Metalated Nitriles: Internal 1,2-Asymmetric Induction
Fleming, Fraser F.; Liu, Wang; Ghosh, Somraj; Steward, Omar W.; The Journal of Organic Chemistry 73 (2008) 2803–2810; doi:10.1021/jo702681e

data_4028908
_publ_section_title
;
 Metalated Nitriles:&#x00A0; Internal 1,2-Asymmetric Induction
;
_journal_issue                   7
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              2803
_journal_page_last               2810
_journal_paper_doi               10.1021/jo702681e
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C17 H20 N2 O4'
_chemical_formula_sum            'C17 H20 N2 O4'
_chemical_formula_weight         316.35
_chemical_melting_point          349.0(10)
_chemical_name_systematic
; 
 (2R,3R,E)-2-cyano-2,3,4-trimethylhex-4-enyl 4-nitrobenzoate 
;
_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   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            8
_cell_length_a                   14.316(11)
_cell_length_b                   7.443(6)
_cell_length_c                   31.78(3)
_cell_measurement_temperature    296(2)
_cell_volume                     3386(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0921
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4850
_diffrn_reflns_theta_full        18.84
_diffrn_reflns_theta_max         18.84
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         1332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0436
_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^)+(0.1000P)^2^+0.1474P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1517
_reflns_number_gt                1084
_reflns_number_total             1332
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702681esup1.cif
_cod_data_source_block           som010
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '348 - 350 k' was changed to
'349.0(10)' - the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4028908