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_1573571
_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         'C42 H40 Br4 N12 Ni2 O6'
_chemical_formula_sum            'C42 H40 Br4 N12 Ni2 O6'
_chemical_formula_weight         1245.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 137.895(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.4927(8)
_cell_length_b                   9.5220(2)
_cell_length_c                   24.7089(14)
_cell_measurement_reflns_used    9163
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      72.9250
_cell_measurement_theta_min      3.5990
_cell_volume                     2286.3(5)
_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 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.970
_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     49.00 115.00   0.50    0.62    --   75.21  15.00   0.00  132
  2  \w     45.00 100.00   0.50    0.62    --   75.63  15.00 -90.00  110
  3  \w     45.00 107.00   0.50    0.62    --   75.63  15.00-150.00  124
  4  \w     54.00 104.00   0.50    0.62    --   75.21  15.00  60.00  100
  5  \w     51.00 107.00   0.50    0.62    --   75.63  15.00 120.00  112
  6  \w     39.00  84.00   0.50    0.62    --   75.63 -95.00 150.00   90
  7  \w     25.00  70.00   0.50    0.16    --   62.57 -95.00 120.00   90
  8  \w     26.00  60.00   0.50    0.16    --   62.57 -95.00  60.00   68
  9  \w     26.00  57.00   0.50    0.16    --   62.57 -95.00   0.00   62
 10  \w     45.00  80.00   0.50    0.62    --   75.21 -95.00  60.00   70
 11  \w     39.00  84.00   0.50    0.62    --   75.63 -95.00  90.00   90
 12  \w     36.00  71.00   0.50    0.16    --   62.57 -95.00-150.00   70
 13  \w     47.00  84.00   0.50    0.62    --   75.63 -95.00-150.00   74
 14  \w    -97.00 -33.00   0.50    0.16    --  -64.16 -15.00  90.00  128
 15  \w    -98.00 -38.00   0.50    0.16    --  -64.16 -15.00-180.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13704
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.516
_diffrn_reflns_theta_min         3.626
_exptl_absorpt_coefficient_mu    5.636
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.392
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_description       cube
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0717P)^2^+1.1857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4093
_reflns_number_total             4466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04257c2.cif
_cod_data_source_block           sdx94_mecn_sd2
_cod_depositor_comments
'Adding full bibliography for 1573571--1573578.cif.'
_cod_original_cell_volume        2286.2(4)
_cod_database_code               1573571
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.399
_shelx_estimated_absorpt_t_min   0.399
_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:
 C00E(H00E), C00H(H00H), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00S(H00S), C00T(H00T)
2.b Idealised Me refined as rotating group:
 C00R(H00A,H00B,H00C), C00U(H00D,H00F,H00G), C00W(H00I,H00J,H00K), C00X(H00L,
 H00M,H00R)
;
_shelx_res_checksum              62849
_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
;