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_1566673
_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_absolute_configuration ad
_chemical_formula_moiety         'C10 H11 F O3 S'
_chemical_formula_sum            'C10 H11 F O3 S'
_chemical_formula_weight         230.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-23
_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                90
_cell_angle_beta                 91.7220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.71650(10)
_cell_length_b                   12.1828(2)
_cell_length_c                   14.7356(2)
_cell_measurement_reflns_used    14719
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3720
_cell_measurement_theta_min      3.6020
_cell_volume                     1025.77(3)
_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 2018/2 (Sheldrick, 2018)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.974
_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    -91.00 -16.00   0.50    0.06    --  -46.87 131.00-107.00  150
  2  \w   -120.00 -70.00   0.50    0.06    --  -46.87-131.00-177.00  100
  3  \w    -95.00 -19.00   0.50    0.06    --  -46.87 137.00  69.00  152
  4  \w   -120.00 -66.00   0.50    0.06    --  -46.87-137.00   6.00  108
  5  \w     38.00  99.00   0.50    0.06    --   46.87-131.00-177.00  122
  6  \w    -90.00 -16.00   0.50    0.24    --  -88.50 131.00-107.00  148
  7  \w   -160.00 -70.00   0.50    0.24    --  -88.50-131.00-177.00  180
  8  \w    -95.00 -19.00   0.50    0.24    --  -88.50 137.00  69.00  152
  9  \w     41.00 120.00   0.50    0.24    --  106.69-137.00   6.00  158
 10  \w     87.00 178.00   0.50    0.24    --  106.69 137.00  69.00  182
 11  \w     38.00 116.00   0.50    0.24    --  106.69-131.00-177.00  156
 12  \w     91.00 178.00   0.50    0.24    --  106.69 131.00-107.00  174
 13  \w   -120.00 -87.00   0.50    0.06    --  -46.87-125.00 -60.00   66
 14  \w   -120.00 -83.00   0.50    0.06    --  -46.87 -57.00   0.00   74
 15  \w   -120.00 -83.00   0.50    0.06    --  -46.87 -57.00 -90.00   74
 16  \w     83.00 120.00   0.50    0.06    --   46.87  57.00 120.00   74
 17  \w     41.00 102.00   0.50    0.06    --   46.87-137.00   6.00  122
 18  \w    -51.00 -16.00   0.50    0.24    --  -88.50  45.00 120.00   70
 19  \w   -160.00 -91.00   0.50    0.24    --  -88.50 -61.00 -90.00  138
 20  \w    -51.00 -16.00   0.50    0.24    --  -88.50  45.00  30.00   70
 21  \w    -51.00 -16.00   0.50    0.24    --  -88.50  45.00  60.00   70
 22  \w     92.00 178.00   0.50    0.24    --  106.69  45.00   0.00  172
 23  \w     34.00 105.00   0.50    0.24    --  106.69 -94.00-150.00  142
 24  \w     34.00  71.00   0.50    0.24    --  106.69 -61.00-120.00   74
 25  \w     34.00  71.00   0.50    0.24    --  106.69 -61.00-180.00   74
 26  \w     34.00  71.00   0.50    0.24    --  106.69 -61.00 -60.00   74
 27  \w     95.00 178.00   0.50    0.24    --  106.69 125.00 -60.00  166
 28  \w     34.00 101.00   0.50    0.24    --  106.69 -77.00 150.00  134
 29  \w   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 -60.00  178
 30  \w   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 150.00  178
 31  \w   -121.00 -56.00   0.50    0.06    --  -46.87 -37.00-150.00  130
 32  \w   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00  60.00  178
 33  \w     53.00  78.00   0.50    0.24    --  106.69-132.00-177.00   50
 34  \w   -118.00 -91.00   0.50    0.06    --  -46.87-125.00 120.00   54
 35  \w   -150.00-108.00   0.50    0.24    --  -88.50 -77.00  30.00   84
 36  \w    -41.00 -16.00   0.50    0.24    --  -88.50  45.00 -60.00   50
 37  \w   -158.00-109.00   0.50    0.24    --  -88.50 -94.00 -60.00   98
 38  \w    -51.00 -26.00   0.50    0.24    --  -88.50  45.00  90.00   50
 39  \w   -149.00-123.00   0.50    0.24    --  -88.50 -77.00-120.00   52
 40  \w     34.00  59.00   0.50    0.24    --  106.69 -61.00  90.00   50
 41  \w     47.00 100.00   0.50    0.24    --  106.69 -77.00 -30.00  106
 42  \w     36.00 111.00   0.50    0.24    --  106.69-125.00  90.00  150
 43  \w    149.00 175.00   0.50    0.24    --  106.69  45.00-120.00   52
 44  \w     76.00 101.00   0.50    0.24    --  106.69 -77.00-150.00   50
 45  \w     98.00 125.00   0.50    0.24    --  106.69  45.00-120.00   54
 46  \w     34.00  59.00   0.50    0.24    --  106.69 -61.00-150.00   50
 47  \w     34.00  60.00   0.50    0.24    --  106.69 -61.00  60.00   52
 48  \w     34.00  68.00   0.50    0.24    --  106.69 -61.00   0.00   68
 49  \w   -119.00 -94.00   0.50    0.06    --  -46.87-132.00-177.00   50
 50  \w   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 120.00  178
 51  \w   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 -90.00  178
 52  \w   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00   0.00  178
 53  \w   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00-120.00  178
 54  \w   -120.00 -83.00   0.50    0.06    --  -46.87 -57.00 120.00   74
 55  \w     32.00 121.00   0.50    0.06    --   46.87  37.00  90.00  178
 56  \w     32.00 121.00   0.50    0.06    --   46.87  37.00 -60.00  178
 57  \w     32.00 121.00   0.50    0.06    --   46.87  37.00 -90.00  178
 58  \w     32.00 121.00   0.50    0.06    --   46.87  37.00-180.00  178
;
_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      0.0212245000
_diffrn_orient_matrix_UB_12      0.1000643000
_diffrn_orient_matrix_UB_13      -0.0631181000
_diffrn_orient_matrix_UB_21      -0.0356939000
_diffrn_orient_matrix_UB_22      0.0772927000
_diffrn_orient_matrix_UB_23      0.0811861000
_diffrn_orient_matrix_UB_31      0.2663755000
_diffrn_orient_matrix_UB_32      0.0023743000
_diffrn_orient_matrix_UB_33      0.0191126000
_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  0.0501
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22324
_diffrn_reflns_point_group_measured_fraction_full 0.798
_diffrn_reflns_point_group_measured_fraction_max 0.752
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.622
_diffrn_reflns_theta_min         3.628
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.841
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.763
_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    1.491
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1091 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0528P)^2^+0.3443P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.540
_reflns_Friedel_fraction_full    0.595
_reflns_Friedel_fraction_max     0.530
_reflns_number_gt                3185
_reflns_number_total             3241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00789d2.cif
_cod_data_source_block           hpd130b
_cod_database_code               1566673
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O S F'
_chemical_oxdiff_usercomment     'K44-9 FLou'
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C2(H2A,H2B), C13(H13A,H13B), C1(H1A,H1B),
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C6(H6), C7(H7), C10(H10), C17(H17), C18(H18), C8(H8), C16(H16),
 C9(H9), C19(H19)
;
_shelx_res_checksum              2007
_shelx_hkl_checksum              33996
_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 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.807