#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/02/2230232.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_2230232
loop_
_publ_author_name
'Liu, Yan'
'Wang, Zuoxiang'
'Zhang, Hai'
_publ_section_title
;
 Bis(2-hydroxybenzoato-κO)bis[3-(4-methoxyphenyl)-4-(4-methylphenyl)-5-(2-pyridyl)-4H-1,2,4-triazole-κ²N¹,N⁵]copper(II)
 dihydrate
;
_journal_coeditor_code           BR2165
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m697
_journal_paper_doi               10.1107/S1600536811016126
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (C7 H5 O3)2 (C21 H18 N4 O)2], 2H2 O'
_chemical_formula_moiety         'C56 H46 Cu N8 O8, 2(H2 O)'
_chemical_formula_sum            'C56 H50 Cu N8 O10'
_chemical_formula_weight         1058.58
_chemical_name_systematic
;
Bis(2-hydroxybenzoato-κO)bis[3-(4-methoxyphenyl)-4-(4-methylphenyl)-
5-(2-pyridyl)-4H-1,2,4-triazole-κ²N¹,N⁵]copper(II)
dihydrate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.556(2)
_cell_angle_beta                 91.501(2)
_cell_angle_gamma                101.843(2)
_cell_formula_units_Z            1
_cell_length_a                   8.5933(12)
_cell_length_b                   10.6467(15)
_cell_length_c                   14.578(2)
_cell_measurement_reflns_used    9999
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.434
_cell_volume                     1265.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       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  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9025
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  0.9423
_exptl_absorpt_correction_T_min  0.9332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            'blue '
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             551
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.334
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0365
_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)+(0.0507P)²+0.3303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                3891
_reflns_number_total             4413
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            br2165.cif
_cod_data_source_block           I
_cod_database_code               2230232
_cod_database_fobs_code          2230232
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.0000 1.0000 1.0000 0.03718(13) Uani d S 1 1 . .
N N1 0.01756(19) 0.84131(16) 0.90177(11) 0.0371(4) Uani d . 1 2 . .
O O3 0.10103(18) 0.91416(16) 1.12470(12) 0.0527(4) Uani d . 1 2 . .
N N3 0.15216(19) 0.73762(16) 0.79657(11) 0.0358(4) Uani d . 1 2 . .
C C8 0.2813(2) 0.70780(19) 0.73920(13) 0.0352(4) Uani d . 1 2 . .
N N4 0.22652(19) 1.06205(16) 0.96344(11) 0.0361(4) Uani d . 1 2 . .
O O2 -0.0191(2) 0.70109(16) 1.08112(12) 0.0595(4) Uani d . 1 2 . .
C C10 0.4232(3) 0.7231(2) 0.60350(15) 0.0441(5) Uani d . 1 2 . .
H H10 0.4341 0.7492 0.5470 0.053 Uiso calc R 1 2 . .
N N2 -0.0804(2) 0.72205(16) 0.85894(12) 0.0394(4) Uani d . 1 2 . .
C C2 0.0031(2) 0.6597(2) 0.79623(14) 0.0374(5) Uani d . 1 2 . .
C C20 -0.1732(3) 0.4437(2) 0.77843(15) 0.0444(5) Uani d . 1 2 . .
H H20 -0.1991 0.4751 0.8399 0.053 Uiso calc R 1 2 . .
O O1 -0.2764(2) 0.14805(16) 0.58065(12) 0.0675(5) Uani d . 1 2 . .
C C13 0.3854(3) 0.6414(2) 0.76912(15) 0.0434(5) Uani d . 1 2 . .
H H13 0.3714 0.6120 0.8242 0.052 Uiso calc R 1 2 . .
C C22 0.0056(3) 0.8111(2) 1.13733(16) 0.0449(5) Uani d . 1 2 . .
C C15 -0.0608(2) 0.5241(2) 0.73933(14) 0.0390(5) Uani d . 1 2 . .
C C3 0.2794(2) 0.97083(19) 0.89747(13) 0.0343(4) Uani d . 1 2 . .
C C9 0.2979(3) 0.7490(2) 0.65663(15) 0.0415(5) Uani d . 1 2 . .
H H9 0.2259 0.7936 0.6370 0.050 Uiso calc R 1 2 . .
C C1 0.1555(2) 0.85032(19) 0.86417(13) 0.0351(4) Uani d . 1 2 . .
C C12 0.5121(3) 0.6189(2) 0.71555(16) 0.0503(6) Uani d . 1 2 . .
H H12 0.5848 0.5757 0.7361 0.060 Uiso calc R 1 2 . .
C C23 -0.0796(3) 0.8294(2) 1.22638(15) 0.0449(5) Uani d . 1 2 . .
C C6 0.4775(3) 1.2099(2) 0.97157(16) 0.0483(5) Uani d . 1 2 . .
H H6 0.5423 1.2933 0.9965 0.058 Uiso calc R 1 2 . .
O O4 0.0620(3) 1.05550(18) 1.28368(14) 0.0759(6) Uani d . 1 2 . .
H H4 0.1018 1.0359 1.2332 0.114 Uiso calc R 1 2 . .
C C16 -0.0206(3) 0.4745(2) 0.64802(15) 0.0492(5) Uani d . 1 2 . .
H H16 0.0558 0.5268 0.6208 0.059 Uiso calc R 1 2 . .
C C7 0.3238(3) 1.1798(2) 0.99837(15) 0.0440(5) Uani d . 1 2 . .
H H7 0.2871 1.2438 1.0421 0.053 Uiso calc R 1 2 . .
C C11 0.5333(3) 0.6588(2) 0.63257(16) 0.0449(5) Uani d . 1 2 . .
C C4 0.4326(2) 0.9949(2) 0.86936(15) 0.0439(5) Uani d . 1 2 . .
H H4A 0.4676 0.9305 0.8250 0.053 Uiso calc R 1 2 . .
C C17 -0.0932(3) 0.3490(2) 0.59781(16) 0.0543(6) Uani d . 1 2 . .
H H17 -0.0652 0.3164 0.5370 0.065 Uiso calc R 1 2 . .
C C26 -0.2262(5) 0.8563(4) 1.3948(2) 0.0911(11) Uani d . 1 2 . .
H H26 -0.2734 0.8640 1.4520 0.109 Uiso calc R 1 2 . .
C C18 -0.2082(3) 0.2706(2) 0.63742(16) 0.0486(6) Uani d . 1 2 . .
C C19 -0.2477(3) 0.3182(2) 0.72827(16) 0.0477(5) Uani d . 1 2 . .
H H19 -0.3240 0.2658 0.7554 0.057 Uiso calc R 1 2 . .
C C5 0.5333(3) 1.1165(2) 0.90825(16) 0.0479(5) Uani d . 1 2 . .
H H5 0.6377 1.1343 0.8914 0.058 Uiso calc R 1 2 . .
C C25 -0.1175(4) 0.9602(3) 1.38054(19) 0.0770(9) Uani d . 1 2 . .
H H25 -0.0921 1.0390 1.4273 0.092 Uiso calc R 1 2 . .
C C14 0.6730(3) 0.6345(3) 0.5758(2) 0.0704(8) Uani d . 1 2 . .
H H14A 0.6468 0.6308 0.5107 0.106 Uiso calc R 1 2 . .
H H14B 0.6971 0.5520 0.5806 0.106 Uiso calc R 1 2 . .
H H14C 0.7641 0.7051 0.5999 0.106 Uiso calc R 1 2 . .
C C28 -0.1937(3) 0.7267(3) 1.24335(19) 0.0616(7) Uani d . 1 2 . .
H H28 -0.2207 0.6470 1.1976 0.074 Uiso calc R 1 2 . .
C C24 -0.0433(3) 0.9495(2) 1.29565(17) 0.0553(6) Uani d . 1 2 . .
C C27 -0.2678(4) 0.7400(4) 1.3262(2) 0.0855(10) Uani d . 1 2 . .
H H27 -0.3457 0.6705 1.3358 0.103 Uiso calc R 1 2 . .
C C21 -0.3755(4) 0.0575(3) 0.6233(2) 0.0760(8) Uani d . 1 2 . .
H H21A -0.3161 0.0441 0.6756 0.114 Uiso calc R 1 2 . .
H H21B -0.4118 -0.0255 0.5776 0.114 Uiso calc R 1 2 . .
H H21C -0.4657 0.0925 0.6457 0.114 Uiso calc R 1 2 . .
O O1W 0.1915(2) 0.5712(2) 0.96350(16) 0.0732(6) Uani d . 1 2 . .
H H1F 0.145(5) 0.488(4) 0.949(3) 0.110 Uiso d . 1 2 . .
H H1E 0.139(5) 0.611(4) 0.997(3) 0.110 Uiso d . 1 2 . .
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
N1 Cu1 N4 . . 80.33(6) .
N1 Cu1 O3 . . 91.91(6) .
N4 Cu1 O3 . . 91.28(6) .
C1 N1 N2 . . 109.27(16) .
C1 N1 Cu1 . . 114.35(13) .
N2 N1 Cu1 . . 136.33(13) .
C22 O3 Cu1 . . 112.82(13) .
C1 N3 C2 . . 105.25(16) .
C1 N3 C8 . . 126.29(16) .
C2 N3 C8 . . 128.45(16) .
C13 C8 C9 . . 121.51(19) .
C13 C8 N3 . . 119.36(18) .
C9 C8 N3 . . 119.12(17) .
C7 N4 C3 . . 118.56(17) .
C7 N4 Cu1 . . 126.69(14) .
C3 N4 Cu1 . . 114.75(13) .
C9 C10 C11 . . 121.3(2) .
C9 C10 H10 . . 119.3 .
C11 C10 H10 . . 119.3 .
C2 N2 N1 . . 106.23(17) .
N2 C2 N3 . . 110.19(17) .
N2 C2 C15 . . 121.90(19) .
N3 C2 C15 . . 127.87(18) .
C19 C20 C15 . . 121.4(2) .
C19 C20 H20 . . 119.3 .
C15 C20 H20 . . 119.3 .
C18 O1 C21 . . 117.3(2) .
C8 C13 C12 . . 118.6(2) .
C8 C13 H13 . . 120.7 .
C12 C13 H13 . . 120.7 .
O2 C22 O3 . . 124.0(2) .
O2 C22 C23 . . 119.7(2) .
O3 C22 C23 . . 116.2(2) .
C20 C15 C16 . . 118.57(19) .
C20 C15 C2 . . 117.05(18) .
C16 C15 C2 . . 124.3(2) .
N4 C3 C4 . . 121.70(19) .
N4 C3 C1 . . 111.19(17) .
C4 C3 C1 . . 127.11(18) .
C8 C9 C10 . . 118.85(19) .
C8 C9 H9 . . 120.6 .
C10 C9 H9 . . 120.6 .
N1 C1 N3 . . 109.03(17) .
N1 C1 C3 . . 119.30(17) .
N3 C1 C3 . . 131.67(17) .
C11 C12 C13 . . 121.7(2) .
C11 C12 H12 . . 119.1 .
C13 C12 H12 . . 119.1 .
C28 C23 C24 . . 118.2(2) .
C28 C23 C22 . . 120.7(2) .
C24 C23 C22 . . 121.1(2) .
C5 C6 C7 . . 119.5(2) .
C5 C6 H6 . . 120.3 .
C7 C6 H6 . . 120.3 .
C24 O4 H4 . . 109.5 .
C17 C16 C15 . . 120.4(2) .
C17 C16 H16 . . 119.8 .
C15 C16 H16 . . 119.8 .
N4 C7 C6 . . 122.09(19) .
N4 C7 H7 . . 119.0 .
C6 C7 H7 . . 119.0 .
C12 C11 C10 . . 118.0(2) .
C12 C11 C14 . . 120.9(2) .
C10 C11 C14 . . 121.1(2) .
C3 C4 C5 . . 118.87(19) .
C3 C4 H4A . . 120.6 .
C5 C4 H4A . . 120.6 .
C16 C17 C18 . . 120.2(2) .
C16 C17 H17 . . 119.9 .
C18 C17 H17 . . 119.9 .
C25 C26 C27 . . 120.9(3) .
C25 C26 H26 . . 119.5 .
C27 C26 H26 . . 119.5 .
O1 C18 C19 . . 124.4(2) .
O1 C18 C17 . . 115.7(2) .
C19 C18 C17 . . 119.8(2) .
C20 C19 C18 . . 119.5(2) .
C20 C19 H19 . . 120.2 .
C18 C19 H19 . . 120.2 .
C6 C5 C4 . . 119.2(2) .
C6 C5 H5 . . 120.4 .
C4 C5 H5 . . 120.4 .
C26 C25 C24 . . 120.2(3) .
C26 C25 H25 . . 119.9 .
C24 C25 H25 . . 119.9 .
C11 C14 H14A . . 109.5 .
C11 C14 H14B . . 109.5 .
H14A C14 H14B . . 109.5 .
C11 C14 H14C . . 109.5 .
H14A C14 H14C . . 109.5 .
H14B C14 H14C . . 109.5 .
C27 C28 C23 . . 121.4(3) .
C27 C28 H28 . . 119.3 .
C23 C28 H28 . . 119.3 .
O4 C24 C25 . . 118.4(3) .
O4 C24 C23 . . 122.1(2) .
C25 C24 C23 . . 119.5(3) .
C28 C27 C26 . . 119.6(3) .
C28 C27 H27 . . 120.2 .
C26 C27 H27 . . 120.2 .
O1 C21 H21A . . 109.5 .
O1 C21 H21B . . 109.5 .
H21A C21 H21B . . 109.5 .
O1 C21 H21C . . 109.5 .
H21A C21 H21C . . 109.5 .
H21B C21 H21C . . 109.5 .
H1F O1W H1E . . 109(4) .
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 . 1.9773(16) n
Cu1 N4 . 2.0497(16) n
Cu1 O3 . 2.4322(16) n
N1 C1 . 1.314(2) n
N1 N2 . 1.368(2) n
O3 C22 . 1.282(3) n
N3 C1 . 1.357(2) n
N3 C2 . 1.375(3) n
N3 C8 . 1.449(2) n
C8 C13 . 1.369(3) n
C8 C9 . 1.376(3) n
N4 C7 . 1.334(3) n
N4 C3 . 1.357(2) n
O2 C22 . 1.236(3) n
C10 C9 . 1.378(3) n
C10 C11 . 1.387(3) n
C10 H10 . 0.9300 n
N2 C2 . 1.318(3) n
C2 C15 . 1.471(3) n
C20 C19 . 1.378(3) n
C20 C15 . 1.381(3) n
C20 H20 . 0.9300 n
O1 C18 . 1.373(3) n
O1 C21 . 1.419(3) n
C13 C12 . 1.384(3) n
C13 H13 . 0.9300 n
C22 C23 . 1.500(3) n
C15 C16 . 1.392(3) n
C3 C4 . 1.381(3) n
C3 C1 . 1.461(3) n
C9 H9 . 0.9300 n
C12 C11 . 1.378(3) n
C12 H12 . 0.9300 n
C23 C28 . 1.385(3) n
C23 C24 . 1.402(3) n
C6 C5 . 1.364(3) n
C6 C7 . 1.383(3) n
C6 H6 . 0.9300 n
O4 C24 . 1.344(3) n
O4 H4 . 0.8200 n
C16 C17 . 1.374(3) n
C16 H16 . 0.9300 n
C7 H7 . 0.9300 n
C11 C14 . 1.508(3) n
C4 C5 . 1.384(3) n
C4 H4A . 0.9300 n
C17 C18 . 1.387(3) n
C17 H17 . 0.9300 n
C26 C25 . 1.354(5) n
C26 C27 . 1.372(5) n
C26 H26 . 0.9300 n
C18 C19 . 1.380(3) n
C19 H19 . 0.9300 n
C5 H5 . 0.9300 n
C25 C24 . 1.398(4) n
C25 H25 . 0.9300 n
C14 H14A . 0.9600 n
C14 H14B . 0.9600 n
C14 H14C . 0.9600 n
C28 C27 . 1.372(4) n
C28 H28 . 0.9300 n
C27 H27 . 0.9300 n
C21 H21A . 0.9600 n
C21 H21B . 0.9600 n
C21 H21C . 0.9600 n
O1W H1F . 0.87(4) n
O1W H1E . 0.78(4) n
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
O1W H1F O2 2_567 0.87(4) 2.02(4) 2.885(3) 175(4)
O1W H1E O2 . 0.78(4) 2.08(4) 2.865(3) 174(4)
O4 H4 O3 . 0.82 1.79 2.522(3) 147
