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_7718588
_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         'C15 H22 Cl N O'
_chemical_formula_sum            'C15 H22 Cl N O'
_chemical_formula_weight         267.78
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-11-30 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                63.890(3)
_cell_angle_beta                 79.910(2)
_cell_angle_gamma                75.149(2)
_cell_formula_units_Z            4
_cell_length_a                   10.8183(3)
_cell_length_b                   11.9929(3)
_cell_length_c                   12.8554(4)
_cell_measurement_reflns_used    18315
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      78.2210
_cell_measurement_theta_min      4.1730
_cell_volume                     1443.91(8)
_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      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_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    -76.00  10.00   0.50    0.15    --  -38.50 106.00  19.00  172
  2  \w     12.00  87.00   0.50    0.15    --   49.56-106.00 -79.00  150
  3  \w     41.00 107.00   0.50    0.60    --  107.46-106.00 -79.00  132
  4  \w    104.00 174.00   0.50    0.60    --  107.46 106.00  19.00  140
  5  \w   -101.00 -27.00   0.50    0.15    --  -38.50 -57.00  30.00  148
  6  \w   -101.00 -20.00   0.50    0.15    --  -38.50 -69.00-111.25  162
  7  \w    -62.00  26.00   0.50    0.15    --  -38.50  77.00 -30.00  176
  8  \w    -44.00  31.00   0.50    0.15    --  -38.50  19.00-150.00  150
  9  \w     46.00 116.00   0.50    0.15    --   49.56  37.00  60.00  140
 10  \w    -17.00  53.00   0.50    0.15    --   49.56 -37.00  90.00  140
 11  \w     28.00  99.00   0.50    0.15    --   49.56-125.00-180.00  142
 12  \w     99.00 176.00   0.50    0.60    --  107.46  15.00 120.00  154
 13  \w     39.00 116.00   0.50    0.60    --  107.46 -15.00 -30.00  154
 14  \w     39.00 107.00   0.50    0.60    --  107.46 -94.00  90.00  136
 15  \w     43.00 112.00   0.50    0.60    --  107.46 -45.00 -90.00  138
 16  \w     39.00 107.00   0.50    0.60    --  107.46 -94.00 150.00  136
 17  \w    103.00 172.00   0.50    0.60    --  107.46  45.00 -90.00  138
 18  \w     39.00 111.00   0.50    0.60    --  107.46 -30.00   0.00  144
 19  \w     39.00 111.00   0.50    0.60    --  107.46 -30.00 120.00  144
 20  \w     45.00 121.00   0.50    0.60    --  107.46 -61.00-120.00  152
 21  \w     39.00 107.00   0.50    0.60    --  107.46 -94.00   0.00  136
 22  \w     45.00 113.00   0.50    0.60    --  107.46-125.00 -90.00  136
 23  \w     96.00 170.00   0.50    0.60    --  107.46  58.00  15.38  148
 24  \w     39.00 111.00   0.50    0.60    --  107.46 -30.00  60.00  144
 25  \w     45.00 121.00   0.50    0.60    --  107.46 -61.00-150.00  152
 26  \w     39.00 107.00   0.50    0.60    --  107.46 -94.00-120.00  136
 27  \w     39.00 107.00   0.50    0.60    --  107.46 -94.00  60.00  136
 28  \w     39.00 107.00   0.50    0.60    --  107.46 -94.00  30.00  136
 29  \w     43.00 112.00   0.50    0.60    --  107.46 -45.00  90.00  138
 30  \w     45.00 121.00   0.50    0.60    --  107.46 -61.00-180.00  152
 31  \w     45.00 113.00   0.50    0.60    --  107.46-125.00  30.00  136
 32  \w     39.00 116.00   0.50    0.60    --  107.46 -15.00 -90.00  154
 33  \w    104.00 176.00   0.50    0.60    --  107.46  30.00 -60.00  144
;
_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      0.0731356000
_diffrn_orient_matrix_UB_12      -0.0065365000
_diffrn_orient_matrix_UB_13      -0.1119928000
_diffrn_orient_matrix_UB_21      0.1225225000
_diffrn_orient_matrix_UB_22      -0.0714432000
_diffrn_orient_matrix_UB_23      0.0654685000
_diffrn_orient_matrix_UB_31      -0.0381693000
_diffrn_orient_matrix_UB_32      -0.1272581000
_diffrn_orient_matrix_UB_33      0.0327844000
_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  0.0420
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23123
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.283
_diffrn_reflns_theta_min         3.839
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64843
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0008(2)
_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   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0516P)^2^+0.3838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5609
_reflns_number_total             6032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00299k2.cif
_cod_data_source_block           ska-op-3_auto
_cod_depositor_comments
'Adding full bibliography for 7718585--7718588.cif.'
_cod_original_cell_volume        1443.91(7)
_cod_database_code               7718588
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C H N O Cl'
_chemical_oxdiff_usercomment     'light colourless block'
_shelx_estimated_absorpt_t_max   0.639
_shelx_estimated_absorpt_t_min   0.534
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C2(H2A,H2B), C3(H3A,H3B),
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C29(H29), C30(H30), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              25558
_shelx_hkl_checksum              32939
_olex2_exptl_crystal_mounting_method 'mounted on a 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 1.427
_oxdiff_exptl_absorpt_empirical_full_min 0.695