#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/15/2201580.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_2201580
loop_
_publ_author_name
' Yasushi Kawai '
' Motoko Hayashi '
' Norihiro Tokitoh '
_publ_section_title
;
 Propanone 2-chloro-4,6-dinitrophenylhydrazone
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1098
_journal_page_last               o1099
_journal_paper_doi               10.1107/S1600536802016483
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C9 H9 Cl N4 O4 '
_chemical_formula_sum            'C9 H9 Cl N4 O4'
_chemical_formula_weight         272.65
_chemical_name_systematic
;
propane-2-one 6-chloro-2,4-dinitrophenylhydrazone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90
_cell_angle_beta                 115.557(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6057(11)
_cell_length_b                   16.1100(10)
_cell_length_c                   8.9967(11)
_cell_measurement_reflns_used    3753
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      13.7
_cell_measurement_theta_min      1.5
_cell_volume                     1125.2(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection
'CrystalClear (Rigaku/MSC and Rigaku Corporation, 2001)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2001)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'please supply'
_computing_structure_refinement  'CRYSTALS (Watkin et al., 1999)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8602
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560.00
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2545
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.0040
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0012Fo² + 1.0000σ²(Fo)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                2376
_reflns_number_total             2545
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            ob6175.cif
_cod_data_source_block           I
_cod_original_cell_volume        1125.3(2)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_original_formula_sum        'C9 H9 Cl N4 O4 '
_cod_database_code               2201580
_cod_database_fobs_code          2201580
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z
x+1/2,-y+1/2,z
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
Cl1 0.33699(3) 0.43411(2) 0.45674(4) 0.02049(10) Uani d . 1.00 . . Cl
O1 -0.31962(12) 0.60709(6) 0.13845(12) 0.0231(3) Uani d . 1.00 . . O
O2 -0.35061(11) 0.51900(6) -0.05483(11) 0.0198(2) Uani d . 1.00 . . O
O3 -0.36916(11) 0.32077(6) 0.42289(11) 0.0197(2) Uani d . 1.00 . . O
O4 -0.11639(12) 0.27118(6) 0.58146(11) 0.0205(2) Uani d . 1.00 . . O
N1 0.00184(13) 0.60166(6) 0.08574(12) 0.0143(2) Uani d . 1.00 . . N
N2 0.09849(13) 0.54896(6) 0.21565(13) 0.0146(2) Uani d . 1.00 . . N
N3 -0.28442(12) 0.54264(6) 0.08914(13) 0.0142(2) Uani d . 1.00 . . N
N4 -0.21164(13) 0.31848(6) 0.47281(12) 0.0137(2) Uani d . 1.00 . . N
C1 -0.0154(2) 0.71643(8) -0.0845(2) 0.0197(3) Uani d . 1.00 . . C
C2 0.0865(2) 0.66020(7) 0.05650(10) 0.0144(3) Uani d . 1.00 . . C
C3 0.2764(2) 0.67653(8) 0.1505(2) 0.0182(3) Uani d . 1.00 . . C
C4 0.01700(10) 0.49174(7) 0.26720(10) 0.0120(3) Uani d . 1.00 . . C
C5 -0.16240(10) 0.48569(7) 0.21387(13) 0.0115(3) Uani d . 1.00 . . C
C6 -0.2386(2) 0.42925(7) 0.27760(10) 0.0122(3) Uani d . 1.00 . . C
C7 -0.13290(10) 0.37593(7) 0.40036(13) 0.0119(3) Uani d . 1.00 . . C
C8 0.0451(2) 0.37700(7) 0.45770(10) 0.0127(3) Uani d . 1.00 . . C
C9 0.11600(10) 0.43322(7) 0.39060(10) 0.0126(3) Uani d . 1.00 . . C
H1 -0.007(2) 0.7729(11) -0.048(2) 0.028(4) Uiso c . 1.00 . . H
H2 0.040(2) 0.7162(10) -0.158(2) 0.024(4) Uiso c . 1.00 . . H
H3 -0.137(2) 0.6948(10) -0.146(2) 0.027(4) Uiso c . 1.00 . . H
H4 0.299(2) 0.7333(11) 0.134(2) 0.029(4) Uiso c . 1.00 . . H
H5 0.320(2) 0.6666(11) 0.268(2) 0.039(5) Uiso c . 1.00 . . H
H6 0.349(2) 0.6370(12) 0.123(2) 0.035(5) Uiso c . 1.00 . . H
H7 0.206(3) 0.5449(11) 0.243(2) 0.035(5) Uiso c . 1.00 . . H
H8 -0.351(2) 0.4269(9) 0.245(2) 0.020(4) Uiso c . 1.00 . . H
H9 0.115(2) 0.3454(10) 0.537(2) 0.024(4) Uiso c . 1.00 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.174 0.200
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.017 0.010
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.006 0.003
;
International Tables for Crystallography
(1992, 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
N2 N1 C2 115.60(10) yes
N1 N2 C4 119.50(10) yes
N1 N2 H7 117.9(12) no
C4 N2 H7 120.6(12) no
O1 N3 O2 125.00(10) yes
O1 N3 C5 117.30(10) no
O2 N3 C5 117.50(10) no
O3 N4 O4 124.00(10) yes
O3 N4 C7 118.00(9) no
O4 N4 C7 118.00(10) no
C2 C1 H1 110.7(11) no
C2 C1 H2 107.2(10) no
H1 C1 H2 104.3(15) no
C2 C1 H3 110.1(11) no
H1 C1 H3 115.1(15) no
H2 C1 H3 108.9(15) no
N1 C2 C1 116.15(11) yes
N1 C2 C3 125.95(11) yes
C1 C2 C3 117.90(10) yes
C2 C3 H4 108.8(11) no
C2 C3 H5 113.4(12) no
H4 C3 H5 108.6(16) no
C2 C3 H6 113.2(11) no
H4 C3 H6 112.6(15) no
H5 C3 H6 100.0(16) no
N2 C4 C5 125.70(10) yes
N2 C4 C9 119.50(10) yes
C5 C4 C9 114.80(10) no
N3 C5 C4 122.10(10) yes
N3 C5 C6 114.50(10) yes
C4 C5 C6 123.40(10) no
C5 C6 C7 118.24(11) no
C5 C6 H8 122.7(10) no
C7 C6 H8 119.0(10) no
N4 C7 C6 118.60(10) yes
N4 C7 C8 119.50(10) yes
C6 C7 C8 121.90(10) no
C7 C8 C9 118.30(10) no
C7 C8 H9 124.2(10) no
C9 C8 H9 117.5(10) no
Cl1 C9 C4 117.49(9) yes
Cl1 C9 C8 119.09(9) yes
C4 C9 C8 123.40(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C9 . . 1.7303(12) yes
O1 N3 . . 1.2177(14) yes
O2 N3 . . 1.2291(14) yes
O3 N4 . . 1.2310(13) yes
O4 N4 . . 1.2316(13) yes
N1 N2 . . 1.3928(14) yes
N1 C2 . . 1.2865(15) yes
N2 C4 . . 1.3552(15) yes
N2 H7 . . 0.85(2) no
N3 C5 . . 1.4787(14) no
N4 C7 . . 1.4568(14) no
C1 C2 . . 1.4961(16) yes
C1 H1 . . 0.96(2) no
C1 H2 . . 0.97(2) no
C1 H3 . . 1.01(2) no
C2 C3 . . 1.5039(16) yes
C3 H4 . . 0.96(2) no
C3 H5 . . 0.97(2) no
C3 H6 . . 0.99(2) no
C4 C5 . . 1.4088(15) yes
C4 C9 . . 1.4249(15) yes
C5 C6 . . 1.3820(15) no
C6 C7 . . 1.3848(16) no
C6 H8 . . 0.88(2) no
C7 C8 . . 1.3896(15) no
C8 C9 . . 1.3697(16) yes
C8 H9 . . 0.871(13) 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
C2 N1 N2 C4 172.4(2) yes
N2 N1 C2 C1 179.10(10) no
N2 N1 C2 C3 -0.8(2) no
N1 N2 C4 C5 -7.9(2) yes
N1 N2 C4 C9 174.80(10) no
O1 N3 C5 C4 -88.6(2) no
O1 N3 C5 C6 88.7(2) yes
O2 N3 C5 C4 95.8(2) no
O2 N3 C5 C6 -86.8(2) no
O3 N4 C7 C6 -1.0(2) no
O3 N4 C7 C8 177.80(10) no
O4 N4 C7 C6 179.80(10) yes
O4 N4 C7 C8 -1.5(2) no
N2 C4 C5 N3 1.2(3) no
N2 C4 C5 C6 -176.0(2) no
C9 C4 C5 N3 178.70(10) no
C9 C4 C5 C6 1.5(2) no
N2 C4 C9 Cl1 -4.8(2) no
N2 C4 C9 C8 175.4(2) no
C5 C4 C9 Cl1 177.59(12) no
C5 C4 C9 C8 -2.2(2) no
N3 C5 C6 C7 -177.30(10) no
C4 C5 C6 C7 0.0(3) no
C5 C6 C7 N4 177.60(10) no
C5 C6 C7 C8 -1.1(2) no
N4 C7 C8 C9 -178.20(10) no
C6 C7 C8 C9 0.5(3) no
C7 C8 C9 Cl1 -178.54(12) no
C7 C8 C9 C4 1.3(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132143
