Organocatalytic asymmetric inverse-electron-demand 1,3-dipolar cycloaddition of n,n'-cyclic azomethine imines.
Zhu, Ren-Yi; Wang, Cong-Shuai; Zheng, Jian; Shi, Feng; Tu, Shu-Jiang; The Journal of organic chemistry 79 (2014) 9305–9312; doi:10.1021/jo5018469

data_4029997
_publ_section_title
;
 Organocatalytic asymmetric inverse-electron-demand 1,3-dipolar
 cycloaddition of n,n'-cyclic azomethine imines.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9305
_journal_page_last               9312
_journal_paper_doi               10.1021/jo5018469
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H18 Cl2 N2 O2'
_chemical_formula_weight         377.25
_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
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1739(5)
_cell_length_b                   11.6246(7)
_cell_length_c                   22.2901(13)
_cell_measurement_reflns_used    8105
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.67
_cell_measurement_theta_min      2.53
_cell_volume                     2118.0(2)
_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 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27674
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         2.532
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_platon_squeeze_details
;
;
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
; 
 Flack x determined using 1328 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.13(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0941P)^2^+0.2559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1622
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                3654
_reflns_number_total             4754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5018469_si_001.cif
_cod_data_source_block           SF130707_ZRY_0m
_cod_database_code               4029997
_shelx_estimated_absorpt_t_min   0.903
_shelx_estimated_absorpt_t_max   0.939
_shelxl_version_number           2014-3
_shelx_res_checksum              23112
_shelx_hkl_checksum              22386