#------------------------------------------------------------------------------
#$Date: 2022-03-22 01:14:23 +0200 (Tue, 22 Mar 2022) $
#$Revision: 273877 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/66/1566672.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_1566672
loop_
_publ_author_name
'Nguyen, Vu T.'
'Haug, Graham C.'
'Nguyen, Viet D.'
'Vuong, Ngan T. H.'
'Karki, Guna B.'
'Arman, Hadi'
'Larionov, Oleg V.'
_publ_section_title
;
 Functional Group Divergence and the Structural Basis of Acridine
 Photocatalysis Revealed by Direct Decarboxysulfonylation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00789D
_journal_year                    2022
_chemical_formula_moiety         'C11 H14 O3 S'
_chemical_formula_sum            'C11 H14 O3 S'
_chemical_formula_weight         226.28
_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             2020-06-24
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                91.8184(16)
_cell_angle_beta                 91.4466(15)
_cell_angle_gamma                103.4125(17)
_cell_formula_units_Z            2
_cell_length_a                   5.72076(11)
_cell_length_b                   8.13039(16)
_cell_length_c                   11.8424(2)
_cell_measurement_reflns_used    7153
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0380
_cell_measurement_theta_min      3.7250
_cell_volume                     535.219(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00  26.00   0.50    0.05    --  -46.87  50.00 -73.00  166
  2  ω    -57.00 -15.00   0.50    0.05    --  -88.50  50.00 -73.00   84
  3  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-150.00   70
  4  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-120.00   70
  5  ω    -71.00 -15.00   0.50    0.05    --  -88.50  61.00 -30.00  112
  6  ω    -86.00 -15.00   0.50    0.05    --  -88.50 125.00  30.00  142
  7  ω   -119.00 -33.00   0.50    0.05    --  -46.87 -44.00-163.96  172
  8  ω     32.00 120.00   0.50    0.05    --   46.87  50.00 -73.00  176
  9  ω     92.00 178.00   0.50    0.05    --  106.69  50.00 -73.00  172
 10  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00 120.00  134
 11  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00 150.00  142
 12  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00  30.00  134
 13  ω     34.00 178.00   0.50    0.05    --  106.69   0.00  90.00  288
 14  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00  30.00   74
 15  ω     34.00 106.00   0.50    0.05    --  106.69-100.00  29.22  144
 16  ω     34.00 111.00   0.50    0.05    --  106.69-125.00 150.00  154
 17  ω     34.00 111.00   0.50    0.05    --  106.69-125.00  30.00  154
 18  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 150.00   74
 19  ω     32.00 120.00   0.50    0.05    --   46.87  51.00  95.14  176
 20  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 -60.00   74
 21  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00 -90.00  142
 22  ω     34.00 108.00   0.50    0.05    --  106.69-107.00-124.10  148
 23  ω     32.00 120.00   0.50    0.05    --   46.87  49.00 -30.13  176
 24  ω     32.00 120.00   0.50    0.05    --   46.87  54.00 133.94  176
 25  ω     32.00 120.00   0.50    0.05    --   46.87  53.00  23.01  176
 26  ω     32.00 120.00   0.50    0.05    --   46.87  53.00-177.98  176
 27  ω    -28.00  30.00   0.50    0.05    --   46.87 -19.00   0.00  116
 28  ω    -25.00  57.00   0.50    0.05    --   46.87 -50.00 139.00  164
 29  ω    -28.00  30.00   0.50    0.05    --   46.87 -19.00 150.00  116
 30  ω    -28.00  30.00   0.50    0.05    --   46.87 -19.00  30.00  116
 31  ω   -120.00 -32.00   0.50    0.05    --  -46.87 -50.00 139.00  176
 32  ω   -160.00 -73.00   0.50    0.05    --  -88.50 -50.00 139.00  174
 33  ω   -160.00 -91.00   0.50    0.05    --  -88.50 -61.00  90.00  138
 34  ω   -160.00 -73.00   0.50    0.05    --  -88.50 -55.00 -15.55  174
 35  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00-150.00  118
 36  ω   -160.00 -87.00   0.50    0.05    --  -88.50-125.00 -90.00  146
 37  ω   -160.00 -72.00   0.50    0.05    --  -88.50 -54.00-130.79  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1069627000
_diffrn_orient_matrix_UB_12      -0.1290777000
_diffrn_orient_matrix_UB_13      -0.0669140000
_diffrn_orient_matrix_UB_21      -0.2542305000
_diffrn_orient_matrix_UB_22      -0.0923971000
_diffrn_orient_matrix_UB_23      -0.0432786000
_diffrn_orient_matrix_UB_31      0.0255891000
_diffrn_orient_matrix_UB_32      0.1131529000
_diffrn_orient_matrix_UB_33      -0.1029988000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9842
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.351
_diffrn_reflns_theta_min         3.736
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.571
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.354
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0041(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0287
_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)+(0.0416P)²+0.2889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2088
_reflns_number_total             2143
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00789d2.cif
_cod_data_source_block           hpd133
_cod_original_cell_volume        535.218(18)
_cod_database_code               1566672
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O S'
_chemical_oxdiff_usercomment     'VNY 130-1'
_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_max   0.726
_shelx_estimated_absorpt_t_min   0.652
_reflns_odcompleteness_completeness 100.00
_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:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.754
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 0.95023(5) 0.73697(4) 0.91640(2) 0.01300(12) Uani 1 1 d . . . . .
O2 O 0.95260(17) 0.89115(12) 0.85831(8) 0.0183(2) Uani 1 1 d . . . . .
O3 O 1.17817(17) 0.71165(13) 0.95957(8) 0.0198(2) Uani 1 1 d . . . . .
O1 O 0.22259(17) 0.59826(13) 0.61273(8) 0.0201(2) Uani 1 1 d . . . . .
C8 C 0.6449(2) 0.67239(16) 0.65341(11) 0.0139(3) Uani 1 1 d . . . . .
H8A H 0.726036 0.790985 0.674783 0.017 Uiso 1 1 calc R U . . .
H8B H 0.756828 0.623759 0.607745 0.017 Uiso 1 1 calc R U . . .
C1 C 0.4483(2) 0.75969(16) 0.47278(11) 0.0136(3) Uani 1 1 d . . . . .
C7 C 0.4215(2) 0.67083(16) 0.58226(11) 0.0137(3) Uani 1 1 d . . . . .
C9 C 0.5911(2) 0.57265(17) 0.76052(11) 0.0142(3) Uani 1 1 d . . . . .
H9A H 0.494999 0.457413 0.739807 0.017 Uiso 1 1 calc R U . . .
H9B H 0.493560 0.628538 0.810098 0.017 Uiso 1 1 calc R U . . .
C10 C 0.8201(2) 0.55925(16) 0.82585(11) 0.0145(3) Uani 1 1 d . . . . .
H10A H 0.940873 0.542749 0.770808 0.017 Uiso 1 1 calc R U . . .
H10B H 0.782308 0.457427 0.871829 0.017 Uiso 1 1 calc R U . . .
C6 C 0.6698(2) 0.85573(17) 0.43997(11) 0.0157(3) Uani 1 1 d . . . . .
H6 H 0.809387 0.864190 0.487043 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6869(3) 0.93899(18) 0.33866(12) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.837861 1.004443 0.316907 0.023 Uiso 1 1 calc R U . . .
C2 C 0.2445(2) 0.74728(17) 0.40237(11) 0.0161(3) Uani 1 1 d . . . . .
H2 H 0.093330 0.681676 0.423761 0.019 Uiso 1 1 calc R U . . .
C3 C 0.2626(3) 0.83056(17) 0.30126(12) 0.0189(3) Uani 1 1 d . . . . .
H3 H 0.123613 0.821945 0.253765 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4840(3) 0.92677(18) 0.26923(12) 0.0198(3) Uani 1 1 d . . . . .
H4 H 0.495911 0.983803 0.200082 0.024 Uiso 1 1 calc R U . . .
C11 C 0.7559(2) 0.72694(18) 1.03060(11) 0.0174(3) Uani 1 1 d . . . . .
H11A H 0.818074 0.822656 1.083948 0.026 Uiso 1 1 calc R U . . .
H11B H 0.746220 0.620700 1.069036 0.026 Uiso 1 1 calc R U . . .
H11C H 0.595293 0.731880 1.002252 0.026 Uiso 1 1 calc R U . . .
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'
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
-1 2 -7 0.0629
-2 -3 -1 0.0828
1 -2 7 0.1000
2 3 0 0.0502
0 3 -6 0.0637
3 -4 -3 0.0638
0 -2 7 0.0968
-3 3 4 0.0582
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
O2 S1 O3 117.64(6) . . ?
O2 S1 C10 109.66(6) . . ?
O2 S1 C11 108.26(6) . . ?
O3 S1 C10 107.13(6) . . ?
O3 S1 C11 108.00(6) . . ?
C11 S1 C10 105.49(6) . . ?
H8A C8 H8B 107.8 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C7 C8 C9 112.80(10) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C6 C1 C7 121.90(12) . . ?
C6 C1 C2 119.32(12) . . ?
C2 C1 C7 118.78(12) . . ?
O1 C7 C8 121.00(12) . . ?
O1 C7 C1 120.43(12) . . ?
C1 C7 C8 118.58(11) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 C10 112.47(10) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
S1 C10 H10A 108.5 . . ?
S1 C10 H10B 108.5 . . ?
C9 C10 S1 114.89(9) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.26(13) . . ?
C5 C6 H6 119.9 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.22(13) . . ?
C4 C5 H5 119.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.19(13) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.22(13) . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.80(13) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 O2 1.4464(10) . ?
S1 O3 1.4497(10) . ?
S1 C10 1.7759(13) . ?
S1 C11 1.7644(13) . ?
O1 C7 1.2231(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5103(18) . ?
C8 C9 1.5265(17) . ?
C1 C7 1.4981(18) . ?
C1 C6 1.3972(19) . ?
C1 C2 1.3983(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5320(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.3906(19) . ?
C5 H5 0.9500 . ?
C5 C4 1.388(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C4 H4 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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
O2 S1 C10 C9 -44.24(11) . . . . ?
O3 S1 C10 C9 -172.97(9) . . . . ?
C8 C9 C10 S1 82.93(12) . . . . ?
C1 C6 C5 C4 -0.2(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C7 C8 C9 C10 174.03(10) . . . . ?
C7 C1 C6 C5 -178.81(12) . . . . ?
C7 C1 C2 C3 178.88(12) . . . . ?
C9 C8 C7 O1 1.48(18) . . . . ?
C9 C8 C7 C1 -178.26(10) . . . . ?
C6 C1 C7 O1 174.48(12) . . . . ?
C6 C1 C7 C8 -5.78(18) . . . . ?
C6 C1 C2 C3 -0.39(19) . . . . ?
C6 C5 C4 C3 0.0(2) . . . . ?
C2 C1 C7 O1 -4.77(19) . . . . ?
C2 C1 C7 C8 174.97(11) . . . . ?
C2 C1 C6 C5 0.44(19) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C11 S1 C10 C9 72.13(10) . . . . ?
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
-1.0539 2.0126 -6.9703 0.0939 0.3836 0.9187
-2.3157 -3.1625 -0.8971 0.2206 0.9197 -0.3247
0.9772 -2.1242 6.9536 -0.0866 -0.3531 -0.9316
2.1676 3.4499 -0.0909 -0.2074 -0.8659 0.4552
0.1044 2.9235 -6.4489 0.0653 -0.0176 0.9977
2.7606 -3.8563 -2.6111 0.9678 -0.2325 -0.0968
-0.4234 -2.4676 6.7296 -0.1771 0.0444 -0.9832
-2.7477 3.2751 3.7643 -0.9685 0.2330 -0.0874
