#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/49/2224951.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_2224951
loop_
_publ_author_name
'Neunfeldt, Patrícia D.'
'Duval, Auri R.'
'Cunico, Wilson'
'Wardell, Solange M. S. V.'
'Tiekink, Edward R. T.'
'Wardell, James L.'
_publ_section_title
;
 (E)-1-(2,4-Dinitrophenyl)-2-pentylidenehydrazine
;
_journal_coeditor_code           FJ2271
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o483
_journal_page_last               o484
_journal_paper_doi               10.1107/S1600536810002102
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H14 N4 O4'
_chemical_formula_moiety         'C11 H14 N4 O4'
_chemical_formula_sum            'C11 H14 N4 O4'
_chemical_formula_weight         266.26
_chemical_name_systematic
;
(E)-1-(2,4-Dinitrophenyl)-2-pentylidenehydrazine
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 106.159(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.162(3)
_cell_length_b                   4.4930(4)
_cell_length_c                   18.7329(14)
_cell_measurement_reflns_used    14843
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     2519.2(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  '-Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.115
_diffrn_reflns_av_sigmaI/netI    0.084
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8172
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.10
_refine_ls_R_factor_all          0.124
_refine_ls_R_factor_gt           0.078
_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)+(0.0406P)²+14.6755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.157
_refine_ls_wR_factor_ref         0.183
_reflns_number_gt                1451
_reflns_number_total             2174
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2271.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2224951
_cod_database_fobs_code          2224951
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.04985(11) -0.5722(7) 0.23571(16) 0.0294(8) Uani d . 1 . .
O O2 0.11770(10) -0.4264(8) 0.24360(16) 0.0360(9) Uani d . 1 . .
O O3 -0.03340(10) -0.1033(7) 0.37999(16) 0.0263(8) Uani d . 1 . .
O O4 -0.00644(9) 0.2652(7) 0.45386(15) 0.0240(7) Uani d . 1 . .
N N1 0.07910(11) 0.3841(8) 0.49031(18) 0.0194(8) Uani d . 1 . .
H H1N 0.0551(14) 0.401(10) 0.505(2) 0.023 Uiso d . 1 . .
N N2 0.11897(11) 0.5276(8) 0.52633(18) 0.0224(9) Uani d . 1 . .
N N3 0.08254(13) -0.4163(9) 0.26201(19) 0.0267(9) Uani d . 1 . .
N N4 -0.00244(11) 0.0661(8) 0.41033(19) 0.0213(8) Uani d . 1 . .
C C1 0.07833(13) 0.2003(10) 0.4333(2) 0.0197(10) Uani d . 1 . .
C C2 0.04022(13) 0.0353(10) 0.3940(2) 0.0185(9) Uani d . 1 . .
C C3 0.04158(14) -0.1701(9) 0.3391(2) 0.0191(9) Uani d . 1 . .
H H3 0.0161 -0.2868 0.3159 0.023 Uiso calc R 1 . .
C C4 0.08074(14) -0.2003(10) 0.3192(2) 0.0222(10) Uani d . 1 . .
C C5 0.11852(14) -0.0324(10) 0.3534(2) 0.0242(10) Uani d . 1 . .
H H5 0.1450 -0.0528 0.3381 0.029 Uiso calc R 1 . .
C C6 0.11736(14) 0.1613(10) 0.4090(2) 0.0230(10) Uani d . 1 . .
H H6 0.1434 0.2733 0.4321 0.028 Uiso calc R 1 . .
C C7 0.11826(14) 0.6629(11) 0.5855(2) 0.0248(10) Uani d . 1 . .
H H7 0.0922(15) 0.660(11) 0.604(2) 0.030 Uiso d . 1 . .
C C8 0.15800(14) 0.8254(11) 0.6307(2) 0.0281(11) Uani d . 1 . .
H H8A 0.1693 0.7207 0.6788 0.034 Uiso calc R 1 . .
H H8B 0.1485 1.0266 0.6415 0.034 Uiso calc R 1 . .
C C9 0.19629(14) 0.8581(12) 0.5957(2) 0.0292(11) Uani d . 1 . .
H H9A 0.2041 0.6593 0.5802 0.035 Uiso calc R 1 . .
H H9B 0.1863 0.9830 0.5505 0.035 Uiso calc R 1 . .
C C10 0.23763(15) 0.9966(13) 0.6476(3) 0.0382(13) Uani d . 1 . .
H H10A 0.2293 1.1896 0.6655 0.046 Uiso calc R 1 . .
H H10B 0.2485 0.8654 0.6914 0.046 Uiso calc R 1 . .
C C11 0.27528(16) 1.0479(14) 0.6126(3) 0.0481(15) Uani d . 1 . .
H H11A 0.2826 0.8602 0.5921 0.072 Uiso calc R 1 . .
H H11B 0.3016 1.1216 0.6503 0.072 Uiso calc R 1 . .
H H11C 0.2660 1.1951 0.5727 0.072 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 0.0000 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 N1 N2 . . 118.9(3) ?
C1 N1 H1N . . 119(3) ?
N2 N1 H1N . . 122(3) ?
C7 N2 N1 . . 114.4(3) ?
O1 N3 O2 . . 124.8(4) ?
O1 N3 C4 . . 118.7(3) ?
O2 N3 C4 . . 116.6(4) ?
O3 N4 O4 . . 122.6(3) ?
O3 N4 C2 . . 119.2(3) ?
O4 N4 C2 . . 118.2(3) ?
N1 C1 C2 . . 124.0(4) ?
N1 C1 C6 . . 120.1(4) ?
C2 C1 C6 . . 115.8(4) ?
C3 C2 C1 . . 122.5(4) ?
C3 C2 N4 . . 115.9(4) ?
C1 C2 N4 . . 121.6(4) ?
C4 C3 C2 . . 118.5(4) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
C3 C4 C5 . . 121.3(4) ?
C3 C4 N3 . . 118.8(4) ?
C5 C4 N3 . . 119.8(4) ?
C6 C5 C4 . . 119.8(4) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C1 . . 121.9(4) ?
C5 C6 H6 . . 119.0 ?
C1 C6 H6 . . 119.0 ?
N2 C7 C8 . . 121.3(4) ?
N2 C7 H7 . . 122(3) ?
C8 C7 H7 . . 117(3) ?
C7 C8 C9 . . 115.5(4) ?
C7 C8 H8A . . 108.4 ?
C9 C8 H8A . . 108.4 ?
C7 C8 H8B . . 108.4 ?
C9 C8 H8B . . 108.4 ?
H8A C8 H8B . . 107.5 ?
C10 C9 C8 . . 113.0(4) ?
C10 C9 H9A . . 109.0 ?
C8 C9 H9A . . 109.0 ?
C10 C9 H9B . . 109.0 ?
C8 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
C11 C10 C9 . . 114.0(4) ?
C11 C10 H10A . . 108.7 ?
C9 C10 H10A . . 108.7 ?
C11 C10 H10B . . 108.7 ?
C9 C10 H10B . . 108.7 ?
H10A C10 H10B . . 107.6 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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 N3 . 1.221(5) ?
O2 N3 . 1.238(4) ?
O3 N4 . 1.236(4) ?
O4 N4 . 1.240(4) ?
N1 C1 . 1.345(5) ?
N1 N2 . 1.396(5) ?
N1 H1N . 0.87(4) ?
N2 C7 . 1.270(5) ?
N3 C4 . 1.458(5) ?
N4 C2 . 1.451(5) ?
C1 C2 . 1.420(6) ?
C1 C6 . 1.423(5) ?
C2 C3 . 1.391(6) ?
C3 C4 . 1.378(5) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.395(6) ?
C5 C6 . 1.365(6) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.483(6) ?
C7 H7 . 0.96(4) ?
C8 C9 . 1.521(6) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.515(6) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.513(6) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
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 H1n O4 1_555 0.87(4) 1.99(4) 2.616(5) 128(3)
N1 H1n O4 5_566 0.87(4) 2.41(4) 3.166(5) 146(4)
C3 H3 O1 2_555 0.95 2.39 3.335(5) 176
C6 H6 N2 1_555 0.95 2.40 2.735(5) 100
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7875397
