#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/58/2015899.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_2015899
loop_
_publ_author_name
'Chen, Xia'
'Chen, Hong-Feng'
'Xue, Gang'
'Chen, Hong-Yu'
'Yu, Wen-Tao'
'Fang, Qi'
_publ_section_title
;(Croconato-κ²O,O')bis(1,10-phenanthroline-κ²N,N')cobalt(II),
 and the nickel(II) and copper(II) analogues
;
_journal_coeditor_code           GD3090
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m166
_journal_page_last               m168
_journal_paper_doi               10.1107/S0108270107009377
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C5 O5) (C12 H8 N2)2]'
_chemical_formula_moiety         'C29 H16 Cu N4 O5'
_chemical_formula_sum            'C29 H16 Cu N4 O5'
_chemical_formula_weight         564.00
_chemical_name_systematic
;
(Croconato-κ²O,O')bis(1,10-phenanthroline-κ²N,N')copper(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.666(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6737(16)
_cell_length_b                   10.5316(13)
_cell_length_c                   15.7783(17)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.48
_cell_measurement_theta_min      5.24
_cell_volume                     2335.9(5)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Bruker, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3179
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 3
_diffrn_standards_number         97
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  0.8048
_exptl_absorpt_correction_T_min  0.7187
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XSCANS; Bruker, 1996)'
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.343
_refine_ls_extinction_coef       0.0046(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2558
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0391
_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)+(0.0318P)²+2.2378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                1906
_reflns_number_total             2558
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gd3090.cif
_cod_data_source_block           III
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2015899
_cod_database_fobs_code          2015899
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
C C1 0.2046(2) 0.0910(3) 0.3204(2) 0.0501(8) Uani d . 1
H H1 0.2084 0.0878 0.2626 0.060 Uiso calc R 1
C C2 0.2845(2) 0.0565(3) 0.3889(2) 0.0574(9) Uani d . 1
H H2 0.3407 0.0343 0.3765 0.069 Uiso calc R 1
C C3 0.2799(2) 0.0555(3) 0.4740(2) 0.0509(8) Uani d . 1
H H3 0.3326 0.0321 0.5200 0.061 Uiso calc R 1
C C4 0.19446(19) 0.0902(3) 0.49138(18) 0.0402(7) Uani d . 1
C C5 0.11904(18) 0.1279(3) 0.41863(16) 0.0346(6) Uani d . 1
C C6 0.03168(17) 0.1695(3) 0.43275(16) 0.0330(6) Uani d . 1
C C7 0.01969(18) 0.1637(3) 0.51777(16) 0.0370(6) Uani d . 1
C C8 0.0975(2) 0.1216(3) 0.59026(17) 0.0461(7) Uani d . 1
H H8 0.0901 0.1174 0.6468 0.055 Uiso calc R 1
C C9 0.1809(2) 0.0881(3) 0.57737(17) 0.0470(8) Uani d . 1
H H9 0.2308 0.0630 0.6255 0.056 Uiso calc R 1
C C10 -0.06974(19) 0.2009(3) 0.52609(17) 0.0421(7) Uani d . 1
H H10 -0.0819 0.1965 0.5807 0.051 Uiso calc R 1
C C11 -0.13819(19) 0.2435(3) 0.45359(17) 0.0438(7) Uani d . 1
H H11 -0.1974 0.2676 0.4585 0.053 Uiso calc R 1
C C12 -0.11910(19) 0.2509(3) 0.37191(17) 0.0396(7) Uani d . 1
H H12 -0.1657 0.2829 0.3235 0.047 Uiso calc R 1
C C13 0.05073(18) 0.4944(3) 0.27218(16) 0.0377(7) Uani d . 1
C C14 0.08380(18) 0.6244(3) 0.28540(16) 0.0384(6) Uani d . 1
C C15 0.0000 0.7081(4) 0.2500 0.0377(9) Uani d S 1
N N1 0.12381(16) 0.1280(2) 0.33378(14) 0.0390(5) Uani d . 1
N N2 -0.03688(14) 0.2137(2) 0.36118(12) 0.0349(5) Uani d . 1
O O1 0.09782(15) 0.3941(2) 0.29311(13) 0.0541(5) Uani d U 1
O O2 0.16619(13) 0.6606(2) 0.32058(15) 0.0630(7) Uani d . 1
O O3 0.0000 0.8248(3) 0.2500 0.0516(8) Uani d S 1
Cu Cu1 0.0000 0.22050(5) 0.2500 0.03688(17) Uani d SU 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'
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 C1 C2 . . 123.1(3) ?
N1 C1 H1 . . 118.5 ?
C2 C1 H1 . . 118.5 ?
C3 C2 C1 . . 119.8(3) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 119.3(3) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C5 C4 C3 . . 116.8(3) ?
C5 C4 C9 . . 119.3(2) ?
C3 C4 C9 . . 123.9(3) ?
N1 C5 C4 . . 123.6(2) ?
N1 C5 C6 . . 117.0(2) ?
C4 C5 C6 . . 119.4(2) ?
N2 C6 C7 . . 122.9(2) ?
N2 C6 C5 . . 117.2(2) ?
C7 C6 C5 . . 119.9(2) ?
C6 C7 C10 . . 116.8(2) ?
C6 C7 C8 . . 119.1(2) ?
C10 C7 C8 . . 124.1(2) ?
C9 C8 C7 . . 120.7(2) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C4 . . 121.4(3) ?
C8 C9 H9 . . 119.3 ?
C4 C9 H9 . . 119.3 ?
C11 C10 C7 . . 119.6(2) ?
C11 C10 H10 . . 120.2 ?
C7 C10 H10 . . 120.2 ?
C10 C11 C12 . . 119.9(2) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
N2 C12 C11 . . 122.2(2) ?
N2 C12 H12 . . 118.9 ?
C11 C12 H12 . . 118.9 ?
O1 C13 C14 . . 128.5(2) ?
O1 C13 C13 . 2 122.57(16) ?
C14 C13 C13 . 2 108.94(15) ?
O2 C14 C13 . . 126.9(3) ?
O2 C14 C15 . . 125.7(3) ?
C13 C14 C15 . . 107.4(2) ?
O3 C15 C14 . 2 126.38(18) ?
O3 C15 C14 . . 126.38(18) ?
C14 C15 C14 2 . 107.2(4) ?
C1 N1 C5 . . 117.3(2) ?
C1 N1 Cu1 . . 132.40(19) ?
C5 N1 Cu1 . . 109.43(17) ?
C12 N2 C6 . . 118.6(2) ?
C12 N2 Cu1 . . 126.37(17) ?
C6 N2 Cu1 . . 115.00(16) ?
C13 O1 Cu1 . . 109.96(17) ?
N2 Cu1 N2 . 2 175.88(14) y
N2 Cu1 N1 . 2 97.53(8) y
N2 Cu1 N1 2 2 80.58(8) ?
N2 Cu1 N1 . . 80.58(8) y
N2 Cu1 N1 2 . 97.53(8) ?
N1 Cu1 N1 2 . 126.11(13) y
N2 Cu1 O1 . . 94.15(8) y
N2 Cu1 O1 2 . 89.12(8) y
N1 Cu1 O1 2 . 152.44(8) y
N1 Cu1 O1 . . 80.37(8) y
N2 Cu1 O1 . 2 89.12(8) ?
N2 Cu1 O1 2 2 94.15(8) ?
N1 Cu1 O1 2 2 80.37(8) ?
N1 Cu1 O1 . 2 152.44(8) ?
O1 Cu1 O1 . 2 74.93(10) y
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
C1 N1 . 1.322(3) ?
C1 C2 . 1.395(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.363(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.406(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.404(3) ?
C4 C9 . 1.427(4) ?
C5 N1 . 1.361(3) ?
C5 C6 . 1.431(3) ?
C6 N2 . 1.361(3) ?
C6 C7 . 1.403(3) ?
C7 C10 . 1.411(4) ?
C7 C8 . 1.435(4) ?
C8 C9 . 1.344(4) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 C11 . 1.364(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.397(4) ?
C11 H11 . 0.9300 ?
C12 N2 . 1.325(3) ?
C12 H12 . 0.9300 ?
C13 O1 . 1.254(3) y
C13 C14 . 1.447(4) y
C13 C13 2 1.452(5) y
C14 O2 . 1.237(3) y
C14 C15 . 1.485(4) y
C15 O3 . 1.229(5) y
C15 C14 2 1.485(4) ?
Cu1 N2 . 1.9799(19) y
Cu1 N2 2 1.9799(19) ?
Cu1 N1 2 2.149(2) ?
Cu1 N1 . 2.149(2) y
Cu1 O1 . 2.303(2) y
Cu1 O1 2 2.303(2) ?
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_site_symmetry_4
_geom_torsion
N1 C1 C2 C3 . . 2.6(5)
C1 C2 C3 C4 . . -0.4(5)
C2 C3 C4 C5 . . -1.9(5)
C2 C3 C4 C9 . . 177.7(3)
C3 C4 C5 N1 . . 2.4(4)
C9 C4 C5 N1 . . -177.2(3)
C3 C4 C5 C6 . . -177.3(3)
C9 C4 C5 C6 . . 3.1(4)
N1 C5 C6 N2 . . -4.3(4)
C4 C5 C6 N2 . . 175.4(2)
N1 C5 C6 C7 . . 175.7(2)
C4 C5 C6 C7 . . -4.6(4)
N2 C6 C7 C10 . . 2.8(4)
C5 C6 C7 C10 . . -177.3(3)
N2 C6 C7 C8 . . -176.9(3)
C5 C6 C7 C8 . . 3.0(4)
C6 C7 C8 C9 . . 0.0(5)
C10 C7 C8 C9 . . -179.7(3)
C7 C8 C9 C4 . . -1.5(5)
C5 C4 C9 C8 . . -0.1(5)
C3 C4 C9 C8 . . -179.6(3)
C6 C7 C10 C11 . . -1.8(4)
C8 C7 C10 C11 . . 177.8(3)
C7 C10 C11 C12 . . -0.5(4)
C10 C11 C12 N2 . . 2.3(4)
O1 C13 C14 O2 . . -0.1(5)
C13 C13 C14 O2 2 . -179.5(3)
O1 C13 C14 C15 . . -179.3(2)
C13 C13 C14 C15 2 . 1.3(3)
O2 C14 C15 O3 . . 0.3(3)
C13 C14 C15 O3 . . 179.51(12)
O2 C14 C15 C14 . 2 -179.7(3)
C13 C14 C15 C14 . 2 -0.49(12)
C2 C1 N1 C5 . . -2.1(5)
C2 C1 N1 Cu1 . . 166.0(2)
C4 C5 N1 C1 . . -0.4(4)
C6 C5 N1 C1 . . 179.3(3)
C4 C5 N1 Cu1 . . -171.1(2)
C6 C5 N1 Cu1 . . 8.6(3)
N2 Cu1 N1 C1 . . -176.6(3)
N2 Cu1 N1 C1 2 . 7.1(3)
N1 Cu1 N1 C1 2 . 90.9(3)
O1 Cu1 N1 C1 . . -80.7(3)
O1 Cu1 N1 C1 2 . -107.2(3)
N2 Cu1 N1 C5 . . -7.77(18)
N2 Cu1 N1 C5 2 . 175.93(19)
N1 Cu1 N1 C5 2 . -100.26(19)
O1 Cu1 N1 C5 . . 88.11(19)
O1 Cu1 N1 C5 2 . 61.6(3)
C11 C12 N2 C6 . . -1.4(4)
C11 C12 N2 Cu1 . . -179.3(2)
C7 C6 N2 C12 . . -1.2(4)
C5 C6 N2 C12 . . 178.9(2)
C7 C6 N2 Cu1 . . 177.0(2)
C5 C6 N2 Cu1 . . -3.0(3)
N1 Cu1 N2 C12 2 . -50.7(2)
N1 Cu1 N2 C12 . . -176.2(2)
O1 Cu1 N2 C12 . . 104.3(2)
O1 Cu1 N2 C12 2 . 29.5(2)
N1 Cu1 N2 C6 2 . 131.3(2)
N1 Cu1 N2 C6 . . 5.82(19)
O1 Cu1 N2 C6 . . -73.7(2)
O1 Cu1 N2 C6 2 . -148.5(2)
C14 C13 O1 Cu1 . . -179.0(2)
C13 C13 O1 Cu1 2 . 0.4(4)
N2 Cu1 O1 C13 . . -88.10(19)
N2 Cu1 O1 C13 2 . 94.41(19)
N1 Cu1 O1 C13 2 . 26.9(3)
N1 Cu1 O1 C13 . . -167.80(19)
O1 Cu1 O1 C13 2 . -0.13(13)
