# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1_polymorphII
_database_code_depnum_ccdc_archive 'CCDC 2204969'
loop_
_audit_author_name
_audit_author_address
'Roberto Centore'
;University of Naples Federico II
Italy
;
_audit_update_record             
;
2022-09-02 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
5-nitrobenzo[c][1,2,5]thiadiazole 
;
_chemical_melting_point          398
_chemical_formula_moiety         'C6 H3 N3 O2 S'
_chemical_formula_sum            'C6 H3 N3 O2 S'
_chemical_formula_weight         181.17

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

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

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

_cell_length_a                   3.812(3)
_cell_length_b                   8.905(4)
_cell_length_c                   10.498(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.02(4)
_cell_angle_gamma                90
_cell_volume                     355.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    121
_cell_measurement_theta_min      3.875
_cell_measurement_theta_max      20.873

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.409
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2001)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;
_diffrn_reflns_number            2117
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.004
_diffrn_reflns_theta_max         27.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_point_group_measured_fraction_full 0.862
_reflns_number_total             1288
_reflns_number_gt                982
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_max     0.673
_reflns_Friedel_fraction_full    0.726

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Collect (Nonius, 1999)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_structure_solution    
;
SIR97 (Altomare et al., 1999)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 2012),  
Mercury (Macrae et al., 2006), and 
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 
;
 Flack x determined using 336 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1288
_refine_ls_number_parameters     109
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7587(14) 0.4253(6) -0.0686(5) 0.0404(13) Uani 1 1 d . . . . .
C2 C 0.7215(15) 0.2768(7) -0.1147(6) 0.0544(15) Uani 1 1 d . . . . .
H2 H 0.599129 0.257561 -0.193569 0.065 Uiso 1 1 calc R U . . .
C3 C 0.8663(14) 0.1622(7) -0.0427(6) 0.0527(15) Uani 1 1 d . . . . .
H3 H 0.845847 0.063855 -0.072235 0.063 Uiso 1 1 calc R U . . .
C4 C 1.0499(13) 0.1937(7) 0.0787(6) 0.0431(12) Uani 1 1 d . . . . .
C5 C 0.9457(13) 0.4528(6) 0.0542(5) 0.0388(12) Uani 1 1 d . . . . .
C6 C 1.0970(13) 0.3333(6) 0.1278(5) 0.0438(13) Uani 1 1 d . . . . .
H6 H 1.223322 0.349623 0.206467 0.053 Uiso 1 1 calc R U . . .
N1 N 0.6383(13) 0.5505(6) -0.1250(6) 0.0532(14) Uani 1 1 d . . . . .
N2 N 0.9657(12) 0.5973(6) 0.0851(5) 0.0492(14) Uani 1 1 d . . . . .
N3 N 1.2075(15) 0.0675(6) 0.1531(6) 0.0606(15) Uani 1 1 d . . . . .
O1 O 1.180(2) -0.0563(5) 0.1097(8) 0.110(2) Uani 1 1 d . . . . .
O2 O 1.3638(17) 0.0936(6) 0.2558(7) 0.0865(17) Uani 1 1 d . . . . .
S1 S 0.7592(4) 0.68720(16) -0.0308(2) 0.0577(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.325(8) . ?
C1 C2 1.412(8) . ?
C1 C5 1.439(8) . ?
C2 C3 1.358(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.427(9) . ?
C3 H3 0.9300 . ?
C4 C6 1.352(7) . ?
C4 N3 1.467(8) . ?
C5 N2 1.327(7) . ?
C5 C6 1.409(8) . ?
C6 H6 0.9300 . ?
N1 S1 1.610(6) . ?
N2 S1 1.604(6) . ?
N3 O1 1.193(7) . ?
N3 O2 1.208(9) . ?

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
N1 C1 C2 127.9(6) . . ?
N1 C1 C5 112.5(5) . . ?
C2 C1 C5 119.6(5) . . ?
C3 C2 C1 119.3(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C6 C4 C3 124.1(5) . . ?
C6 C4 N3 117.8(5) . . ?
C3 C4 N3 118.0(5) . . ?
N2 C5 C6 125.9(6) . . ?
N2 C5 C1 113.4(5) . . ?
C6 C5 C1 120.7(5) . . ?
C4 C6 C5 116.8(5) . . ?
C4 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
C1 N1 S1 107.0(5) . . ?
C5 N2 S1 106.6(5) . . ?
O1 N3 O2 122.5(6) . . ?
O1 N3 C4 119.2(7) . . ?
O2 N3 C4 118.3(5) . . ?
N2 S1 N1 100.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 179.7(6) . . . . ?
C5 C1 C2 C3 -0.7(7) . . . . ?
C1 C2 C3 C4 0.6(8) . . . . ?
C2 C3 C4 C6 -1.2(8) . . . . ?
C2 C3 C4 N3 -179.1(5) . . . . ?
N1 C1 C5 N2 -1.2(6) . . . . ?
C2 C1 C5 N2 179.1(5) . . . . ?
N1 C1 C5 C6 -179.1(5) . . . . ?
C2 C1 C5 C6 1.1(6) . . . . ?
C3 C4 C6 C5 1.6(8) . . . . ?
N3 C4 C6 C5 179.5(4) . . . . ?
N2 C5 C6 C4 -179.2(5) . . . . ?
C1 C5 C6 C4 -1.5(7) . . . . ?
C2 C1 N1 S1 -179.5(4) . . . . ?
C5 C1 N1 S1 0.8(5) . . . . ?
C6 C5 N2 S1 178.8(4) . . . . ?
C1 C5 N2 S1 1.0(6) . . . . ?
C6 C4 N3 O1 -177.3(7) . . . . ?
C3 C4 N3 O1 0.7(9) . . . . ?
C6 C4 N3 O2 1.8(9) . . . . ?
C3 C4 N3 O2 179.9(6) . . . . ?
C5 N2 S1 N1 -0.4(5) . . . . ?
C1 N1 S1 N2 -0.2(5) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.059



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/ethanol in the presence of CuCl2'
