Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone Acetals.
Hedberg, Christinne; Estrup, Morten; Eikeland, Espen Z.; Jensen, Henrik H.; The Journal of organic chemistry 83 (2018) 2154–2165; doi:10.1021/acs.joc.7b03079

data_4033466
_publ_section_title
;
 Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone
 Acetals.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2154
_journal_page_last               2165
_journal_paper_doi               10.1021/acs.joc.7b03079
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C35 H42 O7'
_chemical_formula_sum            'C35 H42 O7'
_chemical_formula_weight         574.68
_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_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-08
_audit_creation_method
;
Olex2 1.2
(compiled Jan 19 2015 12:28:14 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.296(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2892(15)
_cell_length_b                   8.9842(11)
_cell_length_c                   14.7594(18)
_cell_measurement_reflns_used    9791
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.29
_cell_volume                     1487.9(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            45713
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         23.616
_diffrn_reflns_theta_min         1.095
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1218 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.9538.
The \l/2 correction factor is 0.0015.
;
_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    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 3922 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         9072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0490P)^2^+0.3180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                8663
_reflns_number_total             9072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03079_si_006.cif
_cod_data_source_block           2015_10_12_b_0m2
_cod_depositor_comments
'Adding full bibliography for 4033466--4033471.cif.'
_cod_database_code               4033466
_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:
 C8(H8), C7(H7), C5(H5), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C6(H6A,H6B), C1A(H1AA,H1AB), C9C(H9CA,H9CB), C10C(H10A,H10B),
 C1B(H1BA,H1BB)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C3A(H3A), C7B(H7B), C2(H2), C7A(H7A), C5A(H5A), C5B(H5B), C4A(H4A),
 C6B(H6BA), C6A(H6AA), C4B(H4B), C3B(H3B)
2.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B)
2.e Idealised Me refined as rotating group:
 C5C(H5CA,H5CB,H5CC), C7C(H7CA,H7CB,H7CC), C4C(H4CA,H4CB,H4CC)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              75333
_shelx_hkl_checksum              93197
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'