Electrochemical synthesis of 2-alkyl-4-phenylalkan-2-ols <i>via</i> cathodic reductive coupling of alkynes with unactivated aliphatic ketones.
Dapkekar, Anil Balajirao; Satyanarayana, Gedu; Chemical communications (Cambridge, England) 59 (2023) 2915–2918; doi:10.1039/d2cc06819b

data_7131284
_publ_section_title
;
 Electrochemical synthesis of 2-alkyl-4-phenylalkan-2-ols <i>via</i>
 cathodic reductive coupling of alkynes with unactivated aliphatic
 ketones.
;
_journal_issue                   20
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2915
_journal_page_last               2918
_journal_paper_doi               10.1039/d2cc06819b
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C14 H20 O'
_chemical_formula_sum            'C14 H20 O'
_chemical_formula_weight         204.30
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-24 deposited with the CCDC.	2023-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   19.065(2)
_cell_length_b                   19.065(2)
_cell_length_c                   13.900(3)
_cell_measurement_reflns_used    3842
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.39
_cell_measurement_theta_min      2.80
_cell_volume                     5052.3(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_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  0.0790
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21267
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.813
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1063 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.8846.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.074
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0045(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0724P)^2^+2.0147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1756
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1591
_reflns_number_total             2790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06819b2.cif
_cod_data_source_block           mo_gs_ab_2_219_1_0m
_cod_depositor_comments          'Adding full bibliography for 7131284.cif.'
_cod_original_cell_volume        5052.3(15)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7131284
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.977
_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:
 C13(H13A,H13B), C14(H14A,H14B), C9(H9A,H9B), C8(H8A,H8B), C12(H12A,H12B),
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              61699
_shelx_hkl_checksum              44043
_olex2_exptl_crystal_mounting_method 'NYLON LOOP'
_olex2_submission_special_instructions 'No special instructions were received'