#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/43/2224341.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224341
loop_
_publ_author_name
'Zhang, Xiu-Qing'
'Li, Chun-Ying'
'Bian, He-Dong'
'Yu, Qing'
'Liang, Hong'
_publ_section_title
{N,N-Dimethyl-N'-[phenyl(2-pyridyl)methylene]ethane-1,2-diamine-κ³N,N',N''}dithiocyanato-κN,κS-copper(II)
_journal_coeditor_code           KJ2135
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1610
_journal_paper_doi               10.1107/S1600536809048594
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (N C S)2 (C16 H19 N3)]'
_chemical_formula_sum            'C18 H19 Cu N5 S2'
_chemical_formula_weight         433.04
_chemical_name_systematic
;
{N,N-Dimethyl-N'-[phenyl(2-pyridyl)methylene]ethane-
1,2-diamine-κ³N,N',N''}dithiocyanato-
κN,κS-copper(II)
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6524(13)
_cell_length_b                   9.2048(15)
_cell_length_c                   27.931(5)
_cell_measurement_reflns_used    3480
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.63
_cell_measurement_theta_min      2.65
_cell_volume                     1967.4(6)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            11093
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    1.334
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.748342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.506
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3978
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0567P)²+2.0946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1300
_reflns_number_gt                3035
_reflns_number_total             3978
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2135.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224341
_cod_database_fobs_code          2224341
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.26036(8) 0.95205(6) 0.07382(2) 0.04339(19) Uani d . 1 . .
S S1 -0.0307(2) 0.9109(2) -0.07293(6) 0.0670(5) Uani d . 1 . .
S S2 0.0488(3) 1.1662(2) 0.10308(7) 0.0735(5) Uani d . 1 . .
N N1 0.1524(7) 0.9185(6) 0.01206(16) 0.0609(14) Uani d . 1 . .
N N2 -0.0282(8) 1.0836(9) 0.1945(2) 0.098(2) Uani d U 1 . .
N N3 0.1284(5) 0.7992(5) 0.11202(15) 0.0415(10) Uani d . 1 . .
N N4 0.4058(5) 0.9435(5) 0.13148(14) 0.0391(9) Uani d . 1 . .
N N5 0.4643(6) 1.0786(5) 0.04853(14) 0.0429(10) Uani d . 1 . .
C C1 0.0763(7) 0.9159(6) -0.02339(18) 0.0422(12) Uani d . 1 . .
C C2 0.0070(9) 1.1144(8) 0.1584(3) 0.071(2) Uani d . 1 . .
C C3 -0.0085(7) 0.7208(7) 0.0973(2) 0.0509(14) Uani d . 1 . .
H H3 -0.0606 0.7416 0.0680 0.061 Uiso calc R 1 . .
C C4 -0.0730(9) 0.6097(9) 0.1250(3) 0.078(2) Uani d . 1 . .
H H4 -0.1645 0.5527 0.1137 0.093 Uiso calc R 1 . .
C C5 -0.0016(9) 0.5823(8) 0.1698(3) 0.077(2) Uani d . 1 . .
H H5 -0.0454 0.5080 0.1889 0.092 Uiso calc R 1 . .
C C6 0.1341(8) 0.6666(7) 0.1854(2) 0.0561(16) Uani d . 1 . .
H H6 0.1821 0.6520 0.2156 0.067 Uiso calc R 1 . .
C C7 0.1993(6) 0.7740(6) 0.15551(17) 0.0388(12) Uani d . 1 . .
C C8 0.3525(7) 0.8643(6) 0.16633(16) 0.0376(11) Uani d . 1 . .
C C9 0.4422(7) 0.8568(6) 0.21348(18) 0.0414(12) Uani d . 1 . .
C C10 0.6136(9) 0.8125(9) 0.2169(3) 0.075(2) Uani d . 1 . .
H H10 0.6737 0.7854 0.1894 0.090 Uiso calc R 1 . .
C C11 0.6961(10) 0.8079(9) 0.2600(3) 0.083(2) Uani d . 1 . .
H H11 0.8103 0.7739 0.2618 0.100 Uiso calc R 1 . .
C C12 0.6143(10) 0.8520(9) 0.2999(2) 0.072(2) Uani d . 1 . .
H H12 0.6727 0.8523 0.3291 0.086 Uiso calc R 1 . .
C C13 0.4464(12) 0.8959(10) 0.2973(2) 0.094(3) Uani d . 1 . .
H H13 0.3889 0.9248 0.3250 0.113 Uiso calc R 1 . .
C C14 0.3591(10) 0.8986(9) 0.2545(2) 0.076(2) Uani d . 1 . .
H H14 0.2433 0.9289 0.2534 0.091 Uiso calc R 1 . .
C C15 0.5594(7) 1.0370(7) 0.13190(19) 0.0511(14) Uani d . 1 . .
H H15A 0.6642 0.9799 0.1265 0.061 Uiso calc R 1 . .
H H15B 0.5699 1.0855 0.1626 0.061 Uiso calc R 1 . .
C C16 0.5371(8) 1.1467(6) 0.0926(2) 0.0508(14) Uani d . 1 . .
H H16A 0.4591 1.2232 0.1034 0.061 Uiso calc R 1 . .
H H16B 0.6493 1.1904 0.0853 0.061 Uiso calc R 1 . .
C C17 0.4088(9) 1.1937(7) 0.0152(2) 0.0620(17) Uani d . 1 . .
H H17A 0.5065 1.2552 0.0080 0.093 Uiso calc R 1 . .
H H17B 0.3179 1.2505 0.0298 0.093 Uiso calc R 1 . .
H H17C 0.3656 1.1505 -0.0137 0.093 Uiso calc R 1 . .
C C18 0.5928(9) 0.9836(8) 0.0258(2) 0.0673(18) Uani d . 1 . .
H H18A 0.5454 0.9456 -0.0034 0.101 Uiso calc R 1 . .
H H18B 0.6207 0.9049 0.0470 0.101 Uiso calc R 1 . .
H H18C 0.6969 1.0380 0.0189 0.101 Uiso calc R 1 . .
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'
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'
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 Cu1 N4 . . 165.4(2) ?
N1 Cu1 N3 . . 98.3(2) ?
N4 Cu1 N3 . . 79.81(18) ?
N1 Cu1 N5 . . 96.2(2) ?
N4 Cu1 N5 . . 82.82(17) ?
N3 Cu1 N5 . . 160.36(17) ?
N1 Cu1 S2 . . 97.53(18) ?
N4 Cu1 S2 . . 97.02(13) ?
N3 Cu1 S2 . . 92.79(13) ?
N5 Cu1 S2 . . 98.38(13) ?
C2 S2 Cu1 . . 101.0(3) ?
C1 N1 Cu1 . . 170.7(5) ?
C3 N3 C7 . . 119.9(5) ?
C3 N3 Cu1 . . 127.0(4) ?
C7 N3 Cu1 . . 113.0(3) ?
C8 N4 C15 . . 125.9(4) ?
C8 N4 Cu1 . . 117.8(3) ?
C15 N4 Cu1 . . 116.2(3) ?
C18 N5 C17 . . 110.5(5) ?
C18 N5 C16 . . 111.0(5) ?
C17 N5 C16 . . 109.1(4) ?
C18 N5 Cu1 . . 108.6(4) ?
C17 N5 Cu1 . . 113.7(4) ?
C16 N5 Cu1 . . 103.7(3) ?
N1 C1 S1 . . 179.5(6) ?
N2 C2 S2 . . 176.5(8) ?
N3 C3 C4 . . 120.7(6) ?
N3 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C3 C4 C5 . . 120.0(6) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 118.9(6) ?
C6 C5 H5 . . 120.6 ?
C4 C5 H5 . . 120.6 ?
C5 C6 C7 . . 119.1(6) ?
C5 C6 H6 . . 120.5 ?
C7 C6 H6 . . 120.5 ?
N3 C7 C6 . . 121.3(5) ?
N3 C7 C8 . . 114.1(4) ?
C6 C7 C8 . . 124.5(5) ?
N4 C8 C7 . . 114.8(4) ?
N4 C8 C9 . . 123.5(5) ?
C7 C8 C9 . . 121.7(4) ?
C14 C9 C10 . . 118.0(6) ?
C14 C9 C8 . . 121.0(5) ?
C10 C9 C8 . . 121.0(5) ?
C11 C10 C9 . . 120.8(7) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C12 C11 C10 . . 120.7(7) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 C13 . . 119.3(6) ?
C11 C12 H12 . . 120.4 ?
C13 C12 H12 . . 120.4 ?
C12 C13 C14 . . 121.2(7) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C9 C14 C13 . . 120.0(7) ?
C9 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
N4 C15 C16 . . 107.4(4) ?
N4 C15 H15A . . 110.2 ?
C16 C15 H15A . . 110.2 ?
N4 C15 H15B . . 110.2 ?
C16 C15 H15B . . 110.2 ?
H15A C15 H15B . . 108.5 ?
N5 C16 C15 . . 111.3(5) ?
N5 C16 H16A . . 109.4 ?
C15 C16 H16A . . 109.4 ?
N5 C16 H16B . . 109.4 ?
C15 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
N5 C17 H17A . . 109.5 ?
N5 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N5 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N5 C18 H18A . . 109.5 ?
N5 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N5 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
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 N1 . 1.937(4) ?
Cu1 N4 . 1.959(4) ?
Cu1 N3 . 2.034(4) ?
Cu1 N5 . 2.071(4) ?
Cu1 S2 . 2.679(2) ?
S1 C1 . 1.609(5) ?
S2 C2 . 1.648(9) ?
N1 C1 . 1.149(7) ?
N2 C2 . 1.082(9) ?
N3 C3 . 1.337(7) ?
N3 C7 . 1.351(6) ?
N4 C8 . 1.283(6) ?
N4 C15 . 1.457(7) ?
N5 C18 . 1.461(7) ?
N5 C17 . 1.472(7) ?
N5 C16 . 1.490(7) ?
C3 C4 . 1.373(9) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.389(10) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.368(9) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.386(8) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.468(7) ?
C8 C9 . 1.487(7) ?
C9 C14 . 1.365(8) ?
C9 C10 . 1.376(8) ?
C10 C11 . 1.361(9) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.341(10) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.349(11) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.369(9) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.501(8) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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 Cu1 S2 C2 . . . . 134.4(3) ?
N4 Cu1 S2 C2 . . . . -44.5(3) ?
N3 Cu1 S2 C2 . . . . 35.6(3) ?
N5 Cu1 S2 C2 . . . . -128.2(3) ?
N1 Cu1 N3 C3 . . . . -8.9(5) ?
N4 Cu1 N3 C3 . . . . -174.2(5) ?
N5 Cu1 N3 C3 . . . . -146.0(5) ?
S2 Cu1 N3 C3 . . . . 89.2(4) ?
N1 Cu1 N3 C7 . . . . 167.2(4) ?
N4 Cu1 N3 C7 . . . . 1.9(3) ?
N5 Cu1 N3 C7 . . . . 30.1(7) ?
S2 Cu1 N3 C7 . . . . -94.7(3) ?
N1 Cu1 N4 C8 . . . . -89.6(9) ?
N3 Cu1 N4 C8 . . . . -5.7(4) ?
N5 Cu1 N4 C8 . . . . -176.5(4) ?
S2 Cu1 N4 C8 . . . . 85.9(4) ?
N1 Cu1 N4 C15 . . . . 94.7(9) ?
N3 Cu1 N4 C15 . . . . 178.6(4) ?
N5 Cu1 N4 C15 . . . . 7.8(4) ?
S2 Cu1 N4 C15 . . . . -89.8(4) ?
N1 Cu1 N5 C18 . . . . -75.9(4) ?
N4 Cu1 N5 C18 . . . . 89.4(4) ?
N3 Cu1 N5 C18 . . . . 61.5(7) ?
S2 Cu1 N5 C18 . . . . -174.5(4) ?
N1 Cu1 N5 C17 . . . . 47.6(4) ?
N4 Cu1 N5 C17 . . . . -147.1(4) ?
N3 Cu1 N5 C17 . . . . -175.0(5) ?
S2 Cu1 N5 C17 . . . . -51.0(4) ?
N1 Cu1 N5 C16 . . . . 165.9(4) ?
N4 Cu1 N5 C16 . . . . -28.7(3) ?
N3 Cu1 N5 C16 . . . . -56.7(6) ?
S2 Cu1 N5 C16 . . . . 67.3(3) ?
C7 N3 C3 C4 . . . . -3.2(8) ?
Cu1 N3 C3 C4 . . . . 172.7(5) ?
N3 C3 C4 C5 . . . . 3.2(10) ?
C3 C4 C5 C6 . . . . -0.7(11) ?
C4 C5 C6 C7 . . . . -1.7(10) ?
C3 N3 C7 C6 . . . . 0.7(8) ?
Cu1 N3 C7 C6 . . . . -175.7(4) ?
C3 N3 C7 C8 . . . . 177.9(4) ?
Cu1 N3 C7 C8 . . . . 1.5(5) ?
C5 C6 C7 N3 . . . . 1.7(9) ?
C5 C6 C7 C8 . . . . -175.2(5) ?
C15 N4 C8 C7 . . . . -176.7(5) ?
Cu1 N4 C8 C7 . . . . 8.0(6) ?
C15 N4 C8 C9 . . . . 0.2(8) ?
Cu1 N4 C8 C9 . . . . -175.1(4) ?
N3 C7 C8 N4 . . . . -6.1(6) ?
C6 C7 C8 N4 . . . . 171.0(5) ?
N3 C7 C8 C9 . . . . 176.9(4) ?
C6 C7 C8 C9 . . . . -6.0(8) ?
N4 C8 C9 C14 . . . . 118.4(7) ?
C7 C8 C9 C14 . . . . -64.9(7) ?
N4 C8 C9 C10 . . . . -59.2(8) ?
C7 C8 C9 C10 . . . . 117.5(7) ?
C14 C9 C10 C11 . . . . 1.3(11) ?
C8 C9 C10 C11 . . . . 179.0(7) ?
C9 C10 C11 C12 . . . . -2.7(13) ?
C10 C11 C12 C13 . . . . 2.5(13) ?
C11 C12 C13 C14 . . . . -1.1(14) ?
C10 C9 C14 C13 . . . . 0.1(11) ?
C8 C9 C14 C13 . . . . -177.6(7) ?
C12 C13 C14 C9 . . . . -0.2(14) ?
C8 N4 C15 C16 . . . . -159.8(5) ?
Cu1 N4 C15 C16 . . . . 15.6(6) ?
C18 N5 C16 C15 . . . . -70.3(6) ?
C17 N5 C16 C15 . . . . 167.6(5) ?
Cu1 N5 C16 C15 . . . . 46.1(5) ?
N4 C15 C16 N5 . . . . -41.5(6) ?
