#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/05/2210505.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_2210505
loop_
_publ_author_name
'Shu Qiao'
'Guo-Ping Yong'
'Yu Xie'
'Zhi-Yong Wang'
_publ_section_title
;Zwitterionic
 3-carboxylatomethyl-3-carboxymethyl-2-oxo-2,3-dihydroimidazo[1,2-a]pyridin-1-ium
;
_journal_coeditor_code           BI2060
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4634
_journal_page_last               o4635
_journal_paper_doi               10.1107/S1600536806037421
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H10 N2 O5'
_chemical_formula_moiety         'C11 H10 N2 O5'
_chemical_formula_sum            'C11 H10 N2 O5'
_chemical_formula_weight         250.21
_chemical_name_systematic
;
3-carboxylatomethyl-3-carboxymethyl-2-oxo-2,3-
dihydroimidazo[1,2-a]pyridin-1-ium
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.35(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.735(3)
_cell_length_b                   9.862(2)
_cell_length_c                   18.218(4)
_cell_measurement_reflns_used    11761
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.74
_cell_measurement_theta_min      3.08
_cell_volume                     2313.7(10)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11493
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.74
_diffrn_reflns_theta_min         3.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.693
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0628
_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)+(0.0914P)²+1.0573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                2852
_reflns_number_total             3040
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2060.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210505
_cod_database_fobs_code          2210505
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O O1 0.33812(11) 1.14104(12) -0.01863(6) 0.0500(3) Uani d . 1
O O2 0.24877(10) 0.95654(12) -0.01067(6) 0.0442(3) Uani d . 1
O O3 0.36006(13) 0.97806(13) 0.36872(7) 0.0534(4) Uani d . 1
H H3 0.337(2) 0.918(3) 0.4121(19) 0.092(9) Uiso d . 1
O O4 0.27432(12) 0.82402(13) 0.28046(7) 0.0537(4) Uani d . 1
O O5 0.42479(9) 0.80753(13) 0.14866(9) 0.0516(3) Uani d . 1
N N1 0.24973(10) 0.75758(12) 0.10898(7) 0.0357(3) Uani d . 1
H H1 0.2508 0.6735 0.0967 0.043 Uiso calc R 1
N N2 0.18664(9) 0.95662(11) 0.12851(7) 0.0312(3) Uani d . 1
C C1 0.32810(12) 1.08897(14) 0.10465(8) 0.0353(3) Uani d . 1
H H1A 0.2930 1.1722 0.1091 0.042 Uiso calc R 1
H H1B 0.4022 1.1058 0.1273 0.042 Uiso calc R 1
C C2 0.30152(11) 1.05737(14) 0.01788(8) 0.0330(3) Uani d . 1
C C3 0.34568(12) 1.02036(14) 0.24022(8) 0.0355(3) Uani d . 1
H H3A 0.4205 1.0255 0.2547 0.043 Uiso calc R 1
H H3B 0.3211 1.1108 0.2454 0.043 Uiso calc R 1
C C4 0.32177(12) 0.92958(14) 0.29840(8) 0.0352(3) Uani d . 1
C C5 0.16245(11) 0.82828(13) 0.10250(8) 0.0332(3) Uani d . 1
C C6 0.05945(13) 0.78663(16) 0.07473(10) 0.0438(4) Uani d . 1
H H6A 0.0411 0.6996 0.0552 0.053 Uiso calc R 1
C C7 -0.01440(13) 0.87900(18) 0.07716(13) 0.0516(4) Uani d . 1
H H7A -0.0840 0.8537 0.0590 0.062 Uiso calc R 1
C C8 0.01276(14) 1.01011(18) 0.10627(13) 0.0520(4) Uani d . 1
H H8A -0.0380 1.0709 0.1084 0.062 Uiso calc R 1
C C9 0.11464(13) 1.04777(15) 0.13154(10) 0.0409(3) Uani d . 1
H H9A 0.1343 1.1348 0.1506 0.049 Uiso calc R 1
C C10 0.29988(11) 0.97945(13) 0.15372(7) 0.0304(3) Uani d . 1
C C11 0.33633(12) 0.83859(14) 0.13792(8) 0.0352(3) 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'
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
_geom_angle_publ_flag
C9 N2 C5 122.88(13) n
C9 N2 C10 126.29(12) n
C5 N2 C10 110.81(11) n
C4 O3 H3 112.8(16) n
O2 C2 O1 125.81(13) n
O2 C2 C1 119.69(12) n
O1 C2 C1 114.51(12) n
C5 N1 C11 110.78(11) n
C5 N1 H1 124.6 n
C11 N1 H1 124.6 n
N2 C10 C3 111.76(11) n
N2 C10 C1 112.19(12) n
C3 C10 C1 108.47(11) n
N2 C10 C11 100.38(10) n
C3 C10 C11 112.72(12) n
C1 C10 C11 111.23(11) n
C4 C3 C10 117.01(12) n
C4 C3 H3A 108.0 n
C10 C3 H3A 108.0 n
C4 C3 H3B 108.0 n
C10 C3 H3B 108.0 n
H3A C3 H3B 107.3 n
O4 C4 O3 125.42(14) n
O4 C4 C3 123.28(13) n
O3 C4 C3 111.29(13) n
C2 C1 C10 116.21(11) n
C2 C1 H1A 108.2 n
C10 C1 H1A 108.2 n
C2 C1 H1B 108.2 n
C10 C1 H1B 108.2 n
H1A C1 H1B 107.4 n
O5 C11 N1 127.20(14) n
O5 C11 C10 125.22(14) n
N1 C11 C10 107.57(12) n
N2 C5 N1 110.42(12) n
N2 C5 C6 119.98(13) n
N1 C5 C6 129.60(13) n
N2 C9 C8 118.98(14) n
N2 C9 H9A 120.5 n
C8 C9 H9A 120.5 n
C7 C6 C5 117.50(15) n
C7 C6 H6A 121.3 n
C5 C6 H6A 121.3 n
C6 C7 C8 121.49(16) n
C6 C7 H7A 119.3 n
C8 C7 H7A 119.3 n
C9 C8 C7 119.14(16) n
C9 C8 H8A 120.4 n
C7 C8 H8A 120.4 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N2 C9 1.3517(18) n
N2 C5 1.3518(16) n
N2 C10 1.4779(18) n
O2 C2 1.2338(17) n
O1 C2 1.2683(17) n
O4 C4 1.2113(19) n
O3 C4 1.2953(18) n
O3 H3 1.12(3) n
O5 C11 1.2012(18) n
C2 C1 1.5256(18) n
N1 C5 1.3560(18) n
N1 C11 1.3766(19) n
N1 H1 0.860 n
C10 C3 1.5337(19) n
C10 C1 1.5353(18) n
C10 C11 1.5373(19) n
C3 C4 1.5084(19) n
C3 H3A 0.970 n
C3 H3B 0.970 n
C1 H1A 0.970 n
C1 H1B 0.970 n
C5 C6 1.389(2) n
C9 C8 1.364(2) n
C9 H9A 0.930 n
C6 C7 1.375(2) n
C6 H6A 0.930 n
C7 C8 1.398(3) n
C7 H7A 0.930 n
C8 H8A 0.930 n
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
_geom_hbond_publ_flag
O3 H3 O1 6_576 1.12(3) 1.39(3) 2.4724(16) 162(3) y
N1 H1 O2 7_565 0.86 2.03 2.7734(16) 145 y
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
_geom_torsion_publ_flag
C9 N2 C10 C3 58.44(18) n
C5 N2 C10 C3 -120.28(12) n
C9 N2 C10 C1 -63.65(17) n
C5 N2 C10 C1 117.63(12) n
C9 N2 C10 C11 178.17(14) n
C5 N2 C10 C11 -0.56(13) n
N2 C10 C3 C4 52.54(17) n
C1 C10 C3 C4 176.75(13) n
C11 C10 C3 C4 -59.63(17) n
C10 C3 C4 O4 4.5(2) n
C10 C3 C4 O3 -176.74(14) n
O2 C2 C1 C10 8.7(2) n
O1 C2 C1 C10 -170.99(13) n
N2 C10 C1 C2 -63.80(16) n
C3 C10 C1 C2 172.25(12) n
C11 C10 C1 C2 47.74(17) n
C5 N1 C11 O5 -178.03(15) n
C5 N1 C11 C10 1.31(16) n
N2 C10 C11 O5 178.91(15) n
C3 C10 C11 O5 -62.06(19) n
C1 C10 C11 O5 60.0(2) n
N2 C10 C11 N1 -0.44(13) n
C3 C10 C11 N1 118.58(13) n
C1 C10 C11 N1 -119.34(13) n
C9 N2 C5 N1 -177.37(13) n
C10 N2 C5 N1 1.40(15) n
C9 N2 C5 C6 2.3(2) n
C10 N2 C5 C6 -178.88(13) n
C11 N1 C5 N2 -1.72(16) n
C11 N1 C5 C6 178.60(15) n
C5 N2 C9 C8 -1.0(2) n
C10 N2 C9 C8 -179.59(15) n
N2 C5 C6 C7 -1.8(2) n
N1 C5 C6 C7 177.82(16) n
C5 C6 C7 C8 0.1(3) n
N2 C9 C8 C7 -0.7(3) n
C6 C7 C8 C9 1.2(3) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127350
