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_1547561
_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 syn
_chemical_formula_moiety         'C13 H12 O3'
_chemical_formula_sum            'C13 H12 O3'
_chemical_formula_weight         216.23
_chemical_name_systematic        Q075
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1779(2)
_cell_length_b                   8.8079(2)
_cell_length_c                   15.2085(3)
_cell_measurement_reflns_used    7067
_cell_measurement_temperature    122.99(10)
_cell_measurement_theta_max      66.2810
_cell_measurement_theta_min      5.4350
_cell_volume                     1095.47(4)
_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      122.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3546
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     11.00 115.00   1.00    1.00    --   40.89  57.00 -30.00  104
  2  \w      2.00  98.00   1.00    1.00    --   40.89-125.00-180.00   96
  3  \w   -157.00 -53.00   1.00    1.00    --  -83.00 -61.00-120.00  104
  4  \w     62.00 158.00   1.00    1.00    --   92.64  61.00-120.00   96
  5  \w     18.00 121.00   1.00    1.00    --   92.64-125.00 150.00  103
  6  \w     65.00 158.00   1.00    1.00    --   92.64  45.00 -30.00   93
  7  \w     18.00  77.00   1.00    1.00    --   92.64 -45.00 150.00   59
  8  \w     18.00  76.00   1.00    1.00    --   92.64 -44.00  11.00   58
  9  \w     59.00 158.00   1.00    1.00    --   92.64  77.00 -90.00   99
 10  \w     14.00 126.00   1.00    1.00    --   92.64 -77.00 150.00  112
 11  \w     18.00  77.00   1.00    1.00    --   92.64 -45.00-150.00   59
 12  \w      8.00 109.00   1.00    1.00    --   92.64 -94.00  30.00  101
 13  \w     11.00 115.00   1.00    1.00    --   40.89  57.00 150.00  104
 14  \w     11.00 115.00   1.00    1.00    --   40.89  57.00  60.00  104
 15  \w   -162.00-129.00   1.00    1.00    --  -83.00 -77.00-150.00   33
 16  \w   -162.00 -49.00   1.00    1.00    --  -83.00 -77.00-180.00  113
 17  \w     59.00 158.00   1.00    1.00    --   92.64  77.00  60.00   99
 18  \w     18.00 121.00   1.00    1.00    --   92.64-125.00   0.00  103
 19  \w     65.00 158.00   1.00    1.00    --   92.64  45.00 120.00   93
 20  \w     62.00 158.00   1.00    1.00    --   92.64  61.00   0.00   96
 21  \w     62.00 158.00   1.00    1.00    --   92.64  61.00  30.00   96
;
_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      0.1266315000
_diffrn_orient_matrix_UB_12      -0.0050359000
_diffrn_orient_matrix_UB_13      0.0750304000
_diffrn_orient_matrix_UB_21      0.1151031000
_diffrn_orient_matrix_UB_22      -0.0950457000
_diffrn_orient_matrix_UB_23      -0.0583062000
_diffrn_orient_matrix_UB_31      0.0790267000
_diffrn_orient_matrix_UB_32      0.1465728000
_diffrn_orient_matrix_UB_33      -0.0351642000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13735
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.531
_diffrn_reflns_theta_max         66.531
_diffrn_reflns_theta_min         5.805
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.543
_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_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.101
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 739 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(8)
_refine_ls_extinction_coef       0.0057(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0240
_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^)+(0.0336P)^2^+0.1245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0611
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1846
_reflns_number_total             1920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02009_si_004.cif
_cod_data_source_block           q075_1
_cod_database_code               1547561
_chemical_oxdiff_formula         'C13 H12 O2'
_chemical_oxdiff_usercomment     Lehner_Reiser_VL286
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_olex2_refinement_description
;
;
_shelx_shelxl_version_number     2016/6
_olex2_date_sample_completion    2017-06-16
_olex2_date_sample_data_collection 2017-06-14
_olex2_date_sample_submission    2017-06-12
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems, CryoStream 700'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id 'VL 286'
_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 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.725