#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/89/2018921.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_2018921
loop_
_publ_author_name
'Zhao, Ning'
_publ_section_title
;
 Bis[μ-2-({2-[2-(2-chlorophenoxy)-1-oxidoethylidene]hydrazinylidene}methyl)phenolato]bis[pyridinecopper(II)]
 methanol disolvate
;
_journal_coeditor_code           OV3024
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              348
_journal_page_last               350
_journal_paper_doi               10.1107/S0108270113005118
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac
'[Cu2 (C15 H11 Cl1 N2 O3)2 (C5 H5 N1)2], 2C H4 O'
_chemical_formula_moiety         'C40 H32 Cl2 Cu2 N6 O6, 2(C H4 O)'
_chemical_formula_sum            'C42 H40 Cl2 Cu2 N6 O8'
_chemical_formula_weight         954.78
_chemical_name_systematic
;Bis[μ-2-({2-[2-(2-chlorophenoxy)-1-oxidoethylidene]hydrazinylidene}methyl)phenolato]bis[pyridinecopper(II)]
methanol disolvate
;
_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                111.615(3)
_cell_angle_beta                 92.294(4)
_cell_angle_gamma                101.130(4)
_cell_formula_units_Z            1
_cell_length_a                   7.5570(16)
_cell_length_b                   12.223(3)
_cell_length_c                   12.681(3)
_cell_measurement_reflns_used    13246
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     1060.5(4)
_computing_cell_refinement       'SMART (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenberg & Putz, 2010)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART 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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13246
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.188
_exptl_absorpt_correction_T_max  0.65
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0317
_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)+(0.0810P)²+0.1044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                4282
_reflns_number_total             4837
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ov3024.cif
_cod_data_source_block           I
_cod_database_code               2018921
_cod_database_fobs_code          2018921
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 0.37590(3) 0.061224(18) 0.603002(17) 0.03378(10) Uani d . 1 1
Cl Cl1 0.77810(12) 0.66071(7) 0.85857(8) 0.0776(2) Uani d . 1 1
O O1 0.3539(2) -0.10268(12) 0.49997(11) 0.0386(3) Uani d . 1 1
O O2 0.63343(18) 0.44349(11) 0.89247(12) 0.0428(3) Uani d . 1 1
O O3 0.4260(2) 0.22579(12) 0.72112(11) 0.0406(3) Uani d . 1 1
N N1 0.4589(2) 0.02782(14) 0.73203(13) 0.0351(3) Uani d . 1 1
N N2 0.5186(2) 0.13030(15) 0.83313(13) 0.0404(4) Uani d . 1 1
N N3 0.2259(2) 0.09911(15) 0.49099(14) 0.0378(3) Uani d . 1 1
C C1 0.4044(3) -0.18859(17) 0.64073(16) 0.0362(4) Uani d . 1 1
C C2 0.4012(4) -0.29565(19) 0.66065(19) 0.0497(5) Uani d . 1 1
H H2 0.4378 -0.2897 0.7338 0.060 Uiso calc R 1 1
C C3 0.3463(4) -0.4065(2) 0.5758(2) 0.0648(7) Uani d . 1 1
H H3 0.3440 -0.4756 0.5909 0.078 Uiso calc R 1 1
C C4 0.2933(4) -0.4158(2) 0.4656(2) 0.0648(8) Uani d . 1 1
H H4 0.2568 -0.4915 0.4069 0.078 Uiso calc R 1 1
C C5 0.2946(4) -0.31361(19) 0.44298(18) 0.0493(5) Uani d . 1 1
H H5 0.2569 -0.3220 0.3692 0.059 Uiso calc R 1 1
C C6 0.3513(3) -0.19738(16) 0.52836(15) 0.0349(4) Uani d . 1 1
C C7 0.4607(3) -0.07590(18) 0.73625(16) 0.0380(4) Uani d . 1 1
H H7 0.5011 -0.0775 0.8058 0.046 Uiso calc R 1 1
C C8 0.4931(3) 0.22580(17) 0.81570(16) 0.0352(4) Uani d . 1 1
C C9 0.5449(3) 0.34423(17) 0.91923(17) 0.0410(4) Uani d . 1 1
H H9A 0.4360 0.3625 0.9532 0.049 Uiso calc R 1 1
H H9B 0.6248 0.3348 0.9755 0.049 Uiso calc R 1 1
C C10 0.8075(3) 0.44625(18) 0.86667(15) 0.0394(4) Uani d . 1 1
C C11 0.9012(3) 0.3566(2) 0.85754(19) 0.0482(5) Uani d . 1 1
H H11 0.8464 0.2891 0.8715 0.058 Uiso calc R 1 1
C C12 1.0772(3) 0.3678(3) 0.8275(2) 0.0607(6) Uani d . 1 1
H H12 1.1386 0.3069 0.8205 0.073 Uiso calc R 1 1
C C13 1.1611(4) 0.4679(3) 0.8082(2) 0.0705(8) Uani d . 1 1
H H13 1.2787 0.4748 0.7884 0.085 Uiso calc R 1 1
C C14 1.0693(4) 0.5583(3) 0.8183(2) 0.0648(7) Uani d . 1 1
H H14 1.1256 0.6263 0.8057 0.078 Uiso calc R 1 1
C C15 0.8950(3) 0.5475(2) 0.84694(19) 0.0487(5) Uani d . 1 1
C C16 0.1444(3) 0.0133(2) 0.39119(19) 0.0464(5) Uani d . 1 1
H H16 0.1528 -0.0659 0.3753 0.056 Uiso calc R 1 1
C C17 0.0476(3) 0.0381(3) 0.3103(2) 0.0583(6) Uani d . 1 1
H H17 -0.0078 -0.0236 0.2418 0.070 Uiso calc R 1 1
C C18 0.0351(4) 0.1557(3) 0.3331(2) 0.0630(7) Uani d . 1 1
H H18 -0.0270 0.1745 0.2796 0.076 Uiso calc R 1 1
C C19 0.1153(4) 0.2441(3) 0.4356(3) 0.0626(7) Uani d . 1 1
H H19 0.1064 0.3237 0.4536 0.075 Uiso calc R 1 1
C C20 0.2104(3) 0.2129(2) 0.5123(2) 0.0502(5) Uani d . 1 1
H H20 0.2657 0.2734 0.5816 0.060 Uiso calc R 1 1
O O4 0.6731(5) 0.1342(3) 1.0437(2) 0.1056(9) Uani d . 1 1
H H4A 0.6426 0.1475 0.9875 0.158 Uiso calc R 1 1
C C21 0.7959(6) 0.0597(5) 1.0163(4) 0.1166(16) Uani d . 1 1
H H21A 0.8402 0.0574 0.9458 0.175 Uiso calc R 1 1
H H21B 0.7365 -0.0204 1.0081 0.175 Uiso calc R 1 1
H H21C 0.8959 0.0906 1.0761 0.175 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
O1 Cu1 N1 92.16(6) y
O1 Cu1 O3 171.97(6) y
N1 Cu1 O3 80.88(6) y
O1 Cu1 N3 92.97(7) y
N1 Cu1 N3 163.82(7) y
O3 Cu1 N3 94.80(7) y
C6 O1 Cu1 126.52(12) ?
C10 O2 C9 117.34(16) ?
C8 O3 Cu1 109.78(12) ?
C7 N1 N2 117.42(16) ?
C7 N1 Cu1 127.99(13) ?
N2 N1 Cu1 114.56(12) ?
C8 N2 N1 109.07(15) ?
C16 N3 C20 117.57(19) ?
C16 N3 Cu1 121.48(15) ?
C20 N3 Cu1 120.90(15) ?
C2 C1 C6 119.23(18) ?
C2 C1 C7 117.62(18) ?
C6 C1 C7 123.14(17) ?
C3 C2 C1 121.7(2) ?
C3 C2 H2 119.1 ?
C1 C2 H2 119.1 ?
C2 C3 C4 119.3(2) ?
C2 C3 H3 120.3 ?
C4 C3 H3 120.3 ?
C5 C4 C3 120.6(2) ?
C5 C4 H4 119.7 ?
C3 C4 H4 119.7 ?
C4 C5 C6 121.8(2) ?
C4 C5 H5 119.1 ?
C6 C5 H5 119.1 ?
O1 C6 C5 118.63(17) ?
O1 C6 C1 124.02(16) ?
C5 C6 C1 117.35(17) ?
N1 C7 C1 124.19(17) ?
N1 C7 H7 117.9 ?
C1 C7 H7 117.9 ?
O3 C8 N2 125.54(17) ?
O3 C8 C9 119.02(17) ?
N2 C8 C9 115.42(17) ?
O2 C9 C8 113.26(16) ?
O2 C9 H9A 108.9 ?
C8 C9 H9A 108.9 ?
O2 C9 H9B 108.9 ?
C8 C9 H9B 108.9 ?
H9A C9 H9B 107.7 ?
O2 C10 C11 125.12(19) ?
O2 C10 C15 116.38(19) ?
C11 C10 C15 118.5(2) ?
C10 C11 C12 120.0(2) ?
C10 C11 H11 120.0 ?
C12 C11 H11 120.0 ?
C13 C12 C11 120.7(3) ?
C13 C12 H12 119.6 ?
C11 C12 H12 119.6 ?
C12 C13 C14 119.6(2) ?
C12 C13 H13 120.2 ?
C14 C13 H13 120.2 ?
C15 C14 C13 120.1(3) ?
C15 C14 H14 120.0 ?
C13 C14 H14 120.0 ?
C14 C15 C10 121.1(2) ?
C14 C15 Cl1 120.2(2) ?
C10 C15 Cl1 118.71(18) ?
N3 C16 C17 122.6(2) ?
N3 C16 H16 118.7 ?
C17 C16 H16 118.7 ?
C18 C17 C16 119.0(2) ?
C18 C17 H17 120.5 ?
C16 C17 H17 120.5 ?
C19 C18 C17 119.1(2) ?
C19 C18 H18 120.5 ?
C17 C18 H18 120.5 ?
C18 C19 C20 118.8(2) ?
C18 C19 H19 120.6 ?
C20 C19 H19 120.6 ?
N3 C20 C19 122.9(2) ?
N3 C20 H20 118.5 ?
C19 C20 H20 118.5 ?
C21 O4 H4A 109.5 ?
O4 C21 H21A 109.5 ?
O4 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
O4 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 1.9167(13) y
Cu1 N1 1.9356(16) y
Cu1 O3 1.9683(14) y
Cu1 N3 2.0188(17) y
Cl1 C15 1.746(3) ?
O1 C6 1.330(2) ?
O2 C10 1.365(2) ?
O2 C9 1.429(2) ?
O3 C8 1.283(2) y
N1 C7 1.291(3) ?
N1 N2 1.403(2) ?
N2 C8 1.312(3) y
N3 C16 1.338(3) ?
N3 C20 1.345(3) ?
C1 C2 1.417(3) ?
C1 C6 1.424(3) ?
C1 C7 1.431(3) ?
C2 C3 1.356(3) ?
C2 H2 0.9300 ?
C3 C4 1.396(4) ?
C3 H3 0.9300 ?
C4 C5 1.379(3) ?
C4 H4 0.9300 ?
C5 C6 1.403(3) ?
C5 H5 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.521(3) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.388(3) ?
C10 C15 1.399(3) ?
C11 C12 1.393(3) ?
C11 H11 0.9300 ?
C12 C13 1.376(4) ?
C12 H12 0.9300 ?
C13 C14 1.385(5) ?
C13 H13 0.9300 ?
C14 C15 1.375(4) ?
C14 H14 0.9300 ?
C16 C17 1.391(3) ?
C16 H16 0.9300 ?
C17 C18 1.380(4) ?
C17 H17 0.9300 ?
C18 C19 1.370(4) ?
C18 H18 0.9300 ?
C19 C20 1.390(3) ?
C19 H19 0.9300 ?
C20 H20 0.9300 ?
O4 C21 1.389(5) ?
O4 H4A 0.8200 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O4 H4A N2 0.82 2.06 2.851(3) 163.0
