Copper-catalyzed C(sp<sup>3</sup>)-H alkylation of fluorene with primary and secondary alcohols using a borrowing hydrogen method.
Saha, Ratnakar; Maharana, Suraj Kumar; Jana, Narayan Ch; Bagh, Bidraha; Chemical communications (Cambridge, England) 60 (2024) 10144–10147; doi:10.1039/d4cc03310h

data_7133813
_publ_section_title
;
 Copper-catalyzed C(sp<sup>3</sup>)-H alkylation of fluorene with primary
 and secondary alcohols using a borrowing hydrogen method.
;
_journal_issue                   74
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10144
_journal_page_last               10147
_journal_paper_doi               10.1039/d4cc03310h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C21 H22 Cl Cu N2 S'
_chemical_formula_sum            'C21 H22 Cl Cu N2 S'
_chemical_formula_weight         433.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-14 deposited with the CCDC.	2024-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.56440(10)
_cell_length_b                   9.69930(10)
_cell_length_c                   23.7155(2)
_cell_measurement_reflns_used    43999
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1400
_cell_measurement_theta_min      3.7180
_cell_volume                     1970.02(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -72.00  20.00   0.50    0.50    --  -38.50  95.00  95.00  184
  2  \w      2.00  83.00   0.50    0.50    --   49.56 -95.00 -15.00  162
  3  \w    104.00 171.00   0.50    2.50    --  102.63  95.00  95.00  134
  4  \w     34.00 106.00   0.50    2.50    --  102.63 -95.00 -15.00  144
  5  \w    -45.00  -1.00   0.50    0.50    --    2.00 119.00 -69.61   88
  6  \w    -42.00 -16.00   0.50    0.50    --   22.00 146.00  49.27   52
  7  \w      5.00  31.00   0.50    0.50    --   34.00  87.00-123.16   52
  8  \w      4.00  30.00   0.50    0.50    --   34.00  88.00-172.50   52
  9  \w      5.00  31.00   0.50    0.50    --   34.00  87.00  -1.29   52
 10  \w     13.00  42.00   0.50    0.50    --   38.00  80.00 133.82   58
 11  \w    -86.00  -6.00   0.50    0.50    --  -38.50 125.00 150.00  160
 12  \w    -42.00  28.00   0.50    0.50    --  -38.50  38.00 -30.00  140
 13  \w     16.00  42.00   0.50    0.50    --   42.00  82.00  55.92   52
 14  \w     16.00  42.00   0.50    0.50    --   42.00  82.00 -17.51   52
 15  \w     16.00  42.00   0.50    0.50    --   42.00  82.00 -84.70   52
 16  \w     30.00 114.00   0.50    0.50    --   50.00  73.00-136.29  168
 17  \w     29.00 114.00   0.50    0.50    --   50.00  74.00-179.01  170
 18  \w     33.00 118.00   0.50    0.50    --   54.00  74.00   8.61  170
 19  \w     37.00 122.00   0.50    0.50    --   58.00  74.00 154.84  170
 20  \w     39.00 122.00   0.50    0.50    --   58.00  72.00-102.61  166
 21  \w     37.00 122.00   0.50    0.50    --   58.00  74.00  75.14  170
 22  \w     37.00 122.00   0.50    0.50    --   58.00  74.00 -80.70  170
 23  \w     38.00 122.00   0.50    0.50    --   58.00  73.00 102.47  168
 24  \w     37.00 122.00   0.50    0.50    --   58.00  74.00-136.87  170
 25  \w     38.00 122.00   0.50    0.50    --   58.00  73.00 -50.17  168
 26  \w     38.00 122.00   0.50    0.50    --   58.00  73.00 132.37  168
 27  \w     47.00 125.00   0.50    0.50    --   62.00  65.00 -34.53  156
 28  \w     43.00 126.00   0.50    0.50    --   62.00  72.00  25.75  166
 29  \w     52.00 129.00   0.50    0.50    --   66.00  63.00  10.08  154
 30  \w     48.00 129.00   0.50    0.50    --   66.00  69.00 -22.34  162
 31  \w     45.00 130.00   0.50    0.50    --   66.00  74.00  48.30  170
 32  \w     49.00  88.00   0.50    0.50    --   70.00  74.00 177.15   78
 33  \w     53.00  79.00   0.50    0.50    --   70.00  69.00-129.47   52
 34  \w     50.00  95.00   0.50    0.50    --   70.00  73.00 -92.87   90
 35  \w     50.00  85.00   0.50    0.50    --   70.00  73.00  84.03   70
 36  \w     59.00  99.00   0.50    0.50    --   74.00  65.00 -31.36   80
 37  \w     61.00  87.00   0.50    0.50    --   74.00  61.00 121.62   52
 38  \w     61.00  96.00   0.50    2.50    --   78.00  68.00  77.47   70
 39  \w     68.00 107.00   0.50    2.50    --   78.00  56.00  52.62   78
 40  \w     64.00  90.00   0.50    2.50    --   82.00  69.00-153.88   52
 41  \w     70.00 143.00   0.50    2.50    --   82.00  58.00-112.82  146
 42  \w     67.00  93.00   0.50    2.50    --   82.00  64.00  23.51   52
 43  \w    115.00 141.00   0.50    2.50    --   82.00  64.00  23.51   52
 44  \w    114.00 143.00   0.50    2.50    --   86.00  73.00 141.35   58
 45  \w     65.00  96.00   0.50    2.50    --   86.00  74.00 125.71   62
 46  \w     67.00 110.00   0.50    2.50    --   86.00  73.00 141.35   86
 47  \w    102.00 149.00   0.50    2.50    --   86.00  74.00 125.71   94
 48  \w     70.00 114.00   0.50    2.50    --   86.00  71.00 154.23   88
 49  \w     68.00 106.00   0.50    2.50    --   86.00  69.00 119.93   76
 50  \w     76.00 139.00   0.50    2.50    --   94.00  70.00 -36.89  126
 51  \w    136.00 162.00   0.50    2.50    --  102.63  61.00-150.00   52
 52  \w     90.00 125.00   0.50    2.50    --  102.63  61.00-150.00   70
 53  \w     91.00 166.00   0.50    2.50    --  102.63  57.00 -12.81  150
 54  \w    140.00 165.00   0.50    2.50    --  102.63  61.00 -60.00   50
 55  \w     90.00 120.00   0.50    2.50    --  102.63  61.00 -60.00   60
 56  \w     72.00 107.00   0.50    2.50    --  102.63 -94.00 120.00   70
 57  \w     47.00 111.00   0.50    2.50    --  102.63-125.00   0.00  128
 58  \w     90.00 165.00   0.50    2.50    --  102.63  61.00  90.00  150
 59  \w     76.00 102.00   0.50    2.50    --  102.63 -94.00-180.00   52
 60  \w     54.00 104.00   0.50    2.50    --  102.63 -30.00 150.00  100
 61  \w     39.00  64.00   0.50    2.50    --  102.63 -94.00 120.00   50
 62  \w    137.00 164.00   0.50    2.50    --  102.63  61.00 -90.00   54
 63  \w     90.00 115.00   0.50    2.50    --  102.63  61.00 -90.00   50
 64  \w     71.00 104.00   0.50    2.50    --  102.63 -94.00  60.00   66
 65  \w     35.00  62.00   0.50    2.50    --  102.63 -94.00  60.00   54
 66  \w     38.00  95.00   0.50    2.50    --  102.63 -45.00   0.00  114
 67  \w    103.00 165.00   0.50    2.50    --  102.63  77.00  60.00  124
 68  \w     90.00 164.00   0.50    2.50    --  102.63  61.00-180.00  148
 69  \w     92.00 141.00   0.50    2.50    --  102.63  61.00  30.00   98
 70  \w     81.00 107.00   0.50    2.50    --  102.63 -94.00   0.00   52
 71  \w    102.00 156.00   0.50    2.50    --  102.63 125.00  30.00  108
 72  \w     81.00 115.00   0.50    2.50    --  102.63 -61.00 120.00   68
 73  \w     42.00  67.00   0.50    2.50    --  102.63 -94.00   0.00   50
 74  \w     92.00 127.00   0.50    2.50    --  102.63  59.00  51.54   70
 75  \w     38.00 106.00   0.50    2.50    --  102.63 -45.00 -90.00  136
 76  \w    101.00 151.00   0.50    2.50    --  102.63  45.00 -60.00  100
 77  \w     35.00 107.00   0.50    2.50    --  102.63 -94.00-120.00  144
 78  \w     81.00 107.00   0.50    2.50    --  102.63-125.00-150.00   52
 79  \w     39.00  80.00   0.50    2.50    --  102.63-125.00-150.00   82
 80  \w     38.00 105.00   0.50    2.50    --  102.63 -45.00  60.00  134
 81  \w    111.00 167.00   0.50    2.50    --  102.63  77.00 150.00  112
 82  \w     91.00 164.00   0.50    2.50    --  102.63  61.00   0.00  146
 83  \w     90.00 165.00   0.50    2.50    --  102.63  61.00-120.00  150
 84  \w     41.00  68.00   0.50    2.50    --  102.63 -61.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            55581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         3.728
_exptl_absorpt_coefficient_mu    3.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'whiteish gray'
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1453 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0534
_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^)+5.4201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3595
_reflns_number_total             3620
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03310h2.cif
_cod_data_source_block           complex1
_cod_database_code               7133813
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C7) = Uanis(C1A) = Uanis(C3A) = Uanis(C8)
3. Others
 Fixed Sof: C7(0.5) H7A(0.5) H7B(0.5) C8(0.5) H8A(0.5) H8B(0.5) C3A(0.5)
 H3AA(0.5) H3AB(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5)
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C3A(H3AA,H3AB), C1A(H1AA,H1AB)
4.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C4(H4), C20(H20), C11(H11), C1(H1), C2(H2A), C12(H12), C13(H13),
 C3(H3), C14(H14), C19(H19), C15(H15), C18(H18), C17(H17)
;
_shelx_res_checksum              41811
_shelx_hkl_checksum              71240
_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
;