Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.
Di Mauro, Giovanni; Maryasin, Boris; Kaiser, Daniel; Shaaban, Saad; González, Leticia; Maulide, Nuno; Organic letters 19 (2017) 3815–3818; doi:10.1021/acs.orglett.7b01678

data_1546529
_publ_section_title
;
 Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles
 and Imidazoles.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3815
_journal_page_last               3818
_journal_paper_doi               10.1021/acs.orglett.7b01678
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C26 H27 N3 O2 S'
_chemical_formula_sum            'C26 H27 N3 O2 S'
_chemical_formula_weight         445.56
_chemical_name_systematic
;
N,N-Dibenzyl-1,2-dimethyl-5-tosyl-1H-imidazol-4-amine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                78.305(3)
_cell_angle_beta                 78.596(3)
_cell_angle_gamma                73.067(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3234(9)
_cell_length_b                   9.9427(10)
_cell_length_c                   13.0102(13)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.580
_cell_measurement_theta_min      5.017
_cell_volume                     1117.35(19)
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17436
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.897
_diffrn_reflns_theta_min         5.014
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSCu'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.513
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.1141 before and 0.0436 after correction. 
The Ratio of minimum to maximum transmission is 0.7452. 
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.816
_exptl_crystal_size_mid          0.561
_exptl_crystal_size_min          0.404
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+0.5788P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4244
_reflns_number_total             4389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01678_si_001.cif
_cod_data_source_block           cu_daka1040_p-1
_cod_depositor_comments          'Adding full bibliography for 1546529.cif.'
_cod_database_code               1546529
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.580
_shelx_estimated_absorpt_t_min   0.372