Chromium-catalyzed reductive alkylation of N heteroarenes using alkyl formates as transfer hydroalkylation reagents
Pal, Anit; Borah, Asish; Das, Animesh; Chemical Communications  (2025) –; doi:10.1039/D5CC06076A

data_7135282
_publ_section_title
;
 Chromium-catalyzed reductive alkylation of N heteroarenes using alkyl
 formates as transfer hydroalkylation reagents
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC06076A
_journal_year                    2025
_chemical_formula_moiety         'C24 H21 N'
_chemical_formula_sum            'C24 H21 N'
_chemical_formula_weight         323.42
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-06-14
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_audit_update_record
;
2024-10-30 deposited with the CCDC.	2025-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.258(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1945(9)
_cell_length_b                   21.100(2)
_cell_length_c                   11.3760(13)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      2.69
_cell_volume                     1878.4(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      295.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0455
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            41672
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.036
_diffrn_reflns_theta_max         25.036
_diffrn_reflns_theta_min         2.109
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1233 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.9203.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.6858
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0711
_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^)+(0.0429P)^2^+1.0797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1700
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2281
_reflns_number_total             3314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06076a2.cif
_cod_data_source_block           ad_ap_209_0m_a
_cod_original_cell_volume        1878.4(4)
_cod_database_code               7135282
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_res_checksum              93380
_olex2_submission_special_instructions 'No special instructions were received'