 
data_1
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H20 N2 O5 S2' 
_chemical_formula_weight          408.48

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'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_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                    8.8085(10)
_cell_length_b                    10.3259(12)
_cell_length_c                    22.243(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2023.2(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     4326
_cell_measurement_theta_min       2.69
_cell_measurement_theta_max       26.01
 
_exptl_crystal_description        block
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.341          
_exptl_crystal_F_000              856
_exptl_transmission_factor_min    0.6534  
_exptl_transmission_factor_max    0.7454
_exptl_crystal_size_max           0.300
_exptl_crystal_size_mid           0.300
_exptl_crystal_size_min           0.300
_exptl_absorpt_coefficient_mu     0.294
_shelx_estimated_absorpt_T_min    0.917
_shelx_estimated_absorpt_T_max    0.917
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    SADABS 
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX II area detector' 
_diffrn_measurement_method        'ω scan'
_diffrn_detector_area_resol_mean  'fine-focus sealed tube'
_diffrn_reflns_number             11462
_diffrn_reflns_av_unetI/netI      0.0293
_diffrn_reflns_av_R_equivalents   0.0247
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          1.831
_diffrn_reflns_theta_max          26.330
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   1.000
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              4105
_reflns_number_gt                 3472
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.745
_reflns_Friedel_fraction_max      0.999
_reflns_Friedel_fraction_full     1.000
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker SMART APEX II'
_computing_cell_refinement        'Bruker SMART'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     SHELXTL 
_computing_publication_material   SHELXTL 
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0780P)²+0.4300P] 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 x determined using 1262 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.02(3)
_chemical_absolute_configuration  unk
_refine_ls_number_reflns          4105
_refine_ls_number_parameters      246
_refine_ls_number_restraints      13
_refine_ls_R_factor_all           0.0541
_refine_ls_R_factor_gt            0.0445
_refine_ls_wR_factor_ref          0.1299
_refine_ls_wR_factor_gt           0.1219
_refine_ls_goodness_of_fit_ref    1.001
_refine_ls_restrained_S_all       1.024
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 1.1322(5) -0.1029(3) -0.04037(17) 0.0498(8) Uani 1 1 d . . . . .
C2 C 1.2895(5) -0.1034(4) -0.0377(2) 0.0599(10) Uani 1 1 d . . . . .
H2 H 1.3408 -0.0692 -0.0048 0.072 Uiso 1 1 calc R U . . .
C3 C 1.3671(6) -0.1564(5) -0.0857(2) 0.0705(12) Uani 1 1 d . . . . .
H3 H 1.4726 -0.1594 -0.0851 0.085 Uiso 1 1 calc R U . . .
C4 C 1.2885(6) -0.2050(4) -0.1347(2) 0.0689(12) Uani 1 1 d . . . . .
H4 H 1.3430 -0.2395 -0.1667 0.083 Uiso 1 1 calc R U . . .
C5 C 1.1335(6) -0.2042(4) -0.13747(19) 0.0611(10) Uani 1 1 d . . . . .
H5 H 1.0823 -0.2375 -0.1706 0.073 Uiso 1 1 calc R U . . .
C6 C 1.0563(5) -0.1524(4) -0.08979(18) 0.0513(9) Uani 1 1 d . . . . .
C7 C 0.8918(5) -0.1416(4) -0.07890(19) 0.0544(9) Uani 1 1 d . . . . .
C8 C 1.0195(5) -0.0542(4) 0.00305(17) 0.0529(9) Uani 1 1 d . . . . .
C9 C 0.7415(5) 0.2227(4) 0.0378(2) 0.0661(12) Uani 1 1 d . . . . .
H9A H 0.8492 0.2056 0.0334 0.079 Uiso 1 1 calc R U . . .
H9B H 0.7238 0.3117 0.0257 0.079 Uiso 1 1 calc R U . . .
C10 C 0.6990(5) 0.2087(4) 0.1041(2) 0.0601(10) Uani 1 1 d . . . . .
H10 H 0.7130 0.1182 0.1161 0.072 Uiso 1 1 calc R U . . .
C11 C 0.7949(7) 0.2936(6) 0.1441(3) 0.0949(17) Uani 1 1 d . . . . .
H11A H 0.7727 0.3830 0.1360 0.142 Uiso 1 1 calc R U . . .
H11B H 0.9004 0.2772 0.1364 0.142 Uiso 1 1 calc R U . . .
H11C H 0.7727 0.2748 0.1855 0.142 Uiso 1 1 calc R U . . .
C12 C 0.5324(4) 0.2445(4) 0.11166(16) 0.0486(8) Uani 1 1 d . . . . .
C13 C 0.4748(8) 0.0364(6) 0.1671(4) 0.112(2) Uani 1 1 d . U . . .
H13A H 0.5139 -0.0212 0.1363 0.134 Uiso 1 1 calc R U . . .
H13B H 0.5483 0.0424 0.1995 0.134 Uiso 1 1 calc R U . . .
C14 C 0.3295(8) -0.0082(7) 0.1892(4) 0.125(2) Uani 1 1 d . U . . .
H14A H 0.3004 -0.0856 0.1674 0.151 Uiso 1 1 calc R U . . .
H14B H 0.3395 -0.0311 0.2313 0.151 Uiso 1 1 calc R U . . .
C15 C 0.2137(7) 0.0859(5) 0.1831(2) 0.0788(14) Uani 1 1 d . . . . .
H15A H 0.1730 0.1090 0.2222 0.095 Uiso 1 1 calc R U . . .
H15B H 0.1317 0.0526 0.1584 0.095 Uiso 1 1 calc R U . . .
C16 C 0.2858(5) 0.2033(4) 0.15336(16) 0.0536(9) Uani 1 1 d . . . . .
H16 H 0.2348 0.2213 0.1151 0.064 Uiso 1 1 calc R U . . .
C17 C 0.2791(5) 0.3202(4) 0.19275(17) 0.0555(10) Uani 1 1 d . . . . .
C18 C 0.1301(10) 0.4996(8) 0.2199(3) 0.124(3) Uani 1 1 d . . . . .
H18A H 0.1063 0.4739 0.2603 0.185 Uiso 1 1 calc R U . . .
H18B H 0.0478 0.5496 0.2038 0.185 Uiso 1 1 calc R U . . .
H18C H 0.2209 0.5510 0.2200 0.185 Uiso 1 1 calc R U . . .
N1 N 0.8766(4) -0.0850(3) -0.02191(14) 0.0508(7) Uani 1 1 d . . . . .
N2 N 0.4413(4) 0.1643(3) 0.14221(14) 0.0506(7) Uani 1 1 d . . . . .
O2 O 0.1531(4) 0.3862(4) 0.18353(17) 0.0916(12) Uani 1 1 d . . . . .
O3 O 0.3719(4) 0.3492(3) 0.22953(14) 0.0784(9) Uani 1 1 d . . . . .
O4 O 0.4853(3) 0.3469(3) 0.09184(14) 0.0659(8) Uani 1 1 d . . . . .
O5 O 0.7861(4) -0.1740(4) -0.10987(15) 0.0778(9) Uani 1 1 d . . . . .
O6 O 1.0394(4) 0.0010(4) 0.04970(14) 0.0769(9) Uani 1 1 d . . . . .
S1 S 0.70965(13) -0.05925(10) 0.01377(5) 0.0603(3) Uani 1 1 d . . . . .
S2 S 0.63882(13) 0.11757(11) -0.01198(5) 0.0640(3) 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
C1 C6 1.385(5) . ?
C1 C2 1.387(6) . ?
C1 C8 1.473(6) . ?
C2 C3 1.381(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.473(6) . ?
C7 O5 1.206(5) . ?
C7 N1 1.402(5) . ?
C8 O6 1.197(5) . ?
C8 N1 1.412(5) . ?
C9 C10 1.527(7) . ?
C9 S2 1.796(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.509(7) . ?
C10 C12 1.522(6) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O4 1.219(5) . ?
C12 N2 1.338(5) . ?
C13 C14 1.447(9) . ?
C13 N2 1.462(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.416(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.520(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.449(5) . ?
C16 C17 1.493(6) . ?
C16 H16 0.9800 . ?
C17 O3 1.194(5) . ?
C17 O2 1.319(5) . ?
C18 O2 1.438(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 S1 1.692(3) . ?
S1 S2 2.0126(15) . ?
 
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
C6 C1 C2 121.0(4) . . ?
C6 C1 C8 108.7(3) . . ?
C2 C1 C8 130.3(4) . . ?
C3 C2 C1 117.6(4) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 122.2(5) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 117.6(4) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C5 C6 C1 121.3(4) . . ?
C5 C6 C7 130.2(4) . . ?
C1 C6 C7 108.4(4) . . ?
O5 C7 N1 123.9(4) . . ?
O5 C7 C6 130.2(4) . . ?
N1 C7 C6 105.9(3) . . ?
O6 C8 N1 125.3(4) . . ?
O6 C8 C1 129.3(4) . . ?
N1 C8 C1 105.4(3) . . ?
C10 C9 S2 114.5(3) . . ?
C10 C9 H9A 108.6 . . ?
S2 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
S2 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C12 109.5(4) . . ?
C11 C10 C9 112.2(4) . . ?
C12 C10 C9 108.7(4) . . ?
C11 C10 H10 108.8 . . ?
C12 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 N2 121.1(4) . . ?
O4 C12 C10 119.9(4) . . ?
N2 C12 C10 119.0(3) . . ?
C14 C13 N2 103.7(5) . . ?
C14 C13 H13A 111.0 . . ?
N2 C13 H13A 111.0 . . ?
C14 C13 H13B 111.0 . . ?
N2 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C15 C14 C13 112.7(5) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 106.7(4) . . ?
C14 C15 H15A 110.4 . . ?
C16 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
C16 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
N2 C16 C17 111.2(3) . . ?
N2 C16 C15 104.4(4) . . ?
C17 C16 C15 111.9(3) . . ?
N2 C16 H16 109.7 . . ?
C17 C16 H16 109.7 . . ?
C15 C16 H16 109.7 . . ?
O3 C17 O2 123.6(4) . . ?
O3 C17 C16 125.3(4) . . ?
O2 C17 C16 111.1(4) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 N1 C8 111.4(3) . . ?
C7 N1 S1 124.9(3) . . ?
C8 N1 S1 123.7(3) . . ?
C12 N2 C16 118.8(3) . . ?
C12 N2 C13 129.0(4) . . ?
C16 N2 C13 112.1(4) . . ?
C17 O2 C18 116.9(5) . . ?
N1 S1 S2 106.18(12) . . ?
C9 S2 S1 102.54(16) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(6) . . . . ?
C8 C1 C2 C3 179.9(4) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
C2 C3 C4 C5 -0.7(7) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C4 C5 C6 C7 -177.8(4) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
C8 C1 C6 C5 179.8(3) . . . . ?
C2 C1 C6 C7 178.5(4) . . . . ?
C8 C1 C6 C7 -2.0(4) . . . . ?
C5 C6 C7 O5 -1.3(8) . . . . ?
C1 C6 C7 O5 -179.2(4) . . . . ?
C5 C6 C7 N1 177.7(4) . . . . ?
C1 C6 C7 N1 -0.2(4) . . . . ?
C6 C1 C8 O6 -176.0(4) . . . . ?
C2 C1 C8 O6 3.4(7) . . . . ?
C6 C1 C8 N1 3.4(4) . . . . ?
C2 C1 C8 N1 -177.2(4) . . . . ?
S2 C9 C10 C11 176.7(3) . . . . ?
S2 C9 C10 C12 -62.2(4) . . . . ?
C11 C10 C12 O4 71.0(5) . . . . ?
C9 C10 C12 O4 -51.8(5) . . . . ?
C11 C10 C12 N2 -106.5(5) . . . . ?
C9 C10 C12 N2 130.7(4) . . . . ?
N2 C13 C14 C15 -3.8(10) . . . . ?
C13 C14 C15 C16 1.0(10) . . . . ?
C14 C15 C16 N2 2.3(6) . . . . ?
C14 C15 C16 C17 -118.1(6) . . . . ?
N2 C16 C17 O3 -28.4(6) . . . . ?
C15 C16 C17 O3 87.9(6) . . . . ?
N2 C16 C17 O2 154.1(4) . . . . ?
C15 C16 C17 O2 -89.6(5) . . . . ?
O5 C7 N1 C8 -178.4(4) . . . . ?
C6 C7 N1 C8 2.5(4) . . . . ?
O5 C7 N1 S1 2.9(6) . . . . ?
C6 C7 N1 S1 -176.3(3) . . . . ?
O6 C8 N1 C7 175.9(4) . . . . ?
C1 C8 N1 C7 -3.6(4) . . . . ?
O6 C8 N1 S1 -5.4(6) . . . . ?
C1 C8 N1 S1 175.1(2) . . . . ?
O4 C12 N2 C16 -2.2(6) . . . . ?
C10 C12 N2 C16 175.3(4) . . . . ?
O4 C12 N2 C13 177.3(6) . . . . ?
C10 C12 N2 C13 -5.3(7) . . . . ?
C17 C16 N2 C12 -64.4(4) . . . . ?
C15 C16 N2 C12 174.8(4) . . . . ?
C17 C16 N2 C13 116.1(5) . . . . ?
C15 C16 N2 C13 -4.8(6) . . . . ?
C14 C13 N2 C12 -174.2(6) . . . . ?
C14 C13 N2 C16 5.3(8) . . . . ?
O3 C17 O2 C18 0.7(8) . . . . ?
C16 C17 O2 C18 178.3(5) . . . . ?
C7 N1 S1 S2 -89.3(3) . . . . ?
C8 N1 S1 S2 92.1(3) . . . . ?
C10 C9 S2 S1 -65.1(3) . . . . ?
 
_refine_diff_density_max    0.441
_refine_diff_density_min   -0.618
_refine_diff_density_rms    0.048



