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_1566669
_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         'C18 H22 O2 S'
_chemical_formula_sum            'C18 H22 O2 S'
_chemical_formula_weight         302.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-07
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.33740(10)
_cell_length_b                   6.06610(10)
_cell_length_c                   28.5106(4)
_cell_measurement_reflns_used    5874
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      76.3020
_cell_measurement_theta_min      3.0910
_cell_volume                     1614.89(4)
_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      99.98(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 0.972
_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    -75.00  26.00   0.50    0.05    --  -46.75  86.00 140.00  202
  2  \w   -162.00 -73.00   0.50    0.18    --  -88.50 -37.00 167.00  178
  3  \w    -43.00 -14.00   0.50    0.18    --  -88.50  37.00 -36.00   58
  4  \w     34.00 110.00   0.50    0.18    --  106.69-120.00 -54.00  152
  5  \w    101.00 178.00   0.50    0.18    --  106.69  86.00 140.00  154
  6  \w   -119.00 -83.00   0.50    0.05    --  -46.75 -57.00-150.00   72
  7  \w   -119.00 -54.00   0.50    0.05    --  -46.75-153.00 147.00  130
  8  \w     83.00 119.00   0.50    0.05    --   46.75  57.00-180.00   72
  9  \w    -51.00 -16.00   0.50    0.18    --  -88.50  45.00 150.00   70
 10  \w     34.00  71.00   0.50    0.18    --  106.69 -61.00-150.00   74
 11  \w     34.00  71.00   0.50    0.18    --  106.69 -61.00 -60.00   74
 12  \w     34.00 111.00   0.50    0.18    --  106.69-125.00  90.00  154
 13  \w     34.00  71.00   0.50    0.18    --  106.69 -61.00-180.00   74
 14  \w     34.00  71.00   0.50    0.18    --  106.69 -61.00 150.00   74
 15  \w     34.00  71.00   0.50    0.18    --  106.69 -61.00  60.00   74
 16  \w   -121.00 -32.00   0.50    0.05    --  -46.75 -37.00-120.00  178
 17  \w   -121.00 -32.00   0.50    0.05    --  -46.75 -37.00   0.00  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      0.1602217000
_diffrn_orient_matrix_UB_12      0.0073219000
_diffrn_orient_matrix_UB_13      0.0505188000
_diffrn_orient_matrix_UB_21      -0.0345379000
_diffrn_orient_matrix_UB_22      0.0476175000
_diffrn_orient_matrix_UB_23      0.1079185000
_diffrn_orient_matrix_UB_31      -0.0193847000
_diffrn_orient_matrix_UB_32      -0.0245089000
_diffrn_orient_matrix_UB_33      0.2240752000
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9898
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.594
_diffrn_reflns_theta_min         3.100
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.767
_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    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0402P)^2^+0.4378P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.805
_reflns_Friedel_fraction_max     0.719
_reflns_number_gt                2804
_reflns_number_total             2879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00789d2.cif
_cod_data_source_block           hpd150a
_cod_database_code               1566669
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S O'
_reflns_odcompleteness_completeness 99.71
_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:
 C1(H1A,H1B), C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C14(H14), C18(H18), C16(H16), C17(H17), C7(H7),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              15461
_shelx_hkl_checksum              74427
_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 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.826