Electrochemical esterification reaction of alkynes with diols via cleavage of carbon–carbon triple bonds without catalyst and oxidant
Wang, Pei-Long; Shen, Hui-Zhi; Cheng, Hui-Hui; Gao, Hui; Li, Pin-Hua; Green Chemistry 22 (2020) 6783–6791; doi:10.1039/D0GC02193H

data_7241226
_publ_section_title
;
 Electrochemical esterification reaction of alkynes with diols via
 cleavage of carbon--carbon triple bonds without catalyst and oxidant
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              6783
_journal_page_last               6791
_journal_paper_doi               10.1039/D0GC02193H
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C11 H12 O5'
_chemical_formula_sum            'C11 H12 O5'
_chemical_formula_weight         224.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-09 deposited with the CCDC.	2020-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.450(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3520(9)
_cell_length_b                   5.7066(6)
_cell_length_c                   22.623(2)
_cell_measurement_reflns_used    9629
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.451
_cell_measurement_theta_min      2.439
_cell_volume                     1077.90(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16076
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         0.900
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1013 before and 0.0609 after correction.
The Ratio of minimum to maximum transmission is 0.8613.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1518 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4909
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0450
_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^)+(0.1033P)^2^+0.0981P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3975
_reflns_number_total             4909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc02193h2.cif
_cod_data_source_block           111
_cod_depositor_comments
;
          Adding full bibliography for 7241226.cif.

2025-04-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H48 O20'
_cod_original_formula_weight         896.82
_cod_original_formula_moiety         '4(C11 H12 O5)'
_cod_original_formula_units_Z            1
_cod_database_code               7241226
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.973
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C5(H5A), C8(H8), C19(H19), C16(H16), C15(H15), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O10(H10)
;
_shelx_res_checksum              82604
_shelx_hkl_checksum              32763
_olex2_submission_special_instructions 'No special instructions were received'