# 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.
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data_2rfin

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H32 Br N O6 S, C H2 Cl2'
_chemical_formula_sum            'C23 H34 Br Cl2 N O6 S'
_chemical_formula_weight         603.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   9.7902(6)
_cell_length_b                   11.9074(7)
_cell_length_c                   13.2668(7)
_cell_angle_alpha                77.203(4)
_cell_angle_beta                 73.176(4)
_cell_angle_gamma                71.420(4)
_cell_volume                     1388.92(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3346
_cell_measurement_theta_min      3.96
_cell_measurement_theta_max      66.60

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    4.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.363
_exptl_absorpt_correction_T_max  0.487
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII 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            7816
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.96
_diffrn_reflns_theta_max         66.78
_reflns_number_total             4245
_reflns_number_gt                3493
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_chemical_absolute_configuration rm

_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)+(0.1425P)²+2.0041P] 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         4245
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2331
_refine_ls_wR_factor_gt          0.2204
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Br1 Br 0.26452(8) 0.15753(6) 0.60743(5) 0.0619(3) Uani 1 1 d . . .
S1 S 0.19907(14) 0.56165(11) 0.30095(10) 0.0452(4) Uani 1 1 d . . .
O1 O 0.4810(4) 0.3966(3) 0.1684(3) 0.0439(8) Uani 1 1 d . . .
O2 O 0.9044(7) 0.2580(5) 0.3073(4) 0.0795(15) Uani 1 1 d . . .
O3 O 0.6994(5) 0.4675(4) 0.0103(3) 0.0576(10) Uani 1 1 d . . .
H3O H 0.7352 0.4623 -0.0531 0.086 Uiso 1 1 calc R . .
O4 O 0.5379(5) 0.3417(4) -0.0536(3) 0.0595(11) Uani 1 1 d . . .
H4O H 0.4833 0.4065 -0.0373 0.089 Uiso 1 1 calc R . .
O5 O 0.0810(5) 0.5939(4) 0.3900(3) 0.0645(12) Uani 1 1 d . . .
O6 O 0.1625(4) 0.5611(4) 0.2034(3) 0.0537(10) Uani 1 1 d . . .
N1 N 0.3041(6) 0.6477(4) 0.2706(4) 0.0475(11) Uani 1 1 d . . .
C1 C 0.2551(6) 0.3546(5) 0.4409(4) 0.0435(12) Uani 1 1 d . . .
H1 H 0.1709 0.3926 0.4881 0.052 Uiso 1 1 calc R . .
C2 C 0.3351(6) 0.2391(5) 0.4708(4) 0.0449(12) Uani 1 1 d . . .
C3 C 0.4606(6) 0.1789(5) 0.4031(4) 0.0451(12) Uani 1 1 d . . .
H3 H 0.5131 0.1014 0.4249 0.054 Uiso 1 1 calc R . .
C4 C 0.5051(6) 0.2370(5) 0.3030(4) 0.0410(11) Uani 1 1 d . . .
C5 C 0.6317(6) 0.1931(5) 0.2124(4) 0.0438(12) Uani 1 1 d . . .
C6 C 0.7854(7) 0.1618(5) 0.2364(5) 0.0560(14) Uani 1 1 d . . .
H6A H 0.7823 0.1161 0.3070 0.067 Uiso 1 1 calc R . .
H6B H 0.8576 0.1118 0.1857 0.067 Uiso 1 1 calc R . .
C7 C 0.8334(7) 0.2686(6) 0.2311(5) 0.0585(15) Uani 1 1 d . . .
C8 C 0.8071(7) 0.3617(6) 0.1541(5) 0.0559(14) Uani 1 1 d . . .
C9 C 0.7375(7) 0.3524(5) 0.0712(5) 0.0498(13) Uani 1 1 d . . .
C10 C 0.6049(6) 0.3004(5) 0.1197(4) 0.0448(12) Uani 1 1 d . . .
C11 C 0.4248(6) 0.3521(5) 0.2706(4) 0.0404(11) Uani 1 1 d . . .
C12 C 0.3016(6) 0.4134(4) 0.3399(4) 0.0408(11) Uani 1 1 d . . .
C13 C 0.9631(15) 0.3564(13) 0.3029(10) 0.121(4) Uani 1 1 d . . .
H13A H 1.0294 0.3683 0.2348 0.181 Uiso 1 1 calc R . .
H13B H 1.0158 0.3384 0.3578 0.181 Uiso 1 1 calc R . .
H13C H 0.8830 0.4278 0.3132 0.181 Uiso 1 1 calc R . .
C14 C 0.5540(7) 0.2592(6) 0.0393(5) 0.0539(14) Uani 1 1 d . . .
H14A H 0.6249 0.1851 0.0189 0.065 Uiso 1 1 calc R . .
H14B H 0.4595 0.2421 0.0737 0.065 Uiso 1 1 calc R . .
C15 C 0.3814(8) 0.6797(5) 0.3390(5) 0.0555(15) Uani 1 1 d . . .
C16 C 0.3004(14) 0.6687(9) 0.4540(6) 0.094(3) Uani 1 1 d . . .
H16A H 0.2103 0.7325 0.4640 0.142 Uiso 1 1 calc R . .
H16B H 0.3619 0.6735 0.4967 0.142 Uiso 1 1 calc R . .
H16C H 0.2771 0.5932 0.4748 0.142 Uiso 1 1 calc R . .
C17 C 0.5386(11) 0.5952(7) 0.3241(9) 0.089(3) Uani 1 1 d . . .
H17A H 0.5916 0.6141 0.3658 0.133 Uiso 1 1 calc R . .
H17B H 0.5893 0.6045 0.2504 0.133 Uiso 1 1 calc R . .
H17C H 0.5334 0.5140 0.3468 0.133 Uiso 1 1 calc R . .
C18 C 0.3985(9) 0.8060(6) 0.2903(6) 0.0665(17) Uani 1 1 d . . .
H18A H 0.4711 0.8179 0.3206 0.080 Uiso 1 1 calc R . .
H18B H 0.4436 0.8035 0.2151 0.080 Uiso 1 1 calc R . .
C19 C 0.2693(10) 0.9196(6) 0.2980(8) 0.077(2) Uani 1 1 d . . .
C20 C 0.1453(15) 0.9123(9) 0.2552(16) 0.155(7) Uani 1 1 d . . .
H20A H 0.1811 0.9052 0.1808 0.233 Uiso 1 1 calc R . .
H20B H 0.0645 0.9834 0.2648 0.233 Uiso 1 1 calc R . .
H20C H 0.1116 0.8437 0.2928 0.233 Uiso 1 1 calc R . .
C21 C 0.3398(19) 1.0176(10) 0.2173(14) 0.142(6) Uani 1 1 d . . .
H21A H 0.4007 1.0411 0.2495 0.213 Uiso 1 1 calc R . .
H21B H 0.2621 1.0862 0.1999 0.213 Uiso 1 1 calc R . .
H21C H 0.3994 0.9849 0.1536 0.213 Uiso 1 1 calc R . .
C22 C 0.220(2) 0.9579(11) 0.4079(13) 0.153(6) Uani 1 1 d . . .
H22A H 0.2773 0.9004 0.4540 0.230 Uiso 1 1 calc R . .
H22B H 0.1170 0.9627 0.4366 0.230 Uiso 1 1 calc R . .
H22C H 0.2358 1.0349 0.4026 0.230 Uiso 1 1 calc R . .
C23 C 0.8618(16) 0.7536(14) 0.1203(10) 0.125(4) Uani 1 1 d . . .
H23A H 0.9500 0.6995 0.1411 0.150 Uiso 1 1 calc R . .
H23B H 0.7802 0.7568 0.1829 0.150 Uiso 1 1 calc R . .
Cl1 Cl 0.8263(7) 0.6976(6) 0.0322(5) 0.191(2) Uani 1 1 d . . .
Cl2 Cl 0.8891(9) 0.8960(5) 0.0786(6) 0.221(3) Uani 1 1 d . . .
H1N H 0.359(9) 0.636(7) 0.209(6) 0.06(2) Uiso 1 1 d . . .
H5 H 0.610(6) 0.133(6) 0.191(5) 0.039(14) Uiso 1 1 d . . .
H8 H 0.845(9) 0.428(8) 0.146(6) 0.07(2) Uiso 1 1 d . . .
H9 H 0.821(8) 0.295(6) 0.016(5) 0.053(17) Uiso 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 C2 1.905(5) . ?
S1 O5 1.417(4) . ?
S1 O6 1.441(4) . ?
S1 N1 1.587(5) . ?
S1 C12 1.777(5) . ?
O1 C11 1.363(6) . ?
O1 C10 1.479(6) . ?
O2 C7 1.347(8) . ?
O2 C13 1.444(13) . ?
O3 C9 1.425(7) . ?
O3 H3O 0.8200 . ?
O4 C14 1.409(7) . ?
O4 H4O 0.8200 . ?
N1 C15 1.508(8) . ?
N1 H1N 0.86(8) . ?
C1 C2 1.383(8) . ?
C1 C12 1.389(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(8) . ?
C3 C4 1.372(8) . ?
C3 H3 0.9300 . ?
C4 C11 1.389(7) . ?
C4 C5 1.502(8) . ?
C5 C6 1.540(9) . ?
C5 C10 1.578(7) . ?
C5 H5 0.92(6) . ?
C6 C7 1.472(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.344(9) . ?
C8 C9 1.490(9) . ?
C8 H8 0.95(9) . ?
C9 C10 1.528(9) . ?
C9 H9 1.09(7) . ?
C10 C14 1.524(9) . ?
C11 C12 1.388(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.500(12) . ?
C15 C17 1.532(11) . ?
C15 C18 1.541(10) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.529(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.514(14) . ?
C19 C22 1.521(17) . ?
C19 C21 1.587(16) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 Cl1 1.631(13) . ?
C23 Cl2 1.744(16) . ?
C23 H23A 0.9700 . ?
C23 H23B 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
O5 S1 O6 118.0(3) . . ?
O5 S1 N1 110.9(3) . . ?
O6 S1 N1 105.4(3) . . ?
O5 S1 C12 106.2(2) . . ?
O6 S1 C12 106.8(2) . . ?
N1 S1 C12 109.1(3) . . ?
C11 O1 C10 108.2(4) . . ?
C7 O2 C13 115.9(7) . . ?
C9 O3 H3O 109.5 . . ?
C14 O4 H4O 109.5 . . ?
C15 N1 S1 129.7(4) . . ?
C15 N1 H1N 112(5) . . ?
S1 N1 H1N 107(5) . . ?
C2 C1 C12 119.5(5) . . ?
C2 C1 H1 120.3 . . ?
C12 C1 H1 120.3 . . ?
C1 C2 C3 122.3(5) . . ?
C1 C2 Br1 118.8(4) . . ?
C3 C2 Br1 118.9(4) . . ?
C4 C3 C2 118.0(5) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C11 120.6(5) . . ?
C3 C4 C5 129.7(5) . . ?
C11 C4 C5 109.6(4) . . ?
C4 C5 C6 113.8(5) . . ?
C4 C5 C10 101.8(4) . . ?
C6 C5 C10 114.0(5) . . ?
C4 C5 H5 107(4) . . ?
C6 C5 H5 116(4) . . ?
C10 C5 H5 102(4) . . ?
C7 C6 C5 112.7(5) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 O2 127.4(7) . . ?
C8 C7 C6 119.8(6) . . ?
O2 C7 C6 112.8(6) . . ?
C7 C8 C9 119.4(6) . . ?
C7 C8 H8 121(5) . . ?
C9 C8 H8 119(5) . . ?
O3 C9 C8 108.4(5) . . ?
O3 C9 C10 112.6(5) . . ?
C8 C9 C10 111.8(5) . . ?
O3 C9 H9 106(4) . . ?
C8 C9 H9 108(3) . . ?
C10 C9 H9 110(4) . . ?
O1 C10 C14 108.0(5) . . ?
O1 C10 C9 106.8(4) . . ?
C14 C10 C9 114.1(5) . . ?
O1 C10 C5 106.2(4) . . ?
C14 C10 C5 108.1(5) . . ?
C9 C10 C5 113.3(5) . . ?
O1 C11 C12 125.2(4) . . ?
O1 C11 C4 113.7(5) . . ?
C12 C11 C4 121.1(5) . . ?
C11 C12 C1 118.4(4) . . ?
C11 C12 S1 121.9(4) . . ?
C1 C12 S1 119.7(4) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 C10 115.1(5) . . ?
O4 C14 H14A 108.5 . . ?
C10 C14 H14A 108.5 . . ?
O4 C14 H14B 108.5 . . ?
C10 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C16 C15 N1 111.7(7) . . ?
C16 C15 C17 110.6(7) . . ?
N1 C15 C17 107.3(5) . . ?
C16 C15 C18 114.3(6) . . ?
N1 C15 C18 106.2(5) . . ?
C17 C15 C18 106.3(7) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C15 123.6(7) . . ?
C19 C18 H18A 106.4 . . ?
C15 C18 H18A 106.4 . . ?
C19 C18 H18B 106.4 . . ?
C15 C18 H18B 106.4 . . ?
H18A C18 H18B 106.5 . . ?
C20 C19 C22 114.9(12) . . ?
C20 C19 C18 112.1(7) . . ?
C22 C19 C18 112.3(8) . . ?
C20 C19 C21 106.1(10) . . ?
C22 C19 C21 107.6(10) . . ?
C18 C19 C21 102.9(9) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl1 C23 Cl2 115.3(9) . . ?
Cl1 C23 H23A 108.4 . . ?
Cl2 C23 H23A 108.4 . . ?
Cl1 C23 H23B 108.4 . . ?
Cl2 C23 H23B 108.4 . . ?
H23A C23 H23B 107.5 . . ?

_diffrn_measured_fraction_theta_max 0.863
_diffrn_reflns_theta_full        66.78
_diffrn_measured_fraction_theta_full 0.863
_refine_diff_density_max         1.019
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.110
_database_code_depnum_ccdc_archive 'CCDC 1010318'
#######################################################################
#
#                 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_7fin

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H33 Br N3 O6 S'
_chemical_formula_sum            'C28 H33 Br N3 O6 S'
_chemical_formula_weight         619.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc
_symmetry_space_group_name_Hall  P-2yc

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

_cell_length_a                   8.3521(3)
_cell_length_b                   14.3086(6)
_cell_length_c                   23.7793(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.573(2)
_cell_angle_gamma                90.00
_cell_volume                     2817.00(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5043
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      66.84

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1284
_exptl_absorpt_coefficient_mu    3.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  0.735
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            16276
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         67.28
_reflns_number_total             6485
_reflns_number_gt                5200
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_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)+(0.0000P)²+13.4245P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.42(7)
_refine_ls_number_reflns         6485
_refine_ls_number_parameters     703
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1526
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.179
_refine_ls_shift/su_max          0.017
_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 -0.00144(18) 0.96486(19) 0.47446(7) 0.0684(7) Uani 1 1 d . . .
S1 S -0.5412(5) 1.1206(4) 0.5520(2) 0.0474(12) Uani 1 1 d . . .
O1 O -0.2948(13) 1.1523(9) 0.6606(4) 0.035(3) Uani 1 1 d . . .
O2 O -0.2209(18) 1.3360(10) 0.6673(8) 0.070(5) Uani 1 1 d . . .
O3 O 0.3330(14) 1.2654(10) 0.6936(5) 0.050(3) Uani 1 1 d . . .
O4 O -0.0671(16) 1.1888(16) 0.7968(6) 0.080(5) Uani 1 1 d . . .
O5 O -0.6100(15) 1.0781(10) 0.5989(7) 0.056(4) Uani 1 1 d . . .
O6 O -0.5965(16) 1.0961(13) 0.4952(6) 0.080(5) Uani 1 1 d . . .
N1 N -0.3350(17) 1.1661(12) 0.7676(6) 0.048(4) Uani 1 1 d . . .
H1N H -0.4022 1.1620 0.7370 0.058 Uiso 1 1 calc R . .
N2 N -0.5345(17) 1.1151(11) 0.8163(5) 0.038(3) Uani 1 1 d . . .
N3 N -0.5647(18) 1.2309(11) 0.5611(6) 0.047(4) Uani 1 1 d . . .
H3N H -0.6000 1.2485 0.5918 0.056 Uiso 1 1 calc R . .
C1 C -0.258(2) 1.0493(13) 0.5243(8) 0.042(4) Uani 1 1 d . . .
H1 H -0.3191 1.0332 0.4901 0.050 Uiso 1 1 calc R . .
C2 C -0.105(2) 1.0257(11) 0.5304(7) 0.035(4) Uiso 1 1 d . . .
C3 C -0.006(2) 1.0435(12) 0.5849(8) 0.042(5) Uani 1 1 d . . .
H3 H 0.1018 1.0256 0.5914 0.050 Uiso 1 1 calc R . .
C4 C -0.079(2) 1.0874(12) 0.6259(8) 0.049(5) Uani 1 1 d . . .
C5 C -0.0218(18) 1.1107(13) 0.6871(7) 0.034(4) Uani 1 1 d . . .
H5 H -0.0338 1.0554 0.7105 0.041 Uiso 1 1 calc R . .
C6 C 0.161(2) 1.1422(12) 0.6956(7) 0.045(4) Uani 1 1 d . . .
H6 H 0.2496 1.1022 0.7019 0.055 Uiso 1 1 calc R . .
C7 C 0.1707(19) 1.2488(12) 0.6921(8) 0.038(4) Uani 1 1 d . . .
C8 C 0.057(2) 1.3075(13) 0.6856(7) 0.047(5) Uani 1 1 d . . .
H8 H 0.0819 1.3707 0.6838 0.057 Uiso 1 1 calc R . .
C9 C -0.110(2) 1.2802(14) 0.6808(7) 0.047(5) Uani 1 1 d . . .
C10 C -0.148(2) 1.1798(12) 0.6964(7) 0.034(3) Uiso 1 1 d . . .
C11 C -0.243(2) 1.1121(12) 0.6165(7) 0.036(4) Uiso 1 1 d . . .
C12 C -0.338(2) 1.0952(13) 0.5630(7) 0.040(4) Uani 1 1 d . . .
C13 C 0.388(2) 1.3618(14) 0.6984(7) 0.057(5) Uani 1 1 d . . .
H13A H 0.3411 1.3962 0.6656 0.085 Uiso 1 1 calc R . .
H13B H 0.5035 1.3635 0.7008 0.085 Uiso 1 1 calc R . .
H13C H 0.3552 1.3894 0.7319 0.085 Uiso 1 1 calc R . .
C14 C -0.183(2) 1.1805(14) 0.7627(6) 0.044(4) Uani 1 1 d . . .
C15 C -0.398(2) 1.1566(14) 0.8217(7) 0.048(5) Uani 1 1 d . . .
C16 C -0.312(2) 1.1894(17) 0.8723(8) 0.056(5) Uani 1 1 d . . .
H16 H -0.2137 1.2200 0.8726 0.067 Uiso 1 1 calc R . .
C17 C -0.377(3) 1.1751(18) 0.9213(8) 0.063(6) Uani 1 1 d . . .
H17 H -0.3247 1.1945 0.9563 0.076 Uiso 1 1 calc R . .
C18 C -0.529(3) 1.1290(18) 0.9162(7) 0.066(6) Uani 1 1 d . . .
H18 H -0.5806 1.1187 0.9480 0.079 Uiso 1 1 calc R . .
C19 C -0.5983(19) 1.0998(15) 0.8632(8) 0.055(5) Uani 1 1 d . . .
C20 C -0.760(3) 1.0477(17) 0.8608(11) 0.074(7) Uani 1 1 d . . .
H20A H -0.7707 1.0044 0.8297 0.111 Uiso 1 1 calc R . .
H20B H -0.8472 1.0919 0.8556 0.111 Uiso 1 1 calc R . .
H20C H -0.7631 1.0143 0.8957 0.111 Uiso 1 1 calc R . .
C21 C -0.530(2) 1.3042(17) 0.5205(9) 0.066(6) Uani 1 1 d D . .
C22 C -0.422(4) 1.366(2) 0.5541(11) 0.25(2) Uani 1 1 d . . .
H22A H -0.3354 1.3831 0.5335 0.376 Uiso 1 1 calc R . .
H22B H -0.3795 1.3355 0.5888 0.376 Uiso 1 1 calc R . .
H22C H -0.4799 1.4213 0.5626 0.376 Uiso 1 1 calc R . .
C23 C -0.466(4) 1.2710(19) 0.4731(11) 0.25(2) Uani 1 1 d . . .
H23A H -0.3548 1.2539 0.4838 0.375 Uiso 1 1 calc R . .
H23B H -0.4726 1.3189 0.4447 0.375 Uiso 1 1 calc R . .
H23C H -0.5258 1.2172 0.4583 0.375 Uiso 1 1 calc R . .
C24 C -0.683(2) 1.3503(18) 0.5026(16) 0.26(2) Uani 1 1 d D . .
H24A H -0.6898 1.3913 0.5347 0.309 Uiso 1 1 calc R . .
H24B H -0.6530 1.3914 0.4732 0.309 Uiso 1 1 calc R . .
C25 C -0.852(2) 1.3356(16) 0.4828(6) 0.061(6) Uani 1 1 d . . .
C26 C -0.923(3) 1.2480(14) 0.4997(13) 0.092(9) Uani 1 1 d . . .
H26A H -0.8737 1.1963 0.4828 0.138 Uiso 1 1 calc R . .
H26B H -1.0370 1.2481 0.4871 0.138 Uiso 1 1 calc R . .
H26C H -0.9048 1.2422 0.5403 0.138 Uiso 1 1 calc R . .
C27 C -0.912(5) 1.409(2) 0.5233(18) 0.181(16) Uani 1 1 d . . .
H27A H -0.8765 1.4700 0.5136 0.271 Uiso 1 1 calc R . .
H27B H -0.8681 1.3945 0.5617 0.271 Uiso 1 1 calc R . .
H27C H -1.0275 1.4076 0.5197 0.271 Uiso 1 1 calc R . .
C28 C -0.891(5) 1.369(3) 0.4268(13) 0.202(19) Uani 1 1 d . . .
H28A H -0.8774 1.4353 0.4263 0.303 Uiso 1 1 calc R . .
H28B H -1.0010 1.3533 0.4131 0.303 Uiso 1 1 calc R . .
H28C H -0.8208 1.3401 0.4029 0.303 Uiso 1 1 calc R . .
Br1A Br -2.15020(19) 0.46498(19) 0.80629(7) 0.0681(7) Uani 1 1 d . . .
S1A S -1.6088(5) 0.6211(4) 0.72787(19) 0.0464(12) Uani 1 1 d . . .
O1A O -1.8553(13) 0.6545(9) 0.6200(5) 0.044(3) Uani 1 1 d . . .
O2A O -1.9296(17) 0.8345(11) 0.6114(8) 0.074(5) Uani 1 1 d . . .
O3A O -2.4901(15) 0.7661(9) 0.5846(7) 0.060(4) Uani 1 1 d . . .
O4A O -2.0824(15) 0.6926(12) 0.4845(5) 0.060(4) Uani 1 1 d . . .
O5A O -1.5426(15) 0.5767(11) 0.6831(7) 0.058(4) Uani 1 1 d . . .
O6A O -1.5507(16) 0.5962(12) 0.7852(6) 0.071(5) Uani 1 1 d . . .
N1A N -1.8154(16) 0.6721(11) 0.5112(6) 0.041(4) Uani 1 1 d . . .
H1AN H -1.7417 0.6753 0.5400 0.049 Uiso 1 1 calc R . .
N2A N -1.6119(19) 0.6135(13) 0.4635(7) 0.054(4) Uani 1 1 d . . .
N3A N -1.5920(19) 0.7307(12) 0.7214(6) 0.053(4) Uani 1 1 d . . .
H3AN H -1.5662 0.7478 0.6891 0.064 Uiso 1 1 calc R . .
C1A C -1.890(2) 0.5496(14) 0.7618(7) 0.040(4) Uani 1 1 d . . .
H1A H -1.8331 0.5387 0.7975 0.048 Uiso 1 1 calc R . .
C2A C -2.059(2) 0.5254(13) 0.7471(8) 0.048(5) Uani 1 1 d . . .
C3A C -2.145(2) 0.5421(12) 0.6973(7) 0.039(4) Uani 1 1 d . . .
H3A H -2.2536 0.5252 0.6906 0.047 Uiso 1 1 calc R . .
C4A C -2.0724(17) 0.5844(11) 0.6565(6) 0.027(3) Uani 1 1 d . . .
C5A C -2.136(2) 0.6085(12) 0.5950(7) 0.038(4) Uani 1 1 d . . .
H5A H -2.1237 0.5524 0.5724 0.046 Uiso 1 1 calc R . .
C6A C -2.3038(17) 0.6435(12) 0.5783(7) 0.040(4) Uani 1 1 d . . .
H6A H -2.3857 0.6044 0.5618 0.048 Uiso 1 1 calc R . .
C7A C -2.333(2) 0.7407(14) 0.5890(6) 0.041(4) Uani 1 1 d . . .
C8A C -2.207(2) 0.8086(13) 0.5977(7) 0.040(4) Uani 1 1 d . . .
H8A H -2.2339 0.8709 0.6030 0.048 Uiso 1 1 calc R . .
C9A C -2.041(2) 0.7830(12) 0.5983(7) 0.042(4) Uani 1 1 d . . .
C10A C -2.0003(18) 0.6810(14) 0.5814(7) 0.041(4) Uani 1 1 d . . .
C11A C -1.9128(18) 0.6094(12) 0.6668(7) 0.034(4) Uani 1 1 d . . .
C12A C -1.821(2) 0.5910(12) 0.7172(8) 0.036(4) Uani 1 1 d . . .
C13A C -2.530(2) 0.8642(16) 0.5806(10) 0.080(7) Uani 1 1 d . . .
H13D H -2.4962 0.8938 0.6165 0.120 Uiso 1 1 calc R . .
H13E H -2.6442 0.8715 0.5708 0.120 Uiso 1 1 calc R . .
H13F H -2.4750 0.8928 0.5520 0.120 Uiso 1 1 calc R . .
C14A C -1.9705(16) 0.6804(12) 0.5236(7) 0.042(4) Uani 1 1 d . . .
C15A C -1.760(2) 0.6595(11) 0.4599(7) 0.037(4) Uani 1 1 d . . .
C16A C -1.839(2) 0.6917(17) 0.4100(8) 0.055(5) Uani 1 1 d . . .
H16A H -1.9351 0.7252 0.4078 0.066 Uiso 1 1 calc R . .
C17A C -1.764(3) 0.670(2) 0.3618(9) 0.076(8) Uani 1 1 d . . .
H17A H -1.8155 0.6891 0.3266 0.091 Uiso 1 1 calc R . .
C18A C -1.630(2) 0.6259(18) 0.3629(9) 0.066(6) Uani 1 1 d . . .
H18A H -1.5894 0.6120 0.3293 0.080 Uiso 1 1 calc R . .
C19A C -1.545(2) 0.5987(14) 0.4152(7) 0.052(5) Uani 1 1 d . . .
C20A C -1.389(3) 0.5526(18) 0.4230(9) 0.071(7) Uani 1 1 d . . .
H20D H -1.3086 0.5941 0.4121 0.106 Uiso 1 1 calc R . .
H20E H -1.3941 0.4973 0.4001 0.106 Uiso 1 1 calc R . .
H20F H -1.3621 0.5358 0.4622 0.106 Uiso 1 1 calc R . .
C21A C -1.6126(19) 0.8112(14) 0.7610(7) 0.045(4) Uani 1 1 d . . .
C22A C -1.639(2) 0.9023(10) 0.7267(8) 0.069(5) Uani 1 1 d . . .
H22D H -1.7452 0.9019 0.7054 0.103 Uiso 1 1 calc R . .
H22E H -1.5598 0.9071 0.7011 0.103 Uiso 1 1 calc R . .
H22F H -1.6294 0.9547 0.7521 0.103 Uiso 1 1 calc R . .
C23A C -1.7725(15) 0.7941(15) 0.7872(10) 0.098(7) Uani 1 1 d . . .
H23D H -1.7922 0.8460 0.8109 0.147 Uiso 1 1 calc R . .
H23E H -1.7624 0.7379 0.8096 0.147 Uiso 1 1 calc R . .
H23F H -1.8610 0.7877 0.7573 0.147 Uiso 1 1 calc R . .
C24A C -1.4758(17) 0.8205(12) 0.8102(4) 0.056(4) Uani 1 1 d . . .
H24C H -1.4735 0.7635 0.8324 0.067 Uiso 1 1 calc R . .
H24D H -1.5041 0.8709 0.8343 0.067 Uiso 1 1 calc R . .
C25A C -1.297(2) 0.8394(13) 0.7968(10) 0.074(7) Uani 1 1 d . . .
C26A C -1.199(4) 0.846(3) 0.8581(13) 0.22(2) Uani 1 1 d . . .
H26D H -1.0958 0.8734 0.8559 0.331 Uiso 1 1 calc R . .
H26E H -1.1846 0.7839 0.8739 0.331 Uiso 1 1 calc R . .
H26F H -1.2579 0.8832 0.8819 0.331 Uiso 1 1 calc R . .
C27A C -1.248(5) 0.924(2) 0.776(2) 0.21(2) Uani 1 1 d . . .
H27D H -1.1319 0.9281 0.7832 0.310 Uiso 1 1 calc R . .
H27E H -1.2941 0.9745 0.7951 0.310 Uiso 1 1 calc R . .
H27F H -1.2822 0.9278 0.7362 0.310 Uiso 1 1 calc R . .
C28A C -1.237(3) 0.752(2) 0.7729(18) 0.164(16) Uani 1 1 d . . .
H28D H -1.2836 0.7453 0.7341 0.245 Uiso 1 1 calc R . .
H28E H -1.2657 0.6994 0.7944 0.245 Uiso 1 1 calc R . .
H28F H -1.1211 0.7551 0.7749 0.245 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
Br1 C2 1.891(18) . ?
S1 O6 1.414(13) . ?
S1 O5 1.453(16) . ?
S1 N3 1.607(16) . ?
S1 C12 1.721(18) . ?
O1 C11 1.32(2) . ?
O1 C10 1.454(18) . ?
O2 C9 1.24(2) . ?
O3 C7 1.372(19) . ?
O3 C13 1.45(2) . ?
O4 C14 1.19(2) . ?
N1 C14 1.30(2) . ?
N1 C15 1.46(2) . ?
N1 H1N 0.8600 . ?
N2 C15 1.28(2) . ?
N2 C19 1.32(2) . ?
N3 C21 1.48(3) . ?
N3 H3N 0.8600 . ?
C1 C2 1.31(2) . ?
C1 C12 1.37(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.47(2) . ?
C3 C4 1.37(3) . ?
C3 H3 0.9300 . ?
C4 C11 1.40(2) . ?
C4 C5 1.51(2) . ?
C5 C10 1.48(2) . ?
C5 C6 1.58(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.53(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.26(2) . ?
C8 C9 1.43(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.53(3) . ?
C10 C14 1.65(2) . ?
C11 C12 1.43(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.40(2) . ?
C16 C17 1.36(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.42(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.38(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.54(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C23 1.39(3) . ?
C21 C22 1.43(3) . ?
C21 C24 1.451(17) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.45(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C28 1.41(3) . ?
C25 C26 1.47(3) . ?
C25 C27 1.55(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
Br1A C2A 1.897(17) . ?
S1A O5A 1.413(17) . ?
S1A O6A 1.430(14) . ?
S1A N3A 1.585(17) . ?
S1A C12A 1.807(18) . ?
O1A C11A 1.425(19) . ?
O1A C10A 1.469(18) . ?
O2A C9A 1.19(2) . ?
O3A C7A 1.35(2) . ?
O3A C13A 1.44(2) . ?
O4A C14A 1.241(18) . ?
N1A C14A 1.37(2) . ?
N1A C15A 1.37(2) . ?
N1A H1AN 0.8600 . ?
N2A C19A 1.36(2) . ?
N2A C15A 1.39(2) . ?
N3A C21A 1.51(2) . ?
N3A H3AN 0.8600 . ?
C1A C12A 1.40(2) . ?
C1A C2A 1.45(3) . ?
C1A H1A 0.9300 . ?
C2A C3A 1.32(3) . ?
C3A C4A 1.35(2) . ?
C3A H3A 0.9300 . ?
C4A C11A 1.37(2) . ?
C4A C5A 1.53(2) . ?
C5A C6A 1.49(2) . ?
C5A C10A 1.60(2) . ?
C5A H5A 0.9800 . ?
C6A C7A 1.44(3) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.43(2) . ?
C8A C9A 1.44(2) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.56(3) . ?
C10A C14A 1.43(2) . ?
C11A C12A 1.36(2) . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?
C15A C16A 1.36(2) . ?
C16A C17A 1.41(3) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.28(3) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.40(3) . ?
C18A H18A 0.9300 . ?
C19A C20A 1.45(3) . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C21A C24A 1.53(2) . ?
C21A C22A 1.54(2) . ?
C21A C23A 1.57(2) . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
C24A C25A 1.59(2) . ?
C24A H24C 0.9700 . ?
C24A H24D 0.9700 . ?
C25A C27A 1.39(4) . ?
C25A C28A 1.49(3) . ?
C25A C26A 1.58(3) . ?
C26A H26D 0.9600 . ?
C26A H26E 0.9600 . ?
C26A H26F 0.9600 . ?
C27A H27D 0.9600 . ?
C27A H27E 0.9600 . ?
C27A H27F 0.9600 . ?
C28A H28D 0.9600 . ?
C28A H28E 0.9600 . ?
C28A H28F 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
O6 S1 O5 121.2(10) . . ?
O6 S1 N3 110.0(10) . . ?
O5 S1 N3 103.9(8) . . ?
O6 S1 C12 106.5(8) . . ?
O5 S1 C12 106.0(9) . . ?
N3 S1 C12 108.8(9) . . ?
C11 O1 C10 104.0(12) . . ?
C7 O3 C13 117.8(14) . . ?
C14 N1 C15 124.0(13) . . ?
C14 N1 H1N 118.0 . . ?
C15 N1 H1N 118.0 . . ?
C15 N2 C19 116.6(14) . . ?
C21 N3 S1 124.7(12) . . ?
C21 N3 H3N 117.6 . . ?
S1 N3 H3N 117.6 . . ?
C2 C1 C12 127.0(16) . . ?
C2 C1 H1 116.5 . . ?
C12 C1 H1 116.5 . . ?
C1 C2 C3 118.7(17) . . ?
C1 C2 Br1 124.8(13) . . ?
C3 C2 Br1 116.5(13) . . ?
C4 C3 C2 117.3(17) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C11 121.2(17) . . ?
C3 C4 C5 132.5(16) . . ?
C11 C4 C5 106.0(15) . . ?
C10 C5 C4 98.7(12) . . ?
C10 C5 C6 119.0(15) . . ?
C4 C5 C6 111.4(14) . . ?
C10 C5 H5 109.0 . . ?
C4 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
C7 C6 C5 109.4(14) . . ?
C7 C6 H6 125.3 . . ?
C5 C6 H6 125.3 . . ?
C8 C7 O3 127.9(18) . . ?
C8 C7 C6 128.8(16) . . ?
O3 C7 C6 103.2(14) . . ?
C7 C8 C9 122.3(18) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
O2 C9 C8 122(2) . . ?
O2 C9 C10 119.8(16) . . ?
C8 C9 C10 117.9(15) . . ?
O1 C10 C5 107.1(13) . . ?
O1 C10 C9 107.4(13) . . ?
C5 C10 C9 114.7(14) . . ?
O1 C10 C14 108.5(13) . . ?
C5 C10 C14 111.7(14) . . ?
C9 C10 C14 107.3(14) . . ?
O1 C11 C4 113.6(15) . . ?
O1 C11 C12 125.4(15) . . ?
C4 C11 C12 121.1(17) . . ?
C1 C12 C11 114.5(16) . . ?
C1 C12 S1 123.8(12) . . ?
C11 C12 S1 121.4(14) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 N1 132.4(15) . . ?
O4 C14 C10 114.8(15) . . ?
N1 C14 C10 112.7(13) . . ?
N2 C15 C16 126.3(18) . . ?
N2 C15 N1 112.0(14) . . ?
C16 C15 N1 121.7(17) . . ?
C17 C16 C15 118(2) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C16 C17 C18 116.6(17) . . ?
C16 C17 H17 121.7 . . ?
C18 C17 H17 121.7 . . ?
C19 C18 C17 118.8(19) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
N2 C19 C18 123.7(19) . . ?
N2 C19 C20 120.1(16) . . ?
C18 C19 C20 116(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C21 C22 113(3) . . ?
C23 C21 C24 110(2) . . ?
C22 C21 C24 110(3) . . ?
C23 C21 N3 115(2) . . ?
C22 C21 N3 103.7(16) . . ?
C24 C21 N3 105.8(17) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C21 145(2) . . ?
C25 C24 H24A 100.8 . . ?
C21 C24 H24A 100.8 . . ?
C25 C24 H24B 100.8 . . ?
C21 C24 H24B 100.8 . . ?
H24A C24 H24B 104.4 . . ?
C28 C25 C24 111(2) . . ?
C28 C25 C26 120(2) . . ?
C24 C25 C26 116.7(17) . . ?
C28 C25 C27 108(3) . . ?
C24 C25 C27 95(2) . . ?
C26 C25 C27 104(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O5A S1A O6A 119.2(9) . . ?
O5A S1A N3A 108.8(9) . . ?
O6A S1A N3A 108.4(10) . . ?
O5A S1A C12A 105.1(8) . . ?
O6A S1A C12A 106.1(9) . . ?
N3A S1A C12A 108.6(8) . . ?
C11A O1A C10A 105.7(11) . . ?
C7A O3A C13A 118.6(15) . . ?
C14A N1A C15A 129.9(13) . . ?
C14A N1A H1AN 115.0 . . ?
C15A N1A H1AN 115.0 . . ?
C19A N2A C15A 118.8(16) . . ?
C21A N3A S1A 132.4(13) . . ?
C21A N3A H3AN 113.8 . . ?
S1A N3A H3AN 113.8 . . ?
C12A C1A C2A 113.8(15) . . ?
C12A C1A H1A 123.1 . . ?
C2A C1A H1A 123.1 . . ?
C3A C2A C1A 124.9(17) . . ?
C3A C2A Br1A 121.2(15) . . ?
C1A C2A Br1A 113.9(13) . . ?
C2A C3A C4A 118.4(18) . . ?
C2A C3A H3A 120.8 . . ?
C4A C3A H3A 120.8 . . ?
C3A C4A C11A 120.5(14) . . ?
C3A C4A C5A 130.8(14) . . ?
C11A C4A C5A 108.6(14) . . ?
C6A C5A C4A 121.8(15) . . ?
C6A C5A C10A 113.2(13) . . ?
C4A C5A C10A 100.0(12) . . ?
C6A C5A H5A 107.0 . . ?
C4A C5A H5A 107.0 . . ?
C10A C5A H5A 107.0 . . ?
C7A C6A C5A 116.9(14) . . ?
C7A C6A H6A 121.6 . . ?
C5A C6A H6A 121.6 . . ?
O3A C7A C8A 121.1(18) . . ?
O3A C7A C6A 115.5(15) . . ?
C8A C7A C6A 123.0(15) . . ?
C7A C8A C9A 121.4(17) . . ?
C7A C8A H8A 119.3 . . ?
C9A C8A H8A 119.3 . . ?
O2A C9A C8A 124.3(17) . . ?
O2A C9A C10A 117.2(16) . . ?
C8A C9A C10A 118.5(15) . . ?
C14A C10A O1A 111.4(12) . . ?
C14A C10A C9A 108.9(16) . . ?
O1A C10A C9A 105.6(14) . . ?
C14A C10A C5A 114.1(15) . . ?
O1A C10A C5A 104.7(13) . . ?
C9A C10A C5A 111.8(14) . . ?
C12A C11A C4A 122.0(16) . . ?
C12A C11A O1A 124.5(14) . . ?
C4A C11A O1A 113.5(13) . . ?
C11A C12A C1A 120.3(16) . . ?
C11A C12A S1A 120.4(14) . . ?
C1A C12A S1A 119.2(13) . . ?
O3A C13A H13D 109.5 . . ?
O3A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
O3A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
O4A C14A N1A 119.5(15) . . ?
O4A C14A C10A 120.7(15) . . ?
N1A C14A C10A 119.7(12) . . ?
C16A C15A N1A 123.1(18) . . ?
C16A C15A N2A 122.7(18) . . ?
N1A C15A N2A 114.2(14) . . ?
C15A C16A C17A 115(2) . . ?
C15A C16A H16A 122.7 . . ?
C17A C16A H16A 122.7 . . ?
C18A C17A C16A 125(2) . . ?
C18A C17A H17A 117.6 . . ?
C16A C17A H17A 117.6 . . ?
C17A C18A C19A 120(2) . . ?
C17A C18A H18A 120.2 . . ?
C19A C18A H18A 120.2 . . ?
N2A C19A C18A 119(2) . . ?
N2A C19A C20A 115.1(16) . . ?
C18A C19A C20A 125.6(18) . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
N3A C21A C24A 114.1(14) . . ?
N3A C21A C22A 109.6(14) . . ?
C24A C21A C22A 111.9(13) . . ?
N3A C21A C23A 107.6(14) . . ?
C24A C21A C23A 107.4(13) . . ?
C22A C21A C23A 105.8(16) . . ?
C21A C22A H22D 109.5 . . ?
C21A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
C21A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C21A C23A H23D 109.5 . . ?
C21A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
C21A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C21A C24A C25A 119.2(12) . . ?
C21A C24A H24C 107.5 . . ?
C25A C24A H24C 107.5 . . ?
C21A C24A H24D 107.5 . . ?
C25A C24A H24D 107.5 . . ?
H24C C24A H24D 107.0 . . ?
C27A C25A C28A 118(3) . . ?
C27A C25A C26A 98(3) . . ?
C28A C25A C26A 104(3) . . ?
C27A C25A C24A 123(2) . . ?
C28A C25A C24A 108.0(16) . . ?
C26A C25A C24A 102(2) . . ?
C25A C26A H26D 109.5 . . ?
C25A C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
C25A C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
C25A C27A H27D 109.5 . . ?
C25A C27A H27E 109.5 . . ?
H27D C27A H27E 109.5 . . ?
C25A C27A H27F 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?
C25A C28A H28D 109.5 . . ?
C25A C28A H28E 109.5 . . ?
H28D C28A H28E 109.5 . . ?
C25A C28A H28F 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        67.28
_diffrn_measured_fraction_theta_full 0.915
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 1010319'
