# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_AY75M
_database_code_depnum_ccdc_archive 'CCDC 1415312'
_audit_update_record             
;
2015-07-27 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-3-chloro-4-(4-chlorophenyl)-7,7-dimethyl-5-oxo-2-((phenylthio)imino)-3,4,5,6,7,8-hexahydro-2H-chromene-3-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Cl2 N2 O2 S'
_chemical_formula_weight         471.38

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'
S S 0.1246 0.1234 '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                   16.6008(8)
_cell_length_b                   13.5612(7)
_cell_length_c                   21.8151(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.9260(10)
_cell_angle_gamma                90
_cell_volume                     4698.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8332
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      21.08

_exptl_crystal_description       DIAMOND
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.388
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45900
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.282
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8595
_reflns_number_gt                6645
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0575P)²+2.4185P] 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         8595
_refine_ls_number_parameters     563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1452
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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
C1 C 0.7405(2) 0.7134(3) 0.20674(17) 0.0582(8) Uani 1 1 d . . . . .
C2 C 0.7498(2) 0.7584(3) 0.27177(19) 0.0771(11) Uani 1 1 d . . . . .
H2A H 0.6947 0.7792 0.2738 0.093 Uiso 1 1 calc R U . . .
H2B H 0.7701 0.7082 0.3042 0.093 Uiso 1 1 calc R U . . .
C3 C 0.8087(2) 0.8454(3) 0.28746(17) 0.0655(9) Uani 1 1 d . . . . .
C4 C 0.8930(2) 0.8164(3) 0.27948(17) 0.0714(10) Uani 1 1 d . . . . .
H4A H 0.9257 0.8755 0.2789 0.086 Uiso 1 1 calc R U . . .
H4B H 0.9234 0.7770 0.3160 0.086 Uiso 1 1 calc R U . . .
C5 C 0.88502(18) 0.7595(2) 0.21991(15) 0.0515(8) Uani 1 1 d . . . . .
C6 C 0.81622(18) 0.7142(2) 0.18466(14) 0.0465(7) Uani 1 1 d . . . . .
C7 C 0.81290(16) 0.6624(2) 0.12365(14) 0.0451(7) Uani 1 1 d . . . . .
H7 H 0.7738 0.6068 0.1188 0.054 Uiso 1 1 calc R U . . .
C8 C 0.90225(18) 0.6202(2) 0.13141(15) 0.0509(7) Uani 1 1 d . . . . .
C9 C 0.96758(17) 0.6997(2) 0.15420(15) 0.0486(7) Uani 1 1 d . . . . .
C10 C 0.78283(17) 0.7270(2) 0.06441(14) 0.0448(7) Uani 1 1 d . . . . .
C11 C 0.8031(2) 0.8257(2) 0.06458(17) 0.0621(9) Uani 1 1 d . . . . .
H11 H 0.8380 0.8538 0.1018 0.075 Uiso 1 1 calc R U . . .
C12 C 0.7727(2) 0.8837(3) 0.01069(18) 0.0696(10) Uani 1 1 d . . . . .
H12 H 0.7874 0.9499 0.0113 0.084 Uiso 1 1 calc R U . . .
C13 C 0.7206(2) 0.8420(2) -0.04376(16) 0.0600(8) Uani 1 1 d . . . . .
C14 C 0.6997(2) 0.7442(3) -0.04584(16) 0.0608(9) Uani 1 1 d . . . . .
H14 H 0.6647 0.7165 -0.0831 0.073 Uiso 1 1 calc R U . . .
C15 C 0.73130(19) 0.6874(2) 0.00825(15) 0.0537(8) Uani 1 1 d . . . . .
H15 H 0.7176 0.6207 0.0069 0.064 Uiso 1 1 calc R U . . .
C16 C 0.90932(19) 0.5740(3) 0.07236(19) 0.0598(9) Uani 1 1 d . . . . .
C17 C 1.16511(17) 0.7701(2) 0.10758(14) 0.0464(7) Uani 1 1 d . . . . .
C18 C 1.16737(18) 0.6792(2) 0.07981(14) 0.0510(7) Uani 1 1 d . . . . .
H18 H 1.1323 0.6286 0.0853 0.061 Uiso 1 1 calc R U . . .
C19 C 1.22222(19) 0.6641(3) 0.04365(15) 0.0557(8) Uani 1 1 d . . . . .
H19 H 1.2235 0.6032 0.0244 0.067 Uiso 1 1 calc R U . . .
C20 C 1.2748(2) 0.7380(3) 0.03590(15) 0.0594(9) Uani 1 1 d . . . . .
H20 H 1.3116 0.7273 0.0116 0.071 Uiso 1 1 calc R U . . .
C21 C 1.2727(2) 0.8276(3) 0.06414(17) 0.0646(9) Uani 1 1 d . . . . .
H21 H 1.3087 0.8776 0.0593 0.078 Uiso 1 1 calc R U . . .
C22 C 1.2178(2) 0.8445(2) 0.09972(16) 0.0588(8) Uani 1 1 d . . . . .
H22 H 1.2164 0.9058 0.1184 0.071 Uiso 1 1 calc R U . . .
C23 C 0.7703(3) 0.9281(3) 0.2381(2) 0.1079(16) Uani 1 1 d . . . . .
H23A H 0.7678 0.9058 0.1958 0.162 Uiso 1 1 calc R U . . .
H23B H 0.8050 0.9859 0.2481 0.162 Uiso 1 1 calc R U . . .
H23C H 0.7146 0.9434 0.2398 0.162 Uiso 1 1 calc R U . . .
C24 C 0.8180(3) 0.8865(4) 0.3533(2) 0.1014(15) Uani 1 1 d . . . . .
H24A H 0.7640 0.9073 0.3561 0.152 Uiso 1 1 calc R U . . .
H24B H 0.8557 0.9418 0.3608 0.152 Uiso 1 1 calc R U . . .
H24C H 0.8402 0.8364 0.3848 0.152 Uiso 1 1 calc R U . . .
C25 C 0.49792(17) 0.7586(2) 0.28031(14) 0.0408(6) Uani 1 1 d . . . . .
C26 C 0.49884(19) 0.7039(2) 0.22091(15) 0.0531(8) Uani 1 1 d . . . . .
H26A H 0.5565 0.6860 0.2241 0.064 Uiso 1 1 calc R U . . .
H26B H 0.4791 0.7476 0.1844 0.064 Uiso 1 1 calc R U . . .
C27 C 0.44508(18) 0.6108(2) 0.20858(14) 0.0452(7) Uani 1 1 d . . . . .
C28 C 0.35552(18) 0.6406(2) 0.20762(13) 0.0452(7) Uani 1 1 d . . . . .
H28A H 0.3293 0.6765 0.1684 0.054 Uiso 1 1 calc R U . . .
H28B H 0.3225 0.5816 0.2078 0.054 Uiso 1 1 calc R U . . .
C29 C 0.35488(16) 0.7028(2) 0.26323(13) 0.0398(6) Uani 1 1 d . . . . .
C30 C 0.41885(16) 0.75663(19) 0.29788(13) 0.0382(6) Uani 1 1 d . . . . .
C31 C 0.41274(16) 0.8180(2) 0.35356(13) 0.0402(6) Uani 1 1 d . . . . .
H31 H 0.4472 0.8772 0.3556 0.048 Uiso 1 1 calc R U . . .
C32 C 0.31945(18) 0.8501(2) 0.33891(13) 0.0433(7) Uani 1 1 d . . . . .
C33 C 0.26252(17) 0.7622(2) 0.32118(14) 0.0439(7) Uani 1 1 d . . . . .
C34 C 0.44281(17) 0.7649(2) 0.41754(14) 0.0428(7) Uani 1 1 d . . . . .
C35 C 0.49613(19) 0.8118(2) 0.47018(15) 0.0537(8) Uani 1 1 d . . . . .
H35 H 0.5126 0.8765 0.4662 0.064 Uiso 1 1 calc R U . . .
C36 C 0.5254(2) 0.7645(3) 0.52849(16) 0.0628(9) Uani 1 1 d . . . . .
H36 H 0.5615 0.7967 0.5635 0.075 Uiso 1 1 calc R U . . .
C37 C 0.5006(2) 0.6694(3) 0.53408(15) 0.0612(9) Uani 1 1 d . . . . .
C38 C 0.4471(2) 0.6211(2) 0.48334(16) 0.0591(9) Uani 1 1 d . . . . .
H38 H 0.4296 0.5571 0.4882 0.071 Uiso 1 1 calc R U . . .
C39 C 0.4192(2) 0.6683(2) 0.42495(15) 0.0518(8) Uani 1 1 d . . . . .
H39 H 0.3841 0.6350 0.3900 0.062 Uiso 1 1 calc R U . . .
C40 C 0.3056(2) 0.9047(2) 0.39321(16) 0.0507(8) Uani 1 1 d . . . . .
C41 C 0.0793(2) 0.6572(3) 0.37691(17) 0.0655(10) Uani 1 1 d . . . . .
C42 C 0.0738(2) 0.7406(3) 0.41084(17) 0.0746(11) Uani 1 1 d . . . . .
H42 H 0.1057 0.7960 0.4083 0.089 Uiso 1 1 calc R U . . .
C43 C 0.0201(2) 0.7413(5) 0.44896(19) 0.1011(17) Uani 1 1 d . . . . .
H43 H 0.0163 0.7970 0.4728 0.121 Uiso 1 1 calc R U . . .
C44 C -0.0276(3) 0.6595(6) 0.4514(3) 0.129(2) Uani 1 1 d . . . . .
H44 H -0.0637 0.6602 0.4770 0.154 Uiso 1 1 calc R U . . .
C45 C -0.0226(4) 0.5783(5) 0.4172(3) 0.134(2) Uani 1 1 d . . . . .
H45 H -0.0560 0.5238 0.4189 0.161 Uiso 1 1 calc R U . . .
C46 C 0.0316(3) 0.5749(4) 0.3797(2) 0.0986(14) Uani 1 1 d . . . . .
H46 H 0.0358 0.5183 0.3568 0.118 Uiso 1 1 calc R U . . .
C47 C 0.4803(2) 0.5345(2) 0.26060(16) 0.0625(9) Uani 1 1 d . . . . .
H47A H 0.5368 0.5180 0.2614 0.094 Uiso 1 1 calc R U . . .
H47B H 0.4459 0.4763 0.2518 0.094 Uiso 1 1 calc R U . . .
H47C H 0.4804 0.5610 0.3014 0.094 Uiso 1 1 calc R U . . .
C48 C 0.4434(2) 0.5672(3) 0.14345(16) 0.0628(9) Uani 1 1 d . . . . .
H48A H 0.4999 0.5534 0.1429 0.094 Uiso 1 1 calc R U . . .
H48B H 0.4181 0.6137 0.1102 0.094 Uiso 1 1 calc R U . . .
H48C H 0.4112 0.5074 0.1364 0.094 Uiso 1 1 calc R U . . .
Cl1 Cl 0.67874(8) 0.91445(8) -0.11155(5) 0.0981(4) Uani 1 1 d . . . . .
Cl2 Cl 0.92282(6) 0.52421(7) 0.19201(5) 0.0756(3) Uani 1 1 d . . . . .
Cl3 Cl 0.53766(9) 0.60788(8) 0.60691(4) 0.1022(4) Uani 1 1 d . . . . .
Cl4 Cl 0.29421(5) 0.93416(6) 0.27133(4) 0.0606(2) Uani 1 1 d . . . . .
N1 N 0.9112(2) 0.5367(3) 0.02643(18) 0.0890(11) Uani 1 1 d . . . . .
N2 N 1.02717(14) 0.70846(19) 0.13030(12) 0.0513(6) Uani 1 1 d . . . . .
N3 N 0.3005(2) 0.9495(2) 0.43538(15) 0.0717(9) Uani 1 1 d . . . . .
N4 N 0.20409(15) 0.74773(19) 0.34594(12) 0.0521(6) Uani 1 1 d . . . . .
O1 O 0.67613(14) 0.6747(2) 0.17460(12) 0.0751(7) Uani 1 1 d . . . . .
O2 O 0.95944(12) 0.75924(17) 0.20298(10) 0.0601(6) Uani 1 1 d . . . . .
O3 O 0.55776(12) 0.80661(15) 0.31180(10) 0.0532(5) Uani 1 1 d . . . . .
O4 O 0.27798(11) 0.69964(15) 0.27651(9) 0.0481(5) Uani 1 1 d . . . . .
S1 S 1.09940(5) 0.79715(7) 0.15647(4) 0.0569(2) Uani 1 1 d . . . . .
S2 S 0.14445(6) 0.64632(8) 0.32574(5) 0.0703(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.214(4) . ?
C1 C6 1.471(4) . ?
C1 C2 1.511(5) . ?
C2 C3 1.506(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C24 1.505(5) . ?
C3 C4 1.512(5) . ?
C3 C23 1.557(6) . ?
C4 C5 1.484(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.328(4) . ?
C5 O2 1.389(3) . ?
C6 C7 1.491(4) . ?
C7 C10 1.520(4) . ?
C7 C8 1.553(4) . ?
C7 H7 0.9800 . ?
C8 C16 1.467(5) . ?
C8 C9 1.508(4) . ?
C8 Cl2 1.815(3) . ?
C9 N2 1.251(3) . ?
C9 O2 1.374(3) . ?
C10 C11 1.380(4) . ?
C10 C15 1.382(4) . ?
C11 C12 1.382(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(5) . ?
C13 Cl1 1.743(3) . ?
C14 C15 1.379(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N1 1.131(4) . ?
C17 C22 1.379(4) . ?
C17 C18 1.379(4) . ?
C17 S1 1.772(3) . ?
C18 C19 1.383(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.367(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O3 1.218(3) . ?
C25 C30 1.471(4) . ?
C25 C26 1.497(4) . ?
C26 C27 1.524(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C47 1.521(4) . ?
C27 C48 1.532(4) . ?
C27 C28 1.535(4) . ?
C28 C29 1.480(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.328(4) . ?
C29 O4 1.389(3) . ?
C30 C31 1.500(4) . ?
C31 C34 1.520(4) . ?
C31 C32 1.550(4) . ?
C31 H31 0.9800 . ?
C32 C40 1.471(4) . ?
C32 C33 1.500(4) . ?
C32 Cl4 1.814(3) . ?
C33 N4 1.255(3) . ?
C33 O4 1.372(3) . ?
C34 C35 1.384(4) . ?
C34 C39 1.389(4) . ?
C35 C36 1.381(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.369(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.368(5) . ?
C37 Cl3 1.741(3) . ?
C38 C39 1.380(4) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 N3 1.126(4) . ?
C41 C42 1.369(5) . ?
C41 C46 1.381(5) . ?
C41 S2 1.772(3) . ?
C42 C43 1.385(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.373(8) . ?
C43 H43 0.9300 . ?
C44 C45 1.346(8) . ?
C44 H44 0.9300 . ?
C45 C46 1.382(6) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
N2 S1 1.677(3) . ?
N4 S2 1.677(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 120.5(3) . . ?
O1 C1 C2 123.3(3) . . ?
C6 C1 C2 116.2(3) . . ?
C3 C2 C1 114.3(3) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C24 C3 C2 112.7(3) . . ?
C24 C3 C4 111.4(3) . . ?
C2 C3 C4 109.3(3) . . ?
C24 C3 C23 107.6(3) . . ?
C2 C3 C23 107.4(3) . . ?
C4 C3 C23 108.3(3) . . ?
C5 C4 C3 112.8(3) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 O2 121.8(3) . . ?
C6 C5 C4 126.2(3) . . ?
O2 C5 C4 112.0(3) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 122.5(3) . . ?
C1 C6 C7 118.4(3) . . ?
C6 C7 C10 113.9(2) . . ?
C6 C7 C8 106.9(2) . . ?
C10 C7 C8 111.8(2) . . ?
C6 C7 H7 108.0 . . ?
C10 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C16 C8 C9 111.2(2) . . ?
C16 C8 C7 112.3(3) . . ?
C9 C8 C7 110.2(2) . . ?
C16 C8 Cl2 106.7(2) . . ?
C9 C8 Cl2 107.9(2) . . ?
C7 C8 Cl2 108.4(2) . . ?
N2 C9 O2 122.4(3) . . ?
N2 C9 C8 120.7(3) . . ?
O2 C9 C8 116.9(2) . . ?
C11 C10 C15 117.8(3) . . ?
C11 C10 C7 122.5(3) . . ?
C15 C10 C7 119.6(3) . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 Cl1 118.9(3) . . ?
C12 C13 Cl1 119.8(3) . . ?
C13 C14 C15 118.9(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C10 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
N1 C16 C8 176.9(4) . . ?
C22 C17 C18 120.0(3) . . ?
C22 C17 S1 116.6(2) . . ?
C18 C17 S1 123.4(2) . . ?
C17 C18 C19 119.3(3) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 119.8(3) . . ?
C21 C22 H22 120.1 . . ?
C17 C22 H22 120.1 . . ?
C3 C23 H23A 109.5 . . ?
C3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 C24 H24A 109.5 . . ?
C3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 C30 120.4(3) . . ?
O3 C25 C26 122.7(2) . . ?
C30 C25 C26 116.8(2) . . ?
C25 C26 C27 114.2(2) . . ?
C25 C26 H26A 108.7 . . ?
C27 C26 H26A 108.7 . . ?
C25 C26 H26B 108.7 . . ?
C27 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C47 C27 C26 110.7(3) . . ?
C47 C27 C48 109.2(2) . . ?
C26 C27 C48 109.6(2) . . ?
C47 C27 C28 110.5(2) . . ?
C26 C27 C28 107.4(2) . . ?
C48 C27 C28 109.5(2) . . ?
C29 C28 C27 112.1(2) . . ?
C29 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C30 C29 O4 122.0(2) . . ?
C30 C29 C28 125.7(2) . . ?
O4 C29 C28 112.3(2) . . ?
C29 C30 C25 119.2(2) . . ?
C29 C30 C31 122.3(2) . . ?
C25 C30 C31 118.5(2) . . ?
C30 C31 C34 113.5(2) . . ?
C30 C31 C32 106.7(2) . . ?
C34 C31 C32 111.3(2) . . ?
C30 C31 H31 108.4 . . ?
C34 C31 H31 108.4 . . ?
C32 C31 H31 108.4 . . ?
C40 C32 C33 111.9(2) . . ?
C40 C32 C31 110.9(2) . . ?
C33 C32 C31 110.3(2) . . ?
C40 C32 Cl4 106.54(19) . . ?
C33 C32 Cl4 108.1(2) . . ?
C31 C32 Cl4 108.95(18) . . ?
N4 C33 O4 122.5(3) . . ?
N4 C33 C32 121.4(3) . . ?
O4 C33 C32 116.1(2) . . ?
C35 C34 C39 118.1(3) . . ?
C35 C34 C31 120.3(3) . . ?
C39 C34 C31 121.7(3) . . ?
C36 C35 C34 121.3(3) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C37 C36 C35 119.0(3) . . ?
C37 C36 H36 120.5 . . ?
C35 C36 H36 120.5 . . ?
C38 C37 C36 121.4(3) . . ?
C38 C37 Cl3 118.8(3) . . ?
C36 C37 Cl3 119.8(3) . . ?
C37 C38 C39 119.2(3) . . ?
C37 C38 H38 120.4 . . ?
C39 C38 H38 120.4 . . ?
C38 C39 C34 121.0(3) . . ?
C38 C39 H39 119.5 . . ?
C34 C39 H39 119.5 . . ?
N3 C40 C32 175.1(4) . . ?
C42 C41 C46 120.9(4) . . ?
C42 C41 S2 124.0(3) . . ?
C46 C41 S2 115.1(3) . . ?
C41 C42 C43 119.1(4) . . ?
C41 C42 H42 120.4 . . ?
C43 C42 H42 120.4 . . ?
C44 C43 C42 119.8(5) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C45 C44 C43 120.7(5) . . ?
C45 C44 H44 119.6 . . ?
C43 C44 H44 119.6 . . ?
C44 C45 C46 120.7(5) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C41 C46 C45 118.7(5) . . ?
C41 C46 H46 120.6 . . ?
C45 C46 H46 120.6 . . ?
C27 C47 H47A 109.5 . . ?
C27 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C27 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C27 C48 H48A 109.5 . . ?
C27 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C27 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C9 N2 S1 120.0(2) . . ?
C33 N4 S2 119.1(2) . . ?
C9 O2 C5 120.2(2) . . ?
C33 O4 C29 120.2(2) . . ?
N2 S1 C17 98.68(13) . . ?
N4 S2 C41 100.82(16) . . ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.050

