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_1566676
_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         'C15 H17 N O2 S'
_chemical_formula_sum            'C15 H17 N O2 S'
_chemical_formula_weight         275.35
_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             2020-10-26
_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                 114.8370(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.06120(12)
_cell_length_b                   15.82137(16)
_cell_length_c                   10.26220(14)
_cell_measurement_reflns_used    9829
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3960
_cell_measurement_theta_min      5.3550
_cell_volume                     1335.12(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 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 0.999
_diffrn_measured_fraction_theta_max 0.966
_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   -121.00 -32.00   0.50    0.05    --  -46.87 -31.00 -82.00  178
  2  \w     33.00 122.00   0.50    0.05    --   46.87  31.00  77.00  178
  3  \w    -28.00  38.00   0.50    0.05    --   46.87 -31.00 -82.00  132
  4  \w   -163.00 -73.00   0.50    0.10    --  -88.50 -31.00 -82.00  180
  5  \w     91.00 178.00   0.50    0.10    --  106.69  31.00  77.00  174
  6  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00  60.00   66
  7  \w    -38.00  28.00   0.50    0.05    --  -46.87  31.00  77.00  132
  8  \w    -28.00  30.00   0.50    0.05    --   46.87 -19.00-180.00  116
  9  \w    -51.00 -16.00   0.50    0.10    --  -88.50  45.00  60.00   70
 10  \w    -71.00 -15.00   0.50    0.10    --  -88.50  61.00-120.00  112
 11  \w   -160.00-100.00   0.50    0.10    --  -88.50 -94.00  30.00  120
 12  \w    -51.00 -16.00   0.50    0.10    --  -88.50  45.00 150.00   70
 13  \w    -51.00 -16.00   0.50    0.10    --  -88.50  45.00 -90.00   70
 14  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00 -60.00   74
 15  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00  30.00   74
 16  \w     34.00 101.00   0.50    0.10    --  106.69 -77.00-180.00  134
 17  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00-180.00   74
 18  \w     95.00 178.00   0.50    0.10    --  106.69 125.00 -90.00  166
 19  \w     92.00 178.00   0.50    0.10    --  106.69  45.00 150.00  172
 20  \w     34.00 101.00   0.50    0.10    --  106.69 -77.00   0.00  134
 21  \w     34.00 101.00   0.50    0.10    --  106.69 -77.00 -90.00  134
 22  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00   0.00   74
 23  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00  30.00   74
 24  \w     32.00 121.00   0.50    0.05    --   46.87  37.00 150.00  178
 25  \w     32.00 121.00   0.50    0.05    --   46.87  37.00 -30.00  178
 26  \w     32.00 121.00   0.50    0.05    --   46.87  37.00 -90.00  178
 27  \w     32.00 121.00   0.50    0.05    --   46.87  37.00-120.00  178
 28  \w   -161.00-136.00   0.50    0.10    --  -88.50 -45.00-150.00   50
;
_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      -0.0581928000
_diffrn_orient_matrix_UB_12      0.0388819000
_diffrn_orient_matrix_UB_13      -0.1510812000
_diffrn_orient_matrix_UB_21      0.1757291000
_diffrn_orient_matrix_UB_22      -0.0019487000
_diffrn_orient_matrix_UB_23      0.0130808000
_diffrn_orient_matrix_UB_31      -0.0291378000
_diffrn_orient_matrix_UB_32      -0.0892249000
_diffrn_orient_matrix_UB_33      -0.0660528000
_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  0.0394
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15529
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.259
_diffrn_reflns_theta_min         5.379
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.130
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.342
_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    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0009(2)
_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   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0309
_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/[\s^2^(Fo^2^)+(0.0415P)^2^+0.5688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2515
_reflns_number_total             2694
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00789d2.cif
_cod_data_source_block           hpd237
_cod_database_code               1566676
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'SO2 small vial'
_shelx_estimated_absorpt_t_max   0.825
_shelx_estimated_absorpt_t_min   0.591
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C11(H11A,H11B), C14(H14A,H14B), C13(H13A,H13B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C9(H9), C6(H6), C3(H3), C5(H5)
;
_shelx_res_checksum              85241
_shelx_hkl_checksum              39453
_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 1.394
_oxdiff_exptl_absorpt_empirical_full_min 0.737