Enantioselective synthesis of 1,2,4-triazolines catalyzed by a cinchona alkaloid-derived organocatalyst
Qian Shao; Jiean Chen; Meihua Tu; David W. Piotrowski; Yong Huang; Chem.Commun. 49 (2013) 11098–; doi:10.1039/c3cc46757k

data_7110043
_publ_section_title
;
 Enantioselective synthesis of 1,2,4-triazolines catalyzed by a cinchona
 alkaloid-derived organocatalyst
;
_journal_name_full               Chem.Commun.
_journal_page_first              11098
_journal_paper_doi               10.1039/c3cc46757k
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H42 N6 O4, C7 H7 O3 S, H2 O'
_chemical_formula_sum            'C43 H51 N6 O8 S'
_chemical_formula_weight         811.95
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8231(3)
_cell_length_b                   25.0117(17)
_cell_length_c                   9.92390(10)
_cell_measurement_reflns_used    25623
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      68.10
_cell_measurement_theta_min      6.70
_cell_volume                     4423.9(3)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28638
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         6.677
_exptl_absorpt_coefficient_mu    1.116
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1724
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.858
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 2527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.031(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.540
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         7924
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.539
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0793
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0908P)^2^+0.7860P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2168
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                6630
_reflns_number_total             7924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc46757k.txt
_cod_data_source_block           shelx
_cod_database_code               7110043
_shelx_estimated_absorpt_t_min   0.760
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2013-2
_shelx_res_checksum              89303
_shelx_hkl_checksum              75395