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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_audit_block_doi                 10.5517/ccz3q4x
_database_code_depnum_ccdc_archive 'CCDC 897299'
_audit_update_record             
;
2015-06-23 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;
#==============================================================

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
4-[(4,5-dihydro-1,3-thiazol-2-ylthio)methyl]
-6-methyl-2H-chromen-2-one
;
_chemical_name_common            ?
_chemical_melting_point          440
_chemical_formula_moiety         'C14 H13 N O2 S2'
_chemical_formula_sum            'C14 H13 N O2 S2'
_chemical_formula_weight         291.37

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.93370(10)
_cell_length_b                   8.09230(10)
_cell_length_c                   10.7299(2)
_cell_angle_alpha                99.1900(10)
_cell_angle_beta                 92.5250(10)
_cell_angle_gamma                96.4970(10)
_cell_volume                     674.313(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2376
_cell_measurement_theta_min      1.926
_cell_measurement_theta_max      24.994

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7700
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10734
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.926
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2376
_reflns_number_gt                2153
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2014/7
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.2300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2376
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.26050(8) 0.54985(7) 1.06939(5) 0.0591(2) Uani 1 1 d . . . . .
S2 S 0.30427(6) 0.58968(6) 0.80172(5) 0.04882(19) Uani 1 1 d . . . . .
O3 O -0.14765(15) 0.20784(17) 0.45602(13) 0.0449(3) Uani 1 1 d . . . . .
O4 O -0.29455(17) 0.3557(2) 0.59226(15) 0.0559(4) Uani 1 1 d . . . . .
N5 N 0.2522(2) 0.2937(2) 0.88498(16) 0.0493(4) Uani 1 1 d . . . . .
C6 C -0.1550(2) 0.3230(2) 0.56297(19) 0.0426(4) Uani 1 1 d . . . . .
C7 C 0.0036(2) 0.3970(2) 0.62975(18) 0.0414(4) Uani 1 1 d . . . . .
H7 H 0.0009 0.4749 0.7032 0.050 Uiso 1 1 calc R U . . .
C8 C 0.1552(2) 0.3592(2) 0.59139(17) 0.0365(4) Uani 1 1 d . . . . .
C9 C 0.1604(2) 0.2350(2) 0.47888(17) 0.0360(4) Uani 1 1 d . . . . .
C10 C 0.0060(2) 0.1618(2) 0.41534(18) 0.0390(4) Uani 1 1 d . . . . .
C11 C 0.3096(2) 0.1788(2) 0.43036(18) 0.0398(4) Uani 1 1 d . . . . .
H11 H 0.4142 0.2261 0.4705 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3053(2) 0.0559(2) 0.32527(19) 0.0438(4) Uani 1 1 d . . . . .
C13 C 0.1465(3) -0.0138(2) 0.26608(19) 0.0485(5) Uani 1 1 d . . . . .
H13 H 0.1416 -0.0976 0.1953 0.058 Uiso 1 1 calc R U . . .
C14 C -0.0021(2) 0.0385(2) 0.30986(19) 0.0467(5) Uani 1 1 d . . . . .
H14 H -0.1064 -0.0085 0.2690 0.056 Uiso 1 1 calc R U . . .
C15 C 0.4663(3) -0.0044(3) 0.2763(2) 0.0585(5) Uani 1 1 d . . . . .
H15A H 0.4390 -0.0898 0.2029 0.088 Uiso 1 1 calc R U . . .
H15B H 0.5383 0.0886 0.2541 0.088 Uiso 1 1 calc R U . . .
H15C H 0.5244 -0.0506 0.3407 0.088 Uiso 1 1 calc R U . . .
C16 C 0.3211(2) 0.4416(3) 0.65983(18) 0.0435(4) Uani 1 1 d . . . . .
H16A H 0.3863 0.4996 0.6019 0.052 Uiso 1 1 calc R U . . .
H16B H 0.3849 0.3537 0.6816 0.052 Uiso 1 1 calc R U . . .
C17 C 0.2680(2) 0.4518(2) 0.91029(18) 0.0424(4) Uani 1 1 d . . . . .
C18 C 0.2395(4) 0.2195(3) 1.0003(2) 0.0672(6) Uani 1 1 d . . . . .
H18A H 0.3462 0.1785 1.0201 0.081 Uiso 1 1 calc R U . . .
H18B H 0.1512 0.1241 0.9866 0.081 Uiso 1 1 calc R U . . .
C19 C 0.1994(4) 0.3456(3) 1.1098(2) 0.0681(6) Uani 1 1 d . . . . .
H19A H 0.2625 0.3326 1.1864 0.082 Uiso 1 1 calc R U . . .
H19B H 0.0790 0.3307 1.1233 0.082 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 C17 1.7705(19) . ?
S1 C19 1.795(3) . ?
S2 C17 1.749(2) . ?
S2 C16 1.801(2) . ?
O3 C6 1.366(2) . ?
O3 C10 1.383(2) . ?
O4 C6 1.210(2) . ?
N5 C17 1.255(3) . ?
N5 C18 1.462(3) . ?
C6 C7 1.438(3) . ?
C7 C8 1.340(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.448(3) . ?
C8 C16 1.509(2) . ?
C9 C10 1.396(2) . ?
C9 C11 1.407(3) . ?
C10 C14 1.378(3) . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.401(3) . ?
C12 C15 1.505(3) . ?
C13 C14 1.374(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C19 1.498(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 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
C17 S1 C19 88.60(10) . . ?
C17 S2 C16 100.45(9) . . ?
C6 O3 C10 121.25(14) . . ?
C17 N5 C18 110.88(18) . . ?
O4 C6 O3 117.07(17) . . ?
O4 C6 C7 125.67(19) . . ?
O3 C6 C7 117.25(16) . . ?
C8 C7 C6 123.26(18) . . ?
C8 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
C7 C8 C9 118.68(16) . . ?
C7 C8 C16 122.83(17) . . ?
C9 C8 C16 118.48(15) . . ?
C10 C9 C11 117.30(17) . . ?
C10 C9 C8 117.85(16) . . ?
C11 C9 C8 124.83(16) . . ?
C14 C10 O3 116.32(15) . . ?
C14 C10 C9 122.02(17) . . ?
O3 C10 C9 121.66(17) . . ?
C12 C11 C9 121.94(17) . . ?
C12 C11 H11 119.0 . . ?
C9 C11 H11 119.0 . . ?
C11 C12 C13 118.16(18) . . ?
C11 C12 C15 121.04(18) . . ?
C13 C12 C15 120.79(19) . . ?
C14 C13 C12 121.72(18) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C10 118.86(17) . . ?
C13 C14 H14 120.6 . . ?
C10 C14 H14 120.6 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 S2 115.89(13) . . ?
C8 C16 H16A 108.3 . . ?
S2 C16 H16A 108.3 . . ?
C8 C16 H16B 108.3 . . ?
S2 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
N5 C17 S2 125.75(16) . . ?
N5 C17 S1 118.99(16) . . ?
S2 C17 S1 115.23(11) . . ?
N5 C18 C19 111.30(19) . . ?
N5 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
N5 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 S1 106.35(17) . . ?
C18 C19 H19A 110.5 . . ?
S1 C19 H19A 110.5 . . ?
C18 C19 H19B 110.5 . . ?
S1 C19 H19B 110.5 . . ?
H19A C19 H19B 108.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O3 C6 O4 -179.68(16) . . . . ?
C10 O3 C6 C7 1.4(2) . . . . ?
O4 C6 C7 C8 -178.29(18) . . . . ?
O3 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C6 C7 C8 C16 178.01(16) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C16 C8 C9 C10 -178.96(15) . . . . ?
C7 C8 C9 C11 -177.64(16) . . . . ?
C16 C8 C9 C11 2.8(2) . . . . ?
C6 O3 C10 C14 176.89(16) . . . . ?
C6 O3 C10 C9 -2.3(2) . . . . ?
C11 C9 C10 C14 0.5(3) . . . . ?
C8 C9 C10 C14 -177.85(16) . . . . ?
C11 C9 C10 O3 179.65(15) . . . . ?
C8 C9 C10 O3 1.3(2) . . . . ?
C10 C9 C11 C12 -0.5(3) . . . . ?
C8 C9 C11 C12 177.70(16) . . . . ?
C9 C11 C12 C13 0.0(3) . . . . ?
C9 C11 C12 C15 -178.95(17) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C15 C12 C13 C14 179.47(19) . . . . ?
C12 C13 C14 C10 -0.5(3) . . . . ?
O3 C10 C14 C13 -179.20(16) . . . . ?
C9 C10 C14 C13 0.0(3) . . . . ?
C7 C8 C16 S2 2.4(2) . . . . ?
C9 C8 C16 S2 -178.07(12) . . . . ?
C17 S2 C16 C8 81.62(15) . . . . ?
C18 N5 C17 S2 174.54(16) . . . . ?
C18 N5 C17 S1 -3.3(2) . . . . ?
C16 S2 C17 N5 -2.85(19) . . . . ?
C16 S2 C17 S1 175.08(10) . . . . ?
C19 S1 C17 N5 -8.03(18) . . . . ?
C19 S1 C17 S2 173.89(13) . . . . ?
C17 N5 C18 C19 16.1(3) . . . . ?
N5 C18 C19 S1 -20.9(3) . . . . ?
C17 S1 C19 C18 15.64(19) . . . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_I
_audit_block_doi                 10.5517/ccz3q5y
_database_code_depnum_ccdc_archive 'CCDC 897300'
_audit_update_record             
;
2015-06-23 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;
#============================================================== 

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
6-chloro-4-[(4,5-dihydro-1,3-thiazol-2-
ylthio)methyl]-2H-chromen-2-one
;
_chemical_name_common            ?
_chemical_melting_point          450
_chemical_formula_moiety         'C13 H10 Cl N O2 S2'
_chemical_formula_sum            'C13 H10 Cl N O2 S2'
_chemical_formula_weight         311.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3443(3)
_cell_length_b                   7.7814(3)
_cell_length_c                   12.6804(4)
_cell_angle_alpha                85.486(2)
_cell_angle_beta                 82.226(2)
_cell_angle_gamma                65.984(2)
_cell_volume                     655.63(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2307
_cell_measurement_theta_min      1.621
_cell_measurement_theta_max      24.992

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7700
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9894
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.621
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_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             2307
_reflns_number_gt                2059
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2014/7
_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+0.2154P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2307
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.13873(8) 0.39032(8) 1.15905(4) 0.05589(19) Uani 1 1 d . . . . .
S2 S 0.08896(13) 0.23750(11) 0.44241(5) 0.0771(2) Uani 1 1 d . . . . .
S3 S 0.36282(8) 0.14751(8) 0.60906(4) 0.04870(18) Uani 1 1 d . . . . .
O4 O 0.3117(2) -0.30694(19) 0.94511(13) 0.0520(4) Uani 1 1 d . . . . .
O5 O 0.3933(3) -0.4802(2) 0.80387(17) 0.0748(5) Uani 1 1 d . . . . .
N6 N -0.0379(3) 0.2587(3) 0.64600(15) 0.0527(4) Uani 1 1 d . . . . .
C7 C 0.3587(3) -0.3283(3) 0.8378(2) 0.0513(5) Uani 1 1 d . . . . .
C8 C 0.3603(3) -0.1669(3) 0.77382(17) 0.0447(5) Uani 1 1 d . . . . .
H8 H 0.3902 -0.1788 0.7004 0.054 Uiso 1 1 calc R U . . .
C9 C 0.3206(2) -0.0006(2) 0.81553(15) 0.0348(4) Uani 1 1 d . . . . .
C10 C 0.2749(2) 0.0168(2) 0.93059(14) 0.0332(4) Uani 1 1 d . . . . .
C11 C 0.2709(3) -0.1392(3) 0.99134(16) 0.0399(4) Uani 1 1 d . . . . .
C12 C 0.2228(3) -0.1327(3) 1.10051(17) 0.0494(5) Uani 1 1 d . . . . .
H12 H 0.2192 -0.2382 1.1391 0.059 Uiso 1 1 calc R U . . .
C13 C 0.1803(3) 0.0302(3) 1.15163(17) 0.0479(5) Uani 1 1 d . . . . .
H13 H 0.1468 0.0365 1.2250 0.057 Uiso 1 1 calc R U . . .
C14 C 0.1879(3) 0.1855(3) 1.09273(15) 0.0398(4) Uani 1 1 d . . . . .
C15 C 0.2341(2) 0.1815(3) 0.98410(14) 0.0356(4) Uani 1 1 d . . . . .
H15 H 0.2382 0.2874 0.9463 0.043 Uiso 1 1 calc R U . . .
C16 C 0.3211(3) 0.1694(3) 0.75140(14) 0.0399(4) Uani 1 1 d . . . . .
H16A H 0.4241 0.2025 0.7732 0.048 Uiso 1 1 calc R U . . .
H16B H 0.1930 0.2734 0.7691 0.048 Uiso 1 1 calc R U . . .
C17 C 0.1167(3) 0.2171(3) 0.57908(15) 0.0423(4) Uani 1 1 d . . . . .
C18 C -0.2182(4) 0.3256(5) 0.5930(3) 0.0869(9) Uani 1 1 d . . . . .
H18A H -0.2946 0.4581 0.6070 0.104 Uiso 1 1 calc R U . . .
H18B H -0.3002 0.2584 0.6226 0.104 Uiso 1 1 calc R U . . .
C19 C -0.1744(5) 0.2997(4) 0.4754(3) 0.0870(10) Uani 1 1 d . . . . .
H19A H -0.2505 0.4153 0.4380 0.104 Uiso 1 1 calc R U . . .
H19B H -0.2104 0.2008 0.4555 0.104 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.7427(19) . ?
S2 C17 1.7595(19) . ?
S2 C19 1.789(3) . ?
S3 C17 1.750(2) . ?
S3 C16 1.7991(18) . ?
O4 C7 1.363(3) . ?
O4 C11 1.375(2) . ?
O5 C7 1.205(3) . ?
N6 C17 1.264(3) . ?
N6 C18 1.449(3) . ?
C7 C8 1.445(3) . ?
C8 C9 1.341(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.456(3) . ?
C9 C16 1.498(3) . ?
C10 C11 1.395(3) . ?
C10 C15 1.400(2) . ?
C11 C12 1.381(3) . ?
C12 C13 1.370(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C19 1.495(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 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
C17 S2 C19 89.31(12) . . ?
C17 S3 C16 100.73(9) . . ?
C7 O4 C11 121.50(16) . . ?
C17 N6 C18 111.0(2) . . ?
O5 C7 O4 117.3(2) . . ?
O5 C7 C8 125.2(2) . . ?
O4 C7 C8 117.54(17) . . ?
C9 C8 C7 122.9(2) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C8 C9 C10 118.25(18) . . ?
C8 C9 C16 124.23(18) . . ?
C10 C9 C16 117.52(15) . . ?
C11 C10 C15 117.86(17) . . ?
C11 C10 C9 118.26(16) . . ?
C15 C10 C9 123.88(16) . . ?
O4 C11 C12 116.59(18) . . ?
O4 C11 C10 121.51(18) . . ?
C12 C11 C10 121.89(18) . . ?
C13 C12 C11 119.59(19) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 119.30(19) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 121.73(18) . . ?
C15 C14 Cl1 119.43(15) . . ?
C13 C14 Cl1 118.84(15) . . ?
C14 C15 C10 119.60(17) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C9 C16 S3 116.35(13) . . ?
C9 C16 H16A 108.2 . . ?
S3 C16 H16A 108.2 . . ?
C9 C16 H16B 108.2 . . ?
S3 C16 H16B 108.2 . . ?
H16A C16 H16B 107.4 . . ?
N6 C17 S3 125.82(15) . . ?
N6 C17 S2 119.00(16) . . ?
S3 C17 S2 115.13(12) . . ?
N6 C18 C19 112.7(2) . . ?
N6 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N6 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 S2 106.87(18) . . ?
C18 C19 H19A 110.3 . . ?
S2 C19 H19A 110.3 . . ?
C18 C19 H19B 110.3 . . ?
S2 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O4 C7 O5 179.65(18) . . . . ?
C11 O4 C7 C8 -1.2(3) . . . . ?
O5 C7 C8 C9 -180.0(2) . . . . ?
O4 C7 C8 C9 0.9(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C7 C8 C9 C16 -179.97(17) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
C16 C9 C10 C11 179.03(15) . . . . ?
C8 C9 C10 C15 178.95(16) . . . . ?
C16 C9 C10 C15 -0.8(2) . . . . ?
C7 O4 C11 C12 179.26(17) . . . . ?
C7 O4 C11 C10 0.2(3) . . . . ?
C15 C10 C11 O4 -179.17(15) . . . . ?
C9 C10 C11 O4 1.0(2) . . . . ?
C15 C10 C11 C12 1.8(3) . . . . ?
C9 C10 C11 C12 -177.99(16) . . . . ?
O4 C11 C12 C13 -179.98(17) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C12 C13 C14 Cl1 -178.67(15) . . . . ?
C13 C14 C15 C10 0.0(3) . . . . ?
Cl1 C14 C15 C10 179.60(12) . . . . ?
C11 C10 C15 C14 -1.3(2) . . . . ?
C9 C10 C15 C14 178.47(15) . . . . ?
C8 C9 C16 S3 4.0(2) . . . . ?
C10 C9 C16 S3 -176.30(12) . . . . ?
C17 S3 C16 C9 88.89(15) . . . . ?
C18 N6 C17 S3 175.04(19) . . . . ?
C18 N6 C17 S2 -2.3(3) . . . . ?
C16 S3 C17 N6 -3.4(2) . . . . ?
C16 S3 C17 S2 173.97(10) . . . . ?
C19 S2 C17 N6 -3.93(19) . . . . ?
C19 S2 C17 S3 178.49(13) . . . . ?
C17 N6 C18 C19 9.0(3) . . . . ?
N6 C18 C19 S2 -11.3(3) . . . . ?
C17 S2 C19 C18 8.2(2) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1059231'
_audit_update_record             
;
2015-06-23 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;
#============================================================== 

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
4-((4,5-dihydrothiazol-2-ylthio)methyl)-7-
methyl-2H-chromen-2-one
;
_chemical_name_common            ?
_chemical_melting_point          442
_chemical_formula_moiety         'C14 H13 N O2 S2'
_chemical_formula_sum            'C14 H13 N O2 S2'
_chemical_formula_weight         291.37

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8774(2)
_cell_length_b                   8.4986(3)
_cell_length_c                   11.2330(3)
_cell_angle_alpha                91.435(2)
_cell_angle_beta                 107.376(2)
_cell_angle_gamma                107.927(2)
_cell_volume                     677.16(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3587
_cell_measurement_theta_min      1.916
_cell_measurement_theta_max      29.019

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7700
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13042
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.916
_diffrn_reflns_theta_max         29.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3587
_reflns_number_gt                2841
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2014/7
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²+0.1591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3587
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.35558(6) 0.78948(6) 0.78493(4) 0.04858(15) Uani 1 1 d . . . . .
S2 S 0.47720(7) 0.72252(7) 1.04767(5) 0.05993(17) Uani 1 1 d . . . . .
O3 O 0.71476(16) 0.72281(16) 0.46773(11) 0.0440(3) Uani 1 1 d . . . . .
O4 O 0.99688(18) 0.8638(2) 0.59845(14) 0.0621(4) Uani 1 1 d . . . . .
N5 N 0.7148(2) 0.8971(2) 0.94110(14) 0.0508(4) Uani 1 1 d . . . . .
C6 C 0.1158(3) 0.4049(3) 0.15844(19) 0.0589(5) Uani 1 1 d . . . . .
H6A H -0.0162 0.3856 0.1419 0.088 Uiso 1 1 calc R U . . .
H6B H 0.1533 0.4542 0.0904 0.088 Uiso 1 1 calc R U . . .
H6C H 0.1398 0.3009 0.1661 0.088 Uiso 1 1 calc R U . . .
C7 C 0.2265(2) 0.5208(2) 0.27879(16) 0.0438(4) Uani 1 1 d . . . . .
C8 C 0.1355(2) 0.5837(2) 0.34841(17) 0.0473(4) Uani 1 1 d . . . . .
H8 H 0.0046 0.5518 0.3201 0.057 Uiso 1 1 calc R U . . .
C9 C 0.2353(2) 0.6913(2) 0.45752(16) 0.0433(4) Uani 1 1 d . . . . .
H9 H 0.1713 0.7303 0.5023 0.052 Uiso 1 1 calc R U . . .
C10 C 0.4330(2) 0.74314(19) 0.50234(14) 0.0351(3) Uani 1 1 d . . . . .
C11 C 0.5215(2) 0.6782(2) 0.43224(14) 0.0366(3) Uani 1 1 d . . . . .
C12 C 0.4211(2) 0.5685(2) 0.32357(16) 0.0417(4) Uani 1 1 d . . . . .
H12 H 0.4845 0.5261 0.2801 0.050 Uiso 1 1 calc R U . . .
C13 C 0.5509(2) 0.8605(2) 0.61373(14) 0.0368(3) Uani 1 1 d . . . . .
C14 C 0.7387(2) 0.9026(2) 0.64474(16) 0.0431(4) Uani 1 1 d . . . . .
H14 H 0.8136 0.9798 0.7154 0.052 Uiso 1 1 calc R U . . .
C15 C 0.8296(2) 0.8333(2) 0.57314(16) 0.0447(4) Uani 1 1 d . . . . .
C16 C 0.4637(2) 0.9355(2) 0.69234(16) 0.0431(4) Uani 1 1 d . . . . .
H16A H 0.3689 0.9752 0.6375 0.052 Uiso 1 1 calc R U . . .
H16B H 0.5602 1.0309 0.7484 0.052 Uiso 1 1 calc R U . . .
C17 C 0.5440(2) 0.8167(2) 0.92257(15) 0.0405(4) Uani 1 1 d . . . . .
C18 C 0.7228(3) 0.7616(3) 1.1321(2) 0.0638(5) Uani 1 1 d . . . . .
H18A H 0.7512 0.7977 1.2205 0.077 Uiso 1 1 calc R U . . .
H18B H 0.7560 0.6618 1.1245 0.077 Uiso 1 1 calc R U . . .
C19 C 0.8295(3) 0.8988(3) 1.07109(18) 0.0565(5) Uani 1 1 d . . . . .
H19A H 0.8606 1.0063 1.1188 0.068 Uiso 1 1 calc R U . . .
H19B H 0.9463 0.8824 1.0717 0.068 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 C17 1.7455(18) . ?
S1 C16 1.8140(18) . ?
S2 C17 1.7693(17) . ?
S2 C18 1.802(2) . ?
O3 C15 1.372(2) . ?
O3 C11 1.3769(19) . ?
O4 C15 1.203(2) . ?
N5 C17 1.257(2) . ?
N5 C19 1.467(2) . ?
C6 C7 1.503(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.384(2) . ?
C7 C8 1.400(2) . ?
C8 C9 1.372(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.404(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.397(2) . ?
C10 C13 1.448(2) . ?
C11 C12 1.378(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.340(2) . ?
C13 C16 1.504(2) . ?
C14 C15 1.445(2) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C19 1.522(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 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
C17 S1 C16 102.01(8) . . ?
C17 S2 C18 88.63(9) . . ?
C15 O3 C11 121.70(12) . . ?
C17 N5 C19 111.16(15) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 118.26(16) . . ?
C12 C7 C6 120.81(17) . . ?
C8 C7 C6 120.93(17) . . ?
C9 C8 C7 121.38(16) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.81(15) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 117.06(15) . . ?
C11 C10 C13 117.99(14) . . ?
C9 C10 C13 124.94(14) . . ?
O3 C11 C12 116.44(14) . . ?
O3 C11 C10 121.44(14) . . ?
C12 C11 C10 122.12(15) . . ?
C11 C12 C7 120.35(15) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C10 119.01(14) . . ?
C14 C13 C16 120.61(15) . . ?
C10 C13 C16 120.37(14) . . ?
C13 C14 C15 122.85(16) . . ?
C13 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
O4 C15 O3 117.49(16) . . ?
O4 C15 C14 125.51(18) . . ?
O3 C15 C14 117.00(14) . . ?
C13 C16 S1 113.00(12) . . ?
C13 C16 H16A 109.0 . . ?
S1 C16 H16A 109.0 . . ?
C13 C16 H16B 109.0 . . ?
S1 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
N5 C17 S1 127.23(14) . . ?
N5 C17 S2 118.81(14) . . ?
S1 C17 S2 113.93(9) . . ?
C19 C18 S2 105.20(15) . . ?
C19 C18 H18A 110.7 . . ?
S2 C18 H18A 110.7 . . ?
C19 C18 H18B 110.7 . . ?
S2 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?
N5 C19 C18 110.36(16) . . ?
N5 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
N5 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C7 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C9 -179.12(17) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 -1.0(2) . . . . ?
C8 C9 C10 C13 177.74(16) . . . . ?
C15 O3 C11 C12 178.97(14) . . . . ?
C15 O3 C11 C10 -0.2(2) . . . . ?
C9 C10 C11 O3 179.32(14) . . . . ?
C13 C10 C11 O3 0.5(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C13 C10 C11 C12 -178.69(14) . . . . ?
O3 C11 C12 C7 -178.01(15) . . . . ?
C10 C11 C12 C7 1.2(2) . . . . ?
C8 C7 C12 C11 -1.6(2) . . . . ?
C6 C7 C12 C11 178.28(16) . . . . ?
C11 C10 C13 C14 0.3(2) . . . . ?
C9 C10 C13 C14 -178.44(16) . . . . ?
C11 C10 C13 C16 179.52(14) . . . . ?
C9 C10 C13 C16 0.8(2) . . . . ?
C10 C13 C14 C15 -1.3(3) . . . . ?
C16 C13 C14 C15 179.47(15) . . . . ?
C11 O3 C15 O4 179.01(15) . . . . ?
C11 O3 C15 C14 -0.7(2) . . . . ?
C13 C14 C15 O4 -178.16(18) . . . . ?
C13 C14 C15 O3 1.6(3) . . . . ?
C14 C13 C16 S1 -107.17(16) . . . . ?
C10 C13 C16 S1 73.65(17) . . . . ?
C17 S1 C16 C13 88.38(13) . . . . ?
C19 N5 C17 S1 176.97(14) . . . . ?
C19 N5 C17 S2 -1.1(2) . . . . ?
C16 S1 C17 N5 -10.16(19) . . . . ?
C16 S1 C17 S2 167.99(9) . . . . ?
C18 S2 C17 N5 -12.40(17) . . . . ?
C18 S2 C17 S1 169.29(12) . . . . ?
C17 S2 C18 C19 20.03(16) . . . . ?
C17 N5 C19 C18 17.6(2) . . . . ?
S2 C18 C19 N5 -25.1(2) . . . . ?

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1059232'
_audit_update_record             
;
2015-06-23 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;
#==============================================================

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
4-((4,5-dihydrothiazol-2-ylthio)methyl)-5,7-dimethyl-
2H-chromen-2-one
;
_chemical_name_common            ?
_chemical_melting_point          457
_chemical_formula_moiety         'C15 H15 N O2 S2'
_chemical_formula_sum            'C15 H15 N O2 S2'
_chemical_formula_weight         305.40

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                   7.2356(8)
_cell_length_b                   7.9426(10)
_cell_length_c                   25.027(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.742(8)
_cell_angle_gamma                90
_cell_volume                     1428.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1769
_cell_measurement_theta_min      1.639
_cell_measurement_theta_max      22.287

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7700
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6194
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.639
_diffrn_reflns_theta_max         22.287
_diffrn_reflns_theta_full        22.287
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             1769
_reflns_number_gt                1338
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2014/7
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+4.4284P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1769
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1491
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_THETM01_I                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE:This structure intrinsically exhibits many weak
reflections at higher theta values.
;
_vrf_PLAT023_I                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      22.29 Degree
RESPONSE: This structure intrinsically exhibits many weak
reflections at higher theta values.
;
# end Validation Reply Form

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 0.1026(2) 0.8080(2) 0.32112(7) 0.0536(6) Uani 1 1 d . . . . .
S2 S 0.3274(2) 0.9523(2) 0.24117(7) 0.0534(6) Uani 1 1 d . . . . .
O3 O -0.3414(5) 0.6005(5) 0.45786(16) 0.0440(11) Uani 1 1 d . . . . .
O4 O -0.4608(6) 0.5279(7) 0.37659(18) 0.0663(15) Uani 1 1 d . . . . .
N5 N 0.4466(7) 0.9375(7) 0.3440(2) 0.0463(14) Uani 1 1 d . . . . .
C6 C -0.1234(9) 0.6972(9) 0.6441(2) 0.0602(19) Uani 1 1 d . . . . .
H6A H -0.2110 0.7813 0.6523 0.090 Uiso 1 1 calc R U . . .
H6B H -0.0066 0.7154 0.6657 0.090 Uiso 1 1 calc R U . . .
H6C H -0.1700 0.5876 0.6515 0.090 Uiso 1 1 calc R U . . .
C8 C -0.0962(8) 0.7088(8) 0.5854(2) 0.0434(16) Uani 1 1 d . . . . .
C9 C 0.0681(8) 0.7730(8) 0.5698(2) 0.0451(16) Uani 1 1 d . . . . .
H9 H 0.1598 0.8095 0.5964 0.054 Uiso 1 1 calc R U . . .
C10 C 0.1020(7) 0.7852(8) 0.5167(2) 0.0407(15) Uani 1 1 d . . . . .
C11 C -0.0351(7) 0.7301(7) 0.4757(2) 0.0355(15) Uani 1 1 d . . . . .
C14 C -0.0279(7) 0.7300(7) 0.4177(2) 0.0340(14) Uani 1 1 d . . . . .
C17 C 0.1384(8) 0.8011(8) 0.3936(2) 0.0437(16) Uani 1 1 d . . . . .
H17A H 0.2468 0.7324 0.4049 0.052 Uiso 1 1 calc R U . . .
H17B H 0.1633 0.9140 0.4073 0.052 Uiso 1 1 calc R U . . .
C18 C 0.3120(8) 0.9032(7) 0.3092(2) 0.0403(15) Uani 1 1 d . . . . .
C19 C 0.5930(8) 1.0239(9) 0.3181(2) 0.0533(18) Uani 1 1 d . . . . .
H19A H 0.7145 0.9886 0.3349 0.064 Uiso 1 1 calc R U . . .
H19B H 0.5827 1.1446 0.3228 0.064 Uiso 1 1 calc R U . . .
C20 C 0.5738(8) 0.9824(9) 0.2589(3) 0.0578(19) Uani 1 1 d . . . . .
H20A H 0.6420 0.8808 0.2524 0.069 Uiso 1 1 calc R U . . .
H20B H 0.6193 1.0741 0.2384 0.069 Uiso 1 1 calc R U . . .
C7 C 0.2895(8) 0.8586(9) 0.5074(3) 0.060(2) Uani 1 1 d . . . . .
H7A H 0.3575 0.8882 0.5414 0.091 Uiso 1 1 calc R U . . .
H7B H 0.2708 0.9572 0.4853 0.091 Uiso 1 1 calc R U . . .
H7C H 0.3587 0.7766 0.4898 0.091 Uiso 1 1 calc R U . . .
C13 C -0.2293(8) 0.6531(8) 0.5457(2) 0.0422(16) Uani 1 1 d . . . . .
H13 H -0.3407 0.6088 0.5546 0.051 Uiso 1 1 calc R U . . .
C12 C -0.1974(7) 0.6632(7) 0.4933(2) 0.0382(15) Uani 1 1 d . . . . .
C16 C -0.3334(9) 0.5925(8) 0.4036(3) 0.0471(17) Uani 1 1 d . . . . .
C15 C -0.1700(8) 0.6675(7) 0.3856(2) 0.0417(16) Uani 1 1 d . . . . .
H15 H -0.1639 0.6723 0.3487 0.050 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 C18 1.750(6) . ?
S1 C17 1.803(6) . ?
S2 C18 1.764(6) . ?
S2 C20 1.802(6) . ?
O3 C16 1.367(7) . ?
O3 C12 1.380(7) . ?
O4 C16 1.193(7) . ?
N5 C18 1.257(7) . ?
N5 C19 1.474(7) . ?
C6 C8 1.507(8) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 C13 1.373(8) . ?
C8 C9 1.391(8) . ?
C9 C10 1.383(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.409(8) . ?
C10 C7 1.519(8) . ?
C11 C12 1.407(7) . ?
C11 C14 1.460(8) . ?
C14 C15 1.324(8) . ?
C14 C17 1.516(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C20 1.509(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 C12 1.360(8) . ?
C13 H13 0.9300 . ?
C16 C15 1.443(8) . ?
C15 H15 0.9300 . ?

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
C18 S1 C17 99.2(3) . . ?
C18 S2 C20 88.0(3) . . ?
C16 O3 C12 122.6(4) . . ?
C18 N5 C19 109.6(5) . . ?
C8 C6 H6A 109.5 . . ?
C8 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C8 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C13 C8 C9 117.7(5) . . ?
C13 C8 C6 121.6(5) . . ?
C9 C8 C6 120.7(6) . . ?
C10 C9 C8 123.4(6) . . ?
C10 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C9 C10 C11 119.2(5) . . ?
C9 C10 C7 115.8(5) . . ?
C11 C10 C7 125.0(5) . . ?
C12 C11 C10 115.6(5) . . ?
C12 C11 C14 116.1(5) . . ?
C10 C11 C14 128.3(5) . . ?
C15 C14 C11 119.2(5) . . ?
C15 C14 C17 119.6(5) . . ?
C11 C14 C17 121.2(5) . . ?
C14 C17 S1 112.6(4) . . ?
C14 C17 H17A 109.1 . . ?
S1 C17 H17A 109.1 . . ?
C14 C17 H17B 109.1 . . ?
S1 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
N5 C18 S1 126.3(5) . . ?
N5 C18 S2 119.2(4) . . ?
S1 C18 S2 114.4(4) . . ?
N5 C19 C20 110.0(5) . . ?
N5 C19 H19A 109.7 . . ?
C20 C19 H19A 109.7 . . ?
N5 C19 H19B 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 S2 104.2(4) . . ?
C19 C20 H20A 110.9 . . ?
S2 C20 H20A 110.9 . . ?
C19 C20 H20B 110.9 . . ?
S2 C20 H20B 110.9 . . ?
H20A C20 H20B 108.9 . . ?
C10 C7 H7A 109.5 . . ?
C10 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C10 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C13 C8 119.6(5) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C13 C12 O3 113.5(5) . . ?
C13 C12 C11 124.5(6) . . ?
O3 C12 C11 122.0(5) . . ?
O4 C16 O3 117.6(5) . . ?
O4 C16 C15 127.4(6) . . ?
O3 C16 C15 115.0(6) . . ?
C14 C15 C16 124.9(6) . . ?
C14 C15 H15 117.5 . . ?
C16 C15 H15 117.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C8 C9 C10 0.9(9) . . . . ?
C6 C8 C9 C10 179.3(6) . . . . ?
C8 C9 C10 C11 -0.1(9) . . . . ?
C8 C9 C10 C7 -180.0(6) . . . . ?
C9 C10 C11 C12 -1.0(8) . . . . ?
C7 C10 C11 C12 178.8(6) . . . . ?
C9 C10 C11 C14 -179.4(5) . . . . ?
C7 C10 C11 C14 0.4(10) . . . . ?
C12 C11 C14 C15 -0.6(8) . . . . ?
C10 C11 C14 C15 177.9(6) . . . . ?
C12 C11 C14 C17 179.1(5) . . . . ?
C10 C11 C14 C17 -2.5(9) . . . . ?
C15 C14 C17 S1 6.2(7) . . . . ?
C11 C14 C17 S1 -173.5(4) . . . . ?
C18 S1 C17 C14 177.4(4) . . . . ?
C19 N5 C18 S1 -177.4(5) . . . . ?
C19 N5 C18 S2 2.7(7) . . . . ?
C17 S1 C18 N5 5.5(6) . . . . ?
C17 S1 C18 S2 -174.6(3) . . . . ?
C20 S2 C18 N5 14.2(6) . . . . ?
C20 S2 C18 S1 -165.7(4) . . . . ?
C18 N5 C19 C20 -22.8(8) . . . . ?
N5 C19 C20 S2 31.3(7) . . . . ?
C18 S2 C20 C19 -24.4(5) . . . . ?
C9 C8 C13 C12 -0.4(9) . . . . ?
C6 C8 C13 C12 -178.8(6) . . . . ?
C8 C13 C12 O3 179.0(5) . . . . ?
C8 C13 C12 C11 -0.9(9) . . . . ?
C16 O3 C12 C13 -177.2(5) . . . . ?
C16 O3 C12 C11 2.7(8) . . . . ?
C10 C11 C12 C13 1.6(9) . . . . ?
C14 C11 C12 C13 -179.8(5) . . . . ?
C10 C11 C12 O3 -178.3(5) . . . . ?
C14 C11 C12 O3 0.3(8) . . . . ?
C12 O3 C16 O4 176.0(6) . . . . ?
C12 O3 C16 C15 -5.0(8) . . . . ?
C11 C14 C15 C16 -2.1(9) . . . . ?
C17 C14 C15 C16 178.3(6) . . . . ?
O4 C16 C15 C14 -176.3(7) . . . . ?
O3 C16 C15 C14 4.8(9) . . . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.065

