#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/69/2236959.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_2236959
loop_
_publ_author_name
'Qiblawi, Sultan H.'
'LaDuca, Robert L.'
_publ_section_title
;
 catena-Poly[[aquabis[N-(pyridin-3-yl)isonicotinamide-κN¹]copper(II)]-μ-fumarato-κ²O¹:O⁴]
;
_journal_coeditor_code           LH5556
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1514
_journal_paper_doi               10.1107/S1600536812047101
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Cu (C4 H2 O4) (C11 H9 N3 O)2 (H2 O)]'
_chemical_formula_moiety         'C26 H22 Cu N6 O7'
_chemical_formula_sum            'C26 H22 Cu N6 O7'
_chemical_formula_weight         594.04
_chemical_name_systematic
;
catena-Poly[[aquabis[N-(pyridin-3-yl)isonicotinamide-
κN¹]copper(II)]-μ-fumarato-κ²O¹:O⁴]
;
_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                 118.686(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   29.854(4)
_cell_length_b                   5.3535(7)
_cell_length_c                   17.353(2)
_cell_measurement_reflns_used    3329
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.68
_cell_volume                     2433.0(5)
_computing_cell_refinement       'SAINT  (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT  (Bruker, 2006)'
_computing_molecular_graphics
;
Crystal Maker (Palmer, 2007)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       ω-φ
_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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9406
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  0.9186
_exptl_absorpt_correction_T_min  0.7940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.363
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2240
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0362
_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)+(0.0303P)²+4.2344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                1758
_reflns_number_total             2240
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            lh5556.cif
_cod_data_source_block           I
_cod_original_cell_volume        2433.0(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236959
_cod_database_fobs_code          2236959
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
_atom_site_symmetry_multiplicity
Cu Cu1 0.0000 0.98462(9) 0.2500 0.01332(15) Uani d S 1 2
O O1 -0.01260(9) 0.5988(4) 0.10232(13) 0.0329(6) Uani d . 1 1
O O2 0.23784(7) 0.6328(4) 0.58520(13) 0.0277(5) Uani d . 1 1
O O3 0.0000 1.3863(5) 0.2500 0.0288(7) Uani d SD 1 2
H H3O -0.0035(12) 1.471(4) 0.2067(12) 0.035 Uiso d D 1 1
O O4 0.01923(7) 0.9749(3) 0.15746(11) 0.0170(4) Uani d . 1 1
N N1 0.34390(10) 0.8621(5) 0.83508(17) 0.0384(7) Uani d . 1 1
N N2 0.24546(9) 1.0496(5) 0.61401(16) 0.0232(6) Uani d D 1 1
H H2N 0.2343(11) 1.199(4) 0.5910(18) 0.028 Uiso d D 1 1
N N3 0.07405(8) 0.9573(4) 0.34350(14) 0.0159(5) Uani d . 1 1
C C1 0.37744(12) 1.0459(6) 0.8530(2) 0.0344(8) Uani d . 1 1
H H1 0.4076 1.0448 0.9083 0.041 Uiso calc R 1 1
C C2 0.37059(12) 1.2372(6) 0.7956(2) 0.0339(8) Uani d . 1 1
H H2 0.3955 1.3652 0.8108 0.041 Uiso calc R 1 1
C C3 0.32648(12) 1.2391(6) 0.7149(2) 0.0295(8) Uani d . 1 1
H H3 0.3203 1.3698 0.6739 0.035 Uiso calc R 1 1
C C4 0.30186(11) 0.8643(6) 0.75726(19) 0.0292(7) Uani d . 1 1
H H4 0.2777 0.7335 0.7438 0.035 Uiso calc R 1 1
C C5 0.29173(10) 1.0479(5) 0.69522(18) 0.0201(6) Uani d . 1 1
C C6 0.16993(10) 0.8946(5) 0.48796(18) 0.0187(6) Uani d . 1 1
C C7 0.09141(10) 1.1150(5) 0.41137(18) 0.0199(6) Uani d . 1 1
H H7 0.0702 1.2498 0.4094 0.024 Uiso calc R 1 1
C C8 0.15215(10) 0.7307(5) 0.41788(18) 0.0195(6) Uani d . 1 1
H H8 0.1725 0.5933 0.4188 0.023 Uiso calc R 1 1
C C9 0.13897(10) 1.0906(5) 0.48445(18) 0.0214(7) Uani d . 1 1
H H9 0.1502 1.2068 0.5315 0.026 Uiso calc R 1 1
C C10 0.10459(10) 0.7686(5) 0.34665(18) 0.0193(6) Uani d . 1 1
H H10 0.0930 0.6575 0.2981 0.023 Uiso calc R 1 1
C C11 0.00282(10) 0.8103(5) 0.09670(18) 0.0180(6) Uani d . 1 1
C C12 0.00079(10) 0.8823(5) 0.01221(17) 0.0169(6) Uani d . 1 1
H H12 0.0006 0.7540 -0.0257 0.020 Uiso calc R 1 1
C C13 0.22077(10) 0.8447(5) 0.56670(18) 0.0205(6) Uani d . 1 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
O4 Cu1 O4 2 . 176.95(12)
O4 Cu1 N3 2 . 88.74(8)
O4 Cu1 N3 . . 91.04(8)
O4 Cu1 N3 2 2 91.04(8)
O4 Cu1 N3 . 2 88.74(8)
N3 Cu1 N3 . 2 171.71(13)
O4 Cu1 O3 2 . 91.52(6)
O4 Cu1 O3 . . 91.52(6)
N3 Cu1 O3 . . 94.15(6)
N3 Cu1 O3 2 . 94.15(6)
H3O O3 Cu1 2 . 122.6(17)
H3O O3 H3O 2 . 115(3)
Cu1 O3 H3O . . 122.6(17)
C11 O4 Cu1 . . 123.39(17)
C1 N1 C4 . . 117.9(3)
C13 N2 C5 . . 125.5(2)
C13 N2 H2N . . 119(2)
C5 N2 H2N . . 115(2)
C7 N3 C10 . . 118.1(2)
C7 N3 Cu1 . . 118.25(18)
C10 N3 Cu1 . . 123.06(18)
N1 C1 C2 . . 123.3(3)
N1 C1 H1 . . 118.4
C2 C1 H1 . . 118.4
C1 C2 C3 . . 118.4(3)
C1 C2 H2 . . 120.8
C3 C2 H2 . . 120.8
C5 C3 C2 . . 118.8(3)
C5 C3 H3 . . 120.6
C2 C3 H3 . . 120.6
N1 C4 C5 . . 123.0(3)
N1 C4 H4 . . 118.5
C5 C4 H4 . . 118.5
C3 C5 C4 . . 118.6(3)
C3 C5 N2 . . 119.8(3)
C4 C5 N2 . . 121.5(3)
C9 C6 C8 . . 118.5(2)
C9 C6 C13 . . 122.6(3)
C8 C6 C13 . . 118.8(2)
N3 C7 C9 . . 122.8(3)
N3 C7 H7 . . 118.6
C9 C7 H7 . . 118.6
C10 C8 C6 . . 119.4(3)
C10 C8 H8 . . 120.3
C6 C8 H8 . . 120.3
C6 C9 C7 . . 118.9(3)
C6 C9 H9 . . 120.5
C7 C9 H9 . . 120.5
N3 C10 C8 . . 122.3(3)
N3 C10 H10 . . 118.9
C8 C10 H10 . . 118.9
O1 C11 O4 . . 125.0(3)
O1 C11 C12 . . 118.1(2)
O4 C11 C12 . . 116.9(2)
C12 C12 C11 5_575 . 122.7(3)
C12 C12 H12 5_575 . 118.6
C11 C12 H12 . . 118.6
O2 C13 N2 . . 123.7(3)
O2 C13 C6 . . 121.1(3)
N2 C13 C6 . . 115.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 O4 2 1.9485(17)
Cu1 O4 . 1.9485(17)
Cu1 N3 . 2.024(2)
Cu1 N3 2 2.024(2)
Cu1 O3 . 2.151(3)
O1 C11 . 1.244(3)
O2 C13 . 1.222(3)
O3 H3O 2 0.839(11)
O3 H3O . 0.839(11)
O4 C11 . 1.278(3)
N1 C1 . 1.330(4)
N1 C4 . 1.331(4)
N2 C13 . 1.356(4)
N2 C5 . 1.423(3)
N2 H2N . 0.883(17)
N3 C7 . 1.335(3)
N3 C10 . 1.344(3)
C1 C2 . 1.374(4)
C1 H1 . 0.9500
C2 C3 . 1.388(4)
C2 H2 . 0.9500
C3 C5 . 1.379(4)
C3 H3 . 0.9500
C4 C5 . 1.380(4)
C4 H4 . 0.9500
C6 C9 . 1.380(4)
C6 C8 . 1.382(4)
C6 C13 . 1.500(4)
C7 C9 . 1.383(4)
C7 H7 . 0.9500
C8 C10 . 1.378(4)
C8 H8 . 0.9500
C9 H9 . 0.9500
C10 H10 . 0.9500
C11 C12 . 1.489(4)
C12 C12 5_575 1.323(5)
C12 H12 . 0.9500
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 H3O O1 1_565 0.839(11) 1.832(10) 2.660(2) 169(3) y
N2 H2N O2 1_565 0.883(17) 2.33(2) 3.153(3) 155(3) y
C2 H2 O4 7_576 0.95 2.48 3.360(4) 153 y
C7 H7 O1 2_565 0.95 2.48 3.430(4) 178 y
C9 H9 N1 4_556 0.95 2.39 3.263(4) 153 y
C12 H12 O1 5_565 0.95 2.43 3.374(4) 171 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
O4 Cu1 O3 H3O 2 2 22(3)
O4 Cu1 O3 H3O . 2 -158(3)
N3 Cu1 O3 H3O . 2 -66(3)
N3 Cu1 O3 H3O 2 2 114(3)
N3 Cu1 O4 C11 . . 121.8(2)
N3 Cu1 O4 C11 2 . -49.9(2)
O3 Cu1 O4 C11 . . -143.99(19)
O4 Cu1 N3 C7 2 . -50.8(2)
O4 Cu1 N3 C7 . . 132.2(2)
O3 Cu1 N3 C7 . . 40.6(2)
O4 Cu1 N3 C10 2 . 120.2(2)
O4 Cu1 N3 C10 . . -56.8(2)
O3 Cu1 N3 C10 . . -148.4(2)
C4 N1 C1 C2 . . 0.4(5)
N1 C1 C2 C3 . . 0.1(5)
C1 C2 C3 C5 . . -0.8(5)
C1 N1 C4 C5 . . -0.1(5)
C2 C3 C5 C4 . . 1.0(5)
C2 C3 C5 N2 . . 178.0(3)
N1 C4 C5 C3 . . -0.6(5)
N1 C4 C5 N2 . . -177.6(3)
C13 N2 C5 C3 . . 146.3(3)
C13 N2 C5 C4 . . -36.8(4)
C10 N3 C7 C9 . . -0.6(4)
Cu1 N3 C7 C9 . . 170.8(2)
C9 C6 C8 C10 . . 0.6(4)
C13 C6 C8 C10 . . 177.4(3)
C8 C6 C9 C7 . . 0.3(4)
C13 C6 C9 C7 . . -176.4(3)
N3 C7 C9 C6 . . -0.3(4)
C7 N3 C10 C8 . . 1.5(4)
Cu1 N3 C10 C8 . . -169.4(2)
C6 C8 C10 N3 . . -1.5(4)
Cu1 O4 C11 O1 . . -24.5(4)
Cu1 O4 C11 C12 . . 153.62(18)
O1 C11 C12 C12 . 5_575 156.4(3)
O4 C11 C12 C12 . 5_575 -21.9(5)
C5 N2 C13 O2 . . -6.2(4)
C5 N2 C13 C6 . . 174.0(2)
C9 C6 C13 O2 . . 150.1(3)
C8 C6 C13 O2 . . -26.5(4)
C9 C6 C13 N2 . . -30.1(4)
C8 C6 C13 N2 . . 153.3(3)
