#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/44/2204414.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_2204414
loop_
_publ_author_name
'Gao, Shan'
'Lu, Zhen-Zhong'
'Huo, Li-Hua'
'Zhang, Xian-Fa'
'Zhao, Hui'
_publ_section_title
;
 A one-dimensional hydrogen-bonding chain of
 diacetatobis(3-hydroxypyridine)copper(II)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1353
_journal_page_last               m1355
_journal_paper_doi               10.1107/S1600536804021154
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '[Cu (C2 H3 O2)2 (C5 H5 N O)2]'
_chemical_formula_moiety         'C14 H16 Cu1 N2 O6'
_chemical_formula_sum            'C14 H16 Cu N2 O6'
_chemical_formula_weight         371.83
_chemical_name_systematic
;
diacetatobis(3-hydroxypyridine)copper(II)
;
_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                114.92(3)
_cell_angle_beta                 100.20(3)
_cell_angle_gamma                100.07(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9725(18)
_cell_length_b                   10.138(2)
_cell_length_c                   10.247(2)
_cell_measurement_reflns_used    7857
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.37
_cell_volume                     798.8(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 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 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7445
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.398
_exptl_absorpt_correction_T_max  0.778
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             382
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.424
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0389
_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)+(0.0653P)²+0.1657P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                2890
_reflns_number_total             3601
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6268.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_original_formula_sum        'C14 H16 Cu1 N2 O6'
_cod_database_code               2204414
_cod_database_fobs_code          2204414
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 0.0000 0.0000 0.0000 0.03470(10) Uani d S 1 Cu
Cu2 0.0000 0.5000 0.5000 0.03470(10) Uani d S 1 Cu
O1 0.1748(2) -0.0948(2) -0.0258(2) 0.0434(4) Uani d . 1 O
O2 0.2423(2) 0.0609(2) 0.2163(2) 0.0532(5) Uani d . 1 O
O3 0.1855(3) 0.5584(2) 0.0742(2) 0.0512(5) Uani d D 1 O
H15 0.156(4) 0.571(4) 0.152(3) 0.077 Uiso d D 1 H
O4 0.0856(2) 0.7116(2) 0.5423(2) 0.0407(4) Uani d . 1 O
O5 0.0886(2) 0.5812(2) 0.3087(2) 0.0492(4) Uani d . 1 O
O6 0.4440(2) 0.2151(2) 0.4832(2) 0.0585(5) Uani d D 1 O
H16 0.380(4) 0.157(4) 0.397(2) 0.088 Uiso d D 1 H
N1 0.1058(2) 0.1543(2) -0.0518(2) 0.0363(4) Uani d . 1 N
N2 0.2198(2) 0.4905(2) 0.5722(2) 0.0379(4) Uani d . 1 N
C1 0.4120(4) -0.0927(4) 0.1238(4) 0.0602(8) Uani d . 1 C
H1A 0.4778 -0.0332 0.2251 0.090 Uiso calc R 1 H
H1B 0.4698 -0.0832 0.0563 0.090 Uiso calc R 1 H
H1C 0.3798 -0.1971 0.1016 0.090 Uiso calc R 1 H
C2 0.2685(3) -0.0372(3) 0.1053(3) 0.0418(6) Uani d . 1 C
C3 0.1072(3) 0.2990(3) 0.0243(3) 0.0377(5) Uani d . 1 C
H3 0.0571 0.3254 0.0999 0.045 Uiso calc R 1 H
C4 0.1806(3) 0.4115(3) -0.0055(3) 0.0386(5) Uani d . 1 C
C5 0.2525(4) 0.3710(3) -0.1190(3) 0.0503(6) Uani d . 1 C
H5 0.3024 0.4436 -0.1418 0.060 Uiso calc R 1 H
C6 0.2497(4) 0.2205(3) -0.1989(3) 0.0536(7) Uani d . 1 C
H6 0.2973 0.1910 -0.2763 0.064 Uiso calc R 1 H
C7 0.1755(3) 0.1151(3) -0.1622(3) 0.0459(6) Uani d . 1 C
H7 0.1739 0.0143 -0.2157 0.055 Uiso calc R 1 H
C8 0.1823(4) 0.8520(3) 0.4233(4) 0.0587(8) Uani d . 1 C
H8A 0.2948 0.8718 0.4431 0.088 Uiso calc R 1 H
H8B 0.1574 0.9327 0.5000 0.088 Uiso calc R 1 H
H8C 0.1383 0.8453 0.3275 0.088 Uiso calc R 1 H
C9 0.1141(3) 0.7044(3) 0.4223(3) 0.0391(5) Uani d . 1 C
C10 0.2582(3) 0.3611(3) 0.5050(3) 0.0398(5) Uani d . 1 C
H10 0.1825 0.2779 0.4249 0.048 Uiso calc R 1 H
C11 0.4070(3) 0.3470(3) 0.5509(3) 0.0415(5) Uani d . 1 C
C12 0.5187(3) 0.4709(3) 0.6690(3) 0.0476(6) Uani d . 1 C
H12 0.6197 0.4651 0.7019 0.057 Uiso calc R 1 H
C13 0.4784(3) 0.6037(3) 0.7376(3) 0.0479(6) Uani d . 1 C
H13 0.5523 0.6883 0.8178 0.058 Uiso calc R 1 H
C14 0.3284(3) 0.6108(3) 0.6872(3) 0.0447(6) Uani d . 1 C
H14 0.3022 0.7009 0.7339 0.054 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O2 . . 55.76(7) yes
O1 Cu1 N1 . . 89.89(8) yes
O2 Cu1 N1 . . 93.72(8) yes
O4 Cu2 O5 . . 55.23(7) yes
O4 Cu2 N2 . . 90.02(8) yes
N2 Cu2 O5 . . 89.87(8) yes
N1 Cu1 N1 . 2 180.0(3) no
N2 Cu2 N2 . 2_566 180.0(3) no
O1 Cu1 O1 . 2 180.00(9) no
O1 Cu1 N1 2 2 89.89(8) no
O1 Cu1 O2 . 2 124.3(3) no
O4 Cu2 O5 . 2_566 124.8(3) no
O4 Cu2 N2 2_566 . 89.98(8) no
O1 Cu1 N1 2 . 90.11(8) no
O1 Cu1 N1 . 2 90.11(8) no
O1 Cu1 O2 2 . 124.3(3) no
O1 Cu1 O2 2 2 55.76(7) no
O1 C2 C1 . . 117.9(3) no
O2 Cu1 O2 . 2 180.0(3) no
O2 C2 O1 . . 121.6(2) no
O2 C2 C1 . . 120.5(3) no
O3 C4 C5 . . 119.3(2) no
O3 C4 C3 . . 122.4(2) no
O4 Cu2 O4 . 2_566 180.0 no
O4 Cu2 O5 2_566 2_566 55.23(7) no
O4 Cu2 O5 2_566 . 124.8(3) no
O4 Cu2 N2 . 2_566 89.98(8) no
O4 Cu2 N2 2_566 2_566 90.02(8) no
O4 C9 C8 . . 117.4(2) no
O5 Cu2 O5 . 2_566 180.0(3) no
O5 C9 O4 . . 121.8(2) no
O5 C9 C8 . . 120.8(3) no
O6 C11 C12 . . 119.7(2) no
O6 C11 C10 . . 121.7(2) no
N1 Cu1 O2 . 2 86.3(2) no
N1 Cu1 O2 2 . 86.3(2) no
N1 Cu1 O2 2 2 93.72(8) no
N1 Cu1 N1 2 . 180.00(10) no
N1 C3 C4 . . 122.5(2) no
N1 C3 H3 . . 118.8 no
N1 C7 C6 . . 121.6(2) no
N1 C7 H7 . . 119.2 no
N2 Cu2 O5 . 2_566 90.1(2) no
N2 Cu2 O5 2_566 2_566 89.87(8) no
N2 Cu2 O5 2_566 . 90.1(2) no
N2 C10 C11 . . 122.2(2) no
N2 C10 H10 . . 118.9 no
N2 C14 C13 . . 121.2(2) no
N2 C14 H14 . . 119.4 no
N2 Cu2 N2 . 2_566 180.0 no
C2 O1 Cu1 . . 105.2(2) no
C4 O3 H15 . . 110(2) no
C2 O2 Cu1 . . 77.5(2) no
C9 O5 Cu2 . . 77.0(2) no
C9 O4 Cu2 . . 106.0(2) no
C11 O6 H16 . . 112(3) no
C3 N1 C7 . . 119.1(2) no
C3 N1 Cu1 . . 119.9(2) no
C7 N1 Cu1 . . 121.0(2) no
C14 N2 C10 . . 119.2(2) no
C14 N2 Cu2 . . 121.3(2) no
C10 N2 Cu2 . . 119.5(2) no
C2 C1 H1A . . 109.5 no
C2 C1 H1B . . 109.5 no
C2 C1 H1C . . 109.5 no
C4 C3 H3 . . 118.8 no
C4 C5 C6 . . 119.2(2) no
C4 C5 H5 . . 120.4 no
C5 C4 C3 . . 118.3(2) no
C5 C6 H6 . . 120.4 no
C6 C5 H5 . . 120.4 no
C6 C7 H7 . . 119.2 no
C7 C6 C5 . . 119.2(3) no
C7 C6 H6 . . 120.4 no
C9 C8 H8A . . 109.5 no
C9 C8 H8B . . 109.5 no
C9 C8 H8C . . 109.5 no
C11 C10 H10 . . 118.9 no
C11 C12 C13 . . 118.9(2) no
C11 C12 H12 . . 120.6 no
C12 C11 C10 . . 118.6(2) no
C12 C13 C14 . . 119.9(2) no
C12 C13 H13 . . 120.0 no
C13 C12 H12 . . 120.6 no
C13 C14 H14 . . 119.4 no
C14 C13 H13 . . 120.0 no
H1A C1 H1B . . 109.5 no
H1A C1 H1C . . 109.5 no
H1B C1 H1C . . 109.5 no
H8A C8 H8B . . 109.5 no
H8A C8 H8C . . 109.5 no
H8B C8 H8C . . 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 . 1.979(2) yes
Cu1 N1 2 1.997(2) yes
Cu1 O2 2 2.586(2) yes
Cu2 O4 . 1.975(2) yes
Cu2 O5 . 2.614(2) yes
Cu2 N2 . 2.014(2) yes
O1 C2 . 1.272(3) yes
O2 C2 . 1.249(3) yes
O4 C9 . 1.275(3) yes
O5 C9 . 1.244(3) yes
Cu1 O1 2 1.979(2) no
Cu1 N1 . 1.997(2) no
Cu1 O2 . 2.586(2) no
Cu2 O4 2_566 1.975(2) no
Cu2 O5 2_566 2.614(2) no
Cu2 N2 2_566 2.014(2) no
O3 C4 . 1.351(3) no
O3 H15 . 0.85(3) no
O6 C11 . 1.354(3) no
O6 H16 . 0.850(10) no
N1 C3 . 1.337(3) no
N1 C7 . 1.337(3) no
N2 C14 . 1.338(3) no
N2 C10 . 1.339(3) no
C1 C2 . 1.506(4) no
C1 H1A . 0.9600 no
C1 H1B . 0.9600 no
C1 H1C . 0.9600 no
C3 C4 . 1.389(3) no
C3 H3 . 0.9300 no
C4 C5 . 1.376(4) no
C5 C6 . 1.387(4) no
C5 H5 . 0.9300 no
C6 C7 . 1.381(4) no
C6 H6 . 0.9300 no
C7 H7 . 0.9300 no
C8 C9 . 1.509(4) no
C8 H8A . 0.9600 no
C8 H8B . 0.9600 no
C8 H8C . 0.9600 no
C10 C11 . 1.388(3) no
C10 H10 . 0.9300 no
C11 C12 . 1.377(4) no
C12 C13 . 1.378(4) no
C12 H12 . 0.9300 no
C13 C14 . 1.380(4) no
C13 H13 . 0.9300 no
C14 H14 . 0.9300 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
O3 H15 O5 0.85(3) 1.78(3) 2.632(3) 175(4) yes
O6 H16 O2 0.85(3) 1.780(10) 2.618(3) 171(4) 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_site_symmetry_1
_geom_torsion
_geom_torsion_publ_flag
Cu1 O1 C2 O2 . -1.7(3) no
Cu1 O1 C2 C1 . 177.4(2) no
Cu1 N1 C3 C4 . 179.2(2) no
Cu1 N1 C7 C6 . -179.7(2) no
Cu2 O4 C9 O5 . -0.4(3) no
Cu2 O4 C9 C8 . -179.6(2) no
Cu2 N2 C10 C11 . -179.2(2) no
Cu2 N2 C14 C13 . 179.3(2) no
O1 Cu1 N1 C3 . -139.2(2) no
O1 Cu1 N1 C3 2 40.8(2) no
O1 Cu1 N1 C7 . 40.9(2) no
O1 Cu1 N1 C7 2 -139.1(2) no
O3 C4 C5 C6 . 178.9(3) no
O4 Cu2 N2 C14 . 36.2(2) no
O4 Cu2 N2 C14 2_566 -143.8(2) no
O4 Cu2 N2 C10 . -144.4(2) no
O4 Cu2 N2 C10 2_566 35.6(2) no
O6 C11 C12 C13 . -179.3(3) no
N1 Cu1 O1 C2 2 -84.6(2) no
N1 Cu1 O1 C2 . 95.4(2) no
N1 C3 C4 O3 . -178.2(2) no
N1 C3 C4 C5 . 0.8(4) no
N2 Cu2 O4 C9 . 90.0(2) no
N2 Cu2 O4 C9 2_566 -90.0(2) no
N2 C10 C11 O6 . 179.3(2) no
N2 C10 C11 C12 . -0.5(4) no
C3 N1 C7 C6 . 0.5(4) no
C3 C4 C5 C6 . -0.2(4) no
C4 C5 C6 C7 . -0.3(5) no
C5 C6 C7 N1 . 0.2(4) no
C7 N1 C3 C4 . -1.0(4) no
C10 N2 C14 C13 . -0.2(4) no
C10 C11 C12 C13 . 0.4(4) no
C11 C12 C13 C14 . -0.3(4) no
C12 C13 C14 N2 . 0.2(4) no
C14 N2 C10 C11 . 0.3(4) no
