Copper(ii) phenalenyl complexes: structures, redox properties and catalytic activity towards Sonogashira coupling reactions
Sarkar, Gayetri; Paramanik, Krishnendu; Bandopadhyay, Nilaj; Chatterjee, Souvik; Saha, Subhajit; Panda, Subhra Jyoti; Purohit, Chandra Shekhar; Biswas, Bhaskar; Das, Hari Sankar; New Journal of Chemistry 49 (2025) 8232–8238; doi:10.1039/D5NJ00906E

data_7063884
_publ_section_title
;
 Copper(ii) phenalenyl complexes: structures, redox properties and
 catalytic activity towards Sonogashira coupling reactions
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8232
_journal_page_last               8238
_journal_paper_doi               10.1039/D5NJ00906E
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C26 H14 Cu O4'
_chemical_formula_sum            'C26 H14 Cu O4'
_chemical_formula_weight         453.91
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-12-16 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.280(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.47210(10)
_cell_length_b                   13.4666(4)
_cell_length_c                   14.7928(4)
_cell_measurement_reflns_used    7869
_cell_measurement_temperature    110(16)
_cell_measurement_theta_max      77.9490
_cell_measurement_theta_min      4.4100
_cell_volume                     889.42(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9805
_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    -79.00   4.00   0.50    0.30    --  -38.50 113.00 168.00  166
  2  \w     18.00  90.00   0.50    0.30    --   49.56-113.00  76.00  144
  3  \w    103.00 173.00   0.50    1.16    --  107.46 113.00 168.00  140
  4  \w     42.00 109.00   0.50    1.16    --  107.46-113.00  76.00  134
  5  \w   -101.00 -27.00   0.50    0.30    --  -38.50 -57.00   0.00  148
  6  \w    -17.00  53.00   0.50    0.30    --   49.56 -37.00-150.00  140
  7  \w     46.00 116.00   0.50    0.30    --   49.56  37.00-180.00  140
  8  \w    -17.00  53.00   0.50    0.30    --   49.56 -37.00  60.00  140
  9  \w     45.00 113.00   0.50    1.16    --  107.46-125.00  60.00  136
 10  \w     97.00 170.00   0.50    1.16    --  107.46 125.00  90.00  146
 11  \w    103.00 172.00   0.50    1.16    --  107.46  77.00-120.00  138
 12  \w     39.00 116.00   0.50    1.16    --  107.46 -15.00  60.00  154
 13  \w     39.00 107.00   0.50    1.16    --  107.46 -94.00-150.00  136
 14  \w     43.00 112.00   0.50    1.16    --  107.46 -45.00  30.00  138
 15  \w     43.00 112.00   0.50    1.16    --  107.46 -45.00 150.00  138
 16  \w     39.00 111.00   0.50    1.16    --  107.46 -30.00-120.00  144
 17  \w     39.00 107.00   0.50    1.16    --  107.46 -94.00  90.00  136
 18  \w     95.00 170.00   0.50    1.16    --  107.46  61.00  60.00  150
 19  \w   -101.00 -58.00   0.50    0.30    --  -38.50 -57.00-180.00   86
 20  \w     38.00 113.00   0.50    0.30    --   49.56  57.00 -60.00  150
 21  \w     38.00 113.00   0.50    0.30    --   49.56  57.00   0.00  150
 22  \w     38.00 113.00   0.50    0.30    --   49.56  57.00  90.00  150
 23  \w     46.00 116.00   0.50    0.30    --   49.56  37.00-120.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0527733000
_diffrn_orient_matrix_UB_12      0.0941086000
_diffrn_orient_matrix_UB_13      0.0561124000
_diffrn_orient_matrix_UB_21      -0.1244253000
_diffrn_orient_matrix_UB_22      0.0537451000
_diffrn_orient_matrix_UB_23      -0.0860522000
_diffrn_orient_matrix_UB_31      -0.3175240000
_diffrn_orient_matrix_UB_32      -0.0366728000
_diffrn_orient_matrix_UB_33      0.0179500000
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8877
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.300
_diffrn_reflns_theta_min         4.443
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.031
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_description       needle
_exptl_crystal_F_000             462
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.0064(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0556P)^2^+0.6517P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1828
_reflns_number_total             1864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00906e2.cif
_cod_data_source_block           sjp-g16_auto
_cod_database_code               7063884
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'Cu O C H N Cl'
_shelx_estimated_absorpt_t_max   0.699
_shelx_estimated_absorpt_t_min   0.554
_diffrn_oxdiff_digest_frames
;
01698a4e355408ddf3bef90d0556d926cc0003682da
;
_diffrn_oxdiff_digest_hkl
;
0166f617710447c7e65c068083d9bff22ea592
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              21971
_olex2_exptl_crystal_mounting_method 'Mounted on the 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 1.642
_oxdiff_exptl_absorpt_empirical_full_min 0.363