Stereocontrolled synthesis of the aconitine D ring from D-glucose.
Pocock, Ian A.; Doulcet, Julien; Rice, Craig R.; Sweeney, Joseph B.; Gill, Duncan M.; Organic & biomolecular chemistry 22 (2024) 4347–4352; doi:10.1039/d4ob00561a

data_7159938
_publ_section_title
;
 Stereocontrolled synthesis of the aconitine D ring from D-glucose.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4347
_journal_page_last               4352
_journal_paper_doi               10.1039/d4ob00561a
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H20 O6'
_chemical_formula_sum            'C17 H20 O6'
_chemical_formula_weight         320.344
_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'
_symmetry_Int_Tables_number      4
_audit_creation_date             2023-06-19
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2024-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.038(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3489(4)
_cell_length_b                   5.0069(2)
_cell_length_c                   18.7570(7)
_cell_measurement_reflns_used    3696
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.46
_cell_measurement_theta_min      4.72
_cell_volume                     783.95(6)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.9653
_diffrn_measured_fraction_theta_max 0.9570
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_Laue_measured_fraction_full 0.9653
_diffrn_reflns_Laue_measured_fraction_max 0.9570
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4136
_diffrn_reflns_point_group_measured_fraction_full 0.7683
_diffrn_reflns_point_group_measured_fraction_max 0.7478
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         72.46
_diffrn_reflns_theta_min         4.72
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       plate
_exptl_crystal_F_000             341.282
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3997
_refine_diff_density_min         -0.5117
_refine_diff_density_rms         0.1258
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_d_res_high            0.8085
_refine_ls_d_res_low             9.3770
_refine_ls_goodness_of_fit_ref   1.0507
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0507
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0881
_refine_ls_shift/su_max          -0.0023
_refine_ls_shift/su_mean         0.0006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1307P)^2^+1.8021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2285
_refine_ls_wR_factor_ref         0.2359
_reflns_Friedel_coverage         0.480
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              6
_reflns_limit_k_min              -5
_reflns_limit_l_max              23
_reflns_limit_l_min              -22
_reflns_number_gt                2111
_reflns_number_total             2327
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob00561a2.cif
_cod_data_source_block           cu_IanP_chiral_0m
_cod_depositor_comments
;
          Adding full bibliography for 7159938.cif.

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C8.5 H10 O3'
_cod_original_formula_weight         160.172
_cod_original_formula_moiety         '0.5(C17 H20 O6)'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7159938
_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 Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5a), C6(H6)
2.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
2.f :
 C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'