Diastereoselective synthesis of atropisomers containing two non-biaryl stereogenic axes: stereochemical relay through stereogenic centres in dihydrostilbene-2,2'-dicarboxamides.
Clayden, Jonathan; Westlund, Neil; Frampton, Christopher S.; Helliwell, Madeleine; Organic & biomolecular chemistry 4 (2006) 455–461; doi:10.1039/b514561a

data_7150404
_publ_section_title
;
 Diastereoselective synthesis of atropisomers containing two non-biaryl
 stereogenic axes: stereochemical relay through stereogenic centres in
 dihydrostilbene-2,2'-dicarboxamides.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              455
_journal_page_last               461
_journal_paper_doi               10.1039/b514561a
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C38 H51 N3 O2'
_chemical_formula_weight         581.82
_chemical_name_common            RWX0315/Wilson/NW-G020/5107/25-9-98.
_chemical_name_systematic
;
?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   15.179(3)
_cell_length_b                   7.728(2)
_cell_length_c                   28.337(6)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      1.44
_cell_volume                     3324.0(13)
_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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            32058
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        0
_diffrn_standards_number         'see text'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Off white'
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
Flack H D (1983), Acta Cryst. A39, 876-881, Absolute structure not
determined
;
_refine_ls_abs_structure_Flack   -1.0(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6795
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0866P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                5943
_reflns_number_total             6795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b514561a.txt
_cod_data_source_block           0330n
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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        3324.3(12)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7150404