# 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_20febb_0m
_database_code_depnum_ccdc_archive 'CCDC 1518181'
_audit_update_record             
;
2016-11-18 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 N2 O3 S'
_chemical_formula_sum            'C26 H30 N2 O3 S'
_chemical_formula_weight         450.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.774(5)
_cell_length_b                   10.058(5)
_cell_length_c                   14.512(5)
_cell_angle_alpha                96.541(5)
_cell_angle_beta                 105.912(5)
_cell_angle_gamma                108.607(5)
_cell_volume                     1138.4(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5693
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      28.4

_exptl_crystal_description       PRISM
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17573
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         28.37
_reflns_number_total             5693
_reflns_number_gt                4399
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_structure_solution    'SIR97(Altomare, et. al. 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0557P)²+0.4403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5693
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
S1 S -0.10770(5) 0.07769(4) 0.64672(3) 0.01397(11) Uani 1 1 d . . .
O1 O 0.24986(14) 0.49908(12) 0.69166(8) 0.0164(2) Uani 1 1 d . . .
O2 O -0.17645(14) 0.04202(12) 0.72330(8) 0.0177(3) Uani 1 1 d . . .
O3 O -0.06372(14) -0.02506(12) 0.59295(8) 0.0183(3) Uani 1 1 d . . .
N2 N 0.06768(16) 0.21956(14) 0.69730(10) 0.0137(3) Uani 1 1 d . . .
N1 N 0.24587(17) 0.38355(14) 0.62123(10) 0.0158(3) Uani 1 1 d . . .
C2 C 0.1052(2) 0.60667(17) 0.77305(12) 0.0162(3) Uani 1 1 d . . .
C14 C 0.5208(2) 0.37272(18) 0.76950(12) 0.0184(3) Uani 1 1 d . . .
H14 H 0.5244 0.4579 0.7494 0.023(5) Uiso 1 1 calc R . .
C8 C 0.0627(2) 0.34103(17) 0.76342(12) 0.0146(3) Uani 1 1 d . . .
C1 C 0.0923(2) 0.46906(17) 0.71293(12) 0.0149(3) Uani 1 1 d . . .
C19 C -0.25213(19) 0.13061(16) 0.56291(11) 0.0142(3) Uani 1 1 d . . .
C18 C 0.3691(2) 0.12506(18) 0.76264(12) 0.0177(3) Uani 1 1 d . . .
H18 H 0.2692 0.0441 0.7395 0.021(5) Uiso 1 1 calc R . .
C12 C 0.2103(2) 0.25144(17) 0.65710(12) 0.0150(3) Uani 1 1 d . . .
C3 C 0.2587(2) 0.70006(18) 0.84162(12) 0.0207(4) Uani 1 1 d . . .
H3 H 0.3574 0.6806 0.8484 0.024(5) Uiso 1 1 calc R . .
C25 C -0.5661(2) 0.30245(19) 0.36966(13) 0.0226(4) Uani 1 1 d . . .
H25A H -0.5544 0.2879 0.3058 0.046(7) Uiso 1 1 calc R . .
H25B H -0.5305 0.4036 0.3960 0.043(6) Uiso 1 1 calc R . .
H25C H -0.6830 0.2554 0.3644 0.035(6) Uiso 1 1 calc R . .
C22 C -0.4571(2) 0.24076(17) 0.43651(12) 0.0174(3) Uani 1 1 d . . .
C20 C -0.3571(2) 0.18800(18) 0.59560(12) 0.0173(3) Uani 1 1 d . . .
H20 H -0.3601 0.1891 0.6592 0.023(5) Uiso 1 1 calc R . .
C13 C 0.3712(2) 0.25207(17) 0.73285(11) 0.0154(3) Uani 1 1 d . . .
C15 C 0.6652(2) 0.3666(2) 0.83605(13) 0.0213(4) Uani 1 1 d . . .
H15 H 0.7636 0.4487 0.8619 0.021(5) Uiso 1 1 calc R . .
C16 C 0.6632(2) 0.2395(2) 0.86401(12) 0.0222(4) Uani 1 1 d . . .
H16 H 0.7606 0.2352 0.9076 0.026(5) Uiso 1 1 calc R . .
C7 C -0.0400(2) 0.64018(19) 0.76166(13) 0.0213(4) Uani 1 1 d . . .
H7 H -0.1427 0.5799 0.7146 0.024(5) Uiso 1 1 calc R . .
C10 C 0.1615(2) 0.24356(18) 0.91551(12) 0.0198(4) Uani 1 1 d . . .
H10A H 0.1481 0.1599 0.8690 0.022(5) Uiso 1 1 calc R . .
H10B H 0.0582 0.2232 0.9325 0.020(5) Uiso 1 1 calc R . .
C9 C 0.1868(2) 0.37240(17) 0.86761(11) 0.0169(3) Uani 1 1 d . . .
H9A H 0.3022 0.4066 0.8656 0.016(5) Uiso 1 1 calc R . .
H9B H 0.1744 0.4491 0.9083 0.012(4) Uiso 1 1 calc R . .
C4 C 0.2650(2) 0.82212(18) 0.89985(13) 0.0255(4) Uani 1 1 d . . .
H4 H 0.3678 0.8836 0.9462 0.033(6) Uiso 1 1 calc R . .
C23 C -0.3542(2) 0.17886(18) 0.40461(12) 0.0192(3) Uani 1 1 d . . .
H23 H -0.3546 0.1741 0.3402 0.022(5) Uiso 1 1 calc R . .
C26 C 0.1379(2) 0.37780(18) 0.52342(12) 0.0186(3) Uani 1 1 d . . .
H26A H 0.0237 0.3598 0.5235 0.020(5) Uiso 1 1 calc R . .
H26B H 0.1381 0.3019 0.4770 0.018(5) Uiso 1 1 calc R . .
H26C H 0.1808 0.4679 0.5054 0.024(5) Uiso 1 1 calc R . .
C17 C 0.5151(2) 0.11848(19) 0.82667(12) 0.0210(4) Uani 1 1 d . . .
H17 H 0.5135 0.0323 0.8446 0.031(6) Uiso 1 1 calc R . .
C24 C -0.2514(2) 0.12427(17) 0.46679(12) 0.0173(3) Uani 1 1 d . . .
H24 H -0.1827 0.0838 0.4446 0.019(5) Uiso 1 1 calc R . .
C6 C -0.0328(3) 0.7628(2) 0.81989(14) 0.0296(4) Uani 1 1 d . . .
H6 H -0.1306 0.7841 0.8120 0.037(6) Uiso 1 1 calc R . .
C5 C 0.1192(3) 0.85319(19) 0.88945(13) 0.0281(4) Uani 1 1 d . . .
H5 H 0.1236 0.9347 0.9292 0.029(5) Uiso 1 1 calc R . .
C11 C 0.3119(2) 0.2710(2) 1.00781(13) 0.0274(4) Uani 1 1 d . . .
H11A H 0.4130 0.2843 0.9905 0.050(7) Uiso 1 1 calc R . .
H11B H 0.2894 0.1901 1.0381 0.040(6) Uiso 1 1 calc R . .
H11C H 0.3281 0.3558 1.0529 0.036(6) Uiso 1 1 calc R . .
C21 C -0.4574(2) 0.24361(18) 0.53259(13) 0.0190(3) Uani 1 1 d . . .
H21 H -0.5263 0.2837 0.5548 0.016(4) Uiso 1 1 calc R . .
H111 H -0.003(2) 0.4407(17) 0.6525(12) 0.008(4) Uiso 1 1 d . . .
H113 H 0.181(2) 0.1770(18) 0.6004(12) 0.005(4) Uiso 1 1 d . . .
H112 H -0.055(2) 0.3132(18) 0.7662(12) 0.014(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4310(12) . ?
S1 O3 1.4360(12) . ?
S1 N2 1.6381(15) . ?
S1 C19 1.7610(17) . ?
O1 N1 1.4422(17) . ?
O1 C1 1.445(2) . ?
N2 C12 1.482(2) . ?
N2 C8 1.485(2) . ?
N1 C12 1.455(2) . ?
N1 C26 1.458(2) . ?
C2 C3 1.390(2) . ?
C2 C7 1.391(2) . ?
C2 C1 1.503(2) . ?
C14 C13 1.390(2) . ?
C14 C15 1.390(2) . ?
C8 C9 1.530(2) . ?
C8 C1 1.539(2) . ?
C19 C20 1.387(2) . ?
C19 C24 1.391(2) . ?
C18 C17 1.387(2) . ?
C18 C13 1.391(2) . ?
C12 C13 1.531(2) . ?
C3 C4 1.385(2) . ?
C25 C22 1.499(2) . ?
C22 C21 1.392(2) . ?
C22 C23 1.393(2) . ?
C20 C21 1.383(2) . ?
C15 C16 1.382(3) . ?
C16 C17 1.385(3) . ?
C7 C6 1.387(3) . ?
C10 C9 1.523(2) . ?
C10 C11 1.525(2) . ?
C4 C5 1.385(3) . ?
C23 C24 1.382(2) . ?
C6 C5 1.379(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 120.13(7) . . ?
O2 S1 N2 106.66(7) . . ?
O3 S1 N2 106.22(8) . . ?
O2 S1 C19 107.39(8) . . ?
O3 S1 C19 108.72(8) . . ?
N2 S1 C19 107.06(8) . . ?
N1 O1 C1 112.91(11) . . ?
C12 N2 C8 116.90(12) . . ?
C12 N2 S1 122.11(11) . . ?
C8 N2 S1 118.12(11) . . ?
O1 N1 C12 110.19(12) . . ?
O1 N1 C26 110.19(12) . . ?
C12 N1 C26 117.27(13) . . ?
C3 C2 C7 119.04(16) . . ?
C3 C2 C1 121.41(15) . . ?
C7 C2 C1 119.53(15) . . ?
C13 C14 C15 120.31(16) . . ?
N2 C8 C9 112.14(13) . . ?
N2 C8 C1 106.79(13) . . ?
C9 C8 C1 114.52(13) . . ?
O1 C1 C2 106.55(13) . . ?
O1 C1 C8 109.72(12) . . ?
C2 C1 C8 114.51(13) . . ?
C20 C19 C24 120.61(15) . . ?
C20 C19 S1 119.33(12) . . ?
C24 C19 S1 119.89(12) . . ?
C17 C18 C13 120.38(16) . . ?
N1 C12 N2 114.50(13) . . ?
N1 C12 C13 110.52(13) . . ?
N2 C12 C13 110.36(13) . . ?
C4 C3 C2 120.19(17) . . ?
C21 C22 C23 118.31(15) . . ?
C21 C22 C25 120.32(15) . . ?
C23 C22 C25 121.36(15) . . ?
C21 C20 C19 119.32(15) . . ?
C14 C13 C18 119.01(15) . . ?
C14 C13 C12 122.47(15) . . ?
C18 C13 C12 118.46(15) . . ?
C16 C15 C14 120.40(17) . . ?
C15 C16 C17 119.47(16) . . ?
C6 C7 C2 120.49(17) . . ?
C9 C10 C11 111.53(15) . . ?
C10 C9 C8 114.24(14) . . ?
C5 C4 C3 120.40(17) . . ?
C24 C23 C22 121.35(15) . . ?
C16 C17 C18 120.38(16) . . ?
C23 C24 C19 119.12(15) . . ?
C5 C6 C7 120.14(18) . . ?
C6 C5 C4 119.71(17) . . ?
C20 C21 C22 121.25(16) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_3decam
_database_code_depnum_ccdc_archive 'CCDC 1489201'
_audit_update_record             
;
2016-06-30 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.31

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'

_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                   5.4942(17)
_cell_length_b                   18.284(6)
_cell_length_c                   6.781(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.824(5)
_cell_angle_gamma                90.00
_cell_volume                     661.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2272
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      28.41

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4022
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         28.41
_reflns_number_total             2817
_reflns_number_gt                2272
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_structure_solution    'SIR97(Altomare, et. al. 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0860P)²+0.7997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_number_reflns         2817
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1826
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.062
_refine_ls_shift/su_mean         0.015

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
O2 O 0.8674(5) 0.31096(14) 0.7460(4) 0.0224(6) Uani 1 1 d . . .
O1 O 0.6013(5) 0.18219(14) 0.7523(4) 0.0254(6) Uani 1 1 d . . .
C7 C 0.8594(7) 0.1888(2) 0.8489(5) 0.0198(7) Uani 1 1 d . . .
H7 H 0.9615 0.1789 0.7515 0.024 Uiso 1 1 calc R . .
N1 N 0.9030(6) 0.26428(17) 0.9267(5) 0.0234(7) Uani 1 1 d . . .
C6 C 0.9235(7) 0.13584(19) 1.0214(6) 0.0216(8) Uani 1 1 d . . .
C11 C 0.5566(7) 0.3630(2) 0.4784(6) 0.0232(8) Uani 1 1 d . . .
C16 C 0.3621(7) 0.4139(2) 0.4557(6) 0.0243(8) Uani 1 1 d . . .
H16 H 0.2653 0.4157 0.5509 0.029 Uiso 1 1 calc R . .
C1 C 1.1242(7) 0.0884(2) 1.0400(6) 0.0225(8) Uani 1 1 d . . .
H1 H 1.2152 0.0875 0.9407 0.027 Uiso 1 1 calc R . .
C9 C 0.5287(7) 0.2326(2) 0.5875(6) 0.0262(8) Uani 1 1 d . . .
H9A H 0.3485 0.2303 0.5345 0.031 Uiso 1 1 calc R . .
H9B H 0.6075 0.2187 0.4794 0.031 Uiso 1 1 calc R . .
C15 C 0.3122(7) 0.4618(2) 0.2925(6) 0.0252(8) Uani 1 1 d . . .
H15 H 0.1816 0.4952 0.2781 0.030 Uiso 1 1 calc R . .
C2 C 1.1899(7) 0.0421(2) 1.2082(6) 0.0265(9) Uani 1 1 d . . .
H2 H 1.3262 0.0108 1.2205 0.032 Uiso 1 1 calc R . .
C4 C 0.8527(7) 0.0886(2) 1.3347(6) 0.0246(8) Uani 1 1 d . . .
H4 H 0.7602 0.0886 1.4330 0.030 Uiso 1 1 calc R . .
C10 C 0.6042(7) 0.3106(2) 0.6548(6) 0.0239(8) Uani 1 1 d . . .
H10 H 0.5119 0.3266 0.7542 0.029 Uiso 1 1 calc R . .
C12 C 0.6988(7) 0.3609(2) 0.3338(6) 0.0234(8) Uani 1 1 d . . .
H12 H 0.8278 0.3271 0.3458 0.028 Uiso 1 1 calc R . .
C14 C 0.4571(7) 0.4599(2) 0.1505(6) 0.0252(8) Uani 1 1 d . . .
H14 H 0.4252 0.4925 0.0420 0.030 Uiso 1 1 calc R . .
C13 C 0.6476(7) 0.4097(2) 0.1710(6) 0.0237(8) Uani 1 1 d . . .
H13 H 0.7436 0.4082 0.0751 0.028 Uiso 1 1 calc R . .
C3 C 1.0573(7) 0.0420(2) 1.3546(6) 0.0252(8) Uani 1 1 d . . .
H3 H 1.1031 0.0111 1.4663 0.030 Uiso 1 1 calc R . .
C5 C 0.7859(7) 0.1352(2) 1.1689(6) 0.0239(8) Uani 1 1 d . . .
H5 H 0.6486 0.1661 1.1564 0.029 Uiso 1 1 calc R . .
C8 C 1.1653(6) 0.2763(2) 1.0292(5) 0.0267(7) Uani 1 1 d . . .
H8A H 1.2705 0.2594 0.9442 0.040 Uiso 1 1 calc R . .
H8B H 1.2043 0.2498 1.1551 0.040 Uiso 1 1 calc R . .
H8C H 1.1936 0.3275 1.0558 0.040 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C10 1.430(5) . ?
O2 N1 1.468(4) . ?
O1 C7 1.418(4) . ?
O1 C9 1.429(4) . ?
C7 N1 1.476(5) . ?
C7 C6 1.494(5) . ?
N1 C8 1.459(4) . ?
C6 C1 1.384(5) . ?
C6 C5 1.390(5) . ?
C11 C12 1.392(5) . ?
C11 C16 1.398(5) . ?
C11 C10 1.506(5) . ?
C16 C15 1.386(6) . ?
C1 C2 1.397(5) . ?
C9 C10 1.524(5) . ?
C15 C14 1.389(6) . ?
C2 C3 1.365(6) . ?
C4 C5 1.388(5) . ?
C4 C3 1.392(5) . ?
C12 C13 1.395(5) . ?
C14 C13 1.374(6) . ?

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
C10 O2 N1 106.1(3) . . ?
C7 O1 C9 111.6(3) . . ?
O1 C7 N1 107.7(3) . . ?
O1 C7 C6 109.2(3) . . ?
N1 C7 C6 109.8(3) . . ?
C8 N1 O2 103.3(3) . . ?
C8 N1 C7 111.6(3) . . ?
O2 N1 C7 105.5(2) . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 120.7(3) . . ?
C5 C6 C7 120.1(3) . . ?
C12 C11 C16 118.9(4) . . ?
C12 C11 C10 121.5(3) . . ?
C16 C11 C10 119.6(3) . . ?
C15 C16 C11 120.6(4) . . ?
C6 C1 C2 119.9(3) . . ?
O1 C9 C10 111.3(3) . . ?
C14 C15 C16 120.1(4) . . ?
C3 C2 C1 121.0(4) . . ?
C5 C4 C3 120.4(3) . . ?
O2 C10 C11 107.8(3) . . ?
O2 C10 C9 108.0(3) . . ?
C11 C10 C9 112.0(3) . . ?
C11 C12 C13 120.0(3) . . ?
C13 C14 C15 119.7(4) . . ?
C14 C13 C12 120.8(3) . . ?
C2 C3 C4 119.2(4) . . ?
C4 C5 C6 120.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.41
_diffrn_measured_fraction_theta_full 0.924
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.351
_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_14mayd_0m
_database_code_depnum_ccdc_archive 'CCDC 1489202'
_audit_update_record             
;
2016-06-30 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H24 N2 O3 S'
_chemical_formula_sum            'C23 H24 N2 O3 S'
_chemical_formula_weight         408.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 '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/n

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

_cell_length_a                   9.9562(6)
_cell_length_b                   12.5624(7)
_cell_length_c                   16.3026(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.165(2)
_cell_angle_gamma                90.00
_cell_volume                     2037.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3753
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      28.3

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20220
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         28.30
_reflns_number_total             5051
_reflns_number_gt                3753
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_structure_solution    'SIR97(Altomare, et. al. 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0566P)²+1.2454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5051
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
C6 C 0.27240(19) 1.23761(15) 0.02271(12) 0.0197(4) Uani 1 1 d . . .
H6 H 0.2664 1.2638 -0.0307 0.024 Uiso 1 1 calc R . .
C13 C 0.55834(18) 0.72785(15) 0.22157(12) 0.0208(4) Uani 1 1 d . . .
H13 H 0.4903 0.6803 0.2062 0.025 Uiso 1 1 calc R . .
C1 C 0.36109(18) 1.28512(14) 0.07962(12) 0.0180(4) Uani 1 1 d . . .
S1 S 0.10720(4) 1.00106(3) 0.15095(3) 0.01451(12) Uani 1 1 d . . .
O1 O 0.09056(13) 1.00612(10) 0.23774(8) 0.0190(3) Uani 1 1 d . . .
O3 O 0.41819(12) 0.79273(10) 0.07126(8) 0.0164(3) Uani 1 1 d . . .
C19 C 0.1897(2) 0.62484(15) 0.06123(13) 0.0252(4) Uani 1 1 d . . .
H19 H 0.2689 0.6267 0.0328 0.030 Uiso 1 1 calc R . .
O2 O -0.00901(12) 0.99502(10) 0.09603(8) 0.0191(3) Uani 1 1 d . . .
C2 C 0.44692(19) 1.37811(15) 0.05652(13) 0.0235(4) Uani 1 1 d . . .
H2A H 0.4151 1.4060 0.0045 0.035 Uiso 1 1 calc R . .
H2B H 0.5384 1.3552 0.0526 0.035 Uiso 1 1 calc R . .
H2C H 0.4420 1.4325 0.0977 0.035 Uiso 1 1 calc R . .
C7 C 0.19285(18) 1.15220(14) 0.04386(12) 0.0189(4) Uani 1 1 d . . .
H7 H 0.1334 1.1216 0.0053 0.023 Uiso 1 1 calc R . .
C5 C 0.20310(17) 1.11275(13) 0.12367(11) 0.0147(4) Uani 1 1 d . . .
N2 N 0.19673(15) 0.89647(11) 0.13376(9) 0.0154(3) Uani 1 1 d . . .
C14 C 0.31416(17) 0.87273(14) 0.18763(11) 0.0156(4) Uani 1 1 d . . .
H14A H 0.3015 0.8050 0.2148 0.019 Uiso 1 1 calc R . .
H14B H 0.3245 0.9274 0.2294 0.019 Uiso 1 1 calc R . .
C15 C 0.43948(17) 0.86835(14) 0.13728(11) 0.0157(4) Uani 1 1 d . . .
H15 H 0.4584 0.9389 0.1148 0.019 Uiso 1 1 calc R . .
C8 C 0.55763(17) 0.83034(14) 0.18946(11) 0.0164(4) Uani 1 1 d . . .
C9 C 0.66208(18) 0.89929(15) 0.21120(12) 0.0199(4) Uani 1 1 d . . .
H9 H 0.6633 0.9674 0.1888 0.024 Uiso 1 1 calc R . .
C10 C 0.76457(18) 0.86785(16) 0.26584(12) 0.0229(4) Uani 1 1 d . . .
H10 H 0.8343 0.9144 0.2798 0.027 Uiso 1 1 calc R . .
C11 C 0.76246(19) 0.76675(17) 0.29951(13) 0.0250(4) Uani 1 1 d . . .
H11 H 0.8294 0.7459 0.3375 0.030 Uiso 1 1 calc R . .
N1 N 0.30654(15) 0.82031(12) 0.01598(9) 0.0162(3) Uani 1 1 d . . .
C16 C 0.18280(17) 0.82846(14) 0.06018(11) 0.0156(4) Uani 1 1 d . . .
H16 H 0.1153 0.8616 0.0230 0.019 Uiso 1 1 calc R . .
C20 C 0.12896(17) 0.71946(14) 0.08385(11) 0.0159(4) Uani 1 1 d . . .
C18 C 0.1329(2) 0.52772(16) 0.08077(14) 0.0284(5) Uani 1 1 d . . .
H18 H 0.1746 0.4649 0.0654 0.034 Uiso 1 1 calc R . .
C23 C 0.0154(2) 0.52322(16) 0.12268(13) 0.0237(4) Uani 1 1 d . . .
H23 H -0.0223 0.4578 0.1355 0.028 Uiso 1 1 calc R . .
C22 C -0.04586(19) 0.61693(16) 0.14559(12) 0.0223(4) Uani 1 1 d . . .
H22 H -0.1253 0.6146 0.1738 0.027 Uiso 1 1 calc R . .
C21 C 0.01074(18) 0.71437(15) 0.12669(11) 0.0188(4) Uani 1 1 d . . .
H21 H -0.0307 0.7769 0.1428 0.023 Uiso 1 1 calc R . .
C17 C 0.33935(19) 0.91557(15) -0.03031(12) 0.0200(4) Uani 1 1 d . . .
H17A H 0.3503 0.9747 0.0066 0.030 Uiso 1 1 calc R . .
H17B H 0.2679 0.9305 -0.0698 0.030 Uiso 1 1 calc R . .
H17C H 0.4214 0.9042 -0.0581 0.030 Uiso 1 1 calc R . .
C12 C 0.66038(19) 0.69654(16) 0.27647(13) 0.0254(4) Uani 1 1 d . . .
H12 H 0.6604 0.6280 0.2980 0.030 Uiso 1 1 calc R . .
C4 C 0.29165(17) 1.15779(14) 0.18148(11) 0.0171(4) Uani 1 1 d . . .
H4 H 0.2989 1.1306 0.2345 0.020 Uiso 1 1 calc R . .
C3 C 0.36942(18) 1.24409(15) 0.15901(12) 0.0183(4) Uani 1 1 d . . .
H3 H 0.4282 1.2751 0.1978 0.022 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 C7 1.385(3) . ?
C6 C1 1.391(3) . ?
C6 H6 0.9300 . ?
C13 C12 1.385(3) . ?
C13 C8 1.390(3) . ?
C13 H13 0.9300 . ?
C1 C3 1.393(3) . ?
C1 C2 1.504(3) . ?
S1 O1 1.4322(14) . ?
S1 O2 1.4380(13) . ?
S1 N2 1.6181(15) . ?
S1 C5 1.7636(18) . ?
O3 N1 1.4464(18) . ?
O3 C15 1.445(2) . ?
C19 C18 1.387(3) . ?
C19 C20 1.390(3) . ?
C19 H19 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C7 C5 1.392(3) . ?
C7 H7 0.9300 . ?
C5 C4 1.387(2) . ?
N2 C14 1.466(2) . ?
N2 C16 1.475(2) . ?
C14 C15 1.520(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C8 1.503(2) . ?
C15 H15 0.9800 . ?
C8 C9 1.389(3) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
N1 C16 1.454(2) . ?
N1 C17 1.458(2) . ?
C16 C20 1.525(2) . ?
C16 H16 0.9800 . ?
C20 C21 1.393(3) . ?
C18 C23 1.378(3) . ?
C18 H18 0.9300 . ?
C23 C22 1.384(3) . ?
C23 H23 0.9300 . ?
C22 C21 1.387(3) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C12 H12 0.9300 . ?
C4 C3 1.389(3) . ?
C4 H4 0.9300 . ?
C3 H3 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
C7 C6 C1 121.39(18) . . ?
C7 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C12 C13 C8 119.97(17) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C6 C1 C3 118.36(17) . . ?
C6 C1 C2 121.25(17) . . ?
C3 C1 C2 120.39(17) . . ?
O1 S1 O2 119.81(8) . . ?
O1 S1 N2 106.99(8) . . ?
O2 S1 N2 106.55(8) . . ?
O1 S1 C5 107.32(8) . . ?
O2 S1 C5 108.39(8) . . ?
N2 S1 C5 107.18(8) . . ?
N1 O3 C15 113.22(12) . . ?
C18 C19 C20 120.43(18) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C6 C7 C5 119.08(17) . . ?
C6 C7 H7 120.5 . . ?
C5 C7 H7 120.5 . . ?
C4 C5 C7 120.81(17) . . ?
C4 C5 S1 119.32(14) . . ?
C7 C5 S1 119.83(14) . . ?
C14 N2 C16 114.69(14) . . ?
C14 N2 S1 119.57(12) . . ?
C16 N2 S1 125.15(12) . . ?
N2 C14 C15 109.64(14) . . ?
N2 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
N2 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O3 C15 C8 107.60(14) . . ?
O3 C15 C14 109.00(14) . . ?
C8 C15 C14 110.28(15) . . ?
O3 C15 H15 110.0 . . ?
C8 C15 H15 110.0 . . ?
C14 C15 H15 110.0 . . ?
C9 C8 C13 119.24(17) . . ?
C9 C8 C15 120.57(16) . . ?
C13 C8 C15 120.01(16) . . ?
C10 C9 C8 120.80(18) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.63(18) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 119.89(18) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
O3 N1 C16 110.71(13) . . ?
O3 N1 C17 109.70(13) . . ?
C16 N1 C17 114.15(14) . . ?
N1 C16 N2 112.85(14) . . ?
N1 C16 C20 112.00(14) . . ?
N2 C16 C20 109.72(14) . . ?
N1 C16 H16 107.3 . . ?
N2 C16 H16 107.3 . . ?
C20 C16 H16 107.3 . . ?
C19 C20 C21 118.57(17) . . ?
C19 C20 C16 122.70(16) . . ?
C21 C20 C16 118.67(16) . . ?
C23 C18 C19 120.72(19) . . ?
C23 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C23 C22 119.35(18) . . ?
C18 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C22 C21 120.25(18) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C21 C20 120.67(18) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C12 C11 120.42(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C5 C4 C3 119.05(17) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C3 C1 121.30(17) . . ?
C4 C3 H3 119.3 . . ?
C1 C3 H3 119.3 . . ?

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
C7 C6 C1 C3 0.6(3) . . . . ?
C7 C6 C1 C2 -179.76(17) . . . . ?
C1 C6 C7 C5 -0.6(3) . . . . ?
C6 C7 C5 C4 -0.1(3) . . . . ?
C6 C7 C5 S1 -177.73(14) . . . . ?
O1 S1 C5 C4 27.10(16) . . . . ?
O2 S1 C5 C4 157.82(14) . . . . ?
N2 S1 C5 C4 -87.53(15) . . . . ?
O1 S1 C5 C7 -155.26(14) . . . . ?
O2 S1 C5 C7 -24.53(17) . . . . ?
N2 S1 C5 C7 90.12(15) . . . . ?
O1 S1 N2 C14 -43.08(15) . . . . ?
O2 S1 N2 C14 -172.36(13) . . . . ?
C5 S1 N2 C14 71.76(15) . . . . ?
O1 S1 N2 C16 146.24(14) . . . . ?
O2 S1 N2 C16 16.97(17) . . . . ?
C5 S1 N2 C16 -98.91(15) . . . . ?
C16 N2 C14 C15 50.30(19) . . . . ?
S1 N2 C14 C15 -121.32(14) . . . . ?
N1 O3 C15 C8 -179.90(13) . . . . ?
N1 O3 C15 C14 60.51(17) . . . . ?
N2 C14 C15 O3 -54.81(18) . . . . ?
N2 C14 C15 C8 -172.73(14) . . . . ?
C12 C13 C8 C9 1.9(3) . . . . ?
C12 C13 C8 C15 -173.29(18) . . . . ?
O3 C15 C8 C9 130.54(17) . . . . ?
C14 C15 C8 C9 -110.68(19) . . . . ?
O3 C15 C8 C13 -54.3(2) . . . . ?
C14 C15 C8 C13 64.4(2) . . . . ?
C13 C8 C9 C10 -1.6(3) . . . . ?
C15 C8 C9 C10 173.55(17) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 2.0(3) . . . . ?
C15 O3 N1 C16 -58.31(17) . . . . ?
C15 O3 N1 C17 68.55(17) . . . . ?
O3 N1 C16 N2 50.20(18) . . . . ?
C17 N1 C16 N2 -74.16(19) . . . . ?
O3 N1 C16 C20 -74.22(17) . . . . ?
C17 N1 C16 C20 161.42(14) . . . . ?
C14 N2 C16 N1 -48.8(2) . . . . ?
S1 N2 C16 N1 122.24(15) . . . . ?
C14 N2 C16 C20 76.82(18) . . . . ?
S1 N2 C16 C20 -112.11(15) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C18 C19 C20 C16 -176.74(19) . . . . ?
N1 C16 C20 C19 -3.0(2) . . . . ?
N2 C16 C20 C19 -129.19(18) . . . . ?
N1 C16 C20 C21 179.93(15) . . . . ?
N2 C16 C20 C21 53.8(2) . . . . ?
C20 C19 C18 C23 0.2(3) . . . . ?
C19 C18 C23 C22 -0.2(3) . . . . ?
C18 C23 C22 C21 -0.2(3) . . . . ?
C23 C22 C21 C20 0.6(3) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C16 C20 C21 C22 176.48(16) . . . . ?
C8 C13 C12 C11 -0.2(3) . . . . ?
C10 C11 C12 C13 -1.7(3) . . . . ?
C7 C5 C4 C3 0.8(3) . . . . ?
S1 C5 C4 C3 178.38(13) . . . . ?
C5 C4 C3 C1 -0.7(3) . . . . ?
C6 C1 C3 C4 0.1(3) . . . . ?
C2 C1 C3 C4 -179.58(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 O2 0.93 2.50 3.414(2) 167.2 3_575
C7 H7 O2 0.93 2.50 3.414(2) 167.2 3_575
C7 H7 O2 0.93 2.50 3.414(2) 167.2 3_575

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.069
