#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/73/2217364.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_2217364
loop_
_publ_author_name
'Lima, Daniel F. de'
'Pérez-Rebolledo, Anayive'
'Ellena, Javier'
'Beraldo, Heloisa'
_publ_section_title
;
 2-Benzoylpyridine semicarbazone
;
_journal_coeditor_code           WW2110
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o177
_journal_page_last               o177
_journal_paper_doi               10.1107/S1600536807064628
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H12 N4 O'
_chemical_formula_moiety         'C13 H12 N4 O'
_chemical_formula_sum            'C13 H12 N4 O'
_chemical_formula_weight         240.27
_chemical_name_systematic
;
2-Benzoylpyridine semicarbazone
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 93.0490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.9281(7)
_cell_length_b                   9.1868(2)
_cell_length_c                   23.1869(7)
_cell_measurement_reflns_used    23344
_cell_measurement_temperature    294
_cell_measurement_theta_max      25.682
_cell_measurement_theta_min      2.91
_cell_volume                     4877.1(2)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Enraf--Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16551
_diffrn_reflns_theta_full        25.69
_diffrn_reflns_theta_max         25.69
_diffrn_reflns_theta_min         3.53
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0842P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1501
_reflns_number_gt                3011
_reflns_number_total             4588
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww2110.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2217364
_cod_database_fobs_code          2217364
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_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
O O1 0.32552(5) 0.15282(12) 0.00628(6) 0.0579(4) Uani d . 1
N N11 0.30310(7) 0.38523(15) 0.02708(7) 0.0638(5) Uani d . 1
H H11A 0.2668 0.3735 0.0168 0.077 Uiso calc R 1
H H11B 0.3154 0.4685 0.0396 0.077 Uiso calc R 1
N N12 0.39721(7) 0.30226(14) 0.03898(7) 0.0560(4) Uani d . 1
H H12 0.4234 0.2373 0.0338 0.067 Uiso calc R 1
N N13 0.41230(6) 0.43452(15) 0.06270(6) 0.0518(4) Uani d . 1
N N14 0.50663(7) 0.22107(17) 0.07080(8) 0.0646(5) Uani d . 1
C C11 0.33995(8) 0.27542(18) 0.02374(8) 0.0472(4) Uani d . 1
C C12 0.46602(8) 0.46234(18) 0.07889(7) 0.0503(4) Uani d . 1
C C13 0.47417(8) 0.60980(18) 0.10515(8) 0.0507(5) Uani d . 1
C C14 0.43912(9) 0.7256(2) 0.08574(9) 0.0615(5) Uani d . 1
H H14 0.4120 0.7117 0.0550 0.074 Uiso calc R 1
C C15 0.44422(10) 0.8602(2) 0.11153(11) 0.0717(6) Uani d . 1
H H15 0.4210 0.9369 0.0977 0.086 Uiso calc R 1
C C16 0.48359(10) 0.8818(2) 0.15773(11) 0.0752(6) Uani d . 1
H H16 0.4864 0.9723 0.1756 0.090 Uiso calc R 1
C C17 0.51862(10) 0.7691(2) 0.17715(10) 0.0728(6) Uani d . 1
H H17 0.5458 0.7840 0.2078 0.087 Uiso calc R 1
C C18 0.51390(9) 0.6347(2) 0.15160(9) 0.0612(5) Uani d . 1
H H18 0.5376 0.5590 0.1655 0.073 Uiso calc R 1
C C19 0.51699(8) 0.36475(18) 0.07344(8) 0.0526(5) Uani d . 1
C C110 0.57304(9) 0.4197(2) 0.07022(8) 0.0625(5) Uani d . 1
H H110 0.5795 0.5196 0.0709 0.075 Uiso calc R 1
C C111 0.61896(9) 0.3247(3) 0.06597(10) 0.0745(6) Uani d . 1
H H111 0.6568 0.3601 0.0642 0.089 Uiso calc R 1
C C112 0.60892(10) 0.1782(3) 0.06428(10) 0.0746(6) Uani d . 1
H H112 0.6395 0.1124 0.0620 0.090 Uiso calc R 1
C C113 0.55268(10) 0.1312(2) 0.06610(10) 0.0732(6) Uani d . 1
H H113 0.5456 0.0316 0.0640 0.088 Uiso calc R 1
O O2 0.24288(6) 0.15322(12) 0.42544(5) 0.0583(4) Uani d . 1
N N21 0.21621(7) 0.38036(15) 0.44999(7) 0.0600(4) Uani d . 1
H H21A 0.2252 0.3660 0.4860 0.072 Uiso calc R 1
H H21B 0.2025 0.4632 0.4386 0.072 Uiso calc R 1
N N22 0.20957(7) 0.30602(15) 0.35554(6) 0.0568(4) Uani d . 1
H H22 0.2161 0.2435 0.3291 0.068 Uiso calc R 1
N N23 0.18510(7) 0.43784(15) 0.34154(6) 0.0529(4) Uani d . 1
N N24 0.17683(8) 0.22916(17) 0.24561(7) 0.0621(4) Uani d . 1
C C21 0.22340(8) 0.27519(17) 0.41217(7) 0.0468(4) Uani d . 1
C C22 0.17017(8) 0.46887(18) 0.28832(7) 0.0507(4) Uani d . 1
C C23 0.14314(8) 0.61504(18) 0.28004(8) 0.0517(5) Uani d . 1
C C24 0.16044(9) 0.7306(2) 0.31577(9) 0.0618(5) Uani d . 1
H H24 0.1901 0.7173 0.3442 0.074 Uiso calc R 1
C C25 0.13392(11) 0.8647(2) 0.30944(9) 0.0726(6) Uani d . 1
H H25 0.1458 0.9412 0.3336 0.087 Uiso calc R 1
C C26 0.09007(11) 0.8860(2) 0.26773(10) 0.0758(7) Uani d . 1
H H26 0.0722 0.9765 0.2637 0.091 Uiso calc R 1
C C27 0.07268(10) 0.7732(2) 0.23192(10) 0.0720(6) Uani d . 1
H H27 0.0430 0.7876 0.2035 0.086 Uiso calc R 1
C C28 0.09885(9) 0.6396(2) 0.23788(9) 0.0620(5) Uani d . 1
H H28 0.0868 0.5641 0.2133 0.074 Uiso calc R 1
C C29 0.17786(8) 0.37337(19) 0.23733(8) 0.0532(5) Uani d . 1
C C210 0.18628(9) 0.4333(2) 0.18346(8) 0.0666(6) Uani d . 1
H H210 0.1890 0.5336 0.1790 0.080 Uiso calc R 1
C C211 0.19057(11) 0.3423(3) 0.13692(10) 0.0781(6) Uani d . 1
H H211 0.1953 0.3808 0.1004 0.094 Uiso calc R 1
C C212 0.18792(10) 0.1954(3) 0.14452(10) 0.0742(6) Uani d . 1
H H212 0.1901 0.1324 0.1133 0.089 Uiso calc R 1
C C213 0.18198(10) 0.1423(2) 0.19957(10) 0.0717(6) Uani d . 1
H H213 0.1815 0.0420 0.2050 0.086 Uiso calc R 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 0 '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 0.006 '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
C11 N11 H11A 120.0 ?
C11 N11 H11B 120.0 ?
H11A N11 H11B 120.0 ?
C11 N12 N13 118.90(14) y
C11 N12 H12 120.6 ?
N13 N12 H12 120.6 ?
C12 N13 N12 120.51(15) y
C19 N14 C113 117.91(17) ?
O1 C11 N11 123.66(17) y
O1 C11 N12 119.14(15) y
N11 C11 N12 117.18(15) ?
N13 C12 C19 126.72(16) ?
N13 C12 C13 113.21(15) ?
C19 C12 C13 120.07(15) ?
C18 C13 C14 117.82(16) ?
C18 C13 C12 121.83(16) ?
C14 C13 C12 120.23(16) ?
C15 C14 C13 120.76(19) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C14 C15 C16 120.3(2) ?
C14 C15 H15 119.8 ?
C16 C15 H15 119.8 ?
C17 C16 C15 119.63(19) ?
C17 C16 H16 120.2 ?
C15 C16 H16 120.2 ?
C16 C17 C18 120.4(2) ?
C16 C17 H17 119.8 ?
C18 C17 H17 119.8 ?
C17 C18 C13 121.05(19) ?
C17 C18 H18 119.5 ?
C13 C18 H18 119.5 ?
N14 C19 C110 121.19(17) ?
N14 C19 C12 117.39(16) ?
C110 C19 C12 121.42(16) ?
C111 C110 C19 119.2(2) ?
C111 C110 H110 120.4 ?
C19 C110 H110 120.4 ?
C112 C111 C110 119.9(2) ?
C112 C111 H111 120.0 ?
C110 C111 H111 120.0 ?
C113 C112 C111 118.0(2) ?
C113 C112 H112 121.0 ?
C111 C112 H112 121.0 ?
N14 C113 C112 123.7(2) ?
N14 C113 H113 118.1 ?
C112 C113 H113 118.1 ?
C21 N21 H21A 120.0 ?
C21 N21 H21B 120.0 ?
H21A N21 H21B 120.0 ?
C21 N22 N23 118.96(14) y
C21 N22 H22 120.5 ?
N23 N22 H22 120.5 ?
C22 N23 N22 120.40(14) y
C29 N24 C213 118.09(17) ?
O2 C21 N21 123.56(16) y
O2 C21 N22 119.28(15) y
N21 C21 N22 117.14(14) ?
N23 C22 C23 114.15(15) ?
N23 C22 C29 126.16(15) ?
C23 C22 C29 119.68(15) ?
C28 C23 C24 117.99(16) ?
C28 C23 C22 121.42(16) ?
C24 C23 C22 120.56(16) ?
C25 C24 C23 120.56(19) ?
C25 C24 H24 119.7 ?
C23 C24 H24 119.7 ?
C26 C25 C24 120.4(2) ?
C26 C25 H25 119.8 ?
C24 C25 H25 119.8 ?
C25 C26 C27 119.81(19) ?
C25 C26 H26 120.1 ?
C27 C26 H26 120.1 ?
C28 C27 C26 120.2(2) ?
C28 C27 H27 119.9 ?
C26 C27 H27 119.9 ?
C27 C28 C23 121.07(19) ?
C27 C28 H28 119.5 ?
C23 C28 H28 119.5 ?
N24 C29 C210 121.71(17) ?
N24 C29 C22 117.71(16) ?
C210 C29 C22 120.57(17) ?
C211 C210 C29 119.1(2) ?
C211 C210 H210 120.5 ?
C29 C210 H210 120.5 ?
C212 C211 C210 119.7(2) ?
C212 C211 H211 120.1 ?
C210 C211 H211 120.1 ?
C211 C212 C213 118.48(19) ?
C211 C212 H212 120.8 ?
C213 C212 H212 120.8 ?
N24 C213 C212 122.8(2) ?
N24 C213 H213 118.6 ?
C212 C213 H213 118.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 1.2360(19) y
N11 C11 1.321(2) y
N11 H11A 0.8600 ?
N11 H11B 0.8600 ?
N12 C11 1.364(2) y
N12 N13 1.3705(19) y
N12 H12 0.8600 ?
N13 C12 1.294(2) y
N14 C19 1.342(2) ?
N14 C113 1.349(3) ?
C12 C19 1.484(2) y
C12 C13 1.493(2) y
C13 C18 1.392(2) ?
C13 C14 1.393(3) ?
C14 C15 1.376(3) ?
C14 H14 0.9300 ?
C15 C16 1.378(3) ?
C15 H15 0.9300 ?
C16 C17 1.371(3) ?
C16 H16 0.9300 ?
C17 C18 1.371(3) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
C19 C110 1.386(3) ?
C110 C111 1.375(3) ?
C110 H110 0.9300 ?
C111 C112 1.366(3) ?
C111 H111 0.9300 ?
C112 C113 1.362(3) ?
C112 H112 0.9300 ?
C113 H113 0.9300 ?
O2 C21 1.2390(19) y
N21 C21 1.321(2) y
N21 H21A 0.8600 ?
N21 H21B 0.8600 ?
N22 C21 1.364(2) y
N22 N23 1.3665(18) y
N22 H22 0.8600 ?
N23 C22 1.295(2) y
N24 C29 1.339(2) ?
N24 C213 1.343(3) ?
C22 C23 1.487(2) y
C22 C29 1.490(2) y
C23 C28 1.390(2) ?
C23 C24 1.392(3) ?
C24 C25 1.378(3) ?
C24 H24 0.9300 ?
C25 C26 1.371(3) ?
C25 H25 0.9300 ?
C26 C27 1.374(3) ?
C26 H26 0.9300 ?
C27 C28 1.370(3) ?
C27 H27 0.9300 ?
C28 H28 0.9300 ?
C29 C210 1.388(3) ?
C210 C211 1.372(3) ?
C210 H210 0.9300 ?
C211 C212 1.363(3) ?
C211 H211 0.9300 ?
C212 C213 1.380(3) ?
C212 H212 0.9300 ?
C213 H213 0.9300 ?
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
_geom_hbond_publ_flag
N11 H11A O1 7_555 0.860 2.169 3.029(2) 178.0 y
N11 H11B O2 4_555 0.860 2.332 2.917(2) 125.5 y
N21 H21B O1 4_555 0.860 2.273 2.883(2) 128.0 y
N21 H21A O2 7_556 0.860 2.150 3.005(2) 172.9 y
N12 H12 N14 . 0.860 2.055 2.683(2) 129.2 y
N22 H22 N24 . 0.860 2.095 2.712(2) 128.2 y
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
C11 N12 N13 C12 178.38(16)
N13 N12 C11 O1 -174.77(15)
N13 N12 C11 N11 7.2(2)
N12 N13 C12 C19 1.8(3)
N12 N13 C12 C13 -178.45(15)
N13 C12 C13 C18 142.89(18)
C19 C12 C13 C18 -37.3(3)
N13 C12 C13 C14 -33.1(2)
C19 C12 C13 C14 146.70(18)
C18 C13 C14 C15 0.6(3)
C12 C13 C14 C15 176.71(19)
C13 C14 C15 C16 -1.1(3)
C14 C15 C16 C17 1.4(3)
C15 C16 C17 C18 -1.2(3)
C16 C17 C18 C13 0.8(3)
C14 C13 C18 C17 -0.4(3)
C12 C13 C18 C17 -176.51(18)
C113 N14 C19 C110 1.3(3)
C113 N14 C19 C12 -179.70(17)
N13 C12 C19 N14 -24.8(3)
C13 C12 C19 N14 155.40(16)
N13 C12 C19 C110 154.13(19)
C13 C12 C19 C110 -25.6(3)
N14 C19 C110 C111 -1.9(3)
C12 C19 C110 C111 179.14(18)
C19 C110 C111 C112 0.8(3)
C110 C111 C112 C113 0.9(3)
C19 N14 C113 C112 0.4(3)
C111 C112 C113 N14 -1.6(3)
C21 N22 N23 C22 -178.29(16)
N23 N22 C21 O2 176.43(15)
N23 N22 C21 N21 -5.0(2)
N22 N23 C22 C23 178.90(15)
N22 N23 C22 C29 -1.2(3)
N23 C22 C23 C28 -145.14(19)
C29 C22 C23 C28 34.9(3)
N23 C22 C23 C24 32.8(3)
C29 C22 C23 C24 -147.07(18)
C28 C23 C24 C25 0.4(3)
C22 C23 C24 C25 -177.65(18)
C23 C24 C25 C26 0.0(3)
C24 C25 C26 C27 -0.3(3)
C25 C26 C27 C28 0.2(3)
C26 C27 C28 C23 0.2(3)
C24 C23 C28 C27 -0.5(3)
C22 C23 C28 C27 177.56(19)
C213 N24 C29 C210 -2.5(3)
C213 N24 C29 C22 178.06(18)
N23 C22 C29 N24 29.3(3)
C23 C22 C29 N24 -150.77(17)
N23 C22 C29 C210 -150.11(19)
C23 C22 C29 C210 29.8(3)
N24 C29 C210 C211 3.5(3)
C22 C29 C210 C211 -177.08(19)
C29 C210 C211 C212 -1.6(3)
C210 C211 C212 C213 -1.2(3)
C29 N24 C213 C212 -0.4(3)
C211 C212 C213 N24 2.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7838777
