Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes.
Esteban, Francisco; Cieślik, Wioleta; Arpa, Enrique M.; Guerrero-Corella, Andrea; Díaz-Tendero, Sergio; Perles, Josefina; Fernández-Salas, José A; Fraile, Alberto; Alemán, José; ACS catalysis 8 (2018) 1884–1890; doi:10.1021/acscatal.7b03553

data_4514381
_publ_section_title
;
 Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed
 Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived
 Azomethine Ylides with Nitroalkenes.
;
_journal_issue                   3
_journal_name_full               'ACS catalysis'
_journal_page_first              1884
_journal_page_last               1890
_journal_paper_doi               10.1021/acscatal.7b03553
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H20 Cl N O4'
_chemical_formula_weight         373.82
_chemical_name_common            AGC-247
_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   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.027(4)
_cell_length_b                   10.076(3)
_cell_length_c                   20.280(8)
_cell_measurement_reflns_used    4155
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      21.7639
_cell_measurement_theta_min      2.2539
_cell_volume                     1844.6(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19368
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.248
_refine_ls_abs_structure_details
;

Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0653
_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^)+(0.0465P)^2^+0.2754P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                2632
_reflns_number_total             3368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b03553_si_003.cif
_cod_data_source_block           02241AndreaGuerrero
_cod_depositor_comments
'Adding full bibliography for 4514381--4514383.cif.'
_cod_original_cell_volume        1844.6(13)
_cod_database_code               4514381
_shelx_res_checksum              49240
_shelx_hkl_checksum              7957