# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c266

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Br N3 O6 S2'
_chemical_formula_weight         594.49

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.4314(17)
_cell_length_b                   8.8602(10)
_cell_length_c                   19.841(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.647(2)
_cell_angle_gamma                90.00
_cell_volume                     2493.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2124
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      21.77

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    1.862
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6236
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17287
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5725
_reflns_number_gt                3506
_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, 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)+(0.0616P)²+4.0594P] 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_number_reflns         5725
_refine_ls_number_parameters     340
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1682
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.325
_refine_ls_shift/su_max          0.001
_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
S4 S 0.9945(4) 0.9419(7) 0.2187(3) 0.0388(16) Uiso 0.18 1 d PD A 3
O7 O 0.9518(11) 1.0869(13) 0.2175(10) 0.043(3) Uiso 0.18 1 d PD A 3
O8 O 1.0869(8) 0.925(2) 0.2587(9) 0.043(3) Uiso 0.18 1 d PD A 3
N4 N 0.9241(7) 0.8148(13) 0.2399(11) 0.043(3) Uiso 0.18 1 d PD A 3
H4N H 0.9453(8) 0.7189(14) 0.246(2) 0.051 Uiso 0.18 1 d PD B 3
N7 N 0.9848(17) 0.755(3) -0.0716(6) 0.102(6) Uiso 0.18 1 d PD A 3
O13 O 0.9201(15) 0.807(3) -0.1094(10) 0.102(6) Uiso 0.18 1 d PD A 3
O14 O 1.0230(19) 0.654(3) -0.0892(12) 0.102(6) Uiso 0.18 1 d PD A 3
C41 C 1.0007(13) 0.896(2) 0.1320(5) 0.065(4) Uiso 0.18 1 d PGD A 3
C42 C 0.9288(13) 0.939(2) 0.0788(7) 0.065(4) Uiso 0.18 1 d PG A 3
H42 H 0.8809 1.0019 0.0876 0.078 Uiso 0.18 1 calc PR A 3
C43 C 0.9284(13) 0.888(3) 0.0125(6) 0.065(4) Uiso 0.18 1 d PG A 3
H43 H 0.8803 0.9169 -0.0230 0.078 Uiso 0.18 1 calc PR A 3
C44 C 1.0000(16) 0.794(2) -0.0007(5) 0.065(4) Uiso 0.18 1 d PGD A 3
C45 C 1.0719(15) 0.750(3) 0.0525(8) 0.065(4) Uiso 0.18 1 d PG A 3
H45 H 1.1198 0.6873 0.0437 0.078 Uiso 0.18 1 calc PR A 3
C46 C 1.0723(13) 0.801(2) 0.1188(6) 0.065(4) Uiso 0.18 1 d PG A 3
H46 H 1.1204 0.7723 0.1543 0.078 Uiso 0.18 1 calc PR A 3
S3 S 0.9641(3) 0.9556(5) 0.1563(2) 0.0389(11) Uiso 0.263(2) 1 d PD A 2
O5 O 0.8990(7) 1.0653(12) 0.1248(6) 0.044(3) Uiso 0.263(2) 1 d PD A 2
O6 O 1.0513(7) 1.0008(15) 0.2007(6) 0.053(3) Uiso 0.263(2) 1 d PD A 2
N3 N 0.9215(6) 0.8358(15) 0.2018(9) 0.062(6) Uiso 0.263(2) 1 d PD A 2
H3N H 0.9584(8) 0.7608(19) 0.2237(14) 0.075 Uiso 0.263(2) 1 d PD A 2
N6 N 1.0653(12) 0.5612(19) -0.0635(7) 0.069(3) Uiso 0.263(2) 1 d PD A 2
O11 O 1.0156(11) 0.567(2) -0.1191(8) 0.069(3) Uiso 0.263(2) 1 d PD A 2
O12 O 1.1331(11) 0.4836(19) -0.0477(9) 0.069(3) Uiso 0.263(2) 1 d PD A 2
C31 C 0.9985(9) 0.8433(16) 0.0911(6) 0.097(4) Uiso 0.263(2) 1 d PGD A 2
C32 C 0.9402(11) 0.8346(19) 0.0271(6) 0.097(4) Uiso 0.263(2) 1 d PGD A 2
H32 H 0.8848 0.8906 0.0181 0.116 Uiso 0.263(2) 1 calc PR A 2
C33 C 0.9646(15) 0.742(2) -0.0235(6) 0.097(4) Uiso 0.263(2) 1 d PG A 2
H33 H 0.9255 0.7362 -0.0663 0.116 Uiso 0.263(2) 1 calc PR A 2
C34 C 1.0474(16) 0.658(2) -0.0100(9) 0.097(4) Uiso 0.263(2) 1 d PGD A 2
C35 C 1.1057(13) 0.667(2) 0.0540(10) 0.097(4) Uiso 0.263(2) 1 d PG A 2
H35 H 1.1611 0.6109 0.0629 0.116 Uiso 0.263(2) 1 calc PR A 2
C36 C 1.0813(10) 0.7595(19) 0.1045(7) 0.097(4) Uiso 0.263(2) 1 d PGD A 2
H36 H 1.1204 0.7653 0.1473 0.116 Uiso 0.263(2) 1 calc PR A 2
S2 S 1.00268(13) 0.8937(2) 0.19195(12) 0.0380(6) Uani 0.557(2) 1 d PD A 1
O3 O 0.9632(4) 1.0389(6) 0.1807(3) 0.0454(16) Uani 0.557(2) 1 d PD A 1
O4 O 1.0923(3) 0.8712(8) 0.2355(3) 0.0469(17) Uani 0.557(2) 1 d PD A 1
N2 N 0.9264(4) 0.7883(9) 0.2197(4) 0.048(2) Uani 0.557(2) 1 d PD A 1
H2N H 0.9443(8) 0.733(2) 0.2579(9) 0.057 Uiso 0.557(2) 1 d PD A 1
C18 C 1.00982(9) 0.83092(19) 0.10821(8) 0.0347(19) Uani 0.557(2) 1 d PGDU A 1
C19 C 1.08762(9) 0.7385(2) 0.10808(9) 0.0331(19) Uani 0.557(2) 1 d PGDU A 1
H19 H 1.1314 0.7242 0.1483 0.040 Uiso 0.557(2) 1 calc PR A 1
C20 C 1.09994(11) 0.6675(2) 0.04790(9) 0.041(2) Uani 0.557(2) 1 d PGU A 1
H20 H 1.1520 0.6056 0.0478 0.049 Uiso 0.557(2) 1 calc PR A 1
C21 C 1.03446(11) 0.6888(2) -0.01214(9) 0.038(2) Uani 0.557(2) 1 d PGDU A 1
C22 C 0.95665(11) 0.7812(2) -0.01201(8) 0.053(3) Uani 0.557(2) 1 d PGU A 1
H22 H 0.9128 0.7955 -0.0522 0.063 Uiso 0.557(2) 1 calc PR A 1
C23 C 0.94433(9) 0.85226(19) 0.04817(7) 0.049(2) Uani 0.557(2) 1 d PGDU A 1
H23 H 0.8923 0.9141 0.0483 0.059 Uiso 0.557(2) 1 calc PR A 1
N5 N 1.0405(6) 0.6162(11) -0.0748(4) 0.070(3) Uani 0.557(2) 1 d PDU A 1
O9 O 0.9756(6) 0.6517(13) -0.1257(4) 0.098(3) Uani 0.557(2) 1 d PU A 1
O10 O 1.1000(6) 0.5278(11) -0.0751(5) 0.089(3) Uani 0.557(2) 1 d PU A 1
Br1 Br 0.60971(4) 0.76034(7) 0.11333(3) 0.05610(17) Uani 1 1 d . . .
S1 S 0.63622(8) 1.07223(12) 0.26282(6) 0.0381(3) Uani 1 1 d . . .
O1 O 0.5418(2) 1.0365(3) 0.26896(17) 0.0428(8) Uani 1 1 d . . .
O2 O 0.6938(3) 1.1626(3) 0.31393(17) 0.0491(9) Uani 1 1 d . . .
N1 N 0.6913(2) 0.9138(4) 0.2589(2) 0.0378(9) Uani 1 1 d . . .
C1 C 0.6717(3) 0.6890(4) 0.3287(2) 0.0286(10) Uani 1 1 d . . .
C2 C 0.6741(3) 0.5324(5) 0.3362(2) 0.0338(10) Uani 1 1 d . . .
H2 H 0.6656 0.4716 0.2974 0.041 Uiso 1 1 calc R . .
C3 C 0.68897(13) 0.4658(2) 0.40039(9) 0.0412(12) Uani 1 1 d G . .
H3 H 0.6891 0.3612 0.4044 0.049 Uiso 1 1 calc R . .
C4 C 0.70363(13) 0.5553(2) 0.45885(8) 0.0424(12) Uani 1 1 d G . .
H4 H 0.7146 0.5111 0.5021 0.051 Uiso 1 1 calc R . .
C5 C 0.70186(13) 0.7087(2) 0.45231(8) 0.0419(12) Uani 1 1 d G . .
H5 H 0.7107 0.7683 0.4915 0.050 Uiso 1 1 calc R . .
C6 C 0.68706(11) 0.77821(19) 0.38779(7) 0.0348(11) Uani 1 1 d G . .
H6 H 0.6875 0.8829 0.3843 0.042 Uiso 1 1 calc R . .
C7 C 0.64587(9) 0.76605(15) 0.25818(7) 0.0291(9) Uani 1 1 d G . .
H7 H 0.5775 0.7816 0.2483 0.035 Uiso 1 1 calc R . .
C8 C 0.67204(9) 0.67210(15) 0.20107(8) 0.0356(11) Uani 1 1 d G . .
H8 H 0.6480 0.5695 0.2044 0.043 Uiso 1 1 calc R . .
C9 C 0.77754(9) 0.66389(14) 0.20393(7) 0.0456(12) Uani 1 1 d G A .
H9A H 0.7899 0.6117 0.1635 0.055 Uiso 1 1 calc R . .
H9B H 0.8061 0.6058 0.2438 0.055 Uiso 1 1 calc R . .
C10 C 0.82263(8) 0.81887(14) 0.20753(7) 0.0566(15) Uani 1 1 d GD . .
H10 H 0.8031 0.8724 0.1640 0.068 Uiso 1 1 calc R A 1
C11 C 0.79541(9) 0.91073(15) 0.26683(7) 0.0541(15) Uani 1 1 d G A .
H11A H 0.8228 0.8649 0.3104 0.065 Uiso 1 1 calc R . .
H11B H 0.8195 1.0128 0.2662 0.065 Uiso 1 1 calc R . .
C12 C 0.63432(10) 1.16412(15) 0.18387(8) 0.0371(11) Uani 1 1 d G . .
C13 C 0.55712(9) 1.14981(17) 0.13198(9) 0.0498(13) Uani 1 1 d G . .
H13 H 0.5060 1.0919 0.1391 0.060 Uiso 1 1 calc R . .
C14 C 0.55446(10) 1.22046(19) 0.06932(9) 0.0541(14) Uani 1 1 d G . .
H14 H 0.5022 1.2091 0.0345 0.065 Uiso 1 1 calc R . .
C15 C 0.63066(11) 1.30891(18) 0.05868(9) 0.0406(11) Uani 1 1 d G . .
C16 C 0.70804(11) 1.31887(15) 0.11060(9) 0.0559(14) Uani 1 1 d G . .
H16 H 0.7600 1.3740 0.1029 0.067 Uiso 1 1 calc R . .
C17 C 0.71205(11) 1.24920(14) 0.17490(9) 0.0513(14) Uani 1 1 d G . .
H17 H 0.7644 1.2597 0.2098 0.062 Uiso 1 1 calc R . .
C24 C 0.62765(13) 1.3930(2) -0.00820(10) 0.0521(14) Uani 1 1 d G . .
H24A H 0.5971 1.4886 -0.0060 0.078 Uiso 1 1 calc R . .
H24B H 0.5932 1.3346 -0.0453 0.078 Uiso 1 1 calc R . .
H24C H 0.6908 1.4090 -0.0157 0.078 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
S4 O7 1.423(10) . ?
S4 O8 1.427(10) . ?
S4 N4 1.623(14) . ?
S4 C41 1.789(9) . ?
S4 H3N 1.696(17) . ?
N4 C10 1.487(10) . ?
N4 H4N 0.903(11) . ?
N4 H3N 0.80(3) . ?
N4 H2N 0.832(17) . ?
N7 O14 1.142(19) . ?
N7 O13 1.179(18) . ?
N7 C44 1.426(11) . ?
C41 C42 1.3900 . ?
C41 C46 1.3900 . ?
C42 C43 1.3900 . ?
C42 H42 0.9300 . ?
C43 C44 1.3900 . ?
C43 H43 0.9300 . ?
C44 C45 1.3900 . ?
C45 C46 1.3900 . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
S3 O5 1.415(9) . ?
S3 O6 1.452(9) . ?
S3 N3 1.589(12) . ?
S3 C31 1.775(9) . ?
N3 C10 1.460(9) . ?
N3 H4N 1.35(2) . ?
N3 H3N 0.909(10) . ?
N3 H2N 1.426(16) . ?
N6 O12 1.189(17) . ?
N6 O11 1.201(17) . ?
N6 C34 1.426(11) . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C32 C33 1.3900 . ?
C32 H32 0.9300 . ?
C33 C34 1.3900 . ?
C33 H33 0.9300 . ?
C34 C35 1.3900 . ?
C35 C36 1.3900 . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
S2 O3 1.408(6) . ?
S2 O4 1.431(5) . ?
S2 N2 1.616(7) . ?
S2 C18 1.773(3) . ?
S2 H3N 1.530(12) . ?
N2 C10 1.498(6) . ?
N2 H4N 0.81(2) . ?
N2 H3N 0.514(12) . ?
N2 H2N 0.897(10) . ?
C18 C19 1.3900 . ?
C18 C23 1.3900 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 C22 1.3900 . ?
C21 N5 1.417(8) . ?
C22 C23 1.3900 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
N5 O10 1.163(13) . ?
N5 O9 1.282(13) . ?
Br1 C8 1.9677(15) . ?
S1 O1 1.427(3) . ?
S1 O2 1.431(3) . ?
S1 N1 1.622(4) . ?
S1 C12 1.7611(19) . ?
N1 C7 1.463(4) . ?
N1 C11 1.482(4) . ?
C1 C2 1.396(6) . ?
C1 C6 1.397(4) . ?
C1 C7 1.540(4) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.3887 . ?
C3 H3 0.9300 . ?
C4 C5 1.3648 . ?
C4 H4 0.9300 . ?
C5 C6 1.4011 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.5092 . ?
C7 H7 0.9800 . ?
C8 C9 1.5148 . ?
C8 H8 0.9800 . ?
C9 C10 1.5156 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.5401 . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.3760 . ?
C12 C17 1.3900 . ?
C13 C14 1.3861 . ?
C13 H13 0.9300 . ?
C14 C15 1.3979 . ?
C14 H14 0.9300 . ?
C15 C16 1.3751 . ?
C15 C24 1.5153 . ?
C16 C17 1.4088 . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
O7 S4 O8 117.5(11) . . ?
O7 S4 N4 110.0(9) . . ?
O8 S4 N4 110.4(9) . . ?
O7 S4 C41 106.8(10) . . ?
O8 S4 C41 107.6(10) . . ?
N4 S4 C41 103.6(10) . . ?
O7 S4 H3N 136.0(9) . . ?
O8 S4 H3N 97.7(10) . . ?
N4 S4 H3N 27.7(9) . . ?
C41 S4 H3N 84.8(12) . . ?
C10 N4 S4 119.0(9) . . ?
C10 N4 H4N 111.1(13) . . ?
S4 N4 H4N 118.2(17) . . ?
C10 N4 H3N 118(2) . . ?
S4 N4 H3N 81.2(15) . . ?
H4N N4 H3N 43(2) . . ?
C10 N4 H2N 116.4(14) . . ?
S4 N4 H2N 121.8(13) . . ?
H4N N4 H2N 18(3) . . ?
H3N N4 H2N 57.4(18) . . ?
O14 N7 O13 119.0(17) . . ?
O14 N7 C44 119.8(18) . . ?
O13 N7 C44 119.5(18) . . ?
C42 C41 C46 120.0 . . ?
C42 C41 S4 120.2(9) . . ?
C46 C41 S4 119.4(9) . . ?
C43 C42 C41 120.0 . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C44 120.0 . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C45 C44 C43 120.0 . . ?
C45 C44 N7 129.7(14) . . ?
C43 C44 N7 110.3(14) . . ?
C44 C45 C46 120.0 . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 C41 120.0 . . ?
C45 C46 H46 120.0 . . ?
C41 C46 H46 120.0 . . ?
O5 S3 O6 120.5(8) . . ?
O5 S3 N3 114.5(6) . . ?
O6 S3 N3 102.9(8) . . ?
O5 S3 C31 108.4(7) . . ?
O6 S3 C31 105.6(7) . . ?
N3 S3 C31 103.3(8) . . ?
C10 N3 S3 126.8(7) . . ?
C10 N3 H4N 90.4(10) . . ?
S3 N3 H4N 142.8(10) . . ?
C10 N3 H3N 112.4(12) . . ?
S3 N3 H3N 120.3(12) . . ?
H4N N3 H3N 22.9(15) . . ?
C10 N3 H2N 87.8(8) . . ?
S3 N3 H2N 144.2(9) . . ?
H4N N3 H2N 11(2) . . ?
H3N N3 H2N 29.9(16) . . ?
O12 N6 O11 126.0(16) . . ?
O12 N6 C34 114.0(16) . . ?
O11 N6 C34 120.0(17) . . ?
C32 C31 C36 120.0 . . ?
C32 C31 S3 119.6(6) . . ?
C36 C31 S3 120.4(6) . . ?
C31 C32 C33 120.0 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.0 . . ?
C35 C34 N6 123.4(15) . . ?
C33 C34 N6 116.6(15) . . ?
C34 C35 C36 120.0 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 120.0 . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
O3 S2 O4 121.2(4) . . ?
O3 S2 N2 107.5(4) . . ?
O4 S2 N2 108.1(4) . . ?
O3 S2 C18 103.3(3) . . ?
O4 S2 C18 108.6(3) . . ?
N2 S2 C18 107.4(3) . . ?
O3 S2 H3N 125.5(6) . . ?
O4 S2 H3N 92.5(6) . . ?
N2 S2 H3N 18.5(5) . . ?
C18 S2 H3N 104.2(11) . . ?
C10 N2 S2 124.3(5) . . ?
C10 N2 H4N 116.5(14) . . ?
S2 N2 H4N 118.8(12) . . ?
C10 N2 H3N 162(2) . . ?
S2 N2 H3N 71.2(15) . . ?
H4N N2 H3N 50(3) . . ?
C10 N2 H2N 110.9(9) . . ?
S2 N2 H2N 119.6(9) . . ?
H4N N2 H2N 18(3) . . ?
H3N N2 H2N 60(3) . . ?
C19 C18 C23 120.0 . . ?
C19 C18 S2 111.93(8) . . ?
C23 C18 S2 127.76(8) . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 N5 116.7(4) . . ?
C20 C21 N5 123.2(4) . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C18 120.0 . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
O10 N5 O9 126.5(10) . . ?
O10 N5 C21 118.3(9) . . ?
O9 N5 C21 115.1(9) . . ?
O1 S1 O2 120.2(2) . . ?
O1 S1 N1 107.25(18) . . ?
O2 S1 N1 107.0(2) . . ?
O1 S1 C12 108.69(15) . . ?
O2 S1 C12 106.46(16) . . ?
N1 S1 C12 106.52(16) . . ?
C7 N1 C11 115.4(2) . . ?
C7 N1 S1 123.5(2) . . ?
C11 N1 S1 120.5(2) . . ?
C2 C1 C6 118.4(4) . . ?
C2 C1 C7 122.4(3) . . ?
C6 C1 C7 119.1(3) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.93(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.5 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.5 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.44(18) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N1 C7 C8 109.06(16) . . ?
N1 C7 C1 110.8(2) . . ?
C8 C7 C1 112.71(16) . . ?
N1 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C1 C7 H7 108.0 . . ?
C7 C8 C9 112.8 . . ?
C7 C8 Br1 107.9 . . ?
C9 C8 Br1 110.1 . . ?
C7 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
Br1 C8 H8 108.6 . . ?
C8 C9 C10 112.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 N4 30.4(10) . . ?
N3 C10 N2 21.3(5) . . ?
N4 C10 N2 18.1(8) . . ?
N3 C10 C9 120.5(5) . . ?
N4 C10 C9 112.2(5) . . ?
N2 C10 C9 104.6(3) . . ?
N3 C10 C11 113.3(7) . . ?
N4 C10 C11 93.0(8) . . ?
N2 C10 C11 111.2(3) . . ?
C9 C10 C11 110.3 . . ?
N3 C10 H10 90.4 . . ?
N4 C10 H10 119.5 . . ?
N2 C10 H10 110.2 . . ?
C9 C10 H10 110.2 . . ?
C11 C10 H10 110.2 . . ?
N1 C11 C10 108.95(16) . . ?
N1 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
N1 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C13 C12 C17 121.0 . . ?
C13 C12 S1 120.02(6) . . ?
C17 C12 S1 118.96(6) . . ?
C12 C13 C14 120.9 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 119.8 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 118.4 . . ?
C16 C15 C24 120.8 . . ?
C14 C15 C24 120.8 . . ?
C15 C16 C17 122.8 . . ?
C15 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C12 C17 C16 117.0 . . ?
C12 C17 H17 121.5 . . ?
C16 C17 H17 121.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
N4 H4N O7 0.903(11) 1.925(19) 2.727(18) 147.0(19) 2_745

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.449
_refine_diff_density_min         -1.231
_refine_diff_density_rms         0.091
_database_code_depnum_ccdc_archive 'CCDC 970435'
