#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:04:46 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180372 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/41/7204112.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_7204112
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            'C15 H23 N O4'
_chemical_formula_weight         281.34
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             19100-04-05
_audit_creation_method           'by teXsan v1.7'
_audit_update_record
;
?
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.14(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.365(11)
_cell_length_b                   11.860(5)
_cell_length_c                   12.158(6)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      16.7
_cell_measurement_theta_min      14.8
_cell_volume                     3283(3)
_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 0.439
_diffrn_measured_fraction_theta_max 0.439
_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           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2953
_diffrn_reflns_theta_full        70.10
_diffrn_reflns_theta_max         70.10
_diffrn_reflns_theta_min         3.88
_diffrn_standards_decay_%        -2.55
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0747
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1447P)²+2.4372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2549
_reflns_number_gt                1898
_reflns_number_total             2886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b101662h.txt
_cod_data_source_block           compound_11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1447P)^2^+2.4372P] 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^)+(0.1447P)^2^+2.4372P] 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        3284(2)
_cod_original_sg_symbol_H-M      'C 2/c      '
_cod_database_code               7204112
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65050(11) 0.3800(2) 0.7258(3) 0.0890(8) Uani 1 d . . .
O2 O 0.66349(14) 0.1924(3) 0.7238(3) 0.1143(11) Uani 1 d . . .
O3 O 0.40388(12) 0.1903(2) 0.2899(2) 0.0858(8) Uani 1 d . . .
O4 O 0.44902(13) 0.3579(2) 0.3315(2) 0.0877(9) Uani 1 d . . .
N1 N 0.47228(11) 0.3499(2) 0.5723(2) 0.0595(7) Uani 1 d . . .
C1 C 0.53120(14) 0.3557(3) 0.6264(3) 0.0585(8) Uani 1 d . . .
H1 H 0.5486 0.4253 0.6559 0.070 Uiso 1 calc R . .
C2 C 0.56707(15) 0.2655(3) 0.6408(3) 0.0649(8) Uani 1 d . . .
C3 C 0.53882(19) 0.1568(3) 0.6063(3) 0.0768(10) Uani 1 d . . .
H3 H 0.5616 0.0917 0.6289 0.092 Uiso 1 calc R . .
C4 C 0.48140(19) 0.1484(3) 0.5435(3) 0.0776(10) Uani 1 d . . .
H4 H 0.4644 0.0771 0.5277 0.093 Uiso 1 calc R . .
C5 C 0.44199(15) 0.2510(3) 0.4958(3) 0.0642(8) Uani 1 d . . .
C6 C 0.38255(18) 0.2294(4) 0.4974(4) 0.0858(12) Uani 1 d . . .
H6A H 0.3885 0.2194 0.5805 0.129 Uiso 1 calc R . .
H6B H 0.3650 0.1627 0.4510 0.129 Uiso 1 calc R . .
H6C H 0.3571 0.2927 0.4619 0.129 Uiso 1 calc R . .
C7 C 0.43700(15) 0.4497(3) 0.5668(3) 0.0685(9) Uani 1 d . . .
H7A H 0.4116 0.4327 0.6043 0.103 Uiso 1 calc R . .
H7B H 0.4138 0.4707 0.4829 0.103 Uiso 1 calc R . .
H7C H 0.4625 0.5109 0.6098 0.103 Uiso 1 calc R . .
C8 C 0.63060(17) 0.2734(3) 0.7004(3) 0.0757(9) Uani 1 d . . .
C9 C 0.71405(17) 0.3967(4) 0.7891(4) 0.0953(13) Uani 1 d . . .
H9 H 0.7341 0.3307 0.7767 0.114 Uiso 1 calc R . .
C10 C 0.7304(2) 0.4104(6) 0.9197(5) 0.140(2) Uani 1 d . . .
H10A H 0.7716 0.4267 0.9627 0.209 Uiso 1 calc R . .
H10B H 0.7220 0.3421 0.9513 0.209 Uiso 1 calc R . .
H10C H 0.7084 0.4714 0.9309 0.209 Uiso 1 calc R . .
C11 C 0.72714(18) 0.4980(5) 0.7326(4) 0.190(4) Uani 1 d . . .
H11A H 0.7064 0.5620 0.7425 0.286 Uiso 1 calc R . .
H11B H 0.7148 0.4845 0.6469 0.286 Uiso 1 calc R . .
H11C H 0.7686 0.5127 0.7720 0.286 Uiso 1 calc R . .
C12 C 0.43217(11) 0.2758(2) 0.3635(2) 0.0649(9) Uani 1 d R . .
C13 C 0.39326(13) 0.1959(2) 0.1611(2) 0.0869(11) Uani 1 d R . .
H13 H 0.4270 0.2361 0.1609 0.104 Uiso 1 calc R A 1
C14 C 0.3965(4) 0.0804(5) 0.1211(5) 0.161(3) Uani 1 d . . .
H14A H 0.3711 0.0323 0.1397 0.242 Uiso 1 calc R . .
H14B H 0.4362 0.0535 0.1630 0.242 Uiso 1 calc R . .
H14C H 0.3845 0.0799 0.0343 0.242 Uiso 1 calc R . .
C15A C 0.3433(4) 0.2620(8) 0.0894(8) 0.124(3) Uiso 0.66 d P B 1
H15A H 0.3110 0.2399 0.1058 0.186 Uiso 0.66 calc PR B 1
H15B H 0.3329 0.2508 0.0041 0.186 Uiso 0.66 calc PR B 1
H15C H 0.3520 0.3402 0.1096 0.186 Uiso 0.66 calc PR B 1
C15B C 0.3190(9) 0.1813(18) 0.093(2) 0.152(7) Uiso 0.34 d P B 2
H15D H 0.3065 0.1520 0.1517 0.228 Uiso 0.34 calc PR B 2
H15E H 0.3075 0.1301 0.0254 0.228 Uiso 0.34 calc PR B 2
H15F H 0.3010 0.2534 0.0644 0.228 Uiso 0.34 calc PR B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
-2 0 4
2 4 1
-7 1 -1
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
C8 O1 C9 117.6(3) . . ?
C12 O3 C13 118.1(2) . . ?
C1 N1 C7 120.4(3) . . ?
C1 N1 C5 120.3(3) . . ?
C7 N1 C5 118.2(3) . . ?
N1 C1 C2 123.9(3) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 116.4(3) . . ?
C1 C2 C8 123.0(3) . . ?
C3 C2 C8 120.2(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 122.3(3) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
N1 C5 C4 108.8(3) . . ?
N1 C5 C6 111.3(3) . . ?
C4 C5 C6 110.3(3) . . ?
N1 C5 C12 107.6(2) . . ?
C4 C5 C12 109.1(3) . . ?
C6 C5 C12 109.6(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 O1 122.5(4) . . ?
O2 C8 C2 124.1(4) . . ?
O1 C8 C2 113.4(3) . . ?
O1 C9 C10 107.8(4) . . ?
O1 C9 C11 106.5(3) . . ?
C10 C9 C11 113.3(5) . . ?
O1 C9 H9 109.7 . . ?
C10 C9 H9 109.7 . . ?
C11 C9 H9 109.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 O3 124.4(3) . . ?
O4 C12 C5 125.3(2) . . ?
O3 C12 C5 110.2(2) . . ?
C15A C13 C14 118.5(5) . . ?
C15A C13 O3 112.1(4) . . ?
C14 C13 O3 107.5(3) . . ?
C15A C13 C15B 42.1(7) . . ?
C14 C13 C15B 87.5(8) . . ?
O3 C13 C15B 99.0(7) . . ?
C15A C13 H13 106.0 . . ?
C14 C13 H13 105.9 . . ?
O3 C13 H13 105.9 . . ?
C15B C13 H13 146.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15A H15A 109.5 . . ?
C13 C15A H15B 109.5 . . ?
C13 C15A H15C 109.5 . . ?
C13 C15B H15D 109.5 . . ?
C13 C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C13 C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 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 C8 1.345(5) . ?
O1 C9 1.462(5) . ?
O2 C8 1.221(4) . ?
O3 C12 1.334(3) . ?
O3 C13 1.468(3) . ?
O4 C12 1.195(3) . ?
N1 C1 1.343(4) . ?
N1 C7 1.467(4) . ?
N1 C5 1.484(4) . ?
C1 C2 1.365(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.444(5) . ?
C2 C8 1.450(5) . ?
C3 C4 1.317(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.518(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.538(5) . ?
C5 C12 1.545(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.463(7) . ?
C9 C11 1.492(5) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C15A 1.417(9) . ?
C13 C14 1.469(6) . ?
C13 C15B 1.70(2) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 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
C7 N1 C1 C2 176.5(3) . . . . ?
C5 N1 C1 C2 -15.9(4) . . . . ?
N1 C1 C2 C3 -6.6(4) . . . . ?
N1 C1 C2 C8 -179.5(3) . . . . ?
C1 C2 C3 C4 12.4(5) . . . . ?
C8 C2 C3 C4 -174.5(3) . . . . ?
C2 C3 C4 C5 4.4(6) . . . . ?
C1 N1 C5 C4 29.4(4) . . . . ?
C7 N1 C5 C4 -162.8(3) . . . . ?
C1 N1 C5 C6 151.1(3) . . . . ?
C7 N1 C5 C6 -41.1(4) . . . . ?
C1 N1 C5 C12 -88.7(3) . . . . ?
C7 N1 C5 C12 79.1(3) . . . . ?
C3 C4 C5 N1 -24.0(5) . . . . ?
C3 C4 C5 C6 -146.3(4) . . . . ?
C3 C4 C5 C12 93.2(4) . . . . ?
C9 O1 C8 O2 -3.0(6) . . . . ?
C9 O1 C8 C2 178.4(3) . . . . ?
C1 C2 C8 O2 173.3(4) . . . . ?
C3 C2 C8 O2 0.7(6) . . . . ?
C1 C2 C8 O1 -8.1(5) . . . . ?
C3 C2 C8 O1 179.4(3) . . . . ?
C8 O1 C9 C10 -97.5(5) . . . . ?
C8 O1 C9 C11 140.5(4) . . . . ?
C13 O3 C12 O4 0.9(5) . . . . ?
C13 O3 C12 C5 -176.9(2) . . . . ?
N1 C5 C12 O4 3.6(4) . . . . ?
C4 C5 C12 O4 -114.3(4) . . . . ?
C6 C5 C12 O4 124.8(3) . . . . ?
N1 C5 C12 O3 -178.7(3) . . . . ?
C4 C5 C12 O3 63.4(3) . . . . ?
C6 C5 C12 O3 -57.5(3) . . . . ?
C12 O3 C13 C15A -81.9(5) . . . . ?
C12 O3 C13 C14 146.1(4) . . . . ?
C12 O3 C13 C15B -123.7(8) . . . . ?
