# Electronic Supplementary Material (ESI) for ChemComm.
# 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_160428d
_audit_block_doi                 10.5517/ccdc.csd.cc1mr25m
_database_code_depnum_ccdc_archive 'CCDC 1511720'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N O2 S'
_chemical_formula_weight         349.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.754(3)
_cell_length_b                   10.149(5)
_cell_length_c                   11.964(5)
_cell_angle_alpha                97.693(9)
_cell_angle_beta                 108.065(8)
_cell_angle_gamma                95.123(9)
_cell_volume                     878.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3646
_cell_measurement_theta_min      3.636
_cell_measurement_theta_max      29.842

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4777
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.045
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3093
_reflns_number_gt                2675
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.9000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3093
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1565
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50441(10) 0.91042(7) 0.23910(7) 0.0489(3) Uani 1 1 d . . . . .
O1 O 0.4747(5) 0.4075(2) 0.1885(3) 0.0887(9) Uani 1 1 d . . . . .
O2 O 0.5777(4) 0.5449(3) 0.3607(2) 0.0790(8) Uani 1 1 d . . . . .
C6 C 0.1349(4) 0.7709(3) -0.0766(2) 0.0426(6) Uani 1 1 d . . . . .
C12 C 0.4384(3) 0.7581(2) 0.2910(2) 0.0395(6) Uani 1 1 d . . . . .
H12 H 0.5434 0.7483 0.3590 0.047 Uiso 1 1 calc R U . . .
C16 C 0.2797(3) 0.7725(2) 0.3388(2) 0.0346(5) Uani 1 1 d . . . . .
C11 C 0.4099(3) 0.6339(2) 0.1979(2) 0.0388(6) Uani 1 1 d . . . . .
C19 C -0.0059(4) 0.7984(3) 0.4327(3) 0.0552(7) Uani 1 1 d . . . . .
H19 H -0.1008 0.8064 0.4642 0.066 Uiso 1 1 calc R U . . .
C17 C 0.1000(3) 0.7179(3) 0.2719(2) 0.0413(6) Uani 1 1 d . . . . .
H17 H 0.0746 0.6718 0.1948 0.050 Uiso 1 1 calc R U . . .
C7 C 0.2566(3) 0.7499(2) 0.0372(2) 0.0376(5) Uani 1 1 d . . . . .
N1 N 0.2817(3) 0.9724(2) 0.0340(2) 0.0471(6) Uani 1 1 d . . . . .
C10 C 0.3132(3) 0.6295(2) 0.0808(2) 0.0364(5) Uani 1 1 d . . . . .
C21 C 0.3115(4) 0.8411(3) 0.4536(2) 0.0438(6) Uani 1 1 d . . . . .
H21 H 0.4300 0.8794 0.4998 0.053 Uiso 1 1 calc R U . . .
C18 C -0.0410(4) 0.7314(3) 0.3186(3) 0.0511(7) Uani 1 1 d . . . . .
H18 H -0.1603 0.6948 0.2725 0.061 Uiso 1 1 calc R U . . .
C13 C 0.2610(4) 0.5031(3) -0.0115(3) 0.0493(7) Uani 1 1 d . . . . .
H13A H 0.3450 0.4407 0.0141 0.074 Uiso 1 1 calc R U . . .
H13B H 0.2658 0.5247 -0.0863 0.074 Uiso 1 1 calc R U . . .
H13C H 0.1391 0.4636 -0.0210 0.074 Uiso 1 1 calc R U . . .
C1 C 0.1550(4) 0.9113(3) -0.0737(3) 0.0458(6) Uani 1 1 d . . . . .
C8 C 0.3384(3) 0.8765(2) 0.0999(2) 0.0392(6) Uani 1 1 d . . . . .
C14 C 0.4847(4) 0.5162(3) 0.2436(3) 0.0470(6) Uani 1 1 d . . . . .
C20 C 0.1708(4) 0.8535(3) 0.5002(2) 0.0530(7) Uani 1 1 d . . . . .
H20 H 0.1951 0.8993 0.5774 0.064 Uiso 1 1 calc R U . . .
C5 C 0.0075(4) 0.6905(3) -0.1785(3) 0.0561(7) Uani 1 1 d . . . . .
H5 H -0.0120 0.5978 -0.1833 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3406(5) 1.1165(3) 0.0709(3) 0.0620(9) Uani 1 1 d . . . . .
H9A H 0.4010 1.1361 0.1557 0.093 Uiso 1 1 calc R U . . .
H9B H 0.2358 1.1632 0.0504 0.093 Uiso 1 1 calc R U . . .
H9C H 0.4237 1.1450 0.0311 0.093 Uiso 1 1 calc R U . . .
C15 C 0.6634(8) 0.4358(5) 0.4113(4) 0.1103(18) Uani 1 1 d . . . . .
H15A H 0.5788 0.3827 0.4370 0.165 Uiso 1 1 calc R U . . .
H15B H 0.7706 0.4718 0.4784 0.165 Uiso 1 1 calc R U . . .
H15C H 0.6978 0.3807 0.3522 0.165 Uiso 1 1 calc R U . . .
C3 C -0.0663(6) 0.8872(5) -0.2663(3) 0.0749(11) Uani 1 1 d . . . . .
H3 H -0.1347 0.9241 -0.3300 0.090 Uiso 1 1 calc R U . . .
C2 C 0.0560(5) 0.9694(4) -0.1677(3) 0.0661(9) Uani 1 1 d . . . . .
H2 H 0.0722 1.0620 -0.1641 0.079 Uiso 1 1 calc R U . . .
C4 C -0.0880(5) 0.7498(4) -0.2709(3) 0.0704(10) Uani 1 1 d . . . . .
H4 H -0.1701 0.6956 -0.3389 0.084 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.728(3) . ?
S1 C12 1.830(3) . ?
O1 C14 1.190(4) . ?
O2 C14 1.339(4) . ?
O2 C15 1.448(4) . ?
C6 C5 1.405(4) . ?
C6 C1 1.413(4) . ?
C6 C7 1.451(4) . ?
C12 C11 1.516(4) . ?
C12 C16 1.520(3) . ?
C12 H12 0.9800 . ?
C16 C21 1.391(4) . ?
C16 C17 1.393(3) . ?
C11 C10 1.362(4) . ?
C11 C14 1.472(4) . ?
C19 C18 1.374(4) . ?
C19 C20 1.377(4) . ?
C19 H19 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C7 C8 1.385(3) . ?
C7 C10 1.443(3) . ?
N1 C8 1.353(3) . ?
N1 C1 1.379(4) . ?
N1 C9 1.458(4) . ?
C10 C13 1.509(3) . ?
C21 C20 1.379(4) . ?
C21 H21 0.9300 . ?
C18 H18 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C1 C2 1.388(4) . ?
C20 H20 0.9300 . ?
C5 C4 1.372(5) . ?
C5 H5 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C3 C2 1.375(6) . ?
C3 C4 1.381(6) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C4 H4 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
C8 S1 C12 96.68(12) . . ?
C14 O2 C15 115.0(3) . . ?
C5 C6 C1 117.5(3) . . ?
C5 C6 C7 136.6(3) . . ?
C1 C6 C7 105.9(2) . . ?
C11 C12 C16 114.41(19) . . ?
C11 C12 S1 111.64(18) . . ?
C16 C12 S1 111.72(17) . . ?
C11 C12 H12 106.1 . . ?
C16 C12 H12 106.1 . . ?
S1 C12 H12 106.1 . . ?
C21 C16 C17 117.6(2) . . ?
C21 C16 C12 120.0(2) . . ?
C17 C16 C12 122.3(2) . . ?
C10 C11 C14 122.2(2) . . ?
C10 C11 C12 122.2(2) . . ?
C14 C11 C12 115.6(2) . . ?
C18 C19 C20 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C8 C7 C10 121.8(2) . . ?
C8 C7 C6 105.9(2) . . ?
C10 C7 C6 131.8(2) . . ?
C8 N1 C1 108.5(2) . . ?
C8 N1 C9 126.1(3) . . ?
C1 N1 C9 125.4(3) . . ?
C11 C10 C7 120.6(2) . . ?
C11 C10 C13 123.7(2) . . ?
C7 C10 C13 115.7(2) . . ?
C20 C21 C16 121.3(2) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C1 C2 129.0(3) . . ?
N1 C1 C6 108.7(2) . . ?
C2 C1 C6 122.2(3) . . ?
N1 C8 C7 111.0(2) . . ?
N1 C8 S1 123.2(2) . . ?
C7 C8 S1 125.6(2) . . ?
O1 C14 O2 120.7(3) . . ?
O1 C14 C11 127.6(3) . . ?
O2 C14 C11 111.6(2) . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C5 C4 C3 122.2(4) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?

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
C8 S1 C12 C11 47.21(19) . . . . ?
C8 S1 C12 C16 -82.32(19) . . . . ?
C11 C12 C16 C21 152.1(2) . . . . ?
S1 C12 C16 C21 -79.9(3) . . . . ?
C11 C12 C16 C17 -27.4(3) . . . . ?
S1 C12 C16 C17 100.7(2) . . . . ?
C16 C12 C11 C10 82.7(3) . . . . ?
S1 C12 C11 C10 -45.4(3) . . . . ?
C16 C12 C11 C14 -94.1(3) . . . . ?
S1 C12 C11 C14 137.84(19) . . . . ?
C21 C16 C17 C18 -0.3(4) . . . . ?
C12 C16 C17 C18 179.2(3) . . . . ?
C5 C6 C7 C8 -176.7(3) . . . . ?
C1 C6 C7 C8 0.6(3) . . . . ?
C5 C6 C7 C10 11.7(5) . . . . ?
C1 C6 C7 C10 -171.0(2) . . . . ?
C14 C11 C10 C7 -174.2(2) . . . . ?
C12 C11 C10 C7 9.2(3) . . . . ?
C14 C11 C10 C13 4.8(4) . . . . ?
C12 C11 C10 C13 -171.8(2) . . . . ?
C8 C7 C10 C11 18.8(4) . . . . ?
C6 C7 C10 C11 -170.7(2) . . . . ?
C8 C7 C10 C13 -160.2(2) . . . . ?
C6 C7 C10 C13 10.3(4) . . . . ?
C17 C16 C21 C20 0.7(4) . . . . ?
C12 C16 C21 C20 -178.7(2) . . . . ?
C20 C19 C18 C17 0.7(5) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C8 N1 C1 C2 177.8(3) . . . . ?
C9 N1 C1 C2 -0.8(4) . . . . ?
C8 N1 C1 C6 -1.6(3) . . . . ?
C9 N1 C1 C6 179.8(2) . . . . ?
C5 C6 C1 N1 178.5(2) . . . . ?
C7 C6 C1 N1 0.6(3) . . . . ?
C5 C6 C1 C2 -1.0(4) . . . . ?
C7 C6 C1 C2 -178.9(2) . . . . ?
C1 N1 C8 C7 2.0(3) . . . . ?
C9 N1 C8 C7 -179.4(2) . . . . ?
C1 N1 C8 S1 177.42(18) . . . . ?
C9 N1 C8 S1 -4.0(4) . . . . ?
C10 C7 C8 N1 171.0(2) . . . . ?
C6 C7 C8 N1 -1.6(3) . . . . ?
C10 C7 C8 S1 -4.2(3) . . . . ?
C6 C7 C8 S1 -176.87(18) . . . . ?
C12 S1 C8 N1 158.4(2) . . . . ?
C12 S1 C8 C7 -26.9(2) . . . . ?
C15 O2 C14 O1 0.7(5) . . . . ?
C15 O2 C14 C11 -177.1(3) . . . . ?
C10 C11 C14 O1 1.0(5) . . . . ?
C12 C11 C14 O1 177.8(3) . . . . ?
C10 C11 C14 O2 178.7(2) . . . . ?
C12 C11 C14 O2 -4.6(3) . . . . ?
C18 C19 C20 C21 -0.3(5) . . . . ?
C16 C21 C20 C19 -0.5(4) . . . . ?
C1 C6 C5 C4 1.5(4) . . . . ?
C7 C6 C5 C4 178.5(3) . . . . ?
C4 C3 C2 C1 -0.5(5) . . . . ?
N1 C1 C2 C3 -178.8(3) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
C6 C5 C4 C3 -1.5(5) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?

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
C9 H9A S1 0.96 2.71 3.170(4) 110.3 .
C12 H12 O2 0.98 2.11 2.623(4) 111.1 .
C12 H12 O2 0.98 2.11 2.623(4) 111.1 .
C9 H9A S1 0.96 2.71 3.170(4) 110.3 .
C12 H12 O2 0.98 2.11 2.623(4) 111.1 .
C12 H12 O2 0.98 2.11 2.623(4) 111.1 .
C12 H12 O2 0.98 2.11 2.623(4) 111.1 .
C9 H9A S1 0.96 2.71 3.170(4) 110.3 .
C12 H12 O2 0.98 2.11 2.623(4) 111.1 .
C9 H9A S1 0.96 2.71 3.170(4) 110.3 .
C12 H12 O2 0.98 2.11 2.623(4) 111.1 .

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6



