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_1547559
_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           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.4716(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.82867(19)
_cell_length_b                   6.11703(12)
_cell_length_c                   11.6406(2)
_cell_measurement_reflns_used    11164
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      63.9850
_cell_measurement_theta_min      4.5580
_cell_volume                     688.20(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2548
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0666296000
_diffrn_orient_matrix_UB_12      0.1091050000
_diffrn_orient_matrix_UB_13      -0.0954931000
_diffrn_orient_matrix_UB_21      0.1360252000
_diffrn_orient_matrix_UB_22      0.0289480000
_diffrn_orient_matrix_UB_23      0.0882073000
_diffrn_orient_matrix_UB_31      0.0497382000
_diffrn_orient_matrix_UB_32      -0.2250275000
_diffrn_orient_matrix_UB_33      -0.0349340000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14187
_diffrn_reflns_theta_full        64.18
_diffrn_reflns_theta_max         64.18
_diffrn_reflns_theta_min         3.86
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.836
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.3063
_exptl_crystal_size_mid          0.1966
_exptl_crystal_size_min          0.0822
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.0434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                2184
_reflns_number_total             2224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b02009_si_002.cif
_cod_data_source_block           n053
_cod_database_code               1547559
_chemical_oxdiff_formula         'C15 H14 O5'
_reflns_odcompleteness_completeness 96.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.84
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C13(H13), C12(H12), C2(H2), C14(H14)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C7(H7A,H7B,H7C)
;