#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:11:36 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281421 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/60/7246064.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246064
loop_
_publ_author_name
'Gentile, Francesco Silvio'
'Parisi, Emmanuele'
'Centore, Roberto'
_publ_section_title
;
 Journeys in crystal energy landscapes: actual and virtual structures in
 polymorphic 5-nitrobenzo[c][1,2,5]thiadiazole
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              859
_journal_page_last               865
_journal_paper_doi               10.1039/D2CE01619B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C6 H3 N3 O2 S'
_chemical_formula_sum            'C6 H3 N3 O2 S'
_chemical_formula_weight         181.17
_chemical_melting_point          398
_chemical_name_systematic
;
5-nitrobenzo[c][1,2,5]thiadiazole 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-09-02 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.02(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.812(3)
_cell_length_b                   8.905(4)
_cell_length_c                   10.498(5)
_cell_measurement_reflns_used    121
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.873
_cell_measurement_theta_min      3.875
_cell_volume                     355.0(4)
_computing_cell_refinement
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_collection       'Collect (Nonius, 1999)'
_computing_data_reduction
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012),  
Mercury (Macrae et al., 2006), and 
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution
;
SIR97 (Altomare et al., 1999)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method
;
CCD rotation images, thick slices
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2117
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.009
_diffrn_reflns_theta_min         3.004
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS (Bruker, 2001)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_description       plate
_exptl_crystal_F_000             184
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/ethanol in the presence of CuCl2'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.059
_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)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1288
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0478
_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)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.726
_reflns_Friedel_fraction_max     0.673
_reflns_number_gt                982
_reflns_number_total             1288
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01619b2.cif
_cod_data_source_block           1_polymorphII
_cod_depositor_comments          'Adding full bibliography for 7246064.cif.'
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7246064
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_min   0.853
_shelx_estimated_absorpt_t_max   0.960
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
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 . . . . .
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'
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_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_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) . . . . ?
