# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mo30415b
_database_code_depnum_ccdc_archive 'CCDC 1581322'
_audit_update_record             
;
2017-10-22 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 Br N O3.50 S'
_chemical_formula_weight         531.45

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'
Br Br -0.2901 2.4595 '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                   12.813(2)
_cell_length_b                   14.490(2)
_cell_length_c                   16.225(4)
_cell_angle_alpha                108.147(3)
_cell_angle_beta                 98.120(4)
_cell_angle_gamma                116.118(2)
_cell_volume                     2429.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    243(2)
_cell_measurement_reflns_used    3244
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.49

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1092
_exptl_absorpt_coefficient_mu    1.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7365
_exptl_absorpt_correction_T_max  0.8838
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      243(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15959
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         26.10
_reflns_number_total             9479
_reflns_number_gt                5961
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0722P)²+4.0025P] where P=(Fo²+2Fc²)/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         9479
_refine_ls_number_parameters     606
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1788
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.28383(5) 0.32776(5) 0.22679(4) 0.04909(19) Uani 1 1 d . . .
S1 S 0.15821(12) 0.51323(10) 0.30490(8) 0.0334(3) Uani 1 1 d . . .
N1 N -0.1411(4) 0.2761(4) 0.2252(3) 0.0454(11) Uani 1 1 d . . .
H1 H -0.2142 0.2510 0.2303 0.054 Uiso 1 1 calc R . .
O1 O -0.1274(4) 0.4195(3) 0.1891(3) 0.0509(10) Uani 1 1 d . . .
O2 O 0.2852(3) 0.6369(3) 0.1884(2) 0.0447(9) Uani 1 1 d . . .
H2 H 0.2891 0.5859 0.1502 0.067 Uiso 1 1 calc R . .
O3 O 0.3274(4) 0.7389(3) 0.4002(3) 0.0564(11) Uani 1 1 d . . .
C1 C -0.0843(4) 0.3648(4) 0.2041(3) 0.0350(11) Uani 1 1 d . . .
C2 C 0.0440(4) 0.3830(4) 0.2030(3) 0.0297(10) Uani 1 1 d . . .
C3 C 0.0411(5) 0.2866(4) 0.2246(3) 0.0329(11) Uani 1 1 d . . .
C4 C 0.1241(5) 0.2514(4) 0.2362(3) 0.0379(12) Uani 1 1 d . . .
C5 C 0.0979(7) 0.1621(5) 0.2590(4) 0.0535(16) Uani 1 1 d . . .
H5 H 0.1554 0.1391 0.2664 0.064 Uiso 1 1 calc R . .
C6 C -0.0139(7) 0.1063(6) 0.2710(5) 0.0674(19) Uani 1 1 d . . .
H6 H -0.0319 0.0448 0.2863 0.081 Uiso 1 1 calc R . .
C7 C -0.1010(6) 0.1382(5) 0.2611(4) 0.0567(16) Uani 1 1 d . . .
H7 H -0.1771 0.1006 0.2696 0.068 Uiso 1 1 calc R . .
C8 C -0.0681(5) 0.2291(4) 0.2379(4) 0.0426(13) Uani 1 1 d . . .
C9 C 0.1465(4) 0.6178(4) 0.2708(3) 0.0320(11) Uani 1 1 d . . .
H9 H 0.0656 0.6101 0.2700 0.038 Uiso 1 1 calc R . .
C10 C 0.1589(4) 0.6038(4) 0.1760(3) 0.0339(11) Uani 1 1 d . . .
H10 H 0.1451 0.6592 0.1603 0.041 Uiso 1 1 calc R . .
C11 C 0.0711(4) 0.4879(4) 0.0993(3) 0.0332(11) Uani 1 1 d . . .
H11A H 0.0899 0.4877 0.0427 0.040 Uiso 1 1 calc R . .
H11B H -0.0126 0.4742 0.0898 0.040 Uiso 1 1 calc R . .
C12 C 0.0737(5) 0.3891(4) 0.1146(3) 0.0329(11) Uani 1 1 d . . .
H12 H 0.1588 0.4046 0.1238 0.039 Uiso 1 1 calc R . .
C13 C 0.2450(5) 0.7305(4) 0.3436(3) 0.0387(12) Uani 1 1 d . . .
C14 C 0.2487(5) 0.8372(4) 0.3485(4) 0.0417(12) Uani 1 1 d . . .
C15 C 0.3554(6) 0.9390(5) 0.3971(4) 0.0577(16) Uani 1 1 d . . .
H15 H 0.4274 0.9407 0.4220 0.069 Uiso 1 1 calc R . .
C16 C 0.3595(8) 1.0386(6) 0.4103(5) 0.077(2) Uani 1 1 d . . .
H16 H 0.4340 1.1079 0.4432 0.092 Uiso 1 1 calc R . .
C17 C 0.2541(9) 1.0372(6) 0.3752(5) 0.085(3) Uani 1 1 d . . .
H17 H 0.2561 1.1055 0.3854 0.102 Uiso 1 1 calc R . .
C18 C 0.1473(7) 0.9366(6) 0.3256(5) 0.070(2) Uani 1 1 d . . .
H18 H 0.0759 0.9359 0.3010 0.084 Uiso 1 1 calc R . .
C19 C 0.1421(6) 0.8343(5) 0.3109(4) 0.0478(14) Uani 1 1 d . . .
H19 H 0.0681 0.7648 0.2762 0.057 Uiso 1 1 calc R . .
C20 C -0.0095(5) 0.2759(4) 0.0324(3) 0.0375(12) Uani 1 1 d . . .
C21 C 0.0295(6) 0.2014(6) 0.0041(4) 0.0577(17) Uani 1 1 d . . .
H21 H 0.1097 0.2228 0.0354 0.069 Uiso 1 1 calc R . .
C22 C -0.0435(7) 0.0959(6) -0.0686(4) 0.069(2) Uani 1 1 d . . .
H22 H -0.0135 0.0466 -0.0856 0.083 Uiso 1 1 calc R . .
C23 C -0.1596(6) 0.0640(6) -0.1156(4) 0.0652(18) Uani 1 1 d . . .
H23 H -0.2110 -0.0080 -0.1646 0.078 Uiso 1 1 calc R . .
C24 C -0.2002(6) 0.1377(6) -0.0906(4) 0.0625(18) Uani 1 1 d . . .
H24 H -0.2789 0.1172 -0.1245 0.075 Uiso 1 1 calc R . .
C25 C -0.1286(5) 0.2416(5) -0.0168(4) 0.0475(14) Uani 1 1 d . . .
H25 H -0.1598 0.2898 0.0006 0.057 Uiso 1 1 calc R . .
Br2 Br 0.87962(6) 0.65251(8) 0.42009(5) 0.0805(3) Uani 1 1 d . . .
S2 S 0.63598(12) 0.47744(12) 0.19895(9) 0.0392(3) Uani 1 1 d . . .
N2 N 0.4660(4) 0.6066(4) 0.2778(3) 0.0358(10) Uani 1 1 d . . .
H2A H 0.3956 0.6034 0.2702 0.043 Uiso 1 1 calc R . .
O4 O 0.4726(3) 0.5755(3) 0.1310(2) 0.0434(9) Uani 1 1 d . . .
O5 O 0.8677(3) 0.5978(4) 0.1459(3) 0.0569(11) Uani 1 1 d . . .
H5A H 0.8720 0.5413 0.1191 0.085 Uiso 1 1 calc R . .
O6 O 0.7040(4) 0.3692(4) -0.0104(3) 0.0552(11) Uani 1 1 d . . .
C26 C 0.5189(4) 0.5956(4) 0.2101(3) 0.0347(11) Uani 1 1 d . . .
C27 C 0.6439(4) 0.6119(4) 0.2531(3) 0.0332(11) Uani 1 1 d . . .
C28 C 0.6462(4) 0.6292(4) 0.3508(3) 0.0334(11) Uani 1 1 d . . .
C29 C 0.7275(5) 0.6416(5) 0.4239(4) 0.0419(12) Uani 1 1 d . . .
C30 C 0.7032(6) 0.6492(5) 0.5053(4) 0.0554(16) Uani 1 1 d . . .
H30 H 0.7600 0.6586 0.5553 0.067 Uiso 1 1 calc R . .
C31 C 0.5937(6) 0.6426(5) 0.5118(4) 0.0545(16) Uani 1 1 d . . .
H31 H 0.5768 0.6473 0.5670 0.065 Uiso 1 1 calc R . .
C32 C 0.5075(5) 0.6291(5) 0.4388(4) 0.0461(13) Uani 1 1 d . . .
H32 H 0.4331 0.6241 0.4433 0.055 Uiso 1 1 calc R . .
C33 C 0.5378(5) 0.6235(4) 0.3600(3) 0.0364(11) Uani 1 1 d . . .
C34 C 0.6416(5) 0.4792(4) 0.0871(3) 0.0359(11) Uani 1 1 d . . .
H34 H 0.5697 0.4823 0.0598 0.043 Uiso 1 1 calc R . .
C35 C 0.7577(5) 0.5850(5) 0.0970(4) 0.0435(13) Uani 1 1 d . . .
H35 H 0.7600 0.5796 0.0350 0.052 Uiso 1 1 calc R . .
C36 C 0.7530(5) 0.6904(5) 0.1478(4) 0.0468(13) Uani 1 1 d . . .
H36A H 0.6790 0.6834 0.1126 0.056 Uiso 1 1 calc R . .
H36B H 0.8242 0.7562 0.1488 0.056 Uiso 1 1 calc R . .
C37 C 0.7523(5) 0.7138(5) 0.2464(3) 0.0393(12) Uani 1 1 d . . .
H37 H 0.8295 0.7237 0.2809 0.047 Uiso 1 1 calc R . .
C38 C 0.6276(5) 0.3694(5) 0.0251(4) 0.0411(13) Uani 1 1 d . . .
C39 C 0.5143(5) 0.2590(5) 0.0044(3) 0.0427(13) Uani 1 1 d . . .
C40 C 0.5156(7) 0.1604(6) -0.0340(5) 0.0669(19) Uani 1 1 d . . .
H40 H 0.5868 0.1641 -0.0458 0.080 Uiso 1 1 calc R . .
C41 C 0.4142(8) 0.0560(7) -0.0556(5) 0.080(2) Uani 1 1 d . . .
H41 H 0.4173 -0.0101 -0.0814 0.096 Uiso 1 1 calc R . .
C42 C 0.3104(7) 0.0485(6) -0.0397(5) 0.0670(18) Uani 1 1 d . . .
H42 H 0.2417 -0.0228 -0.0548 0.080 Uiso 1 1 calc R . .
C43 C 0.3049(6) 0.1468(5) -0.0007(4) 0.0559(16) Uani 1 1 d . . .
H43 H 0.2329 0.1420 0.0100 0.067 Uiso 1 1 calc R . .
C44 C 0.4072(5) 0.2505(5) 0.0215(4) 0.0506(14) Uani 1 1 d . . .
H44 H 0.4049 0.3168 0.0487 0.061 Uiso 1 1 calc R . .
C45 C 0.7522(6) 0.8217(5) 0.2953(4) 0.0517(15) Uani 1 1 d . . .
C46 C 0.8299(7) 0.8966(6) 0.3833(5) 0.075(2) Uani 1 1 d . . .
H46 H 0.8894 0.8845 0.4110 0.090 Uiso 1 1 calc R . .
C47 C 0.8224(11) 0.9898(8) 0.4321(6) 0.107(4) Uani 1 1 d . . .
H47 H 0.8767 1.0406 0.4920 0.128 Uiso 1 1 calc R . .
C48 C 0.7351(13) 1.0068(8) 0.3920(9) 0.122(5) Uani 1 1 d . . .
H48 H 0.7286 1.0688 0.4254 0.146 Uiso 1 1 calc R . .
C49 C 0.6584(9) 0.9362(7) 0.3056(7) 0.087(3) Uani 1 1 d . . .
H49 H 0.5993 0.9495 0.2792 0.104 Uiso 1 1 calc R . .
C50 C 0.6661(7) 0.8431(6) 0.2549(5) 0.0625(17) Uani 1 1 d . . .
H50 H 0.6138 0.7951 0.1939 0.075 Uiso 1 1 calc R . .
C52 C 0.4918(10) 0.8271(10) 0.7921(8) 0.151(5) Uani 1 1 d D . .
H52A H 0.4337 0.8333 0.8225 0.227 Uiso 1 1 calc R . .
H52B H 0.5481 0.9004 0.7944 0.227 Uiso 1 1 calc R . .
H52C H 0.5378 0.8023 0.8228 0.227 Uiso 1 1 calc R . .
C53 C 0.4257(8) 0.7453(9) 0.6970(7) 0.102(3) Uani 1 1 d D . .
H53A H 0.4740 0.7691 0.6580 0.122 Uiso 1 1 calc R . .
H53B H 0.4120 0.6710 0.6905 0.122 Uiso 1 1 calc R . .
C54 C 0.2518(9) 0.6626(9) 0.5750(6) 0.104(3) Uani 1 1 d . . .
H54A H 0.3028 0.6903 0.5387 0.125 Uiso 1 1 calc R . .
H54B H 0.2382 0.5875 0.5657 0.125 Uiso 1 1 calc R . .
C55 C 0.1373(9) 0.6543(9) 0.5451(6) 0.111(3) Uani 1 1 d . . .
H55A H 0.0781 0.6052 0.5659 0.167 Uiso 1 1 calc R . .
H55B H 0.1080 0.6230 0.4786 0.167 Uiso 1 1 calc R . .
H55C H 0.1475 0.7290 0.5704 0.167 Uiso 1 1 calc R . .
O7 O 0.3142(4) 0.7384(5) 0.6701(4) 0.0826(15) 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
Br1 C4 1.907(6) . ?
S1 C9 1.823(5) . ?
S1 C2 1.838(5) . ?
N1 C1 1.348(7) . ?
N1 C8 1.405(7) . ?
N1 H1 0.8700 . ?
O1 C1 1.209(6) . ?
O2 C10 1.434(6) . ?
O2 H2 0.8300 . ?
O3 C13 1.232(6) . ?
C1 C2 1.550(6) . ?
C2 C3 1.528(6) . ?
C2 C12 1.553(6) . ?
C3 C8 1.367(7) . ?
C3 C4 1.380(7) . ?
C4 C5 1.370(7) . ?
C5 C6 1.379(10) . ?
C5 H5 0.9400 . ?
C6 C7 1.391(9) . ?
C6 H6 0.9400 . ?
C7 C8 1.385(8) . ?
C7 H7 0.9400 . ?
C9 C13 1.490(7) . ?
C9 C10 1.528(7) . ?
C9 H9 0.9900 . ?
C10 C11 1.509(7) . ?
C10 H10 0.9900 . ?
C11 C12 1.540(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C20 1.517(7) . ?
C12 H12 0.9900 . ?
C13 C14 1.501(7) . ?
C14 C15 1.365(8) . ?
C14 C19 1.393(7) . ?
C15 C16 1.368(9) . ?
C15 H15 0.9400 . ?
C16 C17 1.378(11) . ?
C16 H16 0.9400 . ?
C17 C18 1.359(10) . ?
C17 H17 0.9400 . ?
C18 C19 1.395(8) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C20 C21 1.363(7) . ?
C20 C25 1.397(7) . ?
C21 C22 1.383(9) . ?
C21 H21 0.9400 . ?
C22 C23 1.365(9) . ?
C22 H22 0.9400 . ?
C23 C24 1.362(9) . ?
C23 H23 0.9400 . ?
C24 C25 1.376(8) . ?
C24 H24 0.9400 . ?
C25 H25 0.9400 . ?
Br2 C29 1.897(5) . ?
S2 C27 1.820(5) . ?
S2 C34 1.834(5) . ?
N2 C26 1.374(6) . ?
N2 C33 1.392(6) . ?
N2 H2A 0.8700 . ?
O4 C26 1.219(6) . ?
O5 C35 1.418(6) . ?
O5 H5A 0.8300 . ?
O6 C38 1.205(6) . ?
C26 C27 1.535(6) . ?
C27 C28 1.519(7) . ?
C27 C37 1.568(7) . ?
C28 C29 1.370(7) . ?
C28 C33 1.388(7) . ?
C29 C30 1.381(8) . ?
C30 C31 1.385(9) . ?
C30 H30 0.9400 . ?
C31 C32 1.399(8) . ?
C31 H31 0.9400 . ?
C32 C33 1.375(7) . ?
C32 H32 0.9400 . ?
C34 C38 1.509(8) . ?
C34 C35 1.536(8) . ?
C34 H34 0.9900 . ?
C35 C36 1.525(8) . ?
C35 H35 0.9900 . ?
C36 C37 1.531(7) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C37 C45 1.516(8) . ?
C37 H37 0.9900 . ?
C38 C39 1.503(8) . ?
C39 C40 1.379(8) . ?
C39 C44 1.399(8) . ?
C40 C41 1.382(11) . ?
C40 H40 0.9400 . ?
C41 C42 1.355(10) . ?
C41 H41 0.9400 . ?
C42 C43 1.405(9) . ?
C42 H42 0.9400 . ?
C43 C44 1.378(9) . ?
C43 H43 0.9400 . ?
C44 H44 0.9400 . ?
C45 C46 1.375(9) . ?
C45 C50 1.404(9) . ?
C46 C47 1.389(12) . ?
C46 H46 0.9400 . ?
C47 C48 1.369(15) . ?
C47 H47 0.9400 . ?
C48 C49 1.345(14) . ?
C48 H48 0.9400 . ?
C49 C50 1.398(10) . ?
C49 H49 0.9400 . ?
C50 H50 0.9400 . ?
C52 C53 1.453(12) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C52 H52C 0.9700 . ?
C53 O7 1.382(9) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C54 C55 1.417(11) . ?
C54 O7 1.431(10) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
C55 H55C 0.9700 . ?

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
C9 S1 C2 99.8(2) . . ?
C1 N1 C8 111.9(4) . . ?
C1 N1 H1 124.1 . . ?
C8 N1 H1 124.1 . . ?
C10 O2 H2 109.5 . . ?
O1 C1 N1 125.2(5) . . ?
O1 C1 C2 126.9(5) . . ?
N1 C1 C2 107.9(4) . . ?
C3 C2 C1 101.3(4) . . ?
C3 C2 C12 116.7(4) . . ?
C1 C2 C12 114.9(4) . . ?
C3 C2 S1 105.1(3) . . ?
C1 C2 S1 107.0(3) . . ?
C12 C2 S1 110.8(3) . . ?
C8 C3 C4 117.1(5) . . ?
C8 C3 C2 108.7(4) . . ?
C4 C3 C2 134.1(5) . . ?
C5 C4 C3 121.7(5) . . ?
C5 C4 Br1 116.1(4) . . ?
C3 C4 Br1 122.2(4) . . ?
C4 C5 C6 119.1(6) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C7 122.1(6) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 115.5(6) . . ?
C8 C7 H7 122.2 . . ?
C6 C7 H7 122.2 . . ?
C3 C8 C7 124.6(5) . . ?
C3 C8 N1 110.2(4) . . ?
C7 C8 N1 125.2(5) . . ?
C13 C9 C10 111.8(4) . . ?
C13 C9 S1 105.9(3) . . ?
C10 C9 S1 112.6(3) . . ?
C13 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
S1 C9 H9 108.8 . . ?
O2 C10 C11 112.7(4) . . ?
O2 C10 C9 104.6(4) . . ?
C11 C10 C9 115.6(4) . . ?
O2 C10 H10 107.9 . . ?
C11 C10 H10 107.9 . . ?
C9 C10 H10 107.9 . . ?
C10 C11 C12 115.3(4) . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C20 C12 C11 112.9(4) . . ?
C20 C12 C2 110.8(4) . . ?
C11 C12 C2 111.8(4) . . ?
C20 C12 H12 107.0 . . ?
C11 C12 H12 107.0 . . ?
C2 C12 H12 107.0 . . ?
O3 C13 C9 120.7(5) . . ?
O3 C13 C14 118.2(5) . . ?
C9 C13 C14 121.1(4) . . ?
C15 C14 C19 119.6(5) . . ?
C15 C14 C13 119.5(5) . . ?
C19 C14 C13 120.7(5) . . ?
C14 C15 C16 121.2(6) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 119.9(7) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 119.8(6) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.9(7) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C18 118.6(6) . . ?
C14 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C21 C20 C25 116.7(5) . . ?
C21 C20 C12 120.4(5) . . ?
C25 C20 C12 122.8(4) . . ?
C20 C21 C22 123.0(6) . . ?
C20 C21 H21 118.5 . . ?
C22 C21 H21 118.5 . . ?
C23 C22 C21 119.3(6) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 119.2(6) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 121.4(6) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C20 120.4(5) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
C27 S2 C34 98.4(2) . . ?
C26 N2 C33 112.2(4) . . ?
C26 N2 H2A 123.9 . . ?
C33 N2 H2A 123.9 . . ?
C35 O5 H5A 109.5 . . ?
O4 C26 N2 125.3(4) . . ?
O4 C26 C27 127.6(5) . . ?
N2 C26 C27 107.1(4) . . ?
C28 C27 C26 102.4(4) . . ?
C28 C27 C37 113.9(4) . . ?
C26 C27 C37 111.6(4) . . ?
C28 C27 S2 106.6(3) . . ?
C26 C27 S2 107.6(3) . . ?
C37 C27 S2 113.9(3) . . ?
C29 C28 C33 118.4(5) . . ?
C29 C28 C27 133.0(5) . . ?
C33 C28 C27 108.5(4) . . ?
C28 C29 C30 121.2(5) . . ?
C28 C29 Br2 122.2(4) . . ?
C30 C29 Br2 116.6(4) . . ?
C29 C30 C31 118.8(5) . . ?
C29 C30 H30 120.6 . . ?
C31 C30 H30 120.6 . . ?
C30 C31 C32 122.1(5) . . ?
C30 C31 H31 119.0 . . ?
C32 C31 H31 119.0 . . ?
C33 C32 C31 116.3(5) . . ?
C33 C32 H32 121.8 . . ?
C31 C32 H32 121.8 . . ?
C32 C33 C28 123.3(5) . . ?
C32 C33 N2 127.0(5) . . ?
C28 C33 N2 109.7(4) . . ?
C38 C34 C35 113.6(4) . . ?
C38 C34 S2 109.0(3) . . ?
C35 C34 S2 111.5(4) . . ?
C38 C34 H34 107.5 . . ?
C35 C34 H34 107.5 . . ?
S2 C34 H34 107.5 . . ?
O5 C35 C36 108.1(5) . . ?
O5 C35 C34 112.9(4) . . ?
C36 C35 C34 109.5(4) . . ?
O5 C35 H35 108.7 . . ?
C36 C35 H35 108.7 . . ?
C34 C35 H35 108.7 . . ?
C35 C36 C37 115.8(4) . . ?
C35 C36 H36A 108.3 . . ?
C37 C36 H36A 108.3 . . ?
C35 C36 H36B 108.3 . . ?
C37 C36 H36B 108.3 . . ?
H36A C36 H36B 107.4 . . ?
C45 C37 C36 114.0(4) . . ?
C45 C37 C27 109.6(4) . . ?
C36 C37 C27 112.7(4) . . ?
C45 C37 H37 106.7 . . ?
C36 C37 H37 106.7 . . ?
C27 C37 H37 106.7 . . ?
O6 C38 C39 119.6(5) . . ?
O6 C38 C34 120.8(5) . . ?
C39 C38 C34 119.5(4) . . ?
C40 C39 C44 117.9(6) . . ?
C40 C39 C38 118.3(5) . . ?
C44 C39 C38 123.8(5) . . ?
C39 C40 C41 121.3(6) . . ?
C39 C40 H40 119.3 . . ?
C41 C40 H40 119.3 . . ?
C42 C41 C40 120.3(6) . . ?
C42 C41 H41 119.8 . . ?
C40 C41 H41 119.8 . . ?
C41 C42 C43 120.3(7) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C44 C43 C42 118.7(6) . . ?
C44 C43 H43 120.6 . . ?
C42 C43 H43 120.6 . . ?
C43 C44 C39 121.4(5) . . ?
C43 C44 H44 119.3 . . ?
C39 C44 H44 119.3 . . ?
C46 C45 C50 118.1(7) . . ?
C46 C45 C37 120.9(6) . . ?
C50 C45 C37 120.9(5) . . ?
C45 C46 C47 121.4(9) . . ?
C45 C46 H46 119.3 . . ?
C47 C46 H46 119.3 . . ?
C48 C47 C46 119.3(9) . . ?
C48 C47 H47 120.4 . . ?
C46 C47 H47 120.4 . . ?
C49 C48 C47 121.1(9) . . ?
C49 C48 H48 119.5 . . ?
C47 C48 H48 119.5 . . ?
C48 C49 C50 120.4(9) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C49 C50 C45 119.7(8) . . ?
C49 C50 H50 120.2 . . ?
C45 C50 H50 120.2 . . ?
C53 C52 H52A 109.5 . . ?
C53 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C53 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
O7 C53 C52 108.8(8) . . ?
O7 C53 H53A 109.9 . . ?
C52 C53 H53A 109.9 . . ?
O7 C53 H53B 109.9 . . ?
C52 C53 H53B 109.9 . . ?
H53A C53 H53B 108.3 . . ?
C55 C54 O7 110.3(7) . . ?
C55 C54 H54A 109.6 . . ?
O7 C54 H54A 109.6 . . ?
C55 C54 H54B 109.6 . . ?
O7 C54 H54B 109.6 . . ?
H54A C54 H54B 108.1 . . ?
C54 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C53 O7 C54 108.9(7) . . ?

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
C8 N1 C1 O1 179.4(5) . . . . ?
C8 N1 C1 C2 -0.8(6) . . . . ?
O1 C1 C2 C3 -178.7(5) . . . . ?
N1 C1 C2 C3 1.5(5) . . . . ?
O1 C1 C2 C12 -52.0(7) . . . . ?
N1 C1 C2 C12 128.1(4) . . . . ?
O1 C1 C2 S1 71.5(6) . . . . ?
N1 C1 C2 S1 -108.4(4) . . . . ?
C9 S1 C2 C3 -177.9(3) . . . . ?
C9 S1 C2 C1 -70.8(3) . . . . ?
C9 S1 C2 C12 55.2(3) . . . . ?
C1 C2 C3 C8 -1.7(5) . . . . ?
C12 C2 C3 C8 -127.2(5) . . . . ?
S1 C2 C3 C8 109.6(4) . . . . ?
C1 C2 C3 C4 -178.6(5) . . . . ?
C12 C2 C3 C4 55.8(7) . . . . ?
S1 C2 C3 C4 -67.4(6) . . . . ?
C8 C3 C4 C5 0.8(7) . . . . ?
C2 C3 C4 C5 177.5(5) . . . . ?
C8 C3 C4 Br1 -176.5(4) . . . . ?
C2 C3 C4 Br1 0.2(8) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
Br1 C4 C5 C6 177.1(5) . . . . ?
C4 C5 C6 C7 -0.3(10) . . . . ?
C5 C6 C7 C8 0.4(9) . . . . ?
C4 C3 C8 C7 -0.7(8) . . . . ?
C2 C3 C8 C7 -178.2(5) . . . . ?
C4 C3 C8 N1 178.9(4) . . . . ?
C2 C3 C8 N1 1.4(6) . . . . ?
C6 C7 C8 C3 0.1(9) . . . . ?
C6 C7 C8 N1 -179.4(5) . . . . ?
C1 N1 C8 C3 -0.4(6) . . . . ?
C1 N1 C8 C7 179.2(5) . . . . ?
C2 S1 C9 C13 -174.0(3) . . . . ?
C2 S1 C9 C10 -51.6(4) . . . . ?
C13 C9 C10 O2 49.4(5) . . . . ?
S1 C9 C10 O2 -69.7(4) . . . . ?
C13 C9 C10 C11 173.9(4) . . . . ?
S1 C9 C10 C11 54.8(5) . . . . ?
O2 C10 C11 C12 64.6(5) . . . . ?
C9 C10 C11 C12 -55.5(5) . . . . ?
C10 C11 C12 C20 -175.8(4) . . . . ?
C10 C11 C12 C2 58.5(5) . . . . ?
C3 C2 C12 C20 51.9(5) . . . . ?
C1 C2 C12 C20 -66.5(5) . . . . ?
S1 C2 C12 C20 172.1(3) . . . . ?
C3 C2 C12 C11 178.7(4) . . . . ?
C1 C2 C12 C11 60.4(5) . . . . ?
S1 C2 C12 C11 -61.1(4) . . . . ?
C10 C9 C13 O3 -109.5(5) . . . . ?
S1 C9 C13 O3 13.5(6) . . . . ?
C10 C9 C13 C14 68.8(6) . . . . ?
S1 C9 C13 C14 -168.2(4) . . . . ?
O3 C13 C14 C15 17.1(8) . . . . ?
C9 C13 C14 C15 -161.3(5) . . . . ?
O3 C13 C14 C19 -157.3(5) . . . . ?
C9 C13 C14 C19 24.3(8) . . . . ?
C19 C14 C15 C16 0.5(10) . . . . ?
C13 C14 C15 C16 -173.9(6) . . . . ?
C14 C15 C16 C17 0.9(12) . . . . ?
C15 C16 C17 C18 -1.7(13) . . . . ?
C16 C17 C18 C19 1.0(12) . . . . ?
C15 C14 C19 C18 -1.2(9) . . . . ?
C13 C14 C19 C18 173.2(6) . . . . ?
C17 C18 C19 C14 0.4(11) . . . . ?
C11 C12 C20 C21 137.4(5) . . . . ?
C2 C12 C20 C21 -96.4(6) . . . . ?
C11 C12 C20 C25 -43.7(7) . . . . ?
C2 C12 C20 C25 82.6(6) . . . . ?
C25 C20 C21 C22 -0.9(10) . . . . ?
C12 C20 C21 C22 178.1(6) . . . . ?
C20 C21 C22 C23 0.8(11) . . . . ?
C21 C22 C23 C24 1.1(11) . . . . ?
C22 C23 C24 C25 -2.7(11) . . . . ?
C23 C24 C25 C20 2.5(10) . . . . ?
C21 C20 C25 C24 -0.7(9) . . . . ?
C12 C20 C25 C24 -179.7(6) . . . . ?
C33 N2 C26 O4 176.7(5) . . . . ?
C33 N2 C26 C27 -2.6(5) . . . . ?
O4 C26 C27 C28 -177.7(5) . . . . ?
N2 C26 C27 C28 1.6(5) . . . . ?
O4 C26 C27 C37 60.1(7) . . . . ?
N2 C26 C27 C37 -120.6(4) . . . . ?
O4 C26 C27 S2 -65.6(6) . . . . ?
N2 C26 C27 S2 113.7(4) . . . . ?
C34 S2 C27 C28 -177.5(3) . . . . ?
C34 S2 C27 C26 73.3(4) . . . . ?
C34 S2 C27 C37 -51.0(4) . . . . ?
C26 C27 C28 C29 175.5(5) . . . . ?
C37 C27 C28 C29 -63.9(7) . . . . ?
S2 C27 C28 C29 62.6(6) . . . . ?
C26 C27 C28 C33 -0.1(5) . . . . ?
C37 C27 C28 C33 120.5(5) . . . . ?
S2 C27 C28 C33 -113.0(4) . . . . ?
C33 C28 C29 C30 -0.5(8) . . . . ?
C27 C28 C29 C30 -175.8(5) . . . . ?
C33 C28 C29 Br2 -179.1(4) . . . . ?
C27 C28 C29 Br2 5.6(8) . . . . ?
C28 C29 C30 C31 0.8(9) . . . . ?
Br2 C29 C30 C31 179.5(5) . . . . ?
C29 C30 C31 C32 -0.3(9) . . . . ?
C30 C31 C32 C33 -0.5(9) . . . . ?
C31 C32 C33 C28 0.8(8) . . . . ?
C31 C32 C33 N2 177.7(5) . . . . ?
C29 C28 C33 C32 -0.3(8) . . . . ?
C27 C28 C33 C32 176.0(5) . . . . ?
C29 C28 C33 N2 -177.7(4) . . . . ?
C27 C28 C33 N2 -1.3(6) . . . . ?
C26 N2 C33 C32 -174.7(5) . . . . ?
C26 N2 C33 C28 2.5(6) . . . . ?
C27 S2 C34 C38 -176.2(3) . . . . ?
C27 S2 C34 C35 57.5(4) . . . . ?
C38 C34 C35 O5 -68.6(6) . . . . ?
S2 C34 C35 O5 55.1(5) . . . . ?
C38 C34 C35 C36 170.9(4) . . . . ?
S2 C34 C35 C36 -65.5(5) . . . . ?
O5 C35 C36 C37 -60.7(6) . . . . ?
C34 C35 C36 C37 62.8(6) . . . . ?
C35 C36 C37 C45 177.9(5) . . . . ?
C35 C36 C37 C27 -56.4(6) . . . . ?
C28 C27 C37 C45 -56.2(5) . . . . ?
C26 C27 C37 C45 59.2(5) . . . . ?
S2 C27 C37 C45 -178.7(4) . . . . ?
C28 C27 C37 C36 175.7(4) . . . . ?
C26 C27 C37 C36 -68.9(5) . . . . ?
S2 C27 C37 C36 53.2(5) . . . . ?
C35 C34 C38 O6 1.3(7) . . . . ?
S2 C34 C38 O6 -123.8(5) . . . . ?
C35 C34 C38 C39 -176.3(4) . . . . ?
S2 C34 C38 C39 58.7(5) . . . . ?
O6 C38 C39 C40 17.2(8) . . . . ?
C34 C38 C39 C40 -165.2(5) . . . . ?
O6 C38 C39 C44 -162.5(5) . . . . ?
C34 C38 C39 C44 15.1(7) . . . . ?
C44 C39 C40 C41 0.3(10) . . . . ?
C38 C39 C40 C41 -179.4(6) . . . . ?
C39 C40 C41 C42 0.4(12) . . . . ?
C40 C41 C42 C43 -0.3(12) . . . . ?
C41 C42 C43 C44 -0.5(11) . . . . ?
C42 C43 C44 C39 1.2(9) . . . . ?
C40 C39 C44 C43 -1.2(9) . . . . ?
C38 C39 C44 C43 178.5(5) . . . . ?
C36 C37 C45 C46 -133.9(6) . . . . ?
C27 C37 C45 C46 98.7(6) . . . . ?
C36 C37 C45 C50 51.3(7) . . . . ?
C27 C37 C45 C50 -76.0(6) . . . . ?
C50 C45 C46 C47 1.4(10) . . . . ?
C37 C45 C46 C47 -173.5(7) . . . . ?
C45 C46 C47 C48 0.6(13) . . . . ?
C46 C47 C48 C49 -1.4(15) . . . . ?
C47 C48 C49 C50 0.3(14) . . . . ?
C48 C49 C50 C45 1.7(11) . . . . ?
C46 C45 C50 C49 -2.5(9) . . . . ?
C37 C45 C50 C49 172.4(6) . . . . ?
C52 C53 O7 C54 176.8(9) . . . . ?
C55 C54 O7 C53 -179.6(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.87 2.11 2.829(5) 138.9 .
N1 H1 O7 0.87 2.21 2.955(7) 143.5 2_566

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.10
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.091
