se1 C8 H8 108.3 . . ?
C8 C9 C11 117.93(13) . . ?
C8 C9 C10 119.21(14) . . ?
C11 C9 C10 57.49(11) . . ?
C8 C9 H9 116.4 . . ?
C11 C9 H9 116.4 . . ?
C10 C9 H9 116.4 . . ?
C20 C10 C11 149.99(18) . . ?
C20 C10 C9 148.73(18) . . ?
C11 C10 C9 61.24(11) . . ?
F2 C11 F1 108.22(14) . . ?
F2 C11 C10 121.96(16) . . ?
F1 C11 C10 120.86(14) . . ?
F2 C11 C9 118.70(13) . . ?
F1 C11 C9 119.44(15) . . ?
C10 C11 C9 61.27(11) . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.75(15) . . ?
C15 C14 Se1 120.25(12) . . ?
C19 C14 Se1 119.90(12) . . ?
C16 C15 C14 119.63(17) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.23(17) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.28(16) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.98(17) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.11(16) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C10 C20 H20A 120.0 . . ?
C10 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
C7 O1 C1 118.38(11) . . ?

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
C6 C1 C2 C3 -0.2(2) . . . . ?
O1 C1 C2 C3 173.98(14) . . . . ?
C6 C1 C2 C12 179.81(16) . . . . ?
O1 C1 C2 C12 -6.0(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C12 C2 C3 C4 179.62(17) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
O1 C1 C6 C5 -173.64(13) . . . . ?
C2 C1 C6 C13 179.79(15) . . . . ?
O1 C1 C6 C13 5.5(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C13 -179.64(16) . . . . ?
O2 C7 C8 C9 34.0(2) . . . . ?
O1 C7 C8 C9 -146.08(12) . . . . ?
O2 C7 C8 Se1 -90.18(16) . . . . ?
O1 C7 C8 Se1 89.74(12) . . . . ?
C7 C8 C9 C11 82.83(17) . . . . ?
Se1 C8 C9 C11 -155.58(12) . . . . ?
C7 C8 C9 C10 149.23(14) . . . . ?
Se1 C8 C9 C10 -89.18(15) . . . . ?
C8 C9 C10 C20 76.0(4) . . . . ?
C11 C9 C10 C20 -177.7(4) . . . . ?
C8 C9 C10 C11 -106.26(16) . . . . ?
C20 C10 C11 F2 -74.7(4) . . . . ?
C9 C10 C11 F2 107.66(16) . . . . ?
C20 C10 C11 F1 68.6(4) . . . . ?
C9 C10 C11 F1 -108.99(18) . . . . ?
C20 C10 C11 C9 177.6(4) . . . . ?
C8 C9 C11 F2 -4.3(2) . . . . ?
C10 C9 C11 F2 -112.84(18) . . . . ?
C8 C9 C11 F1 -140.26(14) . . . . ?
C10 C9 C11 F1 111.24(17) . . . . ?
C8 C9 C11 C10 108.50(16) . . . . ?
C19 C14 C15 C16 -0.4(2) . . . . ?
Se1 C14 C15 C16 175.94(13) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C19 -1.3(3) . . . . ?
C17 C18 C19 C14 0.6(2) . . . . ?
C15 C14 C19 C18 0.2(2) . . . . ?
Se1 C14 C19 C18 -176.15(12) . . . . ?
O2 C7 O1 C1 -3.1(2) . . . . ?
C8 C7 O1 C1 176.99(12) . . . . ?
C6 C1 O1 C7 -94.93(16) . . . . ?
C2 C1 O1 C7 90.47(17) . . . . ?

_refine_diff_density_max         0.966
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.058



