# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1537759'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N2 O3 S'
_chemical_formula_sum            'C25 H22 N2 O3 S'
_chemical_formula_weight         430.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   19.827(7)
_cell_length_b                   7.782(3)
_cell_length_c                   14.742(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.923(7)
_cell_angle_gamma                90
_cell_volume                     2164.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2461
_cell_measurement_theta_min      23.3
_cell_measurement_theta_max      67.8

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.569
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.744
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13507
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.1083
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.342
_diffrn_reflns_theta_max         68.160
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3817
_reflns_number_gt                2806
_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       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_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)+(0.1254P)²+0.3151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3817
_refine_ls_number_parameters     288
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.2291
_refine_ls_wR_factor_gt          0.1905
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.003
_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 0.33336(4) 0.76856(11) 0.11212(5) 0.0644(3) Uani 1 1 d . . . . .
O1 O 0.31154(13) 0.9447(3) 0.10307(17) 0.0855(7) Uani 1 1 d . . . . .
O2 O 0.35858(14) 0.6921(4) 0.04114(16) 0.0939(8) Uani 1 1 d . . . . .
O3 O 0.19413(18) 0.4690(4) -0.05336(15) 0.1096(10) Uani 1 1 d . . . . .
N1 N 0.26487(12) 0.6600(3) 0.11506(17) 0.0596(6) Uani 1 1 d D . . . .
H1 H 0.2412(16) 0.706(4) 0.149(2) 0.072 Uiso 1 1 d D U . . .
N2 N 0.19928(15) 0.6725(4) 0.36740(17) 0.0709(7) Uani 1 1 d D . . . .
H2 H 0.211(2) 0.740(4) 0.4168(19) 0.085 Uiso 1 1 d D U . . .
C1 C 0.5646(3) 0.7044(7) 0.4901(3) 0.1168(16) Uani 1 1 d . . . . .
H1A H 0.5882 0.8130 0.5055 0.175 Uiso 1 1 calc R U . . .
H1B H 0.5980 0.6184 0.4853 0.175 Uiso 1 1 calc R U . . .
H1C H 0.5445 0.6728 0.5393 0.175 Uiso 1 1 calc R U . . .
C2 C 0.50664(18) 0.7183(5) 0.3967(2) 0.0720(9) Uani 1 1 d . . . . .
C3 C 0.44362(17) 0.8051(5) 0.3883(2) 0.0716(8) Uani 1 1 d . . . . .
H3 H 0.4370 0.8550 0.4423 0.086 Uiso 1 1 calc R U . . .
C4 C 0.39102(15) 0.8188(4) 0.3026(2) 0.0647(8) Uani 1 1 d . . . . .
H4 H 0.3496 0.8783 0.2988 0.078 Uiso 1 1 calc R U . . .
C5 C 0.39983(15) 0.7445(4) 0.2226(2) 0.0558(7) Uani 1 1 d . . . . .
C6 C 0.26366(14) 0.4732(3) 0.11437(18) 0.0543(6) Uani 1 1 d . . . . .
H6 H 0.3104 0.4347 0.1130 0.065 Uiso 1 1 calc R U . . .
C7 C 0.24863(13) 0.3807(3) 0.20042(17) 0.0510(6) Uani 1 1 d . . . . .
C8 C 0.21369(13) 0.4974(3) 0.25420(16) 0.0498(6) Uani 1 1 d . . . . .
C9 C 0.14045(13) 0.5505(3) 0.22775(17) 0.0510(6) Uani 1 1 d . . . . .
C10 C 0.13426(16) 0.6588(4) 0.30150(19) 0.0609(7) Uani 1 1 d . . . . .
C11 C 0.0698(2) 0.7316(4) 0.3010(2) 0.0757(9) Uani 1 1 d . . . . .
H11 H 0.0665 0.7991 0.3515 0.091 Uiso 1 1 calc R U . . .
C12 C 0.01198(19) 0.7010(5) 0.2246(3) 0.0785(10) Uani 1 1 d . . . . .
H12 H -0.0314 0.7490 0.2227 0.094 Uiso 1 1 calc R U . . .
C13 C 0.51406(17) 0.6453(5) 0.3150(3) 0.0778(9) Uani 1 1 d . . . . .
H13 H 0.5558 0.5870 0.3186 0.093 Uiso 1 1 calc R U . . .
C14 C 0.46201(16) 0.6556(4) 0.2288(2) 0.0703(8) Uani 1 1 d . . . . .
H14 H 0.4682 0.6038 0.1751 0.084 Uiso 1 1 calc R U . . .
C15 C 0.20925(17) 0.4023(4) 0.02483(19) 0.0658(8) Uani 1 1 d . . . . .
C16 C 0.17909(16) 0.2480(3) 0.05154(19) 0.0564(7) Uani 1 1 d . . . . .
C17 C 0.19881(14) 0.2371(3) 0.15000(18) 0.0520(7) Uani 1 1 d . . . . .
C18 C 0.17154(17) 0.1073(4) 0.1917(2) 0.0677(8) Uani 1 1 d . . . . .
H18 H 0.1839 0.0979 0.2576 0.081 Uiso 1 1 calc R U . . .
C19 C 0.1252(2) -0.0094(4) 0.1330(3) 0.0796(9) Uani 1 1 d . . . . .
H19 H 0.1062 -0.0970 0.1606 0.096 Uiso 1 1 calc R U . . .
C20 C 0.1065(2) 0.0013(4) 0.0351(3) 0.0800(10) Uani 1 1 d . . . . .
H20 H 0.0754 -0.0788 -0.0024 0.096 Uiso 1 1 calc R U . . .
C21 C 0.13353(18) 0.1297(4) -0.0070(2) 0.0709(8) Uani 1 1 d . . . . .
H21 H 0.1217 0.1375 -0.0730 0.085 Uiso 1 1 calc R U . . .
C22 C 0.31806(16) 0.3051(5) 0.2672(2) 0.0701(8) Uani 1 1 d . . . . .
H22A H 0.3509 0.3966 0.2931 0.105 Uiso 1 1 calc R U . . .
H22B H 0.3383 0.2280 0.2319 0.105 Uiso 1 1 calc R U . . .
H22C H 0.3082 0.2438 0.3182 0.105 Uiso 1 1 calc R U . . .
C23 C 0.24658(16) 0.5756(4) 0.33907(18) 0.0645(7) Uani 1 1 d . . . . .
H23 H 0.2944 0.5646 0.3728 0.077 Uiso 1 1 calc R U . . .
C24 C 0.01635(16) 0.5993(4) 0.1491(2) 0.0709(8) Uani 1 1 d . . . . .
H24 H -0.0238 0.5829 0.0969 0.085 Uiso 1 1 calc R U . . .
C25 C 0.07956(14) 0.5217(4) 0.1503(2) 0.0591(7) Uani 1 1 d . . . . .
H25 H 0.0815 0.4512 0.1002 0.071 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 1.422(3) . ?
S1 O1 1.431(3) . ?
S1 N1 1.611(2) . ?
S1 C5 1.762(3) . ?
O3 C15 1.215(3) . ?
N1 C6 1.454(4) . ?
N1 H1 0.862(18) . ?
N2 C10 1.359(4) . ?
N2 C23 1.365(4) . ?
N2 H2 0.870(18) . ?
C1 C2 1.501(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C13 1.379(5) . ?
C2 C3 1.392(5) . ?
C3 C4 1.373(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4 0.9300 . ?
C5 C14 1.392(4) . ?
C6 C15 1.528(4) . ?
C6 C7 1.565(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.507(4) . ?
C7 C17 1.525(4) . ?
C7 C22 1.542(4) . ?
C8 C23 1.364(4) . ?
C8 C9 1.443(4) . ?
C9 C25 1.401(4) . ?
C9 C10 1.410(4) . ?
C10 C11 1.396(4) . ?
C11 C12 1.358(5) . ?
C11 H11 0.9300 . ?
C12 C24 1.390(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.449(4) . ?
C16 C17 1.385(4) . ?
C16 C21 1.389(4) . ?
C17 C18 1.377(4) . ?
C18 C19 1.388(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C24 C25 1.387(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

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 119.80(17) . . ?
O2 S1 N1 106.89(14) . . ?
O1 S1 N1 105.76(14) . . ?
O2 S1 C5 107.68(16) . . ?
O1 S1 C5 107.85(14) . . ?
N1 S1 C5 108.43(13) . . ?
C6 N1 S1 122.4(2) . . ?
C6 N1 H1 114(2) . . ?
S1 N1 H1 115(2) . . ?
C10 N2 C23 109.1(2) . . ?
C10 N2 H2 127(3) . . ?
C23 N2 H2 124(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C2 C3 117.2(3) . . ?
C13 C2 C1 120.9(4) . . ?
C3 C2 C1 121.9(4) . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C14 119.8(3) . . ?
C4 C5 S1 119.5(2) . . ?
C14 C5 S1 120.6(2) . . ?
N1 C6 C15 111.9(2) . . ?
N1 C6 C7 117.5(2) . . ?
C15 C6 C7 105.9(2) . . ?
N1 C6 H6 107.0 . . ?
C15 C6 H6 107.0 . . ?
C7 C6 H6 107.0 . . ?
C8 C7 C17 111.4(2) . . ?
C8 C7 C22 111.0(2) . . ?
C17 C7 C22 110.4(2) . . ?
C8 C7 C6 112.5(2) . . ?
C17 C7 C6 101.45(19) . . ?
C22 C7 C6 109.7(2) . . ?
C23 C8 C9 106.1(2) . . ?
C23 C8 C7 125.8(2) . . ?
C9 C8 C7 128.2(2) . . ?
C25 C9 C10 117.8(2) . . ?
C25 C9 C8 135.8(2) . . ?
C10 C9 C8 106.4(2) . . ?
N2 C10 C11 129.6(3) . . ?
N2 C10 C9 108.0(2) . . ?
C11 C10 C9 122.3(3) . . ?
C12 C11 C10 118.1(3) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C24 121.3(3) . . ?
C11 C12 H12 119.4 . . ?
C24 C12 H12 119.4 . . ?
C14 C13 C2 122.2(3) . . ?
C14 C13 H13 118.9 . . ?
C2 C13 H13 118.9 . . ?
C13 C14 C5 119.3(3) . . ?
C13 C14 H14 120.4 . . ?
C5 C14 H14 120.4 . . ?
O3 C15 C16 127.6(3) . . ?
O3 C15 C6 124.6(3) . . ?
C16 C15 C6 107.8(2) . . ?
C17 C16 C21 122.0(3) . . ?
C17 C16 C15 109.2(2) . . ?
C21 C16 C15 128.6(3) . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 C7 127.2(2) . . ?
C16 C17 C7 113.4(2) . . ?
C17 C18 C19 118.6(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C20 C19 C18 121.7(3) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C16 118.2(3) . . ?
C20 C21 H21 120.9 . . ?
C16 C21 H21 120.9 . . ?
C7 C22 H22A 109.5 . . ?
C7 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C7 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 C23 N2 110.4(2) . . ?
C8 C23 H23 124.8 . . ?
N2 C23 H23 124.8 . . ?
C25 C24 C12 121.1(3) . . ?
C25 C24 H24 119.4 . . ?
C12 C24 H24 119.4 . . ?
C24 C25 C9 119.3(3) . . ?
C24 C25 H25 120.4 . . ?
C9 C25 H25 120.4 . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.095

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1537761'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 N2 O3 S'
_chemical_formula_weight         430.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   12.2496(9)
_cell_length_b                   15.4498(4)
_cell_length_c                   11.5317(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.677(7)
_cell_angle_gamma                90
_cell_volume                     2120.53(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    24046
_cell_measurement_theta_min      6.7
_cell_measurement_theta_max      67.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.601
_shelx_estimated_absorpt_T_min   0.740
_shelx_estimated_absorpt_T_max   0.740
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36188
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         6.679
_diffrn_reflns_theta_max         68.001
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3833
_reflns_number_gt                3168
_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       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_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)+(0.0507P)²+0.5778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3833
_refine_ls_number_parameters     289
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.42199(4) -0.07877(3) 0.83903(4) 0.04396(17) Uani 1 1 d . . . . .
O1 O 0.53404(11) -0.08201(9) 0.91325(13) 0.0553(4) Uani 1 1 d . . . . .
O2 O 0.40556(11) -0.10189(9) 0.71583(12) 0.0525(4) Uani 1 1 d . . . . .
O3 O 0.16968(15) 0.05900(11) 0.90847(15) 0.0747(5) Uani 1 1 d . . . . .
N1 N 0.38041(14) 0.01886(10) 0.84648(14) 0.0464(4) Uani 1 1 d D . . . .
H1 H 0.4035(17) 0.0439(13) 0.9134(15) 0.056 Uiso 1 1 d D U . . .
N2 N 0.41929(19) 0.08508(14) 0.42181(19) 0.0717(6) Uani 1 1 d D . . . .
H2 H 0.4727(19) 0.0876(17) 0.384(2) 0.086 Uiso 1 1 d D U . . .
C1 C 0.15081(19) -0.32700(14) 1.0643(2) 0.0614(6) Uani 1 1 d . . . . .
H1A H 0.1640 -0.3160 1.1484 0.092 Uiso 1 1 calc R U . . .
H1B H 0.1723 -0.3854 1.0517 0.092 Uiso 1 1 calc R U . . .
H1C H 0.0725 -0.3192 1.0278 0.092 Uiso 1 1 calc R U . . .
C2 C 0.21913(16) -0.26517(12) 1.00974(17) 0.0464(5) Uani 1 1 d . . . . .
C3 C 0.23630(18) -0.18074(13) 1.04968(19) 0.0536(5) Uani 1 1 d . . . . .
H3 H 0.2072 -0.1628 1.1132 0.064 Uiso 1 1 calc R U . . .
C4 C 0.29563(18) -0.12230(13) 0.99763(18) 0.0525(5) Uani 1 1 d . . . . .
H4 H 0.3067 -0.0659 1.0262 0.063 Uiso 1 1 calc R U . . .
C5 C 0.33840(15) -0.14871(12) 0.90253(16) 0.0421(4) Uani 1 1 d . . . . .
C6 C 0.28560(15) 0.05764(12) 0.76290(16) 0.0423(4) Uani 1 1 d . . . . .
H6 H 0.2516 0.0129 0.7054 0.051 Uiso 1 1 calc R U . . .
C7 C 0.31565(15) 0.13636(12) 0.69058(17) 0.0445(5) Uani 1 1 d . . . . .
C8 C 0.33589(17) 0.10993(12) 0.57169(18) 0.0472(5) Uani 1 1 d . . . . .
C9 C 0.25508(18) 0.07282(12) 0.47297(17) 0.0468(5) Uani 1 1 d . . . . .
C10 C 0.3114(2) 0.05794(13) 0.3810(2) 0.0582(6) Uani 1 1 d . . . . .
C11 C 0.2573(3) 0.02270(15) 0.2715(2) 0.0732(7) Uani 1 1 d . . . . .
H11 H 0.2956 0.0136 0.2119 0.088 Uiso 1 1 calc R U . . .
C12 C 0.1462(3) 0.00189(15) 0.2540(2) 0.0765(8) Uani 1 1 d . . . . .
H12 H 0.1084 -0.0222 0.1817 0.092 Uiso 1 1 calc R U . . .
C13 C 0.26346(17) -0.29028(13) 0.91505(19) 0.0542(5) Uani 1 1 d . . . . .
H13 H 0.2535 -0.3469 0.8874 0.065 Uiso 1 1 calc R U . . .
C14 C 0.32206(16) -0.23291(13) 0.86110(18) 0.0501(5) Uani 1 1 d . . . . .
H14 H 0.3505 -0.2507 0.7970 0.060 Uiso 1 1 calc R U . . .
C15 C 0.19427(17) 0.09123(13) 0.82221(18) 0.0495(5) Uani 1 1 d . . . . .
C16 C 0.14585(16) 0.16797(12) 0.75539(17) 0.0462(5) Uani 1 1 d . . . . .
C17 C 0.21062(16) 0.19196(12) 0.67694(17) 0.0459(5) Uani 1 1 d . . . . .
C18 C 0.17988(19) 0.26305(13) 0.60318(19) 0.0556(5) Uani 1 1 d . . . . .
H18 H 0.2220 0.2792 0.5494 0.067 Uiso 1 1 calc R U . . .
C19 C 0.0857(2) 0.30931(14) 0.6111(2) 0.0613(6) Uani 1 1 d . . . . .
H19 H 0.0644 0.3571 0.5619 0.074 Uiso 1 1 calc R U . . .
C20 C 0.02217(19) 0.28601(15) 0.6911(2) 0.0609(6) Uani 1 1 d . . . . .
H20 H -0.0403 0.3188 0.6958 0.073 Uiso 1 1 calc R U . . .
C21 C 0.05072(18) 0.21520(14) 0.76312(19) 0.0563(5) Uani 1 1 d . . . . .
H21 H 0.0077 0.1989 0.8160 0.068 Uiso 1 1 calc R U . . .
C22 C 0.4337(2) 0.11591(15) 0.5354(2) 0.0636(6) Uani 1 1 d . . . . .
H22 H 0.5007 0.1379 0.5814 0.076 Uiso 1 1 calc R U . . .
C23 C 0.14135(19) 0.05174(13) 0.45121(19) 0.0546(5) Uani 1 1 d . . . . .
H23 H 0.1014 0.0616 0.5092 0.066 Uiso 1 1 calc R U . . .
C24 C 0.0888(2) 0.01618(15) 0.3427(2) 0.0678(6) Uani 1 1 d . . . . .
H24 H 0.0132 0.0014 0.3286 0.081 Uiso 1 1 calc R U . . .
C25 C 0.41550(18) 0.18741(15) 0.7659(2) 0.0603(6) Uani 1 1 d . . . . .
H25A H 0.4824 0.1528 0.7780 0.090 Uiso 1 1 calc R U . . .
H25B H 0.4006 0.2015 0.8418 0.090 Uiso 1 1 calc R U . . .
H25C H 0.4258 0.2398 0.7250 0.090 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 1.4322(13) . ?
S1 O1 1.4365(14) . ?
S1 N1 1.6009(17) . ?
S1 C5 1.7625(19) . ?
O3 C15 1.213(2) . ?
N1 C6 1.452(2) . ?
N1 H1 0.850(15) . ?
N2 C10 1.360(3) . ?
N2 C22 1.365(3) . ?
N2 H2 0.867(17) . ?
C1 C2 1.503(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.383(3) . ?
C2 C13 1.385(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C14 1.384(3) . ?
C6 C15 1.533(3) . ?
C6 C7 1.567(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.506(3) . ?
C7 C17 1.524(3) . ?
C7 C25 1.540(3) . ?
C8 C22 1.362(3) . ?
C8 C9 1.439(3) . ?
C9 C23 1.395(3) . ?
C9 C10 1.415(3) . ?
C10 C11 1.391(3) . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C24 1.388(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.461(3) . ?
C16 C17 1.387(3) . ?
C16 C21 1.396(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.379(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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 118.21(8) . . ?
O2 S1 N1 108.44(9) . . ?
O1 S1 N1 105.79(8) . . ?
O2 S1 C5 107.46(9) . . ?
O1 S1 C5 107.35(9) . . ?
N1 S1 C5 109.38(9) . . ?
C6 N1 S1 124.61(13) . . ?
C6 N1 H1 117.3(15) . . ?
S1 N1 H1 115.8(15) . . ?
C10 N2 C22 109.52(18) . . ?
C10 N2 H2 128.8(19) . . ?
C22 N2 H2 121.5(19) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C13 118.02(18) . . ?
C3 C2 C1 121.06(18) . . ?
C13 C2 C1 120.88(18) . . ?
C2 C3 C4 121.72(18) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 119.21(18) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C14 119.98(18) . . ?
C4 C5 S1 120.96(14) . . ?
C14 C5 S1 118.92(14) . . ?
N1 C6 C15 113.40(15) . . ?
N1 C6 C7 114.96(15) . . ?
C15 C6 C7 105.23(15) . . ?
N1 C6 H6 107.6 . . ?
C15 C6 H6 107.6 . . ?
C7 C6 H6 107.6 . . ?
C8 C7 C17 112.06(16) . . ?
C8 C7 C25 111.89(16) . . ?
C17 C7 C25 107.94(16) . . ?
C8 C7 C6 112.58(15) . . ?
C17 C7 C6 101.16(14) . . ?
C25 C7 C6 110.64(16) . . ?
C22 C8 C9 105.91(19) . . ?
C22 C8 C7 127.4(2) . . ?
C9 C8 C7 126.69(17) . . ?
C23 C9 C10 118.1(2) . . ?
C23 C9 C8 134.93(18) . . ?
C10 C9 C8 106.96(19) . . ?
N2 C10 C11 130.6(2) . . ?
N2 C10 C9 107.2(2) . . ?
C11 C10 C9 122.2(2) . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C11 C12 C24 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C24 C12 H12 119.5 . . ?
C14 C13 C2 121.26(18) . . ?
C14 C13 H13 119.4 . . ?
C2 C13 H13 119.4 . . ?
C13 C14 C5 119.80(18) . . ?
C13 C14 H14 120.1 . . ?
C5 C14 H14 120.1 . . ?
O3 C15 C16 128.11(19) . . ?
O3 C15 C6 125.17(19) . . ?
C16 C15 C6 106.71(16) . . ?
C17 C16 C21 121.12(19) . . ?
C17 C16 C15 109.70(17) . . ?
C21 C16 C15 129.17(18) . . ?
C18 C17 C16 119.85(19) . . ?
C18 C17 C7 127.62(18) . . ?
C16 C17 C7 112.40(17) . . ?
C19 C18 C17 118.7(2) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C16 118.5(2) . . ?
C20 C21 H21 120.8 . . ?
C16 C21 H21 120.8 . . ?
C8 C22 N2 110.4(2) . . ?
C8 C22 H22 124.8 . . ?
N2 C22 H22 124.8 . . ?
C24 C23 C9 119.2(2) . . ?
C24 C23 H23 120.4 . . ?
C9 C23 H23 120.4 . . ?
C23 C24 C12 121.6(3) . . ?
C23 C24 H24 119.2 . . ?
C12 C24 H24 119.2 . . ?
C7 C25 H25A 109.5 . . ?
C7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3



