#------------------------------------------------------------------------------
#$Date: 2015-05-13 22:41:22 +0300 (Wed, 13 May 2015) $
#$Revision: 136367 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/99/2019947.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_2019947
loop_
_publ_author_name
'Vieira, Rafael P.'
'Thompson, John R.'
'Beraldo, Heloisa'
'Storr, Tim'
_publ_section_title
;
 Partial conversion of thioamide into nitrile in a copper(II) complex of
 2,6-diacetylpyridine bis(thiosemicarbazone), a drug prototype for
 Alzheimer's disease
;
_journal_coeditor_code           KU3154
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961500813X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Cu (C11 H11 N7 S)]'
_chemical_formula_moiety         'C11 H11 Cu N7 S'
_chemical_formula_sum            'C11 H11 Cu N7 S'
_chemical_formula_weight         336.87
_chemical_name_systematic
'[(Z)-2-((E)-1-{6-[1-({[Amino(sulfanidyl-κS)methylidene]amino}imino-κN)ethyl]pyridin-2-yl-κN}ethylidene)-1-cyanohydrazinido-κN¹]copper(II)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90.6740(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.23580(10)
_cell_length_b                   10.5895(2)
_cell_length_c                   17.2664(3)
_cell_measurement_reflns_used    8522
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.74
_cell_measurement_theta_min      4.17
_cell_volume                     1322.92(4)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and POV-Ray
(http://www.povray.org)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b) and Shelxle (Hübschle et al.,
2011)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16824
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.741
_diffrn_reflns_theta_min         4.899
_exptl_absorpt_coefficient_mu    3.824
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_description       plate
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0479P)²+0.8241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                2153
_reflns_number_total             2437
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ku3154sup1.cif
_cod_data_source_block           I
_cod_database_code               2019947
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'
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_occupancy
Cu Cu1 0.21025(5) 0.42580(3) 0.54573(2) 0.03932(15) Uani d 1
S S1 0.13271(10) 0.28767(6) 0.63790(4) 0.04741(19) Uani d 1
C C1 0.2613(4) 0.4392(3) 0.38702(16) 0.0479(6) Uani d 1
N N1 0.2750(3) 0.5146(2) 0.44956(13) 0.0452(5) Uani d 1
C C6 0.2065(4) 0.3072(3) 0.40317(15) 0.0497(6) Uani d 1
C C3 0.3423(5) 0.6089(4) 0.3045(2) 0.0696(9) Uani d 1
H H3 0.3643 0.6415 0.2555 0.084 Uiso calc 1
N N3 0.1117(3) 0.1689(2) 0.49791(12) 0.0430(5) Uani d 1
C C8 0.0899(3) 0.1646(2) 0.57373(14) 0.0398(5) Uani d 1
N N2 0.1706(3) 0.28604(19) 0.47503(12) 0.0400(5) Uani d 1
C C2 0.2936(4) 0.4840(3) 0.31314(19) 0.0633(8) Uani d 1
H H2 0.2826 0.4311 0.2703 0.076 Uiso calc 1
C C7 0.1982(7) 0.2100(3) 0.34233(18) 0.0844(13) Uani d 1
H H7A 0.0722 0.1980 0.3259 0.127 Uiso calc 1
H H7B 0.2465 0.1320 0.3623 0.127 Uiso calc 1
H H7C 0.2705 0.2366 0.2990 0.127 Uiso calc 1
N N4 0.0319(4) 0.0556(2) 0.60451(13) 0.0528(6) Uani d 1
H H4A 0.0103 -0.0084 0.5751 0.063 Uiso calc 1
H H4B 0.0163 0.0496 0.6537 0.063 Uiso calc 1
C C4 0.3582(4) 0.6845(3) 0.3677(2) 0.0681(10) Uani d 1
H H4 0.3925 0.7686 0.3616 0.082 Uiso calc 1
N N5 0.3066(3) 0.6940(2) 0.58342(17) 0.0549(6) Uani d 1
C C5 0.3235(3) 0.6374(3) 0.44223(18) 0.0510(7) Uani d 1
N N7 0.1961(5) 0.5646(3) 0.74737(18) 0.0823(10) Uani d 1
N N6 0.2514(3) 0.5739(2) 0.60608(15) 0.0519(6) Uani d 1
C C9 0.3378(4) 0.7183(3) 0.5114(2) 0.0565(8) Uani d 1
C C10 0.3968(5) 0.8552(3) 0.4991(2) 0.0756(11) Uani d 1
H H10A 0.5143 0.8571 0.4739 0.113 Uiso calc 1
H H10B 0.4069 0.8969 0.5483 0.113 Uiso calc 1
H H10C 0.3063 0.8976 0.4674 0.113 Uiso calc 1
C C11 0.2233(5) 0.5723(3) 0.6824(2) 0.0590(8) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
N6 Cu1 N2 174.13(9)
N6 Cu1 N1 91.77(10)
N2 Cu1 N1 82.45(9)
N6 Cu1 S1 100.83(8)
N2 Cu1 S1 84.97(6)
N1 Cu1 S1 167.36(8)
C8 S1 Cu1 94.65(8)
N1 C1 C2 121.7(3)
N1 C1 C6 115.2(2)
C2 C1 C6 123.1(3)
C1 N1 C5 120.8(2)
C1 N1 Cu1 112.15(18)
C5 N1 Cu1 127.0(2)
N2 C6 C7 123.9(3)
N2 C6 C1 113.7(2)
C7 C6 C1 122.3(3)
C4 C3 C2 120.0(3)
C4 C3 H3 120.0
C2 C3 H3 120.0
C8 N3 N2 111.0(2)
N3 C8 N4 117.6(2)
N3 C8 S1 125.74(19)
N4 C8 S1 116.61(19)
C6 N2 N3 120.1(2)
C6 N2 Cu1 116.31(18)
N3 N2 Cu1 123.62(16)
C3 C2 C1 118.3(3)
C3 C2 H2 120.8
C1 C2 H2 120.8
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
C8 N4 H4A 120.0
C8 N4 H4B 120.0
H4A N4 H4B 120.0
C3 C4 C5 120.8(3)
C3 C4 H4 119.6
C5 C4 H4 119.6
C9 N5 N6 120.4(3)
N1 C5 C4 118.4(3)
N1 C5 C9 119.9(3)
C4 C5 C9 121.6(3)
C11 N6 N5 109.6(2)
C11 N6 Cu1 120.34(19)
N5 N6 Cu1 130.0(2)
N5 C9 C5 130.8(3)
N5 C9 C10 112.0(3)
C5 C9 C10 117.2(3)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N7 C11 N6 176.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu1 N6 1.904(2)
Cu1 N2 1.938(2)
Cu1 N1 1.970(2)
Cu1 S1 2.2379(7)
S1 C8 1.736(3)
C1 N1 1.346(4)
C1 C2 1.383(4)
C1 C6 1.481(4)
N1 C5 1.353(4)
C6 N2 1.290(3)
C6 C7 1.472(4)
C3 C4 1.357(5)
C3 C2 1.378(5)
C3 H3 0.9300
N3 C8 1.321(3)
N3 N2 1.371(3)
C8 N4 1.341(3)
C2 H2 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
N4 H4A 0.8600
N4 H4B 0.8600
C4 C5 1.405(4)
C4 H4 0.9300
N5 C9 1.293(4)
N5 N6 1.391(3)
C5 C9 1.472(5)
N7 C11 1.144(4)
N6 C11 1.336(4)
C9 C10 1.527(4)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
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
N4 H4A N3 3_556 0.86 2.29 3.133(3) 167.7
N4 H4B N7 2_546 0.86 2.32 3.061(4) 145.0

_cod_database_fobs_code 2019947
