Phenalenyl-based copper complex catalyzed direct biarylation of furan.
Paramanik, Krishnendu; Bandopadhyay, Nilaj; Sarkar, Gayetri; Ghosh, Sourav; Panda, Subhra Jyoti; Purohit, Chandra Shekhar; Ghosh, Prasanta; Biswas, Bhaskar; Das, Hari Sankar; Dalton transactions (Cambridge, England : 2003) 54 (2025) 8045–8049; doi:10.1039/d5dt00299k

data_7718587
_publ_section_title
;
 Phenalenyl-based copper complex catalyzed direct biarylation of furan.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8045
_journal_page_last               8049
_journal_paper_doi               10.1039/d5dt00299k
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C23 H15 Cl Cu N2 O2'
_chemical_formula_sum            'C23 H15 Cl Cu N2 O2'
_chemical_formula_weight         450.36
_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             2022-08-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-05-03 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.589(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4040(3)
_cell_length_b                   13.2209(4)
_cell_length_c                   16.2937(6)
_cell_measurement_reflns_used    11131
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      31.7730
_cell_measurement_theta_min      3.9260
_cell_volume                     1804.56(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.835
_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      4.00  75.00   0.50    4.00    --    7.48  34.00 -50.00  142
  2  \w    -60.00   7.00   0.50    4.00    --    7.48 -34.00 152.00  134
  3  \w    -64.00 -38.00   0.50    4.00    --   -8.10 -34.00 152.00   52
  4  \w    -31.00  20.00   0.50    4.00    --   -8.10  77.00 -30.00  102
  5  \w    -30.00  -3.00   0.50    4.00    --   -8.10 -77.00 150.00   54
  6  \w    -30.00  15.00   0.50    4.00    --   -8.10 -77.00-120.00   90
  7  \w    -31.00  -6.00   0.50    4.00    --   -8.10  77.00   0.00   50
  8  \w    -33.00  15.00   0.50    4.00    --   -8.10 -77.00  30.00   96
;
_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      0.0692057000
_diffrn_orient_matrix_UB_12      0.0247514000
_diffrn_orient_matrix_UB_13      -0.0121228000
_diffrn_orient_matrix_UB_21      0.0281090000
_diffrn_orient_matrix_UB_22      -0.0464676000
_diffrn_orient_matrix_UB_23      -0.0150304000
_diffrn_orient_matrix_UB_31      -0.0398080000
_diffrn_orient_matrix_UB_32      0.0102270000
_diffrn_orient_matrix_UB_33      -0.0391705000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9291
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.942
_diffrn_reflns_theta_min         3.327
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.382
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         1.257
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         9291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0546
_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^)+(0.1072P)^2^+0.5296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7659
_reflns_number_total             9291
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00299k2.cif
_cod_data_source_block           sjp-k2-cu_auto
_cod_depositor_comments
'Adding full bibliography for 7718585--7718588.cif.'
_cod_original_cell_volume        1804.57(10)
_cod_database_code               7718587
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C H N O Cu Cl'
_chemical_oxdiff_usercomment     'DARK GREEN BLOCKS'
_shelx_estimated_absorpt_t_max   0.715
_shelx_estimated_absorpt_t_min   0.651
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6691(12)
 0.3309(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C19(H19), C4(H4), C21(H21), C18(H18), C7(H7), C12(H12), C1(H1),
 C22(H22), C8(H8), C2(H2), C3(H3), C9(H9), C17(H17), C10(H10)
;
_shelx_res_checksum              37504
_shelx_hkl_checksum              33734
_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 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.735