#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/08/2220883.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_2220883
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Kia, Reza'
'Kargar, Hadi'
_publ_section_title
;
 2-Methoxybenzaldehyde 2,4-dinitrophenylhydrazone
;
_journal_coeditor_code           PK2139
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o246
_journal_page_last               o247
_journal_paper_doi               10.1107/S1600536809000038
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H12 N4 O5'
_chemical_formula_moiety         'C14 H12 N4 O5'
_chemical_formula_sum            'C14 H12 N4 O5'
_chemical_formula_weight         316.28
_chemical_name_systematic
;
2-Methoxybenzaldehyde 2,4-dinitrophenylhydrazone
;
_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           SHELXL97
_cell_angle_alpha                98.0480(10)
_cell_angle_beta                 97.0640(10)
_cell_angle_gamma                109.4670(10)
_cell_formula_units_Z            2
_cell_length_a                   7.03150(10)
_cell_length_b                   7.6205(2)
_cell_length_c                   14.1896(4)
_cell_measurement_reflns_used    6651
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      40.25
_cell_measurement_theta_min      2.89
_cell_volume                     697.99(3)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEXII 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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14423
_diffrn_reflns_theta_full        32.49
_diffrn_reflns_theta_max         32.49
_diffrn_reflns_theta_min         1.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         5023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0683P)²+0.1626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1260
_reflns_number_gt                4442
_reflns_number_total             5023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2139.cif
_cod_data_source_block           I
_cod_database_code               2220883
_cod_database_fobs_code          2220883
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.52355(11) 0.19077(9) 0.30740(5) 0.01789(14) Uani d . 1 . .
O O2 0.31793(12) 0.47602(10) -0.06604(5) 0.02132(15) Uani d . 1 . .
O O3 0.20422(12) 0.51054(10) -0.20851(5) 0.02350(16) Uani d . 1 . .
O O4 -0.18137(11) -0.00408(11) -0.45869(5) 0.02104(15) Uani d . 1 . .
O O5 -0.19171(12) -0.28928(10) -0.44929(5) 0.02410(16) Uani d . 1 . .
N N1 0.27092(11) 0.00256(11) 0.02604(5) 0.01410(14) Uani d . 1 . .
N N2 0.26656(12) 0.13732(11) -0.02830(5) 0.01416(14) Uani d . 1 . .
N N3 0.22761(12) 0.40930(10) -0.15138(6) 0.01487(15) Uani d . 1 . .
N N4 -0.14093(12) -0.11921(11) -0.41450(5) 0.01611(15) Uani d . 1 . .
C C1 0.46732(13) 0.00043(12) 0.27560(6) 0.01377(15) Uani d . 1 . .
C C2 0.48758(14) -0.12628(13) 0.33510(6) 0.01710(17) Uani d . 1 . .
H H2A 0.5476 -0.0815 0.4001 0.021 Uiso calc R 1 . .
C C3 0.41767(15) -0.31935(14) 0.29676(7) 0.01947(18) Uani d . 1 . .
H H3A 0.4306 -0.4035 0.3365 0.023 Uiso calc R 1 . .
C C4 0.32856(14) -0.38821(13) 0.19954(7) 0.01804(17) Uani d . 1 . .
H H4A 0.2814 -0.5177 0.1745 0.022 Uiso calc R 1 . .
C C5 0.31052(13) -0.26234(12) 0.14015(6) 0.01530(16) Uani d . 1 . .
H H5A 0.2514 -0.3085 0.0751 0.018 Uiso calc R 1 . .
C C6 0.38009(12) -0.06701(12) 0.17671(6) 0.01284(15) Uani d . 1 . .
C C7 0.36703(13) 0.06671(12) 0.11394(6) 0.01371(15) Uani d . 1 . .
H H7A 0.4276 0.1967 0.1373 0.016 Uiso calc R 1 . .
C C8 0.17242(12) 0.07996(12) -0.12228(6) 0.01178(15) Uani d . 1 . .
C C9 0.09189(13) -0.11672(12) -0.16426(6) 0.01378(15) Uani d . 1 . .
H H9A 0.1056 -0.2038 -0.1266 0.017 Uiso calc R 1 . .
C C10 -0.00529(13) -0.18102(12) -0.25882(6) 0.01405(15) Uani d . 1 . .
H H10A -0.0547 -0.3101 -0.2852 0.017 Uiso calc R 1 . .
C C11 -0.02975(12) -0.05112(12) -0.31553(6) 0.01291(15) Uani d . 1 . .
C C12 0.04681(12) 0.14065(12) -0.27956(6) 0.01311(15) Uani d . 1 . .
H H12A 0.0307 0.2253 -0.3184 0.016 Uiso calc R 1 . .
C C13 0.14893(12) 0.20609(11) -0.18400(6) 0.01222(15) Uani d . 1 . .
C C14 0.64623(15) 0.27271(14) 0.40200(7) 0.01993(18) Uani d . 1 . .
H H14A 0.6876 0.4084 0.4120 0.030 Uiso calc R 1 . .
H H14B 0.7657 0.2377 0.4074 0.030 Uiso calc R 1 . .
H H14C 0.5675 0.2269 0.4500 0.030 Uiso calc R 1 . .
H H1N2 0.329(2) 0.256(2) -0.0027(11) 0.035(4) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C14 . . 118.36(7) ?
C7 N1 N2 . . 115.65(7) ?
C8 N2 N1 . . 118.87(7) ?
C8 N2 H1N2 . . 121.6(10) ?
N1 N2 H1N2 . . 119.4(10) ?
O3 N3 O2 . . 122.20(7) ?
O3 N3 C13 . . 119.09(7) ?
O2 N3 C13 . . 118.71(7) ?
O5 N4 O4 . . 123.66(8) ?
O5 N4 C11 . . 118.19(7) ?
O4 N4 C11 . . 118.15(7) ?
O1 C1 C2 . . 123.98(8) ?
O1 C1 C6 . . 115.86(7) ?
C2 C1 C6 . . 120.14(8) ?
C3 C2 C1 . . 119.74(8) ?
C3 C2 H2A . . 120.1 ?
C1 C2 H2A . . 120.1 ?
C2 C3 C4 . . 120.73(8) ?
C2 C3 H3A . . 119.6 ?
C4 C3 H3A . . 119.6 ?
C5 C4 C3 . . 119.58(8) ?
C5 C4 H4A . . 120.2 ?
C3 C4 H4A . . 120.2 ?
C4 C5 C6 . . 120.96(8) ?
C4 C5 H5A . . 119.5 ?
C6 C5 H5A . . 119.5 ?
C5 C6 C1 . . 118.84(8) ?
C5 C6 C7 . . 121.21(7) ?
C1 C6 C7 . . 119.95(7) ?
N1 C7 C6 . . 119.25(8) ?
N1 C7 H7A . . 120.4 ?
C6 C7 H7A . . 120.4 ?
N2 C8 C9 . . 119.67(7) ?
N2 C8 C13 . . 123.82(7) ?
C9 C8 C13 . . 116.51(7) ?
C10 C9 C8 . . 121.61(8) ?
C10 C9 H9A . . 119.2 ?
C8 C9 H9A . . 119.2 ?
C9 C10 C11 . . 119.52(8) ?
C9 C10 H10A . . 120.2 ?
C11 C10 H10A . . 120.2 ?
C12 C11 C10 . . 121.62(8) ?
C12 C11 N4 . . 118.64(7) ?
C10 C11 N4 . . 119.74(7) ?
C11 C12 C13 . . 118.80(8) ?
C11 C12 H12A . . 120.6 ?
C13 C12 H12A . . 120.6 ?
C12 C13 C8 . . 121.90(7) ?
C12 C13 N3 . . 115.84(7) ?
C8 C13 N3 . . 122.26(7) ?
O1 C14 H14A . . 109.5 ?
O1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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
O1 C1 . 1.3618(11) ?
O1 C14 . 1.4344(11) ?
O2 N3 . 1.2456(10) ?
O3 N3 . 1.2274(10) ?
O4 N4 . 1.2329(10) ?
O5 N4 . 1.2328(10) ?
N1 C7 . 1.2858(11) ?
N1 N2 . 1.3736(10) ?
N2 C8 . 1.3545(10) ?
N2 H1N2 . 0.864(16) ?
N3 C13 . 1.4435(11) ?
N4 C11 . 1.4520(11) ?
C1 C2 . 1.3985(12) ?
C1 C6 . 1.4092(11) ?
C2 C3 . 1.3894(14) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.3916(13) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.3883(13) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.4001(12) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.4617(12) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.4224(11) ?
C8 C13 . 1.4227(11) ?
C9 C10 . 1.3692(11) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.3998(12) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.3730(12) ?
C12 C13 . 1.3912(11) ?
C12 H12A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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
N2 H1N2 O2 . 0.864(15) 2.029(15) 2.6253(11) 125.4(13) y
N2 H1N2 O2 2_665 0.864(15) 2.599(15) 3.3475(11) 145.6(13) y
C2 H2A O4 1_656 0.9300 2.4400 3.3113(12) 155.00 y
C5 H5A O2 1_545 0.9300 2.6000 3.3184(11) 135.00 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 N2 C8 . . . . 178.35(7) ?
C14 O1 C1 C2 . . . . 12.61(13) ?
C14 O1 C1 C6 . . . . -168.81(8) ?
O1 C1 C2 C3 . . . . 177.25(8) ?
C6 C1 C2 C3 . . . . -1.27(13) ?
C1 C2 C3 C4 . . . . 0.36(14) ?
C2 C3 C4 C5 . . . . 0.38(14) ?
C3 C4 C5 C6 . . . . -0.21(14) ?
C4 C5 C6 C1 . . . . -0.69(13) ?
C4 C5 C6 C7 . . . . 178.17(8) ?
O1 C1 C6 C5 . . . . -177.21(7) ?
C2 C1 C6 C5 . . . . 1.43(13) ?
O1 C1 C6 C7 . . . . 3.91(12) ?
C2 C1 C6 C7 . . . . -177.45(8) ?
N2 N1 C7 C6 . . . . -179.67(7) ?
C5 C6 C7 N1 . . . . 7.29(13) ?
C1 C6 C7 N1 . . . . -173.86(8) ?
N1 N2 C8 C9 . . . . -3.93(12) ?
N1 N2 C8 C13 . . . . 176.55(8) ?
N2 C8 C9 C10 . . . . 179.68(8) ?
C13 C8 C9 C10 . . . . -0.77(12) ?
C8 C9 C10 C11 . . . . -1.15(13) ?
C9 C10 C11 C12 . . . . 1.96(13) ?
C9 C10 C11 N4 . . . . -177.18(8) ?
O5 N4 C11 C12 . . . . 173.05(8) ?
O4 N4 C11 C12 . . . . -7.77(12) ?
O5 N4 C11 C10 . . . . -7.78(12) ?
O4 N4 C11 C10 . . . . 171.39(8) ?
C10 C11 C12 C13 . . . . -0.75(13) ?
N4 C11 C12 C13 . . . . 178.40(7) ?
C11 C12 C13 C8 . . . . -1.28(13) ?
C11 C12 C13 N3 . . . . 179.24(7) ?
N2 C8 C13 C12 . . . . -178.46(8) ?
C9 C8 C13 C12 . . . . 2.01(12) ?
N2 C8 C13 N3 . . . . 0.98(13) ?
C9 C8 C13 N3 . . . . -178.55(7) ?
O3 N3 C13 C12 . . . . -1.30(12) ?
O2 N3 C13 C12 . . . . 178.99(8) ?
O3 N3 C13 C8 . . . . 179.23(8) ?
O2 N3 C13 C8 . . . . -0.48(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7844028
