# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1424468'
_audit_update_record             
;
2015-09-15 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            5-NTT1
_chemical_melting_point          436.8
_chemical_formula_moiety         'C15 H13 N3 O2 S2'
_chemical_formula_sum            'C15 H13 N3 O2 S2'
_chemical_formula_weight         331.40
_chemical_absolute_configuration rm

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                   5.9198(12)
_cell_length_b                   15.753(3)
_cell_length_c                   16.190(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.91(3)
_cell_angle_gamma                90
_cell_volume                     1509.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2157
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      24.83

_exptl_crystal_description       rectangular
_exptl_crystal_colour            red
_exptl_crystal_density_meas      1.458
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.363
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9466
_exptl_absorpt_correction_T_max  0.9675
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            6413
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.804
_diffrn_reflns_theta_max         26.997
_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             6413
_reflns_number_gt                4577
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+0.7850P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6413
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
C1 C 1.3743(6) 0.1655(2) 0.7546(2) 0.0445(8) Uani 1 1 d . . . . .
C2 C 1.2959(8) 0.2256(3) 0.7037(3) 0.0830(15) Uani 1 1 d . . . . .
H2 H 1.3535 0.2363 0.6519 0.100 Uiso 1 1 calc R U . . .
C3 C 1.1171(8) 0.2708(3) 0.7368(3) 0.0832(15) Uani 1 1 d . . . . .
H3 H 1.0447 0.3154 0.7093 0.100 Uiso 1 1 calc R U . . .
C4 C 1.0588(5) 0.2438(2) 0.8125(2) 0.0416(8) Uani 1 1 d . . . . .
C5 C 0.8821(5) 0.27871(19) 0.8614(2) 0.0389(7) Uani 1 1 d . . . . .
C6 C 0.7952(5) 0.25704(18) 0.93574(18) 0.0361(7) Uani 1 1 d . . . . .
C7 C 0.5633(5) 0.3637(2) 0.9065(2) 0.0434(8) Uani 1 1 d . . . . .
C8 C 0.2603(6) 0.4197(2) 0.9869(2) 0.0601(10) Uani 1 1 d . . . . .
H8A H 0.1111 0.4000 0.9719 0.090 Uiso 1 1 calc R U . . .
H8B H 0.2517 0.4761 1.0091 0.090 Uiso 1 1 calc R U . . .
H8C H 0.3275 0.3825 1.0277 0.090 Uiso 1 1 calc R U . . .
C9 C 0.3424(7) 0.4815(3) 0.8498(3) 0.0765(13) Uani 1 1 d . . . . .
H9A H 0.4793 0.5060 0.8304 0.115 Uiso 1 1 calc R U . . .
H9B H 0.2485 0.5254 0.8713 0.115 Uiso 1 1 calc R U . . .
H9C H 0.2634 0.4533 0.8049 0.115 Uiso 1 1 calc R U . . .
C10 C 0.8687(5) 0.18647(19) 0.99105(18) 0.0351(7) Uani 1 1 d . . . . .
C11 C 1.0847(5) 0.1818(2) 1.0271(2) 0.0418(8) Uani 1 1 d . . . . .
H11 H 1.1924 0.2223 1.0143 0.050 Uiso 1 1 calc R U . . .
C12 C 1.1400(6) 0.1170(2) 1.0821(2) 0.0485(9) Uani 1 1 d . . . . .
H12 H 1.2848 0.1142 1.1060 0.058 Uiso 1 1 calc R U . . .
C13 C 0.9835(6) 0.0573(2) 1.1013(2) 0.0514(9) Uani 1 1 d . . . . .
H13 H 1.0215 0.0142 1.1385 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7688(6) 0.0608(2) 1.0656(2) 0.0519(9) Uani 1 1 d . . . . .
H14 H 0.6623 0.0199 1.0785 0.062 Uiso 1 1 calc R U . . .
C15 C 0.7126(6) 0.12498(19) 1.01108(19) 0.0434(7) Uani 1 1 d . . . . .
H15 H 0.5675 0.1271 0.9873 0.052 Uiso 1 1 calc R U . . .
N1 N 1.5575(5) 0.1096(2) 0.7437(2) 0.0570(8) Uani 1 1 d . . . . .
N2 N 0.6154(4) 0.30462(16) 0.96060(17) 0.0415(6) Uani 1 1 d . . . . .
N3 N 0.3970(5) 0.42054(18) 0.9146(2) 0.0573(9) Uani 1 1 d . . . . .
O1 O 1.6600(5) 0.1144(2) 0.6797(2) 0.0933(11) Uani 1 1 d . . . . .
O2 O 1.6030(6) 0.0583(2) 0.7979(2) 0.0873(10) Uani 1 1 d . . . . .
S1 S 1.23054(16) 0.16143(6) 0.84433(5) 0.0506(3) Uani 1 1 d . . . . .
S2 S 0.73128(16) 0.36559(6) 0.82045(6) 0.0526(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.329(5) . ?
C1 N1 1.412(4) . ?
C1 S1 1.709(3) . ?
C2 C3 1.397(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.352(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.442(4) . ?
C4 S1 1.718(3) . ?
C5 C6 1.368(4) . ?
C5 S2 1.752(3) . ?
C6 N2 1.373(4) . ?
C6 C10 1.484(4) . ?
C7 N2 1.308(4) . ?
C7 N3 1.340(4) . ?
C7 S2 1.739(4) . ?
C8 N3 1.445(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N3 1.450(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.385(4) . ?
C10 C11 1.390(4) . ?
C11 C12 1.387(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N1 O2 1.217(4) . ?
N1 O1 1.222(4) . ?

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
C2 C1 N1 128.3(3) . . ?
C2 C1 S1 112.4(3) . . ?
N1 C1 S1 119.3(3) . . ?
C1 C2 C3 112.2(4) . . ?
C1 C2 H2 123.9 . . ?
C3 C2 H2 123.9 . . ?
C4 C3 C2 114.1(4) . . ?
C4 C3 H3 123.0 . . ?
C2 C3 H3 123.0 . . ?
C3 C4 C5 126.2(3) . . ?
C3 C4 S1 110.0(3) . . ?
C5 C4 S1 123.8(2) . . ?
C6 C5 C4 133.6(3) . . ?
C6 C5 S2 109.0(2) . . ?
C4 C5 S2 117.3(2) . . ?
C5 C6 N2 116.1(3) . . ?
C5 C6 C10 127.3(3) . . ?
N2 C6 C10 116.5(3) . . ?
N2 C7 N3 124.6(3) . . ?
N2 C7 S2 114.9(2) . . ?
N3 C7 S2 120.5(3) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.5(3) . . ?
C15 C10 C6 118.7(3) . . ?
C11 C10 C6 122.7(3) . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O2 N1 O1 123.3(3) . . ?
O2 N1 C1 118.5(3) . . ?
O1 N1 C1 118.2(4) . . ?
C7 N2 C6 111.1(3) . . ?
C7 N3 C8 120.4(3) . . ?
C7 N3 C9 121.2(3) . . ?
C8 N3 C9 118.3(3) . . ?
C1 S1 C4 91.32(17) . . ?
C7 S2 C5 88.92(15) . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_chemical_properties_physical    'Light-sensitive, Photo-sensitive'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1440185'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
5-(5-nitrothiophen-2-yl)-4-phenyl-2-(piperidin-1-yl)thiazole
_chemical_name_common            5-TPTZ-2
_chemical_melting_point          451.8
_chemical_formula_moiety         'C18 H17 N3 O2 S2'
_chemical_formula_sum            'C18 H17 N3 O2 S2'
_chemical_formula_weight         371.46
_chemical_absolute_configuration rm

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

_cell_length_a                   12.6077(7)
_cell_length_b                   7.6101(4)
_cell_length_c                   36.685(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3519.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3409
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      24.66

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      1.401
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.319
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9249
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            16515
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         3.176
_diffrn_reflns_theta_max         26.997
_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             3837
_reflns_number_gt                2604
_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    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0354P)²+2.5839P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3837
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
C1 C 0.8598(2) 0.0679(3) 0.40171(7) 0.0344(6) Uani 1 1 d . . . . .
C2 C 0.9093(2) 0.1478(3) 0.37276(7) 0.0333(6) Uani 1 1 d . . . . .
C3 C 0.7465(2) 0.1560(3) 0.35069(7) 0.0345(6) Uani 1 1 d . . . . .
C4 C 0.9000(2) -0.0249(3) 0.43328(7) 0.0342(6) Uani 1 1 d . . . . .
C5 C 0.8461(2) -0.0695(4) 0.46433(7) 0.0396(6) Uani 1 1 d . . . . .
H5 H 0.7773 -0.0320 0.4692 0.048 Uiso 1 1 calc R U . . .
C6 C 0.9040(2) -0.1766(4) 0.48811(7) 0.0419(7) Uani 1 1 d . . . . .
H6 H 0.8790 -0.2170 0.5104 0.050 Uiso 1 1 calc R U . . .
C7 C 1.0011(2) -0.2138(3) 0.47441(7) 0.0366(6) Uani 1 1 d . . . . .
C8 C 1.0243(2) 0.1917(3) 0.37105(7) 0.0354(6) Uani 1 1 d . . . . .
C9 C 1.0742(2) 0.2763(4) 0.39993(8) 0.0490(8) Uani 1 1 d . . . . .
H9 H 1.0355 0.3052 0.4207 0.059 Uiso 1 1 calc R U . . .
C10 C 1.1805(3) 0.3176(4) 0.39807(10) 0.0609(9) Uani 1 1 d . . . . .
H10 H 1.2133 0.3728 0.4177 0.073 Uiso 1 1 calc R U . . .
C11 C 1.2380(3) 0.2778(5) 0.36754(10) 0.0634(10) Uani 1 1 d . . . . .
H11 H 1.3097 0.3059 0.3664 0.076 Uiso 1 1 calc R U . . .
C12 C 1.1899(2) 0.1965(5) 0.33854(10) 0.0596(9) Uani 1 1 d . . . . .
H12 H 1.2293 0.1694 0.3178 0.072 Uiso 1 1 calc R U . . .
C13 C 1.0828(2) 0.1545(4) 0.33994(8) 0.0452(7) Uani 1 1 d . . . . .
H13 H 1.0503 0.1013 0.3200 0.054 Uiso 1 1 calc R U . . .
C14 C 0.6844(2) 0.2904(4) 0.29396(8) 0.0509(8) Uani 1 1 d . . . . .
H14A H 0.7595 0.2911 0.2881 0.061 Uiso 1 1 calc R U . . .
H14B H 0.6627 0.4105 0.2987 0.061 Uiso 1 1 calc R U . . .
C15 C 0.6229(3) 0.2188(5) 0.26205(8) 0.0597(9) Uani 1 1 d . . . . .
H15A H 0.6521 0.1059 0.2550 0.072 Uiso 1 1 calc R U . . .
H15B H 0.6300 0.2981 0.2415 0.072 Uiso 1 1 calc R U . . .
C16 C 0.5056(3) 0.1972(5) 0.27145(9) 0.0610(9) Uani 1 1 d . . . . .
H16A H 0.4742 0.3115 0.2759 0.073 Uiso 1 1 calc R U . . .
H16B H 0.4686 0.1435 0.2511 0.073 Uiso 1 1 calc R U . . .
C17 C 0.4939(2) 0.0825(4) 0.30518(9) 0.0596(9) Uani 1 1 d . . . . .
H17A H 0.4195 0.0752 0.3118 0.072 Uiso 1 1 calc R U . . .
H17B H 0.5186 -0.0353 0.2997 0.072 Uiso 1 1 calc R U . . .
C18 C 0.5561(2) 0.1552(4) 0.33678(9) 0.0514(8) Uani 1 1 d . . . . .
H18A H 0.5249 0.2655 0.3446 0.062 Uiso 1 1 calc R U . . .
H18B H 0.5527 0.0737 0.3571 0.062 Uiso 1 1 calc R U . . .
N1 N 0.84648(17) 0.1942(3) 0.34370(6) 0.0354(5) Uani 1 1 d . . . . .
N2 N 1.0827(2) -0.3152(3) 0.49116(7) 0.0463(6) Uani 1 1 d . . . . .
N3 N 0.66653(18) 0.1838(3) 0.32657(6) 0.0438(6) Uani 1 1 d . . . . .
O1 O 1.06815(17) -0.3744(3) 0.52204(6) 0.0544(6) Uani 1 1 d . . . . .
O3 O 1.16452(19) -0.3401(4) 0.47355(7) 0.0778(8) Uani 1 1 d . . . . .
S1 S 0.72279(5) 0.06217(9) 0.39321(2) 0.03721(18) Uani 1 1 d . . . . .
S2 S 1.02480(6) -0.12032(10) 0.43275(2) 0.0461(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(3) . ?
C1 C4 1.448(4) . ?
C1 S1 1.756(3) . ?
C2 N1 1.374(3) . ?
C2 C8 1.490(4) . ?
C3 N1 1.318(3) . ?
C3 N3 1.358(3) . ?
C3 S1 1.742(3) . ?
C4 C5 1.369(3) . ?
C4 S2 1.734(3) . ?
C5 C6 1.400(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.353(4) . ?
C6 H6 0.9300 . ?
C7 N2 1.425(3) . ?
C7 S2 1.712(3) . ?
C8 C13 1.388(4) . ?
C8 C9 1.390(4) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N3 1.463(3) . ?
C14 C15 1.506(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.528(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.521(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.505(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N3 1.459(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N2 O3 1.232(3) . ?
N2 O1 1.233(3) . ?

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
C2 C1 C4 132.5(2) . . ?
C2 C1 S1 108.70(19) . . ?
C4 C1 S1 118.28(19) . . ?
C1 C2 N1 116.9(2) . . ?
C1 C2 C8 125.0(2) . . ?
N1 C2 C8 118.1(2) . . ?
N1 C3 N3 123.3(2) . . ?
N1 C3 S1 115.40(19) . . ?
N3 C3 S1 121.3(2) . . ?
C5 C4 C1 127.8(2) . . ?
C5 C4 S2 110.86(19) . . ?
C1 C4 S2 120.9(2) . . ?
C4 C5 C6 113.8(2) . . ?
C4 C5 H5 123.1 . . ?
C6 C5 H5 123.1 . . ?
C7 C6 C5 111.3(2) . . ?
C7 C6 H6 124.4 . . ?
C5 C6 H6 124.4 . . ?
C6 C7 N2 127.3(2) . . ?
C6 C7 S2 113.7(2) . . ?
N2 C7 S2 118.9(2) . . ?
C13 C8 C9 118.8(3) . . ?
C13 C8 C2 120.4(2) . . ?
C9 C8 C2 120.8(3) . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 120.0(3) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N3 C14 C15 110.8(2) . . ?
N3 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 111.2(3) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 109.9(3) . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C16 111.4(3) . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
N3 C18 C17 110.8(3) . . ?
N3 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C3 N1 C2 110.1(2) . . ?
O3 N2 O1 123.4(2) . . ?
O3 N2 C7 117.5(2) . . ?
O1 N2 C7 119.1(2) . . ?
C3 N3 C18 121.2(2) . . ?
C3 N3 C14 120.3(2) . . ?
C18 N3 C14 116.1(2) . . ?
C3 S1 C1 88.83(13) . . ?
C7 S2 C4 90.32(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18B S1 0.97 2.52 3.034(3) 112.9 .

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_chemical_properties_physical    
'Moisture-sensitive, Light-sensitive, Photo-sensitive'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_sree
_database_code_depnum_ccdc_archive 'CCDC 1440186'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4-(furan-2-yl)-5-(5-nitrothiophen-2-yl)-N,N-diphenylthiazol-2-amine '
_chemical_name_common            5-TPTZ-3
_chemical_melting_point          427.5
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 N3 O3 S2'
_chemical_formula_weight         445.50

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                   5.5393(3)
_cell_length_b                   10.8879(5)
_cell_length_c                   17.6155(10)
_cell_angle_alpha                76.715(4)
_cell_angle_beta                 87.017(3)
_cell_angle_gamma                86.648(3)
_cell_volume                     1031.40(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6555
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.4

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.290
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26644
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.378
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.996
_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             4054
_reflns_number_gt                2851
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0306P)²+0.6123P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4054
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.0260(4) 0.4320(2) 0.18085(16) 0.0488(6) Uani 1 1 d . . . . .
C2 C 0.1686(5) 0.4487(3) 0.11548(18) 0.0675(8) Uani 1 1 d . . . . .
H2 H 0.1526 0.4067 0.0757 0.081 Uiso 1 1 calc R U . . .
C3 C 0.3433(5) 0.5364(3) 0.11438(17) 0.0653(8) Uani 1 1 d . . . . .
H3 H 0.4578 0.5586 0.0737 0.078 Uiso 1 1 calc R U . . .
C4 C 0.3294(4) 0.5861(2) 0.17888(14) 0.0409(6) Uani 1 1 d . . . . .
C5 C 0.4790(4) 0.6749(2) 0.20242(13) 0.0382(5) Uani 1 1 d . . . . .
C6 C 0.6224(4) 0.7672(2) 0.16009(13) 0.0373(5) Uani 1 1 d . . . . .
C7 C 0.6591(4) 0.8058(2) 0.07639(13) 0.0410(6) Uani 1 1 d . . . . .
C8 C 0.8472(5) 0.8513(3) 0.03140(16) 0.0711(9) Uani 1 1 d . . . . .
H8 H 0.9968 0.8662 0.0483 0.085 Uiso 1 1 calc R U . . .
C9 C 0.7797(6) 0.8732(3) -0.04685(16) 0.0761(10) Uani 1 1 d . . . . .
H9 H 0.8754 0.9043 -0.0913 0.091 Uiso 1 1 calc R U . . .
C10 C 0.5558(6) 0.8409(3) -0.04429(17) 0.0779(10) Uani 1 1 d . . . . .
H10 H 0.4642 0.8466 -0.0878 0.093 Uiso 1 1 calc R U . . .
C11 C 0.7039(4) 0.7895(2) 0.27717(13) 0.0353(5) Uani 1 1 d . . . . .
C12 C 0.7207(4) 0.7743(2) 0.41463(13) 0.0355(5) Uani 1 1 d . . . . .
C13 C 0.5018(4) 0.8070(3) 0.44648(15) 0.0493(6) Uani 1 1 d . . . . .
H13 H 0.3984 0.8687 0.4177 0.059 Uiso 1 1 calc R U . . .
C14 C 0.4379(5) 0.7463(3) 0.52232(16) 0.0589(8) Uani 1 1 d . . . . .
H14 H 0.2896 0.7672 0.5445 0.071 Uiso 1 1 calc R U . . .
C15 C 0.5893(6) 0.6565(3) 0.56465(16) 0.0589(8) Uani 1 1 d . . . . .
H15 H 0.5437 0.6158 0.6153 0.071 Uiso 1 1 calc R U . . .
C16 C 0.8082(6) 0.6261(3) 0.53273(16) 0.0617(8) Uani 1 1 d . . . . .
H16 H 0.9128 0.5656 0.5620 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8742(5) 0.6848(2) 0.45738(15) 0.0485(6) Uani 1 1 d . . . . .
H17 H 1.0230 0.6638 0.4355 0.058 Uiso 1 1 calc R U . . .
C18 C 0.9579(4) 0.9340(2) 0.32385(13) 0.0355(5) Uani 1 1 d . . . . .
C19 C 0.9484(4) 1.0094(2) 0.37725(16) 0.0527(7) Uani 1 1 d . . . . .
H19 H 0.8320 0.9972 0.4179 0.063 Uiso 1 1 calc R U . . .
C20 C 1.1111(5) 1.1029(3) 0.37054(19) 0.0633(8) Uani 1 1 d . . . . .
H20 H 1.1038 1.1533 0.4067 0.076 Uiso 1 1 calc R U . . .
C21 C 1.2834(5) 1.1219(3) 0.31078(17) 0.0580(7) Uani 1 1 d . . . . .
H21 H 1.3923 1.1853 0.3062 0.070 Uiso 1 1 calc R U . . .
C22 C 1.2938(4) 1.0472(3) 0.25810(15) 0.0525(7) Uani 1 1 d . . . . .
H22 H 1.4112 1.0598 0.2177 0.063 Uiso 1 1 calc R U . . .
C23 C 1.1316(4) 0.9525(2) 0.26391(14) 0.0439(6) Uani 1 1 d . . . . .
H23 H 1.1402 0.9021 0.2277 0.053 Uiso 1 1 calc R U . . .
N1 N -0.1671(4) 0.3483(2) 0.20260(17) 0.0640(7) Uani 1 1 d . . . . .
N2 N 0.7507(3) 0.83066(17) 0.20290(11) 0.0377(4) Uani 1 1 d . . . . .
N3 N 0.7933(3) 0.83423(17) 0.33579(11) 0.0385(5) Uani 1 1 d . . . . .
O1 O -0.2150(4) 0.2844(2) 0.15730(16) 0.0989(8) Uani 1 1 d . . . . .
O2 O -0.2733(4) 0.3463(2) 0.26514(15) 0.0838(7) Uani 1 1 d . . . . .
O3 O 0.4750(3) 0.7979(2) 0.03069(11) 0.0741(6) Uani 1 1 d . . . . .
S1 S 0.09710(11) 0.52301(6) 0.24191(4) 0.04590(18) Uani 1 1 d . . . . .
S2 S 0.50390(11) 0.66734(6) 0.30131(3) 0.04247(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.345(4) . ?
C1 N1 1.425(3) . ?
C1 S1 1.696(2) . ?
C2 C3 1.395(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.451(3) . ?
C4 S1 1.722(2) . ?
C5 C6 1.373(3) . ?
C5 S2 1.737(2) . ?
C6 N2 1.380(3) . ?
C6 C7 1.444(3) . ?
C7 C8 1.324(3) . ?
C7 O3 1.351(3) . ?
C8 C9 1.410(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.304(4) . ?
C9 H9 0.9300 . ?
C10 O3 1.357(3) . ?
C10 H10 0.9300 . ?
C11 N2 1.299(3) . ?
C11 N3 1.364(3) . ?
C11 S2 1.744(2) . ?
C12 C17 1.368(3) . ?
C12 C13 1.372(3) . ?
C12 N3 1.440(3) . ?
C13 C14 1.385(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.379(3) . ?
C18 C19 1.381(3) . ?
C18 N3 1.431(3) . ?
C19 C20 1.379(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.389(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
N1 O2 1.218(3) . ?
N1 O1 1.221(3) . ?

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
C2 C1 N1 127.6(2) . . ?
C2 C1 S1 113.08(18) . . ?
N1 C1 S1 119.4(2) . . ?
C1 C2 C3 112.0(2) . . ?
C1 C2 H2 124.0 . . ?
C3 C2 H2 124.0 . . ?
C4 C3 C2 113.3(2) . . ?
C4 C3 H3 123.4 . . ?
C2 C3 H3 123.4 . . ?
C3 C4 C5 131.2(2) . . ?
C3 C4 S1 110.67(17) . . ?
C5 C4 S1 118.05(17) . . ?
C6 C5 C4 131.9(2) . . ?
C6 C5 S2 109.19(16) . . ?
C4 C5 S2 118.89(17) . . ?
C5 C6 N2 116.0(2) . . ?
C5 C6 C7 128.5(2) . . ?
N2 C6 C7 115.54(19) . . ?
C8 C7 O3 108.9(2) . . ?
C8 C7 C6 132.3(2) . . ?
O3 C7 C6 118.76(19) . . ?
C7 C8 C9 107.6(2) . . ?
C7 C8 H8 126.2 . . ?
C9 C8 H8 126.2 . . ?
C10 C9 C8 106.1(3) . . ?
C10 C9 H9 126.9 . . ?
C8 C9 H9 126.9 . . ?
C9 C10 O3 110.6(3) . . ?
C9 C10 H10 124.7 . . ?
O3 C10 H10 124.7 . . ?
N2 C11 N3 126.05(19) . . ?
N2 C11 S2 115.20(16) . . ?
N3 C11 S2 118.74(16) . . ?
C17 C12 C13 120.6(2) . . ?
C17 C12 N3 118.9(2) . . ?
C13 C12 N3 120.5(2) . . ?
C12 C13 C14 118.7(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 119.9(2) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C23 C18 C19 119.5(2) . . ?
C23 C18 N3 122.4(2) . . ?
C19 C18 N3 118.0(2) . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.5(2) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C18 C23 C22 119.4(2) . . ?
C18 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
O2 N1 O1 124.7(2) . . ?
O2 N1 C1 117.4(2) . . ?
O1 N1 C1 117.9(3) . . ?
C11 N2 C6 110.62(18) . . ?
C11 N3 C18 124.26(18) . . ?
C11 N3 C12 117.31(17) . . ?
C18 N3 C12 118.41(17) . . ?
C7 O3 C10 106.7(2) . . ?
C1 S1 C4 90.99(12) . . ?
C5 S2 C11 88.98(10) . . ?

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
N1 C1 C2 C3 -178.6(3) . . . . ?
S1 C1 C2 C3 0.7(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 177.2(3) . . . . ?
C2 C3 C4 S1 0.2(4) . . . . ?
C3 C4 C5 C6 25.6(5) . . . . ?
S1 C4 C5 C6 -157.6(2) . . . . ?
C3 C4 C5 S2 -151.5(3) . . . . ?
S1 C4 C5 S2 25.3(3) . . . . ?
C4 C5 C6 N2 -176.9(2) . . . . ?
S2 C5 C6 N2 0.4(3) . . . . ?
C4 C5 C6 C7 2.3(4) . . . . ?
S2 C5 C6 C7 179.6(2) . . . . ?
C5 C6 C7 C8 -148.6(3) . . . . ?
N2 C6 C7 C8 30.6(4) . . . . ?
C5 C6 C7 O3 31.9(4) . . . . ?
N2 C6 C7 O3 -148.9(2) . . . . ?
O3 C7 C8 C9 -0.1(4) . . . . ?
C6 C7 C8 C9 -179.7(3) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C9 C10 O3 -0.8(4) . . . . ?
C17 C12 C13 C14 -1.0(4) . . . . ?
N3 C12 C13 C14 179.5(2) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
C13 C12 C17 C16 0.7(4) . . . . ?
N3 C12 C17 C16 -179.8(2) . . . . ?
C15 C16 C17 C12 0.4(4) . . . . ?
C23 C18 C19 C20 0.2(4) . . . . ?
N3 C18 C19 C20 176.8(2) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 -0.4(5) . . . . ?
C20 C21 C22 C23 0.3(4) . . . . ?
C19 C18 C23 C22 -0.3(4) . . . . ?
N3 C18 C23 C22 -176.7(2) . . . . ?
C21 C22 C23 C18 0.0(4) . . . . ?
C2 C1 N1 O2 179.2(3) . . . . ?
S1 C1 N1 O2 -0.1(4) . . . . ?
C2 C1 N1 O1 -1.1(5) . . . . ?
S1 C1 N1 O1 179.6(2) . . . . ?
N3 C11 N2 C6 -177.7(2) . . . . ?
S2 C11 N2 C6 1.3(3) . . . . ?
C5 C6 N2 C11 -1.1(3) . . . . ?
C7 C6 N2 C11 179.6(2) . . . . ?
N2 C11 N3 C18 -1.0(4) . . . . ?
S2 C11 N3 C18 -179.87(17) . . . . ?
N2 C11 N3 C12 -179.3(2) . . . . ?
S2 C11 N3 C12 1.8(3) . . . . ?
C23 C18 N3 C11 -33.5(3) . . . . ?
C19 C18 N3 C11 150.1(2) . . . . ?
C23 C18 N3 C12 144.9(2) . . . . ?
C19 C18 N3 C12 -31.6(3) . . . . ?
C17 C12 N3 C11 98.9(2) . . . . ?
C13 C12 N3 C11 -81.6(3) . . . . ?
C17 C12 N3 C18 -79.6(3) . . . . ?
C13 C12 N3 C18 100.0(2) . . . . ?
C8 C7 O3 C10 -0.3(3) . . . . ?
C6 C7 O3 C10 179.3(2) . . . . ?
C9 C10 O3 C7 0.7(4) . . . . ?
C2 C1 S1 C4 -0.5(2) . . . . ?
N1 C1 S1 C4 178.8(2) . . . . ?
C3 C4 S1 C1 0.2(2) . . . . ?
C5 C4 S1 C1 -177.3(2) . . . . ?
C6 C5 S2 C11 0.24(18) . . . . ?
C4 C5 S2 C11 177.9(2) . . . . ?
N2 C11 S2 C5 -0.91(19) . . . . ?
N3 C11 S2 C5 178.12(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O3 0.93 2.55 3.003(4) 110.6 .
C10 H10 O1 0.93 2.58 3.366(4) 142.8 2_565
C23 H23 N2 0.93 2.43 2.930(3) 113.8 .

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_chemical_properties_physical    'Light-sensitive, Photo-sensitive'
_exptl_crystal_preparation       Luminescent
