Atroposelectivity in the electrophilic substitution reactions of laterally lithiated and silylated tertiary amides
Clayden, Jonathan; Pink, Jennifer H.; Westlund, Neil; Frampton, Christopher S.; Journal of the Chemical Society, Perkin Transactions 1  (2002) 901–; doi:10.1039/b200358a

data_7213537
_publ_section_title
;
 Atroposelectivity in the electrophilic substitution reactions of
 laterally lithiated and silylated tertiary amides
;
_journal_issue                   7
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              901
_journal_paper_doi               10.1039/b200358a
_journal_year                    2002
_chemical_formula_sum            'C26 H29 N O2'
_chemical_formula_weight         387.50
_chemical_name_common
;
RWX0315/Wilson/NW-C076-2/5107/28-9-98.
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 99.39(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4893(18)
_cell_length_b                   13.585(4)
_cell_length_c                   11.005(4)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      1.88
_cell_volume                     1104.7(6)
_computing_cell_refinement       'SMART V5 & SAINT V5 (Bruker AXS, 1997)'
_computing_data_collection       'SMART V5 (Bruker AXS, 1997)'
_computing_data_reduction        'SAINT V5 (Bruker AXS, 1997)'
_computing_molecular_graphics    'SHELXTL V5.10 (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL V5.10 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXTL V5.10 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL V5.10 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(1)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS 1K SMART CCD area detector'
_diffrn_measurement_method       'narrow frame 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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11086
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        none
_diffrn_standards_number         'see text'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Off white'
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 Abolute structure not determined'
_refine_ls_abs_structure_Flack   0.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4494
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0600P)^2^+0.0600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                4153
_reflns_number_total             4494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b200358asup1.cif
_cod_data_source_block           0331s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1104.7(5)
_cod_original_sg_symbol_H-M      P21
_cod_original_formula_sum        'C26 H29 N1 O2'
_cod_database_code               7213537