Control of the stereochemistry of C14 hydroxyl during the total synthesis of withanolide E and physachenolide C
Anees, M.; Nayak, S.; Afarinkia, K.; Vinader, V.; RSC Advances 8 (2018) 39691–; doi:10.1039/C8RA08540D

data_7231897
_publ_section_title
;
 Control of the stereochemistry of C14 hydroxyl during the total synthesis
 of withanolide E and physachenolide C
;
_journal_issue                   69
_journal_name_full               'RSC Advances'
_journal_page_first              39691
_journal_paper_doi               10.1039/C8RA08540D
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H30 O3'
_chemical_formula_sum            'C22 H30 O3'
_chemical_formula_weight         342.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-08-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-08-09 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3071(7)
_cell_length_b                   19.3724(9)
_cell_length_c                   8.0124(4)
_cell_measurement_reflns_used    2815
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      65.07
_cell_measurement_theta_min      4.26
_cell_volume                     1910.30(17)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4706
_diffrn_reflns_theta_full        56.89
_diffrn_reflns_theta_max         56.89
_diffrn_reflns_theta_min         4.26
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0590 before and 0.0462 after correction.
The Ratio of minimum to maximum transmission is 0.8104.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.406
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.3202P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                2260
_reflns_number_total             2391
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ra08540d2.cif
_cod_data_source_block           mxa107_92cut
_cod_database_code               7231897
_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), C9(H9), C11(H11), C12(H12), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2AA(H2AA,H2AB), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C15(H15A,
 H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C3AA(H3AA,H3AB,H3AC), C4AA(H4AA,
 H4AB,H4AC)
;
_olex2_submission_special_instructions 'No special instructions were received'