#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/78/2017871.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_2017871
loop_
_publ_author_name
'Titi, Hatem M.'
'Karmakar, Anirban'
'Goldberg, Israel'
_publ_section_title
;
 Coordination polymers and hydrogen-bonded assemblies of
 2,2'-[2,5-bis(carboxymethoxy)-1,4-phenylene]diacetic acid with ammonium,
 lanthanum and zinc cations
;
_journal_coeditor_code           SU3049
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m238
_journal_page_last               m244
_journal_paper_doi               10.1107/S0108270110031318
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'[Zn2 (C14 H10 O10) (C10 H8 N2) (H2 O)2] , 2H2 O'
_chemical_formula_moiety         'C24 H22 N2 O12 Zn2, 2(H2 O)'
_chemical_formula_sum            'C24 H26 N2 O14 Zn2'
_chemical_formula_weight         697.24
_chemical_name_systematic
;
poly[[diaqua(μ₂-4,4'-bipyridyl){μ₄-2,2'-[2,5-bis(carboxymethyl)-1,4-
phenylenedioxy]diacetato}dizinc(II)] dihydrate]
;
_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           SHELXL97
_cell_angle_alpha                108.621(3)
_cell_angle_beta                 94.915(3)
_cell_angle_gamma                92.412(3)
_cell_formula_units_Z            1
_cell_length_a                   7.7218(4)
_cell_length_b                   8.3520(5)
_cell_length_c                   10.7204(6)
_cell_measurement_reflns_used    2455
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.65
_cell_measurement_theta_min      2.02
_cell_volume                     651.01(6)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1 deg. φ and ω 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  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7281
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.921
_exptl_absorpt_correction_T_max  0.8311
_exptl_absorpt_correction_T_min  0.6999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.712
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0481
_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)+(0.0254P)²+0.9668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                2330
_reflns_number_total             2794
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su3049.cif
_cod_data_source_block           IV
_cod_database_code               2017871
_cod_database_fobs_code          2017871
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Zn Zn1 0.64853(5) 0.35334(5) 0.67884(4) 0.01753(13) Uani d . 1 . .
C C1 1.0378(4) 0.1350(4) -0.0481(3) 0.0155(7) Uani d . 1 . .
C C2 0.9607(4) 0.1625(4) 0.0693(3) 0.0161(7) Uani d . 1 . .
H H2 0.9340 0.2739 0.1176 0.019 Uiso calc R 1 . .
C C3 0.9220(4) 0.0295(4) 0.1168(3) 0.0152(7) Uani d . 1 . .
O O4 0.8396(3) 0.0465(3) 0.2291(2) 0.0197(5) Uani d . 1 . .
C C5 0.8222(4) 0.2147(4) 0.3107(3) 0.0168(7) Uani d . 1 . .
H H5A 0.7530 0.2747 0.2599 0.020 Uiso calc R 1 . .
H H5B 0.9387 0.2759 0.3397 0.020 Uiso calc R 1 . .
C C6 0.7325(4) 0.2128(4) 0.4305(3) 0.0191(7) Uani d . 1 . .
O O7 0.7171(3) 0.3634(3) 0.5098(2) 0.0204(5) Uani d . 1 . .
O O8 0.6809(4) 0.0844(3) 0.4519(2) 0.0292(6) Uani d . 1 . .
C C9 1.0814(4) 0.2794(4) -0.0984(3) 0.0169(7) Uani d . 1 . .
H H9A 1.1850 0.2524 -0.1476 0.020 Uiso calc R 1 . .
H H9B 1.1151 0.3818 -0.0209 0.020 Uiso calc R 1 . .
C C10 0.9401(5) 0.3233(4) -0.1874(3) 0.0180(7) Uani d . 1 . .
O O11 0.7855(3) 0.2555(3) -0.2018(2) 0.0197(5) Uani d . 1 . .
O O12 0.9777(3) 0.4316(3) -0.2403(2) 0.0247(6) Uani d . 1 . .
O O13 0.4125(3) 0.2444(3) 0.6720(2) 0.0217(5) Uani d . 1 . .
H H13A 0.3919 0.1362 0.6293 0.033 Uiso d . 1 . .
H H13B 0.3323 0.2822 0.6100 0.033 Uiso d . 1 . .
N N14 0.5879(3) 0.5959(3) 0.7833(3) 0.0158(6) Uani d . 1 . .
C C15 0.4943(4) 0.6114(4) 0.8861(3) 0.0201(7) Uani d . 1 . .
H H15 0.4500 0.5111 0.8996 0.024 Uiso calc R 1 . .
C C16 0.4594(4) 0.7656(4) 0.9733(3) 0.0184(7) Uani d . 1 . .
H H16 0.3957 0.7698 1.0461 0.022 Uiso calc R 1 . .
C C17 0.5181(4) 0.9151(4) 0.9538(3) 0.0149(7) Uani d . 1 . .
C C18 0.6101(4) 0.8997(4) 0.8445(3) 0.0186(7) Uani d . 1 . .
H H18 0.6494 0.9979 0.8255 0.022 Uiso calc R 1 . .
C C19 0.6437(4) 0.7397(4) 0.7635(3) 0.0195(7) Uani d . 1 . .
H H19 0.7091 0.7316 0.6909 0.023 Uiso calc R 1 . .
O O20 0.8341(3) 0.6429(3) 0.4561(2) 0.0262(6) Uani d . 1 . .
H H20A 0.7952 0.5501 0.4734 0.039 Uiso d R 1 . .
H H20B 0.8955 0.6185 0.3855 0.039 Uiso d R 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'
Zn Zn 0.2839 1.4301 '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
O7 Zn1 O11 . 1_556 124.79(10) ?
O7 Zn1 O13 . . 115.69(10) ?
O11 Zn1 O13 1_556 . 100.83(10) ?
O7 Zn1 N14 . . 106.20(10) ?
O11 Zn1 N14 1_556 . 110.06(10) ?
O13 Zn1 N14 . . 95.44(10) ?
C2 C1 C3 . 2_755 118.5(3) ?
C2 C1 C9 . . 121.0(3) ?
C3 C1 C9 2_755 . 120.5(3) ?
C3 C2 C1 . . 121.1(3) ?
C3 C2 H2 . . 119.4 ?
C1 C2 H2 . . 119.4 ?
O4 C3 C2 . . 124.2(3) ?
O4 C3 C1 . 2_755 115.5(3) ?
C2 C3 C1 . 2_755 120.3(3) ?
C3 O4 C5 . . 116.0(2) ?
O4 C5 C6 . . 109.9(3) ?
O4 C5 H5A . . 109.7 ?
C6 C5 H5A . . 109.7 ?
O4 C5 H5B . . 109.7 ?
C6 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
O8 C6 O7 . . 122.9(3) ?
O8 C6 C5 . . 124.7(3) ?
O7 C6 C5 . . 112.4(3) ?
C6 O7 Zn1 . . 110.4(2) ?
C1 C9 C10 . . 117.2(3) ?
C1 C9 H9A . . 108.0 ?
C10 C9 H9A . . 108.0 ?
C1 C9 H9B . . 108.0 ?
C10 C9 H9B . . 108.0 ?
H9A C9 H9B . . 107.2 ?
O12 C10 O11 . . 121.5(3) ?
O12 C10 C9 . . 118.5(3) ?
O11 C10 C9 . . 119.9(3) ?
C10 O11 Zn1 . 1_554 105.5(2) ?
Zn1 O13 H13A . . 119.1 ?
Zn1 O13 H13B . . 107.4 ?
H13A O13 H13B . . 95.5 ?
C15 N14 C19 . . 117.1(3) ?
C15 N14 Zn1 . . 116.7(2) ?
C19 N14 Zn1 . . 126.0(2) ?
N14 C15 C16 . . 123.5(3) ?
N14 C15 H15 . . 118.3 ?
C16 C15 H15 . . 118.3 ?
C15 C16 C17 . . 119.7(3) ?
C15 C16 H16 . . 120.2 ?
C17 C16 H16 . . 120.2 ?
C16 C17 C18 . . 117.2(3) ?
C16 C17 C17 . 2_677 121.1(3) ?
C18 C17 C17 . 2_677 121.8(4) ?
C19 C18 C17 . . 119.5(3) ?
C19 C18 H18 . . 120.2 ?
C17 C18 H18 . . 120.2 ?
N14 C19 C18 . . 123.1(3) ?
N14 C19 H19 . . 118.5 ?
C18 C19 H19 . . 118.5 ?
H20A O20 H20B . . 112.9 ?
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
Zn1 O7 . 1.957(2) yes
Zn1 O11 1_556 1.983(2) yes
Zn1 O13 . 1.988(2) yes
Zn1 N14 . 2.073(3) yes
C1 C2 . 1.395(4) ?
C1 C3 2_755 1.398(4) ?
C1 C9 . 1.507(5) ?
C2 C3 . 1.394(5) ?
C2 H2 . 0.9500 ?
C3 O4 . 1.380(4) ?
C3 C1 2_755 1.398(4) ?
O4 C5 . 1.417(4) ?
C5 C6 . 1.514(4) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 O8 . 1.225(4) ?
C6 O7 . 1.290(4) ?
C9 C10 . 1.522(5) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 O12 . 1.248(4) ?
C10 O11 . 1.275(4) ?
O11 Zn1 1_554 1.983(2) ?
O13 H13A . 0.8730 ?
O13 H13B . 1.0025 ?
N14 C15 . 1.345(4) ?
N14 C19 . 1.344(4) ?
C15 C16 . 1.381(4) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.394(5) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.396(4) ?
C17 C17 2_677 1.501(6) ?
C18 C19 . 1.391(4) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
O20 H20A . 0.8980 ?
O20 H20B . 0.8998 ?
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
O13 H13A O8 2_656 0.87 1.81 2.676(3) 172
O13 H13B O20 2_666 1.00 1.65 2.632(3) 164
O20 H20A O7 . 0.90 1.82 2.714(3) 179
O20 H20B O12 2_765 0.90 1.85 2.753(3) 180
