# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a51020a
_database_code_depnum_ccdc_archive 'CCDC 1443052'
_audit_update_record             
;
2015-12-17 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H25 Cl2 N3 O4 S'
_chemical_formula_weight         438.36

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'
Cl Cl 0.1484 0.1585 '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                   10.820(6)
_cell_length_b                   10.975(6)
_cell_length_c                   11.163(6)
_cell_angle_alpha                74.634(5)
_cell_angle_beta                 62.808(5)
_cell_angle_gamma                65.132(5)
_cell_volume                     1065.4(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2942
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      26.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.690
_exptl_crystal_size_min          0.500
_exptl_absorpt_coefficient_mu    0.430
_shelx_estimated_absorpt_T_min   0.725
_shelx_estimated_absorpt_T_max   0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.368
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            5239
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.054
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             3666
_reflns_number_gt                2999
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1584P)²+0.8442P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.028(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3666
_refine_ls_number_parameters     252
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2518
_refine_ls_wR_factor_gt          0.2404
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.057
_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
S1 S 0.15308(9) 0.37571(8) 0.11348(9) 0.0477(4) Uani 1 1 d . . . . .
N1 N 0.1883(4) 0.0375(3) 0.0327(3) 0.0519(8) Uani 1 1 d . . . . .
N2 N 0.0838(4) 0.5351(3) 0.1316(3) 0.0562(9) Uani 1 1 d . . . . .
N3 N 0.0574(3) 0.5754(3) 0.2534(3) 0.0468(7) Uani 1 1 d . . . . .
O1 O -0.0322(3) 0.2032(3) 0.0426(3) 0.0653(8) Uani 1 1 d . . . . .
O2 O 0.1652(3) 0.3687(3) -0.0177(3) 0.0645(8) Uani 1 1 d . . . . .
O3 O 0.2821(3) 0.3177(3) 0.1417(3) 0.0667(8) Uani 1 1 d . . . . .
O4 O -0.0336(4) 0.7732(3) 0.4230(3) 0.0723(9) Uani 1 1 d . . . . .
C1 C 0.0620(4) 0.1387(4) 0.0891(4) 0.0503(9) Uani 1 1 d . . . . .
C2 C 0.0523(4) 0.1566(3) 0.2248(3) 0.0439(8) Uani 1 1 d . . . . .
C3 C 0.1993(4) 0.0562(3) 0.2267(3) 0.0427(8) Uani 1 1 d . . . . .
C4 C 0.2590(4) 0.0229(4) 0.3200(4) 0.0494(8) Uani 1 1 d . . . . .
H4 H 0.2085 0.0686 0.3974 0.059 Uiso 1 1 calc R U . . .
C5 C 0.3957(4) -0.0797(4) 0.2994(4) 0.0585(10) Uani 1 1 d . . . . .
C6 C 0.4675(4) -0.1459(4) 0.1831(4) 0.0625(11) Uani 1 1 d . . . . .
H6 H 0.5595 -0.2138 0.1683 0.075 Uiso 1 1 calc R U . . .
C7 C 0.4078(4) -0.1149(4) 0.0883(4) 0.0596(10) Uani 1 1 d . . . . .
H7 H 0.4575 -0.1609 0.0112 0.071 Uiso 1 1 calc R U . . .
C8 C 0.2729(4) -0.0139(3) 0.1118(3) 0.0477(8) Uani 1 1 d . . . . .
C9 C 0.0192(4) 0.3039(3) 0.2368(3) 0.0450(8) Uani 1 1 d . . . . .
H9A H 0.0098 0.3105 0.3258 0.054 Uiso 1 1 calc R U . . .
H9B H -0.0760 0.3577 0.2312 0.054 Uiso 1 1 calc R U . . .
C10 C -0.0986(4) 0.6494(4) 0.3244(4) 0.0592(10) Uani 1 1 d . . . . .
H10A H -0.1560 0.5923 0.3475 0.071 Uiso 1 1 calc R U . . .
H10B H -0.1326 0.7273 0.2667 0.071 Uiso 1 1 calc R U . . .
C11 C -0.1205(5) 0.6944(5) 0.4513(5) 0.0690(12) Uani 1 1 d . . . . .
H11A H -0.2243 0.7466 0.4970 0.083 Uiso 1 1 calc R U . . .
H11B H -0.0940 0.6157 0.5116 0.083 Uiso 1 1 calc R U . . .
C12 C 0.1171(5) 0.7008(5) 0.3541(4) 0.0668(11) Uani 1 1 d . . . . .
H12A H 0.1492 0.6213 0.4113 0.080 Uiso 1 1 calc R U . . .
H12B H 0.1750 0.7564 0.3352 0.080 Uiso 1 1 calc R U . . .
C13 C 0.1452(4) 0.6587(4) 0.2235(4) 0.0551(9) Uani 1 1 d . . . . .
H13A H 0.1175 0.7378 0.1641 0.066 Uiso 1 1 calc R U . . .
H13B H 0.2497 0.6081 0.1783 0.066 Uiso 1 1 calc R U . . .
C14 C -0.0775(4) 0.1169(4) 0.3380(4) 0.0621(10) Uani 1 1 d . . . . .
H14A H -0.0592 0.0240 0.3354 0.093 Uiso 1 1 calc R U . . .
H14B H -0.1675 0.1724 0.3253 0.093 Uiso 1 1 calc R U . . .
H14C H -0.0868 0.1296 0.4239 0.093 Uiso 1 1 calc R U . . .
C15 C 0.4641(6) -0.1172(6) 0.4012(5) 0.0853(15) Uani 1 1 d . . . . .
H15A H 0.3874 -0.1076 0.4907 0.128 Uiso 1 1 calc R U . . .
H15B H 0.5176 -0.0588 0.3832 0.128 Uiso 1 1 calc R U . . .
H15C H 0.5310 -0.2090 0.3946 0.128 Uiso 1 1 calc R U . . .
C16 C 0.2318(6) -0.0121(5) -0.0938(4) 0.0719(12) Uani 1 1 d . . . . .
H16A H 0.1575 0.0388 -0.1300 0.108 Uiso 1 1 calc R U . . .
H16B H 0.2420 -0.1055 -0.0783 0.108 Uiso 1 1 calc R U . . .
H16C H 0.3249 -0.0026 -0.1569 0.108 Uiso 1 1 calc R U . . .
C17 C 0.6150(8) 0.4427(9) 0.1857(7) 0.115(2) Uani 1 1 d . . . . .
H17A H 0.5953 0.5261 0.1285 0.138 Uiso 1 1 calc R U . . .
H17B H 0.7173 0.3868 0.1401 0.138 Uiso 1 1 calc R U . . .
Cl1 Cl 0.5940(3) 0.4799(2) 0.3361(2) 0.1378(8) Uani 1 1 d . . . . .
Cl2 Cl 0.5043(2) 0.3630(3) 0.2025(4) 0.1953(16) Uani 1 1 d . U . . .
H2 H 0.043(5) 0.584(5) 0.082(5) 0.057(12) 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
S1 O3 1.415(3) . ?
S1 O2 1.429(3) . ?
S1 N2 1.615(3) . ?
S1 C9 1.783(4) . ?
N1 C1 1.344(5) . ?
N1 C8 1.405(5) . ?
N1 C16 1.448(5) . ?
N2 N3 1.409(4) . ?
N3 C10 1.449(5) . ?
N3 C13 1.459(5) . ?
O1 C1 1.222(4) . ?
O4 C12 1.404(6) . ?
O4 C11 1.414(6) . ?
C1 C2 1.529(5) . ?
C2 C3 1.513(5) . ?
C2 C9 1.531(5) . ?
C2 C14 1.536(5) . ?
C3 C4 1.360(5) . ?
C3 C8 1.395(5) . ?
C4 C5 1.391(5) . ?
C5 C6 1.386(6) . ?
C5 C15 1.508(6) . ?
C6 C7 1.378(6) . ?
C7 C8 1.368(5) . ?
C10 C11 1.507(6) . ?
C12 C13 1.505(5) . ?
C17 Cl2 1.681(7) . ?
C17 Cl1 1.724(7) . ?

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
O3 S1 O2 119.13(19) . . ?
O3 S1 N2 108.81(17) . . ?
O2 S1 N2 104.47(18) . . ?
O3 S1 C9 108.25(18) . . ?
O2 S1 C9 108.58(16) . . ?
N2 S1 C9 106.98(17) . . ?
C1 N1 C8 111.5(3) . . ?
C1 N1 C16 124.2(3) . . ?
C8 N1 C16 124.3(3) . . ?
N3 N2 S1 118.2(3) . . ?
N2 N3 C10 111.3(3) . . ?
N2 N3 C13 109.0(3) . . ?
C10 N3 C13 110.1(3) . . ?
C12 O4 C11 110.4(3) . . ?
O1 C1 N1 126.1(3) . . ?
O1 C1 C2 125.3(3) . . ?
N1 C1 C2 108.6(3) . . ?
C3 C2 C1 102.2(3) . . ?
C3 C2 C9 116.6(3) . . ?
C1 C2 C9 111.6(3) . . ?
C3 C2 C14 111.0(3) . . ?
C1 C2 C14 108.3(3) . . ?
C9 C2 C14 107.0(3) . . ?
C4 C3 C8 120.4(3) . . ?
C4 C3 C2 131.6(3) . . ?
C8 C3 C2 107.9(3) . . ?
C3 C4 C5 119.8(3) . . ?
C6 C5 C4 118.5(4) . . ?
C6 C5 C15 121.0(4) . . ?
C4 C5 C15 120.6(4) . . ?
C7 C6 C5 122.5(4) . . ?
C8 C7 C6 117.6(4) . . ?
C7 C8 C3 121.1(4) . . ?
C7 C8 N1 129.2(3) . . ?
C3 C8 N1 109.6(3) . . ?
C2 C9 S1 115.8(2) . . ?
N3 C10 C11 109.3(3) . . ?
O4 C11 C10 111.8(4) . . ?
O4 C12 C13 111.4(4) . . ?
N3 C13 C12 108.8(3) . . ?
Cl2 C17 Cl1 114.4(4) . . ?

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
O3 S1 N2 N3 -52.1(3) . . . . ?
O2 S1 N2 N3 179.7(3) . . . . ?
C9 S1 N2 N3 64.6(3) . . . . ?
S1 N2 N3 C10 -119.0(3) . . . . ?
S1 N2 N3 C13 119.4(3) . . . . ?
C8 N1 C1 O1 179.3(4) . . . . ?
C16 N1 C1 O1 -0.6(6) . . . . ?
C8 N1 C1 C2 -2.9(4) . . . . ?
C16 N1 C1 C2 177.2(3) . . . . ?
O1 C1 C2 C3 -177.9(3) . . . . ?
N1 C1 C2 C3 4.3(4) . . . . ?
O1 C1 C2 C9 -52.6(5) . . . . ?
N1 C1 C2 C9 129.6(3) . . . . ?
O1 C1 C2 C14 64.9(4) . . . . ?
N1 C1 C2 C14 -112.9(3) . . . . ?
C1 C2 C3 C4 -179.8(4) . . . . ?
C9 C2 C3 C4 58.3(5) . . . . ?
C14 C2 C3 C4 -64.6(5) . . . . ?
C1 C2 C3 C8 -4.2(3) . . . . ?
C9 C2 C3 C8 -126.1(3) . . . . ?
C14 C2 C3 C8 111.1(3) . . . . ?
C8 C3 C4 C5 1.4(5) . . . . ?
C2 C3 C4 C5 176.6(4) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C3 C4 C5 C15 179.4(4) . . . . ?
C4 C5 C6 C7 -0.8(6) . . . . ?
C15 C5 C6 C7 179.6(4) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C6 C7 C8 C3 0.8(6) . . . . ?
C6 C7 C8 N1 179.9(4) . . . . ?
C4 C3 C8 C7 -1.8(5) . . . . ?
C2 C3 C8 C7 -178.0(3) . . . . ?
C4 C3 C8 N1 179.0(3) . . . . ?
C2 C3 C8 N1 2.8(4) . . . . ?
C1 N1 C8 C7 -179.0(4) . . . . ?
C16 N1 C8 C7 0.9(6) . . . . ?
C1 N1 C8 C3 0.1(4) . . . . ?
C16 N1 C8 C3 180.0(3) . . . . ?
C3 C2 C9 S1 56.2(4) . . . . ?
C1 C2 C9 S1 -60.6(3) . . . . ?
C14 C2 C9 S1 -178.9(3) . . . . ?
O3 S1 C9 C2 -71.4(3) . . . . ?
O2 S1 C9 C2 59.3(3) . . . . ?
N2 S1 C9 C2 171.5(3) . . . . ?
N2 N3 C10 C11 -178.1(3) . . . . ?
C13 N3 C10 C11 -57.0(4) . . . . ?
C12 O4 C11 C10 -57.7(5) . . . . ?
N3 C10 C11 O4 56.9(5) . . . . ?
C11 O4 C12 C13 58.7(5) . . . . ?
N2 N3 C13 C12 -179.7(3) . . . . ?
C10 N3 C13 C12 58.0(4) . . . . ?
O4 C12 C13 N3 -58.9(4) . . . . ?

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
N2 H2 O2 0.81(5) 2.48(4) 3.164(5) 142(4) 2_565
N2 H2 O1 0.81(5) 2.36(5) 3.004(5) 137(4) 2_565

_refine_diff_density_max         1.033
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.092

_shelxl_version_number           2013-2



