Potent pincer-zinc catalyzed homogeneous α-alkylation and Friedländer quinoline synthesis reaction of secondary alcohols/ketones with primary alcohols.
Jana, Debashis; Roy, Sima; Naskar, Srijita; Halder, Supriyo; Kanrar, Gopal; Pramanik, Kausikisankar; Organic & biomolecular chemistry 22 (2024) 6393–6408; doi:10.1039/d4ob00988f

data_7160069
_publ_section_title
;
 Potent pincer-zinc catalyzed homogeneous &#x3b1;-alkylation and
 Friedl&#xe4;nder quinoline synthesis reaction of secondary
 alcohols/ketones with primary alcohols.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6393
_journal_page_last               6408
_journal_paper_doi               10.1039/d4ob00988f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         '0.154(C16 H16 O2)'
_chemical_formula_sum            'C2.46 H2.46 O0.31'
_chemical_formula_weight         36.97
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-04-17 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.297(6)
_cell_angle_gamma                90
_cell_formula_units_Z            26
_cell_length_a                   9.1890(14)
_cell_length_b                   5.6168(9)
_cell_length_c                   24.833(4)
_cell_measurement_reflns_used    6764
_cell_measurement_temperature    183.49
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.36
_cell_volume                     1281.7(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      183.49
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  "'Bruker D8 QUEST SCXRD"
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            15082
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.481
_diffrn_reflns_theta_min         2.359
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.5633
_exptl_absorpt_correction_T_min  0.3508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1420 before and 0.1021 after correction.
The Ratio of minimum to maximum transmission is 0.6228.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0495P)^2^+0.4231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2472
_reflns_number_total             3174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00988f2.cif
_cod_data_source_block           5ag
_cod_depositor_comments
'Adding full bibliography for 7160068--7160071.cif.'
_cod_original_cell_volume        1281.7(3)
_cod_database_code               7160069
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              97028
_olex2_submission_special_instructions 'No special instructions were received'