#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/80/2208090.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_2208090
loop_
_publ_author_name
'Jing, Zuo-Liang'
'Liu, Yu'
'Chen, Xin'
'Ming, Yu'
_publ_section_title
;
 N-(2,4-Dinitrophenyl)-N'-(4-methoxybenzylidene)hydrazine
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o862
_journal_page_last               o863
_journal_paper_doi               10.1107/S160053680600287X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C14 H12 N4 O5'
_chemical_formula_sum            'C14 H12 N4 O5'
_chemical_formula_weight         316.28
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.392(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.189(2)
_cell_length_b                   8.581(3)
_cell_length_c                   26.669(11)
_cell_measurement_reflns_used    2340
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      3.07
_cell_volume                     1407.5(9)
_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  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7349
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0335
_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)+(0.0536P)²+0.1714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1914
_reflns_number_total             2481
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2002.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/n'
_cod_database_code               2208090
_cod_database_fobs_code          2208090
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.3423(2) 0.45260(16) 0.24373(4) 0.0786(4) Uani d . 1 O
O2 0.0374(2) 0.57267(15) 0.24395(4) 0.0732(4) Uani d . 1 O
O3 -0.21341(15) 0.91196(13) 0.11194(4) 0.0544(3) Uani d . 1 O
O4 -0.05330(15) 0.93642(13) 0.04464(4) 0.0485(3) Uani d . 1 O
O5 1.16761(16) 0.67880(13) -0.15044(4) 0.0534(3) Uani d . 1 O
N1 0.2021(2) 0.54176(16) 0.22460(5) 0.0554(4) Uani d . 1 N
N2 -0.06467(17) 0.88067(13) 0.08692(4) 0.0396(3) Uani d . 1 N
N3 0.31318(19) 0.79195(15) 0.03573(4) 0.0410(3) Uani d . 1 N
H3 0.218(3) 0.856(2) 0.0209(6) 0.063(5) Uiso d . 1 H
N4 0.49046(17) 0.74551(14) 0.01246(4) 0.0407(3) Uani d . 1 N
C1 0.4396(2) 0.63427(17) 0.10686(5) 0.0438(4) Uani d . 1 C
H1 0.5617 0.6076 0.0914 0.053 Uiso calc R 1 H
C2 0.4153(2) 0.57340(18) 0.15287(6) 0.0468(4) Uani d . 1 C
H2 0.5199 0.5063 0.1685 0.056 Uiso calc R 1 H
C3 0.2329(2) 0.61192(16) 0.17645(5) 0.0430(3) Uani d . 1 C
C4 0.0793(2) 0.71209(16) 0.15458(5) 0.0413(3) Uani d . 1 C
H4 -0.0409 0.7378 0.1709 0.050 Uiso calc R 1 H
C5 0.1041(2) 0.77512(15) 0.10779(5) 0.0361(3) Uani d . 1 C
C6 0.2851(2) 0.73685(15) 0.08180(5) 0.0369(3) Uani d . 1 C
C7 0.4991(2) 0.80444(17) -0.03114(5) 0.0392(3) Uani d . 1 C
H7 0.3898 0.8727 -0.0439 0.047 Uiso calc R 1 H
C8 0.6728(2) 0.76941(16) -0.06176(5) 0.0366(3) Uani d . 1 C
C9 0.8453(2) 0.66906(16) -0.04617(5) 0.0394(3) Uani d . 1 C
H9 0.8509 0.6203 -0.0149 0.047 Uiso calc R 1 H
C10 1.0061(2) 0.64189(17) -0.07647(5) 0.0407(3) Uani d . 1 C
H10 1.1199 0.5748 -0.0657 0.049 Uiso calc R 1 H
C11 1.0002(2) 0.71415(16) -0.12336(5) 0.0394(3) Uani d . 1 C
C12 0.8303(2) 0.81308(17) -0.13959(5) 0.0405(3) Uani d . 1 C
H12 0.8245 0.8612 -0.1710 0.049 Uiso calc R 1 H
C13 0.6694(2) 0.83953(17) -0.10867(5) 0.0398(3) Uani d . 1 C
H13 0.5554 0.9063 -0.1196 0.048 Uiso calc R 1 H
C14 1.1818(3) 0.7624(2) -0.19634(6) 0.0601(5) Uani d . 1 C
H14A 1.0598 0.7361 -0.2203 0.090 Uiso calc R 1 H
H14B 1.3141 0.7347 -0.2098 0.090 Uiso calc R 1 H
H14C 1.1811 0.8723 -0.1897 0.090 Uiso calc R 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
_geom_angle_publ_flag
C11 O5 C14 117.74(11) ?
O2 N1 O1 123.06(14) ?
O2 N1 C3 118.84(14) ?
O1 N1 C3 118.09(13) ?
O3 N2 O4 122.36(12) ?
O3 N2 C5 118.80(12) ?
O4 N2 C5 118.84(10) ?
C6 N3 N4 119.99(12) yes
C6 N3 H3 119.3(10) ?
N4 N3 H3 120.7(11) ?
C7 N4 N3 114.37(12) yes
C2 C1 C6 122.04(13) ?
C2 C1 H1 119.0 ?
C6 C1 H1 119.0 ?
C1 C2 C3 119.62(14) ?
C1 C2 H2 120.2 ?
C3 C2 H2 120.2 ?
C4 C3 C2 121.22(13) ?
C4 C3 N1 119.09(13) ?
C2 C3 N1 119.67(14) ?
C3 C4 C5 119.35(12) ?
C3 C4 H4 120.3 ?
C5 C4 H4 120.3 ?
C4 C5 C6 121.48(13) ?
C4 C5 N2 116.37(11) ?
C6 C5 N2 122.15(12) no
N3 C6 C1 120.10(12) no
N3 C6 C5 123.62(13) no
C1 C6 C5 116.28(13) ?
N4 C7 C8 122.69(13) no
N4 C7 H7 118.7 ?
C8 C7 H7 118.7 ?
C13 C8 C9 118.03(12) ?
C13 C8 C7 118.68(12) no
C9 C8 C7 123.29(12) no
C10 C9 C8 120.69(13) ?
C10 C9 H9 119.7 ?
C8 C9 H9 119.7 ?
C9 C10 C11 120.37(13) ?
C9 C10 H10 119.8 ?
C11 C10 H10 119.8 ?
O5 C11 C12 124.60(13) ?
O5 C11 C10 115.57(12) ?
C12 C11 C10 119.83(12) ?
C13 C12 C11 119.21(13) ?
C13 C12 H12 120.4 ?
C11 C12 H12 120.4 ?
C12 C13 C8 121.87(13) ?
C12 C13 H13 119.1 ?
C8 C13 H13 119.1 ?
O5 C14 H14A 109.5 ?
O5 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O5 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_distance
_geom_bond_publ_flag
O1 N1 1.2252(18) ?
O2 N1 1.2217(17) ?
O3 N2 1.2254(14) ?
O4 N2 1.2339(15) ?
O5 C11 1.3614(15) yes
O5 C14 1.4298(18) ?
N1 C3 1.4500(19) yes
N2 C5 1.4462(18) yes
N3 C6 1.3457(18) yes
N3 N4 1.3782(15) yes
N3 H3 0.869(18) ?
N4 C7 1.2746(18) yes
C1 C2 1.357(2) ?
C1 C6 1.412(2) no
C1 H1 0.9300 ?
C2 C3 1.392(2) ?
C2 H2 0.9300 ?
C3 C4 1.364(2) ?
C4 C5 1.3841(19) ?
C4 H4 0.9300 ?
C5 C6 1.4199(18) no
C7 C8 1.4516(18) no
C7 H7 0.9300 ?
C8 C13 1.3864(19) no
C8 C9 1.3984(19) no
C9 C10 1.3703(18) ?
C9 H9 0.9300 ?
C10 C11 1.393(2) ?
C10 H10 0.9300 ?
C11 C12 1.383(2) ?
C12 C13 1.3809(18) ?
C12 H12 0.9300 ?
C13 H13 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
N3 H3 O4 . 0.869(18) 1.984(17) 2.6189(17) 129.0(14) yes
N3 H3 O4 3_575 0.869(18) 2.620(18) 3.4419(19) 158.2(14) yes
C2 H2 O5 3_765 0.93 2.59 3.375(2) 143 yes
C14 H14B O2 4_664 0.96 2.56 3.188(3) 123 yes
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 N3 N4 C7 179.55(12)
C6 C1 C2 C3 0.2(2)
C1 C2 C3 C4 -1.1(2)
C1 C2 C3 N1 177.35(13)
O2 N1 C3 C4 1.0(2)
O1 N1 C3 C4 -179.69(14)
O2 N1 C3 C2 -177.49(14)
O1 N1 C3 C2 1.8(2)
C2 C3 C4 C5 0.8(2)
N1 C3 C4 C5 -177.72(12)
C3 C4 C5 C6 0.5(2)
C3 C4 C5 N2 -179.86(12)
O3 N2 C5 C4 2.33(18)
O4 N2 C5 C4 -177.93(12)
O3 N2 C5 C6 -178.05(12)
O4 N2 C5 C6 1.69(19)
N4 N3 C6 C1 1.4(2)
N4 N3 C6 C5 -178.13(12)
C2 C1 C6 N3 -178.59(14)
C2 C1 C6 C5 1.0(2)
C4 C5 C6 N3 178.22(12)
N2 C5 C6 N3 -1.4(2)
C4 C5 C6 C1 -1.4(2)
N2 C5 C6 C1 179.02(12)
N3 N4 C7 C8 -179.74(12)
N4 C7 C8 C13 -179.72(13)
N4 C7 C8 C9 -0.3(2)
C13 C8 C9 C10 0.3(2)
C7 C8 C9 C10 -179.18(13)
C8 C9 C10 C11 0.0(2)
C14 O5 C11 C12 7.1(2)
C14 O5 C11 C10 -173.46(13)
C9 C10 C11 O5 -179.86(12)
C9 C10 C11 C12 -0.4(2)
O5 C11 C12 C13 179.85(13)
C10 C11 C12 C13 0.5(2)
C11 C12 C13 C8 -0.1(2)
C9 C8 C13 C12 -0.2(2)
C7 C8 C13 C12 179.25(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7858926
