Highly diastereoselective synthesis of 1-pyrrolines via SnCl4-promoted [3 + 2] cycloaddition between activated donor-acceptor cyclopropanes and nitriles.
Sathishkannan, Gopal; Srinivasan, Kannupal; Organic letters 13 (2011) 6002–6005; doi:10.1021/ol2024423

data_1502551
_publ_section_title
;
 Highly diastereoselective synthesis of 1-pyrrolines via SnCl4-promoted [3
 + 2] cycloaddition between activated donor-acceptor cyclopropanes and
 nitriles.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6002
_journal_page_last               6005
_journal_paper_doi               10.1021/ol2024423
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C30 H29 N O6'
_chemical_formula_sum            'C30 H29 N O6'
_chemical_formula_weight         499.54
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   17.4100(6)
_cell_length_b                   62.6791(16)
_cell_length_c                   9.6861(2)
_cell_measurement_reflns_used    25037
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.65
_cell_measurement_theta_min      1.30
_cell_volume                     10569.9(5)
_computing_cell_refinement       'SMART (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SMART (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       58
_diffrn_reflns_limit_k_min       -58
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            25037
_diffrn_reflns_theta_full        19.65
_diffrn_reflns_theta_max         19.65
_diffrn_reflns_theta_min         1.30
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9939
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             4224
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.082
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(14)
_refine_ls_extinction_coef       0.00029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         2343
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+10.6003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0731
_reflns_number_gt                2175
_reflns_number_total             2343
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol2024423_si_001.cif
_cod_data_source_block           ksu_3
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               1502551