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_1566668
_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         'C16 H29 N O6 S'
_chemical_formula_sum            'C16 H29 N O6 S'
_chemical_formula_weight         363.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-01
_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                   5.46991(9)
_cell_length_b                   10.15896(14)
_cell_length_c                   34.3303(5)
_cell_measurement_reflns_used    13332
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7780
_cell_measurement_theta_min      2.5690
_cell_volume                     1907.69(5)
_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 0.990
_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    -84.00 -15.00   0.50    0.10    --  -88.50 116.00  60.00  138
  2  \w   -164.00 -72.00   0.50    0.10    --  -88.50 -18.00  62.00  184
  3  \w     34.00 109.00   0.50    0.10    --  106.69-114.00-121.00  150
  4  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 120.00   66
  5  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 -60.00   66
  6  \w    -30.00  29.00   0.50    0.05    --  -46.87  18.00-129.00  118
  7  \w   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 -90.00   66
  8  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00-120.00   74
  9  \w    -30.00  29.00   0.50    0.05    --  -46.87  19.00   0.00  118
 10  \w     34.00 101.00   0.50    0.10    --  106.69 -77.00 120.00  134
 11  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00 120.00   74
 12  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00  30.00   74
 13  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00-150.00   74
 14  \w     89.00 178.00   0.50    0.10    --  106.69  15.00-180.00  178
 15  \w     34.00 101.00   0.50    0.10    --  106.69 -77.00 -90.00  134
 16  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00-120.00   74
 17  \w     34.00 109.00   0.50    0.10    --  106.69-116.00 -28.00  150
 18  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -90.00   74
 19  \w   -121.00 -32.00   0.50    0.05    --  -46.87 -37.00 -30.00  178
 20  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -60.00   74
 21  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -30.00   74
 22  \w   -121.00 -32.00   0.50    0.05    --  -46.87 -37.00 120.00  178
 23  \w   -161.00-104.00   0.50    0.10    --  -88.50 -45.00  30.00  114
 24  \w   -163.00 -73.00   0.50    0.10    --  -88.50 -30.00-180.00  180
 25  \w    -51.00 -16.00   0.50    0.10    --  -88.50  45.00   0.00   70
 26  \w     89.00 178.00   0.50    0.10    --  106.69  15.00   0.00  178
 27  \w     89.00 178.00   0.50    0.10    --  106.69  15.00 -90.00  178
 28  \w     34.00  71.00   0.50    0.10    --  106.69 -61.00   0.00   74
;
_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      -0.0542604000
_diffrn_orient_matrix_UB_12      0.0375610000
_diffrn_orient_matrix_UB_13      -0.0426367000
_diffrn_orient_matrix_UB_21      0.0366031000
_diffrn_orient_matrix_UB_22      -0.1444625000
_diffrn_orient_matrix_UB_23      -0.0123186000
_diffrn_orient_matrix_UB_31      -0.2739165000
_diffrn_orient_matrix_UB_32      -0.0267054000
_diffrn_orient_matrix_UB_33      0.0066772000
_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  0.0472
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            21957
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.533
_diffrn_reflns_theta_min         2.574
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.652
_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    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1475 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(8)
_refine_ls_extinction_coef       0.0010(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   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.6621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                3787
_reflns_number_total             3907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00789d2.cif
_cod_data_source_block           hpd140
_cod_database_code               1566668
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.675
_reflns_odcompleteness_completeness 99.90
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2)
2.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C9(H9A,H9B,
 H9C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              67445
_shelx_hkl_checksum              18330
_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 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.857