#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/90/2019098.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_2019098
loop_
_publ_author_name
'Patra, Ranjan'
'Goldberg, Israel'
_publ_section_title
;
 A three-dimensional coordination polymer of
 3-(3,5-dicarboxybenzyloxy)benzoic acid with zinc
;
_journal_coeditor_code           SK3498
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              819
_journal_page_last               821
_journal_paper_doi               10.1107/S0108270113017204
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Zn2 (C16 H9 O7) (O H) (C3 H7 N O)]'
_chemical_formula_moiety         'C19 H17 N O9 Zn2'
_chemical_formula_sum            'C19 H17 N O9 Zn2'
_chemical_formula_weight         534.12
_chemical_name_systematic
Poly[[μ₆-3-(3,5-dicarboxylatobenzyloxy)benzoato](dimethylformamide)-μ-hydroxido-dizinc(II)]
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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           SHELXL2012
_cell_angle_alpha                109.4630(10)
_cell_angle_beta                 90.6150(10)
_cell_angle_gamma                101.8840(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7417(2)
_cell_length_b                   10.8543(3)
_cell_length_c                   12.5527(3)
_cell_measurement_reflns_used    4319
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.04
_cell_volume                     969.62(4)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material  'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS2012 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 1.75
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX DUO area-detector'
_diffrn_measurement_method       '1° ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8513
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.041
_exptl_absorpt_coefficient_mu    2.529
_exptl_absorpt_correction_T_max  0.703
_exptl_absorpt_correction_T_min  0.518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.514
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0271
_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)+(0.0265P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0568
_reflns_number_gt                3474
_reflns_number_total             4319
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3498.cif
_cod_data_source_block           I
_cod_original_cell_volume        969.61(4)
_cod_database_code               2019098
_cod_database_fobs_code          2019098
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.518
_shelx_estimated_absorpt_t_max   0.703
_shelxl_version_number           .000002012
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
Zn Zn1 0.14134(3) 0.49867(2) 0.10074(2) 0.01016(7) Uani d 1
Zn Zn2 0.50942(3) 0.65047(2) 0.03857(2) 0.00921(7) Uani d 1
O O3 0.32138(18) 0.48139(14) -0.01538(12) 0.0090(3) Uani d 1
H H3 0.2569 0.4639 -0.0842 0.011 Uiso d 1
O O4 0.2794(2) 0.63903(15) 0.24711(13) 0.0154(3) Uani d 1
O O5 0.55968(19) 0.69616(15) 0.20663(12) 0.0143(3) Uani d 1
C C6 0.4393(3) 0.6962(2) 0.27420(18) 0.0124(5) Uani d 1
C C7 0.4942(3) 0.7731(2) 0.39765(19) 0.0144(5) Uani d 1
C C8 0.6711(3) 0.8227(2) 0.43883(19) 0.0188(5) Uani d 1
H H8 0.7621 0.8064 0.3892 0.023 Uiso calc 1
C C9 0.7139(3) 0.8967(2) 0.5541(2) 0.0220(6) Uani d 1
H H9 0.8347 0.9298 0.5828 0.026 Uiso calc 1
C C10 0.5823(3) 0.9224(2) 0.6269(2) 0.0197(5) Uani d 1
H H10 0.6129 0.9733 0.7050 0.024 Uiso calc 1
C C11 0.4056(3) 0.8736(2) 0.5853(2) 0.0172(5) Uani d 1
C C12 0.3619(3) 0.7988(2) 0.47147(19) 0.0163(5) Uani d 1
H H12 0.2409 0.7646 0.4434 0.020 Uiso calc 1
O O13 0.2625(2) 0.89205(17) 0.64821(13) 0.0237(4) Uani d 1
C C14 0.2982(3) 0.9825(2) 0.76311(18) 0.0158(5) Uani d 1
H H14A 0.3633 1.0722 0.7656 0.019 Uiso calc 1
H H14B 0.3705 0.9488 0.8080 0.019 Uiso calc 1
C C15 0.1203(3) 0.9900(2) 0.80975(18) 0.0137(5) Uani d 1
C C16 0.0182(3) 0.8770(2) 0.82545(18) 0.0149(5) Uani d 1
H H16 0.0579 0.7956 0.8017 0.018 Uiso calc 1
C C17 -0.1416(3) 0.8809(2) 0.87551(18) 0.0124(5) Uani d 1
C C18 -0.1999(3) 1.0002(2) 0.90958(18) 0.0135(5) Uani d 1
H H18 -0.3082 1.0042 0.9441 0.016 Uiso calc 1
C C19 -0.0991(3) 1.1143(2) 0.89307(18) 0.0124(5) Uani d 1
C C20 0.0603(3) 1.1081(2) 0.84335(18) 0.0145(5) Uani d 1
H H20 0.1287 1.1856 0.8323 0.017 Uiso calc 1
C C21 -0.1670(3) 1.2417(2) 0.92897(19) 0.0144(5) Uani d 1
O O22 -0.32929(19) 1.22689(15) 0.93683(14) 0.0173(4) Uani d 1
O O23 -0.05636(19) 1.35294(14) 0.94505(13) 0.0126(3) Uani d 1
C C24 -0.2387(3) 0.7582(2) 0.89795(18) 0.0110(5) Uani d 1
O O25 -0.36216(19) 0.77105(14) 0.96256(13) 0.0141(3) Uani d 1
O O26 -0.1881(2) 0.65203(15) 0.85050(13) 0.0161(4) Uani d 1
O O27 -0.09392(19) 0.48666(15) 0.18739(13) 0.0147(3) Uani d 1
C C28 -0.0911(3) 0.5199(2) 0.2922(2) 0.0176(5) Uani d 1
H H28 0.0165 0.5723 0.3356 0.021 Uiso calc 1
N N29 -0.2275(3) 0.4876(2) 0.34796(16) 0.0195(4) Uani d 1
C C30 -0.3948(3) 0.4044(3) 0.2870(2) 0.0303(6) Uani d 1
H H30A -0.4802 0.4607 0.2904 0.045 Uiso calc 1
H H30B -0.4410 0.3372 0.3219 0.045 Uiso calc 1
H H30C -0.3761 0.3593 0.2077 0.045 Uiso calc 1
C C31 -0.2192(4) 0.5367(3) 0.4717(2) 0.0301(6) Uani d 1
H H31A -0.0998 0.5898 0.5026 0.045 Uiso calc 1
H H31B -0.2466 0.4604 0.4987 0.045 Uiso calc 1
H H31C -0.3055 0.5927 0.4969 0.045 Uiso calc 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'
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
O3 Zn1 O26 . 2_566 95.02(6)
O3 Zn1 O4 . . 104.27(6)
O26 Zn1 O4 2_566 . 90.79(6)
O3 Zn1 O23 . 2_576 91.68(6)
O26 Zn1 O23 2_566 2_576 172.05(6)
O4 Zn1 O23 . 2_576 91.70(6)
O3 Zn1 O27 . . 165.64(6)
O26 Zn1 O27 2_566 . 86.77(6)
O4 Zn1 O27 . . 89.94(6)
O23 Zn1 O27 2_576 . 85.68(5)
O3 Zn1 O23 . 1_544 83.70(5)
O26 Zn1 O23 2_566 1_544 93.44(6)
O4 Zn1 O23 . 1_544 170.64(5)
O23 Zn1 O23 2_576 1_544 83.04(6)
O27 Zn1 O23 . 1_544 81.97(5)
O25 Zn2 O3 1_654 . 133.57(6)
O25 Zn2 O5 1_654 . 119.49(6)
O3 Zn2 O5 . . 106.93(6)
O25 Zn2 O22 1_654 2_576 83.93(6)
O3 Zn2 O22 . 2_576 93.68(6)
O5 Zn2 O22 . 2_576 92.08(6)
O25 Zn2 O3 1_654 2_665 99.25(6)
O3 Zn2 O3 . 2_665 83.29(6)
O5 Zn2 O3 . 2_665 87.37(6)
O22 Zn2 O3 2_576 2_665 176.62(6)
O25 Zn2 Zn2 1_654 2_665 124.13(4)
O3 Zn2 Zn2 . 2_665 42.73(4)
O5 Zn2 Zn2 . 2_665 99.17(4)
O22 Zn2 Zn2 2_576 2_665 136.39(4)
O3 Zn2 Zn2 2_665 2_665 40.56(4)
Zn2 O3 Zn1 . . 106.91(6)
Zn2 O3 Zn2 . 2_665 96.71(6)
Zn1 O3 Zn2 . 2_665 122.98(7)
Zn2 O3 H3 . . 116.3
Zn1 O3 H3 . . 105.1
Zn2 O3 H3 2_665 . 109.4
C6 O4 Zn1 . . 133.76(14)
C6 O5 Zn2 . . 123.28(14)
O4 C6 O5 . . 125.9(2)
O4 C6 C7 . . 117.43(19)
O5 C6 C7 . . 116.7(2)
C8 C7 C12 . . 119.7(2)
C8 C7 C6 . . 121.9(2)
C12 C7 C6 . . 118.3(2)
C7 C8 C9 . . 119.3(2)
C7 C8 H8 . . 120.4
C9 C8 H8 . . 120.4
C10 C9 C8 . . 120.9(2)
C10 C9 H9 . . 119.6
C8 C9 H9 . . 119.6
C9 C10 C11 . . 119.7(2)
C9 C10 H10 . . 120.2
C11 C10 H10 . . 120.2
O13 C11 C12 . . 114.6(2)
O13 C11 C10 . . 125.6(2)
C12 C11 C10 . . 119.9(2)
C11 C12 C7 . . 120.6(2)
C11 C12 H12 . . 119.7
C7 C12 H12 . . 119.7
C11 O13 C14 . . 117.18(18)
O13 C14 C15 . . 106.25(18)
O13 C14 H14A . . 110.5
C15 C14 H14A . . 110.5
O13 C14 H14B . . 110.5
C15 C14 H14B . . 110.5
H14A C14 H14B . . 108.7
C20 C15 C16 . . 119.1(2)
C20 C15 C14 . . 122.0(2)
C16 C15 C14 . . 118.82(19)
C15 C16 C17 . . 121.2(2)
C15 C16 H16 . . 119.4
C17 C16 H16 . . 119.4
C18 C17 C16 . . 119.2(2)
C18 C17 C24 . . 122.16(19)
C16 C17 C24 . . 118.51(19)
C17 C18 C19 . . 120.1(2)
C17 C18 H18 . . 120.0
C19 C18 H18 . . 120.0
C20 C19 C18 . . 119.69(19)
C20 C19 C21 . . 121.3(2)
C18 C19 C21 . . 118.98(19)
C15 C20 C19 . . 120.7(2)
C15 C20 H20 . . 119.6
C19 C20 H20 . . 119.6
O22 C21 O23 . . 126.05(19)
O22 C21 C19 . . 115.5(2)
O23 C21 C19 . . 118.38(19)
C21 O22 Zn2 . 2_576 135.66(15)
C21 O23 Zn1 . 2_576 118.31(13)
C21 O23 Zn1 . 1_566 132.63(14)
Zn1 O23 Zn1 2_576 1_566 96.96(6)
O26 C24 O25 . . 125.9(2)
O26 C24 C17 . . 116.45(19)
O25 C24 C17 . . 117.60(18)
C24 O25 Zn2 . 1_456 131.08(14)
C24 O26 Zn1 . 2_566 134.98(14)
C28 O27 Zn1 . . 122.72(15)
O27 C28 N29 . . 124.7(2)
O27 C28 H28 . . 117.7
N29 C28 H28 . . 117.7
C28 N29 C30 . . 120.6(2)
C28 N29 C31 . . 122.1(2)
C30 N29 C31 . . 117.3(2)
N29 C30 H30A . . 109.5
N29 C30 H30B . . 109.5
H30A C30 H30B . . 109.5
N29 C30 H30C . . 109.5
H30A C30 H30C . . 109.5
H30B C30 H30C . . 109.5
N29 C31 H31A . . 109.5
N29 C31 H31B . . 109.5
H31A C31 H31B . . 109.5
N29 C31 H31C . . 109.5
H31A C31 H31C . . 109.5
H31B C31 H31C . . 109.5
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 O3 . 2.0178(13) yes
Zn1 O26 2_566 2.0218(15) yes
Zn1 O4 . 2.0643(15) yes
Zn1 O23 2_576 2.0982(14) yes
Zn1 O27 . 2.1346(14) yes
Zn1 O23 1_544 2.3542(15) yes
Zn2 O25 1_654 1.9821(15) yes
Zn2 O3 . 1.9990(14) yes
Zn2 O5 . 2.0133(15) yes
Zn2 O22 2_576 2.0765(14) yes
Zn2 O3 2_665 2.0861(13) yes
Zn2 Zn2 2_665 3.0531(5) yes
Zn2 Zn1 . 3.2272(3) yes
O3 Zn2 2_665 2.0861(13) yes
O3 H3 . 0.9347 ?
O4 C6 . 1.252(3) ?
O5 C6 . 1.266(2) ?
C6 C7 . 1.502(3) ?
C7 C8 . 1.389(3) ?
C7 C12 . 1.397(3) ?
C8 C9 . 1.398(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.385(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.389(3) ?
C10 H10 . 0.9500 ?
C11 O13 . 1.377(3) ?
C11 C12 . 1.385(3) ?
C12 H12 . 0.9500 ?
O13 C14 . 1.434(3) ?
C14 C15 . 1.510(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C20 . 1.388(3) ?
C15 C16 . 1.390(3) ?
C16 C17 . 1.395(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.393(3) ?
C17 C24 . 1.504(3) ?
C18 C19 . 1.401(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.393(3) ?
C19 C21 . 1.510(3) ?
C20 H20 . 0.9500 ?
C21 O22 . 1.242(3) ?
C21 O23 . 1.281(3) ?
O22 Zn2 2_576 2.0765(14) ?
O23 Zn1 2_576 2.0982(14) ?
O23 Zn1 1_566 2.3542(15) ?
C24 O26 . 1.253(2) ?
C24 O25 . 1.260(2) ?
O25 Zn2 1_456 1.9821(15) ?
O26 Zn1 2_566 2.0218(15) ?
O27 C28 . 1.242(3) ?
C28 N29 . 1.324(3) ?
C28 H28 . 0.9500 ?
N29 C30 . 1.455(3) ?
N29 C31 . 1.461(3) ?
C30 H30A . 0.9800 ?
C30 H30B . 0.9800 ?
C30 H30C . 0.9800 ?
C31 H31A . 0.9800 ?
C31 H31B . 0.9800 ?
C31 H31C . 0.9800 ?
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
O3 H3 O27 2_565 0.93 2.07 2.924(2) 152
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_4
_geom_torsion
Zn1 O4 C6 O5 . 12.6(3)
Zn1 O4 C6 C7 . -167.98(14)
Zn2 O5 C6 O4 . 18.6(3)
Zn2 O5 C6 C7 . -160.84(14)
O4 C6 C7 C8 . 170.0(2)
O5 C6 C7 C8 . -10.6(3)
O4 C6 C7 C12 . -12.3(3)
O5 C6 C7 C12 . 167.2(2)
C12 C7 C8 C9 . 0.5(3)
C6 C7 C8 C9 . 178.2(2)
C7 C8 C9 C10 . -0.8(4)
C8 C9 C10 C11 . 0.3(4)
C9 C10 C11 O13 . -179.9(2)
C9 C10 C11 C12 . 0.4(4)
O13 C11 C12 C7 . 179.6(2)
C10 C11 C12 C7 . -0.7(3)
C8 C7 C12 C11 . 0.2(3)
C6 C7 C12 C11 . -177.6(2)
C12 C11 O13 C14 . -172.3(2)
C10 C11 O13 C14 . 8.0(3)
C11 O13 C14 C15 . 176.94(19)
O13 C14 C15 C20 . -116.2(2)
O13 C14 C15 C16 . 67.5(3)
C20 C15 C16 C17 . -0.8(3)
C14 C15 C16 C17 . 175.5(2)
C15 C16 C17 C18 . 0.4(3)
C15 C16 C17 C24 . -175.5(2)
C16 C17 C18 C19 . 0.3(3)
C24 C17 C18 C19 . 176.0(2)
C17 C18 C19 C20 . -0.5(3)
C17 C18 C19 C21 . 179.0(2)
C16 C15 C20 C19 . 0.5(3)
C14 C15 C20 C19 . -175.7(2)
C18 C19 C20 C15 . 0.1(3)
C21 C19 C20 C15 . -179.4(2)
C20 C19 C21 O22 . 157.3(2)
C18 C19 C21 O22 . -22.2(3)
C20 C19 C21 O23 . -20.6(3)
C18 C19 C21 O23 . 159.9(2)
O23 C21 O22 Zn2 2_576 6.7(4)
C19 C21 O22 Zn2 2_576 -171.11(15)
O22 C21 O23 Zn1 2_576 -33.8(3)
C19 C21 O23 Zn1 2_576 143.94(16)
O22 C21 O23 Zn1 1_566 99.3(3)
C19 C21 O23 Zn1 1_566 -83.0(2)
C18 C17 C24 O26 . 170.7(2)
C16 C17 C24 O26 . -13.5(3)
C18 C17 C24 O25 . -9.6(3)
C16 C17 C24 O25 . 166.2(2)
O26 C24 O25 Zn2 1_456 13.4(3)
C17 C24 O25 Zn2 1_456 -166.27(14)
O25 C24 O26 Zn1 2_566 -43.2(3)
C17 C24 O26 Zn1 2_566 136.49(18)
Zn1 O27 C28 N29 . -164.38(17)
O27 C28 N29 C30 . 1.8(3)
O27 C28 N29 C31 . -176.2(2)
