#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:07:58 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565382.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_1565382
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         'C12 H5.84 Cl2.16 N3 S'
_chemical_formula_sum            'C12 H5.84 Cl2.16 N3 S'
_chemical_formula_weight         300.84
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.796(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4291(4)
_cell_length_b                   18.6148(9)
_cell_length_c                   9.0438(5)
_cell_measurement_reflns_used    14710
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      76.0600
_cell_measurement_theta_min      5.0540
_cell_volume                     1190.83(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    6.50    --  -41.95 -38.00  30.00   99
  2  ω   -115.00 -14.00   1.00    6.50    --  -41.95 -57.00 -60.00  101
  3  ω    -66.00  32.00   1.00    6.50    --  -41.95  38.00-150.00   98
  4  ω     23.00  98.00   1.00    6.50    --   41.95-125.00  30.00   75
  5  ω      1.00  83.00   1.00    6.50    --   41.95 -99.00-120.00   82
  6  ω     28.00 109.00   1.00   27.50    --  111.00 -94.00  90.00   81
  7  ω     35.00 116.00   1.00   27.50    --  111.00-111.00 -30.00   81
  8  ω     35.00 144.00   1.00   27.50    --  111.00 -77.00 150.00  109
  9  ω     38.00 137.00   1.00   27.50    --  111.00 -45.00  60.00   99
 10  ω     38.00 137.00   1.00   27.50    --  111.00 -45.00-180.00   99
 11  ω     35.00 144.00   1.00   27.50    --  111.00 -77.00  30.00  109
 12  ω     28.00 109.00   1.00   27.50    --  111.00 -94.00  30.00   81
 13  ω     35.00 139.00   1.00   27.50    --  111.00 -30.00 120.00  104
 14  ω     83.00 178.00   1.00   27.50    --  111.00  30.00   0.00   95
 15  ω     35.00 116.00   1.00   27.50    --  111.00-111.00-180.00   81
 16  ω    100.00 178.00   1.00   27.50    --  111.00 111.00-180.00   78
 17  ω     35.00 144.00   1.00   27.50    --  111.00 -77.00-150.00  109
 18  ω     58.00 178.00   1.00   27.50    --  111.00  15.00 -30.00  120
 19  ω     35.00 116.00   1.00   27.50    --  111.00-111.00  30.00   81
 20  ω     58.00 178.00   1.00   27.50    --  111.00  15.00-150.00  120
 21  ω     28.00 109.00   1.00   27.50    --  111.00 -94.00 -60.00   81
 22  ω     35.00 116.00   1.00   27.50    --  111.00-111.00 -90.00   81
 23  ω     28.00 109.00   1.00   27.50    --  111.00 -94.00   0.00   81
 24  ω     29.00 164.00   1.00   27.50    --  111.00 -15.00 -30.00  135
 25  ω   -118.00  -9.00   1.00    6.50    --  -41.95 -77.00-180.00  109
 26  ω   -118.00  -9.00   1.00    6.50    --  -41.95 -77.00  90.00  109
 27  ω   -118.00  -9.00   1.00    6.50    --  -41.95 -77.00 -90.00  109
 28  ω      9.00 118.00   1.00    6.50    --   41.95  77.00  30.00  109
 29  ω    -30.00  70.00   1.00    6.50    --   41.95 -57.00  30.00  100
 30  ω      9.00 118.00   1.00    6.50    --   41.95  77.00  90.00  109
 31  ω     83.00 178.00   1.00   27.50    --  111.00  30.00  90.00   95
 32  ω     82.00 178.00   1.00   27.50    --  111.00  61.00-150.00   96
 33  ω     82.00 178.00   1.00   27.50    --  111.00  61.00 120.00   96
 34  ω     78.00 147.00   1.00   27.50    --  111.00  77.00-120.00   69
 35  ω     85.00 178.00   1.00   27.50    --  111.00  45.00  30.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0431329000
_diffrn_orient_matrix_UB_12      0.0798694000
_diffrn_orient_matrix_UB_13      -0.0188816000
_diffrn_orient_matrix_UB_21      -0.1470620000
_diffrn_orient_matrix_UB_22      0.0217747000
_diffrn_orient_matrix_UB_23      0.0805843000
_diffrn_orient_matrix_UB_31      0.1540976000
_diffrn_orient_matrix_UB_32      -0.0015067000
_diffrn_orient_matrix_UB_33      0.1587806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23707
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.330
_diffrn_reflns_theta_min         4.751
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.430
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_description       prism
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0467
_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)+(0.0485P)²+2.1077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2478
_reflns_number_total             2489
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc094-r1-or-fe-rf1
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_original_cell_volume        1190.83(11)
_cod_database_code               1565382
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H5.84 Cl2.16 N3 S'
_chemical_oxdiff_usercomment     'ABS-261 radical/pyridine'
_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.
;
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 H9-C9
 0.93 with sigma of 0.02
3. Restrained planarity
 C8, C9, C10, C11, C12, C7
 with sigma of 0.1
 H9, C9, C8, C7, C12, C11, C10
 with sigma of 0.1
4. Others
 Sof(Cl)=1-FVAR(1)
 Sof(H9)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C11(H11), C3(H3), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.759
_oxdiff_exptl_absorpt_empirical_full_min 0.710
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'
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 0.03039(9) 0.59627(3) 0.36405(7) 0.02929(18) Uani 1 1 d . . . . .
Cl1 Cl 0.53885(11) 0.43016(4) 0.77856(8) 0.0433(2) Uani 1 1 d . . . . .
Cl2 Cl 0.47842(11) 0.71132(4) 0.89656(9) 0.0425(2) Uani 1 1 d . . . . .
N2 N 0.2521(3) 0.45898(12) 0.4855(2) 0.0264(4) Uani 1 1 d . . . . .
N1 N 0.0162(3) 0.51880(12) 0.2772(2) 0.0287(5) Uani 1 1 d . . . . .
N3 N 0.0222(3) 0.26563(13) 0.0892(3) 0.0321(5) Uani 1 1 d . . . . .
C1 C 0.1238(4) 0.46329(14) 0.3451(3) 0.0252(5) Uani 1 1 d . . . . .
C2 C 0.0927(4) 0.39553(14) 0.2536(3) 0.0249(5) Uani 1 1 d . . . . .
C7 C 0.2964(3) 0.51881(14) 0.5768(3) 0.0268(5) Uani 1 1 d . . . . .
C6 C 0.1724(4) 0.33160(14) 0.3231(3) 0.0270(5) Uani 1 1 d . . . . .
H6 H 0.2507 0.3310 0.4254 0.032 Uiso 1 1 calc R . . . .
C5 C 0.1329(4) 0.26888(15) 0.2373(3) 0.0298(5) Uani 1 1 d . . . . .
H5 H 0.1862 0.2264 0.2851 0.036 Uiso 1 1 calc R . . . .
C12 C 0.2141(4) 0.58733(14) 0.5379(3) 0.0272(5) Uani 1 1 d . . . . .
C10 C 0.4095(4) 0.63790(16) 0.7740(3) 0.0326(6) Uani 1 1 d . . . . .
C11 C 0.2700(4) 0.64716(15) 0.6341(3) 0.0307(6) Uani 1 1 d . . . . .
H11 H 0.2149 0.6919 0.6047 0.037 Uiso 1 1 calc R . . . .
C9 C 0.4939(4) 0.57150(16) 0.8205(3) 0.0328(6) Uani 1 1 d D . . . .
C8 C 0.4375(4) 0.51324(15) 0.7230(3) 0.0307(6) Uani 1 1 d . . . . .
C3 C -0.0188(4) 0.39350(15) 0.0984(3) 0.0310(6) Uani 1 1 d . . . . .
H3 H -0.0716 0.4353 0.0469 0.037 Uiso 1 1 calc R . . . .
C4 C -0.0489(4) 0.32797(15) 0.0232(3) 0.0340(6) Uani 1 1 d . . . . .
H4 H -0.1236 0.3271 -0.0801 0.041 Uiso 1 1 calc R . . . .
Cl Cl 0.6747(5) 0.5614(2) 0.9843(4) 0.0330(15) Uani 0.165(4) 1 d . . P A 2
H9 H 0.586(3) 0.5648(19) 0.914(2) 0.025(9) Uiso 0.835(4) 1 d D . P A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 6 0.0222
-5 1 0 0.1461
0 0 -6 0.0541
2 1 4 0.0653
0 -12 0 0.0262
-2 1 -4 0.0957
0 12 0 0.0271
5 -2 -1 0.1209
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 S1 C12 105.49(12) . . ?
C1 N2 C7 119.7(2) . . ?
C1 N1 S1 121.44(18) . . ?
C4 N3 C5 116.4(2) . . ?
N2 C1 C2 115.0(2) . . ?
N1 C1 N2 129.5(2) . . ?
N1 C1 C2 115.5(2) . . ?
C6 C2 C1 120.1(2) . . ?
C6 C2 C3 118.1(2) . . ?
C3 C2 C1 121.8(2) . . ?
N2 C7 C12 125.5(2) . . ?
N2 C7 C8 118.5(2) . . ?
C12 C7 C8 116.0(2) . . ?
C2 C6 H6 120.6 . . ?
C5 C6 C2 118.7(2) . . ?
C5 C6 H6 120.6 . . ?
N3 C5 C6 124.0(2) . . ?
N3 C5 H5 118.0 . . ?
C6 C5 H5 118.0 . . ?
C7 C12 S1 118.04(19) . . ?
C11 C12 S1 119.1(2) . . ?
C11 C12 C7 122.8(2) . . ?
C11 C10 Cl2 118.7(2) . . ?
C11 C10 C9 122.1(3) . . ?
C9 C10 Cl2 119.3(2) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 C12 118.0(3) . . ?
C10 C11 H11 121.0 . . ?
C10 C9 Cl 122.1(3) . . ?
C10 C9 H9 123(2) . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 Cl 118.7(3) . . ?
C8 C9 H9 118(2) . . ?
C7 C8 Cl1 118.0(2) . . ?
C9 C8 Cl1 119.9(2) . . ?
C9 C8 C7 122.1(3) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3 120.8 . . ?
N3 C4 C3 124.3(2) . . ?
N3 C4 H4 117.8 . . ?
C3 C4 H4 117.8 . . ?
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 1.630(2) . ?
S1 C12 1.746(3) . ?
Cl1 C8 1.726(3) . ?
Cl2 C10 1.735(3) . ?
N2 C1 1.337(3) . ?
N2 C7 1.365(3) . ?
N1 C1 1.335(3) . ?
N3 C5 1.342(3) . ?
N3 C4 1.337(4) . ?
C1 C2 1.487(3) . ?
C2 C6 1.391(3) . ?
C2 C3 1.395(3) . ?
C7 C12 1.412(4) . ?
C7 C8 1.418(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(4) . ?
C5 H5 0.9300 . ?
C12 C11 1.396(4) . ?
C10 C11 1.380(4) . ?
C10 C9 1.392(4) . ?
C11 H11 0.9300 . ?
C9 C8 1.379(4) . ?
C9 Cl 1.679(4) . ?
C9 H9 0.92(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9300 . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0434 0.2378 5.5675 -0.0843 0.4474 0.8903
-4.5317 0.8513 -0.2202 -0.1233 0.6672 -0.7346
0.0643 -0.2600 -5.6066 0.0879 -0.4669 -0.8799
2.2186 0.9997 4.1217 0.0977 0.0276 0.9948
0.0358 -12.0699 -0.2056 -0.9586 -0.2847 -0.0089
-2.2355 0.9035 -4.1100 0.0533 0.0172 -0.9984
-0.0358 12.0699 0.2056 0.9586 0.2847 0.0089
5.0069 -1.9960 -1.0104 0.0756 -0.8612 0.6141
