Sc(OTf)3-mediated 1,3-dipolar cycloaddition-ring cleavage-rearrangement: a highly stereoselective access to Z-β-enaminonitriles.
Wang, Ying-chun; Xie, Yu-yang; Tan, Xian-chun; Wang, Heng-shan; Pan, Ying-ming; Organic & biomolecular chemistry 13 (2015) 513–519; doi:10.1039/c4ob01801j

data_7154163
_publ_section_title
;
 Sc(OTf)3-mediated 1,3-dipolar cycloaddition-ring cleavage-rearrangement:
 a highly stereoselective access to Z-\b-enaminonitriles.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              513
_journal_page_last               519
_journal_paper_doi               10.1039/c4ob01801j
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C16 H14 N2'
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-03
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.835(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9757(3)
_cell_length_b                   5.76438(17)
_cell_length_c                   22.7227(7)
_cell_measurement_reflns_used    3192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7614
_cell_measurement_theta_min      3.3197
_cell_volume                     1305.97(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -23.00    2.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791  -57.0000 -120.0000 25

  2 omega  -85.00    9.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791  -77.0000  120.0000 94

  3 omega  -76.00  -46.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791  133.0000  -49.0000 30

  4 omega  -46.00   47.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791   77.0000 -120.0000 93

  5 omega  -52.00   54.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791   19.0000   60.0000 106

  6 omega  -91.00  -66.00   1.0000   12.3800
omega____ theta____ kappa____ phi______ frames
    -      -16.8791 -178.0000   30.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0708139000
_diffrn_orient_matrix_UB_12      -0.0067344000
_diffrn_orient_matrix_UB_13      0.0034452000
_diffrn_orient_matrix_UB_21      -0.0055229000
_diffrn_orient_matrix_UB_22      0.0024691000
_diffrn_orient_matrix_UB_23      0.0310326000
_diffrn_orient_matrix_UB_31      -0.0040032000
_diffrn_orient_matrix_UB_32      -0.1228487000
_diffrn_orient_matrix_UB_33      0.0004333000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9336
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.59
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2662
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+0.4136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                2075
_reflns_number_total             2662
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01801j2.cif
_cod_data_source_block           0901-whs-wyc-1
_cod_depositor_comments
'Adding full bibliography for 7154163--7154164.cif.'
_cod_database_code               7154163
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32