# 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_17a
_database_code_depnum_ccdc_archive 'CCDC 1453249'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-5-(4-methylbenzylidene)-2-(piperidin-1-yl)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O S'
_chemical_formula_sum            'C16 H18 N2 O S'
_chemical_formula_weight         286.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.5012(6)
_cell_length_b                   16.1346(7)
_cell_length_c                   7.6541(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.967(2)
_cell_angle_gamma                90
_cell_volume                     1476.65(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4440
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      23.61

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    0.216
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26765
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.1063
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.525
_diffrn_reflns_theta_max         25.695
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2807
_reflns_number_gt                1923
_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-2014/7 (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)+(0.0458P)²+0.6578P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0061(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2807
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
S1 S 0.52444(5) 0.70557(4) 0.57025(10) 0.0462(2) Uani 1 1 d . . . . .
O1 O 0.39270(16) 0.91749(12) 0.5881(3) 0.0690(6) Uani 1 1 d . . . . .
N2 N 0.34362(17) 0.78158(13) 0.6023(3) 0.0478(6) Uani 1 1 d . . . . .
N1 N 0.33816(18) 0.63771(13) 0.6135(4) 0.0557(7) Uani 1 1 d . . . . .
C10 C 0.7123(2) 0.84999(15) 0.5213(4) 0.0417(6) Uani 1 1 d . . . . .
C8 C 0.5239(2) 0.81361(14) 0.5653(4) 0.0401(6) Uani 1 1 d . . . . .
C6 C 0.3883(2) 0.70809(16) 0.5976(3) 0.0432(6) Uani 1 1 d . . . . .
C9 C 0.6028(2) 0.86508(16) 0.5453(4) 0.0459(7) Uani 1 1 d . . . . .
H9 H 0.5845 0.9209 0.5470 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4145(2) 0.84355(17) 0.5865(4) 0.0482(7) Uani 1 1 d . . . . .
C13 C 0.9246(2) 0.8327(2) 0.4667(4) 0.0579(8) Uani 1 1 d . . . . .
C15 C 0.7579(2) 0.77275(17) 0.5081(4) 0.0590(8) Uani 1 1 d . . . . .
H15 H 0.7179 0.7253 0.5186 0.071 Uiso 1 1 calc R U . . .
C1 C 0.2270(2) 0.63657(19) 0.6413(5) 0.0626(9) Uani 1 1 d . . . . .
H1A H 0.1979 0.6926 0.6345 0.075 Uiso 1 1 calc R U . . .
H1B H 0.2322 0.6146 0.7614 0.075 Uiso 1 1 calc R U . . .
C11 C 0.7764(2) 0.91824(17) 0.5061(4) 0.0584(8) Uani 1 1 d . . . . .
H11 H 0.7487 0.9712 0.5134 0.070 Uiso 1 1 calc R U . . .
C14 C 0.8607(3) 0.76500(19) 0.4798(5) 0.0658(9) Uani 1 1 d . . . . .
H14 H 0.8882 0.7123 0.4691 0.079 Uiso 1 1 calc R U . . .
C12 C 0.8798(3) 0.9091(2) 0.4805(5) 0.0702(10) Uani 1 1 d . . . . .
H12 H 0.9208 0.9563 0.4721 0.084 Uiso 1 1 calc R U . . .
C5 C 0.3882(3) 0.55616(18) 0.6137(5) 0.0754(11) Uani 1 1 d . . . . .
H5A H 0.4017 0.5310 0.7333 0.090 Uiso 1 1 calc R U . . .
H5B H 0.4595 0.5618 0.5885 0.090 Uiso 1 1 calc R U . . .
C2 C 0.1486(3) 0.5833(2) 0.4963(5) 0.0843(11) Uani 1 1 d . . . . .
H2A H 0.0766 0.5799 0.5199 0.101 Uiso 1 1 calc R U . . .
H2B H 0.1373 0.6087 0.3774 0.101 Uiso 1 1 calc R U . . .
C4 C 0.3121(3) 0.5013(2) 0.4716(6) 0.0977(13) Uani 1 1 d . . . . .
H4A H 0.3436 0.4460 0.4809 0.117 Uiso 1 1 calc R U . . .
H4B H 0.3071 0.5227 0.3510 0.117 Uiso 1 1 calc R U . . .
C16 C 1.0374(3) 0.8244(2) 0.4329(6) 0.0870(12) Uani 1 1 d . . . . .
H16A H 1.0493 0.8707 0.3622 0.130 Uiso 1 1 calc R U . . .
H16B H 1.0394 0.7739 0.3675 0.130 Uiso 1 1 calc R U . . .
H16C H 1.0950 0.8232 0.5477 0.130 Uiso 1 1 calc R U . . .
C3 C 0.1958(3) 0.4970(2) 0.4951(6) 0.0914(12) Uani 1 1 d . . . . .
H3A H 0.1471 0.4652 0.3959 0.110 Uiso 1 1 calc R U . . .
H3B H 0.1992 0.4692 0.6089 0.110 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
S1 C8 1.744(2) . ?
S1 C6 1.775(2) . ?
O1 C7 1.225(3) . ?
N2 C6 1.316(3) . ?
N2 C7 1.364(3) . ?
N1 C6 1.319(3) . ?
N1 C5 1.457(3) . ?
N1 C1 1.467(3) . ?
C10 C15 1.386(3) . ?
C10 C11 1.387(4) . ?
C10 C9 1.454(3) . ?
C8 C9 1.332(3) . ?
C8 C7 1.504(4) . ?
C9 H9 0.9300 . ?
C13 C12 1.371(4) . ?
C13 C14 1.374(4) . ?
C13 C16 1.511(4) . ?
C15 C14 1.370(4) . ?
C15 H15 0.9300 . ?
C1 C2 1.515(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C5 C4 1.505(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 C3 1.513(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C3 1.518(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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
C8 S1 C6 88.98(12) . . ?
C6 N2 C7 111.5(2) . . ?
C6 N1 C5 124.2(2) . . ?
C6 N1 C1 121.3(2) . . ?
C5 N1 C1 114.4(2) . . ?
C15 C10 C11 116.6(2) . . ?
C15 C10 C9 125.6(2) . . ?
C11 C10 C9 117.8(2) . . ?
C9 C8 C7 122.7(2) . . ?
C9 C8 S1 128.9(2) . . ?
C7 C8 S1 108.45(18) . . ?
N2 C6 N1 123.8(2) . . ?
N2 C6 S1 116.94(19) . . ?
N1 C6 S1 119.25(19) . . ?
C8 C9 C10 131.8(2) . . ?
C8 C9 H9 114.1 . . ?
C10 C9 H9 114.1 . . ?
O1 C7 N2 124.1(2) . . ?
O1 C7 C8 121.7(2) . . ?
N2 C7 C8 114.1(2) . . ?
C12 C13 C14 116.7(3) . . ?
C12 C13 C16 121.0(3) . . ?
C14 C13 C16 122.2(3) . . ?
C14 C15 C10 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
N1 C1 C2 109.8(3) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C15 C14 C13 122.1(3) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C11 C12 C13 122.1(3) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
N1 C5 C4 110.4(3) . . ?
N1 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C3 C2 C1 110.9(3) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C5 C4 C3 111.5(3) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C3 C4 110.3(3) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_17e
_database_code_depnum_ccdc_archive 'CCDC 1453250'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-2-(piperidin-1-yl)-5-(2,4,5-trimethoxybenzylidene)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O4 S'
_chemical_formula_sum            'C18 H22 N2 O4 S'
_chemical_formula_weight         362.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.0466(4)
_cell_length_b                   7.7834(3)
_cell_length_c                   22.9774(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.920(2)
_cell_angle_gamma                90
_cell_volume                     1792.55(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    8539
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      25.28

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25972
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.764
_diffrn_reflns_theta_max         25.700
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3417
_reflns_number_gt                2616
_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-2014/7 (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)+(0.0470P)²+0.7766P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0069(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3417
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
S1 S 0.58046(5) 0.31279(7) 0.60558(2) 0.04288(18) Uani 1 1 d . . . . .
O1 O 0.85464(15) 0.6094(2) 0.67047(7) 0.0592(5) Uani 1 1 d . . . . .
O3 O 0.81622(15) 0.0653(2) 0.35140(6) 0.0565(4) Uani 1 1 d . . . . .
O2 O 1.06426(14) 0.2868(2) 0.52310(7) 0.0547(4) Uani 1 1 d . . . . .
N1 N 0.44378(16) 0.3806(2) 0.69891(7) 0.0411(4) Uani 1 1 d . . . . .
O4 O 0.59326(15) 0.1350(2) 0.39591(6) 0.0598(5) Uani 1 1 d . . . . .
N2 N 0.65097(15) 0.5132(2) 0.69543(7) 0.0381(4) Uani 1 1 d . . . . .
C7 C 0.75619(19) 0.5194(3) 0.66061(8) 0.0381(5) Uani 1 1 d . . . . .
C6 C 0.55522(19) 0.4129(2) 0.67366(8) 0.0347(4) Uani 1 1 d . . . . .
C8 C 0.73917(19) 0.4068(2) 0.60764(8) 0.0358(4) Uani 1 1 d . . . . .
C13 C 0.8276(2) 0.1384(3) 0.40496(9) 0.0415(5) Uani 1 1 d . . . . .
C10 C 0.83068(19) 0.2929(2) 0.51533(8) 0.0369(4) Uani 1 1 d . . . . .
C9 C 0.83463(19) 0.3839(3) 0.57061(8) 0.0386(5) Uani 1 1 d . . . . .
H9 H 0.9163 0.4341 0.5820 0.046 Uiso 1 1 calc R U . . .
C11 C 0.94942(19) 0.2500(3) 0.49048(9) 0.0396(5) Uani 1 1 d . . . . .
C12 C 0.9471(2) 0.1748(3) 0.43563(9) 0.0433(5) Uani 1 1 d . . . . .
H12 H 1.0269 0.1486 0.4194 0.052 Uiso 1 1 calc R U . . .
C15 C 0.71062(19) 0.2539(3) 0.48312(8) 0.0397(5) Uani 1 1 d . . . . .
H15 H 0.6304 0.2812 0.4989 0.048 Uiso 1 1 calc R U . . .
C14 C 0.7072(2) 0.1773(3) 0.42934(8) 0.0412(5) Uani 1 1 d . . . . .
C16 C 1.1876(2) 0.2335(3) 0.50221(10) 0.0539(6) Uani 1 1 d . . . . .
H16B H 1.1879 0.1108 0.4980 0.081 Uiso 1 1 calc R U . . .
H16A H 1.2594 0.2675 0.5295 0.081 Uiso 1 1 calc R U . . .
H16C H 1.1988 0.2862 0.4651 0.081 Uiso 1 1 calc R U . . .
C5 C 0.3325(2) 0.2812(3) 0.67178(9) 0.0447(5) Uani 1 1 d . . . . .
H5A H 0.3090 0.1893 0.6977 0.054 Uiso 1 1 calc R U . . .
H5B H 0.3584 0.2301 0.6357 0.054 Uiso 1 1 calc R U . . .
C1 C 0.4141(2) 0.4599(3) 0.75426(9) 0.0507(6) Uani 1 1 d . . . . .
H1A H 0.4907 0.5254 0.7698 0.061 Uiso 1 1 calc R U . . .
H1B H 0.3956 0.3714 0.7823 0.061 Uiso 1 1 calc R U . . .
C18 C 0.4703(2) 0.1714(3) 0.41902(10) 0.0566(6) Uani 1 1 d . . . . .
H18A H 0.4633 0.1076 0.4544 0.085 Uiso 1 1 calc R U . . .
H18B H 0.3988 0.1393 0.3913 0.085 Uiso 1 1 calc R U . . .
H18C H 0.4649 0.2921 0.4271 0.085 Uiso 1 1 calc R U . . .
C4 C 0.2146(2) 0.3979(3) 0.65942(10) 0.0552(6) Uani 1 1 d . . . . .
H4A H 0.1396 0.3321 0.6425 0.066 Uiso 1 1 calc R U . . .
H4B H 0.2365 0.4854 0.6316 0.066 Uiso 1 1 calc R U . . .
C2 C 0.2948(2) 0.5769(3) 0.74485(11) 0.0648(7) Uani 1 1 d . . . . .
H2A H 0.3177 0.6737 0.7209 0.078 Uiso 1 1 calc R U . . .
H2B H 0.2705 0.6212 0.7821 0.078 Uiso 1 1 calc R U . . .
C17 C 0.9355(3) 0.0327(4) 0.32275(11) 0.0687(8) Uani 1 1 d . . . . .
H17A H 0.9840 0.1381 0.3192 0.103 Uiso 1 1 calc R U . . .
H17B H 0.9129 -0.0136 0.2846 0.103 Uiso 1 1 calc R U . . .
H17C H 0.9898 -0.0482 0.3452 0.103 Uiso 1 1 calc R U . . .
C3 C 0.1770(2) 0.4823(4) 0.71537(12) 0.0678(7) Uani 1 1 d . . . . .
H3A H 0.1464 0.3953 0.7416 0.081 Uiso 1 1 calc R U . . .
H3B H 0.1044 0.5624 0.7067 0.081 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
S1 C8 1.752(2) . ?
S1 C6 1.7813(19) . ?
O1 C7 1.220(2) . ?
O3 C13 1.353(2) . ?
O3 C17 1.429(3) . ?
O2 C11 1.363(2) . ?
O2 C16 1.421(2) . ?
N1 C6 1.320(2) . ?
N1 C1 1.463(2) . ?
N1 C5 1.464(2) . ?
O4 C14 1.375(2) . ?
O4 C18 1.407(3) . ?
N2 C6 1.311(2) . ?
N2 C7 1.369(2) . ?
C7 C8 1.500(3) . ?
C8 C9 1.337(3) . ?
C13 C12 1.379(3) . ?
C13 C14 1.401(3) . ?
C10 C11 1.398(3) . ?
C10 C15 1.405(3) . ?
C10 C9 1.453(3) . ?
C9 H9 0.9300 . ?
C11 C12 1.389(3) . ?
C12 H12 0.9300 . ?
C15 C14 1.370(3) . ?
C15 H15 0.9300 . ?
C16 H16B 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16C 0.9600 . ?
C5 C4 1.505(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 C2 1.509(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C4 C3 1.514(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 C3 1.514(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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
C8 S1 C6 88.71(9) . . ?
C13 O3 C17 118.16(18) . . ?
C11 O2 C16 118.55(17) . . ?
C6 N1 C1 122.09(16) . . ?
C6 N1 C5 124.03(16) . . ?
C1 N1 C5 113.48(15) . . ?
C14 O4 C18 117.40(16) . . ?
C6 N2 C7 111.93(16) . . ?
O1 C7 N2 124.05(18) . . ?
O1 C7 C8 122.13(17) . . ?
N2 C7 C8 113.81(16) . . ?
N2 C6 N1 124.61(17) . . ?
N2 C6 S1 116.79(14) . . ?
N1 C6 S1 118.60(14) . . ?
C9 C8 C7 123.17(18) . . ?
C9 C8 S1 128.21(16) . . ?
C7 C8 S1 108.60(13) . . ?
O3 C13 C12 124.59(18) . . ?
O3 C13 C14 115.64(18) . . ?
C12 C13 C14 119.77(18) . . ?
C11 C10 C15 117.34(17) . . ?
C11 C10 C9 120.05(18) . . ?
C15 C10 C9 122.50(17) . . ?
C8 C9 C10 130.05(19) . . ?
C8 C9 H9 115.0 . . ?
C10 C9 H9 115.0 . . ?
O2 C11 C12 123.31(17) . . ?
O2 C11 C10 116.05(17) . . ?
C12 C11 C10 120.63(19) . . ?
C13 C12 C11 120.71(18) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C15 C10 122.46(18) . . ?
C14 C15 H15 118.8 . . ?
C10 C15 H15 118.8 . . ?
C15 C14 O4 125.21(18) . . ?
C15 C14 C13 119.07(19) . . ?
O4 C14 C13 115.72(17) . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
N1 C5 C4 109.25(18) . . ?
N1 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N1 C1 C2 109.70(18) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5 C4 C3 109.89(19) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C1 C2 C3 111.1(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C3 C2 111.0(2) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_17f
_database_code_depnum_ccdc_archive 'CCDC 1453251'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-5-(3-hydroxy-4-methoxybenzylidene)-2-(piperidin-1-yl)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O3 S'
_chemical_formula_sum            'C16 H18 N2 O3 S'
_chemical_formula_weight         318.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.303(3)
_cell_length_b                   16.637(5)
_cell_length_c                   12.598(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.725(13)
_cell_angle_gamma                90
_cell_volume                     1516.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5376
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      25.55

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.019
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28807
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.1079
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.448
_diffrn_reflns_theta_max         25.697
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2879
_reflns_number_gt                2127
_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-2014/7 (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)+(0.0433P)²+0.4919P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0085(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2879
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.29555(8) 0.44388(3) 0.32605(4) 0.02913(18) Uani 1 1 d . . . . .
O3 O 0.1538(2) 0.59097(10) 0.82036(11) 0.0443(5) Uani 1 1 d . . . . .
O2 O 0.1881(3) 0.72849(10) 0.72893(13) 0.0523(5) Uani 1 1 d . . . . .
H2 H 0.2330 0.7675 0.7022 0.078 Uiso 1 1 calc R U . . .
N2 N 0.3745(3) 0.50510(10) 0.14354(14) 0.0318(4) Uani 1 1 d . . . . .
O1 O 0.3548(3) 0.63965(9) 0.17367(13) 0.0529(5) Uani 1 1 d . . . . .
N1 N 0.3644(3) 0.36533(10) 0.14979(14) 0.0342(5) Uani 1 1 d . . . . .
C11 C 0.2394(3) 0.66520(12) 0.56270(16) 0.0294(5) Uani 1 1 d . . . . .
H11 H 0.2547 0.7149 0.5312 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3045(3) 0.54875(12) 0.31552(15) 0.0269(5) Uani 1 1 d . . . . .
C12 C 0.2065(3) 0.66238(13) 0.66803(16) 0.0310(5) Uani 1 1 d . . . . .
C10 C 0.2506(3) 0.59507(12) 0.50180(15) 0.0267(5) Uani 1 1 d . . . . .
C6 C 0.3501(3) 0.43681(12) 0.19372(15) 0.0265(5) Uani 1 1 d . . . . .
C13 C 0.1861(3) 0.58752(14) 0.71629(16) 0.0299(5) Uani 1 1 d . . . . .
C9 C 0.2843(3) 0.60393(13) 0.39112(15) 0.0289(5) Uani 1 1 d . . . . .
H9 H 0.2935 0.6569 0.3688 0.035 Uiso 1 1 calc R U . . .
C7 C 0.3466(3) 0.56980(13) 0.20554(17) 0.0316(5) Uani 1 1 d . . . . .
C14 C 0.1979(3) 0.51817(13) 0.65781(17) 0.0352(6) Uani 1 1 d . . . . .
H14 H 0.1849 0.4685 0.6897 0.042 Uiso 1 1 calc R U . . .
C15 C 0.2291(3) 0.52192(13) 0.55208(17) 0.0336(5) Uani 1 1 d . . . . .
H15 H 0.2359 0.4745 0.5137 0.040 Uiso 1 1 calc R U . . .
C1 C 0.4263(4) 0.35610(14) 0.04435(17) 0.0390(6) Uani 1 1 d . . . . .
H1A H 0.5437 0.3279 0.0520 0.047 Uiso 1 1 calc R U . . .
H1B H 0.4440 0.4086 0.0140 0.047 Uiso 1 1 calc R U . . .
C5 C 0.3212(4) 0.28953(14) 0.20122(19) 0.0467(7) Uani 1 1 d . . . . .
H5A H 0.2728 0.3010 0.2676 0.056 Uiso 1 1 calc R U . . .
H5B H 0.4331 0.2580 0.2181 0.056 Uiso 1 1 calc R U . . .
C2 C 0.2842(4) 0.30939(16) -0.02965(19) 0.0508(7) Uani 1 1 d . . . . .
H2A H 0.3299 0.3006 -0.0975 0.061 Uiso 1 1 calc R U . . .
H2B H 0.1712 0.3405 -0.0433 0.061 Uiso 1 1 calc R U . . .
C3 C 0.2432(4) 0.22893(15) 0.0190(2) 0.0519(7) Uani 1 1 d . . . . .
H3A H 0.1474 0.2013 -0.0280 0.062 Uiso 1 1 calc R U . . .
H3B H 0.3533 0.1957 0.0268 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1803(4) 0.24189(15) 0.1277(2) 0.0531(7) Uani 1 1 d . . . . .
H4A H 0.0633 0.2704 0.1186 0.064 Uiso 1 1 calc R U . . .
H4B H 0.1611 0.1902 0.1601 0.064 Uiso 1 1 calc R U . . .
C16 C 0.1466(4) 0.51706(17) 0.8766(2) 0.0513(7) Uani 1 1 d . . . . .
H16A H 0.0432 0.4860 0.8441 0.077 Uiso 1 1 calc R U . . .
H16B H 0.1330 0.5278 0.9499 0.077 Uiso 1 1 calc R U . . .
H16C H 0.2587 0.4875 0.8735 0.077 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
S1 C8 1.752(2) . ?
S1 C6 1.769(2) . ?
O3 C13 1.364(2) . ?
O3 C16 1.423(3) . ?
O2 C12 1.358(2) . ?
O2 H2 0.8200 . ?
N2 C6 1.324(3) . ?
N2 C7 1.361(3) . ?
O1 C7 1.234(3) . ?
N1 C6 1.322(3) . ?
N1 C1 1.468(3) . ?
N1 C5 1.471(3) . ?
C11 C12 1.381(3) . ?
C11 C10 1.405(3) . ?
C11 H11 0.9300 . ?
C8 C9 1.345(3) . ?
C8 C7 1.501(3) . ?
C12 C13 1.403(3) . ?
C10 C15 1.391(3) . ?
C10 C9 1.456(3) . ?
C13 C14 1.378(3) . ?
C9 H9 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C1 C2 1.513(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 C4 1.513(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 C3 1.519(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.517(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C8 S1 C6 88.83(9) . . ?
C13 O3 C16 117.67(19) . . ?
C12 O2 H2 109.5 . . ?
C6 N2 C7 111.38(17) . . ?
C6 N1 C1 121.63(18) . . ?
C6 N1 C5 123.58(18) . . ?
C1 N1 C5 114.79(17) . . ?
C12 C11 C10 121.80(19) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C9 C8 C7 123.37(19) . . ?
C9 C8 S1 128.13(16) . . ?
C7 C8 S1 108.47(14) . . ?
O2 C12 C11 123.96(19) . . ?
O2 C12 C13 116.74(18) . . ?
C11 C12 C13 119.28(19) . . ?
C15 C10 C11 117.37(19) . . ?
C15 C10 C9 124.67(19) . . ?
C11 C10 C9 117.95(18) . . ?
N1 C6 N2 123.30(18) . . ?
N1 C6 S1 119.66(15) . . ?
N2 C6 S1 117.04(15) . . ?
O3 C13 C14 125.5(2) . . ?
O3 C13 C12 114.93(19) . . ?
C14 C13 C12 119.58(18) . . ?
C8 C9 C10 131.1(2) . . ?
C8 C9 H9 114.4 . . ?
C10 C9 H9 114.4 . . ?
O1 C7 N2 122.73(19) . . ?
O1 C7 C8 123.05(19) . . ?
N2 C7 C8 114.22(18) . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
N1 C1 C2 110.0(2) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N1 C5 C4 110.4(2) . . ?
N1 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C1 C2 C3 111.1(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 109.8(2) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 111.3(2) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_17g
_database_code_depnum_ccdc_archive 'CCDC 1453252'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-5-(4-(dimethylamino)benzylidene)-2-(piperidin-1-yl)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H21 N3 O S'
_chemical_formula_sum            'C17 H21 N3 O S'
_chemical_formula_weight         315.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.7194(4)
_cell_length_b                   8.0294(3)
_cell_length_c                   16.4422(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.3040(10)
_cell_angle_gamma                90
_cell_volume                     1619.68(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8398
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      26.34

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25246
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.352
_diffrn_reflns_theta_max         25.692
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3069
_reflns_number_gt                2543
_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-2014/7 (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)+(0.0505P)²+0.9579P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3069
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
S1 S 0.58117(4) 0.35101(7) 0.60466(4) 0.0451(2) Uani 1 1 d . . . . .
O1 O 0.80202(13) 0.6734(2) 0.69655(12) 0.0665(5) Uani 1 1 d . . . . .
N2 N 0.79377(13) 0.4053(2) 0.64658(12) 0.0467(4) Uani 1 1 d . . . . .
N3 N 0.12042(14) 0.6845(2) 0.66432(12) 0.0503(5) Uani 1 1 d . . . . .
N1 N 0.73998(14) 0.1417(2) 0.59390(13) 0.0543(5) Uani 1 1 d . . . . .
C10 C 0.45210(15) 0.6705(2) 0.66567(12) 0.0373(4) Uani 1 1 d . . . . .
C13 C 0.22743(16) 0.6835(2) 0.66307(12) 0.0387(5) Uani 1 1 d . . . . .
C14 C 0.26469(16) 0.5857(3) 0.60557(12) 0.0396(5) Uani 1 1 d . . . . .
H14 H 0.2147 0.5247 0.5650 0.048 Uiso 1 1 calc R U . . .
C8 C 0.62764(15) 0.5427(3) 0.65028(12) 0.0388(5) Uani 1 1 d . . . . .
C15 C 0.37339(16) 0.5780(2) 0.60786(12) 0.0387(5) Uani 1 1 d . . . . .
H15 H 0.3952 0.5092 0.5698 0.046 Uiso 1 1 calc R U . . .
C6 C 0.71924(15) 0.2933(3) 0.61645(13) 0.0417(5) Uani 1 1 d . . . . .
C9 C 0.56835(16) 0.6624(3) 0.67377(13) 0.0404(5) Uani 1 1 d . . . . .
H9 H 0.6079 0.7546 0.6992 0.049 Uiso 1 1 calc R U . . .
C11 C 0.41378(16) 0.7758(3) 0.71910(13) 0.0443(5) Uani 1 1 d . . . . .
H11 H 0.4632 0.8444 0.7560 0.053 Uiso 1 1 calc R U . . .
C7 C 0.74907(16) 0.5499(3) 0.66716(13) 0.0450(5) Uani 1 1 d . . . . .
C17 C 0.04063(17) 0.5892(3) 0.60370(15) 0.0533(6) Uani 1 1 d . . . . .
H17A H 0.0350 0.6313 0.5481 0.080 Uiso 1 1 calc R U . . .
H17B H -0.0288 0.5982 0.6160 0.080 Uiso 1 1 calc R U . . .
H17C H 0.0626 0.4744 0.6066 0.080 Uiso 1 1 calc R U . . .
C12 C 0.30599(17) 0.7817(3) 0.71926(14) 0.0459(5) Uani 1 1 d . . . . .
H12 H 0.2845 0.8515 0.7570 0.055 Uiso 1 1 calc R U . . .
C1 C 0.85198(18) 0.0818(3) 0.60618(17) 0.0629(7) Uani 1 1 d . . . . .
H1A H 0.8683 -0.0009 0.6508 0.076 Uiso 1 1 calc R U . . .
H1B H 0.9025 0.1737 0.6231 0.076 Uiso 1 1 calc R U . . .
C16 C 0.08456(19) 0.7764(4) 0.72759(17) 0.0671(7) Uani 1 1 d . . . . .
H16A H 0.1262 0.7423 0.7826 0.101 Uiso 1 1 calc R U . . .
H16B H 0.0087 0.7545 0.7216 0.101 Uiso 1 1 calc R U . . .
H16C H 0.0949 0.8934 0.7206 0.101 Uiso 1 1 calc R U . . .
C2 C 0.8662(2) 0.0067(3) 0.52650(18) 0.0685(7) Uani 1 1 d . . . . .
H2A H 0.9386 -0.0410 0.5372 0.082 Uiso 1 1 calc R U . . .
H2B H 0.8601 0.0936 0.4845 0.082 Uiso 1 1 calc R U . . .
C5 C 0.6576(2) 0.0135(3) 0.5626(2) 0.0757(9) Uani 1 1 d . . . . .
H5A H 0.5855 0.0615 0.5538 0.091 Uiso 1 1 calc R U . . .
H5B H 0.6654 -0.0744 0.6042 0.091 Uiso 1 1 calc R U . . .
C3 C 0.7829(2) -0.1264(4) 0.4922(2) 0.0761(8) Uani 1 1 d . . . . .
H3A H 0.7947 -0.2205 0.5305 0.091 Uiso 1 1 calc R U . . .
H3B H 0.7907 -0.1648 0.4382 0.091 Uiso 1 1 calc R U . . .
C4 C 0.6694(2) -0.0579(4) 0.4817(2) 0.0859(10) Uani 1 1 d . . . . .
H4A H 0.6549 0.0279 0.4387 0.103 Uiso 1 1 calc R U . . .
H4B H 0.6164 -0.1462 0.4634 0.103 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
S1 C8 1.746(2) . ?
S1 C6 1.7768(19) . ?
O1 C7 1.224(3) . ?
N2 C6 1.306(3) . ?
N2 C7 1.374(3) . ?
N3 C13 1.367(3) . ?
N3 C17 1.441(3) . ?
N3 C16 1.444(3) . ?
N1 C6 1.319(3) . ?
N1 C5 1.462(3) . ?
N1 C1 1.466(3) . ?
C10 C11 1.396(3) . ?
C10 C15 1.398(3) . ?
C10 C9 1.451(3) . ?
C13 C14 1.405(3) . ?
C13 C12 1.409(3) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C8 C9 1.340(3) . ?
C8 C7 1.497(3) . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C12 H12 0.9300 . ?
C1 C2 1.496(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C2 C3 1.506(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C4 1.491(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C3 C4 1.512(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?

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
C8 S1 C6 88.31(10) . . ?
C6 N2 C7 111.69(17) . . ?
C13 N3 C17 120.59(18) . . ?
C13 N3 C16 121.27(18) . . ?
C17 N3 C16 118.11(18) . . ?
C6 N1 C5 124.80(18) . . ?
C6 N1 C1 121.56(19) . . ?
C5 N1 C1 113.39(19) . . ?
C11 C10 C15 116.30(18) . . ?
C11 C10 C9 119.08(18) . . ?
C15 C10 C9 124.62(18) . . ?
N3 C13 C14 121.85(18) . . ?
N3 C13 C12 121.57(18) . . ?
C14 C13 C12 116.58(18) . . ?
C15 C14 C13 121.49(18) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C9 C8 C7 123.41(19) . . ?
C9 C8 S1 127.15(16) . . ?
C7 C8 S1 109.25(15) . . ?
C14 C15 C10 121.95(18) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
N2 C6 N1 124.29(18) . . ?
N2 C6 S1 117.32(16) . . ?
N1 C6 S1 118.39(15) . . ?
C8 C9 C10 130.03(19) . . ?
C8 C9 H9 115.0 . . ?
C10 C9 H9 115.0 . . ?
C12 C11 C10 122.48(19) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
O1 C7 N2 124.15(18) . . ?
O1 C7 C8 122.5(2) . . ?
N2 C7 C8 113.30(18) . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C12 C13 121.01(19) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
N1 C1 C2 110.4(2) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C2 C3 112.3(2) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N1 C5 C4 110.7(2) . . ?
N1 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C2 C3 C4 109.9(2) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 110.9(2) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_17h
_database_code_depnum_ccdc_archive 'CCDC 1453253'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-5-(4-methoxybenzylidene)-2-(piperidin-1-yl)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O2 S'
_chemical_formula_sum            'C16 H18 N2 O2 S'
_chemical_formula_weight         302.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.5748(3)
_cell_length_b                   16.5115(5)
_cell_length_c                   10.8532(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.9220(10)
_cell_angle_gamma                90
_cell_volume                     1508.79(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9092
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      26.39

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.127
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21936
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.467
_diffrn_reflns_theta_max         25.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2873
_reflns_number_gt                2437
_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-2014/7 (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)+(0.0336P)²+0.5418P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2873
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
S1 S 0.19324(5) 0.44442(2) 0.49314(3) 0.03873(15) Uani 1 1 d . . . . .
O2 O 0.72962(15) 0.64072(7) 0.95526(11) 0.0547(3) Uani 1 1 d . . . . .
O1 O 0.13534(17) 0.61033(7) 0.24322(12) 0.0632(4) Uani 1 1 d . . . . .
N2 N 0.04697(16) 0.48090(8) 0.26257(12) 0.0413(3) Uani 1 1 d . . . . .
N1 N -0.00652(17) 0.35227(8) 0.33049(12) 0.0444(3) Uani 1 1 d . . . . .
C6 C 0.06455(18) 0.42356(9) 0.34738(14) 0.0363(3) Uani 1 1 d . . . . .
C9 C 0.31223(18) 0.60175(9) 0.49380(14) 0.0359(3) Uani 1 1 d . . . . .
H9 H 0.3069 0.6488 0.4462 0.043 Uiso 1 1 calc R U . . .
C11 C 0.47785(18) 0.68346(9) 0.65763(14) 0.0367(3) Uani 1 1 d . . . . .
H11 H 0.4506 0.7286 0.6069 0.044 Uiso 1 1 calc R U . . .
C10 C 0.41452(17) 0.60797(9) 0.61655(13) 0.0338(3) Uani 1 1 d . . . . .
C8 C 0.22450(18) 0.54088(9) 0.43676(14) 0.0352(3) Uani 1 1 d . . . . .
C7 C 0.1321(2) 0.54869(9) 0.30498(15) 0.0414(4) Uani 1 1 d . . . . .
C12 C 0.57908(19) 0.69264(9) 0.77080(14) 0.0406(4) Uani 1 1 d . . . . .
H12 H 0.6174 0.7438 0.7966 0.049 Uiso 1 1 calc R U . . .
C13 C 0.62455(18) 0.62600(10) 0.84693(14) 0.0396(4) Uani 1 1 d . . . . .
C14 C 0.5621(2) 0.55070(10) 0.80968(16) 0.0468(4) Uani 1 1 d . . . . .
H14 H 0.5899 0.5057 0.8607 0.056 Uiso 1 1 calc R U . . .
C15 C 0.4582(2) 0.54254(9) 0.69656(16) 0.0449(4) Uani 1 1 d . . . . .
H15 H 0.4161 0.4917 0.6730 0.054 Uiso 1 1 calc R U . . .
C5 C 0.0077(2) 0.28916(10) 0.42663(16) 0.0485(4) Uani 1 1 d . . . . .
H5A H -0.0955 0.2794 0.4481 0.058 Uiso 1 1 calc R U . . .
H5B H 0.0792 0.3073 0.5017 0.058 Uiso 1 1 calc R U . . .
C1 C -0.1067(2) 0.33105(11) 0.20960(16) 0.0497(4) Uani 1 1 d . . . . .
H1A H -0.1043 0.3745 0.1498 0.060 Uiso 1 1 calc R U . . .
H1B H -0.2157 0.3237 0.2200 0.060 Uiso 1 1 calc R U . . .
C2 C -0.0457(2) 0.25365(11) 0.16102(17) 0.0556(5) Uani 1 1 d . . . . .
H2A H 0.0577 0.2636 0.1401 0.067 Uiso 1 1 calc R U . . .
H2B H -0.1173 0.2370 0.0850 0.067 Uiso 1 1 calc R U . . .
C4 C 0.0697(2) 0.21173(10) 0.38046(18) 0.0570(5) Uani 1 1 d . . . . .
H4A H 0.0693 0.1694 0.4423 0.068 Uiso 1 1 calc R U . . .
H4B H 0.1783 0.2196 0.3695 0.068 Uiso 1 1 calc R U . . .
C3 C -0.0321(3) 0.18613(11) 0.2569(2) 0.0678(6) Uani 1 1 d . . . . .
H3A H 0.0145 0.1388 0.2251 0.081 Uiso 1 1 calc R U . . .
H3B H -0.1372 0.1715 0.2702 0.081 Uiso 1 1 calc R U . . .
C16 C 0.7968(3) 0.57263(13) 1.02803(18) 0.0667(6) Uani 1 1 d . . . . .
H16A H 0.7158 0.5460 1.0632 0.100 Uiso 1 1 calc R U . . .
H16B H 0.8798 0.5907 1.0944 0.100 Uiso 1 1 calc R U . . .
H16C H 0.8398 0.5354 0.9752 0.100 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
S1 C8 1.7450(15) . ?
S1 C6 1.7826(15) . ?
O2 C13 1.3608(18) . ?
O2 C16 1.431(2) . ?
O1 C7 1.2218(19) . ?
N2 C6 1.309(2) . ?
N2 C7 1.368(2) . ?
N1 C6 1.3223(19) . ?
N1 C5 1.463(2) . ?
N1 C1 1.468(2) . ?
C9 C8 1.335(2) . ?
C9 C10 1.453(2) . ?
C9 H9 0.9300 . ?
C11 C12 1.372(2) . ?
C11 C10 1.398(2) . ?
C11 H11 0.9300 . ?
C10 C15 1.392(2) . ?
C8 C7 1.504(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(2) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C5 C4 1.507(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 C2 1.513(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.514(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C3 1.515(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C8 S1 C6 88.60(7) . . ?
C13 O2 C16 117.90(14) . . ?
C6 N2 C7 111.86(13) . . ?
C6 N1 C5 124.14(14) . . ?
C6 N1 C1 120.83(14) . . ?
C5 N1 C1 115.02(13) . . ?
N2 C6 N1 123.90(14) . . ?
N2 C6 S1 116.98(11) . . ?
N1 C6 S1 119.12(12) . . ?
C8 C9 C10 131.87(14) . . ?
C8 C9 H9 114.1 . . ?
C10 C9 H9 114.1 . . ?
C12 C11 C10 121.71(14) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C15 C10 C11 116.77(14) . . ?
C15 C10 C9 124.15(13) . . ?
C11 C10 C9 119.06(13) . . ?
C9 C8 C7 121.71(13) . . ?
C9 C8 S1 129.41(12) . . ?
C7 C8 S1 108.88(10) . . ?
O1 C7 N2 124.28(14) . . ?
O1 C7 C8 122.05(14) . . ?
N2 C7 C8 113.67(13) . . ?
C11 C12 C13 120.31(14) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
O2 C13 C14 124.70(15) . . ?
O2 C13 C12 116.00(14) . . ?
C14 C13 C12 119.30(14) . . ?
C15 C14 C13 119.78(14) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 122.08(14) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
N1 C5 C4 110.73(14) . . ?
N1 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C1 C2 109.32(15) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C1 C2 C3 111.69(15) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C5 C4 C3 110.54(16) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C2 C3 C4 111.06(15) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_17i
_database_code_depnum_ccdc_archive 'CCDC 1453254'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-2-(piperidin-1-yl)-5-(4-propoxybenzylidene)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O2 S'
_chemical_formula_sum            'C18 H22 N2 O2 S'
_chemical_formula_weight         330.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.6019(6)
_cell_length_b                   15.8336(5)
_cell_length_c                   7.5085(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.141(2)
_cell_angle_gamma                90
_cell_volume                     1735.96(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6969
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      25.80

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.108
_exptl_absorpt_coefficient_mu    0.197
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30174
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.790
_diffrn_reflns_theta_max         25.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3299
_reflns_number_gt                2427
_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-2014/7 (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)+(0.0473P)²+0.8184P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3299
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.50162(4) 0.29259(3) 0.57974(8) 0.0483(2) Uani 1 1 d . . . . .
O2 O 0.92897(11) 0.22606(10) 0.2529(3) 0.0616(5) Uani 1 1 d . . . . .
O1 O 0.40833(13) 0.06933(10) 0.6381(3) 0.0736(6) Uani 1 1 d . . . . .
N2 N 0.35784(13) 0.20413(11) 0.6824(3) 0.0504(5) Uani 1 1 d . . . . .
N1 N 0.34277(14) 0.35002(12) 0.7058(3) 0.0576(5) Uani 1 1 d . . . . .
C8 C 0.50990(16) 0.18262(13) 0.5680(3) 0.0453(5) Uani 1 1 d . . . . .
C6 C 0.38953(15) 0.28154(13) 0.6633(3) 0.0462(5) Uani 1 1 d . . . . .
C7 C 0.42150(17) 0.14551(14) 0.6322(3) 0.0511(6) Uani 1 1 d . . . . .
C9 C 0.58025(16) 0.13692(13) 0.5083(3) 0.0485(6) Uani 1 1 d . . . . .
H9 H 0.5708 0.0788 0.5086 0.058 Uiso 1 1 calc R U . . .
C10 C 0.66904(16) 0.16356(13) 0.4431(3) 0.0463(6) Uani 1 1 d . . . . .
C13 C 0.84317(15) 0.20939(14) 0.3164(3) 0.0498(6) Uani 1 1 d . . . . .
C11 C 0.73035(17) 0.10348(13) 0.3774(3) 0.0538(6) Uani 1 1 d . . . . .
H11 H 0.7131 0.0469 0.3749 0.065 Uiso 1 1 calc R U . . .
C14 C 0.78385(17) 0.26992(14) 0.3799(4) 0.0583(7) Uani 1 1 d . . . . .
H14 H 0.8012 0.3264 0.3807 0.070 Uiso 1 1 calc R U . . .
C12 C 0.81545(17) 0.12600(14) 0.3163(4) 0.0574(7) Uani 1 1 d . . . . .
H12 H 0.8550 0.0845 0.2744 0.069 Uiso 1 1 calc R U . . .
C16 C 0.95715(17) 0.31276(14) 0.2506(4) 0.0585(7) Uani 1 1 d . . . . .
H16A H 0.9548 0.3359 0.3702 0.070 Uiso 1 1 calc R U . . .
H16B H 0.9161 0.3453 0.1757 0.070 Uiso 1 1 calc R U . . .
C5 C 0.37633(19) 0.43632(15) 0.6814(4) 0.0715(8) Uani 1 1 d . . . . .
H5A H 0.4364 0.4349 0.6265 0.086 Uiso 1 1 calc R U . . .
H5B H 0.3821 0.4638 0.7963 0.086 Uiso 1 1 calc R U . . .
C15 C 0.69919(17) 0.24675(14) 0.4420(4) 0.0608(7) Uani 1 1 d . . . . .
H15 H 0.6604 0.2885 0.4851 0.073 Uiso 1 1 calc R U . . .
C1 C 0.25061(17) 0.34455(18) 0.7799(4) 0.0666(7) Uani 1 1 d . . . . .
H1A H 0.2502 0.3684 0.8989 0.080 Uiso 1 1 calc R U . . .
H1B H 0.2323 0.2858 0.7883 0.080 Uiso 1 1 calc R U . . .
C2 C 0.1839(2) 0.39174(18) 0.6635(5) 0.0808(9) Uani 1 1 d . . . . .
H2A H 0.1238 0.3910 0.7179 0.097 Uiso 1 1 calc R U . . .
H2B H 0.1795 0.3641 0.5485 0.097 Uiso 1 1 calc R U . . .
C17 C 1.05162(19) 0.31829(18) 0.1810(4) 0.0755(8) Uani 1 1 d . . . . .
H17A H 1.0538 0.2936 0.0629 0.091 Uiso 1 1 calc R U . . .
H17B H 1.0924 0.2862 0.2575 0.091 Uiso 1 1 calc R U . . .
C3 C 0.2148(2) 0.48247(19) 0.6382(5) 0.0880(10) Uani 1 1 d . . . . .
H3A H 0.1736 0.5108 0.5562 0.106 Uiso 1 1 calc R U . . .
H3B H 0.2125 0.5119 0.7514 0.106 Uiso 1 1 calc R U . . .
C4 C 0.3115(3) 0.48570(17) 0.5656(4) 0.0883(10) Uani 1 1 d . . . . .
H4A H 0.3122 0.4627 0.4459 0.106 Uiso 1 1 calc R U . . .
H4B H 0.3317 0.5440 0.5594 0.106 Uiso 1 1 calc R U . . .
C18 C 1.0841(2) 0.4090(2) 0.1720(5) 0.0961(11) Uani 1 1 d . . . . .
H18A H 1.0534 0.4374 0.0760 0.144 Uiso 1 1 calc R U . . .
H18B H 1.1490 0.4101 0.1521 0.144 Uiso 1 1 calc R U . . .
H18C H 1.0704 0.4369 0.2822 0.144 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
S1 C8 1.748(2) . ?
S1 C6 1.763(2) . ?
O2 C13 1.367(3) . ?
O2 C16 1.433(3) . ?
O1 C7 1.222(3) . ?
N2 C6 1.318(3) . ?
N2 C7 1.367(3) . ?
N1 C6 1.321(3) . ?
N1 C1 1.460(3) . ?
N1 C5 1.463(3) . ?
C8 C9 1.335(3) . ?
C8 C7 1.499(3) . ?
C9 C10 1.450(3) . ?
C9 H9 0.9300 . ?
C10 C15 1.389(3) . ?
C10 C11 1.397(3) . ?
C13 C14 1.378(3) . ?
C13 C12 1.381(3) . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C16 C17 1.479(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C5 C4 1.502(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C15 H15 0.9300 . ?
C1 C2 1.505(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.518(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C17 C18 1.514(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C3 C4 1.516(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C8 S1 C6 89.05(11) . . ?
C13 O2 C16 116.90(18) . . ?
C6 N2 C7 111.23(19) . . ?
C6 N1 C1 121.4(2) . . ?
C6 N1 C5 124.3(2) . . ?
C1 N1 C5 114.4(2) . . ?
C9 C8 C7 124.0(2) . . ?
C9 C8 S1 127.61(18) . . ?
C7 C8 S1 108.34(16) . . ?
N2 C6 N1 123.7(2) . . ?
N2 C6 S1 117.23(17) . . ?
N1 C6 S1 119.03(17) . . ?
O1 C7 N2 123.6(2) . . ?
O1 C7 C8 122.3(2) . . ?
N2 C7 C8 114.15(19) . . ?
C8 C9 C10 130.2(2) . . ?
C8 C9 H9 114.9 . . ?
C10 C9 H9 114.9 . . ?
C15 C10 C11 116.1(2) . . ?
C15 C10 C9 124.2(2) . . ?
C11 C10 C9 119.71(19) . . ?
O2 C13 C14 124.3(2) . . ?
O2 C13 C12 117.0(2) . . ?
C14 C13 C12 118.7(2) . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
O2 C16 C17 109.2(2) . . ?
O2 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
O2 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
N1 C5 C4 110.4(2) . . ?
N1 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C14 C15 C10 122.8(2) . . ?
C14 C15 H15 118.6 . . ?
C10 C15 H15 118.6 . . ?
N1 C1 C2 110.2(2) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C1 C2 C3 110.5(3) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C16 C17 C18 111.3(2) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C4 C3 C2 110.8(2) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.1(3) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_17j
_database_code_depnum_ccdc_archive 'CCDC 1453255'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-5-(4-methoxy-2,3-dimethylbenzylidene)-2-(piperidin-1-yl)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O2 S'
_chemical_formula_sum            'C18 H22 N2 O2 S'
_chemical_formula_weight         330.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.1879(8)
_cell_length_b                   8.2959(4)
_cell_length_c                   16.8693(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.933(2)
_cell_angle_gamma                90
_cell_volume                     1712.01(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    8034
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.91

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.597
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.267
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26183
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.512
_diffrn_reflns_theta_max         25.700
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3241
_reflns_number_gt                2562
_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-2014/7 (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)+(0.0491P)²+0.7144P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3241
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.27826(4) 0.40930(6) 0.64503(4) 0.04351(18) Uani 1 1 d . . . . .
O1 O 0.18330(12) 0.04118(17) 0.73500(11) 0.0577(4) Uani 1 1 d . . . . .
N2 N 0.12568(12) 0.30052(19) 0.69842(11) 0.0418(4) Uani 1 1 d . . . . .
O2 O 0.74103(12) 0.1220(2) 0.60492(11) 0.0637(5) Uani 1 1 d . . . . .
N1 N 0.10631(13) 0.56816(19) 0.65571(12) 0.0460(4) Uani 1 1 d . . . . .
C10 C 0.45511(14) 0.1053(2) 0.65384(12) 0.0369(4) Uani 1 1 d . . . . .
C8 C 0.28667(14) 0.2077(2) 0.67719(12) 0.0363(4) Uani 1 1 d . . . . .
C7 C 0.19423(15) 0.1726(2) 0.70661(12) 0.0395(4) Uani 1 1 d . . . . .
C11 C 0.49575(14) -0.0333(2) 0.62660(11) 0.0375(4) Uani 1 1 d . . . . .
C9 C 0.35828(14) 0.0946(2) 0.67613(12) 0.0387(4) Uani 1 1 d . . . . .
H9 H 0.3442 -0.0077 0.6922 0.046 Uiso 1 1 calc R U . . .
C6 C 0.15788(14) 0.4284(2) 0.66857(12) 0.0371(4) Uani 1 1 d . . . . .
C15 C 0.51153(14) 0.2495(2) 0.66231(13) 0.0434(5) Uani 1 1 d . . . . .
H15 H 0.4844 0.3414 0.6791 0.052 Uiso 1 1 calc R U . . .
C12 C 0.59194(14) -0.0234(2) 0.61018(12) 0.0406(5) Uani 1 1 d . . . . .
C14 C 0.60677(15) 0.2604(3) 0.64651(14) 0.0487(5) Uani 1 1 d . . . . .
H14 H 0.6436 0.3580 0.6529 0.058 Uiso 1 1 calc R U . . .
C16 C 0.43427(17) -0.1904(3) 0.61201(15) 0.0522(5) Uani 1 1 d . . . . .
H16A H 0.4484 -0.2511 0.5688 0.078 Uiso 1 1 calc R U . . .
H16B H 0.3574 -0.1691 0.5937 0.078 Uiso 1 1 calc R U . . .
H16C H 0.4579 -0.2510 0.6642 0.078 Uiso 1 1 calc R U . . .
C1 C 0.01118(17) 0.5923(3) 0.68016(15) 0.0520(5) Uani 1 1 d . . . . .
H1A H 0.0296 0.6686 0.7270 0.062 Uiso 1 1 calc R U . . .
H1B H -0.0086 0.4910 0.6992 0.062 Uiso 1 1 calc R U . . .
C13 C 0.64650(15) 0.1235(3) 0.62100(13) 0.0460(5) Uani 1 1 d . . . . .
C17 C 0.63802(18) -0.1683(3) 0.58102(15) 0.0575(6) Uani 1 1 d . . . . .
H17A H 0.5858 -0.2065 0.5277 0.086 Uiso 1 1 calc R U . . .
H17B H 0.6532 -0.2520 0.6232 0.086 Uiso 1 1 calc R U . . .
H17C H 0.7043 -0.1384 0.5737 0.086 Uiso 1 1 calc R U . . .
C5 C 0.13960(18) 0.7104(2) 0.62038(17) 0.0588(6) Uani 1 1 d . . . . .
H5A H 0.1986 0.6819 0.6018 0.071 Uiso 1 1 calc R U . . .
H5B H 0.1664 0.7924 0.6643 0.071 Uiso 1 1 calc R U . . .
C2 C -0.08378(17) 0.6551(3) 0.60508(16) 0.0599(6) Uani 1 1 d . . . . .
H2A H -0.1445 0.6773 0.6227 0.072 Uiso 1 1 calc R U . . .
H2B H -0.1071 0.5733 0.5608 0.072 Uiso 1 1 calc R U . . .
C18 C 0.79511(19) 0.2704(4) 0.60724(18) 0.0756(8) Uani 1 1 d . . . . .
H18A H 0.7486 0.3403 0.5633 0.113 Uiso 1 1 calc R U . . .
H18B H 0.8616 0.2513 0.5979 0.113 Uiso 1 1 calc R U . . .
H18C H 0.8118 0.3203 0.6620 0.113 Uiso 1 1 calc R U . . .
C4 C 0.04459(19) 0.7764(3) 0.54566(17) 0.0653(7) Uani 1 1 d . . . . .
H4A H 0.0248 0.7002 0.4987 0.078 Uiso 1 1 calc R U . . .
H4B H 0.0664 0.8762 0.5266 0.078 Uiso 1 1 calc R U . . .
C3 C -0.0537(2) 0.8075(3) 0.56933(19) 0.0708(7) Uani 1 1 d . . . . .
H3A H -0.1150 0.8421 0.5192 0.085 Uiso 1 1 calc R U . . .
H3B H -0.0370 0.8928 0.6116 0.085 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
S1 C8 1.7488(19) . ?
S1 C6 1.7816(17) . ?
O1 C7 1.220(2) . ?
N2 C6 1.311(2) . ?
N2 C7 1.367(2) . ?
O2 C13 1.371(2) . ?
O2 C18 1.416(3) . ?
N1 C6 1.321(2) . ?
N1 C5 1.461(3) . ?
N1 C1 1.473(2) . ?
C10 C15 1.387(3) . ?
C10 C11 1.416(3) . ?
C10 C9 1.462(2) . ?
C8 C9 1.336(2) . ?
C8 C7 1.506(2) . ?
C11 C12 1.398(2) . ?
C11 C16 1.506(3) . ?
C9 H9 0.9300 . ?
C15 C14 1.381(3) . ?
C15 H15 0.9300 . ?
C12 C13 1.392(3) . ?
C12 C17 1.510(3) . ?
C14 C13 1.385(3) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C1 C2 1.503(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 C4 1.510(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 C3 1.517(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C4 C3 1.514(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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
C8 S1 C6 88.53(8) . . ?
C6 N2 C7 111.72(15) . . ?
C13 O2 C18 118.18(18) . . ?
C6 N1 C5 124.14(16) . . ?
C6 N1 C1 120.91(16) . . ?
C5 N1 C1 114.91(16) . . ?
C15 C10 C11 118.68(16) . . ?
C15 C10 C9 120.81(16) . . ?
C11 C10 C9 120.45(17) . . ?
C9 C8 C7 122.09(17) . . ?
C9 C8 S1 129.11(15) . . ?
C7 C8 S1 108.79(12) . . ?
O1 C7 N2 124.22(17) . . ?
O1 C7 C8 122.07(17) . . ?
N2 C7 C8 113.71(16) . . ?
C12 C11 C10 119.86(17) . . ?
C12 C11 C16 119.45(17) . . ?
C10 C11 C16 120.66(16) . . ?
C8 C9 C10 130.54(18) . . ?
C8 C9 H9 114.7 . . ?
C10 C9 H9 114.7 . . ?
N2 C6 N1 123.56(16) . . ?
N2 C6 S1 117.21(13) . . ?
N1 C6 S1 119.24(14) . . ?
C14 C15 C10 121.88(18) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
C13 C12 C11 119.24(17) . . ?
C13 C12 C17 119.24(17) . . ?
C11 C12 C17 121.52(19) . . ?
C15 C14 C13 118.90(19) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C1 C2 109.87(17) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
O2 C13 C14 123.13(19) . . ?
O2 C13 C12 115.45(18) . . ?
C14 C13 C12 121.42(17) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C5 C4 110.57(17) . . ?
N1 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C1 C2 C3 111.4(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5 C4 C3 111.5(2) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C3 C2 109.87(18) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_17k
_database_code_depnum_ccdc_archive 'CCDC 1453256'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-5-(2-methylbenzylidene)-2-(piperidin-1-yl)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O S'
_chemical_formula_sum            'C16 H18 N2 O S'
_chemical_formula_weight         286.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   19.808(2)
_cell_length_b                   19.648(2)
_cell_length_c                   7.5797(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.378(4)
_cell_angle_gamma                90
_cell_volume                     2937.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4981
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      21.92

_exptl_crystal_description       rod
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.351
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    0.218
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58480
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_av_R_equivalents  0.2422
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         25.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5577
_reflns_number_gt                2997
_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-2014/7 (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)+(0.0416P)²+1.5659P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5577
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
S1A S 0.39934(4) 0.22418(4) 0.65740(12) 0.0426(3) Uani 1 1 d . . . . .
S1 S 0.10486(5) 0.44466(4) 0.28725(14) 0.0568(3) Uani 1 1 d . . . . .
O1A O 0.46999(11) 0.40430(11) 0.6248(3) 0.0544(7) Uani 1 1 d . . . . .
O1 O 0.03182(12) 0.61303(12) 0.1031(4) 0.0645(8) Uani 1 1 d . . . . .
N2A N 0.50637(13) 0.29531(13) 0.5817(4) 0.0401(7) Uani 1 1 d . . . . .
N2 N -0.00868(13) 0.51466(13) 0.2180(4) 0.0485(8) Uani 1 1 d . . . . .
N1A N 0.51695(14) 0.17804(13) 0.5561(4) 0.0479(8) Uani 1 1 d . . . . .
N1 N -0.02145(14) 0.40775(14) 0.3411(4) 0.0540(8) Uani 1 1 d . . . . .
C8A C 0.39378(16) 0.31255(14) 0.6700(4) 0.0357(8) Uani 1 1 d . . . . .
C7A C 0.45956(16) 0.34307(16) 0.6236(4) 0.0390(8) Uani 1 1 d . . . . .
C6A C 0.48234(16) 0.23328(16) 0.5922(4) 0.0384(8) Uani 1 1 d . . . . .
C6 C 0.01606(17) 0.45708(16) 0.2816(5) 0.0455(9) Uani 1 1 d . . . . .
C9A C 0.34195(16) 0.35165(16) 0.7097(4) 0.0428(9) Uani 1 1 d . . . . .
H9A H 0.3505 0.3981 0.7060 0.051 Uiso 1 1 calc R U . . .
C10A C 0.27477(16) 0.33431(17) 0.7575(4) 0.0437(9) Uani 1 1 d . . . . .
C9 C 0.16729(17) 0.56237(17) 0.1849(4) 0.0475(9) Uani 1 1 d . . . . .
H9 H 0.1606 0.6061 0.1394 0.057 Uiso 1 1 calc R U . . .
C10 C 0.23790(17) 0.54211(17) 0.2299(4) 0.0444(9) Uani 1 1 d . . . . .
C7 C 0.04146(17) 0.55626(17) 0.1652(5) 0.0468(9) Uani 1 1 d . . . . .
C8 C 0.11149(17) 0.52617(16) 0.2009(5) 0.0440(9) Uani 1 1 d . . . . .
C11 C 0.28605(18) 0.59058(19) 0.2934(5) 0.0506(9) Uani 1 1 d . . . . .
C11A C 0.22545(17) 0.38479(19) 0.7624(5) 0.0511(9) Uani 1 1 d . . . . .
C5A C 0.4927(2) 0.10847(16) 0.5774(5) 0.0589(11) Uani 1 1 d . . . . .
H5A1 H 0.4914 0.0847 0.4650 0.071 Uiso 1 1 calc R U . . .
H5A2 H 0.4471 0.1096 0.6138 0.071 Uiso 1 1 calc R U . . .
C5 C 0.00663(19) 0.34697(17) 0.4338(6) 0.0624(11) Uani 1 1 d . . . . .
H5A H 0.0022 0.3515 0.5596 0.075 Uiso 1 1 calc R U . . .
H5B H 0.0545 0.3433 0.4178 0.075 Uiso 1 1 calc R U . . .
C1A C 0.58646(17) 0.18293(18) 0.5074(5) 0.0570(10) Uani 1 1 d . . . . .
H1A1 H 0.5994 0.2304 0.5005 0.068 Uiso 1 1 calc R U . . .
H1A2 H 0.5893 0.1625 0.3919 0.068 Uiso 1 1 calc R U . . .
C12 C 0.35131(19) 0.5696(2) 0.3448(5) 0.0620(11) Uani 1 1 d . . . . .
H12 H 0.3834 0.6019 0.3858 0.074 Uiso 1 1 calc R U . . .
C15 C 0.2582(2) 0.47465(19) 0.2165(5) 0.0636(11) Uani 1 1 d . . . . .
H15 H 0.2272 0.4423 0.1698 0.076 Uiso 1 1 calc R U . . .
C12A C 0.16148(19) 0.3676(2) 0.8097(5) 0.0691(12) Uani 1 1 d . . . . .
H12A H 0.1286 0.4013 0.8132 0.083 Uiso 1 1 calc R U . . .
C1 C -0.09496(18) 0.4155(2) 0.3351(6) 0.0704(12) Uani 1 1 d . . . . .
H1A H -0.1093 0.4529 0.2570 0.085 Uiso 1 1 calc R U . . .
H1B H -0.1073 0.4264 0.4527 0.085 Uiso 1 1 calc R U . . .
C13 C 0.3704(2) 0.5031(3) 0.3374(6) 0.0765(13) Uani 1 1 d . . . . .
H13 H 0.4144 0.4902 0.3763 0.092 Uiso 1 1 calc R U . . .
C15A C 0.25751(18) 0.2678(2) 0.8027(5) 0.0636(11) Uani 1 1 d . . . . .
H15A H 0.2899 0.2335 0.8013 0.076 Uiso 1 1 calc R U . . .
C4A C 0.5385(2) 0.07127(19) 0.7136(5) 0.0712(12) Uani 1 1 d . . . . .
H4A1 H 0.5241 0.0242 0.7189 0.085 Uiso 1 1 calc R U . . .
H4A2 H 0.5352 0.0916 0.8291 0.085 Uiso 1 1 calc R U . . .
C14A C 0.1938(2) 0.2518(2) 0.8492(6) 0.0787(13) Uani 1 1 d . . . . .
H14A H 0.1833 0.2073 0.8789 0.094 Uiso 1 1 calc R U . . .
C2A C 0.6340(2) 0.1469(2) 0.6435(6) 0.0764(13) Uani 1 1 d . . . . .
H2A1 H 0.6353 0.1709 0.7555 0.092 Uiso 1 1 calc R U . . .
H2A2 H 0.6795 0.1471 0.6056 0.092 Uiso 1 1 calc R U . . .
C4 C -0.0288(2) 0.28425(18) 0.3664(6) 0.0715(13) Uani 1 1 d . . . . .
H4A H -0.0121 0.2457 0.4377 0.086 Uiso 1 1 calc R U . . .
H4B H -0.0188 0.2761 0.2453 0.086 Uiso 1 1 calc R U . . .
C13A C 0.1460(2) 0.3021(3) 0.8511(6) 0.0800(14) Uani 1 1 d . . . . .
H13A H 0.1028 0.2916 0.8808 0.096 Uiso 1 1 calc R U . . .
C16 C 0.2682(2) 0.66483(19) 0.3088(6) 0.0813(14) Uani 1 1 d . . . . .
H16A H 0.3078 0.6898 0.3540 0.122 Uiso 1 1 calc R U . . .
H16B H 0.2335 0.6698 0.3880 0.122 Uiso 1 1 calc R U . . .
H16C H 0.2521 0.6821 0.1941 0.122 Uiso 1 1 calc R U . . .
C14 C 0.3241(2) 0.4553(2) 0.2721(6) 0.0795(14) Uani 1 1 d . . . . .
H14 H 0.3369 0.4099 0.2651 0.095 Uiso 1 1 calc R U . . .
C2 C -0.1306(2) 0.3522(2) 0.2709(6) 0.0785(13) Uani 1 1 d . . . . .
H2A H -0.1248 0.3459 0.1463 0.094 Uiso 1 1 calc R U . . .
H2B H -0.1787 0.3570 0.2825 0.094 Uiso 1 1 calc R U . . .
C3A C 0.6116(2) 0.0740(2) 0.6689(6) 0.0834(14) Uani 1 1 d . . . . .
H3A1 H 0.6407 0.0531 0.7638 0.100 Uiso 1 1 calc R U . . .
H3A2 H 0.6160 0.0484 0.5612 0.100 Uiso 1 1 calc R U . . .
C3 C -0.1043(2) 0.2903(2) 0.3722(6) 0.0815(14) Uani 1 1 d . . . . .
H3A H -0.1264 0.2499 0.3211 0.098 Uiso 1 1 calc R U . . .
H3B H -0.1148 0.2939 0.4944 0.098 Uiso 1 1 calc R U . . .
C16A C 0.2392(2) 0.45797(19) 0.7210(6) 0.0827(14) Uani 1 1 d . . . . .
H16D H 0.1982 0.4839 0.7234 0.124 Uiso 1 1 calc R U . . .
H16E H 0.2551 0.4611 0.6055 0.124 Uiso 1 1 calc R U . . .
H16F H 0.2731 0.4757 0.8078 0.124 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
S1A C8A 1.743(3) . ?
S1A C6A 1.770(3) . ?
S1 C8 1.740(3) . ?
S1 C6 1.772(3) . ?
O1A C7A 1.221(3) . ?
O1 C7 1.219(4) . ?
N2A C6A 1.314(4) . ?
N2A C7A 1.377(4) . ?
N2 C6 1.307(4) . ?
N2 C7 1.374(4) . ?
N1A C6A 1.326(4) . ?
N1A C1A 1.462(4) . ?
N1A C5A 1.463(4) . ?
N1 C6 1.326(4) . ?
N1 C1 1.461(4) . ?
N1 C5 1.468(4) . ?
C8A C9A 1.339(4) . ?
C8A C7A 1.506(4) . ?
C9A C10A 1.452(4) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.395(4) . ?
C10A C15A 1.402(5) . ?
C9 C8 1.329(4) . ?
C9 C10 1.464(4) . ?
C9 H9 0.9300 . ?
C10 C15 1.391(5) . ?
C10 C11 1.401(5) . ?
C7 C8 1.509(4) . ?
C11 C12 1.378(5) . ?
C11 C16 1.508(5) . ?
C11A C12A 1.391(5) . ?
C11A C16A 1.502(5) . ?
C5A C4A 1.499(5) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C5 C4 1.485(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1A C2A 1.508(5) . ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
C12 C13 1.364(5) . ?
C12 H12 0.9300 . ?
C15 C14 1.387(5) . ?
C15 H15 0.9300 . ?
C12A C13A 1.366(5) . ?
C12A H12A 0.9300 . ?
C1 C2 1.490(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C13 C14 1.372(6) . ?
C13 H13 0.9300 . ?
C15A C14A 1.378(5) . ?
C15A H15A 0.9300 . ?
C4A C3A 1.518(5) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C14A C13A 1.369(6) . ?
C14A H14A 0.9300 . ?
C2A C3A 1.516(6) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C4 C3 1.507(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C13A H13A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14 0.9300 . ?
C2 C3 1.503(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?

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
C8A S1A C6A 88.84(15) . . ?
C8 S1 C6 88.51(16) . . ?
C6A N2A C7A 111.3(3) . . ?
C6 N2 C7 111.5(3) . . ?
C6A N1A C1A 121.0(3) . . ?
C6A N1A C5A 124.1(3) . . ?
C1A N1A C5A 114.6(3) . . ?
C6 N1 C1 120.1(3) . . ?
C6 N1 C5 123.9(3) . . ?
C1 N1 C5 115.6(3) . . ?
C9A C8A C7A 121.5(3) . . ?
C9A C8A S1A 129.6(2) . . ?
C7A C8A S1A 108.9(2) . . ?
O1A C7A N2A 123.8(3) . . ?
O1A C7A C8A 122.7(3) . . ?
N2A C7A C8A 113.5(3) . . ?
N2A C6A N1A 123.3(3) . . ?
N2A C6A S1A 117.5(2) . . ?
N1A C6A S1A 119.1(2) . . ?
N2 C6 N1 123.8(3) . . ?
N2 C6 S1 117.7(3) . . ?
N1 C6 S1 118.5(2) . . ?
C8A C9A C10A 131.4(3) . . ?
C8A C9A H9A 114.3 . . ?
C10A C9A H9A 114.3 . . ?
C11A C10A C15A 118.0(3) . . ?
C11A C10A C9A 120.0(3) . . ?
C15A C10A C9A 122.0(3) . . ?
C8 C9 C10 128.2(3) . . ?
C8 C9 H9 115.9 . . ?
C10 C9 H9 115.9 . . ?
C15 C10 C11 118.7(3) . . ?
C15 C10 C9 121.2(3) . . ?
C11 C10 C9 120.0(3) . . ?
O1 C7 N2 124.4(3) . . ?
O1 C7 C8 122.4(3) . . ?
N2 C7 C8 113.1(3) . . ?
C9 C8 C7 122.2(3) . . ?
C9 C8 S1 128.3(3) . . ?
C7 C8 S1 109.1(2) . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 C16 119.2(4) . . ?
C10 C11 C16 121.8(3) . . ?
C12A C11A C10A 119.4(3) . . ?
C12A C11A C16A 118.3(3) . . ?
C10A C11A C16A 122.3(3) . . ?
N1A C5A C4A 110.4(3) . . ?
N1A C5A H5A1 109.6 . . ?
C4A C5A H5A1 109.6 . . ?
N1A C5A H5A2 109.6 . . ?
C4A C5A H5A2 109.6 . . ?
H5A1 C5A H5A2 108.1 . . ?
N1 C5 C4 111.4(3) . . ?
N1 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N1A C1A C2A 109.8(3) . . ?
N1A C1A H1A1 109.7 . . ?
C2A C1A H1A1 109.7 . . ?
N1A C1A H1A2 109.7 . . ?
C2A C1A H1A2 109.7 . . ?
H1A1 C1A H1A2 108.2 . . ?
C13 C12 C11 122.1(4) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C15 C10 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C13A C12A C11A 121.2(4) . . ?
C13A C12A H12A 119.4 . . ?
C11A C12A H12A 119.4 . . ?
N1 C1 C2 111.3(3) . . ?
N1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C14A C15A C10A 121.7(4) . . ?
C14A C15A H15A 119.2 . . ?
C10A C15A H15A 119.2 . . ?
C5A C4A C3A 110.9(3) . . ?
C5A C4A H4A1 109.5 . . ?
C3A C4A H4A1 109.5 . . ?
C5A C4A H4A2 109.5 . . ?
C3A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 108.0 . . ?
C13A C14A C15A 119.2(4) . . ?
C13A C14A H14A 120.4 . . ?
C15A C14A H14A 120.4 . . ?
C1A C2A C3A 111.0(4) . . ?
C1A C2A H2A1 109.4 . . ?
C3A C2A H2A1 109.4 . . ?
C1A C2A H2A2 109.4 . . ?
C3A C2A H2A2 109.4 . . ?
H2A1 C2A H2A2 108.0 . . ?
C5 C4 C3 111.2(3) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C12A C13A C14A 120.5(4) . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A H13A 119.7 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C1 C2 C3 112.2(4) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2A C3A C4A 111.1(3) . . ?
C2A C3A H3A1 109.4 . . ?
C4A C3A H3A1 109.4 . . ?
C2A C3A H3A2 109.4 . . ?
C4A C3A H3A2 109.4 . . ?
H3A1 C3A H3A2 108.0 . . ?
C2 C3 C4 110.3(3) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C11A C16A H16D 109.5 . . ?
C11A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C11A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_17m
_database_code_depnum_ccdc_archive 'CCDC 1453257'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-5-(2,3-dimethoxybenzylidene)-2-(piperidin-1-yl)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 N2 O3 S'
_chemical_formula_sum            'C17 H20 N2 O3 S'
_chemical_formula_weight         332.41

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'

_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                   6.9066(6)
_cell_length_b                   10.3537(10)
_cell_length_c                   12.5514(13)
_cell_angle_alpha                96.955(4)
_cell_angle_beta                 103.338(3)
_cell_angle_gamma                100.576(3)
_cell_volume                     845.87(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      26.38

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.183
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29059
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.411
_diffrn_reflns_theta_max         25.700
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3209
_reflns_number_gt                2735
_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-2014/7 (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)+(0.0555P)²+0.2631P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.055(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3209
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
S1 S 0.65086(6) 0.83215(5) 0.77842(4) 0.05262(19) Uani 1 1 d . . . . .
O2 O 0.78210(17) 0.35822(13) 0.60832(10) 0.0520(3) Uani 1 1 d . . . . .
O1 O 1.1721(2) 0.80706(16) 0.73478(14) 0.0781(5) Uani 1 1 d . . . . .
O3 O 0.4506(2) 0.16206(14) 0.56308(13) 0.0729(4) Uani 1 1 d . . . . .
N2 N 1.0166(2) 0.97263(16) 0.78580(13) 0.0547(4) Uani 1 1 d . . . . .
N1 N 0.7898(2) 1.09519(16) 0.83310(14) 0.0567(4) Uani 1 1 d . . . . .
C11 C 0.6148(2) 0.38220(18) 0.64190(14) 0.0456(4) Uani 1 1 d . . . . .
C10 C 0.6241(2) 0.50696(18) 0.70141(14) 0.0469(4) Uani 1 1 d . . . . .
C9 C 0.8032(2) 0.61388(19) 0.71470(14) 0.0492(4) Uani 1 1 d . . . . .
H9 H 0.9165 0.5865 0.6998 0.059 Uiso 1 1 calc R U . . .
C12 C 0.4411(3) 0.27936(19) 0.62121(16) 0.0537(4) Uani 1 1 d . . . . .
C7 C 1.0237(2) 0.8427(2) 0.75391(15) 0.0538(5) Uani 1 1 d . . . . .
C8 C 0.8273(2) 0.74480(18) 0.74511(14) 0.0470(4) Uani 1 1 d . . . . .
C6 C 0.8376(2) 0.98184(18) 0.80142(14) 0.0479(4) Uani 1 1 d . . . . .
C5 C 0.5897(3) 1.1051(2) 0.85065(18) 0.0611(5) Uani 1 1 d . . . . .
H5A H 0.5038 1.0165 0.8382 0.073 Uiso 1 1 calc R U . . .
H5B H 0.5243 1.1550 0.7979 0.073 Uiso 1 1 calc R U . . .
C14 C 0.4585(3) 0.5240(2) 0.74488(19) 0.0617(5) Uani 1 1 d . . . . .
H14 H 0.4635 0.6050 0.7877 0.074 Uiso 1 1 calc R U . . .
C00G C 0.2782(3) 0.3010(2) 0.66232(19) 0.0645(5) Uani 1 1 d . . . . .
H00G H 0.1613 0.2338 0.6479 0.077 Uiso 1 1 calc R U . . .
C13 C 0.2899(3) 0.4226(2) 0.7248(2) 0.0677(6) Uani 1 1 d . . . . .
H13 H 0.1813 0.4359 0.7538 0.081 Uiso 1 1 calc R U . . .
C1 C 0.9376(3) 1.2229(2) 0.85430(18) 0.0637(5) Uani 1 1 d . . . . .
H1A H 0.8897 1.2783 0.8012 0.076 Uiso 1 1 calc R U . . .
H1B H 1.0677 1.2074 0.8453 0.076 Uiso 1 1 calc R U . . .
C15 C 0.7659(4) 0.3542(3) 0.49262(17) 0.0801(7) Uani 1 1 d . . . . .
H15A H 0.6492 0.2869 0.4506 0.120 Uiso 1 1 calc R U . . .
H15B H 0.8868 0.3335 0.4760 0.120 Uiso 1 1 calc R U . . .
H15C H 0.7508 0.4394 0.4734 0.120 Uiso 1 1 calc R U . . .
C4 C 0.6132(4) 1.1729(2) 0.9660(2) 0.0773(6) Uani 1 1 d . . . . .
H4A H 0.6637 1.1176 1.0184 0.093 Uiso 1 1 calc R U . . .
H4B H 0.4813 1.1847 0.9749 0.093 Uiso 1 1 calc R U . . .
C2 C 0.9637(4) 1.2928(2) 0.9697(2) 0.0812(7) Uani 1 1 d . . . . .
H2A H 1.0532 1.3800 0.9811 0.097 Uiso 1 1 calc R U . . .
H2B H 1.0279 1.2423 1.0224 0.097 Uiso 1 1 calc R U . . .
C3 C 0.7613(4) 1.3090(3) 0.9913(3) 0.0950(8) Uani 1 1 d . . . . .
H3A H 0.7038 1.3680 0.9448 0.114 Uiso 1 1 calc R U . . .
H3B H 0.7826 1.3486 1.0684 0.114 Uiso 1 1 calc R U . . .
C16 C 0.2714(4) 0.0575(3) 0.5313(2) 0.0938(8) Uani 1 1 d . . . . .
H16A H 0.2398 0.0292 0.5966 0.141 Uiso 1 1 calc R U . . .
H16B H 0.2945 -0.0165 0.4855 0.141 Uiso 1 1 calc R U . . .
H16C H 0.1594 0.0893 0.4904 0.141 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
S1 C8 1.7395(17) . ?
S1 C6 1.7707(17) . ?
O2 C11 1.3705(19) . ?
O2 C15 1.425(2) . ?
O1 C7 1.215(2) . ?
O3 C12 1.360(2) . ?
O3 C16 1.428(3) . ?
N2 C6 1.314(2) . ?
N2 C7 1.369(2) . ?
N1 C6 1.317(2) . ?
N1 C5 1.468(2) . ?
N1 C1 1.469(2) . ?
C11 C10 1.394(3) . ?
C11 C12 1.400(2) . ?
C10 C14 1.406(2) . ?
C10 C9 1.463(2) . ?
C9 C8 1.332(3) . ?
C9 H9 0.9300 . ?
C12 C00G 1.383(3) . ?
C7 C8 1.509(2) . ?
C5 C4 1.490(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C14 C13 1.369(3) . ?
C14 H14 0.9300 . ?
C00G C13 1.379(3) . ?
C00G H00G 0.9300 . ?
C13 H13 0.9300 . ?
C1 C2 1.494(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C4 C3 1.531(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 C3 1.519(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C8 S1 C6 88.69(8) . . ?
C11 O2 C15 115.05(15) . . ?
C12 O3 C16 117.79(18) . . ?
C6 N2 C7 111.28(15) . . ?
C6 N1 C5 123.80(15) . . ?
C6 N1 C1 121.33(16) . . ?
C5 N1 C1 114.87(16) . . ?
O2 C11 C10 119.36(15) . . ?
O2 C11 C12 119.70(16) . . ?
C10 C11 C12 120.86(16) . . ?
C11 C10 C14 117.97(16) . . ?
C11 C10 C9 118.90(15) . . ?
C14 C10 C9 123.13(17) . . ?
C8 C9 C10 129.35(15) . . ?
C8 C9 H9 115.3 . . ?
C10 C9 H9 115.3 . . ?
O3 C12 C00G 124.96(17) . . ?
O3 C12 C11 115.46(16) . . ?
C00G C12 C11 119.55(18) . . ?
O1 C7 N2 124.38(17) . . ?
O1 C7 C8 122.09(18) . . ?
N2 C7 C8 113.52(14) . . ?
C9 C8 C7 122.68(15) . . ?
C9 C8 S1 128.39(13) . . ?
C7 C8 S1 108.92(13) . . ?
N2 C6 N1 123.95(16) . . ?
N2 C6 S1 117.59(14) . . ?
N1 C6 S1 118.46(13) . . ?
N1 C5 C4 110.29(17) . . ?
N1 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C13 C14 C10 120.65(19) . . ?
C13 C14 H14 119.7 . . ?
C10 C14 H14 119.7 . . ?
C13 C00G C12 119.76(18) . . ?
C13 C00G H00G 120.1 . . ?
C12 C00G H00G 120.1 . . ?
C14 C13 C00G 121.12(18) . . ?
C14 C13 H13 119.4 . . ?
C00G C13 H13 119.4 . . ?
N1 C1 C2 109.69(17) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C4 C3 110.89(19) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C1 C2 C3 111.9(2) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 109.9(2) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_17n
_database_code_depnum_ccdc_archive 'CCDC 1453258'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-5-(benzo[d][1,3]dioxol-4-ylmethylene)-2-(piperidin-1-yl)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N2 O3 S'
_chemical_formula_sum            'C16 H16 N2 O3 S'
_chemical_formula_weight         316.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.3333(6)
_cell_length_b                   16.8148(12)
_cell_length_c                   10.7927(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.960(2)
_cell_angle_gamma                90
_cell_volume                     1467.64(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    6729
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.98

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.105
_exptl_absorpt_coefficient_mu    0.235
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18776
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         25.700
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2796
_reflns_number_gt                2122
_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-2014/7 (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)+(0.0371P)²+0.5843P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0096(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2796
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.19464(7) 0.55731(3) 0.49252(5) 0.03524(18) Uani 1 1 d . . . . .
O3 O 0.7293(2) 0.36193(9) 0.96817(15) 0.0533(5) Uani 1 1 d . . . . .
O1 O 0.0917(2) 0.39571(9) 0.23633(16) 0.0633(5) Uani 1 1 d . . . . .
O2 O 0.6398(2) 0.48948(9) 0.90955(15) 0.0591(5) Uani 1 1 d . . . . .
N1 N -0.0045(2) 0.65506(9) 0.32697(15) 0.0372(4) Uani 1 1 d . . . . .
N2 N 0.0270(2) 0.52714(10) 0.25605(15) 0.0401(5) Uani 1 1 d . . . . .
C10 C 0.4080(2) 0.38973(11) 0.61632(18) 0.0309(5) Uani 1 1 d . . . . .
C6 C 0.0582(2) 0.58241(12) 0.34349(18) 0.0325(5) Uani 1 1 d . . . . .
C9 C 0.2976(2) 0.39961(12) 0.49074(19) 0.0343(5) Uani 1 1 d . . . . .
H9 H 0.2847 0.3539 0.4408 0.041 Uiso 1 1 calc R U . . .
C15 C 0.4641(2) 0.31335(11) 0.65402(19) 0.0338(5) Uani 1 1 d . . . . .
H15 H 0.4286 0.2712 0.5983 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0182(3) 0.71560(12) 0.42694(19) 0.0385(5) Uani 1 1 d . . . . .
H5A H 0.0922 0.6954 0.5041 0.046 Uiso 1 1 calc R U . . .
H5B H -0.0874 0.7271 0.4459 0.046 Uiso 1 1 calc R U . . .
C11 C 0.4622(3) 0.45379(12) 0.7006(2) 0.0389(5) Uani 1 1 d . . . . .
H11 H 0.4259 0.5054 0.6791 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2112(2) 0.46175(11) 0.43330(18) 0.0326(5) Uani 1 1 d . . . . .
C13 C 0.6232(2) 0.36121(12) 0.8495(2) 0.0367(5) Uani 1 1 d . . . . .
C14 C 0.5711(3) 0.29768(12) 0.7717(2) 0.0380(5) Uani 1 1 d . . . . .
H14 H 0.6057 0.2462 0.7962 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5695(3) 0.43743(12) 0.81434(19) 0.0376(5) Uani 1 1 d . . . . .
C1 C -0.1075(3) 0.67984(13) 0.2024(2) 0.0419(5) Uani 1 1 d . . . . .
H1A H -0.2198 0.6896 0.2094 0.050 Uiso 1 1 calc R U . . .
H1B H -0.1104 0.6379 0.1401 0.050 Uiso 1 1 calc R U . . .
C7 C 0.1051(3) 0.45679(12) 0.2987(2) 0.0404(5) Uani 1 1 d . . . . .
C2 C -0.0366(3) 0.75474(13) 0.1595(2) 0.0438(6) Uani 1 1 d . . . . .
H2A H 0.0699 0.7428 0.1424 0.053 Uiso 1 1 calc R U . . .
H2B H -0.1095 0.7734 0.0808 0.053 Uiso 1 1 calc R U . . .
C4 C 0.0890(3) 0.79104(12) 0.3864(2) 0.0452(6) Uani 1 1 d . . . . .
H4A H 0.2012 0.7814 0.3793 0.054 Uiso 1 1 calc R U . . .
H4B H 0.0925 0.8319 0.4505 0.054 Uiso 1 1 calc R U . . .
C3 C -0.0154(3) 0.81954(13) 0.2590(2) 0.0524(6) Uani 1 1 d . . . . .
H3A H -0.1232 0.8359 0.2691 0.063 Uiso 1 1 calc R U . . .
H3B H 0.0370 0.8653 0.2307 0.063 Uiso 1 1 calc R U . . .
C16 C 0.7531(3) 0.44419(15) 1.0017(2) 0.0627(7) Uani 1 1 d . . . . .
H16A H 0.7343 0.4531 1.0859 0.075 Uiso 1 1 calc R U . . .
H16B H 0.8656 0.4600 1.0033 0.075 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
S1 C8 1.747(2) . ?
S1 C6 1.7818(19) . ?
O3 C13 1.370(2) . ?
O3 C16 1.432(3) . ?
O1 C7 1.218(2) . ?
O2 C12 1.369(2) . ?
O2 C16 1.417(3) . ?
N1 C6 1.324(2) . ?
N1 C5 1.462(3) . ?
N1 C1 1.470(2) . ?
N2 C6 1.305(3) . ?
N2 C7 1.375(3) . ?
C10 C15 1.393(3) . ?
C10 C11 1.412(3) . ?
C10 C9 1.452(3) . ?
C9 C8 1.334(3) . ?
C9 H9 0.9300 . ?
C15 C14 1.390(3) . ?
C15 H15 0.9300 . ?
C5 C4 1.508(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C11 C12 1.361(3) . ?
C11 H11 0.9300 . ?
C8 C7 1.510(3) . ?
C13 C14 1.363(3) . ?
C13 C12 1.380(3) . ?
C14 H14 0.9300 . ?
C1 C2 1.511(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.510(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C3 1.516(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C8 S1 C6 88.69(9) . . ?
C13 O3 C16 105.31(16) . . ?
C12 O2 C16 105.98(17) . . ?
C6 N1 C5 124.51(16) . . ?
C6 N1 C1 120.62(17) . . ?
C5 N1 C1 114.86(16) . . ?
C6 N2 C7 112.02(16) . . ?
C15 C10 C11 118.85(18) . . ?
C15 C10 C9 118.05(17) . . ?
C11 C10 C9 123.09(17) . . ?
N2 C6 N1 123.81(17) . . ?
N2 C6 S1 117.16(15) . . ?
N1 C6 S1 119.03(14) . . ?
C8 C9 C10 132.28(19) . . ?
C8 C9 H9 113.9 . . ?
C10 C9 H9 113.9 . . ?
C14 C15 C10 122.52(19) . . ?
C14 C15 H15 118.7 . . ?
C10 C15 H15 118.7 . . ?
N1 C5 C4 111.20(17) . . ?
N1 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C12 C11 C10 117.73(18) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C9 C8 C7 121.95(18) . . ?
C9 C8 S1 129.19(16) . . ?
C7 C8 S1 108.85(14) . . ?
C14 C13 O3 128.35(19) . . ?
C14 C13 C12 121.64(19) . . ?
O3 C13 C12 110.02(18) . . ?
C13 C14 C15 116.94(18) . . ?
C13 C14 H14 121.5 . . ?
C15 C14 H14 121.5 . . ?
C11 C12 O2 128.07(19) . . ?
C11 C12 C13 122.31(19) . . ?
O2 C12 C13 109.62(17) . . ?
N1 C1 C2 109.31(17) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
O1 C7 N2 124.56(19) . . ?
O1 C7 C8 122.19(19) . . ?
N2 C7 C8 113.25(17) . . ?
C3 C2 C1 111.77(19) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C5 C4 C3 110.48(19) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C2 C3 C4 111.06(18) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O2 C16 O3 108.25(17) . . ?
O2 C16 H16A 110.0 . . ?
O3 C16 H16A 110.0 . . ?
O2 C16 H16B 110.0 . . ?
O3 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_17o
_database_code_depnum_ccdc_archive 'CCDC 1453259'
_audit_update_record             
;
2016-02-14 deposited with the CCDC.
2016-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-5-(naphthalen-1-ylmethylene)-2-(piperidin-1-yl)thiazol-4(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N2 O S'
_chemical_formula_sum            'C19 H18 N2 O S'
_chemical_formula_weight         322.41

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'

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

_cell_length_a                   19.3839(6)
_cell_length_b                   7.7880(3)
_cell_length_c                   20.9133(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3157.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    8202
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      25.32

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.041
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54550
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.1191
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.213
_diffrn_reflns_theta_max         25.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2998
_reflns_number_gt                2211
_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-2014/7 (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)+(0.0343P)²+1.5692P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2998
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
S1 S 0.76609(2) 0.65779(7) 0.60873(2) 0.03525(17) Uani 1 1 d . . . . .
O1 O 0.59111(7) 0.6052(2) 0.52708(7) 0.0438(4) Uani 1 1 d . . . . .
N2 N 0.70402(8) 0.5463(2) 0.50364(7) 0.0316(4) Uani 1 1 d . . . . .
N1 N 0.82336(8) 0.5207(2) 0.50317(8) 0.0365(4) Uani 1 1 d . . . . .
C7 C 0.65183(10) 0.6036(3) 0.54232(9) 0.0318(5) Uani 1 1 d . . . . .
C6 C 0.76474(10) 0.5657(3) 0.53044(9) 0.0304(5) Uani 1 1 d . . . . .
C10 C 0.63981(11) 0.7831(3) 0.71588(9) 0.0361(5) Uani 1 1 d . . . . .
C8 C 0.67603(10) 0.6673(3) 0.60674(9) 0.0316(5) Uani 1 1 d . . . . .
C9 C 0.63065(10) 0.7152(3) 0.65155(9) 0.0347(5) Uani 1 1 d . . . . .
H9 H 0.5848 0.7029 0.6393 0.042 Uiso 1 1 calc R U . . .
C11 C 0.58217(11) 0.7914(3) 0.75943(9) 0.0351(5) Uani 1 1 d . . . . .
C12 C 0.59198(12) 0.8666(3) 0.82080(10) 0.0410(6) Uani 1 1 d . . . . .
C16 C 0.51602(12) 0.7280(3) 0.74467(11) 0.0458(6) Uani 1 1 d . . . . .
H16 H 0.5088 0.6742 0.7056 0.055 Uiso 1 1 calc R U . . .
C1 C 0.82564(11) 0.4529(3) 0.43759(9) 0.0397(5) Uani 1 1 d . . . . .
H1A H 0.7790 0.4356 0.4220 0.048 Uiso 1 1 calc R U . . .
H1B H 0.8491 0.3428 0.4374 0.048 Uiso 1 1 calc R U . . .
C19 C 0.53516(15) 0.8792(3) 0.86324(11) 0.0522(7) Uani 1 1 d . . . . .
H19 H 0.5414 0.9281 0.9034 0.063 Uiso 1 1 calc R U . . .
C15 C 0.70210(12) 0.8488(3) 0.73573(10) 0.0462(6) Uani 1 1 d . . . . .
H15 H 0.7397 0.8439 0.7082 0.055 Uiso 1 1 calc R U . . .
C5 C 0.89178(10) 0.5543(3) 0.53033(11) 0.0426(6) Uani 1 1 d . . . . .
H5A H 0.9178 0.4481 0.5326 0.051 Uiso 1 1 calc R U . . .
H5B H 0.8870 0.5992 0.5734 0.051 Uiso 1 1 calc R U . . .
C17 C 0.46203(13) 0.7439(4) 0.78670(12) 0.0567(7) Uani 1 1 d . . . . .
H17 H 0.4186 0.7030 0.7756 0.068 Uiso 1 1 calc R U . . .
C4 C 0.92978(11) 0.6822(3) 0.48921(11) 0.0488(6) Uani 1 1 d . . . . .
H4A H 0.9759 0.6991 0.5060 0.059 Uiso 1 1 calc R U . . .
H4B H 0.9060 0.7918 0.4904 0.059 Uiso 1 1 calc R U . . .
C18 C 0.47232(15) 0.8216(3) 0.84625(12) 0.0566(7) Uani 1 1 d . . . . .
H18 H 0.4354 0.8336 0.8743 0.068 Uiso 1 1 calc R U . . .
C14 C 0.71042(14) 0.9230(4) 0.79632(11) 0.0577(7) Uani 1 1 d . . . . .
H14 H 0.7531 0.9674 0.8081 0.069 Uiso 1 1 calc R U . . .
C13 C 0.65714(14) 0.9304(3) 0.83765(11) 0.0536(7) Uani 1 1 d . . . . .
H13 H 0.6637 0.9786 0.8779 0.064 Uiso 1 1 calc R U . . .
C2 C 0.86326(11) 0.5770(3) 0.39422(11) 0.0489(6) Uani 1 1 d . . . . .
H2A H 0.8365 0.6816 0.3900 0.059 Uiso 1 1 calc R U . . .
H2B H 0.8681 0.5265 0.3521 0.059 Uiso 1 1 calc R U . . .
C3 C 0.93411(12) 0.6199(4) 0.42073(12) 0.0538(7) Uani 1 1 d . . . . .
H3A H 0.9631 0.5185 0.4189 0.065 Uiso 1 1 calc R U . . .
H3B H 0.9552 0.7081 0.3945 0.065 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
S1 C8 1.7476(19) . ?
S1 C6 1.7878(19) . ?
O1 C7 1.219(2) . ?
N2 C6 1.312(2) . ?
N2 C7 1.370(2) . ?
N1 C6 1.319(2) . ?
N1 C5 1.466(2) . ?
N1 C1 1.470(2) . ?
C7 C8 1.510(3) . ?
C10 C15 1.376(3) . ?
C10 C11 1.443(3) . ?
C10 C9 1.456(3) . ?
C8 C9 1.338(3) . ?
C9 H9 0.9300 . ?
C11 C16 1.408(3) . ?
C11 C12 1.424(3) . ?
C12 C13 1.402(3) . ?
C12 C19 1.418(3) . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C1 C2 1.513(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C19 C18 1.346(3) . ?
C19 H19 0.9300 . ?
C15 C14 1.402(3) . ?
C15 H15 0.9300 . ?
C5 C4 1.509(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C17 C18 1.399(3) . ?
C17 H17 0.9300 . ?
C4 C3 1.515(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C18 H18 0.9300 . ?
C14 C13 1.348(3) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C2 C3 1.518(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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
C8 S1 C6 88.88(9) . . ?
C6 N2 C7 111.88(16) . . ?
C6 N1 C5 124.36(17) . . ?
C6 N1 C1 121.65(17) . . ?
C5 N1 C1 113.47(16) . . ?
O1 C7 N2 124.17(18) . . ?
O1 C7 C8 121.98(18) . . ?
N2 C7 C8 113.85(17) . . ?
N2 C6 N1 123.89(17) . . ?
N2 C6 S1 116.77(14) . . ?
N1 C6 S1 119.34(15) . . ?
C15 C10 C11 118.21(19) . . ?
C15 C10 C9 121.39(19) . . ?
C11 C10 C9 120.32(19) . . ?
C9 C8 C7 120.80(17) . . ?
C9 C8 S1 130.66(16) . . ?
C7 C8 S1 108.52(14) . . ?
C8 C9 C10 131.91(19) . . ?
C8 C9 H9 114.0 . . ?
C10 C9 H9 114.0 . . ?
C16 C11 C12 117.60(19) . . ?
C16 C11 C10 123.45(19) . . ?
C12 C11 C10 118.9(2) . . ?
C13 C12 C19 121.2(2) . . ?
C13 C12 C11 119.5(2) . . ?
C19 C12 C11 119.3(2) . . ?
C17 C16 C11 121.5(2) . . ?
C17 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
N1 C1 C2 110.15(19) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C18 C19 C12 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C12 C19 H19 119.5 . . ?
C10 C15 C14 121.8(2) . . ?
C10 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
N1 C5 C4 109.80(18) . . ?
N1 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C5 C4 C3 110.7(2) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C1 C2 C3 110.95(19) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 111.45(19) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039

