Domino enyne metathesis en route to skeletally diverse, privileged scaffolds: synthesis of the tricyclic core of pseudolaric acid F
Lin, Minggui; Cui, Hao; Hua, Yuhui; Zhang, Yandong; Organic Chemistry Frontiers 6 (2019) 2771–; doi:10.1039/C9QO00477G

data_1554928
_publ_section_title
;
 Domino enyne metathesis en route to skeletally diverse, privileged
 scaffolds: synthesis of the tricyclic core of pseudolaric acid F
;
_journal_issue                   15
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2771
_journal_paper_doi               10.1039/C9QO00477G
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C27 H33.99 O3 Si'
_chemical_formula_sum            'C27 H34 O3 Si'
_chemical_formula_weight         434.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2019-04-04 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.609(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   42.742(3)
_cell_length_b                   10.4771(9)
_cell_length_c                   10.9037(9)
_cell_measurement_reflns_used    3010
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.31
_cell_volume                     4873.1(7)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10004
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.000
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_size_rad          0.0100
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+3.5563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3713
_reflns_number_total             4772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00477g2.cif
_cod_data_source_block           mon
_cod_database_code               1554928
_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. Others
 Sof(C41)=Sof(C42)=Sof(H42)=Sof(C43)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=
 Sof(C46)=Sof(H46)=1-FVAR(1)
 Sof(C31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=
 Sof(H35)=Sof(C36)=Sof(H36)=FVAR(1)
 Fixed Sof: C21(0.4) H21A(0.4) H21B(0.4) H21C(0.4) C23(0.4) H23A(0.4)
 H23B(0.4) H23C(0.4) C1A(0.6) H1AA(0.6) H1AB(0.6) H1AC(0.6) C2A(0.6) H2AA(0.6)
 H2AB(0.6) H2AC(0.6) H43(0.5)
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,
 H16B), C18(H18A,H18B)
3.c Me refined with riding coordinates:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C1A(H1AA,H1AB,
 H1AC), C2A(H2AA,H2AB,H2AC)
3.d Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C7(H7), C9(H9), C14(H14), C17(H17), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36), C42(H42), C44(H44), C45(H45), C46(H46)
3.e Fitted hexagon refined as free rotating group:
 C31(C32,C33,C34,C35,C36), C41(C42,C43,C44,C45,C46)
3.f Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'