data_tetracycle_4a 

_audit_update_record
;
2010-06-01 # Formatted by publCIF
;
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           '184-185oC' 
_chemical_formula_moiety          'C18 H19 N O4 S' 
_chemical_formula_sum 
 'C18 H19 N O4 S' 
_chemical_formula_weight          345.40 
 
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                    9.18680(10) 
_cell_length_b                    13.60830(10) 
_cell_length_c                    14.42970(10) 
_cell_angle_alpha                 67.7380(10) 
_cell_angle_beta                  78.2150(10) 
_cell_angle_gamma                 86.5250(10) 
_cell_volume                      1634.02(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     113(2) 
_cell_measurement_reflns_used     51402
_cell_measurement_theta_min       3.62
_cell_measurement_theta_max       25.39
 
_exptl_crystal_description        needle
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.35 
_exptl_crystal_size_mid           0.33 
_exptl_crystal_size_min           0.25 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.404 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              728 
_exptl_absorpt_coefficient_mu     0.220 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9268 
_exptl_absorpt_correction_T_max   0.9452
_exptl_absorpt_process_details    'SADABS (Sheldrick, 1990)' 
 
_exptl_special_details 
; 
Half sphere of data collected using COLLECT strategy (Nonius, 2000).
 Crystal to detector distance = 40mm; combination of φ and ω scans of
 1.2°, 50s per °, 2 iterations.
; 
 
_diffrn_ambient_temperature       113(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   'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method        '1.2° φ scans and ω scans' 
_diffrn_reflns_number             51402 
_diffrn_reflns_av_R_equivalents   0.0439 
_diffrn_reflns_av_sigmaI/netI     0.0234 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_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          3.62 
_diffrn_reflns_theta_max          25.39 
_reflns_number_total              5962 
_reflns_number_gt                 5003 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection     'COLLECT program (Nonius, 2000)'
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction      'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution  'SHELXS-97 (Sheldrick, 1997)' 
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics   'X-Seed (Barbour, 2001)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 2001)'  
 
_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)+(0.0330P)²+0.7271P] 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        none 
_refine_ls_number_reflns          5962 
_refine_ls_number_parameters      445 
_refine_ls_number_restraints      2 
_refine_ls_R_factor_all           0.0402 
_refine_ls_R_factor_gt            0.0305 
_refine_ls_wR_factor_ref          0.0767 
_refine_ls_wR_factor_gt           0.0718 
_refine_ls_goodness_of_fit_ref    1.039 
_refine_ls_restrained_S_all       1.040 
_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 
S1A S -0.07092(4) 0.31411(3) -0.16862(3) 0.02304(10) Uani 1 1 d . . . 
O1A O -0.19894(13) 0.29833(9) -0.30983(9) 0.0334(3) Uani 1 1 d . . . 
O2A O 0.17117(11) 0.06739(8) -0.15744(8) 0.0220(2) Uani 1 1 d . . . 
O3A O 0.33624(12) 0.13688(8) -0.00654(7) 0.0249(2) Uani 1 1 d . . . 
O4A O 0.19048(12) 0.34352(8) -0.09280(8) 0.0228(2) Uani 1 1 d D . . 
H4A H 0.2556(19) 0.3345(16) -0.0457(13) 0.051(6) Uiso 1 1 d D . . 
N1A N 0.43170(13) 0.17508(9) -0.17704(9) 0.0201(3) Uani 1 1 d . . . 
C1A C -0.10676(16) 0.26021(12) -0.25665(11) 0.0234(3) Uani 1 1 d . . . 
C2A C -0.01666(16) 0.16705(12) -0.25425(11) 0.0218(3) Uani 1 1 d . . . 
C3A C -0.0405(2) 0.11074(14) -0.32206(13) 0.0331(4) Uani 1 1 d . . . 
H3A1 H -0.0549 0.0345 -0.2818 0.050 Uiso 1 1 calc R . . 
H3A2 H 0.0467 0.1224 -0.3773 0.050 Uiso 1 1 calc R . . 
H3A3 H -0.1287 0.1387 -0.3512 0.050 Uiso 1 1 calc R . . 
C4A C 0.07228(15) 0.14465(11) -0.18569(11) 0.0186(3) Uani 1 1 d . . . 
C5A C 0.06320(15) 0.21235(11) -0.12228(11) 0.0187(3) Uani 1 1 d . . . 
C6A C 0.00230(17) 0.14539(12) -0.00985(11) 0.0240(3) Uani 1 1 d . . . 
H6A1 H 0.0705 0.0875 0.0150 0.036 Uiso 1 1 calc R . . 
H6A2 H -0.0956 0.1157 -0.0032 0.036 Uiso 1 1 calc R . . 
H6A3 H -0.0070 0.1902 0.0305 0.036 Uiso 1 1 calc R . . 
C7A C 0.21718(15) 0.26886(11) -0.14022(10) 0.0177(3) Uani 1 1 d . . . 
C8A C 0.33318(15) 0.18506(11) -0.09722(11) 0.0188(3) Uani 1 1 d . . . 
C9A C 0.40743(15) 0.25267(11) -0.27058(11) 0.0192(3) Uani 1 1 d . . . 
C10A C 0.28682(15) 0.31439(11) -0.25254(11) 0.0186(3) Uani 1 1 d . . . 
C11A C 0.24924(17) 0.40063(12) -0.33222(11) 0.0231(3) Uani 1 1 d . . . 
H11A H 0.1696 0.4449 -0.3203 0.028 Uiso 1 1 calc R . . 
C12A C 0.33096(18) 0.42121(13) -0.43074(12) 0.0287(4) Uani 1 1 d . . . 
H12A H 0.3057 0.4794 -0.4867 0.034 Uiso 1 1 calc R . . 
C13A C 0.44842(18) 0.35738(13) -0.44737(12) 0.0295(4) Uani 1 1 d . . . 
H13A H 0.5013 0.3718 -0.5151 0.035 Uiso 1 1 calc R . . 
C14A C 0.49110(17) 0.27268(13) -0.36757(11) 0.0250(3) Uani 1 1 d . . . 
H14A H 0.5738 0.2305 -0.3790 0.030 Uiso 1 1 calc R . . 
C15A C 0.53866(17) 0.08943(13) -0.16694(12) 0.0268(3) Uani 1 1 d . . . 
H15A H 0.5342 0.0473 -0.0934 0.032 Uiso 1 1 calc R . . 
H15B H 0.6399 0.1212 -0.1961 0.032 Uiso 1 1 calc R . . 
C16A C 0.51391(18) 0.01453(13) -0.21894(13) 0.0314(4) Uani 1 1 d . . . 
H16A H 0.5965 -0.0363 -0.2122 0.038 Uiso 1 1 calc R . . 
H16B H 0.5219 0.0572 -0.2927 0.038 Uiso 1 1 calc R . . 
C17A C 0.36797(19) -0.04955(13) -0.18143(14) 0.0336(4) Uani 1 1 d . . . 
H17A H 0.3841 -0.1124 -0.2008 0.040 Uiso 1 1 calc R . . 
H17B H 0.3453 -0.0760 -0.1059 0.040 Uiso 1 1 calc R . . 
C18A C 0.23205(18) 0.00699(13) -0.21981(13) 0.0300(4) Uani 1 1 d . . . 
H18A H 0.2602 0.0550 -0.2923 0.036 Uiso 1 1 calc R . . 
H18B H 0.1573 -0.0454 -0.2144 0.036 Uiso 1 1 calc R . . 
S1B S -0.09679(4) 0.22479(3) 0.28793(3) 0.02435(10) Uani 1 1 d . . . 
O1B O -0.22196(13) 0.24227(11) 0.46164(9) 0.0412(3) Uani 1 1 d . . . 
O2B O 0.21342(11) 0.43094(8) 0.23543(8) 0.0226(2) Uani 1 1 d . . . 
O3B O 0.35923(11) 0.35281(9) 0.04194(8) 0.0260(2) Uani 1 1 d . . . 
O4B O 0.15498(11) 0.16687(8) 0.15933(8) 0.0239(2) Uani 1 1 d D . . 
H4B H 0.2261(19) 0.1669(17) 0.1005(11) 0.055(6) Uiso 1 1 d D . . 
N1B N 0.43924(13) 0.29770(10) 0.19424(9) 0.0202(3) Uani 1 1 d . . . 
C1B C -0.11772(17) 0.27178(13) 0.39000(12) 0.0262(3) Uani 1 1 d . . . 
C2B C 0.00090(16) 0.34723(12) 0.37282(11) 0.0222(3) Uani 1 1 d . . . 
C3B C 0.00016(19) 0.39213(14) 0.45352(12) 0.0322(4) Uani 1 1 d . . . 
H3B1 H 0.0763 0.3574 0.4933 0.048 Uiso 1 1 calc R . . 
H3B2 H -0.0978 0.3795 0.4989 0.048 Uiso 1 1 calc R . . 
H3B3 H 0.0215 0.4687 0.4209 0.048 Uiso 1 1 calc R . . 
C4B C 0.09381(15) 0.36630(11) 0.28259(11) 0.0189(3) Uani 1 1 d . . . 
C5B C 0.06630(15) 0.30918(11) 0.21572(11) 0.0189(3) Uani 1 1 d . . . 
C6B C 0.03239(17) 0.38880(13) 0.11435(11) 0.0257(3) Uani 1 1 d . . . 
H6B1 H -0.0560 0.4290 0.1280 0.039 Uiso 1 1 calc R . . 
H6B2 H 0.0141 0.3504 0.0723 0.039 Uiso 1 1 calc R . . 
H6B3 H 0.1174 0.4378 0.0779 0.039 Uiso 1 1 calc R . . 
C7B C 0.20129(15) 0.23448(11) 0.20204(11) 0.0181(3) Uani 1 1 d . . . 
C8B C 0.34028(15) 0.30318(11) 0.13423(11) 0.0192(3) Uani 1 1 d . . . 
C9B C 0.39173(15) 0.22204(11) 0.29392(11) 0.0189(3) Uani 1 1 d . . . 
C10B C 0.25464(15) 0.17769(11) 0.30144(11) 0.0182(3) Uani 1 1 d . . . 
C11B C 0.19174(17) 0.09585(12) 0.39009(11) 0.0231(3) Uani 1 1 d . . . 
H11B H 0.1002 0.0635 0.3950 0.028 Uiso 1 1 calc R . . 
C12B C 0.26494(18) 0.06148(12) 0.47227(12) 0.0282(4) Uani 1 1 d . . . 
H12B H 0.2231 0.0052 0.5337 0.034 Uiso 1 1 calc R . . 
C13B C 0.39832(18) 0.10899(13) 0.46480(12) 0.0294(4) Uani 1 1 d . . . 
H13B H 0.4449 0.0863 0.5223 0.035 Uiso 1 1 calc R . . 
C14B C 0.46561(17) 0.18920(12) 0.37482(12) 0.0250(3) Uani 1 1 d . . . 
H14B H 0.5586 0.2201 0.3692 0.030 Uiso 1 1 calc R . . 
C15B C 0.56999(17) 0.36818(13) 0.16006(12) 0.0272(3) Uani 1 1 d . . . 
H15C H 0.5753 0.4141 0.0873 0.033 Uiso 1 1 calc R . . 
H15D H 0.6602 0.3243 0.1646 0.033 Uiso 1 1 calc R . . 
C16B C 0.57145(18) 0.43856(13) 0.22053(13) 0.0305(4) Uani 1 1 d . . . 
H16C H 0.6654 0.4808 0.1929 0.037 Uiso 1 1 calc R . . 
H16D H 0.5739 0.3918 0.2920 0.037 Uiso 1 1 calc R . . 
C17B C 0.44303(18) 0.51540(13) 0.22229(14) 0.0331(4) Uani 1 1 d . . . 
H17C H 0.4754 0.5711 0.2426 0.040 Uiso 1 1 calc R . . 
H17D H 0.4254 0.5507 0.1518 0.040 Uiso 1 1 calc R . . 
C18B C 0.29626(17) 0.46888(13) 0.29164(13) 0.0275(3) Uani 1 1 d . . . 
H18C H 0.3139 0.4095 0.3539 0.033 Uiso 1 1 calc R . . 
H18D H 0.2392 0.5237 0.3125 0.033 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 
S1A C1A 1.7793(15) . ? 
S1A C5A 1.8196(14) . ? 
O1A C1A 1.2189(19) . ? 
O2A C4A 1.3445(17) . ? 
O2A C18A 1.4484(17) . ? 
O3A C8A 1.2270(17) . ? 
O4A C7A 1.4102(16) . ? 
O4A H4A 0.964(9) . ? 
N1A C8A 1.3572(18) . ? 
N1A C9A 1.4146(18) . ? 
N1A C15A 1.4616(19) . ? 
C1A C2A 1.465(2) . ? 
C2A C4A 1.346(2) . ? 
C2A C3A 1.506(2) . ? 
C3A H3A1 0.9800 . ? 
C3A H3A2 0.9800 . ? 
C3A H3A3 0.9800 . ? 
C4A C5A 1.5135(19) . ? 
C5A C6A 1.532(2) . ? 
C5A C7A 1.5783(19) . ? 
C6A H6A1 0.9800 . ? 
C6A H6A2 0.9800 . ? 
C6A H6A3 0.9800 . ? 
C7A C10A 1.5112(19) . ? 
C7A C8A 1.552(2) . ? 
C9A C14A 1.386(2) . ? 
C9A C10A 1.391(2) . ? 
C10A C11A 1.382(2) . ? 
C11A C12A 1.397(2) . ? 
C11A H11A 0.9500 . ? 
C12A C13A 1.384(2) . ? 
C12A H12A 0.9500 . ? 
C13A C14A 1.390(2) . ? 
C13A H13A 0.9500 . ? 
C14A H14A 0.9500 . ? 
C15A C16A 1.527(2) . ? 
C15A H15A 0.9900 . ? 
C15A H15B 0.9900 . ? 
C16A C17A 1.529(2) . ? 
C16A H16A 0.9900 . ? 
C16A H16B 0.9900 . ? 
C17A C18A 1.517(2) . ? 
C17A H17A 0.9900 . ? 
C17A H17B 0.9900 . ? 
C18A H18A 0.9900 . ? 
C18A H18B 0.9900 . ? 
S1B C1B 1.7883(15) . ? 
S1B C5B 1.8203(14) . ? 
O1B C1B 1.2143(19) . ? 
O2B C4B 1.3426(18) . ? 
O2B C18B 1.4564(17) . ? 
O3B C8B 1.2240(17) . ? 
O4B C7B 1.4113(16) . ? 
O4B H4B 0.960(9) . ? 
N1B C8B 1.3587(18) . ? 
N1B C9B 1.4126(18) . ? 
N1B C15B 1.4647(19) . ? 
C1B C2B 1.461(2) . ? 
C2B C4B 1.345(2) . ? 
C2B C3B 1.505(2) . ? 
C3B H3B1 0.9800 . ? 
C3B H3B2 0.9800 . ? 
C3B H3B3 0.9800 . ? 
C4B C5B 1.5136(19) . ? 
C5B C6B 1.535(2) . ? 
C5B C7B 1.5842(19) . ? 
C6B H6B1 0.9800 . ? 
C6B H6B2 0.9800 . ? 
C6B H6B3 0.9800 . ? 
C7B C10B 1.5153(19) . ? 
C7B C8B 1.550(2) . ? 
C9B C14B 1.384(2) . ? 
C9B C10B 1.396(2) . ? 
C10B C11B 1.381(2) . ? 
C11B C12B 1.395(2) . ? 
C11B H11B 0.9500 . ? 
C12B C13B 1.386(2) . ? 
C12B H12B 0.9500 . ? 
C13B C14B 1.393(2) . ? 
C13B H13B 0.9500 . ? 
C14B H14B 0.9500 . ? 
C15B C16B 1.523(2) . ? 
C15B H15C 0.9900 . ? 
C15B H15D 0.9900 . ? 
C16B C17B 1.531(2) . ? 
C16B H16C 0.9900 . ? 
C16B H16D 0.9900 . ? 
C17B C18B 1.514(2) . ? 
C17B H17C 0.9900 . ? 
C17B H17D 0.9900 . ? 
C18B H18C 0.9900 . ? 
C18B H18D 0.9900 . ? 
 
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 
C1A S1A C5A 92.67(7) . . ? 
C4A O2A C18A 122.13(11) . . ? 
C7A O4A H4A 112.1(12) . . ? 
C8A N1A C9A 110.77(11) . . ? 
C8A N1A C15A 123.84(12) . . ? 
C9A N1A C15A 125.17(12) . . ? 
O1A C1A C2A 126.20(14) . . ? 
O1A C1A S1A 121.57(12) . . ? 
C2A C1A S1A 112.21(11) . . ? 
C4A C2A C1A 111.20(13) . . ? 
C4A C2A C3A 130.97(14) . . ? 
C1A C2A C3A 117.77(13) . . ? 
C2A C3A H3A1 109.5 . . ? 
C2A C3A H3A2 109.5 . . ? 
H3A1 C3A H3A2 109.5 . . ? 
C2A C3A H3A3 109.5 . . ? 
H3A1 C3A H3A3 109.5 . . ? 
H3A2 C3A H3A3 109.5 . . ? 
O2A C4A C2A 131.87(13) . . ? 
O2A C4A C5A 109.36(11) . . ? 
C2A C4A C5A 118.73(13) . . ? 
C4A C5A C6A 109.74(11) . . ? 
C4A C5A C7A 111.45(11) . . ? 
C6A C5A C7A 113.29(11) . . ? 
C4A C5A S1A 105.13(9) . . ? 
C6A C5A S1A 108.53(10) . . ? 
C7A C5A S1A 108.31(9) . . ? 
C5A C6A H6A1 109.5 . . ? 
C5A C6A H6A2 109.5 . . ? 
H6A1 C6A H6A2 109.5 . . ? 
C5A C6A H6A3 109.5 . . ? 
H6A1 C6A H6A3 109.5 . . ? 
H6A2 C6A H6A3 109.5 . . ? 
O4A C7A C10A 114.95(11) . . ? 
O4A C7A C8A 112.91(11) . . ? 
C10A C7A C8A 101.33(11) . . ? 
O4A C7A C5A 106.80(11) . . ? 
C10A C7A C5A 110.85(11) . . ? 
C8A C7A C5A 109.99(11) . . ? 
O3A C8A N1A 125.82(13) . . ? 
O3A C8A C7A 125.82(12) . . ? 
N1A C8A C7A 108.35(11) . . ? 
C14A C9A C10A 122.19(14) . . ? 
C14A C9A N1A 127.87(13) . . ? 
C10A C9A N1A 109.86(12) . . ? 
C11A C10A C9A 120.11(13) . . ? 
C11A C10A C7A 131.22(13) . . ? 
C9A C10A C7A 108.67(12) . . ? 
C10A C11A C12A 118.52(14) . . ? 
C10A C11A H11A 120.7 . . ? 
C12A C11A H11A 120.7 . . ? 
C13A C12A C11A 120.44(14) . . ? 
C13A C12A H12A 119.8 . . ? 
C11A C12A H12A 119.8 . . ? 
C12A C13A C14A 121.75(14) . . ? 
C12A C13A H13A 119.1 . . ? 
C14A C13A H13A 119.1 . . ? 
C9A C14A C13A 116.93(14) . . ? 
C9A C14A H14A 121.5 . . ? 
C13A C14A H14A 121.5 . . ? 
N1A C15A C16A 114.58(13) . . ? 
N1A C15A H15A 108.6 . . ? 
C16A C15A H15A 108.6 . . ? 
N1A C15A H15B 108.6 . . ? 
C16A C15A H15B 108.6 . . ? 
H15A C15A H15B 107.6 . . ? 
C15A C16A C17A 118.15(13) . . ? 
C15A C16A H16A 107.8 . . ? 
C17A C16A H16A 107.8 . . ? 
C15A C16A H16B 107.8 . . ? 
C17A C16A H16B 107.8 . . ? 
H16A C16A H16B 107.1 . . ? 
C18A C17A C16A 117.22(14) . . ? 
C18A C17A H17A 108.0 . . ? 
C16A C17A H17A 108.0 . . ? 
C18A C17A H17B 108.0 . . ? 
C16A C17A H17B 108.0 . . ? 
H17A C17A H17B 107.2 . . ? 
O2A C18A C17A 107.69(13) . . ? 
O2A C18A H18A 110.2 . . ? 
C17A C18A H18A 110.2 . . ? 
O2A C18A H18B 110.2 . . ? 
C17A C18A H18B 110.2 . . ? 
H18A C18A H18B 108.5 . . ? 
C1B S1B C5B 92.88(7) . . ? 
C4B O2B C18B 121.68(11) . . ? 
C7B O4B H4B 111.5(13) . . ? 
C8B N1B C9B 110.82(11) . . ? 
C8B N1B C15B 123.22(12) . . ? 
C9B N1B C15B 125.78(12) . . ? 
O1B C1B C2B 127.48(14) . . ? 
O1B C1B S1B 120.90(13) . . ? 
C2B C1B S1B 111.61(11) . . ? 
C4B C2B C1B 111.68(13) . . ? 
C4B C2B C3B 130.49(14) . . ? 
C1B C2B C3B 117.82(13) . . ? 
C2B C3B H3B1 109.5 . . ? 
C2B C3B H3B2 109.5 . . ? 
H3B1 C3B H3B2 109.5 . . ? 
C2B C3B H3B3 109.5 . . ? 
H3B1 C3B H3B3 109.5 . . ? 
H3B2 C3B H3B3 109.5 . . ? 
O2B C4B C2B 131.81(13) . . ? 
O2B C4B C5B 109.33(12) . . ? 
C2B C4B C5B 118.86(13) . . ? 
C4B C5B C6B 110.61(12) . . ? 
C4B C5B C7B 109.99(11) . . ? 
C6B C5B C7B 113.62(12) . . ? 
C4B C5B S1B 104.90(9) . . ? 
C6B C5B S1B 109.51(10) . . ? 
C7B C5B S1B 107.80(9) . . ? 
C5B C6B H6B1 109.5 . . ? 
C5B C6B H6B2 109.5 . . ? 
H6B1 C6B H6B2 109.5 . . ? 
C5B C6B H6B3 109.5 . . ? 
H6B1 C6B H6B3 109.5 . . ? 
H6B2 C6B H6B3 109.5 . . ? 
O4B C7B C10B 114.73(12) . . ? 
O4B C7B C8B 112.82(11) . . ? 
C10B C7B C8B 101.33(11) . . ? 
O4B C7B C5B 107.00(11) . . ? 
C10B C7B C5B 111.28(11) . . ? 
C8B C7B C5B 109.64(11) . . ? 
O3B C8B N1B 125.52(13) . . ? 
O3B C8B C7B 125.98(12) . . ? 
N1B C8B C7B 108.49(12) . . ? 
C14B C9B C10B 121.86(13) . . ? 
C14B C9B N1B 128.21(13) . . ? 
C10B C9B N1B 109.89(12) . . ? 
C11B C10B C9B 120.03(13) . . ? 
C11B C10B C7B 131.45(13) . . ? 
C9B C10B C7B 108.52(12) . . ? 
C10B C11B C12B 118.83(14) . . ? 
C10B C11B H11B 120.6 . . ? 
C12B C11B H11B 120.6 . . ? 
C13B C12B C11B 120.37(15) . . ? 
C13B C12B H12B 119.8 . . ? 
C11B C12B H12B 119.8 . . ? 
C12B C13B C14B 121.46(14) . . ? 
C12B C13B H13B 119.3 . . ? 
C14B C13B H13B 119.3 . . ? 
C9B C14B C13B 117.37(14) . . ? 
C9B C14B H14B 121.3 . . ? 
C13B C14B H14B 121.3 . . ? 
N1B C15B C16B 114.53(12) . . ? 
N1B C15B H15C 108.6 . . ? 
C16B C15B H15C 108.6 . . ? 
N1B C15B H15D 108.6 . . ? 
C16B C15B H15D 108.6 . . ? 
H15C C15B H15D 107.6 . . ? 
C15B C16B C17B 117.73(13) . . ? 
C15B C16B H16C 107.9 . . ? 
C17B C16B H16C 107.9 . . ? 
C15B C16B H16D 107.9 . . ? 
C17B C16B H16D 107.9 . . ? 
H16C C16B H16D 107.2 . . ? 
C18B C17B C16B 117.10(14) . . ? 
C18B C17B H17C 108.0 . . ? 
C16B C17B H17C 108.0 . . ? 
C18B C17B H17D 108.0 . . ? 
C16B C17B H17D 108.0 . . ? 
H17C C17B H17D 107.3 . . ? 
O2B C18B C17B 107.94(13) . . ? 
O2B C18B H18C 110.1 . . ? 
C17B C18B H18C 110.1 . . ? 
O2B C18B H18D 110.1 . . ? 
C17B C18B H18D 110.1 . . ? 
H18C C18B H18D 108.4 . . ? 
 
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 
C5A S1A C1A O1A 177.47(14) . . . . ? 
C5A S1A C1A C2A -1.30(11) . . . . ? 
O1A C1A C2A C4A -178.80(15) . . . . ? 
S1A C1A C2A C4A -0.10(16) . . . . ? 
O1A C1A C2A C3A -1.2(2) . . . . ? 
S1A C1A C2A C3A 177.54(11) . . . . ? 
C18A O2A C4A C2A 18.3(2) . . . . ? 
C18A O2A C4A C5A -164.12(12) . . . . ? 
C1A C2A C4A O2A 179.41(14) . . . . ? 
C3A C2A C4A O2A 2.2(3) . . . . ? 
C1A C2A C4A C5A 1.97(18) . . . . ? 
C3A C2A C4A C5A -175.27(15) . . . . ? 
O2A C4A C5A C6A -64.24(14) . . . . ? 
C2A C4A C5A C6A 113.74(15) . . . . ? 
O2A C4A C5A C7A 62.09(14) . . . . ? 
C2A C4A C5A C7A -119.93(14) . . . . ? 
O2A C4A C5A S1A 179.22(9) . . . . ? 
C2A C4A C5A S1A -2.80(16) . . . . ? 
C1A S1A C5A C4A 2.12(10) . . . . ? 
C1A S1A C5A C6A -115.25(10) . . . . ? 
C1A S1A C5A C7A 121.36(10) . . . . ? 
C4A C5A C7A O4A 169.77(11) . . . . ? 
C6A C5A C7A O4A -65.87(14) . . . . ? 
S1A C5A C7A O4A 54.59(12) . . . . ? 
C4A C5A C7A C10A 43.86(15) . . . . ? 
C6A C5A C7A C10A 168.22(12) . . . . ? 
S1A C5A C7A C10A -71.31(12) . . . . ? 
C4A C5A C7A C8A -67.37(14) . . . . ? 
C6A C5A C7A C8A 56.99(15) . . . . ? 
S1A C5A C7A C8A 177.45(9) . . . . ? 
C9A N1A C8A O3A -171.81(13) . . . . ? 
C15A N1A C8A O3A 13.3(2) . . . . ? 
C9A N1A C8A C7A 7.48(15) . . . . ? 
C15A N1A C8A C7A -167.44(12) . . . . ? 
O4A C7A C8A O3A 45.86(19) . . . . ? 
C10A C7A C8A O3A 169.34(13) . . . . ? 
C5A C7A C8A O3A -73.33(17) . . . . ? 
O4A C7A C8A N1A -133.43(12) . . . . ? 
C10A C7A C8A N1A -9.95(14) . . . . ? 
C5A C7A C8A N1A 107.39(13) . . . . ? 
C8A N1A C9A C14A 175.15(14) . . . . ? 
C15A N1A C9A C14A -10.0(2) . . . . ? 
C8A N1A C9A C10A -1.51(16) . . . . ? 
C15A N1A C9A C10A 173.33(13) . . . . ? 
C14A C9A C10A C11A -1.7(2) . . . . ? 
N1A C9A C10A C11A 175.14(12) . . . . ? 
C14A C9A C10A C7A 177.81(13) . . . . ? 
N1A C9A C10A C7A -5.32(15) . . . . ? 
O4A C7A C10A C11A -49.4(2) . . . . ? 
C8A C7A C10A C11A -171.51(14) . . . . ? 
C5A C7A C10A C11A 71.78(18) . . . . ? 
O4A C7A C10A C9A 131.09(12) . . . . ? 
C8A C7A C10A C9A 9.01(14) . . . . ? 
C5A C7A C10A C9A -107.70(13) . . . . ? 
C9A C10A C11A C12A 2.5(2) . . . . ? 
C7A C10A C11A C12A -176.88(14) . . . . ? 
C10A C11A C12A C13A -1.1(2) . . . . ? 
C11A C12A C13A C14A -1.3(2) . . . . ? 
C10A C9A C14A C13A -0.6(2) . . . . ? 
N1A C9A C14A C13A -176.87(14) . . . . ? 
C12A C13A C14A C9A 2.1(2) . . . . ? 
C8A N1A C15A C16A 114.99(16) . . . . ? 
C9A N1A C15A C16A -59.20(19) . . . . ? 
N1A C15A C16A C17A -62.18(19) . . . . ? 
C15A C16A C17A C18A 80.31(19) . . . . ? 
C4A O2A C18A C17A 164.40(13) . . . . ? 
C16A C17A C18A O2A -81.98(17) . . . . ? 
C5B S1B C1B O1B 176.42(14) . . . . ? 
C5B S1B C1B C2B -2.55(12) . . . . ? 
O1B C1B C2B C4B -176.46(16) . . . . ? 
S1B C1B C2B C4B 2.43(17) . . . . ? 
O1B C1B C2B C3B 2.4(2) . . . . ? 
S1B C1B C2B C3B -178.74(11) . . . . ? 
C18B O2B C4B C2B 21.5(2) . . . . ? 
C18B O2B C4B C5B -159.37(12) . . . . ? 
C1B C2B C4B O2B 178.08(14) . . . . ? 
C3B C2B C4B O2B -0.6(3) . . . . ? 
C1B C2B C4B C5B -0.94(19) . . . . ? 
C3B C2B C4B C5B -179.58(14) . . . . ? 
O2B C4B C5B C6B -62.15(15) . . . . ? 
C2B C4B C5B C6B 117.07(15) . . . . ? 
O2B C4B C5B C7B 64.17(14) . . . . ? 
C2B C4B C5B C7B -116.60(14) . . . . ? 
O2B C4B C5B S1B 179.86(9) . . . . ? 
C2B C4B C5B S1B -0.92(16) . . . . ? 
C1B S1B C5B C4B 1.90(10) . . . . ? 
C1B S1B C5B C6B -116.84(11) . . . . ? 
C1B S1B C5B C7B 119.09(10) . . . . ? 
C4B C5B C7B O4B 167.15(11) . . . . ? 
C6B C5B C7B O4B -68.24(15) . . . . ? 
S1B C5B C7B O4B 53.31(12) . . . . ? 
C4B C5B C7B C10B 41.10(15) . . . . ? 
C6B C5B C7B C10B 165.71(12) . . . . ? 
S1B C5B C7B C10B -72.74(12) . . . . ? 
C4B C5B C7B C8B -70.18(14) . . . . ? 
C6B C5B C7B C8B 54.43(15) . . . . ? 
S1B C5B C7B C8B 175.98(9) . . . . ? 
C9B N1B C8B O3B -171.61(13) . . . . ? 
C15B N1B C8B O3B 13.1(2) . . . . ? 
C9B N1B C8B C7B 7.36(15) . . . . ? 
C15B N1B C8B C7B -167.97(12) . . . . ? 
O4B C7B C8B O3B 46.16(19) . . . . ? 
C10B C7B C8B O3B 169.35(13) . . . . ? 
C5B C7B C8B O3B -72.97(17) . . . . ? 
O4B C7B C8B N1B -132.80(12) . . . . ? 
C10B C7B C8B N1B -9.61(14) . . . . ? 
C5B C7B C8B N1B 108.06(12) . . . . ? 
C8B N1B C9B C14B 175.87(14) . . . . ? 
C15B N1B C9B C14B -8.9(2) . . . . ? 
C8B N1B C9B C10B -1.66(16) . . . . ? 
C15B N1B C9B C10B 173.53(13) . . . . ? 
C14B C9B C10B C11B -2.5(2) . . . . ? 
N1B C9B C10B C11B 175.16(12) . . . . ? 
C14B C9B C10B C7B 177.37(13) . . . . ? 
N1B C9B C10B C7B -4.92(15) . . . . ? 
O4B C7B C10B C11B -49.7(2) . . . . ? 
C8B C7B C10B C11B -171.53(14) . . . . ? 
C5B C7B C10B C11B 71.99(18) . . . . ? 
O4B C7B C10B C9B 130.43(12) . . . . ? 
C8B C7B C10B C9B 8.57(14) . . . . ? 
C5B C7B C10B C9B -107.92(13) . . . . ? 
C9B C10B C11B C12B 2.2(2) . . . . ? 
C7B C10B C11B C12B -177.65(14) . . . . ? 
C10B C11B C12B C13B 0.1(2) . . . . ? 
C11B C12B C13B C14B -2.3(2) . . . . ? 
C10B C9B C14B C13B 0.4(2) . . . . ? 
N1B C9B C14B C13B -176.84(14) . . . . ? 
C12B C13B C14B C9B 2.0(2) . . . . ? 
C8B N1B C15B C16B 117.72(15) . . . . ? 
C9B N1B C15B C16B -56.91(19) . . . . ? 
N1B C15B C16B C17B -59.61(19) . . . . ? 
C15B C16B C17B C18B 77.2(2) . . . . ? 
C4B O2B C18B C17B 165.88(12) . . . . ? 
C16B C17B C18B O2B -86.30(17) . . . . ? 
 
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 
O4A H4A O3B  0.964(9) 1.824(11) 2.7641(14) 164.3(18) . 
O4B H4B O3A  0.960(9) 1.834(11) 2.7744(14) 165.7(19) . 
 
_diffrn_measured_fraction_theta_max    0.991 
_diffrn_reflns_theta_full              25.39 
_diffrn_measured_fraction_theta_full   0.991 
_refine_diff_density_max    0.270 
_refine_diff_density_min   -0.277 
_refine_diff_density_rms    0.040 

#===END

 
data_tetracycle_4b 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           '214-215oC'
_chemical_formula_moiety          'C19 H21 N O4 S'
_chemical_formula_sum 
 'C19 H21 N O4 S' 
_chemical_formula_weight          359.43 
 
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' 
 'O'  'O'   0.0106   0.0060 
 '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' 
 '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)/n
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    7.7577(2) 
_cell_length_b                    13.1299(5) 
_cell_length_c                    17.2540(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  100.819(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1726.22(10) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     213(2) 
_cell_measurement_reflns_used     7137 
_cell_measurement_theta_min       3.09
_cell_measurement_theta_max       26.72
 
_exptl_crystal_description        needle
_exptl_crystal_colour             light-yellow
_exptl_crystal_size_max           0.24 
_exptl_crystal_size_mid           0.22 
_exptl_crystal_size_min           0.21 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.383 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              760 
_exptl_absorpt_coefficient_mu     0.212 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9510 
_exptl_absorpt_correction_T_max   0.9569 
_exptl_absorpt_process_details    'SADABS (Sheldrick, 1990)' 
 
_exptl_special_details 
; 
Half sphere of data collected using COLLECT strategy (Nonius, 2000).
 Crystal to detector distance = 40mm; combination of φ and ω scans of
 1.2°, 60s per °, 2 iterations.  
; 
 
_diffrn_ambient_temperature       213(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   'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method        '1.2° φ scans and ω scans' 
_diffrn_reflns_number             7137 
_diffrn_reflns_av_R_equivalents   0.0274 
_diffrn_reflns_av_sigmaI/netI     0.0425 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -16 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -21 
_diffrn_reflns_limit_l_max        21 
_diffrn_reflns_theta_min          3.09 
_diffrn_reflns_theta_max          26.72 
_reflns_number_total              3654 
_reflns_number_gt                 2819 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection     'COLLECT program (Nonius, 2000)'
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction      'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution  'SHELXS-97 (Sheldrick, 1997)' 
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics   'X-Seed (Barbour, 2001)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 2001)'  
 
_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+0.3587P] 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        0.0027(8) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3654 
_refine_ls_number_parameters      233 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0532 
_refine_ls_R_factor_gt            0.0337 
_refine_ls_wR_factor_ref          0.0845 
_refine_ls_wR_factor_gt           0.0782 
_refine_ls_goodness_of_fit_ref    1.047 
_refine_ls_restrained_S_all       1.048 
_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 0.43980(5) 0.48959(3) 0.24583(2) 0.03479(14) Uani 1 1 d . . . 
O1 O 0.31061(15) 0.54045(9) 0.37046(6) 0.0409(3) Uani 1 1 d . . . 
N1 N 0.42486(15) 0.76218(9) 0.04491(7) 0.0256(3) Uani 1 1 d . . . 
C1 C 0.30267(19) 0.55560(11) 0.30024(9) 0.0297(3) Uani 1 1 d . . . 
O2 O 0.11549(13) 0.66783(7) 0.10988(6) 0.0300(2) Uani 1 1 d . . . 
C2 C 0.18548(18) 0.62702(11) 0.25110(8) 0.0271(3) Uani 1 1 d . . . 
O3 O 0.38384(14) 0.61037(8) -0.02092(6) 0.0354(3) Uani 1 1 d . . . 
C3 C 0.0692(2) 0.69033(14) 0.29237(10) 0.0444(4) Uani 1 1 d . . . 
H3A H 0.0776 0.7613 0.2778 0.067 Uiso 1 1 calc R . . 
H3B H 0.1062 0.6831 0.3490 0.067 Uiso 1 1 calc R . . 
H3C H -0.0513 0.6675 0.2770 0.067 Uiso 1 1 calc R . . 
O4 O 0.63800(13) 0.55395(8) 0.12298(6) 0.0315(3) Uani 1 1 d D . . 
C4 C 0.20192(17) 0.62153(10) 0.17523(8) 0.0242(3) Uani 1 1 d . . . 
H4 H 0.612(3) 0.5055(12) 0.0811(8) 0.063(6) Uiso 1 1 d D . . 
C5 C 0.34039(18) 0.55099(10) 0.15350(8) 0.0263(3) Uani 1 1 d . . . 
C6 C 0.2551(2) 0.46903(12) 0.09467(10) 0.0380(4) Uani 1 1 d . . . 
H6A H 0.1720 0.4298 0.1180 0.057 Uiso 1 1 calc R . . 
H6B H 0.3453 0.4241 0.0821 0.057 Uiso 1 1 calc R . . 
H6C H 0.1944 0.5016 0.0468 0.057 Uiso 1 1 calc R . . 
C7 C 0.48743(17) 0.61486(10) 0.12394(8) 0.0244(3) Uani 1 1 d . . . 
C8 C 0.42286(18) 0.65915(11) 0.04024(8) 0.0256(3) Uani 1 1 d . . . 
C9 C 0.49358(17) 0.79465(10) 0.12275(8) 0.0236(3) Uani 1 1 d . . . 
C10 C 0.53672(16) 0.71065(10) 0.17161(8) 0.0222(3) Uani 1 1 d . . . 
C11 C 0.61173(18) 0.72595(11) 0.25018(8) 0.0278(3) Uani 1 1 d . . . 
H11 H 0.6418 0.6702 0.2842 0.033 Uiso 1 1 calc R . . 
C12 C 0.64196(19) 0.82503(12) 0.27806(9) 0.0328(4) Uani 1 1 d . . . 
H12 H 0.6930 0.8361 0.3312 0.039 Uiso 1 1 calc R . . 
C13 C 0.59779(19) 0.90705(11) 0.22854(9) 0.0336(4) Uani 1 1 d . . . 
H13 H 0.6190 0.9734 0.2485 0.040 Uiso 1 1 calc R . . 
C14 C 0.52231(18) 0.89337(11) 0.14946(9) 0.0302(3) Uani 1 1 d . . . 
H14 H 0.4921 0.9492 0.1156 0.036 Uiso 1 1 calc R . . 
C15 C 0.3612(2) 0.83003(11) -0.02138(9) 0.0335(4) Uani 1 1 d . . . 
H15A H 0.3621 0.7937 -0.0709 0.040 Uiso 1 1 calc R . . 
H15B H 0.4404 0.8885 -0.0191 0.040 Uiso 1 1 calc R . . 
C16 C 0.1761(2) 0.86788(12) -0.02043(9) 0.0378(4) Uani 1 1 d . . . 
H16A H 0.1435 0.9181 -0.0626 0.045 Uiso 1 1 calc R . . 
H16B H 0.1751 0.9022 0.0299 0.045 Uiso 1 1 calc R . . 
C17 C 0.0382(2) 0.78245(12) -0.03136(9) 0.0363(4) Uani 1 1 d . . . 
H17A H -0.0350 0.7891 -0.0840 0.044 Uiso 1 1 calc R . . 
H17B H 0.0991 0.7169 -0.0295 0.044 Uiso 1 1 calc R . . 
C18 C -0.0811(2) 0.78085(13) 0.02938(10) 0.0422(4) Uani 1 1 d . . . 
H18A H -0.1396 0.8471 0.0286 0.051 Uiso 1 1 calc R . . 
H18B H -0.1722 0.7293 0.0136 0.051 Uiso 1 1 calc R . . 
C19 C 0.0107(2) 0.75867(12) 0.11311(9) 0.0390(4) Uani 1 1 d . . . 
H19A H 0.0858 0.8160 0.1343 0.047 Uiso 1 1 calc R . . 
H19B H -0.0755 0.7473 0.1471 0.047 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 C1 1.7716(16) . ? 
S1 C5 1.8225(14) . ? 
O1 C1 1.2180(17) . ? 
N1 C8 1.3551(18) . ? 
N1 C9 1.4146(17) . ? 
N1 C15 1.4607(18) . ? 
C1 C2 1.461(2) . ? 
O2 C4 1.3441(16) . ? 
O2 C19 1.4503(17) . ? 
C2 C4 1.341(2) . ? 
C2 C3 1.501(2) . ? 
O3 C8 1.2228(16) . ? 
C3 H3A 0.9700 . ? 
C3 H3B 0.9700 . ? 
C3 H3C 0.9700 . ? 
O4 C7 1.4184(16) . ? 
O4 H4 0.955(9) . ? 
C4 C5 1.5177(19) . ? 
C5 C6 1.541(2) . ? 
C5 C7 1.576(2) . ? 
C6 H6A 0.9700 . ? 
C6 H6B 0.9700 . ? 
C6 H6C 0.9700 . ? 
C7 C10 1.5121(19) . ? 
C7 C8 1.5502(19) . ? 
C9 C14 1.380(2) . ? 
C9 C10 1.3903(19) . ? 
C10 C11 1.3859(19) . ? 
C11 C12 1.391(2) . ? 
C11 H11 0.9400 . ? 
C12 C13 1.377(2) . ? 
C12 H12 0.9400 . ? 
C13 C14 1.392(2) . ? 
C13 H13 0.9400 . ? 
C14 H14 0.9400 . ? 
C15 C16 1.523(2) . ? 
C15 H15A 0.9800 . ? 
C15 H15B 0.9800 . ? 
C16 C17 1.537(2) . ? 
C16 H16A 0.9800 . ? 
C16 H16B 0.9800 . ? 
C17 C18 1.523(2) . ? 
C17 H17A 0.9800 . ? 
C17 H17B 0.9800 . ? 
C18 C19 1.514(2) . ? 
C18 H18A 0.9800 . ? 
C18 H18B 0.9800 . ? 
C19 H19A 0.9800 . ? 
C19 H19B 0.9800 . ? 
 
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 
C1 S1 C5 92.81(7) . . ? 
C8 N1 C9 110.81(11) . . ? 
C8 N1 C15 124.32(12) . . ? 
C9 N1 C15 124.85(12) . . ? 
O1 C1 C2 126.28(14) . . ? 
O1 C1 S1 121.59(12) . . ? 
C2 C1 S1 112.12(11) . . ? 
C4 O2 C19 122.32(11) . . ? 
C4 C2 C1 111.66(13) . . ? 
C4 C2 C3 131.98(14) . . ? 
C1 C2 C3 116.36(13) . . ? 
C2 C3 H3A 109.5 . . ? 
C2 C3 H3B 109.5 . . ? 
H3A C3 H3B 109.5 . . ? 
C2 C3 H3C 109.5 . . ? 
H3A C3 H3C 109.5 . . ? 
H3B C3 H3C 109.5 . . ? 
C7 O4 H4 109.1(12) . . ? 
C2 C4 O2 132.12(13) . . ? 
C2 C4 C5 118.39(12) . . ? 
O2 C4 C5 109.49(11) . . ? 
C4 C5 C6 110.65(11) . . ? 
C4 C5 C7 110.13(11) . . ? 
C6 C5 C7 113.94(12) . . ? 
C4 C5 S1 104.89(10) . . ? 
C6 C5 S1 109.02(10) . . ? 
C7 C5 S1 107.76(9) . . ? 
C5 C6 H6A 109.5 . . ? 
C5 C6 H6B 109.5 . . ? 
H6A C6 H6B 109.5 . . ? 
C5 C6 H6C 109.5 . . ? 
H6A C6 H6C 109.5 . . ? 
H6B C6 H6C 109.5 . . ? 
O4 C7 C10 110.53(11) . . ? 
O4 C7 C8 108.87(11) . . ? 
C10 C7 C8 101.49(11) . . ? 
O4 C7 C5 110.58(10) . . ? 
C10 C7 C5 113.03(11) . . ? 
C8 C7 C5 111.98(11) . . ? 
O3 C8 N1 124.91(13) . . ? 
O3 C8 C7 126.29(13) . . ? 
N1 C8 C7 108.72(11) . . ? 
C14 C9 C10 122.50(13) . . ? 
C14 C9 N1 127.49(13) . . ? 
C10 C9 N1 109.97(12) . . ? 
C11 C10 C9 119.16(12) . . ? 
C11 C10 C7 132.03(12) . . ? 
C9 C10 C7 108.81(11) . . ? 
C10 C11 C12 119.09(13) . . ? 
C10 C11 H11 120.5 . . ? 
C12 C11 H11 120.5 . . ? 
C13 C12 C11 120.69(14) . . ? 
C13 C12 H12 119.7 . . ? 
C11 C12 H12 119.7 . . ? 
C12 C13 C14 121.14(14) . . ? 
C12 C13 H13 119.4 . . ? 
C14 C13 H13 119.4 . . ? 
C9 C14 C13 117.42(13) . . ? 
C9 C14 H14 121.3 . . ? 
C13 C14 H14 121.3 . . ? 
N1 C15 C16 111.82(12) . . ? 
N1 C15 H15A 109.3 . . ? 
C16 C15 H15A 109.3 . . ? 
N1 C15 H15B 109.3 . . ? 
C16 C15 H15B 109.3 . . ? 
H15A C15 H15B 107.9 . . ? 
C15 C16 C17 113.36(12) . . ? 
C15 C16 H16A 108.9 . . ? 
C17 C16 H16A 108.9 . . ? 
C15 C16 H16B 108.9 . . ? 
C17 C16 H16B 108.9 . . ? 
H16A C16 H16B 107.7 . . ? 
C18 C17 C16 115.11(14) . . ? 
C18 C17 H17A 108.5 . . ? 
C16 C17 H17A 108.5 . . ? 
C18 C17 H17B 108.5 . . ? 
C16 C17 H17B 108.5 . . ? 
H17A C17 H17B 107.5 . . ? 
C19 C18 C17 114.93(13) . . ? 
C19 C18 H18A 108.5 . . ? 
C17 C18 H18A 108.5 . . ? 
C19 C18 H18B 108.5 . . ? 
C17 C18 H18B 108.5 . . ? 
H18A C18 H18B 107.5 . . ? 
O2 C19 C18 106.75(12) . . ? 
O2 C19 H19A 110.4 . . ? 
C18 C19 H19A 110.4 . . ? 
O2 C19 H19B 110.4 . . ? 
C18 C19 H19B 110.4 . . ? 
H19A C19 H19B 108.6 . . ? 
 
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 
C5 S1 C1 O1 177.98(12) . . . . ? 
C5 S1 C1 C2 -2.12(10) . . . . ? 
O1 C1 C2 C4 -176.43(14) . . . . ? 
S1 C1 C2 C4 3.68(15) . . . . ? 
O1 C1 C2 C3 2.5(2) . . . . ? 
S1 C1 C2 C3 -177.36(11) . . . . ? 
C1 C2 C4 O2 175.79(13) . . . . ? 
C3 C2 C4 O2 -3.0(3) . . . . ? 
C1 C2 C4 C5 -3.75(18) . . . . ? 
C3 C2 C4 C5 177.50(15) . . . . ? 
C19 O2 C4 C2 17.7(2) . . . . ? 
C19 O2 C4 C5 -162.74(12) . . . . ? 
C2 C4 C5 C6 119.50(14) . . . . ? 
O2 C4 C5 C6 -60.13(15) . . . . ? 
C2 C4 C5 C7 -113.63(14) . . . . ? 
O2 C4 C5 C7 66.74(14) . . . . ? 
C2 C4 C5 S1 2.08(15) . . . . ? 
O2 C4 C5 S1 -177.56(9) . . . . ? 
C1 S1 C5 C4 0.18(9) . . . . ? 
C1 S1 C5 C6 -118.36(11) . . . . ? 
C1 S1 C5 C7 117.51(9) . . . . ? 
C4 C5 C7 O4 164.91(11) . . . . ? 
C6 C5 C7 O4 -70.08(15) . . . . ? 
S1 C5 C7 O4 51.03(13) . . . . ? 
C4 C5 C7 C10 40.40(15) . . . . ? 
C6 C5 C7 C10 165.41(12) . . . . ? 
S1 C5 C7 C10 -73.48(12) . . . . ? 
C4 C5 C7 C8 -73.49(14) . . . . ? 
C6 C5 C7 C8 51.52(15) . . . . ? 
S1 C5 C7 C8 172.63(9) . . . . ? 
C9 N1 C8 O3 -173.71(13) . . . . ? 
C15 N1 C8 O3 7.4(2) . . . . ? 
C9 N1 C8 C7 3.26(15) . . . . ? 
C15 N1 C8 C7 -175.61(12) . . . . ? 
O4 C7 C8 O3 56.07(18) . . . . ? 
C10 C7 C8 O3 172.66(13) . . . . ? 
C5 C7 C8 O3 -66.51(17) . . . . ? 
O4 C7 C8 N1 -120.85(12) . . . . ? 
C10 C7 C8 N1 -4.26(14) . . . . ? 
C5 C7 C8 N1 116.57(12) . . . . ? 
C8 N1 C9 C14 177.22(14) . . . . ? 
C15 N1 C9 C14 -3.9(2) . . . . ? 
C8 N1 C9 C10 -0.73(15) . . . . ? 
C15 N1 C9 C10 178.13(12) . . . . ? 
C14 C9 C10 C11 -0.1(2) . . . . ? 
N1 C9 C10 C11 177.98(11) . . . . ? 
C14 C9 C10 C7 179.74(12) . . . . ? 
N1 C9 C10 C7 -2.19(15) . . . . ? 
O4 C7 C10 C11 -61.02(19) . . . . ? 
C8 C7 C10 C11 -176.39(14) . . . . ? 
C5 C7 C10 C11 63.52(18) . . . . ? 
O4 C7 C10 C9 119.18(12) . . . . ? 
C8 C7 C10 C9 3.80(14) . . . . ? 
C5 C7 C10 C9 -116.28(12) . . . . ? 
C9 C10 C11 C12 0.0(2) . . . . ? 
C7 C10 C11 C12 -179.83(14) . . . . ? 
C10 C11 C12 C13 0.2(2) . . . . ? 
C11 C12 C13 C14 -0.1(2) . . . . ? 
C10 C9 C14 C13 0.1(2) . . . . ? 
N1 C9 C14 C13 -177.61(13) . . . . ? 
C12 C13 C14 C9 0.0(2) . . . . ? 
C8 N1 C15 C16 98.75(16) . . . . ? 
C9 N1 C15 C16 -79.96(16) . . . . ? 
N1 C15 C16 C17 -64.19(17) . . . . ? 
C15 C16 C17 C18 129.68(14) . . . . ? 
C16 C17 C18 C19 -64.97(18) . . . . ? 
C4 O2 C19 C18 -173.80(12) . . . . ? 
C17 C18 C19 O2 -50.37(19) . . . . ? 
 
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 
O4 H4 O3  0.955(9) 1.846(11) 2.7700(14) 162.0(17) 3_665 
 
_diffrn_measured_fraction_theta_max    0.997 
_diffrn_reflns_theta_full              26.72 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.216 
_refine_diff_density_min   -0.304 
_refine_diff_density_rms    0.052 

#===END

 
data_tetracycle_4c
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           '198oC' 
_chemical_formula_moiety          'C20 H23 N O4 S' 
_chemical_formula_sum 
 'C20 H23 N O4 S' 
_chemical_formula_weight          373.45 
 
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)/n
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    7.9966(3) 
_cell_length_b                    13.1259(4) 
_cell_length_c                    17.3410(7) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  97.644(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1803.98(11) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     6705
_cell_measurement_theta_min       2.68
_cell_measurement_theta_max       25.69
 
_exptl_crystal_description        needle
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.33 
_exptl_crystal_size_mid           0.26 
_exptl_crystal_size_min           0.22 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.375 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              792 
_exptl_absorpt_coefficient_mu     0.205 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9353 
_exptl_absorpt_correction_T_max   0.9492 
_exptl_absorpt_process_details    'SADABS (Sheldrick, 1990)' 
 
_exptl_special_details 
; 
Half sphere of data collected using COLLECT strategy (Nonius, 2000).
 Crystal to detector distance = 40mm; combination of φ and ω scans of
 1.2°, 60s per °, 2 iterations.  
; 
 
_diffrn_ambient_temperature       173(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   'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method        '1.2° φ scans and ω scans' 
_diffrn_reflns_number             6705 
_diffrn_reflns_av_R_equivalents   0.0330 
_diffrn_reflns_av_sigmaI/netI     0.0495 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -21 
_diffrn_reflns_limit_l_max        21 
_diffrn_reflns_theta_min          2.68 
_diffrn_reflns_theta_max          25.69 
_reflns_number_total              3432 
_reflns_number_gt                 2362 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection     'COLLECT program (Nonius, 2000)'
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction      'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution  'SHELXS-97 (Sheldrick, 1997)' 
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics   'X-Seed (Barbour, 2001)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 2001)'  
 
_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)+(0.0532P)²+0.4335P] 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        none 
_refine_ls_number_reflns          3432 
_refine_ls_number_parameters      239 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0723 
_refine_ls_R_factor_gt            0.0411 
_refine_ls_wR_factor_ref          0.1089 
_refine_ls_wR_factor_gt           0.0974 
_refine_ls_goodness_of_fit_ref    1.043 
_refine_ls_restrained_S_all       1.044 
_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 0.92649(7) 0.49723(4) 0.26202(3) 0.02971(18) Uani 1 1 d . . . 
O1 O 0.7861(2) 0.56172(12) 0.38254(8) 0.0372(4) Uani 1 1 d . . . 
N1 N 0.9313(2) 0.75483(12) 0.04992(9) 0.0219(4) Uani 1 1 d . . . 
C1 C 0.7844(3) 0.56751(16) 0.31237(12) 0.0269(5) Uani 1 1 d . . . 
O2 O 0.61365(17) 0.65571(11) 0.11872(8) 0.0253(4) Uani 1 1 d . . . 
C2 C 0.6702(3) 0.63049(15) 0.25978(12) 0.0236(5) Uani 1 1 d . . . 
O3 O 0.88141(19) 0.59873(11) -0.00861(8) 0.0291(4) Uani 1 1 d . . . 
C3 C 0.5509(3) 0.69728(19) 0.29715(13) 0.0360(6) Uani 1 1 d . . . 
H3A H 0.5686 0.6869 0.3536 0.054 Uiso 1 1 calc R . . 
H3B H 0.4344 0.6796 0.2767 0.054 Uiso 1 1 calc R . . 
H3C H 0.5720 0.7688 0.2855 0.054 Uiso 1 1 calc R . . 
O4 O 1.12126(18) 0.54774(11) 0.12998(8) 0.0268(4) Uani 1 1 d D . . 
C4 C 0.6948(3) 0.61765(15) 0.18537(11) 0.0205(5) Uani 1 1 d . . . 
H4 H 1.098(4) 0.4998(16) 0.0880(11) 0.064(9) Uiso 1 1 d D . . 
C5 C 0.8368(3) 0.54883(15) 0.16740(11) 0.0220(5) Uani 1 1 d . . . 
C6 C 0.7674(3) 0.46045(16) 0.11451(13) 0.0305(5) Uani 1 1 d . . . 
H6A H 0.8609 0.4170 0.1033 0.046 Uiso 1 1 calc R . . 
H6B H 0.7084 0.4877 0.0657 0.046 Uiso 1 1 calc R . . 
H6C H 0.6886 0.4202 0.1408 0.046 Uiso 1 1 calc R . . 
C7 C 0.9776(3) 0.61112(15) 0.13305(12) 0.0214(5) Uani 1 1 d . . . 
C8 C 0.9199(3) 0.65136(16) 0.04923(11) 0.0218(5) Uani 1 1 d . . . 
C9 C 0.9987(2) 0.79055(16) 0.12457(11) 0.0211(5) Uani 1 1 d . . . 
C10 C 1.0289(2) 0.70898(15) 0.17605(12) 0.0200(5) Uani 1 1 d . . . 
C11 C 1.0991(3) 0.72766(17) 0.25225(12) 0.0263(5) Uani 1 1 d . . . 
H11 H 1.1207 0.6732 0.2883 0.032 Uiso 1 1 calc R . . 
C12 C 1.1376(3) 0.82771(17) 0.27511(12) 0.0290(5) Uani 1 1 d . . . 
H12 H 1.1851 0.8413 0.3272 0.035 Uiso 1 1 calc R . . 
C13 C 1.1075(3) 0.90716(17) 0.22308(13) 0.0309(5) Uani 1 1 d . . . 
H13 H 1.1355 0.9747 0.2398 0.037 Uiso 1 1 calc R . . 
C14 C 1.0367(3) 0.88993(16) 0.14629(13) 0.0274(5) Uani 1 1 d . . . 
H14 H 1.0155 0.9445 0.1103 0.033 Uiso 1 1 calc R . . 
C15 C 0.9020(3) 0.81626(17) -0.02120(12) 0.0283(5) Uani 1 1 d . . . 
H15A H 0.8742 0.7700 -0.0661 0.034 Uiso 1 1 calc R . . 
H15B H 1.0079 0.8520 -0.0281 0.034 Uiso 1 1 calc R . . 
C16 C 0.7604(3) 0.89552(17) -0.02229(12) 0.0297(5) Uani 1 1 d . . . 
H16A H 0.8081 0.9583 0.0036 0.036 Uiso 1 1 calc R . . 
H16B H 0.7190 0.9129 -0.0771 0.036 Uiso 1 1 calc R . . 
C17 C 0.6118(3) 0.86146(16) 0.01717(12) 0.0290(5) Uani 1 1 d . . . 
H17A H 0.5290 0.9179 0.0142 0.035 Uiso 1 1 calc R . . 
H17B H 0.6521 0.8493 0.0729 0.035 Uiso 1 1 calc R . . 
C18 C 0.5212(3) 0.76584(17) -0.01622(12) 0.0281(5) Uani 1 1 d . . . 
H18A H 0.6051 0.7111 -0.0195 0.034 Uiso 1 1 calc R . . 
H18B H 0.4659 0.7803 -0.0696 0.034 Uiso 1 1 calc R . . 
C19 C 0.3889(3) 0.72898(18) 0.03313(13) 0.0309(5) Uani 1 1 d . . . 
H19A H 0.2964 0.7796 0.0299 0.037 Uiso 1 1 calc R . . 
H19B H 0.3404 0.6641 0.0113 0.037 Uiso 1 1 calc R . . 
C20 C 0.4579(3) 0.71267(17) 0.11773(12) 0.0272(5) Uani 1 1 d . . . 
H20A H 0.4799 0.7789 0.1444 0.033 Uiso 1 1 calc R . . 
H20B H 0.3762 0.6740 0.1445 0.033 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 C1 1.780(2) . ? 
S1 C5 1.831(2) . ? 
O1 C1 1.218(3) . ? 
N1 C8 1.361(3) . ? 
N1 C9 1.414(2) . ? 
N1 C15 1.466(3) . ? 
C1 C2 1.458(3) . ? 
O2 C4 1.344(2) . ? 
O2 C20 1.451(2) . ? 
C2 C4 1.341(3) . ? 
C2 C3 1.504(3) . ? 
O3 C8 1.223(2) . ? 
C3 H3A 0.9800 . ? 
C3 H3B 0.9800 . ? 
C3 H3C 0.9800 . ? 
O4 C7 1.425(2) . ? 
O4 H4 0.961(10) . ? 
C4 C5 1.515(3) . ? 
C5 C6 1.536(3) . ? 
C5 C7 1.572(3) . ? 
C6 H6A 0.9800 . ? 
C6 H6B 0.9800 . ? 
C6 H6C 0.9800 . ? 
C7 C10 1.514(3) . ? 
C7 C8 1.558(3) . ? 
C9 C14 1.380(3) . ? 
C9 C10 1.395(3) . ? 
C10 C11 1.387(3) . ? 
C11 C12 1.394(3) . ? 
C11 H11 0.9500 . ? 
C12 C13 1.379(3) . ? 
C12 H12 0.9500 . ? 
C13 C14 1.394(3) . ? 
C13 H13 0.9500 . ? 
C14 H14 0.9500 . ? 
C15 C16 1.536(3) . ? 
C15 H15A 0.9900 . ? 
C15 H15B 0.9900 . ? 
C16 C17 1.515(3) . ? 
C16 H16A 0.9900 . ? 
C16 H16B 0.9900 . ? 
C17 C18 1.524(3) . ? 
C17 H17A 0.9900 . ? 
C17 H17B 0.9900 . ? 
C18 C19 1.526(3) . ? 
C18 H18A 0.9900 . ? 
C18 H18B 0.9900 . ? 
C19 C20 1.512(3) . ? 
C19 H19A 0.9900 . ? 
C19 H19B 0.9900 . ? 
C20 H20A 0.9900 . ? 
C20 H20B 0.9900 . ? 
 
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 
C1 S1 C5 92.77(9) . . ? 
C8 N1 C9 110.84(16) . . ? 
C8 N1 C15 122.57(17) . . ? 
C9 N1 C15 125.91(17) . . ? 
O1 C1 C2 125.7(2) . . ? 
O1 C1 S1 122.34(18) . . ? 
C2 C1 S1 111.99(16) . . ? 
C4 O2 C20 121.14(16) . . ? 
C4 C2 C1 111.76(19) . . ? 
C4 C2 C3 132.1(2) . . ? 
C1 C2 C3 116.18(18) . . ? 
C2 C3 H3A 109.5 . . ? 
C2 C3 H3B 109.5 . . ? 
H3A C3 H3B 109.5 . . ? 
C2 C3 H3C 109.5 . . ? 
H3A C3 H3C 109.5 . . ? 
H3B C3 H3C 109.5 . . ? 
C7 O4 H4 109.7(17) . . ? 
C2 C4 O2 131.67(19) . . ? 
C2 C4 C5 118.82(18) . . ? 
O2 C4 C5 109.50(16) . . ? 
C4 C5 C6 110.61(17) . . ? 
C4 C5 C7 111.24(16) . . ? 
C6 C5 C7 112.75(17) . . ? 
C4 C5 S1 104.55(13) . . ? 
C6 C5 S1 108.84(14) . . ? 
C7 C5 S1 108.48(13) . . ? 
C5 C6 H6A 109.5 . . ? 
C5 C6 H6B 109.5 . . ? 
H6A C6 H6B 109.5 . . ? 
C5 C6 H6C 109.5 . . ? 
H6A C6 H6C 109.5 . . ? 
H6B C6 H6C 109.5 . . ? 
O4 C7 C10 110.30(16) . . ? 
O4 C7 C8 107.67(16) . . ? 
C10 C7 C8 101.49(16) . . ? 
O4 C7 C5 109.41(16) . . ? 
C10 C7 C5 114.53(17) . . ? 
C8 C7 C5 113.05(16) . . ? 
O3 C8 N1 125.46(18) . . ? 
O3 C8 C7 125.78(19) . . ? 
N1 C8 C7 108.60(16) . . ? 
C14 C9 C10 122.52(19) . . ? 
C14 C9 N1 127.33(19) . . ? 
C10 C9 N1 110.12(17) . . ? 
C11 C10 C9 119.20(19) . . ? 
C11 C10 C7 131.91(19) . . ? 
C9 C10 C7 108.87(17) . . ? 
C10 C11 C12 118.9(2) . . ? 
C10 C11 H11 120.5 . . ? 
C12 C11 H11 120.5 . . ? 
C13 C12 C11 120.91(19) . . ? 
C13 C12 H12 119.5 . . ? 
C11 C12 H12 119.5 . . ? 
C12 C13 C14 121.0(2) . . ? 
C12 C13 H13 119.5 . . ? 
C14 C13 H13 119.5 . . ? 
C9 C14 C13 117.43(19) . . ? 
C9 C14 H14 121.3 . . ? 
C13 C14 H14 121.3 . . ? 
N1 C15 C16 114.73(17) . . ? 
N1 C15 H15A 108.6 . . ? 
C16 C15 H15A 108.6 . . ? 
N1 C15 H15B 108.6 . . ? 
C16 C15 H15B 108.6 . . ? 
H15A C15 H15B 107.6 . . ? 
C17 C16 C15 114.55(18) . . ? 
C17 C16 H16A 108.6 . . ? 
C15 C16 H16A 108.6 . . ? 
C17 C16 H16B 108.6 . . ? 
C15 C16 H16B 108.6 . . ? 
H16A C16 H16B 107.6 . . ? 
C16 C17 C18 115.66(19) . . ? 
C16 C17 H17A 108.4 . . ? 
C18 C17 H17A 108.4 . . ? 
C16 C17 H17B 108.4 . . ? 
C18 C17 H17B 108.4 . . ? 
H17A C17 H17B 107.4 . . ? 
C17 C18 C19 112.23(18) . . ? 
C17 C18 H18A 109.2 . . ? 
C19 C18 H18A 109.2 . . ? 
C17 C18 H18B 109.2 . . ? 
C19 C18 H18B 109.2 . . ? 
H18A C18 H18B 107.9 . . ? 
C20 C19 C18 113.45(18) . . ? 
C20 C19 H19A 108.9 . . ? 
C18 C19 H19A 108.9 . . ? 
C20 C19 H19B 108.9 . . ? 
C18 C19 H19B 108.9 . . ? 
H19A C19 H19B 107.7 . . ? 
O2 C20 C19 106.64(17) . . ? 
O2 C20 H20A 110.4 . . ? 
C19 C20 H20A 110.4 . . ? 
O2 C20 H20B 110.4 . . ? 
C19 C20 H20B 110.4 . . ? 
H20A C20 H20B 108.6 . . ? 
 
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 
C5 S1 C1 O1 179.51(19) . . . . ? 
C5 S1 C1 C2 -0.50(16) . . . . ? 
O1 C1 C2 C4 -177.6(2) . . . . ? 
S1 C1 C2 C4 2.4(2) . . . . ? 
O1 C1 C2 C3 3.1(3) . . . . ? 
S1 C1 C2 C3 -176.88(16) . . . . ? 
C1 C2 C4 O2 176.2(2) . . . . ? 
C3 C2 C4 O2 -4.7(4) . . . . ? 
C1 C2 C4 C5 -3.7(3) . . . . ? 
C3 C2 C4 C5 175.4(2) . . . . ? 
C20 O2 C4 C2 -8.5(3) . . . . ? 
C20 O2 C4 C5 171.36(17) . . . . ? 
C2 C4 C5 C6 120.2(2) . . . . ? 
O2 C4 C5 C6 -59.7(2) . . . . ? 
C2 C4 C5 C7 -113.7(2) . . . . ? 
O2 C4 C5 C7 66.4(2) . . . . ? 
C2 C4 C5 S1 3.2(2) . . . . ? 
O2 C4 C5 S1 -176.73(13) . . . . ? 
C1 S1 C5 C4 -1.27(14) . . . . ? 
C1 S1 C5 C6 -119.49(15) . . . . ? 
C1 S1 C5 C7 117.50(14) . . . . ? 
C4 C5 C7 O4 169.74(15) . . . . ? 
C6 C5 C7 O4 -65.3(2) . . . . ? 
S1 C5 C7 O4 55.28(18) . . . . ? 
C4 C5 C7 C10 45.3(2) . . . . ? 
C6 C5 C7 C10 170.24(17) . . . . ? 
S1 C5 C7 C10 -69.14(18) . . . . ? 
C4 C5 C7 C8 -70.3(2) . . . . ? 
C6 C5 C7 C8 54.6(2) . . . . ? 
S1 C5 C7 C8 175.26(14) . . . . ? 
C9 N1 C8 O3 -172.73(19) . . . . ? 
C15 N1 C8 O3 -1.6(3) . . . . ? 
C9 N1 C8 C7 2.8(2) . . . . ? 
C15 N1 C8 C7 173.93(17) . . . . ? 
O4 C7 C8 O3 56.9(3) . . . . ? 
C10 C7 C8 O3 172.79(19) . . . . ? 
C5 C7 C8 O3 -64.1(3) . . . . ? 
O4 C7 C8 N1 -118.60(18) . . . . ? 
C10 C7 C8 N1 -2.7(2) . . . . ? 
C5 C7 C8 N1 120.43(18) . . . . ? 
C8 N1 C9 C14 176.3(2) . . . . ? 
C15 N1 C9 C14 5.6(3) . . . . ? 
C8 N1 C9 C10 -1.7(2) . . . . ? 
C15 N1 C9 C10 -172.46(18) . . . . ? 
C14 C9 C10 C11 0.3(3) . . . . ? 
N1 C9 C10 C11 178.45(18) . . . . ? 
C14 C9 C10 C7 -178.35(19) . . . . ? 
N1 C9 C10 C7 -0.2(2) . . . . ? 
O4 C7 C10 C11 -62.8(3) . . . . ? 
C8 C7 C10 C11 -176.7(2) . . . . ? 
C5 C7 C10 C11 61.2(3) . . . . ? 
O4 C7 C10 C9 115.64(18) . . . . ? 
C8 C7 C10 C9 1.7(2) . . . . ? 
C5 C7 C10 C9 -120.42(19) . . . . ? 
C9 C10 C11 C12 0.0(3) . . . . ? 
C7 C10 C11 C12 178.3(2) . . . . ? 
C10 C11 C12 C13 -0.4(3) . . . . ? 
C11 C12 C13 C14 0.5(3) . . . . ? 
C10 C9 C14 C13 -0.2(3) . . . . ? 
N1 C9 C14 C13 -178.0(2) . . . . ? 
C12 C13 C14 C9 -0.2(3) . . . . ? 
C8 N1 C15 C16 121.7(2) . . . . ? 
C9 N1 C15 C16 -68.6(3) . . . . ? 
N1 C15 C16 C17 -36.0(3) . . . . ? 
C15 C16 C17 C18 -59.1(2) . . . . ? 
C16 C17 C18 C19 172.47(18) . . . . ? 
C17 C18 C19 C20 -54.2(3) . . . . ? 
C4 O2 C20 C19 -171.33(17) . . . . ? 
C18 C19 C20 O2 -46.7(2) . . . . ? 
 
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 
O4 H4 O3  0.961(10) 1.912(13) 2.849(2) 164(3) 3_765 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              25.69 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.366 
_refine_diff_density_min   -0.376 
_refine_diff_density_rms    0.054 

#===END

