Asymmetric Organocatalytic Approach to 2,4-Disubstituted 1,2,3-Triazoles by N2-Selective Aza-Michael Addition.
Bhagat, Ujjawal Kumar; Peddinti, Rama Krishna; The Journal of organic chemistry 83 (2018) 793–804; doi:10.1021/acs.joc.7b02793

data_4033346
_publ_section_title
;
 Asymmetric Organocatalytic Approach to 2,4-Disubstituted 1,2,3-Triazoles
 by N2-Selective Aza-Michael Addition.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              793
_journal_page_last               804
_journal_paper_doi               10.1021/acs.joc.7b02793
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C14 H14 Cl N3 O'
_chemical_formula_sum            'C14 H14 Cl N3 O'
_chemical_formula_weight         275.73
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2637(3)
_cell_length_b                   7.1660(4)
_cell_length_c                   29.5658(13)
_cell_measurement_reflns_used    5339
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.55
_cell_measurement_theta_min      2.76
_cell_volume                     1327.08(11)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            17459
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.322
_diffrn_reflns_theta_min         1.377
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 882 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0461P)^2^+0.3459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                2630
_reflns_number_total             3263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02793_si_003.cif
_cod_data_source_block           ups2828rkp_ukb_epo_809_0m
_cod_depositor_comments          'Adding full bibliography for 4033346.cif.'
_cod_database_code               4033346
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.905
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_shelx_res_checksum              39577
_shelx_hkl_checksum              64679
_olex2_submission_special_instructions 'No special instructions were received'