##############################################################################
###                                                                        ###
###        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
;
Bis(nitrato-κO)(5,7,12,14-tetramethyl-1,4,8,11-
tetraazacyclotetradecane-6,13-diaminium-
κ⁴N¹,N⁴,N⁸,N¹¹)copper(II) dinitrate
tetrahydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H36 Cu N8 O6, 2(N O3), 4(H2 O)'
_chemical_formula_sum     'C14 H44 Cu N10 O16'
_chemical_formula_iupac     '[Cu (N O3)2 (C14 H36 N6)] (N O3)2, 4H2 O'
_chemical_formula_weight     672.14
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     9.201(2)
_cell_length_b     16.576(4)
_cell_length_c     9.278(2)
_cell_angle_alpha     90.00
_cell_angle_beta     98.788(4)
_cell_angle_gamma     90.00
_cell_volume     1398.4(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2543
_cell_measurement_theta_min     2.46
_cell_measurement_theta_max     26.98
_cell_measurement_temperature     123(2)
_exptl_crystal_description     block
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.31
_exptl_crystal_density_diffrn     1.596
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     710
_exptl_absorpt_coefficient_mu     0.870
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.7390
_exptl_absorpt_correction_T_max     0.7742
_diffrn_ambient_temperature     123(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 SMART 1000 CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6071
_diffrn_reflns_av_R_equivalents     0.0270
_diffrn_reflns_av_sigmaI/netI     0.0463
_diffrn_reflns_theta_min     2.46
_diffrn_reflns_theta_max     27.09
_diffrn_reflns_theta_full     27.09
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3021
_reflns_number_gt     2269
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0683
_refine_ls_R_factor_gt     0.0464
_refine_ls_wR_factor_gt     0.1200
_refine_ls_wR_factor_ref     0.1327
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     3021
_refine_ls_number_parameters     202
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0649P)²+2.4391P] 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     0.036
_refine_ls_shift/su_mean     0.005
_refine_diff_density_max     1.244
_refine_diff_density_min     -0.807
_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, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_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
    C C1 0.8753(4) 0.0883(2) 0.2521(3) 0.0169(7) Uani d . 1 . .
    H H1A 0.9413 0.1356 0.2695 0.020 Uiso calc R 1 . .
    H H1B 0.7886 0.1039 0.1807 0.020 Uiso calc R 1 . .
    C C2 0.7676(3) 0.13149(18) 0.4684(3) 0.0136(6) Uani d . 1 . .
    H H2 0.8477 0.1722 0.4930 0.016 Uiso calc R 1 . .
    C C3 0.6400(4) 0.1717(2) 0.3687(3) 0.0234(8) Uani d . 1 . .
    H H3A 0.6749 0.1921 0.2809 0.035 Uiso calc R 1 . .
    H H3B 0.6019 0.2167 0.4205 0.035 Uiso calc R 1 . .
    H H3C 0.5616 0.1322 0.3408 0.035 Uiso calc R 1 . .
    C C4 0.7205(3) 0.10160(19) 0.6114(3) 0.0129(6) Uani d . 1 . .
    H H4 0.6574 0.0527 0.5888 0.016 Uiso calc R 1 . .
    C C5 0.8448(3) 0.08013(19) 0.7366(3) 0.0137(6) Uani d . 1 . .
    H H5 0.7973 0.0642 0.8224 0.016 Uiso calc R 1 . .
    C C6 0.9474(3) 0.15076(19) 0.7843(3) 0.0167(7) Uani d . 1 . .
    H H6A 1.0086 0.1378 0.8774 0.025 Uiso calc R 1 . .
    H H6B 0.8889 0.1991 0.7960 0.025 Uiso calc R 1 . .
    H H6C 1.0105 0.1608 0.7102 0.025 Uiso calc R 1 . .
    C C7 1.0453(3) -0.0192(2) 0.8066(3) 0.0170(7) Uani d . 1 . .
    H H7A 1.0050 -0.0366 0.8947 0.020 Uiso calc R 1 . .
    H H7B 1.1144 0.0259 0.8342 0.020 Uiso calc R 1 . .
    Cu Cu1 1.0000 0.0000 0.5000 0.01124(16) Uani d S 1 . .
    N N1 0.8274(3) 0.06223(16) 0.3922(2) 0.0120(5) Uani d . 1 . .
    H H1C 0.7509 0.0256 0.3683 0.014 Uiso calc R 1 . .
    N N2 0.9236(3) 0.00785(15) 0.6924(3) 0.0128(5) Uani d . 1 . .
    H H2A 0.8545 -0.0334 0.6882 0.015 Uiso calc R 1 . .
    N N3 0.6297(3) 0.16570(17) 0.6691(3) 0.0173(6) Uani d . 1 . .
    H H3D 0.6722 0.2147 0.6611 0.026 Uiso calc R 1 . .
    H H3E 0.6241 0.1555 0.7645 0.026 Uiso calc R 1 . .
    H H3F 0.5376 0.1657 0.6167 0.026 Uiso calc R 1 . .
    N N5 0.7860(3) 0.36290(18) 0.6169(3) 0.0214(6) Uani d . 1 . .
    O O4 0.6922(3) 0.33861(18) 0.6897(3) 0.0377(7) Uani d . 1 . .
    O O5 0.8513(3) 0.31313(17) 0.5511(3) 0.0399(7) Uani d . 1 . .
    O O6 0.8117(3) 0.43623(16) 0.6061(4) 0.0402(7) Uani d . 1 . .
    O O1W 0.1266(3) 0.33514(16) 0.4647(3) 0.0236(5) Uani d D 1 . .
    O O2W 0.4173(4) 0.0272(3) 0.8131(4) 0.0592(10) Uani d D 1 . .
    H H1WA 0.168(5) 0.291(2) 0.489(6) 0.071 Uiso d D 1 . .
    H H1WB 0.039(3) 0.334(3) 0.481(6) 0.071 Uiso d D 1 . .
    H H2WA 0.494(5) -0.008(3) 0.846(6) 0.071 Uiso d D 1 . .
    H H2WB 0.396(6) 0.045(3) 0.901(3) 0.071 Uiso d D 1 . .
    N N4 0.7300(3) -0.14301(18) 0.4733(3) 0.0233(6) Uani d . 1 . .
    O O1 0.8658(2) -0.13506(15) 0.4843(2) 0.0226(5) Uani d . 1 . .
    O O2 0.6711(3) -0.21048(15) 0.4441(3) 0.0252(6) Uani d . 1 . .
    O O3 0.6522(3) -0.08487(18) 0.4963(4) 0.0520(9) Uani d . 1 . .
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
    C1 N1 . 1.499(4) ?
    C1 C7 3_756 1.505(4) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 N1 . 1.496(4) ?
    C2 C3 . 1.532(4) ?
    C2 C4 . 1.539(4) ?
    C2 H2 . 1.0000 ?
    C3 H3A . 0.9800 ?
    C3 H3B . 0.9800 ?
    C3 H3C . 0.9800 ?
    C4 N3 . 1.500(4) ?
    C4 C5 . 1.542(4) ?
    C4 H4 . 1.0000 ?
    C5 N2 . 1.491(4) ?
    C5 C6 . 1.526(4) ?
    C5 H5 . 1.0000 ?
    C6 H6A . 0.9800 ?
    C6 H6B . 0.9800 ?
    C6 H6C . 0.9800 ?
    C7 N2 . 1.488(3) ?
    C7 C1 3_756 1.505(4) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    Cu1 N2 . 2.020(2) ?
    Cu1 N1 . 2.025(2) ?
    Cu1 O1 . 2.550(2) ?
    N1 H1C . 0.9300 ?
    N2 H2A . 0.9300 ?
    N3 H3D . 0.9100 ?
    N3 H3E . 0.9100 ?
    N3 H3F . 0.9100 ?
    N5 O5 . 1.235(4) ?
    N5 O4 . 1.241(4) ?
    N5 O6 . 1.245(4) ?
    O1W H1WA . 0.84(4) ?
    O1W H1WB . 0.84(2) ?
    O2W H2WA . 0.93(5) ?
    O2W H2WB . 0.91(2) ?
    N4 O3 . 1.239(4) ?
    N4 O1 . 1.245(4) ?
    N4 O2 . 1.254(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
    N1 C1 C7 . 3_756 108.5(2) ?
    N1 C1 H1A . . 110.0 ?
    C7 C1 H1A 3_756 . 110.0 ?
    N1 C1 H1B . . 110.0 ?
    C7 C1 H1B 3_756 . 110.0 ?
    H1A C1 H1B . . 108.4 ?
    N1 C2 C3 . . 110.6(2) ?
    N1 C2 C4 . . 109.4(2) ?
    C3 C2 C4 . . 111.7(3) ?
    N1 C2 H2 . . 108.3 ?
    C3 C2 H2 . . 108.3 ?
    C4 C2 H2 . . 108.3 ?
    C2 C3 H3A . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 109.5 ?
    C2 C3 H3C . . 109.5 ?
    H3A C3 H3C . . 109.5 ?
    H3B C3 H3C . . 109.5 ?
    N3 C4 C2 . . 109.0(2) ?
    N3 C4 C5 . . 106.5(2) ?
    C2 C4 C5 . . 116.8(3) ?
    N3 C4 H4 . . 108.1 ?
    C2 C4 H4 . . 108.1 ?
    C5 C4 H4 . . 108.1 ?
    N2 C5 C6 . . 113.0(2) ?
    N2 C5 C4 . . 108.3(2) ?
    C6 C5 C4 . . 113.3(3) ?
    N2 C5 H5 . . 107.3 ?
    C6 C5 H5 . . 107.3 ?
    C4 C5 H5 . . 107.3 ?
    C5 C6 H6A . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C5 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    N2 C7 C1 . 3_756 109.0(2) ?
    N2 C7 H7A . . 109.9 ?
    C1 C7 H7A 3_756 . 109.9 ?
    N2 C7 H7B . . 109.9 ?
    C1 C7 H7B 3_756 . 109.9 ?
    H7A C7 H7B . . 108.3 ?
    N2 Cu1 N1 3_756 . 87.06(10) ?
    N2 Cu1 N1 . . 92.94(10) ?
    O1 Cu1 N1 . . 94.74(9) ?
    O1 Cu1 N2 . . 82.89(8) ?
    O1 Cu1 N1 . 3_756 85.26(9) ?
    O1 Cu1 N2 . 3_756 97.11(8) ?
    C2 N1 C1 . . 111.5(2) ?
    C2 N1 Cu1 . . 118.36(17) ?
    C1 N1 Cu1 . . 105.27(18) ?
    C2 N1 H1C . . 107.1 ?
    C1 N1 H1C . . 107.1 ?
    Cu1 N1 H1C . . 107.1 ?
    C7 N2 C5 . . 113.0(2) ?
    C7 N2 Cu1 . . 106.55(18) ?
    C5 N2 Cu1 . . 123.02(18) ?
    C7 N2 H2A . . 104.1 ?
    C5 N2 H2A . . 104.1 ?
    Cu1 N2 H2A . . 104.1 ?
    C4 N3 H3D . . 109.5 ?
    C4 N3 H3E . . 109.5 ?
    H3D N3 H3E . . 109.5 ?
    C4 N3 H3F . . 109.5 ?
    H3D N3 H3F . . 109.5 ?
    H3E N3 H3F . . 109.5 ?
    O5 N5 O4 . . 118.9(3) ?
    O5 N5 O6 . . 120.0(3) ?
    O4 N5 O6 . . 121.1(3) ?
    H1WA O1W H1WB . . 109(4) ?
    H2WA O2W H2WB . . 99(4) ?
    O3 N4 O1 . . 120.2(3) ?
    O3 N4 O2 . . 119.3(3) ?
    O1 N4 O2 . . 120.5(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_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 C2 C4 N3 . . . . -167.0(2) ?
    C3 C2 C4 N3 . . . . -44.1(3) ?
    N1 C2 C4 C5 . . . . 72.4(3) ?
    C3 C2 C4 C5 . . . . -164.7(3) ?
    N3 C4 C5 N2 . . . . 171.2(2) ?
    C2 C4 C5 N2 . . . . -66.9(3) ?
    N3 C4 C5 C6 . . . . -62.6(3) ?
    C2 C4 C5 C6 . . . . 59.3(3) ?
    C3 C2 N1 C1 . . . . 56.7(3) ?
    C4 C2 N1 C1 . . . . -179.9(2) ?
    C3 C2 N1 Cu1 . . . . 178.9(2) ?
    C4 C2 N1 Cu1 . . . . -57.6(3) ?
    C7 C1 N1 C2 3_756 . . . 171.5(2) ?
    C7 C1 N1 Cu1 3_756 . . . 42.0(3) ?
    N2 Cu1 N1 C2 3_756 . . . -142.1(2) ?
    N2 Cu1 N1 C2 . . . . 37.9(2) ?
    N2 Cu1 N1 C1 3_756 . . . -16.78(19) ?
    N2 Cu1 N1 C1 . . . . 163.22(19) ?
    C1 C7 N2 C5 3_756 . . . -175.9(3) ?
    C1 C7 N2 Cu1 3_756 . . . -37.9(3) ?
    C6 C5 N2 C7 . . . . 54.5(3) ?
    C4 C5 N2 C7 . . . . -179.2(2) ?
    C6 C5 N2 Cu1 . . . . -75.7(3) ?
    C4 C5 N2 Cu1 . . . . 50.7(3) ?
    N1 Cu1 N2 C7 3_756 . . . 11.4(2) ?
    N1 Cu1 N2 C7 . . . . -168.6(2) ?
    N1 Cu1 N2 C5 3_756 . . . 144.2(2) ?
    N1 Cu1 N2 C5 . . . . -35.8(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
    N1 H1C O3 . 0.93 2.43 3.155(4) 134.4
    N1 H1C O2W 3_656 0.93 2.28 3.096(4) 146.1
    N2 H2A O3 . 0.93 2.52 3.244(4) 134.8
    N2 H2A O4 2_646 0.93 2.47 3.249(4) 140.9
    N3 H3D O4 . 0.91 2.08 2.924(4) 154.7
    N3 H3E O1W 4_666 0.91 1.86 2.748(4) 164.1
    N3 H3F O2 3_656 0.91 2.06 2.902(4) 154.3
    N3 H3F O3 3_656 0.91 2.32 3.108(4) 144.7
    O1W H1WA O2 3_656 0.84(4) 2.01(3) 2.823(4) 160(5)
    O1W H1WB O5 1_455 0.84(2) 1.97(2) 2.795(4) 168(5)
    O2W H2WA O6 2_646 0.93(5) 2.00(5) 2.913(5) 166(5)
    O2W H2WB O6 4_566 0.92(2) 2.18(2) 3.084(5) 167(5)
data_global
_journal_date_recd_electronic     2010-05-27
_journal_date_accepted     2010-06-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     m837
_journal_page_last     m837
_journal_paper_category     QM
_journal_coeditor_code     HY2316
_publ_contact_author_name     'Xiang-Yun Liu'
_publ_contact_author_address
;
Department of Chemistry and Chemical Engineering
Henan University of Urban Construction
Pingdingshan 467044
People's Republic of China
;
_publ_contact_author_email     tianlin1288@163.com
_publ_contact_author_fax     '86 0375 2089043'
_publ_contact_author_phone     '86 0375 2089041'
_publ_section_title
;\
Bis(nitrato-κO)(5,7,12,14-tetramethyl-1,4,8,11-\
tetraazacyclotetradecane-6,13-diaminium-κ⁴N¹,N⁴,\
N⁸,N¹¹)copper(II) dinitrate tetrahydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Xiang-Yun Liu' .
;
Department of Chemistry and Chemical Engineering
Henan University of Urban Construction
Pingdingshan 467044
People's Republic of China
;
    'Hong-Ying Chu' .
;
Department of Environment and Chemical Engineering
Yellow River Conservancy Technical Institute
Kaifeng 475004
People's Republic of China
;
