# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_WAKABAYASHI3_1
_database_code_depnum_ccdc_archive 'CCDC 1037532'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;
#data_k141 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H27 N O4 S'
_chemical_formula_weight         437.54
_chemical_absolute_configuration rmad

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.9244(7)
_cell_length_b                   13.4171(16)
_cell_length_c                   29.058(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2309.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4774
_cell_measurement_theta_min      2.5935
_cell_measurement_theta_max      27.2975

_exptl_crystal_description       column
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9364
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   
;
SADABS; Sheldrick 1996
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         158
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12794
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.01
_reflns_number_total             4541
_reflns_number_gt                3839
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0770P)²+2.9045P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         4541
_refine_ls_number_parameters     284
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0882
_refine_ls_wR_factor_ref         0.2097
_refine_ls_wR_factor_gt          0.2018
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.180
_refine_ls_shift/su_max          0.001
_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 0.3476(8) 1.0731(3) 0.06671(14) 0.0333(10) Uani 1 1 d . . .
H1 H 0.3001 1.1351 0.0832 0.040 Uiso 1 1 calc R . .
C2 C 0.2228(7) 1.0693(3) 0.02041(14) 0.0310(9) Uani 1 1 d . . .
H2 H 0.0577 1.0766 0.0267 0.037 Uiso 1 1 calc R . .
C3 C 0.2877(7) 0.9848(3) 0.09662(14) 0.0314(10) Uani 1 1 d . . .
C4 C 0.4336(10) 0.9048(4) 0.10251(18) 0.0494(13) Uani 1 1 d . . .
H4 H 0.5746 0.9044 0.0869 0.059 Uiso 1 1 calc R . .
C5 C 0.3782(12) 0.8270(4) 0.1302(2) 0.0626(16) Uani 1 1 d . . .
H5 H 0.4832 0.7743 0.1347 0.075 Uiso 1 1 calc R . .
C6 C 0.1730(13) 0.8234(5) 0.15184(19) 0.0645(17) Uani 1 1 d . . .
H6 H 0.1327 0.7678 0.1704 0.077 Uiso 1 1 calc R . .
C7 C 0.0254(11) 0.9023(6) 0.1461(2) 0.0699(18) Uani 1 1 d . . .
H7 H -0.1170 0.9018 0.1611 0.084 Uiso 1 1 calc R . .
C8 C 0.0847(9) 0.9809(5) 0.11883(17) 0.0526(14) Uani 1 1 d . . .
H8 H -0.0184 1.0346 0.1152 0.063 Uiso 1 1 calc R . .
C9 C 0.2570(7) 0.9730(3) -0.00645(14) 0.0306(9) Uani 1 1 d . . .
C10 C 0.4598(8) 0.9514(3) -0.02820(16) 0.0383(11) Uani 1 1 d . . .
H10 H 0.5821 0.9970 -0.0260 0.046 Uiso 1 1 calc R . .
C11 C 0.4854(8) 0.8649(3) -0.05279(17) 0.0430(11) Uani 1 1 d . . .
H11 H 0.6243 0.8514 -0.0679 0.052 Uiso 1 1 calc R . .
C12 C 0.3111(9) 0.7977(4) -0.05571(17) 0.0470(13) Uani 1 1 d . . .
H12 H 0.3300 0.7376 -0.0726 0.056 Uiso 1 1 calc R . .
C13 C 0.1093(9) 0.8175(4) -0.03420(17) 0.0457(12) Uani 1 1 d . . .
H13 H -0.0119 0.7714 -0.0363 0.055 Uiso 1 1 calc R . .
C14 C 0.0837(8) 0.9048(4) -0.00961(16) 0.0392(10) Uani 1 1 d . . .
H14 H -0.0556 0.9181 0.0054 0.047 Uiso 1 1 calc R . .
C15 C 0.2341(11) 0.3358(6) 0.20208(16) 0.0816(16) Uani 1 1 d DU . .
H15 H 0.1151 0.2886 0.1998 0.098 Uiso 1 1 calc R . .
C16 C 0.2976(11) 0.3914(5) 0.16556(19) 0.0677(13) Uani 1 1 d U . .
C17 C 0.4797(15) 0.4565(5) 0.17926(19) 0.0764(10) Uani 1 1 d U . .
C18 C 0.5968(14) 0.5261(5) 0.15342(19) 0.0740(13) Uani 1 1 d U . .
H18 H 0.5579 0.5364 0.1221 0.089 Uiso 1 1 calc R . .
C19 C 0.7702(17) 0.5810(6) 0.1730(3) 0.095(3) Uani 1 1 d . . .
H19 H 0.8497 0.6283 0.1548 0.114 Uiso 1 1 calc R . .
C20 C 0.8285(18) 0.5676(6) 0.2183(3) 0.104(3) Uani 1 1 d . . .
H20 H 0.9484 0.6055 0.2312 0.124 Uiso 1 1 calc R . .
C21 C 0.7152(16) 0.5000(6) 0.2452(2) 0.093(2) Uani 1 1 d U . .
H21 H 0.7567 0.4917 0.2766 0.111 Uiso 1 1 calc R . .
C22 C 0.5308(14) 0.4406(5) 0.2259(2) 0.0919(8) Uani 1 1 d DU . .
C23 C 0.1923(9) 0.3891(4) 0.11872(17) 0.0473(9) Uani 1 1 d U . .
H23A H 0.1509 0.4582 0.1102 0.057 Uiso 1 1 calc R . .
H23B H 0.0507 0.3502 0.1206 0.057 Uiso 1 1 calc R . .
C24 C 0.3351(8) 0.3458(4) 0.08027(17) 0.0448(9) Uani 1 1 d U . .
C25 C 0.6695(19) 0.1524(7) 0.1781(3) 0.109(3) Uani 1 1 d . . .
H25A H 0.7309 0.1966 0.2019 0.164 Uiso 1 1 calc R . .
H25B H 0.7222 0.0841 0.1836 0.164 Uiso 1 1 calc R . .
H25C H 0.5043 0.1540 0.1793 0.164 Uiso 1 1 calc R . .
N1 N 0.2958(6) 1.1567(2) -0.00774(12) 0.0307(8) Uani 1 1 d . . .
H1A H 0.4380 1.1460 -0.0185 0.046 Uiso 1 1 calc R . .
H1B H 0.2944 1.2125 0.0100 0.046 Uiso 1 1 calc R . .
H1C H 0.1996 1.1647 -0.0319 0.046 Uiso 1 1 calc R . .
O1 O 0.5819(5) 1.0801(3) 0.05749(11) 0.0420(8) Uani 1 1 d . . .
H1D H 0.6434 1.1165 0.0774 0.063 Uiso 1 1 calc R . .
O2 O 0.5390(5) 0.3306(3) 0.08737(10) 0.0438(8) Uani 1 1 d . . .
O3 O 0.2399(6) 0.3309(2) 0.04280(11) 0.0431(8) Uani 1 1 d . . .
O4 O 0.7427(8) 0.1843(3) 0.13473(15) 0.0725(12) Uani 1 1 d . . .
H4A H 0.6820 0.2392 0.1284 0.109 Uiso 1 1 calc R . .
S1 S 0.3732(4) 0.35351(17) 0.25127(6) 0.0968(7) Uani 1 1 d DU . .


_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 O1 1.417(5) . ?
C1 C3 1.511(6) . ?
C1 C2 1.536(6) . ?
C1 H1 1.0000 . ?
C2 N1 1.494(5) . ?
C2 C9 1.523(6) . ?
C2 H2 1.0000 . ?
C3 C8 1.366(7) . ?
C3 C4 1.389(7) . ?
C4 C5 1.359(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.366(8) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.378(6) . ?
C9 C10 1.388(6) . ?
C10 C11 1.371(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.350(9) . ?
C15 S1 1.667(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.444(10) . ?
C16 C23 1.498(8) . ?
C17 C18 1.385(10) . ?
C17 C22 1.406(8) . ?
C18 C19 1.386(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.374(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.373(12) . ?
C20 H20 0.9500 . ?
C21 C22 1.464(11) . ?
C21 H21 0.9500 . ?
C22 S1 1.667(5) . ?
C23 C24 1.517(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O3 1.243(6) . ?
C24 O2 1.243(6) . ?
C25 O4 1.401(9) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
O1 H1D 0.8400 . ?
O4 H4A 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
O1 C1 C3 113.0(4) . . ?
O1 C1 C2 108.0(3) . . ?
C3 C1 C2 111.4(3) . . ?
O1 C1 H1 108.1 . . ?
C3 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
N1 C2 C9 110.3(3) . . ?
N1 C2 C1 108.3(3) . . ?
C9 C2 C1 114.4(3) . . ?
N1 C2 H2 107.9 . . ?
C9 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
C8 C3 C4 117.4(5) . . ?
C8 C3 C1 120.6(4) . . ?
C4 C3 C1 122.0(4) . . ?
C5 C4 C3 121.1(5) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.9(6) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 118.6(5) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 119.9(6) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C3 C8 C7 122.0(6) . . ?
C3 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C14 C9 C10 118.4(4) . . ?
C14 C9 C2 119.9(4) . . ?
C10 C9 C2 121.7(4) . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.3(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 121.0(5) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 S1 117.2(6) . . ?
C16 C15 H15 121.4 . . ?
S1 C15 H15 121.4 . . ?
C15 C16 C17 109.0(5) . . ?
C15 C16 C23 125.9(6) . . ?
C17 C16 C23 125.0(6) . . ?
C18 C17 C22 121.2(7) . . ?
C18 C17 C16 129.3(6) . . ?
C22 C17 C16 109.5(6) . . ?
C17 C18 C19 120.5(6) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 120.7(8) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.6(8) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.4(6) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 116.6(6) . . ?
C17 C22 S1 114.3(6) . . ?
C21 C22 S1 129.1(5) . . ?
C16 C23 C24 116.4(4) . . ?
C16 C23 H23A 108.2 . . ?
C24 C23 H23A 108.2 . . ?
C16 C23 H23B 108.2 . . ?
C24 C23 H23B 108.2 . . ?
H23A C23 H23B 107.3 . . ?
O3 C24 O2 124.1(5) . . ?
O3 C24 C23 117.0(4) . . ?
O2 C24 C23 118.9(4) . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 O1 H1D 109.5 . . ?
C25 O4 H4A 109.5 . . ?
C22 S1 C15 89.9(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
O1 C1 C2 N1 -53.6(4) . . . . ?
C3 C1 C2 N1 -178.2(3) . . . . ?
O1 C1 C2 C9 69.9(5) . . . . ?
C3 C1 C2 C9 -54.8(5) . . . . ?
O1 C1 C3 C8 162.5(4) . . . . ?
C2 C1 C3 C8 -75.8(5) . . . . ?
O1 C1 C3 C4 -17.9(6) . . . . ?
C2 C1 C3 C4 103.8(5) . . . . ?
C8 C3 C4 C5 -1.6(8) . . . . ?
C1 C3 C4 C5 178.8(5) . . . . ?
C3 C4 C5 C6 2.5(9) . . . . ?
C4 C5 C6 C7 -2.1(9) . . . . ?
C5 C6 C7 C8 0.9(9) . . . . ?
C4 C3 C8 C7 0.4(8) . . . . ?
C1 C3 C8 C7 -180.0(5) . . . . ?
C6 C7 C8 C3 -0.1(9) . . . . ?
N1 C2 C9 C14 -130.4(4) . . . . ?
C1 C2 C9 C14 107.2(5) . . . . ?
N1 C2 C9 C10 49.5(5) . . . . ?
C1 C2 C9 C10 -72.9(5) . . . . ?
C14 C9 C10 C11 1.0(7) . . . . ?
C2 C9 C10 C11 -179.0(4) . . . . ?
C9 C10 C11 C12 -0.9(7) . . . . ?
C10 C11 C12 C13 0.5(8) . . . . ?
C11 C12 C13 C14 -0.3(8) . . . . ?
C10 C9 C14 C13 -0.7(7) . . . . ?
C2 C9 C14 C13 179.2(4) . . . . ?
C12 C13 C14 C9 0.4(7) . . . . ?
S1 C15 C16 C17 -0.5(8) . . . . ?
S1 C15 C16 C23 -178.5(5) . . . . ?
C15 C16 C17 C18 -179.9(7) . . . . ?
C23 C16 C17 C18 -1.9(11) . . . . ?
C15 C16 C17 C22 0.1(8) . . . . ?
C23 C16 C17 C22 178.1(6) . . . . ?
C22 C17 C18 C19 0.9(12) . . . . ?
C16 C17 C18 C19 -179.1(7) . . . . ?
C17 C18 C19 C20 -0.3(12) . . . . ?
C18 C19 C20 C21 -0.4(14) . . . . ?
C19 C20 C21 C22 0.3(14) . . . . ?
C18 C17 C22 C21 -0.9(11) . . . . ?
C16 C17 C22 C21 179.1(7) . . . . ?
C18 C17 C22 S1 -179.7(6) . . . . ?
C16 C17 C22 S1 0.3(9) . . . . ?
C20 C21 C22 C17 0.3(12) . . . . ?
C20 C21 C22 S1 178.8(7) . . . . ?
C15 C16 C23 C24 -111.2(7) . . . . ?
C17 C16 C23 C24 71.2(8) . . . . ?
C16 C23 C24 O3 170.4(5) . . . . ?
C16 C23 C24 O2 -11.9(8) . . . . ?
C17 C22 S1 C15 -0.5(7) . . . . ?
C21 C22 S1 C15 -179.1(8) . . . . ?
C16 C15 S1 C22 0.6(7) . . . . ?

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 H1D O4 0.84 1.99 2.811(5) 166.3 1_565
N1 H1C O2 0.91 1.87 2.774(5) 170.2 4_465
N1 H1B O3 0.91 1.88 2.781(4) 170.0 1_565
N1 H1A O3 0.91 1.95 2.826(5) 161.8 4_565
O4 H4A O2 0.84 1.91 2.684(5) 152.9 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.061
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_WAKABAYASHI3_2
_database_code_depnum_ccdc_archive 'CCDC 1037533'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;
#data_k142b 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H29 N O4 S'
_chemical_formula_weight         451.56
_chemical_absolute_configuration rmad

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)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   15.071(5)
_cell_length_b                   5.840(2)
_cell_length_c                   15.398(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.293(6)
_cell_angle_gamma                90.00
_cell_volume                     1193.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1520
_cell_measurement_theta_min      2.6075
_cell_measurement_theta_max      25.1765

_exptl_crystal_description       column
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9593
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_process_details   
;
SADABS; Sheldrick 1996
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         49
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6033
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_sigmaI/netI    0.1745
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.35
_reflns_number_total             4117
_reflns_number_gt                2552
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0540P)²+0.5944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_number_reflns         4117
_refine_ls_number_parameters     293
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.0840
_refine_ls_wR_factor_ref         0.2016
_refine_ls_wR_factor_gt          0.1765
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.027
_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 0.8401(5) -0.0380(11) 1.0765(4) 0.0238(16) Uani 1 1 d . . .
H1D H 0.9052 0.0131 1.1330 0.029 Uiso 1 1 calc R . .
C2 C 0.8253(4) 0.0900(12) 0.9824(4) 0.0224(15) Uani 1 1 d . . .
H2 H 0.8363 0.2569 0.9985 0.027 Uiso 1 1 calc R . .
C3 C 0.7561(5) 0.0196(12) 1.0997(4) 0.0224(15) Uani 1 1 d . . .
C4 C 0.7580(5) 0.2254(13) 1.1482(4) 0.0293(17) Uani 1 1 d . . .
H4A H 0.8143 0.3252 1.1692 0.035 Uiso 1 1 calc R . .
C5 C 0.6783(6) 0.2839(13) 1.1655(5) 0.0337(19) Uani 1 1 d . . .
H5 H 0.6807 0.4231 1.1984 0.040 Uiso 1 1 calc R . .
C6 C 0.5944(6) 0.1396(15) 1.1348(5) 0.041(2) Uani 1 1 d . . .
H6 H 0.5400 0.1803 1.1465 0.049 Uiso 1 1 calc R . .
C7 C 0.5919(5) -0.0657(14) 1.0865(4) 0.0358(19) Uani 1 1 d . . .
H7 H 0.5356 -0.1652 1.0655 0.043 Uiso 1 1 calc R . .
C8 C 0.6723(5) -0.1249(12) 1.0692(4) 0.0262(16) Uani 1 1 d . . .
H8 H 0.6700 -0.2643 1.0364 0.031 Uiso 1 1 calc R . .
C9 C 0.7196(5) 0.0613(12) 0.8945(4) 0.0223(15) Uani 1 1 d . . .
C10 C 0.6900(5) -0.1494(11) 0.8413(4) 0.0233(16) Uani 1 1 d . . .
H10 H 0.7374 -0.2701 0.8566 0.028 Uiso 1 1 calc R . .
C11 C 0.5911(5) -0.1768(12) 0.7669(5) 0.0272(17) Uani 1 1 d . . .
H11 H 0.5715 -0.3172 0.7316 0.033 Uiso 1 1 calc R . .
C12 C 0.5208(5) -0.0023(12) 0.7435(4) 0.0258(17) Uani 1 1 d . . .
H12 H 0.4536 -0.0230 0.6924 0.031 Uiso 1 1 calc R . .
C13 C 0.5495(5) 0.2046(13) 0.7959(5) 0.0299(17) Uani 1 1 d . . .
H13 H 0.5020 0.3249 0.7810 0.036 Uiso 1 1 calc R . .
C14 C 0.6497(5) 0.2316(12) 0.8709(4) 0.0241(15) Uani 1 1 d . . .
H14 H 0.6693 0.3722 0.9061 0.029 Uiso 1 1 calc R . .
C15 C 0.8335(5) 0.5683(13) 0.5524(4) 0.0300(17) Uani 1 1 d U . .
H15 H 0.8797 0.6920 0.5695 0.036 Uiso 1 1 calc R . .
C16 C 0.7931(5) 0.4989(11) 0.6106(4) 0.0205(15) Uani 1 1 d U . .
C17 C 0.7249(5) 0.3024(11) 0.5674(4) 0.0251(16) Uani 1 1 d . . .
C18 C 0.6652(5) 0.1854(13) 0.6007(5) 0.0313(18) Uani 1 1 d . . .
H18 H 0.6674 0.2284 0.6613 0.038 Uiso 1 1 calc R . .
C19 C 0.6030(5) 0.0074(13) 0.5455(4) 0.0320(17) Uani 1 1 d U . .
H19 H 0.5622 -0.0704 0.5679 0.038 Uiso 1 1 calc R . .
C20 C 0.6004(5) -0.0579(14) 0.4560(5) 0.0379(19) Uani 1 1 d . . .
H20 H 0.5586 -0.1822 0.4195 0.046 Uiso 1 1 calc R . .
C21 C 0.6569(5) 0.0542(13) 0.4201(4) 0.0317(18) Uani 1 1 d . . .
H21 H 0.6540 0.0091 0.3595 0.038 Uiso 1 1 calc R . .
C22 C 0.7196(5) 0.2385(12) 0.4759(4) 0.0255(16) Uani 1 1 d U . .
C23 C 0.8138(5) 0.6108(11) 0.7071(4) 0.0262(17) Uani 1 1 d . . .
H23A H 0.7486 0.6540 0.7034 0.031 Uiso 1 1 calc R . .
H23B H 0.8522 0.7536 0.7148 0.031 Uiso 1 1 calc R . .
C24 C 0.8727(5) 0.4620(12) 0.7999(4) 0.0248(16) Uani 1 1 d . . .
C25 C 0.9802(6) 0.5857(15) 0.3459(5) 0.039(2) Uani 1 1 d . . .
H25A H 1.0512 0.6044 0.3972 0.047 Uiso 1 1 calc R . .
H25B H 0.9527 0.4488 0.3628 0.047 Uiso 1 1 calc R . .
C26 C 0.9198(6) 0.7968(14) 0.3454(5) 0.043(2) Uani 1 1 d . . .
H26A H 0.9459 0.9321 0.3273 0.064 Uiso 1 1 calc R . .
H26B H 0.9262 0.8186 0.4112 0.064 Uiso 1 1 calc R . .
H26C H 0.8487 0.7748 0.2974 0.064 Uiso 1 1 calc R . .
N1 N 0.9046(4) 0.0114(9) 0.9551(3) 0.0231(13) Uani 1 1 d . . .
H1A H 0.8922 -0.1363 0.9338 0.035 Uiso 1 1 calc R . .
H1B H 0.9666 0.0212 1.0088 0.035 Uiso 1 1 calc R . .
H1C H 0.9026 0.1021 0.9061 0.035 Uiso 1 1 calc R . .
O1 O 0.8477(3) -0.2775(8) 1.0603(3) 0.0269(11) Uani 1 1 d . . .
H1 H 0.8704 -0.3479 1.1142 0.040 Uiso 1 1 calc R . .
O2 O 0.8899(3) 0.2562(8) 0.7920(3) 0.0254(11) Uani 1 1 d . . .
O3 O 0.9026(3) 0.5655(8) 0.8825(3) 0.0272(11) Uani 1 1 d . . .
O4 O 0.9765(4) 0.5510(9) 0.2516(3) 0.0386(13) Uani 1 1 d . . .
H4 H 1.0299 0.6002 0.2538 0.058 Uiso 1 1 calc R . .
S1 S 0.79355(14) 0.4118(3) 0.44430(11) 0.0358(5) 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 O1 1.435(8) . ?
C1 C3 1.507(9) . ?
C1 C2 1.550(8) . ?
C1 H1D 1.0000 . ?
C2 N1 1.513(8) . ?
C2 C9 1.535(8) . ?
C2 H2 1.0000 . ?
C3 C8 1.401(9) . ?
C3 C4 1.407(9) . ?
C4 C5 1.392(9) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(9) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.366(9) . ?
C9 C10 1.427(9) . ?
C10 C11 1.393(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.402(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.410(9) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.362(9) . ?
C15 S1 1.737(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.472(9) . ?
C16 C23 1.515(8) . ?
C17 C18 1.407(9) . ?
C17 C22 1.422(8) . ?
C18 C19 1.388(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.413(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.421(9) . ?
C21 H21 0.9500 . ?
C22 S1 1.737(7) . ?
C23 C24 1.543(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O2 1.247(8) . ?
C24 O3 1.282(7) . ?
C25 O4 1.440(8) . ?
C25 C26 1.530(11) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
O1 H1 0.8400 . ?
O4 H4 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
O1 C1 C3 113.9(5) . . ?
O1 C1 C2 107.1(5) . . ?
C3 C1 C2 110.5(5) . . ?
O1 C1 H1D 108.4 . . ?
C3 C1 H1D 108.4 . . ?
C2 C1 H1D 108.4 . . ?
N1 C2 C9 110.4(5) . . ?
N1 C2 C1 109.4(5) . . ?
C9 C2 C1 113.6(5) . . ?
N1 C2 H2 107.8 . . ?
C9 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C8 C3 C4 118.8(6) . . ?
C8 C3 C1 120.7(6) . . ?
C4 C3 C1 120.5(6) . . ?
C5 C4 C3 120.5(7) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.7(7) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.1(7) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C6 120.3(7) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C3 C8 C7 120.7(7) . . ?
C3 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C14 C9 C10 118.9(6) . . ?
C14 C9 C2 120.1(6) . . ?
C10 C9 C2 120.8(6) . . ?
C11 C10 C9 119.5(6) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 121.1(6) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.6(6) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 119.1(6) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 121.8(6) . . ?
C9 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C16 C15 S1 114.5(5) . . ?
C16 C15 H15 122.8 . . ?
S1 C15 H15 122.8 . . ?
C15 C16 C17 111.6(6) . . ?
C15 C16 C23 124.7(6) . . ?
C17 C16 C23 123.7(6) . . ?
C18 C17 C22 119.3(6) . . ?
C18 C17 C16 130.1(6) . . ?
C22 C17 C16 110.6(6) . . ?
C19 C18 C17 120.2(6) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.9(7) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 121.7(7) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 118.4(6) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C21 C22 C17 120.5(6) . . ?
C21 C22 S1 127.1(5) . . ?
C17 C22 S1 112.5(5) . . ?
C16 C23 C24 115.2(5) . . ?
C16 C23 H23A 108.5 . . ?
C24 C23 H23A 108.5 . . ?
C16 C23 H23B 108.5 . . ?
C24 C23 H23B 108.5 . . ?
H23A C23 H23B 107.5 . . ?
O2 C24 O3 124.0(6) . . ?
O2 C24 C23 120.5(5) . . ?
O3 C24 C23 115.5(6) . . ?
O4 C25 C26 111.7(6) . . ?
O4 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
O4 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C25 O4 H4 109.5 . . ?
C15 S1 C22 90.9(3) . . ?

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
O1 C1 C2 N1 -49.9(6) . . . . ?
C3 C1 C2 N1 -174.4(5) . . . . ?
O1 C1 C2 C9 73.9(7) . . . . ?
C3 C1 C2 C9 -50.6(7) . . . . ?
O1 C1 C3 C8 -24.2(8) . . . . ?
C2 C1 C3 C8 96.5(7) . . . . ?
O1 C1 C3 C4 159.1(5) . . . . ?
C2 C1 C3 C4 -80.3(7) . . . . ?
C8 C3 C4 C5 0.1(9) . . . . ?
C1 C3 C4 C5 176.9(6) . . . . ?
C3 C4 C5 C6 -0.2(10) . . . . ?
C4 C5 C6 C7 0.2(10) . . . . ?
C5 C6 C7 C8 -0.1(10) . . . . ?
C4 C3 C8 C7 0.0(9) . . . . ?
C1 C3 C8 C7 -176.8(5) . . . . ?
C6 C7 C8 C3 0.0(10) . . . . ?
N1 C2 C9 C14 -135.9(6) . . . . ?
C1 C2 C9 C14 100.8(7) . . . . ?
N1 C2 C9 C10 49.3(8) . . . . ?
C1 C2 C9 C10 -74.0(8) . . . . ?
C14 C9 C10 C11 0.1(9) . . . . ?
C2 C9 C10 C11 174.9(6) . . . . ?
C9 C10 C11 C12 0.0(9) . . . . ?
C10 C11 C12 C13 -0.3(10) . . . . ?
C11 C12 C13 C14 0.5(10) . . . . ?
C10 C9 C14 C13 0.1(9) . . . . ?
C2 C9 C14 C13 -174.8(6) . . . . ?
C12 C13 C14 C9 -0.4(10) . . . . ?
S1 C15 C16 C17 0.7(7) . . . . ?
S1 C15 C16 C23 -178.4(5) . . . . ?
C15 C16 C17 C18 -177.0(7) . . . . ?
C23 C16 C17 C18 2.1(11) . . . . ?
C15 C16 C17 C22 -0.2(7) . . . . ?
C23 C16 C17 C22 178.9(6) . . . . ?
C22 C17 C18 C19 1.0(10) . . . . ?
C16 C17 C18 C19 177.6(6) . . . . ?
C17 C18 C19 C20 0.6(10) . . . . ?
C18 C19 C20 C21 -1.4(11) . . . . ?
C19 C20 C21 C22 0.5(11) . . . . ?
C20 C21 C22 C17 1.2(10) . . . . ?
C20 C21 C22 S1 -177.4(6) . . . . ?
C18 C17 C22 C21 -1.9(9) . . . . ?
C16 C17 C22 C21 -179.1(6) . . . . ?
C18 C17 C22 S1 176.8(5) . . . . ?
C16 C17 C22 S1 -0.4(7) . . . . ?
C15 C16 C23 C24 -113.2(7) . . . . ?
C17 C16 C23 C24 67.8(9) . . . . ?
C16 C23 C24 O2 -8.3(10) . . . . ?
C16 C23 C24 O3 170.7(6) . . . . ?
C16 C15 S1 C22 -0.8(6) . . . . ?
C21 C22 S1 C15 179.3(6) . . . . ?
C17 C22 S1 C15 0.7(5) . . . . ?

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 O2 0.84 1.90 2.688(7) 156.5 2_756
O1 H1 O4 0.84 2.04 2.833(6) 156.4 1_546
N1 H1C O2 0.91 1.90 2.805(6) 172.0 .
N1 H1B O3 0.91 1.90 2.813(6) 175.3 2_747
N1 H1A O3 0.91 1.95 2.828(7) 161.9 1_545

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.077
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_WAKABAYASHI3_3
_database_code_depnum_ccdc_archive 'CCDC 1037534'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;
#data_k143 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H31 N O4 S'
_chemical_formula_weight         465.59
_chemical_absolute_configuration rmad

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)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   15.057(3)
_cell_length_b                   5.8260(11)
_cell_length_c                   15.588(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.035(3)
_cell_angle_gamma                90.00
_cell_volume                     1218.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2817
_cell_measurement_theta_min      2.5465
_cell_measurement_theta_max      27.0575

_exptl_crystal_description       column
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9350
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_process_details   
;
SADABS; Sheldrick 1996
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         90
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6730
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         26.02
_reflns_number_total             3805
_reflns_number_gt                3109
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0821P)²+0.1179P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(14)
_refine_ls_number_reflns         3805
_refine_ls_number_parameters     302
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1558
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.001
_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 0.7322(3) 0.5665(8) 0.5717(3) 0.0332(9) Uani 1 1 d . . .
H1D H 0.7202 0.5195 0.6273 0.040 Uiso 1 1 calc R . .
C2 C 0.6568(3) 0.4400(7) 0.4811(3) 0.0287(9) Uani 1 1 d . . .
H2 H 0.6596 0.2732 0.4971 0.034 Uiso 1 1 calc R . .
C3 C 0.8389(3) 0.5038(7) 0.5948(3) 0.0327(9) Uani 1 1 d . . .
C4 C 0.8801(4) 0.3060(9) 0.6444(3) 0.0523(12) Uani 1 1 d . . .
H4A H 0.8432 0.2119 0.6665 0.063 Uiso 1 1 calc R . .
C5 C 0.9766(4) 0.2428(10) 0.6626(4) 0.0641(15) Uani 1 1 d . . .
H5 H 1.0049 0.1045 0.6963 0.077 Uiso 1 1 calc R . .
C6 C 1.0298(4) 0.3777(11) 0.6324(4) 0.0664(16) Uani 1 1 d . . .
H6 H 1.0951 0.3337 0.6441 0.080 Uiso 1 1 calc R . .
C7 C 0.9897(4) 0.5761(12) 0.5854(4) 0.0638(15) Uani 1 1 d . . .
H7 H 1.0282 0.6727 0.5661 0.077 Uiso 1 1 calc R . .
C8 C 0.8935(3) 0.6407(9) 0.5649(3) 0.0498(12) Uani 1 1 d . . .
H8 H 0.8658 0.7784 0.5305 0.060 Uiso 1 1 calc R . .
C9 C 0.6785(3) 0.4634(7) 0.3961(3) 0.0287(9) Uani 1 1 d . . .
C10 C 0.7240(3) 0.2832(9) 0.3732(3) 0.0425(11) Uani 1 1 d . . .
H10 H 0.7369 0.1430 0.4080 0.051 Uiso 1 1 calc R . .
C11 C 0.7507(4) 0.3076(10) 0.2995(3) 0.0535(14) Uani 1 1 d . . .
H11 H 0.7823 0.1845 0.2841 0.064 Uiso 1 1 calc R . .
C12 C 0.7315(3) 0.5093(9) 0.2489(3) 0.0484(13) Uani 1 1 d . . .
H12 H 0.7505 0.5262 0.1989 0.058 Uiso 1 1 calc R . .
C13 C 0.6853(3) 0.6853(9) 0.2699(3) 0.0444(11) Uani 1 1 d . . .
H13 H 0.6708 0.8237 0.2338 0.053 Uiso 1 1 calc R . .
C14 C 0.6594(3) 0.6626(8) 0.3439(3) 0.0340(10) Uani 1 1 d . . .
H14 H 0.6279 0.7868 0.3588 0.041 Uiso 1 1 calc R . .
C15 C 0.2547(4) -0.0487(10) 0.0698(3) 0.0490(12) Uani 1 1 d . . .
H15 H 0.2302 -0.1795 0.0888 0.059 Uiso 1 1 calc R . .
C16 C 0.3454(3) 0.0417(8) 0.1242(3) 0.0375(10) Uani 1 1 d . . .
C17 C 0.3650(3) 0.2355(8) 0.0788(3) 0.0345(10) Uani 1 1 d . . .
C18 C 0.4500(3) 0.3699(8) 0.1089(3) 0.0418(11) Uani 1 1 d . . .
H18 H 0.5063 0.3391 0.1688 0.050 Uiso 1 1 calc R . .
C19 C 0.4530(4) 0.5474(9) 0.0522(3) 0.0512(13) Uani 1 1 d . . .
H19 H 0.5114 0.6390 0.0733 0.061 Uiso 1 1 calc R . .
C20 C 0.3713(4) 0.5939(10) -0.0356(3) 0.0552(13) Uani 1 1 d . . .
H20 H 0.3746 0.7158 -0.0745 0.066 Uiso 1 1 calc R . .
C21 C 0.2864(4) 0.4666(10) -0.0666(3) 0.0494(13) Uani 1 1 d . . .
H21 H 0.2301 0.5016 -0.1259 0.059 Uiso 1 1 calc R . .
C22 C 0.2834(3) 0.2863(9) -0.0107(3) 0.0406(11) Uani 1 1 d . . .
C23 C 0.4197(4) -0.0631(8) 0.2187(3) 0.0458(11) Uani 1 1 d . . .
H23A H 0.3947 -0.2162 0.2250 0.055 Uiso 1 1 calc R . .
H23B H 0.4834 -0.0866 0.2159 0.055 Uiso 1 1 calc R . .
C24 C 0.4405(3) 0.0744(8) 0.3080(3) 0.0297(9) Uani 1 1 d . . .
C25 C 0.8392(5) 0.9242(13) 0.8275(4) 0.0849(15) Uani 1 1 d DU . .
H25A H 0.8144 0.8782 0.8739 0.102 Uiso 1 1 calc R . .
H25B H 0.8817 1.0616 0.8540 0.102 Uiso 1 1 calc R . .
C26 C 0.9024(6) 0.7335(15) 0.8201(5) 0.105(2) Uani 1 1 d DU . .
H26A H 0.8582 0.5988 0.7932 0.126 Uiso 1 1 calc R . .
H26B H 0.9238 0.7809 0.7714 0.126 Uiso 1 1 calc R . .
C27 C 0.9907(5) 0.6542(16) 0.9036(5) 0.101(2) Uani 1 1 d U . .
H27A H 1.0481 0.7479 0.9118 0.152 Uiso 1 1 calc R . .
H27B H 1.0033 0.4933 0.8944 0.152 Uiso 1 1 calc R . .
H27C H 0.9803 0.6677 0.9611 0.152 Uiso 1 1 calc R . .
N1 N 0.5549(2) 0.5239(5) 0.4566(2) 0.0293(8) Uani 1 1 d . . .
H1A H 0.5487 0.6724 0.4365 0.044 Uiso 1 1 calc R . .
H1B H 0.5444 0.5149 0.5095 0.044 Uiso 1 1 calc R . .
H1C H 0.5092 0.4358 0.4087 0.044 Uiso 1 1 calc R . .
O1 O 0.7129(2) 0.8031(5) 0.5559(2) 0.0409(7) Uani 1 1 d . . .
H1 H 0.7305 0.8699 0.6089 0.061 Uiso 1 1 calc R . .
O2 O 0.4167(2) 0.2802(5) 0.30141(19) 0.0399(7) Uani 1 1 d . . .
O3 O 0.4860(2) -0.0293(6) 0.38697(19) 0.0422(8) Uani 1 1 d . . .
O4 O 0.7597(2) 0.9825(8) 0.7427(2) 0.0683(11) Uani 1 1 d U . .
H4 H 0.7066 0.9534 0.7458 0.102 Uiso 1 1 calc R . .
S1 S 0.18685(9) 0.0940(3) -0.03724(8) 0.0527(4) 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 O1 1.407(5) . ?
C1 C3 1.523(6) . ?
C1 C2 1.539(5) . ?
C1 H1D 1.0000 . ?
C2 N1 1.485(5) . ?
C2 C9 1.507(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.370(6) . ?
C3 C8 1.370(6) . ?
C4 C5 1.397(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.351(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.355(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(7) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.371(6) . ?
C9 C10 1.386(6) . ?
C10 C11 1.385(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.372(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.361(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.346(6) . ?
C15 S1 1.724(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.433(6) . ?
C16 C23 1.515(6) . ?
C17 C18 1.388(6) . ?
C17 C22 1.409(6) . ?
C18 C19 1.373(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.362(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(7) . ?
C21 H21 0.9500 . ?
C22 S1 1.730(5) . ?
C23 C24 1.510(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O2 1.242(5) . ?
C24 O3 1.258(5) . ?
C25 O4 1.363(6) . ?
C25 C26 1.501(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.450(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
O1 H1 0.8400 . ?
O4 H4 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
O1 C1 C3 112.8(3) . . ?
O1 C1 C2 107.5(3) . . ?
C3 C1 C2 111.2(3) . . ?
O1 C1 H1D 108.4 . . ?
C3 C1 H1D 108.4 . . ?
C2 C1 H1D 108.4 . . ?
N1 C2 C9 110.9(3) . . ?
N1 C2 C1 108.9(3) . . ?
C9 C2 C1 113.5(3) . . ?
N1 C2 H2 107.8 . . ?
C9 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C4 C3 C8 119.6(4) . . ?
C4 C3 C1 119.6(4) . . ?
C8 C3 C1 120.8(4) . . ?
C3 C4 C5 119.9(5) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 120.2(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 119.7(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 121.3(5) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 119.3(5) . . ?
C3 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C14 C9 C10 118.9(4) . . ?
C14 C9 C2 121.8(4) . . ?
C10 C9 C2 119.2(4) . . ?
C11 C10 C9 119.9(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.1(5) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.9(5) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.9(4) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 S1 114.0(4) . . ?
C16 C15 H15 123.0 . . ?
S1 C15 H15 123.0 . . ?
C15 C16 C17 112.0(4) . . ?
C15 C16 C23 122.9(4) . . ?
C17 C16 C23 124.9(4) . . ?
C18 C17 C22 118.1(4) . . ?
C18 C17 C16 130.0(4) . . ?
C22 C17 C16 111.9(4) . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.5(5) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.1(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C21 C22 C17 121.4(4) . . ?
C21 C22 S1 127.4(4) . . ?
C17 C22 S1 111.1(3) . . ?
C24 C23 C16 115.8(4) . . ?
C24 C23 H23A 108.3 . . ?
C16 C23 H23A 108.3 . . ?
C24 C23 H23B 108.3 . . ?
C16 C23 H23B 108.3 . . ?
H23A C23 H23B 107.4 . . ?
O2 C24 O3 123.6(4) . . ?
O2 C24 C23 120.3(4) . . ?
O3 C24 C23 116.1(4) . . ?
O4 C25 C26 114.7(6) . . ?
O4 C25 H25A 108.6 . . ?
C26 C25 H25A 108.6 . . ?
O4 C25 H25B 108.6 . . ?
C26 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
C27 C26 C25 121.4(6) . . ?
C27 C26 H26A 107.0 . . ?
C25 C26 H26A 107.0 . . ?
C27 C26 H26B 107.0 . . ?
C25 C26 H26B 107.0 . . ?
H26A C26 H26B 106.7 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C25 O4 H4 109.5 . . ?
C15 S1 C22 91.0(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
O1 C1 C2 N1 -50.8(4) . . . . ?
C3 C1 C2 N1 -174.7(3) . . . . ?
O1 C1 C2 C9 73.2(4) . . . . ?
C3 C1 C2 C9 -50.7(5) . . . . ?
O1 C1 C3 C4 156.7(4) . . . . ?
C2 C1 C3 C4 -82.5(5) . . . . ?
O1 C1 C3 C8 -24.5(5) . . . . ?
C2 C1 C3 C8 96.3(5) . . . . ?
C8 C3 C4 C5 -1.3(7) . . . . ?
C1 C3 C4 C5 177.5(4) . . . . ?
C3 C4 C5 C6 0.8(8) . . . . ?
C4 C5 C6 C7 0.8(9) . . . . ?
C5 C6 C7 C8 -2.0(9) . . . . ?
C4 C3 C8 C7 0.1(7) . . . . ?
C1 C3 C8 C7 -178.7(4) . . . . ?
C6 C7 C8 C3 1.5(8) . . . . ?
N1 C2 C9 C14 47.9(5) . . . . ?
C1 C2 C9 C14 -75.0(5) . . . . ?
N1 C2 C9 C10 -135.6(4) . . . . ?
C1 C2 C9 C10 101.5(4) . . . . ?
C14 C9 C10 C11 1.0(6) . . . . ?
C2 C9 C10 C11 -175.6(4) . . . . ?
C9 C10 C11 C12 -0.5(7) . . . . ?
C10 C11 C12 C13 -0.7(7) . . . . ?
C11 C12 C13 C14 1.3(7) . . . . ?
C10 C9 C14 C13 -0.4(6) . . . . ?
C2 C9 C14 C13 176.1(4) . . . . ?
C12 C13 C14 C9 -0.8(6) . . . . ?
S1 C15 C16 C17 -1.0(5) . . . . ?
S1 C15 C16 C23 -176.8(3) . . . . ?
C15 C16 C17 C18 -177.4(4) . . . . ?
C23 C16 C17 C18 -1.6(7) . . . . ?
C15 C16 C17 C22 1.3(5) . . . . ?
C23 C16 C17 C22 177.0(4) . . . . ?
C22 C17 C18 C19 0.3(6) . . . . ?
C16 C17 C18 C19 178.8(4) . . . . ?
C17 C18 C19 C20 -0.1(7) . . . . ?
C18 C19 C20 C21 0.9(8) . . . . ?
C19 C20 C21 C22 -1.7(7) . . . . ?
C20 C21 C22 C17 1.9(7) . . . . ?
C20 C21 C22 S1 -176.9(4) . . . . ?
C18 C17 C22 C21 -1.2(6) . . . . ?
C16 C17 C22 C21 -180.0(4) . . . . ?
C18 C17 C22 S1 177.8(3) . . . . ?
C16 C17 C22 S1 -1.0(4) . . . . ?
C15 C16 C23 C24 -111.5(5) . . . . ?
C17 C16 C23 C24 73.2(5) . . . . ?
C16 C23 C24 O2 -16.3(6) . . . . ?
C16 C23 C24 O3 166.6(4) . . . . ?
O4 C25 C26 C27 178.9(7) . . . . ?
C16 C15 S1 C22 0.3(4) . . . . ?
C21 C22 S1 C15 179.3(5) . . . . ?
C17 C22 S1 C15 0.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_WAKABAYASHI3_4
_database_code_depnum_ccdc_archive 'CCDC 1037535'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;
# data_im1781a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H33 N O4 S'
_chemical_formula_weight         479.61
_chemical_absolute_configuration rm

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   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   15.102(3)
_cell_length_b                   5.8480(9)
_cell_length_c                   15.421(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.810(3)
_cell_angle_gamma                90.00
_cell_volume                     1246.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6078
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      31.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Rigaku Saturn'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11260
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         31.00
_reflns_number_total             6564
_reflns_number_gt                6078
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0437P)²+0.2346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_number_reflns         6564
_refine_ls_number_parameters     311
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_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 0.81248(10) -0.1246(3) 0.60163(10) 0.0145(3) Uani 1 1 d . . .
C2 C 0.76767(11) -0.3085(3) 0.62465(11) 0.0194(3) Uani 1 1 d . . .
H2 H 0.7554 -0.4448 0.5882 0.023 Uiso 1 1 calc R . .
C3 C 0.74065(11) -0.2939(3) 0.70109(11) 0.0232(3) Uani 1 1 d . . .
H3 H 0.7095 -0.4197 0.7160 0.028 Uiso 1 1 calc R . .
C4 C 0.75923(11) -0.0964(3) 0.75531(11) 0.0220(3) Uani 1 1 d . . .
H4 H 0.7407 -0.0863 0.8072 0.026 Uiso 1 1 calc R . .
C5 C 0.80497(11) 0.0866(3) 0.73331(10) 0.0202(3) Uani 1 1 d . . .
H5 H 0.8189 0.2212 0.7710 0.024 Uiso 1 1 calc R . .
C6 C 0.83049(10) 0.0735(3) 0.65608(10) 0.0169(3) Uani 1 1 d . . .
H6 H 0.8604 0.2008 0.6405 0.020 Uiso 1 1 calc R . .
C7 C 0.83656(10) -0.1403(3) 0.51565(9) 0.0136(3) Uani 1 1 d . . .
H7 H 0.8347 -0.3051 0.4978 0.016 Uiso 1 1 calc R . .
C8 C 0.76531(9) -0.0084(3) 0.42883(9) 0.0147(2) Uani 1 1 d . . .
H8 H 0.7795 -0.0480 0.3726 0.018 Uiso 1 1 calc R . .
N9 N 0.93689(8) -0.0524(2) 0.53907(8) 0.0141(2) Uani 1 1 d . . .
H9A H 0.9404 0.0973 0.5563 0.021 Uiso 1 1 calc R . .
H9B H 0.9512 -0.0658 0.4873 0.021 Uiso 1 1 calc R . .
H9C H 0.9800 -0.1352 0.5878 0.021 Uiso 1 1 calc R . .
O10 O 0.78273(8) 0.22919(18) 0.44775(7) 0.0179(2) Uani 1 1 d . . .
H10 H 0.7750 0.2980 0.3974 0.027 Uiso 1 1 calc R . .
C11 C 0.66156(10) -0.0757(3) 0.40771(10) 0.0155(3) Uani 1 1 d . . .
C12 C 0.60238(11) 0.0603(3) 0.43544(11) 0.0195(3) Uani 1 1 d . . .
H12 H 0.6265 0.2005 0.4674 0.023 Uiso 1 1 calc R . .
C13 C 0.50776(11) -0.0067(3) 0.41691(11) 0.0236(3) Uani 1 1 d . . .
H13 H 0.4676 0.0881 0.4357 0.028 Uiso 1 1 calc R . .
C14 C 0.47253(12) -0.2122(3) 0.37092(12) 0.0239(3) Uani 1 1 d . . .
H14 H 0.4083 -0.2587 0.3587 0.029 Uiso 1 1 calc R . .
C15 C 0.53078(12) -0.3493(3) 0.34284(12) 0.0230(3) Uani 1 1 d . . .
H15 H 0.5065 -0.4897 0.3112 0.028 Uiso 1 1 calc R . .
C16 C 0.62494(11) -0.2818(3) 0.36093(10) 0.0186(3) Uani 1 1 d . . .
H16 H 0.6647 -0.3763 0.3414 0.022 Uiso 1 1 calc R . .
C17 C 0.86604(11) -0.0359(2) 0.13677(10) 0.0161(3) Uani 1 1 d . . .
C18 C 0.77799(11) -0.1320(3) 0.08828(10) 0.0191(3) Uani 1 1 d . . .
H18 H 0.7562 -0.2641 0.1098 0.023 Uiso 1 1 calc R . .
S19 S 0.70877(3) 0.00788(7) -0.01642(2) 0.01875(8) Uani 1 1 d . . .
C20 C 0.79971(11) 0.3865(3) -0.05690(10) 0.0176(3) Uani 1 1 d . . .
H20 H 0.7446 0.4149 -0.1139 0.021 Uiso 1 1 calc R . .
C21 C 0.88101(11) 0.5237(3) -0.03035(10) 0.0195(3) Uani 1 1 d . . .
H21 H 0.8821 0.6464 -0.0703 0.023 Uiso 1 1 calc R . .
C22 C 0.96195(11) 0.4847(3) 0.05462(10) 0.0191(3) Uani 1 1 d . . .
H22 H 1.0170 0.5811 0.0717 0.023 Uiso 1 1 calc R . .
C23 C 0.96193(10) 0.3063(3) 0.11378(10) 0.0168(3) Uani 1 1 d . . .
H23 H 1.0165 0.2818 0.1716 0.020 Uiso 1 1 calc R . .
C24 C 0.88110(10) 0.1619(2) 0.08805(10) 0.0146(3) Uani 1 1 d . . .
C25 C 0.80084(10) 0.2052(3) 0.00242(10) 0.0151(3) Uani 1 1 d . . .
C26 C 0.94013(11) -0.1361(3) 0.22629(10) 0.0187(3) Uani 1 1 d . . .
H26A H 1.0020 -0.1509 0.2189 0.022 Uiso 1 1 calc R . .
H26B H 0.9190 -0.2921 0.2342 0.022 Uiso 1 1 calc R . .
C27 C 0.95879(9) -0.0007(3) 0.31649(9) 0.0141(2) Uani 1 1 d . . .
O28 O 1.00082(8) -0.10475(19) 0.39433(7) 0.0180(2) Uani 1 1 d . . .
O29 O 0.93467(7) 0.20610(19) 0.31005(7) 0.0172(2) Uani 1 1 d . . .
C30 C 0.45909(12) 0.0066(4) 0.11223(12) 0.0283(3) Uani 1 1 d . . .
H30A H 0.4890 -0.1451 0.1205 0.042 Uiso 1 1 calc R . .
H30B H 0.3993 0.0080 0.0544 0.042 Uiso 1 1 calc R . .
H30C H 0.4441 0.0420 0.1670 0.042 Uiso 1 1 calc R . .
C31 C 0.52888(11) 0.1851(3) 0.10411(11) 0.0218(3) Uani 1 1 d . . .
H31A H 0.5446 0.1469 0.0494 0.026 Uiso 1 1 calc R . .
H31B H 0.4968 0.3365 0.0919 0.026 Uiso 1 1 calc R . .
C32 C 0.62200(11) 0.1990(3) 0.19297(10) 0.0183(3) Uani 1 1 d . . .
H32A H 0.6060 0.2254 0.2484 0.022 Uiso 1 1 calc R . .
H32B H 0.6566 0.0512 0.2025 0.022 Uiso 1 1 calc R . .
C33 C 0.68803(11) 0.3887(3) 0.18770(10) 0.0193(3) Uani 1 1 d . . .
H33A H 0.7121 0.3502 0.1385 0.023 Uiso 1 1 calc R . .
H33B H 0.6505 0.5324 0.1685 0.023 Uiso 1 1 calc R . .
O34 O 0.76908(8) 0.4239(2) 0.27642(8) 0.0201(2) Uani 1 1 d . . .
H34 H 0.8169 0.3495 0.2769 0.030 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.391(2) . ?
C1 C6 1.392(2) . ?
C1 C7 1.5125(19) . ?
C2 C3 1.397(2) . ?
C3 C4 1.387(3) . ?
C4 C5 1.388(2) . ?
C5 C6 1.394(2) . ?
C7 N9 1.4995(17) . ?
C7 C8 1.5434(19) . ?
C8 O10 1.4222(19) . ?
C8 C11 1.5178(19) . ?
C11 C12 1.387(2) . ?
C11 C16 1.399(2) . ?
C12 C13 1.396(2) . ?
C13 C14 1.387(3) . ?
C14 C15 1.383(2) . ?
C15 C16 1.391(2) . ?
C17 C18 1.357(2) . ?
C17 C24 1.447(2) . ?
C17 C26 1.501(2) . ?
C18 S19 1.7338(16) . ?
S19 C25 1.7386(15) . ?
C20 C21 1.383(2) . ?
C20 C25 1.396(2) . ?
C21 C22 1.404(2) . ?
C22 C23 1.386(2) . ?
C23 C24 1.403(2) . ?
C24 C25 1.4087(19) . ?
C26 C27 1.5249(19) . ?
C27 O29 1.255(2) . ?
C27 O28 1.2644(17) . ?
C30 C31 1.524(2) . ?
C31 C32 1.519(2) . ?
C32 C33 1.515(2) . ?
C33 O34 1.4354(18) . ?

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 C6 119.09(13) . . ?
C2 C1 C7 119.41(13) . . ?
C6 C1 C7 121.44(13) . . ?
C1 C2 C3 120.43(15) . . ?
C4 C3 C2 120.16(15) . . ?
C3 C4 C5 119.63(14) . . ?
C4 C5 C6 120.20(15) . . ?
C1 C6 C5 120.46(14) . . ?
N9 C7 C1 110.20(11) . . ?
N9 C7 C8 108.69(11) . . ?
C1 C7 C8 113.58(11) . . ?
O10 C8 C11 112.75(12) . . ?
O10 C8 C7 107.68(11) . . ?
C11 C8 C7 110.76(12) . . ?
C12 C11 C16 118.90(13) . . ?
C12 C11 C8 121.55(14) . . ?
C16 C11 C8 119.54(13) . . ?
C11 C12 C13 120.65(15) . . ?
C14 C13 C12 119.85(15) . . ?
C15 C14 C13 120.07(15) . . ?
C14 C15 C16 120.04(15) . . ?
C15 C16 C11 120.48(14) . . ?
C18 C17 C24 111.69(13) . . ?
C18 C17 C26 123.10(14) . . ?
C24 C17 C26 125.07(13) . . ?
C17 C18 S19 113.97(12) . . ?
C18 S19 C25 90.95(7) . . ?
C21 C20 C25 118.17(13) . . ?
C20 C21 C22 121.11(14) . . ?
C23 C22 C21 120.35(14) . . ?
C22 C23 C24 119.88(13) . . ?
C23 C24 C25 118.55(13) . . ?
C23 C24 C17 129.46(13) . . ?
C25 C24 C17 111.98(13) . . ?
C20 C25 C24 121.93(13) . . ?
C20 C25 S19 126.67(11) . . ?
C24 C25 S19 111.40(11) . . ?
C17 C26 C27 115.51(12) . . ?
O29 C27 O28 123.86(13) . . ?
O29 C27 C26 119.16(12) . . ?
O28 C27 C26 116.94(14) . . ?
C32 C31 C30 112.45(13) . . ?
C33 C32 C31 112.37(12) . . ?
O34 C33 C32 112.35(12) . . ?

_diffrn_measured_fraction_theta_max 0.887
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.047

#===END
