Rhodium-catalyzed [2 + 2] cycloaddition of ynamides with nitroalkenes.
Smith, Donna L.; Chidipudi, Suresh Reddy; Goundry, William R.; Lam, Hon Wai; Organic letters 14 (2012) 4934–4937; doi:10.1021/ol302259v

data_1508663
_publ_section_title
;
 Rhodium-catalyzed [2 + 2] cycloaddition of ynamides with nitroalkenes.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4934
_journal_page_last               4937
_journal_paper_doi               10.1021/ol302259v
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C19 H15 F N2 O4'
_chemical_formula_sum            'C19 H15 F N2 O4'
_chemical_formula_weight         354.33
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0313(3)
_cell_length_b                   9.5234(2)
_cell_length_c                   31.3481(8)
_cell_measurement_reflns_used    5832
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.7747
_cell_measurement_theta_min      2.8169
_cell_volume                     3293.29(14)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2011)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.1574
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            12433
_diffrn_reflns_theta_full        73.93
_diffrn_reflns_theta_max         73.93
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  0.9335
_exptl_absorpt_correction_T_min  0.8428
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'CrysAlisPro; Agilent Technologies, 2011'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0491P)^2^+0.8012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                2860
_reflns_number_total             3286
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol302259v_si_001.cif
_cod_data_source_block           hl1009
_cod_database_code               1508663