#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/78/2017868.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_2017868
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          '2N H4 + , C14 H12 O10 2-'
_chemical_formula_moiety         '2(H4 N +), C14 H12 O10 2-'
_chemical_formula_sum            'C14 H20 N2 O10'
_chemical_formula_weight         376.32
_chemical_name_systematic
;
diammonium 2,2'-[2,5-bis(carboxymethyl)-1,4-phenylenedioxy]diacetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.855(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8188(3)
_cell_length_b                   14.6889(8)
_cell_length_c                   11.2087(8)
_cell_measurement_reflns_used    1652
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.29
_cell_volume                     792.97(9)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9862
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0487P)²+0.3554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                1243
_reflns_number_total             1598
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su3049.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017868
_cod_database_fobs_code          2017868
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8294(4) 0.04845(12) 0.07567(17) 0.0166(4) Uani d . 1 . .
C C2 0.8154(4) 0.06322(13) -0.04671(17) 0.0168(4) Uani d . 1 . .
H H2 0.696(5) 0.1067(15) -0.0789(19) 0.020 Uiso d . 1 . .
C C3 1.0173(4) -0.01523(12) 0.12399(17) 0.0168(4) Uani d . 1 . .
O O4 0.6641(3) 0.09384(8) 0.15602(11) 0.0181(3) Uani d . 1 . .
C C5 0.4886(4) 0.16176(13) 0.10272(18) 0.0183(4) Uani d . 1 . .
H H5A 0.378(5) 0.1356(14) 0.039(2) 0.022 Uiso d . 1 . .
H H5B 0.606(5) 0.2098(15) 0.0682(19) 0.022 Uiso d . 1 . .
C C6 0.2924(4) 0.20441(12) 0.19049(17) 0.0173(4) Uani d . 1 . .
O O7 0.1458(3) 0.26711(9) 0.14113(12) 0.0214(3) Uani d . 1 . .
O O8 0.2751(3) 0.17838(9) 0.29544(12) 0.0200(3) Uani d . 1 . .
C C9 1.0489(4) -0.03077(13) 0.25620(18) 0.0185(4) Uani d . 1 . .
H H9A 1.074(4) 0.0274(15) 0.2995(19) 0.022 Uiso d . 1 . .
H H9B 1.220(5) -0.0699(14) 0.2726(19) 0.022 Uiso d . 1 . .
C C10 0.8145(4) -0.08245(12) 0.31195(17) 0.0186(4) Uani d . 1 . .
O O11 0.7183(3) -0.15015(9) 0.24562(12) 0.0216(3) Uani d . 1 . .
H H11 0.567(5) -0.1823(15) 0.287(2) 0.032 Uiso d . 1 . .
O O12 0.7324(3) -0.06467(9) 0.41152(12) 0.0249(4) Uani d . 1 . .
N N13 0.7511(4) 0.13651(13) 0.42955(17) 0.0211(4) Uani d . 1 . .
H H13A 0.714(5) 0.1672(16) 0.500(2) 0.032 Uiso d . 1 . .
H H13B 0.596(6) 0.1456(16) 0.380(2) 0.032 Uiso d . 1 . .
H H13C 0.753(5) 0.0723(18) 0.443(2) 0.032 Uiso d . 1 . .
H H13D 0.915(6) 0.1590(15) 0.393(2) 0.032 Uiso 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'
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'
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
C2 C1 O4 . . 123.64(17) ?
C2 C1 C3 . . 119.82(17) ?
O4 C1 C3 . . 116.54(16) ?
C1 C2 C3 . 3_755 121.63(18) ?
C1 C2 H2 . . 120.2(13) ?
C3 C2 H2 3_755 . 118.1(13) ?
C2 C3 C1 3_755 . 118.54(18) ?
C2 C3 C9 3_755 . 119.61(17) ?
C1 C3 C9 . . 121.82(17) ?
C1 O4 C5 . . 114.08(14) ?
O4 C5 C6 . . 112.93(16) ?
O4 C5 H5A . . 109.9(13) ?
C6 C5 H5A . . 107.7(13) ?
O4 C5 H5B . . 108.9(13) ?
C6 C5 H5B . . 109.5(12) ?
H5A C5 H5B . . 107.7(18) ?
O8 C6 O7 . . 125.44(17) ?
O8 C6 C5 . . 123.20(17) ?
O7 C6 C5 . . 111.33(16) ?
C3 C9 C10 . . 115.51(16) ?
C3 C9 H9A . . 111.1(12) ?
C10 C9 H9A . . 108.3(12) ?
C3 C9 H9B . . 108.7(12) ?
C10 C9 H9B . . 104.6(12) ?
H9A C9 H9B . . 108.2(18) ?
O12 C10 O11 . . 123.89(18) ?
O12 C10 C9 . . 122.49(17) ?
O11 C10 C9 . . 113.55(16) ?
C10 O11 H11 . . 110.2(13) ?
H13A N13 H13B . . 106(2) ?
H13A N13 H13C . . 110(2) ?
H13B N13 H13C . . 104(2) ?
H13A N13 H13D . . 112(2) ?
H13B N13 H13D . . 111(2) ?
H13C N13 H13D . . 114(2) ?
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
C1 C2 . 1.388(3) ?
C1 O4 . 1.392(2) ?
C1 C3 . 1.399(3) ?
C2 C3 3_755 1.394(3) ?
C2 H2 . 0.92(2) ?
C3 C2 3_755 1.394(3) ?
C3 C9 . 1.502(3) ?
O4 C5 . 1.426(2) ?
C5 C6 . 1.522(3) ?
C5 H5A . 0.96(2) ?
C5 H5B . 0.99(2) ?
C6 O8 . 1.242(2) ?
C6 O7 . 1.276(2) ?
C9 C10 . 1.513(3) ?
C9 H9A . 0.99(2) ?
C9 H9B . 1.02(2) ?
C10 O12 . 1.224(2) ?
C10 O11 . 1.317(2) ?
O11 H11 . 0.99(2) ?
N13 H13A . 0.93(3) ?
N13 H13B . 0.93(3) ?
N13 H13C . 0.96(3) ?
N13 H13D . 0.96(3) ?
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
O11 H11 O7 2_545 0.99(2) 1.52(2) 2.5123(19) 175(2)
N13 H13A O7 4_666 0.93(3) 1.89(3) 2.822(2) 178(2)
N13 H13B O8 . 0.93(3) 1.85(3) 2.771(2) 171(2)
N13 H13C O12 . 0.96(3) 2.05(3) 2.963(2) 160(2)
N13 H13D O8 1_655 0.96(3) 2.10(3) 3.043(2) 167(2)
