# Supplementary Information (SI) for Chemical Science.
# 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_H72_120K_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2404132'
loop_
_audit_author_name
_audit_author_address
'Shashikanth J'
;Indian Institute of Science
India
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.77 H2.15 Cl0.15 F0.23 N0.08 O0.31'
_chemical_formula_weight         51.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   23.2091(7)
_cell_length_b                   10.1744(3)
_cell_length_c                   14.2246(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.8370(10)
_cell_angle_gamma                90
_cell_volume                     3072.45(17)
_cell_formula_units_Z            52
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9254
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      30.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.272
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43797
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.932
_diffrn_reflns_theta_max         30.520
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             8756
_reflns_number_gt                8066
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_max     0.869
_reflns_Friedel_fraction_full    0.954

_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0899P)²+2.9056P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3273 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.068(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8756
_refine_ls_number_parameters     416
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1462
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_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
Cl1 Cl 0.73231(6) 0.32332(12) 0.54785(9) 0.0429(3) Uani 1 1 d . . . . .
Cl2 Cl 0.71788(7) 0.25487(14) 0.73625(11) 0.0526(3) Uani 1 1 d . . . . .
F1 F 0.48360(11) 0.2236(2) 0.58784(17) 0.0265(5) Uani 1 1 d . . . . .
F2 F 0.49823(16) 0.0255(2) 0.5489(2) 0.0447(7) Uani 1 1 d . . . . .
F3 F 0.56002(11) 0.1795(3) 0.5446(2) 0.0361(6) Uani 1 1 d . . . . .
O1 O 0.46177(12) 0.7706(2) 0.26589(19) 0.0207(5) Uani 1 1 d . . . . .
O2 O 0.62964(12) 0.5707(2) 0.5174(2) 0.0235(5) Uani 1 1 d . . . . .
O3 O 0.35269(12) 0.2996(2) 0.4882(2) 0.0224(5) Uani 1 1 d . . . . .
O4 O 0.38807(12) 0.4939(2) 0.5652(2) 0.0219(5) Uani 1 1 d . . . . .
N1 N 0.55316(13) 0.6996(3) 0.3982(2) 0.0167(5) Uani 1 1 d . . . . .
C1 C 0.59140(15) 0.8126(3) 0.4070(3) 0.0202(6) Uani 1 1 d . . . . .
C2 C 0.62223(19) 0.8709(4) 0.5020(3) 0.0278(7) Uani 1 1 d . . . . .
H2 H 0.616852 0.838585 0.560566 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6616(2) 0.9786(4) 0.5103(4) 0.0340(9) Uani 1 1 d . . . . .
H3 H 0.683020 1.020247 0.574930 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6692(2) 1.0246(4) 0.4244(4) 0.0356(9) Uani 1 1 d . . . . .
H4 H 0.696505 1.096769 0.430707 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6375(2) 0.9662(4) 0.3297(4) 0.0355(9) Uani 1 1 d . . . . .
H5 H 0.642072 0.999617 0.270771 0.043 Uiso 1 1 calc R U . . .
C6 C 0.59881(18) 0.8586(4) 0.3210(3) 0.0265(7) Uani 1 1 d . . . . .
H6 H 0.577576 0.816885 0.256328 0.032 Uiso 1 1 calc R U . . .
C7 C 0.49104(15) 0.6863(3) 0.3250(2) 0.0165(6) Uani 1 1 d . . . . .
C8 C 0.46773(15) 0.5500(3) 0.3356(2) 0.0158(5) Uani 1 1 d . . . . .
H8 H 0.450148 0.496560 0.271147 0.019 Uiso 1 1 calc R U . . .
C9 C 0.52305(15) 0.4873(3) 0.4262(2) 0.0158(5) Uani 1 1 d . . . . .
H9 H 0.533860 0.395402 0.414358 0.019 Uiso 1 1 calc R U . . .
C10 C 0.57642(15) 0.5847(3) 0.4553(3) 0.0166(6) Uani 1 1 d . . . . .
C11 C 0.42755(14) 0.5528(3) 0.4008(2) 0.0148(5) Uani 1 1 d . . . . .
C12 C 0.48513(14) 0.5001(3) 0.4937(2) 0.0143(5) Uani 1 1 d . . . . .
C13 C 0.42600(14) 0.4130(3) 0.4418(2) 0.0156(5) Uani 1 1 d . . . . .
C14 C 0.37647(15) 0.6519(3) 0.3826(3) 0.0173(6) Uani 1 1 d . . . . .
C15 C 0.38957(17) 0.7832(3) 0.4075(3) 0.0216(6) Uani 1 1 d . . . . .
H15 H 0.432144 0.811206 0.440022 0.026 Uiso 1 1 calc R U . . .
C16 C 0.34109(18) 0.8752(4) 0.3855(3) 0.0287(8) Uani 1 1 d . . . . .
H16 H 0.350729 0.964668 0.404341 0.034 Uiso 1 1 calc R U . . .
C17 C 0.2789(2) 0.8353(4) 0.3361(4) 0.0341(9) Uani 1 1 d . . . . .
H17 H 0.245837 0.897286 0.321537 0.041 Uiso 1 1 calc R U . . .
C18 C 0.26505(17) 0.7043(5) 0.3077(3) 0.0323(9) Uani 1 1 d . . . . .
H18 H 0.222485 0.677498 0.271983 0.039 Uiso 1 1 calc R U . . .
C19 C 0.31361(16) 0.6118(4) 0.3318(3) 0.0240(7) Uani 1 1 d . . . . .
H19 H 0.303991 0.522102 0.313657 0.029 Uiso 1 1 calc R U . . .
C20 C 0.51903(14) 0.5425(3) 0.6029(2) 0.0149(5) Uani 1 1 d . . . . .
C21 C 0.50681(17) 0.6633(3) 0.6374(3) 0.0215(6) Uani 1 1 d . . . . .
H21 H 0.470954 0.712804 0.595243 0.026 Uiso 1 1 calc R U . . .
C22 C 0.54681(19) 0.7120(4) 0.7333(3) 0.0264(7) Uani 1 1 d . . . . .
H22 H 0.538295 0.794920 0.755675 0.032 Uiso 1 1 calc R U . . .
C23 C 0.59880(17) 0.6404(4) 0.7961(3) 0.0258(7) Uani 1 1 d . . . . .
H23 H 0.626489 0.674719 0.860747 0.031 Uiso 1 1 calc R U . . .
C24 C 0.61029(16) 0.5172(4) 0.7638(3) 0.0243(7) Uani 1 1 d . . . . .
H24 H 0.644921 0.466074 0.807873 0.029 Uiso 1 1 calc R U . . .
C25 C 0.57137(15) 0.4691(3) 0.6677(3) 0.0197(6) Uani 1 1 d . . . . .
H25 H 0.580150 0.386330 0.645500 0.024 Uiso 1 1 calc R U . . .
C26 C 0.42404(16) 0.2953(3) 0.3758(3) 0.0186(6) Uani 1 1 d . . . . .
C27 C 0.45799(17) 0.1777(3) 0.4124(3) 0.0207(6) Uani 1 1 d . . . . .
C28 C 0.45645(19) 0.0768(3) 0.3445(3) 0.0259(7) Uani 1 1 d . . . . .
H28 H 0.479733 -0.001594 0.370454 0.031 Uiso 1 1 calc R U . . .
C29 C 0.4213(2) 0.0902(4) 0.2400(3) 0.0315(8) Uani 1 1 d . . . . .
H29 H 0.420582 0.021816 0.194106 0.038 Uiso 1 1 calc R U . . .
C30 C 0.38746(19) 0.2033(4) 0.2033(3) 0.0283(7) Uani 1 1 d . . . . .
H30 H 0.363367 0.213368 0.131614 0.034 Uiso 1 1 calc R U . . .
C31 C 0.38821(17) 0.3039(3) 0.2707(3) 0.0227(7) Uani 1 1 d . . . . .
H31 H 0.363512 0.380361 0.243853 0.027 Uiso 1 1 calc R U . . .
C32 C 0.38742(15) 0.4087(3) 0.5059(2) 0.0167(6) Uani 1 1 d . . . . .
C33 C 0.31679(19) 0.2874(4) 0.5522(4) 0.0291(8) Uani 1 1 d . . . . .
H33A H 0.286194 0.360453 0.537488 0.035 Uiso 1 1 calc R U . . .
H33B H 0.345554 0.290762 0.625866 0.035 Uiso 1 1 calc R U . . .
C34 C 0.2827(3) 0.1576(5) 0.5272(4) 0.0453(12) Uani 1 1 d . . . . .
H34A H 0.254429 0.151311 0.562791 0.068 Uiso 1 1 calc R U . . .
H34B H 0.313451 0.085826 0.549711 0.068 Uiso 1 1 calc R U . . .
H34C H 0.258126 0.151327 0.452860 0.068 Uiso 1 1 calc R U . . .
C35 C 0.49893(18) 0.1536(3) 0.5223(3) 0.0251(7) Uani 1 1 d . . . . .
C36 C 0.7345(2) 0.3828(4) 0.6656(3) 0.0348(9) Uani 1 1 d . . . . .
H36A H 0.703138 0.454055 0.652324 0.042 Uiso 1 1 calc R U . . .
H36B H 0.776704 0.419782 0.706713 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C36 1.762(5) . ?
Cl2 C36 1.779(5) . ?
F1 C35 1.331(4) . ?
F2 C35 1.358(4) . ?
F3 C35 1.348(5) . ?
O1 C7 1.201(4) . ?
O2 C10 1.201(4) . ?
O3 C32 1.335(4) . ?
O3 C33 1.466(4) . ?
O4 C32 1.205(4) . ?
N1 C10 1.402(4) . ?
N1 C7 1.403(4) . ?
N1 C1 1.426(4) . ?
C1 C2 1.382(5) . ?
C1 C6 1.384(5) . ?
C2 C3 1.400(5) . ?
C3 C4 1.385(7) . ?
C4 C5 1.381(7) . ?
C5 C6 1.389(5) . ?
C7 C8 1.518(4) . ?
C8 C9 1.542(5) . ?
C8 C11 1.558(4) . ?
C9 C10 1.508(4) . ?
C9 C12 1.548(4) . ?
C11 C14 1.497(4) . ?
C11 C13 1.544(4) . ?
C11 C12 1.547(4) . ?
C12 C20 1.494(4) . ?
C12 C13 1.548(4) . ?
C13 C26 1.511(4) . ?
C13 C32 1.515(4) . ?
C14 C15 1.383(5) . ?
C14 C19 1.402(5) . ?
C15 C16 1.399(5) . ?
C16 C17 1.386(6) . ?
C17 C18 1.392(7) . ?
C18 C19 1.400(5) . ?
C20 C21 1.395(4) . ?
C20 C25 1.406(4) . ?
C21 C22 1.395(5) . ?
C22 C23 1.383(6) . ?
C23 C24 1.397(6) . ?
C24 C25 1.388(5) . ?
C26 C31 1.389(5) . ?
C26 C27 1.411(5) . ?
C27 C28 1.400(5) . ?
C27 C35 1.486(6) . ?
C28 C29 1.384(6) . ?
C29 C30 1.372(6) . ?
C30 C31 1.397(5) . ?
C33 C34 1.506(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
C32 O3 C33 113.9(3) . . ?
C10 N1 C7 112.9(3) . . ?
C10 N1 C1 122.8(3) . . ?
C7 N1 C1 124.0(3) . . ?
C2 C1 C6 121.3(3) . . ?
C2 C1 N1 119.3(3) . . ?
C6 C1 N1 119.4(3) . . ?
C1 C2 C3 118.7(4) . . ?
C4 C3 C2 120.1(4) . . ?
C5 C4 C3 120.5(4) . . ?
C4 C5 C6 119.8(4) . . ?
C1 C6 C5 119.6(4) . . ?
O1 C7 N1 124.8(3) . . ?
O1 C7 C8 126.8(3) . . ?
N1 C7 C8 108.4(3) . . ?
C7 C8 C9 104.5(2) . . ?
C7 C8 C11 111.4(2) . . ?
C9 C8 C11 90.4(2) . . ?
C10 C9 C8 105.8(2) . . ?
C10 C9 C12 112.6(3) . . ?
C8 C9 C12 89.6(2) . . ?
O2 C10 N1 124.4(3) . . ?
O2 C10 C9 127.6(3) . . ?
N1 C10 C9 107.9(3) . . ?
C14 C11 C13 123.2(2) . . ?
C14 C11 C12 137.0(3) . . ?
C13 C11 C12 60.09(19) . . ?
C14 C11 C8 122.2(3) . . ?
C13 C11 C8 108.6(2) . . ?
C12 C11 C8 89.1(2) . . ?
C20 C12 C13 130.8(3) . . ?
C20 C12 C11 134.3(3) . . ?
C13 C12 C11 59.9(2) . . ?
C20 C12 C9 118.5(3) . . ?
C13 C12 C9 105.9(2) . . ?
C11 C12 C9 90.6(2) . . ?
C26 C13 C32 118.4(3) . . ?
C26 C13 C11 119.6(3) . . ?
C32 C13 C11 111.3(2) . . ?
C26 C13 C12 123.2(3) . . ?
C32 C13 C12 110.8(2) . . ?
C11 C13 C12 60.04(19) . . ?
C15 C14 C19 119.2(3) . . ?
C15 C14 C11 122.0(3) . . ?
C19 C14 C11 118.6(3) . . ?
C14 C15 C16 121.0(3) . . ?
C17 C16 C15 119.7(4) . . ?
C16 C17 C18 119.9(3) . . ?
C17 C18 C19 120.2(4) . . ?
C18 C19 C14 119.8(4) . . ?
C21 C20 C25 118.8(3) . . ?
C21 C20 C12 121.6(3) . . ?
C25 C20 C12 118.7(3) . . ?
C20 C21 C22 120.5(3) . . ?
C23 C22 C21 120.4(3) . . ?
C22 C23 C24 119.5(3) . . ?
C25 C24 C23 120.4(3) . . ?
C24 C25 C20 120.3(3) . . ?
C31 C26 C27 116.9(3) . . ?
C31 C26 C13 118.3(3) . . ?
C27 C26 C13 124.8(3) . . ?
C28 C27 C26 120.8(3) . . ?
C28 C27 C35 115.6(3) . . ?
C26 C27 C35 123.6(3) . . ?
C29 C28 C27 120.5(4) . . ?
C30 C29 C28 119.4(3) . . ?
C29 C30 C31 120.5(4) . . ?
C26 C31 C30 121.9(3) . . ?
O4 C32 O3 124.5(3) . . ?
O4 C32 C13 123.9(3) . . ?
O3 C32 C13 111.7(3) . . ?
O3 C33 C34 107.7(3) . . ?
F1 C35 F3 106.5(3) . . ?
F1 C35 F2 106.4(3) . . ?
F3 C35 F2 104.6(3) . . ?
F1 C35 C27 114.2(3) . . ?
F3 C35 C27 112.3(3) . . ?
F2 C35 C27 112.1(3) . . ?
Cl1 C36 Cl2 110.9(2) . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_H93_LT_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2425129'
loop_
_audit_author_name
_audit_author_address
'Shashikanth J'
;Indian Institute of Science
India
;
_audit_update_record             
;
2025-02-19 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 F4 O4'
_chemical_formula_weight         444.37

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'

_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                   8.5086(7)
_cell_length_b                   10.3951(9)
_cell_length_c                   11.7700(10)
_cell_angle_alpha                94.161(3)
_cell_angle_beta                 106.191(3)
_cell_angle_gamma                91.831(3)
_cell_volume                     995.62(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9795
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.46

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35748
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.783
_diffrn_reflns_theta_max         27.657
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4545
_reflns_number_gt                4169
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0539P)²+0.4658P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4545
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_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
F1 F 0.90682(11) 0.20912(9) 0.78639(8) 0.0344(2) Uani 1 1 d . . . . .
F2 F 0.78606(15) 1.02598(9) 0.53933(10) 0.0519(3) Uani 1 1 d . . . . .
F3 F 0.79941(14) 0.06645(8) 0.86944(9) 0.0440(3) Uani 1 1 d . . . . .
F4 F 0.86263(11) 0.25793(8) 0.95505(8) 0.0345(2) Uani 1 1 d . . . . .
O2 O 0.77598(11) 0.51222(9) 0.95221(8) 0.0219(2) Uani 1 1 d . . . . .
O3 O 0.75509(11) 0.35208(9) 0.55835(8) 0.0242(2) Uani 1 1 d . . . . .
O4 O 0.32930(14) 0.88254(10) 0.87675(11) 0.0380(3) Uani 1 1 d . . . . .
O5 O 0.97527(11) 0.47668(9) 0.66605(9) 0.0262(2) Uani 1 1 d . . . . .
C1 C 0.75781(15) 0.70198(12) 0.71447(11) 0.0199(2) Uani 1 1 d . . . . .
C2 C 0.61922(17) 0.74274(14) 0.63369(12) 0.0279(3) Uani 1 1 d . . . . .
H2 H 0.517670 0.694601 0.618659 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6272(2) 0.85250(15) 0.57491(14) 0.0358(3) Uani 1 1 d . . . . .
H3 H 0.532333 0.881118 0.520761 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7766(2) 0.91868(14) 0.59731(13) 0.0334(3) Uani 1 1 d . . . . .
C5 C 0.91701(19) 0.88140(13) 0.67533(14) 0.0314(3) Uani 1 1 d . . . . .
H5 H 1.018508 0.928973 0.688091 0.038 Uiso 1 1 calc R U . . .
C6 C 0.90660(16) 0.77231(13) 0.73503(12) 0.0250(3) Uani 1 1 d . . . . .
H6 H 1.001694 0.745506 0.790281 0.030 Uiso 1 1 calc R U . . .
C7 C 0.73968(14) 0.59152(12) 0.78338(10) 0.0180(2) Uani 1 1 d . . . . .
C8 C 0.74526(14) 0.44644(12) 0.74387(11) 0.0190(2) Uani 1 1 d . . . . .
C9 C 0.85761(15) 0.50732(12) 0.86095(11) 0.0194(2) Uani 1 1 d . . . . .
H9 H 0.979290 0.518408 0.877421 0.023 Uiso 1 1 calc R U . . .
C10 C 0.66428(15) 0.60678(12) 0.89154(11) 0.0199(2) Uani 1 1 d . . . . .
C11 C 0.48798(15) 0.57078(12) 0.87606(11) 0.0216(3) Uani 1 1 d . . . . .
H11 H 0.453212 0.482023 0.868385 0.026 Uiso 1 1 calc R U . . .
C12 C 0.37788(16) 0.66001(13) 0.87273(12) 0.0243(3) Uani 1 1 d . . . . .
H12 H 0.264952 0.633939 0.854392 0.029 Uiso 1 1 calc R U . . .
C13 C 0.42888(17) 0.79837(13) 0.89708(12) 0.0260(3) Uani 1 1 d . . . . .
C14 C 0.60577(17) 0.82937(13) 0.95167(12) 0.0251(3) Uani 1 1 d . . . . .
H14 H 0.642360 0.913827 0.987707 0.030 Uiso 1 1 calc R U . . .
C15 C 0.71429(16) 0.74039(13) 0.95094(11) 0.0232(3) Uani 1 1 d . . . . .
H15 H 0.826937 0.761980 0.989154 0.028 Uiso 1 1 calc R U . . .
C16 C 0.60722(15) 0.34862(13) 0.73317(11) 0.0223(3) Uani 1 1 d . . . . .
C17 C 0.44948(17) 0.37521(15) 0.66923(14) 0.0311(3) Uani 1 1 d . . . . .
H17 H 0.432808 0.451573 0.628674 0.037 Uiso 1 1 calc R U . . .
C18 C 0.31583(19) 0.29207(19) 0.66363(16) 0.0439(4) Uani 1 1 d . . . . .
H18 H 0.208601 0.312857 0.621231 0.053 Uiso 1 1 calc R U . . .
C19 C 0.3391(2) 0.17951(19) 0.71961(17) 0.0464(4) Uani 1 1 d . . . . .
H19 H 0.247427 0.123958 0.717895 0.056 Uiso 1 1 calc R U . . .
C20 C 0.4951(2) 0.14732(16) 0.77814(14) 0.0383(4) Uani 1 1 d . . . . .
H20 H 0.510983 0.067867 0.813813 0.046 Uiso 1 1 calc R U . . .
C21 C 0.63004(17) 0.23099(13) 0.78525(12) 0.0268(3) Uani 1 1 d . . . . .
C22 C 0.84003(15) 0.42886(12) 0.65351(11) 0.0199(2) Uani 1 1 d . . . . .
C23 C 0.84256(17) 0.31856(15) 0.47196(12) 0.0296(3) Uani 1 1 d . . . . .
H23A H 0.770200 0.264304 0.405052 0.044 Uiso 1 1 calc R U . . .
H23B H 0.938674 0.271142 0.509076 0.044 Uiso 1 1 calc R U . . .
H23C H 0.878014 0.397564 0.443294 0.044 Uiso 1 1 calc R U . . .
C24 C 0.79766(19) 0.19134(13) 0.84849(13) 0.0291(3) 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 C24 1.3484(16) . ?
F2 C4 1.3608(16) . ?
F3 C24 1.3386(16) . ?
F4 C24 1.3494(17) . ?
O2 C9 1.4315(14) . ?
O2 C10 1.4706(15) . ?
O3 C22 1.3401(15) . ?
O3 C23 1.4479(15) . ?
O4 C13 1.2269(17) . ?
O5 C22 1.2046(16) . ?
C1 C2 1.3925(18) . ?
C1 C6 1.3929(18) . ?
C1 C7 1.4811(17) . ?
C2 C3 1.386(2) . ?
C3 C4 1.374(2) . ?
C4 C5 1.375(2) . ?
C5 C6 1.3898(19) . ?
C7 C9 1.5059(17) . ?
C7 C8 1.5518(16) . ?
C7 C10 1.5779(16) . ?
C8 C16 1.5007(17) . ?
C8 C22 1.5081(17) . ?
C8 C9 1.5209(17) . ?
C10 C11 1.4917(17) . ?
C10 C15 1.5014(17) . ?
C11 C12 1.3341(18) . ?
C12 C13 1.4731(19) . ?
C13 C14 1.477(2) . ?
C14 C15 1.3289(19) . ?
C16 C17 1.3909(19) . ?
C16 C21 1.4022(19) . ?
C17 C18 1.390(2) . ?
C18 C19 1.377(3) . ?
C19 C20 1.379(3) . ?
C20 C21 1.3978(19) . ?
C21 C24 1.499(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 C10 91.05(8) . . ?
C22 O3 C23 115.33(10) . . ?
C2 C1 C6 119.14(12) . . ?
C2 C1 C7 118.85(11) . . ?
C6 C1 C7 121.80(11) . . ?
C3 C2 C1 120.98(13) . . ?
C4 C3 C2 118.00(14) . . ?
F2 C4 C3 118.47(15) . . ?
F2 C4 C5 118.44(14) . . ?
C3 C4 C5 123.09(13) . . ?
C4 C5 C6 118.27(13) . . ?
C5 C6 C1 120.51(13) . . ?
C1 C7 C9 134.49(11) . . ?
C1 C7 C8 126.30(10) . . ?
C9 C7 C8 59.63(8) . . ?
C1 C7 C10 121.56(10) . . ?
C9 C7 C10 84.35(9) . . ?
C8 C7 C10 110.27(10) . . ?
C16 C8 C22 116.45(10) . . ?
C16 C8 C9 124.50(11) . . ?
C22 C8 C9 109.89(10) . . ?
C16 C8 C7 123.42(10) . . ?
C22 C8 C7 111.13(10) . . ?
C9 C8 C7 58.68(8) . . ?
O2 C9 C7 94.24(9) . . ?
O2 C9 C8 111.19(10) . . ?
C7 C9 C8 61.68(8) . . ?
O2 C10 C11 113.37(10) . . ?
O2 C10 C15 110.75(10) . . ?
C11 C10 C15 112.65(10) . . ?
O2 C10 C7 89.79(8) . . ?
C11 C10 C7 120.87(10) . . ?
C15 C10 C7 107.22(10) . . ?
C12 C11 C10 121.70(12) . . ?
C11 C12 C13 120.96(12) . . ?
O4 C13 C12 121.80(13) . . ?
O4 C13 C14 122.12(13) . . ?
C12 C13 C14 116.04(12) . . ?
C15 C14 C13 120.72(12) . . ?
C14 C15 C10 122.00(12) . . ?
C17 C16 C21 118.25(13) . . ?
C17 C16 C8 118.94(12) . . ?
C21 C16 C8 122.81(12) . . ?
C18 C17 C16 121.17(16) . . ?
C19 C18 C17 119.91(16) . . ?
C18 C19 C20 120.10(15) . . ?
C19 C20 C21 120.34(16) . . ?
C20 C21 C16 120.06(14) . . ?
C20 C21 C24 118.52(14) . . ?
C16 C21 C24 121.41(12) . . ?
O5 C22 O3 124.52(11) . . ?
O5 C22 C8 124.25(11) . . ?
O3 C22 C8 111.23(10) . . ?
F3 C24 F1 106.11(11) . . ?
F3 C24 F4 105.94(12) . . ?
F1 C24 F4 105.67(12) . . ?
F3 C24 C21 112.73(12) . . ?
F1 C24 C21 112.52(11) . . ?
F4 C24 C21 113.26(11) . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2409070'
loop_
_audit_author_name
_audit_author_address
'Shashikanth J'
;Indian Institute of Science
India
;
_audit_update_record             
;
2024-12-10 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form

_vrf_PLAT043_shelx               
;
PROBLEM: Calculated and Reported Mol. Weight Differ by .. 7.08
RESPONSE: In the molecules, the correponding atoms of ortho -OMe-phenyl ring
were having positional disorderness. To solve this problem, we have share the 
occupancy of non-hydrogen atoms. Because of this, we were not able to locate 
seven hydrogen atoms attched with the disordered ring. This is why, Mol. Wt 
is differ by 7 units.
;
# end Validation Reply Form
#============================================================================== 

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H26 Cl N O5'
_chemical_formula_sum            'C34 H26 Cl N O5'
_chemical_formula_weight         564.01

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.0072(7)
_cell_length_b                   11.2445(9)
_cell_length_c                   20.5394(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.189(3)
_cell_angle_gamma                90
_cell_volume                     2772.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1500
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.7

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      1.35
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   0.663400
_exptl_transmission_factor_max   0.745700
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Smart APEX 3'
_diffrn_measurement_method       'φ and ω Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17518
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.156
_diffrn_reflns_theta_max         27.687
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             6282
_reflns_number_gt                4513
_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 Apex 3'
_computing_cell_refinement       'Bruker Apex 3'
_computing_data_reduction        'Bruker Apex 3'
_computing_structure_solution    'SHELXT 2019/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEP 3 for windows'
_computing_publication_material  WinGX
_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)+(0.0747P)²+11.5364P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6282
_refine_ls_number_parameters     438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1466
_refine_ls_R_factor_gt           0.1115
_refine_ls_wR_factor_ref         0.2710
_refine_ls_wR_factor_gt          0.2520
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.40151(15) 0.75630(19) 0.85589(11) 0.0794(7) Uani 1 1 d . . . . .
O1 O 0.4492(3) 0.2649(3) 0.61455(18) 0.0356(9) Uani 1 1 d . . . . .
O2 O 0.6613(3) 0.5531(3) 0.70083(17) 0.0317(8) Uani 1 1 d . . . . .
O3 O 0.4706(3) 0.2169(3) 0.75285(15) 0.0247(7) Uani 1 1 d . . . . .
O4 O 0.4847(3) 0.1025(3) 0.55673(18) 0.0343(9) Uani 1 1 d . . . . .
N1 N 0.5416(3) 0.4017(3) 0.72647(17) 0.0192(7) Uani 1 1 d . . . . .
C1 C 0.4489(4) 0.4728(4) 0.7450(2) 0.0215(9) Uani 1 1 d . . . . .
C2 C 0.3437(4) 0.4499(4) 0.7189(2) 0.0266(10) Uani 1 1 d . . . . .
H2 H 0.338(5) 0.378(5) 0.685(3) 0.043(16) Uiso 1 1 d . . . . .
C3 C 0.2560(4) 0.5224(5) 0.7369(3) 0.0317(11) Uani 1 1 d . . . . .
H3 H 0.188(5) 0.507(5) 0.726(3) 0.030(14) Uiso 1 1 d . . . . .
C4 C 0.2717(4) 0.6155(5) 0.7803(3) 0.0369(12) Uani 1 1 d . . . . .
H4 H 0.215(4) 0.670(5) 0.793(2) 0.028(13) Uiso 1 1 d . . . . .
C5 C 0.3775(5) 0.6360(5) 0.8039(3) 0.0398(13) Uani 1 1 d . . . . .
C6 C 0.4673(4) 0.5658(4) 0.7879(2) 0.0299(11) Uani 1 1 d . . . . .
H6 H 0.544(5) 0.580(5) 0.805(3) 0.038(15) Uiso 1 1 d . . . . .
C7 C 0.6407(4) 0.4481(4) 0.7042(2) 0.0210(9) Uani 1 1 d . . . . .
C8 C 0.7159(3) 0.3454(4) 0.6858(2) 0.0195(8) Uani 1 1 d . . . . .
H8 H 0.773(4) 0.354(4) 0.716(2) 0.017(11) Uiso 1 1 d . . . . .
C9 C 0.6463(3) 0.2332(4) 0.6956(2) 0.0186(8) Uani 1 1 d . . . . .
H9 H 0.679(4) 0.167(5) 0.721(2) 0.023(12) Uiso 1 1 d . . . . .
C10 C 0.5404(3) 0.2756(4) 0.7278(2) 0.0200(9) Uani 1 1 d . . . . .
C11 C 0.7463(3) 0.3458(4) 0.6149(2) 0.0190(8) Uani 1 1 d . . . . .
C12 C 0.7040(3) 0.2505(4) 0.5830(2) 0.0191(8) Uani 1 1 d . . . . .
C13 C 0.6303(3) 0.1720(4) 0.62745(19) 0.0179(8) Uani 1 1 d . . . . .
C14 C 0.8137(4) 0.4432(4) 0.5886(2) 0.0214(9) Uani 1 1 d . . . . .
C15 C 0.9016(4) 0.4926(4) 0.6264(3) 0.0290(10) Uani 1 1 d . . . . .
H15 H 0.924(4) 0.454(5) 0.670(3) 0.038(15) Uiso 1 1 d . . . . .
C16 C 0.9646(4) 0.5849(5) 0.6010(3) 0.0374(12) Uani 1 1 d . . . . .
H16 H 1.020(4) 0.619(4) 0.628(2) 0.021(12) Uiso 1 1 d . . . . .
C17 C 0.9413(5) 0.6314(5) 0.5403(3) 0.0393(13) Uani 1 1 d . . . . .
H17 H 0.982(5) 0.701(6) 0.518(3) 0.057(19) Uiso 1 1 d . . . . .
C18 C 0.8537(6) 0.5856(6) 0.5043(3) 0.0469(15) Uani 1 1 d . . . . .
H18 H 0.834(6) 0.620(7) 0.466(4) 0.07(2) Uiso 1 1 d . . . . .
C19 C 0.7914(5) 0.4921(5) 0.5273(3) 0.0369(12) Uani 1 1 d . . . . .
H19 H 0.733(5) 0.460(6) 0.497(3) 0.052(18) Uiso 1 1 d . . . . .
C26 C 0.6651(4) 0.0423(4) 0.6329(2) 0.0204(9) Uani 1 1 d . . . . .
C27 C 0.5929(4) -0.0440(4) 0.6564(2) 0.0250(9) Uani 1 1 d . . . . .
H27 H 0.514(4) -0.018(5) 0.664(3) 0.029(14) Uiso 1 1 d . . . . .
C28 C 0.6265(4) -0.1606(4) 0.6644(3) 0.0306(11) Uani 1 1 d . . . . .
H28 H 0.570(5) -0.207(6) 0.683(3) 0.044(17) Uiso 1 1 d . . . . .
C29 C 0.7334(4) -0.1958(4) 0.6479(2) 0.0300(11) Uani 1 1 d . . . . .
H29 H 0.745(4) -0.292(5) 0.655(3) 0.032(14) Uiso 1 1 d . . . . .
C30 C 0.8065(4) -0.1113(5) 0.6274(2) 0.0301(11) Uani 1 1 d . . . . .
H30 H 0.883(5) -0.141(5) 0.619(3) 0.041(16) Uiso 1 1 d . . . . .
C31 C 0.7733(4) 0.0082(4) 0.6202(2) 0.0237(9) Uani 1 1 d . . . . .
H31 H 0.826(5) 0.079(6) 0.613(3) 0.045(17) Uiso 1 1 d . . . . .
C32 C 0.5106(3) 0.1856(4) 0.5997(2) 0.0184(8) Uani 1 1 d . . . . .
C33 C 0.3747(5) 0.1126(6) 0.5268(3) 0.0401(14) Uani 1 1 d . . . . .
H33A H 0.362(7) 0.041(9) 0.510(5) 0.09(3) Uiso 1 1 d . . . . .
H33B H 0.359(5) 0.197(7) 0.511(3) 0.054(19) Uiso 1 1 d . . . . .
H33C H 0.319(5) 0.080(6) 0.558(3) 0.045(17) Uiso 1 1 d . . . . .
C34A C 0.4818(8) 0.4009(9) 0.4439(5) 0.052(2) Uiso 0.7 1 d . . P . .
C34B C 1.002(2) 0.076(2) 0.5212(12) 0.058(6) Uiso 0.3 1 d . . P . .
O5A O 0.5541(4) 0.3345(5) 0.4897(2) 0.0339(11) Uiso 0.7 1 d . . P . .
O5B O 0.9062(10) 0.1577(11) 0.5332(6) 0.036(3) Uiso 0.3 1 d . . P . .
C20A C 0.7079(11) 0.2349(11) 0.5094(6) 0.019(3) Uiso 0.5 1 d . . P . .
C20B C 0.7274(11) 0.2197(11) 0.5138(6) 0.019(3) Uiso 0.5 1 d . . P . .
C21A C 0.8302(11) 0.1678(12) 0.4946(7) 0.032(3) Uiso 0.5 1 d . . P . .
C21B C 0.8052(9) 0.1766(9) 0.4845(5) 0.013(2) Uiso 0.5 1 d . . P . .
C22A C 0.8443(12) 0.1484(13) 0.4265(7) 0.037(4) Uiso 0.5 1 d . . P . .
C22B C 0.8204(11) 0.1629(11) 0.4179(6) 0.023(3) Uiso 0.5 1 d . . P . .
C23A C 0.7619(12) 0.1829(13) 0.3819(7) 0.035(3) Uiso 0.5 1 d . . P . .
C23B C 0.7382(12) 0.2095(13) 0.3758(6) 0.032(3) Uiso 0.5 1 d . . P . .
C24A C 0.6468(11) 0.2693(13) 0.3974(6) 0.035(3) Uiso 0.5 1 d . . P . .
C24B C 0.6644(12) 0.2362(14) 0.3991(7) 0.040(4) Uiso 0.5 1 d . . P . .
C25A C 0.6342(9) 0.2791(11) 0.4645(5) 0.019(2) Uiso 0.5 1 d . . P . .
C25B C 0.6425(14) 0.2482(16) 0.4693(9) 0.051(5) Uiso 0.5 1 d . . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.744(5) . ?
O1 C32 1.201(5) . ?
O2 C7 1.208(5) . ?
O3 C10 1.192(5) . ?
O4 C32 1.318(5) . ?
O4 C33 1.450(6) . ?
N1 C7 1.386(5) . ?
N1 C10 1.418(6) . ?
N1 C1 1.428(5) . ?
C1 C6 1.382(6) . ?
C1 C2 1.386(6) . ?
C2 C3 1.388(7) . ?
C3 C4 1.386(7) . ?
C4 C5 1.369(8) . ?
C5 C6 1.382(7) . ?
C7 C8 1.518(6) . ?
C8 C11 1.510(6) . ?
C8 C9 1.529(6) . ?
C9 C10 1.521(6) . ?
C9 C13 1.568(6) . ?
C11 C12 1.350(6) . ?
C11 C14 1.472(6) . ?
C12 C20B 1.494(13) . ?
C12 C20A 1.522(13) . ?
C12 C13 1.558(6) . ?
C13 C26 1.521(6) . ?
C13 C32 1.543(6) . ?
C14 C19 1.395(7) . ?
C14 C15 1.410(6) . ?
C15 C16 1.392(7) . ?
C16 C17 1.375(8) . ?
C17 C18 1.374(9) . ?
C18 C19 1.379(8) . ?
C26 C31 1.384(6) . ?
C26 C27 1.394(6) . ?
C27 C28 1.381(7) . ?
C28 C29 1.391(7) . ?
C29 C30 1.366(7) . ?
C30 C31 1.408(7) . ?
C34A O5A 1.470(11) . ?
C34B O5B 1.49(3) . ?
C34B C34B 1.92(5) 3_756 ?
O5A C25A 1.266(12) . ?
O5A C25B 1.504(18) . ?
O5B C21A 1.202(18) . ?
O5B C21B 1.570(16) . ?
C20A C25B 1.14(2) . ?
C20A C25A 1.359(18) . ?
C20A C21B 1.443(16) . ?
C20A C21A 1.684(19) . ?
C20B C21B 1.223(16) . ?
C20B C25B 1.39(2) . ?
C20B C21A 1.429(18) . ?
C20B C25A 1.636(18) . ?
C21A C22A 1.43(2) . ?
C21A C22B 1.578(18) . ?
C21B C22A 1.328(17) . ?
C21B C22B 1.393(15) . ?
C22A C22B 0.372(18) . ?
C22A C23A 1.39(2) . ?
C22A C23B 1.77(2) . ?
C22B C23A 1.033(16) . ?
C22B C23B 1.400(18) . ?
C22B C24B 2.08(2) . ?
C23A C24B 1.37(2) . ?
C23A C24A 1.73(2) . ?
C23B C24B 1.060(17) . ?
C23B C24A 1.370(19) . ?
C24A C25A 1.393(17) . ?
C24A C25B 1.50(2) . ?
C24B C25B 1.48(2) . ?
C24B C25A 1.479(18) . ?

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
C32 O4 C33 115.4(4) . . ?
C7 N1 C10 113.1(3) . . ?
C7 N1 C1 123.8(4) . . ?
C10 N1 C1 123.1(4) . . ?
C6 C1 C2 121.2(4) . . ?
C6 C1 N1 118.6(4) . . ?
C2 C1 N1 120.2(4) . . ?
C1 C2 C3 118.7(4) . . ?
C2 C3 C4 121.4(5) . . ?
C5 C4 C3 117.9(5) . . ?
C4 C5 C6 122.8(5) . . ?
C4 C5 Cl1 119.2(4) . . ?
C6 C5 Cl1 118.0(4) . . ?
C5 C6 C1 118.0(5) . . ?
O2 C7 N1 124.4(4) . . ?
O2 C7 C8 127.3(4) . . ?
N1 C7 C8 108.3(4) . . ?
C11 C8 C7 113.2(4) . . ?
C11 C8 C9 105.8(3) . . ?
C7 C8 C9 105.4(3) . . ?
C10 C9 C8 105.2(3) . . ?
C10 C9 C13 116.0(3) . . ?
C8 C9 C13 107.6(3) . . ?
O3 C10 N1 124.7(4) . . ?
O3 C10 C9 128.0(4) . . ?
N1 C10 C9 107.2(3) . . ?
C12 C11 C14 128.2(4) . . ?
C12 C11 C8 111.8(4) . . ?
C14 C11 C8 120.1(4) . . ?
C11 C12 C20B 124.7(6) . . ?
C11 C12 C20A 123.6(6) . . ?
C20B C12 C20A 11.4(7) . . ?
C11 C12 C13 112.1(4) . . ?
C20B C12 C13 123.1(6) . . ?
C20A C12 C13 123.1(6) . . ?
C26 C13 C32 112.0(3) . . ?
C26 C13 C12 115.3(3) . . ?
C32 C13 C12 105.2(3) . . ?
C26 C13 C9 109.1(3) . . ?
C32 C13 C9 112.5(3) . . ?
C12 C13 C9 102.4(3) . . ?
C19 C14 C15 118.0(4) . . ?
C19 C14 C11 121.8(4) . . ?
C15 C14 C11 120.2(4) . . ?
C16 C15 C14 119.5(5) . . ?
C17 C16 C15 121.4(5) . . ?
C18 C17 C16 119.0(5) . . ?
C17 C18 C19 121.1(6) . . ?
C18 C19 C14 120.9(5) . . ?
C31 C26 C27 117.7(4) . . ?
C31 C26 C13 120.6(4) . . ?
C27 C26 C13 121.4(4) . . ?
C28 C27 C26 121.3(4) . . ?
C27 C28 C29 120.6(5) . . ?
C30 C29 C28 118.6(4) . . ?
C29 C30 C31 120.9(5) . . ?
C26 C31 C30 120.6(4) . . ?
O1 C32 O4 124.0(4) . . ?
O1 C32 C13 123.5(4) . . ?
O4 C32 C13 112.5(3) . . ?
O5B C34B C34B 128(2) . 3_756 ?
C25A O5A C34A 115.6(7) . . ?
C25A O5A C25B 12.0(9) . . ?
C34A O5A C25B 124.1(9) . . ?
C21A O5B C34B 121.7(15) . . ?
C21A O5B C21B 2.8(9) . . ?
C34B O5B C21B 124.4(13) . . ?
C25B C20A C25A 13.9(11) . . ?
C25B C20A C21B 110.8(13) . . ?
C25A C20A C21B 116.5(11) . . ?
C25B C20A C12 132.0(14) . . ?
C25A C20A C12 126.8(10) . . ?
C21B C20A C12 116.5(10) . . ?
C25B C20A C21A 121.3(14) . . ?
C25A C20A C21A 126.7(11) . . ?
C21B C20A C21A 10.5(7) . . ?
C12 C20A C21A 106.1(9) . . ?
C21B C20B C25B 108.9(12) . . ?
C21B C20B C21A 13.5(7) . . ?
C25B C20B C21A 122.5(13) . . ?
C21B C20B C12 136.1(11) . . ?
C25B C20B C12 114.9(11) . . ?
C21A C20B C12 122.6(10) . . ?
C21B C20B C25A 112.1(11) . . ?
C25B C20B C25A 10.8(9) . . ?
C21A C20B C25A 125.4(11) . . ?
C12 C20B C25A 110.8(9) . . ?
O5B C21A C20B 120.3(13) . . ?
O5B C21A C22A 121.8(13) . . ?
C20B C21A C22A 117.0(13) . . ?
O5B C21A C20A 125.2(12) . . ?
C20B C21A C20A 5.9(8) . . ?
C22A C21A C20A 111.6(11) . . ?
O5B C21A C22B 134.0(13) . . ?
C20B C21A C22B 104.1(11) . . ?
C22A C21A C22B 13.0(7) . . ?
C20A C21A C22B 98.6(10) . . ?
C20B C21B C22A 145.6(13) . . ?
C20B C21B C20A 8.9(9) . . ?
C22A C21B C20A 136.9(12) . . ?
C20B C21B O5B 109.2(10) . . ?
C22A C21B O5B 104.8(10) . . ?
C20A C21B O5B 117.1(9) . . ?
C20B C21B C22B 130.1(12) . . ?
C22A C21B C22B 15.5(8) . . ?
C20A C21B C22B 121.5(11) . . ?
O5B C21B C22B 119.7(10) . . ?
C22B C22A C23A 14(3) . . ?
C22B C22A C21B 92(4) . . ?
C23A C22A C21B 105.3(12) . . ?
C22B C22A C21A 107(4) . . ?
C23A C22A C21A 120.3(13) . . ?
C21B C22A C21A 15.0(7) . . ?
C22B C22A C23B 8(3) . . ?
C23A C22A C23B 7.5(8) . . ?
C21B C22A C23B 99.9(11) . . ?
C21A C22A C23B 114.7(11) . . ?
C22A C22B C23A 160(4) . . ?
C22A C22B C23B 170(4) . . ?
C23A C22B C23B 10.7(11) . . ?
C22A C22B C21B 72(4) . . ?
C23A C22B C21B 125.3(14) . . ?
C23B C22B C21B 117.4(11) . . ?
C22A C22B C24B 161(4) . . ?
C23A C22B C24B 35.2(9) . . ?
C23B C22B C24B 27.7(7) . . ?
C21B C22B C24B 90.2(9) . . ?
C22A C22B C21A 60(4) . . ?
C23A C22B C21A 137.8(14) . . ?
C23B C22B C21A 129.8(11) . . ?
C21B C22B C21A 12.6(6) . . ?
C24B C22B C21A 102.7(9) . . ?
C22B C23A C22A 5.1(11) . . ?
C22B C23A C24B 118.9(14) . . ?
C22A C23A C24B 123.7(13) . . ?
C22B C23A C24A 121.7(13) . . ?
C22A C23A C24A 126.7(12) . . ?
C24B C23A C24A 8.9(9) . . ?
C22B C23B C24B 114.4(14) . . ?
C22B C23B C24A 122.9(12) . . ?
C24B C23B C24A 14.1(11) . . ?
C22B C23B C22A 2.0(9) . . ?
C24B C23B C22A 116.3(13) . . ?
C24A C23B C22A 124.9(11) . . ?
C23B C24A C25A 117.6(12) . . ?
C23B C24A C25B 106.6(13) . . ?
C25A C24A C25B 14.3(8) . . ?
C23B C24A C23A 9.0(8) . . ?
C25A C24A C23A 109.3(11) . . ?
C25B C24A C23A 97.9(11) . . ?
C23B C24B C23A 14.3(10) . . ?
C23B C24B C25B 129.4(16) . . ?
C23A C24B C25B 117.5(14) . . ?
C23B C24B C25A 136.5(15) . . ?
C23A C24B C25A 127.1(13) . . ?
C25B C24B C25A 14.5(8) . . ?
C23B C24B C22B 37.9(9) . . ?
C23A C24B C22B 25.8(7) . . ?
C25B C24B C22B 91.9(10) . . ?
C25A C24B C22B 101.4(9) . . ?
O5A C25A C20A 113.1(10) . . ?
O5A C25A C24A 122.8(11) . . ?
C20A C25A C24A 124.1(11) . . ?
O5A C25A C24B 137.2(11) . . ?
C20A C25A C24B 109.2(11) . . ?
C24A C25A C24B 16.8(8) . . ?
O5A C25A C20B 117.6(9) . . ?
C20A C25A C20B 4.6(9) . . ?
C24A C25A C20B 119.6(10) . . ?
C24B C25A C20B 104.6(10) . . ?
C20A C25B C20B 7.3(10) . . ?
C20A C25B C24B 124.2(16) . . ?
C20B C25B C24B 118.5(14) . . ?
C20A C25B C24A 134.3(16) . . ?
C20B C25B C24A 130.1(14) . . ?
C24B C25B C24A 16.6(7) . . ?
C20A C25B O5A 111.3(15) . . ?
C20B C25B O5A 118.5(14) . . ?
C24B C25B O5A 118.1(14) . . ?
C24A C25B O5A 102.2(12) . . ?

_refine_diff_density_max         0.616
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_HN10_rpt_a
_database_code_depnum_ccdc_archive 'CCDC 2448186'
loop_
_audit_author_name
_audit_author_address
'Shashikanth J'
;Indian Institute of Science
India
;
_audit_update_record             
;
2025-05-01 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27.50 H21 Cl F3 N O3'
_chemical_formula_weight         505.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.8938(8)
_cell_length_b                   7.7392(5)
_cell_length_c                   25.6881(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.182(2)
_cell_angle_gamma                90
_cell_volume                     2346.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      30.53

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             1044
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.218
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67605
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.751
_diffrn_reflns_theta_max         30.530
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             13963
_reflns_number_gt                12349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.985

_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-2019/2 (Sheldrick, 2019)'
_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)+(0.1585P)²+2.4767P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4671 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.51(2)
_chemical_absolute_configuration .
_refine_ls_number_reflns         13963
_refine_ls_number_parameters     648
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1756
_refine_ls_wR_factor_gt          0.1638
_refine_ls_goodness_of_fit_ref   0.745
_refine_ls_restrained_S_all      0.745
_refine_ls_shift/su_max          0.000
_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
Cl1 Cl 0.53740(12) 0.98295(18) 0.19581(4) 0.0484(3) Uani 1 1 d . . . . .
Cl2 Cl 0.45128(14) 0.9601(3) 0.29654(5) 0.0619(4) Uani 1 1 d . . . . .
F2 F 0.63811(16) 0.4849(4) 0.10266(9) 0.0344(6) Uani 1 1 d . . . . .
F3 F 0.50686(18) 0.6494(3) 0.12383(8) 0.0241(4) Uani 1 1 d . . . . .
F4 F 0.49129(19) 0.3746(3) 0.13024(8) 0.0271(5) Uani 1 1 d . . . . .
F5 F 0.4976(2) 0.6423(3) 0.37549(8) 0.0285(5) Uani 1 1 d . . . . .
F6 F 0.35888(16) 0.5080(4) 0.40278(9) 0.0346(6) Uani 1 1 d . . . . .
F7 F 0.49629(17) 0.3653(3) 0.37741(8) 0.0241(4) Uani 1 1 d . . . . .
O1 O -0.03053(18) 0.8105(3) 0.02719(9) 0.0190(5) Uani 1 1 d . . . . .
O2 O 0.22284(19) 0.9344(3) 0.17131(9) 0.0197(5) Uani 1 1 d . . . . .
O3 O 0.7720(2) 0.0778(3) 0.32814(9) 0.0217(5) Uani 1 1 d . . . . .
O4 O 1.02667(19) 0.1908(3) 0.47278(9) 0.0194(5) Uani 1 1 d . . . . .
O5 O 0.7785(2) 0.8666(3) 0.46149(9) 0.0190(5) Uani 1 1 d . . . . .
H5A H 0.845(4) 0.822(4) 0.4799(14) 0.028 Uiso 1 1 calc R U . . .
O6 O 0.2233(2) 0.1393(3) 0.03991(9) 0.0176(4) Uani 1 1 d . . . . .
H1 H 0.172(4) 0.193(7) 0.0223(18) 0.026 Uiso 1 1 d . U . . .
N1 N 0.07646(19) 0.8893(3) 0.10479(9) 0.0127(5) Uani 1 1 d . . . . .
N2 N 0.9186(2) 0.1126(3) 0.39553(10) 0.0133(5) Uani 1 1 d . . . . .
C1 C -0.0078(2) 0.9912(4) 0.12606(11) 0.0149(5) Uani 1 1 d . . . . .
C2 C -0.0530(2) 1.1347(4) 0.09807(13) 0.0169(6) Uani 1 1 d . . . . .
H2 H -0.028470 1.165398 0.065514 0.020 Uiso 1 1 calc R U . . .
C3 C -0.1352(3) 1.2319(5) 0.11900(15) 0.0235(7) Uani 1 1 d . . . . .
H3 H -0.167646 1.329497 0.100338 0.028 Uiso 1 1 calc R U . . .
C4 C -0.1700(3) 1.1881(5) 0.16648(16) 0.0293(8) Uani 1 1 d . . . . .
H4 H -0.225508 1.256134 0.180502 0.035 Uiso 1 1 calc R U . . .
C5 C -0.1240(3) 1.0446(6) 0.19393(14) 0.0290(8) Uani 1 1 d . . . . .
H5 H -0.148612 1.014240 0.226513 0.035 Uiso 1 1 calc R U . . .
C6 C -0.0420(3) 0.9451(5) 0.17372(13) 0.0223(7) Uani 1 1 d . . . . .
H6 H -0.009954 0.847229 0.192360 0.027 Uiso 1 1 calc R U . . .
C7 C 0.0584(2) 0.8084(4) 0.05647(11) 0.0126(5) Uani 1 1 d . . . . .
C8 C 0.1631(2) 0.7111(4) 0.04759(11) 0.0122(5) Uani 1 1 d . . . . .
H8 H 0.190979 0.728844 0.012827 0.015 Uiso 1 1 calc R U . . .
C9 C 0.2499(2) 0.7486(4) 0.09700(11) 0.0128(5) Uani 1 1 d . . . . .
H9 H 0.326978 0.787122 0.090173 0.015 Uiso 1 1 calc R U . . .
C10 C 0.1880(2) 0.8675(4) 0.12998(11) 0.0123(5) Uani 1 1 d . . . . .
C11 C 0.1543(2) 0.5235(4) 0.06550(10) 0.0113(5) Uani 1 1 d . . . . .
H11 H 0.080739 0.461582 0.066325 0.014 Uiso 1 1 calc R U . . .
C12 C 0.2398(2) 0.5584(4) 0.11474(10) 0.0104(5) Uani 1 1 d . . . . .
C13 C 0.2683(2) 0.4344(4) 0.07163(11) 0.0126(5) Uani 1 1 d . . . . .
C14 C 0.2355(2) 0.5069(4) 0.17031(11) 0.0124(5) Uani 1 1 d . . . . .
C15 C 0.1422(3) 0.4225(5) 0.18532(13) 0.0238(7) Uani 1 1 d . . . . .
H15 H 0.078268 0.401055 0.160090 0.029 Uiso 1 1 calc R U . . .
C16 C 0.1408(4) 0.3686(6) 0.23688(15) 0.0349(9) Uani 1 1 d . . . . .
H16 H 0.076709 0.308906 0.246466 0.042 Uiso 1 1 calc R U . . .
C17 C 0.2325(4) 0.4016(5) 0.27429(14) 0.0329(9) Uani 1 1 d . . . . .
H17 H 0.232539 0.362523 0.309348 0.040 Uiso 1 1 calc R U . . .
C18 C 0.3236(3) 0.4917(6) 0.26013(12) 0.0274(7) Uani 1 1 d . . . . .
H18 H 0.385713 0.517682 0.285923 0.033 Uiso 1 1 calc R U . . .
C19 C 0.3262(3) 0.5455(5) 0.20861(12) 0.0202(6) Uani 1 1 d . . . . .
H19 H 0.389547 0.608257 0.199462 0.024 Uiso 1 1 calc R U . . .
C20 C 0.3502(2) 0.4686(4) 0.03241(10) 0.0115(5) Uani 1 1 d . . . . .
C21 C 0.4681(2) 0.4930(4) 0.04438(11) 0.0144(5) Uani 1 1 d . . . . .
C22 C 0.5355(2) 0.5164(4) 0.00428(13) 0.0181(6) Uani 1 1 d . . . . .
H22 H 0.614425 0.536465 0.012815 0.022 Uiso 1 1 calc R U . . .
C23 C 0.4888(3) 0.5106(5) -0.04784(13) 0.0212(7) Uani 1 1 d . . . . .
H23 H 0.535411 0.525265 -0.074953 0.025 Uiso 1 1 calc R U . . .
C24 C 0.3730(3) 0.4833(5) -0.06014(12) 0.0182(6) Uani 1 1 d . . . . .
H24 H 0.340279 0.478200 -0.095786 0.022 Uiso 1 1 calc R U . . .
C25 C 0.3056(2) 0.4636(4) -0.02051(11) 0.0146(5) Uani 1 1 d . . . . .
H25 H 0.226451 0.446062 -0.029507 0.018 Uiso 1 1 calc R U . . .
C26 C 0.2556(2) 0.2441(4) 0.08480(12) 0.0131(5) Uani 1 1 d . . . . .
H26A H 0.328545 0.201265 0.103033 0.016 Uiso 1 1 calc R U . . .
H26B H 0.197981 0.232507 0.109244 0.016 Uiso 1 1 calc R U . . .
C27 C 0.5253(2) 0.5004(4) 0.09976(12) 0.0164(6) Uani 1 1 d . . . . .
C28 C 1.0014(2) 0.0081(4) 0.37475(11) 0.0140(5) Uani 1 1 d . . . . .
C29 C 1.0474(3) -0.1323(4) 0.40346(13) 0.0188(6) Uani 1 1 d . . . . .
H29 H 1.023565 -0.159575 0.436430 0.023 Uiso 1 1 calc R U . . .
C30 C 1.1293(3) -0.2332(5) 0.38334(15) 0.0250(7) Uani 1 1 d . . . . .
H30 H 1.161365 -0.329952 0.402527 0.030 Uiso 1 1 calc R U . . .
C31 C 1.1636(3) -0.1914(5) 0.33507(16) 0.0289(8) Uani 1 1 d . . . . .
H31 H 1.219604 -0.259683 0.321516 0.035 Uiso 1 1 calc R U . . .
C32 C 1.1169(3) -0.0512(6) 0.30654(14) 0.0298(8) Uani 1 1 d . . . . .
H32 H 1.140917 -0.023463 0.273628 0.036 Uiso 1 1 calc R U . . .
C33 C 1.0347(3) 0.0488(5) 0.32639(13) 0.0241(7) Uani 1 1 d . . . . .
H33 H 1.001605 0.144327 0.306899 0.029 Uiso 1 1 calc R U . . .
C34 C 0.8079(3) 0.1394(4) 0.37008(12) 0.0147(5) Uani 1 1 d . . . . .
C35 C 0.7471(2) 0.2589(4) 0.40382(11) 0.0124(5) Uani 1 1 d . . . . .
H35 H 0.669477 0.221894 0.410350 0.015 Uiso 1 1 calc R U . . .
C36 C 0.9376(2) 0.1939(4) 0.44382(11) 0.0134(5) Uani 1 1 d . . . . .
C37 C 0.7590(2) 0.4504(4) 0.38660(10) 0.0114(5) Uani 1 1 d . . . . .
C38 C 0.8443(2) 0.4808(4) 0.43578(10) 0.0116(5) Uani 1 1 d . . . . .
H38 H 0.918621 0.540911 0.435465 0.014 Uiso 1 1 calc R U . . .
C39 C 0.7314(2) 0.5720(4) 0.42985(11) 0.0107(5) Uani 1 1 d . . . . .
C40 C 0.7674(2) 0.5026(4) 0.33153(11) 0.0138(5) Uani 1 1 d . . . . .
C41 C 0.6714(3) 0.5116(6) 0.29444(13) 0.0292(8) Uani 1 1 d . . . . .
H41 H 0.599387 0.482445 0.304246 0.035 Uiso 1 1 calc R U . . .
C42 C 0.6803(3) 0.5628(7) 0.24315(13) 0.0364(10) Uani 1 1 d . . . . .
H42 H 0.614065 0.570750 0.218437 0.044 Uiso 1 1 calc R U . . .
C43 C 0.7841(3) 0.6020(5) 0.22802(13) 0.0290(8) Uani 1 1 d . . . . .
H43 H 0.789654 0.637022 0.192978 0.035 Uiso 1 1 calc R U . . .
C44 C 0.8809(3) 0.5903(6) 0.26410(14) 0.0317(9) Uani 1 1 d . . . . .
H44 H 0.952970 0.616208 0.253765 0.038 Uiso 1 1 calc R U . . .
C45 C 0.8720(3) 0.5404(6) 0.31551(13) 0.0263(7) Uani 1 1 d . . . . .
H45 H 0.938555 0.531975 0.340029 0.032 Uiso 1 1 calc R U . . .
C46 C 0.6506(2) 0.5385(4) 0.46970(11) 0.0128(5) Uani 1 1 d . . . . .
C47 C 0.6978(2) 0.5450(4) 0.52227(11) 0.0153(5) Uani 1 1 d . . . . .
H47 H 0.777205 0.561280 0.530302 0.018 Uiso 1 1 calc R U . . .
C48 C 0.6324(3) 0.5286(4) 0.56318(12) 0.0182(6) Uani 1 1 d . . . . .
H48 H 0.666617 0.536111 0.598567 0.022 Uiso 1 1 calc R U . . .
C49 C 0.5167(3) 0.5011(4) 0.55182(12) 0.0188(6) Uani 1 1 d . . . . .
H49 H 0.471356 0.488218 0.579523 0.023 Uiso 1 1 calc R U . . .
C50 C 0.4673(2) 0.4923(5) 0.50036(13) 0.0190(6) Uani 1 1 d . . . . .
H50 H 0.388133 0.472519 0.492835 0.023 Uiso 1 1 calc R U . . .
C51 C 0.5325(2) 0.5122(4) 0.45930(11) 0.0140(5) Uani 1 1 d . . . . .
C52 C 0.7449(3) 0.7628(4) 0.41637(12) 0.0163(6) Uani 1 1 d . . . . .
H52A H 0.802260 0.773574 0.391748 0.020 Uiso 1 1 calc R U . . .
H52B H 0.672037 0.806718 0.398381 0.020 Uiso 1 1 calc R U . . .
C53 C 0.4720(2) 0.5079(4) 0.40444(12) 0.0179(6) Uani 1 1 d . . . . .
C54 C 0.4870(8) 1.0930(8) 0.2466(2) 0.100(4) Uani 1 1 d . . . . .
H54A H 0.419192 1.160118 0.232309 0.120 Uiso 1 1 calc R U . . .
H54B H 0.545435 1.176233 0.261636 0.120 Uiso 1 1 calc R U . . .
C55 C 0.8324(2) 0.2930(4) 0.45301(11) 0.0115(5) Uani 1 1 d . . . . .
H1A H 0.815(3) 0.272(6) 0.4879(15) 0.017 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C54 1.728(5) . ?
Cl2 C54 1.738(5) . ?
F2 C27 1.340(3) . ?
F3 C27 1.339(4) . ?
F4 C27 1.342(4) . ?
F5 C53 1.336(4) . ?
F6 C53 1.340(3) . ?
F7 C53 1.354(4) . ?
O1 C7 1.219(4) . ?
O2 C10 1.207(4) . ?
O3 C34 1.206(4) . ?
O4 C36 1.216(4) . ?
O5 C52 1.426(4) . ?
O6 C26 1.423(4) . ?
N1 C7 1.383(4) . ?
N1 C10 1.411(3) . ?
N1 C1 1.436(4) . ?
N2 C36 1.384(4) . ?
N2 C34 1.410(4) . ?
N2 C28 1.428(4) . ?
C1 C6 1.384(4) . ?
C1 C2 1.394(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.378(6) . ?
C4 C5 1.391(6) . ?
C5 C6 1.393(5) . ?
C7 C8 1.497(4) . ?
C8 C11 1.530(4) . ?
C8 C9 1.560(4) . ?
C9 C10 1.504(4) . ?
C9 C12 1.551(4) . ?
C11 C13 1.512(4) . ?
C11 C12 1.545(4) . ?
C12 C14 1.489(4) . ?
C12 C13 1.535(4) . ?
C13 C20 1.510(4) . ?
C13 C26 1.523(4) . ?
C14 C15 1.384(4) . ?
C14 C19 1.399(4) . ?
C15 C16 1.391(5) . ?
C16 C17 1.385(6) . ?
C17 C18 1.375(6) . ?
C18 C19 1.391(4) . ?
C20 C25 1.397(4) . ?
C20 C21 1.409(4) . ?
C21 C22 1.394(4) . ?
C21 C27 1.499(4) . ?
C22 C23 1.385(5) . ?
C23 C24 1.390(4) . ?
C24 C25 1.381(4) . ?
C28 C33 1.387(4) . ?
C28 C29 1.387(4) . ?
C29 C30 1.396(4) . ?
C30 C31 1.391(5) . ?
C31 C32 1.386(6) . ?
C32 C33 1.393(5) . ?
C34 C35 1.512(4) . ?
C35 C55 1.541(4) . ?
C35 C37 1.558(4) . ?
C36 C55 1.511(4) . ?
C37 C40 1.487(4) . ?
C37 C39 1.523(4) . ?
C37 C38 1.537(4) . ?
C38 C39 1.508(4) . ?
C38 C55 1.531(4) . ?
C39 C46 1.512(4) . ?
C39 C52 1.529(4) . ?
C40 C45 1.389(4) . ?
C40 C41 1.394(4) . ?
C41 C42 1.393(5) . ?
C42 C43 1.374(6) . ?
C43 C44 1.387(5) . ?
C44 C45 1.393(4) . ?
C46 C47 1.397(4) . ?
C46 C51 1.411(4) . ?
C47 C48 1.389(4) . ?
C48 C49 1.388(4) . ?
C49 C50 1.379(4) . ?
C50 C51 1.393(4) . ?
C51 C53 1.501(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
C7 N1 C10 112.9(2) . . ?
C7 N1 C1 123.6(2) . . ?
C10 N1 C1 123.5(2) . . ?
C36 N2 C34 112.8(2) . . ?
C36 N2 C28 123.3(2) . . ?
C34 N2 C28 123.9(2) . . ?
C6 C1 C2 121.6(3) . . ?
C6 C1 N1 119.4(3) . . ?
C2 C1 N1 118.9(3) . . ?
C1 C2 C3 118.4(3) . . ?
C4 C3 C2 120.7(3) . . ?
C3 C4 C5 120.2(3) . . ?
C4 C5 C6 120.1(3) . . ?
C1 C6 C5 119.0(3) . . ?
O1 C7 N1 125.0(3) . . ?
O1 C7 C8 125.9(3) . . ?
N1 C7 C8 109.0(2) . . ?
C7 C8 C11 110.0(2) . . ?
C7 C8 C9 105.1(2) . . ?
C11 C8 C9 89.7(2) . . ?
C10 C9 C12 110.7(2) . . ?
C10 C9 C8 104.6(2) . . ?
C12 C9 C8 89.7(2) . . ?
O2 C10 N1 123.5(3) . . ?
O2 C10 C9 128.2(3) . . ?
N1 C10 C9 108.2(2) . . ?
C13 C11 C8 111.7(2) . . ?
C13 C11 C12 60.26(18) . . ?
C8 C11 C12 91.0(2) . . ?
C14 C12 C13 124.2(3) . . ?
C14 C12 C11 129.8(2) . . ?
C13 C12 C11 58.80(17) . . ?
C14 C12 C9 123.3(2) . . ?
C13 C12 C9 110.4(2) . . ?
C11 C12 C9 89.5(2) . . ?
C20 C13 C11 119.7(2) . . ?
C20 C13 C26 114.0(2) . . ?
C11 C13 C26 110.6(2) . . ?
C20 C13 C12 126.2(3) . . ?
C11 C13 C12 60.94(18) . . ?
C26 C13 C12 114.0(2) . . ?
C15 C14 C19 118.7(3) . . ?
C15 C14 C12 121.2(3) . . ?
C19 C14 C12 120.1(3) . . ?
C14 C15 C16 120.8(3) . . ?
C17 C16 C15 120.2(3) . . ?
C18 C17 C16 119.2(3) . . ?
C17 C18 C19 121.0(3) . . ?
C18 C19 C14 119.9(3) . . ?
C25 C20 C21 117.6(2) . . ?
C25 C20 C13 116.5(2) . . ?
C21 C20 C13 125.8(2) . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 C27 117.5(3) . . ?
C20 C21 C27 122.2(3) . . ?
C23 C22 C21 120.8(3) . . ?
C22 C23 C24 119.4(3) . . ?
C25 C24 C23 120.0(3) . . ?
C24 C25 C20 121.9(3) . . ?
O6 C26 C13 113.3(2) . . ?
F3 C27 F2 105.8(3) . . ?
F3 C27 F4 106.0(2) . . ?
F2 C27 F4 106.0(3) . . ?
F3 C27 C21 113.0(3) . . ?
F2 C27 C21 112.4(3) . . ?
F4 C27 C21 113.1(3) . . ?
C33 C28 C29 121.1(3) . . ?
C33 C28 N2 119.6(3) . . ?
C29 C28 N2 119.3(3) . . ?
C28 C29 C30 119.2(3) . . ?
C31 C30 C29 119.7(3) . . ?
C32 C31 C30 120.7(3) . . ?
C31 C32 C33 119.6(3) . . ?
C28 C33 C32 119.6(3) . . ?
O3 C34 N2 124.2(3) . . ?
O3 C34 C35 127.8(3) . . ?
N2 C34 C35 108.0(2) . . ?
C34 C35 C55 105.2(2) . . ?
C34 C35 C37 110.6(2) . . ?
C55 C35 C37 89.8(2) . . ?
O4 C36 N2 124.9(3) . . ?
O4 C36 C55 126.1(3) . . ?
N2 C36 C55 109.0(2) . . ?
C40 C37 C39 124.9(3) . . ?
C40 C37 C38 128.6(2) . . ?
C39 C37 C38 59.07(17) . . ?
C40 C37 C35 123.2(2) . . ?
C39 C37 C35 110.2(2) . . ?
C38 C37 C35 89.2(2) . . ?
C39 C38 C55 111.1(2) . . ?
C39 C38 C37 60.01(18) . . ?
C55 C38 C37 91.0(2) . . ?
C38 C39 C46 119.0(2) . . ?
C38 C39 C37 60.92(18) . . ?
C46 C39 C37 127.0(3) . . ?
C38 C39 C52 110.9(2) . . ?
C46 C39 C52 114.4(2) . . ?
C37 C39 C52 113.2(2) . . ?
C45 C40 C41 118.3(3) . . ?
C45 C40 C37 120.6(3) . . ?
C41 C40 C37 121.1(3) . . ?
C42 C41 C40 120.5(3) . . ?
C43 C42 C41 120.5(3) . . ?
C42 C43 C44 119.7(3) . . ?
C43 C44 C45 119.8(3) . . ?
C40 C45 C44 121.1(3) . . ?
C47 C46 C51 117.3(3) . . ?
C47 C46 C39 115.8(2) . . ?
C51 C46 C39 126.8(3) . . ?
C48 C47 C46 122.2(3) . . ?
C49 C48 C47 119.3(3) . . ?
C50 C49 C48 120.1(3) . . ?
C49 C50 C51 120.6(3) . . ?
C50 C51 C46 120.5(3) . . ?
C50 C51 C53 117.5(3) . . ?
C46 C51 C53 122.0(3) . . ?
O5 C52 C39 112.7(2) . . ?
F5 C53 F6 106.2(3) . . ?
F5 C53 F7 105.7(2) . . ?
F6 C53 F7 105.2(3) . . ?
F5 C53 C51 112.9(3) . . ?
F6 C53 C51 113.1(3) . . ?
F7 C53 C51 113.0(3) . . ?
Cl1 C54 Cl2 113.9(3) . . ?
C36 C55 C38 109.1(2) . . ?
C36 C55 C35 105.0(2) . . ?
C38 C55 C35 90.1(2) . . ?

_refine_diff_density_max         0.931
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.126

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2451397'
loop_
_audit_author_name
_audit_author_address
'Shashikanth J'
;Indian Institute of Science
India
;
_audit_update_record             
;
2025-05-15 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;

#==============================================================================
# start Validation Reply Form

_vrf_PLAT097_shelx               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.12 eA-3 
RESPONSE: In the molecules, the residual Q peak is situated near the two
 fluorine atoms, which appears to be somewhat disordered.
;
# end Validation Reply Form
#============================================================================== 

_audit_creation_method           
;FinalCif 2024.9-0 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C54 H40 F6 N2 O6'
_chemical_formula_moiety         C54H40F6N2O6
_chemical_formula_weight         926.88
_chemical_melting_point          ?
_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                   11.3001(7)
_cell_length_b                   13.4126(8)
_cell_length_c                   16.3714(9)
_cell_angle_alpha                76.397(2)
_cell_angle_beta                 75.850(2)
_cell_angle_gamma                67.123(2)
_cell_volume                     2189.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9868
_cell_measurement_theta_min      2.7657
_cell_measurement_theta_max      31.567
_cell_measurement_wavelength     0.71073
_exptl_crystal_description       block
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             960
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6787
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   
;Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal
 structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_exptl_bruker_absorpt_correction_T_ratio 0.9094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      120(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'flat graphite'
_bruker_diffrn_measurement_temperature_device 'Oxford Cryostream 1000'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'sealed tube'
_diffrn_source_type              ?
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_diffrn_source_current           40.0
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_detector_area_resol_mean 7.391
_diffrn_measurement_device       'FIXED KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_measurement_details      
;<Phi   scan: start=   0.0; len= 360.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 50.00 mm theta=   6.489 deg omega=  16.040 deg chi=  54.736 deg] 
measure for 32.0 seconds; frame angle 0.60 degrees, wavelength=0.71076>
<Omega scan: start= 190.0; len= 186.0; end= 376.0 at [Counterclockwise Eulerian 
angles: dx= 50.00 mm theta=   6.489 deg phi=  50.999 deg chi=  54.736 deg] 
measure for 32.0 seconds; frame angle 0.60 degrees, wavelength=0.71076>
<Omega scan: start= 190.0; len= 186.0; end= 376.0 at [Counterclockwise Eulerian 
angles: dx= 50.00 mm theta=   6.489 deg phi=   0.000 deg chi=  54.736 deg] 
measure for 32.0 seconds; frame angle 0.60 degrees, wavelength=0.71076>
<Phi   scan: start=   0.0; len= 360.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 50.00 mm theta=   6.489 deg omega= 189.915 deg chi=  54.736 deg] 
measure for 32.0 seconds; frame angle 0.60 degrees, wavelength=0.71076>
;
_diffrn_measurement_bruker_total_exposure_time 58240.0
_diffrn_reflns_number            91255
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_theta_min         2.552
_diffrn_reflns_theta_max         31.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_reduction_process narrow-frame
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_bruker_av_norm_I  426.757
_diffrn_reflns_bruker_number_gt  69797
_reflns_number_total             14303
_reflns_number_gt                12031
_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       ?
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC)'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  ?
_computing_bruker_data_scaling   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_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)+(0.0680P)²+2.3123P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Intrinsic Phasing'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         14303
_refine_ls_number_parameters     619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0829
_refine_ls_wR_factor_ref         0.1858
_refine_ls_wR_factor_gt          0.1774
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.122
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_geom_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.
;
_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_
_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 0.78711(15) 0.09731(19) 0.15423(11) 0.0658(7) Uani 1 1 d . . . . .
F2 F 0.94665(13) -0.03618(13) 0.19743(10) 0.0369(4) Uani 1 1 d . . . . .
F3 F 0.87522(18) 0.10808(16) 0.25277(14) 0.0570(5) Uani 1 1 d . . . . .
F4 F 0.62723(15) 0.60967(16) 0.15435(12) 0.0513(5) Uani 1 1 d . . . . .
F5 F 0.63767(14) 0.55918(14) 0.03947(9) 0.0370(4) Uani 1 1 d . . . . .
F6 F 0.56240(17) 0.47849(14) 0.15484(15) 0.0687(7) Uani 1 1 d . . . . .
O1 O 0.15282(14) 0.19242(13) 0.20908(9) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.51937(14) 0.12592(12) 0.00620(9) 0.0190(3) Uani 1 1 d . . . . .
O3 O 0.53269(17) 0.24765(12) 0.39455(9) 0.0233(3) Uani 1 1 d . . . . .
H1 H 0.521(3) 0.310(3) 0.4068(19) 0.035 Uiso 1 1 d . U . . .
O4 O 0.44392(14) 0.45039(11) 0.44864(9) 0.0191(3) Uani 1 1 d . . . . .
O5 O 0.04639(13) 0.72396(12) 0.45198(9) 0.0204(3) Uani 1 1 d . . . . .
O6 O 0.40866(16) 0.92933(12) 0.15756(9) 0.0207(3) Uani 1 1 d . . . . .
H1B H 0.419(3) 0.916(2) 0.111(2) 0.031 Uiso 1 1 d . U . . .
N1 N 0.31824(15) 0.17456(13) 0.09282(10) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.24536(16) 0.58898(13) 0.47303(10) 0.0151(3) Uani 1 1 d . . . . .
C1 C 0.23780(18) 0.21205(16) 0.02846(12) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.2580(2) 0.14548(19) -0.02999(13) 0.0229(4) Uani 1 1 d . . . . .
H2 H 0.323424 0.074583 -0.027065 0.028 Uiso 1 1 calc R U . . .
C3 C 0.1810(2) 0.1837(2) -0.09338(15) 0.0317(5) Uani 1 1 d . . . . .
H3 H 0.195002 0.139380 -0.134811 0.038 Uiso 1 1 calc R U . . .
C4 C 0.0847(2) 0.2856(2) -0.09602(17) 0.0357(6) Uani 1 1 d . . . . .
H4 H 0.032557 0.311435 -0.139437 0.043 Uiso 1 1 calc R U . . .
C5 C 0.0634(3) 0.3504(2) -0.03616(18) 0.0352(6) Uani 1 1 d . . . . .
H5 H -0.004281 0.420168 -0.037920 0.042 Uiso 1 1 calc R U . . .
C6 C 0.1404(2) 0.31416(18) 0.02681(16) 0.0270(4) Uani 1 1 d . . . . .
H6 H 0.126370 0.358760 0.068041 0.032 Uiso 1 1 calc R U . . .
C7 C 0.26688(18) 0.16556(15) 0.18103(12) 0.0147(3) Uani 1 1 d . . . . .
C8 C 0.37957(17) 0.12004(14) 0.22930(11) 0.0122(3) Uani 1 1 d . . . . .
H8 H 0.380353 0.055155 0.274538 0.015 Uiso 1 1 calc R U . . .
C9 C 0.50250(17) 0.10422(14) 0.15936(11) 0.0127(3) Uani 1 1 d . . . . .
H9 H 0.574112 0.031579 0.167350 0.015 Uiso 1 1 calc R U . . .
C10 C 0.45298(18) 0.13377(14) 0.07640(11) 0.0133(3) Uani 1 1 d . . . . .
C11 C 0.40552(17) 0.21230(14) 0.25503(11) 0.0120(3) Uani 1 1 d . . . . .
C12 C 0.52368(17) 0.19970(14) 0.18273(11) 0.0123(3) Uani 1 1 d . . . . .
H12 H 0.541590 0.261721 0.140701 0.015 Uiso 1 1 calc R U . . .
C13 C 0.54383(17) 0.17211(14) 0.27411(11) 0.0121(3) Uani 1 1 d . . . . .
C14 C 0.30078(17) 0.31403(15) 0.28032(12) 0.0145(3) Uani 1 1 d . . . . .
C15 C 0.2287(2) 0.31436(17) 0.36255(13) 0.0216(4) Uani 1 1 d . . . . .
H15 H 0.247542 0.249354 0.403321 0.026 Uiso 1 1 calc R U . . .
C16 C 0.1293(2) 0.40963(19) 0.38514(16) 0.0267(5) Uani 1 1 d . . . . .
H16 H 0.080125 0.409426 0.441236 0.032 Uiso 1 1 calc R U . . .
C17 C 0.1017(2) 0.50477(18) 0.32608(18) 0.0284(5) Uani 1 1 d . . . . .
H17 H 0.034671 0.570035 0.341894 0.034 Uiso 1 1 calc R U . . .
C18 C 0.1717(2) 0.50460(17) 0.24435(16) 0.0259(4) Uani 1 1 d . . . . .
H18 H 0.152315 0.569764 0.203771 0.031 Uiso 1 1 calc R U . . .
C19 C 0.2709(2) 0.40939(16) 0.22088(13) 0.0189(4) Uani 1 1 d . . . . .
H19 H 0.318085 0.409575 0.164246 0.023 Uiso 1 1 calc R U . . .
C20 C 0.61138(18) 0.05591(15) 0.31428(11) 0.0142(3) Uani 1 1 d . . . . .
C21 C 0.74547(19) -0.00305(16) 0.29163(12) 0.0180(4) Uani 1 1 d . . . . .
C22 C 0.8029(2) -0.10731(17) 0.33587(14) 0.0252(4) Uani 1 1 d . . . . .
H22 H 0.893581 -0.145864 0.320779 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7290(2) -0.15500(17) 0.40150(14) 0.0269(5) Uani 1 1 d . . . . .
H23 H 0.768807 -0.226121 0.431074 0.032 Uiso 1 1 calc R U . . .
C24 C 0.5971(2) -0.09909(16) 0.42401(13) 0.0224(4) Uani 1 1 d . . . . .
H24 H 0.545782 -0.131786 0.468659 0.027 Uiso 1 1 calc R U . . .
C25 C 0.5401(2) 0.00561(15) 0.38068(12) 0.0171(3) Uani 1 1 d . . . . .
H25 H 0.449628 0.043863 0.397001 0.021 Uiso 1 1 calc R U . . .
C26 C 0.57197(19) 0.25745(15) 0.30452(12) 0.0157(3) Uani 1 1 d . . . . .
H26A H 0.666247 0.245718 0.289291 0.019 Uiso 1 1 calc R U . . .
H26B H 0.523331 0.331692 0.277088 0.019 Uiso 1 1 calc R U . . .
C27 C 0.8360(2) 0.0420(2) 0.22384(16) 0.0276(5) Uani 1 1 d . . . . .
C28 C 0.21586(18) 0.56322(16) 0.56408(12) 0.0175(4) Uani 1 1 d . . . . .
C29 C 0.1636(2) 0.64797(19) 0.61184(14) 0.0243(4) Uani 1 1 d . . . . .
H29 H 0.149152 0.721461 0.584412 0.029 Uiso 1 1 calc R U . . .
C30 C 0.1325(2) 0.6248(2) 0.69989(15) 0.0314(5) Uani 1 1 d . . . . .
H30 H 0.094976 0.682610 0.732935 0.038 Uiso 1 1 calc R U . . .
C31 C 0.1563(2) 0.5176(2) 0.73932(14) 0.0336(6) Uani 1 1 d . . . . .
H31 H 0.135869 0.501726 0.799665 0.040 Uiso 1 1 calc R U . . .
C32 C 0.2097(2) 0.4330(2) 0.69153(15) 0.0303(5) Uani 1 1 d . . . . .
H32 H 0.226015 0.359428 0.719274 0.036 Uiso 1 1 calc R U . . .
C33 C 0.23967(19) 0.45528(18) 0.60299(14) 0.0218(4) Uani 1 1 d . . . . .
H33 H 0.275728 0.397592 0.569886 0.026 Uiso 1 1 calc R U . . .
C34 C 0.35923(18) 0.53178(15) 0.42229(12) 0.0147(3) Uani 1 1 d . . . . .
C35 C 0.35865(18) 0.58917(14) 0.33103(12) 0.0141(3) Uani 1 1 d . . . . .
H35 H 0.378457 0.541827 0.286957 0.017 Uiso 1 1 calc R U . . .
C36 C 0.22747(17) 0.68671(14) 0.33413(11) 0.0134(3) Uani 1 1 d . . . . .
H36 H 0.175962 0.697029 0.289121 0.016 Uiso 1 1 calc R U . . .
C37 C 0.15771(18) 0.67299(15) 0.42444(12) 0.0145(3) Uani 1 1 d . . . . .
C38 C 0.43217(18) 0.66902(15) 0.31174(11) 0.0142(3) Uani 1 1 d . . . . .
H38 H 0.506418 0.658225 0.339865 0.017 Uiso 1 1 calc R U . . .
C39 C 0.30215(17) 0.76683(14) 0.31882(11) 0.0120(3) Uani 1 1 d . . . . .
C40 C 0.39564(17) 0.75330(14) 0.23443(11) 0.0128(3) Uani 1 1 d . . . . .
C41 C 0.25610(17) 0.86062(15) 0.36612(11) 0.0132(3) Uani 1 1 d . . . . .
C42 C 0.2970(2) 0.84775(17) 0.44301(13) 0.0203(4) Uani 1 1 d . . . . .
H42 H 0.360023 0.780468 0.462863 0.024 Uiso 1 1 calc R U . . .
C43 C 0.2459(2) 0.93310(18) 0.49081(14) 0.0242(4) Uani 1 1 d . . . . .
H43 H 0.275024 0.923950 0.542738 0.029 Uiso 1 1 calc R U . . .
C44 C 0.1531(2) 1.03096(17) 0.46310(13) 0.0216(4) Uani 1 1 d . . . . .
H44 H 0.117248 1.088480 0.496362 0.026 Uiso 1 1 calc R U . . .
C45 C 0.1128(2) 1.04464(16) 0.38663(13) 0.0214(4) Uani 1 1 d . . . . .
H45 H 0.049842 1.112104 0.367016 0.026 Uiso 1 1 calc R U . . .
C46 C 0.16405(19) 0.95997(16) 0.33831(12) 0.0174(4) Uani 1 1 d . . . . .
H46 H 0.135882 0.970170 0.285840 0.021 Uiso 1 1 calc R U . . .
C47 C 0.35424(18) 0.73426(14) 0.16022(11) 0.0134(3) Uani 1 1 d . . . . .
C48 C 0.23323(19) 0.80610(16) 0.14062(12) 0.0178(4) Uani 1 1 d . . . . .
H48 H 0.182760 0.861618 0.174798 0.021 Uiso 1 1 calc R U . . .
C49 C 0.1836(2) 0.79963(18) 0.07308(13) 0.0224(4) Uani 1 1 d . . . . .
H49 H 0.101008 0.850171 0.061284 0.027 Uiso 1 1 calc R U . . .
C50 C 0.2562(2) 0.71848(19) 0.02307(13) 0.0249(4) Uani 1 1 d . . . . .
H50 H 0.222322 0.711381 -0.022126 0.030 Uiso 1 1 calc R U . . .
C51 C 0.3775(2) 0.64827(17) 0.03940(13) 0.0222(4) Uani 1 1 d . . . . .
H51 H 0.427857 0.593715 0.004350 0.027 Uiso 1 1 calc R U . . .
C52 C 0.42796(19) 0.65590(15) 0.10662(12) 0.0164(3) Uani 1 1 d . . . . .
C53 C 0.47253(19) 0.83080(16) 0.20925(12) 0.0168(3) Uani 1 1 d . . . . .
H53A H 0.484244 0.848549 0.261450 0.020 Uiso 1 1 calc R U . . .
H53B H 0.560028 0.793651 0.177763 0.020 Uiso 1 1 calc R U . . .
C54 C 0.5629(2) 0.57748(17) 0.11550(13) 0.0217(4) Uani 1 1 d . . . . .


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 C27 1.321(3) . ?
F2 C27 1.334(3) . ?
F3 C27 1.346(3) . ?
F4 C54 1.311(3) . ?
F5 C54 1.339(2) . ?
F6 C54 1.334(3) . ?
O1 C7 1.196(2) . ?
O2 C10 1.212(2) . ?
O3 C26 1.422(2) . ?
O4 C34 1.209(2) . ?
O5 C37 1.205(2) . ?
O6 C53 1.419(2) . ?
N1 C10 1.382(2) . ?
N1 C7 1.414(2) . ?
N1 C1 1.433(2) . ?
N2 C34 1.394(2) . ?
N2 C37 1.407(2) . ?
N2 C28 1.434(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.383(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.376(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.389(3) . ?
C7 C8 1.510(3) . ?
C8 C11 1.544(2) . ?
C8 C9 1.547(2) . ?
C9 C10 1.504(2) . ?
C9 C12 1.535(2) . ?
C11 C14 1.485(2) . ?
C11 C13 1.528(2) . ?
C11 C12 1.536(2) . ?
C12 C13 1.506(2) . ?
C13 C20 1.511(2) . ?
C13 C26 1.512(2) . ?
C14 C19 1.391(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.391(3) . ?
C16 C17 1.385(4) . ?
C17 C18 1.378(4) . ?
C18 C19 1.393(3) . ?
C20 C25 1.391(3) . ?
C20 C21 1.411(3) . ?
C21 C22 1.396(3) . ?
C21 C27 1.501(3) . ?
C22 C23 1.384(3) . ?
C23 C24 1.382(3) . ?
C24 C25 1.394(3) . ?
C28 C33 1.386(3) . ?
C28 C29 1.386(3) . ?
C29 C30 1.387(3) . ?
C30 C31 1.380(4) . ?
C31 C32 1.385(4) . ?
C32 C33 1.393(3) . ?
C34 C35 1.512(3) . ?
C35 C38 1.530(3) . ?
C35 C36 1.549(2) . ?
C36 C37 1.502(3) . ?
C36 C39 1.551(2) . ?
C38 C40 1.507(2) . ?
C38 C39 1.544(2) . ?
C39 C41 1.485(2) . ?
C39 C40 1.521(2) . ?
C40 C47 1.509(2) . ?
C40 C53 1.527(3) . ?
C41 C46 1.390(3) . ?
C41 C42 1.396(3) . ?
C42 C43 1.394(3) . ?
C43 C44 1.382(3) . ?
C44 C45 1.384(3) . ?
C45 C46 1.392(3) . ?
C47 C48 1.395(3) . ?
C47 C52 1.402(3) . ?
C48 C49 1.390(3) . ?
C49 C50 1.387(3) . ?
C50 C51 1.377(3) . ?
C51 C52 1.397(3) . ?
C52 C54 1.498(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C7 112.75(15) . . ?
C10 N1 C1 124.21(15) . . ?
C7 N1 C1 122.76(15) . . ?
C34 N2 C37 112.32(15) . . ?
C34 N2 C28 124.77(16) . . ?
C37 N2 C28 122.84(16) . . ?
C2 C1 C6 121.31(19) . . ?
C2 C1 N1 119.53(17) . . ?
C6 C1 N1 119.16(18) . . ?
C1 C2 C3 119.0(2) . . ?
C4 C3 C2 120.0(2) . . ?
C3 C4 C5 120.5(2) . . ?
C4 C5 C6 120.3(2) . . ?
C1 C6 C5 118.9(2) . . ?
O1 C7 N1 123.61(17) . . ?
O1 C7 C8 128.32(17) . . ?
N1 C7 C8 108.05(15) . . ?
C7 C8 C11 111.42(14) . . ?
C7 C8 C9 104.78(14) . . ?
C11 C8 C9 89.68(13) . . ?
C10 C9 C12 112.76(14) . . ?
C10 C9 C8 105.21(14) . . ?
C12 C9 C8 89.84(13) . . ?
O2 C10 N1 125.14(17) . . ?
O2 C10 C9 126.05(17) . . ?
N1 C10 C9 108.79(15) . . ?
C14 C11 C13 123.84(15) . . ?
C14 C11 C12 128.96(15) . . ?
C13 C11 C12 58.87(11) . . ?
C14 C11 C8 123.51(15) . . ?
C13 C11 C8 110.71(14) . . ?
C12 C11 C8 89.95(13) . . ?
C13 C12 C9 109.15(14) . . ?
C13 C12 C11 60.31(11) . . ?
C9 C12 C11 90.41(13) . . ?
C12 C13 C20 121.74(15) . . ?
C12 C13 C26 114.73(15) . . ?
C20 C13 C26 113.97(15) . . ?
C12 C13 C11 60.81(11) . . ?
C20 C13 C11 122.58(15) . . ?
C26 C13 C11 112.91(14) . . ?
C19 C14 C15 119.29(18) . . ?
C19 C14 C11 120.04(17) . . ?
C15 C14 C11 120.64(17) . . ?
C16 C15 C14 120.2(2) . . ?
C17 C16 C15 120.2(2) . . ?
C18 C17 C16 119.89(19) . . ?
C17 C18 C19 120.4(2) . . ?
C14 C19 C18 120.1(2) . . ?
C25 C20 C21 117.54(17) . . ?
C25 C20 C13 118.72(16) . . ?
C21 C20 C13 123.64(17) . . ?
C22 C21 C20 120.33(19) . . ?
C22 C21 C27 115.89(19) . . ?
C20 C21 C27 123.71(18) . . ?
C23 C22 C21 120.6(2) . . ?
C24 C23 C22 119.97(19) . . ?
C23 C24 C25 119.5(2) . . ?
C20 C25 C24 122.10(19) . . ?
O3 C26 C13 108.17(15) . . ?
F1 C27 F2 105.6(2) . . ?
F1 C27 F3 107.4(2) . . ?
F2 C27 F3 104.17(19) . . ?
F1 C27 C21 114.47(19) . . ?
F2 C27 C21 112.52(19) . . ?
F3 C27 C21 111.9(2) . . ?
C33 C28 C29 121.07(19) . . ?
C33 C28 N2 120.14(18) . . ?
C29 C28 N2 118.79(18) . . ?
C28 C29 C30 119.6(2) . . ?
C31 C30 C29 119.8(2) . . ?
C30 C31 C32 120.5(2) . . ?
C31 C32 C33 120.3(2) . . ?
C28 C33 C32 118.7(2) . . ?
O4 C34 N2 124.55(18) . . ?
O4 C34 C35 126.63(17) . . ?
N2 C34 C35 108.82(15) . . ?
C34 C35 C38 110.25(15) . . ?
C34 C35 C36 104.47(14) . . ?
C38 C35 C36 90.02(13) . . ?
C37 C36 C35 105.33(14) . . ?
C37 C36 C39 112.34(15) . . ?
C35 C36 C39 89.74(13) . . ?
O5 C37 N2 124.92(17) . . ?
O5 C37 C36 127.01(17) . . ?
N2 C37 C36 108.07(15) . . ?
C40 C38 C35 111.18(15) . . ?
C40 C38 C39 59.80(11) . . ?
C35 C38 C39 90.69(13) . . ?
C41 C39 C40 127.04(15) . . ?
C41 C39 C38 130.91(15) . . ?
C40 C39 C38 58.89(11) . . ?
C41 C39 C36 122.20(15) . . ?
C40 C39 C36 108.20(14) . . ?
C38 C39 C36 89.45(13) . . ?
C38 C40 C47 124.81(15) . . ?
C38 C40 C39 61.31(11) . . ?
C47 C40 C39 119.72(15) . . ?
C38 C40 C53 113.23(15) . . ?
C47 C40 C53 113.79(15) . . ?
C39 C40 C53 114.00(15) . . ?
C46 C41 C42 118.74(17) . . ?
C46 C41 C39 120.76(16) . . ?
C42 C41 C39 120.32(16) . . ?
C43 C42 C41 120.34(19) . . ?
C44 C43 C42 120.40(19) . . ?
C43 C44 C45 119.59(18) . . ?
C44 C45 C46 120.29(19) . . ?
C41 C46 C45 120.62(18) . . ?
C48 C47 C52 117.11(17) . . ?
C48 C47 C40 116.25(16) . . ?
C52 C47 C40 126.55(17) . . ?
C49 C48 C47 122.58(18) . . ?
C50 C49 C48 119.19(19) . . ?
C51 C50 C49 119.55(19) . . ?
C50 C51 C52 121.13(19) . . ?
C51 C52 C47 120.37(18) . . ?
C51 C52 C54 115.81(17) . . ?
C47 C52 C54 123.81(17) . . ?
O6 C53 C40 111.90(15) . . ?
F4 C54 F6 108.8(2) . . ?
F4 C54 F5 105.34(18) . . ?
F6 C54 F5 103.93(18) . . ?
F4 C54 C52 114.88(17) . . ?
F6 C54 C52 111.49(18) . . ?
F5 C54 C52 111.66(18) . . ?

####################################################################### 
# 
# 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_test1_a
_database_code_depnum_ccdc_archive 'CCDC 2449293'
loop_
_audit_author_name
_audit_author_address
'Shashikanth J'
;Indian Institute of Science
India
;
_audit_update_record             
;
2025-05-07 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif 2024.9-0 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C37.12 H28.61 N1.12 O3.38'
_chemical_formula_moiety         ?
_chemical_formula_weight         544.47
_chemical_melting_point          ?
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'
_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   35.3662(15)
_cell_length_b                   35.3662(15)
_cell_length_c                   9.9973(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10829.0(12)
_cell_formula_units_Z            16
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.6921
_cell_measurement_theta_max      27.0648
_cell_measurement_wavelength     0.71073
_exptl_crystal_description       block
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             4580
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.7092
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal
 structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_exptl_bruker_absorpt_correction_T_ratio 0.9513
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      120(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'flat graphite'
_bruker_diffrn_measurement_temperature_device 'Oxford Cryostream 1000'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'sealed tube'
_diffrn_source_type              ?
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.391
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_measurement_details      
;<Phi   scan: start=   0.0; len= 360.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 47.00 mm theta=   5.567 deg omega=  11.384 deg chi=  54.736 deg] 
measure for 50.0 seconds; frame angle 0.60 degrees, wavelength=0.71076>
<Omega scan: start= 191.4; len= 180.0; end= 371.4 at [Counterclockwise Eulerian 
angles: dx= 47.00 mm theta=   5.567 deg phi=   0.000 deg chi=  54.736 deg] 
measure for 50.0 seconds; frame angle 0.60 degrees, wavelength=0.71076>
<Omega scan: start= 191.4; len= 180.0; end= 371.4 at [Counterclockwise Eulerian 
angles: dx= 47.00 mm theta=   5.567 deg phi=  72.000 deg chi=  54.736 deg] 
measure for 50.0 seconds; frame angle 0.60 degrees, wavelength=0.71076>
;
_diffrn_measurement_bruker_total_exposure_time 60000.0
_diffrn_reflns_number            91396
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_theta_min         2.692
_diffrn_reflns_theta_max         27.265
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_reduction_process narrow-frame
_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
_diffrn_reflns_bruker_av_norm_I  105.419
_diffrn_reflns_bruker_number_gt  55664
_reflns_number_total             5391
_reflns_number_gt                4546
_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       APEX4
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC)'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  ?
_computing_bruker_data_scaling   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_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)+(0.0790P)²+32.4660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Intrinsic Phasing'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5391
_refine_ls_number_parameters     351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_geom_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.
;
_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_
_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
O1 O 0.37924(5) 0.57372(5) 0.73175(17) 0.0319(4) Uani 1 1 d . . . . .
O2 O 0.28624(5) 0.48910(5) 0.40135(14) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.33881(5) 0.53821(5) 0.54534(17) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.36166(7) 0.57307(7) 0.4522(3) 0.0347(5) Uani 1 1 d . . . . .
C2 C 0.37913(8) 0.56630(11) 0.3388(3) 0.0496(7) Uani 1 1 d . . . . .
H2 H 0.376413 0.538640 0.321489 0.059 Uiso 1 1 calc R U . . .
C3 C 0.40104(9) 0.60085(15) 0.2491(4) 0.0774(13) Uani 1 1 d . . . . .
H3 H 0.413119 0.596612 0.169447 0.093 Uiso 1 1 calc R U . . .
C4 C 0.40516(11) 0.64022(15) 0.2748(5) 0.0891(16) Uani 1 1 d . . . . .
H4 H 0.419611 0.663258 0.212035 0.107 Uiso 1 1 calc R U . . .
C5 C 0.38911(14) 0.64727(12) 0.3879(6) 0.0876(15) Uani 1 1 d . . . . .
H5 H 0.393133 0.675449 0.405482 0.105 Uiso 1 1 calc R U . . .
C6 C 0.36664(11) 0.61372(9) 0.4797(4) 0.0594(9) Uani 1 1 d . . . . .
H6 H 0.355011 0.618587 0.559322 0.071 Uiso 1 1 calc R U . . .
C7 C 0.34967(6) 0.54150(6) 0.6810(2) 0.0234(4) Uani 1 1 d . . . . .
C8 C 0.31844(6) 0.49893(6) 0.74779(19) 0.0204(4) Uani 1 1 d . . . . .
H8 H 0.304954 0.502016 0.831989 0.024 Uiso 1 1 calc R U . . .
C9 C 0.28524(6) 0.47127(6) 0.63749(18) 0.0190(4) Uani 1 1 d . . . . .
H9 H 0.253977 0.460689 0.660105 0.023 Uiso 1 1 calc R U . . .
C10 C 0.30145(6) 0.49859(6) 0.51214(19) 0.0206(4) Uani 1 1 d . . . . .
C11 C 0.33410(6) 0.46491(6) 0.75555(18) 0.0203(4) Uani 1 1 d . . . . .
C12 C 0.29932(6) 0.43647(6) 0.64832(19) 0.0203(4) Uani 1 1 d . . . . .
C13 C 0.29367(7) 0.42106(6) 0.79290(19) 0.0224(4) Uani 1 1 d . . . . .
C14 C 0.37991(7) 0.47564(7) 0.77987(19) 0.0225(4) Uani 1 1 d . . . . .
C15 C 0.40655(7) 0.51040(7) 0.86467(19) 0.0246(4) Uani 1 1 d . . . . .
H15 H 0.395659 0.527704 0.902633 0.030 Uiso 1 1 calc R U . . .
C16 C 0.44888(7) 0.51982(7) 0.8938(2) 0.0281(4) Uani 1 1 d . . . . .
H16 H 0.466756 0.543737 0.950597 0.034 Uiso 1 1 calc R U . . .
C17 C 0.46513(7) 0.49471(8) 0.8410(2) 0.0297(5) Uani 1 1 d . . . . .
H17 H 0.493628 0.500580 0.863985 0.036 Uiso 1 1 calc R U . . .
C18 C 0.43966(8) 0.46105(8) 0.7546(2) 0.0304(5) Uani 1 1 d . . . . .
H18 H 0.450935 0.444097 0.716498 0.036 Uiso 1 1 calc R U . . .
C19 C 0.39774(7) 0.45179(7) 0.7231(2) 0.0270(4) Uani 1 1 d . . . . .
H19 H 0.380805 0.428896 0.662042 0.032 Uiso 1 1 calc R U . . .
C20 C 0.30199(7) 0.41190(6) 0.53115(18) 0.0216(4) Uani 1 1 d . . . . .
C21 C 0.33688(7) 0.43177(7) 0.4428(2) 0.0255(4) Uani 1 1 d . . . . .
H21 H 0.359536 0.460879 0.458724 0.031 Uiso 1 1 calc R U . . .
C22 C 0.33890(8) 0.40936(8) 0.3310(2) 0.0324(5) Uani 1 1 d . . . . .
H22 H 0.363173 0.423081 0.272109 0.039 Uiso 1 1 calc R U . . .
C23 C 0.30583(9) 0.36731(8) 0.3052(2) 0.0362(5) Uani 1 1 d . . . . .
H23 H 0.307314 0.352085 0.228907 0.043 Uiso 1 1 calc R U . . .
C24 C 0.27040(8) 0.34743(7) 0.3914(2) 0.0344(5) Uani 1 1 d . . . . .
H24 H 0.247343 0.318665 0.373438 0.041 Uiso 1 1 calc R U . . .
C25 C 0.26860(8) 0.36948(7) 0.5038(2) 0.0291(5) Uani 1 1 d . . . . .
H25 H 0.244380 0.355560 0.562792 0.035 Uiso 1 1 calc R U . . .
C26 C 0.25822(7) 0.41883(6) 0.8817(2) 0.0239(4) Uani 1 1 d . . . . .
C27 C 0.21513(7) 0.39656(7) 0.8357(2) 0.0266(4) Uani 1 1 d . . . . .
H27 H 0.209352 0.385816 0.746619 0.032 Uiso 1 1 calc R U . . .
C28 C 0.18070(7) 0.38984(7) 0.9173(2) 0.0303(5) Uani 1 1 d . . . . .
H28 H 0.151644 0.374853 0.884156 0.036 Uiso 1 1 calc R U . . .
C29 C 0.18885(8) 0.40503(8) 1.0470(2) 0.0365(5) Uani 1 1 d . . . . .
H29 H 0.165358 0.400199 1.104035 0.044 Uiso 1 1 calc R U . . .
C30 C 0.23132(8) 0.42733(8) 1.0940(2) 0.0357(5) Uani 1 1 d . . . . .
H30 H 0.236578 0.437841 1.183434 0.043 Uiso 1 1 calc R U . . .
C31 C 0.26669(8) 0.43478(7) 1.0134(2) 0.0298(5) Uani 1 1 d . . . . .
C32 C 0.30113(9) 0.38273(8) 0.8174(2) 0.0359(6) Uani 1 1 d . . . . .
H1 H 0.3226(10) 0.3824(10) 0.750(3) 0.054 Uiso 1 1 d . U . . .
C34 C 0.31218(8) 0.46059(8) 1.0713(2) 0.0356(5) Uani 1 1 d . . . . .
H34A H 0.310534 0.459210 1.169142 0.053 Uiso 1 1 calc R U . . .
H34B H 0.325536 0.491090 1.042356 0.053 Uiso 1 1 calc R U . . .
H34C H 0.329932 0.448204 1.039808 0.053 Uiso 1 1 calc R U . . .
O3A O 0.26815(12) 0.34580(11) 0.8163(4) 0.0253(10) Uani 0.429(5) 1 d . . P A 1
H50A H 0.271(3) 0.334(3) 0.792(8) 0.038 Uiso 0.429(5) 1 d . U P A 1
O3B O 0.31102(9) 0.37806(9) 0.9461(3) 0.0314(8) Uani 0.571(5) 1 d . . P A 2


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 C7 1.207(2) . ?
O2 C10 1.203(2) . ?
N1 C7 1.399(3) . ?
N1 C10 1.403(3) . ?
N1 C1 1.429(3) . ?
C1 C2 1.368(4) . ?
C1 C6 1.386(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.350(7) . ?
C4 C5 1.344(7) . ?
C5 C6 1.392(5) . ?
C7 C8 1.506(3) . ?
C8 C9 1.550(3) . ?
C8 C11 1.558(3) . ?
C9 C10 1.509(3) . ?
C9 C12 1.545(3) . ?
C11 C14 1.488(3) . ?
C11 C13 1.540(3) . ?
C11 C12 1.561(3) . ?
C12 C20 1.489(3) . ?
C12 C13 1.522(3) . ?
C13 C26 1.506(3) . ?
C13 C32 1.525(3) . ?
C14 C15 1.400(3) . ?
C14 C19 1.401(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.379(3) . ?
C18 C19 1.385(3) . ?
C20 C21 1.389(3) . ?
C20 C25 1.396(3) . ?
C21 C22 1.392(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.388(4) . ?
C24 C25 1.387(3) . ?
C26 C27 1.398(3) . ?
C26 C31 1.404(3) . ?
C27 C28 1.384(3) . ?
C28 C29 1.377(3) . ?
C29 C30 1.384(4) . ?
C30 C31 1.398(3) . ?
C31 C34 1.513(3) . ?
C32 O3A 1.242(4) . ?
C32 O3B 1.365(3) . ?

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
C7 N1 C10 113.25(16) . . ?
C7 N1 C1 123.14(18) . . ?
C10 N1 C1 123.46(17) . . ?
C2 C1 C6 120.8(3) . . ?
C2 C1 N1 119.9(2) . . ?
C6 C1 N1 119.3(3) . . ?
C1 C2 C3 118.7(3) . . ?
C4 C3 C2 120.4(4) . . ?
C5 C4 C3 120.9(3) . . ?
C4 C5 C6 120.7(4) . . ?
C1 C6 C5 118.4(4) . . ?
O1 C7 N1 123.93(19) . . ?
O1 C7 C8 127.82(19) . . ?
N1 C7 C8 108.25(16) . . ?
C7 C8 C9 105.12(15) . . ?
C7 C8 C11 115.34(16) . . ?
C9 C8 C11 89.86(14) . . ?
C10 C9 C12 113.42(15) . . ?
C10 C9 C8 105.14(15) . . ?
C12 C9 C8 90.51(14) . . ?
O2 C10 N1 124.25(18) . . ?
O2 C10 C9 127.72(18) . . ?
N1 C10 C9 108.03(16) . . ?
C14 C11 C13 124.18(16) . . ?
C14 C11 C8 124.98(17) . . ?
C13 C11 C8 106.28(15) . . ?
C14 C11 C12 133.11(16) . . ?
C13 C11 C12 58.80(12) . . ?
C8 C11 C12 89.63(14) . . ?
C20 C12 C13 124.97(16) . . ?
C20 C12 C9 123.32(16) . . ?
C13 C12 C9 108.35(15) . . ?
C20 C12 C11 131.05(17) . . ?
C13 C12 C11 59.91(12) . . ?
C9 C12 C11 89.93(14) . . ?
C26 C13 C12 122.38(17) . . ?
C26 C13 C32 111.62(17) . . ?
C12 C13 C32 114.88(16) . . ?
C26 C13 C11 121.68(16) . . ?
C12 C13 C11 61.29(12) . . ?
C32 C13 C11 116.61(18) . . ?
C15 C14 C19 117.77(18) . . ?
C15 C14 C11 119.48(17) . . ?
C19 C14 C11 122.74(18) . . ?
C16 C15 C14 120.53(19) . . ?
C17 C16 C15 120.6(2) . . ?
C18 C17 C16 119.5(2) . . ?
C17 C18 C19 120.4(2) . . ?
C18 C19 C14 121.1(2) . . ?
C21 C20 C25 118.63(18) . . ?
C21 C20 C12 120.30(18) . . ?
C25 C20 C12 120.99(18) . . ?
C20 C21 C22 120.5(2) . . ?
C23 C22 C21 120.4(2) . . ?
C22 C23 C24 119.6(2) . . ?
C25 C24 C23 120.1(2) . . ?
C24 C25 C20 120.7(2) . . ?
C27 C26 C31 119.2(2) . . ?
C27 C26 C13 118.70(18) . . ?
C31 C26 C13 121.81(19) . . ?
C28 C27 C26 121.4(2) . . ?
C29 C28 C27 119.6(2) . . ?
C28 C29 C30 119.9(2) . . ?
C29 C30 C31 121.7(2) . . ?
C30 C31 C26 118.3(2) . . ?
C30 C31 C34 118.3(2) . . ?
C26 C31 C34 123.4(2) . . ?
O3A C32 C13 116.4(3) . . ?
O3B C32 C13 115.3(2) . . ?

