Stereoselective Synthesis of 2-Carbamoyl-2-cyanocyclopropanecarboxylates by Tandem Oxidative Cyclization and Neighboring Group-Assisted Decarboxylation
Hua Wang; Renhua Fan; Journal of Organic Chemistry 75 (2010) 6994–6997; doi:10.1021/jo1014245

data_4025731
_publ_section_title
;
 Stereoselective Synthesis of 2-Carbamoyl-2-cyanocyclopropanecarboxylates
 by Tandem Oxidative Cyclization and Neighboring Group-Assisted
 Decarboxylation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6994
_journal_page_last               6997
_journal_paper_doi               10.1021/jo1014245
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C21 H17 F3 N2 O3'
_chemical_formula_weight         402.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.004(7)
_cell_angle_beta                 89.676(7)
_cell_angle_gamma                74.236(7)
_cell_formula_units_Z            2
_cell_length_a                   9.137(5)
_cell_length_b                   9.805(5)
_cell_length_c                   11.580(6)
_cell_measurement_reflns_used    639
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.234
_cell_measurement_theta_min      2.703
_cell_volume                     998.3(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4160
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        4.76
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       layer
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.008(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.709
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.715
_refine_ls_R_factor_all          0.1973
_refine_ls_R_factor_gt           0.1500
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4211
_refine_ls_wR_factor_ref         0.4925
_reflns_number_gt                1957
_reflns_number_total             3452
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1014245_si_002.cif
_cod_data_source_block           a00618b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        998.4(9)
_cod_database_code               4025731