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#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/47/4324740.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4324740
loop_
_publ_author_name
'Chandi Pariya'
'Frank R. Fronczek'
'Andrew W. Maverick'
_publ_section_title
;
 Bis(o-phenylenebis(acetylacetonato))dicopper(II): A Strained Copper(II)
 Dimer Exhibiting a Wide Range of Colors in the Solid State
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2748
_journal_page_last               2753
_journal_paper_doi               10.1021/ic101641r
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C32 H32 Cu2 O8, C10 H8 N2, C7 H8'
_chemical_formula_sum            'C49 H48 Cu2 N2 O8'
_chemical_formula_weight         919.97
_chemical_name_common
;
 copper(II) o-phenylenebis(acetylacetonate) dimer,
 polymer with 1,2-bis(4-pyridyl)ethane, toluene solvate
;
_chemical_name_systematic
; 
 catena(mu-(4,4'-bipyridine)bis(mu-(3,3'-(1,2-phenylene)-
 bis(2,4-pentanedionato)))dicopper) toluene solvate
;
_space_group_IT_number           67
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2a 2'
_symmetry_space_group_name_H-M   'C m m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.978(9)
_cell_length_b                   11.525(4)
_cell_length_c                   16.980(6)
_cell_measurement_reflns_used    4630
_cell_measurement_temperature    115
_cell_measurement_theta_max      22.0
_cell_measurement_theta_min      2.5
_cell_volume                     4105(3)
_computing_cell_refinement
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius 1999)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'Direct_methods (SIR, Altomare, et al., 1994)'
_diffrn_ambient_temperature      115
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Nonius KappaCCD (with Oxford Cryostream)'
_diffrn_measurement_method       ' ω and φ scans '
_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  0.131
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16670
_diffrn_reflns_theta_full        22.1
_diffrn_reflns_theta_max         22.1
_diffrn_reflns_theta_min         3.0
_exptl_absorpt_coefficient_mu    1.096
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            green-blue
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       needle
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.28
_refine_diff_density_min         -1.23
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.589
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1392
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.599
_refine_ls_R_factor_all          0.136
_refine_ls_R_factor_gt           0.097
_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)+(0.1180P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.262
_refine_ls_wR_factor_ref         0.286
_reflns_number_gt                939
_reflns_number_total             1392
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic101641r_si_002_6.cif
_cod_data_source_block           compound_8
_cod_original_sg_symbol_Hall     '-C 2b 2'
_cod_original_sg_symbol_H-M      'C m m a '
_cod_database_code               4324740
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'x, -y, -z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z'
'x+1/2, -y+1/2, -z'
'-x+1, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z'
'-x, y, z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.2500 0.86313(13) 0.0533(10) Uani 1 4 d S . .
Cu2 Cu 0.5000 0.2500 0.54992(14) 0.0667(11) Uani 1 4 d S . .
O1 O 0.4362(4) 0.1315(5) 0.8526(4) 0.061(2) Uani 1 1 d . . .
O2 O 0.4368(4) 0.1305(6) 0.5627(4) 0.086(3) Uani 1 1 d . . .
N1 N 0.5000 0.2500 0.4171(9) 0.048(4) Uani 1 4 d S . .
N2 N 0.5000 0.2500 -0.0015(9) 0.069(5) Uani 1 4 d S . .
C1 C 0.3466(6) 0.0341(9) 0.8109(7) 0.099(4) Uani 1 1 d . . .
H1A H 0.3751 -0.0273 0.7920 0.149 Uiso 1 1 calc R . .
H1B H 0.3118 0.0450 0.7732 0.149 Uiso 1 1 calc R . .
H1C H 0.3291 0.0120 0.8622 0.149 Uiso 1 1 calc R . .
C2 C 0.3830(6) 0.1442(8) 0.8189(6) 0.062(3) Uani 1 1 d . . .
C3 C 0.3565(7) 0.2500 0.7942(8) 0.057(4) Uani 1 2 d S . .
C4 C 0.2934(7) 0.2500 0.7491(9) 0.057(4) Uani 1 2 d S . .
C5 C 0.2934(7) 0.2500 0.6625(9) 0.054(4) Uani 1 2 d S . .
C6 C 0.2342(8) 0.2500 0.6282(8) 0.063(4) Uani 1 2 d S . .
H6 H 0.2327 0.2500 0.5723 0.076 Uiso 1 2 calc SR . .
C7 C 0.1765(7) 0.2500 0.6678(11) 0.065(4) Uani 1 2 d S . .
H7 H 0.1367 0.2500 0.6410 0.078 Uiso 1 2 calc SR . .
C8 C 0.1810(9) 0.2500 0.7498(10) 0.068(5) Uani 1 2 d S . .
H8 H 0.1425 0.2500 0.7793 0.082 Uiso 1 2 calc SR . .
C9 C 0.2379(7) 0.2500 0.7909(9) 0.059(4) Uani 1 2 d S . .
H9 H 0.2384 0.2500 0.8469 0.071 Uiso 1 2 calc SR . .
C10 C 0.3563(8) 0.2500 0.6182(8) 0.067(4) Uani 1 2 d S . .
C11 C 0.3845(7) 0.1415(9) 0.5964(7) 0.083(4) Uani 1 1 d . . .
C12 C 0.3473(7) 0.0302(10) 0.6081(9) 0.159(8) Uani 1 1 d . . .
H12A H 0.3079 0.0333 0.5772 0.238 Uiso 1 1 calc R . .
H12B H 0.3368 0.0212 0.6640 0.238 Uiso 1 1 calc R . .
H12C H 0.3731 -0.0358 0.5907 0.238 Uiso 1 1 calc R . .
C13 C 0.5000 0.3487(12) 0.3778(8) 0.058(4) Uani 1 2 d S . .
H13 H 0.5000 0.4191 0.4069 0.070 Uiso 1 2 calc SR . .
C14 C 0.5000 0.3550(12) 0.2960(8) 0.054(4) Uani 1 2 d S . .
H14 H 0.5000 0.4282 0.2703 0.064 Uiso 1 2 calc SR . .
C15 C 0.5000 0.2500 0.2509(12) 0.054(5) Uani 1 4 d S . .
C16 C 0.5000 0.2500 0.1632(11) 0.057(6) Uani 1 4 d S . .
C17 C 0.5000 0.3483(12) 0.1210(9) 0.093(6) Uani 1 2 d S . .
H17 H 0.5000 0.4217 0.1465 0.112 Uiso 1 2 calc SR . .
C18 C 0.5000 0.3408(9) 0.0395(8) 0.102(7) Uani 1 2 d S . .
H18 H 0.5000 0.4122 0.0116 0.122 Uiso 1 2 calc SR . .
C1S C 0.2500 0.3182(9) 0.0000(8) 0.120(5) Uiso 0.50 2 d SPRD A -1
C2S C 0.3057(7) 0.2605(9) -0.0037(8) 0.120(5) Uiso 0.50 1 d PRD A -1
H2S H 0.3447 0.3024 -0.0063 0.144 Uiso 0.50 1 d PR B -1
C3S C 0.3038(7) 0.1426(12) -0.0015(18) 0.120(5) Uiso 0.50 1 d PD A -1
H3S H 0.3442 0.1056 -0.0030 0.144 Uiso 0.50 1 d PR A -1
C4S C 0.2500 0.0721(12) 0.0000 0.120(5) Uiso 0.50 2 d SPD A -1
H4S H 0.2500 -0.0103 0.0000 0.120(5) Uiso 0.50 2 d SPR A -1
C7S C 0.2500 0.4454(12) 0.0000 0.120(5) Uiso 0.50 2 d SPD A -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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Cu1 O1 169.3(4) . 2_655
O1 Cu1 O1 88.3(4) . 11_655
O1 Cu1 O1 90.7(4) 2_655 11_655
O1 Cu1 O1 90.7(4) . 16
O1 Cu1 O1 88.3(4) 2_655 16
O1 Cu1 O1 169.3(4) 11_655 16
O1 Cu1 N2 95.4(2) . 1_556
O1 Cu1 N2 95.4(2) 2_655 1_556
O1 Cu1 N2 95.4(2) 11_655 1_556
O1 Cu1 N2 95.4(2) 16 1_556
O2 Cu2 O2 91.4(5) 2_655 11_655
O2 Cu2 O2 167.0(5) 2_655 .
O2 Cu2 O2 87.1(5) 11_655 .
O2 Cu2 O2 87.1(5) 2_655 16
O2 Cu2 O2 167.0(5) 11_655 16
O2 Cu2 O2 91.4(5) . 16
O2 Cu2 N1 96.5(2) 2_655 .
O2 Cu2 N1 96.5(2) 11_655 .
O2 Cu2 N1 96.5(2) . .
O2 Cu2 N1 96.5(2) 16 .
C2 O1 Cu1 125.1(6) . .
C11 O2 Cu2 126.0(8) . .
C13 N1 C13 119.2(17) 2_655 .
C13 N1 Cu2 120.4(9) 2_655 .
C13 N1 Cu2 120.4(9) . .
C18 N2 C18 112.7(17) 2_655 .
C18 N2 Cu1 123.6(9) 2_655 1_554
C18 N2 Cu1 123.6(9) . 1_554
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C2 C3 125.9(10) . .
O1 C2 C1 113.3(9) . .
C3 C2 C1 120.7(11) . .
C2 C3 C2 120.6(15) 16 .
C2 C3 C4 119.5(7) 16 .
C2 C3 C4 119.5(7) . .
C9 C4 C5 121.4(14) . .
C9 C4 C3 118.6(13) . .
C5 C4 C3 120.0(13) . .
C6 C5 C4 115.1(12) . .
C6 C5 C10 125.2(14) . .
C4 C5 C10 119.7(14) . .
C5 C6 C7 125.8(13) . .
C5 C6 H6 117.1 . .
C7 C6 H6 117.1 . .
C6 C7 C8 115.1(14) . .
C6 C7 H7 122.4 . .
C8 C7 H7 122.4 . .
C9 C8 C7 124.2(14) . .
C9 C8 H8 117.9 . .
C7 C8 H8 117.9 . .
C4 C9 C8 118.3(14) . .
C4 C9 H9 120.8 . .
C8 C9 H9 120.8 . .
C11 C10 C11 121.7(14) . 16
C11 C10 C5 119.1(7) . .
C11 C10 C5 119.1(7) 16 .
O2 C11 C10 124.9(11) . .
O2 C11 C12 115.4(10) . .
C10 C11 C12 119.5(12) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N1 C13 C14 123.4(14) . .
N1 C13 H13 118.3 . .
C14 C13 H13 118.3 . .
C13 C14 C15 119.3(14) . .
C13 C14 H14 120.4 . .
C15 C14 H14 120.4 . .
C14 C15 C14 115.4(18) 2_655 .
C14 C15 C16 122.3(9) 2_655 .
C14 C15 C16 122.3(9) . .
C17 C16 C17 115.4(18) 2_655 .
C17 C16 C15 122.3(9) 2_655 .
C17 C16 C15 122.3(9) . .
C16 C17 C18 118.7(13) . .
C16 C17 H17 120.6 . .
C18 C17 H17 120.6 . .
N2 C18 C17 127.2(13) . .
N2 C18 H18 116.4 . .
C17 C18 H18 116.4 . .
C2S C1S C7S 119.6(10) . .
C1S C2S C3S 117.8(6) . .
C1S C2S H2S 119.9 . .
C3S C2S H2S 122.3 . .
C2S C3S C4S 127.5(13) . .
C2S C3S H3S 114.9 . .
C4S C3S H3S 117.6 . .
C3S C4S H4S 125.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.920(7) .
Cu1 O1 1.920(7) 2_655
Cu1 O1 1.920(7) 11_655
Cu1 O1 1.920(7) 16
Cu1 N2 2.299(16) 1_556
Cu2 O2 1.924(8) 2_655
Cu2 O2 1.924(8) 11_655
Cu2 O2 1.924(8) .
Cu2 O2 1.924(7) 16
Cu2 N1 2.255(16) .
O1 C2 1.263(12) .
O2 C11 1.244(13) .
N1 C13 1.319(15) 2_655
N1 C13 1.319(15) .
N2 C18 1.257(14) 2_655
N2 C18 1.257(14) .
N2 Cu1 2.299(16) 1_554
C1 C2 1.487(14) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.403(12) .
C3 C2 1.403(12) 16
C3 C4 1.53(2) .
C4 C9 1.362(18) .
C4 C5 1.47(2) .
C5 C6 1.371(19) .
C5 C10 1.519(18) .
C6 C7 1.385(19) .
C6 H6 0.9500 .
C7 C8 1.40(2) .
C7 H7 0.9500 .
C8 C9 1.38(2) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C11 1.432(13) .
C10 C11 1.432(13) 16
C11 C12 1.514(15) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.391(17) .
C13 H13 0.9500 .
C14 C15 1.432(16) .
C14 H14 0.9500 .
C15 C14 1.432(16) 2_655
C15 C16 1.49(3) .
C16 C17 1.341(17) 2_655
C16 C17 1.341(17) .
C17 C18 1.387(18) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C1S C2S 1.346(10) .
C1S C7S 1.466(10) .
C2S C3S 1.360(9) .
C2S H2S 0.9500 .
C3S C4S 1.390(10) .
C3S H3S 0.9500 .
C4S H4S 0.9495 .
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_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 Cu1 O1 C2 -60.6(8) 2_655 .
O1 Cu1 O1 C2 -145.4(7) 11_655 .
O1 Cu1 O1 C2 23.9(9) 16 .
N2 Cu1 O1 C2 119.4(8) 1_556 .
O2 Cu2 O2 C11 60.8(10) 2_655 .
O2 Cu2 O2 C11 144.5(9) 11_655 .
O2 Cu2 O2 C11 -22.5(11) 16 .
N1 Cu2 O2 C11 -119.2(10) . .
O2 Cu2 N1 C13 136.1(2) 2_655 2_655
O2 Cu2 N1 C13 43.9(2) 11_655 2_655
O2 Cu2 N1 C13 -43.9(2) . 2_655
O2 Cu2 N1 C13 -136.1(2) 16 2_655
O2 Cu2 N1 C13 -43.9(2) 2_655 .
O2 Cu2 N1 C13 -136.1(2) 11_655 .
O2 Cu2 N1 C13 136.1(2) . .
O2 Cu2 N1 C13 43.9(2) 16 .
Cu1 O1 C2 C3 -10.7(15) . .
Cu1 O1 C2 C1 172.9(7) . .
O1 C2 C3 C2 -12(2) . 16
C1 C2 C3 C2 164.1(8) . 16
O1 C2 C3 C4 175.9(11) . .
C1 C2 C3 C4 -7.9(17) . .
C2 C3 C4 C9 -86.0(10) 16 .
C2 C3 C4 C9 86.0(10) . .
C2 C3 C4 C5 94.0(10) 16 .
C2 C3 C4 C5 -94.0(10) . .
C9 C4 C5 C6 0.000(4) . .
C3 C4 C5 C6 180.000(3) . .
C9 C4 C5 C10 180.000(3) . .
C3 C4 C5 C10 0.000(4) . .
C4 C5 C6 C7 0.000(4) . .
C10 C5 C6 C7 180.000(3) . .
C5 C6 C7 C8 0.000(4) . .
C6 C7 C8 C9 0.000(4) . .
C5 C4 C9 C8 0.000(4) . .
C3 C4 C9 C8 180.000(4) . .
C7 C8 C9 C4 0.000(5) . .
C6 C5 C10 C11 -88.6(13) . .
C4 C5 C10 C11 91.4(13) . .
C6 C5 C10 C11 88.6(13) . 16
C4 C5 C10 C11 -91.4(13) . 16
Cu2 O2 C11 C10 12.9(19) . .
Cu2 O2 C11 C12 -172.1(9) . .
C11 C10 C11 O2 6(3) 16 .
C5 C10 C11 O2 -177.2(12) . .
C11 C10 C11 C12 -169.3(10) 16 .
C5 C10 C11 C12 8(2) . .
C13 N1 C13 C14 0.000(4) 2_655 .
Cu2 N1 C13 C14 180.000(2) . .
N1 C13 C14 C15 0.000(4) . .
C13 C14 C15 C14 0.000(4) . 2_655
C13 C14 C15 C16 180.000(2) . .
C14 C15 C16 C17 0.000(2) 2_655 2_655
C14 C15 C16 C17 180.000(2) . 2_655
C14 C15 C16 C17 180.000(2) 2_655 .
C14 C15 C16 C17 0.000(3) . .
C17 C16 C17 C18 0.000(2) 2_655 .
C15 C16 C17 C18 180.000(1) . .
C18 N2 C18 C17 0.000(2) 2_655 .
Cu1 N2 C18 C17 180.000(2) 1_554 .
C16 C17 C18 N2 0.000(2) . .
C7S C1S C2S C3S 178(2) . .
C1S C2S C3S C4S 4(3) . .
