Preparation of Vinylcyclopropanes by Sodium Mediated Reductive Isomerization of Methylenecyclopropanes.
Le Jeune, Karel; Chevallier-Michaud, Sabine; Gatineau, David; Giordano, Laurent; Tenaglia, Alphonse; Clavier, Hervé; The Journal of organic chemistry 80 (2015) 8821–8829; doi:10.1021/acs.joc.5b01205

data_4036250
_publ_section_title
;
 Preparation of Vinylcyclopropanes by Sodium Mediated Reductive
 Isomerization of Methylenecyclopropanes.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8821
_journal_page_last               8829
_journal_paper_doi               10.1021/acs.joc.5b01205
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C18 H30 N2 O4'
_chemical_formula_sum            'C18 H30 N2 O4'
_chemical_formula_weight         338.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2014-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.441(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9865(4)
_cell_length_b                   19.5582(8)
_cell_length_c                   11.7897(4)
_cell_measurement_temperature    293(2)
_cell_volume                     2071.50(14)
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -45.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   38.0000  150.0000 78

  2 omega   72.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0146  165.0000   88.0000 46

  3 omega   76.00  119.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   77.0000   60.0000 43

  4 omega   92.00  171.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   45.0000  120.0000 79

  5 omega   97.00  124.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  125.0000  -60.0000 27

  6 omega  150.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  125.0000  -60.0000 27

  7 omega  104.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   30.0000 -150.0000 74

  8 omega   64.00   92.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000  -30.0000 28

  9 omega   45.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000   60.0000 50

 10 omega   65.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000  120.0000 26

 11 omega   35.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000  120.0000 47

 12 omega   47.00  106.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000    0.0000 59

 13 omega   33.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000  -60.0000 50

 14 omega   54.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000 -150.0000 54

 15 omega   40.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000 -150.0000 49

 16 omega   31.00   59.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000 -180.0000 28

 17 omega   33.00  104.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719 -125.0000    0.0000 71

 18 omega   23.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0146 -125.0000   90.0000 57

 19 omega   24.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000   90.0000 84

 20 omega  -95.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146  125.0000 -180.0000 83

 21 omega -108.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146    0.0000   60.0000 155
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0040401000
_diffrn_orient_matrix_UB_12      -0.0166996000
_diffrn_orient_matrix_UB_13      -0.1273874000
_diffrn_orient_matrix_UB_21      0.0254062000
_diffrn_orient_matrix_UB_22      -0.0759947000
_diffrn_orient_matrix_UB_23      0.0286222000
_diffrn_orient_matrix_UB_31      -0.1698872000
_diffrn_orient_matrix_UB_32      -0.0118180000
_diffrn_orient_matrix_UB_33      -0.0020329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1799
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14631
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.083
_diffrn_reflns_theta_min         4.380
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36019
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_description
;
;
_exptl_crystal_F_000             736
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .14
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0885
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2391
_refine_ls_wR_factor_ref         0.2509
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3411
_reflns_number_total             3892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01205_si_002.cif
_cod_data_source_block           klj72014
_cod_database_code               4036250
_shelxl_version_number           2013-4
_cell_oxdiff_twin_number         3
_cell_oxdiff_volume              2071(3)
_diffrn_oxdiff_twin_integration_method simultaneous
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C7(H7)
2.d X=CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'