##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2005-08-18
_journal_date_accepted     2005-08-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      9
_journal_page_first     m1883
_journal_page_last     m1884
_journal_paper_category     EM
_journal_coeditor_code     CI6639
_publ_contact_author_name     'Zhang, Qi'
_publ_contact_author_address
;
      Hainan Province Key Laboratory of Fine Chemicals
      Hainan University
      Hainan 570228
      People's Republic of China
;
_publ_contact_author_email     zhangqi_hainu@163.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
Dichloro[N,N-dimethyl-N'-(2-pyridylmethylidene)ethane-1,2-\
diamine]copper(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Yuan, Wen-Bing'
;     Hainan Province Key Lab of Fine Chemicals
      Hainan University
      Hainan 570228
      People's Republic of China
;
    'Zhang, Qi'
;     Hainan Province Key Lab of Fine Chemicals
      Hainan University
      Hainan 570228
      People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Dichloro[N,N'-dimethyl-N'-(2-pyridylmethylidene)ethane-1,2-diamine]copper(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H15 Cl2 Cu N3'
_chemical_formula_sum     'C10 H15 Cl2 Cu N3'
_chemical_formula_iupac     '[Cu Cl2 (C10 H15 N3)]'
_chemical_formula_weight     311.69
_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     7.3030(10)
_cell_length_b     8.0090(10)
_cell_length_c     11.9950(10)
_cell_angle_alpha     100.1810(10)
_cell_angle_beta     101.9460(10)
_cell_angle_gamma     100.8550(10)
_cell_volume     656.90(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4455
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     28.23
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.576
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     318
_exptl_absorpt_coefficient_mu     2.046
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.6617
_exptl_absorpt_correction_T_max     0.8534
_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 SMART CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7629
_diffrn_reflns_av_R_equivalents     0.0174
_diffrn_reflns_av_sigmaI/netI     0.0213
_diffrn_reflns_theta_min     1.78
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.982
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_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 > 2sigma(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     2972
_reflns_number_gt     2774
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0276
_refine_ls_R_factor_gt     0.0253
_refine_ls_wR_factor_gt     0.0586
_refine_ls_wR_factor_ref     0.0600
_refine_ls_goodness_of_fit_ref     1.086
_refine_ls_restrained_S_all     1.086
_refine_ls_number_reflns     2972
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0265P)²+0.0926P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.235
_refine_diff_density_min     -0.261
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997a)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    Cu1 0.23315(3) 0.89089(3) 0.762315(17) 0.03785(8) Uani d . 1 . . Cu
    Cl1 0.13875(7) 1.10006(6) 0.87363(4) 0.05413(13) Uani d . 1 . . Cl
    Cl2 0.00445(7) 0.73796(8) 0.60076(4) 0.06132(14) Uani d . 1 . . Cl
    N1 0.4034(2) 1.0713(2) 0.67846(13) 0.0467(4) Uani d . 1 . . N
    N2 0.4990(2) 0.8207(2) 0.77508(13) 0.0461(4) Uani d . 1 . . N
    N3 0.2167(2) 0.6904(2) 0.87483(14) 0.0458(3) Uani d . 1 . . N
    C1 0.3496(3) 1.1946(3) 0.62771(18) 0.0555(5) Uani d . 1 . . C
    H1 0.2267 1.2124 0.6253 0.067 Uiso calc R 1 . . H
    C2 0.4694(3) 1.2978(3) 0.57819(19) 0.0634(6) Uani d . 1 . . C
    H2 0.4275 1.3836 0.5435 0.076 Uiso calc R 1 . . H
    C3 0.6506(3) 1.2720(3) 0.58092(19) 0.0674(6) Uani d . 1 . . C
    H3 0.7338 1.3408 0.5489 0.081 Uiso calc R 1 . . H
    C4 0.7073(3) 1.1427(3) 0.63170(19) 0.0615(6) Uani d . 1 . . C
    H4 0.8286 1.1215 0.6336 0.074 Uiso calc R 1 . . H
    C5 0.5809(3) 1.0453(3) 0.67974(16) 0.0486(4) Uani d . 1 . . C
    C6 0.6246(3) 0.9021(3) 0.73319(17) 0.0527(5) Uani d . 1 . . C
    H6 0.7420 0.8716 0.7363 0.063 Uiso calc R 1 . . H
    C7 0.5269(3) 0.6750(3) 0.8296(2) 0.0556(5) Uani d . 1 . . C
    H7A 0.6055 0.7180 0.9091 0.067 Uiso calc R 1 . . H
    H7B 0.5910 0.6010 0.7859 0.067 Uiso calc R 1 . . H
    C8 0.3298(3) 0.5731(3) 0.8291(2) 0.0566(5) Uani d . 1 . . C
    H8A 0.2623 0.5105 0.7500 0.068 Uiso calc R 1 . . H
    H8B 0.3437 0.4882 0.8769 0.068 Uiso calc R 1 . . H
    C9 0.0171(3) 0.5910(3) 0.8577(2) 0.0675(6) Uani d . 1 . . C
    H9A -0.0412 0.5479 0.7756 0.101 Uiso calc R 1 . . H
    H9B -0.0552 0.6658 0.8912 0.101 Uiso calc R 1 . . H
    H9C 0.0180 0.4946 0.8952 0.101 Uiso calc R 1 . . H
    C10 0.2983(3) 0.7676(3) 1.00050(18) 0.0614(5) Uani d . 1 . . C
    H10A 0.3020 0.6763 1.0425 0.092 Uiso calc R 1 . . H
    H10B 0.2197 0.8407 1.0284 0.092 Uiso calc R 1 . . H
    H10C 0.4265 0.8362 1.0125 0.092 Uiso calc R 1 . . H
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 0.03039(11) 0.04033(12) 0.04270(13) 0.00863(8) 0.01185(8) 0.00536(9)
    Cl1 0.0536(3) 0.0512(3) 0.0607(3) 0.0179(2) 0.0230(2) 0.0043(2)
    Cl2 0.0503(3) 0.0737(3) 0.0479(3) 0.0012(2) 0.0063(2) 0.0035(2)
    N1 0.0419(8) 0.0476(9) 0.0485(9) 0.0047(7) 0.0179(7) 0.0038(7)
    N2 0.0362(8) 0.0501(9) 0.0500(9) 0.0102(7) 0.0129(7) 0.0036(7)
    N3 0.0383(8) 0.0473(9) 0.0519(9) 0.0077(7) 0.0122(7) 0.0123(7)
    C1 0.0536(12) 0.0554(12) 0.0578(12) 0.0082(9) 0.0207(10) 0.0103(9)
    C2 0.0735(15) 0.0564(12) 0.0574(13) 0.0019(11) 0.0217(11) 0.0129(10)
    C3 0.0659(14) 0.0705(15) 0.0569(13) -0.0126(12) 0.0269(11) 0.0082(11)
    C4 0.0449(11) 0.0721(14) 0.0615(13) -0.0026(10) 0.0226(10) 0.0057(11)
    C5 0.0392(9) 0.0555(11) 0.0443(10) 0.0010(8) 0.0148(8) -0.0010(8)
    C6 0.0340(9) 0.0644(12) 0.0560(11) 0.0098(9) 0.0139(8) 0.0023(9)
    C7 0.0482(11) 0.0586(12) 0.0636(12) 0.0234(9) 0.0148(9) 0.0106(10)
    C8 0.0577(12) 0.0445(10) 0.0691(13) 0.0166(9) 0.0147(10) 0.0130(9)
    C9 0.0464(12) 0.0759(15) 0.0784(15) -0.0018(11) 0.0153(11) 0.0297(12)
    C10 0.0576(12) 0.0751(15) 0.0515(12) 0.0149(11) 0.0133(10) 0.0156(10)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 N2 . 2.104(2) yes
    Cu1 N1 . 2.236(2) yes
    Cu1 Cl1 . 2.2560(10)
                       yes
    Cu1 Cl2 . 2.2570(10)
                       yes
    Cu1 N3 . 2.275(2) yes
    N1 C1 . 1.327(3) ?
    N1 C5 . 1.348(2) ?
    N2 C6 . 1.265(2) ?
    N2 C7 . 1.461(3) ?
    N3 C8 . 1.470(2) ?
    N3 C10 . 1.473(3) ?
    N3 C9 . 1.477(2) ?
    C1 C2 . 1.385(3) ?
    C1 H1 . 0.93 ?
    C2 C3 . 1.372(3) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.376(3) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.379(3) ?
    C4 H4 . 0.93 ?
    C5 C6 . 1.464(3) ?
    C6 H6 . 0.93 ?
    C7 C8 . 1.514(3) ?
    C7 H7A . 0.97 ?
    C7 H7B . 0.97 ?
    C8 H8A . 0.97 ?
    C8 H8B . 0.97 ?
    C9 H9A . 0.96 ?
    C9 H9B . 0.96 ?
    C9 H9C . 0.96 ?
    C10 H10A . 0.96 ?
    C10 H10B . 0.96 ?
    C10 H10C . 0.96 ?
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
    N2 Cu1 N1 . . 74.25(6) yes
    N2 Cu1 Cl1 . . 132.19(4) yes
    N1 Cu1 Cl1 . . 95.85(4) yes
    N2 Cu1 Cl2 . . 113.68(4) yes
    N1 Cu1 Cl2 . . 98.29(4) yes
    Cl1 Cu1 Cl2 . . 114.01(2) yes
    N2 Cu1 N3 . . 76.84(6) yes
    N1 Cu1 N3 . . 150.35(6) yes
    Cl1 Cu1 N3 . . 98.64(4) yes
    Cl2 Cu1 N3 . . 99.20(4) yes
    C1 N1 C5 . . 118.09(17) ?
    C1 N1 Cu1 . . 128.13(13) ?
    C5 N1 Cu1 . . 113.78(13) ?
    C6 N2 C7 . . 123.01(17) ?
    C6 N2 Cu1 . . 119.30(14) ?
    C7 N2 Cu1 . . 117.66(12) ?
    C8 N3 C10 . . 111.28(16) ?
    C8 N3 C9 . . 109.32(17) ?
    C10 N3 C9 . . 108.68(17) ?
    C8 N3 Cu1 . . 102.47(11) ?
    C10 N3 Cu1 . . 113.11(13) ?
    C9 N3 Cu1 . . 111.85(12) ?
    N1 C1 C2 . . 122.5(2) ?
    N1 C1 H1 . . 118.8 ?
    C2 C1 H1 . . 118.8 ?
    C3 C2 C1 . . 119.2(2) ?
    C3 C2 H2 . . 120.4 ?
    C1 C2 H2 . . 120.4 ?
    C2 C3 C4 . . 119.0(2) ?
    C2 C3 H3 . . 120.5 ?
    C4 C3 H3 . . 120.5 ?
    C3 C4 C5 . . 118.8(2) ?
    C3 C4 H4 . . 120.6 ?
    C5 C4 H4 . . 120.6 ?
    N1 C5 C4 . . 122.5(2) ?
    N1 C5 C6 . . 114.20(16) ?
    C4 C5 C6 . . 123.29(19) ?
    N2 C6 C5 . . 118.45(17) ?
    N2 C6 H6 . . 120.8 ?
    C5 C6 H6 . . 120.8 ?
    N2 C7 C8 . . 107.34(15) ?
    N2 C7 H7A . . 110.2 ?
    C8 C7 H7A . . 110.2 ?
    N2 C7 H7B . . 110.2 ?
    C8 C7 H7B . . 110.2 ?
    H7A C7 H7B . . 108.5 ?
    N3 C8 C7 . . 110.77(16) ?
    N3 C8 H8A . . 109.5 ?
    C7 C8 H8A . . 109.5 ?
    N3 C8 H8B . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 108.1 ?
    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 ?
    N3 C10 H10A . . 109.5 ?
    N3 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    N3 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 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
    N2 Cu1 N1 C1 . . . . 178.28(17) ?
    Cl1 Cu1 N1 C1 . . . . -49.45(16) ?
    Cl2 Cu1 N1 C1 . . . . 65.91(16) ?
    N3 Cu1 N1 C1 . . . . -168.48(15) ?
    N2 Cu1 N1 C5 . . . . -0.51(12) ?
    Cl1 Cu1 N1 C5 . . . . 131.76(12) ?
    Cl2 Cu1 N1 C5 . . . . -112.88(12) ?
    N3 Cu1 N1 C5 . . . . 12.73(19) ?
    N1 Cu1 N2 C6 . . . . -0.53(14) ?
    Cl1 Cu1 N2 C6 . . . . -84.06(15) ?
    Cl2 Cu1 N2 C6 . . . . 91.75(15) ?
    N3 Cu1 N2 C6 . . . . -173.85(16) ?
    N1 Cu1 N2 C7 . . . . -178.70(15) ?
    Cl1 Cu1 N2 C7 . . . . 97.77(14) ?
    Cl2 Cu1 N2 C7 . . . . -86.42(14) ?
    N3 Cu1 N2 C7 . . . . 7.98(13) ?
    N2 Cu1 N3 C8 . . . . -32.14(12) ?
    N1 Cu1 N3 C8 . . . . -45.23(17) ?
    Cl1 Cu1 N3 C8 . . . . -163.61(11) ?
    Cl2 Cu1 N3 C8 . . . . 80.19(11) ?
    N2 Cu1 N3 C10 . . . . 87.75(13) ?
    N1 Cu1 N3 C10 . . . . 74.67(17) ?
    Cl1 Cu1 N3 C10 . . . . -43.71(13) ?
    Cl2 Cu1 N3 C10 . . . . -159.91(12) ?
    N2 Cu1 N3 C9 . . . . -149.13(15) ?
    N1 Cu1 N3 C9 . . . . -162.21(14) ?
    Cl1 Cu1 N3 C9 . . . . 79.41(14) ?
    Cl2 Cu1 N3 C9 . . . . -36.80(14) ?
    C5 N1 C1 C2 . . . . -1.0(3) ?
    Cu1 N1 C1 C2 . . . . -179.70(15) ?
    N1 C1 C2 C3 . . . . 0.3(3) ?
    C1 C2 C3 C4 . . . . 0.7(3) ?
    C2 C3 C4 C5 . . . . -1.0(3) ?
    C1 N1 C5 C4 . . . . 0.7(3) ?
    Cu1 N1 C5 C4 . . . . 179.61(15) ?
    C1 N1 C5 C6 . . . . -177.60(17) ?
    Cu1 N1 C5 C6 . . . . 1.3(2) ?
    C3 C4 C5 N1 . . . . 0.3(3) ?
    C3 C4 C5 C6 . . . . 178.41(19) ?
    C7 N2 C6 C5 . . . . 179.52(17) ?
    Cu1 N2 C6 C5 . . . . 1.5(2) ?
    N1 C5 C6 N2 . . . . -1.9(3) ?
    C4 C5 C6 N2 . . . . 179.87(19) ?
    C6 N2 C7 C8 . . . . -160.19(18) ?
    Cu1 N2 C7 C8 . . . . 17.9(2) ?
    C10 N3 C8 C7 . . . . -67.9(2) ?
    C9 N3 C8 C7 . . . . 172.02(17) ?
    Cu1 N3 C8 C7 . . . . 53.24(18) ?
    N2 C7 C8 N3 . . . . -49.0(2) ?
