#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:07:58 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565374.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_1565374
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         'C16 H12 Cl4 N2 O S'
_chemical_formula_sum            'C16 H12 Cl4 N2 O S'
_chemical_formula_weight         422.14
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-27
_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                115.075(9)
_cell_angle_beta                 91.228(8)
_cell_angle_gamma                95.201(8)
_cell_formula_units_Z            2
_cell_length_a                   7.4264(7)
_cell_length_b                   11.9574(11)
_cell_length_c                   11.9660(9)
_cell_measurement_reflns_used    3110
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      75.2470
_cell_measurement_theta_min      4.3620
_cell_volume                     956.37(16)
_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      99.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  -6.00   1.00   12.50    --  -42.45 125.00  90.00   78
  2  ω   -119.00  -8.00   1.00   12.50    --  -42.45 -19.00   0.00  111
  3  ω   -114.00 -41.00   1.00   12.50    --  -42.45 -38.00 -60.00   73
  4  ω     25.00  50.00   1.00   12.50    --   42.45-125.00 -90.00   25
  5  ω     36.00  96.00   1.00   12.50    --   42.45-125.00   0.00   60
  6  ω     82.00 123.00   1.00   37.50    --  111.00  77.00 -30.00   41
  7  ω     64.00 111.00   1.00   37.50    --  111.00-111.00 -60.00   47
  8  ω     47.00 104.00   1.00   37.50    --  111.00 -94.00  90.00   57
  9  ω     84.00 122.00   1.00   37.50    --  111.00  61.00  60.00   38
 10  ω     43.00 137.00   1.00   37.50    --  111.00 -61.00 150.00   94
 11  ω     76.00 103.00   1.00   37.50    --  111.00-111.00  60.00   27
 12  ω     56.00 102.00   1.00   37.50    --  111.00 -94.00 150.00   46
 13  ω     44.00  71.00   1.00   37.50    --  111.00-111.00  60.00   27
 14  ω    127.00 177.00   1.00   37.50    --  111.00  77.00 -30.00   50
 15  ω     36.00 133.00   1.00   37.50    --  111.00 -30.00  30.00   97
 16  ω     37.00 130.00   1.00   37.50    --  111.00 -77.00 -60.00   93
 17  ω    137.00 164.00   1.00   37.50    --  111.00 111.00  90.00   27
 18  ω     45.00 137.00   1.00   37.50    --  111.00 -15.00-180.00   92
 19  ω     89.00 176.00   1.00   37.50    --  111.00  30.00  30.00   87
;
_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      0.0116791000
_diffrn_orient_matrix_UB_12      0.0654763000
_diffrn_orient_matrix_UB_13      -0.0865942000
_diffrn_orient_matrix_UB_21      -0.0297331000
_diffrn_orient_matrix_UB_22      0.1236541000
_diffrn_orient_matrix_UB_23      0.1090144000
_diffrn_orient_matrix_UB_31      0.2063030000
_diffrn_orient_matrix_UB_32      0.0300649000
_diffrn_orient_matrix_UB_33      0.0301780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6147
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.088
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.697
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.295
_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            'dark yellow'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0546
_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)+(0.0891P)²+0.7585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2906
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04248c2.cif
_cod_data_source_block           serc232-r1-rf
_cod_depositor_comments
'Adding full bibliography for 1565368--1565385.cif.'
_cod_database_code               1565374
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C15 O0.5 S1.5 Cl5 N2 H12'
_chemical_oxdiff_usercomment     ABS-326
_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 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6), C13(H13), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 1.742
_oxdiff_exptl_absorpt_empirical_full_min 0.521
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.79161(11) 0.35654(8) 0.23878(8) 0.0277(2) Uani 1 1 d . . . . .
Cl4 Cl 0.59357(11) 0.69464(8) 0.09023(8) 0.0325(2) Uani 1 1 d . . . . .
Cl3 Cl 0.73734(12) 0.96605(8) 0.36422(9) 0.0356(2) Uani 1 1 d . . . . .
Cl2 Cl 0.78425(13) 0.89984(10) 0.63007(9) 0.0432(3) Uani 1 1 d . . . . .
Cl1 Cl 0.52022(13) 0.24180(9) 0.15522(9) 0.0398(2) Uani 1 1 d . . . . .
O1 O 0.8799(4) 0.3472(3) 0.8957(3) 0.0365(6) Uani 1 1 d . . . . .
N2 N 0.7169(3) 0.5438(3) 0.4935(3) 0.0244(6) Uani 1 1 d . . . . .
N1 N 0.8362(4) 0.3528(3) 0.3659(3) 0.0303(7) Uani 1 1 d . . . . .
C9 C 0.6929(4) 0.5768(3) 0.3978(3) 0.0244(7) Uani 1 1 d . . . . .
C14 C 0.7217(4) 0.5010(3) 0.2748(3) 0.0257(7) Uani 1 1 d . . . . .
C3 C 0.7832(4) 0.5007(3) 0.7027(3) 0.0274(7) Uani 1 1 d . . . . .
H3 H 0.746693 0.576657 0.713007 0.033 Uiso 1 1 calc R . . . .
C7 C 0.8658(4) 0.2996(3) 0.5708(3) 0.0272(7) Uani 1 1 d . . . . .
H7 H 0.887424 0.240718 0.492649 0.033 Uiso 1 1 calc R . . . .
C11 C 0.6077(4) 0.7331(3) 0.3323(3) 0.0245(7) Uani 1 1 d . . . . .
C10 C 0.6349(4) 0.6960(3) 0.4261(3) 0.0247(7) Uani 1 1 d . . . . .
C1 C 0.7825(4) 0.4394(3) 0.4751(3) 0.0256(7) Uani 1 1 d . . . . .
C2 C 0.8115(4) 0.4122(3) 0.5835(3) 0.0252(7) Uani 1 1 d . . . . .
C12 C 0.6355(4) 0.6517(3) 0.2092(3) 0.0266(7) Uani 1 1 d . . . . .
C6 C 0.8888(4) 0.2729(3) 0.6721(3) 0.0280(7) Uani 1 1 d . . . . .
H6 H 0.923063 0.196268 0.661522 0.034 Uiso 1 1 calc R . . . .
C13 C 0.6944(4) 0.5368(3) 0.1788(3) 0.0275(7) Uani 1 1 d . . . . .
H13 H 0.715167 0.485037 0.097666 0.033 Uiso 1 1 calc R . . . .
C15 C 0.6025(5) 0.7761(3) 0.5582(3) 0.0281(7) Uani 1 1 d . . . . .
H15A H 0.592346 0.725439 0.603615 0.034 Uiso 1 1 calc R . . . .
H15B H 0.489127 0.811397 0.561519 0.034 Uiso 1 1 calc R . . . .
C16 C 0.5472(4) 0.8576(3) 0.3583(3) 0.0282(7) Uani 1 1 d . . . . .
H16A H 0.490977 0.889232 0.436635 0.034 Uiso 1 1 calc R . . . .
H16B H 0.457752 0.848878 0.294091 0.034 Uiso 1 1 calc R . . . .
C4 C 0.8083(4) 0.4771(4) 0.8044(4) 0.0311(8) Uani 1 1 d . . . . .
H4 H 0.791169 0.537384 0.882853 0.037 Uiso 1 1 calc R . . . .
C5 C 0.8599(4) 0.3621(3) 0.7900(3) 0.0285(7) Uani 1 1 d . . . . .
C8 C 0.9128(5) 0.2275(4) 0.8859(4) 0.0369(8) Uani 1 1 d . . . . .
H8A H 0.812223 0.167706 0.840268 0.055 Uiso 1 1 calc GR . . . .
H8B H 0.926935 0.230578 0.967170 0.055 Uiso 1 1 calc GR . . . .
H8C H 1.021255 0.203692 0.843756 0.055 Uiso 1 1 calc GR . . . .
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
0 7 0 0.0083
0 -7 0 0.0285
5 1 -1 0.1981
0 -3 8 0.0184
-5 -1 1 0.2010
0 3 -8 0.0092
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 Cl1 108.85(12) . . ?
N1 S1 C14 105.86(17) . . ?
C14 S1 Cl1 97.49(11) . . ?
C5 O1 C8 118.2(3) . . ?
C1 N2 C9 120.7(3) . . ?
C1 N1 S1 121.8(3) . . ?
N2 C9 C14 124.0(3) . . ?
N2 C9 C10 117.9(3) . . ?
C14 C9 C10 118.1(3) . . ?
C9 C14 S1 118.8(3) . . ?
C9 C14 C13 122.7(3) . . ?
C13 C14 S1 118.5(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C4 C3 C2 121.2(3) . . ?
C2 C7 H7 119.2 . . ?
C2 C7 C6 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 C16 121.5(3) . . ?
C12 C11 C16 118.9(3) . . ?
C9 C10 C15 117.7(3) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 C15 122.4(3) . . ?
N2 C1 N1 127.3(3) . . ?
N2 C1 C2 117.8(3) . . ?
N1 C1 C2 114.9(3) . . ?
C3 C2 C1 120.3(3) . . ?
C7 C2 C3 118.2(3) . . ?
C7 C2 C1 121.5(3) . . ?
C11 C12 Cl4 120.0(3) . . ?
C13 C12 Cl4 117.9(3) . . ?
C13 C12 C11 122.1(3) . . ?
C7 C6 H6 120.3 . . ?
C7 C6 C5 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C14 C13 H13 121.2 . . ?
C12 C13 C14 117.6(3) . . ?
C12 C13 H13 121.2 . . ?
Cl2 C15 H15A 109.4 . . ?
Cl2 C15 H15B 109.4 . . ?
C10 C15 Cl2 111.4(2) . . ?
C10 C15 H15A 109.4 . . ?
C10 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
Cl3 C16 H16A 109.5 . . ?
Cl3 C16 H16B 109.5 . . ?
C11 C16 Cl3 110.7(2) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
O1 C5 C6 124.8(3) . . ?
O1 C5 C4 115.6(3) . . ?
C6 C5 C4 119.6(3) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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 Cl1 2.2789(12) . ?
S1 N1 1.570(3) . ?
S1 C14 1.726(3) . ?
Cl4 C12 1.736(4) . ?
Cl3 C16 1.808(3) . ?
Cl2 C15 1.806(4) . ?
O1 C5 1.357(4) . ?
O1 C8 1.431(4) . ?
N2 C9 1.373(4) . ?
N2 C1 1.314(4) . ?
N1 C1 1.374(5) . ?
C9 C14 1.398(5) . ?
C9 C10 1.429(5) . ?
C14 C13 1.402(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.405(5) . ?
C3 C4 1.374(5) . ?
C7 H7 0.9300 . ?
C7 C2 1.387(5) . ?
C7 C6 1.389(5) . ?
C11 C10 1.387(5) . ?
C11 C12 1.412(5) . ?
C11 C16 1.499(5) . ?
C10 C15 1.499(5) . ?
C1 C2 1.481(5) . ?
C12 C13 1.380(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.398(5) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.401(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
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
0.0312 7.1692 -0.4688 0.5104 0.8345 0.2078
0.0997 -7.1988 0.4965 -0.5132 -0.8390 -0.1809
4.7206 0.8631 -0.6378 0.1669 -0.1032 0.9806
0.1614 -2.6202 7.7175 -0.8380 0.5125 0.1874
-4.7074 -0.9746 0.9688 -0.2027 0.1251 -0.9712
-0.1614 2.6202 -7.7175 0.8380 -0.5125 -0.1874
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.233 0.000 0.000 150.7 60.2 ?
