# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_e3732a_a
_database_code_depnum_ccdc_archive 'CCDC 1555873'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2018-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 N O3 S'
_chemical_formula_sum            'C27 H25 N O3 S'
_chemical_formula_weight         443.54

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.892(12)
_cell_length_b                   9.668(10)
_cell_length_c                   13.91(2)
_cell_angle_alpha                86.33(5)
_cell_angle_beta                 86.29(4)
_cell_angle_gamma                67.91(4)
_cell_volume                     1105(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8282
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.468
_diffrn_reflns_theta_max         27.592
_diffrn_reflns_theta_full        25.042
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4865
_reflns_number_gt                3155
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.3418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4865
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65030(8) 1.02069(6) 0.13650(4) 0.04652(17) Uani 1 1 d . . . . .
O1 O 0.5487(2) 1.17300(17) 0.11555(13) 0.0612(5) Uani 1 1 d . . . . .
O2 O 0.7997(2) 0.95404(18) 0.08254(12) 0.0566(5) Uani 1 1 d . . . . .
C1 C 0.6945(3) 0.9990(2) 0.25932(16) 0.0405(5) Uani 1 1 d . . . . .
C2 C 0.8309(3) 0.8822(2) 0.29162(17) 0.0467(6) Uani 1 1 d . . . . .
H2 H 0.9000 0.8120 0.2477 0.056 Uiso 1 1 calc R U . . .
C3 C 0.8659(3) 0.8686(3) 0.38783(18) 0.0508(6) Uani 1 1 d . . . . .
H3 H 0.9598 0.7887 0.4095 0.061 Uiso 1 1 calc R U . . .
C4 C 0.7668(3) 0.9691(3) 0.45324(17) 0.0470(6) Uani 1 1 d . . . . .
C5 C 0.6282(3) 1.0830(3) 0.42008(18) 0.0501(6) Uani 1 1 d . . . . .
H5 H 0.5568 1.1509 0.4644 0.060 Uiso 1 1 calc R U . . .
C6 C 0.5924(3) 1.0994(2) 0.32408(17) 0.0471(6) Uani 1 1 d . . . . .
H6 H 0.4982 1.1790 0.3024 0.057 Uiso 1 1 calc R U . . .
C7 C 0.8092(4) 0.9573(3) 0.55774(19) 0.0679(8) Uani 1 1 d . . . . .
H7A H 0.7242 0.9388 0.5987 0.102 Uiso 1 1 calc R U . . .
H7B H 0.8174 1.0508 0.5750 0.102 Uiso 1 1 calc R U . . .
H7C H 0.9134 0.8746 0.5672 0.102 Uiso 1 1 calc R U . . .
N1 N 0.5368(2) 0.92322(19) 0.12138(13) 0.0423(4) Uani 1 1 d . . . . .
C8 C 0.3622(3) 0.9957(2) 0.14882(18) 0.0499(6) Uani 1 1 d . . . . .
H8A H 0.3072 1.0807 0.1037 0.060 Uiso 1 1 calc R U . . .
H8B H 0.3462 1.0316 0.2152 0.060 Uiso 1 1 calc R U . . .
C9 C 0.3009(3) 0.8710(2) 0.14190(17) 0.0464(6) Uani 1 1 d . . . . .
H9A H 0.2696 0.8669 0.0754 0.056 Uiso 1 1 calc R U . . .
H9B H 0.2056 0.8851 0.1866 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4458(3) 0.7256(2) 0.17047(15) 0.0371(5) Uani 1 1 d . . . . .
C11 C 0.5927(3) 0.7638(2) 0.13884(14) 0.0380(5) Uani 1 1 d . . . . .
C12 C 0.4336(3) 0.7034(2) 0.27972(15) 0.0379(5) Uani 1 1 d . . . . .
O3 O 0.4888(2) 0.76680(18) 0.33269(11) 0.0527(4) Uani 1 1 d . . . . .
C13 C 0.3439(2) 0.6085(2) 0.31989(15) 0.0386(5) Uani 1 1 d . . . . .
C14 C 0.3327(3) 0.5872(3) 0.41992(17) 0.0505(6) Uani 1 1 d . . . . .
H14 H 0.3823 0.6319 0.4602 0.061 Uiso 1 1 calc R U . . .
C15 C 0.2498(4) 0.5012(3) 0.4600(2) 0.0663(8) Uani 1 1 d . . . . .
H15 H 0.2426 0.4858 0.5280 0.080 Uiso 1 1 calc R U . . .
C16 C 0.1776(4) 0.4379(3) 0.4013(2) 0.0690(8) Uani 1 1 d . . . . .
H16 H 0.1186 0.3801 0.4291 0.083 Uiso 1 1 calc R U . . .
C17 C 0.1894(3) 0.4569(3) 0.3027(2) 0.0597(7) Uani 1 1 d . . . . .
H17 H 0.1397 0.4109 0.2633 0.072 Uiso 1 1 calc R U . . .
C18 C 0.2730(3) 0.5425(2) 0.25970(17) 0.0424(5) Uani 1 1 d . . . . .
C19 C 0.2867(3) 0.5623(3) 0.15195(17) 0.0487(6) Uani 1 1 d . . . . .
H19A H 0.1898 0.6470 0.1296 0.058 Uiso 1 1 calc R U . . .
H19B H 0.2895 0.4711 0.1221 0.058 Uiso 1 1 calc R U . . .
C20 C 0.4384(3) 0.5921(2) 0.11960(16) 0.0440(5) Uani 1 1 d . . . . .
H20A H 0.4391 0.6127 0.0490 0.053 Uiso 1 1 calc R U . . .
H20B H 0.5357 0.5022 0.1342 0.053 Uiso 1 1 calc R U . . .
C21 C 0.7454(3) 0.6709(2) 0.12370(15) 0.0424(5) Uani 1 1 d . . . . .
H21 H 0.8186 0.7111 0.0918 0.051 Uiso 1 1 calc R U . . .
C22 C 0.8109(3) 0.5096(2) 0.15256(16) 0.0397(5) Uani 1 1 d . . . . .
C23 C 0.7965(3) 0.4620(3) 0.24778(17) 0.0470(6) Uani 1 1 d . . . . .
H23 H 0.7449 0.5339 0.2949 0.056 Uiso 1 1 calc R U . . .
C24 C 0.8560(3) 0.3117(3) 0.2751(2) 0.0585(7) Uani 1 1 d . . . . .
H24 H 0.8428 0.2811 0.3404 0.070 Uiso 1 1 calc R U . . .
C25 C 0.9332(3) 0.2078(3) 0.2091(2) 0.0646(8) Uani 1 1 d . . . . .
H25 H 0.9740 0.1047 0.2281 0.077 Uiso 1 1 calc R U . . .
C26 C 0.9525(3) 0.2517(3) 0.1144(2) 0.0609(7) Uani 1 1 d . . . . .
H26 H 1.0070 0.1790 0.0683 0.073 Uiso 1 1 calc R U . . .
C27 C 0.8924(3) 0.4017(3) 0.08674(18) 0.0481(6) Uani 1 1 d . . . . .
H27 H 0.9072 0.4314 0.0215 0.058 Uiso 1 1 calc R U . . .


_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 1.425(2) . ?
S1 O1 1.431(2) . ?
S1 N1 1.649(2) . ?
S1 C1 1.760(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.387(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C4 C7 1.512(4) . ?
C5 C6 1.379(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N1 C11 1.440(3) . ?
N1 C8 1.479(4) . ?
C8 C9 1.509(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.558(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.518(3) . ?
C10 C12 1.524(4) . ?
C10 C20 1.536(3) . ?
C11 C21 1.329(3) . ?
C12 O3 1.221(3) . ?
C12 C13 1.490(3) . ?
C13 C18 1.395(3) . ?
C13 C14 1.396(4) . ?
C14 C15 1.376(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.371(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.502(4) . ?
C19 C20 1.517(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.483(3) . ?
C21 H21 0.9500 . ?
C22 C27 1.386(3) . ?
C22 C23 1.388(4) . ?
C23 C24 1.383(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.358(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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 119.87(12) . . ?
O2 S1 N1 107.75(13) . . ?
O1 S1 N1 105.33(14) . . ?
O2 S1 C1 107.59(14) . . ?
O1 S1 C1 108.89(12) . . ?
N1 S1 C1 106.72(10) . . ?
C6 C1 C2 119.9(2) . . ?
C6 C1 S1 119.76(19) . . ?
C2 C1 S1 120.39(18) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 C7 121.0(2) . . ?
C5 C4 C7 120.7(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
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 111.12(18) . . ?
C11 N1 S1 122.98(17) . . ?
C8 N1 S1 116.13(17) . . ?
N1 C8 C9 102.61(19) . . ?
N1 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
N1 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.2 . . ?
C8 C9 C10 105.1(2) . . ?
C8 C9 H9A 110.7 . . ?
C10 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
C10 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C11 C10 C12 111.21(17) . . ?
C11 C10 C20 113.59(18) . . ?
C12 C10 C20 111.31(18) . . ?
C11 C10 C9 102.79(19) . . ?
C12 C10 C9 107.17(18) . . ?
C20 C10 C9 110.2(2) . . ?
C21 C11 N1 124.2(2) . . ?
C21 C11 C10 128.2(2) . . ?
N1 C11 C10 107.56(18) . . ?
O3 C12 C13 121.0(2) . . ?
O3 C12 C10 121.2(2) . . ?
C13 C12 C10 117.71(18) . . ?
C18 C13 C14 120.7(2) . . ?
C18 C13 C12 121.2(2) . . ?
C14 C13 C12 118.0(2) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 117.9(2) . . ?
C17 C18 C19 120.9(2) . . ?
C13 C18 C19 121.2(2) . . ?
C18 C19 C20 111.55(19) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C10 111.11(19) . . ?
C19 C20 H20A 109.4 . . ?
C10 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C10 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C11 C21 C22 125.3(2) . . ?
C11 C21 H21 117.3 . . ?
C22 C21 H21 117.3 . . ?
C27 C22 C23 117.6(2) . . ?
C27 C22 C21 121.6(2) . . ?
C23 C22 C21 120.7(2) . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.1(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 119.9(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C22 121.1(3) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.039

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_e4355A_a
_database_code_depnum_ccdc_archive 'CCDC 1864130'
_audit_update_record             
;
2018-08-27 deposited with the CCDC.
2018-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 N O3 S'
_chemical_formula_sum            'C22 H25 N O3 S'
_chemical_formula_weight         383.49

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6023(4)
_cell_length_b                   7.8229(4)
_cell_length_c                   16.7412(9)
_cell_angle_alpha                85.307(2)
_cell_angle_beta                 84.129(2)
_cell_angle_gamma                85.070(2)
_cell_volume                     984.06(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10272
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.453
_diffrn_reflns_theta_max         30.098
_diffrn_reflns_theta_full        25.042
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             5291
_reflns_number_gt                4278
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.4338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5291
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.003

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36649(15) 0.28281(16) 0.25330(8) 0.0274(3) Uani 1 1 d . . . . .
C1 C 0.23628(19) 0.4025(2) 0.29563(10) 0.0372(4) Uani 1 1 d . . . . .
H1A H 0.1168 0.3590 0.3023 0.045 Uiso 1 1 calc R U . . .
H1B H 0.2301 0.5179 0.2665 0.045 Uiso 1 1 calc R U . . .
C2 C 0.30972(18) 0.4073(2) 0.37648(9) 0.0331(3) Uani 1 1 d . . . . .
H2A H 0.2735 0.3092 0.4140 0.040 Uiso 1 1 calc R U . . .
H2B H 0.2697 0.5161 0.4014 0.040 Uiso 1 1 calc R U . . .
C3 C 0.51004(17) 0.39402(18) 0.35411(8) 0.0242(3) Uani 1 1 d . . . . .
C4 C 0.53454(16) 0.25398(17) 0.29221(8) 0.0230(3) Uani 1 1 d . . . . .
H4 H 0.6356 0.2806 0.2513 0.028 Uiso 1 1 calc R U . . .
C5 C 0.62138(19) 0.35209(19) 0.42525(9) 0.0273(3) Uani 1 1 d . . . . .
O1 O 0.57412(16) 0.27249(16) 0.48764(7) 0.0376(3) Uani 1 1 d . . . . .
C6 C 0.7942(2) 0.4361(2) 0.40700(10) 0.0364(4) Uani 1 1 d . . . . .
H6A H 0.8962 0.3484 0.4070 0.044 Uiso 1 1 calc R U . . .
H6B H 0.8067 0.5185 0.4475 0.044 Uiso 1 1 calc R U . . .
C7 C 0.78508(19) 0.5294(2) 0.32344(9) 0.0300(3) Uani 1 1 d . . . . .
H7A H 0.8433 0.4568 0.2810 0.036 Uiso 1 1 calc R U . . .
H7B H 0.8423 0.6391 0.3196 0.036 Uiso 1 1 calc R U . . .
C8 C 0.58565(19) 0.56135(18) 0.31590(9) 0.0279(3) Uani 1 1 d . . . . .
H8A H 0.5615 0.5817 0.2588 0.034 Uiso 1 1 calc R U . . .
H8B H 0.5344 0.6615 0.3454 0.034 Uiso 1 1 calc R U . . .
C9 C 0.56225(18) 0.06518(18) 0.32549(9) 0.0275(3) Uani 1 1 d . . . . .
H9A H 0.4905 0.0501 0.3780 0.033 Uiso 1 1 calc R U . . .
H9B H 0.5183 -0.0095 0.2882 0.033 Uiso 1 1 calc R U . . .
C10 C 0.75355(18) 0.00735(18) 0.33666(9) 0.0271(3) Uani 1 1 d . . . . .
C11 C 0.8039(3) -0.0602(2) 0.41098(12) 0.0416(4) Uani 1 1 d . . . . .
H11 H 0.7178 -0.0664 0.4562 0.050 Uiso 1 1 calc R U . . .
C12 C 0.9789(3) -0.1186(3) 0.41983(16) 0.0580(6) Uani 1 1 d . . . . .
H12 H 1.0114 -0.1663 0.4708 0.070 Uiso 1 1 calc R U . . .
C13 C 1.1047(3) -0.1078(2) 0.35565(19) 0.0656(8) Uani 1 1 d . . . . .
H13 H 1.2247 -0.1459 0.3623 0.079 Uiso 1 1 calc R U . . .
C14 C 1.0580(3) -0.0420(3) 0.28159(18) 0.0647(7) Uani 1 1 d . . . . .
H14 H 1.1455 -0.0353 0.2369 0.078 Uiso 1 1 calc R U . . .
C15 C 0.8825(2) 0.0148(2) 0.27192(12) 0.0434(4) Uani 1 1 d . . . . .
H15 H 0.8507 0.0592 0.2204 0.052 Uiso 1 1 calc R U . . .
S1 S 0.37263(5) 0.27862(5) 0.15594(2) 0.03167(11) Uani 1 1 d . . . . .
O2 O 0.46662(19) 0.11900(15) 0.13586(8) 0.0439(3) Uani 1 1 d . . . . .
O3 O 0.19421(17) 0.31861(18) 0.13643(8) 0.0459(3) Uani 1 1 d . . . . .
C16 C 0.5042(2) 0.4437(2) 0.11417(9) 0.0294(3) Uani 1 1 d . . . . .
C17 C 0.4266(2) 0.6100(2) 0.10041(10) 0.0356(3) Uani 1 1 d . . . . .
H17 H 0.3014 0.6324 0.1076 0.043 Uiso 1 1 calc R U . . .
C18 C 0.5342(3) 0.7422(2) 0.07611(11) 0.0431(4) Uani 1 1 d . . . . .
H18 H 0.4817 0.8555 0.0659 0.052 Uiso 1 1 calc R U . . .
C19 C 0.7171(3) 0.7125(2) 0.06628(10) 0.0432(4) Uani 1 1 d . . . . .
C20 C 0.7924(2) 0.5447(3) 0.07920(11) 0.0420(4) Uani 1 1 d . . . . .
H20 H 0.9176 0.5225 0.0721 0.050 Uiso 1 1 calc R U . . .
C21 C 0.6871(2) 0.4105(2) 0.10222(10) 0.0357(4) Uani 1 1 d . . . . .
H21 H 0.7393 0.2964 0.1098 0.043 Uiso 1 1 calc R U . . .
C22 C 0.8323(4) 0.8588(3) 0.04058(15) 0.0656(7) Uani 1 1 d . . . . .
H22A H 0.9502 0.8304 0.0592 0.098 Uiso 1 1 calc R U . . .
H22B H 0.7783 0.9638 0.0641 0.098 Uiso 1 1 calc R U . . .
H22C H 0.8433 0.8773 -0.0183 0.098 Uiso 1 1 calc R U . . .


_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
N1 C1 1.471(2) . ?
N1 C4 1.4846(16) . ?
N1 S1 1.6287(13) . ?
C1 C2 1.520(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5273(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C5 1.5288(19) . ?
C3 C8 1.540(2) . ?
C3 C4 1.556(2) . ?
C4 C9 1.5402(19) . ?
C4 H4 1.0000 . ?
C5 O1 1.2095(18) . ?
C5 C6 1.512(2) . ?
C6 C7 1.529(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5316(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5111(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.386(2) . ?
C10 C11 1.389(2) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.365(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
S1 O3 1.4302(12) . ?
S1 O2 1.4314(13) . ?
S1 C16 1.7575(16) . ?
C16 C21 1.389(2) . ?
C16 C17 1.393(2) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.395(3) . ?
C19 C22 1.509(3) . ?
C20 C21 1.381(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 112.30(12) . . ?
C1 N1 S1 119.60(10) . . ?
C4 N1 S1 119.23(9) . . ?
N1 C1 C2 102.71(11) . . ?
N1 C1 H1A 111.2 . . ?
C2 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
C1 C2 C3 102.84(12) . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C5 114.80(12) . . ?
C2 C3 C8 114.88(12) . . ?
C5 C3 C8 101.42(11) . . ?
C2 C3 C4 102.50(12) . . ?
C5 C3 C4 113.50(11) . . ?
C8 C3 C4 110.13(11) . . ?
N1 C4 C9 110.39(11) . . ?
N1 C4 C3 101.90(10) . . ?
C9 C4 C3 117.33(12) . . ?
N1 C4 H4 108.9 . . ?
C9 C4 H4 108.9 . . ?
C3 C4 H4 108.9 . . ?
O1 C5 C6 125.73(14) . . ?
O1 C5 C3 125.24(14) . . ?
C6 C5 C3 108.92(12) . . ?
C5 C6 C7 105.43(12) . . ?
C5 C6 H6A 110.7 . . ?
C7 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 . . ?
C7 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C6 C7 C8 103.57(12) . . ?
C6 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
C7 C8 C3 103.64(11) . . ?
C7 C8 H8A 111.0 . . ?
C3 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C3 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C10 C9 C4 113.54(11) . . ?
C10 C9 H9A 108.9 . . ?
C4 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C4 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C15 C10 C11 118.24(15) . . ?
C15 C10 C9 120.56(14) . . ?
C11 C10 C9 121.16(15) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.11(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.71(19) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O3 S1 O2 120.45(9) . . ?
O3 S1 N1 106.14(7) . . ?
O2 S1 N1 106.49(7) . . ?
O3 S1 C16 109.45(7) . . ?
O2 S1 C16 107.12(8) . . ?
N1 S1 C16 106.36(7) . . ?
C21 C16 C17 120.43(15) . . ?
C21 C16 S1 119.47(12) . . ?
C17 C16 S1 119.83(13) . . ?
C18 C17 C16 119.14(16) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C19 C18 C17 121.26(16) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 118.81(17) . . ?
C18 C19 C22 120.5(2) . . ?
C20 C19 C22 120.7(2) . . ?
C21 C20 C19 120.79(17) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C16 119.53(15) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.048

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_e4384a_a
_database_code_depnum_ccdc_archive 'CCDC 1844757'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H27 N O3 S'
_chemical_formula_sum            'C28 H27 N O3 S'
_chemical_formula_weight         457.56

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.5059(6)
_cell_length_b                   11.5524(5)
_cell_length_c                   19.3292(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.812(2)
_cell_angle_gamma                90
_cell_volume                     2311.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    23000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23138
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.967
_diffrn_reflns_theta_max         30.180
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6794
_reflns_number_gt                4773
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.5260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6794
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.87018(4) 0.44190(4) 0.75361(2) 0.03208(12) Uani 1 1 d . . . . .
O1 O 0.99646(14) 0.40530(11) 0.78569(7) 0.0459(4) Uani 1 1 d . . . . .
O2 O 0.78540(15) 0.49035(11) 0.79633(6) 0.0432(3) Uani 1 1 d . . . . .
C1 C 0.78975(16) 0.32241(14) 0.70983(8) 0.0272(3) Uani 1 1 d . . . . .
C2 C 0.65705(17) 0.31190(15) 0.70425(9) 0.0330(4) Uani 1 1 d . . . . .
H2 H 0.6084 0.3710 0.7218 0.040 Uiso 1 1 calc R U . . .
C3 C 0.59610(18) 0.21447(16) 0.67279(10) 0.0384(4) Uani 1 1 d . . . . .
H3 H 0.5050 0.2075 0.6687 0.046 Uiso 1 1 calc R U . . .
C4 C 0.66508(19) 0.12722(15) 0.64726(9) 0.0355(4) Uani 1 1 d . . . . .
C5 C 0.79757(19) 0.13932(16) 0.65339(10) 0.0382(4) Uani 1 1 d . . . . .
H5 H 0.8462 0.0799 0.6361 0.046 Uiso 1 1 calc R U . . .
C6 C 0.86059(17) 0.23626(15) 0.68429(9) 0.0346(4) Uani 1 1 d . . . . .
H6 H 0.9516 0.2436 0.6879 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5968(2) 0.02229(19) 0.61258(14) 0.0602(6) Uani 1 1 d . . . . .
H7A H 0.5054 0.0249 0.6173 0.090 Uiso 1 1 calc R U . . .
H7B H 0.6365 -0.0479 0.6352 0.090 Uiso 1 1 calc R U . . .
H7C H 0.6041 0.0216 0.5627 0.090 Uiso 1 1 calc R U . . .
N1 N 0.89465(13) 0.53902(12) 0.69542(7) 0.0284(3) Uani 1 1 d . . . . .
C8 C 0.79608(15) 0.59591(13) 0.64706(8) 0.0242(3) Uani 1 1 d . . . . .
C9 C 0.86128(15) 0.64783(13) 0.58870(8) 0.0237(3) Uani 1 1 d . . . . .
C10 C 1.00632(15) 0.64205(14) 0.62200(8) 0.0282(3) Uani 1 1 d . . . . .
H10A H 1.0607 0.6334 0.5852 0.034 Uiso 1 1 calc R U . . .
H10B H 1.0328 0.7131 0.6493 0.034 Uiso 1 1 calc R U . . .
C11 C 1.01924(16) 0.53721(14) 0.66952(9) 0.0302(3) Uani 1 1 d . . . . .
H11A H 1.0294 0.4653 0.6431 0.036 Uiso 1 1 calc R U . . .
H11B H 1.0932 0.5452 0.7085 0.036 Uiso 1 1 calc R U . . .
C12 C 0.84083(15) 0.56552(13) 0.52507(8) 0.0234(3) Uani 1 1 d . . . . .
O3 O 0.85351(12) 0.46167(9) 0.53494(6) 0.0316(3) Uani 1 1 d . . . . .
C13 C 0.80320(15) 0.60992(13) 0.45116(8) 0.0252(3) Uani 1 1 d . . . . .
C14 C 0.84846(16) 0.71349(14) 0.42650(9) 0.0301(4) Uani 1 1 d . . . . .
C15 C 0.94893(18) 0.78601(15) 0.47145(10) 0.0356(4) Uani 1 1 d . . . . .
H15A H 0.9793 0.8459 0.4415 0.043 Uiso 1 1 calc R U . . .
H15B H 1.0237 0.7360 0.4896 0.043 Uiso 1 1 calc R U . . .
C16 C 0.90463(19) 0.84606(15) 0.53381(10) 0.0357(4) Uani 1 1 d . . . . .
H16A H 0.9819 0.8681 0.5681 0.043 Uiso 1 1 calc R U . . .
H16B H 0.8586 0.9182 0.5170 0.043 Uiso 1 1 calc R U . . .
C17 C 0.81616(16) 0.77270(13) 0.57137(9) 0.0284(3) Uani 1 1 d . . . . .
H17A H 0.7296 0.7699 0.5417 0.034 Uiso 1 1 calc R U . . .
H17B H 0.8067 0.8121 0.6157 0.034 Uiso 1 1 calc R U . . .
C18 C 0.72060(16) 0.53861(15) 0.40565(8) 0.0297(3) Uani 1 1 d . . . . .
H18 H 0.6911 0.4681 0.4227 0.036 Uiso 1 1 calc R U . . .
C19 C 0.68091(17) 0.56909(18) 0.33589(9) 0.0381(4) Uani 1 1 d . . . . .
H19 H 0.6246 0.5201 0.3052 0.046 Uiso 1 1 calc R U . . .
C20 C 0.72455(18) 0.67169(19) 0.31171(9) 0.0427(5) Uani 1 1 d . . . . .
H20 H 0.6984 0.6934 0.2640 0.051 Uiso 1 1 calc R U . . .
C21 C 0.80569(18) 0.74264(17) 0.35631(10) 0.0386(4) Uani 1 1 d . . . . .
H21 H 0.8334 0.8135 0.3389 0.046 Uiso 1 1 calc R U . . .
C22 C 0.67490(16) 0.60649(14) 0.65829(8) 0.0275(3) Uani 1 1 d . . . . .
H22 H 0.6585 0.5764 0.7016 0.033 Uiso 1 1 calc R U . . .
C23 C 0.56276(15) 0.65864(14) 0.61245(8) 0.0265(3) Uani 1 1 d . . . . .
C24 C 0.53317(17) 0.63787(17) 0.54046(9) 0.0345(4) Uani 1 1 d . . . . .
H24 H 0.5876 0.5889 0.5189 0.041 Uiso 1 1 calc R U . . .
C25 C 0.42577(19) 0.68756(19) 0.49997(10) 0.0444(5) Uani 1 1 d . . . . .
H25 H 0.4074 0.6727 0.4509 0.053 Uiso 1 1 calc R U . . .
C26 C 0.34543(19) 0.75824(18) 0.53019(11) 0.0442(5) Uani 1 1 d . . . . .
H26 H 0.2727 0.7935 0.5021 0.053 Uiso 1 1 calc R U . . .
C27 C 0.37122(18) 0.77763(17) 0.60165(11) 0.0419(4) Uani 1 1 d . . . . .
H27 H 0.3157 0.8258 0.6230 0.050 Uiso 1 1 calc R U . . .
C28 C 0.47731(16) 0.72715(15) 0.64199(9) 0.0341(4) Uani 1 1 d . . . . .
H28 H 0.4926 0.7394 0.6913 0.041 Uiso 1 1 calc R U . . .


_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 1.4279(14) . ?
S1 O1 1.4293(14) . ?
S1 N1 1.6398(14) . ?
S1 C1 1.7584(17) . ?
C1 C6 1.383(2) . ?
C1 C2 1.385(2) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 C7 1.506(3) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N1 C8 1.4311(19) . ?
N1 C11 1.479(2) . ?
C8 C22 1.333(2) . ?
C8 C9 1.538(2) . ?
C9 C17 1.537(2) . ?
C9 C12 1.541(2) . ?
C9 C10 1.551(2) . ?
C10 C11 1.512(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.2186(18) . ?
C12 C13 1.506(2) . ?
C13 C18 1.395(2) . ?
C13 C14 1.401(2) . ?
C14 C21 1.396(2) . ?
C14 C15 1.503(2) . ?
C15 C16 1.530(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.529(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.477(2) . ?
C22 H22 0.9500 . ?
C23 C28 1.390(2) . ?
C23 C24 1.394(2) . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.374(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.376(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

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 119.31(8) . . ?
O2 S1 N1 108.34(7) . . ?
O1 S1 N1 104.92(8) . . ?
O2 S1 C1 106.86(8) . . ?
O1 S1 C1 108.12(8) . . ?
N1 S1 C1 109.01(7) . . ?
C6 C1 C2 120.31(16) . . ?
C6 C1 S1 119.54(13) . . ?
C2 C1 S1 120.07(13) . . ?
C3 C2 C1 119.33(16) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 121.28(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.50(17) . . ?
C3 C4 C7 120.48(18) . . ?
C5 C4 C7 121.01(18) . . ?
C6 C5 C4 121.27(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 119.31(17) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
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 . . ?
C8 N1 C11 111.66(12) . . ?
C8 N1 S1 125.57(12) . . ?
C11 N1 S1 118.28(11) . . ?
C22 C8 N1 122.73(14) . . ?
C22 C8 C9 129.85(14) . . ?
N1 C8 C9 107.15(13) . . ?
C17 C9 C8 111.50(12) . . ?
C17 C9 C12 114.16(12) . . ?
C8 C9 C12 109.02(12) . . ?
C17 C9 C10 112.05(13) . . ?
C8 C9 C10 101.99(12) . . ?
C12 C9 C10 107.35(12) . . ?
C11 C10 C9 105.46(13) . . ?
C11 C10 H10A 110.6 . . ?
C9 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
N1 C11 C10 101.61(13) . . ?
N1 C11 H11A 111.4 . . ?
C10 C11 H11A 111.4 . . ?
N1 C11 H11B 111.4 . . ?
C10 C11 H11B 111.4 . . ?
H11A C11 H11B 109.3 . . ?
O3 C12 C13 119.20(14) . . ?
O3 C12 C9 119.08(13) . . ?
C13 C12 C9 121.71(13) . . ?
C18 C13 C14 120.05(14) . . ?
C18 C13 C12 115.57(14) . . ?
C14 C13 C12 124.35(15) . . ?
C21 C14 C13 117.72(17) . . ?
C21 C14 C15 120.36(16) . . ?
C13 C14 C15 121.68(15) . . ?
C14 C15 C16 115.48(15) . . ?
C14 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
C17 C16 C15 114.44(14) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C9 115.70(14) . . ?
C16 C17 H17A 108.4 . . ?
C9 C17 H17A 108.4 . . ?
C16 C17 H17B 108.4 . . ?
C9 C17 H17B 108.4 . . ?
H17A C17 H17B 107.4 . . ?
C19 C18 C13 120.98(17) . . ?
C19 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C20 C19 C18 119.00(18) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 120.37(16) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C14 121.87(17) . . ?
C20 C21 H21 119.1 . . ?
C14 C21 H21 119.1 . . ?
C8 C22 C23 128.77(14) . . ?
C8 C22 H22 115.6 . . ?
C23 C22 H22 115.6 . . ?
C28 C23 C24 117.28(16) . . ?
C28 C23 C22 119.40(14) . . ?
C24 C23 C22 123.24(15) . . ?
C25 C24 C23 120.99(17) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C26 C25 C24 120.46(17) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 119.47(18) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C28 C27 C26 120.02(18) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C23 121.72(16) . . ?
C27 C28 H28 119.1 . . ?
C23 C28 H28 119.1 . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.056

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_e4386b_a
_database_code_depnum_ccdc_archive 'CCDC 1844758'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H29 N O3 S'
_chemical_formula_sum            'C25 H29 N O3 S'
_chemical_formula_weight         423.55

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.6751(5)
_cell_length_b                   21.9074(13)
_cell_length_c                   12.3550(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.8930(10)
_cell_angle_gamma                90
_cell_volume                     2234.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    40000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42885
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.859
_diffrn_reflns_theta_max         30.104
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6408
_reflns_number_gt                4676
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+1.7386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6408
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1784
_refine_ls_wR_factor_gt          0.1575
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.49068(7) 0.51139(2) 0.79572(5) 0.04771(17) Uani 1 1 d . . . . .
O1 O 0.64689(19) 0.53968(7) 0.83829(15) 0.0520(4) Uani 1 1 d . . . . .
O2 O 0.4775(3) 0.44668(7) 0.80502(18) 0.0708(6) Uani 1 1 d . . . . .
C1 C 0.4080(3) 0.53216(9) 0.6524(2) 0.0437(5) Uani 1 1 d . . . . .
C2 C 0.4639(3) 0.58074(14) 0.6095(3) 0.0801(10) Uani 1 1 d . . . . .
H2 H 0.5495 0.6047 0.6568 0.096 Uiso 1 1 calc R U . . .
C3 C 0.3962(4) 0.59560(15) 0.4960(3) 0.0913(12) Uani 1 1 d . . . . .
H3 H 0.4376 0.6298 0.4667 0.110 Uiso 1 1 calc R U . . .
C4 C 0.2723(3) 0.56306(12) 0.4246(2) 0.0550(6) Uani 1 1 d . . . . .
C5 C 0.2181(6) 0.5154(2) 0.4702(3) 0.1128(17) Uani 1 1 d . . . . .
H5 H 0.1316 0.4916 0.4232 0.135 Uiso 1 1 calc R U . . .
C6 C 0.2831(6) 0.49970(18) 0.5822(3) 0.1186(18) Uani 1 1 d . . . . .
H6 H 0.2406 0.4657 0.6114 0.142 Uiso 1 1 calc R U . . .
C7 C 0.2004(4) 0.58043(17) 0.3021(2) 0.0778(9) Uani 1 1 d . . . . .
H7A H 0.1784 0.5435 0.2551 0.117 Uiso 1 1 calc R U . . .
H7B H 0.2767 0.6064 0.2789 0.117 Uiso 1 1 calc R U . . .
H7C H 0.0990 0.6027 0.2920 0.117 Uiso 1 1 calc R U . . .
N1 N 0.3734(2) 0.54001(7) 0.86514(16) 0.0422(4) Uani 1 1 d . . . . .
C8 C 0.3383(2) 0.60377(8) 0.86714(16) 0.0347(4) Uani 1 1 d . . . . .
C9 C 0.1739(2) 0.61043(7) 0.88690(14) 0.0289(3) Uani 1 1 d . . . . .
C10 C 0.1432(2) 0.54491(8) 0.92489(17) 0.0374(4) Uani 1 1 d . . . . .
H10A H 0.1841 0.5412 1.0087 0.045 Uiso 1 1 calc R U . . .
H10B H 0.0260 0.5353 0.8991 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2338(3) 0.50261(9) 0.8701(2) 0.0466(5) Uani 1 1 d . . . . .
H11A H 0.2700 0.4655 0.9167 0.056 Uiso 1 1 calc R U . . .
H11B H 0.1660 0.4904 0.7930 0.056 Uiso 1 1 calc R U . . .
C12 C 0.0417(2) 0.62139(9) 0.77370(16) 0.0401(4) Uani 1 1 d . . . . .
O3 O 0.0551(3) 0.59890(8) 0.68710(13) 0.0676(5) Uani 1 1 d . . . . .
C13 C -0.1075(3) 0.65579(14) 0.7753(2) 0.0618(7) Uani 1 1 d . . . . .
H13A H -0.1865 0.6263 0.7883 0.074 Uiso 1 1 calc R U . . .
H13B H -0.1569 0.6743 0.6994 0.074 Uiso 1 1 calc R U . . .
C14 C -0.0798(3) 0.70576(12) 0.8642(2) 0.0597(7) Uani 1 1 d . . . . .
H14A H -0.0194 0.7396 0.8428 0.072 Uiso 1 1 calc R U . . .
H14B H -0.1859 0.7219 0.8653 0.072 Uiso 1 1 calc R U . . .
C15 C 0.0138(3) 0.68346(10) 0.9823(2) 0.0451(5) Uani 1 1 d . . . . .
C16 C 0.1776(2) 0.65860(8) 0.97824(15) 0.0341(4) Uani 1 1 d . . . . .
H16A H 0.2345 0.6407 1.0535 0.041 Uiso 1 1 calc R U . . .
H16B H 0.2434 0.6935 0.9669 0.041 Uiso 1 1 calc R U . . .
C17 C 0.4395(3) 0.64795(9) 0.8576(2) 0.0528(6) Uani 1 1 d . . . . .
H17 H 0.5446 0.6359 0.8574 0.063 Uiso 1 1 calc R U . . .
C18 C 0.4018(3) 0.71400(9) 0.8474(2) 0.0529(6) Uani 1 1 d . . . . .
C19 C 0.4973(4) 0.75501(11) 0.9262(3) 0.0707(8) Uani 1 1 d . . . . .
H19 H 0.5899 0.7408 0.9843 0.085 Uiso 1 1 calc R U . . .
C20 C 0.4573(5) 0.81651(13) 0.9198(4) 0.0938(12) Uani 1 1 d . . . . .
H20 H 0.5204 0.8442 0.9748 0.113 Uiso 1 1 calc R U . . .
C21 C 0.3259(5) 0.83727(13) 0.8336(4) 0.0988(14) Uani 1 1 d . . . . .
H21 H 0.2984 0.8794 0.8298 0.119 Uiso 1 1 calc R U . . .
C22 C 0.2349(4) 0.79819(13) 0.7536(3) 0.0787(10) Uani 1 1 d . . . . .
H22 H 0.1454 0.8131 0.6938 0.094 Uiso 1 1 calc R U . . .
C23 C 0.2733(3) 0.73635(11) 0.7598(3) 0.0616(7) Uani 1 1 d . . . . .
H23 H 0.2106 0.7092 0.7034 0.074 Uiso 1 1 calc R U . . .
C24 C -0.0843(3) 0.63624(12) 1.0253(2) 0.0543(6) Uani 1 1 d . . . . .
H24A H -0.1842 0.6551 1.0304 0.082 Uiso 1 1 calc R U . . .
H24B H -0.0199 0.6217 1.1006 0.082 Uiso 1 1 calc R U . . .
H24C H -0.1115 0.6018 0.9723 0.082 Uiso 1 1 calc R U . . .
C25 C 0.0490(4) 0.73769(12) 1.0654(3) 0.0781(9) Uani 1 1 d . . . . .
H25A H 0.1103 0.7689 1.0391 0.117 Uiso 1 1 calc R U . . .
H25B H 0.1127 0.7236 1.1413 0.117 Uiso 1 1 calc R U . . .
H25C H -0.0534 0.7551 1.0688 0.117 Uiso 1 1 calc R U . . .


_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 1.4297(16) . ?
S1 O1 1.4349(18) . ?
S1 N1 1.6435(18) . ?
S1 C1 1.755(2) . ?
C1 C2 1.344(3) . ?
C1 C6 1.362(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.339(4) . ?
C4 C7 1.499(4) . ?
C5 C6 1.367(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N1 C8 1.431(2) . ?
N1 C11 1.479(3) . ?
C8 C17 1.336(3) . ?
C8 C9 1.526(3) . ?
C9 C12 1.531(2) . ?
C9 C16 1.538(2) . ?
C9 C10 1.558(2) . ?
C10 C11 1.503(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.216(3) . ?
C12 C13 1.503(3) . ?
C13 C14 1.517(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C24 1.535(3) . ?
C15 C16 1.536(3) . ?
C15 C25 1.539(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.480(3) . ?
C17 H17 0.9500 . ?
C18 C23 1.383(4) . ?
C18 C19 1.394(4) . ?
C19 C20 1.387(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.377(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.361(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.26(12) . . ?
O2 S1 N1 104.98(10) . . ?
O1 S1 N1 108.09(10) . . ?
O2 S1 C1 108.68(12) . . ?
O1 S1 C1 107.77(10) . . ?
N1 S1 C1 107.53(10) . . ?
C2 C1 C6 118.4(3) . . ?
C2 C1 S1 121.21(19) . . ?
C6 C1 S1 120.4(2) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 122.6(3) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C5 C4 C3 116.4(3) . . ?
C5 C4 C7 122.1(3) . . ?
C3 C4 C7 121.5(3) . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 120.9(3) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
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 . . ?
C8 N1 C11 111.03(16) . . ?
C8 N1 S1 123.38(13) . . ?
C11 N1 S1 117.16(14) . . ?
C17 C8 N1 123.83(18) . . ?
C17 C8 C9 128.06(17) . . ?
N1 C8 C9 108.06(15) . . ?
C8 C9 C12 110.10(15) . . ?
C8 C9 C16 111.91(14) . . ?
C12 C9 C16 113.80(15) . . ?
C8 C9 C10 102.39(14) . . ?
C12 C9 C10 105.68(14) . . ?
C16 C9 C10 112.21(15) . . ?
C11 C10 C9 105.73(15) . . ?
C11 C10 H10A 110.6 . . ?
C9 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
N1 C11 C10 102.99(15) . . ?
N1 C11 H11A 111.2 . . ?
C10 C11 H11A 111.2 . . ?
N1 C11 H11B 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
O3 C12 C13 122.0(2) . . ?
O3 C12 C9 119.5(2) . . ?
C13 C12 C9 118.26(18) . . ?
C12 C13 C14 115.21(18) . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 112.52(19) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C24 111.1(2) . . ?
C14 C15 C16 108.09(17) . . ?
C24 C15 C16 112.90(17) . . ?
C14 C15 C25 109.4(2) . . ?
C24 C15 C25 107.9(2) . . ?
C16 C15 C25 107.4(2) . . ?
C15 C16 C9 117.12(16) . . ?
C15 C16 H16A 108.0 . . ?
C9 C16 H16A 108.0 . . ?
C15 C16 H16B 108.0 . . ?
C9 C16 H16B 108.0 . . ?
H16A C16 H16B 107.3 . . ?
C8 C17 C18 125.60(19) . . ?
C8 C17 H17 117.2 . . ?
C18 C17 H17 117.2 . . ?
C23 C18 C19 118.8(2) . . ?
C23 C18 C17 121.1(2) . . ?
C19 C18 C17 120.1(3) . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 119.8(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 120.6(3) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C25 H25A 109.5 . . ?
C15 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C15 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6



