#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/59/2015957.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_2015957
loop_
_publ_author_name
'Yasodha, Vaduganathan'
'Govindarajan, Subbaiah'
'Low, John N.'
'Glidewell, Christopher'
_publ_section_title
;
 Cationic, neutral and anionic metal(II) complexes derived from
 4-oxo-4H-pyran-2,6-dicarboxylic acid (chelidonic acid)
;
_journal_coeditor_code           LN3043
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m207
_journal_page_last               m215
_journal_paper_doi               10.1107/S010827010701459X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C7 H2 O6) (H2 O)4]'
_chemical_formula_moiety         'C7 H10 Cu O10'
_chemical_formula_sum            'C7 H10 Cu O10'
_chemical_formula_weight         317.70
_chemical_name_systematic
;
tetraaqua(4-oxo-4H-pyran-2,6-dicarboxylato)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                94.237(9)
_cell_angle_beta                 94.955(9)
_cell_angle_gamma                97.353(6)
_cell_formula_units_Z            2
_cell_length_a                   4.9593(6)
_cell_length_b                   9.8973(14)
_cell_length_c                   10.4697(12)
_cell_measurement_reflns_used    2264
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.98
_cell_volume                     505.88(11)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6400
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.73
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.211
_exptl_absorpt_correction_T_max  0.809
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.086
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.424
_refine_diff_density_min         -1.419
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0763P)²+2.2295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1559
_reflns_number_gt                2043
_reflns_number_total             2264
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln3043.cif
_cod_data_source_block           IV
_cod_database_code               2015957
_cod_database_fobs_code          2015957
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
Cu Cu1 0.0000 0.0000 0.5000 0.0106(2) Uani d S 1
O O1A 0.2978(6) -0.0275(3) 0.6286(3) 0.0144(6) Uani d . 1
O O1B 0.1358(8) -0.1487(3) 0.3266(4) 0.0238(8) Uani d . 1
Cu Cu2 0.5000 0.0000 0.0000 0.0108(2) Uani d S 1
O O2A 0.3739(7) 0.1700(3) -0.0507(3) 0.0175(7) Uani d . 1
O O2B 0.2379(6) -0.0106(3) 0.1229(3) 0.0179(7) Uani d . 1
O O1 0.5368(6) 0.2869(3) 0.2755(3) 0.0132(6) Uani d . 1
C C2 0.3774(8) 0.3563(4) 0.3476(4) 0.0119(8) Uani d . 1
C C21 0.2055(9) 0.2683(4) 0.4303(4) 0.0143(8) Uani d . 1
O O21 0.2528(6) 0.1442(3) 0.4337(3) 0.0140(6) Uani d . 1
O O22 0.0323(8) 0.3231(4) 0.4846(4) 0.0273(8) Uani d . 1
C C3 0.3702(9) 0.4924(4) 0.3446(4) 0.0150(8) Uani d . 1
C C4 0.5389(10) 0.5700(4) 0.2643(5) 0.0172(9) Uani d . 1
O O4 0.5466(9) 0.6975(4) 0.2634(4) 0.0292(9) Uani d . 1
C C5 0.7043(9) 0.4922(5) 0.1875(5) 0.0167(9) Uani d . 1
C C6 0.6990(8) 0.3571(4) 0.1981(4) 0.0122(8) Uani d . 1
C C61 0.8765(8) 0.2673(4) 0.1289(4) 0.0119(8) Uani d . 1
O O61 0.8556(6) 0.1442(3) 0.1577(3) 0.0149(6) Uani d . 1
O O62 1.0274(7) 0.3210(3) 0.0545(3) 0.0179(7) Uani d . 1
H H11A 0.4442 -0.0615 0.6064 0.022 Uiso d R 1
H H12A 0.2531 -0.0696 0.6963 0.022 Uiso d R 1
H H11B -0.0203 -0.2028 0.3091 0.036 Uiso d R 1
H H12B 0.2808 -0.1903 0.3401 0.036 Uiso d R 1
H H21A 0.2306 0.2025 -0.0229 0.026 Uiso d R 1
H H22A 0.4215 0.2072 -0.1206 0.026 Uiso d R 1
H H21B 0.1092 0.0428 0.1254 0.027 Uiso d R 1
H H22B 0.1985 -0.0713 0.1781 0.027 Uiso d R 1
H H3 0.2527 0.5364 0.3959 0.018 Uiso calc R 1
H H5 0.8165 0.5364 0.1296 0.020 Uiso calc R 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'
Cu Cu 0.3201 1.2651 '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'
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
O1A Cu1 O1A . 2_556 180.0 no
O1A Cu1 O21 . . 88.68(13) no
O1A Cu1 O21 2_556 . 91.32(13) no
O1A Cu1 O21 . 2_556 91.32(13) no
O1A Cu1 O21 2_556 2_556 88.68(13) no
O21 Cu1 O21 . 2_556 180.00(13) no
Cu1 O1A H11A . . 121.8 no
Cu1 O1A H12A . . 117.6 no
H11A O1A H12A . . 104.6 no
H11B O1B H12B . . 115.4 no
O2B Cu2 O2B . 2_655 180.0(3) no
O2B Cu2 O2A . 2_655 91.08(13) no
O2B Cu2 O2A 2_655 2_655 88.92(13) no
O2B Cu2 O2A . . 88.92(13) no
O2B Cu2 O2A 2_655 . 91.08(13) no
O2A Cu2 O2A 2_655 . 180.00(19) no
Cu2 O2A H21A . . 124.2 no
Cu2 O2A H22A . . 122.0 no
H21A O2A H22A . . 111.2 no
Cu2 O2B H21B . . 122.9 no
Cu2 O2B H22B . . 131.3 no
H21B O2B H22B . . 105.2 no
C2 O1 C6 . . 118.5(3) no
O1 C2 C3 . . 122.9(4) no
O1 C2 C21 . . 114.1(4) no
C3 C2 C21 . . 123.0(4) no
O22 C21 O21 . . 127.4(4) no
O22 C21 C2 . . 116.3(4) no
O21 C21 C2 . . 116.3(4) no
C21 O21 Cu1 . . 123.0(3) no
C2 C3 C4 . . 120.2(4) no
C2 C3 H3 . . 119.9 no
C4 C3 H3 . . 119.9 no
O4 C4 C3 . . 122.0(4) no
O4 C4 C5 . . 122.7(4) no
C3 C4 C5 . . 115.3(4) no
C6 C5 C4 . . 120.0(4) no
C6 C5 H5 . . 120.0 no
C4 C5 H5 . . 120.0 no
C5 C6 O1 . . 123.0(4) no
C5 C6 C61 . . 124.5(4) no
O1 C6 C61 . . 112.4(3) no
O62 C61 O61 . . 127.3(4) no
O62 C61 C6 . . 117.4(4) no
O61 C61 C6 . . 115.3(4) 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 O1A . 1.970(3) y
Cu1 O1A 2_556 1.970(3) no
Cu1 O21 . 1.982(3) y
Cu1 O21 2_556 1.982(3) no
Cu1 O1B . 2.447(4) y
Cu1 O1B 2_556 2.447(4) no
O1A H11A . 0.8797 no
O1A H12A . 0.8794 no
O1B H11B . 0.88 no
O1B H12B . 0.8798 no
Cu2 O2A 2_655 1.961(3) no
Cu2 O2A . 1.961(3) y
Cu2 O2B . 1.906(3) y
Cu2 O2B 2_655 1.906(3) no
Cu2 O61 . 2.525(3) y
Cu2 O61 2_655 2.525(3) no
O2A H21A . 0.88 no
O2A H22A . 0.8801 no
O2B H21B . 0.8801 no
O2B H22B . 0.88 no
O1 C2 . 1.353(5) no
O1 C6 . 1.357(5) no
C2 C3 . 1.355(6) no
C2 C21 . 1.511(6) no
C21 O22 . 1.230(6) no
C21 O21 . 1.282(5) no
C3 C4 . 1.432(6) no
C3 H3 . 0.95 no
C4 O4 . 1.258(6) no
C4 C5 . 1.449(6) no
C5 C6 . 1.346(6) no
C5 H5 . 0.95 no
C6 C61 . 1.518(6) no
C61 O62 . 1.228(6) no
C61 O61 . 1.271(5) no
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
_geom_hbond_publ_flag
O1A H11A O21 2_656 0.88 1.86 2.743(4) 176 y
O1A H12A O61 2_656 0.88 1.84 2.715(4) 175 y
O1B H11B O4 1_445 0.88 2.24 3.110(6) 169 y
O1B H12B O4 1_545 0.88 2.01 2.790(5) 147 y
O2A H21A O62 1_455 0.88 1.83 2.672(4) 160 y
O2A H22A O4 2_665 0.88 1.83 2.699(5) 168 y
O2B H21B O61 1_455 0.88 1.75 2.618(4) 170 y
O2B H22B O1B . 0.88 1.82 2.666(5) 162 y
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
C6 O1 C2 C3 . 0.9(6) no
C6 O1 C2 C21 . -179.9(4) no
O1 C2 C21 O22 . -171.0(4) no
C3 C2 C21 O22 . 8.2(7) no
O1 C2 C21 O21 . 7.6(6) no
C3 C2 C21 O21 . -173.2(4) no
O22 C21 O21 Cu1 . 13.4(7) no
C2 C21 O21 Cu1 . -165.0(3) no
O1A Cu1 O21 C21 . -121.0(3) no
O1A Cu1 O21 C21 2_556 59.0(3) no
O1 C2 C3 C4 . -1.0(7) no
C21 C2 C3 C4 . 179.8(4) no
C2 C3 C4 O4 . -176.8(5) no
C2 C3 C4 C5 . 1.6(7) no
O4 C4 C5 C6 . 176.2(5) no
C3 C4 C5 C6 . -2.2(7) no
C4 C5 C6 O1 . 2.3(7) no
C4 C5 C6 C61 . -176.0(4) no
C2 O1 C6 C5 . -1.5(6) no
C2 O1 C6 C61 . 176.9(3) no
C5 C6 C61 O62 . -2.9(6) no
O1 C6 C61 O62 . 178.7(4) no
C5 C6 C61 O61 . 175.4(4) no
O1 C6 C61 O61 . -3.0(5) no
