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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1059158'
_audit_update_record             
;
2015-04-11 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;
#==========================================================================
# CHEMICAL DATA
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H9 N S2'
_chemical_formula_sum            'C15 H9 N S2'
_chemical_formula_weight         267.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# CRYSTAL DATA 
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   25.831(3)
_cell_length_b                   11.8166(11)
_cell_length_c                   3.9035(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1191.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      37.796
_cell_measurement_theta_min      2.927
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.6180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
#==========================================================================

# Experimental data 
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1352 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.8266.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            55390
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.720
_diffrn_reflns_theta_min         1.577
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                6004
_reflns_number_total             6578
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 2436 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         6578
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+0.2544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0892
#==========================================================================

# Refinement data 
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT 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 0.45757(2) 0.59409(2) 0.26380(11) 0.01527(6) Uani 1 1 d . . . . .
S2 S 0.39685(2) 0.20926(3) 0.26413(13) 0.02192(8) Uani 1 1 d . . . . .
N1 N 0.36858(4) 0.61865(10) 0.5707(3) 0.0163(2) Uani 1 1 d . . . . .
C1 C 0.44112(5) 0.72800(11) 0.4057(4) 0.0149(2) Uani 1 1 d . . . . .
C2 C 0.39201(5) 0.72460(11) 0.5622(4) 0.0150(2) Uani 1 1 d . . . . .
C3 C 0.37065(6) 0.82408(12) 0.6987(4) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.3378 0.8230 0.8076 0.024 Uiso 1 1 calc R . . . .
C4 C 0.39859(6) 0.92424(13) 0.6714(5) 0.0230(3) Uani 1 1 d . . . . .
H4 H 0.3844 0.9923 0.7609 0.028 Uiso 1 1 calc R . . . .
C5 C 0.44727(7) 0.92625(13) 0.5141(5) 0.0225(3) Uani 1 1 d . . . . .
H5 H 0.4655 0.9959 0.4974 0.027 Uiso 1 1 calc R . . . .
C6 C 0.46954(6) 0.82844(12) 0.3817(4) 0.0193(2) Uani 1 1 d . . . . .
H6 H 0.5029 0.8298 0.2788 0.023 Uiso 1 1 calc R . . . .
C7 C 0.39820(5) 0.54267(11) 0.4291(4) 0.0141(2) Uani 1 1 d . . . . .
C8 C 0.38599(5) 0.42257(11) 0.4017(4) 0.0150(2) Uani 1 1 d . . . . .
C9 C 0.42018(5) 0.34554(11) 0.2691(5) 0.0180(2) Uani 1 1 d . . . . .
H9 H 0.4536 0.3655 0.1875 0.022 Uiso 1 1 calc R . . . .
C10 C 0.33865(6) 0.25211(12) 0.4447(4) 0.0192(2) Uani 1 1 d . . . . .
C11 C 0.33794(5) 0.36981(12) 0.5078(4) 0.0163(2) Uani 1 1 d . . . . .
C12 C 0.29636(7) 0.18264(14) 0.5260(5) 0.0257(3) Uani 1 1 d . . . . .
H12 H 0.2973 0.1036 0.4814 0.031 Uiso 1 1 calc R . . . .
C13 C 0.25325(7) 0.23262(16) 0.6731(5) 0.0287(3) Uani 1 1 d . . . . .
H13 H 0.2243 0.1872 0.7321 0.034 Uiso 1 1 calc R . . . .
C14 C 0.25183(6) 0.34911(15) 0.7361(5) 0.0273(3) Uani 1 1 d . . . . .
H14 H 0.2217 0.3815 0.8358 0.033 Uiso 1 1 calc R . . . .
C15 C 0.29357(6) 0.41844(14) 0.6556(4) 0.0212(3) Uani 1 1 d . . . . .
H15 H 0.2921 0.4974 0.6998 0.025 Uiso 1 1 calc R . . . .

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

# 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 C1 1.7294(14) . ?
S1 C7 1.7713(13) . ?
S2 C9 1.7195(13) . ?
S2 C10 1.7358(16) . ?
N1 C2 1.3910(18) . ?
N1 C7 1.3028(18) . ?
C1 C2 1.409(2) . ?
C1 C6 1.3987(19) . ?
C2 C3 1.4036(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.400(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.4577(19) . ?
C8 C9 1.3698(19) . ?
C8 C11 1.4494(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.413(2) . ?
C10 C12 1.403(2) . ?
C11 C15 1.406(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.399(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(2) . ?
C15 H15 0.9500 . ?

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
C1 S1 C7 89.11(6) . . ?
C9 S2 C10 91.48(7) . . ?
C7 N1 C2 110.77(12) . . ?
C2 C1 S1 109.52(10) . . ?
C6 C1 S1 128.75(11) . . ?
C6 C1 C2 121.73(13) . . ?
N1 C2 C1 115.33(12) . . ?
N1 C2 C3 125.01(13) . . ?
C3 C2 C1 119.66(13) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.66(14) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.97(14) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.37(14) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 121.2 . . ?
C5 C6 C1 117.60(14) . . ?
C5 C6 H6 121.2 . . ?
N1 C7 S1 115.25(10) . . ?
N1 C7 C8 125.10(12) . . ?
C8 C7 S1 119.64(10) . . ?
C9 C8 C7 122.36(12) . . ?
C9 C8 C11 111.98(12) . . ?
C11 C8 C7 125.67(12) . . ?
S2 C9 H9 123.2 . . ?
C8 C9 S2 113.62(10) . . ?
C8 C9 H9 123.2 . . ?
C11 C10 S2 111.67(10) . . ?
C12 C10 S2 126.55(13) . . ?
C12 C10 C11 121.78(15) . . ?
C10 C11 C8 111.26(13) . . ?
C15 C11 C8 129.76(14) . . ?
C15 C11 C10 118.98(13) . . ?
C10 C12 H12 121.0 . . ?
C13 C12 C10 118.05(16) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.90(15) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.33(16) . . ?
C15 C14 H14 119.3 . . ?
C11 C15 H15 120.5 . . ?
C14 C15 C11 118.96(15) . . ?
C14 C15 H15 120.5 . . ?

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
S1 C1 C2 N1 0.45(16) . . . . ?
S1 C1 C2 C3 179.74(11) . . . . ?
S1 C1 C6 C5 179.35(12) . . . . ?
S1 C7 C8 C9 3.8(2) . . . . ?
S1 C7 C8 C11 -176.41(12) . . . . ?
S2 C10 C11 C8 0.43(16) . . . . ?
S2 C10 C11 C15 -179.71(12) . . . . ?
S2 C10 C12 C13 179.29(14) . . . . ?
N1 C2 C3 C4 179.99(14) . . . . ?
N1 C7 C8 C9 -175.77(16) . . . . ?
N1 C7 C8 C11 4.0(2) . . . . ?
C1 S1 C7 N1 1.11(12) . . . . ?
C1 S1 C7 C8 -178.51(12) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 N1 C7 S1 -1.03(16) . . . . ?
C2 N1 C7 C8 178.56(13) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 1.2(2) . . . . ?
C6 C1 C2 N1 -179.30(14) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C7 S1 C1 C2 -0.82(11) . . . . ?
C7 S1 C1 C6 178.92(15) . . . . ?
C7 N1 C2 C1 0.37(18) . . . . ?
C7 N1 C2 C3 -178.88(14) . . . . ?
C7 C8 C9 S2 179.98(12) . . . . ?
C7 C8 C11 C10 179.81(14) . . . . ?
C7 C8 C11 C15 0.0(3) . . . . ?
C8 C11 C15 C14 -179.95(16) . . . . ?
C9 S2 C10 C11 -0.29(12) . . . . ?
C9 S2 C10 C12 -179.87(17) . . . . ?
C9 C8 C11 C10 -0.38(19) . . . . ?
C9 C8 C11 C15 179.77(16) . . . . ?
C10 S2 C9 C8 0.07(14) . . . . ?
C10 C11 C15 C14 0.2(2) . . . . ?
C10 C12 C13 C14 0.5(3) . . . . ?
C11 C8 C9 S2 0.17(19) . . . . ?
C11 C10 C12 C13 -0.3(3) . . . . ?
C12 C10 C11 C8 -179.96(15) . . . . ?
C12 C10 C11 C15 -0.1(2) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C11 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# End of CIF  ============================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1059159'
_audit_update_record             
;
2015-04-11 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;
#==========================================================================
# CHEMICAL DATA

_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H7 N3 S'
_chemical_formula_sum            'C11 H7 N3 S'
_chemical_formula_weight         213.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# CRYSTAL DATA 
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.203(6)
_cell_length_b                   6.233(3)
_cell_length_c                   11.730(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.518(4)
_cell_angle_gamma                90
_cell_volume                     934.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6232
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.543
_cell_measurement_theta_min      3.188
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.851
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
#==========================================================================

# Experimental data  
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1342 before and 0.0810 after correction.
The Ratio of minimum to maximum transmission is 0.6038.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10092
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         1.593
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1962
_reflns_number_total             2146
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.4262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1066
#==========================================================================

# Refinement data 
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C9(H9), C4(H4), C10(H10), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT 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 0.20662(3) 0.38537(6) 0.59105(3) 0.01948(16) Uani 1 1 d . . . . .
N2 N 0.24696(9) 0.3378(2) 0.38493(10) 0.0164(3) Uani 1 1 d . . . . .
N3 N 0.41971(10) -0.2367(2) 0.46548(11) 0.0198(3) Uani 1 1 d . . . . .
N1 N 0.09428(11) 0.7387(2) 0.49424(11) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.32939(10) 0.0622(2) 0.52660(12) 0.0150(3) Uani 1 1 d . . . . .
C8 C 0.36131(11) -0.0047(2) 0.64398(12) 0.0167(3) Uani 1 1 d . . . . .
H8 H 0.3416 0.0740 0.7044 0.020 Uiso 1 1 calc R . . . .
C2 C 0.18376(11) 0.5179(2) 0.37713(12) 0.0152(3) Uani 1 1 d . . . . .
C6 C 0.26499(11) 0.2549(2) 0.49026(12) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.15350(11) 0.5713(2) 0.48081(12) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.36057(11) -0.0600(2) 0.44108(12) 0.0170(3) Uani 1 1 d . . . . .
H11 H 0.3385 -0.0149 0.3613 0.020 Uiso 1 1 calc R . . . .
C9 C 0.42251(11) -0.1884(2) 0.67073(13) 0.0195(3) Uani 1 1 d . . . . .
H9 H 0.4453 -0.2379 0.7496 0.023 Uiso 1 1 calc R . . . .
C4 C 0.08598(11) 0.8231(3) 0.29031(13) 0.0198(3) Uani 1 1 d . . . . .
H4 H 0.0597 0.9155 0.2252 0.024 Uiso 1 1 calc R . . . .
C10 C 0.44959(12) -0.2980(2) 0.57931(13) 0.0195(3) Uani 1 1 d . . . . .
H10 H 0.4915 -0.4232 0.5981 0.023 Uiso 1 1 calc R . . . .
C3 C 0.14827(11) 0.6494(2) 0.27877(13) 0.0181(3) Uani 1 1 d . . . . .
H3 H 0.1661 0.6209 0.2067 0.022 Uiso 1 1 calc R . . . .
C5 C 0.06176(12) 0.8622(2) 0.39846(13) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.0198 0.9836 0.4040 0.026 Uiso 1 1 calc R . . . .

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

# 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 C6 1.7636(15) . ?
S1 C1 1.7473(16) . ?
N2 C2 1.3880(19) . ?
N2 C6 1.3048(19) . ?
N3 C11 1.3391(19) . ?
N3 C10 1.349(2) . ?
N1 C1 1.337(2) . ?
N1 C5 1.341(2) . ?
C7 C8 1.399(2) . ?
C7 C6 1.471(2) . ?
C7 C11 1.401(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(2) . ?
C2 C1 1.4118(19) . ?
C2 C3 1.397(2) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.392(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.387(2) . ?
C4 C5 1.405(2) . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?

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
C1 S1 C6 88.37(7) . . ?
C6 N2 C2 110.28(12) . . ?
C11 N3 C10 117.04(12) . . ?
C1 N1 C5 115.04(13) . . ?
C8 C7 C6 122.56(12) . . ?
C8 C7 C11 118.21(13) . . ?
C11 C7 C6 119.23(13) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.81(13) . . ?
C9 C8 H8 120.6 . . ?
N2 C2 C1 115.43(12) . . ?
N2 C2 C3 126.91(12) . . ?
C3 C2 C1 117.65(13) . . ?
N2 C6 S1 116.45(11) . . ?
N2 C6 C7 123.54(12) . . ?
C7 C6 S1 120.00(10) . . ?
N1 C1 S1 124.66(11) . . ?
N1 C1 C2 125.88(13) . . ?
C2 C1 S1 109.46(11) . . ?
N3 C11 C7 123.67(13) . . ?
N3 C11 H11 118.2 . . ?
C7 C11 H11 118.2 . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.50(13) . . ?
C10 C9 H9 120.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.90(14) . . ?
C5 C4 H4 120.0 . . ?
N3 C10 C9 123.75(14) . . ?
N3 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.51(13) . . ?
C4 C3 H3 121.2 . . ?
N1 C5 C4 124.01(14) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?

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
N2 C2 C1 S1 -0.38(16) . . . . ?
N2 C2 C1 N1 179.06(14) . . . . ?
N2 C2 C3 C4 -179.59(13) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C7 C6 S1 -10.75(19) . . . . ?
C8 C7 C6 N2 169.70(13) . . . . ?
C8 C7 C11 N3 -0.4(2) . . . . ?
C8 C9 C10 N3 -0.1(2) . . . . ?
C2 N2 C6 S1 0.36(15) . . . . ?
C2 N2 C6 C7 179.92(12) . . . . ?
C6 S1 C1 N1 -178.99(14) . . . . ?
C6 S1 C1 C2 0.45(11) . . . . ?
C6 N2 C2 C1 0.02(18) . . . . ?
C6 N2 C2 C3 179.70(14) . . . . ?
C6 C7 C8 C9 -179.74(13) . . . . ?
C6 C7 C11 N3 179.52(13) . . . . ?
C1 S1 C6 N2 -0.49(12) . . . . ?
C1 S1 C6 C7 179.93(12) . . . . ?
C1 N1 C5 C4 0.4(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C11 N3 C10 C9 -0.1(2) . . . . ?
C11 C7 C8 C9 0.1(2) . . . . ?
C11 C7 C6 S1 169.38(10) . . . . ?
C11 C7 C6 N2 -10.2(2) . . . . ?
C10 N3 C11 C7 0.3(2) . . . . ?
C3 C2 C1 S1 179.92(11) . . . . ?
C3 C2 C1 N1 -0.6(2) . . . . ?
C3 C4 C5 N1 -0.9(2) . . . . ?
C5 N1 C1 S1 179.78(12) . . . . ?
C5 N1 C1 C2 0.4(2) . . . . ?
C5 C4 C3 C2 0.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# End of CIF  ============================================================
