#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/59/2015917.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_2015917
loop_
_publ_author_name
'Wardell, James L.'
'Low, John N.'
'Glidewell, Christopher'
_publ_section_title
;
 A re-examination of supramolecular aggregation in two polymorphs of
 acetone 2,4-dinitrophenylhydrazone
;
_journal_coeditor_code           SK3098
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o231
_journal_page_last               o233
_journal_paper_doi               10.1107/S0108270107006981
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H10 N4 O4'
_chemical_formula_moiety         'C9 H10 N4 O4'
_chemical_formula_sum            'C9 H10 N4 O4'
_chemical_formula_weight         238.21
_chemical_name_systematic
;
Acetone 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
_cell_angle_alpha                66.613(2)
_cell_angle_beta                 88.822(3)
_cell_angle_gamma                77.387(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0932(3)
_cell_length_b                   8.2032(4)
_cell_length_c                   10.0526(4)
_cell_measurement_reflns_used    2396
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.21
_cell_volume                     522.49(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12000
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0820P)²+0.0909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                1957
_reflns_number_total             2393
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3098.cif
_cod_data_source_block           I
_cod_database_code               2015917
_cod_database_fobs_code          2015917
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
O O21 0.79883(13) 0.43025(14) 0.35357(10) 0.0264(2) Uani d . 1
O O22 0.68045(14) 0.47172(13) 0.14315(10) 0.0269(2) Uani d . 1
O O41 0.14892(16) 0.23433(16) 0.08958(10) 0.0335(3) Uani d . 1
O O42 -0.00269(13) 0.09926(13) 0.27652(10) 0.0243(2) Uani d . 1
N N1 0.63130(15) 0.27688(14) 0.58865(11) 0.0183(2) Uani d . 1
N N2 0.60008(15) 0.21548(15) 0.73545(11) 0.0192(3) Uani d . 1
N N12 0.67715(15) 0.41367(15) 0.27552(12) 0.0196(3) Uani d . 1
N N14 0.12470(16) 0.18034(15) 0.21951(12) 0.0204(3) Uani d . 1
C C1 0.50745(17) 0.26031(16) 0.49651(13) 0.0161(3) Uani d . 1
C C2 0.52596(17) 0.32171(16) 0.34472(13) 0.0161(3) Uani d . 1
C C3 0.40033(17) 0.29639(17) 0.25365(13) 0.0173(3) Uani d . 1
C C4 0.25470(17) 0.21064(17) 0.31336(13) 0.0167(3) Uani d . 1
C C5 0.22706(18) 0.15232(17) 0.46174(14) 0.0179(3) Uani d . 1
C C6 0.35066(17) 0.17739(17) 0.55101(13) 0.0184(3) Uani d . 1
C C11 0.72963(18) 0.22764(17) 0.81669(14) 0.0198(3) Uani d . 1
C C12 0.7005(2) 0.1620(2) 0.97499(15) 0.0279(3) Uani d . 1
C C13 0.90674(18) 0.29973(19) 0.76374(15) 0.0236(3) Uani d . 1
H H1 0.7452 0.3232 0.5534 0.022 Uiso d R 1
H H3 0.4153 0.3377 0.1522 0.021 Uiso calc R 1
H H5 0.1233 0.0957 0.5003 0.021 Uiso calc R 1
H H6 0.3309 0.1384 0.6517 0.022 Uiso calc R 1
H H12A 0.5738 0.1311 0.9922 0.042 Uiso calc R 1
H H12B 0.7059 0.2583 1.0083 0.042 Uiso calc R 1
H H12C 0.8026 0.0536 1.0286 0.042 Uiso calc R 1
H H13A 0.9932 0.2165 0.7291 0.035 Uiso calc R 1
H H13B 0.9743 0.3090 0.8436 0.035 Uiso calc R 1
H H13C 0.8682 0.4206 0.6840 0.035 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O21 0.0217(5) 0.0343(6) 0.0269(5) -0.0139(4) 0.0016(4) -0.0124(4)
O22 0.0305(5) 0.0307(6) 0.0186(5) -0.0133(4) 0.0070(4) -0.0061(4)
O41 0.0415(6) 0.0465(7) 0.0160(5) -0.0225(5) -0.0001(4) -0.0096(5)
O42 0.0233(5) 0.0269(5) 0.0258(5) -0.0131(4) 0.0008(4) -0.0099(4)
N1 0.0181(5) 0.0226(6) 0.0155(5) -0.0064(4) 0.0007(4) -0.0080(4)
N2 0.0208(5) 0.0209(6) 0.0166(5) -0.0054(4) 0.0006(4) -0.0080(4)
N12 0.0190(5) 0.0195(5) 0.0205(6) -0.0058(4) 0.0030(4) -0.0075(4)
N14 0.0222(6) 0.0202(6) 0.0189(6) -0.0060(4) -0.0011(4) -0.0073(5)
C1 0.0154(6) 0.0142(6) 0.0183(6) -0.0013(5) -0.0005(5) -0.0072(5)
C2 0.0151(6) 0.0145(6) 0.0182(6) -0.0036(5) 0.0025(5) -0.0059(5)
C3 0.0189(6) 0.0161(6) 0.0154(6) -0.0024(5) 0.0015(5) -0.0057(5)
C4 0.0175(6) 0.0164(6) 0.0169(6) -0.0038(5) -0.0022(5) -0.0071(5)
C5 0.0167(6) 0.0171(6) 0.0188(6) -0.0049(5) 0.0016(5) -0.0058(5)
C6 0.0188(6) 0.0196(6) 0.0158(6) -0.0045(5) 0.0020(5) -0.0062(5)
C11 0.0207(6) 0.0176(6) 0.0215(7) -0.0016(5) -0.0021(5) -0.0095(5)
C12 0.0296(7) 0.0357(8) 0.0217(7) -0.0092(6) -0.0002(5) -0.0139(6)
C13 0.0202(6) 0.0272(7) 0.0265(7) -0.0063(5) -0.0019(5) -0.0135(6)
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
N1 C1 C6 119.92(11) no
N1 C1 C2 123.20(11) no
C6 C1 C2 116.88(11) no
C1 N1 N2 119.23(10) no
C1 N1 H1 120.2 no
N2 N1 H1 120.4 no
C11 N2 N1 115.35(11) no
N2 C11 C12 116.60(12) no
N2 C11 C13 124.89(12) no
C12 C11 C13 118.51(11) no
C11 C12 H12A 109.5 no
C11 C12 H12B 109.5 no
H12A C12 H12B 109.5 no
C11 C12 H12C 109.5 no
H12A C12 H12C 109.5 no
H12B C12 H12C 109.5 no
C11 C13 H13A 109.5 no
C11 C13 H13B 109.5 no
H13A C13 H13B 109.5 no
C11 C13 H13C 109.5 no
H13A C13 H13C 109.5 no
H13B C13 H13C 109.5 no
C3 C2 C1 121.76(11) no
C3 C2 N12 116.26(11) no
C1 C2 N12 121.98(10) no
O22 N12 O21 122.43(10) no
O22 N12 C2 119.14(10) no
O21 N12 C2 118.43(10) no
C4 C3 C2 118.65(11) no
C4 C3 H3 120.7 no
C2 C3 H3 120.7 no
C3 C4 C5 121.73(11) no
C3 C4 N14 119.10(11) no
C5 C4 N14 119.17(11) no
O41 N14 O42 123.72(11) no
O41 N14 C4 118.46(10) no
O42 N14 C4 117.81(10) no
C6 C5 C4 119.50(11) no
C6 C5 H5 120.2 no
C4 C5 H5 120.2 no
C5 C6 C1 121.43(11) no
C5 C6 H6 119.3 no
C1 C6 H6 119.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.3542(15) no
C1 C6 1.4174(17) no
C1 C2 1.4176(17) no
N1 N2 1.3876(15) no
N1 H1 0.9687 no
N2 C11 1.2872(16) no
C11 C12 1.4899(19) no
C11 C13 1.5028(18) no
C12 H12A 0.98 no
C12 H12B 0.98 no
C12 H12C 0.98 no
C13 H13A 0.98 no
C13 H13B 0.98 no
C13 H13C 0.98 no
C2 C3 1.3931(17) no
C2 N12 1.4523(16) no
N12 O22 1.2241(14) no
N12 O21 1.2421(14) no
C3 C4 1.3707(17) no
C3 H3 0.95 no
C4 C5 1.3982(17) no
C4 N14 1.4574(15) no
N14 O41 1.2233(14) no
N14 O42 1.2353(14) no
C5 C6 1.3688(17) no
C5 H5 0.95 no
C6 H6 0.95 no
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
N1 H1 O21 . 0.97 1.91 2.5994(15) 125 no
C5 H5 O42 2_556 0.95 2.45 3.2660(16) 144 no
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
_geom_torsion_publ_flag
C6 C1 N1 N2 -1.35(17) no
C2 C1 N1 N2 178.96(10) no
C1 N1 N2 C11 176.60(11) no
N1 N2 C11 C12 -179.76(10) no
N1 N2 C11 C13 -0.70(18) no
N1 C1 C2 C3 177.53(11) no
C6 C1 C2 C3 -2.16(17) no
N1 C1 C2 N12 -2.19(18) no
C6 C1 C2 N12 178.12(10) no
C3 C2 N12 O22 3.83(17) no
C1 C2 N12 O22 -176.44(11) no
C3 C2 N12 O21 -176.12(11) no
C1 C2 N12 O21 3.62(18) no
C1 C2 C3 C4 0.40(18) no
N12 C2 C3 C4 -179.86(11) no
C2 C3 C4 C5 1.47(18) no
C2 C3 C4 N14 -178.84(10) no
C3 C4 N14 O41 -0.69(18) no
C5 C4 N14 O41 179.00(11) no
C3 C4 N14 O42 178.46(11) no
C5 C4 N14 O42 -1.84(17) no
C3 C4 C5 C6 -1.47(19) no
N14 C4 C5 C6 178.85(11) no
C4 C5 C6 C1 -0.44(19) no
N1 C1 C6 C5 -177.53(11) no
C2 C1 C6 C5 2.17(18) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 66687
