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_1566677
_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         '2(C12.5 H15 O4 S0.5)'
_chemical_formula_sum            'C25 H30 O8 S'
_chemical_formula_weight         490.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-03
_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                 95.9688(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.04584(4)
_cell_length_b                   19.87397(12)
_cell_length_c                   12.32816(6)
_cell_measurement_reflns_used    43038
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.6100
_cell_measurement_theta_min      3.6070
_cell_volume                     2447.98(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.964
_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   -123.00 -32.00   0.50    0.05    --  -46.87 -24.00 179.00  182
  2  \w    -33.00  29.00   0.50    0.05    --  -46.87  24.00 -16.00  124
  3  \w     33.00 123.00   0.50    0.05    --   46.87  24.00 -16.00  180
  4  \w    -28.00  33.00   0.50    0.05    --   46.87 -24.00 179.00  122
  5  \w   -164.00 -74.00   0.50    0.15    --  -88.50 -24.00 179.00  180
  6  \w     92.00 178.00   0.50    0.15    --  106.69  24.00 -16.00  172
  7  \w    -30.00  29.00   0.50    0.05    --  -46.87  19.00 120.00  118
  8  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 -90.00   66
  9  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00  30.00   66
 10  \w     31.00 120.00   0.50    0.05    --   46.87  55.00 162.28  178
 11  \w     32.00 120.00   0.50    0.05    --   46.87  54.00 120.31  176
 12  \w     32.00 120.00   0.50    0.05    --   46.87  52.00 136.78  176
 13  \w     31.00 120.00   0.50    0.05    --   46.87  55.00  74.74  178
 14  \w     32.00 120.00   0.50    0.05    --   46.87  52.00 112.72  176
 15  \w     32.00 121.00   0.50    0.05    --   46.87  37.00  30.00  178
 16  \w   -101.00 -15.00   0.50    0.15    --  -88.50  77.00 120.00  172
 17  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  91.08  174
 18  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -53.00  64.69  174
 19  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -50.00 104.73  174
 20  \w   -160.00 -72.00   0.50    0.15    --  -88.50 -54.00  58.93  176
 21  \w   -160.00 -72.00   0.50    0.15    --  -88.50 -54.00  54.72  176
 22  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -52.00 114.17  174
 23  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  12.72  174
 24  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00 100.02  174
 25  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -52.00  -1.56  174
 26  \w    -51.00 -16.00   0.50    0.15    --  -88.50  45.00-180.00   70
 27  \w   -161.00 -74.00   0.50    0.15    --  -88.50 -45.00  30.00  174
 28  \w   -160.00 -78.00   0.50    0.15    --  -88.50 -56.00  -4.20  164
 29  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  87.26  174
 30  \w   -160.00 -72.00   0.50    0.15    --  -88.50 -54.00 108.05  176
 31  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  23.91  174
 32  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00 131.52  174
 33  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00 124.56  174
 34  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  75.07  174
 35  \w   -160.00 -78.00   0.50    0.15    --  -88.50 -56.00  50.90  164
 36  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  84.57  174
 37  \w    -71.00 -15.00   0.50    0.15    --  -88.50  61.00 120.00  112
 38  \w   -160.00 -72.00   0.50    0.15    --  -88.50 -54.00   3.66  176
 39  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  33.78  174
 40  \w   -160.00 -73.00   0.50    0.15    --  -88.50 -52.00  23.72  174
 41  \w    -71.00 -15.00   0.50    0.15    --  -88.50  61.00  90.00  112
 42  \w     91.00 178.00   0.50    0.15    --  106.69  61.00 150.00  174
 43  \w     34.00  89.00   0.50    0.15    --  106.69 -77.00 150.00  110
 44  \w    128.00 175.00   0.50    0.15    --  106.69  61.00  30.00   94
 45  \w     92.00 121.00   0.50    0.15    --  106.69  61.00  30.00   58
 46  \w     90.00 160.00   0.50    0.15    --  106.69  54.00 170.45  140
 47  \w     71.00  97.00   0.50    0.15    --  106.69 -77.00-120.00   52
 48  \w     39.00  67.00   0.50    0.15    --  106.69 -77.00-120.00   56
 49  \w     34.00  59.00   0.50    0.15    --  106.69 -61.00-150.00   50
 50  \w     37.00  68.00   0.50    0.15    --  106.69 -61.00-120.00   62
 51  \w     97.00 174.00   0.50    0.15    --  106.69  55.00  80.25  154
 52  \w     34.00 100.00   0.50    0.15    --  106.69 -77.00  60.00  132
 53  \w     34.00  70.00   0.50    0.15    --  106.69 -61.00-180.00   72
 54  \w     58.00 101.00   0.50    0.15    --  106.69-125.00  60.00   86
 55  \w     35.00  68.00   0.50    0.15    --  106.69 -61.00 -90.00   66
;
_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      0.1527324000
_diffrn_orient_matrix_UB_12      0.0036199000
_diffrn_orient_matrix_UB_13      0.0290046000
_diffrn_orient_matrix_UB_21      0.0165796000
_diffrn_orient_matrix_UB_22      0.0242470000
_diffrn_orient_matrix_UB_23      -0.1165627000
_diffrn_orient_matrix_UB_31      -0.0130610000
_diffrn_orient_matrix_UB_32      0.0735175000
_diffrn_orient_matrix_UB_33      0.0369743000
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            71221
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.528
_diffrn_reflns_theta_min         3.605
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.580
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.555
_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    1.331
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 4120 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(6)
_refine_ls_extinction_coef       0.00075(14)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     620
_refine_ls_number_reflns         9458
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0498P)^2^+0.3934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.873
_reflns_number_gt                9233
_reflns_number_total             9458
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00789d2.cif
_cod_data_source_block           hpd144
_cod_database_code               1566677
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     VNy138-14
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.776
_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 Ternary CH refined with riding coordinates:
 C26(H26), C33(H33), C39(H39), C37(H37), C1(H1), C14(H14), C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C31(H31A,H31B), C43(H43A,H43B), C32(H32A,H32B), C28(H28A,
 H28B), C3(H3A,H3B), C15(H15A,H15B), C7(H7A,H7B), C6(H6A,H6B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C35(H35), C41(H41), C36(H36), C10(H10), C11(H11), C16(H16)
2.d X=CH2 refined with riding coordinates:
 C44(H44A,H44B), C42(H42A,H42B), C19(H19A,H19B), C17(H17A,H17B)
2.e Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C49(H49A,H49B,H49C), C46(H46A,H46B,H46C), C25(H25A,H25B,
 H25C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              51771
_shelx_hkl_checksum              50385
_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 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.832