# Supplementary Material (ESI) for Chemical Communications

# This journal is © The Royal Society of Chemistry 2002



data_global



_journal_coden_Cambridge      182



loop_

_publ_author_name

'Suk-Ku Kang'

'Seok-Keun Yoon'



_publ_contact_author_name     	'Prof Suk-Ku Kang'  

_publ_contact_author_address 

;

Department of Chemistry

Sungkyunkwan University

Chunchun-dong, Jangan-gu

Suwon

440-746

SOUTH KOREA

;



_publ_contact_author_email SKKANG@CHEM.SKKU.AC.KR



_publ_requested_journal       'Chemical Communications'





_publ_section_title		

;

cis-Stereoselective Nickel-Catalyzed

Cyclization/Alkylation and Arylation Reactions of Allenyl-Aldehydes and

-Ketones with Organozinc Reagents

;



data_ph 

_database_code_CSD                  188814



_audit_creation_method            SHELXL-97 

_chemical_name_systematic 

; 

? 

; 

_chemical_name_common             ? 

_chemical_melting_point           ? 

_chemical_formula_moiety          ? 

_chemical_formula_sum 

'C38 H42 N2 O6 S2' 

_chemical_formula_weight          686.86 



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                    12.136(2) 

_cell_length_b                    12.7389(17) 

_cell_length_c                    13.752(2) 

_cell_angle_alpha                 65.951(12) 

_cell_angle_beta                  81.600(14) 

_cell_angle_gamma                 65.106(9) 

_cell_volume                      1760.2(5) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     296(2) 

_cell_measurement_reflns_used      23

_cell_measurement_theta_min        5.15

_cell_measurement_theta_max       12.45



_exptl_crystal_description       'BLOCK             '

_exptl_crystal_colour            'COLORLESS         '

_exptl_crystal_size_max          0.44 

_exptl_crystal_size_mid          0.24 

_exptl_crystal_size_min          0.22 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.296 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              728 

_exptl_absorpt_coefficient_mu     0.200 

_exptl_absorpt_correction_type   'none'

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

? 

; 



_diffrn_ambient_temperature       296(2) 

_diffrn_radiation_wavelength      0.71073 

_diffrn_radiation_type           'MoK\a'

_diffrn_radiation_source         'sealed tube'

_diffrn_radiation_monochromator  'graphite'

_diffrn_measurement_device       'Siemens P4'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean  ? 

_diffrn_standards_number            3

_diffrn_standards_interval_count   97

_diffrn_standards_interval_time   ? 

_diffrn_standards_decay_%         ? 

_diffrn_reflns_number             6251 

_diffrn_reflns_av_R_equivalents   0.0213 

_diffrn_reflns_av_sigmaI/netI     0.0361 

_diffrn_reflns_limit_h_min        -14 

_diffrn_reflns_limit_h_max        0 

_diffrn_reflns_limit_k_min        -13 

_diffrn_reflns_limit_k_max        12 

_diffrn_reflns_limit_l_min        -16 

_diffrn_reflns_limit_l_max        16 

_diffrn_reflns_theta_min          1.91 

_diffrn_reflns_theta_max          25.00 

_reflns_number_total              5946 

_reflns_number_gt                 4626 

_reflns_threshold_expression      >2sigma(I) 



_computing_data_collection      'Siemens XSCANS'

_computing_cell_refinement      'Siemens XSCANS'

_computing_data_reduction       'Siemens SHELXTL'

_computing_structure_solution   'Siemens SHELXTL'

_computing_structure_refinement 'Siemens SHELXTL'

_computing_molecular_graphics   'Siemens SHELXTL'

_computing_publication_material 'Siemens SHELXTL'



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme       calc  

_refine_ls_weighting_details 

'calc w=1/[σ²(Fo²)+(0.0537P)²+0.7408P] 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        0.0031(7) 

_refine_ls_extinction_expression 

'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 

_refine_ls_number_reflns          5946 

_refine_ls_number_parameters      560 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0636 

_refine_ls_R_factor_gt            0.0463 

_refine_ls_wR_factor_ref          0.1253 

_refine_ls_wR_factor_gt           0.1135 

_refine_ls_goodness_of_fit_ref    1.031 

_refine_ls_restrained_S_all       1.031 

_refine_ls_shift/su_max           0.006 

_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 0.59902(5) 0.67057(5) 0.46438(5) 0.04591(18) Uani 1 1 d . . . 

O1 O 0.58917(17) 0.79523(15) 0.43849(14) 0.0607(5) Uani 1 1 d . . . 

O2 O 0.49057(15) 0.64838(17) 0.47817(14) 0.0588(5) Uani 1 1 d . . . 

O3 O 0.9462(3) 0.4153(2) 0.5761(2) 0.0857(8) Uani 1 1 d . . . 

N1 N 0.67644(17) 0.58399(18) 0.57576(15) 0.0475(5) Uani 1 1 d . . . 

C1 C 0.6840(2) 0.6188(2) 0.36566(18) 0.0425(5) Uani 1 1 d . . . 

C2 C 0.7610(2) 0.6737(2) 0.30385(19) 0.0496(6) Uani 1 1 d . . . 

C3 C 0.8287(2) 0.6306(3) 0.2285(2) 0.0542(6) Uani 1 1 d . . . 

C4 C 0.8222(2) 0.5324(2) 0.2129(2) 0.0553(6) Uani 1 1 d . . . 

C5 C 0.7451(3) 0.4789(3) 0.2758(2) 0.0604(7) Uani 1 1 d . . . 

C6 C 0.6753(2) 0.5206(2) 0.3516(2) 0.0528(6) Uani 1 1 d . . . 

C7 C 0.8960(4) 0.4872(4) 0.1296(3) 0.0802(10) Uani 1 1 d . . . 

C8 C 0.6964(3) 0.4503(3) 0.6259(2) 0.0594(7) Uani 1 1 d . . . 

C9 C 0.7965(2) 0.3969(2) 0.70864(19) 0.0460(6) Uani 1 1 d . . . 

C10 C 0.8763(2) 0.4678(2) 0.6493(2) 0.0504(6) Uani 1 1 d . . . 

C11 C 0.7867(2) 0.5994(2) 0.5913(2) 0.0500(6) Uani 1 1 d . . . 

C12 C 0.8637(2) 0.2561(2) 0.75569(19) 0.0484(6) Uani 1 1 d . . . 

C13 C 0.8474(3) 0.1813(3) 0.7201(3) 0.0652(8) Uani 1 1 d . . . 

C14 C 0.9517(2) 0.2037(2) 0.84490(19) 0.0480(6) Uani 1 1 d . . . 

C15 C 1.0634(3) 0.1050(3) 0.8515(3) 0.0677(8) Uani 1 1 d . . . 

C16 C 1.1449(3) 0.0535(3) 0.9351(4) 0.0853(11) Uani 1 1 d . . . 

C17 C 1.1177(3) 0.1000(4) 1.0128(3) 0.0837(11) Uani 1 1 d . . . 

C18 C 1.0091(3) 0.1985(4) 1.0080(2) 0.0753(9) Uani 1 1 d . . . 

C19 C 0.9266(3) 0.2501(3) 0.9249(2) 0.0609(7) Uani 1 1 d . . . 

H2 H 0.767(3) 0.740(3) 0.310(2) 0.080 Uiso 1 1 d . . . 

H3 H 0.880(3) 0.665(3) 0.188(2) 0.080 Uiso 1 1 d . . . 

H5 H 0.736(3) 0.416(3) 0.267(2) 0.080 Uiso 1 1 d . . . 

H6 H 0.620(3) 0.482(3) 0.397(2) 0.080 Uiso 1 1 d . . . 

H7A H 0.877(3) 0.425(3) 0.119(3) 0.080 Uiso 1 1 d . . . 

H7B H 0.881(3) 0.542(3) 0.067(3) 0.080 Uiso 1 1 d . . . 

H7C H 0.978(3) 0.451(3) 0.143(2) 0.080 Uiso 1 1 d . . . 

H8A H 0.627(3) 0.440(3) 0.658(2) 0.080 Uiso 1 1 d . . . 

H8B H 0.728(3) 0.414(3) 0.574(3) 0.080 Uiso 1 1 d . . . 

H9 H 0.756(3) 0.430(3) 0.759(2) 0.080 Uiso 1 1 d . . . 

H10 H 0.927(3) 0.468(3) 0.697(2) 0.080 Uiso 1 1 d . . . 

H11A H 0.817(3) 0.639(3) 0.522(3) 0.080 Uiso 1 1 d . . . 

H11B H 0.769(3) 0.649(3) 0.632(2) 0.080 Uiso 1 1 d . . . 

H13A H 0.794(3) 0.211(3) 0.661(3) 0.080 Uiso 1 1 d . . . 

H13B H 0.886(3) 0.093(3) 0.752(2) 0.080 Uiso 1 1 d . . . 

H15 H 1.080(3) 0.078(3) 0.797(2) 0.080 Uiso 1 1 d . . . 

H16 H 1.217(3) -0.011(3) 0.937(3) 0.080 Uiso 1 1 d . . . 

H17 H 1.171(3) 0.065(3) 1.072(3) 0.080 Uiso 1 1 d . . . 

H19 H 0.854(3) 0.314(3) 0.928(2) 0.080 Uiso 1 1 d . . . 

H18 H 0.992(3) 0.227(3) 1.063(3) 0.080 Uiso 1 1 d . . . 

HO3 H 0.963(4) 0.444(4) 0.543(3) 0.080 Uiso 1 1 d . . . 

S2 S 0.65189(6) 0.62835(6) 0.87621(5) 0.05099(19) Uani 1 1 d . . . 

O4 O 0.76658(16) 0.63593(19) 0.84322(15) 0.0644(5) Uani 1 1 d . . . 

O5 O 0.64453(18) 0.50854(16) 0.91941(16) 0.0656(5) Uani 1 1 d . . . 

O6 O 0.3654(2) 0.9880(2) 0.7169(2) 0.0878(8) Uani 1 1 d . . . 

N2 N 0.56146(18) 0.71349(19) 0.77239(16) 0.0507(5) Uani 1 1 d . . . 

C20 C 0.5941(2) 0.6975(2) 0.97041(19) 0.0467(6) Uani 1 1 d . . . 

C21 C 0.4998(3) 0.6755(3) 1.0346(2) 0.0586(7) Uani 1 1 d . . . 

C22 C 0.4507(3) 0.7356(3) 1.1037(2) 0.0605(7) Uani 1 1 d . . . 

C23 C 0.4941(2) 0.8158(2) 1.1127(2) 0.0536(6) Uani 1 1 d . . . 

C24 C 0.5890(3) 0.8347(3) 1.0495(2) 0.0566(7) Uani 1 1 d . . . 

C25 C 0.6391(2) 0.7769(2) 0.9784(2) 0.0529(6) Uani 1 1 d . . . 

C26 C 0.4397(3) 0.8802(3) 1.1894(3) 0.0724(9) Uani 1 1 d . . . 

C27 C 0.5617(3) 0.8374(3) 0.7005(2) 0.0571(7) Uani 1 1 d . . . 

C28 C 0.4331(2) 0.9163(2) 0.6567(2) 0.0554(6) Uani 1 1 d . . . 

C29 C 0.3812(2) 0.8209(2) 0.6719(2) 0.0493(6) Uani 1 1 d . . . 

C30 C 0.4365(3) 0.7190(3) 0.7785(2) 0.0600(7) Uani 1 1 d . . . 

C31 C 0.2445(2) 0.8770(2) 0.6583(2) 0.0531(6) Uani 1 1 d . . . 

C32 C 0.1729(3) 0.8434(3) 0.7367(3) 0.0711(8) Uani 1 1 d . . . 

C33 C 0.1943(2) 0.9749(3) 0.5515(2) 0.0558(6) Uani 1 1 d . . . 

C34 C 0.0984(3) 1.0880(3) 0.5408(3) 0.0872(11) Uani 1 1 d . . . 

C35 C 0.0533(4) 1.1801(4) 0.4423(4) 0.1065(14) Uani 1 1 d . . . 

C36 C 0.1021(4) 1.1620(4) 0.3531(4) 0.0917(12) Uani 1 1 d . . . 

C37 C 0.1970(3) 1.0518(4) 0.3605(3) 0.0817(10) Uani 1 1 d . . . 

C38 C 0.2431(3) 0.9593(3) 0.4583(3) 0.0678(8) Uani 1 1 d . . . 

H21 H 0.472(3) 0.627(3) 1.030(2) 0.080 Uiso 1 1 d . . . 

H22 H 0.391(3) 0.720(3) 1.146(2) 0.080 Uiso 1 1 d . . . 

H24 H 0.622(3) 0.884(3) 1.057(2) 0.080 Uiso 1 1 d . . . 

H25 H 0.702(3) 0.794(3) 0.934(2) 0.080 Uiso 1 1 d . . . 

H26A H 0.372(3) 0.955(3) 1.162(2) 0.080 Uiso 1 1 d . . . 

H26B H 0.423(3) 0.820(3) 1.254(3) 0.080 Uiso 1 1 d . . . 

H26C H 0.490(3) 0.904(3) 1.212(3) 0.080 Uiso 1 1 d . . . 

H27A H 0.584(3) 0.876(3) 0.739(2) 0.080 Uiso 1 1 d . . . 

H27B H 0.617(3) 0.826(3) 0.643(3) 0.080 Uiso 1 1 d . . . 

H28 H 0.432(3) 0.977(3) 0.576(2) 0.080 Uiso 1 1 d . . . 

H29 H 0.414(3) 0.787(3) 0.620(2) 0.080 Uiso 1 1 d . . . 

H30A H 0.442(3) 0.634(3) 0.792(2) 0.080 Uiso 1 1 d . . . 

H30B H 0.385(3) 0.746(3) 0.844(2) 0.080 Uiso 1 1 d . . . 

H32A H 0.094(3) 0.877(3) 0.726(3) 0.080 Uiso 1 1 d . . . 

H32B H 0.209(3) 0.778(3) 0.813(3) 0.080 Uiso 1 1 d . . . 

H34 H 0.068(3) 1.098(3) 0.606(3) 0.080 Uiso 1 1 d . . . 

H35 H -0.003(3) 1.249(3) 0.447(3) 0.080 Uiso 1 1 d . . . 

H36 H 0.073(3) 1.225(3) 0.290(3) 0.080 Uiso 1 1 d . . . 

H37 H 0.228(3) 1.048(3) 0.297(3) 0.080 Uiso 1 1 d . . . 

H38 H 0.309(3) 0.882(3) 0.461(2) 0.080 Uiso 1 1 d . . . 

HO6 H 0.381(3) 1.046(3) 0.692(3) 0.080 Uiso 1 1 d . . . 






_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

S1 O2 1.4300(18) . ? 

S1 O1 1.4334(18) . ? 

S1 N1 1.618(2) . ? 

S1 C1 1.758(2) . ? 

O3 C10 1.415(4) . ? 

N1 C8 1.475(3) . ? 

N1 C11 1.488(3) . ? 

C1 C2 1.385(3) . ? 

C1 C6 1.389(3) . ? 

C2 C3 1.373(4) . ? 

C3 C4 1.386(4) . ? 

C4 C5 1.382(4) . ? 

C4 C7 1.499(4) . ? 

C5 C6 1.379(4) . ? 

C8 C9 1.520(4) . ? 

C9 C12 1.509(3) . ? 

C9 C10 1.525(3) . ? 

C10 C11 1.503(4) . ? 

C12 C13 1.324(4) . ? 

C12 C14 1.485(3) . ? 

C14 C19 1.390(4) . ? 

C14 C15 1.392(4) . ? 

C15 C16 1.379(5) . ? 

C16 C17 1.360(5) . ? 

C17 C18 1.371(5) . ? 

C18 C19 1.382(4) . ? 

S2 O4 1.4301(19) . ? 

S2 O5 1.4319(19) . ? 

S2 N2 1.616(2) . ? 

S2 C20 1.758(2) . ? 

O6 C28 1.408(3) . ? 

N2 C30 1.480(3) . ? 

N2 C27 1.483(3) . ? 

C20 C25 1.381(4) . ? 

C20 C21 1.392(4) . ? 

C21 C22 1.374(4) . ? 

C22 C23 1.382(4) . ? 

C23 C24 1.381(4) . ? 

C23 C26 1.506(4) . ? 

C24 C25 1.381(4) . ? 

C27 C28 1.507(4) . ? 

C28 C29 1.522(4) . ? 

C29 C31 1.510(3) . ? 

C29 C30 1.513(4) . ? 

C31 C32 1.327(4) . ? 

C31 C33 1.488(4) . ? 

C33 C34 1.384(4) . ? 

C33 C38 1.385(4) . ? 

C34 C35 1.376(6) . ? 

C35 C36 1.345(6) . ? 

C36 C37 1.365(5) . ? 

C37 C38 1.373(5) . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

O2 S1 O1 119.07(11) . . ? 

O2 S1 N1 106.72(11) . . ? 

O1 S1 N1 106.28(11) . . ? 

O2 S1 C1 108.33(11) . . ? 

O1 S1 C1 107.98(11) . . ? 

N1 S1 C1 108.02(11) . . ? 

C8 N1 C11 110.04(19) . . ? 

C8 N1 S1 118.85(17) . . ? 

C11 N1 S1 119.36(16) . . ? 

C2 C1 C6 120.2(2) . . ? 

C2 C1 S1 120.30(19) . . ? 

C6 C1 S1 119.48(19) . . ? 

C3 C2 C1 119.7(2) . . ? 

C2 C3 C4 121.4(3) . . ? 

C5 C4 C3 117.8(2) . . ? 

C5 C4 C7 121.4(3) . . ? 

C3 C4 C7 120.7(3) . . ? 

C6 C5 C4 122.1(3) . . ? 

C5 C6 C1 118.7(3) . . ? 

N1 C8 C9 102.4(2) . . ? 

C12 C9 C8 116.8(2) . . ? 

C12 C9 C10 114.4(2) . . ? 

C8 C9 C10 101.9(2) . . ? 

O3 C10 C11 110.5(2) . . ? 

O3 C10 C9 108.8(2) . . ? 

C11 C10 C9 103.8(2) . . ? 

N1 C11 C10 104.3(2) . . ? 

C13 C12 C14 120.7(2) . . ? 

C13 C12 C9 122.8(3) . . ? 

C14 C12 C9 116.5(2) . . ? 

C19 C14 C15 117.3(3) . . ? 

C19 C14 C12 122.0(2) . . ? 

C15 C14 C12 120.7(3) . . ? 

C16 C15 C14 121.4(3) . . ? 

C17 C16 C15 120.1(3) . . ? 

C16 C17 C18 120.0(3) . . ? 

C17 C18 C19 120.2(3) . . ? 

C18 C19 C14 120.9(3) . . ? 

O4 S2 O5 119.45(12) . . ? 

O4 S2 N2 106.55(11) . . ? 

O5 S2 N2 106.76(11) . . ? 

O4 S2 C20 108.41(12) . . ? 

O5 S2 C20 107.67(12) . . ? 

N2 S2 C20 107.46(11) . . ? 

C30 N2 C27 109.7(2) . . ? 

C30 N2 S2 119.95(18) . . ? 

C27 N2 S2 119.88(17) . . ? 

C25 C20 C21 119.9(2) . . ? 

C25 C20 S2 120.1(2) . . ? 

C21 C20 S2 119.9(2) . . ? 

C22 C21 C20 119.4(3) . . ? 

C21 C22 C23 121.6(3) . . ? 

C24 C23 C22 118.1(3) . . ? 

C24 C23 C26 121.1(3) . . ? 

C22 C23 C26 120.8(3) . . ? 

C25 C24 C23 121.6(3) . . ? 

C24 C25 C20 119.3(3) . . ? 

N2 C27 C28 104.9(2) . . ? 

O6 C28 C27 110.8(3) . . ? 

O6 C28 C29 108.3(2) . . ? 

C27 C28 C29 104.1(2) . . ? 

C31 C29 C30 117.5(2) . . ? 

C31 C29 C28 113.6(2) . . ? 

C30 C29 C28 102.9(2) . . ? 

N2 C30 C29 101.7(2) . . ? 

C32 C31 C33 121.8(3) . . ? 

C32 C31 C29 122.6(3) . . ? 

C33 C31 C29 115.6(2) . . ? 

C34 C33 C38 116.8(3) . . ? 

C34 C33 C31 121.2(3) . . ? 

C38 C33 C31 121.9(2) . . ? 

C35 C34 C33 121.5(4) . . ? 

C36 C35 C34 120.3(4) . . ? 

C35 C36 C37 119.8(4) . . ? 

C36 C37 C38 120.4(4) . . ? 

C37 C38 C33 121.1(3) . . ? 



_diffrn_measured_fraction_theta_max    0.961 

_diffrn_reflns_theta_full              25.00 

_diffrn_measured_fraction_theta_full   0.961 

_refine_diff_density_max    0.251 

_refine_diff_density_min   -0.247 

_refine_diff_density_rms    0.040 





data_p-1 

_database_code_CSD                  191653



_audit_creation_method            SHELXL-97 

_chemical_name_systematic 

; 

? 

; 

_chemical_name_common             ? 

_chemical_melting_point           ? 

_chemical_formula_moiety          ? 

_chemical_formula_sum 

'C20 H23 N O3 S' 

_chemical_formula_weight          357.45 



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           'Triclinic'

_symmetry_space_group_name_H-M   'P-1   '



loop_ 

_symmetry_equiv_pos_as_xyz 

'x, y, z' 

'-x, -y, -z' 



_cell_length_a                    9.324(2) 

_cell_length_b                    9.548(3) 

_cell_length_c                    11.620(3) 

_cell_angle_alpha                 81.54(2) 

_cell_angle_beta                  66.499(12) 

_cell_angle_gamma                 85.044(18) 

_cell_volume                      938.0(4) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     295(2) 

_cell_measurement_reflns_used      28

_cell_measurement_theta_min        3.84

_cell_measurement_theta_max       12.35



_exptl_crystal_description       'BLOCK             '

_exptl_crystal_colour            'COLORLESS         '

_exptl_crystal_size_max          0.24 

_exptl_crystal_size_mid          0.10 

_exptl_crystal_size_min          0.08 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.266 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              380 

_exptl_absorpt_coefficient_mu     0.191 

_exptl_absorpt_correction_type   'empirical'

_exptl_absorpt_correction_T_min  0.6937

_exptl_absorpt_correction_T_max  0.7373

_exptl_absorpt_process_details    ? 



_exptl_special_details 

; 

? 

; 



_diffrn_ambient_temperature       295(2) 

_diffrn_radiation_wavelength      0.71073 

_diffrn_radiation_type           'MoK\a'

_diffrn_radiation_source         'sealed tube'

_diffrn_radiation_monochromator  'graphite'

_diffrn_measurement_device       'Siemens P4'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean  ? 

_diffrn_standards_number            3

_diffrn_standards_interval_count   97

_diffrn_standards_interval_time   ? 

_diffrn_standards_decay_%         ? 

_diffrn_reflns_number             3502 

_diffrn_reflns_av_R_equivalents   0.0357 

_diffrn_reflns_av_sigmaI/netI     0.0857 

_diffrn_reflns_limit_h_min        0 

_diffrn_reflns_limit_h_max        11 

_diffrn_reflns_limit_k_min        -11 

_diffrn_reflns_limit_k_max        11 

_diffrn_reflns_limit_l_min        -12 

_diffrn_reflns_limit_l_max        13 

_diffrn_reflns_theta_min          1.93 

_diffrn_reflns_theta_max          25.00 

_reflns_number_total              3281 

_reflns_number_gt                 1903 

_reflns_threshold_expression      >2sigma(I) 



_computing_data_collection      'Siemens XSCANS'

_computing_cell_refinement      'Siemens XSCANS'

_computing_data_reduction       'Siemens SHELXTL'

_computing_structure_solution   'Siemens SHELXTL'

_computing_structure_refinement 'Siemens SHELXTL'

_computing_molecular_graphics   'Siemens SHELXTL'

_computing_publication_material 'Siemens SHELXTL'



_refine_special_details 

; 

Refinement of F² against ALL reflections.  The weighted R-factor wR and 

goodness of fit S are based on F², conventional R-factors R are based 

on F, with F set to zero for negative F². The threshold expression of 

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

not relevant to the choice of reflections for refinement.  R-factors based 

on F² are statistically about twice as large as those based on F, and R- 

factors based on ALL data will be even larger. 

; 



2_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)+(0.0428P)²+0.1531P] 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        0.013(2) 

_refine_ls_extinction_expression 

'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 

_refine_ls_number_reflns          3281 

_refine_ls_number_parameters      307 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.1198 

_refine_ls_R_factor_gt            0.0576 

_refine_ls_wR_factor_ref          0.1277 

_refine_ls_wR_factor_gt           0.1046 

_refine_ls_goodness_of_fit_ref    1.009 

_refine_ls_restrained_S_all       1.009 

_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 0.29203(11) 0.27867(10) 0.76636(9) 0.0516(3) Uani 1 1 d . . . 

O1 O 0.3409(3) 0.4049(3) 0.7930(2) 0.0634(7) Uani 1 1 d . . . 

O2 O 0.3509(3) 0.1424(3) 0.8009(2) 0.0690(8) Uani 1 1 d . . . 

O3 O 0.4628(3) 0.3627(3) 0.3468(3) 0.0613(8) Uani 1 1 d . . . 

C1 C 0.0871(4) 0.2779(4) 0.8393(3) 0.0460(8) Uani 1 1 d . . . 

C2 C 0.0010(5) 0.4023(4) 0.8719(4) 0.0538(10) Uani 1 1 d . . . 

C3 C -0.1608(5) 0.4011(5) 0.9266(4) 0.0609(11) Uani 1 1 d . . . 

C4 C -0.2397(5) 0.2781(5) 0.9490(3) 0.0645(11) Uani 1 1 d . . . 

C5 C -0.1518(5) 0.1543(5) 0.9177(4) 0.0740(13) Uani 1 1 d . . . 

C6 C 0.0102(5) 0.1528(4) 0.8629(4) 0.0647(11) Uani 1 1 d . . . 

C7 C -0.4159(5) 0.2771(6) 1.0082(4) 0.1092(18) Uani 1 1 d . . . 

H7A H -0.4498 0.1827 1.0162 0.131 Uiso 1 1 calc R . . 

H7B H -0.4575 0.3396 0.9557 0.131 Uiso 1 1 calc R . . 

H7C H -0.4526 0.3082 1.0903 0.131 Uiso 1 1 calc R . . 

N1 N 0.3401(3) 0.2960(3) 0.6147(3) 0.0487(7) Uani 1 1 d . . . 

C8 C 0.2981(4) 0.4318(4) 0.5520(3) 0.0468(9) Uani 1 1 d . . . 

C9 C 0.3040(4) 0.3899(3) 0.4286(3) 0.0445(8) Uani 1 1 d . . . 

C10 C 0.2297(4) 0.2436(3) 0.4744(3) 0.0428(8) Uani 1 1 d . . . 

C11 C 0.3147(5) 0.1751(4) 0.5577(4) 0.0526(9) Uani 1 1 d . . . 

C12 C 0.2248(6) 0.4974(5) 0.3622(5) 0.0621(11) Uani 1 1 d . . . 

C13 C 0.2276(4) 0.1605(3) 0.3742(3) 0.0452(8) Uani 1 1 d . . . 

C14 C 0.3456(5) 0.0766(5) 0.3132(4) 0.0651(11) Uani 1 1 d . . . 

C15 C 0.0857(4) 0.1797(3) 0.3440(3) 0.0439(8) Uani 1 1 d . . . 

C16 C -0.0639(4) 0.1788(4) 0.4376(4) 0.0523(9) Uani 1 1 d . . . 

C17 C -0.1949(5) 0.1959(4) 0.4081(5) 0.0646(11) Uani 1 1 d . . . 

C18 C -0.1786(6) 0.2129(4) 0.2839(6) 0.0729(13) Uani 1 1 d . . . 

C19 C -0.0325(6) 0.2137(4) 0.1911(5) 0.0679(12) Uani 1 1 d . . . 

C20 C 0.0996(5) 0.1971(4) 0.2184(4) 0.0557(10) Uani 1 1 d . . . 

HO3 H 0.508(4) 0.431(4) 0.310(3) 0.062(13) Uiso 1 1 d . . . 

H2 H 0.053(3) 0.477(3) 0.858(3) 0.036(9) Uiso 1 1 d . . . 

H3 H -0.219(4) 0.486(4) 0.952(3) 0.064(11) Uiso 1 1 d . . . 

H5 H -0.200(5) 0.067(4) 0.926(4) 0.092(14) Uiso 1 1 d . . . 

H6 H 0.067(4) 0.068(4) 0.844(3) 0.078(13) Uiso 1 1 d . . . 

H8A H 0.376(4) 0.506(3) 0.539(3) 0.061(10) Uiso 1 1 d . . . 

H8B H 0.192(3) 0.467(3) 0.601(3) 0.039(8) Uiso 1 1 d . . . 

H10 H 0.125(3) 0.265(3) 0.526(3) 0.038(8) Uiso 1 1 d . . . 

H11A H 0.257(4) 0.102(3) 0.627(3) 0.048(9) Uiso 1 1 d . . . 

H11B H 0.419(4) 0.134(4) 0.506(3) 0.068(11) Uiso 1 1 d . . . 

H12A H 0.117(5) 0.515(4) 0.417(4) 0.083(14) Uiso 1 1 d . . . 

H12B H 0.274(4) 0.589(4) 0.343(3) 0.063(11) Uiso 1 1 d . . . 

H12C H 0.236(4) 0.471(4) 0.286(4) 0.082(14) Uiso 1 1 d . . . 

H14A H 0.442(4) 0.064(4) 0.326(3) 0.074(12) Uiso 1 1 d . . . 

H14B H 0.336(4) 0.021(4) 0.253(3) 0.068(11) Uiso 1 1 d . . . 

H16 H -0.077(3) 0.164(3) 0.526(3) 0.047(9) Uiso 1 1 d . . . 

H17 H -0.293(4) 0.196(4) 0.475(3) 0.064(12) Uiso 1 1 d . . . 

H18 H -0.279(5) 0.234(4) 0.269(4) 0.105(15) Uiso 1 1 d . . . 

H19 H -0.019(5) 0.223(4) 0.105(4) 0.084(14) Uiso 1 1 d . . . 

H20 H 0.203(4) 0.198(3) 0.154(3) 0.055(10) Uiso 1 1 d . . . 






_geom_special_details 

; 

All esds (except the esd in the dihedral angle between two l.s. planes) 

are estimated using the full covariance matrix.  The cell esds are taken 

into account individually in the estimation of esds in distances, angles 

and torsion angles; correlations between esds in cell parameters are only 

used when they are defined by crystal symmetry.  An approximate (isotropic) 

treatment of cell esds is used for estimating esds involving l.s. planes. 

; 



loop_ 

_geom_bond_atom_site_label_1 

_geom_bond_atom_site_label_2 

_geom_bond_distance 

_geom_bond_site_symmetry_2 

_geom_bond_publ_flag 

S1 O2 1.433(2) . ? 

S1 O1 1.440(2) . ? 

S1 N1 1.622(3) . ? 

S1 C1 1.755(4) . ? 

O3 C9 1.430(4) . ? 

O3 HO3 0.78(4) . ? 

C1 C6 1.382(5) . ? 

C1 C2 1.387(5) . ? 

C2 C3 1.384(5) . ? 

C2 H2 0.86(3) . ? 

C3 C4 1.377(5) . ? 

C3 H3 0.95(3) . ? 

C4 C5 1.387(6) . ? 

C4 C7 1.507(5) . ? 

C5 C6 1.386(6) . ? 

C5 H5 0.95(4) . ? 

C6 H6 0.93(4) . ? 

C7 H7A 0.9600 . ? 

C7 H7B 0.9600 . ? 

C7 H7C 0.9600 . ? 

N1 C11 1.493(4) . ? 

N1 C8 1.493(4) . ? 

C8 C9 1.523(5) . ? 

C8 H8A 1.01(3) . ? 

C8 H8B 0.98(3) . ? 

C9 C12 1.512(5) . ? 

C9 C10 1.539(4) . ? 

C10 C13 1.510(4) . ? 

C10 C11 1.525(5) . ? 

C10 H10 0.94(3) . ? 

C11 H11A 0.99(3) . ? 

C11 H11B 1.00(4) . ? 

C12 H12A 0.97(4) . ? 

C12 H12B 0.98(4) . ? 

C12 H12C 0.92(4) . ? 

C13 C14 1.322(5) . ? 

C13 C15 1.489(5) . ? 

C14 H14A 0.96(4) . ? 

C14 H14B 0.97(3) . ? 

C15 C16 1.385(5) . ? 

C15 C20 1.398(5) . ? 

C16 C17 1.386(5) . ? 

C16 H16 0.97(3) . ? 

C17 C18 1.376(6) . ? 

C17 H17 0.93(3) . ? 

C18 C19 1.359(6) . ? 

C18 H18 1.01(4) . ? 

C19 C20 1.381(5) . ? 

C19 H19 0.94(4) . ? 

C20 H20 0.96(3) . ? 



loop_ 

_geom_angle_atom_site_label_1 

_geom_angle_atom_site_label_2 

_geom_angle_atom_site_label_3 

_geom_angle 

_geom_angle_site_symmetry_1 

_geom_angle_site_symmetry_3 

_geom_angle_publ_flag 

O2 S1 O1 120.10(16) . . ? 

O2 S1 N1 107.18(15) . . ? 

O1 S1 N1 106.35(15) . . ? 

O2 S1 C1 107.77(17) . . ? 

O1 S1 C1 107.24(16) . . ? 

N1 S1 C1 107.65(15) . . ? 

C9 O3 HO3 114(3) . . ? 

C6 C1 C2 119.5(4) . . ? 

C6 C1 S1 119.9(3) . . ? 

C2 C1 S1 120.6(3) . . ? 

C3 C2 C1 120.1(4) . . ? 

C3 C2 H2 123(2) . . ? 

C1 C2 H2 117(2) . . ? 

C4 C3 C2 121.3(4) . . ? 

C4 C3 H3 119(2) . . ? 

C2 C3 H3 120(2) . . ? 

C3 C4 C5 117.8(4) . . ? 

C3 C4 C7 121.3(4) . . ? 

C5 C4 C7 120.9(4) . . ? 

C6 C5 C4 121.9(4) . . ? 

C6 C5 H5 116(3) . . ? 

C4 C5 H5 121(2) . . ? 

C1 C6 C5 119.3(4) . . ? 

C1 C6 H6 120(2) . . ? 

C5 C6 H6 121(2) . . ? 

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 . . ? 

C11 N1 C8 109.3(3) . . ? 

C11 N1 S1 118.5(2) . . ? 

C8 N1 S1 118.6(2) . . ? 

N1 C8 C9 102.7(3) . . ? 

N1 C8 H8A 109.6(18) . . ? 

C9 C8 H8A 113.5(18) . . ? 

N1 C8 H8B 112.3(16) . . ? 

C9 C8 H8B 109.4(16) . . ? 

H8A C8 H8B 109(2) . . ? 

O3 C9 C12 110.8(3) . . ? 

O3 C9 C8 109.8(3) . . ? 

C12 C9 C8 113.5(3) . . ? 

O3 C9 C10 105.3(3) . . ? 

C12 C9 C10 115.7(3) . . ? 

C8 C9 C10 101.0(3) . . ? 

C13 C10 C11 117.2(3) . . ? 

C13 C10 C9 116.8(3) . . ? 

C11 C10 C9 101.7(3) . . ? 

C13 C10 H10 107.9(17) . . ? 

C11 C10 H10 108.9(17) . . ? 

C9 C10 H10 103.4(17) . . ? 

N1 C11 C10 103.7(3) . . ? 

N1 C11 H11A 108.2(18) . . ? 

C10 C11 H11A 116.1(18) . . ? 

N1 C11 H11B 109(2) . . ? 

C10 C11 H11B 111(2) . . ? 

H11A C11 H11B 109(3) . . ? 

C9 C12 H12A 111(2) . . ? 

C9 C12 H12B 110(2) . . ? 

H12A C12 H12B 105(3) . . ? 

C9 C12 H12C 111(2) . . ? 

H12A C12 H12C 113(3) . . ? 

H12B C12 H12C 107(3) . . ? 

C14 C13 C15 120.6(3) . . ? 

C14 C13 C10 122.8(3) . . ? 

C15 C13 C10 116.6(3) . . ? 

C13 C14 H14A 124(2) . . ? 

C13 C14 H14B 120(2) . . ? 

H14A C14 H14B 116(3) . . ? 

C16 C15 C20 117.5(3) . . ? 

C16 C15 C13 122.0(3) . . ? 

C20 C15 C13 120.6(3) . . ? 

C15 C16 C17 121.4(4) . . ? 

C15 C16 H16 119.0(18) . . ? 

C17 C16 H16 119.6(18) . . ? 

C18 C17 C16 120.2(4) . . ? 

C18 C17 H17 122(2) . . ? 

C16 C17 H17 118(2) . . ? 

C19 C18 C17 119.1(4) . . ? 

C19 C18 H18 125(2) . . ? 

C17 C18 H18 116(2) . . ? 

C18 C19 C20 121.6(5) . . ? 

C18 C19 H19 120(2) . . ? 

C20 C19 H19 118(2) . . ? 

C19 C20 C15 120.3(4) . . ? 

C19 C20 H20 123(2) . . ? 

C15 C20 H20 117(2) . . ? 



loop_ 

_geom_torsion_atom_site_label_1 

_geom_torsion_atom_site_label_2 

_geom_torsion_atom_site_label_3 

_geom_torsion_atom_site_label_4 

_geom_torsion 

_geom_torsion_site_symmetry_1 

_geom_torsion_site_symmetry_2 

_geom_torsion_site_symmetry_3 

_geom_torsion_site_symmetry_4 

_geom_torsion_publ_flag 

O2 S1 C1 C6 -29.9(4) . . . . ? 

O1 S1 C1 C6 -160.5(3) . . . . ? 

N1 S1 C1 C6 85.4(3) . . . . ? 

O2 S1 C1 C2 151.1(3) . . . . ? 

O1 S1 C1 C2 20.5(3) . . . . ? 

N1 S1 C1 C2 -93.6(3) . . . . ? 

C6 C1 C2 C3 -0.6(5) . . . . ? 

S1 C1 C2 C3 178.4(3) . . . . ? 

C1 C2 C3 C4 -0.5(6) . . . . ? 

C2 C3 C4 C5 1.5(6) . . . . ? 

C2 C3 C4 C7 -179.8(4) . . . . ? 

C3 C4 C5 C6 -1.5(6) . . . . ? 

C7 C4 C5 C6 179.8(4) . . . . ? 

C2 C1 C6 C5 0.6(6) . . . . ? 

S1 C1 C6 C5 -178.4(3) . . . . ? 

C4 C5 C6 C1 0.4(7) . . . . ? 

O2 S1 N1 C11 45.7(3) . . . . ? 

O1 S1 N1 C11 175.3(2) . . . . ? 

C1 S1 N1 C11 -70.0(3) . . . . ? 

O2 S1 N1 C8 -177.8(3) . . . . ? 

O1 S1 N1 C8 -48.2(3) . . . . ? 

C1 S1 N1 C8 66.5(3) . . . . ? 

C11 N1 C8 C9 -19.5(4) . . . . ? 

S1 N1 C8 C9 -159.6(2) . . . . ? 

N1 C8 C9 O3 -70.8(3) . . . . ? 

N1 C8 C9 C12 164.5(3) . . . . ? 

N1 C8 C9 C10 40.0(3) . . . . ? 

O3 C9 C10 C13 -60.5(4) . . . . ? 

C12 C9 C10 C13 62.1(4) . . . . ? 

C8 C9 C10 C13 -174.8(3) . . . . ? 

O3 C9 C10 C11 68.3(3) . . . . ? 

C12 C9 C10 C11 -169.0(3) . . . . ? 

C8 C9 C10 C11 -46.0(3) . . . . ? 

C8 N1 C11 C10 -9.3(4) . . . . ? 

S1 N1 C11 C10 130.9(3) . . . . ? 

C13 C10 C11 N1 162.6(3) . . . . ? 

C9 C10 C11 N1 34.0(4) . . . . ? 

C11 C10 C13 C14 -34.3(5) . . . . ? 

C9 C10 C13 C14 86.6(4) . . . . ? 

C11 C10 C13 C15 147.1(3) . . . . ? 

C9 C10 C13 C15 -91.9(3) . . . . ? 

C14 C13 C15 C16 136.3(4) . . . . ? 

C10 C13 C15 C16 -45.1(4) . . . . ? 

C14 C13 C15 C20 -42.7(5) . . . . ? 

C10 C13 C15 C20 135.9(3) . . . . ? 

C20 C15 C16 C17 -0.6(5) . . . . ? 

C13 C15 C16 C17 -179.6(3) . . . . ? 

C15 C16 C17 C18 0.6(6) . . . . ? 

C16 C17 C18 C19 -0.5(6) . . . . ? 

C17 C18 C19 C20 0.4(6) . . . . ? 

C18 C19 C20 C15 -0.4(6) . . . . ? 

C16 C15 C20 C19 0.5(5) . . . . ? 

C13 C15 C20 C19 179.5(3) . . . . ? 



_diffrn_measured_fraction_theta_max    0.994 

_diffrn_reflns_theta_full              25.00 

_diffrn_measured_fraction_theta_full   0.994 

_refine_diff_density_max    0.168 

_refine_diff_density_min   -0.201 

_refine_diff_density_rms    0.043 



#======================================================END











