##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
catena-Poly[[bis(3-carboxy-5-nitrobenzoato-κO¹)copper(II)]-μ-
1,3-di-4-pyridylpropane-κ²N:N']
;
_chemical_name_common     ?
_chemical_formula_moiety     'C29 H22 Cu N4 O12'
_chemical_formula_sum     'C29 H22 Cu N4 O12'
_chemical_formula_iupac     '[Cu (C8 H4 N O6)2 (C13 H14 N2)]'
_chemical_formula_weight     682.05
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
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'
_cell_length_a     25.2976(8)
_cell_length_b     5.3702(2)
_cell_length_c     21.3122(7)
_cell_angle_alpha     90
_cell_angle_beta     115.865(2)
_cell_angle_gamma     90
_cell_volume     2605.29(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10349
_cell_measurement_theta_min     1.8
_cell_measurement_theta_max     25.4
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.739
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1396
_exptl_absorpt_coefficient_mu     0.921
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.821
_exptl_absorpt_correction_T_max     0.905
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10349
_diffrn_reflns_av_R_equivalents     0.032
_diffrn_reflns_av_sigmaI/netI     0.028
_diffrn_reflns_theta_min     1.8
_diffrn_reflns_theta_max     25.4
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -30
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     25
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     '< 1'
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2401
_reflns_number_gt     2087
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.048
_refine_ls_R_factor_gt     0.041
_refine_ls_wR_factor_gt     0.108
_refine_ls_wR_factor_ref     0.112
_refine_ls_goodness_of_fit_ref     1.08
_refine_ls_restrained_S_all     1.08
_refine_ls_number_reflns     2401
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0535P)²+8.8582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.10
_refine_diff_density_min     -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'SAINT (Bruker, 2006)'
_computing_data_reduction     'SAINT (Bruker, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'CrystalMaker (Palmer, 2007)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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_disorder_assembly
    _atom_site_disorder_group
    Cu Cu1 0.0000 0.0000 0.0000 0.01865(18) Uani d S 1 . .
    O O1 0.07835(8) -0.1413(4) 0.04676(10) 0.0209(5) Uani d . 1 . .
    O O2 0.11395(9) 0.1584(4) 0.00388(11) 0.0273(5) Uani d . 1 . .
    O O3 0.31946(10) 0.1103(5) 0.04659(13) 0.0332(6) Uani d D 1 . .
    H H3A 0.3473(12) 0.154(7) 0.0365(19) 0.040 Uiso d D 1 . .
    O O4 0.37815(10) -0.2063(5) 0.10363(13) 0.0374(6) Uani d . 1 . .
    O O5 0.30010(10) -0.7828(4) 0.22279(12) 0.0325(6) Uani d . 1 . .
    O O6 0.20769(10) -0.7829(4) 0.19827(11) 0.0279(5) Uani d . 1 . .
    N N1 0.01902(10) 0.2420(5) 0.07966(12) 0.0207(5) Uani d . 1 . .
    N N2 0.25020(11) -0.6974(5) 0.19249(12) 0.0222(6) Uani d . 1 . .
    C C1 0.17873(12) -0.1639(6) 0.07286(14) 0.0180(6) Uani d . 1 . .
    C C2 0.22615(12) -0.0740(6) 0.06286(14) 0.0178(6) Uani d . 1 . .
    H H2 0.2213 0.0694 0.0348 0.021 Uiso calc R 1 . .
    C C3 0.28055(12) -0.1922(6) 0.09360(14) 0.0189(6) Uani d . 1 . .
    C C4 0.28838(12) -0.3992(6) 0.13549(14) 0.0187(6) Uani d . 1 . .
    H H4 0.3252 -0.4823 0.1562 0.022 Uiso calc R 1 . .
    C C5 0.24125(13) -0.4817(5) 0.14633(14) 0.0187(6) Uani d . 1 . .
    C C6 0.18627(12) -0.3712(6) 0.11546(14) 0.0178(6) Uani d . 1 . .
    H H6 0.1545 -0.4349 0.1231 0.021 Uiso calc R 1 . .
    C C7 0.11985(12) -0.0359(6) 0.03800(14) 0.0190(6) Uani d . 1 . .
    C C8 0.33175(12) -0.0985(6) 0.08267(15) 0.0230(7) Uani d . 1 . .
    C C11 0.06442(14) 0.2091(7) 0.14297(17) 0.0299(7) Uani d . 1 . .
    H H11 0.0897 0.0709 0.1492 0.036 Uiso calc R 1 . .
    C C12 0.07641(14) 0.3641(7) 0.19921(16) 0.0300(8) Uani d . 1 . .
    H H12 0.1088 0.3305 0.2428 0.036 Uiso calc R 1 . .
    C C13 0.04037(13) 0.5719(6) 0.19170(16) 0.0255(7) Uani d . 1 . .
    C C14 -0.00464(13) 0.6150(6) 0.12500(16) 0.0270(7) Uani d . 1 . .
    H H14 -0.0290 0.7579 0.1164 0.032 Uiso calc R 1 . .
    C C15 -0.01359(13) 0.4504(6) 0.07206(16) 0.0265(7) Uani d . 1 . .
    H H15 -0.0445 0.4844 0.0274 0.032 Uiso calc R 1 . .
    C C16 0.05196(14) 0.7391(7) 0.25328(16) 0.0297(7) Uani d . 1 . .
    H H16A 0.0841 0.8549 0.2586 0.036 Uiso calc R 1 . .
    H H16B 0.0662 0.6344 0.2957 0.036 Uiso calc R 1 . .
    C C17 0.0000 0.8934(9) 0.2500 0.0293(10) Uani d S 1 . .
    H H17A -0.0137 1.0023 0.2084 0.035 Uiso calc PR 0.50 . .
    H H17B 0.0137 1.0023 0.2916 0.035 Uiso calc PR 0.50 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 O1 . 1.9427(19) ?
    Cu1 O1 5 1.9427(19) ?
    Cu1 N1 5 2.022(2) ?
    Cu1 N1 . 2.022(2) ?
    O1 C7 . 1.276(3) ?
    O2 C7 . 1.243(4) ?
    O3 C8 . 1.318(4) ?
    O3 H3A . 0.85(4) ?
    O4 C8 . 1.206(4) ?
    O5 N2 . 1.229(3) ?
    O6 N2 . 1.224(3) ?
    N1 C11 . 1.349(4) ?
    N1 C15 . 1.358(4) ?
    N2 C5 . 1.472(4) ?
    C1 C2 . 1.393(4) ?
    C1 C6 . 1.396(4) ?
    C1 C7 . 1.509(4) ?
    C2 C3 . 1.392(4) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.385(4) ?
    C3 C8 . 1.500(4) ?
    C4 C5 . 1.383(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.386(4) ?
    C6 H6 . 0.9500 ?
    C11 C12 . 1.380(5) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.405(5) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.399(4) ?
    C13 C16 . 1.510(5) ?
    C14 C15 . 1.372(5) ?
    C14 H14 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.529(4) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 C16 2 1.530(4) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
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
    O1 Cu1 O1 . 5 180.00(11) ?
    O1 Cu1 N1 . 5 89.75(9) ?
    O1 Cu1 N1 5 5 90.25(9) ?
    O1 Cu1 N1 . . 90.25(9) ?
    O1 Cu1 N1 5 . 89.75(9) ?
    N1 Cu1 N1 5 . 180.0 ?
    C7 O1 Cu1 . . 118.18(18) ?
    C8 O3 H3A . . 112(3) ?
    C11 N1 C15 . . 115.8(3) ?
    C11 N1 Cu1 . . 122.9(2) ?
    C15 N1 Cu1 . . 121.3(2) ?
    O6 N2 O5 . . 123.6(3) ?
    O6 N2 C5 . . 118.5(2) ?
    O5 N2 C5 . . 117.9(2) ?
    C2 C1 C6 . . 119.6(3) ?
    C2 C1 C7 . . 119.9(3) ?
    C6 C1 C7 . . 120.6(2) ?
    C3 C2 C1 . . 120.7(3) ?
    C3 C2 H2 . . 119.7 ?
    C1 C2 H2 . . 119.7 ?
    C4 C3 C2 . . 120.2(3) ?
    C4 C3 C8 . . 118.6(3) ?
    C2 C3 C8 . . 121.2(3) ?
    C5 C4 C3 . . 118.3(3) ?
    C5 C4 H4 . . 120.9 ?
    C3 C4 H4 . . 120.9 ?
    C4 C5 C6 . . 122.9(3) ?
    C4 C5 N2 . . 118.1(3) ?
    C6 C5 N2 . . 118.9(3) ?
    C5 C6 C1 . . 118.3(3) ?
    C5 C6 H6 . . 120.9 ?
    C1 C6 H6 . . 120.9 ?
    O2 C7 O1 . . 124.2(3) ?
    O2 C7 C1 . . 120.7(3) ?
    O1 C7 C1 . . 115.1(3) ?
    O4 C8 O3 . . 124.6(3) ?
    O4 C8 C3 . . 123.3(3) ?
    O3 C8 C3 . . 112.1(2) ?
    N1 C11 C12 . . 124.0(3) ?
    N1 C11 H11 . . 118.0 ?
    C12 C11 H11 . . 118.0 ?
    C11 C12 C13 . . 119.6(3) ?
    C11 C12 H12 . . 120.2 ?
    C13 C12 H12 . . 120.2 ?
    C14 C13 C12 . . 116.5(3) ?
    C14 C13 C16 . . 123.2(3) ?
    C12 C13 C16 . . 120.2(3) ?
    C15 C14 C13 . . 119.9(3) ?
    C15 C14 H14 . . 120.1 ?
    C13 C14 H14 . . 120.1 ?
    N1 C15 C14 . . 124.0(3) ?
    N1 C15 H15 . . 118.0 ?
    C14 C15 H15 . . 118.0 ?
    C13 C16 C17 . . 116.5(2) ?
    C13 C16 H16A . . 108.2 ?
    C17 C16 H16A . . 108.2 ?
    C13 C16 H16B . . 108.2 ?
    C17 C16 H16B . . 108.2 ?
    H16A C16 H16B . . 107.3 ?
    C16 C17 C16 . 2 114.4(4) ?
    C16 C17 H17A . . 108.7 ?
    C16 C17 H17A 2 . 108.7 ?
    C16 C17 H17B . . 108.7 ?
    C16 C17 H17B 2 . 108.7 ?
    H17A C17 H17B . . 107.6 ?
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 Cu1 O1 C7 5 . . . 94.8(2) ?
    N1 Cu1 O1 C7 . . . . -85.2(2) ?
    O1 Cu1 N1 C11 . . . . -17.8(2) ?
    O1 Cu1 N1 C11 5 . . . 162.2(2) ?
    O1 Cu1 N1 C15 . . . . 161.9(2) ?
    O1 Cu1 N1 C15 5 . . . -18.1(2) ?
    C6 C1 C2 C3 . . . . 1.5(4) ?
    C7 C1 C2 C3 . . . . -178.9(3) ?
    C1 C2 C3 C4 . . . . -1.0(4) ?
    C1 C2 C3 C8 . . . . 179.4(3) ?
    C2 C3 C4 C5 . . . . -0.8(4) ?
    C8 C3 C4 C5 . . . . 178.9(3) ?
    C3 C4 C5 C6 . . . . 2.1(4) ?
    C3 C4 C5 N2 . . . . -178.3(2) ?
    O6 N2 C5 C4 . . . . -174.7(3) ?
    O5 N2 C5 C4 . . . . 4.8(4) ?
    O6 N2 C5 C6 . . . . 5.0(4) ?
    O5 N2 C5 C6 . . . . -175.5(3) ?
    C4 C5 C6 C1 . . . . -1.5(4) ?
    N2 C5 C6 C1 . . . . 178.8(2) ?
    C2 C1 C6 C5 . . . . -0.3(4) ?
    C7 C1 C6 C5 . . . . -179.9(2) ?
    Cu1 O1 C7 O2 . . . . 3.4(4) ?
    Cu1 O1 C7 C1 . . . . -176.93(17) ?
    C2 C1 C7 O2 . . . . -4.5(4) ?
    C6 C1 C7 O2 . . . . 175.1(3) ?
    C2 C1 C7 O1 . . . . 175.8(2) ?
    C6 C1 C7 O1 . . . . -4.6(4) ?
    C4 C3 C8 O4 . . . . 6.5(5) ?
    C2 C3 C8 O4 . . . . -173.9(3) ?
    C4 C3 C8 O3 . . . . -174.8(3) ?
    C2 C3 C8 O3 . . . . 4.8(4) ?
    C15 N1 C11 C12 . . . . 4.0(5) ?
    Cu1 N1 C11 C12 . . . . -176.3(2) ?
    N1 C11 C12 C13 . . . . -0.7(5) ?
    C11 C12 C13 C14 . . . . -3.1(5) ?
    C11 C12 C13 C16 . . . . 178.3(3) ?
    C12 C13 C14 C15 . . . . 3.4(5) ?
    C16 C13 C14 C15 . . . . -178.0(3) ?
    C11 N1 C15 C14 . . . . -3.6(4) ?
    Cu1 N1 C15 C14 . . . . 176.7(2) ?
    C13 C14 C15 N1 . . . . -0.1(5) ?
    C14 C13 C16 C17 . . . . 24.3(5) ?
    C12 C13 C16 C17 . . . . -157.2(3) ?
    C13 C16 C17 C16 . . . 2 62.0(2) ?
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 7 0.85(4) 1.86(2) 2.668(3) 158(4) y
data_global
_journal_date_recd_electronic     2009-08-07
_journal_date_accepted     2009-08-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      9
_journal_page_first     m1082
_journal_page_last     m1082
_journal_paper_category     QM
_journal_coeditor_code     TK2526
_publ_contact_author_name     'Robert L. LaDuca'
_publ_contact_author_address
;
Lyman Briggs College
Department of Chemistry
E-30 Holmes Hall
Michigan State University
East Lansing, MI 48825 USA
;
_publ_contact_author_email     laduca@msu.edu
_publ_contact_author_fax     517-432-2758
_publ_contact_author_phone     517-432-2268
_publ_section_title
;\
catena-Poly[[bis(3-carboxy-5-nitrobenzoato-κO¹)copper(II)]-μ-\
1,3-di-4-pyridylpropane-κ²N:N']
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sposato, Laura K.' .
;
Lyman Briggs College
Department of Chemistry
Michigan State University
East Lansing, MI 48825
USA
;
    'LaDuca, Robert L.' .
;
Lyman Briggs College
Department of Chemistry
Michigan State University
East Lansing, MI 48825
USA
;
