Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines with methyleneindolinones.
Gerten, Anthony L.; Slade, Michael C.; Pugh, Kelsie M.; Stanley, Levi M.; Organic & biomolecular chemistry 11 (2013) 7834–7837; doi:10.1039/c3ob41815d

data_7153187
_publ_section_title
;
 Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines
 with methyleneindolinones.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7834
_journal_page_last               7837
_journal_paper_doi               10.1039/c3ob41815d
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         '(C39 H35 Br2 N3 O4) 2 (C2 H6O)'
_chemical_formula_sum            'C39 H35 Br2 N3 O4'
_chemical_formula_weight         769.52
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2013.2-0'
_cell_angle_alpha                90
_cell_angle_beta                 110.181(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.458(3)
_cell_length_b                   15.458(3)
_cell_length_c                   18.938(4)
_cell_measurement_reflns_used    3841
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      22.5148
_cell_measurement_theta_min      2.2775
_cell_volume                     3697.9(13)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 Suite (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  ' BRUKER APEX2 CCD Diffractometer'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28783
_diffrn_reflns_theta_full        24.83
_diffrn_reflns_theta_max         24.83
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    2.235
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
SQUEEZE indicates 206 unaccounted electrons in a vois per
cell which is in a good accordance with 2 EtOH solvent 
molecules per titles molecule. This solvent molecules
were included to final content of the cell to obtain
actual metric information
;
_refine_diff_density_max         1.798
_refine_diff_density_min         -0.510
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1437P)^2^+1.0852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2089
_refine_ls_wR_factor_ref         0.2335
_reflns_number_gt                4020
_reflns_number_total             6364
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41815d.txt
_cod_data_source_block           I
_cod_original_cell_volume        3697.9(12)
_cod_database_code               7153187