Mechanistic insights into the visible-light-driven <i>O</i>-arylation of carboxylic acids catalyzed by xanthine-based nickel complexes.
Rodriguez-Lugo, Rafael E; Sander, Joan; Dietzmann, Simon; Rittner, Thomas; Rückel, Jannes; Landaeta, Vanessa R.; Park, Jiyong; Nuernberger, Patrick; Baik, Mu-Hyun; Wolf, Robert; Chemical science 16 (2025) 2751–2762; doi:10.1039/d4sc04257c

data_1573575
_publ_section_title
;
 Mechanistic insights into the visible-light-driven <i>O</i>-arylation of
 carboxylic acids catalyzed by xanthine-based nickel complexes.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2751
_journal_page_last               2762
_journal_paper_doi               10.1039/d4sc04257c
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C17 H14 N6 O2'
_chemical_formula_sum            'C17 H14 N6 O2'
_chemical_formula_weight         334.34
_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   geom
_audit_creation_date             2023-05-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-05-10 deposited with the CCDC.	2025-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                84.188(4)
_cell_angle_beta                 74.575(5)
_cell_angle_gamma                88.159(4)
_cell_formula_units_Z            2
_cell_length_a                   6.6161(4)
_cell_length_b                   11.0537(6)
_cell_length_c                   11.1219(6)
_cell_measurement_reflns_used    4476
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      66.1790
_cell_measurement_theta_min      5.4620
_cell_volume                     780.03(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 4.2047
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.990
_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    -74.00 -49.00   1.00    4.00    --  -42.98 108.00-139.00   25
  2  \w      2.00  77.00   1.00    4.00    --   42.98-108.00 123.00   75
  3  \w     96.00 121.00   1.00   16.00    --   86.50 108.00-139.00   25
  4  \w     21.00  46.00   1.00   16.00    --   86.50-108.00 123.00   25
  5  \w    -85.00 -60.00   1.00   16.00    --  -90.00 108.00-139.00   25
  6  \w   -142.00-116.00   1.00   16.00    --  -90.00-108.00 123.00   26
  7  \w     29.00 111.00   1.00    4.00    --   42.98  57.00 -90.00   82
  8  \w     34.00 111.00   1.00    4.00    --   42.98  37.00-150.00   77
  9  \w     19.00  46.00   1.00   16.00    --   86.50 -30.00  90.00   27
 10  \w     71.00 111.00   1.00   16.00    --   86.50 -30.00  90.00   40
 11  \w    -98.00 -72.00   1.00   16.00    --  -90.00 -30.00  90.00   26
 12  \w   -111.00 -84.00   1.00   16.00    --  -90.00  61.00-120.00   27
 13  \w   -138.00-112.00   1.00   16.00    --  -90.00 -30.00  90.00   26
 14  \w   -105.00 -80.00   1.00   16.00    --  -90.00  89.00  -8.01   25
 15  \w    -88.00 -57.00   1.00   16.00    --  -90.00 125.00   0.00   31
 16  \w    -34.00  -8.00   1.00   16.00    --  -90.00  89.00  -8.01   26
 17  \w   -104.00 -79.00   1.00   16.00    --  -90.00  15.00   0.00   25
 18  \w   -103.00 -57.00   1.00   16.00    --  -90.00 125.00  60.00   46
 19  \w   -147.00-105.00   1.00   16.00    --  -90.00 -77.00-150.00   42
 20  \w    -56.00 -28.00   1.00   16.00    --  -90.00 125.00 120.00   28
 21  \w   -149.00-123.00   1.00   16.00    --  -90.00 -61.00  60.00   26
 22  \w   -139.00-113.00   1.00   16.00    --  -90.00 -45.00-120.00   26
 23  \w   -112.00 -50.00   1.00   16.00    --  -90.00 125.00 -30.00   62
 24  \w   -146.00-107.00   1.00   16.00    --  -90.00 -77.00-180.00   39
 25  \w   -114.00 -69.00   1.00   16.00    --  -90.00  77.00-150.00   45
 26  \w   -160.00-114.00   1.00   16.00    --  -90.00 -77.00 150.00   46
 27  \w   -145.00 -77.00   1.00   16.00    --  -90.00 -45.00  90.00   68
 28  \w   -116.00 -82.00   1.00   16.00    --  -90.00  61.00  30.00   34
 29  \w   -164.00-111.00   1.00   16.00    --  -90.00-125.00 150.00   53
 30  \w    -73.00 -47.00   1.00   16.00    --  -90.00  61.00-120.00   26
 31  \w   -112.00 -41.00   1.00   16.00    --  -90.00 125.00  30.00   71
 32  \w   -113.00 -65.00   1.00   16.00    --  -90.00  61.00 -90.00   48
 33  \w    -89.00 -64.00   1.00   16.00    --  -90.00 -61.00   0.00   25
 34  \w   -117.00 -63.00   1.00   16.00    --  -90.00 -30.00-180.00   54
 35  \w    -92.00 -64.00   1.00   16.00    --  -90.00 125.00 -60.00   28
 36  \w   -102.00 -53.00   1.00   16.00    --  -90.00 114.00-166.81   49
 37  \w   -161.00-121.00   1.00   16.00    --  -90.00-125.00-180.00   40
 38  \w   -140.00-115.00   1.00   16.00    --  -90.00 -30.00 120.00   25
 39  \w   -117.00 -92.00   1.00   16.00    --  -90.00  77.00 120.00   25
 40  \w   -116.00 -22.00   1.00   16.00    --  -90.00  30.00  90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8636
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.700
_diffrn_reflns_theta_max         66.700
_diffrn_reflns_theta_min         4.020
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0704
_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^)+(0.1439P)^2^+0.4170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2363
_reflns_number_total             2740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04257c2.cif
_cod_data_source_block           sdx61_sd1
_cod_depositor_comments
'Adding full bibliography for 1573571--1573578.cif.'
_cod_database_code               1573575
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00B,H00C), C00P(H00D,H00E,H00F)
;
_shelx_res_checksum              18941
_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
;