#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/07/2210738.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_2210738
loop_
_publ_author_name
'Long, Sihui'
'Siegler, Maxime'
'Li, Tonglei'
_publ_section_title
;
 N-(3-Chloro-2-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
;
_journal_coeditor_code           OB2055
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4278
_journal_page_last               o4279
_journal_paper_doi               10.1107/S160053680603488X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H11 Cl N2 O2'
_chemical_formula_moiety         'C13 H11 Cl N2 O2'
_chemical_formula_sum            'C13 H11 Cl N2 O2'
_chemical_formula_weight         262.69
_chemical_melting_point          .583E-305
_chemical_name_systematic
;
N-(3-chloro-2-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
;
_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                87.8186(14)
_cell_angle_beta                 89.5131(14)
_cell_angle_gamma                89.2959(13)
_cell_formula_units_Z            2
_cell_length_a                   7.1514(2)
_cell_length_b                   7.5805(2)
_cell_length_c                   10.3268(3)
_cell_measurement_reflns_used    2523
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     559.36(3)
_computing_cell_refinement       'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        DENZO--SMN
_computing_molecular_graphics    'XP in SHELXTL/PC (Sheldrick, 1995)'
_computing_publication_material  'SHELXL97 and local procedures'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_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  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            4917
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0508P)²+0.1363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                1811
_reflns_number_total             2560
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob2055.cif
_cod_data_source_block           I
_cod_database_code               2210738
_cod_database_fobs_code          2210738
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.1630(3) 0.2470(3) 0.8461(2) 0.0206(5) Uani d . 1
C C2 0.1096(3) 0.0802(3) 0.8107(2) 0.0210(5) Uani d . 1
H H2 0.0807 -0.0090 0.8746 0.025 Uiso calc R 1
C C3 0.0995(3) 0.0470(3) 0.6804(2) 0.0226(5) Uani d . 1
H H3 0.0626 -0.0663 0.6546 0.027 Uiso calc R 1
C C4 0.1422(3) 0.1761(3) 0.5867(2) 0.0214(5) Uani d . 1
H H4 0.1350 0.1514 0.4974 0.026 Uiso calc R 1
C C5 0.1959(3) 0.3427(3) 0.6242(2) 0.0183(5) Uani d . 1
C C6 0.2075(3) 0.3822(3) 0.7570(2) 0.0194(5) Uani d . 1
C C7 0.2635(3) 0.5632(3) 0.7967(2) 0.0225(5) Uani d . 1
H H7A 0.2646 0.5663 0.8915 0.034 Uiso calc R 1
H H7B 0.1738 0.6512 0.7621 0.034 Uiso calc R 1
H H7C 0.3887 0.5898 0.7624 0.034 Uiso calc R 1
C C8 0.2402(3) 0.4806(3) 0.4021(2) 0.0201(5) Uani d . 1
C C9 0.3027(3) 0.6516(3) 0.33807(19) 0.0179(5) Uani d . 1
C C10 0.2890(3) 0.6700(3) 0.2056(2) 0.0208(5) Uani d . 1
H H10 0.2418 0.5749 0.1589 0.025 Uiso calc R 1
C C11 0.3426(3) 0.8252(3) 0.1372(2) 0.0225(5) Uani d . 1
H H11 0.3327 0.8355 0.0456 0.027 Uiso calc R 1
C C12 0.4086(3) 0.9594(3) 0.2054(2) 0.0219(5) Uani d . 1
H H12 0.4448 1.0661 0.1615 0.026 Uiso calc R 1
C C13 0.3757(3) 0.7956(3) 0.4089(2) 0.0182(5) Uani d . 1
N N1 0.2449(2) 0.4785(2) 0.53417(16) 0.0192(4) Uani d . 1
H H1 0.2842 0.5762 0.5679 0.023 Uiso calc R 1
N N2 0.4235(2) 0.9428(2) 0.33554(16) 0.0202(4) Uani d . 1
H H2A 0.4672 1.0333 0.3763 0.024 Uiso calc R 1
O O1 0.1894(2) 0.35796(19) 0.33714(14) 0.0257(4) Uani d . 1
O O2 0.3979(2) 0.79608(18) 0.52985(13) 0.0211(3) Uani d . 1
Cl Cl1 0.16995(8) 0.28285(7) 1.01212(5) 0.02675(19) Uani d . 1
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 123.3(2)
C2 C1 Cl1 116.52(16)
C6 C1 Cl1 120.15(17)
C3 C2 C1 118.42(19)
C3 C2 H2 120.8
C1 C2 H2 120.8
C2 C3 C4 121.1(2)
C2 C3 H3 119.5
C4 C3 H3 119.5
C3 C4 C5 119.6(2)
C3 C4 H4 120.2
C5 C4 H4 120.2
C4 C5 N1 122.50(19)
C4 C5 C6 121.05(19)
N1 C5 C6 116.44(18)
C1 C6 C5 116.50(19)
C1 C6 C7 122.76(19)
C5 C6 C7 120.73(18)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O1 C8 N1 125.2(2)
O1 C8 C9 120.82(19)
N1 C8 C9 113.99(18)
C10 C9 C13 118.95(19)
C10 C9 C8 117.85(19)
C13 C9 C8 123.20(18)
C9 C10 C11 122.0(2)
C9 C10 H10 119.0
C11 C10 H10 119.0
C12 C11 C10 118.1(2)
C12 C11 H11 120.9
C10 C11 H11 120.9
N2 C12 C11 120.5(2)
N2 C12 H12 119.8
C11 C12 H12 119.8
O2 C13 N2 118.73(19)
O2 C13 C9 125.70(19)
N2 C13 C9 115.56(18)
C8 N1 C5 129.28(18)
C8 N1 H1 115.4
C5 N1 H1 115.4
C12 N2 C13 124.84(19)
C12 N2 H2A 117.6
C13 N2 H2A 117.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.388(3) ?
C1 C6 1.389(3) ?
C1 Cl1 1.748(2) ?
C2 C3 1.381(3) ?
C2 H2 0.9500 ?
C3 C4 1.385(3) ?
C3 H3 0.9500 ?
C4 C5 1.394(3) ?
C4 H4 0.9500 ?
C5 N1 1.407(3) ?
C5 C6 1.418(3) ?
C6 C7 1.507(3) ?
C7 H7A 0.9800 ?
C7 H7B 0.9800 ?
C7 H7C 0.9800 ?
C8 O1 1.227(3) ?
C8 N1 1.364(3) ?
C8 C9 1.504(3) ?
C9 C10 1.374(3) yes
C9 C13 1.442(3) yes
C10 C11 1.404(3) yes
C10 H10 0.9500 ?
C11 C12 1.351(3) yes
C11 H11 0.9500 ?
C12 N2 1.350(3) yes
C12 H12 0.9500 ?
C13 O2 1.261(2) yes
C13 N2 1.370(3) yes
N1 H1 0.8800 ?
N2 H2A 0.8800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O2 . 0.88 1.89 2.655(2) 144.3
N2 H2A O2 2_676 0.88 1.92 2.790(2) 169.5
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 C1 C2 C3 -0.2(3) ?
Cl1 C1 C2 C3 179.03(15) ?
C1 C2 C3 C4 0.3(3) ?
C2 C3 C4 C5 -0.2(3) ?
C3 C4 C5 N1 178.63(19) ?
C3 C4 C5 C6 0.0(3) ?
C2 C1 C6 C5 0.0(3) ?
Cl1 C1 C6 C5 -179.18(14) ?
C2 C1 C6 C7 179.41(19) ?
Cl1 C1 C6 C7 0.2(3) ?
C4 C5 C6 C1 0.1(3) ?
N1 C5 C6 C1 -178.65(18) ?
C4 C5 C6 C7 -179.31(19) ?
N1 C5 C6 C7 2.0(3) ?
O1 C8 C9 C10 4.3(3) ?
N1 C8 C9 C10 -175.16(17) ?
O1 C8 C9 C13 -175.69(19) ?
N1 C8 C9 C13 4.8(3) yes
C13 C9 C10 C11 -0.4(3) ?
C8 C9 C10 C11 179.55(18) ?
C9 C10 C11 C12 -0.3(3) ?
C10 C11 C12 N2 0.5(3) ?
C10 C9 C13 O2 -179.12(19) ?
C8 C9 C13 O2 0.9(3) ?
C10 C9 C13 N2 0.9(3) ?
C8 C9 C13 N2 -179.09(17) ?
O1 C8 N1 C5 0.2(3) ?
C9 C8 N1 C5 179.65(19) yes
C4 C5 N1 C8 4.1(3) yes
C6 C5 N1 C8 -177.21(18) ?
C11 C12 N2 C13 0.0(3) ?
O2 C13 N2 C12 179.31(18) ?
C9 C13 N2 C12 -0.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127167
