#------------------------------------------------------------------------------
#$Date: 2023-05-05 03:18:56 +0300 (Fri, 05 May 2023) $
#$Revision: 283064 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/12/7131284.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131284
loop_
_publ_author_name
'Dapkekar, Anil Balajirao'
'Satyanarayana, Gedu'
_publ_section_title
;
 Electrochemical synthesis of 2-alkyl-4-phenylalkan-2-ols via
 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       'φ and ω 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 λ/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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0724P)²+2.0147P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_exptl_crystal_mounting_method 'NYLON LOOP'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54534(9) 0.83989(7) 0.65112(10) 0.0593(4) Uani 1 1 d . . . . .
C13 C 0.57498(15) 0.95979(15) 0.78071(17) 0.0890(8) Uani 1 1 d . . . . .
H13A H 0.579275 1.006083 0.809060 0.107 Uiso 1 1 calc R U . . .
H13B H 0.547228 0.930582 0.823330 0.107 Uiso 1 1 calc R U . . .
C14 C 0.54122(11) 0.96432(10) 0.68312(13) 0.0554(5) Uani 1 1 d . . . . .
H14A H 0.549521 1.009913 0.654326 0.067 Uiso 1 1 calc R U . . .
H14B H 0.491022 0.956713 0.687755 0.067 Uiso 1 1 calc R U . . .
C10 C 0.57591(9) 0.90625(9) 0.62348(13) 0.0473(5) Uani 1 1 d . . . . .
C9 C 0.56792(11) 0.91717(10) 0.51574(13) 0.0550(5) Uani 1 1 d . . . . .
H9A H 0.587902 0.962337 0.498990 0.066 Uiso 1 1 calc R U . . .
H9B H 0.518308 0.918808 0.500399 0.066 Uiso 1 1 calc R U . . .
C8 C 0.60253(13) 0.86076(12) 0.45345(14) 0.0701(7) Uani 1 1 d . . . . .
H8A H 0.652219 0.858825 0.468192 0.084 Uiso 1 1 calc R U . . .
H8B H 0.582315 0.815465 0.468991 0.084 Uiso 1 1 calc R U . . .
C5 C 0.59319(12) 0.87477(11) 0.34749(14) 0.0585(6) Uani 1 1 d . . . . .
C6 C 0.64268(13) 0.91121(12) 0.29611(16) 0.0684(6) Uani 1 1 d . . . . .
H6 H 0.683027 0.926804 0.327051 0.082 Uiso 1 1 calc R U . . .
C7 C 0.63377(15) 0.92526(12) 0.19899(17) 0.0771(7) Uani 1 1 d . . . . .
H7 H 0.668362 0.949893 0.166072 0.092 Uiso 1 1 calc R U . . .
C2 C 0.57533(15) 0.90372(13) 0.15073(16) 0.0724(7) Uani 1 1 d . . . . .
C1 C 0.5653(2) 0.91976(17) 0.04465(18) 0.1210(13) Uani 1 1 d . . . . .
H1A H 0.604356 0.901555 0.008854 0.182 Uiso 1 1 calc R U . . .
H1B H 0.562522 0.969601 0.035630 0.182 Uiso 1 1 calc R U . . .
H1C H 0.522788 0.898263 0.022380 0.182 Uiso 1 1 calc R U . . .
C4 C 0.53458(13) 0.85277(13) 0.29859(17) 0.0736(7) Uani 1 1 d . . . . .
H4 H 0.500149 0.827625 0.331112 0.088 Uiso 1 1 calc R U . . .
C3 C 0.52587(15) 0.86730(14) 0.20211(18) 0.0819(8) Uani 1 1 d . . . . .
H3 H 0.485432 0.852011 0.171114 0.098 Uiso 1 1 calc R U . . .
C12 C 0.64571(16) 0.92818(19) 0.7650(2) 0.1150(12) Uani 1 1 d . . . . .
H12A H 0.651764 0.887557 0.806140 0.138 Uiso 1 1 calc R U . . .
H12B H 0.681994 0.962030 0.780397 0.138 Uiso 1 1 calc R U . . .
C11 C 0.65110(10) 0.90693(12) 0.66117(15) 0.0614(6) Uani 1 1 d . . . . .
H11A H 0.672143 0.860796 0.655390 0.074 Uiso 1 1 calc R U . . .
H11B H 0.679395 0.940258 0.625482 0.074 Uiso 1 1 calc R U . . .
H1 H 0.507(2) 0.833(2) 0.633(3) 0.179(19) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 H1 117(3) . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C12 C13 H13A 110.5 . . ?
C12 C13 H13B 110.5 . . ?
C12 C13 C14 106.1(2) . . ?
C13 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C13 C14 C10 105.17(17) . . ?
H14A C14 H14B 108.8 . . ?
C10 C14 H14A 110.7 . . ?
C10 C14 H14B 110.7 . . ?
O1 C10 C14 108.33(15) . . ?
O1 C10 C9 109.98(15) . . ?
O1 C10 C11 107.15(16) . . ?
C9 C10 C14 113.00(15) . . ?
C9 C10 C11 115.55(16) . . ?
C11 C10 C14 102.33(15) . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C10 C9 C8 114.71(16) . . ?
H9A C9 H9B 107.6 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C5 C8 C9 112.17(17) . . ?
C5 C8 H8A 109.2 . . ?
C5 C8 H8B 109.2 . . ?
C6 C5 C8 121.1(2) . . ?
C6 C5 C4 117.2(2) . . ?
C4 C5 C8 121.7(2) . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.3 . . ?
C2 C7 C6 121.4(2) . . ?
C2 C7 H7 119.3 . . ?
C7 C2 C1 121.3(3) . . ?
C7 C2 C3 117.3(2) . . ?
C3 C2 C1 121.4(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C3 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C13 C12 C11 108.15(19) . . ?
H12A C12 H12B 108.4 . . ?
C11 C12 H12A 110.1 . . ?
C11 C12 H12B 110.1 . . ?
C10 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
C12 C11 C10 105.53(18) . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.445(2) . ?
O1 H1 0.78(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.504(3) . ?
C13 C12 1.493(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C10 1.533(3) . ?
C10 C9 1.520(2) . ?
C10 C11 1.526(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.530(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C5 1.507(3) . ?
C5 C6 1.372(3) . ?
C5 C4 1.374(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.364(3) . ?
C2 C1 1.518(3) . ?
C2 C3 1.372(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.502(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C9 C8 -59.5(2) . . . . ?
O1 C10 C11 C12 -82.2(2) . . . . ?
C13 C14 C10 O1 77.4(2) . . . . ?
C13 C14 C10 C9 -160.49(19) . . . . ?
C13 C14 C10 C11 -35.6(2) . . . . ?
C13 C12 C11 C10 -16.5(3) . . . . ?
C14 C13 C12 C11 -6.0(3) . . . . ?
C14 C10 C9 C8 179.35(18) . . . . ?
C14 C10 C11 C12 31.7(2) . . . . ?
C10 C9 C8 C5 -179.62(19) . . . . ?
C9 C10 C11 C12 154.9(2) . . . . ?
C9 C8 C5 C6 92.9(3) . . . . ?
C9 C8 C5 C4 -86.0(3) . . . . ?
C8 C5 C6 C7 -178.9(2) . . . . ?
C8 C5 C4 C3 178.5(2) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C5 C4 C3 C2 0.5(4) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
C6 C7 C2 C1 179.4(2) . . . . ?
C6 C7 C2 C3 -0.3(4) . . . . ?
C7 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C12 C13 C14 C10 26.1(3) . . . . ?
C11 C10 C9 C8 62.0(2) . . . . ?
