Ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles.
Liu, Kang; Xiong, Yong; Wang, Zuo-Fei; Tao, Hai-Yan; Wang, Chun-Jiang; Chemical communications (Cambridge, England) 52 (2016) 9458–9461; doi:10.1039/c6cc03169b

data_7124649
_publ_section_title
;
 Ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine
 ylides with 3-methyl-4-nitro-5-styrylisoxazoles.
;
_journal_issue                   60
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9458
_journal_page_last               9461
_journal_paper_doi               10.1039/c6cc03169b
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C64 H59 Cl2 N6 O14'
_chemical_formula_weight         1207.07
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-04-12 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8312(4)
_cell_length_b                   18.6954(5)
_cell_length_c                   21.7724(7)
_cell_measurement_reflns_used    8734
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      60.62
_cell_measurement_theta_min      3.12
_cell_volume                     6444.0(3)
_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_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24143
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        62.477
_diffrn_reflns_theta_max         62.477
_diffrn_reflns_theta_min         3.116
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.463
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.4320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             2524
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2889 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     846
_refine_ls_number_reflns         9732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0954P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1516
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                7925
_reflns_number_total             9732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc03169b2.cif
_cod_data_source_block           x_a
_cod_database_code               7124649
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.495
_shelx_estimated_absorpt_t_max   0.868