Metalated nitriles: cation-controlled cyclizations.
Fleming, Fraser F.; Wei, Yunjing; Liu, Wang; Zhang, Zhiyu; Organic letters 9 (2007) 2733–2736; doi:10.1021/ol071084k

data_1505453
_publ_section_title
;
 Metalated nitriles: cation-controlled cyclizations.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2733
_journal_page_last               2736
_journal_paper_doi               10.1021/ol071084k
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         C13H19NO
_chemical_formula_sum            'C13 H19 N O'
_chemical_formula_weight         205.29
_chemical_name_systematic
; 
 1-Hydroxy-1-methyl-6-methylene-octahydro-naphthalene-4a-carbonitrile 
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.3490(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6636(3)
_cell_length_b                   7.7296(2)
_cell_length_c                   15.8534(4)
_cell_measurement_temperature    273(2)
_cell_volume                     1156.78(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.1733
_diffrn_reflns_av_sigmaI/netI    0.0930
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16224
_diffrn_reflns_theta_full        31.02
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.074
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0645
_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^)+(0.1101P)^2^+0.0906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1875
_reflns_number_gt                2777
_reflns_number_total             3649
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol071084ksi20070511_075208.cif
_cod_data_source_block           ffyj002_0m
_cod_original_sg_symbol_H-M      p_21/n
_cod_database_code               1505453