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_1575447
_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         'C29 H30 N2 O2'
_chemical_formula_sum            'C29 H30 N2 O2'
_chemical_formula_weight         438.55
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-05-20
_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                 102.676(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9352(12)
_cell_length_b                   9.6405(11)
_cell_length_c                   22.561(3)
_cell_measurement_reflns_used    7583
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.63
_cell_measurement_theta_min      2.31
_cell_volume                     2532.6(5)
_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 0.999
_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  0.0742
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43661
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.080
_diffrn_reflns_theta_max         25.080
_diffrn_reflns_theta_min         1.850
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5668
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1477 before and 0.0728 after correction.
The Ratio of minimum to maximum transmission is 0.7606.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0617
_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^)+(0.0852P)^2^+1.3773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1850
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3055
_reflns_number_total             4498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cy00779h2.cif
_cod_data_source_block           7r
_cod_depositor_comments
'Adding full bibliography for 1575447--1575450.cif.'
_cod_database_code               1575447
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C19(H19)
1.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C13(H13), C15(H15), C16(H16), C10(H10), C8(H8), C6(H6),
 C5(H5), C1(H1A), C22(H22), C21(H21)
1.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C18(H18A,H18B,H18C), C9(H9A,H9B,H9C), C29(H29A,H29B,
 H29C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              71752
_olex2_submission_special_instructions 'No special instructions were received'