
data_I
_chemical_name_systematic               ?
_chemical_name_common                   u180316mor1
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C22 H20 N2 O4 S2'
_chemical_formula_iupac                 ?
_chemical_formula_weight                440.54

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'C 1 2/c 1'
_space_group_name_Hall                  '-C 2yc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'

_cell_length_a                          32.963(3)
_cell_length_b                          8.7052(9)
_cell_length_c                          15.5575(15)
_cell_angle_alpha                       90
_cell_angle_beta                        114.780(3)
_cell_angle_gamma                       90
_cell_volume                            4053.2(7)
_cell_formula_units_Z                   8
_cell_measurement_reflns_used           9997
_cell_measurement_theta_min             2.95
_cell_measurement_theta_max             68.29
_cell_measurement_temperature           173

_exptl_crystal_description              Prismatic
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.200
_exptl_crystal_size_mid                 0.100
_exptl_crystal_size_min                 0.100
_exptl_crystal_density_diffrn           1.444
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1840

_exptl_absorpt_coefficient_mu           2.663
_exptl_absorpt_correction_type          empirical
_exptl_absorpt_process_details          'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min         0.62
_exptl_absorpt_correction_T_max         0.78

_exptl_special_details                  'SADABS (Sheldrick 1996)' 

_diffrn_ambient_temperature             173

_diffrn_source                          'Bruker TXS fine-focus rotating anode'
_diffrn_source_type                     ?

_diffrn_radiation_type                  CuK\a
_diffrn_radiation_wavelength            1.54178
_diffrn_radiation_monochromator         
    'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type         
    'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method              'Phi and Omega scans'

_diffrn_detector_area_resol_mean        ?

_diffrn_reflns_number                   13824
_diffrn_reflns_av_R_equivalents         0.0182
_diffrn_reflns_av_unetI/netI            0.0187
_diffrn_reflns_theta_min                5.292
_diffrn_reflns_theta_max                68.302
_diffrn_reflns_theta_full               67.679
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full    0.995
_diffrn_reflns_limit_h_min              -37
_diffrn_reflns_limit_h_max              39
_diffrn_reflns_limit_k_min              -10
_diffrn_reflns_limit_k_max              10
_diffrn_reflns_limit_l_min              -18
_diffrn_reflns_limit_l_max              18

_refine_special_details                 
;
;

_reflns_number_total                    3709
_reflns_number_gt                       3563
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0352
_refine_ls_R_factor_gt                  0.0343
_refine_ls_wR_factor_gt                 0.0940
_refine_ls_wR_factor_ref                0.0951
_refine_ls_goodness_of_fit_ref          1.067
_refine_ls_restrained_S_all             1.067
_refine_ls_number_reflns                3709
_refine_ls_number_parameters            277
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           mixed
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0566P)²+3.6684P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          mixed
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.463
_refine_diff_density_min                -0.277
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement              'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction               'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution           'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement         'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics           'XSHEL (Bruker AXS,2002)'
_computing_publication_material         'XCIF (Bruker AXS, 2001)'

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.13802(2) 0.59310(4) 0.34028(2) 0.02666(12) Uani d . . . 1 . .
    S S2 0.06683(2) 1.03610(4) 0.19278(3) 0.02575(12) Uani d . . . 1 . .
    O O2 0.14231(4) 0.47364(14) 0.40711(8) 0.0352(3) Uani d . . . 1 . .
    C C8 0.01809(5) 0.52054(18) 0.15029(11) 0.0248(3) Uani d . . . 1 . .
    C C2 0.05664(5) 0.73560(17) 0.22204(10) 0.0231(3) Uani d . . . 1 . .
    C C1 0.08295(5) 0.60739(17) 0.25712(11) 0.0251(3) Uani d . . . 1 . .
    C C9 0.16780(5) 0.53090(17) 0.27462(11) 0.0259(3) Uani d . . . 1 . .
    C C3 0.01449(5) 0.68209(17) 0.15262(10) 0.0234(3) Uani d . . . 1 . .
    C C16 0.10001(5) 0.99657(18) 0.13155(11) 0.0264(3) Uani d . . . 1 . .
    C C12 0.21481(5) 0.4311(2) 0.17262(12) 0.0349(4) Uani d . . . 1 . .
    C C20 0.16967(6) 1.0144(2) 0.11984(13) 0.0375(4) Uani d . . . 1 . .
    H H20 0.2 1.0469 0.1454 0.045 Uiso calc U . R 1 . .
    C C7 -0.01716(6) 0.42773(19) 0.09086(12) 0.0314(4) Uani d . . . 1 . .
    H H7 -0.0143 0.3192 0.0903 0.038 Uiso calc U . R 1 . .
    C C17 0.08123(6) 0.92009(18) 0.04523(11) 0.0293(3) Uani d . . . 1 . .
    H H17 0.0508 0.8885 0.0196 0.035 Uiso calc U . R 1 . .
    C C14 0.19712(6) 0.4090(2) 0.30815(12) 0.0332(4) Uani d . . . 1 . .
    H H14 0.201 0.3587 0.3653 0.04 Uiso calc U . R 1 . .
    C C5 -0.06052(5) 0.6606(2) 0.03494(12) 0.0342(4) Uani d . . . 1 . .
    H H5 -0.0881 0.7067 -0.0056 0.041 Uiso calc U . R 1 . .
    C C4 -0.02624(5) 0.75201(18) 0.09313(11) 0.0288(3) Uani d . . . 1 . .
    H H4 -0.0298 0.8603 0.0934 0.035 Uiso calc U . R 1 . .
    C C11 0.18484(6) 0.5526(2) 0.14028(12) 0.0358(4) Uani d . . . 1 . .
    H H11 0.1802 0.6012 0.0822 0.043 Uiso calc U . R 1 . .
    C C18 0.10750(6) 0.89068(19) -0.00286(11) 0.0322(4) Uani d . . . 1 . .
    H H18 0.095 0.8374 -0.0615 0.039 Uiso calc U . R 1 . .
    C C13 0.22080(6) 0.3609(2) 0.25743(13) 0.0380(4) Uani d . . . 1 . .
    H H13 0.2415 0.2785 0.281 0.046 Uiso calc U . R 1 . .
    C C10 0.16171(6) 0.6040(2) 0.19069(12) 0.0332(4) Uani d . . . 1 . .
    H H10 0.1418 0.6886 0.1683 0.04 Uiso calc U . R 1 . .
    C C19 0.15182(6) 0.93779(19) 0.03319(12) 0.0324(4) Uani d . . . 1 . .
    C C6 -0.05597(6) 0.5001(2) 0.03366(12) 0.0351(4) Uani d . . . 1 . .
    H H6 -0.0805 0.4404 -0.008 0.042 Uiso calc U . R 1 . .
    C C21 0.14416(6) 1.0439(2) 0.16935(12) 0.0342(4) Uani d . . . 1 . .
    H H21 0.1567 1.096 0.2284 0.041 Uiso calc U . R 1 . .
    C C22 0.18009(7) 0.9079(2) -0.01993(14) 0.0413(4) Uani d . . . 1 . .
    H H22A 0.1639 0.8403 -0.0739 0.062 Uiso calc U . R 1 . .
    H H22B 0.2081 0.8586 0.0223 0.062 Uiso calc U . R 1 . .
    H H22C 0.1867 1.0055 -0.0429 0.062 Uiso calc U . R 1 . .
    C C15 0.23994(7) 0.3761(3) 0.11687(16) 0.0519(5) Uani d . . . 1 . .
    H H15A 0.2653 0.3129 0.1576 0.078 Uiso calc U . R 1 . .
    H H15B 0.2508 0.4648 0.0939 0.078 Uiso calc U . R 1 . .
    H H15C 0.22 0.3148 0.0628 0.078 Uiso calc U . R 1 . .
    N N1 0.05973(4) 0.47722(15) 0.21438(9) 0.0272(3) Uani d . . . 1 . .
    H H1 0.0699 0.3824 0.2261 0.033 Uiso calc U . R 1 . .
    N N2 0.06873(5) 0.88600(15) 0.25841(10) 0.0270(3) Uani d . . . 1 . .
    O O1 0.15200(4) 0.74697(14) 0.37454(8) 0.0369(3) Uani d . . . 1 . .
    O O3 0.02195(4) 1.05610(13) 0.12465(8) 0.0331(3) Uani d . . . 1 . .
    O O4 0.08821(4) 1.15608(13) 0.26043(8) 0.0329(3) Uani d . . . 1 . .
    H H2 0.0907(7) 0.887(2) 0.3055(16) 0.034(5) Uiso d . . . 1 . .


_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.4350(12) ?
    S1 O1 . 1.4438(12) ?
    S1 C1 . 1.7366(16) ?
    S1 C9 . 1.7725(16) ?
    S2 O3 . 1.4239(12) ?
    S2 O4 . 1.4401(12) ?
    S2 N2 . 1.6433(14) ?
    S2 C16 . 1.7595(16) ?
    C8 N1 . 1.369(2) ?
    C8 C7 . 1.399(2) ?
    C8 C3 . 1.413(2) ?
    C2 C1 . 1.378(2) ?
    C2 N2 . 1.4156(19) ?
    C2 C3 . 1.434(2) ?
    C1 N1 . 1.373(2) ?
    C9 C14 . 1.382(2) ?
    C9 C10 . 1.389(2) ?
    C3 C4 . 1.410(2) ?
    C16 C21 . 1.384(2) ?
    C16 C17 . 1.390(2) ?
    C12 C11 . 1.390(3) ?
    C12 C13 . 1.391(3) ?
    C12 C15 . 1.507(3) ?
    C20 C21 . 1.382(3) ?
    C20 C19 . 1.394(3) ?
    C7 C6 . 1.368(2) ?
    C17 C18 . 1.385(2) ?
    C14 C13 . 1.387(3) ?
    C5 C4 . 1.368(2) ?
    C5 C6 . 1.407(3) ?
    C11 C10 . 1.378(3) ?
    C18 C19 . 1.390(3) ?
    C19 C22 . 1.505(2) ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O1 . . 119.05(7) ?
    O2 S1 C1 . . 110.27(7) ?
    O1 S1 C1 . . 106.31(7) ?
    O2 S1 C9 . . 106.62(7) ?
    O1 S1 C9 . . 109.15(7) ?
    C1 S1 C9 . . 104.54(7) ?
    O3 S2 O4 . . 119.53(7) ?
    O3 S2 N2 . . 108.48(7) ?
    O4 S2 N2 . . 104.07(7) ?
    O3 S2 C16 . . 107.97(7) ?
    O4 S2 C16 . . 108.22(7) ?
    N2 S2 C16 . . 108.09(7) ?
    N1 C8 C7 . . 128.60(14) ?
    N1 C8 C3 . . 108.96(13) ?
    C7 C8 C3 . . 122.43(14) ?
    C1 C2 N2 . . 124.46(14) ?
    C1 C2 C3 . . 106.58(13) ?
    N2 C2 C3 . . 128.54(14) ?
    N1 C1 C2 . . 110.26(13) ?
    N1 C1 S1 . . 119.87(11) ?
    C2 C1 S1 . . 129.85(12) ?
    C14 C9 C10 . . 120.61(15) ?
    C14 C9 S1 . . 119.06(12) ?
    C10 C9 S1 . . 120.33(12) ?
    C4 C3 C8 . . 118.68(14) ?
    C4 C3 C2 . . 135.21(14) ?
    C8 C3 C2 . . 106.10(13) ?
    C21 C16 C17 . . 121.08(15) ?
    C21 C16 S2 . . 119.55(12) ?
    C17 C16 S2 . . 119.36(12) ?
    C11 C12 C13 . . 118.33(16) ?
    C11 C12 C15 . . 120.83(17) ?
    C13 C12 C15 . . 120.84(17) ?
    C21 C20 C19 . . 121.29(16) ?
    C6 C7 C8 . . 117.10(16) ?
    C18 C17 C16 . . 118.95(15) ?
    C9 C14 C13 . . 119.23(16) ?
    C4 C5 C6 . . 121.59(15) ?
    C5 C4 C3 . . 118.58(15) ?
    C10 C11 C12 . . 121.34(16) ?
    C17 C18 C19 . . 121.14(16) ?
    C14 C13 C12 . . 121.13(16) ?
    C11 C10 C9 . . 119.33(16) ?
    C18 C19 C20 . . 118.53(16) ?
    C18 C19 C22 . . 121.06(16) ?
    C20 C19 C22 . . 120.42(17) ?
    C7 C6 C5 . . 121.62(16) ?
    C20 C21 C16 . . 119.00(16) ?
    C8 N1 C1 . . 108.10(13) ?
    C2 N2 S2 . . 123.78(11) ?



