##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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.                                        #
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# 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  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Poly[[(N,N-dimethylformamide-κO)(μ₃-pyrazine-2,3-
dicarboxylato-κ⁴N¹,O²:O³:O³)copper(II)]
monohydrate]
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H9 Cu N3 O5, H2 O'
_chemical_formula_sum     'C9 H11 Cu N3 O6'
_chemical_formula_iupac     '[Cu (C6 H2 N2 O4) (C3 H7 N O)], H2 O'
_chemical_formula_weight     320.75
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.1656(5)
_cell_length_b     13.6310(8)
_cell_length_c     9.1461(2)
_cell_angle_alpha     90.00
_cell_angle_beta     91.430(2)
_cell_angle_gamma     90.00
_cell_volume     1266.96(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1111
_cell_measurement_theta_min     2.49
_cell_measurement_theta_max     22.39
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Blue
_exptl_crystal_size_max     0.39
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.682
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     652
_exptl_absorpt_coefficient_mu     1.750
_exptl_absorpt_correction_type     Integration
_exptl_absorpt_process_details     '(SADABS; Bruker, 2002)'
_exptl_absorpt_correction_T_min     0.5485
_exptl_absorpt_correction_T_max     0.9023
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(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 APEX area-detector diffractometer'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6222
_diffrn_reflns_av_R_equivalents     0.0583
_diffrn_reflns_av_sigmaI/netI     0.0747
_diffrn_reflns_theta_min     2.00
_diffrn_reflns_theta_max     25.34
_diffrn_reflns_theta_full     25.34
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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     2283
_reflns_number_gt     1600
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0759
_refine_ls_R_factor_gt     0.0505
_refine_ls_wR_factor_gt     0.1054
_refine_ls_wR_factor_ref     0.1150
_refine_ls_goodness_of_fit_ref     0.982
_refine_ls_restrained_S_all     0.981
_refine_ls_number_reflns     2283
_refine_ls_number_parameters     180
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0482P)²] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.476
_refine_diff_density_min     -0.335
_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     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT (Bruker, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (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 0.59999(5) 0.58784(3) 0.07521(6) 0.0402(2) Uani d . 1 . .
    O O1 0.5775(3) 0.8747(2) 0.1085(4) 0.0526(10) Uani d . 1 . .
    O O2 0.6295(3) 0.7254(2) 0.0382(4) 0.0463(9) Uani d . 1 . .
    O O3 0.4380(3) 0.9489(2) 0.3914(3) 0.0386(8) Uani d . 1 . .
    O O4 0.2821(3) 0.9362(2) 0.2189(4) 0.0511(9) Uani d . 1 . .
    O O5 0.7494(3) 0.5510(2) -0.0435(4) 0.0503(9) Uani d . 1 . .
    O O6 0.2218(5) 0.1287(3) 0.1467(7) 0.121(2) Uani d D 1 . .
    N N1 0.4710(3) 0.6417(2) 0.2162(4) 0.0298(8) Uani d . 1 . .
    N N2 0.3001(3) 0.7442(2) 0.3914(4) 0.0402(9) Uani d . 1 . .
    N N3 0.9066(4) 0.5894(4) -0.2048(5) 0.0655(13) Uani d . 1 . .
    C C1 0.5654(4) 0.7859(3) 0.1145(5) 0.0331(10) Uani d . 1 . .
    C C2 0.4684(4) 0.7404(3) 0.2158(4) 0.0279(9) Uani d . 1 . .
    C C3 0.3821(4) 0.7913(3) 0.3018(5) 0.0316(10) Uani d . 1 . .
    C C4 0.3064(4) 0.6467(3) 0.3912(5) 0.0420(12) Uani d . 1 . .
    H H4 0.2516 0.6118 0.4523 0.050 Uiso calc R 1 . .
    C C5 0.3912(4) 0.5951(3) 0.3039(5) 0.0381(11) Uani d . 1 . .
    H H5 0.3920 0.5269 0.3071 0.046 Uiso calc R 1 . .
    C C6 0.3670(4) 0.9018(3) 0.3005(5) 0.0352(10) Uani d . 1 . .
    C C7 0.8054(5) 0.6097(4) -0.1238(6) 0.0554(14) Uani d . 1 . .
    H H7 0.7732 0.6735 -0.1271 0.066 Uiso calc R 1 . .
    C C8 0.9664(6) 0.6630(5) -0.2983(8) 0.112(3) Uani d . 1 . .
    H H8A 0.9216 0.7244 -0.2874 0.168 Uiso calc R 1 . .
    H H8B 0.9593 0.6421 -0.3985 0.168 Uiso calc R 1 . .
    H H8C 1.0575 0.6707 -0.2706 0.168 Uiso calc R 1 . .
    C C9 0.9607(6) 0.4924(5) -0.2062(7) 0.092(2) Uani d . 1 . .
    H H9A 1.0486 0.4937 -0.1655 0.137 Uiso calc R 1 . .
    H H9B 0.9624 0.4688 -0.3051 0.137 Uiso calc R 1 . .
    H H9C 0.9073 0.4496 -0.1491 0.137 Uiso calc R 1 . .
    H H6A 0.277(5) 0.148(4) 0.089(6) 0.110 Uiso d D 1 . .
    H H6B 0.219(6) 0.0685(9) 0.155(7) 0.110 Uiso d D 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cu1 0.0472(4) 0.0182(3) 0.0560(4) 0.0032(2) 0.0188(3) 0.0026(3)
    O1 0.075(2) 0.0191(15) 0.065(3) -0.0083(15) 0.029(2) -0.0011(16)
    O2 0.0559(19) 0.0221(15) 0.062(2) -0.0013(14) 0.0282(17) 0.0013(16)
    O3 0.0467(17) 0.0189(14) 0.050(2) -0.0034(13) 0.0072(16) -0.0062(15)
    O4 0.060(2) 0.0361(18) 0.057(2) 0.0112(16) -0.0027(19) -0.0003(17)
    O5 0.047(2) 0.0345(17) 0.070(3) 0.0050(15) 0.0268(18) 0.0034(17)
    O6 0.102(4) 0.071(3) 0.192(6) 0.010(3) 0.078(4) 0.054(4)
    N1 0.0353(19) 0.0157(17) 0.039(2) -0.0021(14) 0.0026(17) 0.0003(16)
    N2 0.049(2) 0.029(2) 0.043(2) -0.0043(17) 0.0103(19) -0.0032(18)
    N3 0.041(2) 0.083(3) 0.074(4) 0.010(2) 0.021(2) 0.004(3)
    C1 0.040(2) 0.025(2) 0.034(3) -0.0004(19) 0.008(2) -0.002(2)
    C2 0.036(2) 0.019(2) 0.029(3) -0.0042(17) -0.0021(19) -0.0008(18)
    C3 0.038(2) 0.025(2) 0.032(3) -0.0013(18) -0.001(2) -0.0019(19)
    C4 0.052(3) 0.030(2) 0.045(3) -0.010(2) 0.011(2) 0.002(2)
    C5 0.050(3) 0.021(2) 0.044(3) -0.004(2) 0.007(2) 0.000(2)
    C6 0.039(2) 0.026(2) 0.041(3) 0.004(2) 0.014(2) 0.004(2)
    C7 0.043(3) 0.053(3) 0.070(4) 0.009(2) 0.005(3) -0.007(3)
    C8 0.072(4) 0.144(7) 0.121(7) 0.014(4) 0.049(4) 0.053(5)
    C9 0.062(4) 0.098(5) 0.116(6) 0.011(4) 0.030(4) -0.050(4)
_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 O2 . 1.930(3) ?
    Cu1 O5 . 1.954(3) ?
    Cu1 O3 2_645 1.958(3) ?
    Cu1 N1 . 2.002(3) ?
    Cu1 O3 4_575 2.378(3) ?
    O1 C1 . 1.218(5) ?
    O2 C1 . 1.271(5) ?
    O3 C6 . 1.263(5) ?
    O3 Cu1 2_655 1.958(3) ?
    O3 Cu1 4_576 2.378(3) ?
    O4 C6 . 1.220(5) ?
    O5 C7 . 1.235(6) ?
    O6 H6A . 0.82(5) ?
    O6 H6B . 0.82(5) ?
    N1 C5 . 1.318(5) ?
    N1 C2 . 1.344(4) ?
    N2 C4 . 1.331(5) ?
    N2 C3 . 1.346(5) ?
    N3 C7 . 1.313(6) ?
    N3 C9 . 1.432(6) ?
    N3 C8 . 1.460(7) ?
    C1 C2 . 1.504(5) ?
    C2 C3 . 1.380(5) ?
    C3 C6 . 1.515(5) ?
    C4 C5 . 1.381(6) ?
    C4 H4 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
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
    O2 Cu1 O5 . . 91.48(13) ?
    O2 Cu1 O3 . 2_645 177.39(13) ?
    O5 Cu1 O3 . 2_645 89.82(13) ?
    O2 Cu1 N1 . . 82.17(12) ?
    O5 Cu1 N1 . . 169.37(13) ?
    O3 Cu1 N1 2_645 . 96.87(12) ?
    O2 Cu1 O3 . 4_575 100.87(12) ?
    O5 Cu1 O3 . 4_575 94.99(12) ?
    O3 Cu1 O3 2_645 4_575 76.75(12) ?
    N1 Cu1 O3 . 4_575 94.57(12) ?
    C1 O2 Cu1 . . 116.7(3) ?
    C6 O3 Cu1 . 2_655 118.9(3) ?
    C6 O3 Cu1 . 4_576 137.1(3) ?
    Cu1 O3 Cu1 2_655 4_576 103.25(12) ?
    C7 O5 Cu1 . . 122.7(3) ?
    H6A O6 H6B . . 113.5(19) ?
    C5 N1 C2 . . 118.1(4) ?
    C5 N1 Cu1 . . 129.7(3) ?
    C2 N1 Cu1 . . 112.2(3) ?
    C4 N2 C3 . . 116.4(4) ?
    C7 N3 C9 . . 120.4(5) ?
    C7 N3 C8 . . 121.9(5) ?
    C9 N3 C8 . . 117.6(5) ?
    O1 C1 O2 . . 124.5(4) ?
    O1 C1 C2 . . 120.4(4) ?
    O2 C1 C2 . . 115.1(3) ?
    N1 C2 C3 . . 121.0(4) ?
    N1 C2 C1 . . 113.7(3) ?
    C3 C2 C1 . . 125.4(4) ?
    N2 C3 C2 . . 121.3(4) ?
    N2 C3 C6 . . 114.5(4) ?
    C2 C3 C6 . . 124.2(4) ?
    N2 C4 C5 . . 122.6(4) ?
    N2 C4 H4 . . 118.7 ?
    C5 C4 H4 . . 118.7 ?
    N1 C5 C4 . . 120.6(4) ?
    N1 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    O4 C6 O3 . . 126.2(4) ?
    O4 C6 C3 . . 117.2(4) ?
    O3 C6 C3 . . 116.4(4) ?
    O5 C7 N3 . . 125.4(5) ?
    O5 C7 H7 . . 117.3 ?
    N3 C7 H7 . . 117.3 ?
    N3 C8 H8A . . 109.5 ?
    N3 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    N3 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    N3 C9 H9A . . 109.5 ?
    N3 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    N3 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
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
    O5 Cu1 O2 C1 . . . . -169.1(3) ?
    O3 Cu1 O2 C1 2_645 . . . 71(3) ?
    N1 Cu1 O2 C1 . . . . 2.3(3) ?
    O3 Cu1 O2 C1 4_575 . . . 95.5(3) ?
    O2 Cu1 O5 C7 . . . . -11.7(4) ?
    O3 Cu1 O5 C7 2_645 . . . 166.0(4) ?
    N1 Cu1 O5 C7 . . . . -64.7(9) ?
    O3 Cu1 O5 C7 4_575 . . . 89.4(4) ?
    O2 Cu1 N1 C5 . . . . 179.2(4) ?
    O5 Cu1 N1 C5 . . . . -127.0(7) ?
    O3 Cu1 N1 C5 2_645 . . . 1.7(4) ?
    O3 Cu1 N1 C5 4_575 . . . 78.9(4) ?
    O2 Cu1 N1 C2 . . . . 0.1(3) ?
    O5 Cu1 N1 C2 . . . . 53.8(8) ?
    O3 Cu1 N1 C2 2_645 . . . -177.5(3) ?
    O3 Cu1 N1 C2 4_575 . . . -100.3(3) ?
    Cu1 O2 C1 O1 . . . . 176.6(4) ?
    Cu1 O2 C1 C2 . . . . -4.1(5) ?
    C5 N1 C2 C3 . . . . -1.6(6) ?
    Cu1 N1 C2 C3 . . . . 177.6(3) ?
    C5 N1 C2 C1 . . . . 178.7(4) ?
    Cu1 N1 C2 C1 . . . . -2.1(4) ?
    O1 C1 C2 N1 . . . . -176.6(4) ?
    O2 C1 C2 N1 . . . . 4.1(5) ?
    O1 C1 C2 C3 . . . . 3.7(7) ?
    O2 C1 C2 C3 . . . . -175.6(4) ?
    C4 N2 C3 C2 . . . . -0.4(6) ?
    C4 N2 C3 C6 . . . . 177.3(4) ?
    N1 C2 C3 N2 . . . . 1.5(6) ?
    C1 C2 C3 N2 . . . . -178.8(4) ?
    N1 C2 C3 C6 . . . . -176.0(4) ?
    C1 C2 C3 C6 . . . . 3.7(7) ?
    C3 N2 C4 C5 . . . . -0.5(6) ?
    C2 N1 C5 C4 . . . . 0.8(6) ?
    Cu1 N1 C5 C4 . . . . -178.4(3) ?
    N2 C4 C5 N1 . . . . 0.3(7) ?
    Cu1 O3 C6 O4 2_655 . . . 7.2(6) ?
    Cu1 O3 C6 O4 4_576 . . . 175.4(3) ?
    Cu1 O3 C6 C3 2_655 . . . -167.7(3) ?
    Cu1 O3 C6 C3 4_576 . . . 0.5(6) ?
    N2 C3 C6 O4 . . . . -84.7(5) ?
    C2 C3 C6 O4 . . . . 92.9(5) ?
    N2 C3 C6 O3 . . . . 90.7(4) ?
    C2 C3 C6 O3 . . . . -91.7(5) ?
    Cu1 O5 C7 N3 . . . . 179.4(4) ?
    C9 N3 C7 O5 . . . . 0.6(9) ?
    C8 N3 C7 O5 . . . . 179.3(6) ?
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
    O6 H6B O4 1_545 0.82(5) 2.00(3) 2.771(5) 156(7)
    O6 H6A O1 3_665 0.82(5) 2.38(3) 3.138(6) 153(5)
    O6 H6A O2 3_665 0.82(5) 2.30(3) 3.037(5) 149(5)
data_global
_journal_date_recd_electronic     2009-11-11
_journal_date_accepted     2009-11-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      1
_journal_page_first     m10
_journal_page_last     m11
_journal_paper_category     QM
_journal_coeditor_code     WM2283
_publ_contact_author_name     'Dr Zhen-Zhong Fan'
_publ_contact_author_address
;
Department of Petroleum Engineering
Daqing Petroleum Institute
Heilongjiang 151400
P. R. China
;
_publ_contact_author_email     chem8618@126.com
_publ_section_title
;\
Poly[[(N,N-dimethylformamide-κO)(μ₃-pyrazine-2,3-\
dicarboxylato-κ⁴N¹,O²:O³:O³)copper(II)]
monohydrate]
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhen-Zhong Fan'
;
Department of Petroleum Engineering
Daqing Petroleum Institute
Heilongjiang 151400
People's Republic of China
;
    'Guo-Ping Wang'
;
Department of Chemistry
Zhejiang University
People's Republic of China
;
    'Yu-Sheng Li'
;
Second Oil Recovery Plant
Daqing Oilfields Co
Daqing 163414
People's Republic of China
;
