# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1027031'
_audit_update_record             
;
2014-09-27 deposited with the CCDC.
2015-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H33 Br N4 O5 S'
_chemical_formula_sum            'C27 H33 Br N4 O5 S'
_chemical_formula_weight         605.54
_chemical_absolute_configuration rmad

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           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.7186(2)
_cell_length_b                   15.8096(5)
_cell_length_c                   26.5176(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2816.66(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3356
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      22.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    1.577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5121
_exptl_absorpt_correction_T_max  0.6406
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25564
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_sigmaI/netI    0.1139
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         28.29
_reflns_number_total             6952
_reflns_number_gt                4854
_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)+(0.0357P)²+0.2245P] 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   0.039(10)
_refine_ls_number_reflns         6952
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.81486(9) 0.35667(3) 1.007271(17) 0.04044(16) Uani 1 1 d . . .
S1 S 0.84836(17) 0.07521(7) 0.65009(4) 0.0166(2) Uani 1 1 d . . .
O1 O 0.6724(6) -0.0729(2) 0.86923(12) 0.0365(8) Uani 1 1 d . . .
O2 O 0.9951(5) -0.12319(18) 0.78071(11) 0.0266(8) Uani 1 1 d . . .
O3 O 1.0235(4) 0.08299(19) 0.68052(11) 0.0236(7) Uani 1 1 d . . .
O4 O 0.8626(5) 0.09687(18) 0.59778(10) 0.0288(8) Uani 1 1 d . . .
O5 O 0.6290(4) 0.14275(18) 0.78070(10) 0.0218(7) Uani 1 1 d . . .
N1 N 0.9874(6) -0.0296(2) 0.87133(13) 0.0209(9) Uani 1 1 d . . .
N2 N 0.7796(5) -0.0288(2) 0.74560(11) 0.0172(8) Uani 1 1 d . . .
H2N H 0.7127 0.0166 0.7511 0.021 Uiso 1 1 calc R . .
N3 N 0.6731(5) 0.1274(2) 0.67904(11) 0.0165(8) Uani 1 1 d . . .
N4 N 0.7957(6) 0.2686(2) 0.78452(12) 0.0192(8) Uani 1 1 d . . .
H4N H 0.8583 0.3045 0.7660 0.023 Uiso 1 1 calc R . .
C1 C 0.8312(8) -0.0693(3) 0.89289(15) 0.0215(10) Uani 1 1 d . . .
C2 C 0.9516(7) 0.0098(3) 0.82226(15) 0.0213(11) Uani 1 1 d . . .
H2 H 0.8420 0.0505 0.8244 0.026 Uiso 1 1 calc R . .
C3 C 1.1508(8) 0.0557(3) 0.81060(17) 0.0408(15) Uani 1 1 d . . .
H3A H 1.2311 0.0228 0.7874 0.049 Uiso 1 1 calc R . .
H3B H 1.1264 0.1110 0.7960 0.049 Uiso 1 1 calc R . .
C4 C 1.2550(8) 0.0639(3) 0.8620(2) 0.0413(14) Uani 1 1 d . . .
H4A H 1.3983 0.0673 0.8582 0.050 Uiso 1 1 calc R . .
H4B H 1.2080 0.1130 0.8804 0.050 Uiso 1 1 calc R . .
C5 C 1.1940(8) -0.0169(3) 0.88753(16) 0.0269(11) Uani 1 1 d . . .
H5A H 1.2776 -0.0636 0.8768 0.032 Uiso 1 1 calc R . .
H5B H 1.2023 -0.0115 0.9239 0.032 Uiso 1 1 calc R . .
C6 C 0.9102(6) -0.0555(3) 0.78166(15) 0.0184(10) Uani 1 1 d . . .
C7 C 0.7488(6) -0.0721(3) 0.69969(15) 0.0162(10) Uani 1 1 d . . .
C8 C 0.7617(6) -0.0302(2) 0.65328(15) 0.0133(9) Uani 1 1 d . . .
C9 C 0.7311(6) -0.0738(3) 0.60876(15) 0.0204(10) Uani 1 1 d . . .
H9 H 0.7364 -0.0450 0.5782 0.024 Uiso 1 1 calc R . .
C10 C 0.6924(7) -0.1601(3) 0.60908(16) 0.0240(10) Uani 1 1 d . . .
H10 H 0.6721 -0.1892 0.5790 0.029 Uiso 1 1 calc R . .
C11 C 0.6847(7) -0.2020(3) 0.65473(16) 0.0225(10) Uani 1 1 d . . .
H11 H 0.6623 -0.2600 0.6553 0.027 Uiso 1 1 calc R . .
C12 C 0.7100(6) -0.1586(3) 0.69956(16) 0.0202(10) Uani 1 1 d . . .
H12 H 0.7008 -0.1876 0.7300 0.024 Uiso 1 1 calc R . .
C13 C 0.7275(7) 0.2100(2) 0.70255(15) 0.0168(10) Uani 1 1 d . . .
H13 H 0.8614 0.2275 0.6923 0.020 Uiso 1 1 calc R . .
C14 C 0.5702(7) 0.2702(3) 0.68103(16) 0.0227(11) Uani 1 1 d . . .
H14A H 0.5436 0.3164 0.7041 0.027 Uiso 1 1 calc R . .
H14B H 0.6123 0.2932 0.6489 0.027 Uiso 1 1 calc R . .
C15 C 0.3888(7) 0.2142(3) 0.67491(18) 0.0254(11) Uani 1 1 d . . .
H15A H 0.2935 0.2390 0.6517 0.030 Uiso 1 1 calc R . .
H15B H 0.3242 0.2040 0.7071 0.030 Uiso 1 1 calc R . .
C16 C 0.4772(6) 0.1334(3) 0.65360(18) 0.0288(11) Uani 1 1 d . . .
H16A H 0.3944 0.0849 0.6616 0.035 Uiso 1 1 calc R . .
H16B H 0.4928 0.1372 0.6173 0.035 Uiso 1 1 calc R . .
C17 C 0.7132(7) 0.2024(3) 0.75987(15) 0.0159(9) Uani 1 1 d . . .
C18 C 0.7923(6) 0.2865(3) 0.83668(14) 0.0155(9) Uani 1 1 d . . .
C19 C 0.7960(6) 0.3705(3) 0.85119(15) 0.0204(10) Uani 1 1 d . . .
H19 H 0.7945 0.4130 0.8269 0.024 Uiso 1 1 calc R . .
C20 C 0.8021(7) 0.3916(3) 0.90184(15) 0.0182(9) Uani 1 1 d . . .
H20 H 0.8081 0.4480 0.9117 0.022 Uiso 1 1 calc R . .
C21 C 0.7990(7) 0.3280(3) 0.93770(14) 0.0210(10) Uani 1 1 d . . .
C22 C 0.7934(7) 0.2438(3) 0.92412(15) 0.0247(11) Uani 1 1 d . . .
H22 H 0.7938 0.2016 0.9486 0.030 Uiso 1 1 calc R . .
C23 C 0.7872(7) 0.2233(3) 0.87325(15) 0.0207(10) Uani 1 1 d . . .
H23 H 0.7795 0.1669 0.8635 0.025 Uiso 1 1 calc R . .
C24 C 0.8479(9) -0.1067(3) 0.94574(16) 0.0367(14) Uani 1 1 d . . .
C25 C 0.8823(10) -0.0363(4) 0.98462(19) 0.061(2) Uani 1 1 d . . .
H25A H 1.0058 -0.0082 0.9775 0.092 Uiso 1 1 calc R . .
H25B H 0.8877 -0.0605 1.0178 0.092 Uiso 1 1 calc R . .
H25C H 0.7751 0.0037 0.9829 0.092 Uiso 1 1 calc R . .
C26 C 0.6471(10) -0.1479(5) 0.9587(2) 0.076(2) Uani 1 1 d . . .
H26A H 0.6537 -0.1720 0.9919 0.114 Uiso 1 1 calc R . .
H26B H 0.6182 -0.1915 0.9346 0.114 Uiso 1 1 calc R . .
H26C H 0.5441 -0.1058 0.9577 0.114 Uiso 1 1 calc R . .
C27 C 1.0096(11) -0.1750(4) 0.9486(2) 0.067(2) Uani 1 1 d . . .
H27A H 1.1382 -0.1493 0.9448 0.101 Uiso 1 1 calc R . .
H27B H 0.9895 -0.2154 0.9220 0.101 Uiso 1 1 calc R . .
H27C H 1.0024 -0.2032 0.9806 0.101 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 C21 1.903(4) . ?
S1 O4 1.432(3) . ?
S1 O3 1.432(3) . ?
S1 N3 1.630(3) . ?
S1 C8 1.767(4) . ?
O1 C1 1.239(6) . ?
O2 C6 1.212(5) . ?
O5 C17 1.231(5) . ?
N1 C1 1.350(6) . ?
N1 C2 1.462(5) . ?
N1 C5 1.467(6) . ?
N2 C6 1.365(5) . ?
N2 C7 1.412(5) . ?
N2 H2N 0.8600 . ?
N3 C16 1.482(5) . ?
N3 C13 1.493(5) . ?
N4 C17 1.353(5) . ?
N4 C18 1.412(5) . ?
N4 H4N 0.8600 . ?
C1 C24 1.525(6) . ?
C2 C6 1.518(6) . ?
C2 C3 1.554(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.537(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.503(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C12 1.392(6) . ?
C7 C8 1.400(5) . ?
C8 C9 1.383(5) . ?
C9 C10 1.388(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C17 1.528(5) . ?
C13 C14 1.532(6) . ?
C13 H13 0.9800 . ?
C14 C15 1.515(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.518(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C19 1.383(6) . ?
C18 C23 1.393(5) . ?
C19 C20 1.384(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(6) . ?
C22 C23 1.388(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C27 1.534(8) . ?
C24 C25 1.534(7) . ?
C24 C26 1.537(8) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
O4 S1 O3 118.1(2) . . ?
O4 S1 N3 112.55(18) . . ?
O3 S1 N3 106.54(17) . . ?
O4 S1 C8 107.09(18) . . ?
O3 S1 C8 108.95(19) . . ?
N3 S1 C8 102.51(18) . . ?
C1 N1 C2 116.6(4) . . ?
C1 N1 C5 132.5(4) . . ?
C2 N1 C5 111.0(4) . . ?
C6 N2 C7 123.2(3) . . ?
C6 N2 H2N 118.4 . . ?
C7 N2 H2N 118.4 . . ?
C16 N3 C13 110.6(3) . . ?
C16 N3 S1 117.4(3) . . ?
C13 N3 S1 117.6(3) . . ?
C17 N4 C18 128.5(4) . . ?
C17 N4 H4N 115.8 . . ?
C18 N4 H4N 115.8 . . ?
O1 C1 N1 118.4(4) . . ?
O1 C1 C24 120.7(4) . . ?
N1 C1 C24 120.8(4) . . ?
N1 C2 C6 111.8(3) . . ?
N1 C2 C3 103.6(4) . . ?
C6 C2 C3 109.5(4) . . ?
N1 C2 H2 110.6 . . ?
C6 C2 H2 110.6 . . ?
C3 C2 H2 110.6 . . ?
C4 C3 C2 104.8(3) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C5 C4 C3 101.8(4) . . ?
C5 C4 H4A 111.4 . . ?
C3 C4 H4A 111.4 . . ?
C5 C4 H4B 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.3 . . ?
N1 C5 C4 104.0(4) . . ?
N1 C5 H5A 111.0 . . ?
C4 C5 H5A 111.0 . . ?
N1 C5 H5B 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
O2 C6 N2 124.1(4) . . ?
O2 C6 C2 121.9(4) . . ?
N2 C6 C2 113.8(4) . . ?
C12 C7 C8 118.3(4) . . ?
C12 C7 N2 120.4(4) . . ?
C8 C7 N2 121.3(3) . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 S1 118.6(3) . . ?
C7 C8 S1 120.6(3) . . ?
C8 C9 C10 120.9(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 118.9(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 120.7(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
N3 C13 C17 109.3(3) . . ?
N3 C13 C14 102.7(3) . . ?
C17 C13 C14 112.1(3) . . ?
N3 C13 H13 110.8 . . ?
C17 C13 H13 110.8 . . ?
C14 C13 H13 110.8 . . ?
C15 C14 C13 103.4(3) . . ?
C15 C14 H14A 111.1 . . ?
C13 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.0 . . ?
C14 C15 C16 102.5(3) . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15B 111.3 . . ?
C16 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
N3 C16 C15 103.4(3) . . ?
N3 C16 H16A 111.1 . . ?
C15 C16 H16A 111.1 . . ?
N3 C16 H16B 111.1 . . ?
C15 C16 H16B 111.1 . . ?
H16A C16 H16B 109.0 . . ?
O5 C17 N4 124.4(4) . . ?
O5 C17 C13 122.4(4) . . ?
N4 C17 C13 113.2(4) . . ?
C19 C18 C23 119.7(4) . . ?
C19 C18 N4 117.7(4) . . ?
C23 C18 N4 122.6(4) . . ?
C18 C19 C20 120.1(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 119.5(4) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C22 C21 C20 121.5(4) . . ?
C22 C21 Br1 118.9(3) . . ?
C20 C21 Br1 119.5(3) . . ?
C21 C22 C23 118.6(4) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C22 C23 C18 120.6(4) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C1 C24 C27 111.7(4) . . ?
C1 C24 C25 110.4(4) . . ?
C27 C24 C25 111.8(5) . . ?
C1 C24 C26 107.7(4) . . ?
C27 C24 C26 108.2(5) . . ?
C25 C24 C26 106.8(5) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 S1 N3 C16 45.7(4) . . . . ?
O3 S1 N3 C16 176.6(3) . . . . ?
C8 S1 N3 C16 -69.0(3) . . . . ?
O4 S1 N3 C13 -90.1(3) . . . . ?
O3 S1 N3 C13 40.8(3) . . . . ?
C8 S1 N3 C13 155.2(3) . . . . ?
C2 N1 C1 O1 3.0(6) . . . . ?
C5 N1 C1 O1 -177.3(4) . . . . ?
C2 N1 C1 C24 -175.3(4) . . . . ?
C5 N1 C1 C24 4.4(7) . . . . ?
C1 N1 C2 C6 -67.0(5) . . . . ?
C5 N1 C2 C6 113.2(4) . . . . ?
C1 N1 C2 C3 175.1(4) . . . . ?
C5 N1 C2 C3 -4.6(4) . . . . ?
N1 C2 C3 C4 -19.3(5) . . . . ?
C6 C2 C3 C4 -138.7(4) . . . . ?
C2 C3 C4 C5 35.2(5) . . . . ?
C1 N1 C5 C4 -152.5(5) . . . . ?
C2 N1 C5 C4 27.3(5) . . . . ?
C3 C4 C5 N1 -37.7(5) . . . . ?
C7 N2 C6 O2 -8.8(6) . . . . ?
C7 N2 C6 C2 167.5(4) . . . . ?
N1 C2 C6 O2 -36.8(6) . . . . ?
C3 C2 C6 O2 77.4(5) . . . . ?
N1 C2 C6 N2 146.8(4) . . . . ?
C3 C2 C6 N2 -99.0(4) . . . . ?
C6 N2 C7 C12 50.5(6) . . . . ?
C6 N2 C7 C8 -127.8(4) . . . . ?
C12 C7 C8 C9 1.6(6) . . . . ?
N2 C7 C8 C9 180.0(4) . . . . ?
C12 C7 C8 S1 -170.1(3) . . . . ?
N2 C7 C8 S1 8.3(5) . . . . ?
O4 S1 C8 C9 2.6(4) . . . . ?
O3 S1 C8 C9 -126.2(3) . . . . ?
N3 S1 C8 C9 121.2(3) . . . . ?
O4 S1 C8 C7 174.4(3) . . . . ?
O3 S1 C8 C7 45.7(4) . . . . ?
N3 S1 C8 C7 -67.0(4) . . . . ?
C7 C8 C9 C10 -1.7(6) . . . . ?
S1 C8 C9 C10 170.2(3) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C9 C10 C11 C12 1.6(7) . . . . ?
C10 C11 C12 C7 -1.7(7) . . . . ?
C8 C7 C12 C11 0.0(6) . . . . ?
N2 C7 C12 C11 -178.3(4) . . . . ?
C16 N3 C13 C17 108.9(4) . . . . ?
S1 N3 C13 C17 -112.5(3) . . . . ?
C16 N3 C13 C14 -10.3(4) . . . . ?
S1 N3 C13 C14 128.3(3) . . . . ?
N3 C13 C14 C15 32.1(4) . . . . ?
C17 C13 C14 C15 -85.1(4) . . . . ?
C13 C14 C15 C16 -42.1(4) . . . . ?
C13 N3 C16 C15 -15.5(5) . . . . ?
S1 N3 C16 C15 -154.1(3) . . . . ?
C14 C15 C16 N3 35.2(5) . . . . ?
C18 N4 C17 O5 -4.6(7) . . . . ?
C18 N4 C17 C13 173.2(4) . . . . ?
N3 C13 C17 O5 -14.0(6) . . . . ?
C14 C13 C17 O5 99.1(5) . . . . ?
N3 C13 C17 N4 168.1(3) . . . . ?
C14 C13 C17 N4 -78.7(5) . . . . ?
C17 N4 C18 C19 -149.3(4) . . . . ?
C17 N4 C18 C23 31.3(7) . . . . ?
C23 C18 C19 C20 2.4(7) . . . . ?
N4 C18 C19 C20 -177.1(4) . . . . ?
C18 C19 C20 C21 -1.7(7) . . . . ?
C19 C20 C21 C22 1.1(7) . . . . ?
C19 C20 C21 Br1 178.2(3) . . . . ?
C20 C21 C22 C23 -1.2(7) . . . . ?
Br1 C21 C22 C23 -178.3(3) . . . . ?
C21 C22 C23 C18 1.8(7) . . . . ?
C19 C18 C23 C22 -2.4(7) . . . . ?
N4 C18 C23 C22 177.0(4) . . . . ?
O1 C1 C24 C27 121.2(5) . . . . ?
N1 C1 C24 C27 -60.6(6) . . . . ?
O1 C1 C24 C25 -113.8(5) . . . . ?
N1 C1 C24 C25 64.4(6) . . . . ?
O1 C1 C24 C26 2.5(6) . . . . ?
N1 C1 C24 C26 -179.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.086
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate - Petroleum Ether'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1027032'
_audit_update_record             
;
2014-09-27 deposited with the CCDC.
2015-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H32 N4 O6 S2'
_chemical_formula_sum            'C21 H32 N4 O6 S2'
_chemical_formula_weight         500.63
_Chemical_absolute_configuration rmad

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   18.6244(11)
_cell_length_b                   8.4267(4)
_cell_length_c                   16.0611(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.118(5)
_cell_angle_gamma                90.00
_cell_volume                     2516.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    7309
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      25.49

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8547
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17277
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4429
_reflns_number_gt                4052
_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)+(0.0555P)²+1.3256P] 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     SHELXL
_refine_ls_extinction_coef       0.0050(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_number_reflns         4429
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
S1 S 0.86236(4) 0.45826(8) 0.89605(4) 0.0520(2) Uani 1 1 d . . .
S2 S 1.02670(4) 0.53377(15) 0.65120(6) 0.0835(4) Uani 1 1 d . . .
O1 O 1.0854(2) 0.1277(4) 0.8056(3) 0.1469(17) Uani 1 1 d . . .
O2 O 0.92462(12) 0.5537(2) 0.91223(13) 0.0636(5) Uani 1 1 d . . .
O3 O 0.80123(12) 0.4907(3) 0.94363(14) 0.0766(7) Uani 1 1 d . . .
O4 O 0.74593(14) 0.1361(4) 0.70555(19) 0.0948(9) Uani 1 1 d . . .
O5 O 0.97920(19) 0.6643(7) 0.6394(3) 0.158(2) Uani 1 1 d . . .
O6 O 0.9990(2) 0.3823(5) 0.63495(19) 0.1393(17) Uani 1 1 d . . .
N1 N 1.05594(12) 0.5348(3) 0.74755(15) 0.0585(6) Uani 1 1 d . . .
N2 N 0.99716(13) 0.2953(3) 0.83990(17) 0.0558(6) Uani 1 1 d . . .
H2N H 0.9863(15) 0.383(4) 0.8376(16) 0.037(7) Uiso 1 1 d . . .
N3 N 0.84313(11) 0.4733(3) 0.79512(13) 0.0508(5) Uani 1 1 d . . .
N4 N 0.85949(14) 0.2177(3) 0.68902(16) 0.0592(6) Uani 1 1 d . . .
H4N H 0.8882(18) 0.291(4) 0.699(2) 0.065(10) Uiso 1 1 d . . .
C1 C 1.10223(17) 0.4029(5) 0.7775(2) 0.0697(9) Uani 1 1 d . . .
H1 H 1.1329 0.3696 0.7330 0.084 Uiso 1 1 calc R . .
C2 C 1.1489(2) 0.4810(9) 0.8484(3) 0.117(2) Uani 1 1 d . . .
H2A H 1.1533 0.4117 0.8966 0.140 Uiso 1 1 calc R . .
H2B H 1.1967 0.5039 0.8302 0.140 Uiso 1 1 calc R . .
C3 C 1.1112(3) 0.6297(9) 0.8689(3) 0.129(2) Uani 1 1 d . . .
H3A H 1.0747 0.6098 0.9084 0.154 Uiso 1 1 calc R . .
H3B H 1.1448 0.7079 0.8922 0.154 Uiso 1 1 calc R . .
C4 C 1.0788(3) 0.6831(6) 0.7888(3) 0.0953(13) Uani 1 1 d . . .
H4A H 1.1135 0.7390 0.7568 0.114 Uiso 1 1 calc R . .
H4B H 1.0380 0.7522 0.7966 0.114 Uiso 1 1 calc R . .
C5 C 1.05991(19) 0.2599(5) 0.8071(2) 0.0761(10) Uani 1 1 d . . .
C6 C 0.94947(15) 0.1971(3) 0.87977(16) 0.0504(6) Uani 1 1 d . . .
C7 C 0.88474(15) 0.2568(3) 0.90827(16) 0.0489(6) Uani 1 1 d . . .
C8 C 0.83680(18) 0.1609(4) 0.9483(2) 0.0639(8) Uani 1 1 d . . .
H8 H 0.7945 0.2033 0.9670 0.077 Uiso 1 1 calc R . .
C9 C 0.8523(2) 0.0024(5) 0.9602(2) 0.0794(10) Uani 1 1 d . . .
H9 H 0.8206 -0.0631 0.9869 0.095 Uiso 1 1 calc R . .
C10 C 0.9147(2) -0.0573(4) 0.9324(2) 0.0817(10) Uani 1 1 d . . .
H10 H 0.9247 -0.1646 0.9402 0.098 Uiso 1 1 calc R . .
C11 C 0.9630(2) 0.0356(4) 0.8935(2) 0.0706(8) Uani 1 1 d . . .
H11 H 1.0053 -0.0091 0.8759 0.085 Uiso 1 1 calc R . .
C12 C 0.77747(14) 0.3854(4) 0.76349(18) 0.0578(7) Uani 1 1 d . . .
H12 H 0.7484 0.3593 0.8107 0.069 Uiso 1 1 calc R . .
C13 C 0.73696(19) 0.5060(5) 0.7081(3) 0.0862(12) Uani 1 1 d . . .
H13A H 0.7171 0.4557 0.6576 0.103 Uiso 1 1 calc R . .
H13B H 0.6979 0.5529 0.7372 0.103 Uiso 1 1 calc R . .
C14 C 0.7891(3) 0.6258(7) 0.6883(4) 0.121(2) Uani 1 1 d . . .
H14A H 0.7654 0.7262 0.6758 0.145 Uiso 1 1 calc R . .
H14B H 0.8152 0.5938 0.6405 0.145 Uiso 1 1 calc R . .
C15 C 0.8391(2) 0.6408(4) 0.7641(2) 0.0716(9) Uani 1 1 d . . .
H15A H 0.8197 0.7112 0.8050 0.086 Uiso 1 1 calc R . .
H15B H 0.8860 0.6793 0.7498 0.086 Uiso 1 1 calc R . .
C16 C 0.79440(16) 0.2337(4) 0.71771(19) 0.0615(8) Uani 1 1 d . . .
C17 C 0.8807(2) 0.0812(4) 0.6408(2) 0.0737(9) Uani 1 1 d . . .
H17A H 0.8487 -0.0065 0.6514 0.088 Uiso 1 1 calc R . .
H17B H 0.9289 0.0497 0.6598 0.088 Uiso 1 1 calc R . .
C18 C 0.8792(3) 0.1113(7) 0.5483(3) 0.1162(18) Uani 1 1 d . . .
H18 H 0.9199 0.1818 0.5392 0.139 Uiso 1 1 calc R . .
C19 C 0.8170(5) 0.1891(9) 0.5116(3) 0.156(3) Uani 1 1 d . . .
H19A H 0.7750 0.1270 0.5210 0.234 Uiso 1 1 calc R . .
H19B H 0.8220 0.2006 0.4527 0.234 Uiso 1 1 calc R . .
H19C H 0.8123 0.2920 0.5363 0.234 Uiso 1 1 calc R . .
C20 C 0.8958(4) -0.0452(9) 0.5046(4) 0.165(3) Uani 1 1 d . . .
H20A H 0.8566 -0.1177 0.5098 0.248 Uiso 1 1 calc R . .
H20B H 0.9390 -0.0905 0.5299 0.248 Uiso 1 1 calc R . .
H20C H 0.9023 -0.0253 0.4466 0.248 Uiso 1 1 calc R . .
C21 C 1.0993(2) 0.5658(6) 0.5890(2) 0.0844(11) Uani 1 1 d . . .
H21A H 1.1316 0.4771 0.5940 0.127 Uiso 1 1 calc R . .
H21B H 1.1242 0.6607 0.6069 0.127 Uiso 1 1 calc R . .
H21C H 1.0821 0.5772 0.5319 0.127 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
S1 O2 1.423(2) . ?
S1 O3 1.432(2) . ?
S1 N3 1.646(2) . ?
S1 C7 1.757(3) . ?
S2 O6 1.396(4) . ?
S2 O5 1.418(4) . ?
S2 N1 1.612(2) . ?
S2 C21 1.746(4) . ?
O1 C5 1.212(5) . ?
O4 C16 1.229(4) . ?
N1 C4 1.467(5) . ?
N1 C1 1.471(4) . ?
N2 C5 1.341(4) . ?
N2 C6 1.395(4) . ?
N2 H2N 0.77(3) . ?
N3 C12 1.495(4) . ?
N3 C15 1.498(4) . ?
N4 C16 1.327(4) . ?
N4 C17 1.453(4) . ?
N4 H4N 0.83(4) . ?
C1 C5 1.529(5) . ?
C1 C2 1.542(6) . ?
C1 H1 0.9800 . ?
C2 C3 1.482(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.462(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C11 1.399(4) . ?
C6 C7 1.406(4) . ?
C7 C8 1.388(4) . ?
C8 C9 1.377(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C16 1.516(5) . ?
C12 C13 1.523(5) . ?
C12 H12 0.9800 . ?
C13 C14 1.448(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.497(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.506(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.430(8) . ?
C18 C20 1.533(8) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
O2 S1 O3 117.30(14) . . ?
O2 S1 N3 105.53(13) . . ?
O3 S1 N3 111.98(13) . . ?
O2 S1 C7 109.85(13) . . ?
O3 S1 C7 108.38(15) . . ?
N3 S1 C7 102.83(13) . . ?
O6 S2 O5 117.6(3) . . ?
O6 S2 N1 106.63(17) . . ?
O5 S2 N1 107.5(2) . . ?
O6 S2 C21 108.9(2) . . ?
O5 S2 C21 107.5(2) . . ?
N1 S2 C21 108.48(15) . . ?
C4 N1 C1 110.2(3) . . ?
C4 N1 S2 120.8(3) . . ?
C1 N1 S2 118.1(2) . . ?
C5 N2 C6 129.7(3) . . ?
C5 N2 H2N 115(2) . . ?
C6 N2 H2N 115(2) . . ?
C12 N3 C15 109.2(2) . . ?
C12 N3 S1 115.25(18) . . ?
C15 N3 S1 113.9(2) . . ?
C16 N4 C17 123.0(3) . . ?
C16 N4 H4N 117(2) . . ?
C17 N4 H4N 120(2) . . ?
N1 C1 C5 113.2(2) . . ?
N1 C1 C2 102.5(4) . . ?
C5 C1 C2 112.7(3) . . ?
N1 C1 H1 109.4 . . ?
C5 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
C3 C2 C1 105.7(3) . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C4 C3 C2 104.1(4) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 N1 103.4(4) . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
N1 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
O1 C5 N2 124.3(4) . . ?
O1 C5 C1 120.6(3) . . ?
N2 C5 C1 114.9(3) . . ?
N2 C6 C11 122.4(3) . . ?
N2 C6 C7 121.1(3) . . ?
C11 C6 C7 116.6(3) . . ?
C8 C7 C6 121.8(3) . . ?
C8 C7 S1 117.4(2) . . ?
C6 C7 S1 120.8(2) . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 122.1(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C6 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
N3 C12 C16 113.3(2) . . ?
N3 C12 C13 103.8(3) . . ?
C16 C12 C13 112.9(3) . . ?
N3 C12 H12 108.9 . . ?
C16 C12 H12 108.9 . . ?
C13 C12 H12 108.9 . . ?
C14 C13 C12 106.1(3) . . ?
C14 C13 H13A 110.5 . . ?
C12 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C12 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C13 C14 C15 106.0(4) . . ?
C13 C14 H14A 110.5 . . ?
C15 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
C15 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C14 C15 N3 102.0(3) . . ?
C14 C15 H15A 111.4 . . ?
N3 C15 H15A 111.4 . . ?
C14 C15 H15B 111.4 . . ?
N3 C15 H15B 111.4 . . ?
H15A C15 H15B 109.2 . . ?
O4 C16 N4 123.6(3) . . ?
O4 C16 C12 118.1(3) . . ?
N4 C16 C12 118.2(3) . . ?
N4 C17 C18 113.7(3) . . ?
N4 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
N4 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 117.1(5) . . ?
C19 C18 C20 112.6(5) . . ?
C17 C18 C20 108.3(5) . . ?
C19 C18 H18 106.0 . . ?
C17 C18 H18 106.0 . . ?
C20 C18 H18 106.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S2 C21 H21A 109.5 . . ?
S2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
O6 S2 N1 C4 -170.8(3) . . . . ?
O5 S2 N1 C4 -43.8(3) . . . . ?
C21 S2 N1 C4 72.1(3) . . . . ?
O6 S2 N1 C1 48.4(3) . . . . ?
O5 S2 N1 C1 175.4(3) . . . . ?
C21 S2 N1 C1 -68.7(3) . . . . ?
O2 S1 N3 C12 -178.3(2) . . . . ?
O3 S1 N3 C12 -49.6(3) . . . . ?
C7 S1 N3 C12 66.5(2) . . . . ?
O2 S1 N3 C15 -51.0(2) . . . . ?
O3 S1 N3 C15 77.7(3) . . . . ?
C7 S1 N3 C15 -166.1(2) . . . . ?
C4 N1 C1 C5 128.4(3) . . . . ?
S2 N1 C1 C5 -86.9(3) . . . . ?
C4 N1 C1 C2 6.8(3) . . . . ?
S2 N1 C1 C2 151.5(2) . . . . ?
N1 C1 C2 C3 16.7(4) . . . . ?
C5 C1 C2 C3 -105.3(4) . . . . ?
C1 C2 C3 C4 -34.1(5) . . . . ?
C2 C3 C4 N1 37.6(4) . . . . ?
C1 N1 C4 C3 -27.9(4) . . . . ?
S2 N1 C4 C3 -171.5(3) . . . . ?
C6 N2 C5 O1 1.8(7) . . . . ?
C6 N2 C5 C1 -172.9(3) . . . . ?
N1 C1 C5 O1 153.9(5) . . . . ?
C2 C1 C5 O1 -90.4(6) . . . . ?
N1 C1 C5 N2 -31.2(5) . . . . ?
C2 C1 C5 N2 84.6(5) . . . . ?
C5 N2 C6 C11 1.6(5) . . . . ?
C5 N2 C6 C7 -178.3(3) . . . . ?
N2 C6 C7 C8 -179.8(3) . . . . ?
C11 C6 C7 C8 0.3(4) . . . . ?
N2 C6 C7 S1 -1.0(4) . . . . ?
C11 C6 C7 S1 179.1(2) . . . . ?
O2 S1 C7 C8 138.6(2) . . . . ?
O3 S1 C7 C8 9.3(3) . . . . ?
N3 S1 C7 C8 -109.4(2) . . . . ?
O2 S1 C7 C6 -40.2(3) . . . . ?
O3 S1 C7 C6 -169.5(2) . . . . ?
N3 S1 C7 C6 71.8(2) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
S1 C7 C8 C9 -179.3(3) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C9 C10 C11 C6 -0.7(6) . . . . ?
N2 C6 C11 C10 -179.6(3) . . . . ?
C7 C6 C11 C10 0.3(5) . . . . ?
C15 N3 C12 C16 126.1(3) . . . . ?
S1 N3 C12 C16 -104.2(2) . . . . ?
C15 N3 C12 C13 3.4(3) . . . . ?
S1 N3 C12 C13 133.0(2) . . . . ?
N3 C12 C13 C14 19.0(5) . . . . ?
C16 C12 C13 C14 -104.0(4) . . . . ?
C12 C13 C14 C15 -34.5(6) . . . . ?
C13 C14 C15 N3 35.4(5) . . . . ?
C12 N3 C15 C14 -23.3(4) . . . . ?
S1 N3 C15 C14 -153.7(3) . . . . ?
C17 N4 C16 O4 -0.8(5) . . . . ?
C17 N4 C16 C12 -176.9(3) . . . . ?
N3 C12 C16 O4 164.2(3) . . . . ?
C13 C12 C16 O4 -78.3(4) . . . . ?
N3 C12 C16 N4 -19.4(4) . . . . ?
C13 C12 C16 N4 98.1(3) . . . . ?
C16 N4 C17 C18 100.4(4) . . . . ?
N4 C17 C18 C19 -46.3(7) . . . . ?
N4 C17 C18 C20 -174.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate - Petroleum Ether'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1027033'
_audit_update_record             
;
2014-09-27 deposited with the CCDC.
2015-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 Br N4 O6 S2'
_chemical_formula_sum            'C23 H27 Br N4 O6 S2'
_chemical_formula_weight         599.52
_chemical_absolute_configuration rmad

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)

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

_cell_length_a                   8.1060(12)
_cell_length_b                   10.5928(16)
_cell_length_c                   14.983(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.273(8)
_cell_angle_gamma                90.00
_cell_volume                     1278.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9140
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.41

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    1.817
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3846
_exptl_absorpt_correction_T_max  0.6208
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24792
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         30.42
_reflns_number_total             7389
_reflns_number_gt                5331
_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)+(0.0381P)²+0.0000P] 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   0.015(5)
_refine_ls_number_reflns         7389
_refine_ls_number_parameters     335
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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 1.38152(3) 1.32379(3) 0.28823(2) 0.06817(10) Uani 1 1 d . . .
S1 S 0.59797(7) 0.68080(6) 0.29033(4) 0.04783(14) Uani 1 1 d . . .
S2 S 0.91780(8) 0.73669(6) 0.02920(4) 0.05084(15) Uani 1 1 d . . .
O1 O 0.7373(4) 1.12253(19) 0.15659(17) 0.0967(9) Uani 1 1 d . . .
O2 O 0.5246(2) 0.68865(18) 0.19941(12) 0.0599(5) Uani 1 1 d . . .
O3 O 0.5177(2) 0.6012(2) 0.34929(14) 0.0712(6) Uani 1 1 d . . .
O4 O 1.0344(3) 0.79281(19) 0.46789(12) 0.0690(5) Uani 1 1 d . B .
O5 O 0.8591(3) 0.61213(18) 0.00932(14) 0.0763(6) Uani 1 1 d . . .
O6 O 1.0343(2) 0.7548(2) 0.10575(14) 0.0725(6) Uani 1 1 d . . .
N1 N 0.7578(2) 0.8231(2) 0.04256(13) 0.0498(4) Uani 1 1 d . . .
N2 N 0.7156(2) 0.91945(19) 0.20391(13) 0.0466(4) Uani 1 1 d . . .
H2N H 0.7207 0.8427 0.1856 0.056 Uiso 1 1 calc R . .
N3 N 0.7927(2) 0.63868(18) 0.28528(12) 0.0432(4) Uani 1 1 d . B .
N4 N 1.0496(2) 0.8139(2) 0.31773(12) 0.0456(4) Uani 1 1 d . B .
H4N H 1.0300 0.7744 0.2675 0.055 Uiso 1 1 calc R . .
C1 C 0.7883(3) 0.9612(2) 0.05470(19) 0.0568(6) Uani 1 1 d . . .
H1 H 0.9057 0.9787 0.0499 0.068 Uiso 1 1 calc R . .
C3 C 0.6857(5) 1.0227(4) -0.0216(3) 0.0974(12) Uani 1 1 d . . .
H3A H 0.7417 1.0228 -0.0756 0.117 Uiso 1 1 calc R . .
H3B H 0.6567 1.1086 -0.0071 0.117 Uiso 1 1 calc R . .
C4 C 0.5342(5) 0.9368(6) -0.0311(3) 0.1195(18) Uani 1 1 d . . .
H4A H 0.4736 0.9456 -0.0903 0.143 Uiso 1 1 calc R . .
H4B H 0.4606 0.9576 0.0136 0.143 Uiso 1 1 calc R . .
C5 C 0.6009(4) 0.8031(5) -0.0171(2) 0.0959(14) Uani 1 1 d . . .
H5A H 0.5242 0.7504 0.0115 0.115 Uiso 1 1 calc R . .
H5B H 0.6220 0.7649 -0.0736 0.115 Uiso 1 1 calc R . .
C6 C 0.7444(3) 1.0092(2) 0.14403(19) 0.0554(6) Uani 1 1 d . . .
C7 C 0.6782(3) 0.9354(2) 0.29251(15) 0.0431(5) Uani 1 1 d . . .
C8 C 0.6210(2) 0.8319(3) 0.33885(14) 0.0448(5) Uani 1 1 d . . .
C9 C 0.5791(3) 0.8462(3) 0.42509(17) 0.0596(7) Uani 1 1 d . . .
H9 H 0.5406 0.7773 0.4552 0.071 Uiso 1 1 calc R . .
C10 C 0.5941(4) 0.9627(4) 0.4669(2) 0.0705(9) Uani 1 1 d . . .
H10 H 0.5632 0.9729 0.5244 0.085 Uiso 1 1 calc R . .
C11 C 0.6547(4) 1.0628(3) 0.4228(2) 0.0690(8) Uani 1 1 d . . .
H11 H 0.6673 1.1403 0.4519 0.083 Uiso 1 1 calc R . .
C12 C 0.6980(3) 1.0520(3) 0.33646(19) 0.0553(6) Uani 1 1 d . . .
H12 H 0.7396 1.1212 0.3079 0.066 Uiso 1 1 calc R . .
C13 C 0.9008(3) 0.6352(2) 0.37257(16) 0.0464(5) Uani 1 1 d . B .
H13 H 0.8311 0.6215 0.4211 0.056 Uiso 1 1 calc R . .
C14 C 1.0096(4) 0.5184(3) 0.3644(2) 0.0676(8) Uani 1 1 d . . .
H14A H 1.1078 0.5399 0.3360 0.081 Uiso 1 1 calc R A 1
H14B H 1.0438 0.4827 0.4231 0.081 Uiso 1 1 calc R A 1
C15 C 0.9054(6) 0.4284(5) 0.3087(4) 0.0650(12) Uani 0.60 1 d P B 1
H15A H 0.8299 0.3842 0.3438 0.078 Uiso 0.60 1 calc PR B 1
H15B H 0.9726 0.3673 0.2808 0.078 Uiso 0.60 1 calc PR B 1
C15' C 0.9811(10) 0.4824(7) 0.2655(5) 0.0663(19) Uani 0.40 1 d P B 2
H15C H 1.0557 0.5287 0.2311 0.080 Uiso 0.40 1 calc PR B 2
H15D H 0.9988 0.3927 0.2577 0.080 Uiso 0.40 1 calc PR B 2
C16 C 0.8094(4) 0.5158(3) 0.2371(2) 0.0605(7) Uani 1 1 d . . .
H16A H 0.8712 0.5271 0.1858 0.073 Uiso 1 1 calc R B 1
H16B H 0.7012 0.4809 0.2167 0.073 Uiso 1 1 calc R B 1
C17 C 0.9993(3) 0.7560(2) 0.39120(16) 0.0452(5) Uani 1 1 d . . .
C18 C 1.1311(2) 0.9326(2) 0.31482(16) 0.0416(5) Uani 1 1 d . . .
C19 C 1.2223(3) 0.9556(2) 0.24425(18) 0.0503(6) Uani 1 1 d . B .
H19 H 1.2347 0.8925 0.2023 0.060 Uiso 1 1 calc R . .
C20 C 1.2950(3) 1.0713(3) 0.23562(19) 0.0552(6) Uani 1 1 d . . .
H20 H 1.3559 1.0869 0.1877 0.066 Uiso 1 1 calc R B .
C21 C 1.2776(3) 1.1636(2) 0.29760(17) 0.0463(5) Uani 1 1 d . B .
C22 C 1.1876(3) 1.1431(3) 0.36857(17) 0.0534(6) Uani 1 1 d . . .
H22 H 1.1763 1.2066 0.4103 0.064 Uiso 1 1 calc R B .
C23 C 1.1138(3) 1.0267(2) 0.37726(18) 0.0503(6) Uani 1 1 d . B .
H23 H 1.0524 1.0116 0.4251 0.060 Uiso 1 1 calc R . .
C24 C 1.0005(4) 0.7956(3) -0.0667(2) 0.0705(8) Uani 1 1 d . . .
H24A H 1.0330 0.8820 -0.0567 0.106 Uiso 1 1 calc R . .
H24B H 0.9179 0.7904 -0.1176 0.106 Uiso 1 1 calc R . .
H24C H 1.0955 0.7463 -0.0778 0.106 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 C21 1.906(2) . ?
S1 O2 1.4280(18) . ?
S1 O3 1.4281(19) . ?
S1 N3 1.650(2) . ?
S1 C8 1.759(3) . ?
S2 O6 1.417(2) . ?
S2 O5 1.423(2) . ?
S2 N1 1.618(2) . ?
S2 C24 1.764(3) . ?
O1 C6 1.217(3) . ?
O4 C17 1.217(3) . ?
N1 C5 1.488(4) . ?
N1 C1 1.492(4) . ?
N2 C6 1.345(3) . ?
N2 C7 1.404(3) . ?
N2 H2N 0.8600 . ?
N3 C13 1.493(3) . ?
N3 C16 1.501(3) . ?
N4 C17 1.361(3) . ?
N4 C18 1.424(3) . ?
N4 H4N 0.8600 . ?
C1 C3 1.488(5) . ?
C1 C6 1.510(4) . ?
C1 H1 0.9800 . ?
C3 C4 1.522(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.522(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C12 1.401(4) . ?
C7 C8 1.403(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.383(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C17 1.518(3) . ?
C13 C14 1.532(4) . ?
C13 H13 0.9800 . ?
C14 C15 1.470(6) . ?
C14 C15' 1.523(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.559(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15' C16 1.454(8) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C19 1.376(4) . ?
C18 C23 1.384(4) . ?
C19 C20 1.372(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(4) . ?
C22 C23 1.382(4) . ?
C22 H22 0.9300 . ?
C23 H23 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
O2 S1 O3 117.01(12) . . ?
O2 S1 N3 105.82(11) . . ?
O3 S1 N3 111.80(12) . . ?
O2 S1 C8 110.82(11) . . ?
O3 S1 C8 108.45(12) . . ?
N3 S1 C8 101.90(10) . . ?
O6 S2 O5 118.24(14) . . ?
O6 S2 N1 107.20(12) . . ?
O5 S2 N1 107.20(14) . . ?
O6 S2 C24 109.42(16) . . ?
O5 S2 C24 107.80(14) . . ?
N1 S2 C24 106.37(13) . . ?
C5 N1 C1 109.4(3) . . ?
C5 N1 S2 119.3(2) . . ?
C1 N1 S2 116.42(17) . . ?
C6 N2 C7 128.1(2) . . ?
C6 N2 H2N 116.0 . . ?
C7 N2 H2N 116.0 . . ?
C13 N3 C16 108.93(19) . . ?
C13 N3 S1 116.06(15) . . ?
C16 N3 S1 113.18(16) . . ?
C17 N4 C18 127.1(2) . . ?
C17 N4 H4N 116.4 . . ?
C18 N4 H4N 116.4 . . ?
C3 C1 N1 105.3(3) . . ?
C3 C1 C6 111.5(3) . . ?
N1 C1 C6 112.7(2) . . ?
C3 C1 H1 109.0 . . ?
N1 C1 H1 109.0 . . ?
C6 C1 H1 109.0 . . ?
C1 C3 C4 100.8(3) . . ?
C1 C3 H3A 111.6 . . ?
C4 C3 H3A 111.6 . . ?
C1 C3 H3B 111.6 . . ?
C4 C3 H3B 111.6 . . ?
H3A C3 H3B 109.4 . . ?
C3 C4 C5 105.8(3) . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
N1 C5 C4 102.6(3) . . ?
N1 C5 H5A 111.3 . . ?
C4 C5 H5A 111.3 . . ?
N1 C5 H5B 111.3 . . ?
C4 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
O1 C6 N2 125.4(3) . . ?
O1 C6 C1 119.3(2) . . ?
N2 C6 C1 115.3(2) . . ?
C12 C7 C8 118.9(2) . . ?
C12 C7 N2 121.7(2) . . ?
C8 C7 N2 119.4(2) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 S1 117.4(2) . . ?
C7 C8 S1 122.17(17) . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 122.0(3) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C12 C7 119.0(3) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?
N3 C13 C17 112.78(19) . . ?
N3 C13 C14 103.7(2) . . ?
C17 C13 C14 113.6(2) . . ?
N3 C13 H13 108.9 . . ?
C17 C13 H13 108.9 . . ?
C14 C13 H13 108.9 . . ?
C15 C14 C15' 43.1(4) . . ?
C15 C14 C13 105.6(3) . . ?
C15' C14 C13 104.6(3) . . ?
C15 C14 H14A 110.6 . . ?
C15' C14 H14A 71.2 . . ?
C13 C14 H14A 110.6 . . ?
C15 C14 H14B 110.6 . . ?
C15' C14 H14B 141.5 . . ?
C13 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C14 C15 C16 102.6(3) . . ?
C14 C15 H15A 111.2 . . ?
C16 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C16 C15 H15B 111.2 . . ?
H15A C15 H15B 109.2 . . ?
C16 C15' C14 105.2(5) . . ?
C16 C15' H15C 110.7 . . ?
C14 C15' H15C 110.7 . . ?
C16 C15' H15D 110.7 . . ?
C14 C15' H15D 110.7 . . ?
H15C C15' H15D 108.8 . . ?
C15' C16 N3 101.8(3) . . ?
C15' C16 C15 42.6(4) . . ?
N3 C16 C15 104.4(3) . . ?
C15' C16 H16A 72.6 . . ?
N3 C16 H16A 110.9 . . ?
C15 C16 H16A 110.9 . . ?
C15' C16 H16B 143.4 . . ?
N3 C16 H16B 110.9 . . ?
C15 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
O4 C17 N4 124.0(2) . . ?
O4 C17 C13 120.5(2) . . ?
N4 C17 C13 115.4(2) . . ?
C19 C18 C23 119.7(2) . . ?
C19 C18 N4 118.0(2) . . ?
C23 C18 N4 122.2(2) . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 121.1(2) . . ?
C20 C21 Br1 120.52(19) . . ?
C22 C21 Br1 118.37(18) . . ?
C21 C22 C23 119.1(2) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C18 120.1(2) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
O6 S2 N1 C5 -167.0(2) . . . . ?
O5 S2 N1 C5 -39.0(3) . . . . ?
C24 S2 N1 C5 76.1(3) . . . . ?
O6 S2 N1 C1 58.2(2) . . . . ?
O5 S2 N1 C1 -173.86(19) . . . . ?
C24 S2 N1 C1 -58.7(2) . . . . ?
O2 S1 N3 C13 174.69(16) . . . . ?
O3 S1 N3 C13 -56.9(2) . . . . ?
C8 S1 N3 C13 58.77(18) . . . . ?
O2 S1 N3 C16 -58.27(19) . . . . ?
O3 S1 N3 C16 70.2(2) . . . . ?
C8 S1 N3 C16 -174.20(17) . . . . ?
C5 N1 C1 C3 -19.7(3) . . . . ?
S2 N1 C1 C3 119.4(2) . . . . ?
C5 N1 C1 C6 102.2(3) . . . . ?
S2 N1 C1 C6 -118.8(2) . . . . ?
N1 C1 C3 C4 35.8(4) . . . . ?
C6 C1 C3 C4 -86.8(4) . . . . ?
C1 C3 C4 C5 -40.0(4) . . . . ?
C1 N1 C5 C4 -5.4(3) . . . . ?
S2 N1 C5 C4 -143.0(3) . . . . ?
C3 C4 C5 N1 28.1(4) . . . . ?
C7 N2 C6 O1 -2.5(5) . . . . ?
C7 N2 C6 C1 177.6(2) . . . . ?
C3 C1 C6 O1 -49.8(4) . . . . ?
N1 C1 C6 O1 -168.0(3) . . . . ?
C3 C1 C6 N2 130.1(3) . . . . ?
N1 C1 C6 N2 11.8(3) . . . . ?
C6 N2 C7 C12 -12.8(4) . . . . ?
C6 N2 C7 C8 167.8(2) . . . . ?
C12 C7 C8 C9 2.4(3) . . . . ?
N2 C7 C8 C9 -178.2(2) . . . . ?
C12 C7 C8 S1 -178.13(17) . . . . ?
N2 C7 C8 S1 1.2(3) . . . . ?
O2 S1 C8 C9 136.71(18) . . . . ?
O3 S1 C8 C9 7.0(2) . . . . ?
N3 S1 C8 C9 -111.08(18) . . . . ?
O2 S1 C8 C7 -42.7(2) . . . . ?
O3 S1 C8 C7 -172.47(18) . . . . ?
N3 S1 C8 C7 69.47(19) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
S1 C8 C9 C10 -179.9(2) . . . . ?
C8 C9 C10 C11 -1.7(4) . . . . ?
C9 C10 C11 C12 1.7(5) . . . . ?
C10 C11 C12 C7 0.4(4) . . . . ?
C8 C7 C12 C11 -2.4(4) . . . . ?
N2 C7 C12 C11 178.2(2) . . . . ?
C16 N3 C13 C17 135.3(2) . . . . ?
S1 N3 C13 C17 -95.6(2) . . . . ?
C16 N3 C13 C14 12.0(3) . . . . ?
S1 N3 C13 C14 141.13(19) . . . . ?
N3 C13 C14 C15 -32.3(4) . . . . ?
C17 C13 C14 C15 -155.1(3) . . . . ?
N3 C13 C14 C15' 12.3(4) . . . . ?
C17 C13 C14 C15' -110.4(4) . . . . ?
C15' C14 C15 C16 -56.0(5) . . . . ?
C13 C14 C15 C16 38.9(4) . . . . ?
C15 C14 C15' C16 64.0(5) . . . . ?
C13 C14 C15' C16 -33.3(6) . . . . ?
C14 C15' C16 N3 39.8(5) . . . . ?
C14 C15' C16 C15 -58.7(5) . . . . ?
C13 N3 C16 C15' -32.6(4) . . . . ?
S1 N3 C16 C15' -163.3(4) . . . . ?
C13 N3 C16 C15 11.1(3) . . . . ?
S1 N3 C16 C15 -119.6(3) . . . . ?
C14 C15 C16 C15' 61.1(5) . . . . ?
C14 C15 C16 N3 -30.8(4) . . . . ?
C18 N4 C17 O4 -8.6(4) . . . . ?
C18 N4 C17 C13 174.44(19) . . . . ?
N3 C13 C17 O4 148.4(2) . . . . ?
C14 C13 C17 O4 -93.9(3) . . . . ?
N3 C13 C17 N4 -34.5(3) . . . . ?
C14 C13 C17 N4 83.2(3) . . . . ?
C17 N4 C18 C19 157.7(2) . . . . ?
C17 N4 C18 C23 -26.0(3) . . . . ?
C23 C18 C19 C20 -0.3(4) . . . . ?
N4 C18 C19 C20 176.1(2) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C19 C20 C21 C22 -0.4(4) . . . . ?
C19 C20 C21 Br1 178.66(19) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
Br1 C21 C22 C23 -178.89(18) . . . . ?
C21 C22 C23 C18 0.0(4) . . . . ?
C19 C18 C23 C22 0.1(4) . . . . ?
N4 C18 C23 C22 -176.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        30.42
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate - Petroleum Ether'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1027034'
_audit_update_record             
;
2014-09-27 deposited with the CCDC.
2015-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H26 N4 O6 S2'
_chemical_formula_sum            'C17 H26 N4 O6 S2'
_chemical_formula_weight         446.54
_chemical_absolute_configuration rmad

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.5896(2)
_cell_length_b                   14.7665(3)
_cell_length_c                   14.7848(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2093.60(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9845
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8661
_exptl_absorpt_correction_T_max  0.9035
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32530
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3677
_reflns_number_gt                3525
_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)+(0.0495P)²+0.6229P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_number_reflns         3677
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_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
S1 S 0.38681(7) 0.17961(5) 0.12459(5) 0.04918(18) Uani 1 1 d . . .
S2 S -0.04459(7) 0.22859(4) 0.24011(4) 0.04117(16) Uani 1 1 d . . .
O1 O 0.3052(2) 0.15934(15) 0.04703(15) 0.0646(6) Uani 1 1 d . . .
O2 O 0.3443(2) 0.14592(13) 0.21143(15) 0.0625(5) Uani 1 1 d . . .
O3 O 0.3702(3) 0.41700(15) 0.34386(14) 0.0665(6) Uani 1 1 d . . .
O4 O 0.0228(2) 0.23940(13) 0.15362(11) 0.0530(5) Uani 1 1 d . . .
O5 O -0.1860(2) 0.19873(14) 0.24282(15) 0.0629(6) Uani 1 1 d . . .
O6 O 0.19927(17) 0.23494(14) 0.44298(13) 0.0516(5) Uani 1 1 d . . .
N1 N 0.3898(2) 0.29005(14) 0.13421(14) 0.0442(5) Uani 1 1 d . . .
N2 N 0.2031(2) 0.35791(14) 0.25155(14) 0.0436(5) Uani 1 1 d . . .
N3 N 0.0512(2) 0.15771(12) 0.29419(13) 0.0355(4) Uani 1 1 d . . .
H3 H 0.1204 0.1354 0.2647 0.043 Uiso 1 1 calc R . .
N4 N -0.0098(2) 0.23816(16) 0.50997(14) 0.0409(5) Uani 1 1 d . . .
C1 C 0.4481(3) 0.33179(19) 0.21747(17) 0.0483(6) Uani 1 1 d . . .
H1 H 0.4997 0.2859 0.2517 0.058 Uiso 1 1 calc R . .
C2 C 0.5501(4) 0.4023(3) 0.1812(2) 0.0713(9) Uani 1 1 d . . .
H2A H 0.5563 0.4540 0.2215 0.086 Uiso 1 1 calc R . .
H2B H 0.6424 0.3767 0.1732 0.086 Uiso 1 1 calc R . .
C3 C 0.4886(5) 0.4280(3) 0.0942(2) 0.0883(13) Uani 1 1 d . . .
H3A H 0.5596 0.4528 0.0545 0.106 Uiso 1 1 calc R . .
H3B H 0.4169 0.4734 0.1030 0.106 Uiso 1 1 calc R . .
C4 C 0.4277(4) 0.3451(2) 0.0539(2) 0.0634(8) Uani 1 1 d . . .
H4A H 0.4952 0.3138 0.0163 0.076 Uiso 1 1 calc R . .
H4B H 0.3460 0.3593 0.0179 0.076 Uiso 1 1 calc R . .
C5 C 0.3362(3) 0.37289(17) 0.27763(16) 0.0461(6) Uani 1 1 d . . .
C6 C 0.0808(3) 0.38832(15) 0.29451(16) 0.0421(6) Uani 1 1 d . . .
C7 C -0.0390(3) 0.33598(16) 0.29470(16) 0.0429(6) Uani 1 1 d . . .
C8 C -0.1623(3) 0.3669(2) 0.33391(19) 0.0546(7) Uani 1 1 d . . .
H8 H -0.2416 0.3307 0.3346 0.066 Uiso 1 1 calc R . .
C9 C -0.1642(4) 0.4522(2) 0.3716(2) 0.0674(9) Uani 1 1 d . . .
H9 H -0.2456 0.4738 0.3981 0.081 Uiso 1 1 calc R . .
C10 C -0.0485(4) 0.50508(19) 0.37047(19) 0.0661(9) Uani 1 1 d . . .
H10 H -0.0523 0.5632 0.3946 0.079 Uiso 1 1 calc R . .
C11 C 0.0741(4) 0.47381(17) 0.33420(18) 0.0552(8) Uani 1 1 d . . .
H11 H 0.1535 0.5100 0.3361 0.066 Uiso 1 1 calc R . .
C12 C 0.0350(2) 0.12598(15) 0.38907(16) 0.0371(5) Uani 1 1 d . . .
C13 C 0.1386(3) 0.04798(18) 0.3985(2) 0.0535(7) Uani 1 1 d . . .
H13A H 0.1130 0.0000 0.3580 0.080 Uiso 1 1 calc R . .
H13B H 0.1373 0.0260 0.4596 0.080 Uiso 1 1 calc R . .
H13C H 0.2306 0.0690 0.3839 0.080 Uiso 1 1 calc R . .
C14 C -0.1126(3) 0.0916(2) 0.4072(2) 0.0548(7) Uani 1 1 d . . .
H14A H -0.1775 0.1408 0.4013 0.082 Uiso 1 1 calc R . .
H14B H -0.1177 0.0674 0.4674 0.082 Uiso 1 1 calc R . .
H14C H -0.1355 0.0451 0.3643 0.082 Uiso 1 1 calc R . .
C15 C 0.0817(2) 0.20475(15) 0.45140(16) 0.0348(5) Uani 1 1 d . . .
C16 C 0.0230(3) 0.3171(2) 0.56418(19) 0.0517(6) Uani 1 1 d . . .
H16A H 0.0930 0.3017 0.6080 0.078 Uiso 1 1 calc R . .
H16B H -0.0596 0.3374 0.5948 0.078 Uiso 1 1 calc R . .
H16C H 0.0572 0.3645 0.5257 0.078 Uiso 1 1 calc R . .
C17 C 0.5594(3) 0.1431(3) 0.1031(3) 0.0783(10) Uani 1 1 d . . .
H17A H 0.5630 0.0781 0.1049 0.117 Uiso 1 1 calc R . .
H17B H 0.6207 0.1674 0.1483 0.117 Uiso 1 1 calc R . .
H17C H 0.5882 0.1638 0.0445 0.117 Uiso 1 1 calc R . .
H2N H 0.192(2) 0.3257(17) 0.2092(17) 0.029(6) Uiso 1 1 d . . .
H4N H -0.096(3) 0.2188(18) 0.5141(16) 0.036(6) 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
S1 O1 1.420(2) . ?
S1 O2 1.436(2) . ?
S1 N1 1.637(2) . ?
S1 C17 1.770(3) . ?
S2 O5 1.427(2) . ?
S2 O4 1.442(2) . ?
S2 N3 1.606(2) . ?
S2 C7 1.780(2) . ?
O3 C5 1.220(3) . ?
O6 C15 1.219(3) . ?
N1 C4 1.484(3) . ?
N1 C1 1.486(3) . ?
N2 C5 1.351(4) . ?
N2 C6 1.407(4) . ?
N2 H2N 0.79(3) . ?
N3 C12 1.487(3) . ?
N3 H3 0.8600 . ?
N4 C15 1.327(3) . ?
N4 C16 1.449(3) . ?
N4 H4N 0.88(3) . ?
C1 C5 1.520(4) . ?
C1 C2 1.526(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.465(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.481(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C7 1.385(4) . ?
C6 C11 1.394(4) . ?
C7 C8 1.394(4) . ?
C8 C9 1.378(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.356(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.527(3) . ?
C12 C14 1.528(3) . ?
C12 C15 1.550(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O1 S1 O2 119.48(12) . . ?
O1 S1 N1 106.85(13) . . ?
O2 S1 N1 105.80(12) . . ?
O1 S1 C17 107.85(16) . . ?
O2 S1 C17 108.69(18) . . ?
N1 S1 C17 107.64(15) . . ?
O5 S2 O4 119.03(12) . . ?
O5 S2 N3 109.19(12) . . ?
O4 S2 N3 104.91(11) . . ?
O5 S2 C7 106.92(13) . . ?
O4 S2 C7 106.86(12) . . ?
N3 S2 C7 109.73(11) . . ?
C4 N1 C1 110.08(19) . . ?
C4 N1 S1 118.72(19) . . ?
C1 N1 S1 119.46(18) . . ?
C5 N2 C6 127.3(2) . . ?
C5 N2 H2N 116.8(18) . . ?
C6 N2 H2N 115.8(18) . . ?
C12 N3 S2 127.96(16) . . ?
C12 N3 H3 116.0 . . ?
S2 N3 H3 116.0 . . ?
C15 N4 C16 121.1(2) . . ?
C15 N4 H4N 123.2(17) . . ?
C16 N4 H4N 115.3(17) . . ?
N1 C1 C5 112.6(2) . . ?
N1 C1 C2 103.5(2) . . ?
C5 C1 C2 112.7(2) . . ?
N1 C1 H1 109.3 . . ?
C5 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
C3 C2 C1 103.1(3) . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C4 107.4(3) . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C3 C4 N1 103.1(2) . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
N1 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
O3 C5 N2 124.6(3) . . ?
O3 C5 C1 119.6(3) . . ?
N2 C5 C1 115.8(2) . . ?
C7 C6 C11 117.8(3) . . ?
C7 C6 N2 121.0(2) . . ?
C11 C6 N2 121.2(3) . . ?
C6 C7 C8 121.5(2) . . ?
C6 C7 S2 121.4(2) . . ?
C8 C7 S2 117.0(2) . . ?
C9 C8 C7 118.6(3) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.8(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
N3 C12 C13 104.83(19) . . ?
N3 C12 C14 111.5(2) . . ?
C13 C12 C14 109.6(2) . . ?
N3 C12 C15 107.11(18) . . ?
C13 C12 C15 108.89(19) . . ?
C14 C12 C15 114.4(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6 C15 N4 122.8(2) . . ?
O6 C15 C12 118.7(2) . . ?
N4 C15 C12 118.44(19) . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O1 S1 N1 C4 -50.4(2) . . . . ?
O2 S1 N1 C4 -178.8(2) . . . . ?
C17 S1 N1 C4 65.2(3) . . . . ?
O1 S1 N1 C1 170.19(19) . . . . ?
O2 S1 N1 C1 41.9(2) . . . . ?
C17 S1 N1 C1 -74.2(2) . . . . ?
O5 S2 N3 C12 -55.1(2) . . . . ?
O4 S2 N3 C12 176.22(19) . . . . ?
C7 S2 N3 C12 61.7(2) . . . . ?
C4 N1 C1 C5 109.5(3) . . . . ?
S1 N1 C1 C5 -107.9(2) . . . . ?
C4 N1 C1 C2 -12.4(3) . . . . ?
S1 N1 C1 C2 130.2(2) . . . . ?
N1 C1 C2 C3 29.4(3) . . . . ?
C5 C1 C2 C3 -92.5(3) . . . . ?
C1 C2 C3 C4 -36.9(4) . . . . ?
C2 C3 C4 N1 28.9(4) . . . . ?
C1 N1 C4 C3 -9.3(4) . . . . ?
S1 N1 C4 C3 -152.2(3) . . . . ?
C6 N2 C5 O3 -0.7(4) . . . . ?
C6 N2 C5 C1 -179.8(2) . . . . ?
N1 C1 C5 O3 -173.0(2) . . . . ?
C2 C1 C5 O3 -56.4(3) . . . . ?
N1 C1 C5 N2 6.1(3) . . . . ?
C2 C1 C5 N2 122.7(3) . . . . ?
C5 N2 C6 C7 -145.6(2) . . . . ?
C5 N2 C6 C11 37.7(4) . . . . ?
C11 C6 C7 C8 -0.6(4) . . . . ?
N2 C6 C7 C8 -177.4(2) . . . . ?
C11 C6 C7 S2 176.32(19) . . . . ?
N2 C6 C7 S2 -0.5(3) . . . . ?
O5 S2 C7 C6 -172.6(2) . . . . ?
O4 S2 C7 C6 -44.1(2) . . . . ?
N3 S2 C7 C6 69.1(2) . . . . ?
O5 S2 C7 C8 4.5(2) . . . . ?
O4 S2 C7 C8 133.0(2) . . . . ?
N3 S2 C7 C8 -113.8(2) . . . . ?
C6 C7 C8 C9 1.2(4) . . . . ?
S2 C7 C8 C9 -175.8(2) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 C11 -1.9(5) . . . . ?
C9 C10 C11 C6 2.5(4) . . . . ?
C7 C6 C11 C10 -1.3(4) . . . . ?
N2 C6 C11 C10 175.6(2) . . . . ?
S2 N3 C12 C13 170.50(17) . . . . ?
S2 N3 C12 C14 51.9(3) . . . . ?
S2 N3 C12 C15 -73.9(2) . . . . ?
C16 N4 C15 O6 3.8(4) . . . . ?
C16 N4 C15 C12 -174.2(2) . . . . ?
N3 C12 C15 O6 -57.5(3) . . . . ?
C13 C12 C15 O6 55.3(3) . . . . ?
C14 C12 C15 O6 178.3(2) . . . . ?
N3 C12 C15 N4 120.6(2) . . . . ?
C13 C12 C15 N4 -126.6(2) . . . . ?
C14 C12 C15 N4 -3.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.039
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate - Petroleum Ether'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1027035'
_audit_update_record             
;
2014-09-27 deposited with the CCDC.
2015-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H26 N4 O6 S2'
_chemical_formula_sum            'C17 H26 N4 O6 S2'
_chemical_formula_weight         446.54
_chemical_absolute_configuration rmad

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.7425(4)
_cell_length_b                   10.0108(6)
_cell_length_c                   13.8284(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.033(3)
_cell_angle_gamma                90.00
_cell_volume                     1048.27(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5407
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      30.86

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8738
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10904
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5303
_reflns_number_gt                4850
_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)+(0.0440P)²+0.0715P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_number_reflns         5303
_refine_ls_number_parameters     278
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
S1 S 0.49591(4) 0.41970(4) 0.05433(3) 0.03106(9) Uani 1 1 d . . .
S2 S 1.03461(6) 0.58530(6) 0.37133(4) 0.05096(13) Uani 1 1 d . . .
O1 O 0.55206(19) 0.52525(16) 0.43592(10) 0.0538(3) Uani 1 1 d . . .
O2 O 0.61756(14) 0.52623(13) 0.08874(8) 0.0383(3) Uani 1 1 d . . .
O3 O 0.52914(17) 0.33499(15) -0.02293(10) 0.0467(3) Uani 1 1 d . . .
O4 O -0.00607(19) 0.38202(17) -0.20677(11) 0.0614(4) Uani 1 1 d . . .
O5 O 1.1239(2) 0.5402(2) 0.29736(13) 0.0809(6) Uani 1 1 d . . .
O6 O 0.9707(2) 0.4915(2) 0.43375(15) 0.0835(6) Uani 1 1 d . . .
N1 N 0.5944(2) 0.48541(16) 0.27990(11) 0.0391(3) Uani 1 1 d . . .
H1N H 0.639(3) 0.517(2) 0.2405(15) 0.038(5) Uiso 1 1 d . . .
N2 N 0.30338(16) 0.48911(13) 0.01401(10) 0.0313(3) Uani 1 1 d . . .
N3 N 0.1563(2) 0.5694(2) -0.17276(14) 0.0600(5) Uani 1 1 d . . .
H3N H 0.228(4) 0.597(3) -0.140(2) 0.069(9) Uiso 1 1 d . . .
N4 N 0.86373(19) 0.66927(16) 0.31599(11) 0.0388(3) Uani 1 1 d . . .
H4N H 0.893(3) 0.737(3) 0.2798(17) 0.054(7) Uiso 1 1 d . . .
C1 C 0.7065(2) 0.69213(19) 0.35931(13) 0.0396(4) Uani 1 1 d . . .
C2 C 0.5830(3) 0.7817(2) 0.28538(19) 0.0572(5) Uani 1 1 d . . .
H2A H 0.6288 0.8711 0.2895 0.086 Uiso 1 1 calc R . .
H2B H 0.4676 0.7820 0.3008 0.086 Uiso 1 1 calc R . .
H2C H 0.5752 0.7481 0.2196 0.086 Uiso 1 1 calc R . .
C3 C 0.7480(3) 0.7584(3) 0.46009(16) 0.0622(6) Uani 1 1 d . . .
H3A H 0.8179 0.6991 0.5071 0.093 Uiso 1 1 calc R . .
H3B H 0.6399 0.7785 0.4806 0.093 Uiso 1 1 calc R . .
H3C H 0.8124 0.8395 0.4564 0.093 Uiso 1 1 calc R . .
C4 C 0.6122(2) 0.55768(18) 0.36512(12) 0.0373(4) Uani 1 1 d . . .
C5 C 0.5142(2) 0.36255(18) 0.25561(12) 0.0344(3) Uani 1 1 d . . .
C6 C 0.4761(2) 0.31751(16) 0.15630(12) 0.0324(3) Uani 1 1 d . . .
C7 C 0.4064(2) 0.19004(17) 0.13317(14) 0.0406(4) Uani 1 1 d . . .
H7 H 0.3835 0.1608 0.0679 0.049 Uiso 1 1 calc R . .
C8 C 0.3710(3) 0.10692(19) 0.20647(16) 0.0499(5) Uani 1 1 d . . .
H8 H 0.3245 0.0221 0.1909 0.060 Uiso 1 1 calc R . .
C9 C 0.4057(3) 0.1513(2) 0.30284(16) 0.0509(5) Uani 1 1 d . . .
H9 H 0.3809 0.0959 0.3522 0.061 Uiso 1 1 calc R . .
C10 C 0.4762(3) 0.2758(2) 0.32779(14) 0.0458(4) Uani 1 1 d . . .
H10 H 0.4990 0.3028 0.3936 0.055 Uiso 1 1 calc R . .
C11 C 0.16045(19) 0.40487(18) -0.04278(12) 0.0359(3) Uani 1 1 d . . .
H11 H 0.1995 0.3117 -0.0420 0.043 Uiso 1 1 calc R . .
C12 C 0.0114(2) 0.4184(2) 0.01452(14) 0.0442(4) Uani 1 1 d . . .
H12A H -0.1034 0.4055 -0.0286 0.053 Uiso 1 1 calc R . .
H12B H 0.0256 0.3548 0.0685 0.053 Uiso 1 1 calc R . .
C13 C 0.0335(2) 0.5606(2) 0.05271(14) 0.0435(4) Uani 1 1 d . . .
H13A H -0.0240 0.5732 0.1080 0.052 Uiso 1 1 calc R . .
H13B H -0.0147 0.6240 0.0011 0.052 Uiso 1 1 calc R . .
C14 C 0.2333(2) 0.57616(18) 0.08499(13) 0.0386(4) Uani 1 1 d . . .
H14A H 0.2686 0.6684 0.0798 0.046 Uiso 1 1 calc R . .
H14B H 0.2745 0.5460 0.1525 0.046 Uiso 1 1 calc R . .
C15 C 0.0985(2) 0.4526(2) -0.14943(13) 0.0426(4) Uani 1 1 d . . .
C16 C 0.1027(4) 0.6282(4) -0.2710(2) 0.0901(11) Uani 1 1 d . . .
H16A H 0.0332 0.5648 -0.3148 0.135 Uiso 1 1 calc R . .
H16B H 0.2057 0.6514 -0.2958 0.135 Uiso 1 1 calc R . .
H16C H 0.0338 0.7070 -0.2672 0.135 Uiso 1 1 calc R . .
C17 C 1.1790(3) 0.6985(4) 0.4453(2) 0.0883(10) Uani 1 1 d . . .
H17A H 1.2836 0.6522 0.4780 0.132 Uiso 1 1 calc R . .
H17B H 1.1215 0.7371 0.4938 0.132 Uiso 1 1 calc R . .
H17C H 1.2107 0.7680 0.4044 0.132 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
S1 O3 1.4288(13) . ?
S1 O2 1.4366(12) . ?
S1 N2 1.6338(12) . ?
S1 C6 1.7746(17) . ?
S2 O5 1.4222(17) . ?
S2 O6 1.4314(19) . ?
S2 N4 1.6188(15) . ?
S2 C17 1.762(3) . ?
O1 C4 1.213(2) . ?
O4 C15 1.231(2) . ?
N1 C4 1.365(2) . ?
N1 C5 1.387(2) . ?
N1 H1N 0.77(2) . ?
N2 C11 1.4799(19) . ?
N2 C14 1.496(2) . ?
N3 C15 1.316(3) . ?
N3 C16 1.459(3) . ?
N3 H3N 0.70(3) . ?
N4 C1 1.482(2) . ?
N4 H4N 0.90(3) . ?
C1 C3 1.516(3) . ?
C1 C2 1.535(3) . ?
C1 C4 1.542(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C5 C10 1.399(2) . ?
C5 C6 1.417(2) . ?
C6 C7 1.396(2) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C15 1.529(2) . ?
C11 C12 1.536(2) . ?
C11 H11 0.9800 . ?
C12 C13 1.516(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.526(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O3 S1 O2 118.72(8) . . ?
O3 S1 N2 106.91(7) . . ?
O2 S1 N2 106.61(7) . . ?
O3 S1 C6 108.12(8) . . ?
O2 S1 C6 108.91(7) . . ?
N2 S1 C6 107.00(7) . . ?
O5 S2 O6 120.41(14) . . ?
O5 S2 N4 107.26(9) . . ?
O6 S2 N4 105.93(9) . . ?
O5 S2 C17 106.10(13) . . ?
O6 S2 C17 109.20(14) . . ?
N4 S2 C17 107.31(13) . . ?
C4 N1 C5 129.67(16) . . ?
C4 N1 H1N 114.5(16) . . ?
C5 N1 H1N 115.8(16) . . ?
C11 N2 C14 110.28(12) . . ?
C11 N2 S1 117.83(11) . . ?
C14 N2 S1 116.98(10) . . ?
C15 N3 C16 122.8(2) . . ?
C15 N3 H3N 117(2) . . ?
C16 N3 H3N 119(2) . . ?
C1 N4 S2 123.25(12) . . ?
C1 N4 H4N 115.6(15) . . ?
S2 N4 H4N 112.2(15) . . ?
N4 C1 C3 113.87(15) . . ?
N4 C1 C2 105.74(16) . . ?
C3 C1 C2 109.86(18) . . ?
N4 C1 C4 108.92(14) . . ?
C3 C1 C4 110.23(16) . . ?
C2 C1 C4 107.97(14) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N1 124.65(17) . . ?
O1 C4 C1 122.80(16) . . ?
N1 C4 C1 112.41(15) . . ?
N1 C5 C10 121.82(16) . . ?
N1 C5 C6 120.61(15) . . ?
C10 C5 C6 117.49(16) . . ?
C7 C6 C5 120.35(16) . . ?
C7 C6 S1 115.99(13) . . ?
C5 C6 S1 123.49(13) . . ?
C8 C7 C6 120.55(17) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 119.14(18) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 121.48(18) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C5 120.98(18) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
N2 C11 C15 112.54(14) . . ?
N2 C11 C12 103.60(13) . . ?
C15 C11 C12 110.59(13) . . ?
N2 C11 H11 110.0 . . ?
C15 C11 H11 110.0 . . ?
C12 C11 H11 110.0 . . ?
C13 C12 C11 102.72(14) . . ?
C13 C12 H12A 111.2 . . ?
C11 C12 H12A 111.2 . . ?
C13 C12 H12B 111.2 . . ?
C11 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
C12 C13 C14 103.38(14) . . ?
C12 C13 H13A 111.1 . . ?
C14 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
C14 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
N2 C14 C13 103.47(13) . . ?
N2 C14 H14A 111.1 . . ?
C13 C14 H14A 111.1 . . ?
N2 C14 H14B 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.0 . . ?
O4 C15 N3 124.30(19) . . ?
O4 C15 C11 118.29(18) . . ?
N3 C15 C11 117.36(16) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S2 C17 H17A 109.5 . . ?
S2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O3 S1 N2 C11 40.90(14) . . . . ?
O2 S1 N2 C11 168.83(11) . . . . ?
C6 S1 N2 C11 -74.75(12) . . . . ?
O3 S1 N2 C14 176.01(12) . . . . ?
O2 S1 N2 C14 -56.05(13) . . . . ?
C6 S1 N2 C14 60.36(13) . . . . ?
O5 S2 N4 C1 157.93(17) . . . . ?
O6 S2 N4 C1 28.14(19) . . . . ?
C17 S2 N4 C1 -88.42(18) . . . . ?
S2 N4 C1 C3 56.2(2) . . . . ?
S2 N4 C1 C2 176.96(14) . . . . ?
S2 N4 C1 C4 -67.21(18) . . . . ?
C5 N1 C4 O1 -2.5(3) . . . . ?
C5 N1 C4 C1 -178.26(15) . . . . ?
N4 C1 C4 O1 138.44(17) . . . . ?
C3 C1 C4 O1 12.8(2) . . . . ?
C2 C1 C4 O1 -107.2(2) . . . . ?
N4 C1 C4 N1 -45.69(19) . . . . ?
C3 C1 C4 N1 -171.29(16) . . . . ?
C2 C1 C4 N1 68.69(19) . . . . ?
C4 N1 C5 C10 -17.1(3) . . . . ?
C4 N1 C5 C6 166.26(17) . . . . ?
N1 C5 C6 C7 175.62(15) . . . . ?
C10 C5 C6 C7 -1.2(2) . . . . ?
N1 C5 C6 S1 -9.4(2) . . . . ?
C10 C5 C6 S1 173.81(13) . . . . ?
O3 S1 C6 C7 -31.46(14) . . . . ?
O2 S1 C6 C7 -161.74(12) . . . . ?
N2 S1 C6 C7 83.38(13) . . . . ?
O3 S1 C6 C5 153.36(13) . . . . ?
O2 S1 C6 C5 23.09(15) . . . . ?
N2 S1 C6 C5 -91.79(14) . . . . ?
C5 C6 C7 C8 1.0(2) . . . . ?
S1 C6 C7 C8 -174.32(13) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
N1 C5 C10 C9 -176.32(18) . . . . ?
C6 C5 C10 C9 0.4(3) . . . . ?
C14 N2 C11 C15 105.69(15) . . . . ?
S1 N2 C11 C15 -116.42(13) . . . . ?
C14 N2 C11 C12 -13.79(18) . . . . ?
S1 N2 C11 C12 124.10(13) . . . . ?
N2 C11 C12 C13 33.62(17) . . . . ?
C15 C11 C12 C13 -87.19(16) . . . . ?
C11 C12 C13 C14 -41.01(18) . . . . ?
C11 N2 C14 C13 -11.38(18) . . . . ?
S1 N2 C14 C13 -149.67(12) . . . . ?
C12 C13 C14 N2 32.34(18) . . . . ?
C16 N3 C15 O4 -0.5(3) . . . . ?
C16 N3 C15 C11 -178.0(2) . . . . ?
N2 C11 C15 O4 172.16(15) . . . . ?
C12 C11 C15 O4 -72.5(2) . . . . ?
N2 C11 C15 N3 -10.2(2) . . . . ?
C12 C11 C15 N3 105.11(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate - Petroleum Ether'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1027036'
_audit_update_record             
;
2014-09-27 deposited with the CCDC.
2015-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 Br N3 O4 S'
_chemical_formula_sum            'C19 H20 Br N3 O4 S'
_chemical_formula_weight         466.35
_chemical_absolute_configuration rmad

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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ORTHORHOMBIC
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.2942(10)
_cell_length_b                   13.9119(13)
_cell_length_c                   15.3096(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1979.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2265
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      23.00

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    2.213
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4359
_exptl_absorpt_correction_T_max  0.6785
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11118
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         28.31
_reflns_number_total             4865
_reflns_number_gt                3065
_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)+(0.0122P)²+0.0000P] 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   0.013(8)
_refine_ls_number_reflns         4865
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_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
S1 S 0.63813(10) 0.55350(5) 0.69375(5) 0.0417(2) Uani 1 1 d . . .
O1 O 0.1373(3) 0.39532(17) 0.62865(17) 0.0595(7) Uani 1 1 d . . .
O2 O 0.6289(3) 0.47010(16) 0.74819(14) 0.0565(6) Uani 1 1 d . . .
O3 O 0.7269(3) 0.63151(17) 0.72356(17) 0.0645(8) Uani 1 1 d . . .
O4 O 0.6343(3) 0.32104(15) 0.59200(17) 0.0548(6) Uani 1 1 d . . .
N1 N 0.3712(3) 0.44466(17) 0.62224(17) 0.0442(7) Uani 1 1 d . . .
H1N H 0.4578 0.4246 0.6143 0.053 Uiso 1 1 calc R . .
N2 N 0.6879(3) 0.51540(17) 0.59838(16) 0.0376(6) Uani 1 1 d . . .
N3 N 0.8625(3) 0.28085(16) 0.62881(16) 0.0394(6) Uani 1 1 d . . .
H7N H 0.9450 0.3055 0.6410 0.047 Uiso 1 1 calc R . .
Br1 Br 0.85180(5) -0.15546(2) 0.64940(3) 0.07455(17) Uani 1 1 d . . .
C1 C 0.2643(4) 0.3770(2) 0.6172(2) 0.0431(8) Uani 1 1 d . . .
C2 C 0.3543(4) 0.5436(2) 0.6390(2) 0.0421(7) Uani 1 1 d . . .
C4 C 0.4464(4) 0.6983(2) 0.6861(2) 0.0499(9) Uani 1 1 d . . .
H4 H 0.5228 0.7352 0.7065 0.060 Uiso 1 1 calc R . .
C5 C 0.3152(4) 0.7408(2) 0.6712(2) 0.0590(11) Uani 1 1 d . . .
H5 H 0.3013 0.8057 0.6832 0.071 Uiso 1 1 calc R . .
C6 C 0.2056(5) 0.6862(3) 0.6386(3) 0.0663(12) Uani 1 1 d . . .
H6 H 0.1174 0.7150 0.6269 0.080 Uiso 1 1 calc R . .
C7 C 0.2226(4) 0.5900(3) 0.6229(3) 0.0638(12) Uani 1 1 d . . .
H7 H 0.1456 0.5547 0.6012 0.077 Uiso 1 1 calc R . .
C8 C 0.8104(3) 0.4470(2) 0.5957(2) 0.0384(8) Uani 1 1 d . . .
H8 H 0.8823 0.4633 0.6401 0.046 Uiso 1 1 calc R . .
C9 C 0.8701(5) 0.4635(2) 0.5045(2) 0.0562(9) Uani 1 1 d . . .
H9A H 0.9713 0.4467 0.5018 0.067 Uiso 1 1 calc R . .
H9B H 0.8180 0.4257 0.4617 0.067 Uiso 1 1 calc R . .
C10 C 0.8489(6) 0.5685(3) 0.4889(3) 0.0831(13) Uani 1 1 d . . .
H10A H 0.8493 0.5829 0.4270 0.100 Uiso 1 1 calc R . .
H10B H 0.9235 0.6059 0.5174 0.100 Uiso 1 1 calc R . .
C11 C 0.7038(4) 0.5889(3) 0.5286(3) 0.0596(10) Uani 1 1 d . . .
H11A H 0.7006 0.6533 0.5529 0.072 Uiso 1 1 calc R . .
H11B H 0.6281 0.5826 0.4853 0.072 Uiso 1 1 calc R . .
C12 C 0.7583(4) 0.3439(2) 0.6072(2) 0.0378(7) Uani 1 1 d . . .
C13 C 0.8543(4) 0.1806(2) 0.63399(19) 0.0378(7) Uani 1 1 d . . .
C14 C 0.9773(4) 0.1308(2) 0.6582(3) 0.0480(9) Uani 1 1 d . . .
H14 H 1.0607 0.1648 0.6714 0.058 Uiso 1 1 calc R . .
C15 C 0.9781(4) 0.0316(2) 0.6631(3) 0.0550(10) Uani 1 1 d . . .
H15 H 1.0613 -0.0009 0.6796 0.066 Uiso 1 1 calc R . .
C16 C 0.8547(4) -0.0188(2) 0.6433(2) 0.0469(8) Uani 1 1 d . . .
C17 C 0.7312(4) 0.0291(2) 0.6215(2) 0.0529(10) Uani 1 1 d . . .
H17 H 0.6475 -0.0053 0.6101 0.063 Uiso 1 1 calc R . .
C18 C 0.7300(4) 0.1280(2) 0.6163(2) 0.0506(10) Uani 1 1 d . . .
H18 H 0.6458 0.1598 0.6010 0.061 Uiso 1 1 calc R . .
C19 C 0.3135(4) 0.2782(2) 0.5976(2) 0.0504(9) Uani 1 1 d . . .
H19A H 0.3314 0.2446 0.6513 0.076 Uiso 1 1 calc R . .
H19B H 0.4004 0.2809 0.5638 0.076 Uiso 1 1 calc R . .
H19C H 0.2405 0.2450 0.5650 0.076 Uiso 1 1 calc R . .
C3P C 0.4660(4) 0.6001(2) 0.6706(2) 0.0396(8) 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
S1 O2 1.431(2) . ?
S1 O3 1.438(2) . ?
S1 N2 1.621(3) . ?
S1 C3P 1.762(3) . ?
O1 C1 1.220(4) . ?
O4 C12 1.218(4) . ?
N1 C1 1.372(4) . ?
N1 C2 1.408(4) . ?
N1 H1N 0.8600 . ?
N2 C8 1.485(4) . ?
N2 C11 1.486(4) . ?
N3 C12 1.349(4) . ?
N3 C13 1.399(3) . ?
N3 H7N 0.8600 . ?
Br1 C16 1.904(3) . ?
C1 C19 1.479(5) . ?
C2 C3P 1.389(5) . ?
C2 C7 1.406(5) . ?
C4 C5 1.374(5) . ?
C4 C3P 1.399(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.519(5) . ?
C8 C12 1.523(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.493(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.506(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C14 1.387(4) . ?
C13 C18 1.394(5) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(5) . ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O2 S1 O3 117.48(16) . . ?
O2 S1 N2 106.06(13) . . ?
O3 S1 N2 111.66(16) . . ?
O2 S1 C3P 111.14(17) . . ?
O3 S1 C3P 107.90(15) . . ?
N2 S1 C3P 101.46(14) . . ?
C1 N1 C2 126.9(3) . . ?
C1 N1 H1N 116.6 . . ?
C2 N1 H1N 116.6 . . ?
C8 N2 C11 110.2(3) . . ?
C8 N2 S1 117.0(2) . . ?
C11 N2 S1 116.8(2) . . ?
C12 N3 C13 128.6(3) . . ?
C12 N3 H7N 115.7 . . ?
C13 N3 H7N 115.7 . . ?
O1 C1 N1 123.3(3) . . ?
O1 C1 C19 121.5(3) . . ?
N1 C1 C19 115.2(3) . . ?
C3P C2 C7 116.8(3) . . ?
C3P C2 N1 122.2(3) . . ?
C7 C2 N1 120.9(3) . . ?
C5 C4 C3P 120.5(4) . . ?
C5 C4 H4 119.7 . . ?
C3P C4 H4 119.7 . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 121.5(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C2 121.3(4) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
N2 C8 C9 102.0(3) . . ?
N2 C8 C12 110.9(2) . . ?
C9 C8 C12 111.4(3) . . ?
N2 C8 H8 110.8 . . ?
C9 C8 H8 110.8 . . ?
C12 C8 H8 110.8 . . ?
C10 C9 C8 104.3(3) . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C9 C10 C11 103.8(4) . . ?
C9 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
N2 C11 C10 104.4(3) . . ?
N2 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
N2 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
O4 C12 N3 123.8(3) . . ?
O4 C12 C8 121.7(3) . . ?
N3 C12 C8 114.3(3) . . ?
C14 C13 C18 118.2(3) . . ?
C14 C13 N3 117.9(3) . . ?
C18 C13 N3 123.9(3) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 Br1 119.1(3) . . ?
C15 C16 Br1 120.6(3) . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C1 C19 H19A 109.5 . . ?
C1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C3P C4 121.0(3) . . ?
C2 C3P S1 122.7(2) . . ?
C4 C3P S1 116.3(3) . . ?

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
O2 S1 N2 C8 -47.1(3) . . . . ?
O3 S1 N2 C8 82.0(2) . . . . ?
C3P S1 N2 C8 -163.3(2) . . . . ?
O2 S1 N2 C11 179.2(2) . . . . ?
O3 S1 N2 C11 -51.7(3) . . . . ?
C3P S1 N2 C11 63.0(3) . . . . ?
C2 N1 C1 O1 -1.4(5) . . . . ?
C2 N1 C1 C19 179.3(3) . . . . ?
C1 N1 C2 C3P 158.6(3) . . . . ?
C1 N1 C2 C7 -22.5(5) . . . . ?
C3P C4 C5 C6 -2.0(6) . . . . ?
C4 C5 C6 C7 1.8(7) . . . . ?
C5 C6 C7 C2 -0.5(7) . . . . ?
C3P C2 C7 C6 -0.6(6) . . . . ?
N1 C2 C7 C6 -179.7(4) . . . . ?
C11 N2 C8 C9 -18.1(3) . . . . ?
S1 N2 C8 C9 -154.7(2) . . . . ?
C11 N2 C8 C12 -136.8(3) . . . . ?
S1 N2 C8 C12 86.6(3) . . . . ?
N2 C8 C9 C10 35.1(4) . . . . ?
C12 C8 C9 C10 153.4(3) . . . . ?
C8 C9 C10 C11 -39.4(5) . . . . ?
C8 N2 C11 C10 -5.6(4) . . . . ?
S1 N2 C11 C10 131.1(3) . . . . ?
C9 C10 C11 N2 27.5(4) . . . . ?
C13 N3 C12 O4 3.4(5) . . . . ?
C13 N3 C12 C8 -171.7(3) . . . . ?
N2 C8 C12 O4 21.6(4) . . . . ?
C9 C8 C12 O4 -91.3(4) . . . . ?
N2 C8 C12 N3 -163.1(3) . . . . ?
C9 C8 C12 N3 84.0(4) . . . . ?
C12 N3 C13 C14 -179.8(3) . . . . ?
C12 N3 C13 C18 0.2(5) . . . . ?
C18 C13 C14 C15 1.3(5) . . . . ?
N3 C13 C14 C15 -178.7(3) . . . . ?
C13 C14 C15 C16 0.2(6) . . . . ?
C14 C15 C16 C17 -2.0(6) . . . . ?
C14 C15 C16 Br1 -179.9(3) . . . . ?
C15 C16 C17 C18 2.1(6) . . . . ?
Br1 C16 C17 C18 -179.9(3) . . . . ?
C16 C17 C18 C13 -0.6(6) . . . . ?
C14 C13 C18 C17 -1.1(5) . . . . ?
N3 C13 C18 C17 178.9(3) . . . . ?
C7 C2 C3P C4 0.5(5) . . . . ?
N1 C2 C3P C4 179.5(3) . . . . ?
C7 C2 C3P S1 -179.7(3) . . . . ?
N1 C2 C3P S1 -0.7(4) . . . . ?
C5 C4 C3P C2 0.8(5) . . . . ?
C5 C4 C3P S1 -179.0(3) . . . . ?
O2 S1 C3P C2 -50.9(3) . . . . ?
O3 S1 C3P C2 179.0(3) . . . . ?
N2 S1 C3P C2 61.5(3) . . . . ?
O2 S1 C3P C4 129.0(3) . . . . ?
O3 S1 C3P C4 -1.2(3) . . . . ?
N2 S1 C3P C4 -118.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.057
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane - Methaol'
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1027037'
_audit_update_record             
;
2014-09-27 deposited with the CCDC.
2015-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N2 O5 S'
_chemical_formula_sum            'C14 H20 N2 O5 S'
_chemical_formula_weight         328.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   7.1146(3)
_cell_length_b                   8.0387(3)
_cell_length_c                   15.0865(6)
_cell_angle_alpha                90.323(2)
_cell_angle_beta                 100.054(2)
_cell_angle_gamma                109.252(2)
_cell_volume                     800.21(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    8442
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      29.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8648
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13823
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3852
_reflns_number_gt                3360
_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)+(0.0625P)²+0.1344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3852
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
S1 S 0.88442(5) 0.95608(5) 0.20156(2) 0.03978(12) Uani 1 1 d . . .
O1 O 0.4176(2) 0.65977(19) 0.41717(10) 0.0678(4) Uani 1 1 d . . .
O2 O 0.69357(16) 0.83335(16) 0.15732(7) 0.0507(3) Uani 1 1 d . . .
O3 O 0.9717(2) 1.11319(16) 0.15779(8) 0.0612(3) Uani 1 1 d . . .
O4 O 0.76459(18) 0.49895(15) 0.21703(7) 0.0540(3) Uani 1 1 d . . .
O5 O 0.74047(17) 0.47682(16) 0.06790(7) 0.0536(3) Uani 1 1 d . . .
N1 N 0.69398(19) 0.72491(17) 0.35147(8) 0.0424(3) Uani 1 1 d . . .
H1N H 0.747(3) 0.679(2) 0.3170(12) 0.050(5) Uiso 1 1 d . . .
N2 N 1.04017(17) 0.84152(15) 0.22329(7) 0.0373(2) Uani 1 1 d . . .
C1 C 0.5287(2) 0.6104(2) 0.37875(10) 0.0454(3) Uani 1 1 d . . .
C2 C 0.7668(2) 0.90848(19) 0.37010(9) 0.0404(3) Uani 1 1 d . . .
C3 C 0.8644(2) 1.02505(18) 0.31006(9) 0.0393(3) Uani 1 1 d . . .
C4 C 0.9443(3) 1.2060(2) 0.33274(13) 0.0527(4) Uani 1 1 d . . .
C5 C 0.9290(3) 1.2739(3) 0.41459(15) 0.0638(5) Uani 1 1 d . . .
C6 C 0.8310(3) 1.1619(3) 0.47258(13) 0.0608(5) Uani 1 1 d . . .
C7 C 0.7508(3) 0.9826(3) 0.45146(11) 0.0528(4) Uani 1 1 d . . .
C8 C 1.2478(3) 0.9527(2) 0.26552(14) 0.0541(4) Uani 1 1 d . . .
C9 C 1.0224(2) 0.70640(19) 0.15014(9) 0.0396(3) Uani 1 1 d . . .
C10 C 1.0415(3) 0.7839(3) 0.05842(11) 0.0582(4) Uani 1 1 d . . .
C11 C 1.1854(3) 0.6207(3) 0.17850(13) 0.0545(4) Uani 1 1 d . . .
C12 C 0.8255(2) 0.55406(19) 0.14988(9) 0.0408(3) Uani 1 1 d . . .
C13 C 0.5671(4) 0.3164(3) 0.06413(17) 0.0713(6) Uani 1 1 d . . .
C14 C 0.4892(3) 0.4191(2) 0.35680(15) 0.0602(5) Uani 1 1 d . . .
H4 H 1.002(3) 1.281(3) 0.2915(13) 0.059(5) Uiso 1 1 d . . .
H5 H 0.983(4) 1.399(4) 0.4275(17) 0.094(8) Uiso 1 1 d . . .
H6 H 0.820(3) 1.217(3) 0.5269(15) 0.079(6) Uiso 1 1 d . . .
H7 H 0.689(3) 0.911(3) 0.4891(14) 0.063(6) Uiso 1 1 d . . .
H8A H 1.325(3) 1.017(3) 0.2224(15) 0.075(6) Uiso 1 1 d . . .
H8B H 1.240(3) 1.037(3) 0.3070(13) 0.062(5) Uiso 1 1 d . . .
H8C H 1.318(3) 0.878(3) 0.2957(14) 0.066(6) Uiso 1 1 d . . .
H10A H 0.925(4) 0.814(4) 0.0345(18) 0.097(8) Uiso 1 1 d . . .
H10B H 1.170(3) 0.880(3) 0.0621(13) 0.063(5) Uiso 1 1 d . . .
H10C H 1.051(3) 0.693(3) 0.0150(16) 0.080(7) Uiso 1 1 d . . .
H11A H 1.190(3) 0.589(3) 0.2413(14) 0.058(5) Uiso 1 1 d . . .
H11B H 1.150(3) 0.514(3) 0.1375(15) 0.075(6) Uiso 1 1 d . . .
H11C H 1.318(3) 0.705(3) 0.1797(13) 0.059(5) Uiso 1 1 d . . .
H13A H 0.462(4) 0.354(3) 0.0890(15) 0.074(6) Uiso 1 1 d . . .
H13B H 0.616(4) 0.227(4) 0.0943(18) 0.097(8) Uiso 1 1 d . . .
H13C H 0.518(4) 0.283(4) 0.0039(19) 0.098(8) Uiso 1 1 d . . .
H14A H 0.375(4) 0.340(4) 0.378(2) 0.113(9) Uiso 1 1 d . . .
H14B H 0.426(6) 0.388(5) 0.286(3) 0.151(13) Uiso 1 1 d . . .
H14C H 0.600(5) 0.391(4) 0.3495(19) 0.107(9) 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
S1 O3 1.4325(11) . ?
S1 O2 1.4336(11) . ?
S1 N2 1.6532(12) . ?
S1 C3 1.7694(14) . ?
O1 C1 1.2173(19) . ?
O4 C12 1.2009(17) . ?
O5 C12 1.3280(17) . ?
O5 C13 1.454(2) . ?
N1 C1 1.3636(19) . ?
N1 C2 1.4019(19) . ?
N1 H1N 0.840(19) . ?
N2 C8 1.4769(19) . ?
N2 C9 1.5036(17) . ?
C1 C14 1.493(3) . ?
C2 C7 1.400(2) . ?
C2 C3 1.407(2) . ?
C3 C4 1.392(2) . ?
C4 C5 1.383(3) . ?
C4 H4 0.92(2) . ?
C5 C6 1.368(3) . ?
C5 H5 0.96(3) . ?
C6 C7 1.376(3) . ?
C6 H6 0.96(2) . ?
C7 H7 0.88(2) . ?
C8 H8A 0.97(2) . ?
C8 H8B 0.94(2) . ?
C8 H8C 0.97(2) . ?
C9 C12 1.526(2) . ?
C9 C10 1.530(2) . ?
C9 C11 1.536(2) . ?
C10 H10A 0.95(3) . ?
C10 H10B 0.97(2) . ?
C10 H10C 1.00(2) . ?
C11 H11A 0.98(2) . ?
C11 H11B 0.99(2) . ?
C11 H11C 0.96(2) . ?
C13 H13A 1.01(2) . ?
C13 H13B 0.98(3) . ?
C13 H13C 0.92(3) . ?
C14 H14A 0.96(3) . ?
C14 H14B 1.07(4) . ?
C14 H14C 0.91(3) . ?

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
O3 S1 O2 118.01(7) . . ?
O3 S1 N2 111.75(7) . . ?
O2 S1 N2 106.21(6) . . ?
O3 S1 C3 106.66(7) . . ?
O2 S1 C3 109.85(7) . . ?
N2 S1 C3 103.41(6) . . ?
C12 O5 C13 115.33(14) . . ?
C1 N1 C2 125.28(13) . . ?
C1 N1 H1N 114.8(13) . . ?
C2 N1 H1N 119.7(13) . . ?
C8 N2 C9 116.36(12) . . ?
C8 N2 S1 112.62(10) . . ?
C9 N2 S1 115.59(9) . . ?
O1 C1 N1 122.60(15) . . ?
O1 C1 C14 121.71(15) . . ?
N1 C1 C14 115.68(14) . . ?
C7 C2 N1 120.72(14) . . ?
C7 C2 C3 117.30(14) . . ?
N1 C2 C3 121.94(12) . . ?
C4 C3 C2 120.46(14) . . ?
C4 C3 S1 116.06(12) . . ?
C2 C3 S1 123.42(11) . . ?
C5 C4 C3 120.54(17) . . ?
C5 C4 H4 119.8(12) . . ?
C3 C4 H4 119.6(12) . . ?
C6 C5 C4 119.37(17) . . ?
C6 C5 H5 122.2(15) . . ?
C4 C5 H5 118.4(15) . . ?
C5 C6 C7 121.03(16) . . ?
C5 C6 H6 115.5(14) . . ?
C7 C6 H6 123.5(14) . . ?
C6 C7 C2 121.28(17) . . ?
C6 C7 H7 120.7(14) . . ?
C2 C7 H7 118.0(14) . . ?
N2 C8 H8A 112.7(13) . . ?
N2 C8 H8B 108.8(12) . . ?
H8A C8 H8B 107.1(18) . . ?
N2 C8 H8C 108.9(12) . . ?
H8A C8 H8C 108.6(18) . . ?
H8B C8 H8C 110.7(17) . . ?
N2 C9 C12 107.28(10) . . ?
N2 C9 C10 112.99(13) . . ?
C12 C9 C10 114.10(13) . . ?
N2 C9 C11 108.88(12) . . ?
C12 C9 C11 102.91(12) . . ?
C10 C9 C11 110.10(14) . . ?
C9 C10 H10A 110.5(16) . . ?
C9 C10 H10B 110.9(12) . . ?
H10A C10 H10B 115(2) . . ?
C9 C10 H10C 109.3(13) . . ?
H10A C10 H10C 108(2) . . ?
H10B C10 H10C 103.6(17) . . ?
C9 C11 H11A 110.7(11) . . ?
C9 C11 H11B 107.2(13) . . ?
H11A C11 H11B 110.3(17) . . ?
C9 C11 H11C 110.5(11) . . ?
H11A C11 H11C 103.0(16) . . ?
H11B C11 H11C 115.1(17) . . ?
O4 C12 O5 123.44(14) . . ?
O4 C12 C9 123.84(13) . . ?
O5 C12 C9 112.35(12) . . ?
O5 C13 H13A 105.5(13) . . ?
O5 C13 H13B 107.7(16) . . ?
H13A C13 H13B 119(2) . . ?
O5 C13 H13C 105.9(17) . . ?
H13A C13 H13C 108(2) . . ?
H13B C13 H13C 111(2) . . ?
C1 C14 H14A 114.7(18) . . ?
C1 C14 H14B 109(2) . . ?
H14A C14 H14B 96(2) . . ?
C1 C14 H14C 115.2(18) . . ?
H14A C14 H14C 124(2) . . ?
H14B C14 H14C 91(2) . . ?

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
O3 S1 N2 C8 47.35(13) . . . . ?
O2 S1 N2 C8 177.33(11) . . . . ?
C3 S1 N2 C8 -67.01(12) . . . . ?
O3 S1 N2 C9 -89.78(11) . . . . ?
O2 S1 N2 C9 40.21(11) . . . . ?
C3 S1 N2 C9 155.86(10) . . . . ?
C2 N1 C1 O1 5.7(2) . . . . ?
C2 N1 C1 C14 -175.54(15) . . . . ?
C1 N1 C2 C7 33.6(2) . . . . ?
C1 N1 C2 C3 -148.56(14) . . . . ?
C7 C2 C3 C4 1.2(2) . . . . ?
N1 C2 C3 C4 -176.63(14) . . . . ?
C7 C2 C3 S1 -175.97(11) . . . . ?
N1 C2 C3 S1 6.17(19) . . . . ?
O3 S1 C3 C4 -3.85(14) . . . . ?
O2 S1 C3 C4 -132.85(12) . . . . ?
N2 S1 C3 C4 114.12(12) . . . . ?
O3 S1 C3 C2 173.47(12) . . . . ?
O2 S1 C3 C2 44.47(13) . . . . ?
N2 S1 C3 C2 -68.56(13) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
S1 C3 C4 C5 177.43(14) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
N1 C2 C7 C6 176.58(15) . . . . ?
C3 C2 C7 C6 -1.3(2) . . . . ?
C8 N2 C9 C12 151.74(13) . . . . ?
S1 N2 C9 C12 -72.75(12) . . . . ?
C8 N2 C9 C10 -81.64(17) . . . . ?
S1 N2 C9 C10 53.86(15) . . . . ?
C8 N2 C9 C11 41.03(18) . . . . ?
S1 N2 C9 C11 176.53(11) . . . . ?
C13 O5 C12 O4 -0.9(2) . . . . ?
C13 O5 C12 C9 172.25(16) . . . . ?
N2 C9 C12 O4 -39.06(18) . . . . ?
C10 C9 C12 O4 -165.02(16) . . . . ?
C11 C9 C12 O4 75.71(17) . . . . ?
N2 C9 C12 O5 147.81(12) . . . . ?
C10 C9 C12 O5 21.84(18) . . . . ?
C11 C9 C12 O5 -97.42(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.043


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
