# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ss-bzt
_database_code_depnum_ccdc_archive 'CCDC 2266086'
loop_
_audit_author_name
_audit_author_address
'shuaiqiang Zhao'
;Jilin University
China
;
_audit_update_record             
;
2023-08-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2022-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        thianthreno[2,3-c][1,2,5]thiadiazole
_chemical_formula_moiety         'C12 H6 N2 S3'
_chemical_formula_sum            'C12 H6 N2 S3'
_chemical_formula_weight         274.37
_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.98040(10)
_cell_length_b                   11.8021(4)
_cell_length_c                   12.6373(4)
_cell_angle_alpha                103.6610(10)
_cell_angle_beta                 96.0630(10)
_cell_angle_gamma                98.3570(10)
_cell_volume                     564.66(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/n-hexane'
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23770
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.759
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.992
_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                2454
_reflns_number_total             2572
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.2311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0805
_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:
 C6(H6), C9(H9), C3(H3), C12(H12), C11(H11), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S2 S 0.18795(10) 0.57497(3) 0.13180(3) 0.03487(11) Uani 1 1 d . . . . .
S3 S 0.04057(10) 0.55649(3) 0.37344(3) 0.03506(11) Uani 1 1 d . . . . .
S1 S 0.35328(13) 0.04849(4) 0.14408(4) 0.04977(14) Uani 1 1 d . . . . .
N2 N 0.2609(4) 0.12798(12) 0.25608(12) 0.0444(3) Uani 1 1 d . . . . .
N1 N 0.3806(4) 0.14238(12) 0.06925(12) 0.0446(3) Uani 1 1 d . . . . .
C8 C 0.3075(3) 0.68015(12) 0.35401(11) 0.0286(3) Uani 1 1 d . . . . .
C5 C 0.2342(3) 0.44593(12) 0.17515(11) 0.0280(3) Uani 1 1 d . . . . .
C7 C 0.3713(4) 0.68887(12) 0.25001(11) 0.0295(3) Uani 1 1 d . . . . .
C4 C 0.1651(3) 0.43751(12) 0.28259(11) 0.0273(3) Uani 1 1 d . . . . .
C1 C 0.3143(4) 0.24425(13) 0.13186(12) 0.0335(3) Uani 1 1 d . . . . .
C6 C 0.3138(4) 0.35209(13) 0.10128(11) 0.0337(3) Uani 1 1 d . . . . .
H6 H 0.367353 0.359198 0.031365 0.040 Uiso 1 1 calc R . . . .
C9 C 0.4482(4) 0.77280(13) 0.44603(13) 0.0363(3) Uani 1 1 d . . . . .
H9 H 0.410985 0.766217 0.517534 0.044 Uiso 1 1 calc R . . . .
C2 C 0.2447(4) 0.23553(13) 0.23860(12) 0.0328(3) Uani 1 1 d . . . . .
C3 C 0.1747(4) 0.33500(13) 0.31492(12) 0.0332(3) Uani 1 1 d . . . . .
H3 H 0.135261 0.330770 0.386840 0.040 Uiso 1 1 calc R . . . .
C12 C 0.5715(4) 0.79080(14) 0.23766(14) 0.0390(3) Uani 1 1 d . . . . .
H12 H 0.618270 0.796571 0.166752 0.047 Uiso 1 1 calc R . . . .
C11 C 0.7021(4) 0.88369(14) 0.32932(16) 0.0458(4) Uani 1 1 d . . . . .
H11 H 0.833560 0.954115 0.320956 0.055 Uiso 1 1 calc R . . . .
C10 C 0.6417(4) 0.87418(14) 0.43272(15) 0.0439(4) Uani 1 1 d . . . . .
H10 H 0.734073 0.937889 0.495248 0.053 Uiso 1 1 calc R . . . .


_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
S2 C5 1.7628(14) . ?
S2 C7 1.7628(14) . ?
S3 C8 1.7587(14) . ?
S3 C4 1.7598(14) . ?
S1 N2 1.6130(15) . ?
S1 N1 1.6172(15) . ?
N2 C2 1.3480(19) . ?
N1 C1 1.3522(19) . ?
C8 C7 1.3890(19) . ?
C8 C9 1.395(2) . ?
C5 C4 1.4366(18) . ?
C5 C6 1.369(2) . ?
C7 C12 1.394(2) . ?
C4 C3 1.3695(19) . ?
C1 C6 1.415(2) . ?
C1 C2 1.429(2) . ?
C9 C10 1.381(2) . ?
C2 C3 1.415(2) . ?
C12 C11 1.386(2) . ?
C11 C10 1.381(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S2 C5 102.58(6) . . ?
C8 S3 C4 102.56(6) . . ?
N2 S1 N1 101.24(7) . . ?
C2 N2 S1 106.13(11) . . ?
C1 N1 S1 106.06(11) . . ?
C7 C8 S3 121.77(10) . . ?
C7 C8 C9 119.86(13) . . ?
C9 C8 S3 118.34(11) . . ?
C4 C5 S2 120.28(10) . . ?
C6 C5 S2 118.21(10) . . ?
C6 C5 C4 121.36(12) . . ?
C8 C7 S2 120.91(10) . . ?
C8 C7 C12 119.97(13) . . ?
C12 C7 S2 119.07(11) . . ?
C5 C4 S3 120.57(10) . . ?
C3 C4 S3 118.07(10) . . ?
C3 C4 C5 121.25(12) . . ?
N1 C1 C6 126.40(14) . . ?
N1 C1 C2 113.09(14) . . ?
C6 C1 C2 120.50(13) . . ?
C5 C6 C1 118.22(13) . . ?
C10 C9 C8 119.70(15) . . ?
N2 C2 C1 113.48(14) . . ?
N2 C2 C3 126.31(14) . . ?
C3 C2 C1 120.20(13) . . ?
C4 C3 C2 118.40(13) . . ?
C11 C12 C7 119.69(15) . . ?
C10 C11 C12 120.20(15) . . ?
C11 C10 C9 120.55(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_so-bzt
_database_code_depnum_ccdc_archive 'CCDC 2266087'
loop_
_audit_author_name
_audit_author_address
'shuaiqiang Zhao'
;Jilin University
China
;
_audit_update_record             
;
2023-08-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2022-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        phenoxathiino[2,3-c][1,2,5]thiadiazole
_chemical_formula_moiety         'C12 H6 N2 O S2'
_chemical_formula_sum            'C12 H6 N2 O S2'
_chemical_formula_weight         258.31
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.4489(10)
_cell_length_b                   3.8802(2)
_cell_length_c                   18.6217(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.458(3)
_cell_angle_gamma                90
_cell_volume                     1042.12(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5196
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.50
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.490
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       strip
_exptl_crystal_F_000             528
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21421
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.825
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                1734
_reflns_number_total             2368
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.035
_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)+(0.0457P)²+0.4268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1034
_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), C6(H6), C9(H9), C12(H12), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S2 S 0.65325(4) 0.74412(16) 0.71312(3) 0.03648(17) Uani 1 1 d . . . . .
S1 S 0.89274(4) 0.28438(18) 0.45370(3) 0.0452(2) Uani 1 1 d . . . . .
O1 O 0.53056(11) 0.3795(5) 0.59142(9) 0.0494(5) Uani 1 1 d . . . . .
N1 N 0.78349(15) 0.1890(5) 0.44349(11) 0.0419(5) Uani 1 1 d . . . . .
N2 N 0.89686(14) 0.4660(5) 0.53200(10) 0.0407(5) Uani 1 1 d . . . . .
C3 C 0.77991(15) 0.5928(6) 0.61902(11) 0.0303(5) Uani 1 1 d . . . . .
H3 H 0.822652 0.699870 0.652777 0.036 Uiso 1 1 calc R . . . .
C5 C 0.62355(15) 0.4053(6) 0.58136(12) 0.0319(5) Uani 1 1 d . . . . .
C2 C 0.80993(15) 0.4603(6) 0.55380(11) 0.0307(5) Uani 1 1 d . . . . .
C8 C 0.53862(15) 0.5985(6) 0.71456(11) 0.0301(5) Uani 1 1 d . . . . .
C1 C 0.74475(16) 0.3019(6) 0.50295(11) 0.0325(5) Uani 1 1 d . . . . .
C4 C 0.68854(15) 0.5646(5) 0.63288(11) 0.0294(5) Uani 1 1 d . . . . .
C7 C 0.49156(15) 0.4448(6) 0.65603(12) 0.0330(5) Uani 1 1 d . . . . .
C6 C 0.65015(16) 0.2756(6) 0.51825(12) 0.0351(5) Uani 1 1 d . . . . .
H6 H 0.606431 0.169690 0.485088 0.042 Uiso 1 1 calc R . . . .
C9 C 0.49153(17) 0.6553(6) 0.77676(12) 0.0388(5) Uani 1 1 d . . . . .
H9 H 0.523173 0.754634 0.817913 0.047 Uiso 1 1 calc R . . . .
C12 C 0.39975(16) 0.3520(6) 0.65831(13) 0.0386(5) Uani 1 1 d . . . . .
H12 H 0.368362 0.245060 0.617913 0.046 Uiso 1 1 calc R . . . .
C10 C 0.39933(17) 0.5679(7) 0.77865(13) 0.0436(6) Uani 1 1 d . . . . .
H10 H 0.367116 0.612814 0.820641 0.052 Uiso 1 1 calc R . . . .
C11 C 0.35372(17) 0.4156(7) 0.71985(14) 0.0434(6) Uani 1 1 d . . . . .
H11 H 0.290264 0.354038 0.721598 0.052 Uiso 1 1 calc R . . . .


_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
S2 C8 1.752(2) . ?
S2 C4 1.752(2) . ?
S1 N1 1.621(2) . ?
S1 N2 1.617(2) . ?
O1 C5 1.371(3) . ?
O1 C7 1.383(3) . ?
N1 C1 1.344(3) . ?
N2 C2 1.343(3) . ?
C3 C2 1.411(3) . ?
C3 C4 1.365(3) . ?
C5 C4 1.441(3) . ?
C5 C6 1.355(3) . ?
C2 C1 1.433(3) . ?
C8 C7 1.384(3) . ?
C8 C9 1.396(3) . ?
C1 C6 1.417(3) . ?
C7 C12 1.378(3) . ?
C9 C10 1.377(3) . ?
C12 C11 1.381(3) . ?
C10 C11 1.377(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S2 C4 102.06(10) . . ?
N2 S1 N1 100.83(10) . . ?
C5 O1 C7 124.02(17) . . ?
C1 N1 S1 106.25(16) . . ?
C2 N2 S1 106.32(16) . . ?
C4 C3 C2 119.0(2) . . ?
O1 C5 C4 123.0(2) . . ?
C6 C5 O1 115.00(19) . . ?
C6 C5 C4 122.0(2) . . ?
N2 C2 C3 126.6(2) . . ?
N2 C2 C1 113.4(2) . . ?
C3 C2 C1 120.1(2) . . ?
C7 C8 S2 123.15(17) . . ?
C7 C8 C9 118.7(2) . . ?
C9 C8 S2 118.06(18) . . ?
N1 C1 C2 113.2(2) . . ?
N1 C1 C6 126.7(2) . . ?
C6 C1 C2 120.1(2) . . ?
C3 C4 S2 117.65(16) . . ?
C3 C4 C5 120.5(2) . . ?
C5 C4 S2 121.80(17) . . ?
O1 C7 C8 123.9(2) . . ?
C12 C7 O1 115.0(2) . . ?
C12 C7 C8 121.1(2) . . ?
C5 C6 C1 118.4(2) . . ?
C10 C9 C8 120.2(2) . . ?
C7 C12 C11 119.4(2) . . ?
C11 C10 C9 120.2(2) . . ?
C10 C11 C12 120.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/n-hexane'
_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_m-oo-bzt
_database_code_depnum_ccdc_archive 'CCDC 2266088'
loop_
_audit_author_name
_audit_author_address
'shuaiqiang Zhao'
;Jilin University
China
;
_audit_update_record             
;
2023-08-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2022-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
benzo[5',6'][1,4]dioxino[2',3':4,5]benzo[1,2-c][1,2,5]thiadiazole
_chemical_formula_moiety         'C12 H6 N2 O2 S'
_chemical_formula_sum            'C12 H6 N2 O2 S'
_chemical_formula_weight         242.25
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   22.528(3)
_cell_length_b                   3.9061(4)
_cell_length_c                   22.895(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.977(10)
_cell_angle_gamma                90
_cell_volume                     1999.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8907
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.59
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       strip
_exptl_crystal_F_000             992
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32302
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_min         2.707
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_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                1525
_reflns_number_total             2279
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0836
_refine_ls_restrained_S_all      1.098
_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)+(0.0718P)²+10.7716P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2054
_refine_ls_wR_factor_ref         0.2194
_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:
 C9(H9), C3(H3), C6(H6), C11(H11), C12(H12), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.43146(6) 0.2889(4) 0.69828(6) 0.0594(5) Uani 1 1 d . . . . .
O1 O 0.30424(13) 0.5697(9) 0.45773(13) 0.0495(8) Uani 1 1 d . . . . .
O2 O 0.42152(13) 0.8246(10) 0.45198(14) 0.0537(9) Uani 1 1 d . . . . .
N1 N 0.36763(18) 0.2379(11) 0.65671(17) 0.0524(10) Uani 1 1 d . . . . .
N2 N 0.47102(17) 0.4705(12) 0.65264(17) 0.0542(11) Uani 1 1 d . . . . .
C2 C 0.43482(18) 0.5054(11) 0.60170(19) 0.0404(10) Uani 1 1 d . . . . .
C1 C 0.37538(19) 0.3697(11) 0.6046(2) 0.0418(10) Uani 1 1 d . . . . .
C8 C 0.3767(2) 0.8635(12) 0.40548(19) 0.0432(10) Uani 1 1 d . . . . .
C4 C 0.40693(18) 0.6770(11) 0.50294(19) 0.0403(10) Uani 1 1 d . . . . .
C7 C 0.31921(18) 0.7372(11) 0.40840(19) 0.0395(10) Uani 1 1 d . . . . .
C9 C 0.3902(2) 1.0259(12) 0.3559(2) 0.0472(11) Uani 1 1 d . . . . .
H9 H 0.429523 1.108959 0.353942 0.057 Uiso 1 1 calc R . . . .
C3 C 0.44959(18) 0.6591(12) 0.5498(2) 0.0430(10) Uani 1 1 d . . . . .
H3 H 0.488527 0.748113 0.547738 0.052 Uiso 1 1 calc R . . . .
C6 C 0.33190(19) 0.3936(11) 0.55480(19) 0.0420(10) Uani 1 1 d . . . . .
H6 H 0.292574 0.307846 0.555816 0.050 Uiso 1 1 calc R . . . .
C5 C 0.34783(18) 0.5418(11) 0.50566(19) 0.0389(10) Uani 1 1 d . . . . .
C11 C 0.2893(2) 0.9458(12) 0.3118(2) 0.0511(12) Uani 1 1 d . . . . .
H11 H 0.259296 0.975941 0.279275 0.061 Uiso 1 1 calc R . . . .
C12 C 0.2755(2) 0.7803(12) 0.3613(2) 0.0464(11) Uani 1 1 d . . . . .
H12 H 0.236170 0.696249 0.363102 0.056 Uiso 1 1 calc R . . . .
C10 C 0.3464(2) 1.0692(13) 0.3086(2) 0.0543(12) Uani 1 1 d . . . . .
H10 H 0.355448 1.183228 0.274161 0.065 Uiso 1 1 calc R . . . .


_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 N1 1.637(4) . ?
S1 N2 1.617(4) . ?
O1 C7 1.382(5) . ?
O1 C5 1.385(5) . ?
O2 C8 1.383(5) . ?
O2 C4 1.376(5) . ?
N1 C1 1.329(6) . ?
N2 C2 1.347(6) . ?
C2 C1 1.449(6) . ?
C2 C3 1.407(6) . ?
C1 C6 1.414(6) . ?
C8 C7 1.396(6) . ?
C8 C9 1.365(6) . ?
C4 C3 1.353(6) . ?
C4 C5 1.441(6) . ?
C7 C12 1.380(6) . ?
C9 C10 1.384(7) . ?
C6 C5 1.352(6) . ?
C11 C12 1.373(7) . ?
C11 C10 1.383(7) . ?

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
N2 S1 N1 101.1(2) . . ?
C7 O1 C5 117.7(3) . . ?
C4 O2 C8 118.1(3) . . ?
C1 N1 S1 105.8(3) . . ?
C2 N2 S1 106.3(3) . . ?
N2 C2 C1 112.9(4) . . ?
N2 C2 C3 126.5(4) . . ?
C3 C2 C1 120.7(4) . . ?
N1 C1 C2 114.0(4) . . ?
N1 C1 C6 126.6(4) . . ?
C6 C1 C2 119.5(4) . . ?
O2 C8 C7 121.3(4) . . ?
C9 C8 O2 118.4(4) . . ?
C9 C8 C7 120.3(4) . . ?
O2 C4 C5 120.5(4) . . ?
C3 C4 O2 118.3(4) . . ?
C3 C4 C5 121.2(4) . . ?
O1 C7 C8 121.8(4) . . ?
C12 C7 O1 118.3(4) . . ?
C12 C7 C8 119.9(4) . . ?
C8 C9 C10 119.8(4) . . ?
C4 C3 C2 118.3(4) . . ?
C5 C6 C1 118.2(4) . . ?
O1 C5 C4 120.5(4) . . ?
C6 C5 O1 117.3(4) . . ?
C6 C5 C4 122.2(4) . . ?
C12 C11 C10 120.8(5) . . ?
C11 C12 C7 119.4(4) . . ?
C11 C10 C9 119.7(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/n-hexane'
_exptl_crystal_preparation       Luminescent
