#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/41/7204114.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_7204114
loop_
_publ_author_name
'Donohoe, Timothy J.'
'McRiner, Andrew J.'
'Helliwell, Madeleine'
'Sheldrake, Peter'
_publ_section_title
;
 Use of dissolving metals in the partial reduction of pyridines:
 formation of 2-alkyl-1,2-dihydropyridines 
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1435
_journal_paper_doi               10.1039/b101662h
_journal_year                    2001
_chemical_formula_sum            'C16 H25 N O4'
_chemical_formula_weight         295.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_date             19100-10-24
_audit_creation_method           'by teXsan v1.7'
_audit_update_record
;
?
;
_cell_angle_alpha                111.20
_cell_angle_beta                 93.03
_cell_angle_gamma                95.48
_cell_formula_units_Z            2
_cell_length_a                   7.310
_cell_length_b                   10.038
_cell_length_c                   12.314
_cell_measurement_reflns_used    'one image'
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      5
_cell_volume                     834.847
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1995)'
_computing_publication_material  'teXsan (MSC, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SIR92 (Altomare, et. al. 1993)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.633
_diffrn_measured_fraction_theta_max 0.633
_diffrn_measurement_device       'Rigaku RAXIS'
_diffrn_measurement_method       '90 x 4 degree phi scans'
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14636
_diffrn_reflns_theta_full        26.31
_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0656P)²+0.1042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                1843
_reflns_number_total             2152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b101662h.txt
_cod_data_source_block           compound_29
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.1042P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.1042P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        834.8
_cod_original_sg_symbol_H-M      'P -1       '
_cod_database_code               7204114
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33962(17) 0.23738(13) 0.80089(10) 0.0597(4) Uani 1 d . . .
O2 O 0.47184(19) 0.44647(14) 0.79399(11) 0.0711(4) Uani 1 d . . .
O3 O 0.11872(16) 0.29946(13) 0.31433(11) 0.0590(4) Uani 1 d . . .
O4 O -0.04627(17) 0.16309(15) 0.39216(13) 0.0700(4) Uani 1 d . . .
N1 N 0.25632(19) 0.05066(13) 0.44417(11) 0.0451(4) Uani 1 d . . .
C1 C 0.2946(2) 0.11470(17) 0.56103(14) 0.0434(4) Uani 1 d . . .
H1 H 0.2714 0.0598 0.6067 0.052 Uiso 1 calc R . .
C2 C 0.3657(2) 0.25566(17) 0.61584(14) 0.0448(4) Uani 1 d . . .
C3 C 0.4201(3) 0.34571(18) 0.54458(15) 0.0533(5) Uani 1 d . . .
H3A H 0.5356 0.4060 0.5797 0.064 Uiso 1 calc R . .
H3B H 0.3265 0.4082 0.5452 0.064 Uiso 1 calc R . .
C4 C 0.4419(2) 0.25060(18) 0.41833(15) 0.0518(5) Uani 1 d . . .
H4A H 0.5544 0.2060 0.4158 0.062 Uiso 1 calc R . .
H4B H 0.4519 0.3094 0.3709 0.062 Uiso 1 calc R . .
C5 C 0.2769(2) 0.13374(17) 0.36826(14) 0.0452(4) Uani 1 d . . .
C6 C 0.2977(3) 0.0158(2) 0.24950(16) 0.0600(5) Uani 1 d . . .
H6A H 0.2535 0.0424 0.1854 0.072 Uiso 1 calc R . .
H6B H 0.4255 -0.0015 0.2419 0.072 Uiso 1 calc R . .
C7 C 0.1792(3) -0.1160(2) 0.25156(16) 0.0652(5) Uani 1 d . . .
H7A H 0.2235 -0.2036 0.2017 0.078 Uiso 1 calc R . .
H7B H 0.0516 -0.1167 0.2250 0.078 Uiso 1 calc R . .
C8 C 0.1967(2) -0.10314(17) 0.37898(15) 0.0494(4) Uani 1 d . . .
H8A H 0.0793 -0.1328 0.4017 0.059 Uiso 1 calc R . .
H8B H 0.2876 -0.1614 0.3920 0.059 Uiso 1 calc R . .
C9 C 0.3987(2) 0.32317(19) 0.74247(16) 0.0519(5) Uani 1 d . . .
C10 C 0.3574(3) 0.3031(2) 0.92907(15) 0.0633(5) Uani 1 d . . .
H10 H 0.4777 0.3619 0.9562 0.076 Uiso 1 calc R . .
C11 C 0.3481(4) 0.1811(3) 0.9726(2) 0.0994(8) Uani 1 d . . .
H11A H 0.2332 0.1203 0.9424 0.149 Uiso 1 calc R . .
H11B H 0.3564 0.2190 1.0566 0.149 Uiso 1 calc R . .
H11C H 0.4486 0.1262 0.9467 0.149 Uiso 1 calc R . .
C12 C 0.2064(3) 0.3973(2) 0.96928(18) 0.0804(7) Uani 1 d . . .
H12A H 0.2119 0.4686 0.9341 0.121 Uiso 1 calc R . .
H12B H 0.2226 0.4441 1.0529 0.121 Uiso 1 calc R . .
H12C H 0.0885 0.3391 0.9464 0.121 Uiso 1 calc R . .
C13 C 0.0971(2) 0.19853(17) 0.36112(14) 0.0466(4) Uani 1 d . . .
C14 C -0.0420(2) 0.3714(2) 0.30139(17) 0.0598(5) Uani 1 d . . .
H14 H -0.1184 0.3791 0.3659 0.072 Uiso 1 calc R . .
C15 C 0.0355(3) 0.5196(2) 0.31102(19) 0.0714(6) Uani 1 d . . .
H15A H 0.1006 0.5698 0.3870 0.107 Uiso 1 calc R . .
H15B H -0.0634 0.5713 0.3002 0.107 Uiso 1 calc R . .
H15C H 0.1188 0.5124 0.2520 0.107 Uiso 1 calc R . .
C16 C -0.1533(3) 0.2842(2) 0.1875(2) 0.0918(8) Uani 1 d . . .
H16A H -0.0773 0.2729 0.1242 0.138 Uiso 1 calc R . .
H16B H -0.2563 0.3327 0.1775 0.138 Uiso 1 calc R . .
H16C H -0.1977 0.1912 0.1878 0.138 Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C10 116.76(14) . . ?
C13 O3 C14 117.83(13) . . ?
C1 N1 C8 126.12(13) . . ?
C1 N1 C5 120.86(13) . . ?
C8 N1 C5 113.00(13) . . ?
N1 C1 C2 123.48(15) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C9 122.17(15) . . ?
C1 C2 C3 120.07(15) . . ?
C9 C2 C3 117.71(14) . . ?
C2 C3 C4 111.12(14) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 110.73(13) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C4 109.16(13) . . ?
N1 C5 C13 108.27(13) . . ?
C4 C5 C13 111.62(14) . . ?
N1 C5 C6 101.96(13) . . ?
C4 C5 C6 115.54(14) . . ?
C13 C5 C6 109.66(14) . . ?
C7 C6 C5 103.92(14) . . ?
C7 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
C7 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C6 C7 C8 105.17(14) . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
N1 C8 C7 103.83(14) . . ?
N1 C8 H8A 111.0 . . ?
C7 C8 H8A 111.0 . . ?
N1 C8 H8B 111.0 . . ?
C7 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
O2 C9 O1 121.78(16) . . ?
O2 C9 C2 123.84(17) . . ?
O1 C9 C2 114.38(14) . . ?
O1 C10 C11 106.40(16) . . ?
O1 C10 C12 109.83(15) . . ?
C11 C10 C12 112.6(2) . . ?
O1 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
C12 C10 H10 109.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 O3 123.69(16) . . ?
O4 C13 C5 124.92(15) . . ?
O3 C13 C5 111.39(14) . . ?
O3 C14 C16 109.28(17) . . ?
O3 C14 C15 105.43(14) . . ?
C16 C14 C15 114.33(17) . . ?
O3 C14 H14 109.2 . . ?
C16 C14 H14 109.2 . . ?
C15 C14 H14 109.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.362(2) . ?
O1 C10 1.467(2) . ?
O2 C9 1.221(2) . ?
O3 C13 1.3359(19) . ?
O3 C14 1.467(2) . ?
O4 C13 1.200(2) . ?
N1 C1 1.348(2) . ?
N1 C8 1.468(2) . ?
N1 C5 1.465(2) . ?
C1 C2 1.364(2) . ?
C1 H1 0.9300 . ?
C2 C9 1.454(2) . ?
C2 C3 1.512(2) . ?
C3 C4 1.528(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.530(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C13 1.533(2) . ?
C5 C6 1.539(2) . ?
C6 C7 1.519(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.525(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.501(3) . ?
C10 C12 1.509(3) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C16 1.501(3) . ?
C14 C15 1.500(3) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 173.76(15) . . . . ?
C5 N1 C1 C2 -4.6(2) . . . . ?
N1 C1 C2 C9 177.51(14) . . . . ?
N1 C1 C2 C3 -5.0(2) . . . . ?
C1 C2 C3 C4 -17.8(2) . . . . ?
C9 C2 C3 C4 159.85(14) . . . . ?
C2 C3 C4 C5 47.66(19) . . . . ?
C1 N1 C5 C4 35.20(19) . . . . ?
C8 N1 C5 C4 -143.34(14) . . . . ?
C1 N1 C5 C13 -86.51(17) . . . . ?
C8 N1 C5 C13 94.95(15) . . . . ?
C1 N1 C5 C6 157.89(14) . . . . ?
C8 N1 C5 C6 -20.65(18) . . . . ?
C3 C4 C5 N1 -55.92(17) . . . . ?
C3 C4 C5 C13 63.74(18) . . . . ?
C3 C4 C5 C6 -170.07(14) . . . . ?
N1 C5 C6 C7 32.75(17) . . . . ?
C4 C5 C6 C7 150.98(15) . . . . ?
C13 C5 C6 C7 -81.83(17) . . . . ?
C5 C6 C7 C8 -33.87(18) . . . . ?
C1 N1 C8 C7 -178.41(15) . . . . ?
C5 N1 C8 C7 0.04(18) . . . . ?
C6 C7 C8 N1 21.16(18) . . . . ?
C10 O1 C9 O2 3.8(2) . . . . ?
C10 O1 C9 C2 -175.79(14) . . . . ?
C1 C2 C9 O2 175.59(17) . . . . ?
C3 C2 C9 O2 -2.0(3) . . . . ?
C1 C2 C9 O1 -4.9(2) . . . . ?
C3 C2 C9 O1 177.57(14) . . . . ?
C9 O1 C10 C11 -160.76(18) . . . . ?
C9 O1 C10 C12 77.1(2) . . . . ?
C14 O3 C13 O4 0.6(2) . . . . ?
C14 O3 C13 C5 179.85(14) . . . . ?
N1 C5 C13 O4 -13.9(2) . . . . ?
C4 C5 C13 O4 -134.08(18) . . . . ?
C6 C5 C13 O4 96.6(2) . . . . ?
N1 C5 C13 O3 166.82(13) . . . . ?
C4 C5 C13 O3 46.64(18) . . . . ?
C6 C5 C13 O3 -82.71(17) . . . . ?
C13 O3 C14 C16 -86.3(2) . . . . ?
C13 O3 C14 C15 150.33(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9208938
