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_7718585
_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 H14 Br Cl Cu N2 O2, H2 O'
_chemical_formula_sum            'C23 H16 Br Cl Cu N2 O3'
_chemical_formula_weight         547.28
_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
_audit_creation_date             2022-12-07
_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                 109.0475(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.39210(9)
_cell_length_b                   16.48858(14)
_cell_length_c                   13.74501(13)
_cell_measurement_reflns_used    26508
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.6320
_cell_measurement_theta_min      3.4640
_cell_volume                     2012.04(3)
_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)'
_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 0.9997
_diffrn_measured_fraction_theta_max 0.9897
_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   -105.00 -35.00   0.50    0.12    --  -38.50 -36.00 -31.00  140
  2  \w    -42.00  28.00   0.50    0.12    --  -38.50  36.00 124.00  140
  3  \w     46.00 116.00   0.50    0.12    --   49.31  36.00 124.00  140
  4  \w    -17.00  53.00   0.50    0.12    --   49.31 -36.00 -31.00  140
  5  \w    104.00 174.00   0.50    0.12    --  107.46  36.00 124.00  140
  6  \w     41.00 111.00   0.50    0.12    --  107.46 -36.00 -31.00  140
  7  \w    -86.00  -6.00   0.50    0.12    --  -38.50 125.00 150.00  160
  8  \w   -101.00 -25.00   0.50    0.12    --  -38.50 -62.00 -49.42  152
  9  \w   -108.00 -33.00   0.50    0.12    --  -38.50 -19.00   0.00  150
 10  \w   -105.00 -35.00   0.50    0.12    --  -38.50 -37.00  60.00  140
 11  \w     28.00 100.00   0.50    0.12    --   49.31-125.00-150.00  144
 12  \w     43.00 113.00   0.50    0.12    --  107.46-125.00-120.00  140
 13  \w    103.00 172.00   0.50    0.12    --  107.46  77.00  60.00  138
 14  \w     43.00 113.00   0.50    0.12    --  107.46-125.00   0.00  140
 15  \w     39.00 107.00   0.50    0.12    --  107.46 -94.00  60.00  136
 16  \w     89.00 171.00   0.50    0.12    --  107.46  71.00  75.31  164
 17  \w     45.00 121.00   0.50    0.12    --  107.46 -61.00 -90.00  152
 18  \w     39.00 111.00   0.50    0.12    --  107.46 -30.00-180.00  144
 19  \w     43.00 112.00   0.50    0.12    --  107.46 -45.00 120.00  138
 20  \w     39.00 107.00   0.50    0.12    --  107.46 -94.00 -30.00  136
 21  \w    103.00 172.00   0.50    0.12    --  107.46  45.00   0.00  138
 22  \w    102.00 171.00   0.50    0.12    --  107.46  48.00-153.25  138
 23  \w     43.00 131.00   0.50    0.12    --  107.46 -77.00  60.00  176
 24  \w    104.00 176.00   0.50    0.12    --  107.46  30.00 150.00  144
 25  \w     43.00 112.00   0.50    0.12    --  107.46 -45.00 -90.00  138
 26  \w     43.00 113.00   0.50    0.12    --  107.46-125.00-180.00  140
 27  \w     95.00 170.00   0.50    0.12    --  107.46  61.00-180.00  150
 28  \w    103.00 172.00   0.50    0.12    --  107.46  45.00 150.00  138
 29  \w     45.00 121.00   0.50    0.12    --  107.46 -61.00   0.00  152
 30  \w     39.00 107.00   0.50    0.12    --  107.46 -94.00-150.00  136
 31  \w     43.00 113.00   0.50    0.12    --  107.46-125.00 -60.00  140
 32  \w     45.00 121.00   0.50    0.12    --  107.46 -61.00  60.00  152
 33  \w     47.00 107.00   0.50    0.12    --  107.46-103.00  14.39  120
 34  \w     82.00 108.00   0.50    0.12    --  107.46-103.00 140.35   52
 35  \w    113.00 156.00   0.50    0.12    --  107.46 125.00   0.00   86
;
_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      0.1400326000
_diffrn_orient_matrix_UB_12      0.0549806000
_diffrn_orient_matrix_UB_13      0.0368392000
_diffrn_orient_matrix_UB_21      0.0999035000
_diffrn_orient_matrix_UB_22      -0.0749816000
_diffrn_orient_matrix_UB_23      0.0398402000
_diffrn_orient_matrix_UB_31      0.0228893000
_diffrn_orient_matrix_UB_32      -0.0091528000
_diffrn_orient_matrix_UB_33      -0.1054518000
_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  0.0801
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31687
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.037
_diffrn_reflns_theta_min         4.332
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.337
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59819
_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 greenish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0537P)^2^+3.6364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4192
_reflns_number_total             4254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00299k2.cif
_cod_data_source_block           sjp-kcu-5_auto
_cod_depositor_comments
'Adding full bibliography for 7718585--7718588.cif.'
_cod_original_cell_volume        2012.04(4)
_cod_database_code               7718585
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         ' C H N O Cu Cl'
_chemical_oxdiff_usercomment     'YELLOWISH GREEN BLOCK'
_shelx_estimated_absorpt_t_max   0.337
_shelx_estimated_absorpt_t_min   0.280
_diffrn_oxdiff_digest_frames
;
01f37912e9f12574fe28b6f5b3fb9370b3000500e22
;
_diffrn_oxdiff_digest_hkl
;
013a7cd8c14e10da58cac9380f7d5a40d09ac4
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C10(H10), C18(H18), C7(H7), C19(H19), C23(H23), C1(H1), C4(H4), C3(H3),
 C9(H9), C21(H21), C2(H2), C13(H13), C8(H8), C12(H12)
;
_shelx_res_checksum              90879
_shelx_hkl_checksum              68961
_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 6.158
_oxdiff_exptl_absorpt_empirical_full_min 0.455