# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Xiaofeng Tong'
_publ_contact_author_email       TONGXF@ECUST.EDU.CN

_publ_section_title              
;
PPh3-Catalyzed [2+2+2] and [4+2] Annulations:
Synthesis of Highly Substituted 1,2-Dihydropyridines (DHPs)
;
loop_
_publ_author_name
'Huimin Liu.'
'Qiongmei Zhang.'
'Xiaofeng Tong.'

# Attachment '4ba.cif'

data_cd29198
_database_code_depnum_ccdc_archive 'CCDC 739301'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H27 Cl2 N O4 S'
_chemical_formula_weight         604.52

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7166(13)
_cell_length_b                   12.567(3)
_cell_length_c                   18.230(4)
_cell_angle_alpha                70.430(3)
_cell_angle_beta                 84.280(4)
_cell_angle_gamma                81.087(4)
_cell_volume                     1430.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2903
_cell_measurement_theta_min      4.749
_cell_measurement_theta_max      52.316

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.075
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.60185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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            7546
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5244
_reflns_number_gt                3997
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5244
_refine_ls_number_parameters     356
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0855
_refine_ls_wR_factor_ref         0.2898
_refine_ls_wR_factor_gt          0.2767
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.002

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
S1 S 0.69807(13) 0.66218(7) 0.07218(5) 0.0391(3) Uani 1 1 d . . .
N1 N 0.6418(4) 0.6847(2) 0.15797(17) 0.0395(7) Uani 1 1 d . . .
O1 O 0.5291(5) 0.3646(3) 0.29895(19) 0.0713(10) Uani 1 1 d . . .
O2 O 1.1319(5) 0.7124(3) 0.3123(2) 0.0660(9) Uani 1 1 d . . .
O3 O 0.7971(4) 0.7555(2) 0.02360(15) 0.0503(7) Uani 1 1 d . . .
O4 O 0.5166(4) 0.6404(2) 0.04989(16) 0.0530(7) Uani 1 1 d . . .
C1 C 0.5505(5) 0.5935(3) 0.2199(2) 0.0436(9) Uani 1 1 d . . .
H1A H 0.4915 0.5476 0.1965 0.052 Uiso 1 1 calc R . .
H1B H 0.4435 0.6271 0.2482 0.052 Uiso 1 1 calc R . .
C2 C 0.7639(5) 0.7451(3) 0.1845(2) 0.0369(8) Uani 1 1 d . . .
C3 C 0.8502(5) 0.6923(3) 0.2537(2) 0.0409(8) Uani 1 1 d . . .
C4 C 0.8462(6) 0.5705(3) 0.2919(2) 0.0424(8) Uani 1 1 d . . .
H4 H 0.9419 0.5286 0.3277 0.051 Uiso 1 1 calc R . .
C5 C 0.7049(5) 0.5189(3) 0.2754(2) 0.0421(8) Uani 1 1 d . . .
C6 C 0.6783(6) 0.3989(3) 0.3119(2) 0.0449(9) Uani 1 1 d . . .
C7 C 0.8267(6) 0.3182(3) 0.3676(2) 0.0437(8) Uani 1 1 d . . .
C8 C 1.0333(6) 0.3091(3) 0.3497(2) 0.0510(9) Uani 1 1 d . . .
H8 H 1.0845 0.3569 0.3031 0.061 Uiso 1 1 calc R . .
C9 C 1.1631(7) 0.2288(4) 0.4014(3) 0.0636(12) Uani 1 1 d . . .
H9 H 1.3011 0.2219 0.3890 0.076 Uiso 1 1 calc R . .
C10 C 1.0886(9) 0.1594(5) 0.4707(3) 0.0873(18) Uani 1 1 d . . .
H10 H 1.1765 0.1063 0.5055 0.105 Uiso 1 1 calc R . .
C11 C 0.8841(9) 0.1681(5) 0.4891(3) 0.0830(17) Uani 1 1 d . . .
H11 H 0.8340 0.1218 0.5366 0.100 Uiso 1 1 calc R . .
C12 C 0.7528(7) 0.2464(4) 0.4364(2) 0.0636(12) Uani 1 1 d . . .
H12 H 0.6143 0.2501 0.4478 0.076 Uiso 1 1 calc R . .
C13 C 0.7803(6) 0.8644(3) 0.1370(2) 0.0402(8) Uani 1 1 d . . .
C14 C 0.9626(6) 0.9082(3) 0.1249(2) 0.0499(9) Uani 1 1 d . . .
H14 H 1.0796 0.8599 0.1432 0.060 Uiso 1 1 calc R . .
C15 C 0.9724(8) 1.0218(4) 0.0863(2) 0.0628(12) Uani 1 1 d . . .
H15 H 1.0949 1.0507 0.0793 0.075 Uiso 1 1 calc R . .
C16 C 0.7965(8) 1.0939(3) 0.0576(2) 0.0636(12) Uani 1 1 d . . .
H16 H 0.8020 1.1711 0.0318 0.076 Uiso 1 1 calc R . .
C17 C 0.6203(8) 1.0520(3) 0.0672(2) 0.0579(11) Uani 1 1 d . . .
H17 H 0.5051 1.1005 0.0471 0.069 Uiso 1 1 calc R . .
C18 C 0.6064(6) 0.9368(3) 0.1067(2) 0.0504(9) Uani 1 1 d . . .
H18 H 0.4835 0.9086 0.1127 0.060 Uiso 1 1 calc R . .
C19 C 0.9610(6) 0.7524(3) 0.2920(2) 0.0442(9) Uani 1 1 d . . .
C20 C 0.8607(6) 0.8584(3) 0.3054(2) 0.0430(8) Uani 1 1 d . . .
C21 C 0.9765(7) 0.9395(4) 0.3078(2) 0.0550(10) Uani 1 1 d . . .
H21 H 1.1163 0.9264 0.3017 0.066 Uiso 1 1 calc R . .
C22 C 0.8862(8) 1.0388(4) 0.3190(3) 0.0668(13) Uani 1 1 d . . .
H22 H 0.9655 1.0929 0.3197 0.080 Uiso 1 1 calc R . .
C23 C 0.6806(8) 1.0594(4) 0.3293(3) 0.0684(13) Uani 1 1 d . . .
H23 H 0.6203 1.1275 0.3360 0.082 Uiso 1 1 calc R . .
C24 C 0.5639(8) 0.9778(4) 0.3295(3) 0.0731(14) Uani 1 1 d . . .
H24 H 0.4248 0.9897 0.3386 0.088 Uiso 1 1 calc R . .
C25 C 0.6540(6) 0.8781(4) 0.3163(3) 0.0560(10) Uani 1 1 d . . .
H25 H 0.5746 0.8245 0.3148 0.067 Uiso 1 1 calc R . .
C26 C 0.8699(5) 0.5363(3) 0.0937(2) 0.0381(8) Uani 1 1 d . . .
C27 C 0.8055(6) 0.4326(3) 0.1039(3) 0.0507(10) Uani 1 1 d . . .
H27 H 0.6730 0.4295 0.0950 0.061 Uiso 1 1 calc R . .
C28 C 0.9382(7) 0.3348(3) 0.1273(3) 0.0590(11) Uani 1 1 d . . .
H28 H 0.8937 0.2653 0.1346 0.071 Uiso 1 1 calc R . .
C29 C 1.1366(6) 0.3368(3) 0.1404(2) 0.0502(9) Uani 1 1 d . . .
C30 C 1.1966(6) 0.4418(4) 0.1284(3) 0.0587(11) Uani 1 1 d . . .
H30 H 1.3298 0.4453 0.1362 0.070 Uiso 1 1 calc R . .
C31 C 1.0664(6) 0.5414(3) 0.1053(3) 0.0527(10) Uani 1 1 d . . .
H31 H 1.1109 0.6110 0.0976 0.063 Uiso 1 1 calc R . .
C32 C 1.2798(9) 0.2306(4) 0.1681(3) 0.0778(15) Uani 1 1 d . . .
H32A H 1.4009 0.2373 0.1351 0.117 Uiso 1 1 calc R . .
H32B H 1.2188 0.1672 0.1666 0.117 Uiso 1 1 calc R . .
H32C H 1.3120 0.2186 0.2206 0.117 Uiso 1 1 calc R . .
C33 C 0.2269(18) 0.4096(11) 0.5040(7) 0.174(4) Uiso 1 1 d D . .
H33A H 0.2387 0.3871 0.4576 0.209 Uiso 1 1 calc R . .
H33B H 0.2480 0.3397 0.5477 0.209 Uiso 1 1 calc R . .
Cl1 Cl 0.421(2) 0.4761(14) 0.4985(10) 0.220(8) Uiso 1 1 d D . .
Cl2 Cl -0.019(3) 0.463(3) 0.513(3) 0.287(18) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0429(6) 0.0336(5) 0.0401(5) -0.0099(4) -0.0066(4) -0.0048(4)
N1 0.0408(16) 0.0334(15) 0.0447(16) -0.0114(12) -0.0013(13) -0.0092(12)
O1 0.071(2) 0.0532(18) 0.082(2) 0.0009(15) -0.0190(17) -0.0281(16)
O2 0.0536(18) 0.0627(19) 0.087(2) -0.0310(16) -0.0284(16) 0.0061(14)
O3 0.0626(17) 0.0407(14) 0.0445(14) -0.0091(11) 0.0022(12) -0.0118(12)
O4 0.0492(15) 0.0535(16) 0.0576(16) -0.0163(13) -0.0202(13) -0.0029(12)
C1 0.0398(19) 0.042(2) 0.046(2) -0.0084(15) 0.0013(15) -0.0094(15)
C2 0.0359(17) 0.0308(16) 0.0454(19) -0.0151(14) -0.0022(14) -0.0023(13)
C3 0.044(2) 0.0289(17) 0.048(2) -0.0110(14) -0.0043(16) -0.0034(14)
C4 0.051(2) 0.0328(18) 0.0424(19) -0.0105(14) -0.0068(16) -0.0040(15)
C5 0.049(2) 0.0388(19) 0.0375(18) -0.0117(15) 0.0034(15) -0.0075(15)
C6 0.055(2) 0.040(2) 0.0408(19) -0.0129(15) 0.0038(16) -0.0143(16)
C7 0.054(2) 0.0332(18) 0.0449(19) -0.0114(15) -0.0015(16) -0.0120(15)
C8 0.061(2) 0.039(2) 0.052(2) -0.0124(16) 0.0022(18) -0.0106(17)
C9 0.060(3) 0.050(2) 0.079(3) -0.017(2) -0.013(2) -0.007(2)
C10 0.083(4) 0.067(3) 0.091(4) 0.015(3) -0.040(3) -0.014(3)
C11 0.094(4) 0.081(4) 0.054(3) 0.016(2) -0.018(3) -0.028(3)
C12 0.067(3) 0.063(3) 0.053(2) -0.002(2) -0.001(2) -0.023(2)
C13 0.049(2) 0.0325(18) 0.0397(18) -0.0132(14) -0.0030(15) -0.0044(15)
C14 0.057(2) 0.048(2) 0.046(2) -0.0125(16) -0.0022(17) -0.0161(18)
C15 0.086(3) 0.053(3) 0.053(2) -0.0124(19) 0.001(2) -0.032(2)
C16 0.106(4) 0.034(2) 0.050(2) -0.0087(17) -0.002(2) -0.020(2)
C17 0.082(3) 0.034(2) 0.052(2) -0.0115(17) -0.008(2) 0.007(2)
C18 0.055(2) 0.037(2) 0.058(2) -0.0144(17) -0.0089(18) 0.0006(16)
C19 0.050(2) 0.0391(19) 0.044(2) -0.0135(15) -0.0066(16) -0.0074(16)
C20 0.051(2) 0.0368(18) 0.0421(19) -0.0111(15) -0.0109(16) -0.0079(15)
C21 0.060(2) 0.051(2) 0.063(3) -0.0248(19) -0.010(2) -0.0148(19)
C22 0.091(4) 0.050(2) 0.070(3) -0.025(2) -0.012(3) -0.021(2)
C23 0.084(3) 0.051(3) 0.080(3) -0.037(2) -0.016(3) 0.004(2)
C24 0.059(3) 0.074(3) 0.098(4) -0.048(3) -0.011(3) 0.006(2)
C25 0.052(2) 0.053(2) 0.075(3) -0.035(2) -0.005(2) -0.0077(18)
C26 0.0374(18) 0.0365(18) 0.0410(18) -0.0144(14) -0.0003(14) -0.0041(14)
C27 0.043(2) 0.041(2) 0.075(3) -0.0267(19) -0.0048(19) -0.0061(16)
C28 0.066(3) 0.038(2) 0.077(3) -0.0247(19) 0.001(2) -0.0083(19)
C29 0.054(2) 0.052(2) 0.045(2) -0.0217(17) -0.0036(17) 0.0055(18)
C30 0.040(2) 0.059(3) 0.080(3) -0.027(2) -0.008(2) 0.0000(18)
C31 0.040(2) 0.045(2) 0.077(3) -0.0227(19) -0.0009(19) -0.0099(16)
C32 0.086(4) 0.062(3) 0.078(3) -0.026(2) -0.009(3) 0.026(3)

_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
S1 O4 1.415(3) . ?
S1 O3 1.425(3) . ?
S1 N1 1.678(3) . ?
S1 C26 1.760(4) . ?
N1 C2 1.414(4) . ?
N1 C1 1.475(4) . ?
O1 C6 1.223(4) . ?
O2 C19 1.220(5) . ?
C1 C5 1.500(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.354(5) . ?
C2 C13 1.475(5) . ?
C3 C4 1.458(5) . ?
C3 C19 1.497(5) . ?
C4 C5 1.337(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.462(5) . ?
C6 C7 1.500(5) . ?
C7 C12 1.375(5) . ?
C7 C8 1.390(6) . ?
C8 C9 1.385(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.399(5) . ?
C13 C14 1.387(5) . ?
C14 C15 1.373(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.402(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.342(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.482(5) . ?
C20 C25 1.378(6) . ?
C20 C21 1.388(5) . ?
C21 C22 1.370(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(6) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C31 1.371(5) . ?
C26 C27 1.384(5) . ?
C27 C28 1.368(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.382(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.381(6) . ?
C29 C32 1.486(6) . ?
C30 C31 1.374(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 Cl2 1.701(19) . ?
C33 Cl1 1.635(12) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
Cl1 Cl1 1.31(2) 2_666 ?
Cl2 Cl2 0.95(7) 2_566 ?

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
O4 S1 O3 120.37(16) . . ?
O4 S1 N1 105.81(16) . . ?
O3 S1 N1 106.44(15) . . ?
O4 S1 C26 108.71(16) . . ?
O3 S1 C26 109.58(16) . . ?
N1 S1 C26 104.76(15) . . ?
C2 N1 C1 115.0(3) . . ?
C2 N1 S1 120.5(2) . . ?
C1 N1 S1 115.9(2) . . ?
N1 C1 C5 111.1(3) . . ?
N1 C1 H1A 109.3 . . ?
C5 C1 H1A 109.4 . . ?
N1 C1 H1B 109.5 . . ?
C5 C1 H1B 109.5 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 N1 118.4(3) . . ?
C3 C2 C13 123.8(3) . . ?
N1 C2 C13 117.7(3) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 C19 122.9(3) . . ?
C4 C3 C19 117.3(3) . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 125.5(3) . . ?
C4 C5 C1 116.7(3) . . ?
C6 C5 C1 117.6(3) . . ?
O1 C6 C5 119.5(4) . . ?
O1 C6 C7 119.4(3) . . ?
C5 C6 C7 121.0(3) . . ?
C12 C7 C8 119.4(4) . . ?
C12 C7 C6 118.2(4) . . ?
C8 C7 C6 122.2(3) . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.4(4) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.7 . . ?
C18 C13 C14 119.2(3) . . ?
C18 C13 C2 119.3(3) . . ?
C14 C13 C2 121.4(3) . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.5(4) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.2(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 121.3(4) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C13 119.0(4) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.6 . . ?
O2 C19 C20 121.2(3) . . ?
O2 C19 C3 119.2(3) . . ?
C20 C19 C3 119.6(3) . . ?
C25 C20 C21 119.0(4) . . ?
C25 C20 C19 121.3(3) . . ?
C21 C20 C19 119.7(4) . . ?
C22 C21 C20 120.5(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.8(4) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C24 119.3(4) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.4 . . ?
C23 C24 C25 120.1(5) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 120.2(4) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C31 C26 C27 120.3(3) . . ?
C31 C26 S1 118.9(3) . . ?
C27 C26 S1 120.7(3) . . ?
C28 C27 C26 119.5(4) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 121.6(4) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 H28 119.3 . . ?
C30 C29 C28 117.3(4) . . ?
C30 C29 C32 120.8(4) . . ?
C28 C29 C32 121.9(4) . . ?
C29 C30 C31 122.4(4) . . ?
C29 C30 H30 118.8 . . ?
C31 C30 H30 118.8 . . ?
C26 C31 C30 118.8(4) . . ?
C26 C31 H31 120.5 . . ?
C30 C31 H31 120.7 . . ?
C29 C32 H32A 109.4 . . ?
C29 C32 H32B 109.7 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.3 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
Cl2 C33 Cl1 125.9(16) . . ?
Cl2 C33 H33A 107.3 . . ?
Cl1 C33 H33A 104.7 . . ?
Cl2 C33 H33B 106.8 . . ?
Cl1 C33 H33B 104.7 . . ?
H33A C33 H33B 106.0 . . ?
Cl1 Cl1 C33 174(2) 2_666 . ?
Cl2 Cl2 C33 87(3) 2_566 . ?

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
O4 S1 N1 C2 -158.7(3) . . . . ?
O3 S1 N1 C2 -29.5(3) . . . . ?
C26 S1 N1 C2 86.5(3) . . . . ?
O4 S1 N1 C1 55.1(3) . . . . ?
O3 S1 N1 C1 -175.7(2) . . . . ?
C26 S1 N1 C1 -59.7(3) . . . . ?
C2 N1 C1 C5 -48.3(4) . . . . ?
S1 N1 C1 C5 99.8(3) . . . . ?
C1 N1 C2 C3 25.1(4) . . . . ?
S1 N1 C2 C3 -121.4(3) . . . . ?
C1 N1 C2 C13 -151.5(3) . . . . ?
S1 N1 C2 C13 62.0(4) . . . . ?
N1 C2 C3 C4 11.0(5) . . . . ?
C13 C2 C3 C4 -172.6(3) . . . . ?
N1 C2 C3 C19 -172.3(3) . . . . ?
C13 C2 C3 C19 4.1(6) . . . . ?
C2 C3 C4 C5 -23.2(5) . . . . ?
C19 C3 C4 C5 159.9(3) . . . . ?
C3 C4 C5 C6 -177.1(3) . . . . ?
C3 C4 C5 C1 -2.7(5) . . . . ?
N1 C1 C5 C4 36.8(4) . . . . ?
N1 C1 C5 C6 -148.3(3) . . . . ?
C4 C5 C6 O1 171.2(4) . . . . ?
C1 C5 C6 O1 -3.2(5) . . . . ?
C4 C5 C6 C7 -6.2(6) . . . . ?
C1 C5 C6 C7 179.5(3) . . . . ?
O1 C6 C7 C12 -43.8(5) . . . . ?
C5 C6 C7 C12 133.5(4) . . . . ?
O1 C6 C7 C8 132.0(4) . . . . ?
C5 C6 C7 C8 -50.6(5) . . . . ?
C12 C7 C8 C9 -0.6(6) . . . . ?
C6 C7 C8 C9 -176.4(4) . . . . ?
C7 C8 C9 C10 -1.1(7) . . . . ?
C8 C9 C10 C11 0.8(8) . . . . ?
C9 C10 C11 C12 1.0(9) . . . . ?
C8 C7 C12 C11 2.4(7) . . . . ?
C6 C7 C12 C11 178.4(4) . . . . ?
C10 C11 C12 C7 -2.7(8) . . . . ?
C3 C2 C13 C18 -132.6(4) . . . . ?
N1 C2 C13 C18 43.8(5) . . . . ?
C3 C2 C13 C14 44.0(5) . . . . ?
N1 C2 C13 C14 -139.6(4) . . . . ?
C18 C13 C14 C15 2.4(6) . . . . ?
C2 C13 C14 C15 -174.3(4) . . . . ?
C13 C14 C15 C16 -1.2(6) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C15 C16 C17 C18 0.9(7) . . . . ?
C16 C17 C18 C13 0.3(6) . . . . ?
C14 C13 C18 C17 -2.0(6) . . . . ?
C2 C13 C18 C17 174.8(3) . . . . ?
C2 C3 C19 O2 -127.3(4) . . . . ?
C4 C3 C19 O2 49.5(5) . . . . ?
C2 C3 C19 C20 53.3(5) . . . . ?
C4 C3 C19 C20 -129.9(4) . . . . ?
O2 C19 C20 C25 -150.7(4) . . . . ?
C3 C19 C20 C25 28.7(5) . . . . ?
O2 C19 C20 C21 28.7(6) . . . . ?
C3 C19 C20 C21 -151.9(4) . . . . ?
C25 C20 C21 C22 -1.5(6) . . . . ?
C19 C20 C21 C22 179.1(4) . . . . ?
C20 C21 C22 C23 1.0(7) . . . . ?
C21 C22 C23 C24 1.1(8) . . . . ?
C22 C23 C24 C25 -2.7(8) . . . . ?
C23 C24 C25 C20 2.2(8) . . . . ?
C21 C20 C25 C24 -0.1(6) . . . . ?
C19 C20 C25 C24 179.4(4) . . . . ?
O4 S1 C26 C31 170.2(3) . . . . ?
O3 S1 C26 C31 36.8(4) . . . . ?
N1 S1 C26 C31 -77.0(3) . . . . ?
O4 S1 C26 C27 -14.0(4) . . . . ?
O3 S1 C26 C27 -147.4(3) . . . . ?
N1 S1 C26 C27 98.8(3) . . . . ?
C31 C26 C27 C28 1.4(6) . . . . ?
S1 C26 C27 C28 -174.3(3) . . . . ?
C26 C27 C28 C29 -0.6(7) . . . . ?
C27 C28 C29 C30 -0.4(6) . . . . ?
C27 C28 C29 C32 178.0(4) . . . . ?
C28 C29 C30 C31 0.7(7) . . . . ?
C32 C29 C30 C31 -177.7(4) . . . . ?
C27 C26 C31 C30 -1.1(6) . . . . ?
S1 C26 C31 C30 174.7(3) . . . . ?
C29 C30 C31 C26 0.0(7) . . . . ?
Cl2 C33 Cl1 Cl1 97(23) . . . 2_666 ?
Cl1 C33 Cl2 Cl2 28(7) . . . 2_566 ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.101