Stereochemical control of both C-C and C-N axial chirality in the synthesis of chiral N,O-biaryls.
Oppenheimer, Jossian; Hsung, Richard P.; Figueroa, Ruth; Johnson, Whitney L.; Organic letters 9 (2007) 3969–3972; doi:10.1021/ol701692m

data_1505534
_publ_section_title
;
 Stereochemical control of both C-C and C-N axial chirality in the
 synthesis of chiral N,O-biaryls.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              3969
_journal_page_last               3972
_journal_paper_doi               10.1021/ol701692m
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H47 N O10 S'
_chemical_formula_sum            'C38 H47 N O10 S'
_chemical_formula_weight         709.83
_chemical_name_common            07026
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   9.8046(8)
_cell_length_b                   14.0001(12)
_cell_length_c                   26.276(2)
_cell_measurement_reflns_used    3347
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.87
_cell_measurement_theta_min      2.65
_cell_volume                     3606.8(5)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            42430
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_correction_T_min  0.9160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
'Flack H D (1983), 3613 Friedel Pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         8240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0784P)^2^+1.4953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                7334
_reflns_number_total             8240
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol701692m-file004.cif
_cod_data_source_block           07026
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1505534