#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:08:28 +0200 (vie 13 de oct de 2017) $
#$Revision: 201955 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/84/2008418.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2008418
loop_
_publ_author_name
'Viktor Kettmann'
'Ján Svetlík'
_publ_contact_author
;
 Dr Viktor Kettmann
 Faculty of Pharmacy
 Comenius University
 Odbojárov 10
 832 32 Bratislava
 Slovak Republic
;
_publ_section_title
;
 Methyl
 1,4,5,6-tetrahydro-2-methyl-4-(2-nitrophenyl)-6-oxopyridine-3-carboxylate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              661
_journal_page_last               663
_journal_paper_doi               10.1107/S0108270198015029
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C14 H14 N2 O5'
_chemical_formula_sum            'C14 H14 N2 O5'
_chemical_formula_weight         290.27
_chemical_melting_point          479
_chemical_name_systematic
;
Methyl 1,4,5,6-tetrahydro-2-methyl-4-(2-nitrophenyl)-6-oxo-pyridine-3-
carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                95.83(7)
_cell_angle_beta                 107.27(8)
_cell_angle_gamma                97.34(7)
_cell_formula_units_Z            2
_cell_length_a                   7.328(8)
_cell_length_b                   8.729(9)
_cell_length_c                   11.513(11)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19
_cell_measurement_theta_min      8
_cell_volume                     689.9(13)
_computing_cell_refinement       'Syntex P2₁ software'
_computing_data_collection       'Syntex P2₁ software'
_computing_data_reduction        'XP21 (Pavelčík, 1987)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Syntex P2₁ diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3345
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      1.400(10)
_exptl_crystal_density_method    'flotation in bromoform-hexane'
_exptl_crystal_description       prism
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.271
_refine_ls_extinction_coef       0.020(6)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.041
_refine_ls_goodness_of_fit_obs   1.182
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_restrained_S_obs      1.182
_refine_ls_R_factor_all          0.104
_refine_ls_R_factor_obs          0.060
_refine_ls_shift/esd_max         -0.005
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0838P)²+0.0437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.165
_refine_ls_wR_factor_obs         0.123
_reflns_number_observed          1612
_reflns_number_total             3193
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            sk1228.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'triclinic ' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'noref ' changed
to 'noref' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0838P)^2^+0.0437P] 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^)+(0.0838P)^2^+0.0437P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P-1 '
_cod_original_formula_sum        'C14 H14 N2 O5 '
_cod_database_code               2008418
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 1.0124(3) 0.4702(3) 0.1617(2) 0.0457(6) Uani d . 1 . N
C2 0.8212(4) 0.4434(3) 0.1019(3) 0.0406(6) Uani d . 1 . C
O1 0.7579(3) 0.4537(2) -0.0062(2) 0.0520(5) Uani d . 1 . O
C3 0.6977(4) 0.4077(3) 0.1794(3) 0.0426(7) Uani d . 1 . C
C4 0.7795(3) 0.3007(3) 0.2707(2) 0.0390(6) Uani d . 1 . C
C5 0.9890(4) 0.3645(3) 0.3373(2) 0.0394(6) Uani d . 1 . C
C6 1.0955(4) 0.4487(3) 0.2831(2) 0.0424(7) Uani d . 1 . C
C7 0.7480(4) 0.1347(3) 0.2089(2) 0.0423(6) Uani d . 1 . C
C8 0.5863(4) 0.0255(4) 0.1933(3) 0.0555(8) Uani d . 1 . C
C9 0.5619(5) -0.1251(4) 0.1364(4) 0.0747(11) Uani d . 1 . C
C10 0.7001(7) -0.1699(4) 0.0919(3) 0.0763(12) Uani d . 1 . C
C11 0.8614(6) -0.0671(4) 0.1049(3) 0.0675(10) Uani d . 1 . C
C12 0.8856(4) 0.0819(3) 0.1638(3) 0.0524(8) Uani d . 1 . C
C13 1.0708(4) 0.3303(3) 0.4612(3) 0.0447(7) Uani d . 1 . C
O2 1.2216(3) 0.3907(3) 0.5351(2) 0.0675(7) Uani d . 1 . O
O3 0.9516(3) 0.2188(2) 0.4855(2) 0.0579(6) Uani d . 1 . O
C14 1.0140(6) 0.1712(4) 0.6037(3) 0.0716(10) Uani d . 1 . C
C15 1.3013(4) 0.5207(4) 0.3339(3) 0.0578(8) Uani d . 1 . C
N2 0.4300(4) 0.0641(4) 0.2391(4) 0.0853(10) Uani d . 1 . N
O4 0.3511(6) -0.0340(5) 0.2805(5) 0.185(2) Uani d . 1 . O
O5 0.3805(4) 0.1871(4) 0.2279(3) 0.0934(9) Uani d . 1 . O
H1 1.0959 0.5005 0.1200 0.055 Uiso d . 1 . H
H3A 0.5626 0.3674 0.1276 0.052 Uiso d . 1 . H
H3B 0.6937 0.5066 0.2255 0.052 Uiso d . 1 . H
H4 0.7125 0.3081 0.3318 0.047 Uiso d . 1 . H
H9 0.4541 -0.1907 0.1426 0.091 Uiso d . 1 . H
H10 0.6789 -0.2699 0.0581 0.091 Uiso d . 1 . H
H11 0.9577 -0.0975 0.0774 0.083 Uiso d . 1 . H
H12 0.9974 0.1497 0.1719 0.064 Uiso d . 1 . H
H14A 1.1419 0.1393 0.6056 0.086 Uiso d . 1 . H
H14B 1.0285 0.2532 0.6674 0.086 Uiso d . 1 . H
H14C 0.9261 0.0875 0.6077 0.086 Uiso d . 1 . H
H15A 1.3645 0.5372 0.2757 0.071 Uiso d . 1 . H
H15B 1.3726 0.4854 0.3968 0.071 Uiso d . 1 . H
H15C 1.3126 0.6276 0.3754 0.071 Uiso d . 1 . H
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_publ_flag
C2 N1 C6 124.6(2) yes
O1 C2 N1 121.6(3) yes
O1 C2 C3 123.6(3) yes
N1 C2 C3 114.8(3) yes
C2 C3 C4 112.1(2) n
C5 C4 C7 112.8(2) n
C5 C4 C3 109.1(2) n
C7 C4 C3 111.5(2) n
C6 C5 C13 121.6(3) n
C6 C5 C4 120.5(3) yes
C13 C5 C4 117.9(2) yes
C5 C6 N1 119.0(2) yes
C5 C6 C15 128.1(3) ?
N1 C6 C15 112.8(3) ?
C12 C7 C8 114.9(3) ?
C12 C7 C4 120.5(2) ?
C8 C7 C4 124.6(3) ?
C9 C8 C7 123.2(3) ?
C9 C8 N2 115.8(3) ?
C7 C8 N2 121.0(3) ?
C10 C9 C8 119.3(3) ?
C9 C10 C11 119.7(3) ?
C10 C11 C12 120.3(4) ?
C11 C12 C7 122.4(3) ?
O2 C13 O3 122.2(3) yes
O2 C13 C5 127.3(3) yes
O3 C13 C5 110.5(3) yes
C13 O3 C14 116.9(3) ?
O5 N2 O4 122.9(4) yes
O5 N2 C8 119.2(3) yes
O4 N2 C8 117.7(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.343(4) yes
N1 C6 . 1.392(4) yes
C2 O1 . 1.209(4) yes
C2 C3 . 1.475(4) n
C3 C4 . 1.519(4) n
C4 C5 . 1.500(4) n
C4 C7 . 1.506(4) n
C5 C6 . 1.332(4) n
C5 C13 . 1.452(4) n
C6 C15 . 1.473(4) ?
C7 C12 . 1.371(4) ?
C7 C8 . 1.377(4) ?
C8 C9 . 1.372(5) ?
C8 N2 . 1.458(5) yes
C9 C10 . 1.346(6) ?
C10 C11 . 1.349(5) ?
C11 C12 . 1.369(5) ?
C13 O2 . 1.194(4) yes
C13 O3 . 1.331(4) yes
O3 C14 . 1.423(4) ?
N2 O5 . 1.184(4) yes
N2 O4 . 1.189(4) yes
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_publ_flag
C6 N1 C2 O1 -174.8(3) yes
C6 N1 C2 C3 7.7(4) yes
O1 C2 C3 C4 141.7(3) ?
N1 C2 C3 C4 -40.9(3) ?
C2 C3 C4 C5 49.7(3) yes
C2 C3 C4 C7 -75.5(3) ?
C7 C4 C5 C6 95.6(3) ?
C3 C4 C5 C6 -28.8(3) yes
C7 C4 C5 C13 -83.9(3) ?
C3 C4 C5 C13 151.7(2) ?
C13 C5 C6 N1 176.3(2) ?
C4 C5 C6 N1 -3.2(4) yes
C13 C5 C6 C15 -0.8(4) ?
C4 C5 C6 C15 179.7(3) ?
C2 N1 C6 C5 15.9(4) yes
C2 N1 C6 C15 -166.6(3) ?
C5 C4 C7 C12 -31.9(3) yes
C3 C4 C7 C12 91.3(3) yes
C5 C4 C7 C8 147.8(3) ?
C3 C4 C7 C8 -89.1(3) ?
C12 C7 C8 C9 -0.4(4) ?
C4 C7 C8 C9 180.0(3) ?
C12 C7 C8 N2 178.6(3) ?
C4 C7 C8 N2 -1.0(4) ?
C7 C8 C9 C10 -0.8(5) ?
N2 C8 C9 C10 -179.9(3) ?
C8 C9 C10 C11 0.8(5) ?
C9 C10 C11 C12 0.4(5) ?
C10 C11 C12 C7 -1.7(5) ?
C8 C7 C12 C11 1.6(4) ?
C4 C7 C12 C11 -178.7(3) ?
C6 C5 C13 O2 14.0(5) yes
C4 C5 C13 O2 -166.5(3) ?
C6 C5 C13 O3 -166.6(2) ?
C4 C5 C13 O3 12.8(3) ?
O2 C13 O3 C14 -1.4(4) ?
C5 C13 O3 C14 179.2(2) ?
C9 C8 N2 O5 -139.9(4) ?
C7 C8 N2 O5 41.0(5) yes
C9 C8 N2 O4 36.2(6) ?
C7 C8 N2 O4 -142.9(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2009793
