#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/70/2207053.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_2207053
loop_
_publ_author_name
'Ming Yu'
'Zhi Fan'
'Zuo-Liang Jing'
'Xin Chen'
'Chun-Hua Diao'
'Qi-Liang Deng'
_publ_section_title
;
 N-(2,4-Dinitrophenyl)-N'-(2-pyridylmethylene)hydrazine
;
_journal_coeditor_code           RZ6111
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3342
_journal_page_last               o3343
_journal_paper_doi               10.1107/S160053680502934X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H9 N5 O4'
_chemical_formula_moiety         'C12 H9 N5 O4'
_chemical_formula_sum            'C12 H9 N5 O4'
_chemical_formula_weight         287.24
_chemical_name_common
;
N-(2,4-Dinitrophenyl)-N'-(2-pyridylmethylene)hydrazine
;
_chemical_name_systematic
;
pyridine-2-carbaldehyde 2,4-dinitrophenylhydrazone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.532(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5690(18)
_cell_length_b                   6.3333(13)
_cell_length_c                   23.340(5)
_cell_measurement_reflns_used    1875
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      2.91
_cell_volume                     1266.2(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6807
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0401
_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)+(0.0543P)²+0.1982P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                1567
_reflns_number_total             2564
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6111.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      'P 21/c'
_cod_database_code               2207053
_cod_database_fobs_code          2207053
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
O1 0.26494(16) 0.2947(2) 0.23555(6) 0.0596(4) Uani d . 1 O
O2 0.40822(19) 0.0197(3) 0.24571(6) 0.0798(5) Uani d . 1 O
O3 0.6692(2) -0.1588(3) 0.41983(8) 0.0844(6) Uani d . 1 O
O4 0.67334(18) 0.0620(3) 0.49017(7) 0.0762(5) Uani d . 1 O
N1 -0.06722(18) 1.1709(2) 0.31995(7) 0.0527(4) Uani d . 1 N
N2 0.18293(17) 0.7369(2) 0.34905(7) 0.0438(4) Uani d . 1 N
N3 0.23738(17) 0.5665(2) 0.31952(7) 0.0447(4) Uani d D 1 N
N4 0.35286(18) 0.1818(3) 0.26474(7) 0.0455(4) Uani d . 1 N
N5 0.6303(2) 0.0074(3) 0.44178(8) 0.0574(5) Uani d . 1 N
C1 -0.1236(2) 1.3413(3) 0.34645(11) 0.0629(6) Uani d . 1 C
H1 -0.1865 1.4329 0.3249 0.075 Uiso calc R 1 H
C2 -0.0952(3) 1.3901(3) 0.40282(11) 0.0656(6) Uani d . 1 C
H2 -0.1377 1.5107 0.4189 0.079 Uiso calc R 1 H
C3 -0.0030(3) 1.2570(4) 0.43476(10) 0.0662(6) Uani d . 1 C
H3 0.0192 1.2861 0.4732 0.079 Uiso calc R 1 H
C4 0.0568(2) 1.0800(3) 0.40959(8) 0.0528(5) Uani d . 1 C
H4 0.1189 0.9867 0.4309 0.063 Uiso calc R 1 H
C5 0.02352(19) 1.0417(3) 0.35219(8) 0.0407(4) Uani d . 1 C
C6 0.0859(2) 0.8572(3) 0.32272(8) 0.0431(5) Uani d . 1 C
H6 0.0549 0.8280 0.2851 0.052 Uiso calc R 1 H
C7 0.3331(2) 0.4275(3) 0.34758(7) 0.0399(4) Uani d . 1 C
C8 0.39047(19) 0.2404(3) 0.32318(7) 0.0369(4) Uani d . 1 C
C9 0.48744(19) 0.1024(3) 0.35370(8) 0.0415(4) Uani d . 1 C
H9 0.5242 -0.0198 0.3366 0.050 Uiso calc R 1 H
C10 0.5279(2) 0.1491(3) 0.40914(8) 0.0447(5) Uani d . 1 C
C11 0.4739(3) 0.3304(3) 0.43502(9) 0.0599(6) Uani d . 1 C
H11 0.5024 0.3593 0.4729 0.072 Uiso calc R 1 H
C12 0.3794(2) 0.4666(3) 0.40538(8) 0.0564(6) Uani d . 1 C
H12 0.3443 0.5879 0.4234 0.068 Uiso calc R 1 H
H3A 0.209(2) 0.541(3) 0.2831(5) 0.050(6) Uiso d 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
C1 N1 C5 116.21(18)
C6 N2 N3 117.09(16)
C7 N3 N2 118.51(15)
C7 N3 H3A 119.4(12)
N2 N3 H3A 122.1(12)
O2 N4 O1 121.70(16)
O2 N4 C8 118.80(16)
O1 N4 C8 119.49(15)
O3 N5 O4 123.36(19)
O3 N5 C10 118.63(18)
O4 N5 C10 118.01(18)
N1 C1 C2 124.7(2)
N1 C1 H1 117.7
C2 C1 H1 117.7
C3 C2 C1 118.2(2)
C3 C2 H2 120.9
C1 C2 H2 120.9
C2 C3 C4 119.2(2)
C2 C3 H3 120.4
C4 C3 H3 120.4
C3 C4 C5 119.25(19)
C3 C4 H4 120.4
C5 C4 H4 120.4
N1 C5 C4 122.42(18)
N1 C5 C6 115.81(17)
C4 C5 C6 121.76(17)
N2 C6 C5 119.50(17)
N2 C6 H6 120.3
C5 C6 H6 120.3
N3 C7 C8 124.21(16)
N3 C7 C12 119.68(17)
C8 C7 C12 116.11(16)
C9 C8 C7 122.13(16)
C9 C8 N4 116.04(15)
C7 C8 N4 121.83(16)
C10 C9 C8 118.95(17)
C10 C9 H9 120.5
C8 C9 H9 120.5
C9 C10 C11 121.00(17)
C9 C10 N5 119.84(17)
C11 C10 N5 119.16(17)
C12 C11 C10 120.42(18)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C7 121.39(18)
C11 C12 H12 119.3
C7 C12 H12 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N4 1.2309(19)
O2 N4 1.2200(19)
O3 N5 1.221(2)
O4 N5 1.228(2)
N1 C1 1.341(3)
N1 C5 1.345(2)
N2 C6 1.274(2)
N2 N3 1.369(2)
N3 C7 1.360(2)
N3 H3A 0.894(9)
N4 C8 1.441(2)
N5 C10 1.456(2)
C1 C2 1.367(3)
C1 H1 0.9300
C2 C3 1.364(3)
C2 H2 0.9300
C3 C4 1.371(3)
C3 H3 0.9300
C4 C5 1.384(3)
C4 H4 0.9300
C5 C6 1.465(2)
C6 H6 0.9300
C7 C8 1.409(2)
C7 C12 1.418(2)
C8 C9 1.389(2)
C9 C10 1.363(2)
C9 H9 0.9300
C10 C11 1.383(3)
C11 C12 1.360(3)
C11 H11 0.9300
C12 H12 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
N3 H3A O1 . 0.894(9) 1.982(16) 2.624(2) 127.5(15)
C4 H4 O4 3_666 0.93 2.55 3.368(2) 147
C1 H1 O2 2_565 0.93 2.54 3.402(3) 154
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
C6 N2 N3 C7 -175.76(16)
C5 N1 C1 C2 -0.1(3)
N1 C1 C2 C3 0.1(3)
C1 C2 C3 C4 -0.4(3)
C2 C3 C4 C5 0.8(3)
C1 N1 C5 C4 0.4(3)
C1 N1 C5 C6 -179.39(16)
C3 C4 C5 N1 -0.8(3)
C3 C4 C5 C6 179.03(18)
N3 N2 C6 C5 179.91(15)
N1 C5 C6 N2 174.29(16)
C4 C5 C6 N2 -5.5(3)
N2 N3 C7 C8 176.51(15)
N2 N3 C7 C12 -2.7(3)
N3 C7 C8 C9 -179.62(16)
C12 C7 C8 C9 -0.4(2)
N3 C7 C8 N4 0.9(3)
C12 C7 C8 N4 -179.81(16)
O2 N4 C8 C9 -0.7(2)
O1 N4 C8 C9 178.54(16)
O2 N4 C8 C7 178.76(17)
O1 N4 C8 C7 -2.0(2)
C7 C8 C9 C10 0.3(3)
N4 C8 C9 C10 179.75(16)
C8 C9 C10 C11 0.0(3)
C8 C9 C10 N5 -179.57(16)
O3 N5 C10 C9 -5.1(3)
O4 N5 C10 C9 174.85(18)
O3 N5 C10 C11 175.33(19)
O4 N5 C10 C11 -4.8(3)
C9 C10 C11 C12 -0.3(3)
N5 C10 C11 C12 179.36(19)
C10 C11 C12 C7 0.2(3)
N3 C7 C12 C11 179.44(19)
C8 C7 C12 C11 0.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7844146
