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_1566670
_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 H20 Cl N O3 S'
_chemical_formula_sum            'C15 H20 Cl N O3 S'
_chemical_formula_weight         329.83
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-17
_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                89.487(2)
_cell_angle_beta                 85.132(2)
_cell_angle_gamma                82.136(2)
_cell_formula_units_Z            2
_cell_length_a                   5.01880(10)
_cell_length_b                   9.6241(2)
_cell_length_c                   16.1198(4)
_cell_measurement_reflns_used    7974
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.2340
_cell_measurement_theta_min      2.7280
_cell_volume                     768.50(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      99.99(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 0.949
_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     34.00  95.00   0.50    0.05    --   46.62-125.00 152.00  122
  2  \w     34.00 111.00   0.50    0.05    --  106.69-125.00 152.00  154
  3  \w     34.00 101.00   0.50    0.05    --  106.69 -77.00   0.00  134
  4  \w     45.00 126.00   0.50    0.05    --  106.69-145.00 -15.00  162
  5  \w     45.00 107.00   0.50    0.05    --   46.62-145.00 -15.00  124
  6  \w     34.00 111.00   0.50    0.05    --  106.69-125.00-120.00  154
  7  \w     34.00 101.00   0.50    0.05    --  106.69 -77.00-150.00  134
  8  \w     34.00 105.00   0.50    0.05    --  106.69 -94.00 -30.00  142
  9  \w     34.00 105.00   0.50    0.05    --  106.69 -94.00   0.00  142
 10  \w     34.00  71.00   0.50    0.05    --  106.69 -61.00 150.00   74
 11  \w     34.00 101.00   0.50    0.05    --  106.69 -77.00 150.00  134
 12  \w     34.00  71.00   0.50    0.05    --  106.69 -61.00  30.00   74
 13  \w    101.00 178.00   0.50    0.05    --  106.69  77.00-150.00  154
 14  \w     95.00 178.00   0.50    0.05    --  106.69 125.00-129.00  166
 15  \w     91.00 178.00   0.50    0.05    --  106.69  30.00-180.00  174
 16  \w     81.00 170.00   0.50    0.05    --  106.69 145.00  37.00  178
 17  \w    101.00 178.00   0.50    0.05    --  106.69  77.00  90.00  154
 18  \w    -51.00 -16.00   0.50    0.05    --  -88.50  45.00   0.00   70
 19  \w    -51.00 -16.00   0.50    0.05    --  -88.50  45.00  30.00   70
 20  \w    -71.00 -15.00   0.50    0.05    --  -88.50  61.00  90.00  112
 21  \w   -101.00 -23.00   0.50    0.05    --  -46.62 145.00  37.00  156
 22  \w    -86.00 -15.00   0.50    0.05    --  -88.50 125.00-129.00  142
 23  \w    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-180.00   70
 24  \w    -86.00 -13.00   0.50    0.05    --  -46.62 125.00-129.00  146
 25  \w   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00 -60.00  176
 26  \w   -119.00 -60.00   0.50    0.05    --  -46.62-145.00 -15.00  118
 27  \w   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 120.00   72
 28  \w   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 150.00   72
 29  \w   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00 120.00  176
 30  \w   -119.00 -73.00   0.50    0.05    --  -46.62-125.00 152.00   92
 31  \w   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00-120.00   72
 32  \w   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00-180.00   72
 33  \w   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00-150.00  176
 34  \w   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 -90.00   72
 35  \w   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00 -90.00  176
 36  \w   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00  30.00  176
 37  \w   -120.00 -52.00   0.50    0.05    --  -46.62 -37.00  60.00  136
 38  \w   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00  60.00   72
 39  \w   -152.00 -60.00   0.50    0.05    --  -88.50-145.00 -15.00  184
 40  \w   -160.00 -91.00   0.50    0.05    --  -88.50 -61.00  30.00  138
 41  \w   -160.00-100.00   0.50    0.05    --  -88.50 -94.00   0.00  120
 42  \w   -163.00 -73.00   0.50    0.05    --  -88.50 -30.00-150.00  180
 43  \w   -160.00-101.00   0.50    0.05    --  -88.50 -77.00-180.00  118
;
_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      -0.0131563000
_diffrn_orient_matrix_UB_12      -0.0240891000
_diffrn_orient_matrix_UB_13      -0.0938319000
_diffrn_orient_matrix_UB_21      0.0956847000
_diffrn_orient_matrix_UB_22      0.1433082000
_diffrn_orient_matrix_UB_23      -0.0187491000
_diffrn_orient_matrix_UB_31      0.2956050000
_diffrn_orient_matrix_UB_32      -0.0706753000
_diffrn_orient_matrix_UB_33      -0.0066266000
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14635
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.472
_diffrn_reflns_theta_min         2.751
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.554
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.601
_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    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0400P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2859
_reflns_number_total             3083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00789d2.cif
_cod_data_source_block           hpd124
_cod_database_code               1566670
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Cl'
_chemical_oxdiff_usercomment     VNY138-13
_shelx_estimated_absorpt_t_max   0.812
_shelx_estimated_absorpt_t_min   0.538
_reflns_odcompleteness_completeness 99.96
_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, All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C8(H8A,H8B), C13(H13A,H13B), C9(H9A,H9B), C11(H11A,H11B),
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C14(H14), C2(H2)
;
_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 1.443
_oxdiff_exptl_absorpt_empirical_full_min 0.743