##############################################################################
###                                                                        ###
###        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           #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-03-08
_journal_date_accepted     2010-03-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     m419
_journal_page_last     m419
_journal_paper_category     QM
_journal_coeditor_code     CI5055
_publ_contact_author_name     'Yu Zhu'
_publ_contact_author_address
;
Department of Chemistry
Baicheng Normal College
Baicheng 137000
People's Republic of China
;
_publ_contact_author_email     zhuyu_bcnc@sohu.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
{2-[2-(Ethylamino)ethyliminomethyl]-5-methoxyphenolato}(thiocyanato-κN)\
copper(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Yu Zhu'
;
Department of Chemistry
Baicheng Normal College
Baicheng 137000
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
{2-[2-(Ethylamino)ethyliminomethyl]-5-methoxyphenolato}(thiocyanato-κN)
copper(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H17 Cu N3 O2 S'
_chemical_formula_sum     'C13 H17 Cu N3 O2 S'
_chemical_formula_iupac     '[Cu (C12 H17 N2 O2) (N C S)]'
_chemical_formula_weight     342.90
_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     12.296(6)
_cell_length_b     10.582(5)
_cell_length_c     12.480(6)
_cell_angle_alpha     90.00
_cell_angle_beta     113.810(7)
_cell_angle_gamma     90.00
_cell_volume     1485.7(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2310
_cell_measurement_theta_min     2.6
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'Block cut from needle'
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.533
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     708
_exptl_absorpt_coefficient_mu     1.614
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.6431
_exptl_absorpt_correction_T_max     0.6697
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8523
_diffrn_reflns_av_R_equivalents     0.0389
_diffrn_reflns_av_sigmaI/netI     0.0486
_diffrn_reflns_theta_min     1.81
_diffrn_reflns_theta_max     27.45
_diffrn_reflns_theta_full     27.45
_diffrn_measured_fraction_theta_max     0.966
_diffrn_measured_fraction_theta_full     0.966
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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     3282
_reflns_number_gt     2123
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0812
_refine_ls_R_factor_gt     0.0438
_refine_ls_wR_factor_gt     0.1065
_refine_ls_wR_factor_ref     0.1291
_refine_ls_goodness_of_fit_ref     1.002
_refine_ls_restrained_S_all     1.002
_refine_ls_number_reflns     3282
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0551P)²+1.5145P] 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     0.607
_refine_diff_density_min     -0.342
_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'
    'S' 'S' 0.1246 0.1234
                         '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 (Bruker, 1998)'
_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 0.55890(4) 0.38272(4) 0.94272(4) 0.04744(18) Uani d . 1 . .
    N N1 0.6492(3) 0.3114(3) 1.0844(3) 0.0465(8) Uani d . 1 . .
    N N2 0.4301(3) 0.2831(3) 0.9449(3) 0.0596(9) Uani d . 1 . .
    H H2N 0.3686 0.3382 0.9287 0.072 Uiso calc R 1 . .
    N N3 0.4579(3) 0.4525(3) 0.7995(3) 0.0488(8) Uani d . 1 . .
    O O1 0.6770(2) 0.4836(3) 0.9392(2) 0.0543(7) Uani d . 1 . .
    O O2 1.0326(3) 0.7210(3) 1.0840(3) 0.0718(9) Uani d . 1 . .
    S S1 0.30391(13) 0.57348(14) 0.60132(10) 0.0790(4) Uani d . 1 . .
    C C1 0.7807(3) 0.5063(4) 1.0246(3) 0.0460(9) Uani d . 1 . .
    C C2 0.8513(4) 0.5995(4) 1.0075(3) 0.0516(10) Uani d . 1 . .
    H H2 0.8249 0.6414 0.9360 0.062 Uiso calc R 1 . .
    C C3 0.9598(4) 0.6314(4) 1.0944(4) 0.0552(10) Uani d . 1 . .
    C C4 0.9978(5) 0.7842(5) 0.9760(4) 0.0858(17) Uani d . 1 . .
    H H4A 0.9877 0.7240 0.9152 0.129 Uiso calc R 1 . .
    H H4B 1.0578 0.8443 0.9801 0.129 Uiso calc R 1 . .
    H H4C 0.9240 0.8276 0.9590 0.129 Uiso calc R 1 . .
    C C5 1.0006(4) 0.5683(5) 1.2010(4) 0.0664(12) Uani d . 1 . .
    H H5 1.0740 0.5885 1.2598 0.080 Uiso calc R 1 . .
    C C6 0.9326(4) 0.4776(4) 1.2183(4) 0.0629(12) Uani d . 1 . .
    H H6 0.9605 0.4365 1.2904 0.075 Uiso calc R 1 . .
    C C7 0.8217(4) 0.4421(4) 1.1327(3) 0.0480(9) Uani d . 1 . .
    C C8 0.7542(4) 0.3458(4) 1.1546(3) 0.0510(10) Uani d . 1 . .
    H H8 0.7884 0.3035 1.2258 0.061 Uiso calc R 1 . .
    C C9 0.5884(4) 0.2097(4) 1.1177(4) 0.0597(11) Uani d . 1 . .
    H H9A 0.6175 0.2042 1.2023 0.072 Uiso calc R 1 . .
    H H9B 0.6024 0.1293 1.0880 0.072 Uiso calc R 1 . .
    C C10 0.4593(4) 0.2402(4) 1.0658(4) 0.0630(12) Uani d . 1 . .
    H H10A 0.4129 0.1660 1.0658 0.076 Uiso calc R 1 . .
    H H10B 0.4421 0.3062 1.1106 0.076 Uiso calc R 1 . .
    C C11 0.3850(5) 0.1848(5) 0.8565(4) 0.0792(15) Uani d . 1 . .
    H H11A 0.4379 0.1126 0.8819 0.095 Uiso calc R 1 . .
    H H11B 0.3879 0.2159 0.7845 0.095 Uiso calc R 1 . .
    C C12 0.2620(5) 0.1410(5) 0.8301(4) 0.0816(16) Uani d . 1 . .
    H H12A 0.2569 0.1124 0.9009 0.122 Uiso calc R 1 . .
    H H12B 0.2422 0.0727 0.7748 0.122 Uiso calc R 1 . .
    H H12C 0.2074 0.2095 0.7976 0.122 Uiso calc R 1 . .
    C C13 0.3932(4) 0.5018(4) 0.7173(3) 0.0459(9) Uani 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 0.0569(3) 0.0430(3) 0.0396(3) -0.0019(2) 0.0166(2) 0.00224(19)
    N1 0.063(2) 0.0397(17) 0.0379(16) 0.0056(15) 0.0213(15) 0.0010(13)
    N2 0.077(3) 0.0499(19) 0.0485(19) -0.0137(18) 0.0216(18) 0.0024(15)
    N3 0.055(2) 0.0471(18) 0.0396(17) -0.0061(16) 0.0142(15) 0.0017(14)
    O1 0.0489(16) 0.0666(18) 0.0378(14) -0.0067(14) 0.0073(12) 0.0121(12)
    O2 0.0598(19) 0.089(2) 0.0557(19) -0.0252(18) 0.0123(15) -0.0104(16)
    S1 0.0831(9) 0.1010(10) 0.0463(6) 0.0400(8) 0.0192(6) 0.0180(6)
    C1 0.046(2) 0.050(2) 0.0409(19) 0.0040(18) 0.0167(17) -0.0023(17)
    C2 0.048(2) 0.063(3) 0.040(2) -0.002(2) 0.0142(17) -0.0014(18)
    C3 0.052(2) 0.060(3) 0.051(2) -0.004(2) 0.0181(19) -0.0141(19)
    C4 0.078(4) 0.106(4) 0.069(3) -0.044(3) 0.024(3) -0.008(3)
    C5 0.051(3) 0.078(3) 0.054(3) 0.002(2) 0.004(2) -0.007(2)
    C6 0.063(3) 0.068(3) 0.045(2) 0.010(2) 0.008(2) 0.003(2)
    C7 0.047(2) 0.050(2) 0.043(2) 0.0092(19) 0.0146(17) 0.0009(17)
    C8 0.064(3) 0.048(2) 0.038(2) 0.018(2) 0.0180(19) 0.0068(17)
    C9 0.087(3) 0.044(2) 0.047(2) 0.001(2) 0.025(2) 0.0102(18)
    C10 0.086(4) 0.052(2) 0.052(2) -0.018(2) 0.029(2) 0.002(2)
    C11 0.103(4) 0.073(3) 0.065(3) -0.030(3) 0.037(3) -0.011(3)
    C12 0.078(3) 0.093(4) 0.057(3) -0.029(3) 0.009(2) -0.002(3)
    C13 0.054(2) 0.046(2) 0.038(2) -0.0007(19) 0.0193(18) -0.0025(17)
_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 O1 . 1.817(3) y
    Cu1 N1 . 1.828(3) y
    Cu1 N3 . 1.868(3) y
    Cu1 N2 . 1.912(4) y
    N1 C8 . 1.286(5) ?
    N1 C9 . 1.463(5) ?
    N2 C11 . 1.453(6) ?
    N2 C10 . 1.474(5) ?
    N2 H2N . 0.91 ?
    N3 C13 . 1.139(5) ?
    O1 C1 . 1.313(4) ?
    O2 C3 . 1.346(5) ?
    O2 C4 . 1.409(6) ?
    S1 C13 . 1.610(4) ?
    C1 C2 . 1.386(6) ?
    C1 C7 . 1.409(5) ?
    C2 C3 . 1.379(6) ?
    C2 H2 . 0.93 ?
    C3 C5 . 1.389(6) ?
    C4 H4A . 0.96 ?
    C4 H4B . 0.96 ?
    C4 H4C . 0.96 ?
    C5 C6 . 1.346(6) ?
    C5 H5 . 0.93 ?
    C6 C7 . 1.402(6) ?
    C6 H6 . 0.93 ?
    C7 C8 . 1.410(6) ?
    C8 H8 . 0.93 ?
    C9 C10 . 1.488(6) ?
    C9 H9A . 0.97 ?
    C9 H9B . 0.97 ?
    C10 H10A . 0.97 ?
    C10 H10B . 0.97 ?
    C11 C12 . 1.487(7) ?
    C11 H11A . 0.97 ?
    C11 H11B . 0.97 ?
    C12 H12A . 0.96 ?
    C12 H12B . 0.96 ?
    C12 H12C . 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
    O1 Cu1 N1 . . 94.97(13) ?
    O1 Cu1 N3 . . 88.49(13) ?
    N1 Cu1 N3 . . 176.29(15) ?
    O1 Cu1 N2 . . 177.40(14) ?
    N1 Cu1 N2 . . 86.67(15) ?
    N3 Cu1 N2 . . 89.82(15) ?
    C8 N1 C9 . . 120.1(3) ?
    C8 N1 Cu1 . . 126.4(3) ?
    C9 N1 Cu1 . . 113.4(3) ?
    C11 N2 C10 . . 114.7(3) ?
    C11 N2 Cu1 . . 116.6(3) ?
    C10 N2 Cu1 . . 108.9(3) ?
    C11 N2 H2N . . 105.2 ?
    C10 N2 H2N . . 105.2 ?
    Cu1 N2 H2N . . 105.2 ?
    C13 N3 Cu1 . . 174.4(3) ?
    C1 O1 Cu1 . . 127.7(2) ?
    C3 O2 C4 . . 118.0(3) ?
    O1 C1 C2 . . 118.0(3) ?
    O1 C1 C7 . . 122.9(4) ?
    C2 C1 C7 . . 119.1(4) ?
    C3 C2 C1 . . 121.3(4) ?
    C3 C2 H2 . . 119.3 ?
    C1 C2 H2 . . 119.3 ?
    O2 C3 C2 . . 124.5(4) ?
    O2 C3 C5 . . 115.7(4) ?
    C2 C3 C5 . . 119.8(4) ?
    O2 C4 H4A . . 109.5 ?
    O2 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    O2 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    C6 C5 C3 . . 119.3(4) ?
    C6 C5 H5 . . 120.4 ?
    C3 C5 H5 . . 120.4 ?
    C5 C6 C7 . . 122.9(4) ?
    C5 C6 H6 . . 118.5 ?
    C7 C6 H6 . . 118.5 ?
    C6 C7 C1 . . 117.6(4) ?
    C6 C7 C8 . . 120.9(4) ?
    C1 C7 C8 . . 121.6(4) ?
    N1 C8 C7 . . 125.5(3) ?
    N1 C8 H8 . . 117.3 ?
    C7 C8 H8 . . 117.3 ?
    N1 C9 C10 . . 107.1(3) ?
    N1 C9 H9A . . 110.3 ?
    C10 C9 H9A . . 110.3 ?
    N1 C9 H9B . . 110.3 ?
    C10 C9 H9B . . 110.3 ?
    H9A C9 H9B . . 108.5 ?
    N2 C10 C9 . . 106.8(4) ?
    N2 C10 H10A . . 110.4 ?
    C9 C10 H10A . . 110.4 ?
    N2 C10 H10B . . 110.4 ?
    C9 C10 H10B . . 110.4 ?
    H10A C10 H10B . . 108.6 ?
    N2 C11 C12 . . 115.7(4) ?
    N2 C11 H11A . . 108.4 ?
    C12 C11 H11A . . 108.4 ?
    N2 C11 H11B . . 108.4 ?
    C12 C11 H11B . . 108.4 ?
    H11A C11 H11B . . 107.4 ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    N3 C13 S1 . . 178.8(4) ?
