Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes.
Mondal, Mukulesh; Panda, Manashi; McKee, Vickie; Kerrigan, Nessan J.; The Journal of organic chemistry 84 (2019) 11983–11991; doi:10.1021/acs.joc.9b01854

data_4034468
_publ_section_title
;
 Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed
 [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11983
_journal_page_last               11991
_journal_paper_doi               10.1021/acs.joc.9b01854
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C17 H20 N2 O4'
_chemical_formula_sum            'C17 H20 N2 O4'
_chemical_formula_weight         316.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.086(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5660(2)
_cell_length_b                   17.6181(4)
_cell_length_c                   17.1644(4)
_cell_measurement_reflns_used    7160
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      74.4350
_cell_measurement_theta_min      3.6170
_cell_volume                     3155.11(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material
'Olex2 (Dolomanov et al. 2009), PublCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015a)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -11.00  19.00   1.00    4.12    --  -49.16  19.00  60.00   30
  2  \w    -20.00  14.00   1.00    4.12    --  -49.16  19.00   0.00   34
  3  \w    -17.00  15.00   1.00    4.12    --  -49.16  19.00 120.00   32
  4  \w    -20.00  18.00   1.00    4.12    --  -49.16  19.00 150.00   38
  5  \w    -58.00 -29.00   1.00   16.48    --  -82.50  62.00 150.00   29
  6  \w    -92.00 -10.00   1.00    4.12    --  -49.16 125.00-120.00   82
  7  \w    -23.00  22.00   1.00    4.12    --  -49.16  19.00-150.00   45
  8  \w   -126.00 -92.00   1.00    4.12    --  -49.16   0.00-150.00   34
  9  \w     57.00 109.00   1.00   16.48    --  100.40 -94.00 -90.00   52
 10  \w     72.00 117.00   1.00   16.48    --  100.40-125.00-120.00   45
 11  \w     70.00  97.00   1.00   16.48    --  100.40 -94.00   0.00   27
 12  \w     75.00 117.00   1.00   16.48    --  100.40-125.00  30.00   42
 13  \w     63.00  90.00   1.00   16.48    --  100.40 -94.00 150.00   27
 14  \w     33.00  63.00   1.00   16.48    --  100.40 -61.00 150.00   30
 15  \w     35.00  65.00   1.00   16.48    --  100.40 -61.00 120.00   30
 16  \w    101.00 175.00   1.00   16.48    --  100.40   0.00 150.00   74
 17  \w    106.00 173.00   1.00   16.48    --  100.40   0.00  30.00   67
 18  \w    109.00 171.00   1.00   16.48    --  100.40   0.00 -90.00   62
 19  \w    116.00 161.00   1.00   16.48    --  100.40 125.00  60.00   45
 20  \w    120.00 167.00   1.00   16.48    --  100.40 125.00 150.00   47
 21  \w     34.00  67.00   1.00   16.48    --  100.40 -61.00 -60.00   33
 22  \w     34.00  66.00   1.00   16.48    --  100.40 -61.00 -30.00   32
 23  \w     33.00  58.00   1.00   16.48    --  100.40 -61.00  30.00   25
 24  \w     37.00 118.00   1.00   16.48    --  100.40-125.00 120.00   81
 25  \w     35.00  60.00   1.00   16.48    --  100.40-125.00-120.00   25
 26  \w     34.00  67.00   1.00   16.48    --  100.40 -61.00-150.00   33
 27  \w     42.00  68.00   1.00   16.48    --  100.40 -61.00-180.00   26
 28  \w     34.00  64.00   1.00   16.48    --  100.40 -61.00-120.00   30
 29  \w    120.00 162.00   1.00   16.48    --  100.40 125.00-120.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1171844000
_diffrn_orient_matrix_UB_12      0.0094737000
_diffrn_orient_matrix_UB_13      -0.0651858000
_diffrn_orient_matrix_UB_21      0.0707946000
_diffrn_orient_matrix_UB_22      0.0627052000
_diffrn_orient_matrix_UB_23      -0.0385645000
_diffrn_orient_matrix_UB_31      0.0550493000
_diffrn_orient_matrix_UB_32      -0.0601592000
_diffrn_orient_matrix_UB_33      -0.0504381000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_unetI/netI     0.0087
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14222
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         3.619
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.29a (Rigaku Oxford Diffraction, 2018)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00053(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     1184
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0854P)^2^+2.5228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.1679
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2555
_reflns_number_total             2799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01854_si_003.cif
_cod_data_source_block           MP-IV-27-F2(exp_396)
_cod_original_cell_volume        3155.10(12)
_cod_database_code               4034468
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H15N2O4
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Shared sites
{O2, O2'}
{O3, O3'}
{O4, O4'}
{N1, N1'}
{N2, N2'}
{C4, C4'}
{C5, C5'}
{C15, C15'}
{C16, C16'}
{C17, C17'}
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(O2) = Uanis(O2')
Uanis(O3) = Uanis(O3')
Uanis(O4) = Uanis(O4')
Uanis(N1) = Uanis(N1')
Uanis(N2) = Uanis(N2')
Uanis(C4) = Uanis(C4')
Uanis(C5) = Uanis(C5')
Uanis(C15) = Uanis(C15')
Uanis(C16) = Uanis(C16')
Uanis(C17) = Uanis(C17')
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{O1', O2', O3', O4', N1', N2', C1', C2', C3', C4', C5', C6', C7', C8', C9',
C10', C11', C12', C13', C14', C15', C16', C17'} sigma for 1-2: 0.02, 1-3: 0.04
as
{O1, O2, O3, O4, N1, N2, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12,
C13, C14, C15, C16, C17}
6. Others
 Fixed Sof: O1(0.5) O2(0.5) O3(0.5) O4(0.5) N1(0.5) H1(0.5) N2(0.5) H2(0.5)
 C1(0.5) H1A(0.5) C2(0.5) H2A(0.5) H2B(0.5) C3(0.5) H3A(0.5) H3B(0.5) H3C(0.5)
 C4(0.5) H4A(0.5) H4B(0.5) C5(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5) C8(0.5)
 H8A(0.5) H8B(0.5) H8C(0.5) C9(0.5) C10(0.5) H10(0.5) C11(0.5) H11(0.5)
 C12(0.5) H12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) C16(0.5)
 C17(0.5) O1'(0.5) O2'(0.5) O3'(0.5) O4'(0.5) N1'(0.5) H1'(0.5) N2'(0.5)
 H2'(0.5) C1'(0.5) H1'A(0.5) C2'(0.5) H2'A(0.5) H2'B(0.5) C3'(0.5) H3'A(0.5)
 H3'B(0.5) H3'C(0.5) C4'(0.5) H4'A(0.5) H4'B(0.5) C5'(0.5) C6'(0.5) H6'(0.5)
 C7'(0.5) H7'(0.5) C8'(0.5) H8'A(0.5) H8'B(0.5) H8'C(0.5) C9'(0.5) C10'(0.5)
 H10'(0.5) C11'(0.5) H11'(0.5) C12'(0.5) H12'(0.5) C13'(0.5) H13'(0.5)
 C14'(0.5) H14'(0.5) C15'(0.5) C16'(0.5) C17'(0.5)
7.a Ternary CH refined with riding coordinates:
 C1(H1A), C6(H6), C7(H7), C1'(H1'A), C6'(H6'), C7'(H7')
7.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C2'(H2'A,H2'B), C4'(H4'A,H4'B)
7.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), N1'(H1'),
 N2'(H2'), C10'(H10'), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14')
7.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C3'(H3'A,H3'B,H3'C), C8'(H8'A,H8'B,H8'C)
;
_shelx_res_checksum              91338
_shelx_hkl_checksum              45380
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.821