#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/45/2204507.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_2204507
loop_
_publ_author_name
'Huo, Li-Hua'
'Lu, Zhen-Zhong'
'Gao, Shan'
'Zhao, Hui'
'Zhao, Jing-Gui'
_publ_section_title
;
 Bis[μ-3-methoxysalicylaldehyde
 (4-methoxybenzoyl)hydrazonato]bis[pyridinecopper(II)] methanol
 disolvate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1636
_journal_page_last               m1638
_journal_paper_doi               10.1107/S1600536804025413
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '[Cu2 (C16 H14 N2 O4)2 (C5 H5 N)2], 2C H4 O'
_chemical_formula_moiety         'C42 H38 Cu2 N6 O8, 2C H4 O'
_chemical_formula_sum            'C44 H46 Cu2 N6 O10'
_chemical_formula_weight         945.97
_chemical_name_systematic
;
Bis[μ-3-methoxysalicylaldehyde
(4-methoxybenzoyl)hydrazonato]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                105.25(3)
_cell_angle_beta                 102.68(3)
_cell_angle_gamma                104.42(3)
_cell_formula_units_Z            1
_cell_length_a                   7.8618(16)
_cell_length_b                   11.709(2)
_cell_length_c                   13.231(3)
_cell_measurement_reflns_used    10363
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.18
_cell_volume                     1083.8(5)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scan'
_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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10513
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.046
_exptl_absorpt_correction_T_max  0.842
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0599P)²+0.1918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                4285
_reflns_number_total             4904
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6106.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_database_code               2204507
_cod_database_fobs_code          2204507
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
Cu1 0.07761(3) 0.371755(19) 0.495643(17) 0.04083(9) Uani d . 1 Cu
O1 0.2131(2) 0.54646(12) 0.56161(11) 0.0465(3) Uani d . 1 O
O2 -0.0539(2) 0.19488(12) 0.41417(11) 0.0458(3) Uani d . 1 O
O3 0.4327(2) 0.76335(13) 0.70342(12) 0.0535(4) Uani d . 1 O
O4 -0.4072(2) -0.33815(13) 0.04304(13) 0.0633(4) Uani d . 1 O
O5 -0.0682(3) 0.25805(18) 0.06636(14) 0.0709(5) Uani d . 1 O
N1 0.1418(2) 0.36121(14) 0.36238(12) 0.0396(3) Uani d . 1 N
N2 0.0584(2) 0.24466(14) 0.27894(13) 0.0428(3) Uani d . 1 N
N3 0.0264(2) 0.35821(15) 0.63478(13) 0.0428(3) Uani d . 1 N
C1 0.3390(2) 0.61096(16) 0.52829(15) 0.0391(4) Uani d . 1 C
C2 0.4567(3) 0.73189(17) 0.60147(15) 0.0419(4) Uani d . 1 C
C3 0.5843(3) 0.80772(18) 0.57015(18) 0.0485(4) Uani d . 1 C
C4 0.6063(3) 0.76475(19) 0.46601(18) 0.0516(5) Uani d . 1 C
C5 0.5010(3) 0.64678(19) 0.39552(17) 0.0467(4) Uani d . 1 C
C6 0.3662(2) 0.56813(16) 0.42440(15) 0.0390(4) Uani d . 1 C
C7 0.2637(3) 0.44517(17) 0.34612(15) 0.0420(4) Uani d . 1 C
C8 0.5572(3) 0.8773(2) 0.78264(19) 0.0632(6) Uani d . 1 C
C9 -0.0379(3) 0.16529(17) 0.31703(15) 0.0405(4) Uani d . 1 C
C10 -0.1301(3) 0.03346(17) 0.24294(15) 0.0419(4) Uani d . 1 C
C11 -0.1013(3) -0.01156(18) 0.14212(17) 0.0465(4) Uani d . 1 C
C12 -0.1901(3) -0.13429(18) 0.07315(17) 0.0497(5) Uani d . 1 C
C13 -0.3111(3) -0.21551(17) 0.10474(17) 0.0483(4) Uani d . 1 C
C14 -0.3401(3) -0.1728(2) 0.20597(18) 0.0584(6) Uani d . 1 C
C15 -0.2502(3) -0.05112(19) 0.27387(17) 0.0514(5) Uani d . 1 C
C16 -0.3850(4) -0.3849(2) -0.0631(2) 0.0708(7) Uani d . 1 C
C17 -0.0869(3) 0.2513(2) 0.63504(19) 0.0572(5) Uani d . 1 C
C18 -0.1251(4) 0.2386(3) 0.7287(2) 0.0711(7) Uani d . 1 C
C19 -0.0455(4) 0.3374(3) 0.8253(2) 0.0731(7) Uani d . 1 C
C20 0.0662(4) 0.4468(2) 0.82514(19) 0.0694(7) Uani d . 1 C
C21 0.1007(3) 0.4543(2) 0.72918(17) 0.0533(5) Uani d . 1 C
C22 -0.2536(5) 0.1924(4) 0.0208(3) 0.1075(12) Uani d . 1 C
H3 0.6561 0.8876 0.6182 0.058 Uiso calc R 1 H
H4 0.6921 0.8161 0.4448 0.062 Uiso calc R 1 H
H5 0.5185 0.6180 0.3273 0.056 Uiso calc R 1 H
H7 0.2869 0.4247 0.2788 0.050 Uiso calc R 1 H
H8A 0.6812 0.8763 0.7915 0.095 Uiso calc R 1 H
H8B 0.5319 0.8872 0.8516 0.095 Uiso calc R 1 H
H8C 0.5428 0.9458 0.7585 0.095 Uiso calc R 1 H
H11 -0.0199 0.0423 0.1204 0.056 Uiso calc R 1 H
H12 -0.1686 -0.1620 0.0060 0.060 Uiso calc R 1 H
H14 -0.4208 -0.2270 0.2278 0.070 Uiso calc R 1 H
H15 -0.2694 -0.0243 0.3418 0.062 Uiso calc R 1 H
H17 -0.1410 0.1838 0.5697 0.069 Uiso calc R 1 H
H18 -0.2042 0.1637 0.7265 0.085 Uiso calc R 1 H
H19 -0.0674 0.3300 0.8899 0.088 Uiso calc R 1 H
H20 0.1188 0.5159 0.8894 0.083 Uiso calc R 1 H
H21 0.1786 0.5290 0.7301 0.064 Uiso calc R 1 H
H23 -0.0335 0.2577 0.1294 0.106 Uiso calc R 1 H
H16A -0.4238 -0.3380 -0.1078 0.106 Uiso calc R 1 H
H16B -0.4588 -0.4716 -0.0975 0.106 Uiso calc R 1 H
H16C -0.2577 -0.3766 -0.0550 0.106 Uiso calc R 1 H
H22A -0.3190 0.2241 0.0689 0.161 Uiso calc R 1 H
H22B -0.2736 0.1054 0.0107 0.161 Uiso calc R 1 H
H22C -0.2977 0.2021 -0.0491 0.161 Uiso calc R 1 H
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
_geom_angle_publ_flag
O1 Cu1 N1 . 92.90(7) yes
O1 Cu1 O2 . 173.85(5) yes
O1 Cu1 N3 . 93.09(7) yes
O2 Cu1 N3 . 93.05(7) yes
N1 Cu1 N3 . 170.26(6) yes
N1 Cu1 O2 . 80.97(7) yes
O1 Cu1 O1 2_566 83.61(5) yes
O1 Cu1 O2 2_566 96.42(5) yes
O1 Cu1 N1 2_566 95.63(6) yes
O1 Cu1 N3 2_566 92.71(5) yes
O1 C1 C6 . 124.46(16) no
O1 C1 C2 . 118.13(16) no
O2 C9 N2 . 124.11(16) no
O2 C9 C10 . 118.22(16) no
O3 C8 H8C . 109.5 no
O3 C2 C3 . 124.18(17) no
O3 C2 C1 . 114.36(16) no
O3 C8 H8A . 109.5 no
O3 C8 H8B . 109.5 no
O4 C13 C12 . 124.62(19) no
O4 C13 C14 . 115.95(18) no
O4 C16 H16A . 109.5 no
O4 C16 H16B . 109.5 no
O4 C16 H16C . 109.5 no
O5 C22 H22A . 109.5 no
O5 C22 H22B . 109.5 no
O5 C22 H22C . 109.5 no
N1 C7 C6 . 124.80(17) no
N1 C7 H7 . 117.6 no
N2 N1 Cu1 . 115.01(11) no
N2 C9 C10 . 117.66(16) no
N3 C17 C18 . 122.1(2) no
N3 C17 H17 . 118.9 no
N3 C21 C20 . 122.4(2) no
N3 C21 H21 . 118.8 no
C1 O1 Cu1 . 126.19(12) no
C1 C6 C7 . 122.60(16) no
C2 O3 C8 . 116.79(16) no
C2 C3 C4 . 120.19(18) no
C2 C3 H3 . 119.9 no
C3 C2 C1 . 121.45(17) no
C3 C4 H4 . 120.1 no
C4 C5 C6 . 121.28(18) no
C4 C5 H5 . 119.4 no
C4 C3 H3 . 119.9 no
C5 C6 C1 . 119.79(17) no
C5 C6 C7 . 117.60(17) no
C5 C4 C3 . 119.76(18) no
C5 C4 H4 . 120.1 no
C6 C7 H7 . 117.6 no
C6 C1 C2 . 117.41(16) no
C6 C5 H5 . 119.4 no
C7 N1 N2 . 117.65(15) no
C7 N1 Cu1 . 127.03(13) no
C9 N2 N1 . 108.89(14) no
C9 O2 Cu1 . 110.83(12) no
C10 C11 H11 . 119.1 no
C10 C15 H15 . 119.3 no
C11 C12 C13 . 119.61(18) no
C11 C12 H12 . 120.2 no
C11 C10 C15 . 117.36(17) no
C11 C10 C9 . 122.48(17) no
C12 C11 C10 . 121.88(18) no
C12 C11 H11 . 119.1 no
C12 C13 C14 . 119.42(18) no
C13 C12 H12 . 120.2 no
C13 O4 C16 . 117.71(17) no
C13 C14 H14 . 119.8 no
C14 C15 C10 . 121.34(19) no
C14 C15 H15 . 119.3 no
C15 C14 C13 . 120.4(2) no
C15 C14 H14 . 119.8 no
C15 C10 C9 . 120.15(17) no
C17 N3 Cu1 . 120.51(14) no
C17 C18 H18 . 120.3 no
C18 C17 H17 . 118.9 no
C18 C19 H19 . 120.6 no
C19 C20 H20 . 120.3 no
C19 C20 C21 . 119.4(2) no
C19 C18 C17 . 119.3(2) no
C19 C18 H18 . 120.3 no
C20 C19 C18 . 118.9(2) no
C20 C19 H19 . 120.6 no
C20 C21 H21 . 118.8 no
C21 C20 H20 . 120.3 no
C21 N3 C17 . 117.86(18) no
C21 N3 Cu1 . 121.63(14) no
C22 O5 H23 . 109.5 no
H8A C8 H8B . 109.5 no
H8A C8 H8C . 109.5 no
H8B C8 H8C . 109.5 no
H16A C16 H16B . 109.5 no
H16A C16 H16C . 109.5 no
H16B C16 H16C . 109.5 no
H22A C22 H22C . 109.5 no
H22A C22 H22B . 109.5 no
H22B C22 H22C . 109.5 no
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 O1 . 1.910(2) yes
Cu1 N1 . 1.920(2) yes
Cu1 O2 . 1.947(2) yes
Cu1 N3 . 2.006(2) yes
Cu1 O1 2_566 2.725(3) yes
O2 C9 . 1.283(2) yes
N2 C9 . 1.324(2) yes
N1 N2 . 1.398(2) yes
N1 C7 . 1.290(2) yes
O1 C1 . 1.319(2) no
O3 C2 . 1.369(2) no
O3 C8 . 1.414(3) no
O4 C13 . 1.368(2) no
O4 C16 . 1.432(3) no
O5 C22 . 1.376(4) no
O5 H23 . 0.8200 no
N3 C21 . 1.334(3) no
N3 C17 . 1.345(3) no
C1 C6 . 1.417(3) no
C1 C2 . 1.425(3) no
C2 C3 . 1.378(3) no
C3 C4 . 1.402(3) no
C3 H3 . 0.9300 no
C4 C5 . 1.370(3) no
C4 H4 . 0.9300 no
C5 C6 . 1.412(3) no
C5 H5 . 0.9300 no
C6 C7 . 1.438(3) no
C7 H7 . 0.9300 no
C8 H8A . 0.9600 no
C8 H8B . 0.9600 no
C8 H8C . 0.9600 no
C9 C10 . 1.484(3) no
C10 C11 . 1.390(3) no
C10 C15 . 1.399(3) no
C11 C12 . 1.384(3) no
C11 H11 . 0.9300 no
C12 C13 . 1.385(3) no
C12 H12 . 0.9300 no
C13 C14 . 1.391(3) no
C14 C15 . 1.372(3) no
C14 H14 . 0.9300 no
C15 H15 . 0.9300 no
C16 H16A . 0.9600 no
C16 H16B . 0.9600 no
C16 H16C . 0.9600 no
C17 C18 . 1.374(3) no
C17 H17 . 0.9300 no
C18 C19 . 1.369(4) no
C18 H18 . 0.9300 no
C19 C20 . 1.362(4) no
C19 H19 . 0.9300 no
C20 C21 . 1.375(3) no
C20 H20 . 0.9300 no
C21 H21 . 0.9300 no
C22 H22A . 0.9600 no
C22 H22B . 0.9600 no
C22 H22C . 0.9600 no
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
_geom_hbond_publ_flag
O5 H23 N2 0.82 2.01 2.830(2) 175 yes
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
_geom_torsion_publ_flag
Cu1 O1 C1 C6 14.6(3) no
Cu1 O1 C1 C2 -165.11(13) no
Cu1 O2 C9 N2 1.2(2) no
Cu1 O2 C9 C10 -179.90(10) no
Cu1 N1 N2 C9 -4.41(19) no
Cu1 N1 C7 C6 -4.8(3) no
Cu1 N3 C17 C18 180.0(2) no
Cu1 N3 C21 C20 179.63(19) no
O1 Cu1 N1 C7 11.18(17) no
O1 Cu1 N1 N2 -175.41(12) no
O1 Cu1 N3 C21 -5.84(17) no
O1 Cu1 N3 C17 173.31(17) no
O1 C1 C6 C7 -3.4(3) no
O1 C1 C6 C5 177.74(18) no
O1 C1 C2 O3 4.7(3) no
O1 C1 C2 C3 -176.23(18) no
O2 Cu1 N3 C17 -7.00(17) no
O2 Cu1 N3 C21 173.85(16) no
O2 Cu1 N1 N2 4.07(12) no
O2 Cu1 N1 C7 -169.34(18) no
O2 C9 C10 C15 8.2(3) no
O2 C9 C10 C11 -171.30(18) no
O3 C2 C3 C4 176.34(19) no
O4 C13 C14 C15 -179.9(2) no
N1 Cu1 O1 C1 -15.88(16) no
N1 Cu1 O2 C9 -2.81(13) no
N1 N2 C9 O2 2.1(3) no
N1 N2 C9 C10 -176.84(15) no
N2 C9 C10 C11 7.7(3) no
N2 C9 C10 C15 -172.83(19) no
N2 N1 C7 C6 -178.06(17) no
N3 Cu1 O1 C1 156.43(16) no
N3 Cu1 O2 C9 -175.07(13) no
N3 C17 C18 C19 -0.2(4) no
C1 C2 C3 C4 -2.7(3) no
C1 C6 C7 N1 -1.8(3) no
C2 C3 C4 C5 -0.3(3) no
C2 C1 C6 C5 -2.5(3) no
C2 C1 C6 C7 176.30(17) no
C3 C4 C5 C6 1.7(3) no
C4 C5 C6 C1 -0.3(3) no
C4 C5 C6 C7 -179.16(19) no
C6 C1 C2 O3 -175.09(16) no
C6 C1 C2 C3 4.0(3) no
C5 C6 C7 N1 177.07(19) no
C7 N1 N2 C9 169.65(17) no
C8 O3 C2 C3 -4.7(3) no
C8 O3 C2 C1 174.37(19) no
C9 C10 C11 C12 -179.11(19) no
C9 C10 C15 C14 178.7(2) no
C10 C11 C12 C13 -0.2(3) no
C11 C12 C13 O4 179.5(2) no
C11 C12 C13 C14 -0.7(3) no
C11 C10 C15 C14 -1.9(3) no
C12 C13 C14 C15 0.3(4) no
C13 C14 C15 C10 1.1(4) no
C15 C10 C11 C12 1.4(3) no
C16 O4 C13 C12 -1.8(3) no
C16 O4 C13 C14 178.4(2) no
C17 C18 C19 C20 1.5(5) no
C17 N3 C21 C20 0.5(3) no
C18 C19 C20 C21 -1.9(5) no
C19 C20 C21 N3 0.9(4) no
C21 N3 C17 C18 -0.8(4) no
