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_7063885
_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         'C38 H22 Cu O4, 2(H2 O)'
_chemical_formula_sum            'C38 H26 Cu O6'
_chemical_formula_weight         642.13
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-16 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.719(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.7265(3)
_cell_length_b                   3.75900(10)
_cell_length_c                   21.7296(3)
_cell_measurement_reflns_used    8993
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.4660
_cell_measurement_theta_min      4.1140
_cell_volume                     1356.86(5)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9767
_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   -103.00 -34.00   0.50    0.50    --  -38.50 -44.00 -60.00  138
  2  \w    -43.00  26.00   0.50    0.50    --  -38.50  44.00  90.00  138
  3  \w    -16.00  53.00   0.50    0.50    --   49.06 -44.00 -60.00  138
  4  \w     45.00 114.00   0.50    0.50    --   49.06  44.00  90.00  138
  5  \w     42.00 111.00   0.50    2.00    --  106.83 -44.00 -60.00  138
  6  \w    103.00 172.00   0.50    2.00    --  106.83  44.00  90.00  138
  7  \w    -42.00  28.00   0.50    0.50    --  -38.50  38.00  30.00  140
  8  \w     28.00  98.00   0.50    0.50    --   49.06-125.00 -90.00  140
  9  \w     28.00  98.00   0.50    0.50    --   49.06-125.00 150.00  140
 10  \w     38.00 112.00   0.50    0.50    --   49.06  57.00 120.00  148
 11  \w     44.00 112.00   0.50    2.00    --  106.83-125.00 120.00  136
 12  \w    104.00 175.00   0.50    2.00    --  106.83  30.00-150.00  142
 13  \w     44.00 120.00   0.50    2.00    --  106.83 -61.00  30.00  152
 14  \w     94.00 170.00   0.50    2.00    --  106.83  61.00 -90.00  152
 15  \w    102.00 171.00   0.50    2.00    --  106.83  45.00  60.00  138
 16  \w     39.00 106.00   0.50    2.00    --  106.83 -94.00-180.00  134
 17  \w     42.00 111.00   0.50    2.00    --  106.83 -45.00 150.00  138
 18  \w     39.00 106.00   0.50    2.00    --  106.83 -94.00 150.00  134
 19  \w     44.00 112.00   0.50    2.00    --  106.83-125.00 -30.00  136
 20  \w     39.00 106.00   0.50    2.00    --  106.83 -94.00 120.00  134
 21  \w     38.00  90.00   0.50    0.50    --   49.06  57.00  30.00  104
;
_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      0.0364914000
_diffrn_orient_matrix_UB_12      -0.3197004000
_diffrn_orient_matrix_UB_13      0.0377288000
_diffrn_orient_matrix_UB_21      -0.0852030000
_diffrn_orient_matrix_UB_22      -0.1260576000
_diffrn_orient_matrix_UB_23      0.0099081000
_diffrn_orient_matrix_UB_31      -0.0041235000
_diffrn_orient_matrix_UB_32      -0.2233242000
_diffrn_orient_matrix_UB_33      -0.0597548000
_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  0.0483
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11017
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.669
_diffrn_reflns_theta_min         4.097
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79985
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       block
_exptl_crystal_F_000             662
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0755P)^2^+0.7413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2659
_reflns_number_total             2805
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00906e2.cif
_cod_data_source_block           ska-hsd-gs-_auto
_cod_database_code               7063885
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C H O Cu'
_shelx_estimated_absorpt_t_max   0.743
_shelx_estimated_absorpt_t_min   0.648
_diffrn_oxdiff_ac3_digest_hkl    41e3c815c05c2b5694745b49e6f6566055a988
_diffrn_oxdiff_digest_frames
;
014e09e69adb060a33c18881f060feaf8d000291f65
;
_diffrn_oxdiff_digest_hkl
;
01a18a73ab95271ba16bb1509db17b7d9b0920
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_shelx_res_checksum              87371
_olex2_exptl_crystal_mounting_method 'Mounted on a nylon 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 2.021
_oxdiff_exptl_absorpt_empirical_full_min 0.713