# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_e
_database_code_depnum_ccdc_archive 'CCDC 1970626'
_audit_update_record             
;
2019-12-07 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 Cl N O3'
_chemical_formula_weight         391.83

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   13.2770(9)
_cell_length_b                   10.5088(7)
_cell_length_c                   27.5974(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3850.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9307
_cell_measurement_theta_min      2.9425
_cell_measurement_theta_max      26.2475

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            64778
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.01
_reflns_number_total             6759
_reflns_number_gt                5649
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0909P)²+2.1554P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.34(10)
_refine_ls_number_reflns         6759
_refine_ls_number_parameters     508
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.008

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.31755(13) 0.91604(14) 0.71533(6) 0.0827(4) Uani 1 1 d . . .
Cl2 Cl 0.43837(13) 0.57899(14) 0.69557(6) 0.0837(4) Uani 1 1 d . . .
O1 O 0.7796(2) 0.5217(3) 0.98251(15) 0.0550(9) Uani 1 1 d . . .
O2 O 0.7728(3) 0.9551(3) 0.97582(14) 0.0526(9) Uani 1 1 d . . .
O3 O 0.6390(3) 0.9562(3) 0.80409(15) 0.0680(9) Uani 1 1 d . . .
O4 O 0.1095(3) 0.5417(3) 0.60949(16) 0.0758(11) Uani 1 1 d . . .
O5 O -0.0123(3) 0.9642(3) 0.42917(14) 0.0542(9) Uani 1 1 d . . .
O6 O -0.0329(2) 0.5314(3) 0.43763(14) 0.0500(8) Uani 1 1 d . . .
N1 N 0.7579(3) 0.7392(3) 0.98714(19) 0.0372(10) Uani 1 1 d . . .
N2 N -0.0034(3) 0.7446(3) 0.42555(19) 0.0396(11) Uani 1 1 d . . .
C1 C 0.1829(5) 0.7391(4) 0.3032(3) 0.0568(17) Uani 1 1 d . . .
C2 C 0.2123(4) 0.7962(6) 0.3443(2) 0.0638(13) Uani 1 1 d . . .
H2 H 0.2745 0.8367 0.3452 0.077 Uiso 1 1 calc R . .
C3 C 0.1529(3) 0.7968(5) 0.38542(18) 0.0567(11) Uani 1 1 d . . .
H3 H 0.1747 0.8372 0.4135 0.068 Uiso 1 1 calc R . .
C4 C 0.0613(4) 0.7369(4) 0.3841(2) 0.0392(12) Uani 1 1 d . . .
C5 C 0.0306(3) 0.6723(4) 0.34277(17) 0.0475(10) Uani 1 1 d . . .
H5 H -0.0303 0.6285 0.3425 0.057 Uiso 1 1 d R . .
C6 C 0.0913(4) 0.6735(4) 0.30203(17) 0.0545(11) Uani 1 1 d . . .
H6 H 0.0713 0.6310 0.2741 0.065 Uiso 1 1 calc R . .
C7 C 0.2479(6) 0.7471(5) 0.2568(3) 0.083(3) Uani 1 1 d . . .
H7A H 0.3171 0.7605 0.2655 0.125 Uiso 1 1 calc R . .
H7B H 0.2250 0.8166 0.2371 0.125 Uiso 1 1 calc R . .
H7C H 0.2420 0.6691 0.2389 0.125 Uiso 1 1 calc R . .
C9 C -0.0430(3) 0.6408(4) 0.45000(18) 0.0387(10) Uani 1 1 d . . .
C10 C -0.1016(3) 0.6902(5) 0.49379(17) 0.0449(11) Uani 1 1 d . . .
H10 H -0.1723 0.6636 0.4922 0.054 Uiso 1 1 calc R . .
C11 C -0.0926(3) 0.8361(4) 0.49064(17) 0.0436(11) Uani 1 1 d . . .
H11 H -0.1593 0.8758 0.4885 0.052 Uiso 1 1 calc R . .
C12 C -0.0327(3) 0.8610(4) 0.44588(18) 0.0406(11) Uani 1 1 d . . .
C14 C -0.0568(3) 0.6590(4) 0.54287(19) 0.0457(12) Uani 1 1 d . . .
H14 H -0.0790 0.5776 0.5565 0.055 Uiso 1 1 calc R . .
C15 C -0.0411(3) 0.8706(4) 0.53807(18) 0.0431(11) Uani 1 1 d . . .
H15 H -0.0499 0.9598 0.5476 0.052 Uiso 1 1 calc R . .
C16 C -0.0898(4) 0.7772(6) 0.5722(2) 0.0600(14) Uani 1 1 d . . .
H16A H -0.1624 0.7868 0.5738 0.072 Uiso 1 1 calc R . .
H16B H -0.0609 0.7795 0.6045 0.072 Uiso 1 1 calc R . .
C17 C 0.4949(6) 0.7528(5) 1.1511(3) 0.078(2) Uani 1 1 d . . .
H17A H 0.5342 0.7611 1.1801 0.117 Uiso 1 1 calc R . .
H17B H 0.4548 0.6769 1.1529 0.117 Uiso 1 1 calc R . .
H17C H 0.4516 0.8254 1.1477 0.117 Uiso 1 1 calc R . .
C18 C 0.5377(4) 0.8042(5) 1.06483(18) 0.0562(12) Uani 1 1 d . . .
H18 H 0.4766 0.8469 1.0625 0.067 Uiso 1 1 d R . .
C19 C 0.5626(5) 0.7449(4) 1.1087(3) 0.0519(15) Uani 1 1 d . . .
C20 C 0.6544(4) 0.6819(4) 1.10938(17) 0.0554(11) Uani 1 1 d . . .
H20 H 0.6734 0.6397 1.1375 0.066 Uiso 1 1 calc R . .
C21 C 0.7182(3) 0.6791(4) 1.07047(16) 0.0482(10) Uani 1 1 d . . .
H21 H 0.7790 0.6355 1.0726 0.058 Uiso 1 1 d R . .
C22 C 0.6929(4) 0.7403(3) 1.0284(2) 0.0374(12) Uani 1 1 d . . .
C23 C 0.6004(3) 0.8020(5) 1.02506(18) 0.0536(11) Uani 1 1 d . . .
H23 H 0.5811 0.8412 0.9963 0.064 Uiso 1 1 d R . .
C24 C 0.1692(4) 0.9836(4) 0.59261(16) 0.0521(11) Uani 1 1 d . . .
H24 H 0.1564 1.0530 0.5726 0.062 Uiso 1 1 d R . .
C25 C 0.2264(4) 0.9979(4) 0.63355(16) 0.0561(11) Uani 1 1 d . . .
H25 H 0.2533 1.0773 0.6411 0.067 Uiso 1 1 calc R . .
C26 C 0.2449(3) 0.8946(4) 0.66410(15) 0.0505(10) Uani 1 1 d . . .
C27 C 0.2065(4) 0.7761(5) 0.6542(2) 0.0480(11) Uani 1 1 d . . .
H27 H 0.2179 0.7077 0.6748 0.058 Uiso 1 1 calc R . .
C28 C 0.1496(4) 0.7620(4) 0.61192(19) 0.0351(11) Uani 1 1 d . . .
C29 C 0.1304(3) 0.8652(4) 0.58123(16) 0.0382(10) Uani 1 1 d . . .
C30 C 0.1080(3) 0.6457(5) 0.59040(18) 0.0454(11) Uani 1 1 d . . .
C31 C 0.7922(3) 0.8483(4) 0.96222(19) 0.0416(11) Uani 1 1 d . . .
C32 C 0.7935(3) 0.6263(4) 0.9656(2) 0.0415(11) Uani 1 1 d . . .
C33 C 0.8511(3) 0.8073(4) 0.91972(18) 0.0443(11) Uani 1 1 d . . .
H33 H 0.9207 0.8376 0.9224 0.053 Uiso 1 1 calc R . .
C34 C 0.8070(3) 0.8403(4) 0.86818(19) 0.0459(11) Uani 1 1 d . . .
H34 H 0.8269 0.9234 0.8552 0.055 Uiso 1 1 calc R . .
C35 C 0.8426(4) 0.7262(5) 0.8392(2) 0.0497(12) Uani 1 1 d . . .
H35A H 0.9155 0.7198 0.8380 0.060 Uiso 1 1 calc R . .
H35B H 0.8153 0.7251 0.8066 0.060 Uiso 1 1 calc R . .
C36 C 0.7951(3) 0.6249(4) 0.87166(19) 0.0440(11) Uani 1 1 d . . .
H36 H 0.8047 0.5369 0.8609 0.053 Uiso 1 1 calc R . .
C37 C 0.8483(3) 0.6602(4) 0.9206(2) 0.0471(12) Uani 1 1 d . . .
H37 H 0.9168 0.6256 0.9214 0.057 Uiso 1 1 calc R . .
C38 C 0.6930(3) 0.8163(4) 0.87033(16) 0.0367(10) Uani 1 1 d . . .
H38 H 0.6611 0.8598 0.8977 0.044 Uiso 1 1 calc R . .
C39 C 0.6845(3) 0.6697(4) 0.87424(16) 0.0334(9) Uani 1 1 d . . .
H39 H 0.6516 0.6431 0.9044 0.040 Uiso 1 1 calc R . .
C40 C 0.6245(3) 0.6312(5) 0.82993(16) 0.0395(11) Uani 1 1 d . . .
C41 C 0.6026(4) 0.7326(4) 0.8006(2) 0.0390(11) Uani 1 1 d . . .
C42 C 0.6430(3) 0.8497(5) 0.82181(17) 0.0425(11) Uani 1 1 d . . .
C43 C 0.5467(3) 0.7212(5) 0.75816(18) 0.0440(10) Uani 1 1 d . . .
H43 H 0.5337 0.7908 0.7383 0.053 Uiso 1 1 calc R . .
C44 C 0.5114(3) 0.6007(4) 0.74709(15) 0.0507(10) Uani 1 1 d . . .
C45 C 0.5313(4) 0.4967(4) 0.77659(17) 0.0562(11) Uani 1 1 d . . .
H45 H 0.5056 0.4172 0.7685 0.067 Uiso 1 1 calc R . .
C46 C 0.5889(4) 0.5107(4) 0.81765(16) 0.0527(11) Uani 1 1 d . . .
H46 H 0.6038 0.4407 0.8370 0.063 Uiso 1 1 calc R . .
C47 C 0.0697(3) 0.8261(4) 0.53795(17) 0.0346(10) Uani 1 1 d . . .
H47 H 0.1036 0.8491 0.5076 0.042 Uiso 1 1 calc R . .
C48 C 0.0590(3) 0.6792(4) 0.54315(19) 0.0410(11) Uani 1 1 d . . .
H48 H 0.0911 0.6348 0.5160 0.049 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 C26 1.726(4) . ?
Cl2 C44 1.736(4) . ?
O1 C32 1.208(5) . ?
O2 C31 1.212(6) . ?
O3 C42 1.223(6) . ?
O4 C30 1.214(6) . ?
O5 C12 1.209(5) . ?
O6 C9 1.208(5) . ?
N1 C32 1.408(6) . ?
N1 C31 1.412(6) . ?
N1 C22 1.428(8) . ?
N2 C9 1.386(6) . ?
N2 C12 1.401(6) . ?
N2 C4 1.432(8) . ?
C1 C2 1.342(9) . ?
C1 C6 1.399(8) . ?
C1 C7 1.547(9) . ?
C2 C3 1.381(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(7) . ?
C5 C6 1.384(6) . ?
C5 H5 0.9299 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.528(6) . ?
C10 C14 1.515(7) . ?
C10 C11 1.541(7) . ?
C10 H10 0.9800 . ?
C11 C12 1.492(7) . ?
C11 C15 1.521(7) . ?
C11 H11 0.9800 . ?
C14 C16 1.546(7) . ?
C14 C48 1.552(6) . ?
C14 H14 0.9800 . ?
C15 C16 1.506(8) . ?
C15 C47 1.543(6) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C19 1.478(11) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.377(7) . ?
C18 C19 1.401(8) . ?
C18 H18 0.9301 . ?
C19 C20 1.386(8) . ?
C20 C21 1.368(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(7) . ?
C23 H23 0.9301 . ?
C24 C25 1.370(6) . ?
C24 C29 1.382(6) . ?
C24 H24 0.9299 . ?
C25 C26 1.397(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.373(7) . ?
C27 C28 1.397(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.400(7) . ?
C28 C30 1.467(7) . ?
C29 C47 1.499(6) . ?
C30 C48 1.499(7) . ?
C31 C33 1.474(7) . ?
C32 C37 1.482(7) . ?
C33 C37 1.547(7) . ?
C33 C34 1.577(7) . ?
C33 H33 0.9800 . ?
C34 C35 1.518(7) . ?
C34 C38 1.535(6) . ?
C34 H34 0.9800 . ?
C35 C36 1.528(7) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C39 1.544(6) . ?
C36 C37 1.570(7) . ?
C36 H36 0.9800 . ?
C37 H37 0.9800 . ?
C38 C42 1.536(6) . ?
C38 C39 1.549(7) . ?
C38 H38 0.9800 . ?
C39 C40 1.514(6) . ?
C39 H39 0.9800 . ?
C40 C41 1.369(7) . ?
C40 C46 1.393(7) . ?
C41 C43 1.392(7) . ?
C41 C42 1.464(7) . ?
C43 C44 1.384(7) . ?
C43 H43 0.9300 . ?
C44 C45 1.388(6) . ?
C45 C46 1.375(6) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 C48 1.557(7) . ?
C47 H47 0.9800 . ?
C48 H48 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
C32 N1 C31 111.7(5) . . ?
C32 N1 C22 123.1(4) . . ?
C31 N1 C22 125.2(4) . . ?
C9 N2 C12 112.7(5) . . ?
C9 N2 C4 124.9(3) . . ?
C12 N2 C4 122.4(4) . . ?
C2 C1 C6 119.5(6) . . ?
C2 C1 C7 120.9(6) . . ?
C6 C1 C7 119.5(6) . . ?
C1 C2 C3 122.0(5) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.5(5) . . ?
C3 C4 N2 119.1(5) . . ?
C5 C4 N2 120.4(4) . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.2 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O6 C9 N2 124.7(5) . . ?
O6 C9 C10 127.1(4) . . ?
N2 C9 C10 108.1(4) . . ?
C14 C10 C9 115.7(4) . . ?
C14 C10 C11 103.6(3) . . ?
C9 C10 C11 104.7(3) . . ?
C14 C10 H10 110.8 . . ?
C9 C10 H10 110.8 . . ?
C11 C10 H10 110.8 . . ?
C12 C11 C15 115.5(4) . . ?
C12 C11 C10 105.2(3) . . ?
C15 C11 C10 102.9(3) . . ?
C12 C11 H11 110.9 . . ?
C15 C11 H11 110.9 . . ?
C10 C11 H11 110.9 . . ?
O5 C12 N2 124.6(5) . . ?
O5 C12 C11 126.3(5) . . ?
N2 C12 C11 109.0(4) . . ?
C10 C14 C16 100.6(4) . . ?
C10 C14 C48 111.3(4) . . ?
C16 C14 C48 99.6(4) . . ?
C10 C14 H14 114.5 . . ?
C16 C14 H14 114.5 . . ?
C48 C14 H14 114.5 . . ?
C16 C15 C11 100.9(4) . . ?
C16 C15 C47 102.3(4) . . ?
C11 C15 C47 110.8(3) . . ?
C16 C15 H15 113.8 . . ?
C11 C15 H15 113.8 . . ?
C47 C15 H15 113.8 . . ?
C15 C16 C14 94.3(4) . . ?
C15 C16 H16A 112.9 . . ?
C14 C16 H16A 112.9 . . ?
C15 C16 H16B 112.9 . . ?
C14 C16 H16B 112.9 . . ?
H16A C16 H16B 110.3 . . ?
C19 C17 H17A 109.5 . . ?
C19 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C19 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 122.6(5) . . ?
C23 C18 H18 118.7 . . ?
C19 C18 H18 118.7 . . ?
C20 C19 C18 115.5(6) . . ?
C20 C19 C17 123.4(6) . . ?
C18 C19 C17 121.0(6) . . ?
C21 C20 C19 123.0(5) . . ?
C21 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?
C20 C21 C22 120.2(4) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 119.4(5) . . ?
C21 C22 N1 121.6(5) . . ?
C23 C22 N1 119.1(5) . . ?
C18 C23 C22 119.3(5) . . ?
C18 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C25 C24 C29 119.5(4) . . ?
C25 C24 H24 120.2 . . ?
C29 C24 H24 120.2 . . ?
C24 C25 C26 120.6(4) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C27 C26 C25 121.3(4) . . ?
C27 C26 Cl1 119.3(4) . . ?
C25 C26 Cl1 119.4(3) . . ?
C26 C27 C28 117.6(5) . . ?
C26 C27 H27 121.2 . . ?
C28 C27 H27 121.2 . . ?
C27 C28 C29 121.4(4) . . ?
C27 C28 C30 129.0(4) . . ?
C29 C28 C30 109.4(5) . . ?
C24 C29 C28 119.5(4) . . ?
C24 C29 C47 128.9(4) . . ?
C28 C29 C47 111.6(4) . . ?
O4 C30 C28 124.6(5) . . ?
O4 C30 C48 126.6(5) . . ?
C28 C30 C48 108.7(4) . . ?
O2 C31 N1 122.2(5) . . ?
O2 C31 C33 129.0(4) . . ?
N1 C31 C33 108.8(4) . . ?
O1 C32 N1 123.6(5) . . ?
O1 C32 C37 128.0(5) . . ?
N1 C32 C37 108.4(4) . . ?
C31 C33 C37 105.4(3) . . ?
C31 C33 C34 117.2(4) . . ?
C37 C33 C34 103.0(3) . . ?
C31 C33 H33 110.3 . . ?
C37 C33 H33 110.3 . . ?
C34 C33 H33 110.3 . . ?
C35 C34 C38 101.4(4) . . ?
C35 C34 C33 100.8(4) . . ?
C38 C34 C33 107.2(4) . . ?
C35 C34 H34 115.2 . . ?
C38 C34 H34 115.2 . . ?
C33 C34 H34 115.2 . . ?
C34 C35 C36 96.4(4) . . ?
C34 C35 H35A 112.5 . . ?
C36 C35 H35A 112.5 . . ?
C34 C35 H35B 112.5 . . ?
C36 C35 H35B 112.5 . . ?
H35A C35 H35B 110.0 . . ?
C35 C36 C39 102.0(4) . . ?
C35 C36 C37 98.9(4) . . ?
C39 C36 C37 108.4(4) . . ?
C35 C36 H36 115.2 . . ?
C39 C36 H36 115.2 . . ?
C37 C36 H36 115.2 . . ?
C32 C37 C33 105.4(4) . . ?
C32 C37 C36 116.4(3) . . ?
C33 C37 C36 103.5(3) . . ?
C32 C37 H37 110.4 . . ?
C33 C37 H37 110.4 . . ?
C36 C37 H37 110.4 . . ?
C34 C38 C42 110.8(4) . . ?
C34 C38 C39 103.8(3) . . ?
C42 C38 C39 104.9(3) . . ?
C34 C38 H38 112.3 . . ?
C42 C38 H38 112.3 . . ?
C39 C38 H38 112.3 . . ?
C40 C39 C36 112.4(4) . . ?
C40 C39 C38 104.3(3) . . ?
C36 C39 C38 103.3(3) . . ?
C40 C39 H39 112.1 . . ?
C36 C39 H39 112.1 . . ?
C38 C39 H39 112.1 . . ?
C41 C40 C46 119.4(4) . . ?
C41 C40 C39 112.4(4) . . ?
C46 C40 C39 128.1(4) . . ?
C40 C41 C43 122.9(4) . . ?
C40 C41 C42 109.9(5) . . ?
C43 C41 C42 127.2(5) . . ?
O3 C42 C41 126.4(5) . . ?
O3 C42 C38 125.2(4) . . ?
C41 C42 C38 108.3(4) . . ?
C44 C43 C41 116.4(5) . . ?
C44 C43 H43 121.8 . . ?
C41 C43 H43 121.8 . . ?
C43 C44 C45 121.8(4) . . ?
C43 C44 Cl2 119.3(4) . . ?
C45 C44 Cl2 118.9(3) . . ?
C46 C45 C44 120.3(4) . . ?
C46 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C45 C46 C40 119.1(4) . . ?
C45 C46 H46 120.4 . . ?
C40 C46 H46 120.5 . . ?
C29 C47 C15 115.3(4) . . ?
C29 C47 C48 104.4(3) . . ?
C15 C47 C48 102.3(3) . . ?
C29 C47 H47 111.4 . . ?
C15 C47 H47 111.4 . . ?
C48 C47 H47 111.4 . . ?
C30 C48 C14 113.7(4) . . ?
C30 C48 C47 105.9(3) . . ?
C14 C48 C47 103.1(3) . . ?
C30 C48 H48 111.3 . . ?
C14 C48 H48 111.3 . . ?
C47 C48 H48 111.3 . . ?

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 -2.6(9) . . . . ?
C7 C1 C2 C3 176.1(6) . . . . ?
C1 C2 C3 C4 0.2(9) . . . . ?
C2 C3 C4 C5 2.6(8) . . . . ?
C2 C3 C4 N2 -175.8(5) . . . . ?
C9 N2 C4 C3 -124.7(5) . . . . ?
C12 N2 C4 C3 54.8(7) . . . . ?
C9 N2 C4 C5 56.9(7) . . . . ?
C12 N2 C4 C5 -123.6(5) . . . . ?
C3 C4 C5 C6 -2.8(7) . . . . ?
N2 C4 C5 C6 175.6(4) . . . . ?
C4 C5 C6 C1 0.4(7) . . . . ?
C2 C1 C6 C5 2.3(7) . . . . ?
C7 C1 C6 C5 -176.4(5) . . . . ?
C12 N2 C9 O6 175.6(4) . . . . ?
C4 N2 C9 O6 -4.8(8) . . . . ?
C12 N2 C9 C10 -3.4(6) . . . . ?
C4 N2 C9 C10 176.1(5) . . . . ?
O6 C9 C10 C14 68.9(6) . . . . ?
N2 C9 C10 C14 -112.0(4) . . . . ?
O6 C9 C10 C11 -177.7(4) . . . . ?
N2 C9 C10 C11 1.3(4) . . . . ?
C14 C10 C11 C12 122.7(4) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C14 C10 C11 C15 1.4(4) . . . . ?
C9 C10 C11 C15 -120.3(3) . . . . ?
C9 N2 C12 O5 -175.5(4) . . . . ?
C4 N2 C12 O5 4.9(8) . . . . ?
C9 N2 C12 C11 4.2(6) . . . . ?
C4 N2 C12 C11 -175.4(5) . . . . ?
C15 C11 C12 O5 -70.6(6) . . . . ?
C10 C11 C12 O5 176.6(4) . . . . ?
C15 C11 C12 N2 109.6(4) . . . . ?
C10 C11 C12 N2 -3.1(4) . . . . ?
C9 C10 C14 C16 148.0(4) . . . . ?
C11 C10 C14 C16 34.1(4) . . . . ?
C9 C10 C14 C48 43.2(5) . . . . ?
C11 C10 C14 C48 -70.8(4) . . . . ?
C12 C11 C15 C16 -151.6(4) . . . . ?
C10 C11 C15 C16 -37.5(4) . . . . ?
C12 C11 C15 C47 -43.7(5) . . . . ?
C10 C11 C15 C47 70.3(4) . . . . ?
C11 C15 C16 C14 57.3(4) . . . . ?
C47 C15 C16 C14 -57.0(5) . . . . ?
C10 C14 C16 C15 -56.2(4) . . . . ?
C48 C14 C16 C15 57.8(5) . . . . ?
C23 C18 C19 C20 -0.8(8) . . . . ?
C23 C18 C19 C17 178.1(5) . . . . ?
C18 C19 C20 C21 1.3(7) . . . . ?
C17 C19 C20 C21 -177.6(5) . . . . ?
C19 C20 C21 C22 0.0(7) . . . . ?
C20 C21 C22 C23 -2.0(7) . . . . ?
C20 C21 C22 N1 180.0(4) . . . . ?
C32 N1 C22 C21 55.4(7) . . . . ?
C31 N1 C22 C21 -126.4(5) . . . . ?
C32 N1 C22 C23 -122.7(5) . . . . ?
C31 N1 C22 C23 55.5(7) . . . . ?
C19 C18 C23 C22 -1.0(8) . . . . ?
C21 C22 C23 C18 2.4(7) . . . . ?
N1 C22 C23 C18 -179.5(4) . . . . ?
C29 C24 C25 C26 -0.8(7) . . . . ?
C24 C25 C26 C27 -0.1(7) . . . . ?
C24 C25 C26 Cl1 179.9(4) . . . . ?
C25 C26 C27 C28 1.1(7) . . . . ?
Cl1 C26 C27 C28 -178.9(4) . . . . ?
C26 C27 C28 C29 -1.3(7) . . . . ?
C26 C27 C28 C30 173.8(5) . . . . ?
C25 C24 C29 C28 0.6(7) . . . . ?
C25 C24 C29 C47 -177.5(4) . . . . ?
C27 C28 C29 C24 0.5(7) . . . . ?
C30 C28 C29 C24 -175.5(4) . . . . ?
C27 C28 C29 C47 178.9(4) . . . . ?
C30 C28 C29 C47 2.9(5) . . . . ?
C27 C28 C30 O4 7.4(9) . . . . ?
C29 C28 C30 O4 -177.0(5) . . . . ?
C27 C28 C30 C48 -176.0(5) . . . . ?
C29 C28 C30 C48 -0.4(5) . . . . ?
C32 N1 C31 O2 -177.5(4) . . . . ?
C22 N1 C31 O2 4.2(8) . . . . ?
C32 N1 C31 C33 2.7(6) . . . . ?
C22 N1 C31 C33 -175.7(5) . . . . ?
C31 N1 C32 O1 174.9(4) . . . . ?
C22 N1 C32 O1 -6.7(8) . . . . ?
C31 N1 C32 C37 -5.2(6) . . . . ?
C22 N1 C32 C37 173.2(4) . . . . ?
O2 C31 C33 C37 -179.0(4) . . . . ?
N1 C31 C33 C37 0.8(4) . . . . ?
O2 C31 C33 C34 -65.1(6) . . . . ?
N1 C31 C33 C34 114.7(4) . . . . ?
C31 C33 C34 C35 -146.7(4) . . . . ?
C37 C33 C34 C35 -31.5(4) . . . . ?
C31 C33 C34 C38 -41.1(5) . . . . ?
C37 C33 C34 C38 74.1(4) . . . . ?
C38 C34 C35 C36 -54.4(5) . . . . ?
C33 C34 C35 C36 55.7(4) . . . . ?
C34 C35 C36 C39 53.0(4) . . . . ?
C34 C35 C36 C37 -58.1(4) . . . . ?
O1 C32 C37 C33 -174.7(4) . . . . ?
N1 C32 C37 C33 5.4(4) . . . . ?
O1 C32 C37 C36 71.4(6) . . . . ?
N1 C32 C37 C36 -108.6(4) . . . . ?
C31 C33 C37 C32 -3.7(4) . . . . ?
C34 C33 C37 C32 -127.1(4) . . . . ?
C31 C33 C37 C36 118.9(4) . . . . ?
C34 C33 C37 C36 -4.4(4) . . . . ?
C35 C36 C37 C32 153.6(4) . . . . ?
C39 C36 C37 C32 47.6(5) . . . . ?
C35 C36 C37 C33 38.5(4) . . . . ?
C39 C36 C37 C33 -67.4(4) . . . . ?
C35 C34 C38 C42 -76.5(5) . . . . ?
C33 C34 C38 C42 178.4(4) . . . . ?
C35 C34 C38 C39 35.6(4) . . . . ?
C33 C34 C38 C39 -69.5(4) . . . . ?
C35 C36 C39 C40 80.4(4) . . . . ?
C37 C36 C39 C40 -175.8(4) . . . . ?
C35 C36 C39 C38 -31.5(4) . . . . ?
C37 C36 C39 C38 72.3(4) . . . . ?
C34 C38 C39 C40 -120.1(4) . . . . ?
C42 C38 C39 C40 -3.8(4) . . . . ?
C34 C38 C39 C36 -2.4(4) . . . . ?
C42 C38 C39 C36 114.0(4) . . . . ?
C36 C39 C40 C41 -108.1(4) . . . . ?
C38 C39 C40 C41 3.1(4) . . . . ?
C36 C39 C40 C46 74.0(6) . . . . ?
C38 C39 C40 C46 -174.8(4) . . . . ?
C46 C40 C41 C43 -0.8(7) . . . . ?
C39 C40 C41 C43 -178.9(4) . . . . ?
C46 C40 C41 C42 177.0(4) . . . . ?
C39 C40 C41 C42 -1.0(5) . . . . ?
C40 C41 C42 O3 177.7(4) . . . . ?
C43 C41 C42 O3 -4.6(8) . . . . ?
C40 C41 C42 C38 -1.5(5) . . . . ?
C43 C41 C42 C38 176.1(4) . . . . ?
C34 C38 C42 O3 -64.5(6) . . . . ?
C39 C38 C42 O3 -175.9(4) . . . . ?
C34 C38 C42 C41 114.8(4) . . . . ?
C39 C38 C42 C41 3.4(4) . . . . ?
C40 C41 C43 C44 1.3(7) . . . . ?
C42 C41 C43 C44 -176.1(5) . . . . ?
C41 C43 C44 C45 -0.4(7) . . . . ?
C41 C43 C44 Cl2 178.4(3) . . . . ?
C43 C44 C45 C46 -1.2(7) . . . . ?
Cl2 C44 C45 C46 -180.0(4) . . . . ?
C44 C45 C46 C40 1.8(7) . . . . ?
C41 C40 C46 C45 -0.8(7) . . . . ?
C39 C40 C46 C45 176.9(4) . . . . ?
C24 C29 C47 C15 -74.5(6) . . . . ?
C28 C29 C47 C15 107.3(4) . . . . ?
C24 C29 C47 C48 174.1(4) . . . . ?
C28 C29 C47 C48 -4.1(4) . . . . ?
C16 C15 C47 C29 -78.3(5) . . . . ?
C11 C15 C47 C29 174.9(4) . . . . ?
C16 C15 C47 C48 34.3(4) . . . . ?
C11 C15 C47 C48 -72.6(4) . . . . ?
O4 C30 C48 C14 62.0(7) . . . . ?
C28 C30 C48 C14 -114.6(4) . . . . ?
O4 C30 C48 C47 174.4(5) . . . . ?
C28 C30 C48 C47 -2.1(5) . . . . ?
C10 C14 C48 C30 -178.1(4) . . . . ?
C16 C14 C48 C30 76.5(5) . . . . ?
C10 C14 C48 C47 67.8(4) . . . . ?
C16 C14 C48 C47 -37.6(5) . . . . ?
C29 C47 C48 C30 3.6(4) . . . . ?
C15 C47 C48 C30 -116.9(4) . . . . ?
C29 C47 C48 C14 123.3(4) . . . . ?
C15 C47 C48 C14 2.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.058
