# 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_l12516t5
_database_code_depnum_ccdc_archive 'CCDC 1579175'
_audit_update_record             
;
2017-10-10 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H29 N4 O4 S2, Cl'
_chemical_formula_sum            'C28 H29 Cl N4 O4 S2'
_chemical_formula_weight         585.12

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                   7.7992(3)
_cell_length_b                   9.5520(4)
_cell_length_c                   9.6675(4)
_cell_angle_alpha                90.026(2)
_cell_angle_beta                 112.7594(17)
_cell_angle_gamma                93.5164(16)
_cell_volume                     662.65(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      40.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             306
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.218
_exptl_absorpt_coefficient_mu    0.346
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.803156
_exptl_absorpt_correction_T_max  0.862764
_exptl_absorpt_process_details   'TWINABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            30030
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.137
_diffrn_reflns_theta_max         40.410
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             30030
_reflns_number_gt                27041
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0256P)²+1.0332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         30030
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1312
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_restrained_S_all      1.227
_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 0.42448(5) 0.73509(3) 0.20828(4) 0.00935(7) Uani 1 1 d . . . . .
O1 O 0.59366(17) 0.78870(12) 0.19642(14) 0.0148(2) Uani 1 1 d . . . . .
O2 O 0.24954(17) 0.78859(11) 0.11813(13) 0.0154(2) Uani 1 1 d . . . . .
N1 N 0.30843(18) 1.01550(13) 0.44678(15) 0.0107(2) Uani 1 1 d . . . . .
N2 N 0.45261(18) 0.76440(13) 0.38224(15) 0.0107(2) Uani 1 1 d . . . . .
C1 C 0.2383(2) 1.14192(15) 0.43460(17) 0.0117(2) Uani 1 1 d . . . . .
C2 C 0.0489(2) 1.15663(17) 0.3601(2) 0.0167(3) Uani 1 1 d . . . . .
H2 H 0.0000 1.2464 0.3512 0.020 Uiso 1 1 calc R U . . .
C3 C -0.0676(2) 1.03812(19) 0.2989(2) 0.0216(4) Uani 1 1 d . . . . .
H3 H -0.1977 1.0460 0.2468 0.026 Uiso 1 1 calc R U . . .
C4 C 0.0061(2) 0.90756(18) 0.3138(2) 0.0193(3) Uani 1 1 d . . . . .
H4 H -0.0727 0.8255 0.2725 0.023 Uiso 1 1 calc R U . . .
C5 C 0.1949(2) 0.89904(15) 0.38944(18) 0.0128(3) Uani 1 1 d . . . . .
C6 C 0.2848(2) 0.76097(16) 0.4173(2) 0.0147(3) Uani 1 1 d . . . . .
H6A H 0.3189 0.7371 0.5239 0.018 Uiso 1 1 calc R U . . .
H6B H 0.1937 0.6865 0.3550 0.018 Uiso 1 1 calc R U . . .
C7 C 0.6302(2) 0.73083(15) 0.49883(18) 0.0129(3) Uani 1 1 d . . . . .
H7A H 0.6915 0.6658 0.4556 0.016 Uiso 1 1 calc R U . . .
H7B H 0.6055 0.6817 0.5800 0.016 Uiso 1 1 calc R U . . .
C8 C 0.4038(2) 0.55269(14) 0.17746(17) 0.0109(2) Uani 1 1 d . . . . .
C9 C 0.2287(2) 0.48270(15) 0.13360(18) 0.0137(3) Uani 1 1 d . . . . .
H9 H 0.1228 0.5331 0.1217 0.016 Uiso 1 1 calc R U . . .
C10 C 0.2097(2) 0.33862(15) 0.10732(19) 0.0157(3) Uani 1 1 d . . . . .
H10 H 0.0902 0.2905 0.0767 0.019 Uiso 1 1 calc R U . . .
C11 C 0.3652(3) 0.26384(15) 0.12562(18) 0.0152(3) Uani 1 1 d . . . . .
C12 C 0.5387(2) 0.33643(16) 0.16941(19) 0.0155(3) Uani 1 1 d . . . . .
H12 H 0.6448 0.2861 0.1818 0.019 Uiso 1 1 calc R U . . .
C13 C 0.5608(2) 0.48072(15) 0.19560(18) 0.0134(3) Uani 1 1 d . . . . .
H13 H 0.6801 0.5291 0.2251 0.016 Uiso 1 1 calc R U . . .
C14 C 0.3456(3) 0.10731(16) 0.1026(2) 0.0227(4) Uani 1 1 d . . . . .
H14A H 0.3831 0.0823 0.0205 0.034 Uiso 1 1 calc R U . . .
H14B H 0.2155 0.0738 0.0774 0.034 Uiso 1 1 calc R U . . .
H14C H 0.4254 0.0636 0.1949 0.034 Uiso 1 1 calc R U . . .
Cl1 Cl 0.0000 0.5000 0.5000 0.01837(12) Uani 1 2 d S . P . .
H1 H 0.421(6) 1.003(5) 0.483(5) 0.013(10) Uiso 0.5 1 d . . P A -1


_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 O2 1.4312(12) . ?
S1 O1 1.4319(13) . ?
S1 N2 1.6314(14) . ?
S1 C8 1.7545(14) . ?
N1 C1 1.3427(19) . ?
N1 C5 1.3518(19) . ?
N1 H1 0.82(4) . ?
N2 C7 1.4625(19) . ?
N2 C6 1.472(2) . ?
C1 C2 1.387(2) . ?
C1 C7 1.510(2) 2_676 ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.507(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C1 1.510(2) 2_676 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.390(2) . ?
C8 C13 1.393(2) . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(2) . ?
C11 C14 1.501(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
O2 S1 O1 120.90(8) . . ?
O2 S1 N2 106.01(7) . . ?
O1 S1 N2 105.87(7) . . ?
O2 S1 C8 107.71(7) . . ?
O1 S1 C8 108.09(7) . . ?
N2 S1 C8 107.62(7) . . ?
C1 N1 C5 120.56(14) . . ?
C1 N1 H1 124(3) . . ?
C5 N1 H1 115(3) . . ?
C7 N2 C6 119.33(13) . . ?
C7 N2 S1 117.27(11) . . ?
C6 N2 S1 117.78(10) . . ?
N1 C1 C2 120.95(14) . . ?
N1 C1 C7 118.86(13) . 2_676 ?
C2 C1 C7 120.18(13) . 2_676 ?
C3 C2 C1 118.75(15) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.84(16) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.94(15) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 120.93(14) . . ?
N1 C5 C6 116.73(14) . . ?
C4 C5 C6 122.30(14) . . ?
N2 C6 C5 112.31(13) . . ?
N2 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C1 113.51(12) . 2_676 ?
N2 C7 H7A 108.9 . . ?
C1 C7 H7A 108.9 2_676 . ?
N2 C7 H7B 108.9 . . ?
C1 C7 H7B 108.9 2_676 . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C13 121.14(13) . . ?
C9 C8 S1 118.80(11) . . ?
C13 C8 S1 120.06(11) . . ?
C10 C9 C8 119.48(14) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.50(15) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 118.84(13) . . ?
C12 C11 C14 120.73(16) . . ?
C10 C11 C14 120.41(16) . . ?
C13 C12 C11 121.67(15) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C8 118.37(15) . . ?
C12 C13 H13 120.8 . . ?
C8 C13 H13 120.8 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O2 S1 N2 C7 -174.62(11) . . . . ?
O1 S1 N2 C7 -45.05(12) . . . . ?
C8 S1 N2 C7 70.35(12) . . . . ?
O2 S1 N2 C6 31.94(12) . . . . ?
O1 S1 N2 C6 161.51(11) . . . . ?
C8 S1 N2 C6 -83.09(12) . . . . ?
C5 N1 C1 C2 -1.5(3) . . . . ?
C5 N1 C1 C7 179.57(15) . . . 2_676 ?
N1 C1 C2 C3 0.4(3) . . . . ?
C7 C1 C2 C3 179.28(18) 2_676 . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C1 N1 C5 C4 1.8(3) . . . . ?
C1 N1 C5 C6 -176.15(15) . . . . ?
C3 C4 C5 N1 -0.9(3) . . . . ?
C3 C4 C5 C6 176.90(18) . . . . ?
C7 N2 C6 C5 122.84(14) . . . . ?
S1 N2 C6 C5 -84.28(14) . . . . ?
N1 C5 C6 N2 -48.4(2) . . . . ?
C4 C5 C6 N2 133.67(17) . . . . ?
C6 N2 C7 C1 -104.31(16) . . . 2_676 ?
S1 N2 C7 C1 102.68(14) . . . 2_676 ?
O2 S1 C8 C9 -26.58(15) . . . . ?
O1 S1 C8 C9 -158.76(13) . . . . ?
N2 S1 C8 C9 87.32(14) . . . . ?
O2 S1 C8 C13 152.82(13) . . . . ?
O1 S1 C8 C13 20.64(15) . . . . ?
N2 S1 C8 C13 -93.28(14) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
S1 C8 C9 C10 179.35(13) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 C14 177.75(17) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C14 C11 C12 C13 -178.08(17) . . . . ?
C11 C12 C13 C8 0.2(3) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
S1 C8 C13 C12 -179.67(13) . . . . ?

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
#C6 H6B Cl1  0.99 2.96 3.5330(16) 118.3 . 
#C7 H7A Cl1  0.99 2.85 3.7327(15) 148.2 1_655 
#C13 H13 Cl1  0.95 2.88 3.5425(16) 127.4 1_655 
C2 H2 Cl1 0.95 2.82 3.6443(16) 146.1 1_565
C4 H4 O1 0.95 2.42 3.106(2) 129.2 1_455
N1 H1 N1 0.82(4) 1.97(4) 2.794(3) 174(5) 2_676

_refine_diff_density_max         1.164
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.103

