#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:59:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178454 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/75/4027517.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_4027517
loop_
_publ_author_name
'Sharavathi G. Parameswarappa'
'F. Christopher Pigge'
_publ_section_title
;
 Intramolecular Cyclization Manifolds of 4-Alkylpyridines Bearing
 Ambiphilic Side Chains: Construction of Spirodihydropyridines or Benzylic
 Cyclization via Anhydrobase Intermediates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8038
_journal_page_last               8048
_journal_paper_doi               10.1021/jo301247c
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.235(5)
_cell_angle_beta                 93.780(5)
_cell_angle_gamma                93.453(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3151(8)
_cell_length_b                   7.7610(9)
_cell_length_c                   11.2261(12)
_cell_measurement_temperature    200(2)
_cell_volume                     594.35(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3967
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9867
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       0.27(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.391
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.391
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.2008
_reflns_number_gt                1561
_reflns_number_total             2163
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301247c_si_002.cif
_cod_data_source_block           fcp116
_cod_original_cell_volume        594.35(11)
_cod_database_code               4027517
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O4 O 0.1240(2) 0.3770(2) 0.29936(16) 0.0359(5) Uani 1 1 d .
O3 O 0.7704(2) 1.0879(2) 0.73154(17) 0.0392(5) Uani 1 1 d .
N1 N 0.5266(3) 0.8931(3) 0.6224(2) 0.0324(6) Uani 1 1 d .
O2 O 0.4992(3) 1.1097(3) 0.81828(18) 0.0461(6) Uani 1 1 d .
C12 C 0.3469(4) 0.8168(4) 0.6139(3) 0.0358(6) Uani 1 1 d .
H12A H 0.2743 0.8656 0.6830 0.043 Uiso 1 1 calc R
C11 C 0.3031(3) 0.4509(3) 0.2965(2) 0.0309(6) Uani 1 1 d .
C10 C 0.2739(4) 0.6758(3) 0.5103(2) 0.0351(7) Uani 1 1 d .
H10A H 0.1512 0.6265 0.5083 0.042 Uiso 1 1 calc R
C9 C 0.3769(3) 0.5967(3) 0.4012(2) 0.0315(6) Uani 1 1 d .
C8 C 0.5925(4) 1.0394(3) 0.7344(2) 0.0341(7) Uani 1 1 d .
C7 C 0.5613(4) 0.6818(4) 0.4139(3) 0.0351(6) Uani 1 1 d .
H7A H 0.6359 0.6384 0.3453 0.042 Uiso 1 1 calc R
C6 C 0.6306(4) 0.8212(4) 0.5202(2) 0.0348(6) Uani 1 1 d .
H6A H 0.7537 0.8715 0.5255 0.042 Uiso 1 1 calc R
C5 C 0.0765(3) 0.2350(3) 0.1842(3) 0.0355(7) Uani 1 1 d .
C14 C 0.3664(3) 0.3491(3) 0.1766(2) 0.0335(7) Uani 1 1 d .
C3 C 0.8551(4) 1.2339(4) 0.8455(3) 0.0411(7) Uani 1 1 d .
H3A H 0.8665 1.1892 0.9179 0.049 Uiso 1 1 calc R
H3B H 0.7796 1.3404 0.8684 0.049 Uiso 1 1 calc R
C2 C 1.0408(4) 1.2892(4) 0.8157(3) 0.0492(8) Uani 1 1 d .
H2A H 1.1027 1.3878 0.8905 0.074 Uiso 1 1 calc R
H2B H 1.0275 1.3333 0.7439 0.074 Uiso 1 1 calc R
H2C H 1.1140 1.1827 0.7931 0.074 Uiso 1 1 calc R
C1 C 0.2299(4) 0.2201(3) 0.1090(2) 0.0363(7) Uani 1 1 d .
H1A H 0.2348 0.1338 0.0254 0.044 Uiso 1 1 calc R
O1 O -0.0753(3) 0.1504(3) 0.16413(18) 0.0466(6) Uiso 1 1 d .
C4 C 0.5481(4) 0.3809(4) 0.1303(3) 0.0427(7) Uiso 1 1 d .
H4C H 0.5545 0.2911 0.0445 0.064 Uiso 1 1 calc R
H4D H 0.6473 0.3663 0.1882 0.064 Uiso 1 1 calc R
H4A H 0.5617 0.5059 0.1278 0.064 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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C5 O4 C11 107.73(19)
C8 O3 C3 115.2(2)
C6 N1 C12 118.6(2)
C6 N1 C8 123.6(2)
C12 N1 C8 117.8(2)
C10 C12 N1 121.5(2)
C9 C11 O4 117.5(2)
C9 C11 C14 134.5(2)
O4 C11 C14 108.0(2)
C12 C10 C9 121.9(2)
C11 C9 C7 123.7(2)
C11 C9 C10 121.7(2)
C7 C9 C10 114.5(2)
O2 C8 O3 126.0(2)
O2 C8 N1 123.5(2)
O3 C8 N1 110.5(2)
C6 C7 C9 121.8(2)
C7 C6 N1 121.7(2)
O1 C5 O4 119.6(2)
O1 C5 C1 132.7(3)
O4 C5 C1 107.7(2)
C1 C14 C11 107.8(2)
C1 C14 C4 125.2(2)
C11 C14 C4 126.9(2)
O3 C3 C2 106.9(2)
C14 C1 C5 108.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C5 1.384(3)
O4 C11 1.405(3)
O3 C8 1.339(3)
O3 C3 1.453(3)
N1 C6 1.389(3)
N1 C12 1.393(3)
N1 C8 1.403(3)
O2 C8 1.194(3)
C12 C10 1.343(4)
C11 C9 1.369(4)
C11 C14 1.429(4)
C10 C9 1.449(4)
C9 C7 1.442(4)
C7 C6 1.346(4)
C5 O1 1.221(3)
C5 C1 1.435(4)
C14 C1 1.353(4)
C14 C4 1.496(4)
C3 C2 1.493(4)
