Rhodium-catalyzed highly enantio- and diastereoselective cotrimerization of alkenes and dialkyl acetylenedicarboxylates leading to furylcyclopropanes.
Shibata, Yu; Noguchi, Keiichi; Hirano, Masao; Tanaka, Ken; Organic letters 10 (2008) 2825–2828; doi:10.1021/ol800966f

data_1504733
_publ_section_title
;
 Rhodium-catalyzed highly enantio- and diastereoselective cotrimerization
 of alkenes and dialkyl acetylenedicarboxylates leading to
 furylcyclopropanes.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2825
_journal_page_last               2828
_journal_paper_doi               10.1021/ol800966f
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C17 H19 Br N4 O8), 0.5(C H4 O)'
_chemical_formula_sum            'C17.25 H20 Br N4 O8.25'
_chemical_formula_weight         495.28
_chemical_name_systematic
;
 2,4-dinitro phenyl hydorazone of (+)-2-(3-Bromopropyl)-
 1-methoxyoxalylcyclopropanecarboxylic acid methyl ester 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.2780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.6745(6)
_cell_length_b                   6.89073(12)
_cell_length_c                   18.7222(3)
_cell_measurement_reflns_used    35978
_cell_measurement_temperature    193
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.5
_cell_volume                     4208.43(13)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37967
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    3.149
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.387
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2020
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 3267 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.024(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         7469
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+3.4037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                6830
_reflns_number_total             7469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800966f-file002.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C34.50 H40 Br2 N8 O16.50'
_cod_database_code               1504733