#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202268.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_2202268
loop_
_publ_author_name
'Reinoso, Santiago'
'Vitoria, Pablo'
'San Felices, Leire'
'Lezama, Luis'
'Gutiérrez-Zorrilla, Juan M.'
_publ_section_title
;
 Bis(di-2-pyridylmethanediol-κ³N,O,N')copper(II) diacetate
 tetrahydrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m548
_journal_page_last               m550
_journal_paper_doi               10.1107/S1600536803014399
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '[Cu (C11 H10 N2 O2)2] (C2 H3 O2)2, 4H2 O'
_chemical_formula_moiety         'C22 H20 Cu N4 O4, 2(C2 H3 O2), 4(H2 O)'
_chemical_formula_sum            'C26 H34 Cu N4 O12'
_chemical_formula_weight         658.11
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6170(10)
_cell_length_b                   7.8765(9)
_cell_length_c                   23.103(3)
_cell_measurement_reflns_used    6500
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3.5
_cell_volume                     1552.8(3)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2002)'
_computing_data_reduction        CrysAlisRED
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF99.2 (Beurskens et al., 1999)'
_diffrn_detector_area_resol_mean '1024 \\times 1024 with blocks 2 \\times 2'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  Xcalibur
_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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12971
_diffrn_reflns_theta_full        30
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_min         3.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlisRED; Oxford Diffraction, 2002)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             686
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.343
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4480
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0490
_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)+(0.0588P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                2765
_reflns_number_total             4484
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6048.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2202268
_cod_database_fobs_code          2202268
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.0000 0.0000 0.0000 0.03418(12) Uani d S 1 . . Cu
O14 -0.03830(18) 0.26003(18) -0.05417(6) 0.0367(3) Uani d . 1 . . O
H14 -0.0435 0.2576 -0.0899 0.055 Uiso calc R 1 . . H
O15 -0.2598(2) 0.43429(19) -0.06184(7) 0.0479(4) Uani d . 1 . . O
H15 -0.2623 0.4341 -0.0975 0.072 Uiso calc R 1 . . H
N1 -0.2177(2) -0.0169(2) -0.04184(7) 0.0342(4) Uani d . 1 . . N
N13 -0.0808(2) 0.1706(2) 0.05422(7) 0.0362(4) Uani d . 1 . . N
C2 -0.2932(3) -0.1636(3) -0.05549(11) 0.0448(6) Uani d . 1 . . C
H2 -0.2429 -0.2654 -0.0445 0.054 Uiso calc R 1 . . H
C3 -0.4424(3) -0.1677(3) -0.08517(13) 0.0568(7) Uani d . 1 . . C
H3 -0.4919 -0.2708 -0.0949 0.068 Uiso calc R 1 . . H
C4 -0.5179(3) -0.0169(3) -0.10027(13) 0.0607(7) Uani d . 1 . . C
H4 -0.6198 -0.0171 -0.1198 0.073 Uiso calc R 1 . . H
C5 -0.4416(3) 0.1343(3) -0.08622(11) 0.0479(6) Uani d . 1 . . C
H5 -0.4909 0.2372 -0.0964 0.058 Uiso calc R 1 . . H
C6 -0.2907(2) 0.1307(3) -0.05680(9) 0.0339(5) Uani d . 1 . . C
C7 -0.1888(3) 0.2873(2) -0.03881(9) 0.0352(5) Uani d . 1 . . C
C8 -0.1650(2) 0.2981(2) 0.02719(10) 0.0356(5) Uani d . 1 . . C
C9 -0.2239(3) 0.4264(3) 0.05854(11) 0.0462(6) Uani d . 1 . . C
H9 -0.2825 0.5141 0.0394 0.055 Uiso calc R 1 . . H
C10 -0.1942(3) 0.4222(3) 0.11879(12) 0.0547(7) Uani d . 1 . . C
H10 -0.2319 0.5080 0.1407 0.066 Uiso calc R 1 . . H
C11 -0.1092(3) 0.2917(3) 0.14599(11) 0.0563(7) Uani d . 1 . . C
H11 -0.0891 0.2868 0.1866 0.068 Uiso calc R 1 . . H
C12 -0.0535(3) 0.1673(3) 0.11248(10) 0.0458(6) Uani d . 1 . . C
H12 0.0047 0.0784 0.1310 0.055 Uiso calc R 1 . . H
C20 -0.1655(3) 0.3480(3) -0.19680(11) 0.0532(7) Uani d . 1 . . C
C21 -0.1604(5) 0.3642(5) -0.26154(13) 0.0883(11) Uani d . 1 . . C
H21A -0.1804 0.2554 -0.2798 0.132 Uiso calc R 1 . . H
H21B -0.0588 0.4037 -0.2679 0.132 Uiso calc R 1 . . H
H21C -0.2387 0.4437 -0.2781 0.132 Uiso calc R 1 . . H
O1 -0.0614(2) 0.2591(2) -0.16774(8) 0.0582(5) Uani d . 1 . . O
O2 -0.2713(2) 0.4210(3) -0.17510(8) 0.0656(5) Uani d . 1 . . O
O10 -0.5910(3) 0.3908(3) -0.21450(10) 0.0762(6) Uani d D 1 . . O
O11 0.2041(3) 0.1290(3) -0.20391(11) 0.0742(6) Uani d D 1 . . O
H10A -0.4931(14) 0.409(5) -0.2079(14) 0.089 Uiso d D 1 . . H
H10B -0.619(4) 0.473(3) -0.2368(13) 0.089 Uiso d D 1 . . H
H11A 0.124(3) 0.184(4) -0.1972(15) 0.089 Uiso d D 1 . . H
H11B 0.263(3) 0.210(3) -0.2101(16) 0.089 Uiso d D 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 0 '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 0.006 '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 N1 3 . 180.00(14) ?
N1 Cu1 N13 3 3 87.86(7) y
N1 Cu1 N13 . 3 92.14(7) ?
N1 Cu1 N13 3 . 92.14(7) y
N1 Cu1 N13 . . 87.86(7) y
N13 Cu1 N13 3 . 180.00(11) ?
N1 Cu1 O14 3 3 75.63(6) y
N1 Cu1 O14 . 3 104.37(6) y
N13 Cu1 O14 3 3 73.86(6) y
N13 Cu1 O14 . 3 106.14(6) y
C7 O14 H14 . . 109.5 ?
C7 O15 H15 . . 109.5 ?
C2 N1 C6 . . 119.38(18) ?
C2 N1 Cu1 . . 124.37(15) y
C6 N1 Cu1 . . 116.25(13) y
C12 N13 C8 . . 119.5(2) ?
C12 N13 Cu1 . . 125.69(16) y
C8 N13 Cu1 . . 114.77(14) y
N1 C2 C3 . . 121.9(2) ?
N1 C2 H2 . . 119.1 ?
C3 C2 H2 . . 119.1 ?
C2 C3 C4 . . 118.9(2) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C3 C4 C5 . . 119.6(2) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C5 C6 . . 119.0(2) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
N1 C6 C5 . . 121.25(19) ?
N1 C6 C7 . . 113.31(18) ?
C5 C6 C7 . . 125.43(19) ?
O15 C7 O14 . . 113.88(17) ?
O15 C7 C8 . . 109.37(17) ?
O14 C7 C8 . . 105.19(17) ?
O15 C7 C6 . . 111.29(17) ?
O14 C7 C6 . . 108.72(16) ?
C8 C7 C6 . . 108.08(16) ?
N13 C8 C9 . . 121.2(2) ?
N13 C8 C7 . . 114.58(18) ?
C9 C8 C7 . . 124.2(2) ?
C10 C9 C8 . . 118.8(2) ?
C10 C9 H9 . . 120.6 ?
C8 C9 H9 . . 120.6 ?
C11 C10 C9 . . 119.7(2) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C10 C11 C12 . . 119.0(2) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
N13 C12 C11 . . 121.8(2) ?
N13 C12 H12 . . 119.1 ?
C11 C12 H12 . . 119.1 ?
O2 C20 O1 . . 123.5(2) ?
O2 C20 C21 . . 119.1(3) ?
O1 C20 C21 . . 117.4(3) ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
H10A O10 H10B . . 100(3) ?
H11A O11 H11B . . 100(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 N1 3 1.9918(17) y
Cu1 N1 . 1.9918(17) ?
Cu1 N13 3 2.0257(18) y
Cu1 N13 . 2.0257(18) ?
Cu1 O14 3 2.3990(14) y
O14 C7 . 1.408(3) y
O14 H14 . 0.8200 ?
O15 C7 . 1.381(2) y
O15 H15 . 0.8200 ?
N1 C2 . 1.342(3) ?
N1 C6 . 1.344(3) ?
N13 C12 . 1.334(3) ?
N13 C8 . 1.341(3) ?
C2 C3 . 1.371(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.377(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.537(3) ?
C7 C8 . 1.512(3) ?
C8 C9 . 1.381(3) ?
C9 C10 . 1.380(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.364(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.376(4) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C20 O2 . 1.240(3) ?
C20 O1 . 1.257(3) ?
C20 C21 . 1.508(4) ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
O10 H10A . 0.848(10) ?
O10 H10B . 0.845(10) ?
O11 H11A . 0.848(10) ?
O11 H11B . 0.842(10) ?
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
O14 H14 O1 . 0.82 1.78 2.603(2) 178
O15 H15 O2 . 0.82 1.79 2.607(3) 177
O10 H10A O2 . 0.848(10) 1.958(13) 2.788(3) 166(3)
O10 H10B O11 2_454 0.845(10) 1.906(12) 2.741(3) 169(3)
O11 H11A O1 . 0.848(10) 1.915(14) 2.741(3) 164(3)
O11 H11B O10 1_655 0.842(10) 1.910(11) 2.748(3) 173(4)
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
N13 Cu1 N1 C2 3 49.06(18)
N13 Cu1 N1 C2 . -130.94(18)
O14 Cu1 N1 C2 3 -24.82(19)
N13 Cu1 N1 C6 3 -130.93(15)
N13 Cu1 N1 C6 . 49.07(15)
O14 Cu1 N1 C6 3 155.19(14)
N1 Cu1 N13 C12 3 -49.05(18)
N1 Cu1 N13 C12 . 130.95(18)
O14 Cu1 N13 C12 3 26.61(19)
N1 Cu1 N13 C8 3 129.10(15)
N1 Cu1 N13 C8 . -50.90(15)
O14 Cu1 N13 C8 3 -155.24(14)
C6 N1 C2 C3 . 1.0(3)
Cu1 N1 C2 C3 . -179.0(2)
N1 C2 C3 C4 . -1.4(4)
C2 C3 C4 C5 . 1.1(4)
C3 C4 C5 C6 . -0.4(4)
C2 N1 C6 C5 . -0.3(3)
Cu1 N1 C6 C5 . 179.67(17)
C2 N1 C6 C7 . -179.4(2)
Cu1 N1 C6 C7 . 0.6(2)
C4 C5 C6 N1 . 0.0(4)
C4 C5 C6 C7 . 179.0(2)
N1 C6 C7 O15 . 171.84(18)
C5 C6 C7 O15 . -7.2(3)
N1 C6 C7 O14 . 45.6(2)
C5 C6 C7 O14 . -133.4(2)
N1 C6 C7 C8 . -68.0(2)
C5 C6 C7 C8 . 112.9(2)
C12 N13 C8 C9 . 0.1(3)
Cu1 N13 C8 C9 . -178.18(16)
C12 N13 C8 C7 . -179.62(19)
Cu1 N13 C8 C7 . 2.1(2)
O15 C7 C8 N13 . -172.77(18)
O14 C7 C8 N13 . -50.1(2)
C6 C7 C8 N13 . 65.9(2)
O15 C7 C8 C9 . 7.5(3)
O14 C7 C8 C9 . 130.2(2)
C6 C7 C8 C9 . -113.8(2)
N13 C8 C9 C10 . 0.3(3)
C7 C8 C9 C10 . 180.0(2)
C8 C9 C10 C11 . -0.6(4)
C9 C10 C11 C12 . 0.6(4)
C8 N13 C12 C11 . -0.1(3)
Cu1 N13 C12 C11 . 177.93(18)
C10 C11 C12 N13 . -0.2(4)
