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_1575450
_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 H17 Br2 N O2'
_chemical_formula_sum            'C26 H17 Br2 N O2'
_chemical_formula_weight         535.237
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_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                90
_cell_angle_beta                 91.136(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1389(11)
_cell_length_b                   11.2656(13)
_cell_length_c                   18.8705(17)
_cell_measurement_reflns_used    1686
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      23.71
_cell_measurement_theta_min      2.82
_cell_volume                     2155.0(4)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.9939
_diffrn_measured_fraction_theta_max 0.9939
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1493
_diffrn_reflns_av_unetI/netI     0.1669
_diffrn_reflns_Laue_measured_fraction_full 0.9939
_diffrn_reflns_Laue_measured_fraction_max 0.9939
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15724
_diffrn_reflns_point_group_measured_fraction_full 0.9939
_diffrn_reflns_point_group_measured_fraction_max 0.9939
_diffrn_reflns_theta_full        24.9963
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.785
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2055
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1660 before and 0.0835 after correction.
The Ratio of minimum to maximum transmission is 0.2756.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       block
_exptl_crystal_F_000             1062.964
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.7847
_refine_diff_density_min         -0.8877
_refine_diff_density_rms         0.2040
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             9.6725
_refine_ls_goodness_of_fit_ref   0.9936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9936
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0295P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              -9
_reflns_number_gt                2432
_reflns_number_total             3761
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cy00779h2.cif
_cod_data_source_block           P6
_cod_depositor_comments
'Adding full bibliography for 1575447--1575450.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               1575450
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
1.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C11(H11), C23(H23), C26(H26), C9(H9), C2(H2), C20(H20), C8(H8),
 C25(H25), C5(H5), C4(H4), C18(H18), C19(H19), C17(H17), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'