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

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

data_sad
_database_code_depnum_ccdc_archive 'CCDC 1409591'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N2 O2'
_chemical_formula_weight         369.43

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/C

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

_cell_length_a                   29.4790(8)
_cell_length_b                   12.0530(3)
_cell_length_c                   11.6531(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.029(2)
_cell_angle_gamma                90.00
_cell_volume                     3937.17(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    571(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      5.99
_cell_measurement_theta_max      62.68

_exptl_crystal_description       plane
_exptl_crystal_colour            coreless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8422
_exptl_absorpt_correction_T_max  0.8835
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      571(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART (Bruker, 1998)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8227
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.99
_diffrn_reflns_theta_max         62.68
_reflns_number_total             3109
_reflns_number_gt                2772
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAIRT (Bruker, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.1053P)²+3.6159P] 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         3109
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   0.674
_refine_ls_restrained_S_all      0.674
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37959(5) 0.38240(9) 0.07569(12) 0.0752(4) Uani 1 1 d . . .
O2 O 0.41328(4) 0.48062(9) -0.03795(11) 0.0654(3) Uani 1 1 d . . .
N1 N 0.35033(4) 0.75117(9) 0.08762(9) 0.0429(3) Uani 1 1 d . . .
C17 C 0.35040(5) 0.87015(11) 0.08162(12) 0.0439(3) Uani 1 1 d . . .
C1 C 0.41427(5) 0.73353(11) -0.00834(13) 0.0467(3) Uani 1 1 d . . .
C2 C 0.41596(6) 0.70898(13) -0.12365(14) 0.0537(4) Uani 1 1 d . . .
H2A H 0.3938 0.6604 -0.1726 0.064 Uiso 1 1 calc R . .
C3 C 0.45039(7) 0.75627(14) -0.16577(17) 0.0660(5) Uani 1 1 d . . .
H3A H 0.4514 0.7387 -0.2427 0.079 Uiso 1 1 calc R . .
C4 C 0.48309(7) 0.82869(15) -0.0956(2) 0.0730(5) Uani 1 1 d . . .
H4A H 0.5060 0.8607 -0.1251 0.088 Uiso 1 1 calc R . .
C5 C 0.48200(6) 0.85413(14) 0.01909(18) 0.0696(5) Uani 1 1 d . . .
H5A H 0.5042 0.9032 0.0671 0.084 Uiso 1 1 calc R . .
C6 C 0.44785(6) 0.80654(12) 0.06254(15) 0.0568(4) Uani 1 1 d . . .
H6A H 0.4474 0.8236 0.1400 0.068 Uiso 1 1 calc R . .
C7 C 0.37796(5) 0.68398(11) 0.04005(12) 0.0429(3) Uani 1 1 d . . .
C8 C 0.36752(5) 0.57522(11) 0.06204(12) 0.0451(3) Uani 1 1 d . . .
C9 C 0.33339(5) 0.57892(11) 0.12464(13) 0.0478(3) Uani 1 1 d . . .
H9A H 0.3202 0.5176 0.1508 0.057 Uiso 1 1 calc R . .
C10 C 0.32303(5) 0.68670(11) 0.14028(12) 0.0443(3) Uani 1 1 d . . .
C11 C 0.28853(5) 0.72918(11) 0.19769(12) 0.0446(3) Uani 1 1 d . . .
C12 C 0.28442(6) 0.67260(13) 0.29844(13) 0.0542(4) Uani 1 1 d . . .
H12A H 0.3051 0.6143 0.3307 0.065 Uiso 1 1 calc R . .
C13 C 0.25019(6) 0.70189(15) 0.35072(15) 0.0634(4) Uani 1 1 d . . .
H13A H 0.2474 0.6622 0.4167 0.076 Uiso 1 1 calc R . .
C14 C 0.21999(6) 0.78972(14) 0.30584(15) 0.0618(4) Uani 1 1 d . . .
H14A H 0.1970 0.8097 0.3415 0.074 Uiso 1 1 calc R . .
C15 C 0.22418(6) 0.84743(13) 0.20817(14) 0.0572(4) Uani 1 1 d . . .
H15A H 0.2041 0.9072 0.1782 0.069 Uiso 1 1 calc R . .
C16 C 0.25797(5) 0.81773(12) 0.15376(13) 0.0491(3) Uani 1 1 d . . .
H16A H 0.2602 0.8574 0.0873 0.059 Uiso 1 1 calc R . .
N2 N 0.36697(5) 0.92166(10) 0.18699(11) 0.0574(3) Uani 1 1 d . . .
C18 C 0.36905(7) 1.03234(14) 0.18140(18) 0.0726(5) Uani 1 1 d . . .
H18A H 0.3798 1.0714 0.2536 0.087 Uiso 1 1 calc R . .
C19 C 0.35633(7) 1.09206(14) 0.07564(19) 0.0762(6) Uani 1 1 d . . .
H19A H 0.3597 1.1688 0.0767 0.091 Uiso 1 1 calc R . .
C20 C 0.33858(7) 1.03618(14) -0.03121(18) 0.0699(5) Uani 1 1 d . . .
H20A H 0.3291 1.0744 -0.1041 0.084 Uiso 1 1 calc R . .
C21 C 0.33505(6) 0.92203(12) -0.02858(14) 0.0542(4) Uani 1 1 d . . .
H21A H 0.3227 0.8815 -0.0993 0.065 Uiso 1 1 calc R . .
C22 C 0.38700(5) 0.47014(11) 0.03577(13) 0.0496(4) Uani 1 1 d . . .
C23 C 0.43311(8) 0.38043(16) -0.0714(2) 0.0807(6) Uani 1 1 d . . .
H23B H 0.4077 0.3306 -0.1146 0.097 Uiso 1 1 calc R . .
H23C H 0.4529 0.3427 0.0001 0.097 Uiso 1 1 calc R . .
C24 C 0.46196(8) 0.4134(2) -0.14945(18) 0.0883(7) Uani 1 1 d . . .
H24C H 0.4757 0.3486 -0.1733 0.133 Uiso 1 1 calc R . .
H24D H 0.4870 0.4626 -0.1058 0.133 Uiso 1 1 calc R . .
H24A H 0.4420 0.4505 -0.2199 0.133 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
O1 C22 1.2023(18) . ?
O2 C22 1.3290(19) . ?
O2 C23 1.4468(19) . ?
N1 C7 1.3806(17) . ?
N1 C10 1.3904(17) . ?
N1 C17 1.4359(17) . ?
C17 N2 1.3268(18) . ?
C17 C21 1.373(2) . ?
C1 C6 1.389(2) . ?
C1 C2 1.392(2) . ?
C1 C7 1.4812(19) . ?
C2 C3 1.380(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.3884(19) . ?
C8 C9 1.414(2) . ?
C8 C22 1.4618(19) . ?
C9 C10 1.3597(19) . ?
C9 H9A 0.9300 . ?
C10 C11 1.4715(19) . ?
C11 C16 1.388(2) . ?
C11 C12 1.3951(19) . ?
C12 C13 1.377(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.378(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.372(2) . ?
C14 H14A 0.9300 . ?
C15 C16 1.383(2) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
N2 C18 1.338(2) . ?
C18 C19 1.375(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.369(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.381(2) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C23 C24 1.479(3) . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 H24C 0.9600 . ?
C24 H24D 0.9600 . ?
C24 H24A 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
C22 O2 C23 117.38(13) . . ?
C7 N1 C10 110.08(11) . . ?
C7 N1 C17 123.80(11) . . ?
C10 N1 C17 126.12(11) . . ?
N2 C17 C21 124.95(13) . . ?
N2 C17 N1 115.33(12) . . ?
C21 C17 N1 119.69(12) . . ?
C6 C1 C2 118.48(14) . . ?
C6 C1 C7 119.66(13) . . ?
C2 C1 C7 121.86(13) . . ?
C3 C2 C1 120.37(16) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 120.73(17) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 119.78(16) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C6 C5 C4 119.96(17) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 120.68(16) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
N1 C7 C8 106.71(11) . . ?
N1 C7 C1 120.14(12) . . ?
C8 C7 C1 132.73(12) . . ?
C7 C8 C9 107.41(11) . . ?
C7 C8 C22 130.96(13) . . ?
C9 C8 C22 121.58(12) . . ?
C10 C9 C8 108.92(12) . . ?
C10 C9 H9A 125.5 . . ?
C8 C9 H9A 125.5 . . ?
C9 C10 N1 106.87(12) . . ?
C9 C10 C11 127.50(12) . . ?
N1 C10 C11 125.60(12) . . ?
C16 C11 C12 118.07(13) . . ?
C16 C11 C10 124.11(12) . . ?
C12 C11 C10 117.70(13) . . ?
C13 C12 C11 120.90(15) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C14 C13 C12 120.34(14) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C15 C14 C13 119.40(14) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
C14 C15 C16 120.78(15) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C15 C16 C11 120.47(13) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?
C17 N2 C18 115.51(14) . . ?
N2 C18 C19 124.16(16) . . ?
N2 C18 H18A 117.9 . . ?
C19 C18 H18A 117.9 . . ?
C20 C19 C18 118.62(15) . . ?
C20 C19 H19A 120.7 . . ?
C18 C19 H19A 120.7 . . ?
C19 C20 C21 118.69(16) . . ?
C19 C20 H20A 120.7 . . ?
C21 C20 H20A 120.7 . . ?
C17 C21 C20 117.98(15) . . ?
C17 C21 H21A 121.0 . . ?
C20 C21 H21A 121.0 . . ?
O1 C22 O2 123.09(13) . . ?
O1 C22 C8 123.42(14) . . ?
O2 C22 C8 113.48(12) . . ?
O2 C23 C24 107.38(16) . . ?
O2 C23 H23B 110.2 . . ?
C24 C23 H23B 110.2 . . ?
O2 C23 H23C 110.2 . . ?
C24 C23 H23C 110.2 . . ?
H23B C23 H23C 108.5 . . ?
C23 C24 H24C 109.5 . . ?
C23 C24 H24D 109.5 . . ?
H24C C24 H24D 109.5 . . ?
C23 C24 H24A 109.5 . . ?
H24C C24 H24A 109.5 . . ?
H24D C24 H24A 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        62.68
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.027
####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1409592'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O2 S'
_chemical_formula_weight         388.47

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/C

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

_cell_length_a                   15.4468(4)
_cell_length_b                   12.2137(3)
_cell_length_c                   10.5709(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.313(3)
_cell_angle_gamma                90.00
_cell_volume                     1994.30(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    571(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      4.62
_cell_measurement_theta_max      62.60

_exptl_crystal_description       plane
_exptl_crystal_colour            coloeless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    1.606
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_T_max  0.7292
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      571(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART (Bruker, 1998)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5045
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.62
_diffrn_reflns_theta_max         62.60
_reflns_number_total             2672
_reflns_number_gt                2416
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAIRT (Bruker, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0952P)²+1.3150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0250(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2672
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1537
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.71612(5) 0.96470(5) 0.03699(8) 0.0506(3) Uani 1 1 d . . .
O1 O 0.65830(16) 0.98229(18) 0.1399(2) 0.0674(7) Uani 1 1 d . . .
O2 O 0.78513(15) 0.88678(17) 0.0530(2) 0.0662(7) Uani 1 1 d . . .
N1 N 0.87944(19) 1.4207(2) 0.0453(3) 0.0663(8) Uani 1 1 d . . .
N2 N 0.79783(14) 1.26173(17) -0.0255(2) 0.0403(6) Uani 1 1 d . . .
C1 C 0.80337(17) 1.3777(2) -0.0027(3) 0.0421(7) Uani 1 1 d . . .
C2 C 0.73375(17) 1.4341(2) -0.0317(3) 0.0516(8) Uani 1 1 d . . .
H2A H 0.6843 1.4011 -0.0647 0.062 Uiso 1 1 calc R . .
C3 C 0.7382(3) 1.5427(3) -0.0106(5) 0.0851(13) Uani 1 1 d . . .
H3A H 0.6897 1.5850 -0.0291 0.102 Uiso 1 1 calc R . .
C4 C 0.8097(3) 1.5939(3) 0.0362(4) 0.0739(11) Uani 1 1 d . . .
H4A H 0.8099 1.6693 0.0486 0.089 Uiso 1 1 calc R . .
C5 C 0.8812(2) 1.5329(2) 0.0647(3) 0.0584(9) Uani 1 1 d . . .
H5A H 0.9307 1.5664 0.0968 0.070 Uiso 1 1 calc R . .
C6 C 0.85284(18) 1.2032(2) -0.1052(3) 0.0424(7) Uani 1 1 d . . .
C7 C 0.82980(19) 1.0955(2) -0.0956(3) 0.0454(7) Uani 1 1 d . . .
H7A H 0.8547 1.0374 -0.1391 0.055 Uiso 1 1 calc R . .
C8 C 0.76158(18) 1.0884(2) -0.0081(3) 0.0438(7) Uani 1 1 d . . .
C9 C 0.74178(17) 1.1921(2) 0.0356(3) 0.0419(7) Uani 1 1 d . . .
C10 C 0.6812(2) 1.2310(3) 0.1345(3) 0.0561(8) Uani 1 1 d . . .
H10A H 0.6838 1.3094 0.1398 0.084 Uiso 1 1 calc R . .
H10B H 0.6972 1.1998 0.2146 0.084 Uiso 1 1 calc R . .
H10C H 0.6233 1.2089 0.1130 0.084 Uiso 1 1 calc R . .
C11 C 0.92040(18) 1.2510(2) -0.1849(3) 0.0425(7) Uani 1 1 d . . .
C12 C 0.9073(2) 1.3444(2) -0.2585(3) 0.0489(7) Uani 1 1 d . . .
H12A H 0.8559 1.3838 -0.2521 0.059 Uiso 1 1 calc R . .
C13 C 0.9712(2) 1.3781(3) -0.3412(3) 0.0610(9) Uani 1 1 d . . .
H13A H 0.9620 1.4399 -0.3910 0.073 Uiso 1 1 calc R . .
C14 C 1.0484(2) 1.3216(3) -0.3511(3) 0.0627(9) Uani 1 1 d . . .
H14A H 1.0903 1.3445 -0.4083 0.075 Uiso 1 1 calc R . .
C15 C 1.0630(2) 1.2316(3) -0.2760(3) 0.0596(9) Uani 1 1 d . . .
H15A H 1.1153 1.1942 -0.2804 0.072 Uiso 1 1 calc R . .
C16 C 0.9991(2) 1.1969(2) -0.1938(3) 0.0517(8) Uani 1 1 d . . .
H16A H 1.0092 1.1359 -0.1433 0.062 Uiso 1 1 calc R . .
C17 C 0.65426(18) 0.9225(2) -0.0954(3) 0.0526(8) Uani 1 1 d . . .
C18 C 0.6760(3) 0.8287(3) -0.1605(4) 0.0739(11) Uani 1 1 d . . .
H18A H 0.7245 0.7884 -0.1367 0.089 Uiso 1 1 calc R . .
C19 C 0.6256(3) 0.7952(3) -0.2604(5) 0.0903(13) Uani 1 1 d . . .
H19A H 0.6404 0.7315 -0.3034 0.108 Uiso 1 1 calc R . .
C20 C 0.5542(2) 0.8528(4) -0.2984(4) 0.0829(12) Uani 1 1 d . . .
C21 C 0.5335(2) 0.9459(4) -0.2323(5) 0.0910(14) Uani 1 1 d . . .
H21A H 0.4850 0.9862 -0.2563 0.109 Uiso 1 1 calc R . .
C22 C 0.5828(2) 0.9806(3) -0.1315(4) 0.0784(12) Uani 1 1 d . . .
H22A H 0.5675 1.0437 -0.0879 0.094 Uiso 1 1 calc R . .
C23 C 0.4991(4) 0.8149(6) -0.4079(6) 0.128(2) Uani 1 1 d . . .
H23A H 0.5229 0.7487 -0.4422 0.192 Uiso 1 1 calc R . .
H23B H 0.4980 0.8705 -0.4721 0.192 Uiso 1 1 calc R . .
H23C H 0.4412 0.8014 -0.3791 0.192 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
S1 O1 1.427(3) . ?
S1 O2 1.438(2) . ?
S1 C8 1.734(3) . ?
S1 C17 1.767(3) . ?
N1 C1 1.381(4) . ?
N1 C5 1.386(4) . ?
N2 C9 1.377(3) . ?
N2 C6 1.397(4) . ?
N2 C1 1.440(3) . ?
C1 C2 1.312(4) . ?
C2 C3 1.346(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.360(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.364(5) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.366(4) . ?
C6 C11 1.466(4) . ?
C7 C8 1.409(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.383(4) . ?
C9 C10 1.485(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.387(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.384(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.383(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.384(4) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C22 1.365(5) . ?
C17 C18 1.378(4) . ?
C18 C19 1.371(6) . ?
C18 H18A 0.9300 . ?
C19 C20 1.367(6) . ?
C19 H19A 0.9300 . ?
C20 C21 1.373(6) . ?
C20 C23 1.506(7) . ?
C21 C22 1.374(6) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
O1 S1 O2 118.42(15) . . ?
O1 S1 C8 109.52(14) . . ?
O2 S1 C8 107.94(13) . . ?
O1 S1 C17 108.04(15) . . ?
O2 S1 C17 107.30(14) . . ?
C8 S1 C17 104.76(14) . . ?
C1 N1 C5 116.5(3) . . ?
C9 N2 C6 110.6(2) . . ?
C9 N2 C1 124.5(2) . . ?
C6 N2 C1 124.7(2) . . ?
C2 C1 N1 125.5(3) . . ?
C2 C1 N2 115.5(2) . . ?
N1 C1 N2 119.0(2) . . ?
C1 C2 C3 115.9(3) . . ?
C1 C2 H2A 122.0 . . ?
C3 C2 H2A 122.0 . . ?
C2 C3 C4 123.6(3) . . ?
C2 C3 H3A 118.2 . . ?
C4 C3 H3A 118.2 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 N1 119.5(3) . . ?
C4 C5 H5A 120.2 . . ?
N1 C5 H5A 120.2 . . ?
C7 C6 N2 106.8(2) . . ?
C7 C6 C11 127.8(3) . . ?
N2 C6 C11 125.4(2) . . ?
C6 C7 C8 107.7(2) . . ?
C6 C7 H7A 126.1 . . ?
C8 C7 H7A 126.1 . . ?
C9 C8 C7 109.3(2) . . ?
C9 C8 S1 128.0(2) . . ?
C7 C8 S1 122.7(2) . . ?
N2 C9 C8 105.6(2) . . ?
N2 C9 C10 122.2(2) . . ?
C8 C9 C10 132.0(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 118.4(3) . . ?
C16 C11 C6 118.4(3) . . ?
C12 C11 C6 123.0(3) . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C15 C16 C11 121.7(3) . . ?
C15 C16 H16A 119.2 . . ?
C11 C16 H16A 119.2 . . ?
C22 C17 C18 119.4(3) . . ?
C22 C17 S1 120.2(3) . . ?
C18 C17 S1 120.4(3) . . ?
C19 C18 C17 119.6(4) . . ?
C19 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
C20 C19 C18 121.8(4) . . ?
C20 C19 H19A 119.1 . . ?
C18 C19 H19A 119.1 . . ?
C19 C20 C21 117.8(4) . . ?
C19 C20 C23 121.3(4) . . ?
C21 C20 C23 120.8(5) . . ?
C20 C21 C22 121.3(4) . . ?
C20 C21 H21A 119.3 . . ?
C22 C21 H21A 119.3 . . ?
C17 C22 C21 120.1(3) . . ?
C17 C22 H22A 120.0 . . ?
C21 C22 H22A 120.0 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.97
_diffrn_reflns_theta_full        62.60
_diffrn_measured_fraction_theta_full 0.97
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.048
