#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/87/2218732.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_2218732
loop_
_publ_author_name
'Chen, Rui-Zhan'
'Guo, Fei-Jun'
'Meng, Fan-Lei'
_publ_section_title
;(5,5'-Dicarboxybiphenyl-2,2'-dicarboxylato-κ²O²,O^2'^)bis(1,10-phenanthroline-κ²N,N')zinc(II)
 dihydrate
;
_journal_coeditor_code           HY2133
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m855
_journal_paper_doi               10.1107/S1600536808015742
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Zn (C16 H8 O8) (C12 H8 N2)2], 2H2 O'
_chemical_formula_moiety         'C40 H24 N4 O8 Zn, 2(H2 O)'
_chemical_formula_sum            'C40 H28 N4 O10 Zn'
_chemical_formula_weight         790.03
_chemical_name_systematic
;
(5,5'-Dicarboxybiphenyl-2,2'-dicarboxylato-κ²O²,O^2'^)bis(1,10-
phenanthroline-κ²N,N')zinc(II) dihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 96.429(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.901(5)
_cell_length_b                   9.473(3)
_cell_length_c                   22.126(7)
_cell_measurement_reflns_used    3487
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.03
_cell_volume                     3520.2(19)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9664
_diffrn_reflns_theta_full        26.18
_diffrn_reflns_theta_max         26.18
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0573
_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)+(0.0505P)²+0.8309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                2437
_reflns_number_total             3487
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2133.cif
_cod_data_source_block           I
_cod_original_cell_volume        3520.4(19)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2218732
_cod_database_fobs_code          2218732
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C C1 0.3739(2) 0.3651(5) 0.63923(18) 0.0637(11) Uani d . 1
H H1 0.3543 0.2958 0.6634 0.076 Uiso calc R 1
C C2 0.3354(3) 0.3873(6) 0.5804(2) 0.0880(16) Uani d . 1
H H2 0.2913 0.3337 0.5656 0.106 Uiso calc R 1
C C3 0.3645(3) 0.4896(6) 0.5454(2) 0.0926(17) Uani d . 1
H H3 0.3390 0.5077 0.5067 0.111 Uiso calc R 1
C C4 0.4311(3) 0.5664(5) 0.5667(2) 0.0762(14) Uani d . 1
C C5 0.4663(4) 0.6727(6) 0.5317(2) 0.0988(19) Uani d . 1
H H5 0.4424 0.6948 0.4929 0.119 Uiso calc R 1
C C6 0.5326(4) 0.7401(6) 0.5538(3) 0.106(2) Uani d . 1
H H6 0.5542 0.8074 0.5298 0.127 Uiso calc R 1
C C7 0.5713(3) 0.7116(4) 0.6134(2) 0.0776(14) Uani d . 1
C C8 0.6414(4) 0.7740(5) 0.6377(3) 0.098(2) Uani d . 1
H H8 0.6659 0.8408 0.6152 0.117 Uiso calc R 1
C C9 0.6744(3) 0.7386(5) 0.6936(3) 0.0906(17) Uani d . 1
H H9 0.7222 0.7793 0.7098 0.109 Uiso calc R 1
C C10 0.6361(3) 0.6400(4) 0.7274(2) 0.0722(13) Uani d . 1
H H10 0.6593 0.6164 0.7661 0.087 Uiso calc R 1
C C11 0.5368(3) 0.6116(4) 0.6493(2) 0.0600(11) Uani d . 1
C C12 0.4662(3) 0.5378(4) 0.62567(18) 0.0588(11) Uani d . 1
C C13 0.40756(18) 0.1983(3) 0.81456(14) 0.0328(7) Uani d . 1
C C14 0.47901(16) 0.1060(3) 0.82887(12) 0.0264(7) Uani d . 1
C C15 0.51756(16) 0.0460(3) 0.78249(12) 0.0240(6) Uani d . 1
C C16 0.58975(17) -0.0230(3) 0.79802(13) 0.0299(7) Uani d . 1
H H16 0.6169 -0.0613 0.7676 0.036 Uiso calc R 1
C C17 0.62178(18) -0.0353(3) 0.85843(14) 0.0335(7) Uani d . 1
C C18 0.58141(19) 0.0192(4) 0.90393(14) 0.0421(9) Uani d . 1
H H18 0.6021 0.0094 0.9445 0.051 Uiso calc R 1
C C19 0.51007(18) 0.0882(3) 0.88893(13) 0.0383(8) Uani d . 1
H H19 0.4824 0.1235 0.9197 0.046 Uiso calc R 1
C C20 0.6999(2) -0.1096(4) 0.87475(16) 0.0460(9) Uani d . 1
N N1 0.43688(18) 0.4390(3) 0.66158(13) 0.0510(8) Uani d . 1
N N2 0.5682(2) 0.5791(3) 0.70633(15) 0.0563(8) Uani d . 1
O O1 0.40798(12) 0.2849(2) 0.77191(9) 0.0370(5) Uani d . 1
O O2 0.35134(14) 0.1861(3) 0.84667(11) 0.0646(8) Uani d . 1
O O1W 0.33466(18) 0.0544(3) 0.95823(12) 0.0704(8) Uani d D 1
O O3 0.73266(15) -0.1494(3) 0.82746(11) 0.0707(9) Uani d . 1
H H3A 0.7749 -0.1893 0.8384 0.106 Uiso calc R 1
O O4 0.72855(15) -0.1289(3) 0.92612(11) 0.0786(10) Uani d . 1
Zn Zn1 0.5000 0.41820(6) 0.7500 0.0430(2) Uani d S 1
H H1B 0.315(2) 0.112(3) 0.9823(14) 0.064 Uiso d D 1
H H1A 0.333(2) 0.110(3) 0.9282(12) 0.064 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'
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
N1 C1 C2 . . 122.5(4) ?
N1 C1 H1 . . 118.8 ?
C2 C1 H1 . . 118.8 ?
C3 C2 C1 . . 118.2(5) ?
C3 C2 H2 . . 120.9 ?
C1 C2 H2 . . 120.9 ?
C2 C3 C4 . . 120.8(5) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C3 C4 C12 . . 117.5(4) ?
C3 C4 C5 . . 123.8(5) ?
C12 C4 C5 . . 118.7(5) ?
C6 C5 C4 . . 121.3(5) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C7 . . 121.7(5) ?
C5 C6 H6 . . 119.1 ?
C7 C6 H6 . . 119.1 ?
C8 C7 C11 . . 117.4(5) ?
C8 C7 C6 . . 124.2(5) ?
C11 C7 C6 . . 118.3(5) ?
C9 C8 C7 . . 120.2(5) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C8 C9 C10 . . 119.3(5) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
N2 C10 C9 . . 122.6(5) ?
N2 C10 H10 . . 118.7 ?
C9 C10 H10 . . 118.7 ?
N2 C11 C7 . . 122.7(5) ?
N2 C11 C12 . . 117.1(3) ?
C7 C11 C12 . . 120.2(5) ?
N1 C12 C4 . . 122.4(4) ?
N1 C12 C11 . . 117.8(4) ?
C4 C12 C11 . . 119.7(4) ?
O1 C13 O2 . . 123.8(3) ?
O1 C13 C14 . . 118.1(3) ?
O2 C13 C14 . . 118.1(3) ?
C19 C14 C15 . . 119.9(3) ?
C19 C14 C13 . . 119.0(3) ?
C15 C14 C13 . . 121.0(2) ?
C16 C15 C14 . . 118.5(3) ?
C16 C15 C15 . 2_656 118.7(3) ?
C14 C15 C15 . 2_656 122.7(3) ?
C17 C16 C15 . . 120.9(3) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
C18 C17 C16 . . 120.0(3) ?
C18 C17 C20 . . 119.5(3) ?
C16 C17 C20 . . 120.5(3) ?
C17 C18 C19 . . 119.5(3) ?
C17 C18 H18 . . 120.2 ?
C19 C18 H18 . . 120.2 ?
C18 C19 C14 . . 121.1(3) ?
C18 C19 H19 . . 119.5 ?
C14 C19 H19 . . 119.5 ?
O4 C20 O3 . . 124.0(3) ?
O4 C20 C17 . . 123.3(3) ?
O3 C20 C17 . . 112.7(3) ?
C1 N1 C12 . . 118.5(4) ?
C1 N1 Zn1 . . 126.4(3) ?
C12 N1 Zn1 . . 115.1(3) ?
C10 N2 C11 . . 117.7(4) ?
C10 N2 Zn1 . . 128.7(3) ?
C11 N2 Zn1 . . 113.5(3) ?
C13 O1 Zn1 . . 129.41(19) ?
H1B O1W H1A . . 96(4) ?
C20 O3 H3A . . 109.5 ?
O1 Zn1 O1 . 2_656 106.16(11) y
O1 Zn1 N1 . 2_656 98.70(10) y
O1 Zn1 N1 2_656 2_656 87.72(10) ?
O1 Zn1 N1 . . 87.72(10) y
O1 Zn1 N1 2_656 . 98.70(10) ?
N1 Zn1 N1 2_656 . 169.36(16) y
O1 Zn1 N2 . . 162.88(11) y
O1 Zn1 N2 2_656 . 82.94(10) ?
N1 Zn1 N2 2_656 . 96.08(12) ?
N1 Zn1 N2 . . 76.44(13) y
O1 Zn1 N2 . 2_656 82.94(10) y
O1 Zn1 N2 2_656 2_656 162.88(11) ?
N1 Zn1 N2 2_656 2_656 76.44(13) ?
N1 Zn1 N2 . 2_656 96.08(12) y
N2 Zn1 N2 . 2_656 92.23(15) y
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 N1 . 1.323(5) ?
C1 C2 . 1.405(6) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.366(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.378(7) ?
C3 H3 . 0.9300 ?
C4 C12 . 1.399(6) ?
C4 C5 . 1.439(7) ?
C5 C6 . 1.334(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.431(7) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.378(7) ?
C7 C11 . 1.404(5) ?
C8 C9 . 1.341(7) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.399(6) ?
C9 H9 . 0.9300 ?
C10 N2 . 1.321(5) ?
C10 H10 . 0.9300 ?
C11 N2 . 1.348(5) ?
C11 C12 . 1.431(6) ?
C12 N1 . 1.357(4) ?
C13 O1 . 1.251(3) ?
C13 O2 . 1.254(4) ?
C13 C14 . 1.496(4) ?
C14 C19 . 1.383(4) ?
C14 C15 . 1.396(4) ?
C15 C16 . 1.393(4) ?
C15 C15 2_656 1.493(5) ?
C16 C17 . 1.390(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.378(4) ?
C17 C20 . 1.504(4) ?
C18 C19 . 1.379(4) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 O4 . 1.198(4) ?
C20 O3 . 1.294(4) ?
N1 Zn1 . 2.130(3) ?
N2 Zn1 . 2.199(3) ?
O1 Zn1 . 2.102(2) ?
O1W H1B . 0.86(3) ?
O1W H1A . 0.85(3) ?
O3 H3A . 0.8200 ?
Zn1 O1 . 2.102(2) y
Zn1 N1 . 2.130(3) y
Zn1 N2 . 2.199(3) y
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
_geom_hbond_publ_flag
O3 H3A O2 3_545 0.82 1.74 2.538(3) 162 y
O1W H1B O4 5_657 0.86(3) 2.24(2) 2.966(4) 143(3) y
O1W H1A O2 . 0.85(3) 2.00(2) 2.808(4) 159(4) y
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_4
_geom_torsion
N1 C1 C2 C3 . . -0.2(7)
C1 C2 C3 C4 . . 1.7(8)
C2 C3 C4 C12 . . -1.5(7)
C2 C3 C4 C5 . . 178.1(4)
C3 C4 C5 C6 . . -177.5(5)
C12 C4 C5 C6 . . 2.2(8)
C4 C5 C6 C7 . . -0.8(9)
C5 C6 C7 C8 . . 177.4(5)
C5 C6 C7 C11 . . -1.3(8)
C11 C7 C8 C9 . . 0.1(7)
C6 C7 C8 C9 . . -178.6(5)
C7 C8 C9 C10 . . -1.2(7)
C8 C9 C10 N2 . . 0.2(7)
C8 C7 C11 N2 . . 2.2(6)
C6 C7 C11 N2 . . -179.1(4)
C8 C7 C11 C12 . . -176.9(4)
C6 C7 C11 C12 . . 1.9(6)
C3 C4 C12 N1 . . -0.2(6)
C5 C4 C12 N1 . . -179.8(4)
C3 C4 C12 C11 . . 178.2(4)
C5 C4 C12 C11 . . -1.5(6)
N2 C11 C12 N1 . . -1.2(5)
C7 C11 C12 N1 . . 177.9(3)
N2 C11 C12 C4 . . -179.6(3)
C7 C11 C12 C4 . . -0.5(6)
O1 C13 C14 C19 . . 134.7(3)
O2 C13 C14 C19 . . -44.2(4)
O1 C13 C14 C15 . . -40.9(4)
O2 C13 C14 C15 . . 140.3(3)
C19 C14 C15 C16 . . -4.1(4)
C13 C14 C15 C16 . . 171.4(3)
C19 C14 C15 C15 . 2_656 172.4(2)
C13 C14 C15 C15 . 2_656 -12.1(4)
C14 C15 C16 C17 . . 1.7(4)
C15 C15 C16 C17 2_656 . -175.0(2)
C15 C16 C17 C18 . . 1.1(5)
C15 C16 C17 C20 . . -179.8(3)
C16 C17 C18 C19 . . -1.3(5)
C20 C17 C18 C19 . . 179.5(3)
C17 C18 C19 C14 . . -1.1(5)
C15 C14 C19 C18 . . 3.9(5)
C13 C14 C19 C18 . . -171.7(3)
C18 C17 C20 O4 . . 2.6(6)
C16 C17 C20 O4 . . -176.6(4)
C18 C17 C20 O3 . . -177.0(3)
C16 C17 C20 O3 . . 3.8(5)
C2 C1 N1 C12 . . -1.4(6)
C2 C1 N1 Zn1 . . 179.3(3)
C4 C12 N1 C1 . . 1.6(5)
C11 C12 N1 C1 . . -176.8(3)
C4 C12 N1 Zn1 . . -179.0(3)
C11 C12 N1 Zn1 . . 2.6(4)
C9 C10 N2 C11 . . 2.0(6)
C9 C10 N2 Zn1 . . 178.0(3)
C7 C11 N2 C10 . . -3.2(5)
C12 C11 N2 C10 . . 175.9(3)
C7 C11 N2 Zn1 . . -179.8(3)
C12 C11 N2 Zn1 . . -0.8(4)
O2 C13 O1 Zn1 . . 135.8(3)
C14 C13 O1 Zn1 . . -42.9(4)
C13 O1 Zn1 O1 . 2_656 63.6(2)
C13 O1 Zn1 N1 . 2_656 -26.5(3)
C13 O1 Zn1 N1 . . 162.0(3)
C13 O1 Zn1 N2 . . -176.0(3)
C13 O1 Zn1 N2 . 2_656 -101.6(3)
C1 N1 Zn1 O1 . . -9.4(3)
C12 N1 Zn1 O1 . . 171.3(2)
C1 N1 Zn1 O1 . 2_656 96.6(3)
C12 N1 Zn1 O1 . 2_656 -82.7(2)
C1 N1 Zn1 N1 . 2_656 -136.8(3)
C12 N1 Zn1 N1 . 2_656 43.9(2)
C1 N1 Zn1 N2 . . 177.1(3)
C12 N1 Zn1 N2 . . -2.2(2)
C1 N1 Zn1 N2 . 2_656 -92.1(3)
C12 N1 Zn1 N2 . 2_656 88.6(2)
C10 N2 Zn1 O1 . . 162.7(3)
C11 N2 Zn1 O1 . . -21.1(5)
C10 N2 Zn1 O1 . 2_656 -73.9(3)
C11 N2 Zn1 O1 . 2_656 102.3(2)
C10 N2 Zn1 N1 . 2_656 13.1(3)
C11 N2 Zn1 N1 . 2_656 -170.7(2)
C10 N2 Zn1 N1 . . -174.6(3)
C11 N2 Zn1 N1 . . 1.6(2)
C10 N2 Zn1 N2 . 2_656 89.7(3)
C11 N2 Zn1 N2 . 2_656 -94.1(3)
