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_4033470
_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         'C39 H38 N2 O10'
_chemical_formula_sum            'C39 H38 N2 O10'
_chemical_formula_weight         694.71
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-04-23
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4650(5)
_cell_length_b                   14.7263(10)
_cell_length_c                   31.5337(18)
_cell_measurement_reflns_used    3445
_cell_measurement_temperature    99.97(13)
_cell_measurement_theta_max      24.2230
_cell_measurement_theta_min      3.0410
_cell_volume                     3466.6(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_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_temperature      99.97(13)
_diffrn_detector_area_resol_mean 5.1795
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_details
;
  1 omega  -15.00   16.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9364  -99.0000   90.0000 31

  2 omega  -88.00  -44.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9364  -19.0000  -30.0000 44

  3 omega  -19.00    8.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9364  -19.0000  -30.0000 27

  4 omega  -64.00  -24.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9364  -38.0000  -90.0000 40

  5 omega  -63.00   12.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8426  -57.0000   30.0000 75
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0229353000
_diffrn_orient_matrix_UB_12      -0.0124449000
_diffrn_orient_matrix_UB_13      0.0210348000
_diffrn_orient_matrix_UB_21      -0.0741684000
_diffrn_orient_matrix_UB_22      -0.0300717000
_diffrn_orient_matrix_UB_23      0.0006565000
_diffrn_orient_matrix_UB_31      0.0548157000
_diffrn_orient_matrix_UB_32      -0.0354979000
_diffrn_orient_matrix_UB_33      -0.0079380000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            17375
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.38
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94586
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.1648
_exptl_crystal_size_mid          0.0901
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         5837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0336P)^2^+0.1165P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                4608
_reflns_number_total             5837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03079_si_002.cif
_cod_data_source_block           c39h38o10n2_100k
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033466--4033471.cif.
;
_cod_original_cell_volume        3466.5(4)
_cod_database_code               4033470
_chemical_oxdiff_formula         'C39 H38 O10 N2'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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:
 C3(H3), C8(H8), C1(H1), C4(H4A), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1C(H1CA,H1CB), C1A(H1AA,H1AB), C1B(H1BA,H1BB), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C7C(H7C), C3A(H3A), C7D(H7D), C5C(H5C), C3B(H3B), C3C(H3C),
 C7B(H7B), C4A(H4AA), C6A(H6A), C5A(H5A), C6B(H6B), C6(H6), C4C(H4C), C5B(H5B),
 C7A(H7AA), C5D(H5D), C3D(H3D), C4B(H4B), C6C(H6C)
2.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B), C7(H7A,H7E)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;