#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/38/2013813.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_2013813
loop_
_publ_author_name
'Baughman, Russell G.'
'Martin, Kenneth L.'
'Singh, Rajendra K.'
'Stoffer, James O.'
_publ_section_title
;
 2,4-Dinitrophenylhydrazones of 2,4-dihydroxybenzaldehyde,
 2,4-dihydroxyacetophenone and 2,4-dihydroxybenzophenone
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o103
_journal_page_last               o106
_journal_paper_doi               10.1107/S0108270103027197
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C13 H10 N4 O6 , C3 H7 N O'
_chemical_formula_moiety         'C13 H10 N4 O6 , C3 H7 N O'
_chemical_formula_sum            'C16 H17 N5 O7'
_chemical_formula_weight         391.35
_chemical_name_common
;
4-[(2,4-dinitrophenyl)hydrazonomethyl]benzene-1,3-diol N,N-dimethylformamide
solvate
;
_chemical_name_systematic
;
2,4-dihydroxybenzaldehyde 2,4-dinitrophenylhydrazone N,N-dimethylformamide
solvate
;
_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           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 100.34(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.697(4)
_cell_length_b                   7.1520(10)
_cell_length_c                   12.949(3)
_cell_measurement_reflns_used    49
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      7.8
_cell_volume                     1794.5(6)
_computing_cell_refinement       'P3/P4-PC Diffractometer Program'
_computing_data_collection
'P3/P4-PC Diffractometer Program (Siemens, 1991)'
_computing_data_reduction        'XDISK (Siemens, 1991)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990b)'
_computing_publication_material  'SHELXTL/PC and SHELXL97'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.013
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3504
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        2.3
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block cut from larger crystal'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.16
_refine_ls_extinction_coef       0.0059(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.109
_refine_ls_R_factor_gt           0.051
_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)+(0.0658P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.113
_refine_ls_wR_factor_ref         0.137
_reflns_number_gt                1774
_reflns_number_total             3119
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln1175.cif
_cod_data_source_block           X
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013813
_cod_database_fobs_code          2013813
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 -0.20622(9) 0.4970(3) 0.63510(14) 0.0618(6) Uani d . 1 . . O
H1A -0.2393 0.5232 0.5893 0.093 Uiso calc R 1 . . H
O2 0.01956(10) 0.2631(4) 0.68351(14) 0.0707(7) Uani d . 1 . . O
H2A 0.0494 0.2288 0.6509 0.106 Uiso calc R 1 . . H
O3 0.16439(11) 0.0749(3) 0.27547(15) 0.0693(7) Uani d . 1 . . O
O4 0.26547(12) -0.0371(4) 0.27488(17) 0.0992(10) Uani d . 1 . . O
O5 0.41862(12) -0.2099(4) 0.5822(2) 0.0946(9) Uani d . 1 . . O
O6 0.38850(12) -0.1867(4) 0.7335(2) 0.1021(10) Uani d . 1 . . O
N1 0.07225(11) 0.1772(3) 0.51162(16) 0.0425(6) Uani d . 1 . . N
N2 0.12061(11) 0.1243(3) 0.45155(17) 0.0447(6) Uani d . 1 . . N
H2B 0.1103 0.1332 0.3843 0.054 Uiso calc R 1 . . H
N3 0.22003(13) 0.0131(4) 0.32216(19) 0.0594(7) Uani d . 1 . . N
N4 0.37704(13) -0.1689(4) 0.6381(3) 0.0692(8) Uani d . 1 . . N
C1 -0.15366(13) 0.4325(4) 0.5899(2) 0.0442(7) Uani d . 1 . . C
C2 -0.09374(14) 0.3789(4) 0.6552(2) 0.0489(7) Uani d . 1 . . C
H2 -0.0906 0.3878 0.7276 0.059 Uiso calc R 1 . . H
C3 -0.03840(13) 0.3122(4) 0.6147(2) 0.0452(7) Uani d . 1 . . C
C4 -0.04186(12) 0.2989(4) 0.50534(19) 0.0378(6) Uani d . 1 . . C
C5 -0.10279(13) 0.3554(4) 0.4422(2) 0.0439(7) Uani d . 1 . . C
H5 -0.1061 0.3480 0.3697 0.053 Uiso calc R 1 . . H
C6 -0.15855(13) 0.4217(4) 0.4815(2) 0.0456(7) Uani d . 1 . . C
H6 -0.1986 0.4585 0.4367 0.055 Uiso calc R 1 . . H
C7 0.01475(13) 0.2344(4) 0.4583(2) 0.0413(7) Uani d . 1 . . C
H7 0.0094 0.2342 0.3855 0.050 Uiso calc R 1 . . H
C8 0.18308(13) 0.0594(4) 0.4956(2) 0.0403(7) Uani d . 1 . . C
C9 0.20271(13) 0.0459(4) 0.6059(2) 0.0491(8) Uani d . 1 . . C
H9 0.1726 0.0885 0.6485 0.059 Uiso calc R 1 . . H
C10 0.26483(14) -0.0283(4) 0.6514(2) 0.0526(8) Uani d . 1 . . C
H10 0.2764 -0.0374 0.7241 0.063 Uiso calc R 1 . . H
C11 0.31078(13) -0.0903(4) 0.5886(2) 0.0505(8) Uani d . 1 . . C
C12 0.29525(14) -0.0766(4) 0.4821(2) 0.0519(8) Uani d . 1 . . C
H12 0.3266 -0.1175 0.4411 0.062 Uiso calc R 1 . . H
C13 0.23262(13) -0.0015(4) 0.43541(19) 0.0440(7) Uani d . 1 . . C
O7 -0.32368(12) 0.6028(4) 0.5204(2) 0.0875(8) Uani d . 1 . . O
N5 -0.40595(14) 0.6777(4) 0.3823(3) 0.0777(9) Uani d . 1 . . N
C14 -0.34287(19) 0.6195(5) 0.4276(3) 0.0757(10) Uani d . 1 . . C
H14 -0.3118 0.5899 0.3838 0.091 Uiso calc R 1 . . H
C15 -0.45853(19) 0.7223(7) 0.4422(3) 0.1127(16) Uani d . 1 . . C
H15A -0.4430 0.6880 0.5142 0.169 Uiso calc R 1 . . H
H15B -0.4999 0.6547 0.4146 0.169 Uiso calc R 1 . . H
H15C -0.4678 0.8541 0.4377 0.169 Uiso calc R 1 . . H
C16 -0.4236(2) 0.6872(6) 0.2695(4) 0.1119(15) Uani d . 1 . . C
H16A -0.3832 0.6642 0.2396 0.168 Uiso calc R 1 . . H
H16B -0.4415 0.8091 0.2489 0.168 Uiso calc R 1 . . H
H16C -0.4580 0.5945 0.2448 0.168 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -2 0
0 -2 3
0 0 5
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1A 109.5
C3 O2 H2A 109.5
C7 N1 N2 114.5(2)
C8 N2 N1 121.7(2)
C8 N2 H2B 119.2
N1 N2 H2B 119.2
O4 N3 O3 121.6(3)
O4 N3 C13 118.5(3)
O3 N3 C13 119.9(2)
O6 N4 O5 123.5(3)
O6 N4 C11 118.2(3)
O5 N4 C11 118.3(3)
O1 C1 C2 117.8(2)
O1 C1 C6 122.2(2)
C2 C1 C6 120.0(3)
C1 C2 C3 120.8(2)
C1 C2 H2 119.6
C3 C2 H2 119.6
O2 C3 C2 117.9(2)
O2 C3 C4 121.6(2)
C2 C3 C4 120.5(2)
C5 C4 C3 117.0(2)
C5 C4 C7 119.9(2)
C3 C4 C7 123.1(2)
C6 C5 C4 123.1(2)
C6 C5 H5 118.4
C4 C5 H5 118.4
C5 C6 C1 118.5(3)
C5 C6 H6 120.7
C1 C6 H6 120.7
N1 C7 C4 123.4(2)
N1 C7 H7 118.3
C4 C7 H7 118.3
N2 C8 C9 121.1(2)
N2 C8 C13 122.6(2)
C9 C8 C13 116.3(2)
C10 C9 C8 121.6(2)
C10 C9 H9 119.2
C8 C9 H9 119.2
C9 C10 C11 119.8(3)
C9 C10 H10 120.1
C11 C10 H10 120.1
C12 C11 C10 121.1(3)
C12 C11 N4 119.5(3)
C10 C11 N4 119.3(3)
C11 C12 C13 119.5(3)
C11 C12 H12 120.3
C13 C12 H12 120.3
C12 C13 C8 121.7(2)
C12 C13 N3 116.7(2)
C8 C13 N3 121.6(2)
C14 N5 C15 122.3(4)
C14 N5 C16 119.6(4)
C15 N5 C16 118.0(3)
O7 C14 N5 124.7(4)
O7 C14 H14 117.7
N5 C14 H14 117.7
N5 C15 H15A 109.5
N5 C15 H15B 109.5
H15A C15 H15B 109.5
N5 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
N5 C16 H16A 109.5
N5 C16 H16B 109.5
H16A C16 H16B 109.5
N5 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 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 . 1.358(3) ?
O1 H1A . 0.8200 ?
O2 C3 . 1.362(3) ?
O2 H2A . 0.8200 ?
O3 N3 . 1.234(3) ?
O4 N3 . 1.225(3) ?
O5 N4 . 1.223(3) ?
O6 N4 . 1.221(3) ?
N1 C7 . 1.283(3) ?
N1 N2 . 1.386(3) ?
N2 C8 . 1.343(3) ?
N2 H2B . 0.8600 ?
N3 C13 . 1.447(3) ?
N4 C11 . 1.459(4) ?
C1 C2 . 1.377(4) ?
C1 C6 . 1.392(3) ?
C2 C3 . 1.377(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.408(3) ?
C4 C5 . 1.386(3) ?
C4 C7 . 1.439(3) ?
C5 C6 . 1.375(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.414(4) ?
C8 C13 . 1.422(3) ?
C9 C10 . 1.366(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.393(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.362(4) ?
C12 C13 . 1.381(4) ?
C12 H12 . 0.9300 ?
O7 C14 . 1.200(4) ?
N5 C14 . 1.341(4) ?
N5 C15 . 1.436(4) ?
N5 C16 . 1.442(5) ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1A O7 0.82 1.83 2.626(3) 163
O2 H2A N1 0.82 1.97 2.691(3) 146
N2 H2B O3 0.86 1.96 2.603(3) 131
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
C7 N1 N2 C8 -179.3(2)
O1 C1 C2 C3 -180.0(3)
C6 C1 C2 C3 -0.7(4)
C1 C2 C3 O2 179.4(3)
C1 C2 C3 C4 0.5(4)
O2 C3 C4 C5 -178.9(3)
C2 C3 C4 C5 0.0(4)
O2 C3 C4 C7 -0.3(4)
C2 C3 C4 C7 178.6(3)
C3 C4 C5 C6 -0.1(4)
C7 C4 C5 C6 -178.8(3)
C4 C5 C6 C1 -0.1(4)
O1 C1 C6 C5 179.8(3)
C2 C1 C6 C5 0.5(4)
N2 N1 C7 C4 -178.8(2)
C5 C4 C7 N1 -178.8(3)
C3 C4 C7 N1 2.6(4)
N1 N2 C8 C9 -1.3(4)
N1 N2 C8 C13 177.8(2)
N2 C8 C9 C10 176.8(3)
C13 C8 C9 C10 -2.4(4)
C8 C9 C10 C11 0.9(4)
C9 C10 C11 C12 0.7(4)
C9 C10 C11 N4 179.9(3)
O6 N4 C11 C12 -177.0(3)
O5 N4 C11 C12 4.4(5)
O6 N4 C11 C10 3.8(5)
O5 N4 C11 C10 -174.8(3)
C10 C11 C12 C13 -0.6(4)
N4 C11 C12 C13 -179.7(3)
C11 C12 C13 C8 -1.1(4)
C11 C12 C13 N3 178.6(3)
N2 C8 C13 C12 -176.7(3)
C9 C8 C13 C12 2.5(4)
N2 C8 C13 N3 3.7(4)
C9 C8 C13 N3 -177.1(3)
O4 N3 C13 C12 -1.6(4)
O3 N3 C13 C12 178.3(3)
O4 N3 C13 C8 178.0(3)
O3 N3 C13 C8 -2.1(4)
C15 N5 C14 O7 -1.7(6)
C16 N5 C14 O7 -178.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21181433
