Atropisomerism in the 2-Arylimino-N-(2-hydroxyphenyl)thiazoline Series: Influence of Hydrogen Bonding on the Racemization Process
Christian Roussel; Nicolas Vanthuyne; Mohamed Bouchekara; Ayada Djafri; José Elguero; Ibon Alkorta; Journal of Organic Chemistry 73 (2008) 403–411; doi:10.1021/jo701756u

data_4023193
_publ_section_title
;
 Atropisomerism in the 2-Arylimino-N-(2-hydroxyphenyl)thiazoline
 Series: Influence of Hydrogen Bonding on the Racemization Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              403
_journal_page_last               411
_journal_paper_doi               10.1021/jo701756u
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C19 H18 N2 O2 S'
_chemical_formula_weight         338.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 93.455(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   9.6170(6)
_cell_length_b                   7.2900(2)
_cell_length_c                   23.937(1)
_cell_measurement_reflns_used    3363
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.12
_cell_volume                     1675.1(1)
_computing_cell_refinement       'Denzo and Scalepak (Otwinowski&Minor, 1997)'
_computing_data_collection       'KappaCCD (Nonius, 1998)'
_computing_data_reduction        'Denzo and Scalepak (Otwinowski&Minor, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Phi scan'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            3139
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+0.5276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1495
_reflns_number_gt                2720
_reflns_number_total             3139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701756u-File003.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023193