#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/18/2011887.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_2011887
loop_
_publ_author_name
'Gzella, Andrzej'
'Wrzeciono, Urszula'
'Pöppel, Wolfram'
_publ_section_title
;
 Azole. 45. Über 2,4-Dinitrophenylhydrazone von
 Morpholinonitroimidazolderivaten
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              462
_journal_page_last               466
_journal_paper_doi               10.1107/S0108270101000270
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C16 H17 N9 O9'
_chemical_formula_sum            'C16 H17 N9 O9'
_chemical_formula_weight         479.39
_chemical_name_systematic
;
(Z)-1-(4,5-dinitroimidazol-1-yl)-3-morpholinopropan-2-one
2,4-dinitrophenylhydrazone
;
_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'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 96.579(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0382(7)
_cell_length_b                   19.2008(13)
_cell_length_c                   11.9087(8)
_cell_measurement_reflns_used    49
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.9
_cell_measurement_theta_min      14.4
_cell_volume                     2053.0(3)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma Diffraction, 1991)'
_computing_data_reduction        'KM-4 Software'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .957
_diffrn_measured_fraction_theta_max .957
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .017
_diffrn_reflns_av_sigmaI/netI    .017
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4027
_diffrn_reflns_theta_full        70.13
_diffrn_reflns_theta_max         70.13
_diffrn_reflns_theta_min         4.39
_diffrn_standards_decay_%        3.7
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          .43
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .18
_refine_diff_density_max         .34
_refine_diff_density_min         -.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          .055
_refine_ls_R_factor_gt           .042
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0674P)²+0.5232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .127
_reflns_number_gt                3135
_reflns_number_total             3851
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz1436.cif
_cod_data_source_block           IV
_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:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.5232P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.5232P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2011887
_cod_database_fobs_code          2011887
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 .25752(15) .65795(8) 1.11034(11) .0415(3) Uani d . 1 . . N
C2 .2022(2) .71521(11) 1.15519(17) .0541(5) Uani d . 1 . . C
N3 .2722(2) .73276(8) 1.25267(15) .0578(4) Uani d . 1 . . N
C4 .37949(19) .68461(9) 1.27170(14) .0444(4) Uani d . 1 . . C
C5 .37352(18) .63746(9) 1.18701(13) .0393(4) Uani d . 1 . . C
C6 .2061(2) .62955(12) .99913(15) .0492(4) Uani d . 1 . . C
C7 .29988(17) .65246(9) .90886(14) .0394(4) Uani d . 1 . . C
C8 .41305(19) .70944(9) .93221(15) .0422(4) Uani d . 1 . . C
N9 .28839(15) .62582(8) .81027(12) .0439(3) Uani d . 1 . . N
N10 .18812(17) .57209(8) .78763(13) .0469(4) Uani d . 1 . . N
C11 .19044(17) .53541(9) .69125(13) .0410(4) Uani d . 1 . . C
C12 .10082(18) .47585(9) .66530(15) .0447(4) Uani d . 1 . . C
C13 .1098(2) .43736(10) .56836(16) .0489(4) Uani d . 1 . . C
C14 .2066(2) .45791(10) .49539(16) .0510(4) Uani d . 1 . . C
C15 .2943(2) .51690(11) .51555(17) .0529(4) Uani d . 1 . . C
C16 .2867(2) .55486(10) .61103(15) .0491(4) Uani d . 1 . . C
N17 -.00566(19) .45181(10) .73865(14) .0582(4) Uani d . 1 . . N
O18 -.01693(17) .48265(9) .82804(13) .0700(4) Uani d . 1 . . O
O19 -.0826(2) .40184(12) .70885(17) .1019(7) Uani d . 1 . . O
N20 .2155(2) .41769(11) .39266(17) .0718(5) Uani d . 1 . . N
O21 .1312(3) .36869(11) .37305(19) .1066(7) Uani d . 1 . . O
O22 .3060(3) .43594(13) .33007(18) .1137(8) Uani d . 1 . . O
N23 .54698(14) .68306(7) .99897(11) .0388(3) Uani d . 1 . . N
C24 .6390(2) .74094(11) 1.04680(18) .0517(5) Uani d . 1 . . C
C25 .7778(2) .71309(16) 1.1134(2) .0704(7) Uani d . 1 . . C
O26 .86181(15) .67108(11) 1.04582(16) .0840(6) Uani d . 1 . . O
C27 .7726(2) .61397(15) 1.0000(3) .0738(7) Uani d . 1 . . C
C28 .6340(2) .63977(11) .92951(18) .0494(4) Uani d . 1 . . C
N29 .4856(2) .68843(10) 1.37304(14) .0615(5) Uani d . 1 . . N
O30 .4647(3) .65756(14) 1.45398(16) .1131(8) Uani d . 1 . . O
O31 .5875(3) .72788(17) 1.36971(19) .1423(12) Uani d . 1 . . O
N32 .4635(2) .57824(9) 1.17602(15) .0572(4) Uani d . 1 . . N
O33 .5700(2) .57225(12) 1.24768(17) .1012(7) Uani d . 1 . . O
O34 .4326(2) .53839(8) 1.09758(16) .0814(5) Uani d . 1 . . O
H2A .121(3) .7411(13) 1.115(2) .072(7) Uiso d . 1 . . H
H6A .206(3) .5790(13) 1.008(2) .067(7) Uiso d . 1 . . H
H6B .104(3) .6484(13) .979(2) .074(7) Uiso d . 1 . . H
H8A .371(2) .7485(10) .9772(16) .046(5) Uiso d . 1 . . H
H8B .435(2) .7302(10) .8578(17) .048(5) Uiso d . 1 . . H
H10A .130(3) .5591(11) .8327(19) .057(6) Uiso d . 1 . . H
H13A .055(3) .3988(13) .5556(18) .061(6) Uiso d . 1 . . H
H15A .360(3) .5293(13) .464(2) .074(7) Uiso d . 1 . . H
H16A .351(3) .5942(12) .6306(19) .062(6) Uiso d . 1 . . H
H24A .663(2) .7742(12) .9842(19) .061(6) Uiso d . 1 . . H
H24B .586(3) .7672(12) 1.0971(19) .062(6) Uiso d . 1 . . H
H25A .753(3) .6824(12) 1.180(2) .066(7) Uiso d . 1 . . H
H25B .838(3) .7492(14) 1.147(2) .077(7) Uiso d . 1 . . H
H27A .832(3) .5897(14) .945(2) .087(8) Uiso d . 1 . . H
H27B .745(3) .5818(15) 1.063(2) .093(9) Uiso d . 1 . . H
H28A .578(2) .6009(11) .9030(17) .050(5) Uiso d . 1 . . H
H28B .650(3) .6671(11) .8631(19) .060(6) Uiso d . 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 .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 '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
C2 N1 C5 105.17(15) yes
C2 N1 C6 124.94(16) ?
C5 N1 C6 129.74(15) ?
N3 C2 N1 113.67(18) yes
N3 C2 H2A 124.8(14) ?
N1 C2 H2A 121.5(14) ?
C2 N3 C4 103.92(16) yes
N3 C4 C5 111.70(16) yes
N3 C4 N29 120.06(17) ?
C5 C4 N29 128.24(17) ?
C4 C5 N1 105.53(15) yes
C4 C5 N32 129.35(16) ?
N1 C5 N32 125.12(15) ?
N1 C6 C7 113.06(14) ?
N1 C6 H6A 105.8(14) ?
C7 C6 H6A 112.1(14) ?
N1 C6 H6B 105.9(14) ?
C7 C6 H6B 107.6(14) ?
H6A C6 H6B 112(2) ?
N9 C7 C8 116.43(15) ?
N9 C7 C6 123.13(15) ?
C8 C7 C6 120.44(15) ?
N23 C8 C7 110.64(13) ?
N23 C8 H8A 107.8(11) ?
C7 C8 H8A 110.1(11) ?
N23 C8 H8B 112.5(11) ?
C7 C8 H8B 108.7(11) ?
H8A C8 H8B 107.0(15) ?
C7 N9 N10 117.57(14) ?
C11 N10 N9 118.88(15) ?
C11 N10 H10A 117.8(15) ?
N9 N10 H10A 123.2(15) ?
N10 C11 C16 120.51(16) ?
N10 C11 C12 122.93(16) ?
C16 C11 C12 116.55(16) ?
C13 C12 C11 121.89(17) ?
C13 C12 N17 116.13(17) ?
C11 C12 N17 121.98(16) ?
C14 C13 C12 118.84(18) ?
C14 C13 H13A 121.2(15) ?
C12 C13 H13A 119.9(15) ?
C13 C14 C15 121.52(18) ?
C13 C14 N20 118.96(19) ?
C15 C14 N20 119.50(19) ?
C16 C15 C14 120.00(19) ?
C16 C15 H15A 120.7(15) ?
C14 C15 H15A 119.3(15) ?
C15 C16 C11 121.17(18) ?
C15 C16 H16A 122.2(13) ?
C11 C16 H16A 116.5(13) ?
O19 N17 O18 122.07(18) ?
O19 N17 C12 118.29(18) ?
O18 N17 C12 119.63(16) ?
O21 N20 O22 123.7(2) ?
O21 N20 C14 118.5(2) ?
O22 N20 C14 117.8(2) ?
C8 N23 C24 110.30(14) ?
C8 N23 C28 110.78(14) ?
C24 N23 C28 109.45(14) ?
N23 C24 C25 109.73(18) ?
N23 C24 H24A 110.4(13) ?
C25 C24 H24A 111.8(13) ?
N23 C24 H24B 109.9(14) ?
C25 C24 H24B 107.9(14) ?
H24A C24 H24B 107.0(18) ?
O26 C25 C24 111.80(18) ?
O26 C25 H25A 106.7(14) ?
C24 C25 H25A 111.3(14) ?
O26 C25 H25B 109.6(16) ?
C24 C25 H25B 111.8(16) ?
H25A C25 H25B 105(2) ?
C25 O26 C27 109.66(17) ?
O26 C27 C28 110.8(2) ?
O26 C27 H27A 106.3(16) ?
C28 C27 H27A 105.0(16) ?
O26 C27 H27B 110.6(17) ?
C28 C27 H27B 110.7(17) ?
H27A C27 H27B 113(2) ?
N23 C28 C27 109.71(17) ?
N23 C28 H28A 109.9(12) ?
C27 C28 H28A 107.8(12) ?
N23 C28 H28B 107.1(13) ?
C27 C28 H28B 115.8(14) ?
H28A C28 H28B 106.4(17) ?
O30 N29 O31 123.2(2) ?
O30 N29 C4 120.43(17) ?
O31 N29 C4 116.18(19) ?
O34 N32 O33 124.97(19) ?
O34 N32 C5 119.62(17) ?
O33 N32 C5 115.39(18) ?
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
N1 C2 . 1.344(2) yes
N1 C5 . 1.367(2) yes
N1 C6 . 1.458(2) ?
C2 N3 . 1.301(3) yes
C2 H2A . .97(3) ?
N3 C4 . 1.340(2) yes
C4 C5 . 1.352(2) yes
C4 N29 . 1.455(2) yes
C5 N32 . 1.413(2) yes
C6 C7 . 1.509(2) ?
C6 H6A . .98(2) ?
C6 H6B . .99(3) ?
C7 N9 . 1.274(2) yes
C7 C8 . 1.502(2) ?
C8 N23 . 1.461(2) yes
C8 H8A . 1.02(2) ?
C8 H8B . 1.01(2) ?
N9 N10 . 1.379(2) yes
N10 C11 . 1.349(2) yes
N10 H10A . .83(2) ?
C11 C16 . 1.414(2) ?
C11 C12 . 1.415(2) ?
C12 C13 . 1.381(3) ?
C12 N17 . 1.447(2) yes
C13 C14 . 1.360(3) ?
C13 H13A . .90(2) ?
C14 C15 . 1.388(3) ?
C14 N20 . 1.457(3) yes
C15 C16 . 1.359(3) ?
C15 H15A . .93(3) ?
C16 H16A . .97(2) ?
N17 O19 . 1.214(2) ?
N17 O18 . 1.233(2) ?
N20 O21 . 1.216(3) ?
N20 O22 . 1.220(3) ?
N23 C24 . 1.464(2) ?
N23 C28 . 1.464(2) ?
C24 C25 . 1.504(3) ?
C24 H24A . 1.02(2) ?
C24 H24B . .96(2) ?
C25 O26 . 1.420(3) ?
C25 H25A . 1.03(2) ?
C25 H25B . .94(3) ?
O26 C27 . 1.432(3) ?
C27 C28 . 1.509(3) ?
C27 H27A . 1.01(3) ?
C27 H27B . 1.03(3) ?
C28 H28A . .94(2) ?
C28 H28B . .97(2) ?
N29 O30 . 1.165(2) ?
N29 O31 . 1.197(2) ?
N32 O34 . 1.215(2) ?
N32 O33 . 1.217(2) ?
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
N10 H10A O18 . .83(2) 1.98(2) 2.611(2) 133(2) yes
C6 H6A O34 . .98(2) 2.33(2) 2.842(2) 112.0(18) yes
C6 H6B O26 1_455 .99(3) 2.46(3) 3.320(2) 145.4(19) yes
C13 H13A O19 . .90(2) 2.32(2) 2.637(3) 100.6(16) .
C16 H16A N9 . .98(2) 2.36(2) 2.735(2) 102.5(16) .
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
C5 N1 C2 N3 .0(2)
C6 N1 C2 N3 -175.99(17)
N1 C2 N3 C4 .5(2)
C2 N3 C4 C5 -.8(2)
C2 N3 C4 N29 178.02(17)
N3 C4 C5 N1 .87(19)
N29 C4 C5 N1 -177.87(16)
N3 C4 C5 N32 -178.40(17)
N29 C4 C5 N32 2.9(3)
C2 N1 C5 C4 -.52(18)
C6 N1 C5 C4 175.22(16)
C2 N1 C5 N32 178.78(17)
C6 N1 C5 N32 -5.5(3)
C2 N1 C6 C7 96.5(2)
C5 N1 C6 C7 -78.5(2)
N1 C6 C7 N9 169.24(16)
N1 C6 C7 C8 -11.1(2)
N9 C7 C8 N23 -102.43(17)
C6 C7 C8 N23 77.9(2)
C8 C7 N9 N10 178.28(14)
C6 C7 N9 N10 -2.0(2)
C7 N9 N10 C11 -169.32(15)
N9 N10 C11 C16 -4.5(2)
N9 N10 C11 C12 174.50(15)
N10 C11 C12 C13 -177.15(16)
C16 C11 C12 C13 1.9(2)
N10 C11 C12 N17 3.0(3)
C16 C11 C12 N17 -178.03(16)
C11 C12 C13 C14 -.7(3)
N17 C12 C13 C14 179.20(16)
C12 C13 C14 C15 -.9(3)
C12 C13 C14 N20 -179.56(17)
C13 C14 C15 C16 1.3(3)
N20 C14 C15 C16 179.91(19)
C14 C15 C16 C11 .0(3)
N10 C11 C16 C15 177.54(17)
C12 C11 C16 C15 -1.5(3)
C13 C12 N17 O19 -2.6(3)
C11 C12 N17 O19 177.3(2)
C13 C12 N17 O18 178.20(17)
C11 C12 N17 O18 -1.9(3)
C13 C14 N20 O21 3.2(3)
C15 C14 N20 O21 -175.5(2)
C13 C14 N20 O22 -178.0(2)
C15 C14 N20 O22 3.3(3)
C7 C8 N23 C24 -164.91(14)
C7 C8 N23 C28 73.76(18)
C8 N23 C24 C25 -178.91(16)
C28 N23 C24 C25 -56.8(2)
N23 C24 C25 O26 58.2(3)
C24 C25 O26 C27 -58.8(3)
C25 O26 C27 C28 58.9(3)
C8 N23 C28 C27 179.28(17)
C24 N23 C28 C27 57.4(2)
O26 C27 C28 N23 -58.9(3)
N3 C4 N29 O30 94.2(3)
C5 C4 N29 O30 -87.2(3)
N3 C4 N29 O31 -81.2(3)
C5 C4 N29 O31 97.4(3)
C4 C5 N32 O34 173.61(19)
N1 C5 N32 O34 -5.5(3)
C4 C5 N32 O33 -7.6(3)
N1 C5 N32 O33 173.31(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21182169
