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_1573572
_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         'C38 H34 Br4 N10 Ni2 O6, 2(C H2 Cl2)'
_chemical_formula_sum            'C40 H38 Br4 Cl4 N12 Ni2 O4'
_chemical_formula_weight         1329.68
_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                 108.664(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.4368(3)
_cell_length_b                   9.1144(2)
_cell_length_c                   20.4830(4)
_cell_measurement_reflns_used    6962
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      75.2140
_cell_measurement_theta_min      3.4870
_cell_volume                     2376.60(9)
_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 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.911
_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     53.00 111.00   0.50    0.05    --   79.50  12.00 158.34  116
  2  \w     56.00 122.00   0.50    0.05    --   79.50  17.00  71.60  132
  3  \w     50.00 110.00   0.50    0.05    --   79.50  14.00  -7.12  120
  4  \w     60.00  92.00   0.50    0.05    --   79.50  20.00 -85.51   64
  5  \w     46.00  83.00   0.50    0.05    --   79.50   6.00 -88.17   74
  6  \w     42.00  68.00   0.50    0.05    --   79.50 -72.00 -87.90   52
  7  \w     42.00  84.00   0.50    0.05    --   75.78 -95.00-120.00   84
  8  \w     35.00  60.00   0.50    0.05    --   63.51 -95.00 -60.00   50
  9  \w     27.00  64.00   0.50    0.05    --   63.51 -95.00   0.00   74
 10  \w     26.00  57.00   0.50    0.05    --   63.51 -95.00  60.00   62
 11  \w     43.00  95.00   0.50    0.05    --   79.50-114.00 120.11  104
 12  \w     44.00  69.00   0.50    0.05    --   79.50 -75.00 168.68   50
 13  \w     28.00  67.00   0.50    0.05    --   63.51 -95.00 150.00   78
 14  \w    -60.00 -34.00   0.50    0.05    --  -70.29 125.00-180.00   52
 15  \w    -98.00 -72.00   0.50    0.05    --  -70.29 125.00-180.00   52
;
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12001
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         75.767
_diffrn_reflns_theta_min         3.472
_exptl_absorpt_coefficient_mu    7.455
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70507
_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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_description       plate
_exptl_crystal_F_000             1316
_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0548P)^2^+2.0313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3962
_reflns_number_total             4510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04257c2.cif
_cod_data_source_block           sdx94sd_1
_cod_depositor_comments
'Adding full bibliography for 1573571--1573578.cif.'
_cod_database_code               1573572
_shelx_shelxl_version_number     2018/3
_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:
 C00X(H00J,H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00T(H00A,H00B,H00C), C00V(H00D,H00E,H00F), C00W(H00G,H00H,H00I)
;
_shelx_res_checksum              81235
_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
;