#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/40/2224002.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_2224002
loop_
_publ_author_name
'Shang, Shao-Ming'
'Li, Su-Yun'
'Ren, Chun-Xia'
'Wang, Xin'
'Lu, Lu-De'
_publ_section_title
;
 1,4-Bis(4,5-dihydro-1H-imidazol-2-yl)benzene--terephthalic
 acid--water (1/1/4)
;
_journal_coeditor_code           SI2204
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2682
_journal_page_last               o2683
_journal_paper_doi               10.1107/S1600536809040616
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H14 N4, C8 H6 O4, 4H2 O'
_chemical_formula_moiety         'C12 H14 N4, C8 H6 O4, 4(H2 O)'
_chemical_formula_sum            'C20 H28 N4 O8'
_chemical_formula_weight         452.46
_chemical_name_systematic
;
1,4-Bis(4,5-dihydro-1H-imidazol-2-yl)benzene--terephthalic acid--water
(1/1/4)
;
_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                 94.899(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9929(13)
_cell_length_b                   16.847(3)
_cell_length_c                   7.9615(12)
_cell_measurement_reflns_used    978
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.17
_cell_measurement_theta_min      2.42
_cell_volume                     1068.2(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0746
_diffrn_reflns_av_sigmaI/netI    0.1144
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5588
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_correction_T_min  0.9472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.427
_refine_ls_extinction_coef       0.12(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.790
_refine_ls_R_factor_all          0.1591
_refine_ls_R_factor_gt           0.0895
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1628P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2037
_refine_ls_wR_factor_ref         0.2570
_reflns_number_gt                832
_reflns_number_total             2300
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2204.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 21/c'
_cod_database_code               2224002
_cod_database_fobs_code          2224002
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-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 0.2209(4) 0.83842(17) 0.1428(4) 0.0622(10) Uani d . 1 . .
N N2 0.0932(4) 0.95122(17) 0.1837(4) 0.0621(10) Uani d . 1 . .
H H2C 0.0744 1.0015 0.1797 0.074 Uiso calc R 1 . .
C C1 -0.0182(6) 0.8931(2) 0.2516(6) 0.0704(13) Uani d . 1 . .
H H1A -0.1318 0.8981 0.1991 0.085 Uiso calc R 1 . .
H H1B -0.0199 0.8989 0.3726 0.085 Uiso calc R 1 . .
C C2 0.0597(6) 0.8138(2) 0.2069(6) 0.0692(13) Uani d . 1 . .
H H2A 0.0785 0.7800 0.3053 0.083 Uiso calc R 1 . .
H H2B -0.0109 0.7860 0.1208 0.083 Uiso calc R 1 . .
C C3 0.2264(5) 0.9167(2) 0.1292(4) 0.0558(11) Uani d . 1 . .
C C4 0.3678(5) 0.9588(2) 0.0625(4) 0.0541(11) Uani d . 1 . .
C C5 0.4927(6) 0.9183(2) -0.0102(5) 0.0684(13) Uani d . 1 . .
H H5 0.4886 0.8632 -0.0177 0.082 Uiso d R 1 . .
O O1 0.4731(4) 0.71811(16) 0.0453(4) 0.0702(9) Uani d . 1 . .
O O2 0.2324(5) 0.66542(18) 0.1033(4) 0.0915(11) Uani d . 1 . .
H H2D 0.2110 0.7124 0.1183 0.137 Uiso calc R 1 . .
C C6 0.3758(6) 1.0410(2) 0.0723(5) 0.0659(12) Uani d . 1 . .
H H6 0.2921 1.0689 0.1212 0.079 Uiso d R 1 . .
C C7 0.3793(7) 0.6590(2) 0.0620(5) 0.0649(12) Uani d . 1 . .
C C8 0.4386(5) 0.5771(2) 0.0299(5) 0.0570(11) Uani d . 1 . .
C C9 0.6008(6) 0.5648(2) -0.0226(5) 0.0647(12) Uani d . 1 . .
H H9 0.6694 0.6082 -0.0391 0.078 Uiso d R 1 . .
C C10 0.3416(6) 0.5107(2) 0.0509(5) 0.0644(12) Uani d . 1 . .
H H10 0.2339 0.5170 0.0849 0.077 Uiso d R 1 . .
O O1W 0.9737(5) 0.61448(19) 0.2736(5) 0.0901(12) Uani d D 1 . .
H H1WA 1.053(4) 0.627(2) 0.212(5) 0.11(2) Uiso d D 1 . .
H H1WB 0.904(5) 0.6509(19) 0.296(6) 0.10(2) Uiso d D 1 . .
O O2W 0.7204(4) 0.76340(18) 0.8161(5) 0.0821(11) Uani d D 1 . .
H H2WA 0.6459 0.7691 0.7341 0.098 Uiso d RD 1 . .
H H2WB 0.700(6) 0.776(7) 0.916(3) 0.31(7) Uiso d 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 C2 . . 110.0(3) ?
C3 N2 C1 . . 111.2(3) ?
C3 N2 H2C . . 124.4 ?
C1 N2 H2C . . 124.4 ?
N2 C1 C2 . . 103.1(3) ?
N2 C1 H1A . . 111.1 ?
C2 C1 H1A . . 111.1 ?
N2 C1 H1B . . 111.1 ?
C2 C1 H1B . . 111.1 ?
H1A C1 H1B . . 109.1 ?
N1 C2 C1 . . 102.7(3) ?
N1 C2 H2A . . 111.2 ?
C1 C2 H2A . . 111.2 ?
N1 C2 H2B . . 111.2 ?
C1 C2 H2B . . 111.2 ?
H2A C2 H2B . . 109.1 ?
N2 C3 N1 . . 112.3(4) ?
N2 C3 C4 . . 124.9(3) ?
N1 C3 C4 . . 122.8(4) ?
C5 C4 C6 . . 119.1(4) ?
C5 C4 C3 . . 121.3(3) ?
C6 C4 C3 . . 119.6(4) ?
C4 C5 C6 . 3_675 120.4(3) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 3_675 . 119.7 ?
C7 O2 H2D . . 109.5 ?
C5 C6 C4 3_675 . 120.5(4) ?
C5 C6 H6 3_675 . 119.7 ?
C4 C6 H6 . . 119.8 ?
O2 C7 O1 . . 122.7(4) ?
O2 C7 C8 . . 116.4(4) ?
O1 C7 C8 . . 120.9(4) ?
C10 C8 C9 . . 117.1(3) ?
C10 C8 C7 . . 122.8(4) ?
C9 C8 C7 . . 120.1(4) ?
C10 C9 C8 3_665 . 120.9(4) ?
C10 C9 H9 3_665 . 119.6 ?
C8 C9 H9 . . 119.5 ?
C9 C10 C8 3_665 . 122.0(4) ?
C9 C10 H10 3_665 . 118.8 ?
C8 C10 H10 . . 119.1 ?
H1WA O1W H1WB . . 118(2) ?
H2WA O2W H2WB . . 120.8 ?
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 C3 . 1.324(5) ?
N1 C2 . 1.485(5) ?
N2 C3 . 1.319(5) ?
N2 C1 . 1.458(5) ?
N2 H2C . 0.8600 ?
C1 C2 . 1.528(5) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.472(6) ?
C4 C5 . 1.377(5) ?
C4 C6 . 1.389(5) ?
C5 C6 3_675 1.381(5) ?
C5 H5 . 0.9299 ?
O1 C7 . 1.260(5) ?
O2 C7 . 1.251(5) ?
O2 H2D . 0.8200 ?
C6 C5 3_675 1.381(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.487(6) ?
C8 C10 . 1.379(5) ?
C8 C9 . 1.412(6) ?
C9 C10 3_665 1.377(5) ?
C9 H9 . 0.9300 ?
C10 C9 3_665 1.377(5) ?
C10 H10 . 0.9300 ?
O1W H1WA . 0.86(3) ?
O1W H1WB . 0.86(4) ?
O2W H2WA . 0.85 ?
O2W H2WB . 0.85(4) ?
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
O2W H2WB O1 1_556 0.85(4) 2.37(6) 2.904(5) 121(7)
O2W H2WA O1 4_576 0.85 1.96 2.815(5) 179.7
O1W H1WB O2W 4_575 0.85(4) 2.08(4) 2.926(5) 172(5)
O1W H1WA O2 1_655 0.86(3) 1.851(15) 2.707(5) 172(3)
O2 H2D N1 . 0.82 2.13 2.934(4) 165.2
N2 H2C O1W 2_655 0.86 1.98 2.828(4) 166.9
C5 H5 O1 . 0.93 2.50 3.407(4) 165
C6 H6 O1W 2_655 0.93 2.47 3.380(6) 166
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
C3 N2 C1 C2 . . . . -7.5(4) ?
C3 N1 C2 C1 . . . . -7.6(4) ?
N2 C1 C2 N1 . . . . 8.6(4) ?
C1 N2 C3 N1 . . . . 2.9(5) ?
C1 N2 C3 C4 . . . . -176.3(4) ?
C2 N1 C3 N2 . . . . 3.3(5) ?
C2 N1 C3 C4 . . . . -177.5(3) ?
N2 C3 C4 C5 . . . . -172.2(4) ?
N1 C3 C4 C5 . . . . 8.6(6) ?
N2 C3 C4 C6 . . . . 7.6(6) ?
N1 C3 C4 C6 . . . . -171.6(4) ?
C6 C4 C5 C6 . . . 3_675 0.1(7) ?
C3 C4 C5 C6 . . . 3_675 179.9(4) ?
C5 C4 C6 C5 . . . 3_675 -0.1(7) ?
C3 C4 C6 C5 . . . 3_675 -179.9(4) ?
O2 C7 C8 C10 . . . . -2.8(6) ?
O1 C7 C8 C10 . . . . 178.3(4) ?
O2 C7 C8 C9 . . . . 177.9(4) ?
O1 C7 C8 C9 . . . . -1.0(6) ?
C10 C8 C9 C10 . . . 3_665 -0.1(6) ?
C7 C8 C9 C10 . . . 3_665 179.2(4) ?
C9 C8 C10 C9 . . . 3_665 0.1(6) ?
C7 C8 C10 C9 . . . 3_665 -179.2(4) ?
