# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_nb7154
_database_code_depnum_ccdc_archive 'CCDC 1500282'
_audit_update_record             
;
2016-08-21 deposited with the CCDC.
2017-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H22 N2 O2 S'
_chemical_formula_sum            'C25 H22 N2 O2 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         414.51

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'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

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

_cell_length_a                   8.8691(4)
_cell_length_b                   9.8046(5)
_cell_length_c                   12.4019(6)
_cell_angle_alpha                99.836(2)
_cell_angle_beta                 102.889(2)
_cell_angle_gamma                94.239(2)
_cell_volume                     1028.75(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      26.39
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9209
_exptl_absorpt_correction_T_max  0.9373
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18292
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         26.42
_reflns_number_total             4204
_reflns_number_gt                3632
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0652P)²+0.5836P] 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         4204
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
S S 0.40936(5) 0.80138(4) 0.66298(3) 0.02053(13) Uani 1 1 d . . .
O1 O 0.28011(13) 0.70515(12) 0.59497(9) 0.0264(3) Uani 1 1 d . . .
O2 O 0.39314(15) 0.94724(12) 0.68700(10) 0.0285(3) Uani 1 1 d . . .
N1 N 0.45980(15) 0.75032(13) 0.78393(10) 0.0192(3) Uani 1 1 d . . .
N2 N 0.53092(15) 0.79208(14) 1.14328(11) 0.0181(3) Uani 1 1 d . . .
C1 C 0.56803(19) 0.78435(16) 0.59902(12) 0.0204(3) Uani 1 1 d . . .
C2 C 0.6180(2) 0.65401(17) 0.57522(14) 0.0254(4) Uani 1 1 d . . .
H2C H 0.5709 0.5760 0.5967 0.031 Uiso 1 1 calc R . .
C3 C 0.7368(2) 0.63866(18) 0.52009(14) 0.0282(4) Uani 1 1 d . . .
H3A H 0.7720 0.5498 0.5049 0.034 Uiso 1 1 calc R . .
C4 C 0.8059(2) 0.7514(2) 0.48649(14) 0.0287(4) Uani 1 1 d . . .
C5 C 0.7558(2) 0.88103(19) 0.51281(15) 0.0314(4) Uani 1 1 d . . .
H5A H 0.8028 0.9591 0.4914 0.038 Uiso 1 1 calc R . .
C6 C 0.6385(2) 0.89905(18) 0.56975(14) 0.0273(4) Uani 1 1 d . . .
H6A H 0.6069 0.9888 0.5885 0.033 Uiso 1 1 calc R . .
C7 C 0.9311(2) 0.7304(3) 0.42255(18) 0.0447(5) Uani 1 1 d . . .
H7A H 0.9675 0.8197 0.4061 0.067 Uiso 1 1 calc R . .
H7B H 0.8887 0.6637 0.3517 0.067 Uiso 1 1 calc R . .
H7C H 1.0184 0.6942 0.4683 0.067 Uiso 1 1 calc R . .
C8 C 0.43629(18) 0.59936(15) 0.78685(13) 0.0191(3) Uani 1 1 d . . .
H8A H 0.5387 0.5662 0.8122 0.023 Uiso 1 1 calc R . .
H8B H 0.3876 0.5466 0.7099 0.023 Uiso 1 1 calc R . .
C9 C 0.33408(18) 0.57108(16) 0.86517(13) 0.0203(3) Uani 1 1 d . . .
H9A H 0.2290 0.5966 0.8353 0.024 Uiso 1 1 calc R . .
H9B H 0.3233 0.4699 0.8653 0.024 Uiso 1 1 calc R . .
C10 C 0.39431(17) 0.64850(15) 0.98406(13) 0.0169(3) Uani 1 1 d . . .
C11 C 0.32792(17) 0.62591(15) 1.07556(13) 0.0179(3) Uani 1 1 d . . .
C12 C 0.20187(18) 0.53584(17) 1.08416(14) 0.0221(3) Uani 1 1 d . . .
H12A H 0.1412 0.4727 1.0196 0.026 Uiso 1 1 calc R . .
C13 C 0.16795(19) 0.54098(18) 1.18820(15) 0.0260(4) Uani 1 1 d . . .
H13A H 0.0822 0.4815 1.1946 0.031 Uiso 1 1 calc R . .
C14 C 0.25783(19) 0.63251(17) 1.28474(14) 0.0243(3) Uani 1 1 d . . .
H14A H 0.2318 0.6335 1.3551 0.029 Uiso 1 1 calc R . .
C15 C 0.38335(19) 0.72113(16) 1.27923(13) 0.0214(3) Uani 1 1 d . . .
H15A H 0.4452 0.7819 1.3447 0.026 Uiso 1 1 calc R . .
C16 C 0.41574(17) 0.71789(15) 1.17357(13) 0.0177(3) Uani 1 1 d . . .
C17 C 0.51749(17) 0.75226(15) 1.02800(12) 0.0165(3) Uani 1 1 d . . .
C18 C 0.61858(17) 0.83051(15) 0.97524(12) 0.0166(3) Uani 1 1 d . . .
C19 C 0.58553(17) 0.83369(15) 0.86472(12) 0.0182(3) Uani 1 1 d . . .
H19A H 0.6507 0.8959 0.8391 0.022 Uiso 1 1 calc R . .
C20 C 0.76106(17) 0.91856(16) 1.04911(12) 0.0180(3) Uani 1 1 d . . .
C21 C 0.86473(19) 0.86573(18) 1.12989(14) 0.0243(3) Uani 1 1 d . . .
H21A H 0.8453 0.7718 1.1379 0.029 Uiso 1 1 calc R . .
C22 C 0.9959(2) 0.9494(2) 1.19849(14) 0.0298(4) Uani 1 1 d . . .
H22A H 1.0655 0.9124 1.2531 0.036 Uiso 1 1 calc R . .
C23 C 1.02561(19) 1.08638(19) 1.18770(14) 0.0291(4) Uani 1 1 d . . .
H23A H 1.1134 1.1444 1.2364 0.035 Uiso 1 1 calc R . .
C24 C 0.92662(19) 1.13813(18) 1.10549(15) 0.0273(4) Uani 1 1 d . . .
H24A H 0.9488 1.2310 1.0960 0.033 Uiso 1 1 calc R . .
C25 C 0.79523(18) 1.05540(16) 1.03683(14) 0.0222(3) Uani 1 1 d . . .
H25A H 0.7278 1.0923 0.9809 0.027 Uiso 1 1 calc R . .
H2A H 0.585(2) 0.863(2) 1.1842(16) 0.023(5) 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
S O1 1.4327(12) . ?
S O2 1.4348(12) . ?
S N1 1.6404(13) . ?
S C1 1.7677(17) . ?
N1 C19 1.4151(19) . ?
N1 C8 1.4872(19) . ?
N2 C16 1.367(2) . ?
N2 C17 1.3918(19) . ?
N2 H2A 0.83(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.387(2) . ?
C2 C3 1.382(2) . ?
C2 H2C 0.9500 . ?
C3 C4 1.394(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(3) . ?
C4 C7 1.508(3) . ?
C5 C6 1.387(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.513(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.497(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C17 1.381(2) . ?
C10 C11 1.431(2) . ?
C11 C16 1.413(2) . ?
C11 C12 1.407(2) . ?
C12 C13 1.382(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.406(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.382(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.399(2) . ?
C15 H15A 0.9500 . ?
C17 C18 1.467(2) . ?
C18 C19 1.343(2) . ?
C18 C20 1.494(2) . ?
C19 H19A 0.9500 . ?
C20 C25 1.395(2) . ?
C20 C21 1.398(2) . ?
C21 C22 1.388(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.385(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.387(2) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S O2 119.79(7) . . ?
O1 S N1 106.80(7) . . ?
O2 S N1 107.52(7) . . ?
O1 S C1 108.24(7) . . ?
O2 S C1 107.07(8) . . ?
N1 S C1 106.76(7) . . ?
C19 N1 C8 117.93(12) . . ?
C19 N1 S 115.79(10) . . ?
C8 N1 S 119.24(10) . . ?
C16 N2 C17 109.52(13) . . ?
C16 N2 H2A 123.9(13) . . ?
C17 N2 H2A 124.9(13) . . ?
C2 C1 C6 120.44(16) . . ?
C2 C1 S 119.22(12) . . ?
C6 C1 S 120.30(13) . . ?
C1 C2 C3 119.51(16) . . ?
C1 C2 H2C 120.2 . . ?
C3 C2 H2C 120.2 . . ?
C2 C3 C4 121.09(17) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 118.35(17) . . ?
C5 C4 C7 121.72(17) . . ?
C3 C4 C7 119.92(18) . . ?
C4 C5 C6 121.41(16) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C1 C6 C5 119.14(16) . . ?
C1 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 111.67(12) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 114.11(13) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C17 C10 C11 106.76(13) . . ?
C17 C10 C9 129.20(14) . . ?
C11 C10 C9 124.04(13) . . ?
C16 C11 C12 118.89(14) . . ?
C16 C11 C10 107.45(13) . . ?
C12 C11 C10 133.65(15) . . ?
C13 C12 C11 118.78(15) . . ?
C13 C12 H12A 120.6 . . ?
C11 C12 H12A 120.6 . . ?
C12 C13 C14 121.32(15) . . ?
C12 C13 H13A 119.3 . . ?
C14 C13 H13A 119.3 . . ?
C15 C14 C13 121.25(15) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C14 C15 C16 117.41(15) . . ?
C14 C15 H15A 121.3 . . ?
C16 C15 H15A 121.3 . . ?
N2 C16 C15 130.16(14) . . ?
N2 C16 C11 107.49(13) . . ?
C15 C16 C11 122.32(14) . . ?
C10 C17 N2 108.76(13) . . ?
C10 C17 C18 132.44(14) . . ?
N2 C17 C18 118.50(13) . . ?
C19 C18 C17 123.50(14) . . ?
C19 C18 C20 117.93(13) . . ?
C17 C18 C20 118.46(13) . . ?
C18 C19 N1 124.17(14) . . ?
C18 C19 H19A 117.9 . . ?
N1 C19 H19A 117.9 . . ?
C25 C20 C21 118.42(14) . . ?
C25 C20 C18 120.26(14) . . ?
C21 C20 C18 121.30(14) . . ?
C20 C21 C22 120.55(16) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C21 C22 C23 120.34(16) . . ?
C21 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
C24 C23 C22 119.52(16) . . ?
C24 C23 H23A 120.2 . . ?
C22 C23 H23A 120.2 . . ?
C23 C24 C25 120.45(16) . . ?
C23 C24 H24A 119.8 . . ?
C25 C24 H24A 119.8 . . ?
C24 C25 C20 120.65(15) . . ?
C24 C25 H25A 119.7 . . ?
C20 C25 H25A 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.059


