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_1547560
_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_formula_moiety         'C14 H16 O4'
_chemical_formula_sum            'C14 H16 O4'
_chemical_formula_weight         248.27
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2017-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.364(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.22602(16)
_cell_length_b                   15.4712(3)
_cell_length_c                   10.0483(2)
_cell_measurement_reflns_used    7562
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.3920
_cell_measurement_theta_min      4.4540
_cell_volume                     1244.18(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.37b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.37b (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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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 -17.00   1.00    5.00    --  -41.23 -37.00-180.00   99
  2  \w    -35.00  74.00   1.00    5.00    --   41.23 -77.00  90.00  109
  3  \w    -20.00  82.00   1.00    5.00    --   41.23 -99.00 -30.00  102
  4  \w     77.00 158.00   1.00   20.00    --  106.46  61.00-180.00   81
  5  \w     30.00  69.00   1.00   20.00    --  106.46 -30.00 150.00   39
  6  \w     30.00  69.00   1.00   20.00    --  106.46 -30.00  90.00   39
  7  \w     81.00 158.00   1.00   20.00    --  106.46  45.00  30.00   77
  8  \w     33.00  77.00   1.00   20.00    --  106.46 -45.00  30.00   44
  9  \w     30.00  69.00   1.00   20.00    --  106.46 -30.00 -90.00   39
 10  \w     30.00  69.00   1.00   20.00    --  106.46 -30.00-120.00   39
 11  \w     77.00 158.00   1.00   20.00    --  106.46  61.00-150.00   81
 12  \w     73.00 158.00   1.00   20.00    --  106.46 125.00  30.00   85
 13  \w     81.00 158.00   1.00   20.00    --  106.46  45.00 -90.00   77
 14  \w     77.00 158.00   1.00   20.00    --  106.46  61.00 150.00   81
 15  \w     33.00  77.00   1.00   20.00    --  106.46 -45.00-180.00   44
 16  \w     77.00 158.00   1.00   20.00    --  106.46  61.00-120.00   81
 17  \w     33.00  77.00   1.00   20.00    --  106.46 -45.00  60.00   44
 18  \w     33.00 121.00   1.00   20.00    --  106.46-125.00  90.00   88
 19  \w    -97.00  -2.00   1.00    5.00    --  -41.23 125.00 150.00   95
 20  \w   -114.00 -13.00   1.00    5.00    --  -41.23 -57.00 -90.00  101
 21  \w   -117.00  -9.00   1.00    5.00    --  -41.23 -77.00  30.00  108
 22  \w   -114.00 -13.00   1.00    5.00    --  -41.23 -57.00  90.00  101
 23  \w     24.00 109.00   1.00   20.00    --  106.46 -94.00-180.00   85
 24  \w     77.00 158.00   1.00   20.00    --  106.46  61.00  90.00   81
 25  \w     77.00 158.00   1.00   20.00    --  106.46  61.00 -30.00   81
 26  \w     81.00 158.00   1.00   20.00    --  106.46  45.00 -60.00   77
 27  \w     77.00 102.00   1.00   20.00    --  106.46  61.00  60.00   25
 28  \w     30.00 139.00   1.00   20.00    --  106.46 -77.00 -90.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0324776000
_diffrn_orient_matrix_UB_12      -0.0338144000
_diffrn_orient_matrix_UB_13      -0.1480429000
_diffrn_orient_matrix_UB_21      -0.1380471000
_diffrn_orient_matrix_UB_22      -0.0599590000
_diffrn_orient_matrix_UB_23      0.0278002000
_diffrn_orient_matrix_UB_31      -0.1301303000
_diffrn_orient_matrix_UB_32      0.0719345000
_diffrn_orient_matrix_UB_33      -0.0463905000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15266
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.436
_diffrn_reflns_theta_min         5.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.37b (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0344P)^2^+0.4215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2235
_reflns_number_total             2480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02009_si_005.cif
_cod_data_source_block           p165
_cod_original_cell_volume        1244.17(4)
_cod_database_code               1547560
_chemical_oxdiff_formula         'C14 H16 O4'
_chemical_oxdiff_usercomment     Lehner_Reiser_VL203/2
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-10-19
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems, CryoStream 700'
_olex2_submission_original_sample_id 'P165 (VL203/2)'
_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 1.138
_oxdiff_exptl_absorpt_empirical_full_min 0.902