# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mx2930
_database_code_depnum_ccdc_archive 'CCDC 1479438'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-06-10 downloaded from the CCDC.
;
_audit_creation_date             2014-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H19 N O3 S'
_chemical_formula_sum            'C24 H19 N O3 S'
_chemical_formula_weight         401.46
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   11.908(2)
_cell_length_b                   12.416(3)
_cell_length_c                   13.154(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1944.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5570
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4782
_cell_measurement_theta_min      1.6401
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12161
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.26
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             2544
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0327
_diffrn_orient_matrix_UB_12      0.0705
_diffrn_orient_matrix_UB_13      0.0319
_diffrn_orient_matrix_UB_21      -0.0452
_diffrn_orient_matrix_UB_22      -0.0437
_diffrn_orient_matrix_UB_23      0.0503
_diffrn_orient_matrix_UB_31      0.0555
_diffrn_orient_matrix_UB_32      0.0023
_diffrn_orient_matrix_UB_33      0.0519
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4309
_reflns_number_total             4428
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;

 'XS (Sheldrick, 2008)'
;
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(6)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0338P)²+0.4943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0838
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S -0.38530(3) -0.92940(3) -0.23003(3) 0.02375(10) Uani 1 1 d . . .
O1 O -0.33769(12) -0.97482(11) -0.31956(10) 0.0358(3) Uani 1 1 d . . .
O2 O -0.47384(11) -0.85258(11) -0.24157(11) 0.0365(3) Uani 1 1 d . . .
O3 O -0.21401(12) -0.76226(10) -0.27360(10) 0.0336(3) Uani 1 1 d . . .
N1 N -0.28389(12) -0.87776(11) -0.15516(11) 0.0233(3) Uani 1 1 d . . .
C1 C -0.42077(13) -1.02547(13) -0.13794(13) 0.0221(3) Uani 1 1 d . . .
C2 C -0.49139(14) -1.11288(13) -0.15179(14) 0.0264(4) Uani 1 1 d . . .
H2 H -0.5232 -1.1279 -0.2148 0.032 Uiso 1 1 calc . . R
C3 C -0.51267(15) -1.17699(14) -0.06767(15) 0.0293(4) Uani 1 1 d . . .
H3 H -0.5598 -1.2363 -0.0740 0.035 Uiso 1 1 calc . . R
C4 C -0.46422(15) -1.15355(14) 0.02623(14) 0.0277(4) Uani 1 1 d . . .
H4 H -0.4797 -1.1975 0.0817 0.033 Uiso 1 1 calc . . R
C5 C -0.39315(14) -1.06570(13) 0.03845(13) 0.0249(3) Uani 1 1 d . . .
H5 H -0.3612 -1.0505 0.1014 0.030 Uiso 1 1 calc . . R
C6 C -0.37088(13) -1.00093(12) -0.04558(13) 0.0211(3) Uani 1 1 d . . .
C7 C -0.29636(13) -0.90736(13) -0.05052(12) 0.0209(3) Uani 1 1 d . . .
C8 C -0.24983(14) -0.84868(13) 0.02291(13) 0.0226(3) Uani 1 1 d . . .
H8 H -0.2596 -0.8683 0.0906 0.027 Uiso 1 1 calc . . R
C9 C -0.18145(14) -0.75067(13) -0.00329(13) 0.0224(3) Uani 1 1 d . . .
H9 H -0.1223 -0.7436 0.0480 0.027 Uiso 1 1 calc . . R
C10 C -0.12359(14) -0.76805(13) -0.10805(13) 0.0234(3) Uani 1 1 d . . .
H10 H -0.0734 -0.8300 -0.1004 0.028 Uiso 1 1 calc . . R
C11 C -0.20910(15) -0.79804(13) -0.18853(14) 0.0240(3) Uani 1 1 d . . .
C12 C -0.25198(14) -0.64812(13) -0.00047(13) 0.0242(3) Uani 1 1 d . . .
C13 C -0.35518(15) -0.64133(15) -0.05008(14) 0.0305(4) Uani 1 1 d . . .
H13 H -0.3830 -0.7012 -0.0843 0.037 Uiso 1 1 calc . . R
C14 C -0.41703(18) -0.54680(16) -0.04918(16) 0.0386(5) Uani 1 1 d . . .
H14 H -0.4853 -0.5431 -0.0833 0.046 Uiso 1 1 calc . . R
C15 C -0.37667(19) -0.45810(15) 0.0026(2) 0.0453(5) Uani 1 1 d . . .
H15 H -0.4175 -0.3943 0.0030 0.054 Uiso 1 1 calc . . R
C16 C -0.27619(19) -0.46423(16) 0.0537(2) 0.0498(6) Uani 1 1 d . . .
H16 H -0.2499 -0.4048 0.0894 0.060 Uiso 1 1 calc . . R
C17 C -0.21385(16) -0.55820(15) 0.05218(17) 0.0365(5) Uani 1 1 d . . .
H17 H -0.1458 -0.5613 0.0867 0.044 Uiso 1 1 calc . . R
C18 C -0.05066(15) -0.67293(14) -0.13911(15) 0.0291(4) Uani 1 1 d . . .
H18A H -0.0996 -0.6154 -0.1621 0.035 Uiso 1 1 calc . . R
H18B H -0.0115 -0.6471 -0.0792 0.035 Uiso 1 1 calc . . R
C19 C 0.03560(14) -0.69431(14) -0.22157(14) 0.0268(4) Uani 1 1 d . . .
C20 C 0.10336(16) -0.78524(15) -0.22121(14) 0.0318(4) Uani 1 1 d . . .
H20 H 0.0930 -0.8375 -0.1715 0.038 Uiso 1 1 calc . . R
C21 C 0.18656(16) -0.79926(18) -0.29413(16) 0.0377(5) Uani 1 1 d . . .
H21 H 0.2317 -0.8603 -0.2925 0.045 Uiso 1 1 calc . . R
C22 C 0.20233(16) -0.72266(18) -0.36900(16) 0.0391(5) Uani 1 1 d . . .
H22 H 0.2582 -0.7318 -0.4176 0.047 Uiso 1 1 calc . . R
C23 C 0.13497(16) -0.63294(16) -0.37114(16) 0.0384(5) Uani 1 1 d . . .
H23 H 0.1446 -0.5817 -0.4220 0.046 Uiso 1 1 calc . . R
C24 C 0.05250(16) -0.61816(15) -0.29782(16) 0.0336(4) Uani 1 1 d . . .
H24 H 0.0080 -0.5566 -0.2996 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
S1 O1 1.4236(13) . ?
S1 O2 1.4298(14) . ?
S1 N1 1.6850(14) . ?
S1 C1 1.7518(17) . ?
O3 C11 1.205(2) . ?
N1 C7 1.432(2) . ?
N1 C11 1.402(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.386(2) . ?
C2 C3 1.387(3) . ?
C3 C4 1.394(3) . ?
C4 C5 1.390(2) . ?
C5 C6 1.392(2) . ?
C6 C7 1.463(2) . ?
C7 C8 1.331(2) . ?
C8 C9 1.504(2) . ?
C9 C10 1.556(2) . ?
C9 C12 1.526(2) . ?
C10 C11 1.515(2) . ?
C10 C18 1.522(2) . ?
C12 C13 1.394(2) . ?
C12 C17 1.390(2) . ?
C13 C14 1.386(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.374(3) . ?
C16 C17 1.383(3) . ?
C18 C19 1.517(2) . ?
C19 C20 1.388(3) . ?
C19 C24 1.393(3) . ?
C20 C21 1.390(3) . ?
C21 C22 1.382(3) . ?
C22 C23 1.373(3) . ?
C23 C24 1.389(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
O1 S1 O2 118.05(9) . . ?
O1 S1 N1 110.42(8) . . ?
O1 S1 C1 113.47(8) . . ?
O2 S1 N1 109.67(8) . . ?
O2 S1 C1 110.48(8) . . ?
N1 S1 C1 91.59(8) . . ?
C7 N1 S1 112.94(11) . . ?
C11 N1 S1 122.75(12) . . ?
C11 N1 C7 123.22(14) . . ?
C2 C1 S1 126.09(14) . . ?
C2 C1 C6 123.21(16) . . ?
C6 C1 S1 110.67(12) . . ?
C1 C2 C3 117.12(17) . . ?
C2 C3 C4 120.78(16) . . ?
C5 C4 C3 121.22(16) . . ?
C4 C5 C6 118.51(16) . . ?
C1 C6 C5 119.15(15) . . ?
C1 C6 C7 113.30(14) . . ?
C5 C6 C7 127.53(15) . . ?
N1 C7 C6 108.01(13) . . ?
C8 C7 N1 120.92(15) . . ?
C8 C7 C6 130.92(15) . . ?
C7 C8 C9 120.14(15) . . ?
C8 C9 C10 109.29(13) . . ?
C8 C9 C12 111.81(13) . . ?
C12 C9 C10 112.40(14) . . ?
C11 C10 C9 110.81(14) . . ?
C11 C10 C18 112.74(15) . . ?
C18 C10 C9 112.51(13) . . ?
O3 C11 N1 121.33(16) . . ?
O3 C11 C10 126.20(16) . . ?
N1 C11 C10 112.44(14) . . ?
C13 C12 C9 121.63(15) . . ?
C17 C12 C9 120.17(16) . . ?
C17 C12 C13 118.20(16) . . ?
C14 C13 C12 121.05(18) . . ?
C15 C14 C13 119.6(2) . . ?
C16 C15 C14 119.99(19) . . ?
C15 C16 C17 120.5(2) . . ?
C16 C17 C12 120.6(2) . . ?
C19 C18 C10 116.26(14) . . ?
C20 C19 C18 122.25(17) . . ?
C20 C19 C24 118.07(17) . . ?
C24 C19 C18 119.59(16) . . ?
C19 C20 C21 120.93(18) . . ?
C22 C21 C20 120.17(19) . . ?
C23 C22 C21 119.58(19) . . ?
C22 C23 C24 120.40(19) . . ?
C23 C24 C19 120.84(19) . . ?

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
S1 N1 C7 C6 18.35(16) . . . . ?
S1 N1 C7 C8 -157.65(13) . . . . ?
S1 N1 C11 O3 0.0(2) . . . . ?
S1 N1 C11 C10 -178.06(11) . . . . ?
S1 C1 C2 C3 -177.19(14) . . . . ?
S1 C1 C6 C5 177.26(12) . . . . ?
S1 C1 C6 C7 -4.11(17) . . . . ?
O1 S1 N1 C7 -133.92(12) . . . . ?
O1 S1 N1 C11 57.72(15) . . . . ?
O1 S1 C1 C2 -56.23(17) . . . . ?
O1 S1 C1 C6 125.70(12) . . . . ?
O2 S1 N1 C7 94.33(13) . . . . ?
O2 S1 N1 C11 -74.03(15) . . . . ?
O2 S1 C1 C2 78.95(16) . . . . ?
O2 S1 C1 C6 -99.12(13) . . . . ?
N1 S1 C1 C2 -169.34(15) . . . . ?
N1 S1 C1 C6 12.59(12) . . . . ?
N1 C7 C8 C9 -1.0(2) . . . . ?
C1 S1 N1 C7 -18.10(12) . . . . ?
C1 S1 N1 C11 173.54(14) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C7 N1 -8.61(19) . . . . ?
C1 C6 C7 C8 166.85(17) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C1 C6 C7 177.75(15) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C4 C5 C6 C7 -177.86(15) . . . . ?
C5 C6 C7 N1 169.88(15) . . . . ?
C5 C6 C7 C8 -14.7(3) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C6 C7 C8 C9 -175.94(16) . . . . ?
C7 N1 C11 O3 -167.17(17) . . . . ?
C7 N1 C11 C10 14.8(2) . . . . ?
C7 C8 C9 C10 -30.9(2) . . . . ?
C7 C8 C9 C12 94.20(19) . . . . ?
C8 C9 C10 C11 53.89(17) . . . . ?
C8 C9 C10 C18 -178.86(14) . . . . ?
C8 C9 C12 C13 -49.3(2) . . . . ?
C8 C9 C12 C17 130.92(18) . . . . ?
C9 C10 C11 O3 135.70(18) . . . . ?
C9 C10 C11 N1 -46.36(18) . . . . ?
C9 C10 C18 C19 162.01(15) . . . . ?
C9 C12 C13 C14 -178.28(17) . . . . ?
C9 C12 C17 C16 178.82(18) . . . . ?
C10 C9 C12 C13 74.1(2) . . . . ?
C10 C9 C12 C17 -105.73(19) . . . . ?
C10 C18 C19 C20 -45.0(2) . . . . ?
C10 C18 C19 C24 138.50(18) . . . . ?
C11 N1 C7 C6 -173.35(14) . . . . ?
C11 N1 C7 C8 10.7(2) . . . . ?
C11 C10 C18 C19 -71.8(2) . . . . ?
C12 C9 C10 C11 -70.86(17) . . . . ?
C12 C9 C10 C18 56.39(18) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C12 C17 C16 -1.0(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C15 C16 C17 C12 -0.3(3) . . . . ?
C17 C12 C13 C14 1.6(3) . . . . ?
C18 C10 C11 O3 8.6(3) . . . . ?
C18 C10 C11 N1 -173.48(14) . . . . ?
C18 C19 C20 C21 -175.83(17) . . . . ?
C18 C19 C24 C23 176.56(17) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C19 C24 C23 -0.1(3) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C21 C22 C23 C24 0.9(3) . . . . ?
C22 C23 C24 C19 -0.7(3) . . . . ?
C24 C19 C20 C21 0.7(3) . . . . ?

