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###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Di-μ-azido-bis({N'-[1-(2-pyridyl-
κN)ethylidene]acetohydrazidato-κ²N',O}dicopper(II))
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H20 Cu2 N12 O2'
_chemical_formula_sum     'C18 H20 Cu2 N12 O2'
_chemical_formula_iupac     '[Cu2 (C9 H10 N3 O)2 (N3)2]'
_chemical_formula_weight     563.54
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.589(3)
_cell_length_b     8.955(3)
_cell_length_c     9.693(4)
_cell_angle_alpha     66.534(15)
_cell_angle_beta     69.461(13)
_cell_angle_gamma     81.468(16)
_cell_volume     565.8(4)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     3185
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     28.5
_cell_measurement_temperature     150(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     brown
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.654
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     286
_exptl_absorpt_coefficient_mu     1.923
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.6450
_exptl_absorpt_correction_T_max     0.6997
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEXII'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3858
_diffrn_reflns_av_R_equivalents     0.0397
_diffrn_reflns_av_sigmaI/netI     0.2939
_diffrn_reflns_theta_min     3.10
_diffrn_reflns_theta_max     26.99
_diffrn_reflns_theta_full     26.99
_diffrn_measured_fraction_theta_max     0.956
_diffrn_measured_fraction_theta_full     0.956
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_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     2358
_reflns_number_gt     1591
_reflns_threshold_expression     I>2σ
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.2586
_refine_ls_R_factor_gt     0.0265
_refine_ls_wR_factor_gt     0.0728
_refine_ls_wR_factor_ref     0.0934
_refine_ls_goodness_of_fit_ref     1.078
_refine_ls_restrained_S_all     1.078
_refine_ls_number_reflns     2358
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0597P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     2.082
_refine_diff_density_min     -2.810
_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, 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     'DIAMOND (Brandenburg, 2006)'
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 0.34274(3) 0.93665(3) 0.95880(3) 0.02989(14) Uani d . 1 . .
    N N5 0.2011(2) 0.7390(2) 1.0402(2) 0.0307(5) Uani d . 1 . .
    O O1 0.4938(2) 0.8357(2) 0.8052(2) 0.0380(5) Uani d . 1 . .
    N N1 0.4648(3) 1.1498(2) 0.8642(2) 0.0329(5) Uani d . 1 . .
    N N6 0.2719(3) 0.6294(3) 0.9663(2) 0.0367(6) Uani d . 1 . .
    C C8 0.4270(3) 0.6937(3) 0.8443(3) 0.0314(6) Uani d . 1 . .
    N N2 0.5605(3) 1.2073(2) 0.7250(2) 0.0358(6) Uani d . 1 . .
    N N4 0.1206(2) 0.9791(2) 1.1350(2) 0.0315(5) Uani d . 1 . .
    C C1 -0.0012(3) 0.8504(3) 1.2187(3) 0.0341(6) Uani d . 1 . .
    C C2 -0.1553(3) 0.8504(4) 1.3488(3) 0.0438(8) Uani d . 1 . .
    H H2 -0.2404 0.7619 1.4036 0.053 Uiso calc R 1 . .
    C C9 0.5264(3) 0.5944(3) 0.7465(3) 0.0436(7) Uani d . 1 . .
    H H9A 0.4938 0.6357 0.6483 0.065 Uiso calc R 1 . .
    H H9B 0.4881 0.4806 0.8067 0.065 Uiso calc R 1 . .
    H H9C 0.6627 0.6019 0.7202 0.065 Uiso calc R 1 . .
    C C5 0.0911(3) 1.1048(3) 1.1831(3) 0.0390(7) Uani d . 1 . .
    H H5 0.1758 1.1935 1.1254 0.047 Uiso calc R 1 . .
    C C6 0.0467(3) 0.7153(3) 1.1593(3) 0.0351(7) Uani d . 1 . .
    C C3 -0.1850(3) 0.9815(4) 1.3992(3) 0.0470(9) Uani d . 1 . .
    H H3 -0.2888 0.9825 1.4891 0.056 Uiso calc R 1 . .
    C C4 -0.0596(4) 1.1095(4) 1.3148(3) 0.0449(7) Uani d . 1 . .
    H H4 -0.0761 1.1997 1.3465 0.054 Uiso calc R 1 . .
    N N3 0.6520(4) 1.2683(4) 0.5959(3) 0.0644(10) Uani d . 1 . .
    C C7 -0.0748(4) 0.5681(4) 1.2321(4) 0.0564(10) Uani d . 1 . .
    H H7A -0.0411 0.5099 1.1594 0.085 Uiso calc R 1 . .
    H H7B -0.2073 0.6022 1.2516 0.085 Uiso calc R 1 . .
    H H7C -0.0556 0.4962 1.3328 0.085 Uiso calc R 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 0.03078(16) 0.0297(2) 0.02843(18) -0.00779(10) -0.00486(12) -0.01154(14)
    N5 0.0319(7) 0.0317(10) 0.0289(9) -0.0042(7) -0.0062(7) -0.0133(8)
    O1 0.0400(8) 0.0382(10) 0.0350(9) -0.0100(6) -0.0044(7) -0.0163(8)
    N1 0.0386(8) 0.0306(10) 0.0287(9) -0.0063(7) -0.0068(8) -0.0117(9)
    N6 0.0383(9) 0.0368(11) 0.0351(10) -0.0048(8) -0.0079(9) -0.0154(9)
    C8 0.0389(9) 0.0296(11) 0.0318(10) -0.0017(8) -0.0140(9) -0.0148(9)
    N2 0.0404(9) 0.0327(10) 0.0316(10) -0.0034(7) -0.0105(8) -0.0091(9)
    N4 0.0303(7) 0.0331(10) 0.0310(9) -0.0027(6) -0.0079(7) -0.0126(8)
    C1 0.0286(8) 0.0403(12) 0.0295(11) -0.0040(7) -0.0073(8) -0.0098(10)
    C2 0.0346(10) 0.0535(16) 0.0353(12) -0.0070(9) -0.0012(9) -0.0150(13)
    C9 0.0495(12) 0.0421(15) 0.0402(13) -0.0022(10) -0.0097(11) -0.0200(12)
    C5 0.0395(10) 0.0399(14) 0.0386(12) -0.0032(9) -0.0109(10) -0.0162(12)
    C6 0.0323(9) 0.0352(12) 0.0343(11) -0.0074(8) -0.0070(9) -0.0102(10)
    C3 0.0388(10) 0.0623(19) 0.0358(13) 0.0030(10) -0.0028(10) -0.0234(14)
    C4 0.0484(12) 0.0489(16) 0.0437(14) 0.0071(10) -0.0130(11) -0.0277(12)
    N3 0.0746(16) 0.0654(19) 0.0323(12) -0.0125(13) -0.0042(12) -0.0045(14)
    C7 0.0493(13) 0.0495(18) 0.0599(19) -0.0198(12) 0.0053(13) -0.0229(16)
_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 N5 . 1.941(2) ?
    Cu1 N1 . 1.969(2) ?
    Cu1 O1 . 1.979(2) ?
    Cu1 N4 . 2.051(2) ?
    Cu1 N1 2_677 2.4574(18) ?
    N5 C6 . 1.297(3) ?
    N5 N6 . 1.377(4) ?
    O1 C8 . 1.300(3) ?
    N1 N2 . 1.218(3) ?
    N1 Cu1 2_677 2.4574(18) ?
    N6 C8 . 1.341(3) ?
    C8 C9 . 1.493(5) ?
    N2 N3 . 1.142(3) ?
    N4 C5 . 1.343(4) ?
    N4 C1 . 1.374(3) ?
    C1 C2 . 1.387(4) ?
    C1 C6 . 1.484(4) ?
    C2 C3 . 1.403(5) ?
    C2 H2 . 0.9500 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C5 C4 . 1.394(4) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.500(3) ?
    C3 C4 . 1.386(4) ?
    C3 H3 . 0.9500 ?
    C4 H4 . 0.9500 ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
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
    N5 Cu1 N1 . . 173.44(6) ?
    N5 Cu1 O1 . . 79.78(9) ?
    N1 Cu1 O1 . . 101.14(9) ?
    N5 Cu1 N4 . . 80.27(9) ?
    N1 Cu1 N4 . . 98.12(10) ?
    O1 Cu1 N4 . . 159.42(8) ?
    N5 Cu1 N1 . 2_677 99.67(7) ?
    N1 Cu1 N1 . 2_677 86.64(6) ?
    O1 Cu1 N1 . 2_677 98.75(8) ?
    N4 Cu1 N1 . 2_677 89.51(8) ?
    C6 N5 N6 . . 123.0(2) ?
    C6 N5 Cu1 . . 119.7(2) ?
    N6 N5 Cu1 . . 117.28(14) ?
    C8 O1 Cu1 . . 110.27(16) ?
    N2 N1 Cu1 . . 122.4(2) ?
    N2 N1 Cu1 . 2_677 111.79(13) ?
    Cu1 N1 Cu1 . 2_677 93.36(6) ?
    C8 N6 N5 . . 107.9(2) ?
    O1 C8 N6 . . 124.6(3) ?
    O1 C8 C9 . . 118.6(2) ?
    N6 C8 C9 . . 116.8(2) ?
    N3 N2 N1 . . 176.3(3) ?
    C5 N4 C1 . . 119.0(2) ?
    C5 N4 Cu1 . . 128.98(15) ?
    C1 N4 Cu1 . . 111.8(2) ?
    N4 C1 C2 . . 121.1(3) ?
    N4 C1 C6 . . 114.9(2) ?
    C2 C1 C6 . . 124.0(2) ?
    C1 C2 C3 . . 119.8(2) ?
    C1 C2 H2 . . 120.1 ?
    C3 C2 H2 . . 120.1 ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    N4 C5 C4 . . 122.3(2) ?
    N4 C5 H5 . . 118.9 ?
    C4 C5 H5 . . 118.9 ?
    N5 C6 C1 . . 113.21(19) ?
    N5 C6 C7 . . 124.6(3) ?
    C1 C6 C7 . . 122.2(3) ?
    C4 C3 C2 . . 118.5(3) ?
    C4 C3 H3 . . 120.7 ?
    C2 C3 H3 . . 120.7 ?
    C3 C4 C5 . . 119.4(3) ?
    C3 C4 H4 . . 120.3 ?
    C5 C4 H4 . . 120.3 ?
    C6 C7 H7A . . 109.5 ?
    C6 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C6 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
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
    C9 H9A N3 2_676 0.98 2.74 3.710(4) 171
data_global
_journal_date_recd_electronic     2010-08-24
_journal_date_accepted     2010-08-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     10
_journal_page_first     m1271
_journal_page_last     m1271
_journal_paper_category     QM
_journal_coeditor_code     PV2324
_publ_contact_author_name     'Hon Man Lee'
_publ_contact_author_address
;
National Changhua University of Education
Department of Chemistry
Changhua 50058
Taiwan
;
_publ_contact_author_email     'leehm@cc.ncue.edu.tw'
_publ_contact_author_fax     '886-4-7211190'
_publ_contact_author_phone     '886-47232105x3523'
_publ_section_title
;\
Seed
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Datta, Amitabha' .
;
National Changhua University of Education
Department of Chemistry
Changhua
Taiwan 50058
;
    'Das, Kuheli' .
;
National Changhua University of Education
Department of Chemistry
Changhua
Taiwan 50058
;
    'Jhou, Yan-Ming' .
;
National Changhua University of Education
Department of Chemistry
Changhua
Taiwan 50058
;
    'Huang, Jui-Hsien' .
;
National Changhua University of Education
Department of Chemistry
Changhua
Taiwan 50058
;
    'Lee, Hon Man' .
;
National Changhua University of Education
Department of Chemistry
Changhua
Taiwan 50058
;
