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_7718586
_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         'C17 H13 Cl O'
_chemical_formula_sum            'C17 H13 Cl O'
_chemical_formula_weight         268.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_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
;
2023-11-30 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0745(5)
_cell_length_b                   29.885(2)
_cell_length_c                   7.2125(5)
_cell_measurement_reflns_used    3408
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.7780
_cell_measurement_theta_min      5.8920
_cell_volume                     1309.33(17)
_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      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9959
_diffrn_measured_fraction_theta_max 0.9624
_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    -91.00  -9.00   0.50    0.20    --  -38.50 130.00 -10.00  164
  2  \w    -97.00 -13.00   0.50    0.20    --  -38.50 139.00 163.00  168
  3  \w     35.00 109.00   0.50    0.20    --   49.56-139.00 103.00  148
  4  \w     73.00 118.00   0.50    0.76    --  107.46-139.00 103.00   90
  5  \w    130.00 155.00   0.50    0.76    --  107.46 139.00 163.00   50
  6  \w     95.00 164.00   0.50    0.76    --  107.46 130.00 -10.00  138
  7  \w   -101.00 -74.00   0.50    0.20    --  -38.50 -57.00   0.00   54
  8  \w    -62.00 -33.00   0.50    0.20    --  -38.50 -19.00 -30.00   58
  9  \w    -63.00 -28.00   0.50    0.20    --  -38.50 -57.00   0.00   70
 10  \w    -64.00 -28.00   0.50    0.20    --  -38.50 -57.00 -90.00   72
 11  \w   -100.00 -66.00   0.50    0.20    --  -38.50 -57.00 -90.00   68
 12  \w   -108.00 -68.00   0.50    0.20    --  -38.50 -19.00 -30.00   80
 13  \w    111.00 169.00   0.50    0.76    --  107.46  77.00-120.00  116
 14  \w     74.00 111.00   0.50    0.76    --  107.46 -45.00 -90.00   74
 15  \w     95.00 161.00   0.50    0.76    --  107.46  61.00 -90.00  132
 16  \w     43.00  70.00   0.50    0.76    --  107.46 -45.00 -90.00   54
 17  \w     58.00 101.00   0.50    0.76    --  107.46 -94.00 -60.00   86
 18  \w     41.00  69.00   0.50    0.76    --  107.46 -15.00   0.00   56
;
_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      -0.0426113000
_diffrn_orient_matrix_UB_12      -0.0352576000
_diffrn_orient_matrix_UB_13      0.1513748000
_diffrn_orient_matrix_UB_21      -0.0248035000
_diffrn_orient_matrix_UB_22      0.0374869000
_diffrn_orient_matrix_UB_23      0.1450393000
_diffrn_orient_matrix_UB_31      -0.2490153000
_diffrn_orient_matrix_UB_32      0.0023382000
_diffrn_orient_matrix_UB_33      -0.0406052000
_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  0.0546
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5818
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.830
_diffrn_reflns_theta_min         5.923
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40724
_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    1.363
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_preparation       'As per the reaction scheme'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0613
_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^)+(0.1045P)^2^+0.8036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1240
_reflns_number_total             1377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00299k2.cif
_cod_data_source_block           sjp-cp74_auto
_cod_depositor_comments
'Adding full bibliography for 7718585--7718588.cif.'
_cod_database_code               7718586
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'O C H N Cl'
_chemical_oxdiff_usercomment     'COLOULESS LONG PLATE'
_shelx_estimated_absorpt_t_max   0.651
_shelx_estimated_absorpt_t_min   0.506
_diffrn_oxdiff_ac3_digest_hkl    012a9013524d19d71cf17721fe0ce8d7287b0c
_diffrn_oxdiff_digest_frames
;
01934f458d833095402cf31dac062dfe94000369829
;
_diffrn_oxdiff_digest_hkl
;
014591878e2797d11bbfde8a60c219d57aca9c
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Cl1(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              31140
_shelx_hkl_checksum              56888
_olex2_exptl_crystal_mounting_method 'Mounted on the 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 1.810
_oxdiff_exptl_absorpt_empirical_full_min 0.524