# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_mkv58
_database_code_depnum_ccdc_archive 'CCDC 2284904'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;

_audit_update_record             
;
2023-07-27 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_publcif_datablock.id            {fdb98139-d94f-41b2-bccd-ef3935afb2e6}

# publcif _publ_body_element loop end
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 F3 O4'
_chemical_formula_sum            'C20 H17 F3 O4'
_chemical_formula_weight         378.33
_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'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   38.220(9)
_cell_length_b                   5.6457(12)
_cell_length_c                   16.281(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.503(8)
_cell_angle_gamma                90
_cell_volume                     3464.8(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9688
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1768
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            73737
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_min         2.537
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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                3121
_reflns_number_total             3776
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0982
_refine_ls_restrained_S_all      1.242
_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)+(0.0576P)²+13.6936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1920
_refine_ls_wR_factor_ref         0.2011
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C16(H16), C19(H19)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C20(H20A,H20B,H20C)
;
_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
C1 C 0.63298(9) 0.0085(7) 0.4168(2) 0.0242(8) Uani 1 1 d . . . . .
C2 C 0.64970(8) 0.1968(6) 0.4781(2) 0.0214(7) Uani 1 1 d . . . . .
H2 H 0.652743 0.345808 0.446757 0.026 Uiso 1 1 calc R U . . .
C3 C 0.68607(9) 0.1128(6) 0.5218(2) 0.0211(7) Uani 1 1 d . . . . .
H3A H 0.683127 -0.028204 0.556142 0.025 Uiso 1 1 calc R U . . .
H3B H 0.700704 0.066442 0.479568 0.025 Uiso 1 1 calc R U . . .
C4 C 0.70478(9) 0.3056(6) 0.5765(2) 0.0186(7) Uani 1 1 d . . . . .
C5 C 0.74167(8) 0.2589(6) 0.6200(2) 0.0167(7) Uani 1 1 d . . . . .
C6 C 0.75946(9) 0.0490(6) 0.6082(2) 0.0192(7) Uani 1 1 d . . . . .
H6 H 0.748203 -0.068191 0.571041 0.023 Uiso 1 1 calc R U . . .
C7 C 0.79352(9) 0.0115(6) 0.6505(2) 0.0220(7) Uani 1 1 d . . . . .
H7 H 0.805488 -0.131246 0.641475 0.026 Uiso 1 1 calc R U . . .
C8 C 0.81060(9) 0.1792(6) 0.7062(2) 0.0213(7) Uani 1 1 d . . . . .
C9 C 0.79256(9) 0.3867(6) 0.7173(2) 0.0220(7) Uani 1 1 d . . . . .
H9 H 0.803811 0.503650 0.754493 0.026 Uiso 1 1 calc R U . . .
C10 C 0.75854(9) 0.4275(6) 0.6754(2) 0.0195(7) Uani 1 1 d . . . . .
H10 H 0.746667 0.570584 0.684448 0.023 Uiso 1 1 calc R U . . .
C11 C 0.84733(9) 0.1317(7) 0.7537(2) 0.0266(8) Uani 1 1 d . . . . .
H11A H 0.856308 0.274376 0.784433 0.040 Uiso 1 1 calc R U . . .
H11B H 0.863197 0.088752 0.714548 0.040 Uiso 1 1 calc R U . . .
H11C H 0.846300 0.001217 0.792912 0.040 Uiso 1 1 calc R U . . .
C12 C 0.62402(9) 0.2442(6) 0.5393(2) 0.0208(7) Uani 1 1 d . . . . .
C13 C 0.60051(9) 0.4601(7) 0.5204(2) 0.0241(8) Uani 1 1 d . . . . .
H13A H 0.614948 0.602992 0.537211 0.029 Uiso 1 1 calc R U . . .
H13B H 0.592689 0.468799 0.459388 0.029 Uiso 1 1 calc R U . . .
C14 C 0.56839(9) 0.4675(7) 0.5616(2) 0.0249(8) Uani 1 1 d . . . . .
C15 C 0.54296(10) 0.2934(7) 0.5472(3) 0.0293(9) Uani 1 1 d . . . . .
C16 C 0.51160(10) 0.2915(8) 0.5801(3) 0.0366(10) Uani 1 1 d . . . . .
H16 H 0.495136 0.164611 0.569841 0.044 Uiso 1 1 calc R U . . .
C17 C 0.50570(10) 0.4814(8) 0.6280(3) 0.0338(9) Uani 1 1 d . . . . .
C18 C 0.53029(10) 0.6605(8) 0.6439(3) 0.0323(9) Uani 1 1 d . . . . .
C19 C 0.56128(9) 0.6550(7) 0.6115(2) 0.0271(8) Uani 1 1 d . . . . .
H19 H 0.577937 0.780266 0.623284 0.033 Uiso 1 1 calc R U . . .
C20 C 0.58324(12) -0.0827(10) 0.3162(3) 0.0527(14) Uani 1 1 d . . . . .
H20A H 0.594742 -0.093888 0.266788 0.079 Uiso 1 1 calc R U . . .
H20B H 0.558675 -0.029567 0.299618 0.079 Uiso 1 1 calc R U . . .
H20C H 0.583433 -0.238487 0.342792 0.079 Uiso 1 1 calc R U . . .
F1 F 0.54844(6) 0.1112(4) 0.49637(17) 0.0402(6) Uani 1 1 d . . . . .
F2 F 0.47552(6) 0.4940(5) 0.66021(17) 0.0478(7) Uani 1 1 d . . . . .
F3 F 0.52230(6) 0.8486(5) 0.68912(17) 0.0479(7) Uani 1 1 d . . . . .
O1 O 0.64494(7) -0.1841(5) 0.40831(18) 0.0321(7) Uani 1 1 d . . . . .
O2 O 0.60233(7) 0.0863(6) 0.37452(17) 0.0366(7) Uani 1 1 d . . . . .
O3 O 0.69030(6) 0.4944(4) 0.58490(16) 0.0256(6) Uani 1 1 d . . . . .
O4 O 0.62292(7) 0.1142(5) 0.59771(16) 0.0279(6) 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
C1 C2 1.524(5) . ?
C1 O1 1.196(5) . ?
C1 O2 1.331(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.529(5) . ?
C2 C12 1.534(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.510(5) . ?
C4 C5 1.493(5) . ?
C4 O3 1.219(4) . ?
C5 C6 1.395(5) . ?
C5 C10 1.394(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.396(5) . ?
C8 C9 1.386(5) . ?
C8 C11 1.511(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(5) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.515(5) . ?
C12 O4 1.207(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.494(5) . ?
C14 C15 1.375(5) . ?
C14 C19 1.388(5) . ?
C15 C16 1.391(6) . ?
C15 F1 1.358(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.366(6) . ?
C17 C18 1.376(6) . ?
C17 F2 1.346(4) . ?
C18 C19 1.374(5) . ?
C18 F3 1.356(5) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 O2 1.455(6) . ?

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
O1 C1 C2 125.7(3) . . ?
O1 C1 O2 124.1(4) . . ?
O2 C1 C2 110.3(3) . . ?
C1 C2 H2 109.0 . . ?
C1 C2 C3 109.8(3) . . ?
C1 C2 C12 107.6(3) . . ?
C3 C2 H2 109.0 . . ?
C3 C2 C12 112.4(3) . . ?
C12 C2 H2 109.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.9(3) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C5 C4 C3 118.1(3) . . ?
O3 C4 C3 121.2(3) . . ?
O3 C4 C5 120.8(3) . . ?
C6 C5 C4 121.9(3) . . ?
C10 C5 C4 119.1(3) . . ?
C10 C5 C6 119.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.3(3) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C11 120.5(3) . . ?
C9 C8 C7 117.9(3) . . ?
C9 C8 C11 121.5(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C5 C10 H10 119.9 . . ?
C9 C10 C5 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C2 115.4(3) . . ?
O4 C12 C2 121.0(3) . . ?
O4 C12 C13 123.6(3) . . ?
C12 C13 H13A 108.3 . . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 C12 115.8(3) . . ?
C14 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 C19 116.3(3) . . ?
C19 C14 C13 122.6(3) . . ?
C14 C15 C16 124.7(4) . . ?
F1 C15 C14 118.0(3) . . ?
F1 C15 C16 117.3(3) . . ?
C15 C16 H16 121.7 . . ?
C17 C16 C15 116.6(4) . . ?
C17 C16 H16 121.7 . . ?
C16 C17 C18 120.8(4) . . ?
F2 C17 C16 119.8(4) . . ?
F2 C17 C18 119.4(4) . . ?
C19 C18 C17 121.1(4) . . ?
F3 C18 C17 118.0(3) . . ?
F3 C18 C19 120.8(3) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
C1 O2 C20 115.2(4) . . ?

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
C1 C2 C3 C4 174.4(3) . . . . ?
C1 C2 C12 C13 -98.5(4) . . . . ?
C1 C2 C12 O4 80.8(4) . . . . ?
C2 C1 O2 C20 -177.8(3) . . . . ?
C2 C3 C4 C5 -176.3(3) . . . . ?
C2 C3 C4 O3 3.5(4) . . . . ?
C2 C12 C13 C14 161.6(3) . . . . ?
C3 C2 C12 C13 140.4(3) . . . . ?
C3 C2 C12 O4 -40.2(5) . . . . ?
C3 C4 C5 C6 3.1(5) . . . . ?
C3 C4 C5 C10 -175.5(3) . . . . ?
C4 C5 C6 C7 -179.2(3) . . . . ?
C4 C5 C10 C9 179.1(3) . . . . ?
C5 C6 C7 C8 0.7(5) . . . . ?
C6 C5 C10 C9 0.6(5) . . . . ?
C6 C7 C8 C9 -0.7(5) . . . . ?
C6 C7 C8 C11 178.1(3) . . . . ?
C7 C8 C9 C10 0.6(5) . . . . ?
C8 C9 C10 C5 -0.5(5) . . . . ?
C10 C5 C6 C7 -0.7(5) . . . . ?
C11 C8 C9 C10 -178.2(3) . . . . ?
C12 C2 C3 C4 -65.8(4) . . . . ?
C12 C13 C14 C15 -60.1(5) . . . . ?
C12 C13 C14 C19 124.2(4) . . . . ?
C13 C14 C15 C16 -177.2(4) . . . . ?
C13 C14 C15 F1 1.9(6) . . . . ?
C13 C14 C19 C18 176.0(4) . . . . ?
C14 C15 C16 C17 2.0(7) . . . . ?
C15 C14 C19 C18 0.1(6) . . . . ?
C15 C16 C17 C18 -1.6(6) . . . . ?
C15 C16 C17 F2 178.4(4) . . . . ?
C16 C17 C18 C19 0.7(7) . . . . ?
C16 C17 C18 F3 177.5(4) . . . . ?
C17 C18 C19 C14 0.1(6) . . . . ?
C19 C14 C15 C16 -1.3(6) . . . . ?
C19 C14 C15 F1 177.8(3) . . . . ?
F1 C15 C16 C17 -177.0(4) . . . . ?
F2 C17 C18 C19 -179.4(4) . . . . ?
F2 C17 C18 F3 -2.6(6) . . . . ?
F3 C18 C19 C14 -176.6(4) . . . . ?
O1 C1 C2 C3 5.4(5) . . . . ?
O1 C1 C2 C12 -117.3(4) . . . . ?
O1 C1 O2 C20 0.9(5) . . . . ?
O2 C1 C2 C3 -176.0(3) . . . . ?
O2 C1 C2 C12 61.4(4) . . . . ?
O3 C4 C5 C6 -176.8(3) . . . . ?
O3 C4 C5 C10 4.7(5) . . . . ?
O4 C12 C13 C14 -17.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_mkv55b
_database_code_depnum_ccdc_archive 'CCDC 2284905'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2023-07-27 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H17 F3 O5)'
_chemical_formula_sum            'C40 H34 F6 O10'
_chemical_formula_weight         788.67
_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'
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      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                   5.5852(10)
_cell_length_b                   8.4012(14)
_cell_length_c                   18.790(3)
_cell_angle_alpha                83.603(6)
_cell_angle_beta                 82.238(6)
_cell_angle_gamma                89.317(7)
_cell_volume                     868.2(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9688
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31105
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.563
_diffrn_ambient_temperature      103.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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                3473
_reflns_number_total             3759
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.042(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.027
_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)+(0.0372P)²+0.4073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0844
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C17(H17), C20(H20)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C12(H12A,H12B,H12C)
;
_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
C1 C 0.8096(2) 0.67516(13) 0.26497(6) 0.0156(2) Uani 1 1 d . . . . .
C2 C 0.8942(3) 0.89365(16) 0.17435(7) 0.0261(3) Uani 1 1 d . . . . .
H2A H 0.901014 0.973587 0.208249 0.039 Uiso 1 1 calc R U . . .
H2B H 0.831794 0.943468 0.130914 0.039 Uiso 1 1 calc R U . . .
H2C H 1.056846 0.852049 0.160980 0.039 Uiso 1 1 calc R U . . .
C3 C 0.6222(2) 0.54700(13) 0.29565(6) 0.0144(2) Uani 1 1 d . . . . .
H3 H 0.460610 0.599261 0.304179 0.017 Uiso 1 1 calc R U . . .
C4 C 0.6789(2) 0.45987(13) 0.36685(6) 0.0150(2) Uani 1 1 d . . . . .
H4A H 0.825201 0.393361 0.358093 0.018 Uiso 1 1 calc R U . . .
H4B H 0.711105 0.538748 0.399835 0.018 Uiso 1 1 calc R U . . .
C5 C 0.4669(2) 0.35455(13) 0.40125(6) 0.0145(2) Uani 1 1 d . . . . .
C6 C 0.4700(2) 0.26896(13) 0.47474(6) 0.0138(2) Uani 1 1 d . . . . .
C7 C 0.6582(2) 0.28289(13) 0.51559(6) 0.0144(2) Uani 1 1 d . . . . .
H7 H 0.789508 0.353049 0.496971 0.017 Uiso 1 1 calc R U . . .
C8 C 0.6568(2) 0.19560(13) 0.58323(6) 0.0148(2) Uani 1 1 d . . . . .
H8 H 0.785670 0.206080 0.610625 0.018 Uiso 1 1 calc R U . . .
C9 C 0.4637(2) 0.09270(13) 0.61015(6) 0.0149(2) Uani 1 1 d . . . . .
C10 C 0.2723(2) 0.07967(13) 0.56998(6) 0.0158(2) Uani 1 1 d . . . . .
H10 H 0.139622 0.010866 0.588826 0.019 Uiso 1 1 calc R U . . .
C11 C 0.2764(2) 0.16621(13) 0.50344(6) 0.0152(2) Uani 1 1 d . . . . .
H11 H 0.146304 0.156384 0.476440 0.018 Uiso 1 1 calc R U . . .
C12 C 0.6419(2) -0.01239(15) 0.71435(6) 0.0209(3) Uani 1 1 d . . . . .
H12A H 0.778248 -0.060981 0.686096 0.031 Uiso 1 1 calc R U . . .
H12B H 0.597706 -0.079317 0.760309 0.031 Uiso 1 1 calc R U . . .
H12C H 0.687934 0.094657 0.723829 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6147(2) 0.43091(13) 0.23809(6) 0.0138(2) Uani 1 1 d . . . . .
C14 C 0.4136(2) 0.46056(13) 0.19147(6) 0.0155(2) Uani 1 1 d . . . . .
H14A H 0.258343 0.426346 0.220833 0.019 Uiso 1 1 calc R U . . .
H14B H 0.403331 0.577052 0.176766 0.019 Uiso 1 1 calc R U . . .
C15 C 0.4459(2) 0.37473(13) 0.12470(6) 0.0139(2) Uani 1 1 d . . . . .
C16 C 0.6505(2) 0.40085(13) 0.07406(6) 0.0151(2) Uani 1 1 d . . . . .
C17 C 0.6914(2) 0.33043(14) 0.01058(6) 0.0170(2) Uani 1 1 d . . . . .
H17 H 0.835398 0.350433 -0.022294 0.020 Uiso 1 1 calc R U . . .
C18 C 0.5136(2) 0.22967(13) -0.00294(6) 0.0168(2) Uani 1 1 d . . . . .
C19 C 0.3062(2) 0.20058(13) 0.04557(6) 0.0161(2) Uani 1 1 d . . . . .
C20 C 0.2709(2) 0.27116(13) 0.10922(6) 0.0150(2) Uani 1 1 d . . . . .
H20 H 0.127899 0.249246 0.142332 0.018 Uiso 1 1 calc R U . . .
F1 F 0.81827(12) 0.50632(8) 0.08675(4) 0.02034(17) Uani 1 1 d . . . . .
F2 F 0.53878(14) 0.16095(9) -0.06514(4) 0.02366(18) Uani 1 1 d . . . . .
F3 F 0.13608(13) 0.10301(8) 0.02928(4) 0.02204(17) Uani 1 1 d . . . . .
O1 O 0.99776(15) 0.69434(10) 0.28732(5) 0.0223(2) Uani 1 1 d . . . . .
O2 O 0.73622(16) 0.76335(10) 0.20824(4) 0.0211(2) Uani 1 1 d . . . . .
O3 O 0.76294(15) 0.32633(10) 0.23096(4) 0.01732(18) Uani 1 1 d . . . . .
O4 O 0.29486(15) 0.33945(10) 0.36841(4) 0.02019(19) Uani 1 1 d . . . . .
O5 O 0.43958(15) 0.00000(10) 0.67458(4) 0.01924(19) 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
C1 C3 1.5209(15) . ?
C1 O1 1.2019(14) . ?
C1 O2 1.3374(14) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 O2 1.4487(14) . ?
C3 H3 1.0000 . ?
C3 C4 1.5222(15) . ?
C3 C13 1.5398(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5147(15) . ?
C5 C6 1.4864(15) . ?
C5 O4 1.2247(14) . ?
C6 C7 1.3958(15) . ?
C6 C11 1.4024(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3940(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3943(16) . ?
C9 C10 1.4011(16) . ?
C9 O5 1.3560(13) . ?
C10 H10 0.9500 . ?
C10 C11 1.3720(16) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 O5 1.4329(14) . ?
C13 C14 1.5169(15) . ?
C13 O3 1.2061(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5046(15) . ?
C15 C16 1.3876(15) . ?
C15 C20 1.3968(15) . ?
C16 C17 1.3803(16) . ?
C16 F1 1.3591(13) . ?
C17 H17 0.9500 . ?
C17 C18 1.3795(16) . ?
C18 C19 1.3800(17) . ?
C18 F2 1.3504(13) . ?
C19 C20 1.3828(16) . ?
C19 F3 1.3496(13) . ?
C20 H20 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
O1 C1 C3 125.63(10) . . ?
O1 C1 O2 124.46(11) . . ?
O2 C1 C3 109.91(9) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
C1 C3 H3 108.7 . . ?
C1 C3 C4 111.82(9) . . ?
C1 C3 C13 107.40(8) . . ?
C4 C3 H3 108.7 . . ?
C4 C3 C13 111.54(9) . . ?
C13 C3 H3 108.7 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 109.60(9) . . ?
C5 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C6 C5 C4 119.55(9) . . ?
O4 C5 C4 120.08(10) . . ?
O4 C5 C6 120.37(10) . . ?
C7 C6 C5 123.33(10) . . ?
C7 C6 C11 118.65(10) . . ?
C11 C6 C5 118.00(10) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.12(10) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.11(10) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 120.16(10) . . ?
O5 C9 C8 125.43(10) . . ?
O5 C9 C10 114.41(10) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.05(10) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.90(10) . . ?
C10 C11 H11 119.6 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
C14 C13 C3 115.32(9) . . ?
O3 C13 C3 121.05(10) . . ?
O3 C13 C14 123.62(10) . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.08(9) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C16 C15 C14 120.56(10) . . ?
C16 C15 C20 116.99(10) . . ?
C20 C15 C14 122.40(10) . . ?
C17 C16 C15 124.29(10) . . ?
F1 C16 C15 117.85(10) . . ?
F1 C16 C17 117.83(10) . . ?
C16 C17 H17 121.5 . . ?
C18 C17 C16 116.95(10) . . ?
C18 C17 H17 121.5 . . ?
C17 C18 C19 120.94(10) . . ?
F2 C18 C17 119.95(10) . . ?
F2 C18 C19 119.09(10) . . ?
C18 C19 C20 120.98(10) . . ?
F3 C19 C18 118.62(10) . . ?
F3 C19 C20 120.39(10) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.85(10) . . ?
C19 C20 H20 120.1 . . ?
C1 O2 C2 116.22(9) . . ?
C9 O5 C12 118.12(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
C1 C3 C4 C5 170.37(9) . . . . ?
C1 C3 C13 C14 -97.99(11) . . . . ?
C1 C3 C13 O3 80.87(12) . . . . ?
C3 C1 O2 C2 178.43(10) . . . . ?
C3 C4 C5 C6 -174.26(9) . . . . ?
C3 C4 C5 O4 6.19(14) . . . . ?
C3 C13 C14 C15 165.43(9) . . . . ?
C4 C3 C13 C14 139.16(9) . . . . ?
C4 C3 C13 O3 -41.99(14) . . . . ?
C4 C5 C6 C7 1.55(16) . . . . ?
C4 C5 C6 C11 -176.85(10) . . . . ?
C5 C6 C7 C8 -177.67(10) . . . . ?
C5 C6 C11 C10 177.84(10) . . . . ?
C6 C7 C8 C9 0.09(16) . . . . ?
C7 C6 C11 C10 -0.64(16) . . . . ?
C7 C8 C9 C10 -1.00(16) . . . . ?
C7 C8 C9 O5 179.47(10) . . . . ?
C8 C9 C10 C11 1.09(16) . . . . ?
C8 C9 O5 C12 -9.47(16) . . . . ?
C9 C10 C11 C6 -0.26(16) . . . . ?
C10 C9 O5 C12 170.98(10) . . . . ?
C11 C6 C7 C8 0.72(16) . . . . ?
C13 C3 C4 C5 -69.34(11) . . . . ?
C13 C14 C15 C16 -58.28(14) . . . . ?
C13 C14 C15 C20 124.20(11) . . . . ?
C14 C15 C16 C17 -178.24(10) . . . . ?
C14 C15 C16 F1 -0.30(15) . . . . ?
C14 C15 C20 C19 177.39(10) . . . . ?
C15 C16 C17 C18 0.97(17) . . . . ?
C16 C15 C20 C19 -0.22(16) . . . . ?
C16 C17 C18 C19 -0.55(16) . . . . ?
C16 C17 C18 F2 177.88(10) . . . . ?
C17 C18 C19 C20 -0.20(17) . . . . ?
C17 C18 C19 F3 178.98(10) . . . . ?
C18 C19 C20 C15 0.60(17) . . . . ?
C20 C15 C16 C17 -0.59(17) . . . . ?
C20 C15 C16 F1 177.36(9) . . . . ?
F1 C16 C17 C18 -176.97(9) . . . . ?
F2 C18 C19 C20 -178.65(10) . . . . ?
F2 C18 C19 F3 0.54(16) . . . . ?
F3 C19 C20 C15 -178.57(9) . . . . ?
O1 C1 C3 C4 9.44(16) . . . . ?
O1 C1 C3 C13 -113.24(12) . . . . ?
O1 C1 O2 C2 -2.41(16) . . . . ?
O2 C1 C3 C4 -171.40(9) . . . . ?
O2 C1 C3 C13 65.91(11) . . . . ?
O3 C13 C14 C15 -13.39(15) . . . . ?
O4 C5 C6 C7 -178.91(10) . . . . ?
O4 C5 C6 C11 2.69(16) . . . . ?
O5 C9 C10 C11 -179.33(10) . . . . ?

_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_MKV_54
_database_code_depnum_ccdc_archive 'CCDC 2303221'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H17 Cl2 F3 O4'
_chemical_formula_weight         533.31

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'
Cl Cl 0.1484 0.1585 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.2659(9)
_cell_length_b                   14.989(2)
_cell_length_c                   24.786(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.532(5)
_cell_angle_gamma                90
_cell_volume                     2320.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    5329
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      26.86

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.338
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6142
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      115(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35836
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_av_R_equivalents  0.1025
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5037
_reflns_number_gt                3549
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0315P)²+2.0305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0046(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5037
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
C1 C 0.4796(4) 0.35529(16) 0.62789(9) 0.0148(5) Uani 1 1 d . . . . .
C2 C 0.3664(3) 0.43991(16) 0.64831(9) 0.0147(5) Uani 1 1 d . . . . .
C3 C 0.3439(3) 0.42802(16) 0.70682(9) 0.0149(5) Uani 1 1 d . . . . .
C4 C 0.4383(4) 0.35142(16) 0.72426(9) 0.0152(5) Uani 1 1 d . . . . .
C5 C 0.5456(4) 0.30370(17) 0.68014(9) 0.0175(5) Uani 1 1 d . . . . .
H5A H 0.4967 0.2410 0.6771 0.021 Uiso 1 1 calc R U . . .
H5B H 0.7031 0.3044 0.6877 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2252(4) 0.49406(15) 0.73720(9) 0.0148(5) Uani 1 1 d . . . . .
C7 C 0.0212(4) 0.52128(16) 0.71699(9) 0.0172(5) Uani 1 1 d . . . . .
H7 H -0.0380 0.4994 0.6831 0.021 Uiso 1 1 calc R U . . .
C8 C -0.0943(4) 0.57969(17) 0.74610(10) 0.0198(5) Uani 1 1 d . . . . .
C9 C -0.0087(4) 0.61336(17) 0.79460(10) 0.0226(6) Uani 1 1 d . . . . .
C10 C 0.1922(4) 0.58978(17) 0.81578(10) 0.0215(6) Uani 1 1 d . . . . .
H10 H 0.2510 0.6130 0.8494 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3052(4) 0.53075(17) 0.78611(9) 0.0180(5) Uani 1 1 d . . . . .
C12 C 0.6716(4) 0.38449(16) 0.59846(9) 0.0159(5) Uani 1 1 d . . . . .
C13 C 0.7854(4) 0.44991(18) 0.51930(10) 0.0242(6) Uani 1 1 d . . . . .
H13A H 0.8631 0.4945 0.5421 0.036 Uiso 1 1 calc R U . . .
H13B H 0.7248 0.4782 0.4859 0.036 Uiso 1 1 calc R U . . .
H13C H 0.8840 0.4024 0.5104 0.036 Uiso 1 1 calc R U . . .
C14 C 0.3107(4) 0.30652(16) 0.59061(9) 0.0154(5) Uani 1 1 d . . . . .
H14A H 0.1885 0.2908 0.6118 0.019 Uiso 1 1 calc R U . . .
H14B H 0.2569 0.3479 0.5615 0.019 Uiso 1 1 calc R U . . .
C15 C 0.3904(4) 0.22265(16) 0.56504(9) 0.0170(5) Uani 1 1 d . . . . .
C16 C 0.2399(4) 0.17407(16) 0.52600(9) 0.0172(5) Uani 1 1 d . . . . .
C17 C 0.0264(4) 0.19974(17) 0.51662(10) 0.0216(5) Uani 1 1 d . . . . .
H17 H -0.0290 0.2460 0.5377 0.026 Uiso 1 1 calc R U . . .
C18 C -0.1057(4) 0.15815(18) 0.47664(10) 0.0235(6) Uani 1 1 d . . . . .
H18 H -0.2508 0.1761 0.4699 0.028 Uiso 1 1 calc R U . . .
C19 C -0.0235(4) 0.09048(17) 0.44679(9) 0.0218(6) Uani 1 1 d . . . . .
C20 C 0.1860(4) 0.06144(17) 0.45638(10) 0.0244(6) Uani 1 1 d . . . . .
H20 H 0.2387 0.0135 0.4362 0.029 Uiso 1 1 calc R U . . .
C21 C 0.3169(4) 0.10381(17) 0.49611(9) 0.0202(5) Uani 1 1 d . . . . .
H21 H 0.4611 0.0848 0.5031 0.024 Uiso 1 1 calc R U . . .
C22 C 0.4376(4) 0.30988(16) 0.77815(9) 0.0168(5) Uani 1 1 d . . . . .
C23 C 0.6116(4) 0.25871(17) 0.79869(9) 0.0203(5) Uani 1 1 d . . . . .
H23 H 0.7337 0.2532 0.7785 0.024 Uiso 1 1 calc R U . . .
C24 C 0.6085(4) 0.21583(17) 0.84817(9) 0.0230(6) Uani 1 1 d . . . . .
H24 H 0.7285 0.1821 0.8623 0.028 Uiso 1 1 calc R U . . .
C25 C 0.4279(4) 0.22294(17) 0.87662(9) 0.0233(6) Uani 1 1 d . . . . .
C26 C 0.2520(4) 0.27204(17) 0.85697(10) 0.0246(6) Uani 1 1 d . . . . .
H26 H 0.1287 0.2757 0.8768 0.030 Uiso 1 1 calc R U . . .
C27 C 0.2578(4) 0.31568(17) 0.80803(9) 0.0218(6) Uani 1 1 d . . . . .
H27 H 0.1380 0.3501 0.7945 0.026 Uiso 1 1 calc R U . . .
Cl1 Cl 0.42059(13) 0.16731(5) 0.93800(3) 0.0375(2) Uani 1 1 d . . . . .
Cl2 Cl -0.18814(11) 0.04146(5) 0.39522(3) 0.03271(19) Uani 1 1 d . . . . .
F1 F 0.5034(2) 0.50704(10) 0.80655(5) 0.0248(3) Uani 1 1 d . . . . .
F2 F -0.1269(3) 0.67091(11) 0.82244(6) 0.0371(4) Uani 1 1 d . . . . .
F3 F -0.2942(2) 0.60359(11) 0.72701(6) 0.0301(4) Uani 1 1 d . . . . .
O1 O 0.8533(3) 0.38654(12) 0.61863(6) 0.0227(4) Uani 1 1 d . . . . .
O2 O 0.6142(2) 0.41234(11) 0.54821(6) 0.0188(4) Uani 1 1 d . . . . .
O3 O 0.3018(3) 0.50104(11) 0.61993(6) 0.0204(4) Uani 1 1 d . . . . .
O4 O 0.5748(3) 0.19663(12) 0.57529(6) 0.0211(4) 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
C1 C12 1.520(3) . ?
C1 C14 1.535(3) . ?
C1 C5 1.537(3) . ?
C1 C2 1.557(3) . ?
C2 O3 1.206(3) . ?
C2 C3 1.479(3) . ?
C3 C4 1.347(3) . ?
C3 C6 1.479(3) . ?
C4 C22 1.474(3) . ?
C4 C5 1.508(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.388(3) . ?
C6 C7 1.396(3) . ?
C7 C8 1.376(3) . ?
C7 H7 0.9500 . ?
C8 F3 1.352(3) . ?
C8 C9 1.373(4) . ?
C9 F2 1.360(3) . ?
C9 C10 1.371(4) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 F1 1.351(3) . ?
C12 O1 1.207(3) . ?
C12 O2 1.336(3) . ?
C13 O2 1.450(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.510(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O4 1.227(3) . ?
C15 C16 1.487(3) . ?
C16 C17 1.393(3) . ?
C16 C21 1.396(3) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(4) . ?
C19 Cl2 1.741(2) . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.396(3) . ?
C22 C27 1.399(3) . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(4) . ?
C25 Cl1 1.739(2) . ?
C26 C27 1.381(3) . ?
C26 H26 0.9500 . ?
C27 H27 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
C12 C1 C14 112.50(18) . . ?
C12 C1 C5 112.27(19) . . ?
C14 C1 C5 113.3(2) . . ?
C12 C1 C2 108.64(19) . . ?
C14 C1 C2 105.87(18) . . ?
C5 C1 C2 103.59(17) . . ?
O3 C2 C3 127.6(2) . . ?
O3 C2 C1 124.7(2) . . ?
C3 C2 C1 107.58(19) . . ?
C4 C3 C2 110.1(2) . . ?
C4 C3 C6 129.3(2) . . ?
C2 C3 C6 120.6(2) . . ?
C3 C4 C22 128.2(2) . . ?
C3 C4 C5 112.41(19) . . ?
C22 C4 C5 119.4(2) . . ?
C4 C5 C1 105.46(19) . . ?
C4 C5 H5A 110.6 . . ?
C1 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
C1 C5 H5B 110.6 . . ?
H5A C5 H5B 108.8 . . ?
C11 C6 C7 117.1(2) . . ?
C11 C6 C3 123.2(2) . . ?
C7 C6 C3 119.7(2) . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
F3 C8 C9 119.7(2) . . ?
F3 C8 C7 119.7(2) . . ?
C9 C8 C7 120.5(2) . . ?
F2 C9 C10 119.3(2) . . ?
F2 C9 C8 119.1(2) . . ?
C10 C9 C8 121.6(2) . . ?
C9 C10 C11 117.1(2) . . ?
C9 C10 H10 121.5 . . ?
C11 C10 H10 121.5 . . ?
F1 C11 C10 117.6(2) . . ?
F1 C11 C6 118.8(2) . . ?
C10 C11 C6 123.6(2) . . ?
O1 C12 O2 123.6(2) . . ?
O1 C12 C1 124.4(2) . . ?
O2 C12 C1 111.89(19) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C1 114.44(19) . . ?
C15 C14 H14A 108.7 . . ?
C1 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C1 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
O4 C15 C16 121.2(2) . . ?
O4 C15 C14 121.0(2) . . ?
C16 C15 C14 117.8(2) . . ?
C17 C16 C21 119.2(2) . . ?
C17 C16 C15 121.6(2) . . ?
C21 C16 C15 119.1(2) . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.1(2) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 121.9(2) . . ?
C18 C19 Cl2 118.6(2) . . ?
C20 C19 Cl2 119.5(2) . . ?
C21 C20 C19 118.6(2) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C16 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C23 C22 C27 118.7(2) . . ?
C23 C22 C4 120.3(2) . . ?
C27 C22 C4 120.9(2) . . ?
C24 C23 C22 120.8(2) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 119.0(2) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C26 C25 C24 121.5(2) . . ?
C26 C25 Cl1 119.24(19) . . ?
C24 C25 Cl1 119.2(2) . . ?
C27 C26 C25 119.1(2) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C26 C27 C22 120.9(2) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
C12 O2 C13 115.28(18) . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.067

