Efficient C(sp3)–H alkylation of fluorene and bisindolylmethane synthesis catalysed by a PNN-Ni complex using alcohols
Mohite, Manali A.; Balakrishna, Maravanji S.; Catalysis Science & Technology 15 (2025) 5713–5723; doi:10.1039/D5CY00779H

data_1575448
_publ_section_title
;
 Efficient C(sp3)--H alkylation of fluorene and bisindolylmethane
 synthesis catalysed by a PNN-Ni complex using alcohols
;
_journal_issue                   19
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              5713
_journal_page_last               5723
_journal_paper_doi               10.1039/D5CY00779H
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C26 H19 N O2'
_chemical_formula_sum            'C26 H19 N O2'
_chemical_formula_weight         377.42
_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             2025-05-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-05-30 deposited with the CCDC.	2025-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                82.918(4)
_cell_angle_beta                 72.624(4)
_cell_angle_gamma                69.889(4)
_cell_formula_units_Z            2
_cell_length_a                   9.1620(4)
_cell_length_b                   9.3673(5)
_cell_length_c                   12.3869(6)
_cell_measurement_reflns_used    13305
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.7440
_cell_measurement_theta_min      1.7140
_cell_volume                     952.46(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -10.27 349.73   1.00    5.00  77.88 -12.98  31.50    --   360
  2  \w    -68.91   0.09   1.00    5.00    --  -19.47  94.56 -34.84   69
  3  \w    -65.46  -0.46   1.00    5.00    --  -16.01  94.56 145.16   65
  4  \w   -108.63  15.37   1.00    5.00    --  -12.98 -59.25  20.08  124
  5  \w    -65.46  -0.46   1.00    5.00    --  -16.01  94.56  73.16   65
  6  \f   -349.73  10.27   1.00    5.00   9.42 -12.98 -31.50    --   360
  7  \w    -65.46  -0.46   1.00    5.00    --  -16.01  94.56   1.16   65
  8  \f   -339.92  19.85   1.00    5.00  16.12 -12.98 -59.25    --   360
  9  \w   -108.63  15.37   1.00    5.00    --  -12.98 -59.25 -33.92  124
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0047573000
_diffrn_orient_matrix_UB_12      -0.0775444000
_diffrn_orient_matrix_UB_13      0.0089771000
_diffrn_orient_matrix_UB_21      0.0596063000
_diffrn_orient_matrix_UB_22      -0.0179130000
_diffrn_orient_matrix_UB_23      -0.0526613000
_diffrn_orient_matrix_UB_31      0.0614612000
_diffrn_orient_matrix_UB_32      -0.0131058000
_diffrn_orient_matrix_UB_33      0.0273516000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            38238
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.723
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0298P)^2^+0.3515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2935
_reflns_number_total             3338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cy00779h2.cif
_cod_data_source_block           P5
_cod_depositor_comments
'Adding full bibliography for 1575447--1575450.cif.'
_cod_database_code               1575448
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C23(H23), C11(H11), C22(H22), C26(H26), C25(H25), C20(H20), C3(H3),
 C19(H19), C8(H8), C5(H5), C16(H16), C10(H10), C18(H18), C4(H4), C9(H9),
 C17(H17)
;
_shelx_res_checksum              6168
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.592