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_4034467
_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_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 N2 O4'
_chemical_formula_sum            'C17 H16 N2 O4'
_chemical_formula_weight         312.32
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.0660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.80150(10)
_cell_length_b                   8.11190(10)
_cell_length_c                   15.13410(10)
_cell_measurement_reflns_used    22636
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.6150
_cell_measurement_theta_min      3.9330
_cell_volume                     1494.11(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_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 0.993
_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     -8.00  20.00   1.00    0.84    --   26.00  97.00 131.04   28
  2  \w      8.00  33.00   1.00    0.84    --   42.00  94.00 -53.48   25
  3  \w     31.00 100.00   1.00    0.84    --   48.91-125.00  30.00   69
  4  \w      6.00  76.00   1.00    0.84    --   48.91 -99.00-180.00   70
  5  \w    -75.00 -31.00   1.00    0.84    --  -49.16 -45.00-154.10   44
  6  \w   -121.00 -94.00   1.00    0.84    --  -49.16 -19.00 120.00   27
  7  \w    -81.00 -35.00   1.00    0.84    --  -49.16 -38.00  60.00   46
  8  \w   -116.00 -77.00   1.00    0.84    --  -49.16 -45.00-154.10   39
  9  \w    -69.00 -34.00   1.00    0.84    --  -49.16 -38.00 -90.00   35
 10  \w   -114.00 -77.00   1.00    0.84    --  -49.16 -57.00  30.00   37
 11  \w    -69.00 -28.00   1.00    0.84    --  -49.16 -57.00  30.00   41
 12  \w    -93.00 -35.00   1.00    0.84    --  -49.16 -19.00 120.00   58
 13  \w     18.00  43.00   1.00    0.84    --   50.00  90.00 138.43   25
 14  \w     19.00  46.00   1.00    0.84    --   50.00  88.00  14.15   27
 15  \w     19.00  45.00   1.00    0.84    --   50.00  91.00 177.56   26
 16  \w     26.00  63.00   1.00    0.84    --   54.00  83.00 -65.68   37
 17  \w     78.00 123.00   1.00    0.84    --   54.00  83.00 -65.68   45
 18  \w     29.00  58.00   1.00    0.84    --   58.00  83.00-134.94   29
 19  \w     34.00  61.00   1.00    0.84    --   62.00  82.00 129.36   27
 20  \w     34.00  61.00   1.00    0.84    --   62.00  80.00 -98.71   27
 21  \w     34.00  60.00   1.00    0.84    --   62.00  81.00  54.92   26
 22  \w     90.00 119.00   1.00    0.84    --   62.00  81.00  54.92   29
 23  \w     78.00 118.00   1.00    0.84    --   62.00  80.00 -98.71   40
 24  \w     38.00  64.00   1.00    0.84    --   66.00  80.00  -1.47   26
 25  \w     38.00  64.00   1.00    0.84    --   66.00  81.00  90.83   26
 26  \w     39.00  65.00   1.00    0.84    --   66.00  77.00 178.28   26
 27  \w     39.00  64.00   1.00    0.84    --   66.00  79.00  69.12   25
 28  \w    -78.00 -51.00   1.00    0.84    --  -78.00 -75.00 -17.57   27
 29  \w    -81.00 -55.00   1.00    0.84    --  -82.00 -76.00  78.30   26
 30  \w    -81.00 -55.00   1.00    0.84    --  -82.50 -77.00  37.08   26
 31  \w    -85.00 -56.00   1.00    0.84    --  -82.50 -77.00 -60.00   29
 32  \w    -82.00 -55.00   1.00    0.84    --  -82.50 -77.00-180.00   27
 33  \w    -85.00 -55.00   1.00    0.84    --  -82.50 -77.00  60.00   30
 34  \w    -83.00 -55.00   1.00    0.84    --  -82.50 -79.00 118.34   28
 35  \w    -85.00 -58.00   1.00    0.84    --  -82.50 -71.00   5.64   27
 36  \w    -81.00 -55.00   1.00    0.84    --  -82.50 -77.00-150.00   26
 37  \w    -81.00 -56.00   1.00    0.84    --  -82.50 -76.00 131.04   25
 38  \w    -84.00 -55.00   1.00    0.84    --  -82.50 -77.00-120.00   29
 39  \w    -83.00 -55.00   1.00    0.84    --  -82.50 -77.00 161.10   28
 40  \w    -82.00 -55.00   1.00    0.84    --  -82.50 -77.00 -41.27   27
 41  \w    -82.00 -55.00   1.00    0.84    --  -82.50 -78.00-163.69   27
 42  \w    -82.00 -55.00   1.00    0.84    --  -82.50 -77.00 -30.00   27
 43  \w    -84.00 -56.00   1.00    0.84    --  -82.50 -77.00 -90.00   28
 44  \w    118.00 154.00   1.00    0.84    --  100.40  77.00  90.00   36
 45  \w     75.00 108.00   1.00    0.84    --  100.40  77.00  90.00   33
 46  \w     73.00 168.00   1.00    0.84    --  100.40  77.00 -60.00   95
 47  \w     34.00  63.00   1.00    0.84    --  100.40 -61.00 -30.00   29
 48  \w     32.00 110.00   1.00    0.84    --  100.40 -94.00-120.00   78
 49  \w     62.00 117.00   1.00    0.84    --  100.40-125.00  90.00   55
 50  \w     73.00 146.00   1.00    0.84    --  100.40  77.00 -30.00   73
 51  \w     33.00  59.00   1.00    0.84    --  100.40 -56.00 164.00   26
 52  \w     35.00  68.00   1.00    0.84    --  100.40 -61.00   0.00   33
 53  \w    106.00 146.00   1.00    0.84    --  100.40  77.00 -90.00   40
 54  \w     28.00 109.00   1.00    0.84    --  100.40 -94.00 150.00   81
 55  \w     73.00 103.00   1.00    0.84    --  100.40  77.00 -90.00   30
 56  \w     38.00  96.00   1.00    0.84    --  100.40 -94.00 -30.00   58
 57  \w    120.00 156.00   1.00    0.84    --  100.40  77.00-180.00   36
 58  \w     73.00  99.00   1.00    0.84    --  100.40  77.00-180.00   26
 59  \w     28.00 101.00   1.00    0.84    --  100.40 -94.00  90.00   73
 60  \w     96.00 167.00   1.00    0.84    --  100.40  61.00 120.00   71
 61  \w     41.00  66.00   1.00    0.84    --  100.40 -61.00 -90.00   25
 62  \w     73.00 148.00   1.00    0.84    --  100.40  77.00   0.00   75
 63  \w     73.00 168.00   1.00    0.84    --  100.40  77.00  60.00   95
 64  \w     74.00 161.00   1.00    0.84    --  100.40  77.00  30.00   87
 65  \w     73.00 168.00   1.00    0.84    --  100.40  77.00-120.00   95
 66  \w     82.00 159.00   1.00    0.84    --  100.40  61.00-150.00   77
 67  \w     93.00 118.00   1.00    0.84    --  100.40-125.00 -60.00   25
 68  \w     43.00  68.00   1.00    0.84    --  100.40-125.00 -60.00   25
 69  \w     79.00 165.00   1.00    0.84    --  100.40  61.00 150.00   86
;
_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      -0.0713529000
_diffrn_orient_matrix_UB_12      -0.1104698000
_diffrn_orient_matrix_UB_13      0.0409901000
_diffrn_orient_matrix_UB_21      0.1038690000
_diffrn_orient_matrix_UB_22      -0.0903204000
_diffrn_orient_matrix_UB_23      0.0595253000
_diffrn_orient_matrix_UB_31      0.0119268000
_diffrn_orient_matrix_UB_32      0.1253436000
_diffrn_orient_matrix_UB_33      0.0789856000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34812
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.548
_diffrn_reflns_theta_min         3.071
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.21a (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_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2599 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         6005
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0426P)^2^+0.3366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0754
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                5808
_reflns_number_total             6005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01854_si_002.cif
_cod_data_source_block           MP-IV-29(exp_368)
_cod_database_code               4034467
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1BA)
2.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C4B(H4BA,H4BB)
2.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A),
 C2B(H2B), C10B(H10B), C11B(H11B), C12B(H12B), C13B(H13B), C14B(H14B)
2.d X=CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C3B(H3BA,H3BB)
2.e Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C8B(H8BA,H8BB,H8BC)
;
_shelx_res_checksum              75415
_shelx_hkl_checksum              23541
_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 1.148
_oxdiff_exptl_absorpt_empirical_full_min 0.927