Electrophile-Dependent Alkylations of Lithiated 4-Alkoxyalk-4-enenitriles.
Pitta, Bhaskar R.; Steward, Omar W.; Fleming, Fraser F.; The Journal of organic chemistry 83 (2018) 2753–2762; doi:10.1021/acs.joc.7b03205

data_4034977
_publ_section_title
;
 Electrophile-Dependent Alkylations of Lithiated
 4-Alkoxyalk-4-enenitriles.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2753
_journal_page_last               2762
_journal_paper_doi               10.1021/acs.joc.7b03205
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C23 H24 N2 O5'
_chemical_formula_sum            'C23 H24 N2 O5'
_chemical_formula_weight         408.44
_chemical_melting_point          352.2(8)
_chemical_name_systematic
; 
(2S,3R)-4-(benzoyloxy)-2-cyano-
2-ethyl-3-methylpent-4-en-1-yl 4-nitrobenzoate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'Jan. 7 2011'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.237(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.4903(10)
_cell_length_b                   6.4729(3)
_cell_length_c                   14.3144(7)
_cell_measurement_reflns_used    24541
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.0
_cell_measurement_theta_min      2.4
_cell_volume                     2118.68(17)
_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 and \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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24542
_diffrn_reflns_theta_full        19.07
_diffrn_reflns_theta_max         19.07
_diffrn_reflns_theta_min         0.89
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         1714
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.432
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         1714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.432
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                1449
_reflns_number_total             1714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03205_si_001.cif
_cod_data_source_block           ffbrp2c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '351.5-353.0 K ' was
changed to '352.2(8)' -- the average value was taken and precision
was estimated.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      ' P21/c'
_cod_database_code               4034977