#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/11/2011138.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_2011138
loop_
_publ_author_name
'Taycher, Hellena'
'Shteiman, Vitaly'
'Botoshansky, Mark'
'Kaftory, Menahem'
_publ_section_title
;3,5-Dimethyl-6-(4-nitroanilino)-2,3,4,5-tetrahydro-1,3,5-triazine-2,4-dione,
 (II),
 3,5-dimethyl-6-(N-methyl-4-nitroanilino)-2,3,4,5-tetrahydro-1,3,5-triazine-2,4-dione,
 (III), and 1,3,5-trimethyl-6-(4-nitrophenylimino)-1,3,5-triazinane-2,4-dione,
 (IV)
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              832
_journal_page_last               835
_journal_paper_doi               10.1107/S0108270100004303
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C11 H13 N5 O5'
_chemical_formula_weight         295.26
_chemical_name_common            Lena-3h
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.170(4)
_cell_length_b                   10.530(3)
_cell_length_c                   6.972(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.7
_cell_measurement_theta_min      3.2
_cell_volume                     1334.0(6)
_computing_cell_refinement       'Philips PW 1110/20'
_computing_data_collection       'Philips PW 1110/20 (Philips, 1973)'
_computing_data_reduction        'PROCN (Philips, 1973)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and TEXSAN (Molecular Structure Corporation, 1995)'
_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 .973
_diffrn_measured_fraction_theta_max .973
_diffrn_measurement_device       'Philips PW 1100 diffractometer'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .0000
_diffrn_reflns_av_sigmaI/netI    .0503
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1339
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        2.1
_diffrn_standards_interval_count '120 min'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          .80
_exptl_crystal_size_mid          .50
_exptl_crystal_size_min          .40
_refine_diff_density_max         .203
_refine_diff_density_min         -.197
_refine_ls_extinction_coef       .024(3)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         1339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          .0676
_refine_ls_R_factor_gt           .0487
_refine_ls_shift/su_max          .030
_refine_ls_shift/su_mean         .002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0499P)²+0.9787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1297
_reflns_number_gt                1152
_reflns_number_total             1339
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1458.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      P_21_21_21
_cod_original_formula_sum        'C11 H11 N5 O4 , H2 O'
_cod_database_code               2011138
_cod_database_fobs_code          2011138
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
O1 .78975(17) .3631(3) .1258(7) .0577(11) Uani d . 1 . . O
O2 .54559(15) .2910(3) .1905(6) .0533(10) Uani d . 1 . . O
O3 1.02148(19) -.3010(4) .1898(8) .0930(16) Uani d . 1 . . O
O4 .9512(2) -.4611(4) .1494(8) .0876(15) Uani d . 1 . . O
O5 .60984(19) -.2423(4) .3599(7) .0629(12) Uani d . 1 . . O
N1 .66752(18) .3310(3) .1619(6) .0372(9) Uani d . 1 . . N
N2 .75229(17) .1604(3) .1721(6) .0348(9) Uani d . 1 . . N
N3 .62488(16) .1245(3) .2113(6) .0335(9) Uani d . 1 . . N
N4 .70773(18) -.0424(3) .2157(6) .0353(9) Uani d . 1 . . N
N5 .9609(2) -.3478(4) .1737(7) .0580(12) Uani d . 1 . . N
C1 .7403(2) .2863(4) .1523(7) .0384(11) Uani d . 1 . . C
C2 .6969(2) .0845(4) .2002(6) .0296(9) Uani d . 1 . . C
C3 .6085(2) .2528(4) .1892(7) .0348(10) Uani d . 1 . . C
C4 .7747(2) -.1104(4) .2001(6) .0318(10) Uani d . 1 . . C
C5 .8446(2) -.0583(4) .2259(7) .0372(10) Uani d . 1 . . C
H5 .8502 .0281 .2501 .045 Uiso calc . 1 . . H
C6 .9055(2) -.1370(4) .2148(7) .0411(11) Uani d . 1 . . C
H6 .9524 -.1035 .2308 .049 Uiso calc . 1 . . H
C7 .8966(2) -.2643(4) .1804(7) .0385(10) Uani d . 1 . . C
C8 .8276(2) -.3176(4) .1545(8) .0433(12) Uani d . 1 . . C
H8 .8224 -.4043 .1324 .052 Uiso calc . 1 . . H
C9 .7672(2) -.2396(4) .1621(7) .0373(10) Uani d . 1 . . C
H9 .7206 -.2735 .1415 .045 Uiso calc . 1 . . H
C10 .6534(3) .4680(4) .1406(10) .0593(15) Uani d . 1 . . C
H10A .6794 .4995 .0306 .089 Uiso calc R 1 . . H
H10B .6699 .5118 .2533 .089 Uiso calc R 1 . . H
H10C .6015 .4819 .1238 .089 Uiso calc R 1 . . H
C11 .5629(2) .0363(4) .2329(9) .0518(14) Uani d . 1 . . C
H11A .5176 .0834 .2362 .078 Uiso calc R 1 . . H
H11B .5683 -.0106 .3501 .078 Uiso calc R 1 . . H
H11C .5621 -.0215 .1264 .078 Uiso calc R 1 . . H
H1N4 .674(2) -.089(4) .241(7) .037(13) Uiso d . 1 . . H
H1O5 .621(3) -.277(6) .463(9) .07(2) Uiso d . 1 . . H
H2O5 .559(5) -.243(8) .358(12) .16(3) 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
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C .0033 .0016 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1O5 O5 H2O5 104(6)
C3 N1 C1 122.9(3)
C3 N1 C10 117.9(3)
C1 N1 C10 119.2(4)
C2 N2 C1 119.5(3)
C2 N3 C3 119.6(3)
C2 N3 C11 122.8(3)
C3 N3 C11 117.5(3)
C2 N4 C4 128.2(4)
C2 N4 H1N4 121(3)
C4 N4 H1N4 111(3)
O3 N5 O4 122.9(4)
O3 N5 C7 118.6(4)
O4 N5 C7 118.5(4)
O1 C1 N2 123.0(4)
O1 C1 N1 118.5(4)
N2 C1 N1 118.4(4)
N2 C2 N4 120.4(4)
N2 C2 N3 123.8(3)
N4 C2 N3 115.8(4)
O2 C3 N1 122.8(4)
O2 C3 N3 121.6(4)
N1 C3 N3 115.6(3)
C9 C4 C5 119.8(4)
C9 C4 N4 115.2(3)
C5 C4 N4 125.0(3)
C6 C5 C4 119.0(4)
C6 C5 H5 120.5
C4 C5 H5 120.5
C7 C6 C5 120.1(4)
C7 C6 H6 120.0
C5 C6 H6 120.0
C6 C7 C8 121.7(4)
C6 C7 N5 120.0(4)
C8 C7 N5 118.4(4)
C9 C8 C7 118.4(4)
C9 C8 H8 120.8
C7 C8 H8 120.8
C8 C9 C4 121.0(4)
C8 C9 H9 119.5
C4 C9 H9 119.5
N1 C10 H10A 109.5
N1 C10 H10B 109.5
H10A C10 H10B 109.5
N1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N3 C11 H11A 109.5
N3 C11 H11B 109.5
H11A C11 H11B 109.5
N3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 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 . 1.223(5) ?
O2 C3 . 1.212(5) ?
O3 N5 . 1.210(6) ?
O4 N5 . 1.218(6) ?
O5 H1O5 . .83(6) ?
O5 H2O5 . .93(8) ?
N1 C3 . 1.365(5) ?
N1 C1 . 1.404(5) ?
N1 C10 . 1.473(5) ?
N2 C2 . 1.300(5) ?
N2 C1 . 1.351(5) ?
N3 C2 . 1.377(5) ?
N3 C3 . 1.391(5) ?
N3 C11 . 1.468(5) ?
N4 C2 . 1.355(5) ?
N4 C4 . 1.416(5) ?
N4 H1N4 . .80(4) ?
N5 C7 . 1.462(5) ?
C4 C9 . 1.393(6) ?
C4 C5 . 1.395(6) ?
C5 C6 . 1.385(6) ?
C5 H5 . .9300 ?
C6 C7 . 1.372(7) ?
C6 H6 . .9300 ?
C7 C8 . 1.386(6) ?
C8 C9 . 1.372(6) ?
C8 H8 . .9300 ?
C9 H9 . .9300 ?
C10 H10A . .9600 ?
C10 H10B . .9600 ?
C10 H10C . .9600 ?
C11 H11A . .9600 ?
C11 H11B . .9600 ?
C11 H11C . .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
N4 H1N4 O5 1_555 .81(5) 2.16(5) 2.933(5) 162(5)
O5 H2O5 O2 3_645 .92(11) 1.96(11) 2.867(5) 166(10)
O5 H1O5 O1 2_655 .83(6) 2.18(6) 2.895(6) 145(5)
O9 H9 O5 1_555 .93(5) 2.55(5) 3.175(6) 125(4)
C5 H5 N2 1_555 .93(5) 2.32(4) 2.874(5) 117(4)
C6 H6 O4 3_755 .93(5) 2.45(5) 3.333(6) 158(4)
C8 H8 O1 1_545 .93(5) 2.52(5) 3.438(6) 169(4)
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
C2 N2 C1 O1 179.9(5)
C2 N2 C1 N1 -.3(7)
C3 N1 C1 O1 179.4(5)
C10 N1 C1 O1 -.2(8)
C3 N1 C1 N2 -.4(7)
C10 N1 C1 N2 -180.0(5)
C1 N2 C2 N4 178.4(5)
C1 N2 C2 N3 .1(7)
C4 N4 C2 N2 -1.8(8)
C4 N4 C2 N3 176.6(4)
C3 N3 C2 N2 .9(7)
C11 N3 C2 N2 176.6(5)
C3 N3 C2 N4 -177.5(4)
C11 N3 C2 N4 -1.7(7)
C1 N1 C3 O2 -177.2(5)
C10 N1 C3 O2 2.3(7)
C1 N1 C3 N3 1.3(7)
C10 N1 C3 N3 -179.1(5)
C2 N3 C3 O2 177.1(4)
C11 N3 C3 O2 1.1(8)
C2 N3 C3 N1 -1.5(7)
C11 N3 C3 N1 -177.5(4)
C2 N4 C4 C9 -160.6(5)
C2 N4 C4 C5 21.5(8)
C9 C4 C5 C6 -.6(7)
N4 C4 C5 C6 177.2(4)
C4 C5 C6 C7 -.5(7)
C5 C6 C7 C8 .5(8)
C5 C6 C7 N5 -178.4(5)
O3 N5 C7 C6 -3.5(8)
O4 N5 C7 C6 177.5(6)
O3 N5 C7 C8 177.5(6)
O4 N5 C7 C8 -1.4(8)
C6 C7 C8 C9 .6(8)
N5 C7 C8 C9 179.5(5)
C7 C8 C9 C4 -1.7(8)
C5 C4 C9 C8 1.8(8)
N4 C4 C9 C8 -176.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135670
