# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Jie Wu'
_publ_contact_author_email       JIE_WU@FUDAN.EDU.CN

_publ_section_title              
;
Multicatalytic Tandem Reaction
of N'-(2-Alkynylbenzylidene)hydrazide with Indole
;
loop_
_publ_author_name
'Jie Wu.'
'Xiaodi Yang.'
'Xingxin Yu.'

# Attachment '6_3j.cif'

data_wujie090408_0m
_database_code_depnum_ccdc_archive 'CCDC 735059'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 Br Cl F4 N3 O4 S'
_chemical_formula_weight         661.87

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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   11.839(2)
_cell_length_b                   10.8146(18)
_cell_length_c                   21.529(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.293(2)
_cell_angle_gamma                90.00
_cell_volume                     2720.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4134
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      23.72

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1332
_exptl_absorpt_coefficient_mu    1.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.616222
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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            14327
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5342
_reflns_number_gt                3710
_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 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^)+(0.0503P)^2^+1.6405P] 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     SHELXL
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5342
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.041
_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
Br1 Br 0.65462(4) 0.48335(4) 0.063454(19) 0.08594(19) Uani 1 1 d . . .
C12 C 0.8642(2) 0.0949(3) 0.24820(13) 0.0436(6) Uani 1 1 d . . .
N1 N 0.92944(17) 0.1634(2) 0.29230(11) 0.0445(5) Uani 1 1 d . . .
C19 C 0.6751(2) 0.2002(2) 0.19344(12) 0.0418(6) Uani 1 1 d . . .
C10 C 1.0362(2) -0.0147(3) 0.23100(13) 0.0450(6) Uani 1 1 d . . .
C8 C 1.0477(2) 0.1517(3) 0.30669(13) 0.0453(6) Uani 1 1 d . . .
C9 C 1.0982(2) 0.0628(3) 0.27674(14) 0.0486(7) Uani 1 1 d . . .
H15 H 1.1770 0.0524 0.2867 0.058 Uiso 1 1 calc R . .
C18 C 0.7391(2) 0.1153(2) 0.23745(13) 0.0463(7) Uani 1 1 d . . .
C11 C 0.9167(2) 0.0041(2) 0.21584(13) 0.0437(6) Uani 1 1 d . . .
F1 F 0.84516(17) -0.23723(19) 0.09996(10) 0.0811(6) Uani 1 1 d . . .
C24 C 0.7051(2) 0.2869(3) 0.15122(13) 0.0490(7) Uani 1 1 d . . .
H26 H 0.7807 0.2978 0.1455 0.059 Uiso 1 1 calc R . .
C1 C 1.1132(2) 0.2350(3) 0.35392(13) 0.0472(7) Uani 1 1 d . . .
N3 N 0.55454(18) 0.0962(2) 0.24534(12) 0.0559(6) Uani 1 1 d . . .
H2A H 0.4931 0.0707 0.2578 0.067 Uiso 1 1 calc R . .
C16 C 0.8519(2) -0.0713(3) 0.16962(14) 0.0524(7) Uani 1 1 d . . .
H13 H 0.7735 -0.0592 0.1580 0.063 Uiso 1 1 calc R . .
N2 N 0.87716(19) 0.2538(2) 0.32452(12) 0.0617(7) Uani 1 1 d . . .
H2B H 0.8044 0.2650 0.3160 0.074 Uiso 1 1 calc R . .
H2C H 0.9178 0.2983 0.3528 0.074 Uiso 1 1 calc R . .
C2 C 1.1165(2) 0.3615(3) 0.34534(14) 0.0540(7) Uani 1 1 d . . .
H2 H 1.0679 0.3971 0.3119 0.065 Uiso 1 1 calc R . .
C21 C 0.4725(2) 0.2539(3) 0.16506(15) 0.0571(8) Uani 1 1 d . . .
H23 H 0.3962 0.2423 0.1692 0.069 Uiso 1 1 calc R . .
C13 C 1.0876(2) -0.1100(3) 0.20091(15) 0.0566(8) Uani 1 1 d . . .
H10 H 1.1661 -0.1230 0.2109 0.068 Uiso 1 1 calc R . .
C17 C 0.6623(2) 0.0548(3) 0.26731(15) 0.0545(7) Uani 1 1 d . . .
H20 H 0.6806 -0.0055 0.2980 0.065 Uiso 1 1 calc R . .
C15 C 0.9067(3) -0.1612(3) 0.14284(14) 0.0554(7) Uani 1 1 d . . .
C22 C 0.5034(3) 0.3394(3) 0.12410(15) 0.0612(8) Uani 1 1 d . . .
H24 H 0.4473 0.3870 0.0999 0.073 Uiso 1 1 calc R . .
C20 C 0.5594(2) 0.1848(3) 0.20031(14) 0.0478(7) Uani 1 1 d . . .
C23 C 0.6171(3) 0.3561(3) 0.11815(13) 0.0560(7) Uani 1 1 d . . .
O1 O 1.3389(2) 0.4486(2) 0.47629(13) 0.0869(8) Uani 1 1 d . . .
C4 C 1.2613(2) 0.3848(3) 0.43525(15) 0.0576(8) Uani 1 1 d . . .
F3 F 0.4905(2) 0.8206(2) 0.44871(11) 0.1090(8) Uani 1 1 d . . .
C3 C 1.1900(3) 0.4365(3) 0.38511(15) 0.0561(7) Uani 1 1 d . . .
H3 H 1.1913 0.5213 0.3781 0.067 Uiso 1 1 calc R . .
C5 C 1.2555(3) 0.2587(3) 0.44607(16) 0.0694(9) Uani 1 1 d . . .
H6 H 1.3009 0.2240 0.4810 0.083 Uiso 1 1 calc R . .
C6 C 1.1836(2) 0.1847(3) 0.40566(15) 0.0636(9) Uani 1 1 d . . .
H5 H 1.1819 0.1000 0.4130 0.076 Uiso 1 1 calc R . .
C25 C 0.4443(4) 0.9119(4) 0.41467(18) 0.0771(10) Uani 1 1 d . . .
C14 C 1.0241(3) -0.1832(3) 0.15746(15) 0.0607(8) Uani 1 1 d . . .
H9 H 1.0581 -0.2467 0.1379 0.073 Uiso 1 1 calc R . .
F4 F 0.5181(3) 1.0029(3) 0.42181(14) 0.1467(14) Uani 1 1 d . . .
C7 C 1.3644(4) 0.5730(4) 0.4600(2) 0.0956(13) Uani 1 1 d . . .
H7A H 1.3871 0.5738 0.4192 0.143 Uiso 1 1 calc R . .
H7B H 1.4255 0.6047 0.4906 0.143 Uiso 1 1 calc R . .
H7C H 1.2976 0.6236 0.4594 0.143 Uiso 1 1 calc R . .
F2 F 0.3553(3) 0.9466(4) 0.43955(13) 0.1599(15) Uani 1 1 d . . .
Cl1 Cl 0.59189(13) 0.83156(14) 1.02095(6) 0.1266(5) Uani 1 1 d . . .
C26 C 0.4879(4) 0.9422(5) 0.9842(2) 0.1163(18) Uani 1 1 d . . .
H34A H 0.4933 0.9506 0.9399 0.140 Uiso 1 1 calc R . .
H34B H 0.4112 0.9150 0.9878 0.140 Uiso 1 1 calc R . .
S1 S 0.40448(6) 0.87253(8) 0.33249(4) 0.0537(2) Uani 1 1 d . . .
O2 O 0.37260(18) 0.9905(2) 0.30363(11) 0.0693(6) Uani 1 1 d . . .
O3 O 0.50790(18) 0.8235(2) 0.31649(11) 0.0744(7) Uani 1 1 d . . .
O4 O 0.3132(2) 0.7874(3) 0.33094(13) 0.0924(8) Uani 1 1 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
Br1 0.1061(4) 0.0748(3) 0.0718(3) 0.01797(19) -0.0011(2) 0.0117(2)
C12 0.0301(12) 0.0461(15) 0.0538(16) 0.0095(12) 0.0050(11) 0.0028(11)
N1 0.0301(10) 0.0477(13) 0.0556(13) 0.0047(11) 0.0064(10) 0.0033(10)
C19 0.0285(12) 0.0426(15) 0.0519(16) -0.0082(12) -0.0010(11) 0.0011(11)
C10 0.0324(13) 0.0514(16) 0.0521(16) 0.0112(13) 0.0096(12) 0.0056(12)
C8 0.0274(12) 0.0531(16) 0.0543(16) 0.0115(13) 0.0032(11) 0.0012(12)
C9 0.0284(13) 0.0573(17) 0.0600(17) 0.0109(14) 0.0063(12) 0.0032(12)
C18 0.0304(13) 0.0466(15) 0.0611(18) 0.0010(13) 0.0050(12) 0.0021(11)
C11 0.0339(13) 0.0466(16) 0.0515(16) 0.0116(12) 0.0095(12) 0.0017(11)
F1 0.0706(12) 0.0832(14) 0.0876(14) -0.0264(11) 0.0067(10) -0.0042(11)
C24 0.0389(14) 0.0501(16) 0.0553(17) -0.0039(13) -0.0005(12) 0.0007(12)
C1 0.0300(13) 0.0542(17) 0.0564(17) 0.0076(13) 0.0039(12) 0.0010(12)
N3 0.0292(11) 0.0597(15) 0.0800(18) -0.0046(14) 0.0127(11) -0.0036(11)
C16 0.0376(14) 0.0575(18) 0.0619(18) 0.0047(15) 0.0069(13) -0.0023(13)
N2 0.0333(12) 0.0659(17) 0.0843(19) -0.0184(14) 0.0045(12) 0.0061(12)
C2 0.0480(16) 0.0589(19) 0.0534(17) 0.0072(14) 0.0038(13) 0.0062(14)
C21 0.0284(13) 0.066(2) 0.073(2) -0.0232(17) -0.0050(13) 0.0083(13)
C13 0.0368(14) 0.070(2) 0.0659(19) 0.0052(16) 0.0160(14) 0.0086(14)
C17 0.0378(15) 0.0521(17) 0.074(2) 0.0041(15) 0.0094(14) -0.0003(13)
C15 0.0536(17) 0.0576(18) 0.0559(18) -0.0022(15) 0.0114(14) -0.0040(15)
C22 0.0513(17) 0.064(2) 0.0604(19) -0.0116(16) -0.0135(15) 0.0204(15)
C20 0.0297(13) 0.0506(16) 0.0613(17) -0.0153(14) 0.0021(12) 0.0012(12)
C23 0.0572(18) 0.0553(18) 0.0508(17) -0.0049(14) -0.0050(13) 0.0066(14)
O1 0.0789(17) 0.0783(17) 0.0918(19) -0.0007(14) -0.0215(14) -0.0214(14)
C4 0.0420(15) 0.066(2) 0.0630(19) -0.0003(16) 0.0023(14) -0.0064(14)
F3 0.128(2) 0.1026(18) 0.0817(15) 0.0210(13) -0.0268(14) 0.0119(15)
C3 0.0541(17) 0.0504(17) 0.0643(19) 0.0011(15) 0.0111(15) 0.0011(14)
C5 0.0540(18) 0.071(2) 0.073(2) 0.0185(18) -0.0184(16) -0.0043(16)
C6 0.0479(16) 0.0571(18) 0.078(2) 0.0169(16) -0.0124(15) -0.0048(14)
C25 0.081(2) 0.074(2) 0.071(2) 0.001(2) -0.001(2) 0.013(2)
C14 0.0526(18) 0.066(2) 0.068(2) -0.0008(16) 0.0227(15) 0.0081(15)
F4 0.215(4) 0.107(2) 0.100(2) -0.0170(15) -0.030(2) -0.059(2)
C7 0.089(3) 0.081(3) 0.111(3) -0.018(2) -0.001(2) -0.025(2)
F2 0.175(3) 0.231(4) 0.0805(18) 0.000(2) 0.041(2) 0.099(3)
Cl1 0.1486(12) 0.1428(12) 0.0885(8) 0.0225(8) 0.0193(7) 0.0466(9)
C26 0.093(3) 0.173(6) 0.088(3) -0.018(3) 0.031(3) -0.024(3)
S1 0.0322(3) 0.0707(5) 0.0570(4) -0.0007(4) 0.0032(3) -0.0013(3)
O2 0.0474(12) 0.0893(17) 0.0731(15) 0.0224(12) 0.0153(11) 0.0177(11)
O3 0.0484(12) 0.0852(17) 0.0901(17) -0.0108(13) 0.0126(11) 0.0125(11)
O4 0.0534(13) 0.115(2) 0.105(2) 0.0069(17) 0.0004(13) -0.0318(14)

_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
Br1 C23 1.910(3) . ?
C12 N1 1.346(3) . ?
C12 C11 1.406(4) . ?
C12 C18 1.477(3) . ?
N1 C8 1.390(3) . ?
N1 N2 1.400(3) . ?
C19 C24 1.391(4) . ?
C19 C20 1.411(4) . ?
C19 C18 1.443(4) . ?
C10 C13 1.407(4) . ?
C10 C9 1.406(4) . ?
C10 C11 1.415(3) . ?
C8 C9 1.350(4) . ?
C8 C1 1.481(4) . ?
C9 H15 0.9300 . ?
C18 C17 1.363(4) . ?
C11 C16 1.413(4) . ?
F1 C15 1.357(3) . ?
C24 C23 1.383(4) . ?
C24 H26 0.9300 . ?
C1 C2 1.381(4) . ?
C1 C6 1.390(4) . ?
N3 C17 1.362(3) . ?
N3 C20 1.371(4) . ?
N3 H2A 0.8600 . ?
C16 C15 1.349(4) . ?
C16 H13 0.9300 . ?
N2 H2B 0.8600 . ?
N2 H2C 0.8600 . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C21 C22 1.368(4) . ?
C21 C20 1.394(4) . ?
C21 H23 0.9300 . ?
C13 C14 1.356(4) . ?
C13 H10 0.9300 . ?
C17 H20 0.9300 . ?
C15 C14 1.396(4) . ?
C22 C23 1.385(4) . ?
C22 H24 0.9300 . ?
O1 C4 1.356(4) . ?
O1 C7 1.434(5) . ?
C4 C3 1.377(4) . ?
C4 C5 1.387(5) . ?
F3 C25 1.297(4) . ?
C3 H3 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H6 0.9300 . ?
C6 H5 0.9300 . ?
C25 F4 1.308(5) . ?
C25 F2 1.312(5) . ?
C25 S1 1.807(4) . ?
C14 H9 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
Cl1 C26 1.805(6) . ?
C26 C26 1.431(10) 3_677 ?
C26 H34A 0.9700 . ?
C26 H34B 0.9700 . ?
S1 O4 1.416(2) . ?
S1 O3 1.427(2) . ?
S1 O2 1.442(2) . ?

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
N1 C12 C11 119.0(2) . . ?
N1 C12 C18 118.4(2) . . ?
C11 C12 C18 122.6(2) . . ?
C12 N1 C8 123.4(2) . . ?
C12 N1 N2 119.0(2) . . ?
C8 N1 N2 117.6(2) . . ?
C24 C19 C20 120.2(2) . . ?
C24 C19 C18 134.1(2) . . ?
C20 C19 C18 105.8(2) . . ?
C13 C10 C9 122.9(2) . . ?
C13 C10 C11 119.4(3) . . ?
C9 C10 C11 117.7(2) . . ?
C9 C8 N1 117.8(2) . . ?
C9 C8 C1 122.6(2) . . ?
N1 C8 C1 119.6(2) . . ?
C8 C9 C10 122.5(2) . . ?
C8 C9 H15 118.7 . . ?
C10 C9 H15 118.7 . . ?
C17 C18 C19 107.2(2) . . ?
C17 C18 C12 125.6(3) . . ?
C19 C18 C12 127.2(2) . . ?
C12 C11 C16 121.2(2) . . ?
C12 C11 C10 119.5(2) . . ?
C16 C11 C10 119.2(3) . . ?
C23 C24 C19 116.8(3) . . ?
C23 C24 H26 121.6 . . ?
C19 C24 H26 121.6 . . ?
C2 C1 C6 118.0(3) . . ?
C2 C1 C8 122.3(2) . . ?
C6 C1 C8 119.4(3) . . ?
C17 N3 C20 109.3(2) . . ?
C17 N3 H2A 125.3 . . ?
C20 N3 H2A 125.3 . . ?
C15 C16 C11 118.2(3) . . ?
C15 C16 H13 120.9 . . ?
C11 C16 H13 120.9 . . ?
N1 N2 H2B 120.0 . . ?
N1 N2 H2C 120.0 . . ?
H2B N2 H2C 120.0 . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C22 C21 C20 117.6(3) . . ?
C22 C21 H23 121.2 . . ?
C20 C21 H23 121.2 . . ?
C14 C13 C10 120.8(3) . . ?
C14 C13 H10 119.6 . . ?
C10 C13 H10 119.6 . . ?
N3 C17 C18 109.7(3) . . ?
N3 C17 H20 125.1 . . ?
C18 C17 H20 125.1 . . ?
C16 C15 F1 119.0(3) . . ?
C16 C15 C14 123.8(3) . . ?
F1 C15 C14 117.1(3) . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H24 119.6 . . ?
C23 C22 H24 119.6 . . ?
N3 C20 C21 130.4(3) . . ?
N3 C20 C19 108.0(2) . . ?
C21 C20 C19 121.6(3) . . ?
C24 C23 C22 123.0(3) . . ?
C24 C23 Br1 118.5(2) . . ?
C22 C23 Br1 118.5(2) . . ?
C4 O1 C7 117.7(3) . . ?
O1 C4 C3 124.7(3) . . ?
O1 C4 C5 115.9(3) . . ?
C3 C4 C5 119.4(3) . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H6 119.7 . . ?
C4 C5 H6 119.7 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H5 119.7 . . ?
C1 C6 H5 119.7 . . ?
F3 C25 F4 107.1(3) . . ?
F3 C25 F2 106.3(4) . . ?
F4 C25 F2 107.6(4) . . ?
F3 C25 S1 113.1(3) . . ?
F4 C25 S1 110.9(3) . . ?
F2 C25 S1 111.6(3) . . ?
C13 C14 C15 118.5(3) . . ?
C13 C14 H9 120.8 . . ?
C15 C14 H9 120.8 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C26 C26 Cl1 107.5(5) 3_677 . ?
C26 C26 H34A 110.2 3_677 . ?
Cl1 C26 H34A 110.2 . . ?
C26 C26 H34B 110.2 3_677 . ?
Cl1 C26 H34B 110.2 . . ?
H34A C26 H34B 108.5 . . ?
O4 S1 O3 115.71(17) . . ?
O4 S1 O2 114.80(15) . . ?
O3 S1 O2 113.58(14) . . ?
O4 S1 C25 104.73(19) . . ?
O3 S1 C25 103.04(16) . . ?
O2 S1 C25 102.82(16) . . ?

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
C11 C12 N1 C8 1.8(4) . . . . ?
C18 C12 N1 C8 179.6(2) . . . . ?
C11 C12 N1 N2 180.0(2) . . . . ?
C18 C12 N1 N2 -2.3(4) . . . . ?
C12 N1 C8 C9 -3.3(4) . . . . ?
N2 N1 C8 C9 178.6(2) . . . . ?
C12 N1 C8 C1 177.2(2) . . . . ?
N2 N1 C8 C1 -1.0(4) . . . . ?
N1 C8 C9 C10 1.7(4) . . . . ?
C1 C8 C9 C10 -178.7(3) . . . . ?
C13 C10 C9 C8 -178.0(3) . . . . ?
C11 C10 C9 C8 1.0(4) . . . . ?
C24 C19 C18 C17 178.7(3) . . . . ?
C20 C19 C18 C17 0.3(3) . . . . ?
C24 C19 C18 C12 -2.2(5) . . . . ?
C20 C19 C18 C12 179.4(3) . . . . ?
N1 C12 C18 C17 -90.5(4) . . . . ?
C11 C12 C18 C17 87.2(4) . . . . ?
N1 C12 C18 C19 90.6(3) . . . . ?
C11 C12 C18 C19 -91.7(4) . . . . ?
N1 C12 C11 C16 179.3(2) . . . . ?
C18 C12 C11 C16 1.6(4) . . . . ?
N1 C12 C11 C10 1.1(4) . . . . ?
C18 C12 C11 C10 -176.6(2) . . . . ?
C13 C10 C11 C12 176.6(3) . . . . ?
C9 C10 C11 C12 -2.5(4) . . . . ?
C13 C10 C11 C16 -1.6(4) . . . . ?
C9 C10 C11 C16 179.4(3) . . . . ?
C20 C19 C24 C23 0.9(4) . . . . ?
C18 C19 C24 C23 -177.3(3) . . . . ?
C9 C8 C1 C2 117.6(3) . . . . ?
N1 C8 C1 C2 -62.9(4) . . . . ?
C9 C8 C1 C6 -55.6(4) . . . . ?
N1 C8 C1 C6 124.0(3) . . . . ?
C12 C11 C16 C15 -176.4(3) . . . . ?
C10 C11 C16 C15 1.8(4) . . . . ?
C6 C1 C2 C3 2.4(4) . . . . ?
C8 C1 C2 C3 -170.8(3) . . . . ?
C9 C10 C13 C14 179.4(3) . . . . ?
C11 C10 C13 C14 0.4(4) . . . . ?
C20 N3 C17 C18 0.2(3) . . . . ?
C19 C18 C17 N3 -0.3(3) . . . . ?
C12 C18 C17 N3 -179.4(3) . . . . ?
C11 C16 C15 F1 177.7(3) . . . . ?
C11 C16 C15 C14 -0.9(5) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C17 N3 C20 C21 -179.4(3) . . . . ?
C17 N3 C20 C19 0.0(3) . . . . ?
C22 C21 C20 N3 178.2(3) . . . . ?
C22 C21 C20 C19 -1.2(4) . . . . ?
C24 C19 C20 N3 -178.8(2) . . . . ?
C18 C19 C20 N3 -0.2(3) . . . . ?
C24 C19 C20 C21 0.7(4) . . . . ?
C18 C19 C20 C21 179.3(3) . . . . ?
C19 C24 C23 C22 -2.1(4) . . . . ?
C19 C24 C23 Br1 176.2(2) . . . . ?
C21 C22 C23 C24 1.7(5) . . . . ?
C21 C22 C23 Br1 -176.6(2) . . . . ?
C7 O1 C4 C3 -12.5(5) . . . . ?
C7 O1 C4 C5 167.7(3) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
O1 C4 C3 C2 178.1(3) . . . . ?
C5 C4 C3 C2 -2.0(5) . . . . ?
O1 C4 C5 C6 -177.0(3) . . . . ?
C3 C4 C5 C6 3.1(5) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?
C8 C1 C6 C5 172.1(3) . . . . ?
C10 C13 C14 C15 0.5(5) . . . . ?
C16 C15 C14 C13 -0.3(5) . . . . ?
F1 C15 C14 C13 -179.0(3) . . . . ?
F3 C25 S1 O4 68.1(3) . . . . ?
F4 C25 S1 O4 -171.5(3) . . . . ?
F2 C25 S1 O4 -51.6(4) . . . . ?
F3 C25 S1 O3 -53.3(3) . . . . ?
F4 C25 S1 O3 67.0(3) . . . . ?
F2 C25 S1 O3 -173.1(3) . . . . ?
F3 C25 S1 O2 -171.6(3) . . . . ?
F4 C25 S1 O2 -51.2(3) . . . . ?
F2 C25 S1 O2 68.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.047