Stereoselective total syntheses of (-)-hygrophorone A<sup>12</sup>, 4-<i>O</i>-acetyl-hygrophorone A<sup>12</sup> and (+)-hygrophorone B<sup>12</sup>.
Das, Sayani; Dalal, Anu; Gholap, Shivajirao L.; Organic & biomolecular chemistry 19 (2021) 1100–1108; doi:10.1039/d0ob02303e

data_7157831
_publ_section_title
;
 Stereoselective total syntheses of (-)-hygrophorone A<sup>12</sup>,
 4-<i>O</i>-acetyl-hygrophorone A<sup>12</sup> and (+)-hygrophorone
 B<sup>12</sup>.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1100
_journal_page_last               1108
_journal_paper_doi               10.1039/d0ob02303e
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration R
_chemical_formula_moiety         'C18 H32 O4'
_chemical_formula_sum            'C18 H32 O4'
_chemical_formula_weight         312.44
_chemical_name_systematic        'Hygrophorone A12'
_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     direct
_audit_creation_date             2020-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2020-10-05 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.464(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9985(6)
_cell_length_b                   10.3197(6)
_cell_length_c                   22.4140(14)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.17
_cell_volume                     1846.7(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            48074
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_min         2.173
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1453 before and 0.0737 after correction.
The Ratio of minimum to maximum transmission is 0.9220.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         9176
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0435P)^2^+0.2008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6378
_reflns_number_total             9176
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02303e2.cif
_cod_data_source_block           pm185_0m_a
_cod_depositor_comments          'Adding full bibliography for 7157831.cif.'
_cod_database_code               7157831
_shelxl_version_number           2013-4
_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:
 C24(H24), C5(H5A), C22(H22), C6(H6A)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C7(H7A,H7B), C9(H9A,H9B), C8(H8A,H8B), C10(H10A,H10B),
 C26(H26A,H26B), C34(H34A,H34B), C31(H31A,H31B), C30(H30A,H30B), C14(H14A,H14B),
  C32(H32A,H32B), C12(H12A,H12B), C11(H11A,H11B), C29(H29A,H29B), C28(H28A,
 H28B), C33(H33A,H33B), C16(H16A,H16B), C15(H15A,H15B), C35(H35A,H35B),
 C13(H13A,H13B), C27(H27A,H27B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C3(H3), C4(H4A)
2.d Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O8(H8), O1(H1), O5(H5), O4(H4), O6(H6), O2(H2)
;
_shelx_res_checksum              5657
_shelx_hkl_checksum              4688
_olex2_submission_special_instructions 'No special instructions were received'