# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1400219'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-07-02 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         ?
_chemical_formula_sum            'C14 H19 Cd N3 O2 S'
_chemical_formula_weight         405.78

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   13.9096(3)
_cell_length_b                   10.5234(2)
_cell_length_c                   22.6923(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3321.61(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      24.78

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.447
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44700
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.795
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_full        25.003
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2930
_reflns_number_gt                2585
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0171P)²+4.7289P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2930
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0645
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_restrained_S_all      1.246
_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
Cd1 Cd 0.61193(2) 0.04017(2) 0.47048(2) 0.03194(9) Uani 1 1 d . . . . .
O2 O 0.5700(2) -0.0608(3) 0.67453(11) 0.0524(7) Uani 1 1 d . . . . .
N2 N 0.6243(2) 0.1407(3) 0.37751(14) 0.0426(7) Uani 1 1 d . . . . .
N3 N 0.5585(2) 0.2434(3) 0.48668(13) 0.0370(7) Uani 1 1 d . . . . .
C4 C 0.6216(3) 0.2784(4) 0.38833(17) 0.0490(10) Uani 1 1 d . . . . .
H4A H 0.6089 0.3231 0.3507 0.059 Uiso 1 1 calc R U . . .
H4B H 0.6852 0.3065 0.4030 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5461(3) 0.3146(3) 0.43227(17) 0.0501(10) Uani 1 1 d . . . . .
H5A H 0.5503 0.4067 0.4406 0.060 Uiso 1 1 calc R U . . .
H5B H 0.4816 0.2969 0.4157 0.060 Uiso 1 1 calc R U . . .
C6 C 0.5478(2) 0.2996(3) 0.53561(17) 0.0425(9) Uani 1 1 d . . . . .
H6 H 0.5353 0.3883 0.5341 0.051 Uiso 1 1 calc R U . . .
C7 C 0.5528(3) 0.2425(3) 0.59346(16) 0.0412(8) Uani 1 1 d . . . . .
C8 C 0.5534(3) 0.3253(4) 0.6420(2) 0.0631(12) Uani 1 1 d . . . . .
H8 H 0.5508 0.4143 0.6352 0.076 Uiso 1 1 calc R U . . .
C9 C 0.5575(4) 0.2816(5) 0.6986(2) 0.0739(15) Uani 1 1 d . . . . .
H9 H 0.5550 0.3391 0.7308 0.089 Uiso 1 1 calc R U . . .
C10 C 0.5653(3) 0.1522(5) 0.70818(18) 0.0660(13) Uani 1 1 d . . . . .
H10 H 0.5708 0.1209 0.7473 0.079 Uiso 1 1 calc R U . . .
C11 C 0.5652(3) 0.0688(4) 0.66194(16) 0.0446(9) Uani 1 1 d . . . . .
C13 C 0.6577(4) -0.1186(5) 0.6562(2) 0.0712(13) Uani 1 1 d . . . . .
H13A H 0.7129 -0.0666 0.6694 0.085 Uiso 1 1 calc R U . . .
H13B H 0.6596 -0.1243 0.6127 0.085 Uiso 1 1 calc R U . . .
C14 C 0.6640(4) -0.2481(5) 0.6824(3) 0.0879(17) Uani 1 1 d . . . . .
H14A H 0.7242 -0.2886 0.6700 0.132 Uiso 1 1 calc R U . . .
H14B H 0.6626 -0.2418 0.7254 0.132 Uiso 1 1 calc R U . . .
H14C H 0.6094 -0.2993 0.6689 0.132 Uiso 1 1 calc R U . . .
C3 C 0.7038(3) 0.1050(5) 0.33796(19) 0.0642(12) Uani 1 1 d . . . . .
H3A H 0.7069 0.1661 0.3048 0.077 Uiso 1 1 calc R U . . .
H3B H 0.7653 0.1101 0.3598 0.077 Uiso 1 1 calc R U . . .
C2 C 0.6918(4) -0.0243(5) 0.3145(2) 0.0856(17) Uani 1 1 d . . . . .
H2A H 0.7459 -0.0446 0.2885 0.128 Uiso 1 1 calc R U . . .
H2B H 0.6900 -0.0851 0.3472 0.128 Uiso 1 1 calc R U . . .
H2C H 0.6316 -0.0292 0.2922 0.128 Uiso 1 1 calc R U . . .
O1 O 0.54345(16) 0.02391(19) 0.56101(9) 0.0329(5) Uani 1 1 d . . . . .
C12 C 0.5544(2) 0.1084(3) 0.60296(14) 0.0347(8) Uani 1 1 d . . . . .
S1 S 0.70307(8) -0.41035(9) 0.50717(6) 0.0648(3) Uani 1 1 d . . . . .
N1 N 0.6651(2) -0.1616(3) 0.47251(15) 0.0458(6) Uani 1 1 d . . . . .
C1 C 0.6822(3) -0.2634(3) 0.48737(18) 0.0458(6) Uani 1 1 d . . . . .
H2 H 0.576(3) 0.126(4) 0.3616(19) 0.059(15) 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
Cd1 N1 2.249(3) . ?
Cd1 O1 2.271(2) . ?
Cd1 N3 2.294(3) . ?
Cd1 N2 2.366(3) . ?
Cd1 O1 2.374(2) 5_656 ?
Cd1 S1 2.7543(11) 6_765 ?
O2 C11 1.395(5) . ?
O2 C13 1.425(5) . ?
N2 C4 1.471(5) . ?
N2 C3 1.473(5) . ?
N2 H2 0.77(4) . ?
N3 C6 1.267(4) . ?
N3 C5 1.454(4) . ?
C4 C5 1.498(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.446(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.404(5) . ?
C7 C12 1.428(5) . ?
C8 C9 1.365(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.368(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.410(5) . ?
C13 C14 1.489(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C3 C2 1.471(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
O1 C12 1.311(4) . ?
O1 Cd1 2.374(2) 5_656 ?
S1 C1 1.636(4) . ?
S1 Cd1 2.7544(10) 6_755 ?
N1 C1 1.148(5) . ?

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
N1 Cd1 O1 92.76(10) . . ?
N1 Cd1 N3 169.60(11) . . ?
O1 Cd1 N3 77.84(9) . . ?
N1 Cd1 N2 114.62(12) . . ?
O1 Cd1 N2 150.54(10) . . ?
N3 Cd1 N2 75.50(11) . . ?
N1 Cd1 O1 92.12(9) . 5_656 ?
O1 Cd1 O1 82.47(8) . 5_656 ?
N3 Cd1 O1 91.03(9) . 5_656 ?
N2 Cd1 O1 85.69(10) . 5_656 ?
N1 Cd1 S1 82.26(8) . 6_765 ?
O1 Cd1 S1 97.62(6) . 6_765 ?
N3 Cd1 S1 94.48(7) . 6_765 ?
N2 Cd1 S1 96.73(9) . 6_765 ?
O1 Cd1 S1 174.38(5) 5_656 6_765 ?
C11 O2 C13 113.5(3) . . ?
C4 N2 C3 111.8(3) . . ?
C4 N2 Cd1 106.8(2) . . ?
C3 N2 Cd1 118.9(3) . . ?
C4 N2 H2 105(3) . . ?
C3 N2 H2 108(3) . . ?
Cd1 N2 H2 105(3) . . ?
C6 N3 C5 119.3(3) . . ?
C6 N3 Cd1 127.9(2) . . ?
C5 N3 Cd1 112.5(2) . . ?
N2 C4 C5 112.3(3) . . ?
N2 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N3 C5 C4 110.6(3) . . ?
N3 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N3 C6 C7 126.6(3) . . ?
N3 C6 H6 116.7 . . ?
C7 C6 H6 116.7 . . ?
C8 C7 C12 119.7(4) . . ?
C8 C7 C6 117.0(4) . . ?
C12 C7 C6 123.3(3) . . ?
C9 C8 C7 121.9(4) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 118.9(4) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 O2 118.0(4) . . ?
C10 C11 C12 122.6(4) . . ?
O2 C11 C12 119.3(3) . . ?
O2 C13 C14 109.0(4) . . ?
O2 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
O2 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 N2 111.8(4) . . ?
C2 C3 H3A 109.3 . . ?
N2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
N2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C12 O1 Cd1 123.85(19) . . ?
C12 O1 Cd1 121.10(19) . 5_656 ?
Cd1 O1 Cd1 97.53(8) . 5_656 ?
O1 C12 C11 120.1(3) . . ?
O1 C12 C7 124.0(3) . . ?
C11 C12 C7 115.9(3) . . ?
C1 S1 Cd1 105.13(13) . 6_755 ?
C1 N1 Cd1 162.8(3) . . ?
N1 C1 S1 177.8(4) . . ?

_refine_diff_density_max         0.624
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.069

