#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227460.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_2227460
loop_
_publ_author_name
'Wang, Gaolei'
'Li, Dongmei'
'Li, He'
_publ_section_title
;
 2-[(E)-2-(Nitromethylidene)imidazolidin-1-yl]ethanol
;
_journal_coeditor_code           GK2305
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2759
_journal_paper_doi               10.1107/S1600536810039280
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H11 N3 O3'
_chemical_formula_moiety         'C6 H11 N3 O3'
_chemical_formula_sum            'C6 H11 N3 O3'
_chemical_formula_weight         173.18
_chemical_name_systematic
;
2-[(E)-2-(Nitromethylidene)imidazolidin-1-yl]ethanol
;
_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                 94.153(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9422(2)
_cell_length_b                   8.7142(3)
_cell_length_c                   12.9698(4)
_cell_measurement_reflns_used    2585
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8228
_cell_measurement_theta_min      3.2285
_cell_volume                     782.56(4)
_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      293.0
_diffrn_detector_area_resol_mean 16.0355
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4832
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.96673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0378
_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)+(0.0606P)²+0.0450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                1186
_reflns_number_total             1539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            gk2305.cif
_cod_data_source_block           I
_cod_original_cell_volume        782.55(4)
_cod_database_code               2227460
_cod_database_fobs_code          2227460
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
C C1 0.7352(2) 0.66673(18) 0.73309(13) 0.0428(4) Uani d . 1 . .
H H1A 0.7010 0.7696 0.7099 0.051 Uiso calc R 1 . .
H H1B 0.8709 0.6509 0.7230 0.051 Uiso calc R 1 . .
C C2 0.70406(19) 0.65267(18) 0.84644(12) 0.0387(4) Uani d . 1 . .
H H2A 0.7338 0.5485 0.8687 0.046 Uiso calc R 1 . .
H H2B 0.7932 0.7207 0.8851 0.046 Uiso calc R 1 . .
C C3 0.4516(2) 0.84632(17) 0.89333(14) 0.0481(4) Uani d . 1 . .
H H3A 0.4536 0.9106 0.8324 0.058 Uiso calc R 1 . .
H H3B 0.5364 0.8904 0.9483 0.058 Uiso calc R 1 . .
C C4 0.2490(3) 0.82924(18) 0.92650(15) 0.0519(5) Uani d . 1 . .
H H4A 0.1570 0.8840 0.8802 0.062 Uiso calc R 1 . .
H H4B 0.2396 0.8668 0.9964 0.062 Uiso calc R 1 . .
C C5 0.36609(19) 0.59107(16) 0.88760(10) 0.0296(3) Uani d . 1 . .
C C6 0.3790(2) 0.43186(17) 0.87112(11) 0.0358(4) Uani d . 1 . .
H H6 0.4933 0.3920 0.8490 0.043 Uiso calc R 1 . .
N N1 0.50847(16) 0.68944(13) 0.87087(9) 0.0336(3) Uani d . 1 . .
N N2 0.21646(17) 0.66554(14) 0.92072(10) 0.0403(3) Uani d . 1 . .
H H2 0.1119 0.6216 0.9370 0.048 Uiso calc R 1 . .
N N3 0.23318(18) 0.33545(14) 0.88605(10) 0.0371(3) Uani d . 1 . .
O O1 0.62388(16) 0.55935(12) 0.67291(8) 0.0481(3) Uani d . 1 . .
H H1 0.5161 0.5949 0.6580 0.072 Uiso calc R 1 . .
O O2 0.07390(15) 0.38210(13) 0.91700(9) 0.0480(3) Uani d . 1 . .
O O3 0.25342(18) 0.19348(13) 0.86750(10) 0.0580(4) Uani d . 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'
O O 0.0106 0.0060 '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'
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 O1 H1 . . 109.5 ?
C1 C2 H2A . . 108.9 ?
C1 C2 H2B . . 108.9 ?
H1A C1 H1B . . 107.9 ?
C2 N1 C3 . . 121.44(12) ?
C2 C1 H1A . . 109.2 ?
C2 C1 H1B . . 109.2 ?
H2A C2 H2B . . 107.7 ?
C3 C4 H4B . . 111.1 ?
C3 C4 H4A . . 111.1 ?
H3A C3 H3B . . 109.0 ?
C4 N2 H2 . . 123.9 ?
C4 C3 H3A . . 111.0 ?
C4 C3 H3B . . 111.0 ?
H4B C4 H4A . . 109.1 ?
C5 N1 C2 . . 127.40(12) ?
C5 N1 C3 . . 110.75(12) ?
C5 N2 H2 . . 123.9 ?
C5 N2 C4 . . 112.19(12) ?
C5 C6 H6 . . 118.7 ?
N1 C5 C6 . . 123.43(13) ?
N1 C2 C1 . . 113.42(12) ?
N1 C2 H2A . . 108.9 ?
N1 C2 H2B . . 108.9 ?
N1 C3 H3A . . 111.0 ?
N1 C3 H3B . . 111.0 ?
N1 C3 C4 . . 103.67(12) ?
N2 C5 N1 . . 110.19(12) ?
N2 C5 C6 . . 126.39(13) ?
N2 C4 C3 . . 103.18(12) ?
N2 C4 H4B . . 111.1 ?
N2 C4 H4A . . 111.1 ?
N3 C6 C5 . . 122.59(13) ?
N3 C6 H6 . . 118.7 ?
O1 C1 H1A . . 109.2 ?
O1 C1 H1B . . 109.2 ?
O1 C1 C2 . . 111.96(12) ?
O2 N3 C6 . . 121.94(12) ?
O3 N3 O2 . . 118.84(12) ?
O3 N3 C6 . . 119.21(13) ?
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
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C1 C2 . 1.506(2) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C3 C4 . 1.508(2) ?
C4 H4B . 0.9700 ?
C4 H4A . 0.9700 ?
C5 N1 . 1.3379(17) ?
C5 N2 . 1.3227(17) ?
C5 C6 . 1.408(2) ?
C6 H6 . 0.9300 ?
N1 C2 . 1.4523(17) ?
N1 C3 . 1.4582(19) ?
N2 H2 . 0.8600 ?
N2 C4 . 1.445(2) ?
N3 O3 . 1.2701(16) ?
N3 C6 . 1.3406(18) ?
O1 H1 . 0.8200 ?
O1 C1 . 1.4123(19) ?
O2 N3 . 1.2702(15) ?
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 3_567 0.86 2.37 3.0463(16) 136
N2 H2 O2 . 0.86 2.12 2.6600(16) 121
O1 H1 O3 2_556 0.82 2.06 2.8814(16) 175
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
O1 C1 C2 N1 . . . . -64.63(17) ?
O2 N3 C6 C5 . . . . -0.6(2) ?
O3 N3 C6 C5 . . . . 178.47(14) ?
N1 C5 N2 C4 . . . . 1.41(17) ?
N1 C5 C6 N3 . . . . -178.43(12) ?
N1 C3 C4 N2 . . . . 0.97(18) ?
N2 C5 N1 C2 . . . . 171.93(13) ?
N2 C5 N1 C3 . . . . -0.69(16) ?
N2 C5 C6 N3 . . . . 1.4(2) ?
C2 N1 C3 C4 . . . . -173.37(14) ?
C3 N1 C2 C1 . . . . -87.91(16) ?
C5 N1 C2 C1 . . . . 100.19(16) ?
C5 N1 C3 C4 . . . . -0.24(17) ?
C5 N2 C4 C3 . . . . -1.48(19) ?
C6 C5 N1 C2 . . . . -8.2(2) ?
C6 C5 N1 C3 . . . . 179.16(14) ?
C6 C5 N2 C4 . . . . -178.44(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8550334
