#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/07/4500741.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_4500741
loop_
_publ_author_name
'Kohmoto, Shigeo'
'Okuyama, Shinpei'
'Yokota, Nobuyuki,'
'Takahashi, Masahiro'
'Kishikawa, Keiki'
'Masu, Hyuma'
'Azumaya, Isao'
_publ_section_title
;
 Generation of Zwitterionic Water Channels: Biszwitterionic Imidazolium
 Carboxylates as Hydrogen-Bonding Acceptors
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3698
_journal_paper_doi               10.1021/cg200232b
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C22 H20 N4 O4, 5.5(O)'
_chemical_formula_sum            'C22 H20 N4 O9.5'
_chemical_formula_weight         492.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.692(2)
_cell_angle_beta                 77.323(2)
_cell_angle_gamma                73.387(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5978(14)
_cell_length_b                   9.7222(14)
_cell_length_c                   13.736(2)
_cell_measurement_reflns_used    1845
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.45
_cell_volume                     1198.2(3)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega 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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7107
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9785
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0592
_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)+(0.0999P)²+0.5027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1602
_refine_ls_wR_factor_ref         0.1813
_reflns_number_gt                3540
_reflns_number_total             5144
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200232b_si_002.cif
_cod_data_source_block           2b(0064mas)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_original_formula_sum        'C22 H20 N4 O9.50'
_cod_database_code               4500741
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.2605(3) 0.7178(2) 0.32410(17) 0.0205(5) Uani 1 1 d .
H1A H 0.3626 0.6662 0.3318 0.025 Uiso 1 1 calc R
H1B H 0.2596 0.7248 0.2520 0.025 Uiso 1 1 calc R
C2 C 0.1540(2) 0.6338(2) 0.37694(17) 0.0200(5) Uani 1 1 d .
C3 C 0.0560(3) 0.5994(2) 0.32497(17) 0.0223(5) Uani 1 1 d .
H3 H 0.0589 0.6277 0.2570 0.027 Uiso 1 1 calc R
C4 C -0.0428(3) 0.5256(2) 0.37215(17) 0.0215(5) Uani 1 1 d .
H4 H -0.1074 0.5026 0.3365 0.026 Uiso 1 1 calc R
C5 C 0.0492(2) 0.5166(2) 0.52623(17) 0.0186(5) Uani 1 1 d .
C6 C 0.1509(3) 0.5924(2) 0.47497(17) 0.0210(5) Uani 1 1 d .
H6 H 0.2177 0.6146 0.5091 0.025 Uiso 1 1 calc R
C7 C 0.2854(3) 0.9045(2) 0.42903(17) 0.0205(5) Uani 1 1 d .
H7 H 0.3692 0.8465 0.4530 0.025 Uiso 1 1 calc R
C8 C 0.1000(3) 1.0875(2) 0.40343(17) 0.0235(5) Uani 1 1 d .
H8 H 0.0319 1.1805 0.4070 0.028 Uiso 1 1 calc R
C9 C 0.1018(3) 0.9773(2) 0.34832(17) 0.0220(5) Uani 1 1 d .
H9 H 0.0353 0.9780 0.3061 0.026 Uiso 1 1 calc R
C10 C 0.2573(3) 1.1246(3) 0.52017(18) 0.0258(5) Uani 1 1 d .
H10A H 0.2960 1.0603 0.5734 0.031 Uiso 1 1 calc R
H10B H 0.1675 1.1982 0.5525 0.031 Uiso 1 1 calc R
C11 C 0.3750(3) 1.1995(2) 0.46789(17) 0.0217(5) Uani 1 1 d .
C12 C 0.2529(3) 0.2853(2) 0.18971(17) 0.0213(5) Uani 1 1 d .
H12A H 0.2591 0.2802 0.2609 0.026 Uiso 1 1 calc R
H12B H 0.1488 0.3343 0.1850 0.026 Uiso 1 1 calc R
C13 C 0.3536(2) 0.3701(2) 0.13204(17) 0.0197(5) Uani 1 1 d .
C14 C 0.4556(3) 0.4088(2) 0.17802(18) 0.0227(5) Uani 1 1 d .
H14 H 0.4571 0.3842 0.2461 0.027 Uiso 1 1 calc R
C15 C 0.5517(3) 0.4812(2) 0.12515(18) 0.0228(5) Uani 1 1 d .
H15 H 0.6192 0.5066 0.1569 0.027 Uiso 1 1 calc R
C16 C 0.4486(2) 0.4814(2) -0.02330(17) 0.0196(5) Uani 1 1 d .
C17 C 0.3495(3) 0.4079(2) 0.03426(18) 0.0213(5) Uani 1 1 d .
H17 H 0.2790 0.3843 0.0045 0.026 Uiso 1 1 calc R
C18 C 0.2341(3) 0.0960(2) 0.08404(17) 0.0195(5) Uani 1 1 d .
H18 H 0.1526 0.1529 0.0572 0.023 Uiso 1 1 calc R
C19 C 0.4160(2) -0.0866(2) 0.11699(17) 0.0213(5) Uani 1 1 d .
H19 H 0.4831 -0.1798 0.1164 0.026 Uiso 1 1 calc R
C20 C 0.4096(3) 0.0261(2) 0.17208(17) 0.0217(5) Uani 1 1 d .
H20 H 0.4718 0.0270 0.2170 0.026 Uiso 1 1 calc R
C21 C 0.2577(3) -0.1295(2) 0.00212(17) 0.0214(5) Uani 1 1 d .
H21A H 0.3391 -0.2180 -0.0173 0.026 Uiso 1 1 calc R
H21B H 0.2360 -0.0765 -0.0597 0.026 Uiso 1 1 calc R
C22 C 0.1189(3) -0.1703(2) 0.05948(17) 0.0215(5) Uani 1 1 d .
N1 N 0.2189(2) 0.86380(19) 0.36518(13) 0.0179(4) Uani 1 1 d .
N2 N 0.2146(2) 1.04015(19) 0.45345(14) 0.0210(4) Uani 1 1 d .
N3 N 0.2952(2) 0.13895(19) 0.15033(14) 0.0184(4) Uani 1 1 d .
N4 N 0.3067(2) -0.04011(19) 0.06190(14) 0.0187(4) Uani 1 1 d .
O1 O 0.4282(2) 1.1790(2) 0.37820(14) 0.0412(5) Uani 1 1 d .
O2 O 0.40874(19) 1.27481(17) 0.52515(13) 0.0262(4) Uani 1 1 d .
O3 O 0.0640(2) -0.23796(19) 0.01097(13) 0.0312(4) Uani 1 1 d .
O4 O 0.0716(2) -0.1340(2) 0.14837(13) 0.0349(5) Uani 1 1 d .
O5 O 0.3734(2) 0.2237(2) 0.72863(14) 0.0350(5) Uani 1 1 d .
O6 O 0.8574(2) 0.6327(2) 0.12764(14) 0.0352(5) Uani 1 1 d .
O7 O 0.0903(2) 0.65800(19) 0.82933(15) 0.0388(5) Uani 1 1 d .
O8 O 0.7778(2) 0.9866(2) 0.22576(15) 0.0412(5) Uani 1 1 d .
O9 O 0.2470(3) 0.7770(2) 0.66647(16) 0.0663(8) Uani 1 1 d .
O10 O 0.4598(4) 0.5330(4) 0.5869(3) 0.0290(8) Uani 0.50 1 d P
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_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 111.15(18) . .
N1 C1 H1A 109.4 . .
C2 C1 H1A 109.4 . .
N1 C1 H1B 109.4 . .
C2 C1 H1B 109.4 . .
H1A C1 H1B 108.0 . .
C6 C2 C3 119.9(2) . .
C6 C2 C1 120.3(2) . .
C3 C2 C1 119.8(2) . .
C4 C3 C2 120.5(2) . .
C4 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
C3 C4 C5 120.4(2) . 2_566
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 2_566 .
C4 C5 C6 121.8(2) 2_566 .
C4 C5 C5 119.4(3) 2_566 2_566
C6 C5 C5 118.7(3) . 2_566
C2 C6 C5 120.9(2) . .
C2 C6 H6 119.5 . .
C5 C6 H6 119.5 . .
N2 C7 N1 108.40(19) . .
N2 C7 H7 125.8 . .
N1 C7 H7 125.8 . .
C9 C8 N2 107.5(2) . .
C9 C8 H8 126.3 . .
N2 C8 H8 126.3 . .
C8 C9 N1 106.7(2) . .
C8 C9 H9 126.7 . .
N1 C9 H9 126.7 . .
N2 C10 C11 114.15(19) . .
N2 C10 H10A 108.7 . .
C11 C10 H10A 108.7 . .
N2 C10 H10B 108.7 . .
C11 C10 H10B 108.7 . .
H10A C10 H10B 107.6 . .
O1 C11 O2 127.1(2) . .
O1 C11 C10 118.9(2) . .
O2 C11 C10 113.9(2) . .
N3 C12 C13 110.70(18) . .
N3 C12 H12A 109.5 . .
C13 C12 H12A 109.5 . .
N3 C12 H12B 109.5 . .
C13 C12 H12B 109.5 . .
H12A C12 H12B 108.1 . .
C17 C13 C14 119.7(2) . .
C17 C13 C12 120.2(2) . .
C14 C13 C12 120.1(2) . .
C15 C14 C13 120.6(2) . .
C15 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C14 C15 C16 120.5(2) . 2_665
C14 C15 H15 119.7 . .
C16 C15 H15 119.7 2_665 .
C15 C16 C17 122.2(2) 2_665 .
C15 C16 C16 119.3(3) 2_665 2_665
C17 C16 C16 118.5(3) . 2_665
C13 C17 C16 121.3(2) . .
C13 C17 H17 119.3 . .
C16 C17 H17 119.3 . .
N4 C18 N3 108.39(19) . .
N4 C18 H18 125.8 . .
N3 C18 H18 125.8 . .
C20 C19 N4 107.10(19) . .
C20 C19 H19 126.4 . .
N4 C19 H19 126.4 . .
C19 C20 N3 106.75(19) . .
C19 C20 H20 126.6 . .
N3 C20 H20 126.6 . .
N4 C21 C22 111.91(18) . .
N4 C21 H21A 109.2 . .
C22 C21 H21A 109.2 . .
N4 C21 H21B 109.2 . .
C22 C21 H21B 109.2 . .
H21A C21 H21B 107.9 . .
O4 C22 O3 126.4(2) . .
O4 C22 C21 117.9(2) . .
O3 C22 C21 115.7(2) . .
C7 N1 C9 108.80(18) . .
C7 N1 C1 124.89(19) . .
C9 N1 C1 126.24(19) . .
C7 N2 C8 108.67(19) . .
C7 N2 C10 124.7(2) . .
C8 N2 C10 126.57(19) . .
C18 N3 C20 108.92(18) . .
C18 N3 C12 125.50(19) . .
C20 N3 C12 125.50(19) . .
C18 N4 C19 108.83(19) . .
C18 N4 C21 123.69(19) . .
C19 N4 C21 126.65(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.480(3) .
C1 C2 1.517(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C6 1.373(3) .
C2 C3 1.420(3) .
C3 C4 1.373(3) .
C3 H3 0.9500 .
C4 C5 1.418(3) 2_566
C4 H4 0.9500 .
C5 C4 1.418(3) 2_566
C5 C6 1.422(3) .
C5 C5 1.422(4) 2_566
C6 H6 0.9500 .
C7 N2 1.329(3) .
C7 N1 1.333(3) .
C7 H7 0.9500 .
C8 C9 1.351(3) .
C8 N2 1.374(3) .
C8 H8 0.9500 .
C9 N1 1.379(3) .
C9 H9 0.9500 .
C10 N2 1.467(3) .
C10 C11 1.536(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 O1 1.233(3) .
C11 O2 1.263(3) .
C12 N3 1.473(3) .
C12 C13 1.504(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C17 1.371(3) .
C13 C14 1.420(3) .
C14 C15 1.369(3) .
C14 H14 0.9500 .
C15 C16 1.419(3) 2_665
C15 H15 0.9500 .
C16 C15 1.419(3) 2_665
C16 C17 1.420(3) .
C16 C16 1.424(4) 2_665
C17 H17 0.9500 .
C18 N4 1.330(3) .
C18 N3 1.334(3) .
C18 H18 0.9500 .
C19 C20 1.357(3) .
C19 N4 1.380(3) .
C19 H19 0.9500 .
C20 N3 1.380(3) .
C20 H20 0.9500 .
C21 N4 1.470(3) .
C21 C22 1.532(3) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 O4 1.246(3) .
C22 O3 1.254(3) .
