# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_TMCA222
_database_code_depnum_ccdc_archive 'CCDC 1523441'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H21 N3 O2 S'
_chemical_formula_moiety         'C21 H21 N3 O2 S'
_chemical_formula_weight         379.48
_chemical_melting_point          401.15-401.75

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.401(5)
_cell_length_b                   10.660(5)
_cell_length_c                   11.058(5)
_cell_angle_alpha                107.936(5)
_cell_angle_beta                 98.134(3)
_cell_angle_gamma                110.383(3)
_cell_volume                     949.1(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3040
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      30.28
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.400
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400.00
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_T_max  0.926

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            6870
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         3.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4148
_reflns_number_gt                3701
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1274
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4148
_refine_ls_number_parameters     244
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0768P)²+0.2783P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.00072(5) 0.83865(4) 0.04982(4) 0.03417(15) Uani 1 1 d . . . . .
O1 O 0.07649(14) 1.25028(13) 0.35928(13) 0.0450(3) Uani 1 1 d . . . . .
O2 O 0.07695(12) 1.42255(11) 0.28128(11) 0.0323(3) Uani 1 1 d . . . . .
N1 N -0.14943(13) 1.22737(12) 0.22763(11) 0.0229(2) Uani 1 1 d . . . . .
N2 N -0.07605(14) 0.95204(13) 0.10357(12) 0.0277(3) Uani 1 1 d . . . . .
N3 N -0.01904(17) 0.75847(15) 0.15274(14) 0.0351(3) Uani 1 1 d . . . . .
C1 C -0.24300(16) 1.28212(14) 0.16686(13) 0.0232(3) Uani 1 1 d . . . . .
C2 C -0.20242(19) 1.39590(16) 0.12258(15) 0.0307(3) Uani 1 1 d . . . . .
H2 H -0.0963 1.4560 0.1355 0.037 Uiso 1 1 calc R U . . .
C3 C -0.3258(2) 1.41625(17) 0.05855(17) 0.0373(4) Uani 1 1 d . . . . .
H3 H -0.3020 1.4919 0.0276 0.045 Uiso 1 1 calc R U . . .
C4 C -0.4841(2) 1.32798(18) 0.03874(16) 0.0382(4) Uani 1 1 d . . . . .
H4 H -0.5643 1.3445 -0.0060 0.046 Uiso 1 1 calc R U . . .
C5 C -0.52413(18) 1.21667(17) 0.08414(15) 0.0322(3) Uani 1 1 d . . . . .
H5 H -0.6305 1.1580 0.0718 0.039 Uiso 1 1 calc R U . . .
C6 C -0.40194(16) 1.19338(15) 0.14911(13) 0.0249(3) Uani 1 1 d . . . . .
C7 C -0.40551(16) 1.08331(14) 0.19962(13) 0.0245(3) Uani 1 1 d . . . . .
C8 C -0.25362(16) 1.10343(14) 0.24381(13) 0.0231(3) Uani 1 1 d . . . . .
C9 C -0.20031(16) 1.00423(14) 0.28431(13) 0.0245(3) Uani 1 1 d . . . . .
C10 C -0.23848(19) 0.96453(17) 0.38684(15) 0.0326(3) Uani 1 1 d . . . . .
H10 H -0.2910 1.0101 0.4387 0.039 Uiso 1 1 calc R U . . .
C11 C -0.2014(2) 0.85711(19) 0.41724(17) 0.0390(4) Uani 1 1 d . . . . .
H11 H -0.2282 0.8358 0.4895 0.047 Uiso 1 1 calc R U . . .
C12 C -0.1287(2) 0.78452(18) 0.34559(17) 0.0370(4) Uani 1 1 d . . . . .
H12 H -0.1059 0.7133 0.3666 0.044 Uiso 1 1 calc R U . . .
C13 C -0.08825(17) 0.81996(15) 0.23746(15) 0.0280(3) Uani 1 1 d . . . . .
C14 C -0.12155(15) 0.93081(14) 0.20868(13) 0.0232(3) Uani 1 1 d . . . . .
C15 C -0.55344(17) 0.96852(16) 0.20056(15) 0.0303(3) Uani 1 1 d . . . . .
H15A H -0.5298 0.8898 0.2124 0.036 Uiso 1 1 calc R U . . .
H15B H -0.6325 0.9281 0.1150 0.036 Uiso 1 1 calc R U . . .
C16 C -0.6220(2) 1.02830(19) 0.31089(17) 0.0396(4) Uani 1 1 d . . . . .
H16A H -0.7170 0.9511 0.3082 0.047 Uiso 1 1 calc R U . . .
H16B H -0.5449 1.0667 0.3959 0.047 Uiso 1 1 calc R U . . .
H16C H -0.6475 1.1050 0.2985 0.047 Uiso 1 1 calc R U . . .
C17 C 0.01134(16) 1.29830(14) 0.29630(13) 0.0246(3) Uani 1 1 d . . . . .
C18 C 0.24285(17) 1.52495(16) 0.35602(15) 0.0308(3) Uani 1 1 d . . . . .
C19 C 0.2633(3) 1.6524(2) 0.3164(3) 0.0663(7) Uani 1 1 d . . . . .
H19A H 0.3697 1.7272 0.3604 0.080 Uiso 1 1 calc R U . . .
H19B H 0.2457 1.6210 0.2213 0.080 Uiso 1 1 calc R U . . .
H19C H 0.1877 1.6908 0.3420 0.080 Uiso 1 1 calc R U . . .
C20 C 0.3520(2) 1.4581(3) 0.3103(3) 0.0687(7) Uani 1 1 d . . . . .
H20A H 0.4605 1.5252 0.3593 0.082 Uiso 1 1 calc R U . . .
H20B H 0.3275 1.3690 0.3256 0.082 Uiso 1 1 calc R U . . .
H20C H 0.3387 1.4369 0.2166 0.082 Uiso 1 1 calc R U . . .
C21 C 0.2620(3) 1.5676(2) 0.5027(2) 0.0645(7) Uani 1 1 d . . . . .
H21A H 0.3707 1.6346 0.5509 0.077 Uiso 1 1 calc R U . . .
H21B H 0.1925 1.6140 0.5278 0.077 Uiso 1 1 calc R U . . .
H21C H 0.2352 1.4818 0.5237 0.077 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 N3 1.6152(15) . ?
S1 N2 1.6192(14) . ?
O1 C17 1.1997(18) . ?
O2 C17 1.3259(17) . ?
O2 C18 1.4835(18) . ?
N1 C17 1.3993(18) . ?
N1 C1 1.4135(17) . ?
N1 C8 1.4251(17) . ?
N2 C14 1.3492(18) . ?
N3 C13 1.350(2) . ?
C1 C2 1.397(2) . ?
C1 C6 1.409(2) . ?
C2 C3 1.390(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.404(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.439(2) . ?
C7 C8 1.359(2) . ?
C7 C15 1.5027(19) . ?
C8 C9 1.4722(19) . ?
C9 C10 1.3777(19) . ?
C9 C14 1.427(2) . ?
C10 C11 1.424(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.355(3) . ?
C11 H11 0.9400 . ?
C12 C13 1.423(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.4342(19) . ?
C15 C16 1.529(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C18 C20 1.500(3) . ?
C18 C21 1.509(3) . ?
C18 C19 1.511(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 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
N3 S1 N2 100.90(7) . . ?
C17 O2 C18 120.55(11) . . ?
C17 N1 C1 127.93(11) . . ?
C17 N1 C8 121.97(11) . . ?
C1 N1 C8 107.69(11) . . ?
C14 N2 S1 106.29(10) . . ?
C13 N3 S1 106.57(10) . . ?
C2 C1 C6 121.44(13) . . ?
C2 C1 N1 131.54(13) . . ?
C6 C1 N1 106.96(12) . . ?
C3 C2 C1 117.06(14) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 122.16(15) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 120.74(14) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.39(14) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 120.20(13) . . ?
C5 C6 C7 131.36(14) . . ?
C1 C6 C7 108.34(12) . . ?
C8 C7 C6 107.51(12) . . ?
C8 C7 C15 127.84(13) . . ?
C6 C7 C15 124.66(13) . . ?
C7 C8 N1 109.47(12) . . ?
C7 C8 C9 126.86(12) . . ?
N1 C8 C9 123.12(12) . . ?
C10 C9 C14 116.22(13) . . ?
C10 C9 C8 122.41(13) . . ?
C14 C9 C8 120.98(12) . . ?
C9 C10 C11 122.48(15) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C12 C11 C10 122.32(14) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C13 117.59(14) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
N3 C13 C12 126.77(14) . . ?
N3 C13 C14 112.95(13) . . ?
C12 C13 C14 120.28(14) . . ?
N2 C14 C9 125.59(12) . . ?
N2 C14 C13 113.29(13) . . ?
C9 C14 C13 121.08(12) . . ?
C7 C15 C16 112.02(12) . . ?
C7 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C7 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 O2 126.45(13) . . ?
O1 C17 N1 123.17(13) . . ?
O2 C17 N1 110.38(11) . . ?
O2 C18 C20 109.56(14) . . ?
O2 C18 C21 109.91(14) . . ?
C20 C18 C21 112.69(19) . . ?
O2 C18 C19 102.50(13) . . ?
C20 C18 C19 110.51(18) . . ?
C21 C18 C19 111.18(18) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 S1 N2 C14 0.17(11) . . . . ?
N2 S1 N3 C13 -0.42(12) . . . . ?
C17 N1 C1 C2 21.5(2) . . . . ?
C8 N1 C1 C2 -176.12(14) . . . . ?
C17 N1 C1 C6 -161.25(13) . . . . ?
C8 N1 C1 C6 1.11(14) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
N1 C1 C2 C3 175.98(14) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C4 C5 C6 C7 -175.85(14) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
N1 C1 C6 C5 -176.69(12) . . . . ?
C2 C1 C6 C7 177.60(13) . . . . ?
N1 C1 C6 C7 0.03(14) . . . . ?
C5 C6 C7 C8 175.00(14) . . . . ?
C1 C6 C7 C8 -1.22(15) . . . . ?
C5 C6 C7 C15 -4.7(2) . . . . ?
C1 C6 C7 C15 179.10(12) . . . . ?
C6 C7 C8 N1 1.92(15) . . . . ?
C15 C7 C8 N1 -178.41(12) . . . . ?
C6 C7 C8 C9 -169.65(12) . . . . ?
C15 C7 C8 C9 10.0(2) . . . . ?
C17 N1 C8 C7 161.72(12) . . . . ?
C1 N1 C8 C7 -1.93(15) . . . . ?
C17 N1 C8 C9 -26.33(19) . . . . ?
C1 N1 C8 C9 170.02(12) . . . . ?
C7 C8 C9 C10 -60.2(2) . . . . ?
N1 C8 C9 C10 129.33(15) . . . . ?
C7 C8 C9 C14 112.36(16) . . . . ?
N1 C8 C9 C14 -58.14(18) . . . . ?
C14 C9 C10 C11 0.3(2) . . . . ?
C8 C9 C10 C11 173.21(15) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
S1 N3 C13 C12 -179.84(14) . . . . ?
S1 N3 C13 C14 0.54(16) . . . . ?
C11 C12 C13 N3 -178.45(16) . . . . ?
C11 C12 C13 C14 1.1(2) . . . . ?
S1 N2 C14 C9 -177.72(11) . . . . ?
S1 N2 C14 C13 0.13(14) . . . . ?
C10 C9 C14 N2 179.05(13) . . . . ?
C8 C9 C14 N2 6.1(2) . . . . ?
C10 C9 C14 C13 1.4(2) . . . . ?
C8 C9 C14 C13 -171.62(12) . . . . ?
N3 C13 C14 N2 -0.46(18) . . . . ?
C12 C13 C14 N2 179.89(13) . . . . ?
N3 C13 C14 C9 177.50(12) . . . . ?
C12 C13 C14 C9 -2.2(2) . . . . ?
C8 C7 C15 C16 103.53(18) . . . . ?
C6 C7 C15 C16 -76.85(18) . . . . ?
C18 O2 C17 O1 -6.2(2) . . . . ?
C18 O2 C17 N1 173.59(12) . . . . ?
C1 N1 C17 O1 170.03(15) . . . . ?
C8 N1 C17 O1 9.9(2) . . . . ?
C1 N1 C17 O2 -9.75(19) . . . . ?
C8 N1 C17 O2 -169.86(12) . . . . ?
C17 O2 C18 C20 66.3(2) . . . . ?
C17 O2 C18 C21 -58.0(2) . . . . ?
C17 O2 C18 C19 -176.29(16) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'tert-Butyl 2-(2,1,3-benzothiadiazol-4-yl)-3-ethyl-1H-indole-1-carboxylate'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/diethyl ether'
_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_TMCA268_3-Me-N-Me_20160926
_database_code_depnum_ccdc_archive 'CCDC 1523447'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H13 N3 S'
_chemical_formula_moiety         'C16 H13 N3 S'
_chemical_formula_weight         279.36
_chemical_melting_point          413.35-413.95

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.367(3)
_cell_length_b                   8.840(3)
_cell_length_c                   10.153(3)
_cell_angle_alpha                80.099(13)
_cell_angle_beta                 67.010(11)
_cell_angle_gamma                82.285(14)
_cell_volume                     679.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2006
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.38
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292.00
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.933

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            4962
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.906
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2968
_reflns_number_gt                2718
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1750
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2968
_refine_ls_number_parameters     181
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0947P)²+0.4590P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.49937(9) 0.72024(8) 0.94620(7) 0.0517(3) Uani 1 1 d . . . . .
N1 N 0.2742(2) 0.7511(2) 1.45584(19) 0.0336(4) Uani 1 1 d . . . . .
N2 N 0.3936(2) 0.7161(2) 1.1178(2) 0.0388(4) Uani 1 1 d . . . . .
N3 N 0.4147(3) 0.8756(3) 0.8847(2) 0.0489(5) Uani 1 1 d . . . . .
C1 C 0.2123(3) 0.6537(2) 1.5847(2) 0.0303(4) Uani 1 1 d . . . . .
C2 C 0.2939(3) 0.5809(3) 1.6789(3) 0.0400(5) Uani 1 1 d . . . . .
H2 H 0.4101 0.5963 1.6605 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1979(4) 0.4864(3) 1.7988(3) 0.0468(6) Uani 1 1 d . . . . .
H3 H 0.2494 0.4371 1.8638 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0247(4) 0.4620(3) 1.8266(2) 0.0450(6) Uani 1 1 d . . . . .
H4 H -0.0365 0.3952 1.9085 0.054 Uiso 1 1 calc R U . . .
C5 C -0.0573(3) 0.5342(2) 1.7360(2) 0.0376(5) Uani 1 1 d . . . . .
H5 H -0.1736 0.5179 1.7555 0.045 Uiso 1 1 calc R U . . .
C6 C 0.0368(2) 0.6326(2) 1.6140(2) 0.0293(4) Uani 1 1 d . . . . .
C7 C -0.0075(2) 0.7219(2) 1.5021(2) 0.0269(4) Uani 1 1 d . . . . .
C8 C 0.1396(2) 0.7910(2) 1.4065(2) 0.0289(4) Uani 1 1 d . . . . .
C9 C 0.1582(2) 0.8874(2) 1.2687(2) 0.0292(4) Uani 1 1 d . . . . .
C10 C 0.0539(3) 1.0191(2) 1.2602(2) 0.0351(5) Uani 1 1 d . . . . .
H10 H -0.0304 1.0503 1.3460 0.042 Uiso 1 1 calc R U . . .
C11 C 0.0678(3) 1.1109(2) 1.1265(3) 0.0411(5) Uani 1 1 d . . . . .
H11 H -0.0063 1.2009 1.1274 0.049 Uiso 1 1 calc R U . . .
C12 C 0.1847(3) 1.0720(3) 0.9984(3) 0.0425(5) Uani 1 1 d . . . . .
H12 H 0.1928 1.1334 0.9110 0.051 Uiso 1 1 calc R U . . .
C13 C 0.2944(3) 0.9356(2) 1.0008(2) 0.0364(5) Uani 1 1 d . . . . .
C14 C 0.2828(3) 0.8438(2) 1.1345(2) 0.0309(4) Uani 1 1 d . . . . .
C15 C 0.4450(3) 0.8147(3) 1.3956(3) 0.0410(5) Uani 1 1 d . . . . .
H15A H 0.5139 0.7659 1.4512 0.049 Uiso 1 1 calc R U . . .
H15B H 0.5043 0.7954 1.2960 0.049 Uiso 1 1 calc R U . . .
H15C H 0.4300 0.9247 1.3995 0.049 Uiso 1 1 calc R U . . .
C16 C -0.1822(3) 0.7370(3) 1.4938(3) 0.0385(5) Uani 1 1 d . . . . .
H16A H -0.2605 0.6750 1.5763 0.046 Uiso 1 1 calc R U . . .
H16B H -0.2271 0.8440 1.4940 0.046 Uiso 1 1 calc R U . . .
H16C H -0.1733 0.7017 1.4057 0.046 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 N3 1.602(2) . ?
S1 N2 1.613(2) . ?
N1 C8 1.385(2) . ?
N1 C1 1.387(3) . ?
N1 C15 1.465(3) . ?
N2 C14 1.351(3) . ?
N3 C13 1.352(3) . ?
C1 C2 1.406(3) . ?
C1 C6 1.412(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.403(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.400(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.412(3) . ?
C7 C8 1.377(3) . ?
C7 C16 1.484(3) . ?
C8 C9 1.471(3) . ?
C9 C10 1.369(3) . ?
C9 C14 1.434(3) . ?
C10 C11 1.428(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.355(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.417(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.432(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 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
N3 S1 N2 101.65(10) . . ?
C8 N1 C1 107.93(16) . . ?
C8 N1 C15 126.88(17) . . ?
C1 N1 C15 124.73(17) . . ?
C14 N2 S1 105.77(15) . . ?
C13 N3 S1 106.36(17) . . ?
N1 C1 C2 131.27(19) . . ?
N1 C1 C6 107.75(17) . . ?
C2 C1 C6 120.97(19) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.4(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 120.14(19) . . ?
C5 C6 C7 132.40(19) . . ?
C1 C6 C7 107.45(17) . . ?
C8 C7 C6 107.14(16) . . ?
C8 C7 C16 127.75(18) . . ?
C6 C7 C16 125.11(18) . . ?
C7 C8 N1 109.70(17) . . ?
C7 C8 C9 126.48(17) . . ?
N1 C8 C9 123.77(17) . . ?
C10 C9 C14 116.33(18) . . ?
C10 C9 C8 122.44(18) . . ?
C14 C9 C8 121.17(17) . . ?
C9 C10 C11 122.8(2) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C12 C11 C10 121.9(2) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 117.6(2) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
N3 C13 C12 126.3(2) . . ?
N3 C13 C14 112.8(2) . . ?
C12 C13 C14 120.8(2) . . ?
N2 C14 C13 113.38(19) . . ?
N2 C14 C9 126.08(19) . . ?
C13 C14 C9 120.50(19) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 S1 N2 C14 -0.47(17) . . . . ?
N2 S1 N3 C13 0.38(19) . . . . ?
C8 N1 C1 C2 -179.8(2) . . . . ?
C15 N1 C1 C2 -7.2(4) . . . . ?
C8 N1 C1 C6 0.5(2) . . . . ?
C15 N1 C1 C6 173.15(19) . . . . ?
N1 C1 C2 C3 -178.5(2) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
N1 C1 C6 C5 177.70(18) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
N1 C1 C6 C7 -1.3(2) . . . . ?
C2 C1 C6 C7 178.93(19) . . . . ?
C5 C6 C7 C8 -177.2(2) . . . . ?
C1 C6 C7 C8 1.6(2) . . . . ?
C5 C6 C7 C16 3.4(3) . . . . ?
C1 C6 C7 C16 -177.79(18) . . . . ?
C6 C7 C8 N1 -1.3(2) . . . . ?
C16 C7 C8 N1 178.07(19) . . . . ?
C6 C7 C8 C9 176.06(18) . . . . ?
C16 C7 C8 C9 -4.6(3) . . . . ?
C1 N1 C8 C7 0.5(2) . . . . ?
C15 N1 C8 C7 -171.91(19) . . . . ?
C1 N1 C8 C9 -176.97(18) . . . . ?
C15 N1 C8 C9 10.6(3) . . . . ?
C7 C8 C9 C10 58.3(3) . . . . ?
N1 C8 C9 C10 -124.7(2) . . . . ?
C7 C8 C9 C14 -118.9(2) . . . . ?
N1 C8 C9 C14 58.1(3) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
C8 C9 C10 C11 -178.14(19) . . . . ?
C9 C10 C11 C12 0.8(4) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
S1 N3 C13 C12 -178.93(19) . . . . ?
S1 N3 C13 C14 -0.2(2) . . . . ?
C11 C12 C13 N3 177.8(2) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
S1 N2 C14 C13 0.4(2) . . . . ?
S1 N2 C14 C9 178.17(17) . . . . ?
N3 C13 C14 N2 -0.2(3) . . . . ?
C12 C13 C14 N2 178.67(19) . . . . ?
N3 C13 C14 C9 -178.06(18) . . . . ?
C12 C13 C14 C9 0.8(3) . . . . ?
C10 C9 C14 N2 -177.55(19) . . . . ?
C8 C9 C14 N2 -0.2(3) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C8 C9 C14 C13 177.41(18) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
4-(1,3-Dimethyl-1H-indol-2-yl)-2,1,3-benzothiadiazole
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/diethyl ether'
_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_TMCA068
_database_code_depnum_ccdc_archive 'CCDC 1523444'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H18 Cl3 N3 O2 S2'
_chemical_formula_moiety         'C23 H18 Cl3 N3 O2 S2'
_chemical_formula_weight         538.89
_chemical_melting_point          450.65-451.45

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.305(8)
_cell_length_b                   11.319(8)
_cell_length_c                   11.788(8)
_cell_angle_alpha                109.674(6)
_cell_angle_beta                 98.760(4)
_cell_angle_gamma                115.528(4)
_cell_volume                     1200.7(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3628
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      30.51
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.400
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552.00
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_T_max  0.792

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            8608
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.077
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             5216
_reflns_number_gt                4317
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1911
_refine_ls_wR_factor_gt          0.1810
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5216
_refine_ls_number_parameters     298
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1080P)²+0.4990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.90
_refine_diff_density_min         -0.70
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.70561(11) 0.66744(11) 0.32412(10) 0.0705(3) Uani 1 1 d . . . . .
Cl2 Cl 0.84182(13) 0.52624(13) 0.3899(2) 0.1337(8) Uani 1 1 d . . . . .
Cl3 Cl 0.54191(12) 0.37126(14) 0.28626(12) 0.0958(4) Uani 1 1 d . . . . .
S1 S 0.28701(6) 0.73431(6) 0.04198(5) 0.0343(2) Uani 1 1 d . . . . .
S2 S 0.34654(8) 0.28278(8) -0.03771(7) 0.0482(2) Uani 1 1 d . . . . .
O1 O 0.3597(2) 0.8102(2) -0.02307(18) 0.0490(5) Uani 1 1 d . . . . .
O2 O 0.1890(2) 0.58015(19) -0.02783(16) 0.0423(4) Uani 1 1 d . . . . .
N1 N 0.4098(2) 0.7590(2) 0.16176(18) 0.0313(4) Uani 1 1 d . . . . .
N2 N 0.3735(2) 0.4426(2) 0.0485(2) 0.0383(5) Uani 1 1 d . . . . .
N3 N 0.2125(3) 0.1799(2) -0.0122(2) 0.0458(6) Uani 1 1 d . . . . .
C1 C 0.5310(2) 0.9003(3) 0.2427(2) 0.0337(5) Uani 1 1 d . . . . .
C2 C 0.6100(3) 1.0114(3) 0.2135(3) 0.0436(6) Uani 1 1 d . . . . .
H2 H 0.5840 1.0045 0.1308 0.052 Uiso 1 1 calc R U . . .
C3 C 0.7297(3) 1.1335(3) 0.3124(4) 0.0566(9) Uani 1 1 d . . . . .
H3 H 0.7857 1.2113 0.2961 0.068 Uiso 1 1 calc R U . . .
C4 C 0.7696(3) 1.1447(3) 0.4351(4) 0.0599(9) Uani 1 1 d . . . . .
H4 H 0.8525 1.2284 0.4992 0.072 Uiso 1 1 calc R U . . .
C5 C 0.6891(3) 1.0349(3) 0.4635(3) 0.0516(7) Uani 1 1 d . . . . .
H5 H 0.7152 1.0427 0.5465 0.062 Uiso 1 1 calc R U . . .
C6 C 0.5670(3) 0.9109(3) 0.3657(2) 0.0364(5) Uani 1 1 d . . . . .
C7 C 0.4659(3) 0.7783(3) 0.3639(2) 0.0352(5) Uani 1 1 d . . . . .
C8 C 0.3720(2) 0.6885(3) 0.2422(2) 0.0310(5) Uani 1 1 d . . . . .
C9 C 0.2625(2) 0.5339(3) 0.1918(2) 0.0316(5) Uani 1 1 d . . . . .
C10 C 0.1554(3) 0.4895(3) 0.2380(3) 0.0407(6) Uani 1 1 d . . . . .
H10 H 0.1446 0.5610 0.2969 0.049 Uiso 1 1 calc R U . . .
C11 C 0.0596(3) 0.3385(3) 0.1999(3) 0.0501(7) Uani 1 1 d . . . . .
H11 H -0.0128 0.3135 0.2336 0.060 Uiso 1 1 calc R U . . .
C12 C 0.0702(3) 0.2295(3) 0.1161(3) 0.0450(6) Uani 1 1 d . . . . .
H12 H 0.0061 0.1303 0.0913 0.054 Uiso 1 1 calc R U . . .
C13 C 0.1808(3) 0.2703(3) 0.0676(2) 0.0377(5) Uani 1 1 d . . . . .
C14 C 0.2746(2) 0.4209(3) 0.1028(2) 0.0316(5) Uani 1 1 d . . . . .
C15 C 0.4734(3) 0.7421(4) 0.4749(3) 0.0497(7) Uani 1 1 d . . . . .
H15A H 0.5507 0.8266 0.5505 0.060 Uiso 1 1 calc R U . . .
H15B H 0.3867 0.7164 0.4919 0.060 Uiso 1 1 calc R U . . .
H15C H 0.4878 0.6599 0.4541 0.060 Uiso 1 1 calc R U . . .
C16 C 0.2067(2) 0.8214(3) 0.1210(2) 0.0338(5) Uani 1 1 d . . . . .
C17 C 0.2610(3) 0.9699(3) 0.1584(3) 0.0399(6) Uani 1 1 d . . . . .
H17 H 0.3375 1.0234 0.1379 0.048 Uiso 1 1 calc R U . . .
C18 C 0.1997(3) 1.0378(3) 0.2269(3) 0.0427(6) Uani 1 1 d . . . . .
H18 H 0.2358 1.1384 0.2528 0.051 Uiso 1 1 calc R U . . .
C19 C 0.0864(3) 0.9606(3) 0.2581(2) 0.0422(6) Uani 1 1 d . . . . .
C20 C 0.0339(3) 0.8117(3) 0.2179(3) 0.0434(6) Uani 1 1 d . . . . .
H20 H -0.0432 0.7579 0.2376 0.052 Uiso 1 1 calc R U . . .
C21 C 0.0926(3) 0.7409(3) 0.1495(2) 0.0385(5) Uani 1 1 d . . . . .
H21 H 0.0558 0.6401 0.1227 0.046 Uiso 1 1 calc R U . . .
C22 C 0.0216(4) 1.0361(4) 0.3326(3) 0.0597(8) Uani 1 1 d . . . . .
H22A H 0.0715 1.1391 0.3523 0.072 Uiso 1 1 calc R U . . .
H22B H -0.0757 0.9908 0.2814 0.072 Uiso 1 1 calc R U . . .
H22C H 0.0273 1.0271 0.4119 0.072 Uiso 1 1 calc R U . . .
C23 C 0.6964(4) 0.5005(4) 0.2849(3) 0.0589(8) Uani 1 1 d . . . . .
H23 H 0.6988 0.4634 0.1968 0.071 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C23 1.738(4) . ?
Cl2 C23 1.745(4) . ?
Cl3 C23 1.736(4) . ?
S1 O1 1.425(2) . ?
S1 O2 1.428(2) . ?
S1 N1 1.674(2) . ?
S1 C16 1.754(3) . ?
S2 N2 1.610(2) . ?
S2 N3 1.611(3) . ?
N1 C1 1.426(3) . ?
N1 C8 1.434(3) . ?
N2 C14 1.344(3) . ?
N3 C13 1.353(3) . ?
C1 C2 1.384(4) . ?
C1 C6 1.395(4) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.393(6) . ?
C3 H3 0.9400 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.400(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.432(4) . ?
C7 C8 1.357(3) . ?
C7 C15 1.498(4) . ?
C8 C9 1.468(3) . ?
C9 C10 1.370(3) . ?
C9 C14 1.431(3) . ?
C10 C11 1.427(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.363(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.414(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.427(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C17 1.388(4) . ?
C16 C21 1.390(4) . ?
C17 C18 1.392(4) . ?
C17 H17 0.9400 . ?
C18 C19 1.391(4) . ?
C18 H18 0.9400 . ?
C19 C20 1.390(4) . ?
C19 C22 1.506(4) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23 0.9900 . ?

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
O1 S1 O2 119.11(12) . . ?
O1 S1 N1 106.22(12) . . ?
O2 S1 N1 106.79(11) . . ?
O1 S1 C16 110.25(13) . . ?
O2 S1 C16 109.34(13) . . ?
N1 S1 C16 103.97(11) . . ?
N2 S2 N3 100.95(12) . . ?
C1 N1 C8 106.54(19) . . ?
C1 N1 S1 120.92(17) . . ?
C8 N1 S1 120.92(16) . . ?
C14 N2 S2 106.28(18) . . ?
C13 N3 S2 106.59(19) . . ?
C2 C1 C6 122.2(2) . . ?
C2 C1 N1 130.2(2) . . ?
C6 C1 N1 107.5(2) . . ?
C1 C2 C3 116.6(3) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 118.3(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 C7 108.5(2) . . ?
C5 C6 C7 131.4(3) . . ?
C8 C7 C6 107.9(2) . . ?
C8 C7 C15 126.9(3) . . ?
C6 C7 C15 124.9(2) . . ?
C7 C8 N1 109.5(2) . . ?
C7 C8 C9 126.6(2) . . ?
N1 C8 C9 123.2(2) . . ?
C10 C9 C14 116.7(2) . . ?
C10 C9 C8 122.7(2) . . ?
C14 C9 C8 120.1(2) . . ?
C9 C10 C11 122.2(3) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C12 C11 C10 121.9(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 117.9(3) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
N3 C13 C12 127.1(2) . . ?
N3 C13 C14 112.4(2) . . ?
C12 C13 C14 120.5(2) . . ?
N2 C14 C13 113.7(2) . . ?
N2 C14 C9 125.5(2) . . ?
C13 C14 C9 120.8(2) . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 121.2(2) . . ?
C17 C16 S1 119.7(2) . . ?
C21 C16 S1 119.00(19) . . ?
C16 C17 C18 118.5(3) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C19 C18 C17 121.7(2) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C20 C19 C18 118.2(2) . . ?
C20 C19 C22 120.9(3) . . ?
C18 C19 C22 120.9(3) . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C16 118.9(2) . . ?
C20 C21 H21 120.5 . . ?
C16 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl3 C23 Cl1 111.6(2) . . ?
Cl3 C23 Cl2 111.0(2) . . ?
Cl1 C23 Cl2 109.78(18) . . ?
Cl3 C23 H23 108.1 . . ?
Cl1 C23 H23 108.1 . . ?
Cl2 C23 H23 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
O1 S1 N1 C1 45.9(2) . . . . ?
O2 S1 N1 C1 173.94(17) . . . . ?
C16 S1 N1 C1 -70.5(2) . . . . ?
O1 S1 N1 C8 -175.93(17) . . . . ?
O2 S1 N1 C8 -47.8(2) . . . . ?
C16 S1 N1 C8 67.7(2) . . . . ?
N3 S2 N2 C14 -0.1(2) . . . . ?
N2 S2 N3 C13 0.6(2) . . . . ?
C8 N1 C1 C2 179.3(2) . . . . ?
S1 N1 C1 C2 -37.3(3) . . . . ?
C8 N1 C1 C6 2.3(2) . . . . ?
S1 N1 C1 C6 145.73(17) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
N1 C1 C2 C3 -175.2(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
N1 C1 C6 C5 175.3(2) . . . . ?
C2 C1 C6 C7 -179.3(2) . . . . ?
N1 C1 C6 C7 -2.1(3) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C4 C5 C6 C7 177.5(3) . . . . ?
C1 C6 C7 C8 1.0(3) . . . . ?
C5 C6 C7 C8 -176.0(3) . . . . ?
C1 C6 C7 C15 175.3(2) . . . . ?
C5 C6 C7 C15 -1.6(4) . . . . ?
C6 C7 C8 N1 0.5(3) . . . . ?
C15 C7 C8 N1 -173.7(2) . . . . ?
C6 C7 C8 C9 170.5(2) . . . . ?
C15 C7 C8 C9 -3.7(4) . . . . ?
C1 N1 C8 C7 -1.8(2) . . . . ?
S1 N1 C8 C7 -145.17(18) . . . . ?
C1 N1 C8 C9 -172.2(2) . . . . ?
S1 N1 C8 C9 44.4(3) . . . . ?
C7 C8 C9 C10 62.7(4) . . . . ?
N1 C8 C9 C10 -128.6(3) . . . . ?
C7 C8 C9 C14 -108.9(3) . . . . ?
N1 C8 C9 C14 59.8(3) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
C8 C9 C10 C11 -172.0(2) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
S2 N3 C13 C12 179.6(2) . . . . ?
S2 N3 C13 C14 -0.9(3) . . . . ?
C11 C12 C13 N3 177.4(3) . . . . ?
C11 C12 C13 C14 -2.1(4) . . . . ?
S2 N2 C14 C13 -0.5(3) . . . . ?
S2 N2 C14 C9 177.2(2) . . . . ?
N3 C13 C14 N2 1.0(3) . . . . ?
C12 C13 C14 N2 -179.5(2) . . . . ?
N3 C13 C14 C9 -176.9(2) . . . . ?
C12 C13 C14 C9 2.7(4) . . . . ?
C10 C9 C14 N2 -179.0(2) . . . . ?
C8 C9 C14 N2 -7.0(4) . . . . ?
C10 C9 C14 C13 -1.5(3) . . . . ?
C8 C9 C14 C13 170.6(2) . . . . ?
O1 S1 C16 C17 -25.8(2) . . . . ?
O2 S1 C16 C17 -158.5(2) . . . . ?
N1 S1 C16 C17 87.7(2) . . . . ?
O1 S1 C16 C21 156.80(19) . . . . ?
O2 S1 C16 C21 24.0(2) . . . . ?
N1 S1 C16 C21 -89.7(2) . . . . ?
C21 C16 C17 C18 0.8(4) . . . . ?
S1 C16 C17 C18 -176.61(19) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C20 -0.6(4) . . . . ?
C17 C18 C19 C22 179.9(3) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C22 C19 C20 C21 -180.0(3) . . . . ?
C19 C20 C21 C16 0.1(4) . . . . ?
C17 C16 C21 C20 -0.8(4) . . . . ?
S1 C16 C21 C20 176.58(19) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014-3



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
' 4-(3-Methyl-1-tosyl-1H-indol-2-yl)-2,1,3-benzothiaziazole'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/diethyl ether'
_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_TMCA213
_database_code_depnum_ccdc_archive 'CCDC 1523442'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H23 N3 O2 S'
_chemical_formula_moiety         'C22 H23 N3 O2 S'
_chemical_formula_weight         393.50
_chemical_melting_point          '>418 (decomposed)'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.3836
_cell_length_b                   9.5084(5)
_cell_length_c                   12.6685(3)
_cell_angle_alpha                84.707(12)
_cell_angle_beta                 69.198(7)
_cell_angle_gamma                77.736(12)
_cell_volume                     1032.35(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3138
_cell_measurement_theta_min      1.72
_cell_measurement_theta_max      30.36
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.600
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416.00
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_T_max  0.898

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            7509
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         4.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4499
_reflns_number_gt                3999
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1187
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4499
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0566P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.41078(5) 0.90010(5) 0.90581(3) 0.04919(15) Uani 1 1 d . . . . .
O1 O 0.50866(12) 0.83315(11) 1.28845(10) 0.0391(3) Uani 1 1 d . . . . .
O2 O 0.32595(11) 0.74359(10) 1.25236(9) 0.0331(2) Uani 1 1 d . . . . .
N1 N 0.27455(12) 0.97496(11) 1.29954(9) 0.0273(2) Uani 1 1 d . . . . .
N2 N 0.34017(15) 0.95227(13) 1.03525(10) 0.0366(3) Uani 1 1 d . . . . .
N3 N 0.2760(2) 0.82249(17) 0.90111(12) 0.0515(4) Uani 1 1 d . . . . .
C1 C 0.27412(15) 1.08207(13) 1.36909(11) 0.0272(3) Uani 1 1 d . . . . .
C2 C 0.38220(16) 1.09420(15) 1.41836(12) 0.0328(3) Uani 1 1 d . . . . .
H2 H 0.4764 1.0276 1.4036 0.039 Uiso 1 1 calc R U . . .
C3 C 0.34520(18) 1.20827(15) 1.49000(13) 0.0373(3) Uani 1 1 d . . . . .
H3 H 0.4156 1.2190 1.5247 0.045 Uiso 1 1 calc R U . . .
C4 C 0.2061(2) 1.30728(16) 1.51182(13) 0.0403(3) Uani 1 1 d . . . . .
H4 H 0.1835 1.3825 1.5620 0.048 Uiso 1 1 calc R U . . .
C5 C 0.10090(18) 1.29680(15) 1.46090(13) 0.0371(3) Uani 1 1 d . . . . .
H5 H 0.0081 1.3652 1.4750 0.044 Uiso 1 1 calc R U . . .
C6 C 0.13467(15) 1.18259(14) 1.38790(11) 0.0291(3) Uani 1 1 d . . . . .
C7 C 0.05130(15) 1.13899(14) 1.32383(11) 0.0295(3) Uani 1 1 d . . . . .
C8 C 0.13592(14) 1.01270(14) 1.27367(11) 0.0274(3) Uani 1 1 d . . . . .
C9 C 0.10034(15) 0.93209(14) 1.19526(11) 0.0290(3) Uani 1 1 d . . . . .
C10 C -0.03669(17) 0.88395(16) 1.22530(14) 0.0380(3) Uani 1 1 d . . . . .
H10 H -0.1075 0.8984 1.2994 0.046 Uiso 1 1 calc R U . . .
C11 C -0.0755(2) 0.8128(2) 1.14815(17) 0.0508(4) Uani 1 1 d . . . . .
H11 H -0.1713 0.7825 1.1727 0.061 Uiso 1 1 calc R U . . .
C12 C 0.0217(2) 0.7875(2) 1.04017(17) 0.0529(4) Uani 1 1 d . . . . .
H12 H -0.0050 0.7393 0.9905 0.063 Uiso 1 1 calc R U . . .
C13 C 0.1647(2) 0.83606(17) 1.00456(13) 0.0408(3) Uani 1 1 d . . . . .
C14 C 0.20302(16) 0.90948(14) 1.08151(12) 0.0309(3) Uani 1 1 d . . . . .
C15 C -0.09405(16) 1.22417(15) 1.30690(13) 0.0350(3) Uani 1 1 d . . . . .
H15 H -0.1185 1.1701 1.2545 0.042 Uiso 1 1 calc R U . . .
C16 C -0.06690(19) 1.37070(17) 1.25116(15) 0.0433(4) Uani 1 1 d . . . . .
H16A H -0.1616 1.4239 1.2410 0.052 Uiso 1 1 calc R U . . .
H16B H -0.0374 1.4245 1.2990 0.052 Uiso 1 1 calc R U . . .
H16C H 0.0156 1.3565 1.1783 0.052 Uiso 1 1 calc R U . . .
C17 C -0.23242(19) 1.2396(2) 1.41727(16) 0.0542(5) Uani 1 1 d . . . . .
H17A H -0.3238 1.2948 1.4034 0.065 Uiso 1 1 calc R U . . .
H17B H -0.2513 1.1449 1.4469 0.065 Uiso 1 1 calc R U . . .
H17C H -0.2101 1.2888 1.4717 0.065 Uiso 1 1 calc R U . . .
C18 C 0.38331(15) 0.84548(13) 1.27933(11) 0.0282(3) Uani 1 1 d . . . . .
C19 C 0.42397(18) 0.59920(14) 1.21711(14) 0.0389(3) Uani 1 1 d . . . . .
C20 C 0.5600(2) 0.6134(2) 1.11078(16) 0.0599(5) Uani 1 1 d . . . . .
H20A H 0.6233 0.5189 1.0883 0.072 Uiso 1 1 calc R U . . .
H20B H 0.5221 0.6562 1.0509 0.072 Uiso 1 1 calc R U . . .
H20C H 0.6221 0.6743 1.1248 0.072 Uiso 1 1 calc R U . . .
C21 C 0.3099(3) 0.52292(19) 1.1968(2) 0.0633(6) Uani 1 1 d . . . . .
H21A H 0.3609 0.4254 1.1729 0.076 Uiso 1 1 calc R U . . .
H21B H 0.2222 0.5203 1.2661 0.076 Uiso 1 1 calc R U . . .
H21C H 0.2737 0.5743 1.1385 0.076 Uiso 1 1 calc R U . . .
C22 C 0.4751(2) 0.52576(17) 1.31219(16) 0.0531(4) Uani 1 1 d . . . . .
H22A H 0.5388 0.4319 1.2882 0.064 Uiso 1 1 calc R U . . .
H22B H 0.5349 0.5838 1.3321 0.064 Uiso 1 1 calc R U . . .
H22C H 0.3844 0.5144 1.3774 0.064 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 N3 1.6143(17) . ?
S1 N2 1.6164(13) . ?
O1 C18 1.2026(16) . ?
O2 C18 1.3260(16) . ?
O2 C19 1.4884(16) . ?
N1 C18 1.4006(16) . ?
N1 C1 1.4053(16) . ?
N1 C8 1.4182(16) . ?
N2 C14 1.3446(19) . ?
N3 C13 1.352(2) . ?
C1 C2 1.3943(18) . ?
C1 C6 1.4042(18) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.4021(18) . ?
C5 H5 0.9400 . ?
C6 C7 1.4469(18) . ?
C7 C8 1.3615(18) . ?
C7 C15 1.5063(18) . ?
C8 C9 1.4732(18) . ?
C9 C10 1.3704(19) . ?
C9 C14 1.4263(19) . ?
C10 C11 1.423(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.357(3) . ?
C11 H11 0.9400 . ?
C12 C13 1.419(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.4313(19) . ?
C15 C17 1.526(2) . ?
C15 C16 1.532(2) . ?
C15 H15 0.9900 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C19 C20 1.510(3) . ?
C19 C22 1.511(2) . ?
C19 C21 1.516(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 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
N3 S1 N2 100.87(7) . . ?
C18 O2 C19 120.86(11) . . ?
C18 N1 C1 122.80(11) . . ?
C18 N1 C8 128.59(11) . . ?
C1 N1 C8 107.77(10) . . ?
C14 N2 S1 106.34(10) . . ?
C13 N3 S1 106.52(11) . . ?
C2 C1 C6 122.12(12) . . ?
C2 C1 N1 130.29(12) . . ?
C6 C1 N1 107.55(11) . . ?
C3 C2 C1 117.33(13) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.50(13) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.02(13) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.96(13) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.04(12) . . ?
C5 C6 C7 133.16(13) . . ?
C1 C6 C7 107.79(11) . . ?
C8 C7 C6 107.24(11) . . ?
C8 C7 C15 126.20(12) . . ?
C6 C7 C15 126.33(12) . . ?
C7 C8 N1 109.57(11) . . ?
C7 C8 C9 126.48(12) . . ?
N1 C8 C9 123.71(11) . . ?
C10 C9 C14 116.83(13) . . ?
C10 C9 C8 121.92(13) . . ?
C14 C9 C8 121.10(12) . . ?
C9 C10 C11 122.26(15) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C12 C11 C10 121.97(15) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 118.01(15) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
N3 C13 C12 127.11(15) . . ?
N3 C13 C14 112.77(15) . . ?
C12 C13 C14 120.12(15) . . ?
N2 C14 C9 125.73(12) . . ?
N2 C14 C13 113.49(13) . . ?
C9 C14 C13 120.77(13) . . ?
C7 C15 C17 111.61(13) . . ?
C7 C15 C16 110.69(12) . . ?
C17 C15 C16 111.80(13) . . ?
C7 C15 H15 107.5 . . ?
C17 C15 H15 107.5 . . ?
C16 C15 H15 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 O2 126.97(12) . . ?
O1 C18 N1 122.57(12) . . ?
O2 C18 N1 110.44(11) . . ?
O2 C19 C20 109.95(13) . . ?
O2 C19 C22 110.28(12) . . ?
C20 C19 C22 112.18(15) . . ?
O2 C19 C21 101.38(12) . . ?
C20 C19 C21 112.16(16) . . ?
C22 C19 C21 110.39(15) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 S1 N2 C14 -0.08(11) . . . . ?
N2 S1 N3 C13 0.67(13) . . . . ?
C18 N1 C1 C2 8.8(2) . . . . ?
C8 N1 C1 C2 179.10(14) . . . . ?
C18 N1 C1 C6 -168.92(12) . . . . ?
C8 N1 C1 C6 1.43(14) . . . . ?
C6 C1 C2 C3 1.7(2) . . . . ?
N1 C1 C2 C3 -175.69(13) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C7 178.74(15) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
N1 C1 C6 C5 176.19(12) . . . . ?
C2 C1 C6 C7 179.42(13) . . . . ?
N1 C1 C6 C7 -2.67(15) . . . . ?
C5 C6 C7 C8 -175.68(15) . . . . ?
C1 C6 C7 C8 2.95(15) . . . . ?
C5 C6 C7 C15 9.5(2) . . . . ?
C1 C6 C7 C15 -171.84(13) . . . . ?
C6 C7 C8 N1 -2.08(15) . . . . ?
C15 C7 C8 N1 172.72(13) . . . . ?
C6 C7 C8 C9 -176.53(12) . . . . ?
C15 C7 C8 C9 -1.7(2) . . . . ?
C18 N1 C8 C7 170.05(12) . . . . ?
C1 N1 C8 C7 0.45(15) . . . . ?
C18 N1 C8 C9 -15.3(2) . . . . ?
C1 N1 C8 C9 175.09(12) . . . . ?
C7 C8 C9 C10 -58.4(2) . . . . ?
N1 C8 C9 C10 127.86(15) . . . . ?
C7 C8 C9 C14 117.10(15) . . . . ?
N1 C8 C9 C14 -56.62(18) . . . . ?
C14 C9 C10 C11 0.8(2) . . . . ?
C8 C9 C10 C11 176.54(14) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
S1 N3 C13 C12 178.39(15) . . . . ?
S1 N3 C13 C14 -1.05(17) . . . . ?
C11 C12 C13 N3 -179.48(18) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
S1 N2 C14 C9 179.67(11) . . . . ?
S1 N2 C14 C13 -0.53(15) . . . . ?
C10 C9 C14 N2 178.05(13) . . . . ?
C8 C9 C14 N2 2.3(2) . . . . ?
C10 C9 C14 C13 -1.74(19) . . . . ?
C8 C9 C14 C13 -177.48(12) . . . . ?
N3 C13 C14 N2 1.08(19) . . . . ?
C12 C13 C14 N2 -178.40(14) . . . . ?
N3 C13 C14 C9 -179.11(13) . . . . ?
C12 C13 C14 C9 1.4(2) . . . . ?
C8 C7 C15 C17 119.32(17) . . . . ?
C6 C7 C15 C17 -66.84(19) . . . . ?
C8 C7 C15 C16 -115.47(16) . . . . ?
C6 C7 C15 C16 58.36(18) . . . . ?
C19 O2 C18 O1 -6.8(2) . . . . ?
C19 O2 C18 N1 174.63(11) . . . . ?
C1 N1 C18 O1 -23.9(2) . . . . ?
C8 N1 C18 O1 167.88(13) . . . . ?
C1 N1 C18 O2 154.75(12) . . . . ?
C8 N1 C18 O2 -13.46(19) . . . . ?
C18 O2 C19 C20 -61.63(18) . . . . ?
C18 O2 C19 C22 62.59(18) . . . . ?
C18 O2 C19 C21 179.54(14) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'tert-Butyl 2-(2,1,3-benzothiadiazol-4-yl)-3-isopropyl-1H-indole-1-carboxylate'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/diethyl ether'
_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_ymd302
_database_code_depnum_ccdc_archive 'CCDC 1523443'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H15 N3 O2 S'
_chemical_formula_moiety         'C18 H15 N3 O2 S'
_chemical_formula_weight         337.40
_chemical_melting_point          370.15-371.15

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.028(7)
_cell_length_b                   14.215(8)
_cell_length_c                   11.554(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 114.243(7)
_cell_angle_gamma                90.0000
_cell_volume                     1651.5(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3988
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      30.67
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704.00
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.959

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            12326
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         3.458
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3762
_reflns_number_gt                2834
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2121
_refine_ls_wR_factor_gt          0.1900
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3762
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1098P)²+0.2681P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.13663(7) 0.03120(6) 0.67746(6) 0.0665(3) Uani 1 4 d . . .
O1 O 0.74568(17) 0.01250(12) 0.64391(15) 0.0510(4) Uani 1 4 d . . .
O21 O 0.6368(3) -0.05844(14) 0.45715(19) 0.0829(8) Uani 1 4 d . . .
N1 N 0.68049(19) 0.09788(14) 0.46405(17) 0.0444(5) Uani 1 4 d . . .
N2 N 0.9879(2) 0.07187(15) 0.60174(17) 0.0489(5) Uani 1 4 d . . .
N3 N 1.1840(2) 0.0901(2) 0.8079(2) 0.0659(7) Uani 1 4 d . . .
C1 C 0.5937(2) 0.11964(19) 0.3379(2) 0.0482(6) Uani 1 4 d . . .
C2 C 0.5247(3) 0.0604(2) 0.2349(3) 0.0626(8) Uani 1 4 d . . .
C3 C 0.4524(3) 0.1038(3) 0.1197(3) 0.0709(9) Uani 1 4 d . . .
C4 C 0.4487(3) 0.2008(3) 0.1060(3) 0.0730(9) Uani 1 4 d . . .
C5 C 0.5166(3) 0.2583(2) 0.2075(3) 0.0643(8) Uani 1 4 d . . .
C6 C 0.5913(2) 0.21727(19) 0.3259(2) 0.0508(6) Uani 1 4 d . . .
C7 C 0.6821(3) 0.25672(18) 0.4444(2) 0.0501(6) Uani 1 4 d . . .
C8 C 0.7369(2) 0.18431(16) 0.5264(2) 0.0432(5) Uani 1 4 d . . .
C9 C 0.8498(2) 0.18932(17) 0.6507(2) 0.0435(5) Uani 1 4 d . . .
C10 C 0.8525(3) 0.25265(19) 0.7410(2) 0.0547(6) Uani 1 4 d . . .
C11 C 0.9666(3) 0.2633(2) 0.8589(3) 0.0634(8) Uani 1 4 d . . .
C12 C 1.0779(3) 0.2117(2) 0.8883(2) 0.0620(8) Uani 1 4 d . . .
C13 C 1.0815(3) 0.14644(19) 0.7970(2) 0.0511(6) Uani 1 4 d . . .
C14 C 0.9684(2) 0.13527(16) 0.67867(19) 0.0422(5) Uani 1 4 d . . .
C15 C 0.7146(4) 0.3589(2) 0.4649(3) 0.0718(9) Uani 1 4 d . . .
C16 C 0.6836(3) 0.01018(18) 0.5180(2) 0.0500(6) Uani 1 4 d . . .
C17 C 0.7762(3) -0.0790(2) 0.7054(3) 0.0659(8) Uani 1 4 d . . .
C18 C 0.8847(4) -0.0679(3) 0.8319(3) 0.0902(12) Uani 1 4 d . . .
H2 H 0.52734 -0.00541 0.24347 0.0752 Uiso 1 4 calc R . .
H3 H 0.40418 0.06637 0.04848 0.0851 Uiso 1 4 calc R . .
H4 H 0.39901 0.22752 0.02598 0.0875 Uiso 1 4 calc R . .
H5 H 0.51311 0.32406 0.19783 0.0772 Uiso 1 4 calc R . .
H10 H 0.77717 0.29025 0.72516 0.0656 Uiso 1 4 calc R . .
H11 H 0.96369 0.30786 0.9179 0.0761 Uiso 1 4 calc R . .
H12 H 1.15096 0.21873 0.96691 0.0744 Uiso 1 4 calc R . .
H15A H 0.65916 0.39371 0.38944 0.0861 Uiso 1 4 calc R . .
H15B H 0.69822 0.38093 0.53663 0.0861 Uiso 1 4 calc R . .
H15C H 0.80744 0.36843 0.48183 0.0861 Uiso 1 4 calc R . .
H17A H 0.80302 -0.12267 0.6546 0.0791 Uiso 1 4 calc R . .
H17B H 0.69729 -0.10463 0.71295 0.0791 Uiso 1 4 calc R . .
H18A H 0.90592 -0.1286 0.8739 0.1082 Uiso 1 4 calc R . .
H18B H 0.9626 -0.04291 0.82367 0.1082 Uiso 1 4 calc R . .
H18C H 0.8572 -0.02493 0.88183 0.1082 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 N2 1.616(2) yes . .
S1 N3 1.613(3) yes . .
O1 C16 1.330(3) yes . .
O1 C17 1.453(3) yes . .
O21 C16 1.189(3) yes . .
N1 C1 1.410(3) yes . .
N1 C8 1.431(3) yes . .
N1 C16 1.388(3) yes . .
N2 C14 1.344(3) yes . .
N3 C13 1.348(4) yes . .
C1 C2 1.401(4) yes . .
C1 C6 1.394(4) yes . .
C2 C3 1.385(4) yes . .
C3 C4 1.385(5) yes . .
C4 C5 1.373(4) yes . .
C5 C6 1.402(4) yes . .
C6 C7 1.438(3) yes . .
C7 C8 1.361(3) yes . .
C7 C15 1.491(4) yes . .
C8 C9 1.466(3) yes . .
C9 C10 1.369(4) yes . .
C9 C14 1.434(4) yes . .
C10 C11 1.434(3) yes . .
C11 C12 1.349(5) yes . .
C12 C13 1.416(4) yes . .
C13 C14 1.432(3) yes . .
C17 C18 1.469(4) yes . .
C2 H2 0.940 no . .
C3 H3 0.940 no . .
C4 H4 0.940 no . .
C5 H5 0.940 no . .
C10 H10 0.940 no . .
C11 H11 0.940 no . .
C12 H12 0.940 no . .
C15 H15A 0.970 no . .
C15 H15B 0.970 no . .
C15 H15C 0.970 no . .
C17 H17A 0.980 no . .
C17 H17B 0.980 no . .
C18 H18A 0.970 no . .
C18 H18B 0.970 no . .
C18 H18C 0.970 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N2 S1 N3 100.78(13) yes . . .
C16 O1 C17 115.1(2) yes . . .
C1 N1 C8 107.59(19) yes . . .
C1 N1 C16 122.82(19) yes . . .
C8 N1 C16 128.30(18) yes . . .
S1 N2 C14 106.53(14) yes . . .
S1 N3 C13 106.49(15) yes . . .
N1 C1 C2 130.4(2) yes . . .
N1 C1 C6 107.36(19) yes . . .
C2 C1 C6 122.2(2) yes . . .
C1 C2 C3 116.5(3) yes . . .
C2 C3 C4 122.1(3) yes . . .
C3 C4 C5 121.0(3) yes . . .
C4 C5 C6 118.8(3) yes . . .
C1 C6 C5 119.4(2) yes . . .
C1 C6 C7 108.4(2) yes . . .
C5 C6 C7 131.9(3) yes . . .
C6 C7 C8 107.7(2) yes . . .
C6 C7 C15 124.0(2) yes . . .
C8 C7 C15 128.1(2) yes . . .
N1 C8 C7 108.78(18) yes . . .
N1 C8 C9 123.62(19) yes . . .
C7 C8 C9 126.9(2) yes . . .
C8 C9 C10 121.5(2) yes . . .
C8 C9 C14 121.6(2) yes . . .
C10 C9 C14 116.63(19) yes . . .
C9 C10 C11 122.0(3) yes . . .
C10 C11 C12 122.3(3) yes . . .
C11 C12 C13 118.0(2) yes . . .
N3 C13 C12 126.7(2) yes . . .
N3 C13 C14 113.1(2) yes . . .
C12 C13 C14 120.3(2) yes . . .
N2 C14 C9 126.08(18) yes . . .
N2 C14 C13 113.1(2) yes . . .
C9 C14 C13 120.8(2) yes . . .
O1 C16 O21 124.8(2) yes . . .
O1 C16 N1 112.1(2) yes . . .
O21 C16 N1 123.2(2) yes . . .
O1 C17 C18 108.8(3) yes . . .
C1 C2 H2 121.739 no . . .
C3 C2 H2 121.734 no . . .
C2 C3 H3 118.947 no . . .
C4 C3 H3 118.956 no . . .
C3 C4 H4 119.502 no . . .
C5 C4 H4 119.499 no . . .
C4 C5 H5 120.608 no . . .
C6 C5 H5 120.606 no . . .
C9 C10 H10 119.014 no . . .
C11 C10 H10 119.010 no . . .
C10 C11 H11 118.863 no . . .
C12 C11 H11 118.851 no . . .
C11 C12 H12 120.988 no . . .
C13 C12 H12 120.993 no . . .
C7 C15 H15A 109.466 no . . .
C7 C15 H15B 109.469 no . . .
C7 C15 H15C 109.477 no . . .
H15A C15 H15B 109.471 no . . .
H15A C15 H15C 109.470 no . . .
H15B C15 H15C 109.474 no . . .
O1 C17 H17A 109.932 no . . .
O1 C17 H17B 109.937 no . . .
C18 C17 H17A 109.937 no . . .
C18 C17 H17B 109.941 no . . .
H17A C17 H17B 108.334 no . . .
C17 C18 H18A 109.471 no . . .
C17 C18 H18B 109.476 no . . .
C17 C18 H18C 109.470 no . . .
H18A C18 H18B 109.469 no . . .
H18A C18 H18C 109.471 no . . .
H18B C18 H18C 109.472 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N2 S1 N3 C13 -0.2(2) no . . . .
N3 S1 N2 C14 -0.29(18) no . . . .
C16 O1 C17 C18 158.6(2) no . . . .
C17 O1 C16 O21 11.1(4) no . . . .
C17 O1 C16 N1 -168.3(2) no . . . .
C1 N1 C8 C7 3.0(3) no . . . .
C1 N1 C8 C9 -168.2(2) no . . . .
C8 N1 C1 C2 172.9(2) no . . . .
C8 N1 C1 C6 -3.4(3) no . . . .
C1 N1 C16 O1 -163.6(2) no . . . .
C1 N1 C16 O21 17.0(4) no . . . .
C16 N1 C1 C2 -19.1(4) no . . . .
C16 N1 C1 C6 164.6(2) no . . . .
C8 N1 C16 O1 1.8(4) no . . . .
C8 N1 C16 O21 -177.7(2) no . . . .
C16 N1 C8 C7 -164.1(2) no . . . .
C16 N1 C8 C9 24.7(4) no . . . .
S1 N2 C14 C9 179.99(18) no . . . .
S1 N2 C14 C13 0.7(2) no . . . .
S1 N3 C13 C12 -179.4(2) no . . . .
S1 N3 C13 C14 0.6(3) no . . . .
N1 C1 C2 C3 -176.3(3) no . . . .
N1 C1 C6 C5 177.2(2) no . . . .
N1 C1 C6 C7 2.5(3) no . . . .
C2 C1 C6 C5 0.6(4) no . . . .
C2 C1 C6 C7 -174.1(3) no . . . .
C6 C1 C2 C3 -0.5(4) no . . . .
C1 C2 C3 C4 0.5(5) no . . . .
C2 C3 C4 C5 -0.5(5) no . . . .
C3 C4 C5 C6 0.6(5) no . . . .
C4 C5 C6 C1 -0.6(5) no . . . .
C4 C5 C6 C7 172.7(3) no . . . .
C1 C6 C7 C8 -0.6(3) no . . . .
C1 C6 C7 C15 174.9(2) no . . . .
C5 C6 C7 C8 -174.5(3) no . . . .
C5 C6 C7 C15 1.1(5) no . . . .
C6 C7 C8 N1 -1.5(3) no . . . .
C6 C7 C8 C9 169.4(2) no . . . .
C15 C7 C8 N1 -176.8(3) no . . . .
C15 C7 C8 C9 -5.9(5) no . . . .
N1 C8 C9 C10 -138.0(2) no . . . .
N1 C8 C9 C14 48.6(4) no . . . .
C7 C8 C9 C10 52.4(4) no . . . .
C7 C8 C9 C14 -121.0(3) no . . . .
C8 C9 C10 C11 -175.0(2) no . . . .
C8 C9 C14 N2 -4.1(4) no . . . .
C8 C9 C14 C13 175.2(2) no . . . .
C10 C9 C14 N2 -177.8(2) no . . . .
C10 C9 C14 C13 1.5(4) no . . . .
C14 C9 C10 C11 -1.3(4) no . . . .
C9 C10 C11 C12 -0.2(5) no . . . .
C10 C11 C12 C13 1.4(5) no . . . .
C11 C12 C13 N3 178.7(3) no . . . .
C11 C12 C13 C14 -1.2(4) no . . . .
N3 C13 C14 N2 -0.8(3) no . . . .
N3 C13 C14 C9 179.8(2) no . . . .
C12 C13 C14 N2 179.1(2) no . . . .
C12 C13 C14 C9 -0.3(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N2 3.025(4) no . .
O1 C1 3.572(3) no . .
O1 C8 2.777(3) no . .
O1 C9 2.751(3) no . .
O1 C14 2.903(3) no . .
O21 C1 2.827(4) no . .
O21 C2 2.893(4) no . .
O21 C17 2.656(4) no . .
N1 N2 3.119(3) no . .
N1 C5 3.585(4) no . .
N1 C14 3.170(3) no . .
N1 C17 3.576(4) no . .
N2 C8 2.999(3) no . .
N2 C16 3.209(4) no . .
C1 C4 2.748(4) no . .
C2 C5 2.828(5) no . .
C2 C16 3.094(4) no . .
C3 C6 2.762(4) no . .
C5 C15 3.212(4) no . .
C6 C16 3.574(4) no . .
C7 C10 3.160(4) no . .
C9 C12 2.880(3) no . .
C9 C15 3.164(4) no . .
C9 C16 3.144(4) no . .
C10 C13 2.781(4) no . .
C10 C15 3.284(4) no . .
C11 C14 2.772(4) no . .
C14 C16 3.418(4) no . .
C16 C18 3.564(4) no . .
S1 O21 3.465(4) no . 3_756
S1 N1 3.580(3) no . 3_756
S1 N2 3.287(3) no . 3_756
O21 S1 3.465(4) no . 3_756
O21 C4 3.546(4) no . 2_645
O21 C5 3.259(4) no . 2_645
N1 S1 3.580(3) no . 3_756
N2 S1 3.287(3) no . 3_756
N2 N2 3.208(3) no . 3_756
N2 C11 3.588(4) no . 4_554
C4 O21 3.546(4) no . 2_655
C5 O21 3.259(4) no . 2_655
C5 C10 3.565(5) no . 4_554
C6 C10 3.429(5) no . 4_554
C7 C10 3.564(5) no . 4_554
C10 C5 3.565(5) no . 4_555
C10 C6 3.429(5) no . 4_555
C10 C7 3.564(5) no . 4_555
C11 N2 3.588(4) no . 4_555
S1 H18B 3.2108 no . .
O1 H18A 3.2173 no . .
O1 H18B 2.5645 no . .
O1 H18C 2.5644 no . .
O21 H2 2.3819 no . .
O21 H17A 2.4423 no . .
O21 H17B 2.8271 no . .
N1 H2 2.8229 no . .
N2 H18B 3.1469 no . .
N3 H12 2.7194 no . .
N3 H18B 3.1516 no . .
C1 H3 3.2230 no . .
C1 H5 3.2670 no . .
C2 H4 3.2624 no . .
C3 H5 3.2507 no . .
C4 H2 3.2761 no . .
C5 H3 3.2386 no . .
C5 H15A 2.8070 no . .
C6 H2 3.2974 no . .
C6 H4 3.2393 no . .
C6 H15A 2.6340 no . .
C6 H15B 3.2206 no . .
C6 H15C 3.1651 no . .
C7 H5 2.8544 no . .
C7 H10 3.0091 no . .
C8 H10 2.6270 no . .
C8 H15A 3.3145 no . .
C8 H15B 2.8371 no . .
C8 H15C 2.8371 no . .
C9 H11 3.2811 no . .
C9 H15B 3.1845 no . .
C9 H15C 3.1237 no . .
C10 H12 3.2904 no . .
C10 H15B 2.9146 no . .
C10 H15C 3.2712 no . .
C12 H10 3.2659 no . .
C13 H11 3.2236 no . .
C13 H18B 3.0641 no . .
C14 H10 3.2432 no . .
C14 H12 3.3236 no . .
C14 H18B 3.0519 no . .
C15 H5 3.0119 no . .
C15 H10 2.9611 no . .
C16 H2 2.9307 no . .
C16 H17A 2.4669 no . .
C16 H17B 2.7357 no . .
H2 H3 2.3343 no . .
H3 H4 2.3035 no . .
H4 H5 2.3146 no . .
H5 H15A 2.3553 no . .
H5 H15C 3.5992 no . .
H10 H11 2.3433 no . .
H10 H15B 2.3680 no . .
H10 H15C 3.1657 no . .
H11 H12 2.2870 no . .
H17A H18A 2.3139 no . .
H17A H18B 2.3185 no . .
H17A H18C 2.8093 no . .
H17B H18A 2.3139 no . .
H17B H18B 2.8094 no . .
H17B H18C 2.3184 no . .
S1 H2 3.4526 no . 3_756
S1 H11 3.3935 no . 2_746
O1 H15A 3.5998 no . 4_555
O21 H4 3.0845 no . 2_645
O21 H5 2.5095 no . 2_645
N2 H11 2.6534 no . 4_554
N3 H3 2.8624 no . 1_656
N3 H4 3.2981 no . 1_656
N3 H15B 3.4412 no . 2_746
C1 H10 3.0980 no . 4_554
C1 H17B 3.0231 no . 3_656
C2 H5 3.5115 no . 2_645
C2 H10 3.5396 no . 4_554
C2 H15A 3.0654 no . 2_645
C2 H17B 2.8218 no . 3_656
C3 H12 3.4658 no . 1_454
C3 H15A 3.2154 no . 2_645
C3 H15B 3.2335 no . 4_554
C3 H17B 3.0140 no . 3_656
C3 H18C 3.5864 no . 3_656
C4 H10 3.3069 no . 4_554
C4 H12 3.0160 no . 1_454
C4 H15B 3.3722 no . 4_554
C4 H17B 3.4063 no . 3_656
C5 H2 3.4729 no . 2_655
C5 H10 2.8797 no . 4_554
C6 H10 2.7438 no . 4_554
C6 H17B 3.4233 no . 3_656
C7 H10 3.1852 no . 4_554
C7 H11 3.3707 no . 4_554
C8 H11 3.2270 no . 4_554
C9 H11 3.4036 no . 4_554
C10 H15C 3.4767 no . 4_555
C11 H15C 3.2632 no . 4_555
C11 H17A 3.0716 no . 2_756
C11 H18A 3.4072 no . 3_757
C12 H4 3.2395 no . 1_656
C12 H17A 2.8373 no . 2_756
C12 H18A 2.9282 no . 3_757
C13 H17A 3.4817 no . 2_756
C14 H11 3.0995 no . 4_554
C15 H2 3.3704 no . 2_655
C15 H3 3.2051 no . 2_655
C15 H18C 3.1947 no . 4_554
C18 H12 3.3020 no . 3_757
C18 H15C 3.3130 no . 2_746
H2 S1 3.4526 no . 3_756
H2 C5 3.4729 no . 2_645
H2 C15 3.3704 no . 2_645
H2 H5 2.6045 no . 2_645
H2 H15A 2.4598 no . 2_645
H2 H15B 3.5582 no . 2_645
H2 H17B 3.1402 no . 3_656
H3 N3 2.8624 no . 1_454
H3 C15 3.2051 no . 2_645
H3 H3 3.3505 no . 3_655
H3 H12 3.3489 no . 1_454
H3 H15A 2.7272 no . 2_645
H3 H15B 2.8773 no . 2_645
H3 H15B 3.3851 no . 4_554
H3 H15C 3.5797 no . 2_645
H3 H17B 3.4175 no . 3_656
H3 H18C 3.3481 no . 3_656
H4 O21 3.0845 no . 2_655
H4 N3 3.2981 no . 1_454
H4 C12 3.2395 no . 1_454
H4 H12 2.5359 no . 1_454
H4 H15B 3.5980 no . 4_554
H4 H17A 3.1677 no . 2_655
H4 H17B 3.4691 no . 2_655
H5 O21 2.5095 no . 2_655
H5 C2 3.5115 no . 2_655
H5 H2 2.6045 no . 2_655
H5 H10 3.2349 no . 4_554
H10 C1 3.0980 no . 4_555
H10 C2 3.5396 no . 4_555
H10 C4 3.3069 no . 4_555
H10 C5 2.8797 no . 4_555
H10 C6 2.7438 no . 4_555
H10 C7 3.1852 no . 4_555
H10 H5 3.2349 no . 4_555
H11 S1 3.3935 no . 2_756
H11 N2 2.6534 no . 4_555
H11 C7 3.3707 no . 4_555
H11 C8 3.2270 no . 4_555
H11 C9 3.4036 no . 4_555
H11 C14 3.0995 no . 4_555
H11 H15C 3.2923 no . 4_555
H11 H17A 3.1726 no . 2_756
H11 H18A 3.3922 no . 3_757
H12 C3 3.4658 no . 1_656
H12 C4 3.0160 no . 1_656
H12 C18 3.3020 no . 3_757
H12 H3 3.3489 no . 1_656
H12 H4 2.5359 no . 1_656
H12 H17A 2.8101 no . 2_756
H12 H18A 2.5230 no . 3_757
H12 H18C 3.2834 no . 3_757
H15A O1 3.5998 no . 4_554
H15A C2 3.0654 no . 2_655
H15A C3 3.2154 no . 2_655
H15A H2 2.4598 no . 2_655
H15A H3 2.7272 no . 2_655
H15A H18C 2.9007 no . 4_554
H15B N3 3.4412 no . 2_756
H15B C3 3.2335 no . 4_555
H15B C4 3.3722 no . 4_555
H15B H2 3.5582 no . 2_655
H15B H3 2.8773 no . 2_655
H15B H3 3.3851 no . 4_555
H15B H4 3.5980 no . 4_555
H15B H18B 3.5791 no . 2_756
H15C C10 3.4767 no . 4_554
H15C C11 3.2632 no . 4_554
H15C C18 3.3130 no . 2_756
H15C H3 3.5797 no . 2_655
H15C H11 3.2923 no . 4_554
H15C H18A 2.9060 no . 2_756
H15C H18B 2.8965 no . 2_756
H15C H18C 2.6657 no . 4_554
H17A C11 3.0716 no . 2_746
H17A C12 2.8373 no . 2_746
H17A C13 3.4817 no . 2_746
H17A H4 3.1677 no . 2_645
H17A H11 3.1726 no . 2_746
H17A H12 2.8101 no . 2_746
H17B C1 3.0231 no . 3_656
H17B C2 2.8218 no . 3_656
H17B C3 3.0140 no . 3_656
H17B C4 3.4063 no . 3_656
H17B C6 3.4233 no . 3_656
H17B H2 3.1402 no . 3_656
H17B H3 3.4175 no . 3_656
H17B H4 3.4691 no . 2_645
H18A C11 3.4072 no . 3_757
H18A C12 2.9282 no . 3_757
H18A H11 3.3922 no . 3_757
H18A H12 2.5230 no . 3_757
H18A H15C 2.9060 no . 2_746
H18B H15B 3.5791 no . 2_746
H18B H15C 2.8965 no . 2_746
H18B H18C 3.3022 no . 3_757
H18C C3 3.5864 no . 3_656
H18C C15 3.1947 no . 4_555
H18C H3 3.3481 no . 3_656
H18C H12 3.2834 no . 3_757
H18C H15A 2.9007 no . 4_555
H18C H15C 2.6657 no . 4_555
H18C H18B 3.3022 no . 3_757
H18C H18C 3.2888 no . 3_757

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
' Ethyl 2-(2,1,3-benzothiadiazol-4-yl)-3-methyl-1H-indole-1-carboxylate'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/chloroform'
_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_TMCA069
_database_code_depnum_ccdc_archive 'CCDC 1523446'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H19 N3 O S'
_chemical_formula_moiety         'C20 H19 N3 O S'
_chemical_formula_weight         349.45
_chemical_melting_point          408.75-410.35

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.119(5)
_cell_length_b                   13.780(5)
_cell_length_c                   21.310(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.941(7)
_cell_angle_gamma                90.0000
_cell_volume                     3516(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10055
_cell_measurement_theta_min      2.08
_cell_measurement_theta_max      30.23
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472.00
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  0.961

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            27090
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.129
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             8018
_reflns_number_gt                6550
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1178
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         8018
_refine_ls_number_parameters     475
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0523P)²+0.9487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.22473(4) 0.16211(4) 0.34900(2) 0.04262(14) Uani 1 1 d . . . . .
S2 S 0.57913(4) 0.21916(4) 0.41771(3) 0.05101(16) Uani 1 1 d . . . . .
O1 O 0.51755(11) 0.26982(10) 0.25450(7) 0.0494(3) Uani 1 1 d . . . . .
O2 O 0.32832(12) 0.43543(10) 0.46539(7) 0.0522(4) Uani 1 1 d . . . . .
N1 N 0.51561(11) 0.10790(10) 0.24034(7) 0.0329(3) Uani 1 1 d . . . . .
N2 N 0.32477(11) 0.12639(11) 0.31264(7) 0.0356(3) Uani 1 1 d . . . . .
N3 N 0.12244(12) 0.09730(12) 0.31413(8) 0.0426(4) Uani 1 1 d . . . . .
N4 N 0.24921(11) 0.29723(10) 0.49434(7) 0.0311(3) Uani 1 1 d . . . . .
N5 N 0.45867(12) 0.22682(11) 0.44035(7) 0.0385(3) Uani 1 1 d . . . . .
N6 N 0.64584(13) 0.15136(12) 0.47277(9) 0.0479(4) Uani 1 1 d . . . . .
C1 C 0.62951(13) 0.08867(13) 0.26178(8) 0.0337(4) Uani 1 1 d . . . . .
C2 C 0.71816(14) 0.15210(14) 0.28107(9) 0.0395(4) Uani 1 1 d . . . . .
H2A H 0.7079 0.2197 0.2809 0.047 Uiso 1 1 calc R U . . .
C3 C 0.82211(15) 0.11040(16) 0.30046(10) 0.0475(5) Uani 1 1 d . . . . .
H3A H 0.8836 0.1508 0.3143 0.057 Uiso 1 1 calc R U . . .
C4 C 0.83766(16) 0.01086(17) 0.30002(10) 0.0497(5) Uani 1 1 d . . . . .
H4A H 0.9092 -0.0148 0.3137 0.060 Uiso 1 1 calc R U . . .
C5 C 0.75061(16) -0.05108(15) 0.27998(10) 0.0461(5) Uani 1 1 d . . . . .
H5A H 0.7623 -0.1185 0.2793 0.055 Uiso 1 1 calc R U . . .
C6 C 0.64374(14) -0.01207(13) 0.26061(8) 0.0363(4) Uani 1 1 d . . . . .
C7 C 0.53633(15) -0.05607(13) 0.24165(9) 0.0364(4) Uani 1 1 d . . . . .
C8 C 0.46005(14) 0.01765(12) 0.23075(8) 0.0329(4) Uani 1 1 d . . . . .
C9 C 0.33834(14) 0.00786(12) 0.22673(8) 0.0326(4) Uani 1 1 d . . . . .
C10 C 0.27713(15) -0.05739(13) 0.18722(9) 0.0380(4) Uani 1 1 d . . . . .
H10 H 0.3128 -0.0921 0.1581 0.046 Uiso 1 1 calc R U . . .
C11 C 0.16179(16) -0.07477(14) 0.18843(9) 0.0428(4) Uani 1 1 d . . . . .
H11 H 0.1238 -0.1207 0.1604 0.051 Uiso 1 1 calc R U . . .
C12 C 0.10513(15) -0.02677(14) 0.22902(9) 0.0407(4) Uani 1 1 d . . . . .
H12 H 0.0290 -0.0392 0.2297 0.049 Uiso 1 1 calc R U . . .
C13 C 0.16389(14) 0.04247(13) 0.27027(8) 0.0350(4) Uani 1 1 d . . . . .
C14 C 0.28031(13) 0.05965(12) 0.26978(8) 0.0308(3) Uani 1 1 d . . . . .
C15 C 0.5131(2) -0.16229(15) 0.24216(13) 0.0499(5) Uani 1 1 d . . . . .
H1 H 0.570(3) -0.196(2) 0.2710(15) 0.099(10) Uiso 1 1 d . . . . .
H2 H 0.441(2) -0.1746(19) 0.2524(12) 0.077(8) Uiso 1 1 d . . . . .
H3 H 0.508(2) -0.192(2) 0.1998(16) 0.100(10) Uiso 1 1 d . . . . .
C16 C 0.47932(14) 0.20333(13) 0.22118(9) 0.0354(4) Uani 1 1 d . . . . .
C17 C 0.40590(16) 0.22126(13) 0.15635(9) 0.0400(4) Uani 1 1 d . . . . .
C18 C 0.28403(18) 0.23887(17) 0.16462(11) 0.0572(6) Uani 1 1 d . . . . .
H18A H 0.2809 0.2900 0.1956 0.069 Uiso 1 1 calc R U . . .
H18B H 0.2412 0.2581 0.1242 0.069 Uiso 1 1 calc R U . . .
H18C H 0.2529 0.1797 0.1793 0.069 Uiso 1 1 calc R U . . .
C19 C 0.4492(2) 0.31563(15) 0.13020(11) 0.0574(6) Uani 1 1 d . . . . .
H19A H 0.4449 0.3679 0.1602 0.069 Uiso 1 1 calc R U . . .
H19B H 0.5262 0.3069 0.1240 0.069 Uiso 1 1 calc R U . . .
H19C H 0.4038 0.3316 0.0899 0.069 Uiso 1 1 calc R U . . .
C20 C 0.4141(2) 0.14125(16) 0.10797(10) 0.0653(7) Uani 1 1 d . . . . .
H20A H 0.4918 0.1314 0.1036 0.078 Uiso 1 1 calc R U . . .
H20B H 0.3838 0.0815 0.1223 0.078 Uiso 1 1 calc R U . . .
H20C H 0.3720 0.1599 0.0673 0.078 Uiso 1 1 calc R U . . .
C21 C 0.13587(13) 0.31068(12) 0.47145(8) 0.0300(3) Uani 1 1 d . . . . .
C22 C 0.07732(15) 0.39509(13) 0.45195(9) 0.0373(4) Uani 1 1 d . . . . .
H22 H 0.1136 0.4555 0.4524 0.045 Uiso 1 1 calc R U . . .
C23 C -0.03613(15) 0.38651(15) 0.43188(9) 0.0430(4) Uani 1 1 d . . . . .
H23 H -0.0778 0.4421 0.4180 0.052 Uiso 1 1 calc R U . . .
C24 C -0.09043(15) 0.29719(15) 0.43177(9) 0.0436(4) Uani 1 1 d . . . . .
H24 H -0.1676 0.2935 0.4170 0.052 Uiso 1 1 calc R U . . .
C25 C -0.03296(14) 0.21463(14) 0.45286(9) 0.0390(4) Uani 1 1 d . . . . .
H25 H -0.0704 0.1549 0.4531 0.047 Uiso 1 1 calc R U . . .
C26 C 0.08234(13) 0.22050(12) 0.47407(8) 0.0308(3) Uani 1 1 d . . . . .
C27 C 0.16554(13) 0.15087(12) 0.49909(8) 0.0326(4) Uani 1 1 d . . . . .
C28 C 0.26564(13) 0.19916(12) 0.51146(8) 0.0310(3) Uani 1 1 d . . . . .
C29 C 0.37707(13) 0.15671(12) 0.53024(8) 0.0317(3) Uani 1 1 d . . . . .
C30 C 0.40051(15) 0.09499(13) 0.58099(9) 0.0385(4) Uani 1 1 d . . . . .
H30 H 0.3440 0.0818 0.6054 0.046 Uiso 1 1 calc R U . . .
C31 C 0.50651(16) 0.04997(14) 0.59847(9) 0.0440(4) Uani 1 1 d . . . . .
H31 H 0.5173 0.0075 0.6334 0.053 Uiso 1 1 calc R U . . .
C32 C 0.59248(16) 0.06686(14) 0.56583(10) 0.0435(4) Uani 1 1 d . . . . .
H32 H 0.6628 0.0382 0.5783 0.052 Uiso 1 1 calc R U . . .
C33 C 0.57255(14) 0.12912(13) 0.51235(9) 0.0376(4) Uani 1 1 d . . . . .
C34 C 0.46520(13) 0.17293(12) 0.49373(8) 0.0324(4) Uani 1 1 d . . . . .
C35 C 0.14532(18) 0.04488(14) 0.50527(13) 0.0467(5) Uani 1 1 d . . . . .
H4 H 0.104(2) 0.0184(18) 0.4652(13) 0.074(8) Uiso 1 1 d . . . . .
H5 H 0.212(2) 0.0082(18) 0.5133(12) 0.071(7) Uiso 1 1 d . . . . .
H6 H 0.100(2) 0.0289(17) 0.5418(12) 0.068(7) Uiso 1 1 d . . . . .
C36 C 0.32129(14) 0.38004(13) 0.50817(9) 0.0350(4) Uani 1 1 d . . . . .
C37 C 0.37300(16) 0.40153(14) 0.57701(9) 0.0419(4) Uani 1 1 d . . . . .
C38 C 0.49465(18) 0.36686(17) 0.59069(12) 0.0613(6) Uani 1 1 d . . . . .
H38A H 0.5368 0.3963 0.5605 0.074 Uiso 1 1 calc R U . . .
H38B H 0.5271 0.3856 0.6335 0.074 Uiso 1 1 calc R U . . .
H38C H 0.4970 0.2968 0.5867 0.074 Uiso 1 1 calc R U . . .
C39 C 0.3721(2) 0.51279(16) 0.58358(12) 0.0607(6) Uani 1 1 d . . . . .
H39A H 0.4153 0.5414 0.5536 0.073 Uiso 1 1 calc R U . . .
H39B H 0.2958 0.5362 0.5748 0.073 Uiso 1 1 calc R U . . .
H39C H 0.4047 0.5308 0.6265 0.073 Uiso 1 1 calc R U . . .
C40 C 0.3050(2) 0.3560(2) 0.62408(10) 0.0678(7) Uani 1 1 d . . . . .
H40A H 0.3399 0.3709 0.6671 0.081 Uiso 1 1 calc R U . . .
H40B H 0.2297 0.3820 0.6168 0.081 Uiso 1 1 calc R U . . .
H40C H 0.3023 0.2862 0.6182 0.081 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 N3 1.6126(17) . ?
S1 N2 1.6139(15) . ?
S2 N5 1.6107(15) . ?
S2 N6 1.6151(19) . ?
O1 C16 1.207(2) . ?
O2 C36 1.202(2) . ?
N1 C1 1.410(2) . ?
N1 C8 1.414(2) . ?
N1 C16 1.426(2) . ?
N2 C14 1.348(2) . ?
N3 C13 1.357(2) . ?
N4 C21 1.397(2) . ?
N4 C28 1.406(2) . ?
N4 C36 1.440(2) . ?
N5 C34 1.350(2) . ?
N6 C33 1.352(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.400(3) . ?
C2 C3 1.388(3) . ?
C2 H2A 0.9400 . ?
C3 C4 1.385(3) . ?
C3 H3A 0.9400 . ?
C4 C5 1.372(3) . ?
C4 H4A 0.9400 . ?
C5 C6 1.404(3) . ?
C5 H5A 0.9400 . ?
C6 C7 1.436(3) . ?
C7 C8 1.369(2) . ?
C7 C15 1.491(3) . ?
C8 C9 1.470(2) . ?
C9 C10 1.369(2) . ?
C9 C14 1.430(2) . ?
C10 C11 1.422(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.357(3) . ?
C11 H11 0.9400 . ?
C12 C13 1.413(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.432(2) . ?
C15 H1 0.96(3) . ?
C15 H2 0.95(3) . ?
C15 H3 0.99(3) . ?
C16 C17 1.542(3) . ?
C17 C20 1.523(3) . ?
C17 C18 1.534(3) . ?
C17 C19 1.539(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.392(2) . ?
C21 C26 1.407(2) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9400 . ?
C23 C24 1.396(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.373(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.402(2) . ?
C25 H25 0.9400 . ?
C26 C27 1.433(2) . ?
C27 C28 1.373(2) . ?
C27 C35 1.490(3) . ?
C28 C29 1.469(2) . ?
C29 C30 1.370(2) . ?
C29 C34 1.433(2) . ?
C30 C31 1.423(3) . ?
C30 H30 0.9400 . ?
C31 C32 1.360(3) . ?
C31 H31 0.9400 . ?
C32 C33 1.417(3) . ?
C32 H32 0.9400 . ?
C33 C34 1.433(2) . ?
C35 H4 0.99(3) . ?
C35 H5 0.95(3) . ?
C35 H6 1.04(2) . ?
C36 C37 1.532(3) . ?
C37 C40 1.528(3) . ?
C37 C38 1.534(3) . ?
C37 C39 1.540(3) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 H38C 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 H39C 0.9700 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 H40C 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
N3 S1 N2 101.01(8) . . ?
N5 S2 N6 101.24(8) . . ?
C1 N1 C8 107.57(14) . . ?
C1 N1 C16 120.58(14) . . ?
C8 N1 C16 130.62(15) . . ?
C14 N2 S1 106.40(11) . . ?
C13 N3 S1 106.57(12) . . ?
C21 N4 C28 108.07(13) . . ?
C21 N4 C36 119.93(14) . . ?
C28 N4 C36 130.69(14) . . ?
C34 N5 S2 106.20(12) . . ?
C33 N6 S2 106.33(13) . . ?
C2 C1 C6 122.34(16) . . ?
C2 C1 N1 130.35(17) . . ?
C6 C1 N1 107.31(15) . . ?
C3 C2 C1 116.72(18) . . ?
C3 C2 H2A 121.6 . . ?
C1 C2 H2A 121.6 . . ?
C4 C3 C2 121.76(19) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 H3A 119.1 . . ?
C5 C4 C3 121.28(18) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 118.87(19) . . ?
C4 C5 H5A 120.6 . . ?
C6 C5 H5A 120.6 . . ?
C1 C6 C5 119.02(17) . . ?
C1 C6 C7 108.36(15) . . ?
C5 C6 C7 132.51(18) . . ?
C8 C7 C6 107.05(16) . . ?
C8 C7 C15 127.35(18) . . ?
C6 C7 C15 125.19(17) . . ?
C7 C8 N1 109.53(15) . . ?
C7 C8 C9 125.93(16) . . ?
N1 C8 C9 122.70(14) . . ?
C10 C9 C14 116.66(15) . . ?
C10 C9 C8 122.62(15) . . ?
C14 C9 C8 120.36(15) . . ?
C9 C10 C11 122.66(17) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C12 C11 C10 121.70(18) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 118.01(16) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
N3 C13 C12 126.84(16) . . ?
N3 C13 C14 112.55(16) . . ?
C12 C13 C14 120.59(16) . . ?
N2 C14 C9 126.18(15) . . ?
N2 C14 C13 113.47(14) . . ?
C9 C14 C13 120.35(16) . . ?
C7 C15 H1 110.9(18) . . ?
C7 C15 H2 111.0(16) . . ?
H1 C15 H2 111(2) . . ?
C7 C15 H3 113.1(18) . . ?
H1 C15 H3 109(2) . . ?
H2 C15 H3 102(2) . . ?
O1 C16 N1 117.30(17) . . ?
O1 C16 C17 121.38(16) . . ?
N1 C16 C17 120.89(15) . . ?
C20 C17 C18 110.96(19) . . ?
C20 C17 C19 107.74(17) . . ?
C18 C17 C19 107.26(17) . . ?
C20 C17 C16 113.64(17) . . ?
C18 C17 C16 110.75(15) . . ?
C19 C17 C16 106.13(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N4 130.03(15) . . ?
C22 C21 C26 122.22(15) . . ?
N4 C21 C26 107.67(14) . . ?
C23 C22 C21 117.26(17) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C22 C23 C24 121.52(17) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C25 C24 C23 121.02(17) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 119.15(17) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C26 C21 118.73(16) . . ?
C25 C26 C27 133.57(16) . . ?
C21 C26 C27 107.69(14) . . ?
C28 C27 C26 107.25(15) . . ?
C28 C27 C35 127.64(17) . . ?
C26 C27 C35 124.97(16) . . ?
C27 C28 N4 109.32(15) . . ?
C27 C28 C29 127.36(16) . . ?
N4 C28 C29 122.73(14) . . ?
C30 C29 C34 116.39(16) . . ?
C30 C29 C28 122.09(15) . . ?
C34 C29 C28 121.41(15) . . ?
C29 C30 C31 123.04(17) . . ?
C29 C30 H30 118.5 . . ?
C31 C30 H30 118.5 . . ?
C32 C31 C30 121.58(18) . . ?
C32 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
C31 C32 C33 117.82(17) . . ?
C31 C32 H32 121.1 . . ?
C33 C32 H32 121.1 . . ?
N6 C33 C32 126.35(17) . . ?
N6 C33 C34 112.83(17) . . ?
C32 C33 C34 120.78(16) . . ?
N5 C34 C33 113.37(15) . . ?
N5 C34 C29 126.29(15) . . ?
C33 C34 C29 120.33(16) . . ?
C27 C35 H4 110.7(15) . . ?
C27 C35 H5 113.1(15) . . ?
H4 C35 H5 105(2) . . ?
C27 C35 H6 112.7(13) . . ?
H4 C35 H6 107.8(19) . . ?
H5 C35 H6 107(2) . . ?
O2 C36 N4 117.41(16) . . ?
O2 C36 C37 122.47(16) . . ?
N4 C36 C37 119.61(15) . . ?
C40 C37 C36 111.54(16) . . ?
C40 C37 C38 110.3(2) . . ?
C36 C37 C38 111.09(16) . . ?
C40 C37 C39 109.70(18) . . ?
C36 C37 C39 105.78(16) . . ?
C38 C37 C39 108.24(17) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 S1 N2 C14 0.16(14) . . . . ?
N2 S1 N3 C13 -0.19(14) . . . . ?
N6 S2 N5 C34 -1.06(14) . . . . ?
N5 S2 N6 C33 1.30(15) . . . . ?
C8 N1 C1 C2 -176.27(17) . . . . ?
C16 N1 C1 C2 15.1(3) . . . . ?
C8 N1 C1 C6 4.25(18) . . . . ?
C16 N1 C1 C6 -164.38(15) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
N1 C1 C2 C3 179.39(17) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
N1 C1 C6 C5 -179.92(15) . . . . ?
C2 C1 C6 C7 177.22(16) . . . . ?
N1 C1 C6 C7 -3.25(19) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -175.15(19) . . . . ?
C1 C6 C7 C8 1.0(2) . . . . ?
C5 C6 C7 C8 177.03(19) . . . . ?
C1 C6 C7 C15 -172.09(18) . . . . ?
C5 C6 C7 C15 4.0(3) . . . . ?
C6 C7 C8 N1 1.70(19) . . . . ?
C15 C7 C8 N1 174.57(19) . . . . ?
C6 C7 C8 C9 -163.03(16) . . . . ?
C15 C7 C8 C9 9.8(3) . . . . ?
C1 N1 C8 C7 -3.73(19) . . . . ?
C16 N1 C8 C7 163.34(16) . . . . ?
C1 N1 C8 C9 161.59(15) . . . . ?
C16 N1 C8 C9 -31.3(3) . . . . ?
C7 C8 C9 C10 -52.8(3) . . . . ?
N1 C8 C9 C10 144.34(17) . . . . ?
C7 C8 C9 C14 120.2(2) . . . . ?
N1 C8 C9 C14 -42.7(2) . . . . ?
C14 C9 C10 C11 -0.6(3) . . . . ?
C8 C9 C10 C11 172.65(17) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
S1 N3 C13 C12 178.83(16) . . . . ?
S1 N3 C13 C14 0.16(18) . . . . ?
C11 C12 C13 N3 -179.74(18) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
S1 N2 C14 C9 -179.84(14) . . . . ?
S1 N2 C14 C13 -0.08(18) . . . . ?
C10 C9 C14 N2 179.66(17) . . . . ?
C8 C9 C14 N2 6.3(3) . . . . ?
C10 C9 C14 C13 -0.1(2) . . . . ?
C8 C9 C14 C13 -173.47(15) . . . . ?
N3 C13 C14 N2 -0.1(2) . . . . ?
C12 C13 C14 N2 -178.81(16) . . . . ?
N3 C13 C14 C9 179.72(15) . . . . ?
C12 C13 C14 C9 1.0(3) . . . . ?
C1 N1 C16 O1 -44.2(2) . . . . ?
C8 N1 C16 O1 150.13(17) . . . . ?
C1 N1 C16 C17 128.37(17) . . . . ?
C8 N1 C16 C17 -37.3(2) . . . . ?
O1 C16 C17 C20 150.33(19) . . . . ?
N1 C16 C17 C20 -21.9(2) . . . . ?
O1 C16 C17 C18 -84.0(2) . . . . ?
N1 C16 C17 C18 103.76(18) . . . . ?
O1 C16 C17 C19 32.1(2) . . . . ?
N1 C16 C17 C19 -140.14(16) . . . . ?
C28 N4 C21 C22 176.21(17) . . . . ?
C36 N4 C21 C22 7.9(3) . . . . ?
C28 N4 C21 C26 -0.37(17) . . . . ?
C36 N4 C21 C26 -168.63(14) . . . . ?
N4 C21 C22 C23 -179.36(16) . . . . ?
C26 C21 C22 C23 -3.2(3) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C22 C23 C24 C25 1.2(3) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C24 C25 C26 C21 -1.6(3) . . . . ?
C24 C25 C26 C27 179.28(18) . . . . ?
C22 C21 C26 C25 3.7(2) . . . . ?
N4 C21 C26 C25 -179.39(15) . . . . ?
C22 C21 C26 C27 -176.98(15) . . . . ?
N4 C21 C26 C27 -0.08(18) . . . . ?
C25 C26 C27 C28 179.67(18) . . . . ?
C21 C26 C27 C28 0.51(19) . . . . ?
C25 C26 C27 C35 3.8(3) . . . . ?
C21 C26 C27 C35 -175.38(18) . . . . ?
C26 C27 C28 N4 -0.74(19) . . . . ?
C35 C27 C28 N4 175.00(18) . . . . ?
C26 C27 C28 C29 -172.00(16) . . . . ?
C35 C27 C28 C29 3.7(3) . . . . ?
C21 N4 C28 C27 0.70(18) . . . . ?
C36 N4 C28 C27 167.25(16) . . . . ?
C21 N4 C28 C29 172.45(15) . . . . ?
C36 N4 C28 C29 -21.0(3) . . . . ?
C27 C28 C29 C30 -53.2(3) . . . . ?
N4 C28 C29 C30 136.58(18) . . . . ?
C27 C28 C29 C34 122.66(19) . . . . ?
N4 C28 C29 C34 -47.5(2) . . . . ?
C34 C29 C30 C31 1.3(3) . . . . ?
C28 C29 C30 C31 177.38(17) . . . . ?
C29 C30 C31 C32 0.9(3) . . . . ?
C30 C31 C32 C33 -1.7(3) . . . . ?
S2 N6 C33 C32 176.50(16) . . . . ?
S2 N6 C33 C34 -1.13(19) . . . . ?
C31 C32 C33 N6 -177.20(19) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
S2 N5 C34 C33 0.49(18) . . . . ?
S2 N5 C34 C29 -178.75(14) . . . . ?
N6 C33 C34 N5 0.4(2) . . . . ?
C32 C33 C34 N5 -177.35(17) . . . . ?
N6 C33 C34 C29 179.73(16) . . . . ?
C32 C33 C34 C29 1.9(3) . . . . ?
C30 C29 C34 N5 176.55(17) . . . . ?
C28 C29 C34 N5 0.4(3) . . . . ?
C30 C29 C34 C33 -2.6(2) . . . . ?
C28 C29 C34 C33 -178.76(16) . . . . ?
C21 N4 C36 O2 -58.9(2) . . . . ?
C28 N4 C36 O2 135.85(19) . . . . ?
C21 N4 C36 C37 113.13(18) . . . . ?
C28 N4 C36 C37 -52.1(2) . . . . ?
O2 C36 C37 C40 148.7(2) . . . . ?
N4 C36 C37 C40 -23.0(2) . . . . ?
O2 C36 C37 C38 -87.8(2) . . . . ?
N4 C36 C37 C38 100.6(2) . . . . ?
O2 C36 C37 C39 29.5(2) . . . . ?
N4 C36 C37 C39 -142.19(17) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
' 2-(2,1,3-Benzothiadiazol-4-yl)-3-methyl-1H-indol-1-yl-2,2-dimethylpropan-1-one'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/diethyl ether'
_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_TMCA077_Bz
_database_code_depnum_ccdc_archive 'CCDC 1523445'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H15 N3 O S'
_chemical_formula_moiety         'C22 H15 N3 O S'
_chemical_formula_weight         369.44
_chemical_melting_point          464.35-464.75

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   20.828(7)
_cell_length_b                   11.825(4)
_cell_length_c                   15.926(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.203(4)
_cell_angle_gamma                90.0000
_cell_volume                     3657(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3733
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      30.41
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536.00
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_T_max  0.981

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            13776
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.085
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4172
_reflns_number_gt                2931
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0843
_refine_ls_wR_factor_ref         0.2476
_refine_ls_wR_factor_gt          0.2211
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4172
_refine_ls_number_parameters     244
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1160P)²+1.5111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.15667(5) 0.36893(8) 0.04703(7) 0.0648(4) Uani 1 8 d . . .
O1 O 0.18919(11) 0.23470(19) 0.33890(15) 0.0513(6) Uani 1 8 d . . .
N1 N 0.26607(12) 0.1381(2) 0.29507(16) 0.0403(6) Uani 1 8 d . . .
N2 N 0.20704(14) 0.2890(2) 0.12535(18) 0.0501(7) Uani 1 8 d . . .
N3 N 0.13068(15) 0.2815(3) -0.03670(19) 0.0588(8) Uani 1 8 d . . .
C1 C 0.32487(15) 0.1490(2) 0.37410(19) 0.0402(7) Uani 1 8 d . . .
C2 C 0.33122(17) 0.1868(3) 0.4595(2) 0.0480(7) Uani 1 8 d . . .
C3 C 0.39688(19) 0.1835(3) 0.5258(2) 0.0559(9) Uani 1 8 d . . .
C4 C 0.45321(19) 0.1459(3) 0.5067(2) 0.0574(9) Uani 1 8 d . . .
C5 C 0.44626(17) 0.1064(3) 0.4225(2) 0.0528(8) Uani 1 8 d . . .
C6 C 0.38107(16) 0.1066(3) 0.3548(2) 0.0436(7) Uani 1 8 d . . .
C7 C 0.35636(16) 0.0712(3) 0.2616(2) 0.0454(7) Uani 1 8 d . . .
C8 C 0.28738(15) 0.0916(3) 0.22647(19) 0.0409(7) Uani 1 8 d . . .
C9 C 0.24130(15) 0.0878(3) 0.1315(2) 0.0409(7) Uani 1 8 d . . .
C10 C 0.23239(17) -0.0079(3) 0.0800(2) 0.0487(8) Uani 1 8 d . . .
C11 C 0.18897(18) -0.0106(3) -0.0122(2) 0.0536(8) Uani 1 8 d . . .
C12 C 0.15418(17) 0.0817(3) -0.0553(2) 0.0532(8) Uani 1 8 d . . .
C13 C 0.16192(16) 0.1831(3) -0.0054(2) 0.0460(7) Uani 1 8 d . . .
C14 C 0.20476(15) 0.1865(3) 0.08734(19) 0.0404(7) Uani 1 8 d . . .
C15 C 0.40093(18) 0.0255(3) 0.2146(2) 0.0601(9) Uani 1 8 d . . .
C16 C 0.19899(16) 0.1632(3) 0.2899(2) 0.0411(7) Uani 1 8 d . . .
C17 C 0.14215(15) 0.0916(3) 0.23087(19) 0.0405(7) Uani 1 8 d . . .
C18 C 0.15012(16) -0.0238(3) 0.2220(2) 0.0476(8) Uani 1 8 d . . .
C19 C 0.09503(18) -0.0895(3) 0.1712(3) 0.0596(9) Uani 1 8 d . . .
C20 C 0.03220(19) -0.0391(4) 0.1270(3) 0.0745(13) Uani 1 8 d . . .
C21 C 0.02398(19) 0.0747(4) 0.1343(3) 0.0785(13) Uani 1 8 d . . .
C22 C 0.07770(17) 0.1403(3) 0.1872(3) 0.0593(9) Uani 1 8 d . . .
H2 H 0.29261 0.21366 0.47196 0.0576 Uiso 1 8 calc R . .
H3 H 0.40319 0.20759 0.58514 0.0670 Uiso 1 8 calc R . .
H4 H 0.49758 0.14727 0.55279 0.0689 Uiso 1 8 calc R . .
H5 H 0.48516 0.07954 0.41076 0.0633 Uiso 1 8 calc R . .
H10 H 0.25614 -0.07491 0.10693 0.0585 Uiso 1 8 calc R . .
H11 H 0.18418 -0.07943 -0.04463 0.0643 Uiso 1 8 calc R . .
H12 H 0.12545 0.07861 -0.1171 0.0638 Uiso 1 8 calc R . .
H15A H 0.44849 0.02003 0.2573 0.0721 Uiso 1 8 calc R . .
H15B H 0.38452 -0.04972 0.19055 0.0721 Uiso 1 8 calc R . .
H15C H 0.39913 0.07615 0.16511 0.0721 Uiso 1 8 calc R . .
H18 H 0.1939 -0.05785 0.25114 0.0571 Uiso 1 8 calc R . .
H19 H 0.10038 -0.16884 0.16686 0.0715 Uiso 1 8 calc R . .
H20 H -0.0057 -0.0838 0.09107 0.0894 Uiso 1 8 calc R . .
H21 H -0.01934 0.10876 0.10236 0.0941 Uiso 1 8 calc R . .
H22 H 0.07098 0.2187 0.19408 0.0711 Uiso 1 8 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 N2 1.613(3) yes . .
S1 N3 1.618(3) yes . .
O1 C16 1.217(4) yes . .
N1 C1 1.409(3) yes . .
N1 C8 1.430(4) yes . .
N1 C16 1.401(4) yes . .
N2 C14 1.348(4) yes . .
N3 C13 1.338(4) yes . .
C1 C2 1.391(5) yes . .
C1 C6 1.406(5) yes . .
C2 C3 1.394(4) yes . .
C3 C4 1.387(6) yes . .
C4 C5 1.376(5) yes . .
C5 C6 1.396(4) yes . .
C6 C7 1.446(4) yes . .
C7 C8 1.362(4) yes . .
C7 C15 1.488(6) yes . .
C8 C9 1.470(4) yes . .
C9 C10 1.370(5) yes . .
C9 C14 1.431(4) yes . .
C10 C11 1.418(4) yes . .
C11 C12 1.352(5) yes . .
C12 C13 1.415(5) yes . .
C13 C14 1.424(4) yes . .
C16 C17 1.482(4) yes . .
C17 C18 1.389(4) yes . .
C17 C22 1.393(4) yes . .
C18 C19 1.379(4) yes . .
C19 C20 1.378(5) yes . .
C20 C21 1.368(6) yes . .
C21 C22 1.372(5) yes . .
C2 H2 0.950 no . .
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C5 H5 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .
C15 H15A 0.980 no . .
C15 H15B 0.980 no . .
C15 H15C 0.980 no . .
C18 H18 0.950 no . .
C19 H19 0.950 no . .
C20 H20 0.950 no . .
C21 H21 0.950 no . .
C22 H22 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N2 S1 N3 101.13(15) yes . . .
C1 N1 C8 107.9(2) yes . . .
C1 N1 C16 124.0(3) yes . . .
C8 N1 C16 127.9(2) yes . . .
S1 N2 C14 105.79(19) yes . . .
S1 N3 C13 106.0(2) yes . . .
N1 C1 C2 130.3(3) yes . . .
N1 C1 C6 107.2(3) yes . . .
C2 C1 C6 122.4(3) yes . . .
C1 C2 C3 116.9(3) yes . . .
C2 C3 C4 121.3(3) yes . . .
C3 C4 C5 121.5(3) yes . . .
C4 C5 C6 118.8(4) yes . . .
C1 C6 C5 119.1(3) yes . . .
C1 C6 C7 108.2(2) yes . . .
C5 C6 C7 132.7(3) yes . . .
C6 C7 C8 107.5(3) yes . . .
C6 C7 C15 124.5(3) yes . . .
C8 C7 C15 128.0(3) yes . . .
N1 C8 C7 109.1(2) yes . . .
N1 C8 C9 122.1(3) yes . . .
C7 C8 C9 128.0(3) yes . . .
C8 C9 C10 122.6(3) yes . . .
C8 C9 C14 120.9(3) yes . . .
C10 C9 C14 116.5(3) yes . . .
C9 C10 C11 122.3(3) yes . . .
C10 C11 C12 122.1(3) yes . . .
C11 C12 C13 117.9(3) yes . . .
N3 C13 C12 125.9(3) yes . . .
N3 C13 C14 113.6(3) yes . . .
C12 C13 C14 120.5(3) yes . . .
N2 C14 C9 125.9(2) yes . . .
N2 C14 C13 113.5(3) yes . . .
C9 C14 C13 120.6(3) yes . . .
O1 C16 N1 120.3(2) yes . . .
O1 C16 C17 121.5(3) yes . . .
N1 C16 C17 117.9(3) yes . . .
C16 C17 C18 121.9(3) yes . . .
C16 C17 C22 119.0(3) yes . . .
C18 C17 C22 119.0(3) yes . . .
C17 C18 C19 120.6(3) yes . . .
C18 C19 C20 119.4(4) yes . . .
C19 C20 C21 120.5(3) yes . . .
C20 C21 C22 120.6(3) yes . . .
C17 C22 C21 119.9(3) yes . . .
C1 C2 H2 121.571 no . . .
C3 C2 H2 121.574 no . . .
C2 C3 H3 119.367 no . . .
C4 C3 H3 119.370 no . . .
C3 C4 H4 119.247 no . . .
C5 C4 H4 119.256 no . . .
C4 C5 H5 120.582 no . . .
C6 C5 H5 120.579 no . . .
C9 C10 H10 118.828 no . . .
C11 C10 H10 118.827 no . . .
C10 C11 H11 118.947 no . . .
C12 C11 H11 118.946 no . . .
C11 C12 H12 121.054 no . . .
C13 C12 H12 121.043 no . . .
C7 C15 H15A 109.468 no . . .
C7 C15 H15B 109.478 no . . .
C7 C15 H15C 109.473 no . . .
H15A C15 H15B 109.471 no . . .
H15A C15 H15C 109.468 no . . .
H15B C15 H15C 109.470 no . . .
C17 C18 H18 119.712 no . . .
C19 C18 H18 119.711 no . . .
C18 C19 H19 120.286 no . . .
C20 C19 H19 120.296 no . . .
C19 C20 H20 119.755 no . . .
C21 C20 H20 119.754 no . . .
C20 C21 H21 119.697 no . . .
C22 C21 H21 119.686 no . . .
C17 C22 H22 120.069 no . . .
C21 C22 H22 120.069 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N2 S1 N3 C13 -0.4(3) no . . . .
N3 S1 N2 C14 -0.5(2) no . . . .
C1 N1 C8 C7 1.6(3) no . . . .
C1 N1 C8 C9 -169.0(2) no . . . .
C8 N1 C1 C2 -178.1(3) no . . . .
C8 N1 C1 C6 -1.6(3) no . . . .
C1 N1 C16 O1 29.2(4) no . . . .
C1 N1 C16 C17 -144.1(2) no . . . .
C16 N1 C1 C2 -1.7(5) no . . . .
C16 N1 C1 C6 174.8(2) no . . . .
C8 N1 C16 O1 -155.1(3) no . . . .
C8 N1 C16 C17 31.6(4) no . . . .
C16 N1 C8 C7 -174.6(2) no . . . .
C16 N1 C8 C9 14.8(4) no . . . .
S1 N2 C14 C9 -179.8(2) no . . . .
S1 N2 C14 C13 1.2(3) no . . . .
S1 N3 C13 C12 179.6(3) no . . . .
S1 N3 C13 C14 1.1(4) no . . . .
N1 C1 C2 C3 177.5(3) no . . . .
N1 C1 C6 C5 -179.4(2) no . . . .
N1 C1 C6 C7 1.1(3) no . . . .
C2 C1 C6 C5 -2.6(4) no . . . .
C2 C1 C6 C7 178.0(3) no . . . .
C6 C1 C2 C3 1.5(4) no . . . .
C1 C2 C3 C4 1.0(5) no . . . .
C2 C3 C4 C5 -2.3(5) no . . . .
C3 C4 C5 C6 1.2(5) no . . . .
C4 C5 C6 C1 1.2(5) no . . . .
C4 C5 C6 C7 -179.5(3) no . . . .
C1 C6 C7 C8 -0.2(3) no . . . .
C1 C6 C7 C15 177.6(2) no . . . .
C5 C6 C7 C8 -179.5(3) no . . . .
C5 C6 C7 C15 -1.8(6) no . . . .
C6 C7 C8 N1 -0.9(3) no . . . .
C6 C7 C8 C9 169.0(3) no . . . .
C15 C7 C8 N1 -178.5(3) no . . . .
C15 C7 C8 C9 -8.7(5) no . . . .
N1 C8 C9 C10 -131.9(3) no . . . .
N1 C8 C9 C14 50.0(4) no . . . .
C7 C8 C9 C10 59.4(5) no . . . .
C7 C8 C9 C14 -118.7(4) no . . . .
C8 C9 C10 C11 -178.7(3) no . . . .
C8 C9 C14 N2 -1.0(5) no . . . .
C8 C9 C14 C13 178.0(3) no . . . .
C10 C9 C14 N2 -179.2(3) no . . . .
C10 C9 C14 C13 -0.2(5) no . . . .
C14 C9 C10 C11 -0.5(5) no . . . .
C9 C10 C11 C12 0.8(6) no . . . .
C10 C11 C12 C13 -0.3(6) no . . . .
C11 C12 C13 N3 -178.9(3) no . . . .
C11 C12 C13 C14 -0.4(5) no . . . .
N3 C13 C14 N2 -1.6(4) no . . . .
N3 C13 C14 C9 179.3(3) no . . . .
C12 C13 C14 N2 179.8(3) no . . . .
C12 C13 C14 C9 0.7(5) no . . . .
O1 C16 C17 C18 -136.6(3) no . . . .
O1 C16 C17 C22 39.5(4) no . . . .
N1 C16 C17 C18 36.6(4) no . . . .
N1 C16 C17 C22 -147.3(3) no . . . .
C16 C17 C18 C19 175.7(3) no . . . .
C16 C17 C22 C21 -178.3(3) no . . . .
C18 C17 C22 C21 -2.0(6) no . . . .
C22 C17 C18 C19 -0.4(5) no . . . .
C17 C18 C19 C20 1.9(6) no . . . .
C18 C19 C20 C21 -1.1(7) no . . . .
C19 C20 C21 C22 -1.3(7) no . . . .
C20 C21 C22 C17 2.9(7) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 C1 2.860(4) no . .
O1 C2 2.941(4) no . .
O1 C8 3.592(4) no . .
O1 C18 3.518(4) no . .
O1 C22 2.901(4) no . .
N1 N2 3.098(4) no . .
N1 C5 3.583(4) no . .
N1 C14 3.138(4) no . .
N1 C18 2.970(4) no . .
N2 C8 2.982(4) no . .
N2 C16 3.070(5) no . .
N2 C17 3.427(5) no . .
C1 C4 2.743(4) no . .
C2 C5 2.830(6) no . .
C2 C16 3.095(4) no . .
C3 C6 2.775(5) no . .
C5 C15 3.242(5) no . .
C7 C10 3.242(4) no . .
C8 C17 3.051(5) no . .
C8 C18 3.146(5) no . .
C9 C12 2.870(4) no . .
C9 C15 3.188(5) no . .
C9 C16 3.089(5) no . .
C9 C17 3.023(5) no . .
C9 C18 3.067(5) no . .
C10 C13 2.769(4) no . .
C10 C15 3.411(4) no . .
C10 C18 3.300(6) no . .
C11 C14 2.770(5) no . .
C14 C16 3.282(5) no . .
C14 C17 3.216(5) no . .
C14 C22 3.588(6) no . .
C17 C20 2.763(5) no . .
C18 C21 2.749(5) no . .
C19 C22 2.765(5) no . .
S1 C1 3.513(3) no . 6_555
S1 C6 3.442(4) no . 6_555
O1 C2 3.513(5) no . 7_556
O1 C3 3.404(5) no . 7_556
O1 C10 3.475(4) no . 6_555
O1 C11 3.558(4) no . 4_555
N3 C15 3.510(5) no . 7_555
C1 S1 3.513(3) no . 6_545
C2 O1 3.513(5) no . 7_556
C3 O1 3.404(5) no . 7_556
C4 C5 3.584(5) no . 3_656
C5 C4 3.584(5) no . 3_656
C6 S1 3.442(4) no . 6_545
C10 O1 3.475(4) no . 6_545
C11 O1 3.558(4) no . 4_554
C12 C18 3.583(5) no . 4_554
C15 N3 3.510(5) no . 7_555
C18 C12 3.583(5) no . 4_555
O1 H2 2.4270 no . .
O1 H22 2.7036 no . .
N1 H2 2.8129 no . .
N1 H18 2.7129 no . .
N2 H22 3.4878 no . .
N3 H12 2.7030 no . .
C1 H3 3.2360 no . .
C1 H5 3.2789 no . .
C2 H4 3.2725 no . .
C3 H5 3.2686 no . .
C4 H2 3.2863 no . .
C5 H3 3.2591 no . .
C5 H15A 2.8389 no . .
C6 H2 3.3113 no . .
C6 H4 3.2445 no . .
C6 H15A 2.6474 no . .
C6 H15B 3.2252 no . .
C6 H15C 3.1969 no . .
C7 H5 2.8705 no . .
C7 H10 3.1129 no . .
C8 H10 2.6513 no . .
C8 H15A 3.3206 no . .
C8 H15B 2.8375 no . .
C8 H15C 2.8375 no . .
C8 H18 2.7609 no . .
C9 H11 3.2826 no . .
C9 H15B 3.2244 no . .
C9 H15C 3.1366 no . .
C9 H18 2.9889 no . .
C10 H12 3.2865 no . .
C10 H15B 3.0577 no . .
C10 H15C 3.3885 no . .
C10 H18 3.1629 no . .
C12 H10 3.2628 no . .
C13 H11 3.2332 no . .
C14 H10 3.2491 no . .
C14 H12 3.3266 no . .
C15 H5 3.0461 no . .
C15 H10 3.1153 no . .
C16 H2 2.9118 no . .
C16 H18 2.6789 no . .
C16 H22 2.6315 no . .
C17 H19 3.2621 no . .
C17 H21 3.2502 no . .
C18 H10 3.3951 no . .
C18 H20 3.2387 no . .
C18 H22 3.2571 no . .
C19 H21 3.2382 no . .
C20 H18 3.2381 no . .
C20 H22 3.2352 no . .
C21 H19 3.2405 no . .
C22 H18 3.2560 no . .
C22 H20 3.2341 no . .
H2 H3 2.3571 no . .
H3 H4 2.3177 no . .
H4 H5 2.3241 no . .
H5 H15A 2.3877 no . .
H10 H11 2.3363 no . .
H10 H15B 2.5370 no . .
H10 H15C 3.3050 no . .
H10 H18 3.0248 no . .
H11 H12 2.3021 no . .
H18 H19 2.3296 no . .
H19 H20 2.3283 no . .
H20 H21 2.3097 no . .
H21 H22 2.3184 no . .
S1 H4 3.3533 no . 8_454
S1 H5 3.4978 no . 8_454
S1 H15C 3.2166 no . 7_555
O1 H2 2.9604 no . 7_556
O1 H3 2.7046 no . 7_556
O1 H10 2.5296 no . 6_555
O1 H11 2.6387 no . 4_555
O1 H15B 2.9249 no . 6_555
N1 H19 3.4778 no . 6_555
N2 H18 2.9101 no . 6_555
N3 H5 3.2791 no . 8_454
N3 H15C 2.5462 no . 7_555
N3 H20 3.3705 no . 3_555
C1 H19 2.8679 no . 6_555
C2 H2 3.3566 no . 7_556
C2 H10 3.5170 no . 4_555
C2 H10 3.3128 no . 6_555
C2 H11 3.2943 no . 4_555
C2 H11 3.1459 no . 6_555
C2 H19 3.3260 no . 6_555
C3 H11 3.3412 no . 6_555
C3 H15B 3.1539 no . 4_555
C3 H19 3.5478 no . 6_555
C3 H21 3.0042 no . 8_555
C4 H5 3.0428 no . 3_656
C4 H19 3.3847 no . 6_555
C4 H21 3.2308 no . 8_555
C4 H22 3.4918 no . 8_555
C5 H4 3.1921 no . 3_656
C5 H5 3.3438 no . 3_656
C5 H19 3.0055 no . 6_555
C6 H19 2.7232 no . 6_555
C7 H19 3.2891 no . 6_555
C10 H2 3.4655 no . 4_554
C10 H2 3.3884 no . 6_545
C11 H2 3.2992 no . 4_554
C11 H2 3.3185 no . 6_545
C11 H21 3.4961 no . 3_555
C12 H18 3.4804 no . 4_554
C12 H20 2.9350 no . 3_555
C12 H21 3.4642 no . 3_555
C13 H20 3.2584 no . 3_555
C15 H3 3.4530 no . 4_554
C15 H15A 3.0044 no . 2_655
C16 H10 3.4721 no . 6_555
C16 H11 2.9346 no . 4_555
C17 H11 3.3624 no . 4_555
C17 H12 3.2626 no . 4_555
C18 H12 2.8640 no . 4_555
C19 H12 3.1993 no . 4_555
C20 H12 3.2637 no . 3_555
C21 H3 3.4847 no . 8_454
C21 H4 3.5036 no . 8_454
C21 H12 3.5263 no . 3_555
C21 H20 3.4705 no . 3_555
C22 H4 3.3307 no . 8_454
H2 O1 2.9604 no . 7_556
H2 C2 3.3566 no . 7_556
H2 C10 3.4655 no . 4_555
H2 C10 3.3884 no . 6_555
H2 C11 3.2992 no . 4_555
H2 C11 3.3185 no . 6_555
H2 H2 2.4153 no . 7_556
H2 H10 3.0117 no . 4_555
H2 H10 2.8174 no . 6_555
H2 H11 2.6941 no . 4_555
H2 H11 2.6749 no . 6_555
H3 O1 2.7046 no . 7_556
H3 C15 3.4530 no . 4_555
H3 C21 3.4847 no . 8_555
H3 H10 3.5681 no . 4_555
H3 H11 3.0367 no . 6_555
H3 H15B 2.6318 no . 4_555
H3 H21 2.6599 no . 8_555
H3 H22 3.4704 no . 7_556
H3 H22 3.4055 no . 8_555
H4 S1 3.3533 no . 8_555
H4 C5 3.1921 no . 3_656
H4 C21 3.5036 no . 8_555
H4 C22 3.3307 no . 8_555
H4 H5 2.7402 no . 3_656
H4 H15A 3.4446 no . 3_656
H4 H21 3.0449 no . 8_555
H4 H22 2.7247 no . 8_555
H5 S1 3.4978 no . 8_555
H5 N3 3.2791 no . 8_555
H5 C4 3.0428 no . 3_656
H5 C5 3.3438 no . 3_656
H5 H4 2.7402 no . 3_656
H5 H5 3.2755 no . 3_656
H5 H15A 3.4991 no . 2_655
H5 H15C 3.0621 no . 2_655
H5 H19 3.4587 no . 6_555
H10 O1 2.5296 no . 6_545
H10 C2 3.5170 no . 4_554
H10 C2 3.3128 no . 6_545
H10 C16 3.4721 no . 6_545
H10 H2 3.0117 no . 4_554
H10 H2 2.8174 no . 6_545
H10 H3 3.5681 no . 4_554
H11 O1 2.6387 no . 4_554
H11 C2 3.2943 no . 4_554
H11 C2 3.1459 no . 6_545
H11 C3 3.3412 no . 6_545
H11 C16 2.9346 no . 4_554
H11 C17 3.3624 no . 4_554
H11 H2 2.6941 no . 4_554
H11 H2 2.6749 no . 6_545
H11 H3 3.0367 no . 6_545
H11 H21 3.2358 no . 3_555
H12 C17 3.2626 no . 4_554
H12 C18 2.8640 no . 4_554
H12 C19 3.1993 no . 4_554
H12 C20 3.2637 no . 3_555
H12 C21 3.5263 no . 3_555
H12 H18 2.9428 no . 4_554
H12 H19 3.4567 no . 4_554
H12 H20 2.6729 no . 3_555
H12 H21 3.1975 no . 3_555
H15A C15 3.0044 no . 2_655
H15A H4 3.4446 no . 3_656
H15A H5 3.4991 no . 2_655
H15A H15A 2.2403 no . 2_655
H15A H15B 3.3731 no . 2_655
H15A H15C 3.0337 no . 2_655
H15B O1 2.9249 no . 6_545
H15B C3 3.1539 no . 4_554
H15B H3 2.6318 no . 4_554
H15B H15A 3.3731 no . 2_655
H15B H22 3.2407 no . 6_545
H15C S1 3.2166 no . 7_555
H15C N3 2.5462 no . 7_555
H15C H5 3.0621 no . 2_655
H15C H15A 3.0337 no . 2_655
H18 N2 2.9101 no . 6_545
H18 C12 3.4804 no . 4_555
H18 H12 2.9428 no . 4_555
H19 N1 3.4778 no . 6_545
H19 C1 2.8679 no . 6_545
H19 C2 3.3260 no . 6_545
H19 C3 3.5478 no . 6_545
H19 C4 3.3847 no . 6_545
H19 C5 3.0055 no . 6_545
H19 C6 2.7232 no . 6_545
H19 C7 3.2891 no . 6_545
H19 H5 3.4587 no . 6_545
H19 H12 3.4567 no . 4_555
H20 N3 3.3705 no . 3_555
H20 C12 2.9350 no . 3_555
H20 C13 3.2584 no . 3_555
H20 C21 3.4705 no . 3_555
H20 H12 2.6729 no . 3_555
H20 H20 3.5912 no . 3_555
H20 H21 3.3182 no . 3_555
H21 C3 3.0042 no . 8_454
H21 C4 3.2308 no . 8_454
H21 C11 3.4961 no . 3_555
H21 C12 3.4642 no . 3_555
H21 H3 2.6599 no . 8_454
H21 H4 3.0449 no . 8_454
H21 H11 3.2358 no . 3_555
H21 H12 3.1975 no . 3_555
H21 H20 3.3182 no . 3_555
H22 C4 3.4918 no . 8_454
H22 H3 3.4704 no . 7_556
H22 H3 3.4055 no . 8_454
H22 H4 2.7247 no . 8_454
H22 H15B 3.2407 no . 6_555

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
2-(2,1,3-Benzothiadiazol-4-yl)-3-methyl-1H-indol-1-yl(phenyl)methanone
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/chloroform'
_exptl_crystal_preparation       ', Luminescent'
