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_1573578
_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         'C37 H32 Br N5 Ni O3 P'
_chemical_formula_sum            'C37 H32 Br N5 Ni O3 P'
_chemical_formula_weight         764.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 93.2970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.3695(2)
_cell_length_b                   17.6564(2)
_cell_length_c                   19.5992(3)
_cell_measurement_reflns_used    19472
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      70.8340
_cell_measurement_theta_min      2.5030
_cell_volume                     6691.75(15)
_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 0.959
_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     21.00  71.00   0.50    3.00    --   60.44 -95.00 -30.00  100
  2  \w     11.00  47.00   0.50    3.00    --   60.44 -30.00  60.00   72
  3  \w     11.00  47.00   0.50    3.00    --   60.44 -30.00 -30.00   72
  4  \w     62.00 110.00   0.50    3.00    --   60.44  30.00  90.00   96
  5  \w     21.00  71.00   0.50    3.00    --   60.44 -95.00 -90.00  100
  6  \w     62.00 110.00   0.50    3.00    --   60.44  30.00-180.00   96
  7  \w   -111.00 -63.00   0.50    3.00    --  -62.03 -30.00 -60.00   96
  8  \w     41.00 121.00   0.50    3.00    --   73.92  15.00-150.00  160
  9  \w     75.00 123.00   0.50    3.00    --   73.92  30.00  60.00   96
 10  \w     34.00  85.00   0.50    3.00    --   73.92 -95.00   0.00  102
 11  \w     34.00  85.00   0.50    3.00    --   73.92 -95.00-120.00  102
 12  \w   -120.00 -74.00   0.50    3.00    --  -74.27-125.00 120.00   92
 13  \w     76.00 124.00   0.50    3.00    --   74.67  30.00-120.00   96
 14  \w     35.00  85.00   0.50    3.00    --   74.67 -95.00 -90.00  100
 15  \w     35.00  85.00   0.50    3.00    --   74.67 -95.00-180.00  100
 16  \w     76.00 124.00   0.50    3.00    --   74.67  30.00   0.00   96
 17  \w     62.00 110.00   0.50    3.00    --   60.44  30.00 150.00   96
 18  \w     11.00  47.00   0.50    3.00    --   60.44 -30.00  30.00   72
 19  \w     11.00  47.00   0.50    3.00    --   60.44 -30.00  90.00   72
 20  \w     11.00  47.00   0.50    3.00    --   60.44 -30.00 150.00   72
 21  \w     21.00  51.00   0.50    3.00    --   60.44 -95.00  60.00   60
 22  \w   -111.00 -63.00   0.50    3.00    --  -62.03 -30.00-120.00   96
;
_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  0.0416
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            56036
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.660
_diffrn_reflns_theta_min         3.119
_exptl_absorpt_coefficient_mu    3.056
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75666
_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            'dark black'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             3128
_exptl_crystal_size_max          0.067
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     871
_refine_ls_number_reflns         12747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0594P)^2^+5.0683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9348
_reflns_number_total             12747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04257c2.cif
_cod_data_source_block           sd-x71_sd1
_cod_depositor_comments
'Adding full bibliography for 1573571--1573578.cif.'
_cod_database_code               1573578
_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:
 C00T(H00T), C00Z(H00Z), C010(H010), C013(H013), C016(H016), C017(H017),
 C01A(H01E), C01B(H01B), C01C(H01F), C01F(H01H), C01G(H01G), C01H(H01I),
 C01K(H01K), C01L(H01N), C01M(H01O), C01O(H01Q), C01P(H01P), C01Q(H01R),
 C01S(H01S), C01T(H01T), C01U(H01U), C01V(H01V), C01W(H01W), C01X(H01X),
 C01Y(H01Y), C020(H020), C021(H021), C022(H022), C023(H023), C024(H024),
 C025(H025), C027(H027), C028(H028), C029(H029), C02A(H02P), C02B(H02Q),
 C02D(H02R), C02F(H02F), C02G(H02G), C02I(H02I), C02J(H02V), C02K(H02W),
 C02L(H02X), C02M(H02M), C02N(H02N), C02O(H02O)
2.b Idealised Me refined as rotating group:
 C01E(H01A,H01C,H01D), C01I(H01J,H01L,H01M), C026(H02J,H02K,H02L), C02C(H02A,
 H02B,H02C), C02E(H02S,H02T,H02U), C02H(H02D,H02E,H02H)
;
_shelx_res_checksum              76444
_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
;