# 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_CAP1
_database_code_depnum_ccdc_archive 'CCDC 1497315'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2016-09-16 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         'C18 H24 Cl N3 O2 S'
_chemical_formula_sum            'C18 H24 Cl N3 O2 S'
_chemical_formula_weight         381.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1970 0.2290 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.2300 0.2930 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   38.822(8)
_cell_length_b                   4.5920(9)
_cell_length_c                   10.705(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.08(3)
_cell_angle_gamma                90
_cell_volume                     1884.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      32.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.775
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96990
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'MAR CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13010
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.450
_diffrn_reflns_theta_max         38.476
_diffrn_reflns_theta_full        35.587
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.931
_reflns_number_total             3654
_reflns_number_gt                3288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.812
_reflns_Friedel_fraction_full    0.876

_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       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0774P)²+0.7148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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_abs_structure_details 
;
 Flack x determined using 1415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.185(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3654
_refine_ls_number_parameters     235
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.71381(2) 0.91658(17) 0.81474(4) 0.0446(2) Uani 1 1 d . . . . .
S1 S 0.47520(2) 0.58908(14) 0.23669(5) 0.03807(19) Uani 1 1 d . . . . .
O1 O 0.55608(6) 0.6194(4) 0.5940(2) 0.0383(5) Uani 1 1 d . . . . .
O2 O 0.38967(5) 0.4946(5) 0.1877(2) 0.0352(5) Uani 1 1 d . . . . .
N1 N 0.53030(6) 1.0522(5) 0.5304(2) 0.0326(6) Uani 1 1 d . . . . .
H1 H 0.5301(9) 1.232(8) 0.537(3) 0.039 Uiso 1 1 d . U . . .
N2 N 0.58254(7) 1.0444(5) 0.6663(3) 0.0352(6) Uani 1 1 d . . . . .
H2 H 0.5815(9) 1.217(8) 0.659(4) 0.042 Uiso 1 1 d . U . . .
N3 N 0.31141(6) 0.2995(5) 0.1951(2) 0.0371(6) Uani 1 1 d . . . . .
C1 C 0.55624(8) 0.8892(6) 0.5962(3) 0.0323(7) Uani 1 1 d . . . . .
C2 C 0.50011(8) 0.9126(6) 0.4554(3) 0.0345(7) Uani 1 1 d . . . . .
H2A H 0.4800 1.0479 0.4460 0.041 Uiso 1 1 calc R U . . .
H2B H 0.4938 0.7367 0.5001 0.041 Uiso 1 1 calc R U . . .
C3 C 0.50775(7) 0.8266(7) 0.3241(3) 0.0359(7) Uani 1 1 d . . . . .
H3A H 0.5307 0.7278 0.3339 0.043 Uiso 1 1 calc R U . . .
H3B H 0.5094 1.0058 0.2740 0.043 Uiso 1 1 calc R U . . .
C4 C 0.43799(7) 0.8379(7) 0.1931(3) 0.0371(7) Uani 1 1 d . . . . .
H4A H 0.4304 0.9188 0.2701 0.044 Uiso 1 1 calc R U . . .
H4B H 0.4447 1.0015 0.1418 0.044 Uiso 1 1 calc R U . . .
C5 C 0.40919(7) 0.6677(6) 0.1190(3) 0.0337(7) Uani 1 1 d . . . . .
C6 C 0.39791(8) 0.6346(7) -0.0060(3) 0.0412(8) Uani 1 1 d . . . . .
H6 H 0.4069 0.7286 -0.0730 0.049 Uiso 1 1 calc R U . . .
C7 C 0.36960(8) 0.4294(6) -0.0180(3) 0.0401(8) Uani 1 1 d . . . . .
H7 H 0.3562 0.3624 -0.0947 0.048 Uiso 1 1 calc R U . . .
C8 C 0.36556(7) 0.3494(6) 0.1009(3) 0.0346(7) Uani 1 1 d . . . . .
C9 C 0.34173(8) 0.1494(6) 0.1573(3) 0.0372(7) Uani 1 1 d . . . . .
H9A H 0.3333 -0.0039 0.0949 0.045 Uiso 1 1 calc R U . . .
H9B H 0.3551 0.0530 0.2324 0.045 Uiso 1 1 calc R U . . .
C10 C 0.29551(9) 0.1148(7) 0.2830(3) 0.0442(8) Uani 1 1 d . . . . .
H10A H 0.2894 -0.0746 0.2435 0.066 Uiso 1 1 calc R U . . .
H10B H 0.2744 0.2095 0.3031 0.066 Uiso 1 1 calc R U . . .
H10C H 0.3122 0.0867 0.3610 0.066 Uiso 1 1 calc R U . . .
C11 C 0.28578(8) 0.3678(8) 0.0822(3) 0.0433(8) Uani 1 1 d . . . . .
H11A H 0.2970 0.4832 0.0230 0.065 Uiso 1 1 calc R U . . .
H11B H 0.2665 0.4793 0.1073 0.065 Uiso 1 1 calc R U . . .
H11C H 0.2768 0.1864 0.0412 0.065 Uiso 1 1 calc R U . . .
C12 C 0.60941(8) 0.9077(6) 0.7512(3) 0.0342(7) Uani 1 1 d . . . . .
C13 C 0.64419(8) 0.9688(6) 0.7442(3) 0.0358(7) Uani 1 1 d . . . . .
H13 H 0.6501 1.0976 0.6814 0.043 Uiso 1 1 calc R U . . .
C14 C 0.67011(7) 0.8384(7) 0.8305(3) 0.0363(7) Uani 1 1 d . . . . .
C15 C 0.66352(8) 0.6491(7) 0.9249(3) 0.0378(7) Uani 1 1 d . . . . .
C16 C 0.62820(8) 0.5902(6) 0.9290(3) 0.0385(8) Uani 1 1 d . . . . .
H16 H 0.6224 0.4591 0.9911 0.046 Uiso 1 1 calc R U . . .
C17 C 0.60149(7) 0.7172(6) 0.8453(3) 0.0375(7) Uani 1 1 d . . . . .
H17 H 0.5779 0.6754 0.8516 0.045 Uiso 1 1 calc R U . . .
C18 C 0.69203(8) 0.5153(8) 1.0191(3) 0.0448(8) Uani 1 1 d . . . . .
H18A H 0.7091 0.4210 0.9740 0.067 Uiso 1 1 calc R U . . .
H18B H 0.6819 0.3703 1.0699 0.067 Uiso 1 1 calc R U . . .
H18C H 0.7036 0.6677 1.0746 0.067 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
Cl1 C14 1.768(3) . ?
S1 C3 1.813(3) . ?
S1 C4 1.843(3) . ?
O1 C1 1.239(3) . ?
O2 C8 1.382(4) . ?
O2 C5 1.387(4) . ?
N1 C1 1.359(4) . ?
N1 C2 1.460(4) . ?
N1 H1 0.83(4) . ?
N2 C1 1.368(4) . ?
N2 C12 1.417(4) . ?
N2 H2 0.80(4) . ?
N3 C11 1.473(4) . ?
N3 C10 1.473(4) . ?
N3 C9 1.475(4) . ?
C2 C3 1.534(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.487(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.349(5) . ?
C6 C7 1.438(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.358(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.497(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.392(4) . ?
C12 C17 1.404(4) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C15 C16 1.405(4) . ?
C15 C18 1.505(4) . ?
C16 C17 1.388(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C3 S1 C4 102.25(14) . . ?
C8 O2 C5 106.8(2) . . ?
C1 N1 C2 120.5(2) . . ?
C1 N1 H1 121(2) . . ?
C2 N1 H1 118(2) . . ?
C1 N2 C12 122.1(2) . . ?
C1 N2 H2 116(3) . . ?
C12 N2 H2 122(3) . . ?
C11 N3 C10 110.5(2) . . ?
C11 N3 C9 109.8(3) . . ?
C10 N3 C9 109.9(2) . . ?
O1 C1 N1 122.7(3) . . ?
O1 C1 N2 122.2(3) . . ?
N1 C1 N2 115.2(2) . . ?
N1 C2 C3 111.3(3) . . ?
N1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 S1 114.1(2) . . ?
C2 C3 H3A 108.7 . . ?
S1 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
S1 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 S1 107.6(2) . . ?
C5 C4 H4A 110.2 . . ?
S1 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
S1 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C6 C5 O2 110.0(2) . . ?
C6 C5 C4 133.4(3) . . ?
O2 C5 C4 116.5(3) . . ?
C5 C6 C7 106.6(3) . . ?
C5 C6 H6 126.7 . . ?
C7 C6 H6 126.7 . . ?
C8 C7 C6 107.0(3) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
C7 C8 O2 109.5(3) . . ?
C7 C8 C9 135.6(3) . . ?
O2 C8 C9 114.9(3) . . ?
N3 C9 C8 113.3(2) . . ?
N3 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
N3 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 119.2(3) . . ?
C13 C12 N2 119.9(3) . . ?
C17 C12 N2 120.9(3) . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 123.9(3) . . ?
C15 C14 Cl1 119.1(2) . . ?
C13 C14 Cl1 117.0(2) . . ?
C14 C15 C16 115.9(3) . . ?
C14 C15 C18 122.9(3) . . ?
C16 C15 C18 121.3(3) . . ?
C17 C16 C15 122.2(3) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C12 119.9(3) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C2 N1 C1 O1 1.7(5) . . . . ?
C2 N1 C1 N2 -177.9(3) . . . . ?
C12 N2 C1 O1 -6.8(5) . . . . ?
C12 N2 C1 N1 172.7(3) . . . . ?
C1 N1 C2 C3 -83.9(3) . . . . ?
N1 C2 C3 S1 168.33(19) . . . . ?
C4 S1 C3 C2 72.3(2) . . . . ?
C3 S1 C4 C5 179.6(2) . . . . ?
C8 O2 C5 C6 0.2(3) . . . . ?
C8 O2 C5 C4 -177.8(2) . . . . ?
S1 C4 C5 C6 -97.6(4) . . . . ?
S1 C4 C5 O2 79.7(3) . . . . ?
O2 C5 C6 C7 0.1(3) . . . . ?
C4 C5 C6 C7 177.5(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 O2 0.4(3) . . . . ?
C6 C7 C8 C9 179.9(3) . . . . ?
C5 O2 C8 C7 -0.3(3) . . . . ?
C5 O2 C8 C9 -179.9(2) . . . . ?
C11 N3 C9 C8 75.6(3) . . . . ?
C10 N3 C9 C8 -162.7(3) . . . . ?
C7 C8 C9 N3 -95.7(4) . . . . ?
O2 C8 C9 N3 83.7(3) . . . . ?
C1 N2 C12 C13 128.5(3) . . . . ?
C1 N2 C12 C17 -53.5(4) . . . . ?
C17 C12 C13 C14 0.2(4) . . . . ?
N2 C12 C13 C14 178.3(3) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C12 C13 C14 Cl1 178.4(2) . . . . ?
C13 C14 C15 C16 0.6(5) . . . . ?
Cl1 C14 C15 C16 -178.0(2) . . . . ?
C13 C14 C15 C18 -178.7(3) . . . . ?
Cl1 C14 C15 C18 2.7(4) . . . . ?
C14 C15 C16 C17 -1.1(5) . . . . ?
C18 C15 C16 C17 178.2(3) . . . . ?
C15 C16 C17 C12 1.1(5) . . . . ?
C13 C12 C17 C16 -0.7(4) . . . . ?
N2 C12 C17 C16 -178.7(3) . . . . ?

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
N1 H1 O1 0.83(4) 2.09(4) 2.835(3) 150(3) 1_565
N2 H2 O1 0.80(4) 2.16(4) 2.894(3) 154(3) 1_565

_refine_diff_density_max         0.624
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.067

