Glyoxylic acid monohydrate promoted reductive addition of sodium sulfinates to pillar[4]arene[1]quinone.
Zhang, Enfu; Ma, Da; Zhu, Chenghao; Organic & biomolecular chemistry 23 (2025) 1146–1149; doi:10.1039/d4ob01908c

data_7160302
_publ_section_title
;
 Glyoxylic acid monohydrate promoted reductive addition of sodium
 sulfinates to pillar[4]arene[1]quinone.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1146
_journal_page_last               1149
_journal_paper_doi               10.1039/d4ob01908c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C55 H54 O12 S'
_chemical_formula_sum            'C55 H54 O12 S'
_chemical_formula_weight         939.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-09-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2024-11-25 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.361(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.9910(19)
_cell_length_b                   14.3060(11)
_cell_length_c                   14.7845(11)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      57.00
_cell_measurement_theta_min      4.21
_cell_volume                     5481.4(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            75666
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        52.981
_diffrn_reflns_theta_max         52.981
_diffrn_reflns_theta_min         3.956
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1119 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.8788.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_description       polyhedral
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         9553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0538P)^2^+2.1962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8531
_reflns_number_total             9553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01908c2.cif
_cod_data_source_block           platon_sq
_cod_depositor_comments          'Adding full bibliography for 7160302.cif.'
_cod_database_code               7160302
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.927
_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:
 C7(H7A,H7B), C14(H14A,H14B), C21(H21A,H21B), C28(H28A,H28B), C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C9(H9), C12(H12), C16(H16), C19(H19), C23(H23), C26(H26),
 C30(H30), C33(H33), C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44),
  C45(H45), C46(H46), C47(H47)
2.c Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C51(H51A,H51B,
 H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C55(H55A,
 H55B,H55C)
;
_shelx_res_checksum              3619
_shelx_fab_checksum              37645
_shelx_shelxl_version_number     2019/2
_olex2_submission_special_instructions 'No special instructions were received'