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_4033467
_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 syn
_chemical_formula_moiety         'C32 H36 O5'
_chemical_formula_sum            'C32 H36 O5'
_chemical_formula_weight         500.61
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-09
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_angle_alpha                90
_cell_angle_beta                 90.099(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9952(5)
_cell_length_b                   10.1174(6)
_cell_length_c                   15.1830(8)
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    100.00(16)
_cell_measurement_theta_max      28.1860
_cell_measurement_theta_min      2.6140
_cell_volume                     1381.77(13)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.881
_diffrn_measured_fraction_theta_max 0.738
_diffrn_measurement_details
;
  1 omega  -63.00    6.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8426  -38.0000  -90.0000 69

  2 omega  -20.00   18.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9364  -99.0000 -180.0000 38

  3 omega   35.00   67.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8426  178.0000  150.0000 32
;
_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      0.0482070000
_diffrn_orient_matrix_UB_12      -0.0536069000
_diffrn_orient_matrix_UB_13      -0.0094481000
_diffrn_orient_matrix_UB_21      -0.0555442000
_diffrn_orient_matrix_UB_22      -0.0286759000
_diffrn_orient_matrix_UB_23      -0.0271552000
_diffrn_orient_matrix_UB_31      0.0284197000
_diffrn_orient_matrix_UB_32      0.0348962000
_diffrn_orient_matrix_UB_33      -0.0368338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.881
_diffrn_reflns_Laue_measured_fraction_max 0.738
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5400
_diffrn_reflns_point_group_measured_fraction_full 0.647
_diffrn_reflns_point_group_measured_fraction_max 0.519
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.220
_diffrn_reflns_theta_min         2.419
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_type              'Agilent Mova'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.983
_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    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3146
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.0768
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0343P)^2^+0.1567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.335
_reflns_Friedel_fraction_full    0.382
_reflns_Friedel_fraction_max     0.276
_reflns_number_gt                3387
_reflns_number_total             3897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03079_si_003.cif
_cod_data_source_block           exp_2488
_cod_depositor_comments
'Adding full bibliography for 4033466--4033471.cif.'
_cod_original_cell_volume        1381.77(14)
_cod_database_code               4033467
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C32 H36 O5'
_reflns_odcompleteness_completeness 86.64
_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:
 C00B(H00D), C00D(H00E), C00F(H00G), C00G(H00H), C00K(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00M(H00O,H00P), C00Q(H00S,H00T), C00X(H00,H)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00C), C00E(H00F), C00I(H00K), C00J(H00L), C00L(H00N),
 C00O(H00Q), C00P(H00R), C00R(H00U), C00S(H00V), C00T(H00W), C00U(H00X),
 C00V(H00Y), C00W(H00Z), C00Y(H0AA), C00Z(H1AA), C011(H011)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_olex2_date_sample_data_collection 2015-04-09
_olex2_submission_original_sample_id 2015_04_09
_olex2_submission_special_instructions 'No special instructions were received'