#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:07:58 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565371.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_1565371
loop_
_publ_author_name
'Borys, Andryj M.'
'Clark, Ewan R.'
'Saines, Paul J.'
'Alberola, Antonio'
'Rawson, Jeremy M.'
_publ_section_title
;
 A short, versatile route towards benzothiadiazinyl radicals.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              149
_journal_page_last               158
_journal_paper_doi               10.1039/d1sc04248c
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         'C13 H6 Cl4 N2 S'
_chemical_formula_sum            'C13 H6 Cl4 N2 S'
_chemical_formula_weight         364.06
_chemical_properties_physical    Moisture-sensitive
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.564(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.4699(8)
_cell_length_b                   13.6411(7)
_cell_length_c                   16.045(1)
_cell_measurement_reflns_used    81408
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2857.0(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26565
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0374P)²+2.8105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                3443
_reflns_number_total             5023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           jr0710
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1565368--1565385.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1565371
loop_
_symmetry_equiv_pos_as_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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.17946(8) 0.46545(7) -0.00344(7) 0.0541(3) Uani 1 1 d . . .
S1 S 0.35281(7) 0.46812(7) 0.09177(7) 0.0404(3) Uani 1 1 d . . .
C1 C 0.3523(3) 0.5575(3) 0.1680(3) 0.0367(9) Uani 1 1 d . . .
C2 C 0.3417(3) 0.6559(3) 0.1408(3) 0.0402(9) Uani 1 1 d . . .
H2A H 0.3319 0.6735 0.0803 0.048 Uiso 1 1 calc R . .
C3 C 0.3458(3) 0.7258(2) 0.2030(3) 0.0397(9) Uani 1 1 d . . .
C4 C 0.3613(3) 0.7008(3) 0.2930(3) 0.0393(10) Uani 1 1 d . . .
C5 C 0.3696(3) 0.6028(3) 0.3184(3) 0.0362(9) Uani 1 1 d . . .
C6 C 0.3653(3) 0.5276(2) 0.2561(3) 0.0348(9) Uani 1 1 d . . .
N1 N 0.3747(2) 0.4326(2) 0.2859(2) 0.0366(7) Uani 1 1 d . . .
C7 C 0.3812(3) 0.3622(3) 0.2334(3) 0.0353(9) Uani 1 1 d . . .
N2 N 0.3833(2) 0.3707(2) 0.1486(2) 0.0409(8) Uani 1 1 d . . .
C8 C 0.3949(3) 0.2602(3) 0.2689(3) 0.0368(9) Uani 1 1 d . . .
C9 C 0.4162(3) 0.2427(3) 0.3606(3) 0.0445(10) Uani 1 1 d . . .
H9A H 0.4228 0.2957 0.4012 0.053 Uiso 1 1 calc R . .
C10 C 0.4277(3) 0.1465(3) 0.3925(3) 0.0502(11) Uani 1 1 d . . .
H10A H 0.4423 0.1339 0.4552 0.060 Uiso 1 1 calc R . .
C11 C 0.4182(3) 0.0693(3) 0.3337(3) 0.0529(12) Uani 1 1 d . . .
H11A H 0.4254 0.0038 0.3557 0.063 Uiso 1 1 calc R . .
C12 C 0.3983(3) 0.0875(3) 0.2434(3) 0.0515(11) Uani 1 1 d . . .
H12A H 0.3926 0.0344 0.2033 0.062 Uiso 1 1 calc R . .
C13 C 0.3864(3) 0.1823(3) 0.2103(3) 0.0438(10) Uani 1 1 d . . .
H13A H 0.3725 0.1942 0.1477 0.053 Uiso 1 1 calc R . .
Cl2 Cl 0.33116(9) 0.84697(7) 0.16971(8) 0.0587(3) Uani 1 1 d . . .
Cl3 Cl 0.36828(8) 0.79009(7) 0.37065(7) 0.0485(3) Uani 1 1 d . . .
Cl4 Cl 0.38611(8) 0.57061(7) 0.42737(7) 0.0522(3) Uani 1 1 d . . .
Cl5 Cl 0.16549(8) 0.69907(10) 0.54090(8) 0.0669(4) Uani 1 1 d . . .
S2 S 0.33503(8) 0.68732(8) 0.60071(7) 0.0482(3) Uani 1 1 d . . .
C14 C 0.3587(3) 0.7304(3) 0.7098(3) 0.0421(10) Uani 1 1 d . . .
C15 C 0.3592(3) 0.8314(3) 0.7248(3) 0.0495(11) Uani 1 1 d . . .
H15A H 0.3454 0.8765 0.6757 0.059 Uiso 1 1 calc R . .
C16 C 0.3800(3) 0.8636(3) 0.8118(3) 0.0476(11) Uani 1 1 d . . .
C17 C 0.3973(3) 0.7969(3) 0.8837(3) 0.0443(10) Uani 1 1 d . . .
C18 C 0.3978(3) 0.6971(3) 0.8675(3) 0.0426(10) Uani 1 1 d . . .
C19 C 0.3775(3) 0.6603(3) 0.7790(3) 0.0406(10) Uani 1 1 d . . .
N3 N 0.3771(2) 0.5601(2) 0.7671(2) 0.0420(8) Uani 1 1 d . . .
C20 C 0.3698(3) 0.5245(3) 0.6893(3) 0.0433(10) Uani 1 1 d . . .
N4 N 0.3635(2) 0.5758(2) 0.6130(2) 0.0484(9) Uani 1 1 d . . .
C21 C 0.3725(3) 0.4161(3) 0.6807(3) 0.0431(10) Uani 1 1 d . . .
C22 C 0.3615(3) 0.3724(3) 0.5985(3) 0.0526(11) Uani 1 1 d . . .
H22A H 0.3533 0.4120 0.5470 0.063 Uiso 1 1 calc R . .
C23 C 0.3624(3) 0.2709(3) 0.5918(3) 0.0569(12) Uani 1 1 d . . .
H23A H 0.3546 0.2416 0.5354 0.068 Uiso 1 1 calc R . .
C24 C 0.3743(3) 0.2128(3) 0.6646(4) 0.0578(13) Uani 1 1 d . . .
H24A H 0.3757 0.1436 0.6592 0.069 Uiso 1 1 calc R . .
C25 C 0.3842(3) 0.2549(3) 0.7464(3) 0.0554(12) Uani 1 1 d . . .
H25A H 0.3914 0.2144 0.7970 0.066 Uiso 1 1 calc R . .
C26 C 0.3838(3) 0.3564(3) 0.7549(3) 0.0470(10) Uani 1 1 d . . .
H26A H 0.3913 0.3851 0.8115 0.056 Uiso 1 1 calc R . .
Cl6 Cl 0.38438(9) 0.98785(8) 0.83294(10) 0.0666(4) Uani 1 1 d . . .
Cl7 Cl 0.41618(8) 0.83921(8) 0.99069(8) 0.0575(3) Uani 1 1 d . . .
Cl8 Cl 0.42545(9) 0.61411(8) 0.95596(8) 0.0584(3) 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N2 S1 C1 105.84(18) . . ?
N2 S1 Cl1 108.99(12) . . ?
C1 S1 Cl1 98.30(13) . . ?
C2 C1 C6 122.8(3) . . ?
C2 C1 S1 119.3(3) . . ?
C6 C1 S1 117.9(3) . . ?
C3 C2 C1 118.6(4) . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 Cl2 119.0(3) . . ?
C4 C3 Cl2 119.8(3) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 Cl3 120.1(3) . . ?
C3 C4 Cl3 120.5(3) . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 Cl4 120.1(3) . . ?
C6 C5 Cl4 118.6(3) . . ?
N1 C6 C1 125.2(3) . . ?
N1 C6 C5 118.3(3) . . ?
C1 C6 C5 116.5(3) . . ?
C7 N1 C6 119.7(3) . . ?
N1 C7 N2 127.8(3) . . ?
N1 C7 C8 118.4(3) . . ?
N2 C7 C8 113.7(3) . . ?
C7 N2 S1 121.7(3) . . ?
C9 C8 C13 120.0(3) . . ?
C9 C8 C7 120.0(3) . . ?
C13 C8 C7 120.0(4) . . ?
C8 C9 C10 119.3(4) . . ?
C11 C10 C9 120.4(4) . . ?
C12 C11 C10 119.8(4) . . ?
C11 C12 C13 120.7(4) . . ?
C12 C13 C8 119.8(4) . . ?
N4 S2 C14 105.99(19) . . ?
N4 S2 Cl5 107.80(13) . . ?
C14 S2 Cl5 96.41(14) . . ?
C15 C14 C19 123.6(4) . . ?
C15 C14 S2 119.4(3) . . ?
C19 C14 S2 117.0(3) . . ?
C16 C15 C14 118.3(4) . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 Cl6 119.3(3) . . ?
C17 C16 Cl6 119.8(3) . . ?
C18 C17 C16 119.7(4) . . ?
C18 C17 Cl7 120.4(3) . . ?
C16 C17 Cl7 119.9(3) . . ?
C17 C18 C19 121.4(4) . . ?
C17 C18 Cl8 120.6(3) . . ?
C19 C18 Cl8 118.0(3) . . ?
N3 C19 C14 125.4(4) . . ?
N3 C19 C18 118.6(4) . . ?
C14 C19 C18 116.0(4) . . ?
C20 N3 C19 119.8(4) . . ?
N3 C20 N4 127.6(4) . . ?
N3 C20 C21 117.8(4) . . ?
N4 C20 C21 114.6(4) . . ?
C20 N4 S2 121.2(3) . . ?
C22 C21 C26 119.0(4) . . ?
C22 C21 C20 121.1(4) . . ?
C26 C21 C20 119.9(4) . . ?
C23 C22 C21 119.9(4) . . ?
C24 C23 C22 121.1(5) . . ?
C23 C24 C25 119.8(4) . . ?
C24 C25 C26 120.2(4) . . ?
C25 C26 C21 120.1(4) . . ?
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 S1 2.3065(17) . ?
S1 N2 1.564(3) . ?
S1 C1 1.729(4) . ?
C1 C2 1.399(5) . ?
C1 C6 1.404(5) . ?
C2 C3 1.364(5) . ?
C3 C4 1.405(6) . ?
C3 Cl2 1.721(4) . ?
C4 C5 1.387(5) . ?
C4 Cl3 1.714(4) . ?
C5 C6 1.413(5) . ?
C5 Cl4 1.717(4) . ?
C6 N1 1.368(4) . ?
N1 C7 1.308(5) . ?
C7 N2 1.379(5) . ?
C7 C8 1.484(5) . ?
C8 C9 1.388(5) . ?
C8 C13 1.388(5) . ?
C9 C10 1.392(5) . ?
C10 C11 1.381(6) . ?
C11 C12 1.372(6) . ?
C12 C13 1.380(5) . ?
Cl5 S2 2.2211(17) . ?
S2 N4 1.567(4) . ?
S2 C14 1.735(4) . ?
C14 C15 1.397(5) . ?
C14 C19 1.400(5) . ?
C15 C16 1.368(6) . ?
C16 C17 1.404(6) . ?
C16 Cl6 1.725(4) . ?
C17 C18 1.387(5) . ?
C17 Cl7 1.717(4) . ?
C18 C19 1.413(5) . ?
C18 Cl8 1.722(4) . ?
C19 N3 1.380(5) . ?
N3 C20 1.299(5) . ?
C20 N4 1.379(5) . ?
C20 C21 1.488(5) . ?
C21 C22 1.392(6) . ?
C21 C26 1.392(6) . ?
C22 C23 1.390(6) . ?
C23 C24 1.359(6) . ?
C24 C25 1.383(6) . ?
C25 C26 1.391(6) . ?
