# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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 
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data_test1006_01_a
_database_code_depnum_ccdc_archive 'CCDC 2190321'
loop_
_audit_author_name
_audit_author_address
'Sanjay singh'
;IIT Delhi
India
;
_audit_update_record             
;
2022-07-14 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_audit_creation_date             2022-07-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 F5 O4'
_chemical_formula_sum            'C24 H20 F5 O4'
_chemical_formula_weight         467.40
_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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3761(5)
_cell_length_b                   8.4007(5)
_cell_length_c                   16.0336(9)
_cell_angle_alpha                98.767(2)
_cell_angle_beta                 99.704(2)
_cell_angle_gamma                91.221(2)
_cell_volume                     1097.79(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.265
_cell_measurement_theta_min      2.456
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1196 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.9488.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             482
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            43739
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_min         2.456
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  multi-scan
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3146
_reflns_number_total             5456
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         5456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.029
_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)+(0.0737P)²+0.3491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1702
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C17(H17), C21(H21)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.8088(3) 0.7709(3) 0.55927(13) 0.1372(9) Uani 1 1 d . . . . .
F2 F 0.5117(2) 0.85560(17) 0.29894(10) 0.0720(5) Uani 1 1 d . . . . .
F3 F 0.54032(18) 0.33187(18) 0.37080(10) 0.0669(4) Uani 1 1 d . . . . .
F4 F 0.7309(3) 0.4487(3) 0.51876(12) 0.1098(7) Uani 1 1 d . . . . .
F5 F 0.6944(3) 0.9711(2) 0.44741(13) 0.1260(9) Uani 1 1 d . . . . .
O1 O -0.1990(2) 0.2896(2) 0.27467(13) 0.0658(5) Uani 1 1 d . . . . .
O2 O 0.4651(2) 0.7881(2) -0.05715(11) 0.0658(5) Uani 1 1 d . . . . .
H2 H 0.553945 0.775935 -0.071575 0.099 Uiso 1 1 calc R U . . .
O3 O 0.31167(18) 0.18983(17) 0.17921(11) 0.0514(4) Uani 1 1 d . . . . .
O4 O 0.20477(19) 0.70576(18) 0.30540(11) 0.0548(4) Uani 1 1 d . . . . .
C1 C 0.7163(4) 0.7110(4) 0.48358(18) 0.0829(9) Uani 1 1 d . . . . .
C2 C 0.6582(4) 0.8108(4) 0.42744(18) 0.0776(9) Uani 1 1 d . . . . .
C3 C 0.5639(3) 0.7480(3) 0.34955(15) 0.0533(6) Uani 1 1 d . . . . .
C4 C 0.5249(2) 0.5858(3) 0.32541(13) 0.0425(5) Uani 1 1 d . . . . .
C5 C 0.4297(2) 0.5028(2) 0.23903(12) 0.0376(5) Uani 1 1 d . . . . .
H5 H 0.485439 0.402932 0.226287 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2596(2) 0.4460(2) 0.24671(12) 0.0366(4) Uani 1 1 d . . . . .
C7 C 0.1506(3) 0.5489(2) 0.28213(13) 0.0407(5) Uani 1 1 d . . . . .
C8 C -0.0012(3) 0.4934(3) 0.29089(14) 0.0451(5) Uani 1 1 d . . . . .
H8 H -0.071813 0.563506 0.314736 0.054 Uiso 1 1 calc R U . . .
C9 C -0.0467(2) 0.3327(3) 0.26381(14) 0.0433(5) Uani 1 1 d . . . . .
C10 C -0.2545(3) 0.1248(3) 0.2497(2) 0.0777(9) Uani 1 1 d . . . . .
H10A H -0.251299 0.092080 0.190020 0.117 Uiso 1 1 calc R U . . .
H10B H -0.363782 0.112350 0.259426 0.117 Uiso 1 1 calc R U . . .
H10C H -0.185785 0.058883 0.282972 0.117 Uiso 1 1 calc R U . . .
C11 C 0.4389(2) 0.5898(2) 0.16306(12) 0.0374(5) Uani 1 1 d . . . . .
C12 C 0.5877(3) 0.6393(3) 0.14627(14) 0.0454(5) Uani 1 1 d . . . . .
H12 H 0.681158 0.626379 0.184687 0.054 Uiso 1 1 calc R U . . .
C13 C 0.6020(3) 0.7075(3) 0.07402(15) 0.0471(5) Uani 1 1 d . . . . .
C14 C 0.7648(3) 0.7635(4) 0.05868(18) 0.0690(8) Uani 1 1 d . . . . .
H14A H 0.784446 0.708180 0.004658 0.104 Uiso 1 1 calc R U . . .
H14B H 0.847775 0.740435 0.103750 0.104 Uiso 1 1 calc R U . . .
H14C H 0.766134 0.877504 0.057840 0.104 Uiso 1 1 calc R U . . .
C15 C 0.4618(3) 0.7220(3) 0.01642(14) 0.0456(5) Uani 1 1 d . . . . .
C16 C 0.3112(3) 0.6730(3) 0.03014(14) 0.0460(5) Uani 1 1 d . . . . .
C17 C 0.3020(3) 0.6091(3) 0.10403(13) 0.0416(5) Uani 1 1 d . . . . .
H17 H 0.200782 0.578220 0.114402 0.050 Uiso 1 1 calc R U . . .
C18 C 0.1619(3) 0.6880(4) -0.03399(17) 0.0693(8) Uani 1 1 d . . . . .
H18A H 0.141383 0.799963 -0.034233 0.104 Uiso 1 1 calc R U . . .
H18B H 0.071008 0.634564 -0.018843 0.104 Uiso 1 1 calc R U . . .
H18C H 0.177831 0.639163 -0.089947 0.104 Uiso 1 1 calc R U . . .
C19 C 0.2060(2) 0.2863(2) 0.21826(13) 0.0380(5) Uani 1 1 d . . . . .
C20 C 0.2761(4) 0.0218(3) 0.1592(2) 0.0703(8) Uani 1 1 d . . . . .
H20A H 0.261294 -0.019569 0.210121 0.106 Uiso 1 1 calc R U . . .
H20B H 0.364274 -0.029974 0.136558 0.106 Uiso 1 1 calc R U . . .
H20C H 0.178682 0.000656 0.117298 0.106 Uiso 1 1 calc R U . . .
C21 C 0.0547(3) 0.2272(3) 0.22706(13) 0.0428(5) Uani 1 1 d . . . . .
H21 H 0.022611 0.119119 0.208604 0.051 Uiso 1 1 calc R U . . .
C22 C 0.1087(4) 0.8152(3) 0.3497(2) 0.0828(9) Uani 1 1 d . . . . .
H22A H 0.007922 0.825967 0.312841 0.124 Uiso 1 1 calc R U . . .
H22B H 0.165800 0.918524 0.366220 0.124 Uiso 1 1 calc R U . . .
H22C H 0.087648 0.775006 0.399896 0.124 Uiso 1 1 calc R U . . .
C23 C 0.5814(3) 0.4905(3) 0.38591(15) 0.0509(6) Uani 1 1 d . . . . .
C24 C 0.6775(3) 0.5499(4) 0.46349(17) 0.0699(8) 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
F1 C1 1.344(3) . ?
F2 C3 1.337(3) . ?
F3 C23 1.344(3) . ?
F4 C24 1.349(3) . ?
F5 C2 1.351(3) . ?
O1 C9 1.365(2) . ?
O1 C10 1.427(3) . ?
O2 H2 0.8200 . ?
O2 C15 1.382(3) . ?
O3 C19 1.377(2) . ?
O3 C20 1.413(3) . ?
O4 C7 1.359(2) . ?
O4 C22 1.422(3) . ?
C1 C2 1.360(4) . ?
C1 C24 1.362(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.375(3) . ?
C4 C5 1.533(3) . ?
C4 C23 1.380(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.523(3) . ?
C5 C11 1.524(3) . ?
C6 C7 1.401(3) . ?
C6 C19 1.389(3) . ?
C7 C8 1.382(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(3) . ?
C9 C21 1.376(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.387(3) . ?
C11 C17 1.388(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(3) . ?
C13 C14 1.505(3) . ?
C13 C15 1.386(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.382(3) . ?
C16 C17 1.386(3) . ?
C16 C18 1.500(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C21 1.388(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.378(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C10 118.38(19) . . ?
C15 O2 H2 109.5 . . ?
C19 O3 C20 119.05(17) . . ?
C7 O4 C22 118.64(19) . . ?
F1 C1 C2 120.4(3) . . ?
F1 C1 C24 120.0(3) . . ?
C2 C1 C24 119.6(3) . . ?
F5 C2 C1 120.0(3) . . ?
F5 C2 C3 120.1(3) . . ?
C1 C2 C3 120.0(3) . . ?
F2 C3 C2 115.6(2) . . ?
F2 C3 C4 121.8(2) . . ?
C4 C3 C2 122.6(2) . . ?
C3 C4 C5 126.76(19) . . ?
C3 C4 C23 115.2(2) . . ?
C23 C4 C5 118.1(2) . . ?
C4 C5 H5 104.3 . . ?
C6 C5 C4 111.75(16) . . ?
C6 C5 H5 104.3 . . ?
C6 C5 C11 115.03(16) . . ?
C11 C5 C4 115.58(16) . . ?
C11 C5 H5 104.3 . . ?
C7 C6 C5 122.76(18) . . ?
C19 C6 C5 120.43(17) . . ?
C19 C6 C7 116.81(18) . . ?
O4 C7 C6 115.01(18) . . ?
O4 C7 C8 123.30(19) . . ?
C8 C7 C6 121.69(19) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.4 . . ?
O1 C9 C8 114.78(19) . . ?
O1 C9 C21 123.7(2) . . ?
C21 C9 C8 121.46(19) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C5 120.54(18) . . ?
C12 C11 C17 117.46(19) . . ?
C17 C11 C5 121.74(17) . . ?
C11 C12 H12 118.9 . . ?
C11 C12 C13 122.2(2) . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C14 120.9(2) . . ?
C15 C13 C12 118.06(19) . . ?
C15 C13 C14 121.0(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 C13 121.8(2) . . ?
C16 C15 O2 116.5(2) . . ?
C16 C15 C13 121.7(2) . . ?
C15 C16 C17 118.4(2) . . ?
C15 C16 C18 120.5(2) . . ?
C17 C16 C18 121.1(2) . . ?
C11 C17 H17 118.9 . . ?
C16 C17 C11 122.14(19) . . ?
C16 C17 H17 118.9 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 C6 115.67(17) . . ?
O3 C19 C21 121.76(18) . . ?
C21 C19 C6 122.56(19) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C21 C19 118.31(19) . . ?
C9 C21 H21 120.8 . . ?
C19 C21 H21 120.8 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F3 C23 C4 119.7(2) . . ?
F3 C23 C24 117.0(2) . . ?
C24 C23 C4 123.3(2) . . ?
F4 C24 C1 120.8(3) . . ?
F4 C24 C23 120.0(3) . . ?
C1 C24 C23 119.3(3) . . ?

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 F5 0.5(5) . . . . ?
F1 C1 C2 C3 179.7(3) . . . . ?
F1 C1 C24 F4 -0.1(5) . . . . ?
F1 C1 C24 C23 179.4(3) . . . . ?
F2 C3 C4 C5 4.1(4) . . . . ?
F2 C3 C4 C23 -177.1(2) . . . . ?
F3 C23 C24 F4 2.5(4) . . . . ?
F3 C23 C24 C1 -177.0(3) . . . . ?
F5 C2 C3 F2 -1.2(4) . . . . ?
F5 C2 C3 C4 179.2(3) . . . . ?
O1 C9 C21 C19 178.9(2) . . . . ?
O2 C15 C16 C17 -178.7(2) . . . . ?
O2 C15 C16 C18 1.7(3) . . . . ?
O3 C19 C21 C9 -177.46(19) . . . . ?
O4 C7 C8 C9 178.6(2) . . . . ?
C1 C2 C3 F2 179.6(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C1 C24 F4 -178.7(3) . . . . ?
C2 C1 C24 C23 0.8(5) . . . . ?
C2 C3 C4 C5 -176.3(2) . . . . ?
C2 C3 C4 C23 2.4(4) . . . . ?
C3 C4 C5 C6 -107.6(2) . . . . ?
C3 C4 C5 C11 26.5(3) . . . . ?
C3 C4 C23 F3 175.5(2) . . . . ?
C3 C4 C23 C24 -3.4(4) . . . . ?
C4 C5 C6 C7 54.1(3) . . . . ?
C4 C5 C6 C19 -125.8(2) . . . . ?
C4 C5 C11 C12 51.1(3) . . . . ?
C4 C5 C11 C17 -135.0(2) . . . . ?
C4 C23 C24 F4 -178.6(2) . . . . ?
C4 C23 C24 C1 1.9(4) . . . . ?
C5 C4 C23 F3 -5.7(3) . . . . ?
C5 C4 C23 C24 175.5(2) . . . . ?
C5 C6 C7 O4 3.1(3) . . . . ?
C5 C6 C7 C8 -177.92(19) . . . . ?
C5 C6 C19 O3 -3.7(3) . . . . ?
C5 C6 C19 C21 177.29(18) . . . . ?
C5 C11 C12 C13 174.9(2) . . . . ?
C5 C11 C17 C16 -173.22(19) . . . . ?
C6 C5 C11 C12 -176.33(18) . . . . ?
C6 C5 C11 C17 -2.4(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C6 C19 C21 C9 1.4(3) . . . . ?
C7 C6 C19 O3 176.35(17) . . . . ?
C7 C6 C19 C21 -2.6(3) . . . . ?
C7 C8 C9 O1 -179.65(19) . . . . ?
C7 C8 C9 C21 -1.1(3) . . . . ?
C8 C9 C21 C19 0.5(3) . . . . ?
C10 O1 C9 C8 -178.9(2) . . . . ?
C10 O1 C9 C21 2.6(3) . . . . ?
C11 C5 C6 C7 -80.3(2) . . . . ?
C11 C5 C6 C19 99.8(2) . . . . ?
C11 C12 C13 C14 178.6(2) . . . . ?
C11 C12 C13 C15 -1.6(3) . . . . ?
C12 C11 C17 C16 0.9(3) . . . . ?
C12 C13 C15 O2 -179.9(2) . . . . ?
C12 C13 C15 C16 1.0(3) . . . . ?
C13 C15 C16 C17 0.5(3) . . . . ?
C13 C15 C16 C18 -179.1(2) . . . . ?
C14 C13 C15 O2 0.0(3) . . . . ?
C14 C13 C15 C16 -179.2(2) . . . . ?
C15 C16 C17 C11 -1.5(3) . . . . ?
C17 C11 C12 C13 0.7(3) . . . . ?
C18 C16 C17 C11 178.1(2) . . . . ?
C19 C6 C7 O4 -176.97(18) . . . . ?
C19 C6 C7 C8 2.0(3) . . . . ?
C20 O3 C19 C6 171.3(2) . . . . ?
C20 O3 C19 C21 -9.7(3) . . . . ?
C22 O4 C7 C6 -173.8(2) . . . . ?
C22 O4 C7 C8 7.3(3) . . . . ?
C23 C4 C5 C6 73.7(2) . . . . ?
C23 C4 C5 C11 -152.20(19) . . . . ?
C24 C1 C2 F5 179.1(3) . . . . ?
C24 C1 C2 C3 -1.7(5) . . . . ?

_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_sanjay_ckh_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2190324'
loop_
_audit_author_name
_audit_author_address
'Sanjay singh'
;IIT Delhi
India
;
_audit_update_record             
;
2022-07-14 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_audit_creation_date             2022-06-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_chemical_formula_moiety         'C18 H22 O4'
_chemical_formula_sum            'C18 H22 O4'
_chemical_formula_weight         302.373
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.0243(6)
_cell_length_b                   20.5740(16)
_cell_length_c                   11.0931(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.591(4)
_cell_angle_gamma                90
_cell_volume                     1602.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9804
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.360
_cell_measurement_theta_min      2.70
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0780 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.9635.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             648.433
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            52044
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9965
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.98
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -9
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -7
_reflns_number_gt                3483
_reflns_number_total             4007
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 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         0.2036
_refine_diff_density_min         -0.1665
_refine_diff_density_rms         0.0340
_refine_ls_d_res_high            0.7482
_refine_ls_d_res_low             10.2870
_refine_ls_goodness_of_fit_ref   1.0649
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     205
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.0649
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+0.2712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1244
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C12(H12), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C14(H14a,H14b,H14c),
 C17(H17a,H17b,H17c)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O1 O 0.63235(13) 0.53172(4) 0.11899(9) 0.0565(3) Uani 1.000000 .
O2 O 0.92591(13) 0.33811(5) 0.29469(11) 0.0633(3) Uani 1.000000 .
O3 O 0.36175(13) 0.42004(4) 0.44616(9) 0.0528(2) Uani 1.000000 .
O4 O 0.19836(16) 0.10706(5) 0.31883(11) 0.0680(3) Uani 1.000000 .
H4 H 0.0990(15) 0.1046(6) 0.3557(15) 0.1020(5) Uiso 1.000000 GR
C1 C 0.7711(2) 0.53660(8) 0.02891(14) 0.0636(4) Uani 1.000000 .
H1a H 0.8948(3) 0.5421(6) 0.06652(15) 0.0954(6) Uiso 1.000000 GR
H1b H 0.7698(12) 0.4977(3) -0.0188(7) 0.0954(6) Uiso 1.000000 GR
H1c H 0.7426(10) 0.5733(4) -0.0219(7) 0.0954(6) Uiso 1.000000 GR
C2 C 0.64532(17) 0.48029(5) 0.19855(11) 0.0435(3) Uani 1.000000 .
C3 C 0.79218(16) 0.43511(6) 0.20009(12) 0.0470(3) Uani 1.000000 .
H3 H 0.89040(16) 0.43794(6) 0.14581(12) 0.0564(3) Uiso 1.000000 R
C4 C 0.78815(16) 0.38517(5) 0.28571(12) 0.0453(3) Uani 1.000000 .
C5 C 0.64343(16) 0.37989(5) 0.36829(11) 0.0415(3) Uani 1.000000 .
C6 C 0.49913(16) 0.42691(5) 0.36271(10) 0.0407(2) Uani 1.000000 .
C7 C 0.49866(17) 0.47679(5) 0.27917(11) 0.0438(3) Uani 1.000000 .
H7 H 0.40144(17) 0.50749(5) 0.27715(11) 0.0526(3) Uiso 1.000000 R
C8 C 1.08042(19) 0.33923(7) 0.21537(15) 0.0590(4) Uani 1.000000 .
H8a H 1.0329(2) 0.3357(6) 0.13365(16) 0.0885(5) Uiso 1.000000 GR
H8b H 1.1489(10) 0.3793(3) 0.2253(7) 0.0885(5) Uiso 1.000000 GR
H8c H 1.1641(9) 0.3034(3) 0.2334(7) 0.0885(5) Uiso 1.000000 GR
C9 C 0.2152(2) 0.46762(7) 0.44946(13) 0.0550(3) Uani 1.000000 .
H9a H 0.2709(2) 0.50979(10) 0.4618(10) 0.0826(5) Uiso 1.000000 GR
H9b H 0.1437(10) 0.4672(4) 0.3745(4) 0.0826(5) Uiso 1.000000 GR
H9c H 0.1321(10) 0.4580(3) 0.5143(7) 0.0826(5) Uiso 1.000000 GR
C10 C 0.63950(18) 0.32638(6) 0.46141(11) 0.0466(3) Uani 1.000000 .
H10a H 0.76866(18) 0.31141(6) 0.47751(11) 0.0559(3) Uiso 1.000000 R
H10b H 0.59204(18) 0.34404(6) 0.53588(11) 0.0559(3) Uiso 1.000000 R
C11 C 0.51712(17) 0.26874(5) 0.42363(10) 0.0420(3) Uani 1.000000 .
C12 C 0.57571(18) 0.22652(5) 0.33410(11) 0.0453(3) Uani 1.000000 .
H12 H 0.69006(18) 0.23461(5) 0.29656(11) 0.0543(3) Uiso 1.000000 R
C13 C 0.46855(19) 0.17254(5) 0.29895(11) 0.0457(3) Uani 1.000000 .
C14 C 0.5355(2) 0.12694(7) 0.20239(13) 0.0601(4) Uani 1.000000 .
H14a H 0.4651(12) 0.1351(4) 0.1285(3) 0.0902(5) Uiso 1.000000 GR
H14b H 0.6687(4) 0.1338(4) 0.1901(8) 0.0902(5) Uiso 1.000000 GR
H14c H 0.5152(16) 0.08283(7) 0.2271(5) 0.0902(5) Uiso 1.000000 GR
C15 C 0.29775(18) 0.16143(5) 0.35597(11) 0.0461(3) Uani 1.000000 .
C16 C 0.23247(17) 0.20258(6) 0.44558(11) 0.0445(3) Uani 1.000000 .
C17 C 0.04791(19) 0.18940(7) 0.50716(14) 0.0588(3) Uani 1.000000 .
H17a H -0.0550(3) 0.1894(6) 0.4484(2) 0.0881(5) Uiso 1.000000 GR
H17b H 0.0546(7) 0.1478(3) 0.5462(9) 0.0881(5) Uiso 1.000000 GR
H17c H 0.0266(9) 0.2226(3) 0.5661(8) 0.0881(5) Uiso 1.000000 GR
C18 C 0.34543(17) 0.25601(5) 0.47748(11) 0.0447(3) Uani 1.000000 .
H18 H 0.30398(17) 0.28407(5) 0.53700(11) 0.0536(3) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4186(15) . ?
O1 C2 1.3794(14) . ?
O2 C4 1.3706(14) . ?
O2 C8 1.4162(17) . ?
O3 C6 1.3631(14) . ?
O3 C9 1.4218(15) . ?
O4 H4 0.8200 . ?
O4 C15 1.3756(14) . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C2 C3 1.3883(16) . ?
C2 C7 1.3847(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.4000(18) . ?
C4 C5 1.3915(17) . ?
C5 C6 1.4012(15) . ?
C5 C10 1.5105(16) . ?
C6 C7 1.3827(16) . ?
C7 H7 0.9300 . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9c 0.9600 . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C10 C11 1.5169(16) . ?
C11 C12 1.3902(17) . ?
C11 C18 1.3856(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.3913(16) . ?
C13 C14 1.5088(18) . ?
C13 C15 1.3907(18) . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C15 C16 1.3931(17) . ?
C16 C17 1.5066(18) . ?
C16 C18 1.3955(16) . ?
C17 H17a 0.9600 . ?
C17 H17b 0.9600 . ?
C17 H17c 0.9600 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 118.06(10) . . ?
C8 O2 C4 119.66(11) . . ?
C9 O3 C6 118.21(9) . . ?
C15 O4 H4 109.5 . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
C3 C2 O1 123.87(11) . . ?
C7 C2 O1 114.58(10) . . ?
C7 C2 C3 121.55(11) . . ?
H3 C3 C2 120.96(7) . . ?
C4 C3 C2 118.08(11) . . ?
C4 C3 H3 120.96(7) . . ?
C3 C4 O2 122.70(11) . . ?
C5 C4 O2 115.10(11) . . ?
C5 C4 C3 122.19(10) . . ?
C6 C5 C4 117.25(10) . . ?
C10 C5 C4 122.32(10) . . ?
C10 C5 C6 120.43(11) . . ?
C5 C6 O3 115.04(10) . . ?
C7 C6 O3 122.93(10) . . ?
C7 C6 C5 122.02(11) . . ?
C6 C7 C2 118.91(10) . . ?
H7 C7 C2 120.55(6) . . ?
H7 C7 C6 120.55(7) . . ?
H8a C8 O2 109.5 . . ?
H8b C8 O2 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 O2 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
H9a C9 O3 109.5 . . ?
H9b C9 O3 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 O3 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
H10a C10 C5 108.82(6) . . ?
H10b C10 C5 108.82(7) . . ?
H10b C10 H10a 107.7 . . ?
C11 C10 C5 113.70(9) . . ?
C11 C10 H10a 108.82(6) . . ?
C11 C10 H10b 108.82(7) . . ?
C12 C11 C10 120.60(11) . . ?
C18 C11 C10 121.47(11) . . ?
C18 C11 C12 117.93(11) . . ?
H12 C12 C11 118.99(7) . . ?
C13 C12 C11 122.03(11) . . ?
C13 C12 H12 118.99(7) . . ?
C14 C13 C12 121.24(12) . . ?
C15 C13 C12 118.08(11) . . ?
C15 C13 C14 120.69(11) . . ?
H14a C14 C13 109.5 . . ?
H14b C14 C13 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C13 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C13 C15 O4 115.75(11) . . ?
C16 C15 O4 122.24(11) . . ?
C16 C15 C13 122.00(11) . . ?
C17 C16 C15 121.24(11) . . ?
C18 C16 C15 117.61(11) . . ?
C18 C16 C17 121.14(12) . . ?
H17a C17 C16 109.5 . . ?
H17b C17 C16 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C16 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
C16 C18 C11 122.36(11) . . ?
H18 C18 C11 118.82(7) . . ?
H18 C18 C16 118.82(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.99(12) . . . . ?
O1 C2 C7 C6 -179.93(10) . . . . ?
O2 C4 C3 C2 179.90(12) . . . . ?
O2 C4 C5 C6 180.00(10) . . . . ?
O2 C4 C5 C10 0.35(13) . . . . ?
O3 C6 C5 C4 -179.38(10) . . . . ?
O3 C6 C5 C10 0.28(12) . . . . ?
O3 C6 C7 C2 179.34(12) . . . . ?
O4 C15 C13 C12 -179.31(11) . . . . ?
O4 C15 C13 C14 0.30(14) . . . . ?
O4 C15 C16 C17 0.11(15) . . . . ?
O4 C15 C16 C18 179.27(12) . . . . ?
C2 C3 C4 C5 -0.26(14) . . . . ?
C2 C7 C6 C5 0.05(14) . . . . ?
C3 C4 C5 C6 0.14(14) . . . . ?
C3 C4 C5 C10 -179.51(11) . . . . ?
C4 C5 C6 C7 -0.03(13) . . . . ?
C4 C5 C10 C11 -96.16(12) . . . . ?
C5 C10 C11 C12 71.57(12) . . . . ?
C5 C10 C11 C18 -109.09(11) . . . . ?
C10 C11 C12 C13 178.78(11) . . . . ?
C10 C11 C18 C16 -178.79(10) . . . . ?
C11 C12 C13 C14 -179.42(12) . . . . ?
C11 C12 C13 C15 0.19(14) . . . . ?
C11 C18 C16 C15 -0.15(13) . . . . ?
C11 C18 C16 C17 179.01(12) . . . . ?
C12 C13 C15 C16 0.25(14) . . . . ?
C13 C15 C16 C17 -179.42(12) . . . . ?
C13 C15 C16 C18 -0.26(14) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
