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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2294665'
loop_
_audit_author_name
_audit_author_address
'Bholey Singh'
;University of Delhi
India
;
_audit_update_record             
;
2023-09-13 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.87 H4.13 Cl0.13 F0.13 N0.52 O0.65'
_chemical_formula_weight         75.23

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.5711(4)
_cell_length_b                   37.8741(14)
_cell_length_c                   7.8420(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.890(4)
_cell_angle_gamma                90
_cell_volume                     2781.71(19)
_cell_formula_units_Z            31
_cell_measurement_temperature    107(2)
_cell_measurement_reflns_used    12140
_cell_measurement_theta_min      3.416
_cell_measurement_theta_max      31.1620

_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellowish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.60945
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      107(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22390
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.059
_diffrn_reflns_theta_max         31.063
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.797
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7106
_reflns_number_gt                5657
_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       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0626P)²+1.0253P] 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         7106
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
CL Cl 0.36095(4) 0.71662(2) 0.49574(5) 0.02199(11) Uani 1 1 d . . . . .
F F 0.11131(12) 0.27781(3) 0.35261(15) 0.0277(2) Uani 1 1 d . . . . .
O4 O 0.52896(12) 0.66300(3) 0.26360(15) 0.0172(2) Uani 1 1 d . . . . .
O1 O 0.36656(12) 0.51964(3) 0.13732(15) 0.0176(2) Uani 1 1 d . . . . .
O3 O 0.29110(14) 0.65801(3) 0.73741(15) 0.0216(3) Uani 1 1 d . . . . .
O5 O 0.54786(13) 0.61665(3) 0.09069(16) 0.0229(3) Uani 1 1 d . . . . .
O2 O 0.19771(15) 0.60899(3) 0.83246(16) 0.0265(3) Uani 1 1 d . . . . .
N4 N 0.29609(14) 0.41547(3) 0.33381(17) 0.0158(3) Uani 1 1 d . . . . .
N1 N 0.29365(14) 0.55936(3) 0.37772(17) 0.0165(3) Uani 1 1 d . . . . .
H1 H 0.263010 0.538039 0.344519 0.020 Uiso 1 1 calc R U . . .
N2 N 0.30962(16) 0.47018(4) 0.40500(19) 0.0215(3) Uani 1 1 d . . . . .
N3 N 0.25081(16) 0.44028(4) 0.43514(19) 0.0219(3) Uani 1 1 d . . . . .
C00C C 0.22752(16) 0.65672(4) 0.34430(19) 0.0140(3) Uani 1 1 d . . . . .
C6 C 0.39278(17) 0.46489(4) 0.2847(2) 0.0168(3) Uani 1 1 d . . . . .
C10 C 0.41160(16) 0.61128(4) 0.3142(2) 0.0142(3) Uani 1 1 d . . . . .
C00F C 0.22494(17) 0.69348(4) 0.3575(2) 0.0170(3) Uani 1 1 d . . . . .
C00G C 0.24927(17) 0.37983(4) 0.3391(2) 0.0154(3) Uani 1 1 d . . . . .
C5 C 0.38388(17) 0.43007(4) 0.2371(2) 0.0167(3) Uani 1 1 d . . . . .
H5 H 0.428922 0.418655 0.154920 0.020 Uiso 1 1 calc R U . . .
C9 C 0.37722(16) 0.57691(4) 0.2818(2) 0.0150(3) Uani 1 1 d . . . . .
C16 C 0.50201(17) 0.62925(4) 0.2117(2) 0.0162(3) Uani 1 1 d . . . . .
C3 C 0.31381(17) 0.35343(4) 0.2583(2) 0.0173(3) Uani 1 1 d . . . . .
H3 H 0.388874 0.359053 0.200388 0.021 Uiso 1 1 calc R U . . .
C11 C 0.34678(17) 0.63277(4) 0.4436(2) 0.0140(3) Uani 1 1 d . . . . .
C15 C 0.25228(17) 0.62356(4) 0.7245(2) 0.0176(3) Uani 1 1 d . . . . .
C12 C 0.28622(17) 0.60803(4) 0.5651(2) 0.0156(3) Uani 1 1 d . . . . .
C20 C 0.11319(17) 0.64094(4) 0.2296(2) 0.0167(3) Uani 1 1 d . . . . .
H20 H 0.111269 0.615972 0.218036 0.020 Uiso 1 1 calc R U . . .
C00P C 0.15826(18) 0.31162(4) 0.3487(2) 0.0191(3) Uani 1 1 d . . . . .
C13 C 0.25556(17) 0.57373(4) 0.5241(2) 0.0160(3) Uani 1 1 d . . . . .
C00R C 0.11471(19) 0.71363(4) 0.2610(2) 0.0214(3) Uani 1 1 d . . . . .
H00R H 0.115875 0.738609 0.272458 0.026 Uiso 1 1 calc R U . . .
C2 C 0.26712(18) 0.31886(4) 0.2636(2) 0.0188(3) Uani 1 1 d . . . . .
H2 H 0.309636 0.300482 0.209393 0.023 Uiso 1 1 calc R U . . .
C00T C 0.00240(18) 0.66061(4) 0.1322(2) 0.0203(3) Uani 1 1 d . . . . .
H00T H -0.073657 0.649174 0.054963 0.024 Uiso 1 1 calc R U . . .
C7 C 0.47107(17) 0.49516(4) 0.2267(2) 0.0173(3) Uani 1 1 d . . . . .
H7A H 0.532303 0.506720 0.328560 0.021 Uiso 1 1 calc R U . . .
H7B H 0.532509 0.486783 0.147755 0.021 Uiso 1 1 calc R U . . .
C8 C 0.41897(18) 0.55490(4) 0.1374(2) 0.0180(3) Uani 1 1 d . . . . .
H8A H 0.379942 0.566025 0.023277 0.022 Uiso 1 1 calc R U . . .
H8B H 0.524298 0.554402 0.153573 0.022 Uiso 1 1 calc R U . . .
C14 C 0.18183(19) 0.54800(4) 0.6225(2) 0.0210(3) Uani 1 1 d . . . . .
H14A H 0.173659 0.525039 0.563673 0.031 Uiso 1 1 calc R U . . .
H14B H 0.237549 0.545367 0.741554 0.031 Uiso 1 1 calc R U . . .
H14C H 0.086307 0.556840 0.626398 0.031 Uiso 1 1 calc R U . . .
C4 C 0.13973(19) 0.37191(4) 0.4258(2) 0.0216(3) Uani 1 1 d . . . . .
H4 H 0.097050 0.390114 0.480991 0.026 Uiso 1 1 calc R U . . .
C00Y C 0.00371(18) 0.69721(5) 0.1486(2) 0.0224(3) Uani 1 1 d . . . . .
H00Y H -0.071655 0.710875 0.082491 0.027 Uiso 1 1 calc R U . . .
C1 C 0.09349(19) 0.33731(4) 0.4310(2) 0.0229(4) Uani 1 1 d . . . . .
H1A H 0.019169 0.331393 0.489617 0.027 Uiso 1 1 calc R U . . .
C17 C 0.61432(19) 0.68279(4) 0.1641(2) 0.0231(4) Uani 1 1 d . . . . .
H17A H 0.569627 0.681998 0.038539 0.028 Uiso 1 1 calc R U . . .
H17B H 0.711174 0.672459 0.180223 0.028 Uiso 1 1 calc R U . . .
C18 C 0.6232(2) 0.72029(4) 0.2281(3) 0.0255(4) Uani 1 1 d . . . . .
H18A H 0.680540 0.734230 0.162641 0.038 Uiso 1 1 calc R U . . .
H18B H 0.526870 0.730291 0.211179 0.038 Uiso 1 1 calc R U . . .
H18C H 0.667892 0.720787 0.352338 0.038 Uiso 1 1 calc R U . . .
C19 C 0.2520(2) 0.67762(5) 0.8776(2) 0.0248(4) Uani 1 1 d . . . . .
H19A H 0.285115 0.702059 0.874675 0.037 Uiso 1 1 calc R U . . .
H19B H 0.147956 0.677368 0.864527 0.037 Uiso 1 1 calc R U . . .
H19C H 0.296357 0.666804 0.989191 0.037 Uiso 1 1 calc R U . . .
C21 C 0.0296(2) 0.49117(5) -0.0696(2) 0.0275(4) Uani 1 1 d . . . . .
H21A H 0.124297 0.501463 -0.072085 0.033 Uiso 1 1 calc R U . . .
H21B H -0.033949 0.495905 -0.183841 0.033 Uiso 1 1 calc R U . . .
C22 C 0.0453(2) 0.45178(6) -0.0438(3) 0.0359(5) Uani 1 1 d . . . . .
H22A H -0.050300 0.440854 -0.056965 0.043 Uiso 1 1 calc R U . . .
H22B H 0.099475 0.446750 0.075458 0.043 Uiso 1 1 calc R U . . .
C23 C 0.1237(3) 0.43576(8) -0.1776(4) 0.0532(6) Uani 1 1 d . . . . .
H23A H 0.061134 0.436347 -0.293483 0.080 Uiso 1 1 calc R U . . .
H23B H 0.149738 0.411262 -0.145627 0.080 Uiso 1 1 calc R U . . .
H23C H 0.210311 0.449457 -0.179199 0.080 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
CL C00F 1.7481(17) . ?
F C00P 1.3597(18) . ?
O4 C16 1.3503(19) . ?
O4 C17 1.4493(18) . ?
O1 C8 1.4264(18) . ?
O1 C7 1.4363(19) . ?
O3 C15 1.355(2) . ?
O3 C19 1.4390(19) . ?
O5 C16 1.2215(19) . ?
O2 C15 1.215(2) . ?
N4 N3 1.3581(18) . ?
N4 C5 1.360(2) . ?
N4 C00G 1.426(2) . ?
N1 C9 1.3766(19) . ?
N1 C13 1.386(2) . ?
N1 H1 0.8800 . ?
N2 N3 1.3074(19) . ?
N2 C6 1.368(2) . ?
C00C C00F 1.397(2) . ?
C00C C20 1.399(2) . ?
C00C C11 1.538(2) . ?
C6 C5 1.369(2) . ?
C6 C7 1.491(2) . ?
C10 C9 1.354(2) . ?
C10 C16 1.465(2) . ?
C10 C11 1.529(2) . ?
C00F C00R 1.393(2) . ?
C00G C3 1.394(2) . ?
C00G C4 1.395(2) . ?
C5 H5 0.9500 . ?
C9 C8 1.525(2) . ?
C3 C2 1.387(2) . ?
C3 H3 0.9500 . ?
C11 C12 1.533(2) . ?
C15 C12 1.477(2) . ?
C12 C13 1.356(2) . ?
C20 C00T 1.389(2) . ?
C20 H20 0.9500 . ?
C00P C2 1.375(2) . ?
C00P C1 1.383(2) . ?
C13 C14 1.506(2) . ?
C00R C00Y 1.381(3) . ?
C00R H00R 0.9500 . ?
C2 H2 0.9500 . ?
C00T C00Y 1.392(2) . ?
C00T H00T 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 C1 1.386(2) . ?
C4 H4 0.9500 . ?
C00Y H00Y 0.9500 . ?
C1 H1A 0.9500 . ?
C17 C18 1.503(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C21 1.489(4) 3_565 ?
C21 C22 1.509(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.535(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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 O4 C17 114.90(12) . . ?
C8 O1 C7 113.25(12) . . ?
C15 O3 C19 116.35(13) . . ?
N3 N4 C5 110.69(13) . . ?
N3 N4 C00G 119.88(13) . . ?
C5 N4 C00G 129.43(13) . . ?
C9 N1 C13 123.00(13) . . ?
C9 N1 H1 118.5 . . ?
C13 N1 H1 118.5 . . ?
N3 N2 C6 109.35(13) . . ?
N2 N3 N4 106.99(13) . . ?
C00F C00C C20 116.74(14) . . ?
C00F C00C C11 124.95(14) . . ?
C20 C00C C11 118.31(13) . . ?
N2 C6 C5 108.46(14) . . ?
N2 C6 C7 119.88(14) . . ?
C5 C6 C7 131.65(14) . . ?
C9 C10 C16 119.50(13) . . ?
C9 C10 C11 121.34(13) . . ?
C16 C10 C11 118.91(13) . . ?
C00R C00F C00C 121.93(15) . . ?
C00R C00F CL 116.50(12) . . ?
C00C C00F CL 121.57(12) . . ?
C3 C00G C4 121.00(14) . . ?
C3 C00G N4 119.64(14) . . ?
C4 C00G N4 119.35(14) . . ?
N4 C5 C6 104.50(13) . . ?
N4 C5 H5 127.7 . . ?
C6 C5 H5 127.7 . . ?
C10 C9 N1 120.55(14) . . ?
C10 C9 C8 125.04(13) . . ?
N1 C9 C8 114.36(13) . . ?
O5 C16 O4 121.83(14) . . ?
O5 C16 C10 126.31(14) . . ?
O4 C16 C10 111.85(13) . . ?
C2 C3 C00G 119.20(14) . . ?
C2 C3 H3 120.4 . . ?
C00G C3 H3 120.4 . . ?
C10 C11 C12 110.14(12) . . ?
C10 C11 C00C 109.78(12) . . ?
C12 C11 C00C 109.81(12) . . ?
O2 C15 O3 122.42(15) . . ?
O2 C15 C12 127.59(15) . . ?
O3 C15 C12 109.98(13) . . ?
C13 C12 C15 120.49(14) . . ?
C13 C12 C11 121.98(14) . . ?
C15 C12 C11 117.39(13) . . ?
C00T C20 C00C 122.14(15) . . ?
C00T C20 H20 118.9 . . ?
C00C C20 H20 118.9 . . ?
F C00P C2 119.07(14) . . ?
F C00P C1 118.03(14) . . ?
C2 C00P C1 122.90(15) . . ?
C12 C13 N1 119.45(14) . . ?
C12 C13 C14 126.89(14) . . ?
N1 C13 C14 113.66(13) . . ?
C00Y C00R C00F 119.82(15) . . ?
C00Y C00R H00R 120.1 . . ?
C00F C00R H00R 120.1 . . ?
C00P C2 C3 118.93(15) . . ?
C00P C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C20 C00T C00Y 119.46(16) . . ?
C20 C00T H00T 120.3 . . ?
C00Y C00T H00T 120.3 . . ?
O1 C7 C6 107.58(13) . . ?
O1 C7 H7A 110.2 . . ?
C6 C7 H7A 110.2 . . ?
O1 C7 H7B 110.2 . . ?
C6 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
O1 C8 C9 111.48(12) . . ?
O1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
O1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C4 C00G 119.61(15) . . ?
C1 C4 H4 120.2 . . ?
C00G C4 H4 120.2 . . ?
C00R C00Y C00T 119.91(15) . . ?
C00R C00Y H00Y 120.0 . . ?
C00T C00Y H00Y 120.0 . . ?
C00P C1 C4 118.35(15) . . ?
C00P C1 H1A 120.8 . . ?
C4 C1 H1A 120.8 . . ?
O4 C17 C18 107.94(13) . . ?
O4 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
O4 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C21 C22 112.82(19) 3_565 . ?
C21 C21 H21A 109.0 3_565 . ?
C22 C21 H21A 109.0 . . ?
C21 C21 H21B 109.0 3_565 . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 C23 110.36(19) . . ?
C21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 N2 N3 N4 -0.01(19) . . . . ?
C5 N4 N3 N2 -0.55(18) . . . . ?
C00G N4 N3 N2 179.87(14) . . . . ?
N3 N2 C6 C5 0.55(19) . . . . ?
N3 N2 C6 C7 179.53(15) . . . . ?
C20 C00C C00F C00R -0.3(2) . . . . ?
C11 C00C C00F C00R 178.70(14) . . . . ?
C20 C00C C00F CL -179.98(11) . . . . ?
C11 C00C C00F CL -0.9(2) . . . . ?
N3 N4 C00G C3 -169.25(15) . . . . ?
C5 N4 C00G C3 11.3(2) . . . . ?
N3 N4 C00G C4 10.5(2) . . . . ?
C5 N4 C00G C4 -169.00(16) . . . . ?
N3 N4 C5 C6 0.87(18) . . . . ?
C00G N4 C5 C6 -179.61(15) . . . . ?
N2 C6 C5 N4 -0.85(18) . . . . ?
C7 C6 C5 N4 -179.66(17) . . . . ?
C16 C10 C9 N1 179.31(14) . . . . ?
C11 C10 C9 N1 -6.5(2) . . . . ?
C16 C10 C9 C8 -3.4(2) . . . . ?
C11 C10 C9 C8 170.73(15) . . . . ?
C13 N1 C9 C10 -8.5(2) . . . . ?
C13 N1 C9 C8 173.98(14) . . . . ?
C17 O4 C16 O5 0.6(2) . . . . ?
C17 O4 C16 C10 -178.15(14) . . . . ?
C9 C10 C16 O5 3.0(3) . . . . ?
C11 C10 C16 O5 -171.32(16) . . . . ?
C9 C10 C16 O4 -178.36(14) . . . . ?
C11 C10 C16 O4 7.3(2) . . . . ?
C4 C00G C3 C2 0.5(2) . . . . ?
N4 C00G C3 C2 -179.76(15) . . . . ?
C9 C10 C11 C12 18.8(2) . . . . ?
C16 C10 C11 C12 -166.98(14) . . . . ?
C9 C10 C11 C00C -102.20(16) . . . . ?
C16 C10 C11 C00C 71.99(17) . . . . ?
C00F C00C C11 C10 -121.42(15) . . . . ?
C20 C00C C11 C10 57.61(17) . . . . ?
C00F C00C C11 C12 117.35(16) . . . . ?
C20 C00C C11 C12 -63.63(17) . . . . ?
C19 O3 C15 O2 -5.7(2) . . . . ?
C19 O3 C15 C12 174.18(14) . . . . ?
O2 C15 C12 C13 0.5(3) . . . . ?
O3 C15 C12 C13 -179.45(14) . . . . ?
O2 C15 C12 C11 176.25(16) . . . . ?
O3 C15 C12 C11 -3.7(2) . . . . ?
C10 C11 C12 C13 -19.2(2) . . . . ?
C00C C11 C12 C13 101.84(17) . . . . ?
C10 C11 C12 C15 165.11(13) . . . . ?
C00C C11 C12 C15 -73.88(17) . . . . ?
C00F C00C C20 C00T 0.4(2) . . . . ?
C11 C00C C20 C00T -178.70(14) . . . . ?
C15 C12 C13 N1 -177.39(14) . . . . ?
C11 C12 C13 N1 7.0(2) . . . . ?
C15 C12 C13 C14 2.6(3) . . . . ?
C11 C12 C13 C14 -173.03(15) . . . . ?
C9 N1 C13 C12 8.2(2) . . . . ?
C9 N1 C13 C14 -171.75(14) . . . . ?
C00C C00F C00R C00Y 0.1(2) . . . . ?
CL C00F C00R C00Y 179.80(13) . . . . ?
F C00P C2 C3 179.36(15) . . . . ?
C1 C00P C2 C3 -0.6(3) . . . . ?
C00G C3 C2 C00P 0.0(2) . . . . ?
C00C C20 C00T C00Y -0.3(2) . . . . ?
C8 O1 C7 C6 155.85(12) . . . . ?
N2 C6 C7 O1 -64.65(19) . . . . ?
C5 C6 C7 O1 114.05(19) . . . . ?
C7 O1 C8 C9 -97.30(15) . . . . ?
C10 C9 C8 O1 -179.98(15) . . . . ?
N1 C9 C8 O1 -2.56(19) . . . . ?
C3 C00G C4 C1 -0.4(3) . . . . ?
N4 C00G C4 C1 179.84(16) . . . . ?
C00F C00R C00Y C00T 0.0(2) . . . . ?
C20 C00T C00Y C00R 0.0(2) . . . . ?
F C00P C1 C4 -179.28(16) . . . . ?
C2 C00P C1 C4 0.6(3) . . . . ?
C00G C4 C1 C00P -0.1(3) . . . . ?
C16 O4 C17 C18 175.12(14) . . . . ?
C21 C21 C22 C23 -173.0(2) 3_565 . . . ?

_refine_diff_density_max         1.029
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.064


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
