data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. C. D. Gabbutt
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C28 H27 N O3 S'
_chemical_formula_sum
 'C28 H27 N O3 S'
_chemical_formula_weight          457.57
 
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)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    13.7943(9)
_cell_length_b                    12.3387(7)
_cell_length_c                    13.7156(8)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.203(4)
_cell_angle_gamma                 90.00
_cell_volume                      2334.4(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     5568
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Shard
_exptl_crystal_colour             Yellow
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.14
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.302
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              968
_exptl_absorpt_coefficient_mu     0.169
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9734
_exptl_absorpt_correction_T_max   0.9933
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)'

_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             32198
_diffrn_reflns_av_R_equivalents   0.0448
_diffrn_reflns_av_sigmaI/netI     0.0411
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.31
_diffrn_reflns_theta_max          27.48
_reflns_number_total              5311
_reflns_number_gt                 4166
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   ?
 
_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)+(0.0354P)²+1.1377P] 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      SHELXL
_refine_ls_extinction_coef        0.0060(9)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5311
_refine_ls_number_parameters      306
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0660
_refine_ls_R_factor_gt            0.0460
_refine_ls_wR_factor_ref          0.1014
_refine_ls_wR_factor_gt           0.0943
_refine_ls_goodness_of_fit_ref    1.037
_refine_ls_restrained_S_all       1.037
_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
C1 C 0.32744(10) 0.45313(13) -0.00332(11) 0.0236(3) Uani 1 1 d . . .
C2 C 0.29610(10) 0.45316(12) 0.09173(11) 0.0205(3) Uani 1 1 d . . .
C3 C 0.32086(10) 0.55681(12) 0.13223(11) 0.0210(3) Uani 1 1 d . . .
C4 C 0.37027(11) 0.61511(13) 0.06159(11) 0.0238(3) Uani 1 1 d . . .
C5 C 0.42243(12) 0.57971(16) -0.11058(12) 0.0346(4) Uani 1 1 d . . .
H5A H 0.4287 0.6587 -0.1149 0.052 Uiso 1 1 calc R . .
H5B H 0.3845 0.5531 -0.1662 0.052 Uiso 1 1 calc R . .
H5C H 0.4870 0.5466 -0.1114 0.052 Uiso 1 1 calc R . .
C6 C 0.31223(12) 0.37281(15) -0.08289(12) 0.0315(4) Uani 1 1 d . . .
H6A H 0.2860 0.3056 -0.0555 0.047 Uiso 1 1 calc R . .
H6B H 0.3742 0.3577 -0.1148 0.047 Uiso 1 1 calc R . .
H6C H 0.2664 0.4023 -0.1308 0.047 Uiso 1 1 calc R . .
C7 C 0.42222(12) 0.72140(14) 0.06628(13) 0.0323(4) Uani 1 1 d . . .
H7A H 0.4885 0.7124 0.0420 0.048 Uiso 1 1 calc R . .
H7B H 0.4244 0.7468 0.1340 0.048 Uiso 1 1 calc R . .
H7C H 0.3879 0.7747 0.0260 0.048 Uiso 1 1 calc R . .
C8 C 0.24543(10) 0.36333(12) 0.14261(11) 0.0211(3) Uani 1 1 d . . .
C9 C 0.29790(11) 0.25745(12) 0.14528(11) 0.0235(3) Uani 1 1 d . . .
C10 C 0.38768(11) 0.24877(13) 0.19329(11) 0.0241(3) Uani 1 1 d . . .
C11 C 0.44117(13) 0.15359(14) 0.18686(12) 0.0313(4) Uani 1 1 d . . .
H11 H 0.5032 0.1494 0.2170 0.038 Uiso 1 1 calc R . .
C12 C 0.40503(14) 0.06501(15) 0.13706(13) 0.0370(4) Uani 1 1 d . . .
H12 H 0.4425 0.0006 0.1324 0.044 Uiso 1 1 calc R . .
C13 C 0.31459(14) 0.06991(15) 0.09403(13) 0.0383(4) Uani 1 1 d . . .
H13 H 0.2886 0.0082 0.0618 0.046 Uiso 1 1 calc R . .
C14 C 0.26171(13) 0.16589(14) 0.09821(13) 0.0324(4) Uani 1 1 d . . .
H14 H 0.1996 0.1690 0.0683 0.039 Uiso 1 1 calc R . .
C15 C 0.30182(10) 0.58530(12) 0.23375(11) 0.0207(3) Uani 1 1 d . . .
C16 C 0.25638(10) 0.68826(12) 0.26186(11) 0.0222(3) Uani 1 1 d . . .
C17 C 0.23801(11) 0.71045(13) 0.36111(11) 0.0254(3) Uani 1 1 d . . .
C18 C 0.19222(12) 0.80621(14) 0.38843(12) 0.0297(4) Uani 1 1 d . . .
H18 H 0.1809 0.8209 0.4554 0.036 Uiso 1 1 calc R . .
C19 C 0.16338(12) 0.87957(14) 0.31855(13) 0.0313(4) Uani 1 1 d . . .
H19 H 0.1321 0.9448 0.3376 0.038 Uiso 1 1 calc R . .
C20 C 0.17949(12) 0.85922(13) 0.22061(13) 0.0293(4) Uani 1 1 d . . .
H20 H 0.1594 0.9102 0.1728 0.035 Uiso 1 1 calc R . .
C21 C 0.22491(11) 0.76444(13) 0.19285(12) 0.0253(3) Uani 1 1 d . . .
H21 H 0.2350 0.7506 0.1255 0.030 Uiso 1 1 calc R . .
C22 C 0.16085(11) 0.37633(13) 0.18861(12) 0.0257(3) Uani 1 1 d . . .
H22 H 0.1376 0.3167 0.2256 0.031 Uiso 1 1 calc R . .
C23 C 0.10068(11) 0.47478(13) 0.18701(12) 0.0273(4) Uani 1 1 d . . .
C24 C 0.05815(12) 0.51828(14) 0.26790(14) 0.0329(4) Uani 1 1 d . . .
C25 C 0.01909(12) 0.62115(14) 0.11556(14) 0.0344(4) Uani 1 1 d . . .
C26 C 0.07790(11) 0.53446(13) 0.10089(13) 0.0293(4) Uani 1 1 d . . .
H26 H 0.1019 0.5152 0.0384 0.035 Uiso 1 1 calc R . .
C27 C 0.06586(15) 0.48302(17) 0.37196(14) 0.0456(5) Uani 1 1 d . . .
H27A H 0.1139 0.4248 0.3775 0.068 Uiso 1 1 calc R . .
H27B H 0.0027 0.4566 0.3942 0.068 Uiso 1 1 calc R . .
H27C H 0.0861 0.5446 0.4124 0.068 Uiso 1 1 calc R . .
C28 C -0.01874(14) 0.70081(16) 0.04303(17) 0.0469(5) Uani 1 1 d . . .
H28A H 0.0167 0.7693 0.0497 0.070 Uiso 1 1 calc R . .
H28B H -0.0879 0.7134 0.0547 0.070 Uiso 1 1 calc R . .
H28C H -0.0099 0.6721 -0.0230 0.070 Uiso 1 1 calc R . .
N1 N 0.37330(9) 0.55110(11) -0.01979(9) 0.0253(3) Uani 1 1 d . . .
O1 O 0.42556(8) 0.33017(9) 0.24877(8) 0.0268(3) Uani 1 1 d . . .
H1 H 0.3849 0.3806 0.2534 0.040 Uiso 1 1 calc R . .
O2 O 0.32089(8) 0.51576(9) 0.29816(7) 0.0248(2) Uani 1 1 d . . .
O3 O 0.26245(9) 0.63993(10) 0.43265(8) 0.0328(3) Uani 1 1 d . . .
H3 H 0.2880 0.5846 0.4079 0.049 Uiso 1 1 calc R . .
S1 S -0.00857(3) 0.63195(4) 0.23794(4) 0.03984(14) 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 C2 1.375(2) . ?
C1 N1 1.383(2) . ?
C1 C6 1.489(2) . ?
C2 C3 1.435(2) . ?
C2 C8 1.486(2) . ?
C3 C4 1.387(2) . ?
C3 C15 1.461(2) . ?
C4 N1 1.368(2) . ?
C4 C7 1.496(2) . ?
C5 N1 1.463(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C22 1.338(2) . ?
C8 C9 1.494(2) . ?
C9 C14 1.393(2) . ?
C9 C10 1.405(2) . ?
C10 O1 1.3630(19) . ?
C10 C11 1.390(2) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O2 1.2586(18) . ?
C15 C16 1.469(2) . ?
C16 C21 1.402(2) . ?
C16 C17 1.412(2) . ?
C17 O3 1.3532(19) . ?
C17 C18 1.392(2) . ?
C18 C19 1.376(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.471(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.367(2) . ?
C23 C26 1.426(2) . ?
C24 C27 1.496(3) . ?
C24 S1 1.7263(19) . ?
C25 C26 1.358(2) . ?
C25 C28 1.491(3) . ?
C25 S1 1.728(2) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
O1 H1 0.8400 . ?
O3 H3 0.8400 . ?
 
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
C2 C1 N1 107.47(14) . . ?
C2 C1 C6 130.64(15) . . ?
N1 C1 C6 121.70(14) . . ?
C1 C2 C3 106.98(13) . . ?
C1 C2 C8 126.53(14) . . ?
C3 C2 C8 126.49(13) . . ?
C4 C3 C2 107.97(13) . . ?
C4 C3 C15 129.14(14) . . ?
C2 C3 C15 122.69(13) . . ?
N1 C4 C3 106.67(14) . . ?
N1 C4 C7 121.68(14) . . ?
C3 C4 C7 131.37(15) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C22 C8 C2 122.99(14) . . ?
C22 C8 C9 121.10(14) . . ?
C2 C8 C9 115.80(12) . . ?
C14 C9 C10 118.00(15) . . ?
C14 C9 C8 121.68(14) . . ?
C10 C9 C8 120.29(13) . . ?
O1 C10 C11 117.10(14) . . ?
O1 C10 C9 122.76(14) . . ?
C11 C10 C9 120.13(15) . . ?
C12 C11 C10 120.62(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.08(16) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.52(17) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 121.48(17) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
O2 C15 C3 117.85(14) . . ?
O2 C15 C16 119.59(13) . . ?
C3 C15 C16 122.45(13) . . ?
C21 C16 C17 117.69(14) . . ?
C21 C16 C15 122.30(14) . . ?
C17 C16 C15 119.92(14) . . ?
O3 C17 C18 117.57(14) . . ?
O3 C17 C16 121.95(14) . . ?
C18 C17 C16 120.48(15) . . ?
C19 C18 C17 120.08(16) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.61(15) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 119.70(15) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C16 121.43(15) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
C8 C22 C23 125.79(15) . . ?
C8 C22 H22 117.1 . . ?
C23 C22 H22 117.1 . . ?
C24 C23 C26 112.07(15) . . ?
C24 C23 C22 123.77(16) . . ?
C26 C23 C22 124.14(15) . . ?
C23 C24 C27 129.14(17) . . ?
C23 C24 S1 110.84(14) . . ?
C27 C24 S1 119.97(13) . . ?
C26 C25 C28 128.91(18) . . ?
C26 C25 S1 109.80(14) . . ?
C28 C25 S1 121.28(14) . . ?
C25 C26 C23 114.45(16) . . ?
C25 C26 H26 122.8 . . ?
C23 C26 H26 122.8 . . ?
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 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C4 N1 C1 110.85(12) . . ?
C4 N1 C5 124.80(14) . . ?
C1 N1 C5 124.29(14) . . ?
C10 O1 H1 109.5 . . ?
C17 O3 H3 109.5 . . ?
C24 S1 C25 92.82(9) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
O1 H1 O2  0.84 1.99 2.7918(15) 160.6 .
O3 H3 O2  0.84 1.79 2.5319(15) 146.5 .
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.267
_refine_diff_density_min   -0.238
_refine_diff_density_rms    0.042
