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#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/72/2227219.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_2227219
loop_
_publ_author_name
'Tian, Zhongzhen'
'Wang, Gaolei'
'Dong, Haijun'
_publ_section_title
;
 1-(2,2-Dimethoxyethyl)-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol
;
_journal_coeditor_code           BT5332
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2451
_journal_paper_doi               10.1107/S1600536810033660
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H19 N3 O5'
_chemical_formula_moiety         'C11 H19 N3 O5'
_chemical_formula_sum            'C11 H19 N3 O5'
_chemical_formula_weight         273.29
_chemical_name_systematic
;
1-(2,2-Dimethoxyethyl)-8-nitro-1,2,3,5,6,7-
hexahydroimidazo[1,2-a]pyridin-5-ol
;
_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                 113.124(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2337(6)
_cell_length_b                   9.0903(3)
_cell_length_c                   14.2618(7)
_cell_measurement_reflns_used    15115
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9221
_cell_measurement_theta_min      2.9482
_cell_volume                     1339.37(12)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'XP (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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37886
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.92941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0615P)²+0.2341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                2100
_reflns_number_total             2723
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5332.cif
_cod_data_source_block           I
_cod_original_cell_volume        1339.36(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227219
_cod_database_fobs_code          2227219
loop_
_symmetry_equiv_pos_as_xyz
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
N N1 0.29875(12) 0.55756(14) 0.22689(9) 0.0425(3) Uani d . 1 . .
O O1 0.63771(13) 0.70130(14) 0.20749(9) 0.0628(4) Uani d . 1 . .
H H1 0.6117 0.7331 0.1491 0.094 Uiso calc R 1 . .
N N2 0.47152(13) 0.53178(15) 0.19064(9) 0.0445(3) Uani d . 1 . .
C C5 0.42919(14) 0.56183(15) 0.26436(10) 0.0371(3) Uani d . 1 . .
O O4 0.38448(13) 0.73086(14) 0.41241(9) 0.0600(3) Uani d . 1 . .
N N3 0.49381(14) 0.67236(15) 0.43224(9) 0.0480(3) Uani d . 1 . .
O O5 0.58619(14) 0.69576(16) 0.51820(8) 0.0707(4) Uani d . 1 . .
O O2 0.02213(12) 0.59831(16) 0.16524(10) 0.0721(4) Uani d . 1 . .
C C8 0.22221(16) 0.51751(18) 0.28522(12) 0.0475(4) Uani d . 1 . .
H H8B 0.2773 0.5183 0.3573 0.057 Uiso calc R 1 . .
H H8A 0.1892 0.4184 0.2671 0.057 Uiso calc R 1 . .
C C1 0.52149(15) 0.59073(16) 0.36427(10) 0.0406(4) Uani d . 1 . .
C C4 0.60599(16) 0.55202(18) 0.20530(12) 0.0487(4) Uani d . 1 . .
H H4 0.6219 0.5029 0.1502 0.058 Uiso calc R 1 . .
C C6 0.36474(16) 0.5264(2) 0.09100(11) 0.0533(4) Uani d . 1 . .
H H6A 0.3731 0.4436 0.0511 0.064 Uiso calc R 1 . .
H H6B 0.3589 0.6166 0.0531 0.064 Uiso calc R 1 . .
C C2 0.66126(16) 0.5530(2) 0.39249(12) 0.0550(4) Uani d . 1 . .
H H2A 0.6892 0.4865 0.4503 0.066 Uiso calc R 1 . .
H H2B 0.7126 0.6420 0.4133 0.066 Uiso calc R 1 . .
O O3 0.05036(15) 0.58840(17) 0.33329(12) 0.0822(5) Uani d . 1 . .
C C9 0.10981(17) 0.6218(2) 0.26575(14) 0.0533(4) Uani d . 1 . .
H H9 0.1401 0.7240 0.2748 0.064 Uiso calc R 1 . .
C C7 0.25036(17) 0.5085(2) 0.11957(12) 0.0583(5) Uani d . 1 . .
H H7B 0.1784 0.5690 0.0767 0.070 Uiso calc R 1 . .
H H7A 0.2226 0.4066 0.1133 0.070 Uiso calc R 1 . .
C C3 0.68676(18) 0.4813(2) 0.30524(14) 0.0593(5) Uani d . 1 . .
H H3B 0.7777 0.4911 0.3176 0.071 Uiso calc R 1 . .
H H3A 0.6665 0.3772 0.3024 0.071 Uiso calc R 1 . .
C C11 -0.0810(2) 0.7013(3) 0.12986(19) 0.0959(8) Uani d . 1 . .
H H11A -0.1268 0.6905 0.0575 0.144 Uiso calc R 1 . .
H H11C -0.0469 0.7992 0.1449 0.144 Uiso calc R 1 . .
H H11B -0.1391 0.6837 0.1632 0.144 Uiso calc R 1 . .
C C10 0.0604(3) 0.6935(3) 0.40618(19) 0.1038(9) Uani d . 1 . .
H H10C 0.0242 0.7846 0.3732 0.156 Uiso calc R 1 . .
H H10B 0.1499 0.7079 0.4495 0.156 Uiso calc R 1 . .
H H10A 0.0140 0.6611 0.4464 0.156 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
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'
C C 0.0033 0.0016 '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
N1 C5 C1 . . 130.90(13) ?
N1 C8 H8B . . 109.2 ?
N1 C8 H8A . . 109.2 ?
N1 C8 C9 . . 112.03(13) ?
N1 C7 C6 . . 104.03(13) ?
N1 C7 H7B . . 111.0 ?
N1 C7 H7A . . 111.0 ?
O1 C4 N2 . . 111.53(14) ?
O1 C4 H4 . . 109.5 ?
O1 C4 C3 . . 109.90(14) ?
N2 C5 N1 . . 110.37(13) ?
N2 C5 C1 . . 118.73(14) ?
N2 C4 H4 . . 109.5 ?
N2 C4 C3 . . 106.79(13) ?
N2 C6 H6A . . 111.4 ?
N2 C6 H6B . . 111.4 ?
N2 C6 C7 . . 101.74(12) ?
C5 N1 C8 . . 125.00(12) ?
C5 N1 C7 . . 108.64(13) ?
C5 N2 C4 . . 122.00(13) ?
C5 N2 C6 . . 111.22(13) ?
C5 C1 C2 . . 120.14(13) ?
O4 N3 O5 . . 119.82(13) ?
O4 N3 C1 . . 123.22(13) ?
N3 C1 C5 . . 122.62(14) ?
N3 C1 C2 . . 116.43(14) ?
O5 N3 C1 . . 116.87(14) ?
O2 C9 C8 . . 107.03(13) ?
O2 C9 O3 . . 109.65(15) ?
O2 C9 H9 . . 110.4 ?
O2 C11 H11A . . 109.5 ?
O2 C11 H11C . . 109.5 ?
O2 C11 H11B . . 109.5 ?
C8 N1 C7 . . 117.14(13) ?
C8 C9 H9 . . 110.4 ?
H8B C8 H8A . . 107.9 ?
C1 C2 H2A . . 109.0 ?
C1 C2 H2B . . 109.0 ?
C1 C2 C3 . . 112.98(14) ?
C4 O1 H1 . . 109.5 ?
C4 N2 C6 . . 123.77(12) ?
C4 C3 C2 . . 110.73(14) ?
C4 C3 H3B . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C6 C7 H7B . . 111.0 ?
C6 C7 H7A . . 111.0 ?
H6A C6 H6B . . 109.3 ?
C2 C3 H3B . . 109.5 ?
C2 C3 H3A . . 109.5 ?
H2A C2 H2B . . 107.8 ?
O3 C9 C8 . . 109.02(15) ?
O3 C9 H9 . . 110.4 ?
O3 C10 H10C . . 109.5 ?
O3 C10 H10B . . 109.5 ?
O3 C10 H10A . . 109.5 ?
C9 O2 C11 . . 114.29(15) ?
C9 C8 H8B . . 109.2 ?
C9 C8 H8A . . 109.2 ?
C7 C6 H6A . . 111.4 ?
C7 C6 H6B . . 111.4 ?
H7B C7 H7A . . 109.0 ?
C3 C4 H4 . . 109.5 ?
C3 C2 H2A . . 109.0 ?
C3 C2 H2B . . 109.0 ?
H3B C3 H3A . . 108.1 ?
H11A C11 H11C . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11C C11 H11B . . 109.5 ?
C10 O3 C9 . . 116.47(18) ?
H10C C10 H10B . . 109.5 ?
H10C C10 H10A . . 109.5 ?
H10B C10 H10A . . 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
N1 C5 . 1.3488(19) ?
N1 C8 . 1.4579(19) ?
N1 C7 . 1.4777(19) ?
O1 H1 . 0.8200 ?
O1 C4 . 1.400(2) ?
N2 C5 . 1.3412(19) ?
N2 C4 . 1.453(2) ?
N2 C6 . 1.4566(19) ?
C5 C1 . 1.419(2) ?
O4 N3 . 1.2643(18) ?
N3 O5 . 1.2751(17) ?
N3 C1 . 1.350(2) ?
O2 C9 . 1.400(2) ?
O2 C11 . 1.419(2) ?
C8 H8B . 0.9700 ?
C8 H8A . 0.9700 ?
C8 C9 . 1.515(2) ?
C1 C2 . 1.500(2) ?
C4 H4 . 0.9800 ?
C4 C3 . 1.501(2) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C6 C7 . 1.502(2) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C2 C3 . 1.528(2) ?
O3 C9 . 1.404(2) ?
O3 C10 . 1.384(3) ?
C9 H9 . 0.9800 ?
C7 H7B . 0.9700 ?
C7 H7A . 0.9700 ?
C3 H3B . 0.9700 ?
C3 H3A . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11C . 0.9600 ?
C11 H11B . 0.9600 ?
C10 H10C . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10A . 0.9600 ?
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
O1 H1 O5 4_575 0.82 1.89 2.6966(16) 168.8
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
N1 C5 C1 N3 . . . . -25.8(2) ?
N1 C5 C1 C2 . . . . 164.90(15) ?
N1 C8 C9 O2 . . . . 68.81(18) ?
N1 C8 C9 O3 . . . . -172.66(14) ?
O1 C4 C3 C2 . . . . 61.14(19) ?
N2 C5 C1 N3 . . . . 154.74(15) ?
N2 C5 C1 C2 . . . . -14.6(2) ?
N2 C4 C3 C2 . . . . -59.99(19) ?
N2 C6 C7 N1 . . . . 19.23(18) ?
C5 N1 C8 C9 . . . . 135.02(15) ?
C5 N1 C7 C6 . . . . -15.63(19) ?
C5 N2 C4 O1 . . . . -71.99(18) ?
C5 N2 C4 C3 . . . . 48.10(19) ?
C5 N2 C6 C7 . . . . -17.84(18) ?
C5 C1 C2 C3 . . . . -1.2(2) ?
O4 N3 C1 C5 . . . . -0.8(2) ?
O4 N3 C1 C2 . . . . 168.94(14) ?
N3 C1 C2 C3 . . . . -171.20(15) ?
O5 N3 C1 C5 . . . . -177.19(14) ?
O5 N3 C1 C2 . . . . -7.5(2) ?
C8 N1 C5 N2 . . . . 150.28(14) ?
C8 N1 C5 C1 . . . . -29.3(2) ?
C8 N1 C7 C6 . . . . -164.17(14) ?
C1 C2 C3 C4 . . . . 38.9(2) ?
C4 N2 C5 N1 . . . . 169.82(14) ?
C4 N2 C5 C1 . . . . -10.6(2) ?
C4 N2 C6 C7 . . . . -178.50(15) ?
C6 N2 C5 N1 . . . . 8.77(17) ?
C6 N2 C5 C1 . . . . -171.63(13) ?
C6 N2 C4 O1 . . . . 86.66(18) ?
C6 N2 C4 C3 . . . . -153.26(15) ?
C7 N1 C5 N2 . . . . 4.82(17) ?
C7 N1 C5 C1 . . . . -174.72(15) ?
C7 N1 C8 C9 . . . . -82.11(18) ?
C11 O2 C9 C8 . . . . -171.90(18) ?
C11 O2 C9 O3 . . . . 70.0(2) ?
C10 O3 C9 O2 . . . . -129.9(2) ?
C10 O3 C9 C8 . . . . 113.2(2) ?
