Oxonitriles: a grignard addition-acylation route to enamides.
Fleming, Fraser F.; Wei, Guoqing; Zhang, Zhiyu; Steward, Omar W.; Organic letters 8 (2006) 4903–4906; doi:10.1021/ol0619765

data_1506235
_publ_section_title
;
 Oxonitriles: a grignard addition-acylation route to enamides.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4903
_journal_page_last               4906
_journal_paper_doi               10.1021/ol0619765
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C25 H31 N O2'
_chemical_formula_sum            'C25 H31 N O2'
_chemical_formula_weight         377.51
_chemical_melting_point          398.8(8)
_chemical_name_systematic
;
N-((Z)-1-((2R,3S)-3-hydroxy-3-methyl-2-
phenylcyclohexylidene)(phenyl)methyl)valamide 
;
_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_date             'Mar. 30, 2006'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.6690(10)
_cell_angle_beta                 96.0060(10)
_cell_angle_gamma                106.5260(10)
_cell_formula_units_Z            6
_cell_length_a                   10.10000(10)
_cell_length_b                   17.0482(2)
_cell_length_c                   20.4921(2)
_cell_measurement_reflns_used    11063
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.6
_cell_measurement_theta_min      2.3
_cell_volume                     3247.31(7)
_computing_cell_refinement       'SMART (Bruker 1998)'
_computing_data_collection       'SMART (Bruker 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Shedrick, 2000)'
_computing_publication_material  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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart ApexII'
_diffrn_measurement_method       '\f amd \w 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  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            48940
_diffrn_reflns_theta_full        24.73
_diffrn_reflns_theta_max         24.73
_diffrn_reflns_theta_min         1.04
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         11063
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS sheldrick,2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     772
_refine_ls_number_reflns         11063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0440
_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^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                7347
_reflns_number_total             11063
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0619765si20060809_034237.cif
_cod_data_source_block           one_ffgw009
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '398.0- 399.5 K' was changed to
'398.8(8)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3247.31(6)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506235