#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/64/2216481.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_2216481
loop_
_publ_author_name
'Xiao-Guang Zhou'
_publ_section_title
;
 Poly[[[bis(isonicotinamide)copper(II)]-μ-benzene-1,2-dicarboxylato]
 monohydrate]
;
_journal_coeditor_code           HB2621
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3166
_journal_page_last               m3166
_journal_paper_doi               10.1107/S1600536807060217
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C6 H6 N2 O)2 (C8 H4 O4)], H2 O'
_chemical_formula_moiety         'C20 H16 Cu N4 O6, H2 O'
_chemical_formula_sum            'C20 H18 Cu N4 O7'
_chemical_formula_weight         489.92
_chemical_name_systematic
;
Poly[[[bis(isonicotinamide)copper(II)]-μ-benzene-1,2-dicarboxylato]
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                 97.128(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.023(2)
_cell_length_b                   22.903(6)
_cell_length_c                   11.473(3)
_cell_measurement_reflns_used    3211
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.99
_cell_measurement_theta_min      2.52
_cell_volume                     2091.9(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'bruker APEX I CCD'
_diffrn_measurement_method       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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17837
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    1.095
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.344
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0349P)²+0.9750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                3171
_reflns_number_total             4106
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2621.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2091.7(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2216481
_cod_database_fobs_code          2216481
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
Cu Cu1 0.54119(4) 0.233735(13) 0.83422(3) 0.03007(11) Uani d . 1
O O3 0.6678(2) 0.17280(7) 0.76335(15) 0.0312(4) Uani d . 1
O O2 0.0383(2) -0.01116(8) 0.8689(2) 0.0481(5) Uani d . 1
O O5 0.9281(3) 0.22272(9) 0.57311(18) 0.0487(5) Uani d . 1
O O6 0.8999(2) 0.20366(8) 0.38014(16) 0.0364(4) Uani d . 1
O OW1 0.7108(3) 0.21483(9) 1.0445(2) 0.0541(6) Uani d . 1
H HW1A 0.6272 0.2354 1.0693 0.068(11) Uiso d R 1
H HW1B 0.8019 0.2389 1.0644 0.109(17) Uiso d R 1
O O4 0.5213(3) 0.20936(9) 0.60265(17) 0.0460(5) Uani d . 1
O O1 0.9730(2) 0.47765(8) 0.6720(2) 0.0511(6) Uani d . 1
N N4 -0.1684(3) 0.05588(10) 0.8562(2) 0.0434(6) Uani d . 1
H H4A -0.2454 0.0300 0.8588 0.052 Uiso calc R 1
H H4B -0.1948 0.0923 0.8505 0.052 Uiso calc R 1
N N1 0.7024(3) 0.29483(9) 0.79177(19) 0.0314(5) Uani d . 1
N N2 1.1750(3) 0.41113(10) 0.6543(2) 0.0438(6) Uani d . 1
H H2A 1.2418 0.4367 0.6309 0.053 Uiso calc R 1
H H2B 1.2055 0.3752 0.6612 0.053 Uiso calc R 1
N N3 0.3642(3) 0.17358(9) 0.85260(19) 0.0298(5) Uani d . 1
C C13 0.6209(3) 0.17375(11) 0.6516(2) 0.0315(6) Uani d . 1
C C16 0.6908(4) 0.02106(13) 0.5449(3) 0.0529(8) Uani d . 1
H H16A 0.6550 -0.0165 0.5604 0.063 Uiso calc R 1
C C5 0.7409(3) 0.38399(12) 0.6910(3) 0.0391(7) Uani d . 1
H H5A 0.6936 0.4158 0.6487 0.047 Uiso calc R 1
C C4 1.0243(3) 0.42715(12) 0.6799(2) 0.0357(6) Uani d . 1
C C1 0.8677(3) 0.29098(11) 0.8185(2) 0.0342(6) Uani d . 1
H H1A 0.9113 0.2594 0.8634 0.041 Uiso calc R 1
C C3 0.9141(3) 0.37930(11) 0.7179(2) 0.0311(6) Uani d . 1
C C8 0.0795(4) 0.14272(12) 0.8104(3) 0.0423(7) Uani d . 1
H H8A -0.0303 0.1516 0.7796 0.051 Uiso calc R 1
C C14 0.6898(3) 0.12431(11) 0.5849(2) 0.0309(6) Uani d . 1
C C18 0.8577(4) 0.08515(12) 0.4431(3) 0.0429(7) Uani d . 1
H H18A 0.9314 0.0908 0.3876 0.051 Uiso calc R 1
C C9 0.1188(3) 0.08828(11) 0.8575(2) 0.0301(6) Uani d . 1
C C15 0.6331(4) 0.06837(12) 0.6035(3) 0.0430(7) Uani d . 1
H H15A 0.5552 0.0625 0.6560 0.052 Uiso calc R 1
C C10 -0.0085(3) 0.03971(12) 0.8608(2) 0.0348(6) Uani d . 1
C C19 0.8055(3) 0.13276(11) 0.5048(2) 0.0312(6) Uani d . 1
C C2 0.9782(3) 0.33170(11) 0.7827(2) 0.0344(6) Uani d . 1
H H2C 1.0935 0.3271 0.8019 0.041 Uiso calc R 1
C C11 0.2846(3) 0.07746(11) 0.9010(2) 0.0346(6) Uani d . 1
H H11A 0.3159 0.0412 0.9328 0.042 Uiso calc R 1
C C12 0.4028(3) 0.12067(11) 0.8968(2) 0.0338(6) Uani d . 1
H H12A 0.5139 0.1127 0.9259 0.041 Uiso calc R 1
C C20 0.8826(3) 0.19152(11) 0.4871(3) 0.0316(6) Uani d . 1
C C7 0.2050(3) 0.18376(12) 0.8097(3) 0.0424(7) Uani d . 1
H H7A 0.1772 0.2203 0.7778 0.051 Uiso calc R 1
C C6 0.6409(3) 0.34095(12) 0.7279(3) 0.0393(7) Uani d . 1
H H6A 0.5253 0.3438 0.7079 0.047 Uiso calc R 1
C C17 0.8012(4) 0.02959(13) 0.4637(3) 0.0518(8) Uani d . 1
H H17A 0.8376 -0.0020 0.4228 0.062 Uiso calc 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'
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
O6 Cu1 O3 4_566 . 171.25(8)
O6 Cu1 N1 4_566 . 88.08(8)
O3 Cu1 N1 . . 90.75(8)
O6 Cu1 N3 4_566 . 91.93(8)
O3 Cu1 N3 . . 87.98(8)
N1 Cu1 N3 . . 171.72(9)
C13 O3 Cu1 . . 107.33(16)
C20 O6 Cu1 . 4_665 123.79(18)
HW1A OW1 HW1B . . 102.2
C10 N4 H4A . . 120.0
C10 N4 H4B . . 120.0
H4A N4 H4B . . 120.0
C1 N1 C6 . . 117.8(2)
C1 N1 Cu1 . . 123.62(18)
C6 N1 Cu1 . . 118.47(18)
C4 N2 H2A . . 120.0
C4 N2 H2B . . 120.0
H2A N2 H2B . . 120.0
C7 N3 C12 . . 117.8(2)
C7 N3 Cu1 . . 119.97(18)
C12 N3 Cu1 . . 121.91(17)
O4 C13 O3 . . 123.9(2)
O4 C13 C14 . . 121.7(2)
O3 C13 C14 . . 114.3(2)
C17 C16 C15 . . 120.0(3)
C17 C16 H16A . . 120.0
C15 C16 H16A . . 120.0
C6 C5 C3 . . 118.9(3)
C6 C5 H5A . . 120.6
C3 C5 H5A . . 120.6
O1 C4 N2 . . 123.3(3)
O1 C4 C3 . . 120.2(2)
N2 C4 C3 . . 116.4(2)
N1 C1 C2 . . 123.1(2)
N1 C1 H1A . . 118.5
C2 C1 H1A . . 118.5
C2 C3 C5 . . 118.4(2)
C2 C3 C4 . . 122.5(2)
C5 C3 C4 . . 119.1(2)
C7 C8 C9 . . 119.1(3)
C7 C8 H8A . . 120.4
C9 C8 H8A . . 120.4
C15 C14 C19 . . 119.1(2)
C15 C14 C13 . . 117.9(2)
C19 C14 C13 . . 123.0(2)
C17 C18 C19 . . 120.6(3)
C17 C18 H18A . . 119.7
C19 C18 H18A . . 119.7
C8 C9 C11 . . 117.8(2)
C8 C9 C10 . . 123.5(2)
C11 C9 C10 . . 118.7(2)
C16 C15 C14 . . 120.9(3)
C16 C15 H15A . . 119.6
C14 C15 H15A . . 119.6
O2 C10 N4 . . 123.6(3)
O2 C10 C9 . . 120.0(2)
N4 C10 C9 . . 116.4(2)
C18 C19 C14 . . 119.4(2)
C18 C19 C20 . . 118.5(2)
C14 C19 C20 . . 122.0(2)
C3 C2 C1 . . 118.8(2)
C3 C2 H2C . . 120.6
C1 C2 H2C . . 120.6
C12 C11 C9 . . 119.7(2)
C12 C11 H11A . . 120.2
C9 C11 H11A . . 120.2
N3 C12 C11 . . 122.5(2)
N3 C12 H12A . . 118.7
C11 C12 H12A . . 118.7
O5 C20 O6 . . 125.6(3)
O5 C20 C19 . . 119.7(2)
O6 C20 C19 . . 114.7(2)
N3 C7 C8 . . 123.1(3)
N3 C7 H7A . . 118.4
C8 C7 H7A . . 118.4
N1 C6 C5 . . 123.0(3)
N1 C6 H6A . . 118.5
C5 C6 H6A . . 118.5
C16 C17 C18 . . 119.9(3)
C16 C17 H17A . . 120.0
C18 C17 H17A . . 120.0
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 O6 4_566 1.9409(18) y
Cu1 O3 . 1.9610(17) y
Cu1 N1 . 2.006(2) y
Cu1 N3 . 2.008(2) y
O3 C13 . 1.291(3) ?
O2 C10 . 1.224(3) ?
O5 C20 . 1.237(3) ?
O6 C20 . 1.282(3) ?
O6 Cu1 4_665 1.9409(18) ?
OW1 HW1A . 0.8939 ?
OW1 HW1B . 0.9207 ?
O4 C13 . 1.228(3) ?
O1 C4 . 1.227(3) ?
N4 C10 . 1.330(3) ?
N4 H4A . 0.8600 ?
N4 H4B . 0.8600 ?
N1 C1 . 1.326(3) ?
N1 C6 . 1.344(3) ?
N2 C4 . 1.331(3) ?
N2 H2A . 0.8600 ?
N2 H2B . 0.8600 ?
N3 C7 . 1.331(3) ?
N3 C12 . 1.335(3) ?
C13 C14 . 1.509(4) ?
C16 C17 . 1.377(4) ?
C16 C15 . 1.385(4) ?
C16 H16A . 0.9300 ?
C5 C6 . 1.371(4) ?
C5 C3 . 1.390(4) ?
C5 H5A . 0.9300 ?
C4 C3 . 1.506(4) ?
C1 C2 . 1.384(4) ?
C1 H1A . 0.9300 ?
C3 C2 . 1.382(4) ?
C8 C7 . 1.379(4) ?
C8 C9 . 1.379(4) ?
C8 H8A . 0.9300 ?
C14 C15 . 1.385(4) ?
C14 C19 . 1.399(4) ?
C18 C17 . 1.381(4) ?
C18 C19 . 1.392(4) ?
C18 H18A . 0.9300 ?
C9 C11 . 1.384(4) ?
C9 C10 . 1.514(4) ?
C15 H15A . 0.9300 ?
C19 C20 . 1.505(4) ?
C2 H2C . 0.9300 ?
C11 C12 . 1.375(4) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
C7 H7A . 0.9300 ?
C6 H6A . 0.9300 ?
C17 H17A . 0.9300 ?
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
OW1 HW1A O5 4_566 0.89 1.87 2.735(3) 163
OW1 HW1B O4 4_666 0.92 2.12 3.042(3) 176
N4 H4A O1 2_546 0.86 2.18 3.015(3) 165
N4 H4B O3 1_455 0.86 2.31 3.112(3) 155
N2 H2A O2 2_656 0.86 2.13 2.946(3) 159
N2 H2B OW1 4_665 0.86 2.46 3.175(3) 141
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
N1 Cu1 O3 C13 . -81.57(16)
N3 Cu1 O3 C13 . 90.24(16)
O6 Cu1 N1 C1 4_566 136.7(2)
O3 Cu1 N1 C1 . -52.0(2)
O6 Cu1 N1 C6 4_566 -46.6(2)
O3 Cu1 N1 C6 . 124.8(2)
O6 Cu1 N3 C7 4_566 45.0(2)
O3 Cu1 N3 C7 . -126.2(2)
O6 Cu1 N3 C12 4_566 -141.7(2)
O3 Cu1 N3 C12 . 47.1(2)
Cu1 O3 C13 O4 . 3.4(3)
Cu1 O3 C13 C14 . -172.49(16)
C6 N1 C1 C2 . -0.7(4)
Cu1 N1 C1 C2 . 176.0(2)
C6 C5 C3 C2 . -1.1(4)
C6 C5 C3 C4 . -178.6(3)
O1 C4 C3 C2 . -147.1(3)
N2 C4 C3 C2 . 34.1(4)
O1 C4 C3 C5 . 30.4(4)
N2 C4 C3 C5 . -148.4(3)
O4 C13 C14 C15 . -107.9(3)
O3 C13 C14 C15 . 68.1(3)
O4 C13 C14 C19 . 71.2(4)
O3 C13 C14 C19 . -112.8(3)
C7 C8 C9 C11 . -0.6(4)
C7 C8 C9 C10 . -178.9(3)
C17 C16 C15 C14 . -2.5(5)
C19 C14 C15 C16 . 0.7(4)
C13 C14 C15 C16 . 179.8(3)
C8 C9 C10 O2 . 157.5(3)
C11 C9 C10 O2 . -20.8(4)
C8 C9 C10 N4 . -23.4(4)
C11 C9 C10 N4 . 158.3(3)
C17 C18 C19 C14 . -2.4(4)
C17 C18 C19 C20 . 174.6(3)
C15 C14 C19 C18 . 1.7(4)
C13 C14 C19 C18 . -177.3(3)
C15 C14 C19 C20 . -175.2(3)
C13 C14 C19 C20 . 5.8(4)
C5 C3 C2 C1 . -0.3(4)
C4 C3 C2 C1 . 177.2(2)
N1 C1 C2 C3 . 1.2(4)
C8 C9 C11 C12 . 0.5(4)
C10 C9 C11 C12 . 178.8(2)
C7 N3 C12 C11 . -1.0(4)
Cu1 N3 C12 C11 . -174.5(2)
C9 C11 C12 N3 . 0.4(4)
Cu1 O6 C20 O5 4_665 12.9(4)
Cu1 O6 C20 C19 4_665 -164.68(16)
C18 C19 C20 O5 . -135.5(3)
C14 C19 C20 O5 . 41.5(4)
C18 C19 C20 O6 . 42.3(3)
C14 C19 C20 O6 . -140.8(3)
C12 N3 C7 C8 . 0.9(4)
Cu1 N3 C7 C8 . 174.5(2)
C9 C8 C7 N3 . -0.1(5)
C1 N1 C6 C5 . -0.8(4)
Cu1 N1 C6 C5 . -177.7(2)
C3 C5 C6 N1 . 1.7(4)
C15 C16 C17 C18 . 1.8(5)
C19 C18 C17 C16 . 0.7(5)
