#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/18/2211886.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_2211886
loop_
_publ_author_name
'Fang Jia'
'Jian Li'
'Xiu-Guang Wang'
'Xiao-Jun Zhao'
_publ_section_title
Bis(dicyanamido-κN¹)bis[4-(1,2,4-triazol-1-yl)phenol-κN⁴]copper(II)
_journal_coeditor_code           LH2259
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m31
_journal_page_last               m33
_journal_paper_doi               10.1107/S1600536806051336
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C2 N3)2 (C8 H7 N3 O)2]'
_chemical_formula_moiety         'C20 H14 Cu N12 O2'
_chemical_formula_sum            'C20 H14 Cu N12 O2'
_chemical_formula_weight         517.98
_chemical_name_systematic
;
Bis(dicyanamido-\kN¹)bis[4-(1,2,4-triazol-1-yl)phenol-\kN⁴]copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 95.548(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.9515(17)
_cell_length_b                   7.6960(10)
_cell_length_c                   10.3232(14)
_cell_measurement_reflns_used    2647
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.70
_cell_measurement_theta_min      3.08
_cell_volume                     1024.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX" (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material
;
SHELXTL (Bruker, 2001) and DIAMOND (Brandenburg & Berndt, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5375
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    1.117
_exptl_absorpt_correction_T_max  0.782
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             526
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.039P)²+0.4336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                1537
_reflns_number_total             1801
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2259.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211886
_cod_database_fobs_code          2211886
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_refinement_flags
_atom_site_occupancy
Cu Cu1 0.5000 0.0000 0.0000 0.03856(15) Uani d S 1
O O1 -0.22165(11) 0.2162(2) -0.20100(16) 0.0457(4) Uani d . 1
H H1 -0.2378 0.1517 -0.2629 0.068 Uiso calc R 1
N N1 0.19321(11) 0.1503(2) -0.01241(15) 0.0275(4) Uani d . 1
N N2 0.22549(13) 0.2187(3) 0.10702(17) 0.0407(5) Uani d . 1
N N3 0.35773(12) 0.0897(2) 0.01965(16) 0.0324(4) Uani d . 1
N N4 0.54428(13) 0.0728(3) 0.18080(18) 0.0476(5) Uani d . 1
N N5 0.56265(14) 0.1661(3) 0.40782(17) 0.0459(5) Uani d . 1
N N6 0.68871(18) 0.0517(3) 0.5811(2) 0.0593(6) Uani d . 1
C C1 0.32382(16) 0.1780(3) 0.1207(2) 0.0411(5) Uani d . 1
H H1A 0.3673 0.2075 0.1944 0.049 Uiso calc R 1
C C2 0.27213(14) 0.0746(3) -0.06212(19) 0.0330(5) Uani d . 1
H H2 0.2684 0.0190 -0.1424 0.040 Uiso calc R 1
C C3 0.08631(14) 0.1638(2) -0.06356(18) 0.0254(4) Uani d . 1
C C4 0.04785(15) 0.0628(3) -0.16729(19) 0.0315(4) Uani d . 1
H H4 0.0912 -0.0141 -0.2056 0.038 Uiso calc R 1
C C5 -0.05575(15) 0.0763(3) -0.21430(19) 0.0324(4) Uani d . 1
H H5 -0.0821 0.0079 -0.2841 0.039 Uiso calc R 1
C C6 -0.11979(14) 0.1907(3) -0.15784(19) 0.0291(4) Uani d . 1
C C7 -0.08097(15) 0.2893(3) -0.0520(2) 0.0345(5) Uani d . 1
H H7 -0.1244 0.3647 -0.0124 0.041 Uiso calc R 1
C C8 0.02237(15) 0.2758(3) -0.00503(19) 0.0329(5) Uani d . 1
H H8 0.0486 0.3423 0.0659 0.039 Uiso calc R 1
C C9 0.55701(15) 0.1108(3) 0.2889(2) 0.0387(5) Uani d . 1
C C10 0.63196(16) 0.1004(3) 0.4969(2) 0.0418(5) 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 0.0033 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'
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
N4 Cu1 N4 . 3_655 180 y
N4 Cu1 N3 . 3_655 90.43(7) y
N4 Cu1 N3 3_655 3_655 89.57(7) ?
N4 Cu1 N3 . . 89.57(7) y
N4 Cu1 N3 3_655 . 90.43(7) ?
N3 Cu1 N3 3_655 . 180 y
C6 O1 H1 . . 109.5 ?
C2 N1 N2 . . 109.80(15) ?
C2 N1 C3 . . 129.99(16) ?
N2 N1 C3 . . 120.19(15) ?
C1 N2 N1 . . 102.40(17) ?
C2 N3 C1 . . 102.70(16) ?
C2 N3 Cu1 . . 128.70(14) ?
C1 N3 Cu1 . . 128.58(14) ?
C9 N4 Cu1 . . 171.15(18) ?
C9 N5 C10 . . 120.4(2) ?
N2 C1 N3 . . 115.04(19) ?
N2 C1 H1A . . 122.5 ?
N3 C1 H1A . . 122.5 ?
N1 C2 N3 . . 110.06(17) ?
N1 C2 H2 . . 125.0 ?
N3 C2 H2 . . 125.0 ?
C8 C3 C4 . . 120.51(18) ?
C8 C3 N1 . . 118.93(17) ?
C4 C3 N1 . . 120.55(17) ?
C3 C4 C5 . . 119.69(19) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C6 C5 C4 . . 120.13(19) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
O1 C6 C5 . . 123.79(18) ?
O1 C6 C7 . . 116.40(18) ?
C5 C6 C7 . . 119.80(18) ?
C8 C7 C6 . . 120.05(18) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C3 C8 C7 . . 119.79(18) ?
C3 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
N4 C9 N5 . . 173.4(2) ?
N6 C10 N5 . . 174.6(3) ?
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 N4 . 1.9797(19) y
Cu1 N4 3_655 1.9797(19) ?
Cu1 N3 3_655 1.9964(16) ?
Cu1 N3 . 1.9964(16) y
O1 C6 . 1.365(2) ?
O1 H1 . 0.8200 ?
N1 C2 . 1.322(2) ?
N1 N2 . 1.368(2) ?
N1 C3 . 1.437(2) ?
N2 C1 . 1.306(3) ?
N3 C2 . 1.332(2) ?
N3 C1 . 1.353(3) ?
N4 C9 . 1.150(3) ?
N5 C9 . 1.294(3) ?
N5 C10 . 1.322(3) ?
N6 C10 . 1.145(3) ?
C1 H1A . 0.9300 ?
C2 H2 . 0.9300 ?
C3 C8 . 1.375(3) ?
C3 C4 . 1.377(3) ?
C4 C5 . 1.386(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.377(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.385(3) ?
C7 C8 . 1.383(3) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
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
C8 H8 N2 . 0.93 2.48 2.804(3) 100.6
C1 H1A N4 . 0.93 2.53 2.975(3) 109.6
O1 H1 N6 1_454 0.82 1.948 2.740(3) 161.92
C2 H2 N4 3_655 0.93 2.59 3.001(3) 107
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
C2 N1 N2 C1 . -0.1(2)
C3 N1 N2 C1 . 178.50(18)
N4 Cu1 N3 C2 . -172.9(2)
N4 Cu1 N3 C2 3_655 7.1(2)
N4 Cu1 N3 C1 . 5.6(2)
N4 Cu1 N3 C1 3_655 -174.4(2)
N1 N2 C1 N3 . 0.3(3)
C2 N3 C1 N2 . -0.4(3)
Cu1 N3 C1 N2 . -179.22(16)
N2 N1 C2 N3 . -0.2(2)
C3 N1 C2 N3 . -178.57(18)
C1 N3 C2 N1 . 0.4(2)
Cu1 N3 C2 N1 . 179.15(13)
C2 N1 C3 C8 . -168.3(2)
N2 N1 C3 C8 . 13.5(3)
C2 N1 C3 C4 . 13.4(3)
N2 N1 C3 C4 . -164.82(18)
C8 C3 C4 C5 . 1.0(3)
N1 C3 C4 C5 . 179.28(18)
C3 C4 C5 C6 . 0.3(3)
C4 C5 C6 O1 . 177.67(19)
C4 C5 C6 C7 . -1.5(3)
O1 C6 C7 C8 . -177.75(19)
C5 C6 C7 C8 . 1.5(3)
C4 C3 C8 C7 . -1.0(3)
N1 C3 C8 C7 . -179.32(18)
C6 C7 C8 C3 . -0.2(3)
