#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239129.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2239129
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Chantrapromma, Suchada'
'Ruanwas, Pumsak'
'Kobkeatthawin, Thawanrat'
'Chidan Kumar, C. S.'
_publ_section_title
;
 (E)-1-(2,4-Dinitrophenyl)-2-(3-ethoxy-4-hydroxybenzylidene)hydrazine
;
_journal_coeditor_code           HB7175
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o89
_journal_page_last               o90
_journal_paper_doi               10.1107/S1600536813033989
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C15 H14 N4 O6'
_chemical_formula_moiety         'C15 H14 N4 O6'
_chemical_formula_sum            'C15 H14 N4 O6'
_chemical_formula_weight         346.30
_chemical_melting_point_gt       515
_chemical_melting_point_lt       516
_chemical_name_systematic
;
(E)-1-(2,4-Dinitrophenyl)-2-(3-ethoxy-4-hydroxybenzylidene)hydrazine
;
_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                 129.15(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.245(4)
_cell_length_b                   13.679(5)
_cell_length_c                   14.184(5)
_cell_measurement_reflns_used    4060
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.99
_cell_measurement_theta_min      2.38
_cell_volume                     1541.5(11)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009),
Mercury (Macrae et al., 2006) and publCIF (Westrip,
2010)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16113
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0566P)²+0.0702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                2183
_reflns_number_total             4060
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7175sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239129
_cod_database_fobs_code          2239129
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_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_symmetry_multiplicity
O O1 1.20079(13) -0.22891(8) 0.16025(12) 0.0622(4) Uani d . 1 1
O O2 1.05019(14) -0.35272(9) 0.13142(13) 0.0736(5) Uani d . 1 1
O O3 0.46877(15) -0.32518(12) -0.07366(14) 0.0814(5) Uani d . 1 1
O O4 0.36011(15) -0.18505(11) -0.08629(13) 0.0767(4) Uani d . 1 1
O O5 1.01832(12) 0.42468(8) 0.13492(11) 0.0532(3) Uani d . 1 1
O O6 1.32309(16) 0.49799(9) 0.24070(13) 0.0580(4) Uani d . 1 1
H H1O6 1.230(3) 0.5246(19) 0.209(2) 0.121(10) Uiso d . 1 1
N N1 1.09605(18) -0.05017(10) 0.15152(14) 0.0489(4) Uani d . 1 1
H H1N1 1.183(2) -0.0854(13) 0.1800(17) 0.065(6) Uiso d . 1 1
N N2 1.10133(17) 0.05030(9) 0.15757(13) 0.0472(4) Uani d . 1 1
N N3 1.06865(16) -0.26439(10) 0.13050(13) 0.0494(4) Uani d . 1 1
N N4 0.47883(17) -0.23628(13) -0.05806(14) 0.0594(4) Uani d . 1 1
C C1 0.94828(19) -0.09698(11) 0.10069(14) 0.0411(4) Uani d . 1 1
C C2 0.93039(18) -0.19991(11) 0.09135(14) 0.0409(4) Uani d . 1 1
C C3 0.77777(19) -0.24509(12) 0.04025(14) 0.0452(4) Uani d . 1 1
H H3A 0.7692 -0.3129 0.0357 0.054 Uiso calc R 1 1
C C4 0.63954(19) -0.18842(12) -0.00355(15) 0.0463(4) Uani d . 1 1
C C5 0.6511(2) -0.08732(13) 0.00279(16) 0.0523(5) Uani d . 1 1
H H5A 0.5558 -0.0499 -0.0284 0.063 Uiso calc R 1 1
C C6 0.8015(2) -0.04225(12) 0.05462(16) 0.0509(4) Uani d . 1 1
H H6A 0.8077 0.0256 0.0598 0.061 Uiso calc R 1 1
C C7 1.2451(2) 0.08997(12) 0.20969(15) 0.0474(4) Uani d . 1 1
H H7A 1.3388 0.0507 0.2419 0.057 Uiso calc R 1 1
C C8 1.26408(19) 0.19596(11) 0.21919(14) 0.0432(4) Uani d . 1 1
C C9 1.12420(19) 0.25734(11) 0.17161(15) 0.0437(4) Uani d . 1 1
H H9A 1.0192 0.2301 0.1360 0.052 Uiso calc R 1 1
C C10 1.14273(18) 0.35742(11) 0.17773(15) 0.0432(4) Uani d . 1 1
C C11 1.30253(19) 0.39867(12) 0.23335(15) 0.0448(4) Uani d . 1 1
C C12 1.43888(19) 0.33878(12) 0.28036(16) 0.0510(5) Uani d . 1 1
H H12A 1.5442 0.3661 0.3172 0.061 Uiso calc R 1 1
C C13 1.42040(19) 0.23804(12) 0.27326(15) 0.0485(4) Uani d . 1 1
H H13A 1.5134 0.1982 0.3049 0.058 Uiso calc R 1 1
C C14 0.84992(18) 0.38972(12) 0.07237(16) 0.0509(4) Uani d . 1 1
H H14A 0.8445 0.3497 0.1263 0.061 Uiso calc R 1 1
H H14B 0.8145 0.3504 0.0029 0.061 Uiso calc R 1 1
C C15 0.7378(2) 0.47736(13) 0.03131(17) 0.0573(5) Uani d . 1 1
H H15A 0.6249 0.4563 -0.0071 0.086 Uiso calc R 1 1
H H15B 0.7392 0.5143 -0.0256 0.086 Uiso calc R 1 1
H H15C 0.7775 0.5175 0.1003 0.086 Uiso calc R 1 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
C10 O5 C14 118.10(12)
C11 O6 H1O6 108.7(18)
C1 N1 N2 119.40(13)
C1 N1 H1N1 117.7(12)
N2 N1 H1N1 122.9(12)
C7 N2 N1 116.45(14)
O2 N3 O1 121.84(13)
O2 N3 C2 118.99(13)
O1 N3 C2 119.17(14)
O3 N4 O4 123.46(15)
O3 N4 C4 118.54(14)
O4 N4 C4 118.00(17)
N1 C1 C2 123.64(14)
N1 C1 C6 119.91(15)
C2 C1 C6 116.45(14)
C3 C2 C1 121.96(14)
C3 C2 N3 115.85(14)
C1 C2 N3 122.15(13)
C4 C3 C2 119.08(16)
C4 C3 H3A 120.5
C2 C3 H3A 120.5
C3 C4 C5 120.88(15)
C3 C4 N4 118.90(16)
C5 C4 N4 120.22(14)
C6 C5 C4 120.41(15)
C6 C5 H5A 119.8
C4 C5 H5A 119.8
C5 C6 C1 121.21(16)
C5 C6 H6A 119.4
C1 C6 H6A 119.4
N2 C7 C8 120.86(15)
N2 C7 H7A 119.6
C8 C7 H7A 119.6
C13 C8 C9 119.05(15)
C13 C8 C7 120.17(15)
C9 C8 C7 120.77(14)
C10 C9 C8 120.21(14)
C10 C9 H9A 119.9
C8 C9 H9A 119.9
O5 C10 C9 126.10(14)
O5 C10 C11 114.04(14)
C9 C10 C11 119.86(14)
O6 C11 C12 119.61(14)
O6 C11 C10 120.53(14)
C12 C11 C10 119.86(15)
C11 C12 C13 120.44(15)
C11 C12 H12A 119.8
C13 C12 H12A 119.8
C12 C13 C8 120.57(15)
C12 C13 H13A 119.7
C8 C13 H13A 119.7
O5 C14 C15 107.50(14)
O5 C14 H14A 110.2
C15 C14 H14A 110.2
O5 C14 H14B 110.2
C15 C14 H14B 110.2
H14A C14 H14B 108.5
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.2349(16)
O2 N3 1.2243(17)
O3 N4 1.229(2)
O4 N4 1.2312(18)
O5 C10 1.3647(18)
O5 C14 1.4351(18)
O6 C11 1.369(2)
O6 H1O6 0.84(3)
N1 C1 1.358(2)
N1 N2 1.3759(18)
N1 H1N1 0.858(17)
N2 C7 1.279(2)
N3 C2 1.4490(19)
N4 C4 1.459(2)
C1 C2 1.415(2)
C1 C6 1.417(2)
C2 C3 1.386(2)
C3 C4 1.372(2)
C3 H3A 0.9300
C4 C5 1.386(2)
C5 C6 1.366(2)
C5 H5A 0.9300
C6 H6A 0.9300
C7 C8 1.458(2)
C7 H7A 0.9300
C8 C13 1.390(2)
C8 C9 1.412(2)
C9 C10 1.377(2)
C9 H9A 0.9300
C10 C11 1.411(2)
C11 C12 1.375(2)
C12 C13 1.386(2)
C12 H12A 0.9300
C13 H13A 0.9300
C14 C15 1.500(2)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 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
O6 H1O6 O2 1_565 0.84(3) 2.21(3) 2.986(2) 155(3) y
O6 H1O6 O5 1_555 0.84(3) 2.19(3) 2.663(3) 116(2) y
N1 H1N1 O1 1_555 0.86(2) 2.007(18) 2.641(2) 130.0(18) 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
C1 N1 N2 C7 177.98(15)
N2 N1 C1 C2 -179.34(15)
N2 N1 C1 C6 0.0(2)
N1 C1 C2 C3 179.14(16)
C6 C1 C2 C3 -0.2(2)
N1 C1 C2 N3 -3.1(3)
C6 C1 C2 N3 177.54(15)
O2 N3 C2 C3 -9.4(2)
O1 N3 C2 C3 169.55(15)
O2 N3 C2 C1 172.77(16)
O1 N3 C2 C1 -8.3(2)
C1 C2 C3 C4 0.6(2)
N3 C2 C3 C4 -177.29(15)
C2 C3 C4 C5 0.0(2)
C2 C3 C4 N4 179.57(15)
O3 N4 C4 C3 -7.0(2)
O4 N4 C4 C3 173.20(15)
O3 N4 C4 C5 172.60(17)
O4 N4 C4 C5 -7.2(2)
C3 C4 C5 C6 -1.0(3)
N4 C4 C5 C6 179.47(16)
C4 C5 C6 C1 1.4(3)
N1 C1 C6 C5 179.86(16)
C2 C1 C6 C5 -0.8(2)
N1 N2 C7 C8 178.99(14)
N2 C7 C8 C13 -178.30(15)
N2 C7 C8 C9 0.3(2)
C13 C8 C9 C10 0.7(2)
C7 C8 C9 C10 -177.94(16)
C14 O5 C10 C9 -3.1(2)
C14 O5 C10 C11 177.49(14)
C8 C9 C10 O5 179.66(15)
C8 C9 C10 C11 -0.9(2)
O5 C10 C11 O6 -0.2(2)
C9 C10 C11 O6 -179.65(15)
O5 C10 C11 C12 179.98(15)
C9 C10 C11 C12 0.5(3)
O6 C11 C12 C13 -179.69(16)
C10 C11 C12 C13 0.1(3)
C11 C12 C13 C8 -0.4(3)
C9 C8 C13 C12 -0.1(2)
C7 C8 C13 C12 178.60(16)
C10 O5 C14 C15 -178.05(14)
