Organocatalytic synthesis of enantioenriched 1,2,4-triazolines containing a chiral quaternary carbon center
Zhang, Li-Jun; Zhang, Si-Xiang; Fu, Li-Na; Li, Xiao-Yun; Guo, Qi-Xiang; RSC Adv. 7 (2017) 18714–; doi:10.1039/C6RA28800F

data_7228754
_publ_section_title
;
 Organocatalytic synthesis of enantioenriched 1,2,4-triazolines containing
 a chiral quaternary carbon center
;
_journal_issue                   30
_journal_name_full               'RSC Adv.'
_journal_page_first              18714
_journal_paper_doi               10.1039/C6RA28800F
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C26 H36 Cl N5 O10 S'
_chemical_formula_sum            'C26 H37 Cl N6 O9 S'
_chemical_formula_weight         645.12
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-01-14 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.506(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3480(5)
_cell_length_b                   15.6841(6)
_cell_length_c                   10.7299(5)
_cell_measurement_reflns_used    9647
_cell_measurement_temperature    289.48(10)
_cell_measurement_theta_max      71.2550
_cell_measurement_theta_min      4.5600
_cell_volume                     1641.50(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      289.48(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -32.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203  -77.0000   60.0000 94

  2 omega   16.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203   38.0000  150.0000 88

  3 omega  -32.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203  -57.0000  -60.0000 84

  4 omega   18.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203   57.0000  -90.0000 84

  5 omega  -32.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203  -77.0000 -180.0000 94

  6 omega    1.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203  -99.0000  -60.0000 73

  7 omega    1.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203  -99.0000 -180.0000 73

  8 omega   57.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203  178.0000  -30.0000 50

  9 omega   16.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203   38.0000 -120.0000 88

 10 omega   91.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 85

 11 omega   37.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -180.0000 109

 12 omega   39.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000 -150.0000 71

 13 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 14 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 15 omega   38.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000   60.0000 78

 16 omega   39.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  -60.0000 71

 17 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 18 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 19 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 20 omega   18.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203   57.0000   30.0000 84

 21 omega  -32.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203  -57.0000   90.0000 84

 22 omega    8.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203   77.0000  150.0000 95

 23 omega   18.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203   57.0000  -30.0000 84

 24 omega    8.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203   77.0000   60.0000 95

 25 omega   57.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203  178.0000   90.0000 50

 26 omega    8.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203   77.0000 -120.0000 95

 27 omega    8.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203   77.0000  -30.0000 95

 28 omega    8.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203   77.0000 -180.0000 95

 29 omega  -34.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2203  -38.0000 -150.0000 88

 30 omega   40.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 35

 31 omega   39.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   30.0000 138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0934313000
_diffrn_orient_matrix_UB_12      0.0045319000
_diffrn_orient_matrix_UB_13      0.0854662000
_diffrn_orient_matrix_UB_21      -0.1272618000
_diffrn_orient_matrix_UB_22      0.0010087000
_diffrn_orient_matrix_UB_23      -0.1260207000
_diffrn_orient_matrix_UB_31      -0.0054621000
_diffrn_orient_matrix_UB_32      -0.0981224000
_diffrn_orient_matrix_UB_33      0.0025853000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15049
_diffrn_reflns_point_group_measured_fraction_full 0.747
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.371
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             680
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1319 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4433
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0553P)^2^+0.7706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.451
_reflns_Friedel_fraction_full    0.483
_reflns_Friedel_fraction_max     0.488
_reflns_number_gt                4323
_reflns_number_total             4433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra28800f2.cif
_cod_data_source_block           guoqx20140926
_cod_database_code               7228754
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1 Cl1'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C35(H35), C29(H29), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 N14(H14), C6(H6), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C36(H36A,H36B,H36C), C31(H31A,H31B,H31C), C23(H23A,H23B,
 H23C), C18(H18A,H18B,H18C), C41(H41A,H41B,H41C), C37(H37A,H37B,H37C), C19(H19A,
 H19B,H19C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'