Rh(II)-Catalyzed Cyclopropanation of Furans and Its Application to the Total Synthesis of Natural Product Derivatives.
Lehner, Verena; Davies, Huw M. L.; Reiser, Oliver; Organic letters 19 (2017) 4722–4725; doi:10.1021/acs.orglett.7b02009

data_1547562
_publ_section_title
;
 Rh(II)-Catalyzed Cyclopropanation of Furans and Its Application to the
 Total Synthesis of Natural Product Derivatives.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4722
_journal_page_last               4725
_journal_paper_doi               10.1021/acs.orglett.7b02009
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H14 O5'
_chemical_formula_sum            'C15 H14 O5'
_chemical_formula_weight         274.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.4900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4819(2)
_cell_length_b                   5.77330(10)
_cell_length_c                   14.4387(2)
_cell_measurement_reflns_used    12947
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.2170
_cell_measurement_theta_min      5.5560
_cell_volume                     1317.40(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.2047
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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   -116.00 -20.00   1.00    1.00    --  -43.98 -37.00 -60.00   96
  2  \w    -70.00  26.00   1.00    1.00    --  -43.98  57.00  90.00   96
  3  \w     18.00 114.00   1.00    1.00    --   43.98  57.00  90.00   96
  4  \w      2.00  97.00   1.00    1.00    --   43.98-125.00 -60.00   95
  5  \w     15.00  45.00   1.00    1.00    --   48.00  82.00 -91.75   30
  6  \w     24.00 119.00   1.00    1.00    --   48.00  43.00 -33.17   95
  7  \w     16.00  46.00   1.00    1.00    --   48.00  80.00 172.10   30
  8  \w     20.00  46.00   1.00    1.00    --   52.00  80.00 -28.93   26
  9  \w     20.00  47.00   1.00    1.00    --   52.00  79.00  41.33   27
 10  \w     19.00  45.00   1.00    1.00    --   52.00  82.00 105.96   26
 11  \w     20.00  47.00   1.00    1.00    --   52.00  79.00-114.23   27
 12  \w     29.00 133.00   1.00    1.00    --   60.00  75.00-104.33  104
 13  \w     34.00 137.00   1.00    1.00    --   64.00  73.00  59.33  103
 14  \w     36.00 142.00   1.00    1.00    --   68.00  77.00 -83.41  106
 15  \w     37.00 142.00   1.00    1.00    --   68.00  76.00-170.45  105
 16  \w     40.00 146.00   1.00    1.00    --   72.00  77.00 132.39  106
 17  \w     40.00 146.00   1.00    1.00    --   72.00  77.00 116.55  106
 18  \w     45.00 142.00   1.00    1.00    --   72.00  63.00 -29.85   97
 19  \w     45.00 149.00   1.00    3.00    --   76.00  75.00  27.86  104
 20  \w     50.00 146.00   1.00    3.00    --   76.00  60.00-110.10   96
 21  \w     45.00 150.00   1.00    3.00    --   76.00  76.00 -36.01  105
 22  \w     44.00 150.00   1.00    3.00    --   76.00  77.00 179.74  106
 23  \w     49.00 153.00   1.00    3.00    --   80.00  75.00  23.71  104
 24  \w     65.00 162.00   1.00    3.00    --   92.00  63.00-167.72   97
 25  \w     66.00 169.00   1.00    3.00    --   96.00  73.00  72.49  103
 26  \w     73.00 178.00   1.00    3.00    --  104.50  77.00  90.00  105
 27  \w     73.00 178.00   1.00    3.00    --  104.50  77.00-180.00  105
 28  \w     73.00 178.00   1.00    3.00    --  104.50  77.00 -90.00  105
 29  \w     73.00 178.00   1.00    3.00    --  104.50  77.00-120.00  105
 30  \w     73.00 178.00   1.00    3.00    --  104.50  77.00 -60.00  105
 31  \w     80.00 175.00   1.00    3.00    --  104.50  45.00 150.00   95
 32  \w     73.00 178.00   1.00    3.00    --  104.50  77.00   0.00  105
 33  \w     78.00 174.00   1.00    3.00    --  104.50  61.00  60.00   96
 34  \w     73.00 178.00   1.00    3.00    --  104.50  77.00 -30.00  105
 35  \w     78.00 174.00   1.00    3.00    --  104.50  61.00 150.00   96
 36  \w     21.00 109.00   1.00    3.00    --  104.50 -94.00   0.00   88
 37  \w     73.00 178.00   1.00    3.00    --  104.50  77.00-150.00  105
 38  \w     73.00 178.00   1.00    3.00    --  104.50  77.00  30.00  105
 39  \w     30.00 136.00   1.00    3.00    --  104.50 -77.00  60.00  106
 40  \w     21.00 109.00   1.00    3.00    --  104.50 -94.00-150.00   88
 41  \w     31.00 121.00   1.00    3.00    --  104.50-125.00 -30.00   90
 42  \w     18.00 114.00   1.00    1.00    --   43.98  57.00-180.00   96
 43  \w     12.00 118.00   1.00    1.00    --   43.98  77.00 -30.00  106
 44  \w     20.00  47.00   1.00    1.00    --   52.00  79.00  87.36   27
 45  \w     25.00 129.00   1.00    1.00    --   56.00  75.00 -14.88  104
 46  \w     26.00 128.00   1.00    1.00    --   56.00  71.00  21.46  102
 47  \w     35.00 130.00   1.00    1.00    --   60.00  55.00 110.46   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0715202000
_diffrn_orient_matrix_UB_12      -0.0621876000
_diffrn_orient_matrix_UB_13      0.0912159000
_diffrn_orient_matrix_UB_21      0.0660324000
_diffrn_orient_matrix_UB_22      0.0843799000
_diffrn_orient_matrix_UB_23      -0.0494623000
_diffrn_orient_matrix_UB_31      -0.0046562000
_diffrn_orient_matrix_UB_32      0.2454881000
_diffrn_orient_matrix_UB_33      0.0401078000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19381
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.520
_diffrn_reflns_theta_min         5.599
_diffrn_source                   'gradient vaccum rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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 colourless'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1071 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2593
_refine_ls_number_restraints     217
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0452P)^2^+0.3923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                2495
_reflns_number_total             2593
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02009_si_003.cif
_cod_data_source_block           q072
_cod_database_code               1547562
_chemical_oxdiff_formula         'C15 H14 O5'
_chemical_oxdiff_usercomment     Lehner_Reiser_VL150
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H13(0.032) H9(0.034) H8(0.038) H7(0.036) H6(0.031) H5(0.026)
 H11(0.026) H10(0.031) H15A(0.046) H15B(0.046) H15C(0.046) H1A(0.052)
 H1B(0.052) H1C(0.052) H9A(0.032) H8A(0.038) H7A(0.035) H6A(0.032) H5A(0.029)
 H1AA(0.054) H1AB(0.054) H1AC(0.054)
 Fixed X: H13(0.744229) H9(0.540051) H8(0.415685) H7(0.402616) H6(0.513912)
 H5(0.638279) H11(0.818361) H10(0.756705) H15A(0.913184) H15B(0.849612)
 H15C(0.935548) H1A(0.603854) H1B(0.534639) H1C(0.630015) H9A(0.564815)
 H8A(0.443961) H7A(0.41443) H6A(0.505754) H5A(0.626609) H1AA(0.536351)
 H1AB(0.620995) H1AC(0.623026)
 Fixed Y: H13(0.911907) H9(0.719789) H8(0.715659) H7(0.470596) H6(0.229659)
 H5(0.233784) H11(0.405531) H10(0.726081) H15A(0.025922) H15B(0.143546)
 H15C(0.265367) H1A(0.259719) H1B(0.10313) H1C(0.029009) H9A(0.810256)
 H8A(0.816826) H7A(0.509271) H6A(0.195147) H5A(0.188574) H1AA(0.045418) H1AB(-
 0.078772) H1AC(0.141826)
 Fixed Z: H13(0.874763) H9(0.61055) H8(0.655604) H7(0.777905) H6(0.855153)
 H5(0.8101) H11(0.72974) H10(0.617113) H15A(0.997781) H15B(1.045991)
 H15C(1.050002) H1A(0.406447) H1B(0.430157) H1C(0.464507) H9A(0.655532)
 H8A(0.707545) H7A(0.796211) H6A(0.832865) H5A(0.780854) H1AA(0.431979)
 H1AB(0.486591) H1AC(0.423979)
;
_shelx_shelxl_version_number     2016/6
_olex2_date_sample_data_collection 2017-06-02
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.642