#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/67/2206747.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_2206747
loop_
_publ_author_name
'Wu, Jian-Yi'
'Feng, De-Ming'
'He, Hong-Yin'
'Wang, Qing-Xiang'
'Zhu, Long-Guan'
_publ_section_title
;Poly[[[trans-bis(3-aminopyridine)copper(II)]-μ₃-5-hydroxy-1,3-benzenedicarboxylato]
 monohydrate]
;
_journal_coeditor_code           LH6487
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1779
_journal_page_last               m1781
_journal_paper_doi               10.1107/S1600536805025535
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Cu (C8 H4 O5) (C5 H6 N2)2], H2 O'
_chemical_formula_moiety         'C18 H16 Cu N4 O5, H2 O'
_chemical_formula_sum            'C18 H18 Cu N4 O6'
_chemical_formula_weight         449.90
_chemical_name_systematic
;
Poly[[[trans-bis(3-aminopyridine)copper(II)]-μ₃-5-hydroxy-1,3-
benzenedicarboxylato] monohydrate]
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.197(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3222(9)
_cell_length_b                   11.5993(10)
_cell_length_c                   16.0222(14)
_cell_measurement_reflns_used    2213
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.939
_cell_measurement_theta_min      2.171
_cell_volume                     1881.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX 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  0.0699
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9360
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.206
_exptl_absorpt_correction_T_max  0.8033
_exptl_absorpt_correction_T_min  0.7526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.538
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0656P)²5] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                2556
_reflns_number_total             3313
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6487.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206747
_cod_database_fobs_code          2206747
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_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
_atom_site_type_symbol
Cu1 0.90250(4) 0.88478(4) 0.08551(3) 0.02143(18) Uani d . 1 . . Cu
O1 0.7992(2) 0.9026(2) 0.17569(16) 0.0252(6) Uani d . 1 . . O
O2 0.7631(3) 0.7143(2) 0.18098(18) 0.0413(8) Uani d . 1 . . O
O3 0.6426(3) 1.0720(2) 0.42589(17) 0.0330(7) Uani d . 1 . . O
H3 0.6764 1.1186 0.3981 0.049 Uiso calc R 1 . . H
O4 0.5331(3) 0.5673(2) 0.40923(17) 0.0322(7) Uani d . 1 . . O
O5 0.4911(3) 0.6934(2) 0.50539(16) 0.0306(7) Uani d . 1 . . O
N1 1.0558(3) 0.8425(3) 0.1798(2) 0.0257(7) Uani d . 1 . . N
N2 0.7363(3) 0.9075(3) -0.0030(2) 0.0336(9) Uani d . 1 . . N
N3 0.5948(5) 1.0976(5) -0.1753(4) 0.103(2) Uani d . 1 . . N
H3A 0.5209 1.1098 -0.2096 0.080 Uiso calc R 1 . . H
H3B 0.6614 1.1416 -0.1767 0.080 Uiso calc R 1 . . H
N4 1.2195(5) 0.9641(4) 0.3810(3) 0.0809(16) Uani d . 1 . . N
H4A 1.2811 0.9475 0.4237 0.080 Uiso calc R 1 . . H
H4B 1.1814 1.0303 0.3783 0.080 Uiso calc RD 1 . . H
C1 0.7601(4) 0.8133(3) 0.2094(2) 0.0240(9) Uani d . 1 . . C
C2 0.7030(4) 0.8329(3) 0.2877(2) 0.0225(8) Uani d . 1 . . C
C3 0.6497(3) 0.7420(3) 0.3265(2) 0.0240(9) Uani d . 1 . . C
H3E 0.6507 0.6676 0.3049 0.029 Uiso calc R 1 . . H
C4 0.5946(3) 0.7631(3) 0.3981(2) 0.0211(8) Uani d . 1 . . C
C5 0.5929(4) 0.8734(3) 0.4300(2) 0.0235(9) Uani d . 1 . . C
H5 0.5556 0.8872 0.4775 0.028 Uiso calc R 1 . . H
C6 0.6467(4) 0.9640(3) 0.3913(2) 0.0230(9) Uani d . 1 . . C
C7 0.7015(4) 0.9432(3) 0.3201(2) 0.0242(9) Uani d . 1 . . C
H7 0.7372 1.0039 0.2940 0.029 Uiso calc R 1 . . H
C8 0.5354(4) 0.6649(3) 0.4397(2) 0.0215(8) Uani d . 1 . . C
C9 1.1141(4) 0.7392(4) 0.1826(3) 0.0392(11) Uani d . 1 . . C
H9 1.0912 0.6892 0.1367 0.047 Uiso calc R 1 . . H
C10 1.2060(5) 0.7055(5) 0.2512(3) 0.0539(14) Uani d . 1 . . C
H10 1.2455 0.6334 0.2516 0.065 Uiso calc R 1 . . H
C11 1.2408(5) 0.7788(5) 0.3203(3) 0.0528(14) Uani d . 1 . . C
H11 1.3029 0.7559 0.3675 0.063 Uiso calc R 1 . . H
C12 1.1824(5) 0.8861(4) 0.3185(3) 0.0459(13) Uani d . 1 . . C
C13 1.0895(4) 0.9130(4) 0.2457(3) 0.0369(11) Uani d . 1 . . C
H13 1.0487 0.9847 0.2431 0.044 Uiso calc R 1 . . H
C14 0.6302(4) 0.8386(5) -0.0024(3) 0.0481(12) Uani d . 1 . . C
H14 0.6381 0.7799 0.0378 0.058 Uiso calc R 1 . . H
C15 0.5128(5) 0.8509(5) -0.0576(3) 0.0626(15) Uani d . 1 . . C
H15 0.4429 0.8011 -0.0556 0.075 Uiso calc R 1 . . H
C16 0.5000(5) 0.9380(5) -0.1158(3) 0.0580(15) Uani d . 1 . . C
H16 0.4202 0.9495 -0.1533 0.070 Uiso calc R 1 . . H
C17 0.6061(5) 1.0088(5) -0.1187(3) 0.0490(13) Uani d . 1 . . C
C18 0.7235(4) 0.9902(4) -0.0613(3) 0.0404(11) Uani d . 1 . . C
H18 0.7957 1.0372 -0.0638 0.048 Uiso calc R 1 . . H
O1W 1.0218(6) 1.1469(7) 0.3830(4) 0.107(3) Uani d PDU 0.791(8) A 1 O
H1A 0.943(2) 1.166(6) 0.3571(18) 0.080 Uiso d PD 0.791(8) A 1 H
H1B 1.023(5) 1.154(5) 0.4363(8) 0.080 Uiso d PD 0.791(8) A 1 H
O1W' 1.001(3) 1.054(2) 0.4668(17) 0.095(9) Uani d PDU 0.209(8) . 2 O
H1A' 1.01(3) 0.981(3) 0.468(13) 0.080 Uiso d PD 0.209(8) A 2 H
H1B' 1.01(3) 1.079(17) 0.517(6) 0.080 Uiso d PD 0.209(8) A 2 H
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'
Cu Cu 0.3201 1.2651 '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
O5 Cu1 O1 4_675 . 158.15(11) yes
O5 Cu1 N2 4_675 . 92.38(12) yes
O1 Cu1 N2 . . 89.71(12) yes
O5 Cu1 N1 4_675 . 88.88(12) yes
O1 Cu1 N1 . . 86.18(11) yes
N2 Cu1 N1 . . 171.87(14) yes
O5 Cu1 O4 4_675 2_655 107.16(11) yes
O1 Cu1 O4 . 2_655 94.20(10) yes
N2 Cu1 O4 . 2_655 96.29(13) yes
N1 Cu1 O4 . 2_655 91.01(12) yes
C1 O1 Cu1 . . 119.3(2) ?
C6 O3 H3 . . 109.5 ?
C8 O4 Cu1 . 2_645 151.7(3) ?
C8 O5 Cu1 . 4_576 136.0(2) ?
C13 N1 C9 . . 118.6(4) ?
C13 N1 Cu1 . . 119.4(3) ?
C9 N1 Cu1 . . 121.5(3) ?
C18 N2 C14 . . 117.4(4) ?
C18 N2 Cu1 . . 122.9(3) ?
C14 N2 Cu1 . . 119.6(3) ?
C17 N3 H3A . . 120.0 ?
C17 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
C12 N4 H4A . . 120.0 ?
C12 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
O2 C1 O1 . . 124.6(3) ?
O2 C1 C2 . . 119.3(3) ?
O1 C1 C2 . . 116.1(3) ?
C7 C2 C3 . . 120.0(3) ?
C7 C2 C1 . . 119.2(3) ?
C3 C2 C1 . . 120.8(3) ?
C2 C3 C4 . . 119.5(3) ?
C2 C3 H3E . . 120.2 ?
C4 C3 H3E . . 120.2 ?
C5 C4 C3 . . 120.3(3) ?
C5 C4 C8 . . 120.0(3) ?
C3 C4 C8 . . 119.7(3) ?
C4 C5 C6 . . 120.0(3) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
O3 C6 C7 . . 122.6(3) ?
O3 C6 C5 . . 117.6(3) ?
C7 C6 C5 . . 119.8(3) ?
C2 C7 C6 . . 120.3(3) ?
C2 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
O4 C8 O5 . . 125.8(3) ?
O4 C8 C4 . . 119.8(3) ?
O5 C8 C4 . . 114.4(3) ?
N1 C9 C10 . . 121.5(4) ?
N1 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C9 C10 C11 . . 120.0(5) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C12 C11 C10 . . 119.4(4) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
N4 C12 C11 . . 121.9(5) ?
N4 C12 C13 . . 121.5(5) ?
C11 C12 C13 . . 116.5(5) ?
N1 C13 C12 . . 124.1(4) ?
N1 C13 H13 . . 118.0 ?
C12 C13 H13 . . 118.0 ?
N2 C14 C15 . . 123.5(5) ?
N2 C14 H14 . . 118.3 ?
C15 C14 H14 . . 118.3 ?
C14 C15 C16 . . 118.5(5) ?
C14 C15 H15 . . 120.8 ?
C16 C15 H15 . . 120.8 ?
C15 C16 C17 . . 119.5(5) ?
C15 C16 H16 . . 120.2 ?
C17 C16 H16 . . 120.2 ?
N3 C17 C16 . . 120.5(5) ?
N3 C17 C18 . . 120.6(5) ?
C16 C17 C18 . . 118.9(5) ?
N2 C18 C17 . . 122.2(4) ?
N2 C18 H18 . . 118.9 ?
C17 C18 H18 . . 118.9 ?
H1A O1W H1B . . 106.4(14) ?
O1W' O1W' H1B 3_776 . 161(3) ?
H1B O1W' H1A' . . 151(10) ?
O1W' O1W' H1B' 3_776 . 70(10) ?
H1B O1W' H1B' . . 93(10) ?
H1A' O1W' H1B' . . 109.6(19) ?
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
Cu1 O5 4_675 1.940(2) yes
Cu1 O1 . 1.966(2) yes
Cu1 N2 . 2.020(3) yes
Cu1 N1 . 2.025(3) yes
Cu1 O4 2_655 2.216(3) yes
O1 C1 . 1.270(4) ?
O2 C1 . 1.238(4) ?
O3 C6 . 1.373(4) ?
O3 H3 . 0.8200 ?
O4 C8 . 1.232(4) ?
O4 Cu1 2_645 2.216(3) ?
O5 C8 . 1.269(4) ?
O5 Cu1 4_576 1.940(2) ?
N1 C13 . 1.326(5) ?
N1 C9 . 1.338(5) ?
N2 C18 . 1.327(5) ?
N2 C14 . 1.358(5) ?
N3 C17 . 1.362(7) ?
N3 H3A . 0.8600 ?
N3 H3B . 0.8600 ?
N4 C12 . 1.349(6) ?
N4 H4A . 0.8600 ?
N4 H4B . 0.8600 ?
C1 C2 . 1.504(5) ?
C2 C7 . 1.382(5) ?
C2 C3 . 1.390(5) ?
C3 C4 . 1.397(5) ?
C3 H3E . 0.9300 ?
C4 C5 . 1.380(5) ?
C4 C8 . 1.508(5) ?
C5 C6 . 1.390(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.389(5) ?
C7 H7 . 0.9300 ?
C9 C10 . 1.362(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.388(7) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.381(7) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.394(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.362(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.364(7) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.376(7) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.389(6) ?
C18 H18 . 0.9300 ?
O1W H1A . 0.866(8) ?
O1W H1B . 0.857(10) ?
O1W' O1W' 3_776 1.64(5) ?
O1W' H1B . 1.30(6) ?
O1W' H1A' . 0.851(11) ?
O1W' H1B' . 0.850(11) ?
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 O2 2_655 0.82 1.88 2.693(4) 171
N4 H4A O3 3_776 0.86 2.40 3.172(5) 150
N4 H4B O1W . 0.86 2.14 2.947(8) 155
N4 H4B O1W' . 0.86 2.57 3.05(3) 116
O1W H1A O2 2_655 0.866(8) 2.171(9) 3.023(6) 168(3)
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
O5 Cu1 O1 C1 4_675 1.6(5)
N2 Cu1 O1 C1 . 97.3(3)
N1 Cu1 O1 C1 . -75.7(3)
O4 Cu1 O1 C1 2_655 -166.4(3)
O5 Cu1 N1 C13 4_675 148.1(3)
O1 Cu1 N1 C13 . -53.2(3)
O4 Cu1 N1 C13 2_655 40.9(3)
O5 Cu1 N1 C9 4_675 -40.0(3)
O1 Cu1 N1 C9 . 118.7(3)
O4 Cu1 N1 C9 2_655 -147.1(3)
O5 Cu1 N2 C18 4_675 -79.3(3)
O1 Cu1 N2 C18 . 122.4(3)
O4 Cu1 N2 C18 2_655 28.2(3)
O5 Cu1 N2 C14 4_675 102.9(3)
O1 Cu1 N2 C14 . -55.3(3)
O4 Cu1 N2 C14 2_655 -149.5(3)
Cu1 O1 C1 O2 . -12.3(5)
Cu1 O1 C1 C2 . 169.6(2)
O2 C1 C2 C7 . 179.1(4)
O1 C1 C2 C7 . -2.6(5)
O2 C1 C2 C3 . -2.3(6)
O1 C1 C2 C3 . 175.9(3)
C7 C2 C3 C4 . 0.0(6)
C1 C2 C3 C4 . -178.5(3)
C2 C3 C4 C5 . 0.1(6)
C2 C3 C4 C8 . 179.4(3)
C3 C4 C5 C6 . -0.4(6)
C8 C4 C5 C6 . -179.6(3)
C4 C5 C6 O3 . -179.8(3)
C4 C5 C6 C7 . 0.4(6)
C3 C2 C7 C6 . 0.0(6)
C1 C2 C7 C6 . 178.6(3)
O3 C6 C7 C2 . -180.0(4)
C5 C6 C7 C2 . -0.3(6)
Cu1 O4 C8 O5 2_645 -67.8(7)
Cu1 O4 C8 C4 2_645 112.3(5)
Cu1 O5 C8 O4 4_576 -1.4(6)
Cu1 O5 C8 C4 4_576 178.5(2)
C5 C4 C8 O4 . 177.5(3)
C3 C4 C8 O4 . -1.8(5)
C5 C4 C8 O5 . -2.4(5)
C3 C4 C8 O5 . 178.4(3)
C13 N1 C9 C10 . 0.1(6)
Cu1 N1 C9 C10 . -171.9(3)
N1 C9 C10 C11 . 0.3(7)
C9 C10 C11 C12 . -0.7(7)
C10 C11 C12 N4 . -175.0(5)
C10 C11 C12 C13 . 0.6(7)
C9 N1 C13 C12 . -0.2(6)
Cu1 N1 C13 C12 . 172.0(4)
N4 C12 C13 N1 . 175.4(5)
C11 C12 C13 N1 . -0.2(7)
C18 N2 C14 C15 . -0.6(7)
Cu1 N2 C14 C15 . 177.3(4)
N2 C14 C15 C16 . -1.0(9)
C14 C15 C16 C17 . 1.5(9)
C15 C16 C17 N3 . -178.8(6)
C15 C16 C17 C18 . -0.6(8)
C14 N2 C18 C17 . 1.6(7)
Cu1 N2 C18 C17 . -176.2(3)
N3 C17 C18 N2 . 177.2(5)
C16 C17 C18 N2 . -1.0(7)
