Enantiospecific Total Synthesis of the Highly Strained (-)-Presilphiperfolan-8-ol via a Pd-Catalyzed Tandem Cyclization.
Hu, Pengfei; Snyder, Scott A.; Journal of the American Chemical Society 139 (2017) 5007–5010; doi:10.1021/jacs.7b01454

data_4131242
_publ_section_title
;
 Enantiospecific Total Synthesis of the Highly Strained
 (-)-Presilphiperfolan-8-ol via a Pd-Catalyzed Tandem Cyclization.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5007
_journal_page_last               5010
_journal_paper_doi               10.1021/jacs.7b01454
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H26 O2, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C16.5 H27 Cl O2'
_chemical_formula_weight         292.83
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.047(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9600(3)
_cell_length_b                   18.1329(6)
_cell_length_c                   9.7390(3)
_cell_measurement_reflns_used    4251
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.33
_cell_measurement_theta_min      4.54
_cell_volume                     1581.29(9)
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17656
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.427
_diffrn_reflns_theta_min         4.543
_diffrn_source                   'INCOATEC ImuS micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.112
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1032 before and 0.0695 after correction.
The Ratio of minimum to maximum transmission is 0.7794.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1597 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         6138
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0312P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                4466
_reflns_number_total             6138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b01454_si_002.cif
_cod_data_source_block           0290_pengfei_ss
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C16 H26 O2), C H2 Cl2'
_cod_original_formula_sum        'C33 H54 Cl2 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     585.66
_cod_database_code               4131242
_shelx_estimated_absorpt_t_max   0.801
_shelx_estimated_absorpt_t_min   0.677
_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:
 C2(H2), C5(H5), C7(H7), C18(H18), C21(H21), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C10(H10A,H10B), C13(H13A,H13B),
 C19(H19A,H19B), C20(H20A,H20B), C24(H24A,H24B), C26(H26A,H26B), C29(H29A,H29B),
  C33(H33A,H33B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C28(H28A,H28B,H28C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C)
;
_shelx_res_checksum              79038
_shelx_hkl_checksum              35795
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'