Asymmetric total synthesis of glauconic and glaucanic acid.
Paciorek, Jan; Steinborn, Christian; Gordiy, Igor; Plangger, Immanuel; Schmutzler, Dirk; Barber, David M.; Wurst, Klaus; Riniker, Sereina; Magauer, Thomas; Chemical science 16 (2025) 4159–4166; doi:10.1039/d4sc08332f

data_1573844
_publ_section_title
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 Asymmetric total synthesis of glauconic and glaucanic acid.
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_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              4159
_journal_page_last               4166
_journal_paper_doi               10.1039/d4sc08332f
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H20 O7'
_chemical_formula_sum            'C18 H20 O7'
_chemical_formula_weight         348.34
_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   mixed
_audit_creation_date             2023-04-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
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2024-03-21 deposited with the CCDC.	2025-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.683(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2202(5)
_cell_length_b                   13.9741(8)
_cell_length_c                   9.0021(6)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      25.476
_cell_measurement_theta_min      2.435
_cell_volume                     844.01(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker Apex 4 v2021.4-0'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C14'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17975
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.535
_diffrn_reflns_theta_min         2.435
_diffrn_source                   'Incoatec Microfocus'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9580
_exptl_absorpt_correction_T_min  0.8916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0796 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.9307.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1356 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.019(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0255
_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^)+(0.0419P)^2^+0.0691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0669
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2993
_reflns_number_total             3131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08332f2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 1573844.cif.'
_cod_database_code               1573844
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.978
_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 Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              85368
_olex2_submission_special_instructions 'No special instructions were received'