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_4033469
_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 unk
_chemical_formula_moiety         'C30 H32 O5'
_chemical_formula_sum            'C30 H32 O5'
_chemical_formula_weight         472.56
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-04-24
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr  9 2013 14:10:59, GUI svn.r4456)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   18.8918(3)
_cell_length_b                   18.8918(3)
_cell_length_c                   6.39506(13)
_cell_measurement_reflns_used    9496
_cell_measurement_temperature    100.00(12)
_cell_measurement_theta_max      28.7900
_cell_measurement_theta_min      3.2750
_cell_volume                     1976.61(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9207
_diffrn_measurement_details
;
  1 omega  -14.00   98.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2489   77.0000 -150.0000 112

  2 omega  -14.00   98.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2489   77.0000  120.0000 112

  3 omega   34.00  108.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2489 -178.0000    0.0000 74

  4 omega   -7.00   86.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2489   38.0000   30.0000 93

  5 omega  -20.00   61.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2489  -99.0000  120.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0321063000
_diffrn_orient_matrix_UB_12      0.0069545000
_diffrn_orient_matrix_UB_13      0.0305873000
_diffrn_orient_matrix_UB_21      0.0277075000
_diffrn_orient_matrix_UB_22      0.0332031000
_diffrn_orient_matrix_UB_23      0.0633159000
_diffrn_orient_matrix_UB_31      0.0090012000
_diffrn_orient_matrix_UB_32      0.0269871000
_diffrn_orient_matrix_UB_33      -0.0857882000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            24412
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         5.37
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_type              'Agilent Mova'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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             756
_exptl_crystal_size_max          0.3876
_exptl_crystal_size_mid          0.1235
_exptl_crystal_size_min          0.1106
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         6468
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0981P)^2^+0.1187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1554
_reflns_number_gt                5660
_reflns_number_total             6468
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03079_si_007.cif
_cod_data_source_block           c32h30o5100k
_cod_depositor_comments
'Adding full bibliography for 4033466--4033471.cif.'
_cod_original_cell_volume        1976.62(7)
_cod_database_code               4033469
_chemical_oxdiff_formula         C32H30O5
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1A(H1AA,H1AB), C1B(H1BA,H1BB), C1C(H1CA,H1CB)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5A), C4B(H4B), C6(H6), C3B(H3B), C7B(H7BA), C6B(H6B), C5B(H5B), C7A(H7AA),
  C7C(H7C), C3C(H3C), C6A(H6A), C5A(H5AA), C3A(H3A), C6C(H6C), C4A(H4A),
 C5C(H5C), C4C(H4C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'