# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_KSA_5_230623_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2281105'
loop_
_audit_author_name
_audit_author_address
'Ashokkumar Krishnan'
;Vellore Institute of Technology, Vellore
India
;
_audit_update_record             
;
2023-07-12 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H26 F3 N3 O2'
_chemical_formula_sum            'C35 H26 F3 N3 O2'
_chemical_formula_weight         577.59

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.8114(5)
_cell_length_b                   11.3929(5)
_cell_length_c                   12.8702(6)
_cell_angle_alpha                106.897(2)
_cell_angle_beta                 95.882(2)
_cell_angle_gamma                109.7260(10)
_cell_volume                     1391.96(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9271
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.06

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7038
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39038
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         28.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6939
_reflns_number_gt                4004
_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 APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1168P)²+0.7156P] 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_number_reflns         6939
_refine_ls_number_parameters     396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2429
_refine_ls_wR_factor_gt          0.1951
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.9170(4) 0.0862(4) 0.1053(5) 0.226(3) Uani 1 1 d . . . . .
F2 F 0.7251(4) -0.0333(3) 0.0433(5) 0.222(3) Uani 1 1 d . . . . .
F3 F 0.8279(7) 0.0756(6) -0.0361(4) 0.245(3) Uani 1 1 d . . . . .
O1 O 0.28448(18) 0.1424(2) 0.38781(17) 0.0561(5) Uani 1 1 d . . . . .
O2 O 0.78994(19) 0.50283(19) 0.56949(16) 0.0576(5) Uani 1 1 d . . . . .
N1 N 0.6742(2) 0.2780(2) 0.65010(17) 0.0450(5) Uani 1 1 d . . . . .
N2 N 0.3802(2) 0.3143(2) 0.2915(2) 0.0539(6) Uani 1 1 d . . . . .
H1 H 0.298(4) 0.249(4) 0.279(3) 0.081 Uiso 1 1 d . U . . .
N3 N 0.6513(2) 0.5282(2) 0.39878(18) 0.0464(5) Uani 1 1 d . . . . .
H1B H 0.744(3) 0.575(3) 0.436(3) 0.070 Uiso 1 1 d . U . . .
C1 C 0.4584(3) 0.1261(2) 0.5830(2) 0.0423(6) Uani 1 1 d . . . . .
C2 C 0.5794(3) 0.1663(3) 0.6610(2) 0.0444(6) Uani 1 1 d . . . . .
C3 C 0.5916(3) 0.1000(3) 0.7340(2) 0.0560(7) Uani 1 1 d . . . . .
H3 H 0.672038 0.127141 0.784892 0.067 Uiso 1 1 calc R U . . .
C4 C 0.4802(3) -0.0071(3) 0.7279(3) 0.0603(8) Uani 1 1 d . . . . .
H4 H 0.485426 -0.053210 0.776060 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3592(3) -0.0491(3) 0.6514(2) 0.0573(7) Uani 1 1 d . . . . .
H5 H 0.285599 -0.122000 0.649842 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3471(3) 0.0156(3) 0.5785(2) 0.0484(6) Uani 1 1 d . . . . .
H6 H 0.266558 -0.013340 0.527216 0.058 Uiso 1 1 calc R U . . .
C7 C 0.4837(2) 0.2161(2) 0.5238(2) 0.0412(6) Uani 1 1 d . . . . .
C8 C 0.6146(2) 0.3068(2) 0.5670(2) 0.0419(6) Uani 1 1 d . . . . .
C9 C 0.4018(3) 0.2199(3) 0.4297(2) 0.0429(6) Uani 1 1 d . . . . .
C10 C 0.4666(3) 0.3252(3) 0.3825(2) 0.0432(6) Uani 1 1 d . . . . .
C11 C 0.5921(2) 0.4205(2) 0.4316(2) 0.0407(6) Uani 1 1 d . . . . .
C12 C 0.6751(3) 0.4167(2) 0.5271(2) 0.0425(6) Uani 1 1 d . . . . .
C13 C 0.3842(3) 0.3938(3) 0.2257(2) 0.0465(6) Uani 1 1 d . . . . .
C14 C 0.5034(3) 0.4916(3) 0.2223(2) 0.0446(6) Uani 1 1 d . . . . .
C15 C 0.6391(3) 0.5055(3) 0.2787(2) 0.0457(6) Uani 1 1 d . . . . .
H15 H 0.704783 0.586005 0.273074 0.055 Uiso 1 1 calc R U . . .
C16 C 0.2617(3) 0.3670(3) 0.1589(2) 0.0528(7) Uani 1 1 d . . . . .
H16 H 0.184687 0.298971 0.159611 0.063 Uiso 1 1 calc R U . . .
C17 C 0.2523(3) 0.4398(3) 0.0914(2) 0.0551(7) Uani 1 1 d . . . . .
C18 C 0.3675(3) 0.5428(3) 0.0947(2) 0.0542(7) Uani 1 1 d . . . . .
H18 H 0.361451 0.595911 0.053114 0.065 Uiso 1 1 calc R U . . .
C19 C 0.4920(3) 0.5698(3) 0.1582(2) 0.0482(6) Uani 1 1 d . . . . .
C20 C 0.8148(3) 0.3415(3) 0.7114(2) 0.0498(7) Uani 1 1 d . . . . .
H20A H 0.818643 0.339308 0.786400 0.060 Uiso 1 1 calc R U . . .
H20B H 0.849465 0.434022 0.716921 0.060 Uiso 1 1 calc R U . . .
C21 C 0.9040(3) 0.2766(3) 0.6583(2) 0.0497(7) Uani 1 1 d . . . . .
C22 C 0.9421(3) 0.2925(3) 0.5616(2) 0.0567(7) Uani 1 1 d . . . . .
H22 H 0.910693 0.342632 0.528470 0.068 Uiso 1 1 calc R U . . .
C23 C 1.0259(3) 0.2349(3) 0.5141(3) 0.0693(9) Uani 1 1 d . . . . .
H23 H 1.049193 0.244955 0.448760 0.083 Uiso 1 1 calc R U . . .
C24 C 1.0744(3) 0.1634(3) 0.5630(4) 0.0784(11) Uani 1 1 d . . . . .
H24 H 1.132528 0.126601 0.531599 0.094 Uiso 1 1 calc R U . . .
C25 C 1.0384(3) 0.1450(4) 0.6578(4) 0.0791(11) Uani 1 1 d . . . . .
H25 H 1.070779 0.094791 0.689962 0.095 Uiso 1 1 calc R U . . .
C26 C 0.9529(3) 0.2021(3) 0.7060(3) 0.0629(8) Uani 1 1 d . . . . .
H26 H 0.928752 0.189980 0.770571 0.075 Uiso 1 1 calc R U . . .
C27 C 0.6796(3) 0.3906(3) 0.2194(2) 0.0446(6) Uani 1 1 d . . . . .
C28 C 0.6024(3) 0.2895(3) 0.1209(2) 0.0532(7) Uani 1 1 d . . . . .
H28 H 0.520868 0.288702 0.088970 0.064 Uiso 1 1 calc R U . . .
C29 C 0.6444(3) 0.1894(3) 0.0689(3) 0.0596(8) Uani 1 1 d . . . . .
H29 H 0.590978 0.122523 0.002677 0.071 Uiso 1 1 calc R U . . .
C30 C 0.7642(3) 0.1885(3) 0.1147(3) 0.0604(8) Uani 1 1 d . . . . .
C31 C 0.8428(3) 0.2882(4) 0.2129(3) 0.0692(9) Uani 1 1 d . . . . .
H31 H 0.924420 0.288557 0.244132 0.083 Uiso 1 1 calc R U . . .
C32 C 0.8006(3) 0.3877(3) 0.2649(3) 0.0636(8) Uani 1 1 d . . . . .
H32 H 0.853990 0.453886 0.331510 0.076 Uiso 1 1 calc R U . . .
C33 C 0.1201(3) 0.4078(4) 0.0170(3) 0.0760(10) Uani 1 1 d . . . . .
H33A H 0.132863 0.465828 -0.025567 0.114 Uiso 1 1 calc R U . . .
H33B H 0.056502 0.419987 0.061753 0.114 Uiso 1 1 calc R U . . .
H33C H 0.086334 0.317155 -0.032517 0.114 Uiso 1 1 calc R U . . .
C34 C 0.6131(3) 0.6845(3) 0.1564(3) 0.0599(8) Uani 1 1 d . . . . .
H34A H 0.585251 0.726700 0.109151 0.090 Uiso 1 1 calc R U . . .
H34B H 0.678424 0.651686 0.128209 0.090 Uiso 1 1 calc R U . . .
H34C H 0.652355 0.747713 0.230544 0.090 Uiso 1 1 calc R U . . .
C35 C 0.8056(4) 0.0793(4) 0.0604(4) 0.0848(11) 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 C35 1.248(5) . ?
F2 C35 1.223(5) . ?
F3 C35 1.281(5) . ?
O1 C9 1.227(3) . ?
O2 C12 1.237(3) . ?
N1 C8 1.369(3) . ?
N1 C2 1.394(3) . ?
N1 C20 1.461(3) . ?
N2 C10 1.369(3) . ?
N2 C13 1.402(3) . ?
N2 H1 0.91(4) . ?
N3 C11 1.384(3) . ?
N3 C15 1.475(3) . ?
N3 H1B 0.95(3) . ?
C1 C6 1.399(4) . ?
C1 C2 1.410(4) . ?
C1 C7 1.419(3) . ?
C2 C3 1.387(4) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.378(3) . ?
C7 C9 1.444(4) . ?
C8 C12 1.465(4) . ?
C9 C10 1.498(4) . ?
C10 C11 1.361(3) . ?
C11 C12 1.466(4) . ?
C13 C16 1.388(4) . ?
C13 C14 1.405(4) . ?
C14 C19 1.403(4) . ?
C14 C15 1.503(4) . ?
C15 C27 1.537(4) . ?
C15 H15 0.9800 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(4) . ?
C17 C33 1.502(4) . ?
C18 C19 1.387(4) . ?
C18 H18 0.9300 . ?
C19 C34 1.513(4) . ?
C20 C21 1.505(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C26 1.385(4) . ?
C21 C22 1.393(4) . ?
C22 C23 1.381(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.361(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.397(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.384(4) . ?
C27 C32 1.392(4) . ?
C28 C29 1.386(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.371(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.380(5) . ?
C30 C35 1.473(5) . ?
C31 C32 1.383(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C2 107.8(2) . . ?
C8 N1 C20 127.9(2) . . ?
C2 N1 C20 124.1(2) . . ?
C10 N2 C13 133.8(2) . . ?
C10 N2 H1 111(2) . . ?
C13 N2 H1 114(2) . . ?
C11 N3 C15 118.6(2) . . ?
C11 N3 H1B 111(2) . . ?
C15 N3 H1B 109.2(19) . . ?
C6 C1 C2 119.1(2) . . ?
C6 C1 C7 134.7(3) . . ?
C2 C1 C7 106.2(2) . . ?
C3 C2 N1 129.4(3) . . ?
C3 C2 C1 122.1(3) . . ?
N1 C2 C1 108.5(2) . . ?
C4 C3 C2 117.2(3) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C8 C7 C1 107.7(2) . . ?
C8 C7 C9 120.5(2) . . ?
C1 C7 C9 131.6(2) . . ?
N1 C8 C7 109.8(2) . . ?
N1 C8 C12 127.3(2) . . ?
C7 C8 C12 122.9(2) . . ?
O1 C9 C7 123.7(2) . . ?
O1 C9 C10 119.5(2) . . ?
C7 C9 C10 116.8(2) . . ?
C11 C10 N2 127.2(2) . . ?
C11 C10 C9 121.8(2) . . ?
N2 C10 C9 110.8(2) . . ?
C10 C11 N3 124.3(2) . . ?
C10 C11 C12 121.0(2) . . ?
N3 C11 C12 114.6(2) . . ?
O2 C12 C8 123.3(2) . . ?
O2 C12 C11 120.2(2) . . ?
C8 C12 C11 116.5(2) . . ?
C16 C13 N2 115.7(2) . . ?
C16 C13 C14 120.7(2) . . ?
N2 C13 C14 123.6(2) . . ?
C19 C14 C13 117.7(2) . . ?
C19 C14 C15 121.1(2) . . ?
C13 C14 C15 121.1(2) . . ?
N3 C15 C14 112.7(2) . . ?
N3 C15 C27 112.1(2) . . ?
C14 C15 C27 112.9(2) . . ?
N3 C15 H15 106.2 . . ?
C14 C15 H15 106.2 . . ?
C27 C15 H15 106.2 . . ?
C17 C16 C13 121.1(3) . . ?
C17 C16 H16 119.4 . . ?
C13 C16 H16 119.4 . . ?
C18 C17 C16 118.1(3) . . ?
C18 C17 C33 121.1(3) . . ?
C16 C17 C33 120.8(3) . . ?
C17 C18 C19 122.1(3) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 C34 118.5(3) . . ?
C14 C19 C34 121.6(3) . . ?
N1 C20 C21 113.5(2) . . ?
N1 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
N1 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C26 C21 C22 118.2(3) . . ?
C26 C21 C20 120.8(3) . . ?
C22 C21 C20 121.0(3) . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.1(4) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.5(3) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C32 117.6(3) . . ?
C28 C27 C15 123.2(2) . . ?
C32 C27 C15 119.2(2) . . ?
C27 C28 C29 121.3(3) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.3 . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.4(3) . . ?
C29 C30 C35 119.8(3) . . ?
C31 C30 C35 120.8(3) . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C27 121.2(3) . . ?
C31 C32 H32 119.4 . . ?
C27 C32 H32 119.4 . . ?
C17 C33 H33A 109.5 . . ?
C17 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C17 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C19 C34 H34A 109.5 . . ?
C19 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C19 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
F2 C35 F1 106.5(5) . . ?
F2 C35 F3 103.3(5) . . ?
F1 C35 F3 98.8(4) . . ?
F2 C35 C30 116.2(3) . . ?
F1 C35 C30 116.4(4) . . ?
F3 C35 C30 113.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C2 C3 -179.6(3) . . . . ?
C20 N1 C2 C3 5.6(4) . . . . ?
C8 N1 C2 C1 -0.3(3) . . . . ?
C20 N1 C2 C1 -175.1(2) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C7 C1 C2 C3 180.0(2) . . . . ?
C6 C1 C2 N1 -179.6(2) . . . . ?
C7 C1 C2 N1 0.6(3) . . . . ?
N1 C2 C3 C4 178.9(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C7 C1 C6 C5 -179.5(3) . . . . ?
C6 C1 C7 C8 179.5(3) . . . . ?
C2 C1 C7 C8 -0.7(3) . . . . ?
C6 C1 C7 C9 -4.6(5) . . . . ?
C2 C1 C7 C9 175.2(2) . . . . ?
C2 N1 C8 C7 -0.2(3) . . . . ?
C20 N1 C8 C7 174.4(2) . . . . ?
C2 N1 C8 C12 179.2(2) . . . . ?
C20 N1 C8 C12 -6.3(4) . . . . ?
C1 C7 C8 N1 0.6(3) . . . . ?
C9 C7 C8 N1 -175.9(2) . . . . ?
C1 C7 C8 C12 -178.8(2) . . . . ?
C9 C7 C8 C12 4.7(4) . . . . ?
C8 C7 C9 O1 -179.6(2) . . . . ?
C1 C7 C9 O1 4.9(4) . . . . ?
C8 C7 C9 C10 0.4(3) . . . . ?
C1 C7 C9 C10 -175.1(2) . . . . ?
C13 N2 C10 C11 -4.6(5) . . . . ?
C13 N2 C10 C9 171.8(3) . . . . ?
O1 C9 C10 C11 174.2(2) . . . . ?
C7 C9 C10 C11 -5.8(3) . . . . ?
O1 C9 C10 N2 -2.4(3) . . . . ?
C7 C9 C10 N2 177.6(2) . . . . ?
N2 C10 C11 N3 3.1(4) . . . . ?
C9 C10 C11 N3 -172.8(2) . . . . ?
N2 C10 C11 C12 -178.0(2) . . . . ?
C9 C10 C11 C12 6.0(4) . . . . ?
C15 N3 C11 C10 -43.8(4) . . . . ?
C15 N3 C11 C12 137.3(2) . . . . ?
N1 C8 C12 O2 -3.5(4) . . . . ?
C7 C8 C12 O2 175.8(2) . . . . ?
N1 C8 C12 C11 176.1(2) . . . . ?
C7 C8 C12 C11 -4.6(3) . . . . ?
C10 C11 C12 O2 178.7(2) . . . . ?
N3 C11 C12 O2 -2.4(3) . . . . ?
C10 C11 C12 C8 -0.9(3) . . . . ?
N3 C11 C12 C8 178.1(2) . . . . ?
C10 N2 C13 C16 -163.4(3) . . . . ?
C10 N2 C13 C14 19.0(5) . . . . ?
C16 C13 C14 C19 6.4(4) . . . . ?
N2 C13 C14 C19 -176.1(2) . . . . ?
C16 C13 C14 C15 -169.4(2) . . . . ?
N2 C13 C14 C15 8.2(4) . . . . ?
C11 N3 C15 C14 78.2(3) . . . . ?
C11 N3 C15 C27 -50.4(3) . . . . ?
C19 C14 C15 N3 127.1(3) . . . . ?
C13 C14 C15 N3 -57.3(3) . . . . ?
C19 C14 C15 C27 -104.7(3) . . . . ?
C13 C14 C15 C27 70.9(3) . . . . ?
N2 C13 C16 C17 179.1(3) . . . . ?
C14 C13 C16 C17 -3.1(4) . . . . ?
C13 C16 C17 C18 -2.0(4) . . . . ?
C13 C16 C17 C33 178.4(3) . . . . ?
C16 C17 C18 C19 3.8(4) . . . . ?
C33 C17 C18 C19 -176.6(3) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?
C17 C18 C19 C34 179.7(3) . . . . ?
C13 C14 C19 C18 -4.6(4) . . . . ?
C15 C14 C19 C18 171.2(2) . . . . ?
C13 C14 C19 C34 175.2(2) . . . . ?
C15 C14 C19 C34 -9.0(4) . . . . ?
C8 N1 C20 C21 -90.0(3) . . . . ?
C2 N1 C20 C21 83.7(3) . . . . ?
N1 C20 C21 C26 -108.1(3) . . . . ?
N1 C20 C21 C22 73.5(3) . . . . ?
C26 C21 C22 C23 0.4(4) . . . . ?
C20 C21 C22 C23 178.8(3) . . . . ?
C21 C22 C23 C24 -1.2(5) . . . . ?
C22 C23 C24 C25 1.6(5) . . . . ?
C23 C24 C25 C26 -1.1(5) . . . . ?
C22 C21 C26 C25 0.1(4) . . . . ?
C20 C21 C26 C25 -178.4(3) . . . . ?
C24 C25 C26 C21 0.2(5) . . . . ?
N3 C15 C27 C28 132.0(3) . . . . ?
C14 C15 C27 C28 3.5(3) . . . . ?
N3 C15 C27 C32 -49.0(3) . . . . ?
C14 C15 C27 C32 -177.5(2) . . . . ?
C32 C27 C28 C29 -0.4(4) . . . . ?
C15 C27 C28 C29 178.5(2) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C31 -0.1(5) . . . . ?
C28 C29 C30 C35 178.1(3) . . . . ?
C29 C30 C31 C32 0.4(5) . . . . ?
C35 C30 C31 C32 -177.8(3) . . . . ?
C30 C31 C32 C27 -0.7(5) . . . . ?
C28 C27 C32 C31 0.7(4) . . . . ?
C15 C27 C32 C31 -178.3(3) . . . . ?
C29 C30 C35 F2 -54.7(6) . . . . ?
C31 C30 C35 F2 123.5(5) . . . . ?
C29 C30 C35 F1 178.6(5) . . . . ?
C31 C30 C35 F1 -3.2(7) . . . . ?
C29 C30 C35 F3 64.9(6) . . . . ?
C31 C30 C35 F3 -116.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H1 O1 0.91(4) 2.08(4) 2.598(3) 115(3) . yes
N3 H1B O2 0.95(3) 2.19(3) 2.673(3) 110(2) . yes
C20 H20B O2 0.97 2.36 2.995(3) 122.0 . yes

_refine_diff_density_max         0.715
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_KSA_12_200723_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2288286'
loop_
_audit_author_name
_audit_author_address
'Ashokkumar Krishnan'
;Vellore Institute of Technology, Vellore
India
;
_audit_update_record             
;
2023-08-12 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 N2 O4'
_chemical_formula_sum            'C24 H24 N2 O4'
_chemical_formula_weight         404.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   10.8433(16)
_cell_length_b                   9.7755(12)
_cell_length_c                   19.606(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.988(4)
_cell_angle_gamma                90
_cell_volume                     2032.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    6471
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.158
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_max          0.259
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26574
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5042
_reflns_number_gt                2843
_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 APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+0.6873P] 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_number_reflns         5042
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
O1 O 0.84784(14) 0.66733(17) 0.53359(8) 0.0678(5) Uani 1 1 d . . . . .
O2 O 0.95739(14) 0.48742(17) 0.30041(8) 0.0669(4) Uani 1 1 d . . . . .
O3 O 0.70600(15) 0.34512(15) 0.20529(7) 0.0624(4) Uani 1 1 d . . . . .
O4 O 0.36437(16) 0.69824(19) 0.28434(10) 0.0850(6) Uani 1 1 d . . . . .
N1 N 0.71306(17) 0.46012(19) 0.47534(9) 0.0534(5) Uani 1 1 d . . . . .
H3 H 0.712(2) 0.511(3) 0.5116(13) 0.080 Uiso 1 1 d . U . . .
N2 N 0.79169(15) 0.33670(17) 0.35238(9) 0.0472(4) Uani 1 1 d . . . . .
H1 H 0.826(2) 0.324(2) 0.3145(12) 0.071 Uiso 1 1 d . U . . .
C1 C 0.59564(18) 0.2846(2) 0.39586(10) 0.0466(5) Uani 1 1 d . . . . .
C2 C 0.50087(19) 0.1851(2) 0.38784(12) 0.0561(5) Uani 1 1 d . . . . .
H2 H 0.482832 0.136570 0.346165 0.067 Uiso 1 1 calc R U . . .
C3 C 0.4326(2) 0.1546(2) 0.43791(14) 0.0629(6) Uani 1 1 d . . . . .
C4 C 0.4625(2) 0.2282(3) 0.49956(13) 0.0676(7) Uani 1 1 d . . . . .
H4 H 0.418099 0.211367 0.534502 0.081 Uiso 1 1 calc R U . . .
C5 C 0.5560(2) 0.3255(2) 0.51033(11) 0.0601(6) Uani 1 1 d . . . . .
H5 H 0.574690 0.371734 0.552668 0.072 Uiso 1 1 calc R U . . .
C6 C 0.62349(18) 0.3561(2) 0.45882(10) 0.0479(5) Uani 1 1 d . . . . .
C7 C 0.80457(17) 0.50918(19) 0.44264(9) 0.0432(4) Uani 1 1 d . . . . .
C8 C 0.83894(17) 0.45648(19) 0.38561(9) 0.0420(4) Uani 1 1 d . . . . .
C9 C 0.65480(18) 0.3119(2) 0.33412(10) 0.0454(5) Uani 1 1 d . . . . .
H9 H 0.643609 0.227844 0.306264 0.055 Uiso 1 1 calc R U . . .
C10 C 0.87406(18) 0.6267(2) 0.47910(10) 0.0473(5) Uani 1 1 d . . . . .
C11 C 0.97711(18) 0.6918(2) 0.45129(10) 0.0489(5) Uani 1 1 d . . . . .
C12 C 1.00796(18) 0.6433(2) 0.39335(10) 0.0485(5) Uani 1 1 d . . . . .
C13 C 0.93590(18) 0.5265(2) 0.35629(10) 0.0474(5) Uani 1 1 d . . . . .
C14 C 0.3303(2) 0.0480(3) 0.42688(16) 0.0869(8) Uani 1 1 d . . . . .
H14A H 0.340687 -0.009879 0.467240 0.130 Uiso 1 1 calc R U . . .
H14B H 0.335598 -0.006284 0.386766 0.130 Uiso 1 1 calc R U . . .
H14C H 0.249527 0.091980 0.419595 0.130 Uiso 1 1 calc R U . . .
C15 C 0.58987(17) 0.42458(19) 0.28627(9) 0.0439(5) Uani 1 1 d . . . . .
C16 C 0.62326(19) 0.4411(2) 0.22147(10) 0.0499(5) Uani 1 1 d . . . . .
C17 C 0.5715(2) 0.5454(2) 0.17798(11) 0.0593(6) Uani 1 1 d . . . . .
H17 H 0.595215 0.556747 0.135399 0.071 Uiso 1 1 calc R U . . .
C18 C 0.4841(2) 0.6344(2) 0.19660(12) 0.0606(6) Uani 1 1 d . . . . .
H18 H 0.449465 0.704591 0.166683 0.073 Uiso 1 1 calc R U . . .
C19 C 0.44931(19) 0.6177(2) 0.25977(12) 0.0561(5) Uani 1 1 d . . . . .
C20 C 0.50277(18) 0.5130(2) 0.30403(10) 0.0510(5) Uani 1 1 d . . . . .
H20 H 0.479200 0.502273 0.346693 0.061 Uiso 1 1 calc R U . . .
C21 C 1.0402(2) 0.8119(2) 0.49185(12) 0.0671(6) Uani 1 1 d . . . . .
H21A H 1.078875 0.868037 0.462018 0.101 Uiso 1 1 calc R U . . .
H21B H 1.103395 0.779871 0.530294 0.101 Uiso 1 1 calc R U . . .
H21C H 0.978528 0.864585 0.509170 0.101 Uiso 1 1 calc R U . . .
C22 C 1.1106(2) 0.6989(3) 0.36089(13) 0.0672(6) Uani 1 1 d . . . . .
H22A H 1.162439 0.625114 0.350832 0.101 Uiso 1 1 calc R U . . .
H22B H 1.161188 0.761733 0.392556 0.101 Uiso 1 1 calc R U . . .
H22C H 1.074130 0.745715 0.318436 0.101 Uiso 1 1 calc R U . . .
C23 C 0.7739(2) 0.3775(3) 0.15268(12) 0.0736(7) Uani 1 1 d . . . . .
H23A H 0.835181 0.307363 0.150947 0.110 Uiso 1 1 calc R U . . .
H23B H 0.815953 0.463690 0.163226 0.110 Uiso 1 1 calc R U . . .
H23C H 0.716476 0.383227 0.108353 0.110 Uiso 1 1 calc R U . . .
C24 C 0.3067(2) 0.8075(3) 0.24175(16) 0.0856(8) Uani 1 1 d . . . . .
H24A H 0.250898 0.856049 0.265339 0.128 Uiso 1 1 calc R U . . .
H24B H 0.259726 0.771713 0.198513 0.128 Uiso 1 1 calc R U . . .
H24C H 0.370561 0.868785 0.232587 0.128 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
O1 C10 1.227(2) . ?
O2 C13 1.227(2) . ?
O3 C16 1.380(2) . ?
O3 C23 1.422(3) . ?
O4 C19 1.373(3) . ?
O4 C24 1.419(3) . ?
N1 C7 1.375(2) . ?
N1 C6 1.397(3) . ?
N1 H3 0.87(3) . ?
N2 C8 1.385(2) . ?
N2 C9 1.473(2) . ?
N2 H1 0.90(2) . ?
C1 C6 1.396(3) . ?
C1 C2 1.400(3) . ?
C1 C9 1.507(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(3) . ?
C3 C14 1.505(3) . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.352(2) . ?
C7 C10 1.475(3) . ?
C8 C13 1.468(3) . ?
C9 C15 1.522(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.484(3) . ?
C11 C12 1.336(3) . ?
C11 C21 1.501(3) . ?
C12 C13 1.485(3) . ?
C12 C22 1.495(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.377(3) . ?
C15 C16 1.401(3) . ?
C16 C17 1.372(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O3 C23 118.34(17) . . ?
C19 O4 C24 118.10(19) . . ?
C7 N1 C6 132.86(17) . . ?
C7 N1 H3 108.1(17) . . ?
C6 N1 H3 118.9(17) . . ?
C8 N2 C9 120.60(15) . . ?
C8 N2 H1 109.2(15) . . ?
C9 N2 H1 109.9(14) . . ?
C6 C1 C2 117.79(18) . . ?
C6 C1 C9 124.89(18) . . ?
C2 C1 C9 117.23(18) . . ?
C3 C2 C1 124.1(2) . . ?
C3 C2 H2 118.0 . . ?
C1 C2 H2 118.0 . . ?
C2 C3 C4 116.5(2) . . ?
C2 C3 C14 122.4(2) . . ?
C4 C3 C14 121.1(2) . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 N1 125.57(18) . . ?
C1 C6 C5 118.8(2) . . ?
N1 C6 C5 115.59(19) . . ?
C8 C7 N1 127.05(19) . . ?
C8 C7 C10 119.79(18) . . ?
N1 C7 C10 113.04(16) . . ?
C7 C8 N2 124.92(18) . . ?
C7 C8 C13 119.29(18) . . ?
N2 C8 C13 115.77(16) . . ?
N2 C9 C1 114.17(16) . . ?
N2 C9 C15 110.16(15) . . ?
C1 C9 C15 113.81(16) . . ?
N2 C9 H9 106.0 . . ?
C1 C9 H9 106.0 . . ?
C15 C9 H9 106.0 . . ?
O1 C10 C7 119.12(19) . . ?
O1 C10 C11 120.60(19) . . ?
C7 C10 C11 120.24(17) . . ?
C12 C11 C10 120.05(18) . . ?
C12 C11 C21 124.1(2) . . ?
C10 C11 C21 115.82(18) . . ?
C11 C12 C13 119.31(18) . . ?
C11 C12 C22 125.0(2) . . ?
C13 C12 C22 115.73(18) . . ?
O2 C13 C8 119.25(18) . . ?
O2 C13 C12 119.85(18) . . ?
C8 C13 C12 120.89(17) . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.48(18) . . ?
C20 C15 C9 123.52(17) . . ?
C16 C15 C9 117.98(18) . . ?
C17 C16 O3 124.34(18) . . ?
C17 C16 C15 120.0(2) . . ?
O3 C16 C15 115.64(18) . . ?
C16 C17 C18 121.0(2) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 119.4(2) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
O4 C19 C18 125.2(2) . . ?
O4 C19 C20 115.28(19) . . ?
C18 C19 C20 119.5(2) . . ?
C15 C20 C19 121.58(18) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(3) . . . . ?
C9 C1 C2 C3 -175.86(19) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C14 179.26(19) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C14 C3 C4 C5 179.7(2) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C2 C1 C6 N1 -178.74(18) . . . . ?
C9 C1 C6 N1 -2.4(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C9 C1 C6 C5 176.24(18) . . . . ?
C7 N1 C6 C1 -8.9(3) . . . . ?
C7 N1 C6 C5 172.4(2) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 N1 177.91(19) . . . . ?
C6 N1 C7 C8 -6.7(3) . . . . ?
C6 N1 C7 C10 177.40(19) . . . . ?
N1 C7 C8 N2 -4.2(3) . . . . ?
C10 C7 C8 N2 171.49(16) . . . . ?
N1 C7 C8 C13 177.60(18) . . . . ?
C10 C7 C8 C13 -6.7(3) . . . . ?
C9 N2 C8 C7 48.8(3) . . . . ?
C9 N2 C8 C13 -132.91(18) . . . . ?
C8 N2 C9 C1 -70.7(2) . . . . ?
C8 N2 C9 C15 58.8(2) . . . . ?
C6 C1 C9 N2 42.3(3) . . . . ?
C2 C1 C9 N2 -141.35(17) . . . . ?
C6 C1 C9 C15 -85.4(2) . . . . ?
C2 C1 C9 C15 91.0(2) . . . . ?
C8 C7 C10 O1 -174.83(18) . . . . ?
N1 C7 C10 O1 1.4(3) . . . . ?
C8 C7 C10 C11 3.2(3) . . . . ?
N1 C7 C10 C11 179.46(16) . . . . ?
O1 C10 C11 C12 177.47(19) . . . . ?
C7 C10 C11 C12 -0.5(3) . . . . ?
O1 C10 C11 C21 -2.9(3) . . . . ?
C7 C10 C11 C21 179.08(17) . . . . ?
C10 C11 C12 C13 1.6(3) . . . . ?
C21 C11 C12 C13 -177.96(17) . . . . ?
C10 C11 C12 C22 -179.25(18) . . . . ?
C21 C11 C12 C22 1.2(3) . . . . ?
C7 C8 C13 O2 -172.16(18) . . . . ?
N2 C8 C13 O2 9.5(3) . . . . ?
C7 C8 C13 C12 7.9(3) . . . . ?
N2 C8 C13 C12 -170.46(16) . . . . ?
C11 C12 C13 O2 174.82(19) . . . . ?
C22 C12 C13 O2 -4.4(3) . . . . ?
C11 C12 C13 C8 -5.3(3) . . . . ?
C22 C12 C13 C8 175.54(18) . . . . ?
N2 C9 C15 C20 -116.92(19) . . . . ?
C1 C9 C15 C20 12.8(3) . . . . ?
N2 C9 C15 C16 61.3(2) . . . . ?
C1 C9 C15 C16 -168.96(17) . . . . ?
C23 O3 C16 C17 21.3(3) . . . . ?
C23 O3 C16 C15 -160.62(18) . . . . ?
C20 C15 C16 C17 1.4(3) . . . . ?
C9 C15 C16 C17 -176.98(17) . . . . ?
C20 C15 C16 O3 -176.81(17) . . . . ?
C9 C15 C16 O3 4.8(2) . . . . ?
O3 C16 C17 C18 176.90(19) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C24 O4 C19 C18 0.2(3) . . . . ?
C24 O4 C19 C20 179.7(2) . . . . ?
C17 C18 C19 O4 180.0(2) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C16 C15 C20 C19 -0.7(3) . . . . ?
C9 C15 C20 C19 177.54(18) . . . . ?
O4 C19 C20 C15 -179.73(18) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H3 O1 0.87(3) 2.10(2) 2.617(2) 117(2) . yes
N2 H1 O2 0.90(2) 2.20(2) 2.683(2) 112.9(18) . yes
N2 H1 O3 0.90(2) 2.27(2) 2.841(2) 120.7(18) . yes
C24 H24C O2 0.96 2.40 3.346(3) 170.0 2_655 yes

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038



####################################################################### 
# 
# 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_KSA_28_050722_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2281120'
loop_
_audit_author_name
_audit_author_address
'Ashokkumar Krishnan'
;Vellore Institute of Technology, Vellore
India
;
_audit_update_record             
;
2023-07-12 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 N2 O5, C H Cl3'
_chemical_formula_sum            'C29 H27 Cl3 N2 O5'
_chemical_formula_weight         589.87

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0106(9)
_cell_length_b                   10.5842(10)
_cell_length_c                   14.4812(14)
_cell_angle_alpha                76.236(4)
_cell_angle_beta                 72.035(3)
_cell_angle_gamma                87.625(4)
_cell_volume                     1416.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9868
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.93

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.365
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6874
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61987
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.195
_diffrn_reflns_theta_max         28.355
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7045
_reflns_number_gt                3989
_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 APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0823P)²+1.2343P] 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_number_reflns         7045
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.2205
_refine_ls_wR_factor_gt          0.1846
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
O1_4 O 0.2637(2) 0.7365(2) 0.65305(16) 0.0686(7) Uani 1 1 d . . . . .
O2_4 O 0.7461(2) 0.7509(2) 0.36482(16) 0.0734(7) Uani 1 1 d . . . . .
O3_4 O 0.6798(3) 0.9633(2) 0.25732(16) 0.0711(7) Uani 1 1 d . . . . .
O4_4 O 0.3412(2) 0.5361(2) 0.88986(16) 0.0706(7) Uani 1 1 d . . . . .
O5_4 O 0.8888(3) 0.7294(3) 0.7411(2) 0.0818(8) Uani 1 1 d . . . . .
N1_4 N 0.4222(3) 0.5291(2) 0.67016(17) 0.0491(6) Uani 1 1 d . . . . .
H2_4 H 0.340(4) 0.543(4) 0.706(3) 0.074 Uiso 1 1 d . U . . .
N2_4 N 0.6990(3) 0.5533(2) 0.51190(18) 0.0526(6) Uani 1 1 d . . . . .
H1_4 H 0.759(4) 0.574(4) 0.455(3) 0.079 Uiso 1 1 d . U . . .
C1_4 C 0.4053(3) 0.8505(3) 0.4940(2) 0.0446(6) Uani 1 1 d . . . . .
C2_4 C 0.5303(3) 0.8549(3) 0.41603(19) 0.0446(6) Uani 1 1 d . . . . .
C3_4 C 0.5576(3) 0.9611(3) 0.3323(2) 0.0511(7) Uani 1 1 d . . . . .
C4_4 C 0.4603(4) 1.0587(3) 0.3289(3) 0.0578(8) Uani 1 1 d . . . . .
H1E_4 H 0.475(4) 1.132(4) 0.275(3) 0.087 Uiso 1 1 d . U . . .
C5_4 C 0.3383(4) 1.0521(3) 0.4070(3) 0.0606(8) Uani 1 1 d . . . . .
H1D_4 H 0.275(4) 1.130(4) 0.399(3) 0.091 Uiso 1 1 d . U . . .
C6_4 C 0.3106(3) 0.9495(3) 0.4899(3) 0.0561(8) Uani 1 1 d . . . . .
H1C_4 H 0.227(4) 0.941(4) 0.542(3) 0.084 Uiso 1 1 d . U . . .
C7_4 C 0.3718(3) 0.7395(3) 0.5837(2) 0.0474(7) Uani 1 1 d . . . . .
C8_4 C 0.4693(3) 0.6334(3) 0.58942(18) 0.0419(6) Uani 1 1 d . . . . .
C9_4 C 0.5941(3) 0.6410(3) 0.51631(19) 0.0424(6) Uani 1 1 d . . . . .
C10_4 C 0.6314(3) 0.7507(3) 0.42667(19) 0.0460(6) Uani 1 1 d . . . . .
C11_4 C 0.5140(3) 0.4613(3) 0.7271(2) 0.0460(7) Uani 1 1 d . . . . .
H1F_4 H 0.458(4) 0.402(3) 0.778(3) 0.069 Uiso 1 1 d . U . . .
C12_4 C 0.6306(3) 0.3863(3) 0.6722(2) 0.0453(6) Uani 1 1 d . . . . .
C13_4 C 0.7163(3) 0.4356(3) 0.5736(2) 0.0459(6) Uani 1 1 d . . . . .
C14_4 C 0.6631(3) 0.2657(3) 0.7243(2) 0.0531(7) Uani 1 1 d . . . . .
C15_4 C 0.7789(4) 0.2003(3) 0.6798(2) 0.0590(8) Uani 1 1 d . . . . .
H1I_4 H 0.801(4) 0.111(4) 0.715(3) 0.089 Uiso 1 1 d . U . . .
C16_4 C 0.8661(3) 0.2512(3) 0.5836(2) 0.0573(8) Uani 1 1 d . . . . .
C17_4 C 0.8332(3) 0.3676(3) 0.5317(2) 0.0523(7) Uani 1 1 d . . . . .
H1A_4 H 0.890(4) 0.401(4) 0.466(3) 0.078 Uiso 1 1 d . U . . .
C18_4 C 0.7135(5) 1.0752(5) 0.1758(3) 0.0839(13) Uani 1 1 d . . . . .
H1J_4 H 0.706(5) 1.160(5) 0.202(4) 0.126 Uiso 1 1 d . U . . .
H1K_4 H 0.799(6) 1.058(5) 0.136(4) 0.126 Uiso 1 1 d . U . . .
H1L_4 H 0.654(6) 1.069(5) 0.140(4) 0.126 Uiso 1 1 d . U . . .
C19_4 C 0.5681(3) 0.5526(3) 0.77633(19) 0.0453(6) Uani 1 1 d . . . . .
C20_4 C 0.4749(3) 0.5881(3) 0.8600(2) 0.0513(7) Uani 1 1 d . . . . .
C21_4 C 0.5227(4) 0.6697(3) 0.9059(2) 0.0622(9) Uani 1 1 d . . . . .
H1H_4 H 0.463(4) 0.686(4) 0.959(3) 0.093 Uiso 1 1 d . U . . .
C22_4 C 0.6596(4) 0.7189(4) 0.8686(2) 0.0628(9) Uani 1 1 d . . . . .
H1G_4 H 0.688(4) 0.774(4) 0.899(3) 0.094 Uiso 1 1 d . U . . .
C23_4 C 0.7508(3) 0.6866(3) 0.7860(2) 0.0560(8) Uani 1 1 d . . . . .
C24_4 C 0.7040(3) 0.6025(3) 0.7413(2) 0.0505(7) Uani 1 1 d . . . . .
H1B_4 H 0.771(4) 0.582(3) 0.684(3) 0.076 Uiso 1 1 d . U . . .
C25_4 C 0.5748(5) 0.2047(4) 0.8300(3) 0.0770(11) Uani 1 1 d . . . . .
H1P_4 H 0.610(5) 0.118(5) 0.852(4) 0.115 Uiso 1 1 d . U . . .
H1Q_4 H 0.574(5) 0.262(5) 0.869(4) 0.115 Uiso 1 1 d . U . . .
H1R_4 H 0.473(5) 0.195(5) 0.838(4) 0.115 Uiso 1 1 d . U . . .
C26_4 C 0.9934(4) 0.1796(4) 0.5368(3) 0.0776(11) Uani 1 1 d . . . . .
H26A_4 H 1.013119 0.201443 0.465565 0.116 Uiso 1 1 calc R U . . .
H26B_4 H 0.974943 0.087499 0.561978 0.116 Uiso 1 1 calc R U . . .
H26C_4 H 1.072831 0.204456 0.553200 0.116 Uiso 1 1 calc R U . . .
C27_4 C 0.2416(4) 0.5687(4) 0.9738(3) 0.0825(12) Uani 1 1 d . . . . .
H27A_4 H 0.152313 0.527319 0.985722 0.124 Uiso 1 1 calc R U . . .
H27B_4 H 0.232277 0.661365 0.961017 0.124 Uiso 1 1 calc R U . . .
H27C_4 H 0.272784 0.539432 1.031529 0.124 Uiso 1 1 calc R U . . .
C28_4 C 0.9464(5) 0.8111(5) 0.7838(4) 0.1008(15) Uani 1 1 d . . . . .
H28A_4 H 1.040900 0.837159 0.742747 0.151 Uiso 1 1 calc R U . . .
H28B_4 H 0.946627 0.765149 0.849412 0.151 Uiso 1 1 calc R U . . .
H28C_4 H 0.890816 0.886867 0.788311 0.151 Uiso 1 1 calc R U . . .
Cl2_5 Cl 0.84706(19) 0.7491(2) 0.07600(15) 0.1554(7) Uani 1 1 d . . . . .
Cl10_5 Cl 1.07544(16) 0.86600(18) 0.10187(11) 0.1345(6) Uani 1 1 d . . . . .
C1_5 C 0.9349(5) 0.7526(5) 0.1611(3) 0.0926(14) Uani 1 1 d . . . . .
H1_5 H 0.878(6) 0.781(5) 0.210(4) 0.139 Uiso 1 1 d . U . . .
Cl1 Cl 0.9910(2) 0.60023(17) 0.20467(12) 0.1667(9) 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
O1_4 C7_4 1.224(3) . ?
O2_4 C10_4 1.219(3) . ?
O3_4 C3_4 1.359(4) . ?
O3_4 C18_4 1.426(4) . ?
O4_4 C20_4 1.368(4) . ?
O4_4 C27_4 1.419(4) . ?
O5_4 C23_4 1.376(4) . ?
O5_4 C28_4 1.405(5) . ?
N1_4 C8_4 1.377(4) . ?
N1_4 C11_4 1.474(4) . ?
N1_4 H2_4 0.86(4) . ?
N2_4 C9_4 1.368(4) . ?
N2_4 C13_4 1.389(4) . ?
N2_4 H1_4 0.84(4) . ?
C1_4 C6_4 1.387(4) . ?
C1_4 C2_4 1.396(4) . ?
C1_4 C7_4 1.489(4) . ?
C2_4 C3_4 1.407(4) . ?
C2_4 C10_4 1.480(4) . ?
C3_4 C4_4 1.393(4) . ?
C4_4 C5_4 1.376(5) . ?
C4_4 H1E_4 0.94(4) . ?
C5_4 C6_4 1.377(5) . ?
C5_4 H1D_4 1.03(4) . ?
C6_4 H1C_4 0.93(4) . ?
C7_4 C8_4 1.462(4) . ?
C8_4 C9_4 1.357(4) . ?
C9_4 C10_4 1.481(4) . ?
C11_4 C12_4 1.509(4) . ?
C11_4 C19_4 1.530(4) . ?
C11_4 H1F_4 0.90(4) . ?
C12_4 C14_4 1.401(4) . ?
C12_4 C13_4 1.405(4) . ?
C13_4 C17_4 1.399(4) . ?
C14_4 C15_4 1.386(4) . ?
C14_4 C25_4 1.512(5) . ?
C15_4 C16_4 1.387(5) . ?
C15_4 H1I_4 1.01(4) . ?
C16_4 C17_4 1.368(4) . ?
C16_4 C26_4 1.512(4) . ?
C17_4 H1A_4 0.94(4) . ?
C18_4 H1J_4 1.04(6) . ?
C18_4 H1K_4 0.91(6) . ?
C18_4 H1L_4 0.91(6) . ?
C19_4 C24_4 1.376(4) . ?
C19_4 C20_4 1.403(4) . ?
C20_4 C21_4 1.387(5) . ?
C21_4 C22_4 1.382(5) . ?
C21_4 H1H_4 0.86(4) . ?
C22_4 C23_4 1.370(4) . ?
C22_4 H1G_4 0.91(4) . ?
C23_4 C24_4 1.388(4) . ?
C24_4 H1B_4 0.95(4) . ?
C25_4 H1P_4 0.98(5) . ?
C25_4 H1Q_4 0.93(5) . ?
C25_4 H1R_4 1.00(5) . ?
C26_4 H26A_4 0.9600 . ?
C26_4 H26B_4 0.9600 . ?
C26_4 H26C_4 0.9600 . ?
C27_4 H27A_4 0.9600 . ?
C27_4 H27B_4 0.9600 . ?
C27_4 H27C_4 0.9600 . ?
C28_4 H28A_4 0.9600 . ?
C28_4 H28B_4 0.9600 . ?
C28_4 H28C_4 0.9600 . ?
Cl2_5 C1_5 1.728(5) . ?
Cl10_5 C1_5 1.750(5) . ?
C1_5 Cl1 1.724(5) . ?
C1_5 H1_5 0.86(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
C3_4 O3_4 C18_4 118.1(3) . . ?
C20_4 O4_4 C27_4 118.2(3) . . ?
C23_4 O5_4 C28_4 118.7(3) . . ?
C8_4 N1_4 C11_4 122.5(2) . . ?
C8_4 N1_4 H2_4 110(2) . . ?
C11_4 N1_4 H2_4 115(2) . . ?
C9_4 N2_4 C13_4 134.3(2) . . ?
C9_4 N2_4 H1_4 109(3) . . ?
C13_4 N2_4 H1_4 116(3) . . ?
C6_4 C1_4 C2_4 120.8(3) . . ?
C6_4 C1_4 C7_4 118.7(3) . . ?
C2_4 C1_4 C7_4 120.5(2) . . ?
C1_4 C2_4 C3_4 118.7(3) . . ?
C1_4 C2_4 C10_4 118.6(2) . . ?
C3_4 C2_4 C10_4 122.6(2) . . ?
O3_4 C3_4 C4_4 122.7(3) . . ?
O3_4 C3_4 C2_4 117.7(3) . . ?
C4_4 C3_4 C2_4 119.6(3) . . ?
C5_4 C4_4 C3_4 120.4(3) . . ?
C5_4 C4_4 H1E_4 117(2) . . ?
C3_4 C4_4 H1E_4 122(2) . . ?
C4_4 C5_4 C6_4 120.7(3) . . ?
C4_4 C5_4 H1D_4 115(2) . . ?
C6_4 C5_4 H1D_4 125(2) . . ?
C5_4 C6_4 C1_4 119.7(3) . . ?
C5_4 C6_4 H1C_4 122(2) . . ?
C1_4 C6_4 H1C_4 118(2) . . ?
O1_4 C7_4 C8_4 119.5(3) . . ?
O1_4 C7_4 C1_4 120.7(3) . . ?
C8_4 C7_4 C1_4 119.8(2) . . ?
C9_4 C8_4 N1_4 124.9(3) . . ?
C9_4 C8_4 C7_4 119.8(2) . . ?
N1_4 C8_4 C7_4 115.3(2) . . ?
C8_4 C9_4 N2_4 127.3(3) . . ?
C8_4 C9_4 C10_4 121.7(2) . . ?
N2_4 C9_4 C10_4 111.0(2) . . ?
O2_4 C10_4 C2_4 122.9(3) . . ?
O2_4 C10_4 C9_4 117.7(3) . . ?
C2_4 C10_4 C9_4 119.4(2) . . ?
N1_4 C11_4 C12_4 115.9(2) . . ?
N1_4 C11_4 C19_4 111.3(2) . . ?
C12_4 C11_4 C19_4 112.1(2) . . ?
N1_4 C11_4 H1F_4 105(2) . . ?
C12_4 C11_4 H1F_4 106(2) . . ?
C19_4 C11_4 H1F_4 106(2) . . ?
C14_4 C12_4 C13_4 117.8(3) . . ?
C14_4 C12_4 C11_4 118.6(2) . . ?
C13_4 C12_4 C11_4 123.4(2) . . ?
N2_4 C13_4 C17_4 114.6(3) . . ?
N2_4 C13_4 C12_4 125.2(2) . . ?
C17_4 C13_4 C12_4 120.2(3) . . ?
C15_4 C14_4 C12_4 120.3(3) . . ?
C15_4 C14_4 C25_4 118.5(3) . . ?
C12_4 C14_4 C25_4 121.2(3) . . ?
C14_4 C15_4 C16_4 121.8(3) . . ?
C14_4 C15_4 H1I_4 121(2) . . ?
C16_4 C15_4 H1I_4 117(2) . . ?
C17_4 C16_4 C15_4 118.1(3) . . ?
C17_4 C16_4 C26_4 120.7(3) . . ?
C15_4 C16_4 C26_4 121.1(3) . . ?
C16_4 C17_4 C13_4 121.7(3) . . ?
C16_4 C17_4 H1A_4 119(2) . . ?
C13_4 C17_4 H1A_4 120(2) . . ?
O3_4 C18_4 H1J_4 111(3) . . ?
O3_4 C18_4 H1K_4 104(3) . . ?
H1J_4 C18_4 H1K_4 118(4) . . ?
O3_4 C18_4 H1L_4 105(4) . . ?
H1J_4 C18_4 H1L_4 115(5) . . ?
H1K_4 C18_4 H1L_4 103(5) . . ?
C24_4 C19_4 C20_4 118.5(3) . . ?
C24_4 C19_4 C11_4 122.8(2) . . ?
C20_4 C19_4 C11_4 118.7(3) . . ?
O4_4 C20_4 C21_4 125.3(3) . . ?
O4_4 C20_4 C19_4 115.4(3) . . ?
C21_4 C20_4 C19_4 119.3(3) . . ?
C22_4 C21_4 C20_4 120.7(3) . . ?
C22_4 C21_4 H1H_4 123(3) . . ?
C20_4 C21_4 H1H_4 117(3) . . ?
C23_4 C22_4 C21_4 120.4(3) . . ?
C23_4 C22_4 H1G_4 121(3) . . ?
C21_4 C22_4 H1G_4 119(3) . . ?
C22_4 C23_4 O5_4 126.1(3) . . ?
C22_4 C23_4 C24_4 118.9(3) . . ?
O5_4 C23_4 C24_4 114.9(3) . . ?
C19_4 C24_4 C23_4 122.0(3) . . ?
C19_4 C24_4 H1B_4 121(2) . . ?
C23_4 C24_4 H1B_4 116(2) . . ?
C14_4 C25_4 H1P_4 109(3) . . ?
C14_4 C25_4 H1Q_4 108(3) . . ?
H1P_4 C25_4 H1Q_4 115(4) . . ?
C14_4 C25_4 H1R_4 114(3) . . ?
H1P_4 C25_4 H1R_4 108(4) . . ?
H1Q_4 C25_4 H1R_4 102(4) . . ?
C16_4 C26_4 H26A_4 109.5 . . ?
C16_4 C26_4 H26B_4 109.5 . . ?
H26A_4 C26_4 H26B_4 109.5 . . ?
C16_4 C26_4 H26C_4 109.5 . . ?
H26A_4 C26_4 H26C_4 109.5 . . ?
H26B_4 C26_4 H26C_4 109.5 . . ?
O4_4 C27_4 H27A_4 109.5 . . ?
O4_4 C27_4 H27B_4 109.5 . . ?
H27A_4 C27_4 H27B_4 109.5 . . ?
O4_4 C27_4 H27C_4 109.5 . . ?
H27A_4 C27_4 H27C_4 109.5 . . ?
H27B_4 C27_4 H27C_4 109.5 . . ?
O5_4 C28_4 H28A_4 109.5 . . ?
O5_4 C28_4 H28B_4 109.5 . . ?
H28A_4 C28_4 H28B_4 109.5 . . ?
O5_4 C28_4 H28C_4 109.5 . . ?
H28A_4 C28_4 H28C_4 109.5 . . ?
H28B_4 C28_4 H28C_4 109.5 . . ?
Cl1 C1_5 Cl2_5 111.1(3) . . ?
Cl1 C1_5 Cl10_5 111.7(3) . . ?
Cl2_5 C1_5 Cl10_5 107.6(2) . . ?
Cl1 C1_5 H1_5 111(4) . . ?
Cl2_5 C1_5 H1_5 108(4) . . ?
Cl10_5 C1_5 H1_5 108(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6_4 C1_4 C2_4 C3_4 -0.9(4) . . . . ?
C7_4 C1_4 C2_4 C3_4 179.6(3) . . . . ?
C6_4 C1_4 C2_4 C10_4 176.5(3) . . . . ?
C7_4 C1_4 C2_4 C10_4 -3.0(4) . . . . ?
C18_4 O3_4 C3_4 C4_4 4.9(5) . . . . ?
C18_4 O3_4 C3_4 C2_4 -175.2(3) . . . . ?
C1_4 C2_4 C3_4 O3_4 -179.9(3) . . . . ?
C10_4 C2_4 C3_4 O3_4 2.7(4) . . . . ?
C1_4 C2_4 C3_4 C4_4 0.0(4) . . . . ?
C10_4 C2_4 C3_4 C4_4 -177.4(3) . . . . ?
O3_4 C3_4 C4_4 C5_4 -179.8(3) . . . . ?
C2_4 C3_4 C4_4 C5_4 0.3(5) . . . . ?
C3_4 C4_4 C5_4 C6_4 0.3(5) . . . . ?
C4_4 C5_4 C6_4 C1_4 -1.3(5) . . . . ?
C2_4 C1_4 C6_4 C5_4 1.6(5) . . . . ?
C7_4 C1_4 C6_4 C5_4 -178.9(3) . . . . ?
C6_4 C1_4 C7_4 O1_4 -0.9(4) . . . . ?
C2_4 C1_4 C7_4 O1_4 178.6(3) . . . . ?
C6_4 C1_4 C7_4 C8_4 179.5(3) . . . . ?
C2_4 C1_4 C7_4 C8_4 -1.0(4) . . . . ?
C11_4 N1_4 C8_4 C9_4 42.9(4) . . . . ?
C11_4 N1_4 C8_4 C7_4 -139.2(3) . . . . ?
O1_4 C7_4 C8_4 C9_4 -175.0(3) . . . . ?
C1_4 C7_4 C8_4 C9_4 4.6(4) . . . . ?
O1_4 C7_4 C8_4 N1_4 6.9(4) . . . . ?
C1_4 C7_4 C8_4 N1_4 -173.4(2) . . . . ?
N1_4 C8_4 C9_4 N2_4 -4.8(5) . . . . ?
C7_4 C8_4 C9_4 N2_4 177.4(3) . . . . ?
N1_4 C8_4 C9_4 C10_4 173.9(3) . . . . ?
C7_4 C8_4 C9_4 C10_4 -3.9(4) . . . . ?
C13_4 N2_4 C9_4 C8_4 0.2(5) . . . . ?
C13_4 N2_4 C9_4 C10_4 -178.7(3) . . . . ?
C1_4 C2_4 C10_4 O2_4 -175.8(3) . . . . ?
C3_4 C2_4 C10_4 O2_4 1.5(5) . . . . ?
C1_4 C2_4 C10_4 C9_4 3.6(4) . . . . ?
C3_4 C2_4 C10_4 C9_4 -179.0(3) . . . . ?
C8_4 C9_4 C10_4 O2_4 179.3(3) . . . . ?
N2_4 C9_4 C10_4 O2_4 -1.8(4) . . . . ?
C8_4 C9_4 C10_4 C2_4 -0.2(4) . . . . ?
N2_4 C9_4 C10_4 C2_4 178.7(2) . . . . ?
C8_4 N1_4 C11_4 C12_4 -67.4(4) . . . . ?
C8_4 N1_4 C11_4 C19_4 62.3(3) . . . . ?
N1_4 C11_4 C12_4 C14_4 -140.9(3) . . . . ?
C19_4 C11_4 C12_4 C14_4 89.8(3) . . . . ?
N1_4 C11_4 C12_4 C13_4 44.6(4) . . . . ?
C19_4 C11_4 C12_4 C13_4 -84.7(3) . . . . ?
C9_4 N2_4 C13_4 C17_4 170.3(3) . . . . ?
C9_4 N2_4 C13_4 C12_4 -12.4(5) . . . . ?
C14_4 C12_4 C13_4 N2_4 -179.8(3) . . . . ?
C11_4 C12_4 C13_4 N2_4 -5.2(5) . . . . ?
C14_4 C12_4 C13_4 C17_4 -2.6(4) . . . . ?
C11_4 C12_4 C13_4 C17_4 172.0(3) . . . . ?
C13_4 C12_4 C14_4 C15_4 1.9(4) . . . . ?
C11_4 C12_4 C14_4 C15_4 -173.0(3) . . . . ?
C13_4 C12_4 C14_4 C25_4 -179.0(3) . . . . ?
C11_4 C12_4 C14_4 C25_4 6.1(5) . . . . ?
C12_4 C14_4 C15_4 C16_4 0.2(5) . . . . ?
C25_4 C14_4 C15_4 C16_4 -179.0(3) . . . . ?
C14_4 C15_4 C16_4 C17_4 -1.5(5) . . . . ?
C14_4 C15_4 C16_4 C26_4 179.0(3) . . . . ?
C15_4 C16_4 C17_4 C13_4 0.7(5) . . . . ?
C26_4 C16_4 C17_4 C13_4 -179.8(3) . . . . ?
N2_4 C13_4 C17_4 C16_4 178.8(3) . . . . ?
C12_4 C13_4 C17_4 C16_4 1.3(5) . . . . ?
N1_4 C11_4 C19_4 C24_4 -105.6(3) . . . . ?
C12_4 C11_4 C19_4 C24_4 26.1(4) . . . . ?
N1_4 C11_4 C19_4 C20_4 73.7(3) . . . . ?
C12_4 C11_4 C19_4 C20_4 -154.6(2) . . . . ?
C27_4 O4_4 C20_4 C21_4 0.8(5) . . . . ?
C27_4 O4_4 C20_4 C19_4 -179.7(3) . . . . ?
C24_4 C19_4 C20_4 O4_4 179.2(3) . . . . ?
C11_4 C19_4 C20_4 O4_4 -0.1(4) . . . . ?
C24_4 C19_4 C20_4 C21_4 -1.3(4) . . . . ?
C11_4 C19_4 C20_4 C21_4 179.4(3) . . . . ?
O4_4 C20_4 C21_4 C22_4 -178.8(3) . . . . ?
C19_4 C20_4 C21_4 C22_4 1.7(5) . . . . ?
C20_4 C21_4 C22_4 C23_4 -0.7(5) . . . . ?
C21_4 C22_4 C23_4 O5_4 179.5(3) . . . . ?
C21_4 C22_4 C23_4 C24_4 -0.8(5) . . . . ?
C28_4 O5_4 C23_4 C22_4 2.1(5) . . . . ?
C28_4 O5_4 C23_4 C24_4 -177.7(4) . . . . ?
C20_4 C19_4 C24_4 C23_4 -0.2(4) . . . . ?
C11_4 C19_4 C24_4 C23_4 179.1(3) . . . . ?
C22_4 C23_4 C24_4 C19_4 1.2(5) . . . . ?
O5_4 C23_4 C24_4 C19_4 -179.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1_4 H2_4 O1_4 0.86(4) 2.20(4) 2.663(3) 114(3) . yes
N2_4 H1_4 O2_4 0.84(4) 2.04(4) 2.545(3) 118(3) . yes
C1_5 H1_5 O2_4 0.86(6) 2.18(6) 2.969(4) 151(5) . yes

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.048



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform and diethyl ether'
