Functional Group Divergence and the Structural Basis of Acridine Photocatalysis Revealed by Direct Decarboxysulfonylation
Nguyen, Vu T.; Haug, Graham C.; Nguyen, Viet D.; Vuong, Ngan T. H.; Karki, Guna B.; Arman, Hadi; Larionov, Oleg V.; Chemical Science  (2022) –; doi:10.1039/D2SC00789D

data_1566672
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -57.00  26.00   0.50    0.05    --  -46.87  50.00 -73.00  166
  2  \w    -57.00 -15.00   0.50    0.05    --  -88.50  50.00 -73.00   84
  3  \w    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-150.00   70
  4  \w    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-120.00   70
  5  \w    -71.00 -15.00   0.50    0.05    --  -88.50  61.00 -30.00  112
  6  \w    -86.00 -15.00   0.50    0.05    --  -88.50 125.00  30.00  142
  7  \w   -119.00 -33.00   0.50    0.05    --  -46.87 -44.00-163.96  172
  8  \w     32.00 120.00   0.50    0.05    --   46.87  50.00 -73.00  176
  9  \w     92.00 178.00   0.50    0.05    --  106.69  50.00 -73.00  172
 10  \w     34.00 101.00   0.50    0.05    --  106.69 -77.00 120.00  134
 11  \w     34.00 105.00   0.50    0.05    --  106.69 -94.00 150.00  142
 12  \w     34.00 101.00   0.50    0.05    --  106.69 -77.00  30.00  134
 13  \w     34.00 178.00   0.50    0.05    --  106.69   0.00  90.00  288
 14  \w     34.00  71.00   0.50    0.05    --  106.69 -61.00  30.00   74
 15  \w     34.00 106.00   0.50    0.05    --  106.69-100.00  29.22  144
 16  \w     34.00 111.00   0.50    0.05    --  106.69-125.00 150.00  154
 17  \w     34.00 111.00   0.50    0.05    --  106.69-125.00  30.00  154
 18  \w     34.00  71.00   0.50    0.05    --  106.69 -61.00 150.00   74
 19  \w     32.00 120.00   0.50    0.05    --   46.87  51.00  95.14  176
 20  \w     34.00  71.00   0.50    0.05    --  106.69 -61.00 -60.00   74
 21  \w     34.00 105.00   0.50    0.05    --  106.69 -94.00 -90.00  142
 22  \w     34.00 108.00   0.50    0.05    --  106.69-107.00-124.10  148
 23  \w     32.00 120.00   0.50    0.05    --   46.87  49.00 -30.13  176
 24  \w     32.00 120.00   0.50    0.05    --   46.87  54.00 133.94  176
 25  \w     32.00 120.00   0.50    0.05    --   46.87  53.00  23.01  176
 26  \w     32.00 120.00   0.50    0.05    --   46.87  53.00-177.98  176
 27  \w    -28.00  30.00   0.50    0.05    --   46.87 -19.00   0.00  116
 28  \w    -25.00  57.00   0.50    0.05    --   46.87 -50.00 139.00  164
 29  \w    -28.00  30.00   0.50    0.05    --   46.87 -19.00 150.00  116
 30  \w    -28.00  30.00   0.50    0.05    --   46.87 -19.00  30.00  116
 31  \w   -120.00 -32.00   0.50    0.05    --  -46.87 -50.00 139.00  176
 32  \w   -160.00 -73.00   0.50    0.05    --  -88.50 -50.00 139.00  174
 33  \w   -160.00 -91.00   0.50    0.05    --  -88.50 -61.00  90.00  138
 34  \w   -160.00 -73.00   0.50    0.05    --  -88.50 -55.00 -15.55  174
 35  \w   -160.00-101.00   0.50    0.05    --  -88.50 -77.00-150.00  118
 36  \w   -160.00 -87.00   0.50    0.05    --  -88.50-125.00 -90.00  146
 37  \w   -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       '\w 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0416P)^2^+0.2889P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              21185
_shelx_hkl_checksum              36550
_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