#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/54/1505453.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1505453
loop_
_publ_author_name
'Fleming, Fraser F.'
'Wei, Yunjing'
'Liu, Wang'
'Zhang, Zhiyu'
_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/[σ²(Fo²)+(0.1101P)²+0.0906P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.41966(10) 0.24357(12) 0.77303(6) 0.0266(2) Uani 1 1 d .
H1 H 0.3228 0.1983 0.7575 0.032 Uiso 1 1 calc R
O1 O 0.36337(10) 0.46069(10) 0.87249(6) 0.0410(2) Uani 1 1 d .
H1A H 0.4049 0.5443 0.8579 0.062 Uiso 1 1 calc R
C6 C 0.44506(12) 0.30702(13) 0.86859(7) 0.0303(2) Uani 1 1 d .
C2 C 0.52176(11) 0.09489(13) 0.75924(7) 0.0290(2) Uani 1 1 d .
C7 C 0.42988(13) 0.39508(14) 0.71184(7) 0.0348(3) Uani 1 1 d .
H7A H 0.3596 0.4814 0.7175 0.042 Uiso 1 1 calc R
H7B H 0.5226 0.4482 0.7291 0.042 Uiso 1 1 calc R
C11 C 0.50087(14) 0.04751(15) 0.66156(8) 0.0385(3) Uani 1 1 d .
H11A H 0.5728 -0.0354 0.6544 0.046 Uiso 1 1 calc R
H11B H 0.4091 -0.0070 0.6424 0.046 Uiso 1 1 calc R
C3 C 0.67675(12) 0.14155(15) 0.79845(8) 0.0365(3) Uani 1 1 d .
H3A H 0.7364 0.0426 0.7939 0.044 Uiso 1 1 calc R
H3B H 0.7058 0.2358 0.7657 0.044 Uiso 1 1 calc R
C5 C 0.60180(13) 0.34550(16) 0.90400(8) 0.0392(3) Uani 1 1 d .
H5A H 0.6286 0.4462 0.8747 0.047 Uiso 1 1 calc R
H5B H 0.6158 0.3732 0.9649 0.047 Uiso 1 1 calc R
C4 C 0.69818(13) 0.19488(17) 0.89286(9) 0.0421(3) Uani 1 1 d .
H4A H 0.7962 0.2282 0.9142 0.051 Uiso 1 1 calc R
H4B H 0.6782 0.0971 0.9267 0.051 Uiso 1 1 calc R
C9 C 0.50978(14) 0.20204(17) 0.60663(8) 0.0404(3) Uani 1 1 d .
C12 C 0.48964(13) -0.06856(14) 0.79977(8) 0.0368(3) Uani 1 1 d .
C8 C 0.40705(15) 0.34031(18) 0.61721(8) 0.0447(3) Uani 1 1 d .
H8A H 0.3111 0.2978 0.5977 0.054 Uiso 1 1 calc R
H8B H 0.4194 0.4395 0.5821 0.054 Uiso 1 1 calc R
N1 N 0.46912(16) -0.20063(14) 0.82647(9) 0.0549(3) Uani 1 1 d .
C13 C 0.38645(15) 0.18123(16) 0.92617(8) 0.0422(3) Uani 1 1 d .
H13A H 0.2873 0.1632 0.9031 0.063 Uiso 1 1 calc R
H13B H 0.3995 0.2284 0.9834 0.063 Uiso 1 1 calc R
H13C H 0.4357 0.0729 0.9283 0.063 Uiso 1 1 calc R
C10 C 0.59930(19) 0.2136(2) 0.55408(11) 0.0623(4) Uani 1 1 d .
H10A H 0.6605 0.1226 0.5502 0.075 Uiso 1 1 calc R
H10B H 0.6009 0.3128 0.5211 0.075 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 C1 C2 110.17(9)
C7 C1 C6 110.80(8)
C2 C1 C6 113.23(8)
O1 C6 C13 102.95(9)
O1 C6 C5 109.54(9)
C13 C6 C5 111.75(10)
O1 C6 C1 109.15(8)
C13 C6 C1 112.30(9)
C5 C6 C1 110.82(9)
C12 C2 C3 107.55(9)
C12 C2 C1 111.73(9)
C3 C2 C1 111.18(8)
C12 C2 C11 103.63(9)
C3 C2 C11 111.36(9)
C1 C2 C11 111.11(8)
C8 C7 C1 113.14(9)
C9 C11 C2 112.32(9)
C4 C3 C2 112.14(9)
C4 C5 C6 113.02(9)
C3 C4 C5 111.24(9)
C10 C9 C11 123.21(13)
C10 C9 C8 124.15(13)
C11 C9 C8 112.64(11)
N1 C12 C2 174.88(14)
C9 C8 C7 110.42(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C7 1.5373(14)
C1 C2 1.5603(14)
C1 C6 1.5611(14)
O1 C6 1.4349(13)
C6 C13 1.5232(16)
C6 C5 1.5278(16)
C2 C12 1.4801(15)
C2 C3 1.5367(15)
C2 C11 1.5618(16)
C7 C8 1.5287(17)
C11 C9 1.4916(17)
C3 C4 1.5234(18)
C5 C4 1.5246(18)
C9 C10 1.326(2)
C9 C8 1.4923(18)
C12 N1 1.1386(16)
