#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/94/2019463.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_2019463
loop_
_publ_author_name
'Setifi, Zouaoui'
'Setifi, Fatima'
'Saadi, Mohamed'
'Rouag, Djamil-Azzeddine'
'Glidewell, Christopher'
_publ_section_title
;
 catena-Poly[[[4-amino-3,5-bis(pyridin-2-yl)-4H-1,2,4-triazole-κ²N¹,N⁵](dicyanamido-κN)copper(II)]-μ₂-dicyanamido-κ²N:N']:
 coordination polymer chains linked into a bilayer by hydrogen bonds and
 π--π stacking interactions
;
_journal_coeditor_code           SK3539
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              359
_journal_page_last               363
_journal_paper_doi               10.1107/S205322961400504X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          '[Cu (C2 N3)2 (C12 H10 N6)]'
_chemical_formula_moiety         'C16 H10 Cu N12'
_chemical_formula_sum            'C16 H10 Cu N12'
_chemical_formula_weight         433.91
_chemical_name_systematic
catena-Poly[[[4-amino-3,5-bis(pyridin-2-yl)-4H-1,2,4-triazole-κ²N¹,N⁵](dicyanamido-κN)copper(II)]-μ₂-dicyanamido-κ²N:N']
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                96.668(4)
_cell_angle_beta                 101.019(5)
_cell_angle_gamma                102.962(4)
_cell_formula_units_Z            2
_cell_length_a                   7.5946(5)
_cell_length_b                   8.4284(5)
_cell_length_c                   14.1106(8)
_cell_measurement_reflns_used    6098
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.50
_cell_measurement_theta_min      2.51
_cell_volume                     851.96(9)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Agilent Xcalibur'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13231
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.316
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.585
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         6097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0355P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                4835
_reflns_number_total             6097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3539sup1.cf
_cod_data_source_block           I
_cod_database_code               2019463
_cod_database_fobs_code          2019463
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
Cu Cu1 0.75026(3) 0.22702(3) 0.601776(17) 0.01768(8) Uani d . 1 1
N N1 0.7736(2) 0.2875(2) 0.74376(12) 0.0170(3) Uani d . 1 1
N N2 0.7463(2) 0.4178(2) 0.80088(12) 0.0183(3) Uani d . 1 1
C C3 0.7618(3) 0.3802(2) 0.88962(14) 0.0172(4) Uani d . 1 1
N N4 0.7979(2) 0.2274(2) 0.89006(11) 0.0167(3) Uani d . 1 1
C C5 0.8072(3) 0.1757(2) 0.79761(14) 0.0163(4) Uani d . 1 1
N N11 0.3537(3) 0.5046(2) 0.63214(14) 0.0287(4) Uani d . 1 1
C C12 0.4691(3) 0.4291(3) 0.60224(15) 0.0206(4) Uani d . 1 1
N N13 0.5809(2) 0.3718(2) 0.57711(12) 0.0239(4) Uani d . 1 1
C C14 0.1779(3) 0.4303(3) 0.61239(14) 0.0208(4) Uani d . 1 1
N N15 0.0202(3) 0.3759(2) 0.60091(13) 0.0267(4) Uani d . 1 1
N N21 0.6398(3) -0.0063(2) 0.29552(14) 0.0325(5) Uani d . 1 1
C C22 0.6667(3) 0.0704(3) 0.38353(15) 0.0216(4) Uani d . 1 1
N N23 0.6942(3) 0.1209(2) 0.46577(13) 0.0287(4) Uani d . 1 1
C C24 0.5993(3) 0.0588(3) 0.21636(16) 0.0249(5) Uani d . 1 1
N N25 0.5623(3) 0.0958(3) 0.14076(14) 0.0345(5) Uani d . 1 1
N N31 0.8001(2) 0.4446(2) 1.06232(12) 0.0219(4) Uani d . 1 1
C C32 0.7492(3) 0.4897(2) 0.97524(14) 0.0177(4) Uani d . 1 1
C C33 0.6868(3) 0.6302(3) 0.96337(15) 0.0215(4) Uani d . 1 1
H H33 0.6522 0.6576 0.9002 0.026 Uiso calc R 1 1
C C34 0.6767(3) 0.7294(3) 1.04667(16) 0.0257(5) Uani d . 1 1
H H34 0.6362 0.8275 1.0418 0.031 Uiso calc R 1 1
C C35 0.7263(3) 0.6835(3) 1.13709(16) 0.0260(5) Uani d . 1 1
H H35 0.7199 0.7490 1.1953 0.031 Uiso calc R 1 1
C C36 0.7850(3) 0.5410(3) 1.14086(15) 0.0251(5) Uani d . 1 1
H H36 0.8168 0.5093 1.2030 0.030 Uiso calc R 1 1
N N41 0.8140(3) 0.1338(2) 0.96739(12) 0.0232(4) Uani d . 1 1
H H41A 0.7058 0.0592 0.9580 0.028 Uiso d R 1 1
H H41B 0.8217 0.2051 1.0224 0.028 Uiso d R 1 1
N N51 0.8200(2) 0.0212(2) 0.65314(12) 0.0190(3) Uani d . 1 1
C C52 0.8430(3) 0.0252(2) 0.75076(14) 0.0177(4) Uani d . 1 1
C C53 0.8977(3) -0.0954(3) 0.79808(16) 0.0232(4) Uani d . 1 1
H H53 0.9144 -0.0875 0.8671 0.028 Uiso calc R 1 1
C C54 0.9277(3) -0.2290(3) 0.74188(18) 0.0274(5) Uani d . 1 1
H H54 0.9657 -0.3147 0.7720 0.033 Uiso calc R 1 1
C C55 0.9019(3) -0.2361(3) 0.64206(17) 0.0277(5) Uani d . 1 1
H H55 0.9201 -0.3274 0.6024 0.033 Uiso calc R 1 1
C C56 0.8493(3) -0.1087(3) 0.60037(16) 0.0239(4) Uani d . 1 1
H H56 0.8332 -0.1137 0.5316 0.029 Uiso calc R 1 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'
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_3
_geom_angle
_geom_angle_publ_flag
N1 Cu1 N51 . 78.77(7) y
N1 Cu1 N13 . 89.47(7) y
N13 Cu1 N23 . 94.20(8) y
N23 Cu1 N51 . 92.58(7) y
N1 Cu1 N23 . 167.27(8) y
N13 Cu1 N51 . 152.33(7) y
N1 Cu1 N15 1_655 95.15(7) y
N13 Cu1 N15 1_655 105.20(8) y
N23 Cu1 N15 1_655 95.64(8) y
N51 Cu1 N15 1_655 100.77(7) y
C5 N1 N2 . 109.55(16) ?
C5 N1 Cu1 . 116.22(13) ?
N2 N1 Cu1 . 133.94(13) ?
C3 N2 N1 . 105.99(16) ?
N2 C3 N4 . 110.10(17) ?
N2 C3 C32 . 124.22(18) ?
N4 C3 C32 . 125.63(18) ?
C5 N4 C3 . 105.43(16) ?
C5 N4 N41 . 124.93(16) ?
C3 N4 N41 . 129.57(16) ?
N1 C5 N4 . 108.89(17) ?
N1 C5 C52 . 118.64(17) ?
N4 C5 C52 . 132.45(18) ?
C36 N31 C32 . 116.81(19) ?
N31 C32 C33 . 123.82(18) ?
N31 C32 C3 . 116.13(18) ?
C33 C32 C3 . 120.04(18) ?
C34 C33 C32 . 117.8(2) ?
C34 C33 H33 . 121.1 ?
C32 C33 H33 . 121.1 ?
C35 C34 C33 . 119.1(2) ?
C35 C34 H34 . 120.4 ?
C33 C34 H34 . 120.4 ?
C36 C35 C34 . 118.5(2) ?
C36 C35 H35 . 120.7 ?
C34 C35 H35 . 120.7 ?
N31 C36 C35 . 123.9(2) ?
N31 C36 H36 . 118.0 ?
C35 C36 H36 . 118.0 ?
N4 N41 H41A . 106.8 ?
N4 N41 H41B . 105.2 ?
H41A N41 H41B . 105.8 ?
C56 N51 C52 . 117.69(18) ?
C56 N51 Cu1 . 126.98(14) ?
C52 N51 Cu1 . 115.29(13) ?
N51 C52 C53 . 123.38(19) ?
N51 C52 C5 . 110.82(17) ?
C53 C52 C5 . 125.77(19) ?
C52 C53 C54 . 117.9(2) ?
C52 C53 H53 . 121.0 ?
C54 C53 H53 . 121.0 ?
C55 C54 C53 . 119.3(2) ?
C55 C54 H54 . 120.3 ?
C53 C54 H54 . 120.3 ?
C54 C55 C56 . 119.2(2) ?
C54 C55 H55 . 120.4 ?
C56 C55 H55 . 120.4 ?
N51 C56 C55 . 122.5(2) ?
N51 C56 H56 . 118.7 ?
C55 C56 H56 . 118.7 ?
C12 N11 C14 . 119.6(2) y
N11 C12 N13 . 175.4(3) y
N11 C14 N15 . 173.7(2) y
C22 N21 C24 . 124.3(2) y
N21 C22 N23 . 171.4(2) y
N21 C24 N25 . 171.1(3) y
C12 N13 Cu1 . 147.64(17) y
C14 N15 Cu1 1_455 164.63(18) y
C22 N23 Cu1 . 174.51(19) y
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 . 1.9727(16) y
Cu1 N13 . 1.9737(18) y
Cu1 N23 . 1.9447(18) y
Cu1 N51 . 2.0912(17) y
Cu1 N15 1_655 2.1534(19) y
N1 N2 . 1.364(2) y
N2 C3 . 1.317(2) y
C3 N4 . 1.377(3) y
N4 C5 . 1.347(2) y
C5 N1 . 1.316(2) y
N4 N41 . 1.421(2) y
C3 C32 . 1.464(3) ?
C5 C52 . 1.465(3) ?
N31 C36 . 1.335(3) ?
N31 C32 . 1.340(3) ?
C32 C33 . 1.386(3) ?
C33 C34 . 1.386(3) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.384(3) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.374(3) ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
N41 H41A . 0.8918 ?
N41 H41B . 0.9089 ?
N51 C56 . 1.336(3) ?
N51 C52 . 1.350(2) ?
C52 C53 . 1.376(3) ?
C53 C54 . 1.388(3) ?
C53 H53 . 0.9500 ?
C54 C55 . 1.377(3) ?
C54 H54 . 0.9500 ?
C55 C56 . 1.381(3) ?
C55 H55 . 0.9500 ?
C56 H56 . 0.9500 ?
N11 C12 . 1.297(3) y
C12 N13 . 1.157(3) y
N11 C14 . 1.301(3) y
C14 N15 . 1.155(3) y
N15 Cu1 1_455 2.1534(19) ?
N21 C22 . 1.288(3) y
C22 N23 . 1.151(3) y
N21 C24 . 1.315(3) y
C24 N25 . 1.147(3) y
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
_geom_hbond_publ_flag
N41 H41A N25 2_656 0.89 2.26 3.067(3) 151 y
N41 H41B N31 . 0.91 2.08 2.834(2) 139 y
C35 H35 N21 1_566 0.95 2.61 3.499(3) 155 y
C54 H54 N2 1_545 0.95 2.61 3.260(3) 126 y
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
_geom_torsion_publ_flag
N23 Cu1 N1 C5 . 44.0(4) ?
N13 Cu1 N1 C5 . 150.98(15) ?
N51 Cu1 N1 C5 . -3.82(14) ?
N15 Cu1 N1 C5 1_655 -103.81(15) ?
N23 Cu1 N1 N2 . -128.9(3) ?
N13 Cu1 N1 N2 . -21.96(18) ?
N51 Cu1 N1 N2 . -176.76(19) ?
N15 Cu1 N1 N2 1_655 83.25(18) ?
C5 N1 N2 C3 . -0.9(2) ?
Cu1 N1 N2 C3 . 172.42(15) ?
N1 N2 C3 N4 . -0.2(2) ?
N1 N2 C3 C32 . 177.54(17) ?
N2 C3 N4 C5 . 1.2(2) ?
C32 C3 N4 C5 . -176.55(18) ?
N2 C3 N4 N41 . -175.82(18) ?
C32 C3 N4 N41 . 6.5(3) ?
N2 N1 C5 N4 . 1.6(2) ?
Cu1 N1 C5 N4 . -172.98(12) ?
N2 N1 C5 C52 . -179.29(16) ?
Cu1 N1 C5 C52 . 6.1(2) ?
C3 N4 C5 N1 . -1.7(2) ?
N41 N4 C5 N1 . 175.48(17) ?
C3 N4 C5 C52 . 179.4(2) ?
N41 N4 C5 C52 . -3.4(3) ?
C36 N31 C32 C33 . 1.4(3) ?
C36 N31 C32 C3 . -178.40(18) ?
N2 C3 C32 N31 . -168.69(18) y
N4 C3 C32 N31 . 8.7(3) ?
N2 C3 C32 C33 . 11.5(3) ?
N4 C3 C32 C33 . -171.04(19) ?
N31 C32 C33 C34 . 0.0(3) ?
C3 C32 C33 C34 . 179.72(18) ?
C32 C33 C34 C35 . -0.8(3) ?
C33 C34 C35 C36 . 0.4(3) ?
C32 N31 C36 C35 . -1.9(3) ?
C34 C35 C36 N31 . 1.1(3) ?
N23 Cu1 N51 C56 . 12.70(19) ?
N1 Cu1 N51 C56 . -176.71(19) ?
N13 Cu1 N51 C56 . 116.8(2) ?
N15 Cu1 N51 C56 1_655 -83.54(18) ?
N23 Cu1 N51 C52 . -169.56(15) ?
N1 Cu1 N51 C52 . 1.02(14) ?
N13 Cu1 N51 C52 . -65.5(2) ?
N15 Cu1 N51 C52 1_655 94.20(15) ?
C56 N51 C52 C53 . 1.2(3) ?
Cu1 N51 C52 C53 . -176.76(16) ?
C56 N51 C52 C5 . 179.54(18) ?
Cu1 N51 C52 C5 . 1.6(2) ?
N1 C5 C52 N51 . -5.0(3) y
N4 C5 C52 N51 . 173.8(2) ?
N1 C5 C52 C53 . 173.32(19) ?
N4 C5 C52 C53 . -7.9(4) ?
N51 C52 C53 C54 . -1.1(3) ?
C5 C52 C53 C54 . -179.15(19) ?
C52 C53 C54 C55 . 0.0(3) ?
C53 C54 C55 C56 . 0.9(3) ?
C52 N51 C56 C55 . -0.2(3) ?
Cu1 N51 C56 C55 . 177.45(16) ?
C54 C55 C56 N51 . -0.8(3) ?
N23 Cu1 N13 C12 . 136.6(3) ?
N1 Cu1 N13 C12 . -31.2(3) ?
N51 Cu1 N13 C12 . 32.9(4) ?
N15 Cu1 N13 C12 1_655 -126.4(3) ?
