Highly Selective Rhodium-Catalyzed Conjugate Addition Reactions of 4-Oxobutenamides
Jamie L. Zigterman; Jacqueline C. S. Woo; Shawn D. Walker; Jason S. Tedrow; Christopher J. Borths; Emilio E. Bunel; Margaret M. Faul; Journal of Organic Chemistry 72 (2007) 8870–8876; doi:10.1021/jo701682c

data_4023074
_publ_section_title
;
 Highly Selective Rhodium-Catalyzed Conjugate Addition Reactions
 of 4-Oxobutenamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8870
_journal_page_last               8876
_journal_paper_doi               10.1021/jo701682c
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C20 H20 Br N O3'
_chemical_formula_weight         402.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_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            4
_cell_length_a                   6.436(2)
_cell_length_b                   11.263(4)
_cell_length_c                   24.913(9)
_cell_measurement_reflns_used    719
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      20.96
_cell_measurement_theta_min      3.05
_cell_volume                     1806.0(11)
_computing_cell_refinement       'SMART (BRUKER, V5.625, 2001)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.22, 2001)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 2000, V6.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '\w, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10188
_diffrn_reflns_theta_full        25.11
_diffrn_reflns_theta_max         25.11
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.294
_exptl_absorpt_correction_T_max  0.9138
_exptl_absorpt_correction_T_min  0.8030
_exptl_absorpt_correction_type   Emppirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0607P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                2536
_reflns_number_total             3223
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701682c-File006.cif
_cod_data_source_block           amg2506t
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4023074