Stereospecificity and Stereoselectivity in Electrophilic Substitution Reactions of Non-α-Heterosubstituted Organolithiums and Stannanes: A Rotationally Restricted Amide as an Internal Stereochemical Marker
Jonathan Clayden; Madeleine Helliwell; Jennifer H. Pink; Neil Westlund; Journal of the American Chemical Society 123 (2001) 12449–12457; doi:10.1021/ja0112590

data_4115849
_publ_section_title
;
 Stereospecificity and Stereoselectivity in Electrophilic Substitution
 Reactions of Non-\a-Heterosubstituted Organolithiums and Stannanes: A
 Rotationally Restricted Amide as an Internal Stereochemical Marker
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12449
_journal_page_last               12457
_journal_paper_doi               10.1021/ja0112590
_journal_volume                  123
_journal_year                    2001
_chemical_formula_moiety         'C21 H29 N O '
_chemical_formula_sum            'C21 H29 N O'
_chemical_formula_weight         311.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             1997-02-07
_audit_creation_method           'by teXsan v1.7'
_audit_update_record             ?
_cell_angle_alpha                90
_cell_angle_beta                 92.61(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.638(4)
_cell_length_b                   13.286(4)
_cell_length_c                   18.879(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    292.2
_cell_measurement_theta_max      9.9
_cell_measurement_theta_min      7.7
_cell_volume                     1913.8(12)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1995)'
_computing_publication_material  'teXsan (MSC, 1995)'
_computing_structure_refinement  'teXsan (MSC, 1995)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      292.2
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       \w
_diffrn_orient_matrix_UB_11      0.02818
_diffrn_orient_matrix_UB_12      -0.07275
_diffrn_orient_matrix_UB_13      0.00791
_diffrn_orient_matrix_UB_21      -0.00077
_diffrn_orient_matrix_UB_22      0.01065
_diffrn_orient_matrix_UB_23      0.05242
_diffrn_orient_matrix_UB_31      -0.12799
_diffrn_orient_matrix_UB_32      -0.01608
_diffrn_orient_matrix_UB_33      -0.00105
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.01618
_diffrn_reflns_av_sigmaI/netI    0.090
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3845
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.08
_diffrn_standards_decay_%        0.82
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.081
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             680.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   2.316
_refine_ls_goodness_of_fit_obs   2.855
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1995
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_obs          0.0643
_refine_ls_shift/esd_max         0.0000
_refine_ls_shift/esd_mean        0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) +0.00001|Fo|^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0546
_refine_ls_wR_factor_obs         0.0504
_reflns_number_observed          1995
_reflns_number_total             3562
_reflns_observed_criterion       >3.00\s(I)
_cod_data_source_file            ja0112590_1.cif
_cod_data_source_block           S550
_cod_depositor_comments
;
 Removing strange text fragments ('<bigger><bigger>' and '</bigger></bigger>')
 from the GEOM_TORSION loop.

 Antanas Vaitkus,
 2018-08-08

 Renaming the _geom_torsion_site_symmetry_4 data item to _geom_torsion.
 The initial data name misassignment was cause by the incorrect data name
 order in the loop and the removal of data items containing only unknown
 ('?') or inapplicable ('.') values.

 Antanas Vaitkus,
 2018-08-08

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo)
+0.00001|Fo|^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(Fo) +0.00001|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1913(1)
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_original_formula_sum        'C21 H29 N O '
_cod_database_code               4115849