# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2151147'
loop_
_audit_author_name
_audit_author_address
'Ashoke Sharon'
;Department of Chemistry, Birla Institute of Technology
India
;

_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_publcif_datablock.id            {609c82c1-1688-4f7b-a22a-b36b7e094314}

# publcif _publ_body_element loop end
_audit_creation_date             2022-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(S)-4-((R)-3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)-4-phenyl-1,3-dioxolan-2-one
_chemical_formula_moiety         'C18 H14 Cl N O4'
_chemical_formula_sum            'C18 H14 Cl N O4'
_chemical_formula_weight         343.75
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.777(4)
_cell_length_b                   9.470(4)
_cell_length_c                   10.205(4)
_cell_angle_alpha                110.956(10)
_cell_angle_beta                 90.069(10)
_cell_angle_gamma                90.054(10)
_cell_volume                     792.1(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4755
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.411
_cell_measurement_theta_min      2.6666
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18576
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_min         2.520
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku oxford diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.886
_reflns_number_gt                4755
_reflns_number_total             6086
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1804 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       0.0155(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6086
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0187P)²+0.4234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0958
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C41(H41A,H41B), C47(H47A,H47B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23), C32(H32), C33(H33), C35(H35), C36(H36), C49(H49), C50(H50), C51(H51),
  C52(H52), C53(H53)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.16501(16) 0.24407(18) -0.38269(14) 0.0620(4) Uani 1 1 d . . . . .
C1 C 0.1704(5) 0.3003(6) -0.2008(5) 0.0408(12) Uani 1 1 d . . . . .
C2 C 0.2773(5) 0.2385(6) -0.1389(5) 0.0442(13) Uani 1 1 d . . . . .
H2 H 0.345283 0.166111 -0.193465 0.053 Uiso 1 1 calc R . . . .
Cl2 Cl 0.66473(16) 0.75623(17) 1.38355(14) 0.0621(4) Uani 1 1 d . . . . .
C3 C 0.2823(5) 0.2857(6) 0.0060(5) 0.0425(12) Uani 1 1 d . . . . .
H3 H 0.354061 0.243979 0.048602 0.051 Uiso 1 1 calc R . . . .
C4 C 0.1822(5) 0.3943(5) 0.0887(5) 0.0337(11) Uani 1 1 d . . . . .
C5 C 0.0737(6) 0.4511(6) 0.0216(5) 0.0504(14) Uani 1 1 d . . . . .
H5 H 0.003186 0.521369 0.074951 0.061 Uiso 1 1 calc R . . . .
C6 C 0.0686(6) 0.4053(6) -0.1230(5) 0.0531(14) Uani 1 1 d . . . . .
H6 H -0.003282 0.445734 -0.166652 0.064 Uiso 1 1 calc R . . . .
C7 C 0.1871(5) 0.4479(5) 0.2430(5) 0.0343(11) Uani 1 1 d . . . . .
N8 N 0.3039(5) 0.4279(5) 0.3083(4) 0.0417(10) Uani 1 1 d . . . . .
O9 O 0.2783(4) 0.4917(4) 0.4549(3) 0.0446(9) Uani 1 1 d . . . . .
C10 C 0.1357(5) 0.5770(5) 0.4810(5) 0.0376(12) Uani 1 1 d . . . . .
H10 H 0.072434 0.545985 0.545125 0.045 Uiso 1 1 calc R . . . .
C11 C 0.0589(5) 0.5280(6) 0.3376(5) 0.0382(11) Uani 1 1 d . . . . .
H11A H -0.026115 0.460434 0.331652 0.046 Uiso 1 1 calc R . . . .
H11B H 0.023706 0.614297 0.316053 0.046 Uiso 1 1 calc R . . . .
C12 C 0.1712(5) 0.7451(6) 0.5481(5) 0.0357(11) Uani 1 1 d . . . . .
C13 C 0.0291(6) 0.8440(6) 0.5620(6) 0.0497(13) Uani 1 1 d . . . . .
H13A H -0.063181 0.786035 0.557659 0.060 Uiso 1 1 calc R . . . .
H13B H 0.030566 0.929700 0.649714 0.060 Uiso 1 1 calc R . . . .
O14 O 0.0382(5) 0.8930(4) 0.4448(4) 0.0590(10) Uani 1 1 d . . . . .
C15 C 0.1778(8) 0.8676(7) 0.3901(6) 0.0535(15) Uani 1 1 d . . . . .
O16 O 0.2627(4) 0.7868(4) 0.4485(3) 0.0438(8) Uani 1 1 d . . . . .
O17 O 0.2230(6) 0.9061(5) 0.2983(5) 0.0831(15) Uani 1 1 d . . . . .
C18 C 0.2568(5) 0.7839(5) 0.6864(5) 0.0347(11) Uani 1 1 d . . . . .
C19 C 0.4006(6) 0.8471(5) 0.7056(5) 0.0431(12) Uani 1 1 d . . . . .
H19 H 0.450280 0.862813 0.631539 0.052 Uiso 1 1 calc R . . . .
C20 C 0.4711(7) 0.8874(6) 0.8361(6) 0.0553(15) Uani 1 1 d . . . . .
H20 H 0.568541 0.928938 0.848631 0.066 Uiso 1 1 calc R . . . .
C21 C 0.3981(7) 0.8663(7) 0.9463(6) 0.0600(16) Uani 1 1 d . . . . .
H21 H 0.445036 0.894891 1.033680 0.072 Uiso 1 1 calc R . . . .
C22 C 0.2561(7) 0.8030(8) 0.9272(6) 0.0631(16) Uani 1 1 d . . . . .
H22 H 0.207151 0.787363 1.001703 0.076 Uiso 1 1 calc R . . . .
C23 C 0.1839(6) 0.7617(7) 0.7976(6) 0.0540(15) Uani 1 1 d . . . . .
H23 H 0.086919 0.719273 0.785626 0.065 Uiso 1 1 calc R . . . .
C31 C 0.6703(5) 0.7003(6) 1.2013(5) 0.0412(12) Uani 1 1 d . . . . .
C32 C 0.7775(5) 0.7613(6) 1.1394(5) 0.0430(12) Uani 1 1 d . . . . .
H32 H 0.846063 0.833252 1.194176 0.052 Uiso 1 1 calc R . . . .
C33 C 0.7826(5) 0.7148(6) 0.9949(5) 0.0408(12) Uani 1 1 d . . . . .
H33 H 0.854377 0.756633 0.952374 0.049 Uiso 1 1 calc R . . . .
C34 C 0.6818(5) 0.6064(5) 0.9127(5) 0.0346(11) Uani 1 1 d . . . . .
C35 C 0.5735(6) 0.5492(6) 0.9790(5) 0.0507(14) Uani 1 1 d . . . . .
H35 H 0.503559 0.478033 0.925413 0.061 Uiso 1 1 calc R . . . .
C36 C 0.5678(6) 0.5964(6) 1.1236(5) 0.0531(14) Uani 1 1 d . . . . .
H36 H 0.494661 0.557375 1.167316 0.064 Uiso 1 1 calc R . . . .
C37 C 0.6862(5) 0.5527(5) 0.7577(5) 0.0335(11) Uani 1 1 d . . . . .
N38 N 0.8039(4) 0.5725(5) 0.6926(4) 0.0403(10) Uani 1 1 d . . . . .
O39 O 0.7786(4) 0.5085(4) 0.5461(3) 0.0437(8) Uani 1 1 d . . . . .
C40 C 0.6362(5) 0.4239(5) 0.5194(5) 0.0353(11) Uani 1 1 d . . . . .
H40 H 0.573151 0.454598 0.454857 0.042 Uiso 1 1 calc R . . . .
C41 C 0.5590(5) 0.4726(6) 0.6631(5) 0.0402(12) Uani 1 1 d . . . . .
H41A H 0.473787 0.539693 0.668846 0.048 Uiso 1 1 calc R . . . .
H41B H 0.523975 0.386018 0.684480 0.048 Uiso 1 1 calc R . . . .
C42 C 0.6715(5) 0.2551(5) 0.4532(5) 0.0349(11) Uani 1 1 d . . . . .
O43 O 0.7629(4) 0.2137(4) 0.5521(3) 0.0452(9) Uani 1 1 d . . . . .
C44 C 0.6775(8) 0.1330(7) 0.6102(6) 0.0552(15) Uani 1 1 d . . . . .
O45 O 0.7231(6) 0.0938(6) 0.7022(5) 0.0829(15) Uani 1 1 d . . . . .
O46 O 0.5375(5) 0.1073(4) 0.5559(4) 0.0589(10) Uani 1 1 d . . . . .
C47 C 0.5291(6) 0.1573(6) 0.4392(5) 0.0485(13) Uani 1 1 d . . . . .
H47A H 0.437417 0.215951 0.443796 0.058 Uiso 1 1 calc R . . . .
H47B H 0.529772 0.071993 0.351156 0.058 Uiso 1 1 calc R . . . .
C48 C 0.7570(5) 0.2160(5) 0.3146(5) 0.0359(11) Uani 1 1 d . . . . .
C49 C 0.9003(6) 0.1530(5) 0.2949(5) 0.0440(12) Uani 1 1 d . . . . .
H49 H 0.950000 0.136925 0.368868 0.053 Uiso 1 1 calc R . . . .
C50 C 0.9714(6) 0.1132(6) 0.1643(6) 0.0556(15) Uani 1 1 d . . . . .
H50 H 1.068840 0.072125 0.151937 0.067 Uiso 1 1 calc R . . . .
C51 C 0.8980(7) 0.1344(6) 0.0546(6) 0.0586(15) Uani 1 1 d . . . . .
H51 H 0.944856 0.106256 -0.032686 0.070 Uiso 1 1 calc R . . . .
C52 C 0.7554(7) 0.1973(8) 0.0734(6) 0.0632(16) Uani 1 1 d . . . . .
H52 H 0.706094 0.212497 -0.001159 0.076 Uiso 1 1 calc R . . . .
C53 C 0.6841(6) 0.2383(7) 0.2026(6) 0.0556(15) Uani 1 1 d . . . . .
H53 H 0.587251 0.280848 0.214433 0.067 Uiso 1 1 calc R . . . .


_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 C1 1.739(5) . ?
C1 C2 1.373(7) . ?
C1 C6 1.362(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(7) . ?
Cl2 C31 1.743(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(6) . ?
C4 C5 1.389(7) . ?
C4 C7 1.472(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(7) . ?
C6 H6 0.9300 . ?
C7 N8 1.273(6) . ?
C7 C11 1.501(6) . ?
N8 O9 1.417(5) . ?
O9 C10 1.462(5) . ?
C10 H10 0.9800 . ?
C10 C11 1.524(6) . ?
C10 C12 1.523(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.536(7) . ?
C12 O16 1.458(5) . ?
C12 C18 1.522(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 O14 1.430(6) . ?
O14 C15 1.334(7) . ?
C15 O16 1.350(7) . ?
C15 O17 1.188(7) . ?
C18 C19 1.380(7) . ?
C18 C23 1.383(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.370(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.366(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.390(8) . ?
C23 H23 0.9300 . ?
C31 C32 1.371(7) . ?
C31 C36 1.359(7) . ?
C32 H32 0.9300 . ?
C32 C33 1.380(7) . ?
C33 H33 0.9300 . ?
C33 C34 1.387(6) . ?
C34 C35 1.385(7) . ?
C34 C37 1.479(7) . ?
C35 H35 0.9300 . ?
C35 C36 1.382(7) . ?
C36 H36 0.9300 . ?
C37 N38 1.277(6) . ?
C37 C41 1.492(6) . ?
N38 O39 1.415(5) . ?
O39 C40 1.456(6) . ?
C40 H40 0.9800 . ?
C40 C41 1.531(6) . ?
C40 C42 1.528(7) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 O43 1.448(5) . ?
C42 C47 1.531(7) . ?
C42 C48 1.526(6) . ?
O43 C44 1.350(7) . ?
C44 O45 1.195(7) . ?
C44 O46 1.333(7) . ?
O46 C47 1.432(6) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 C49 1.376(6) . ?
C48 C53 1.390(7) . ?
C49 H49 0.9300 . ?
C49 C50 1.397(7) . ?
C50 H50 0.9300 . ?
C50 C51 1.366(8) . ?
C51 H51 0.9300 . ?
C51 C52 1.371(8) . ?
C52 H52 0.9300 . ?
C52 C53 1.384(7) . ?
C53 H53 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Cl1 119.4(4) . . ?
C6 C1 Cl1 119.1(4) . . ?
C6 C1 C2 121.5(5) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(5) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 117.9(4) . . ?
C3 C4 C7 122.0(4) . . ?
C5 C4 C7 120.0(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C4 C7 C11 124.7(4) . . ?
N8 C7 C4 121.5(4) . . ?
N8 C7 C11 113.8(4) . . ?
C7 N8 O9 109.7(4) . . ?
N8 O9 C10 109.2(3) . . ?
O9 C10 H10 109.3 . . ?
O9 C10 C11 104.1(3) . . ?
O9 C10 C12 109.2(4) . . ?
C11 C10 H10 109.3 . . ?
C12 C10 H10 109.3 . . ?
C12 C10 C11 115.6(4) . . ?
C7 C11 C10 101.4(4) . . ?
C7 C11 H11A 111.5 . . ?
C7 C11 H11B 111.5 . . ?
C10 C11 H11A 111.5 . . ?
C10 C11 H11B 111.5 . . ?
H11A C11 H11B 109.3 . . ?
C10 C12 C13 112.4(4) . . ?
O16 C12 C10 107.4(4) . . ?
O16 C12 C13 101.8(4) . . ?
O16 C12 C18 109.8(4) . . ?
C18 C12 C10 112.6(4) . . ?
C18 C12 C13 112.2(4) . . ?
C12 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
O14 C13 C12 104.3(4) . . ?
O14 C13 H13A 110.9 . . ?
O14 C13 H13B 110.9 . . ?
C15 O14 C13 109.8(4) . . ?
O14 C15 O16 111.6(5) . . ?
O17 C15 O14 125.3(6) . . ?
O17 C15 O16 123.0(6) . . ?
C15 O16 C12 109.9(4) . . ?
C19 C18 C12 122.1(4) . . ?
C19 C18 C23 119.5(4) . . ?
C23 C18 C12 118.4(4) . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(5) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.7(5) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.6(5) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 119.8(5) . . ?
C18 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C32 C31 Cl2 119.7(4) . . ?
C36 C31 Cl2 118.9(4) . . ?
C36 C31 C32 121.4(5) . . ?
C31 C32 H32 120.3 . . ?
C31 C32 C33 119.3(5) . . ?
C33 C32 H32 120.3 . . ?
C32 C33 H33 119.7 . . ?
C32 C33 C34 120.6(5) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C37 121.8(4) . . ?
C35 C34 C33 118.4(4) . . ?
C35 C34 C37 119.8(4) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 C34 121.0(5) . . ?
C36 C35 H35 119.5 . . ?
C31 C36 C35 119.2(5) . . ?
C31 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C34 C37 C41 124.8(4) . . ?
N38 C37 C34 121.3(4) . . ?
N38 C37 C41 113.8(4) . . ?
C37 N38 O39 109.7(4) . . ?
N38 O39 C40 109.3(3) . . ?
O39 C40 H40 109.5 . . ?
O39 C40 C41 104.1(4) . . ?
O39 C40 C42 109.0(4) . . ?
C41 C40 H40 109.5 . . ?
C42 C40 H40 109.5 . . ?
C42 C40 C41 115.0(4) . . ?
C37 C41 C40 101.4(4) . . ?
C37 C41 H41A 111.5 . . ?
C37 C41 H41B 111.5 . . ?
C40 C41 H41A 111.5 . . ?
C40 C41 H41B 111.5 . . ?
H41A C41 H41B 109.3 . . ?
C40 C42 C47 112.1(4) . . ?
O43 C42 C40 107.9(4) . . ?
O43 C42 C47 102.1(4) . . ?
O43 C42 C48 109.7(4) . . ?
C48 C42 C40 112.3(4) . . ?
C48 C42 C47 112.2(4) . . ?
C44 O43 C42 109.6(4) . . ?
O45 C44 O43 122.9(7) . . ?
O45 C44 O46 124.9(6) . . ?
O46 C44 O43 112.2(5) . . ?
C44 O46 C47 109.1(4) . . ?
C42 C47 H47A 110.9 . . ?
C42 C47 H47B 110.9 . . ?
O46 C47 C42 104.5(4) . . ?
O46 C47 H47A 110.9 . . ?
O46 C47 H47B 110.9 . . ?
H47A C47 H47B 108.9 . . ?
C49 C48 C42 122.3(4) . . ?
C49 C48 C53 119.1(4) . . ?
C53 C48 C42 118.5(4) . . ?
C48 C49 H49 119.9 . . ?
C48 C49 C50 120.3(5) . . ?
C50 C49 H49 119.9 . . ?
C49 C50 H50 119.9 . . ?
C51 C50 C49 120.2(5) . . ?
C51 C50 H50 119.9 . . ?
C50 C51 H51 120.0 . . ?
C50 C51 C52 119.9(5) . . ?
C52 C51 H51 120.0 . . ?
C51 C52 H52 119.7 . . ?
C51 C52 C53 120.5(5) . . ?
C53 C52 H52 119.7 . . ?
C48 C53 H53 120.0 . . ?
C52 C53 C48 120.1(5) . . ?
C52 C53 H53 120.0 . . ?

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
Cl1 C1 C2 C3 178.9(4) . . . . ?
Cl1 C1 C6 C5 -179.4(4) . . . . ?
C1 C2 C3 C4 -0.4(8) . . . . ?
C2 C1 C6 C5 0.2(9) . . . . ?
C2 C3 C4 C5 1.8(7) . . . . ?
C2 C3 C4 C7 -179.0(5) . . . . ?
Cl2 C31 C32 C33 179.1(4) . . . . ?
Cl2 C31 C36 C35 -178.7(4) . . . . ?
C3 C4 C5 C6 -2.2(8) . . . . ?
C3 C4 C7 N8 18.1(7) . . . . ?
C3 C4 C7 C11 -161.3(5) . . . . ?
C4 C5 C6 C1 1.3(9) . . . . ?
C4 C7 N8 O9 179.4(4) . . . . ?
C4 C7 C11 C10 -171.5(4) . . . . ?
C5 C4 C7 N8 -162.7(5) . . . . ?
C5 C4 C7 C11 17.9(7) . . . . ?
C6 C1 C2 C3 -0.7(8) . . . . ?
C7 C4 C5 C6 178.5(5) . . . . ?
C7 N8 O9 C10 -7.9(5) . . . . ?
N8 C7 C11 C10 9.2(6) . . . . ?
N8 O9 C10 C11 13.2(5) . . . . ?
N8 O9 C10 C12 -110.8(4) . . . . ?
O9 C10 C11 C7 -12.7(5) . . . . ?
O9 C10 C12 C13 172.8(4) . . . . ?
O9 C10 C12 O16 61.6(4) . . . . ?
O9 C10 C12 C18 -59.4(5) . . . . ?
C10 C12 C13 O14 -99.1(5) . . . . ?
C10 C12 O16 C15 106.5(4) . . . . ?
C10 C12 C18 C19 118.8(5) . . . . ?
C10 C12 C18 C23 -64.6(6) . . . . ?
C11 C7 N8 O9 -1.2(6) . . . . ?
C11 C10 C12 C13 55.8(5) . . . . ?
C11 C10 C12 O16 -55.3(5) . . . . ?
C11 C10 C12 C18 -176.3(4) . . . . ?
C12 C10 C11 C7 107.0(4) . . . . ?
C12 C13 O14 C15 -14.8(6) . . . . ?
C12 C18 C19 C20 176.9(4) . . . . ?
C12 C18 C23 C22 -176.8(5) . . . . ?
C13 C12 O16 C15 -11.8(5) . . . . ?
C13 C12 C18 C19 -113.2(5) . . . . ?
C13 C12 C18 C23 63.4(6) . . . . ?
C13 O14 C15 O16 7.9(6) . . . . ?
C13 O14 C15 O17 -174.3(6) . . . . ?
O14 C15 O16 C12 3.3(6) . . . . ?
O16 C12 C13 O14 15.6(5) . . . . ?
O16 C12 C18 C19 -0.8(6) . . . . ?
O16 C12 C18 C23 175.8(4) . . . . ?
O17 C15 O16 C12 -174.6(5) . . . . ?
C18 C12 C13 O14 132.9(4) . . . . ?
C18 C12 O16 C15 -130.9(4) . . . . ?
C18 C19 C20 C21 -0.7(8) . . . . ?
C19 C18 C23 C22 -0.1(8) . . . . ?
C19 C20 C21 C22 1.1(9) . . . . ?
C20 C21 C22 C23 -0.9(9) . . . . ?
C21 C22 C23 C18 0.4(9) . . . . ?
C23 C18 C19 C20 0.2(7) . . . . ?
C31 C32 C33 C34 -0.7(7) . . . . ?
C32 C31 C36 C35 1.1(8) . . . . ?
C32 C33 C34 C35 1.8(7) . . . . ?
C32 C33 C34 C37 -179.1(4) . . . . ?
C33 C34 C35 C36 -1.4(8) . . . . ?
C33 C34 C37 N38 18.4(7) . . . . ?
C33 C34 C37 C41 -161.6(5) . . . . ?
C34 C35 C36 C31 0.0(9) . . . . ?
C34 C37 N38 O39 179.0(4) . . . . ?
C34 C37 C41 C40 -171.3(4) . . . . ?
C35 C34 C37 N38 -162.4(5) . . . . ?
C35 C34 C37 C41 17.6(7) . . . . ?
C36 C31 C32 C33 -0.8(8) . . . . ?
C37 C34 C35 C36 179.4(5) . . . . ?
C37 N38 O39 C40 -7.9(5) . . . . ?
N38 C37 C41 C40 8.7(5) . . . . ?
N38 O39 C40 C41 12.8(5) . . . . ?
N38 O39 C40 C42 -110.5(4) . . . . ?
O39 C40 C41 C37 -12.3(5) . . . . ?
O39 C40 C42 O43 61.0(4) . . . . ?
O39 C40 C42 C47 172.7(4) . . . . ?
O39 C40 C42 C48 -60.0(5) . . . . ?
C40 C42 O43 C44 106.6(4) . . . . ?
C40 C42 C47 O46 -99.9(4) . . . . ?
C40 C42 C48 C49 119.0(5) . . . . ?
C40 C42 C48 C53 -64.2(6) . . . . ?
C41 C37 N38 O39 -0.9(5) . . . . ?
C41 C40 C42 O43 -55.5(5) . . . . ?
C41 C40 C42 C47 56.2(5) . . . . ?
C41 C40 C42 C48 -176.5(4) . . . . ?
C42 C40 C41 C37 107.0(4) . . . . ?
C42 O43 C44 O45 -174.8(5) . . . . ?
C42 O43 C44 O46 3.4(6) . . . . ?
C42 C48 C49 C50 177.2(5) . . . . ?
C42 C48 C53 C52 -176.9(5) . . . . ?
O43 C42 C47 O46 15.4(5) . . . . ?
O43 C42 C48 C49 -0.9(6) . . . . ?
O43 C42 C48 C53 175.9(5) . . . . ?
O43 C44 O46 C47 7.5(6) . . . . ?
C44 O46 C47 C42 -14.4(5) . . . . ?
O45 C44 O46 C47 -174.4(6) . . . . ?
C47 C42 O43 C44 -11.7(5) . . . . ?
C47 C42 C48 C49 -113.7(5) . . . . ?
C47 C42 C48 C53 63.2(6) . . . . ?
C48 C42 O43 C44 -130.9(4) . . . . ?
C48 C42 C47 O46 132.7(4) . . . . ?
C48 C49 C50 C51 -1.0(8) . . . . ?
C49 C48 C53 C52 0.0(9) . . . . ?
C49 C50 C51 C52 1.1(9) . . . . ?
C50 C51 C52 C53 -0.6(9) . . . . ?
C51 C52 C53 C48 0.0(10) . . . . ?
C53 C48 C49 C50 0.4(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
