#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/75/2227503.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227503
loop_
_publ_author_name
'Tian, Zhongzhen'
'Dong, Haijun'
'Li, Dongmei'
'Wang, Gaolei'
_publ_section_title
;
 (E)-1-[(1,3-Dioxan-4-yl)methyl]-2-(nitromethylidene)imidazolidine
;
_journal_coeditor_code           HB5607
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2359
_journal_paper_doi               10.1107/S1600536810032691
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H15 N3 O4'
_chemical_formula_moiety         'C9 H15 N3 O4'
_chemical_formula_sum            'C9 H15 N3 O4'
_chemical_formula_weight         229.24
_chemical_name_systematic
;
(E)-1-[(1,3-Dioxan-4-yl)methyl]-2-(nitromethylidene)imidazolidine
;
_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'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0138(4)
_cell_length_b                   9.8092(9)
_cell_length_c                   21.7162(18)
_cell_measurement_reflns_used    2831
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.6936
_cell_measurement_theta_min      3.4909
_cell_volume                     1068.03(16)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5866
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0535
_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)+(0.1126P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1630
_refine_ls_wR_factor_ref         0.1736
_reflns_number_gt                1395
_reflns_number_total             1933
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hb5607.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227503
_cod_database_fobs_code          2227503
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_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 O2 0.7955(3) 0.71286(16) 0.23056(8) 0.0532(5) Uani d . 1 . .
N N1 0.7422(4) 0.58813(19) 0.22961(9) 0.0420(5) Uani d . 1 . .
C C2 0.3945(4) 0.6124(2) 0.30617(10) 0.0343(5) Uani d . 1 . .
O O3 0.2691(4) 0.39753(16) 0.44986(7) 0.0536(5) Uani d . 1 . .
N N2 0.4042(4) 0.74655(19) 0.31417(9) 0.0435(5) Uani d . 1 . .
H H2 0.5038 0.8003 0.2930 0.052 Uiso calc R 1 . .
C C1 0.5501(4) 0.5344(2) 0.26581(10) 0.0390(6) Uani d . 1 . .
H H1 0.5196 0.4409 0.2638 0.047 Uiso calc R 1 . .
N N3 0.2104(4) 0.55718(19) 0.34370(8) 0.0421(5) Uani d . 1 . .
O O1 0.8720(4) 0.51016(18) 0.19406(9) 0.0640(6) Uani d . 1 . .
C C5 0.1287(5) 0.4153(2) 0.34624(11) 0.0432(6) Uani d . 1 . .
H H5A 0.1514 0.3753 0.3057 0.052 Uiso calc R 1 . .
H H5B -0.0597 0.4115 0.3563 0.052 Uiso calc R 1 . .
C C6 0.2786(5) 0.3314(2) 0.39185(10) 0.0406(6) Uani d . 1 . .
H H6 0.4653 0.3268 0.3787 0.049 Uiso calc R 1 . .
O O4 0.2921(5) 0.1954(2) 0.50513(9) 0.0741(7) Uani d . 1 . .
C C7 0.1743(5) 0.1882(2) 0.39737(11) 0.0453(6) Uani d . 1 . .
H H7A 0.2109 0.1387 0.3596 0.054 Uiso calc R 1 . .
H H7B -0.0175 0.1904 0.4032 0.054 Uiso calc R 1 . .
C C4 0.0734(5) 0.6627(3) 0.37948(11) 0.0474(6) Uani d . 1 . .
H H4B 0.0835 0.6438 0.4233 0.057 Uiso calc R 1 . .
H H4A -0.1125 0.6699 0.3675 0.057 Uiso calc R 1 . .
C C3 0.2257(5) 0.7920(2) 0.36326(11) 0.0507(7) Uani d . 1 . .
H H3A 0.1061 0.8629 0.3488 0.061 Uiso calc R 1 . .
H H3B 0.3255 0.8258 0.3984 0.061 Uiso calc R 1 . .
C C9 0.4109(7) 0.3220(3) 0.49462(13) 0.0653(8) Uani d . 1 . .
H H9A 0.5930 0.3086 0.4808 0.078 Uiso calc R 1 . .
H H9B 0.4163 0.3731 0.5328 0.078 Uiso calc R 1 . .
C C8 0.3037(7) 0.1152(3) 0.45115(13) 0.0651(8) Uani d . 1 . .
H H8B 0.2132 0.0293 0.4583 0.078 Uiso calc R 1 . .
H H8A 0.4885 0.0956 0.4413 0.078 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
O2 N1 C1 . . 121.61(19) ?
O2 N1 O1 . . 119.35(19) ?
N1 C1 C2 . . 123.2(2) ?
N1 C1 H1 . . 118.4 ?
C2 N2 H2 . . 124.0 ?
C2 N2 C3 . . 112.0(2) ?
C2 C1 H1 . . 118.4 ?
C2 N3 C5 . . 127.03(19) ?
C2 N3 C4 . . 111.03(19) ?
O3 C6 C5 . . 108.72(19) ?
O3 C6 H6 . . 108.2 ?
O3 C6 C7 . . 110.17(18) ?
O3 C9 H9A . . 109.4 ?
O3 C9 H9B . . 109.4 ?
N2 C2 C1 . . 127.1(2) ?
N2 C2 N3 . . 110.1(2) ?
N2 C3 C4 . . 102.82(18) ?
N2 C3 H3A . . 111.2 ?
N2 C3 H3B . . 111.2 ?
N3 C2 C1 . . 122.80(19) ?
N3 C5 H5A . . 108.7 ?
N3 C5 H5B . . 108.7 ?
N3 C5 C6 . . 114.35(18) ?
N3 C4 H4B . . 111.1 ?
N3 C4 H4A . . 111.1 ?
N3 C4 C3 . . 103.34(19) ?
O1 N1 C1 . . 119.04(19) ?
C5 N3 C4 . . 121.66(19) ?
C5 C6 H6 . . 108.2 ?
C5 C6 C7 . . 113.16(18) ?
H5A C5 H5B . . 107.6 ?
C6 C5 H5A . . 108.7 ?
C6 C5 H5B . . 108.7 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
C6 C7 C8 . . 110.7(2) ?
O4 C9 O3 . . 111.3(2) ?
O4 C9 H9A . . 109.4 ?
O4 C9 H9B . . 109.4 ?
O4 C8 C7 . . 111.0(2) ?
O4 C8 H8B . . 109.4 ?
O4 C8 H8A . . 109.4 ?
C7 C6 H6 . . 108.2 ?
C7 C8 H8B . . 109.4 ?
C7 C8 H8A . . 109.4 ?
H7A C7 H7B . . 108.1 ?
C4 C3 H3A . . 111.2 ?
C4 C3 H3B . . 111.2 ?
H4B C4 H4A . . 109.1 ?
C3 N2 H2 . . 124.0 ?
C3 C4 H4B . . 111.1 ?
C3 C4 H4A . . 111.1 ?
H3A C3 H3B . . 109.1 ?
C9 O3 C6 . . 110.8(2) ?
C9 O4 C8 . . 110.0(2) ?
H9A C9 H9B . . 108.0 ?
C8 C7 H7A . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H8B C8 H8A . . 108.0 ?
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
O2 N1 . 1.253(2) ?
N1 C1 . 1.350(3) ?
N1 O1 . 1.267(2) ?
C2 N2 . 1.329(3) ?
C2 C1 . 1.401(3) ?
C2 N3 . 1.345(3) ?
O3 C6 . 1.418(3) ?
O3 C9 . 1.414(3) ?
N2 H2 . 0.8600 ?
N2 C3 . 1.462(3) ?
C1 H1 . 0.9300 ?
N3 C5 . 1.452(3) ?
N3 C4 . 1.465(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C5 C6 . 1.491(3) ?
C6 H6 . 0.9800 ?
C6 C7 . 1.504(3) ?
O4 C9 . 1.396(4) ?
O4 C8 . 1.413(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C7 C8 . 1.516(4) ?
C4 H4B . 0.9700 ?
C4 H4A . 0.9700 ?
C4 C3 . 1.522(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C8 H8B . 0.9700 ?
C8 H8A . 0.9700 ?
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
N2 H2 O2 . 0.86 2.17 2.694(3) 119
N2 H2 O1 2_655 0.86 2.17 2.824(3) 133
C1 H1 O2 2_645 0.93 2.42 3.249(3) 148
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
O2 N1 C1 C2 . . . . 0.9(3) ?
C2 N2 C3 C4 . . . . -7.0(2) ?
C2 N3 C5 C6 . . . . 92.4(3) ?
C2 N3 C4 C3 . . . . -6.3(2) ?
O3 C6 C7 C8 . . . . -49.0(3) ?
N2 C2 C1 N1 . . . . 1.8(3) ?
N2 C2 N3 C5 . . . . 176.06(19) ?
N2 C2 N3 C4 . . . . 2.1(2) ?
C1 C2 N2 C3 . . . . -176.0(2) ?
C1 C2 N3 C5 . . . . -4.5(3) ?
C1 C2 N3 C4 . . . . -178.49(19) ?
N3 C2 N2 C3 . . . . 3.4(2) ?
N3 C2 C1 N1 . . . . -177.49(18) ?
N3 C5 C6 O3 . . . . 52.3(3) ?
N3 C5 C6 C7 . . . . 175.06(19) ?
N3 C4 C3 N2 . . . . 7.6(2) ?
O1 N1 C1 C2 . . . . -179.4(2) ?
C5 N3 C4 C3 . . . . 179.39(19) ?
C5 C6 C7 C8 . . . . -170.9(2) ?
C6 O3 C9 O4 . . . . -64.4(3) ?
C6 C7 C8 O4 . . . . 49.6(3) ?
C4 N3 C5 C6 . . . . -94.3(3) ?
C9 O3 C6 C5 . . . . -179.5(2) ?
C9 O3 C6 C7 . . . . 56.0(3) ?
C9 O4 C8 C7 . . . . -56.4(3) ?
C8 O4 C9 O3 . . . . 64.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079658
