#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:07:58 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565379.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_1565379
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         'Cl4 Ga, C13 H6 Cl3 N2 S'
_chemical_formula_sum            'C13 H6 Cl7 Ga N2 S'
_chemical_formula_weight         540.13
_chemical_properties_physical    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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-15
_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                 94.444(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5753(4)
_cell_length_b                   9.8718(4)
_cell_length_c                   20.0990(7)
_cell_measurement_reflns_used    27045
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      75.9050
_cell_measurement_theta_min      4.2510
_cell_volume                     1894.16(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      100.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    2.00    --  -41.96 -38.00  90.00   99
  2  ω   -122.00  -1.00   1.00    2.00    --  -41.96 -19.00 150.00  121
  3  ω    -96.00  -2.00   1.00    2.00    --  -41.96 125.00-120.00   94
  4  ω     23.00  98.00   1.00    2.00    --   41.96-125.00  60.00   75
  5  ω      1.00  83.00   1.00    2.00    --   41.96 -99.00  60.00   82
  6  ω     23.00  98.00   1.00    2.00    --   41.96-125.00-180.00   75
  7  ω     35.00 116.00   1.00    7.00    --  111.00-111.00 -60.00   81
  8  ω     78.00 178.00   1.00    7.00    --  111.00  77.00 -30.00  100
  9  ω     78.00 178.00   1.00    7.00    --  111.00  77.00  90.00  100
 10  ω     38.00 137.00   1.00    7.00    --  111.00 -45.00  30.00   99
 11  ω     78.00 178.00   1.00    7.00    --  111.00  77.00  60.00  100
 12  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00-120.00   81
 13  ω    100.00 178.00   1.00    7.00    --  111.00 111.00  90.00   78
 14  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00 150.00   81
 15  ω    100.00 178.00   1.00    7.00    --  111.00 111.00 -60.00   78
 16  ω     83.00 178.00   1.00    7.00    --  111.00  30.00 -90.00   95
 17  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00 -30.00   81
 18  ω     83.00 178.00   1.00    7.00    --  111.00  30.00-180.00   95
 19  ω     39.00 140.00   1.00    7.00    --  111.00 -61.00-120.00  101
 20  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00-150.00   81
 21  ω     35.00 116.00   1.00    7.00    --  111.00-111.00  30.00   81
 22  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00  60.00   81
 23  ω     35.00 116.00   1.00    7.00    --  111.00-111.00 120.00   81
 24  ω     35.00 116.00   1.00    7.00    --  111.00-111.00-150.00   81
 25  ω     57.00 151.00   1.00    7.00    --  111.00 178.00 150.00   94
 26  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00 120.00   81
 27  ω    100.00 178.00   1.00    7.00    --  111.00 111.00   0.00   78
 28  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00  30.00   81
 29  ω   -116.00 -17.00   1.00    2.00    --  -41.96 -38.00  30.00   99
 30  ω   -115.00 -14.00   1.00    2.00    --  -41.96 -57.00 -30.00  101
 31  ω      9.00 118.00   1.00    2.00    --   41.96  77.00   0.00  109
 32  ω      9.00 118.00   1.00    2.00    --   41.96  77.00-180.00  109
 33  ω      7.00  35.00   1.00    2.00    --   41.96  86.00 103.25   28
 34  ω      9.00 118.00   1.00    2.00    --   41.96  77.00 -90.00  109
 35  ω     85.00 178.00   1.00    7.00    --  111.00  45.00  30.00   93
 36  ω     82.00 155.00   1.00    7.00    --  111.00  61.00 120.00   73
 37  ω     82.00 178.00   1.00    7.00    --  111.00  61.00-150.00   96
 38  ω     85.00 178.00   1.00    7.00    --  111.00  45.00 -60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1553455000
_diffrn_orient_matrix_UB_12      -0.0145100000
_diffrn_orient_matrix_UB_13      -0.0135588000
_diffrn_orient_matrix_UB_21      -0.0258250000
_diffrn_orient_matrix_UB_22      -0.1489679000
_diffrn_orient_matrix_UB_23      -0.0205929000
_diffrn_orient_matrix_UB_31      -0.0345708000
_diffrn_orient_matrix_UB_32      0.0444373000
_diffrn_orient_matrix_UB_33      -0.0728471000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1269
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36088
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.051
_diffrn_reflns_theta_min         4.413
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.113
_exptl_absorpt_correction_T_max  0.539
_exptl_absorpt_correction_T_min  0.152
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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            'clear blackish violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.917
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0617
_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)+(0.1050P)²+3.5470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3653
_reflns_number_total             3657
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc125-r1-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565379
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C13 N2 S1 Ga1 Cl7 H6'
_chemical_oxdiff_usercomment     ABS-499
_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 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C3(H3), C4(H4), C7(H7), C6(H6), C5(H5)
;
_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.757
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
Ga1 Ga 0.22320(5) 0.46638(5) 0.77578(2) 0.02458(19) Uani 1 1 d . . . . .
Cl1 Cl 0.54545(10) 0.73307(9) 0.44724(4) 0.0270(2) Uani 1 1 d . . . . .
S1 S 0.61386(10) 0.55599(10) 0.69945(5) 0.0258(2) Uani 1 1 d . . . . .
Cl2 Cl 0.31827(10) 0.93653(9) 0.48927(5) 0.0295(2) Uani 1 1 d . . . . .
Cl5 Cl 0.38693(11) 0.60409(11) 0.81539(5) 0.0326(3) Uani 1 1 d . . . . .
Cl6 Cl 0.16806(10) 0.34004(10) 0.85833(5) 0.0335(3) Uani 1 1 d . . . . .
Cl4 Cl 0.31657(11) 0.33904(11) 0.70176(5) 0.0352(3) Uani 1 1 d . . . . .
Cl3 Cl 0.23771(12) 0.94200(12) 0.63737(5) 0.0386(3) Uani 1 1 d . . . . .
Cl7 Cl 0.04736(14) 0.57912(13) 0.73178(6) 0.0481(3) Uani 1 1 d . . . . .
N2 N 0.6616(3) 0.5644(3) 0.55408(16) 0.0226(6) Uani 1 1 d . . . . .
N1 N 0.7213(4) 0.4693(3) 0.66201(17) 0.0266(7) Uani 1 1 d . . . . .
C8 C 0.5668(4) 0.6488(4) 0.57493(17) 0.0206(7) Uani 1 1 d . . . . .
C13 C 0.5282(4) 0.6575(4) 0.64274(19) 0.0225(7) Uani 1 1 d . . . . .
C1 C 0.7344(4) 0.4803(4) 0.59599(19) 0.0227(7) Uani 1 1 d . . . . .
C10 C 0.3989(4) 0.8293(4) 0.54613(19) 0.0240(8) Uani 1 1 d . . . . .
C9 C 0.4986(4) 0.7395(4) 0.52751(18) 0.0217(7) Uani 1 1 d . . . . .
C2 C 0.8365(4) 0.3911(4) 0.5674(2) 0.0245(8) Uani 1 1 d . . . . .
C12 C 0.4255(4) 0.7486(4) 0.6617(2) 0.0267(8) Uani 1 1 d . . . . .
H12 H 0.400541 0.751601 0.705516 0.032 Uiso 1 1 calc R . . . .
C11 C 0.3636(4) 0.8320(4) 0.6144(2) 0.0272(8) Uani 1 1 d . . . . .
C3 C 0.8542(4) 0.3953(4) 0.4994(2) 0.0272(8) Uani 1 1 d . . . . .
H3 H 0.800814 0.455022 0.472140 0.033 Uiso 1 1 calc R . . . .
C4 C 0.9518(4) 0.3106(5) 0.4713(2) 0.0337(9) Uani 1 1 d . . . . .
H4 H 0.962750 0.311955 0.425766 0.040 Uiso 1 1 calc R . . . .
C7 C 0.9183(5) 0.3043(5) 0.6092(2) 0.0364(10) Uani 1 1 d . . . . .
H7 H 0.907268 0.302700 0.654795 0.044 Uiso 1 1 calc R . . . .
C6 C 1.0168(6) 0.2200(6) 0.5823(3) 0.0480(13) Uani 1 1 d . . . . .
H6 H 1.071697 0.161647 0.609596 0.058 Uiso 1 1 calc R . . . .
C5 C 1.0315(5) 0.2246(6) 0.5140(3) 0.0469(12) Uani 1 1 d . . . . .
H5 H 1.096934 0.168157 0.496253 0.056 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 6 -6 0.0887
-1 0 -13 0.1025
1 -6 -6 0.0844
1 -6 6 0.0855
1 -2 12 0.0948
-1 5 9 0.0981
2 2 -12 0.0992
6 0 0 0.0324
-2 -2 12 0.0900
-6 0 0 0.0267
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
Cl5 Ga1 Cl4 106.63(4) . . ?
Cl6 Ga1 Cl5 106.84(4) . . ?
Cl6 Ga1 Cl4 108.98(5) . . ?
Cl7 Ga1 Cl5 110.22(5) . . ?
Cl7 Ga1 Cl6 112.47(5) . . ?
Cl7 Ga1 Cl4 111.43(5) . . ?
N1 S1 C13 107.61(18) . . ?
C8 N2 C1 121.8(3) . . ?
C1 N1 S1 122.8(3) . . ?
N2 C8 C13 124.7(3) . . ?
N2 C8 C9 118.2(3) . . ?
C9 C8 C13 117.1(3) . . ?
C8 C13 S1 117.2(3) . . ?
C12 C13 S1 120.7(3) . . ?
C12 C13 C8 122.0(3) . . ?
N2 C1 N1 125.9(3) . . ?
N2 C1 C2 117.1(3) . . ?
N1 C1 C2 117.0(3) . . ?
C9 C10 Cl2 120.5(3) . . ?
C9 C10 C11 119.4(3) . . ?
C11 C10 Cl2 120.1(3) . . ?
C8 C9 Cl1 117.8(3) . . ?
C10 C9 Cl1 121.3(3) . . ?
C10 C9 C8 120.9(3) . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 C7 120.3(4) . . ?
C7 C2 C1 119.4(4) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 C13 118.3(4) . . ?
C11 C12 H12 120.9 . . ?
C10 C11 Cl3 119.4(3) . . ?
C12 C11 Cl3 118.3(3) . . ?
C12 C11 C10 122.3(3) . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.8(4) . . ?
C5 C4 H4 121.1 . . ?
C2 C7 H7 120.2 . . ?
C2 C7 C6 119.7(4) . . ?
C6 C7 H7 120.2 . . ?
C7 C6 H6 120.5 . . ?
C5 C6 C7 119.1(5) . . ?
C5 C6 H6 120.5 . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.3(4) . . ?
C6 C5 H5 118.8 . . ?
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
Ga1 Cl5 2.1786(11) . ?
Ga1 Cl6 2.1732(11) . ?
Ga1 Cl4 2.1907(11) . ?
Ga1 Cl7 2.1506(12) . ?
Cl1 C9 1.709(4) . ?
S1 N1 1.574(3) . ?
S1 C13 1.683(4) . ?
Cl2 C10 1.699(4) . ?
Cl3 C11 1.712(4) . ?
N2 C8 1.324(5) . ?
N2 C1 1.339(5) . ?
N1 C1 1.347(5) . ?
C8 C13 1.442(5) . ?
C8 C9 1.428(5) . ?
C13 C12 1.407(5) . ?
C1 C2 1.466(5) . ?
C10 C9 1.376(5) . ?
C10 C11 1.439(5) . ?
C2 C3 1.391(6) . ?
C2 C7 1.397(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.359(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.404(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.399(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.390(8) . ?
C5 H5 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
-1.4969 5.5066 -5.6566 -0.2357 -0.6652 0.7085
-0.5038 0.0273 -12.8797 0.0960 0.2742 0.9569
1.0473 -5.5516 -6.2538 0.3280 0.9288 0.1727
1.4986 -5.5290 5.5669 0.2376 0.6703 -0.7030
0.8384 -1.5538 12.3663 -0.0149 -0.0448 -0.9989
-0.7520 4.7018 8.7904 -0.3042 -0.8620 -0.4054
1.5249 1.7664 -12.3348 0.3785 -0.0485 0.9243
6.1949 -0.2377 0.0986 0.9645 -0.1266 -0.2319
-2.0369 -1.7151 12.1126 -0.4558 0.0587 -0.8882
-6.2052 0.1999 0.1602 -0.9690 0.1272 0.2117
