#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:04:46 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180372 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/41/7204113.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_7204113
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 H23 N O4'
_chemical_formula_weight         293.35
_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             19100-05-31
_audit_creation_method           'by teXsan v1.7'
_audit_update_record
;
?
;
_cell_angle_alpha                93.16(3)
_cell_angle_beta                 95.88(3)
_cell_angle_gamma                111.93(3)
_cell_formula_units_Z            2
_cell_length_a                   9.886(5)
_cell_length_b                   12.422(5)
_cell_length_c                   7.391(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      9.6
_cell_measurement_theta_min      7.0
_cell_volume                     833.2(6)
_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
;
SHELXS86 (Sheldrick, 1985)
;
_diffrn_ambient_temperature      296.2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.1117
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3122
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        -2.58
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.2236
_refine_ls_R_factor_gt           0.0878
_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)+(0.0707P)²+0.3567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.2176
_reflns_number_gt                1252
_reflns_number_total             2937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b101662h.txt
_cod_data_source_block           compound_23
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.3567P] 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^)+(0.0707P)^2^+0.3567P] 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        833.3(6)
_cod_original_sg_symbol_H-M      'P -1       '
_cod_database_code               7204113
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 0.7633(4) -0.3031(3) 0.1723(5) 0.0762(11) Uani 1 d . . .
O2 O 0.5554(5) -0.3039(4) 0.0144(5) 0.0991(14) Uani 1 d . . .
O3 O 0.6995(4) 0.1815(3) 0.3926(4) 0.0762(11) Uani 1 d . . .
O4 O 0.8362(4) 0.1004(3) 0.5457(5) 0.0847(12) Uani 1 d . . .
N1 N 0.9432(4) 0.0503(4) 0.2408(5) 0.0548(10) Uani 1 d . . .
C1 C 0.8844(5) -0.0655(5) 0.2099(6) 0.0537(12) Uani 1 d . . .
H1 H 0.9412 -0.1075 0.2465 0.064 Uiso 1 calc R . .
C2 C 0.7445(5) -0.1247(5) 0.1269(6) 0.0550(12) Uani 1 d . . .
C3 C 0.6701(6) -0.0552(5) 0.0452(7) 0.0695(15) Uani 1 d . . .
H3 H 0.5830 -0.0923 -0.0338 0.083 Uiso 1 calc R . .
C4 C 0.7216(6) 0.0586(6) 0.0794(7) 0.0731(16) Uani 1 d . . .
H4 H 0.6781 0.1017 0.0140 0.088 Uiso 1 calc R . .
C5 C 0.8512(5) 0.1196(4) 0.2243(6) 0.0553(13) Uani 1 d . . .
C6 C 0.9622(6) 0.2370(5) 0.1849(7) 0.0809(17) Uani 1 d . . .
H6A H 0.9705 0.2385 0.0553 0.097 Uiso 1 calc R . .
H6B H 0.9339 0.3003 0.2252 0.097 Uiso 1 calc R . .
C7 C 1.1046(6) 0.2462(5) 0.2930(8) 0.0870(17) Uani 1 d . . .
H7A H 1.1878 0.2927 0.2348 0.104 Uiso 1 calc R . .
H7B H 1.1146 0.2822 0.4161 0.104 Uiso 1 calc R . .
C8 C 1.0973(5) 0.1231(4) 0.2970(6) 0.0648(14) Uani 1 d . . .
H8A H 1.1585 0.1073 0.2131 0.078 Uiso 1 calc R . .
H8B H 1.1296 0.1096 0.4190 0.078 Uiso 1 calc R . .
C9 C 0.6766(7) -0.2500(5) 0.0966(7) 0.0734(16) Uani 1 d . . .
C10 C 0.6990(7) -0.4299(5) 0.1556(8) 0.0840(17) Uani 1 d . . .
H10 H 0.6393 -0.4591 0.0359 0.101 Uiso 1 calc R . .
C11 C 0.8261(8) -0.4678(5) 0.1688(11) 0.130(3) Uani 1 d . . .
H11A H 0.8759 -0.4485 0.0631 0.195 Uiso 1 calc R . .
H11B H 0.7909 -0.5506 0.1746 0.195 Uiso 1 calc R . .
H11C H 0.8930 -0.4288 0.2769 0.195 Uiso 1 calc R . .
C12 C 0.6041(8) -0.4682(5) 0.3029(9) 0.119(2) Uani 1 d . . .
H12A H 0.6635 -0.4423 0.4201 0.178 Uiso 1 calc R . .
H12B H 0.5576 -0.5518 0.2899 0.178 Uiso 1 calc R . .
H12C H 0.5303 -0.4353 0.2937 0.178 Uiso 1 calc R . .
C13 C 0.7984(5) 0.1328(4) 0.4085(7) 0.0624(14) Uani 1 d . . .
C14 C 0.6288(6) 0.1935(5) 0.5528(7) 0.0778(17) Uani 1 d . . .
H14 H 0.6195 0.1284 0.6262 0.093 Uiso 1 calc R . .
C15 C 0.7207(7) 0.3060(6) 0.6649(9) 0.126(3) Uani 1 d . . .
H15A H 0.7360 0.3693 0.5903 0.188 Uiso 1 calc R . .
H15B H 0.8140 0.3040 0.7112 0.188 Uiso 1 calc R . .
H15C H 0.6712 0.3170 0.7653 0.188 Uiso 1 calc R . .
C16 C 0.4790(6) 0.1866(5) 0.4783(8) 0.100(2) Uani 1 d . . .
H16A H 0.4268 0.1944 0.5776 0.150 Uiso 1 calc R . .
H16B H 0.4259 0.1126 0.4079 0.150 Uiso 1 calc R . .
H16C H 0.4880 0.2482 0.4017 0.150 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 2 -1
2 -3 -2
3 -2 -2
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 115.9(5) . . ?
C13 O3 C14 118.2(4) . . ?
C1 N1 C8 126.9(4) . . ?
C1 N1 C5 121.2(4) . . ?
C8 N1 C5 111.9(4) . . ?
N1 C1 C2 122.5(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C9 123.7(5) . . ?
C1 C2 C3 116.3(5) . . ?
C9 C2 C3 119.5(5) . . ?
C4 C3 C2 121.9(5) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 109.2(4) . . ?
N1 C5 C6 101.5(4) . . ?
C4 C5 C6 116.8(4) . . ?
N1 C5 C13 108.9(4) . . ?
C4 C5 C13 110.2(4) . . ?
C6 C5 C13 109.8(4) . . ?
C7 C6 C5 103.9(4) . . ?
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 . . ?
C8 C7 C6 105.9(4) . . ?
C8 C7 H7A 110.5 . . ?
C6 C7 H7A 110.5 . . ?
C8 C7 H7B 110.5 . . ?
C6 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
N1 C8 C7 104.7(4) . . ?
N1 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
N1 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
O2 C9 O1 122.7(6) . . ?
O2 C9 C2 124.6(5) . . ?
O1 C9 C2 112.8(5) . . ?
O1 C10 C12 108.8(5) . . ?
O1 C10 C11 105.6(5) . . ?
C12 C10 C11 113.5(6) . . ?
O1 C10 H10 109.6 . . ?
C12 C10 H10 109.6 . . ?
C11 C10 H10 109.6 . . ?
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 124.4(5) . . ?
O4 C13 C5 125.0(4) . . ?
O3 C13 C5 110.5(4) . . ?
O3 C14 C15 109.2(5) . . ?
O3 C14 C16 105.4(4) . . ?
C15 C14 C16 113.7(5) . . ?
O3 C14 H14 109.5 . . ?
C15 C14 H14 109.5 . . ?
C16 C14 H14 109.5 . . ?
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 1.360(6) . ?
O1 C10 1.454(6) . ?
O2 C9 1.208(6) . ?
O3 C13 1.327(5) . ?
O3 C14 1.463(5) . ?
O4 C13 1.187(5) . ?
N1 C1 1.331(5) . ?
N1 C8 1.453(6) . ?
N1 C5 1.469(5) . ?
C1 C2 1.359(6) . ?
C1 H1 0.9300 . ?
C2 C9 1.441(7) . ?
C2 C3 1.446(6) . ?
C3 C4 1.310(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.505(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.527(6) . ?
C5 C13 1.529(6) . ?
C6 C7 1.508(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.506(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C12 1.492(7) . ?
C10 C11 1.494(7) . ?
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 C15 1.495(8) . ?
C14 C16 1.495(7) . ?
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 -167.9(4) . . . . ?
C5 N1 C1 C2 13.7(6) . . . . ?
N1 C1 C2 C9 -178.1(4) . . . . ?
N1 C1 C2 C3 10.2(6) . . . . ?
C1 C2 C3 C4 -13.1(7) . . . . ?
C9 C2 C3 C4 174.8(5) . . . . ?
C2 C3 C4 C5 -7.7(7) . . . . ?
C1 N1 C5 C4 -31.5(6) . . . . ?
C8 N1 C5 C4 149.9(4) . . . . ?
C1 N1 C5 C6 -155.4(4) . . . . ?
C8 N1 C5 C6 26.0(5) . . . . ?
C1 N1 C5 C13 88.8(5) . . . . ?
C8 N1 C5 C13 -89.8(4) . . . . ?
C3 C4 C5 N1 28.2(6) . . . . ?
C3 C4 C5 C6 142.6(5) . . . . ?
C3 C4 C5 C13 -91.4(6) . . . . ?
N1 C5 C6 C7 -34.1(5) . . . . ?
C4 C5 C6 C7 -152.6(4) . . . . ?
C13 C5 C6 C7 81.1(5) . . . . ?
C5 C6 C7 C8 31.2(5) . . . . ?
C1 N1 C8 C7 174.4(4) . . . . ?
C5 N1 C8 C7 -7.1(5) . . . . ?
C6 C7 C8 N1 -15.4(5) . . . . ?
C10 O1 C9 O2 -2.6(7) . . . . ?
C10 O1 C9 C2 176.9(4) . . . . ?
C1 C2 C9 O2 -175.8(5) . . . . ?
C3 C2 C9 O2 -4.3(8) . . . . ?
C1 C2 C9 O1 4.7(6) . . . . ?
C3 C2 C9 O1 176.2(4) . . . . ?
C9 O1 C10 C12 -82.3(6) . . . . ?
C9 O1 C10 C11 155.5(5) . . . . ?
C14 O3 C13 O4 -1.9(8) . . . . ?
C14 O3 C13 C5 175.8(4) . . . . ?
N1 C5 C13 O4 5.9(7) . . . . ?
C4 C5 C13 O4 125.6(6) . . . . ?
C6 C5 C13 O4 -104.5(6) . . . . ?
N1 C5 C13 O3 -171.8(4) . . . . ?
C4 C5 C13 O3 -52.0(6) . . . . ?
C6 C5 C13 O3 77.9(5) . . . . ?
C13 O3 C14 C15 87.6(6) . . . . ?
C13 O3 C14 C16 -149.9(5) . . . . ?
