#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/55/2225595.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_2225595
loop_
_publ_author_name
'Xu, Liang-Zhong'
'Yin, Rui-Feng'
'Li, Hong-Xin'
_publ_section_title
;
 (E)-5-Benzyl-1-methyl-N-nitro-1,3,5-triazinan-2-imine
;
_journal_coeditor_code           IS2529
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o867
_journal_paper_doi               10.1107/S1600536810009426
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H15 N5 O2'
_chemical_formula_moiety         'C11 H15 N5 O2'
_chemical_formula_sum            'C11 H15 N5 O2'
_chemical_formula_weight         249.28
_chemical_name_systematic
;
(E)-5-Benzyl-1-methyl-N-nitro-1,3,5-triazinan-2-imine
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.36(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.293(3)
_cell_length_b                   6.7769(14)
_cell_length_c                   14.858(3)
_cell_measurement_reflns_used    2501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.11
_cell_measurement_theta_min      2.27
_cell_volume                     1181.4(5)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10812
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.33
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.284
_refine_ls_extinction_coef       0.053(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0431
_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)+(0.0641P)²+0.4408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                2215
_reflns_number_total             2697
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2529.cif
_cod_data_source_block           I
_cod_original_cell_volume        1181.5(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225595
_cod_database_fobs_code          2225595
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.08476(12) 0.2664(2) 0.32912(13) 0.0648(5) Uani d . 1 . .
O O2 -0.20472(10) 0.4688(2) 0.23990(9) 0.0491(4) Uani d . 1 . .
N N1 0.13187(12) 0.3877(2) 0.34487(10) 0.0396(4) Uani d . 1 . .
H H1A 0.0946 0.2966 0.3081 0.048 Uiso calc R 1 . .
N N2 0.13204(11) 0.69132(19) 0.41305(9) 0.0337(3) Uani d . 1 . .
N N3 0.29652(11) 0.4822(2) 0.47169(9) 0.0324(3) Uani d . 1 . .
N N4 -0.03718(11) 0.5836(2) 0.31457(11) 0.0399(4) Uani d . 1 . .
N N5 -0.10875(11) 0.4321(2) 0.29433(9) 0.0342(3) Uani d . 1 . .
C C1 0.07548(13) 0.5462(2) 0.35840(10) 0.0320(3) Uani d . 1 . .
C C2 0.07568(15) 0.8650(3) 0.43518(14) 0.0446(4) Uani d . 1 . .
H H2A -0.0053 0.8513 0.4084 0.067 Uiso calc R 1 . .
H H2B 0.1011 0.9799 0.4094 0.067 Uiso calc R 1 . .
H H2C 0.0940 0.8786 0.5024 0.067 Uiso calc R 1 . .
C C3 0.25803(13) 0.6801(2) 0.44754(12) 0.0379(4) Uani d . 1 . .
H H3A 0.2893 0.7288 0.3991 0.046 Uiso calc R 1 . .
H H3B 0.2858 0.7639 0.5025 0.046 Uiso calc R 1 . .
C C4 0.25463(13) 0.3596(3) 0.38930(11) 0.0354(4) Uani d . 1 . .
H H4B 0.2694 0.2222 0.4071 0.043 Uiso calc R 1 . .
H H4C 0.2951 0.3913 0.3443 0.043 Uiso calc R 1 . .
C C5 0.26964(14) 0.4064(3) 0.55497(11) 0.0370(4) Uani d . 1 . .
H H5A 0.1889 0.3765 0.5381 0.044 Uiso calc R 1 . .
H H5B 0.2855 0.5083 0.6030 0.044 Uiso calc R 1 . .
C C6 0.33636(12) 0.2241(2) 0.59520(10) 0.0305(3) Uani d . 1 . .
C C7 0.29232(14) 0.0894(3) 0.64553(11) 0.0366(4) Uani d . 1 . .
H H7A 0.2200 0.1099 0.6516 0.044 Uiso calc R 1 . .
C C8 0.35422(16) -0.0750(3) 0.68681(12) 0.0420(4) Uani d . 1 . .
H H8A 0.3239 -0.1632 0.7209 0.050 Uiso calc R 1 . .
C C9 0.46112(16) -0.1076(3) 0.67726(12) 0.0426(4) Uani d . 1 . .
H H9A 0.5029 -0.2181 0.7046 0.051 Uiso calc R 1 . .
C C10 0.50547(14) 0.0239(3) 0.62723(12) 0.0426(4) Uani d . 1 . .
H H10A 0.5775 0.0018 0.6209 0.051 Uiso calc R 1 . .
C C11 0.44426(13) 0.1892(3) 0.58611(11) 0.0376(4) Uani d . 1 . .
H H11A 0.4753 0.2770 0.5524 0.045 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C4 . . 123.43(14) ?
C1 N1 H1A . . 118.3 ?
C4 N1 H1A . . 118.3 ?
C1 N2 C2 . . 122.62(13) ?
C1 N2 C3 . . 118.34(13) ?
C2 N2 C3 . . 118.93(13) ?
C3 N3 C4 . . 108.64(12) ?
C3 N3 C5 . . 113.51(13) ?
C4 N3 C5 . . 113.66(14) ?
N5 N4 C1 . . 118.25(13) ?
O1 N5 O2 . . 121.13(14) ?
O1 N5 N4 . . 123.34(14) ?
O2 N5 N4 . . 115.48(14) ?
N1 C1 N2 . . 119.30(14) ?
N1 C1 N4 . . 125.42(14) ?
N2 C1 N4 . . 115.07(14) ?
N2 C2 H2A . . 109.5 ?
N2 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
N2 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
N3 C3 N2 . . 111.61(13) ?
N3 C3 H3A . . 109.3 ?
N2 C3 H3A . . 109.3 ?
N3 C3 H3B . . 109.3 ?
N2 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
N3 C4 N1 . . 111.46(13) ?
N3 C4 H4B . . 109.3 ?
N1 C4 H4B . . 109.3 ?
N3 C4 H4C . . 109.3 ?
N1 C4 H4C . . 109.3 ?
H4B C4 H4C . . 108.0 ?
N3 C5 C6 . . 112.94(12) ?
N3 C5 H5A . . 109.0 ?
C6 C5 H5A . . 109.0 ?
N3 C5 H5B . . 109.0 ?
C6 C5 H5B . . 109.0 ?
H5A C5 H5B . . 107.8 ?
C7 C6 C11 . . 118.43(15) ?
C7 C6 C5 . . 120.00(14) ?
C11 C6 C5 . . 121.53(14) ?
C8 C7 C6 . . 121.10(15) ?
C8 C7 H7A . . 119.5 ?
C6 C7 H7A . . 119.5 ?
C9 C8 C7 . . 119.81(16) ?
C9 C8 H8A . . 120.1 ?
C7 C8 H8A . . 120.1 ?
C10 C9 C8 . . 119.68(16) ?
C10 C9 H9A . . 120.2 ?
C8 C9 H9A . . 120.2 ?
C9 C10 C11 . . 120.81(16) ?
C9 C10 H10A . . 119.6 ?
C11 C10 H10A . . 119.6 ?
C10 C11 C6 . . 120.15(15) ?
C10 C11 H11A . . 119.9 ?
C6 C11 H11A . . 119.9 ?
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 N5 . 1.2350(19) ?
O2 N5 . 1.2404(18) ?
N1 C1 . 1.326(2) ?
N1 C4 . 1.468(2) ?
N1 H1A . 0.8600 ?
N2 C1 . 1.332(2) ?
N2 C2 . 1.452(2) ?
N2 C3 . 1.4811(19) ?
N3 C3 . 1.431(2) ?
N3 C4 . 1.442(2) ?
N3 C5 . 1.466(2) ?
N4 N5 . 1.3269(19) ?
N4 C1 . 1.367(2) ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 H4B . 0.9700 ?
C4 H4C . 0.9700 ?
C5 C6 . 1.505(2) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.388(2) ?
C6 C11 . 1.393(2) ?
C7 C8 . 1.385(2) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.381(3) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.373(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.385(2) ?
C10 H10A . 0.9300 ?
C11 H11A . 0.9300 ?
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
N1 H1A N4 2_545 0.86 2.27 3.093(2) 162
C3 H3A O2 2 0.97 2.59 3.305(2) 131
N1 H1A O1 . 0.86 2.33 2.730(2) 109
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N4 N5 O1 . . . . 15.3(2) ?
C1 N4 N5 O2 . . . . -167.27(14) ?
C4 N1 C1 N2 . . . . 1.7(2) ?
C4 N1 C1 N4 . . . . 176.15(15) ?
C2 N2 C1 N1 . . . . -176.81(16) ?
C3 N2 C1 N1 . . . . 7.1(2) ?
C2 N2 C1 N4 . . . . 8.2(2) ?
C3 N2 C1 N4 . . . . -167.92(14) ?
N5 N4 C1 N1 . . . . 34.1(2) ?
N5 N4 C1 N2 . . . . -151.22(15) ?
C4 N3 C3 N2 . . . . 59.01(17) ?
C5 N3 C3 N2 . . . . -68.49(17) ?
C1 N2 C3 N3 . . . . -38.5(2) ?
C2 N2 C3 N3 . . . . 145.25(15) ?
C3 N3 C4 N1 . . . . -49.73(18) ?
C5 N3 C4 N1 . . . . 77.68(17) ?
C1 N1 C4 N3 . . . . 20.6(2) ?
C3 N3 C5 C6 . . . . -164.43(13) ?
C4 N3 C5 C6 . . . . 70.73(17) ?
N3 C5 C6 C7 . . . . -153.33(14) ?
N3 C5 C6 C11 . . . . 28.9(2) ?
C11 C6 C7 C8 . . . . 0.7(2) ?
C5 C6 C7 C8 . . . . -177.09(14) ?
C6 C7 C8 C9 . . . . -0.7(3) ?
C7 C8 C9 C10 . . . . 0.3(3) ?
C8 C9 C10 C11 . . . . 0.0(3) ?
C9 C10 C11 C6 . . . . 0.1(3) ?
C7 C6 C11 C10 . . . . -0.4(2) ?
C5 C6 C11 C10 . . . . 177.37(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 679225
