# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_20180409_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1836025'
_audit_update_record             
;
2018-04-10 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 Cl N O3 S'
_chemical_formula_weight         451.94

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'
Cl Cl 0.1484 0.1585 '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                   10.2719(7)
_cell_length_b                   10.4262(7)
_cell_length_c                   11.7012(8)
_cell_angle_alpha                69.168(2)
_cell_angle_beta                 73.012(2)
_cell_angle_gamma                86.849(2)
_cell_volume                     1118.45(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5562
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.52
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.291
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7679
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3909
_reflns_number_gt                3423
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0596P)²+0.4843P] 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         3909
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_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
C1 C 0.8733(2) 0.29166(18) 0.24471(18) 0.0191(4) Uani 1 1 d . . . . .
C2 C 0.9056(2) 0.42340(19) 0.23880(18) 0.0218(4) Uani 1 1 d . . . . .
H2 H 0.841582 0.465889 0.289089 0.026 Uiso 1 1 calc R U . . .
C3 C 1.0279(2) 0.49183(19) 0.16183(19) 0.0234(4) Uani 1 1 d . . . . .
C4 C 1.1239(2) 0.4339(2) 0.0869(2) 0.0246(4) Uani 1 1 d . . . . .
H4 H 1.208379 0.482226 0.033989 0.030 Uiso 1 1 calc R U . . .
C5 C 1.0947(2) 0.3045(2) 0.0903(2) 0.0241(4) Uani 1 1 d . . . . .
H5 H 1.159805 0.263926 0.038999 0.029 Uiso 1 1 calc R U . . .
C6 C 0.9705(2) 0.23234(19) 0.16831(19) 0.0206(4) Uani 1 1 d . . . . .
C7 C 1.0700(2) 0.0093(2) 0.1713(3) 0.0348(5) Uani 1 1 d . . . . .
H7A H 1.038575 -0.087455 0.217791 0.052 Uiso 1 1 calc R U . . .
H7B H 1.129525 0.035717 0.212096 0.052 Uiso 1 1 calc R U . . .
H7C H 1.120692 0.022114 0.082543 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8376(2) 0.04205(19) 0.16601(19) 0.0222(4) Uani 1 1 d . . . . .
C9 C 0.71739(19) 0.13547(18) 0.16401(18) 0.0183(4) Uani 1 1 d . . . . .
H9 H 0.749922 0.228557 0.098243 0.022 Uiso 1 1 calc R U . . .
C10 C 0.6702(2) 0.14656(18) 0.29455(18) 0.0191(4) Uani 1 1 d . . . . .
H10 H 0.587193 0.099441 0.352982 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7415(2) 0.22066(18) 0.33087(18) 0.0193(4) Uani 1 1 d . . . . .
C12 C 0.6880(2) 0.23564(18) 0.45829(18) 0.0207(4) Uani 1 1 d . . . . .
C13 C 0.5495(2) 0.2479(2) 0.5086(2) 0.0284(5) Uani 1 1 d . . . . .
H13 H 0.489155 0.248785 0.460424 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4982(3) 0.2587(2) 0.6280(2) 0.0362(5) Uani 1 1 d . . . . .
H14 H 0.403104 0.266294 0.661335 0.043 Uiso 1 1 calc R U . . .
C15 C 0.5852(3) 0.2586(2) 0.6988(2) 0.0353(6) Uani 1 1 d . . . . .
H15 H 0.550337 0.265976 0.780792 0.042 Uiso 1 1 calc R U . . .
C16 C 0.7231(3) 0.2478(2) 0.6492(2) 0.0315(5) Uani 1 1 d . . . . .
H16 H 0.783102 0.248039 0.697351 0.038 Uiso 1 1 calc R U . . .
C17 C 0.7749(2) 0.23644(18) 0.5302(2) 0.0252(5) Uani 1 1 d . . . . .
H17 H 0.870070 0.229183 0.497224 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3099(2) 0.13133(19) 0.32029(19) 0.0235(4) Uani 1 1 d . . . . .
H18 H 0.307769 0.039307 0.322970 0.028 Uiso 1 1 calc R U . . .
C19 C 0.2301(2) 0.1660(2) 0.4222(2) 0.0290(5) Uani 1 1 d . . . . .
H19 H 0.174495 0.096896 0.495620 0.035 Uiso 1 1 calc R U . . .
C20 C 0.2310(2) 0.3020(2) 0.4177(2) 0.0286(5) Uani 1 1 d . . . . .
C21 C 0.3142(2) 0.4001(2) 0.3106(2) 0.0298(5) Uani 1 1 d . . . . .
H21 H 0.315118 0.492711 0.306457 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3964(2) 0.36705(19) 0.2090(2) 0.0243(4) Uani 1 1 d . . . . .
H22 H 0.454401 0.435588 0.136798 0.029 Uiso 1 1 calc R U . . .
C23 C 0.3927(2) 0.23269(18) 0.21444(18) 0.0192(4) Uani 1 1 d . . . . .
C24 C 0.1444(3) 0.3398(3) 0.5284(3) 0.0466(7) Uani 1 1 d . . . . .
H24A H 0.179455 0.427798 0.523294 0.070 Uiso 1 1 calc R U . . .
H24B H 0.147486 0.268273 0.608988 0.070 Uiso 1 1 calc R U . . .
H24C H 0.050018 0.347726 0.524916 0.070 Uiso 1 1 calc R U . . .
C25 C 0.6091(2) 0.07500(18) 0.12960(19) 0.0198(4) Uani 1 1 d . . . . .
H25A H 0.560808 -0.004554 0.204846 0.024 Uiso 1 1 calc R U . . .
H25B H 0.654853 0.040434 0.060016 0.024 Uiso 1 1 calc R U . . .
Cl1 Cl 1.06129(6) 0.65556(5) 0.15833(5) 0.03356(17) Uani 1 1 d . . . . .
N1 N 0.95203(17) 0.09534(16) 0.17348(17) 0.0226(4) Uani 1 1 d . . . . .
O1 O 0.83018(16) -0.07395(14) 0.16491(16) 0.0335(4) Uani 1 1 d . . . . .
O2 O 0.55952(16) 0.31584(14) -0.01625(13) 0.0292(4) Uani 1 1 d . . . . .
O3 O 0.39592(15) 0.11865(15) 0.04889(15) 0.0301(4) Uani 1 1 d . . . . .
S1 S 0.48742(5) 0.19199(5) 0.08026(4) 0.01959(15) Uani 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
C1 C2 1.404(3) . ?
C1 C6 1.408(3) . ?
C1 C11 1.476(3) . ?
C2 C3 1.371(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(3) . ?
C3 Cl1 1.7434(19) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9500 . ?
C6 N1 1.429(2) . ?
C7 N1 1.467(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O1 1.221(2) . ?
C8 N1 1.365(3) . ?
C8 C9 1.531(2) . ?
C9 C10 1.506(3) . ?
C9 C25 1.522(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.338(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.492(3) . ?
C12 C13 1.390(3) . ?
C12 C17 1.396(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.388(3) . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.400(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(3) . ?
C20 C24 1.508(3) . ?
C21 C22 1.385(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 S1 1.769(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 S1 1.7713(18) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
O2 S1 1.4389(15) . ?
O3 S1 1.4433(14) . ?

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
C2 C1 C6 117.76(19) . . ?
C2 C1 C11 119.36(17) . . ?
C6 C1 C11 122.88(16) . . ?
C3 C2 C1 121.21(19) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.29(18) . . ?
C2 C3 Cl1 118.89(16) . . ?
C4 C3 Cl1 119.82(16) . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.02(19) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.91(17) . . ?
C5 C6 N1 117.58(17) . . ?
C1 C6 N1 122.36(18) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 122.28(17) . . ?
O1 C8 C9 122.15(17) . . ?
N1 C8 C9 115.54(15) . . ?
C10 C9 C25 114.15(16) . . ?
C10 C9 C8 105.65(15) . . ?
C25 C9 C8 109.32(14) . . ?
C10 C9 H9 109.2 . . ?
C25 C9 H9 109.2 . . ?
C8 C9 H9 109.2 . . ?
C11 C10 C9 122.12(18) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C1 120.72(17) . . ?
C10 C11 C12 120.69(18) . . ?
C1 C11 C12 118.59(16) . . ?
C13 C12 C17 118.43(18) . . ?
C13 C12 C11 120.41(17) . . ?
C17 C12 C11 121.16(19) . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.82(19) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 120.3(2) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C23 C18 C19 119.21(18) . . ?
C23 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 120.6(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 118.50(19) . . ?
C21 C20 C24 120.9(2) . . ?
C19 C20 C24 120.6(2) . . ?
C20 C21 C22 121.75(18) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 118.9(2) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C23 C18 121.04(19) . . ?
C22 C23 S1 119.18(16) . . ?
C18 C23 S1 119.67(14) . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 C25 S1 114.36(12) . . ?
C9 C25 H25A 108.7 . . ?
S1 C25 H25A 108.7 . . ?
C9 C25 H25B 108.7 . . ?
S1 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C8 N1 C6 125.24(15) . . ?
C8 N1 C7 116.43(16) . . ?
C6 N1 C7 117.92(16) . . ?
O2 S1 O3 118.71(9) . . ?
O2 S1 C23 108.00(9) . . ?
O3 S1 C23 107.71(9) . . ?
O2 S1 C25 108.17(9) . . ?
O3 S1 C25 106.69(8) . . ?
C23 S1 C25 107.03(9) . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.057



