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_1575449
_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         'C27 H20 Br2'
_chemical_formula_sum            'C27 H20 Br2'
_chemical_formula_weight         504.25
_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
_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                69.540(3)
_cell_angle_beta                 87.768(4)
_cell_angle_gamma                68.277(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9193(10)
_cell_length_b                   10.1578(11)
_cell_length_c                   13.6811(14)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.29
_cell_volume                     1073.0(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41670
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.516
_diffrn_reflns_theta_min         2.289
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.788
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4950
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1546 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.6638.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark colourless'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0392P)^2^+0.7130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3933
_reflns_number_total             5378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cy00779h2.cif
_cod_data_source_block           P8
_cod_depositor_comments
'Adding full bibliography for 1575447--1575450.cif.'
_cod_database_code               1575449
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.848
_shelx_estimated_absorpt_t_min   0.732
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B)
1.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16),
 C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              35003
_olex2_submission_special_instructions 'No special instructions were received'