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_4033471
_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_formula_moiety         'C42 H48 O8'
_chemical_formula_sum            'C42 H48 O8'
_chemical_formula_weight         680.80
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5718(8)
_cell_length_b                   14.1562(9)
_cell_length_c                   22.0456(15)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.77
_cell_measurement_theta_min      2.27
_cell_volume                     3611.3(4)
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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  0.0458
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            49888
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         22.898
_diffrn_reflns_theta_min         1.568
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6791
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0932 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.9118.
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    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 2710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_coef       0.0075(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         9867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0481P)^2^+0.8156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                7522
_reflns_number_total             9867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03079_si_005.cif
_cod_data_source_block           2015_08_31_0m
_cod_depositor_comments
'Adding full bibliography for 4033466--4033471.cif.'
_cod_original_cell_volume        3611.4(4)
_cod_database_code               4033471
_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:
 C10(H10), C4(H4), C11(H11), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB), C5(H5A,H5B), C3A(H3AA,H3AB), C1C(H1CA,H1CB), C1D(H1DA,H1DB),
 C4A(H4AA,H4AB)
2.c Aromatic/amide H refined with riding coordinates:
 C7D(H7D), C7B(H7B), C6D(H6D), C3B(H3B), C3C(H3C), C3D(H3D), C5D(H5D),
 C4B(H4B), C2(H2), C6B(H6B), C4C(H4C), C7C(H7C), C5B(H5BA), C5C(H5C), C4D(H4D),
 C6C(H6C), C6(H6)
2.d X=CH2 refined with riding coordinates:
 C3(H3A,H3E), C7(H7A,H7E)
2.e Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C10A(H10A,H10B,H10C), C7A(H7AA,H7AB,H7AC)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-08-31
_olex2_submission_special_instructions 'No special instructions were received'