#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:57:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179548 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/17/4501778.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_4501778
loop_
_publ_author_name
'Du, Miao'
'Wang, Qian'
'Li, Cheng-Peng'
'Zhao, Xiao-Jun'
'Ribas, Joan'
_publ_section_title
;
 Coordination Assemblies of CoII/CuII/ZnII/CdIIwith
 2,5-Bipyridyl-1,3,4-Oxadiazole and Dicyanamide Anion: Structural
 Diversification and Properties
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3285
_journal_paper_doi               10.1021/cg100465u
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C14 H14 Cu N8 O7'
_chemical_formula_weight         469.87
_chemical_name_systematic
; 
 ? 
;
_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                 108.087(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.4504(13)
_cell_length_b                   12.1960(6)
_cell_length_c                   11.6371(6)
_cell_measurement_reflns_used    2574
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      2.56
_cell_volume                     3703.4(3)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10491
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    1.239
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.692995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'Dark blue'
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0353
_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)+(0.0588P)²+4.6612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                3220
_reflns_number_total             3631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100465u_si_002.cif
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'None' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4501778
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_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
Cu1 Cu 0.2500 0.2500 1.0000 0.02428(12) Uani 1 2 d S
Cu2 Cu 0.0000 0.0000 0.5000 0.02956(13) Uani 1 2 d S
O1 O 0.40582(6) -0.02943(13) 0.72068(15) 0.0310(4) Uani 1 1 d .
O2 O 0.19281(11) 0.3053(3) 0.5925(3) 0.0955(10) Uani 1 1 d .
O3 O 0.12235(10) 0.2669(2) 0.6184(3) 0.0741(7) Uani 1 1 d .
O4 O 0.14872(10) 0.1687(2) 0.4962(3) 0.0764(7) Uani 1 1 d .
N1 N 0.30294(7) 0.19776(15) 0.92012(17) 0.0271(4) Uani 1 1 d .
N2 N 0.42973(10) 0.13426(17) 0.6799(2) 0.0481(6) Uani 1 1 d .
N3 N 0.45275(10) 0.05508(18) 0.6263(2) 0.0468(6) Uani 1 1 d .
N4 N 0.47917(7) -0.35055(15) 0.55222(17) 0.0293(4) Uani 1 1 d .
N5 N 0.15420(9) 0.00664(19) 0.7537(3) 0.0573(8) Uani 1 1 d .
N6 N 0.06668(8) 0.00864(17) 0.6217(2) 0.0406(5) Uani 1 1 d .
N7 N 0.20098(7) 0.14051(17) 0.90178(19) 0.0357(5) Uani 1 1 d .
N8 N 0.15389(10) 0.24703(19) 0.5680(3) 0.0503(6) Uani 1 1 d .
C1 C 0.31591(9) 0.09177(18) 0.9238(2) 0.0292(5) Uani 1 1 d .
H1A H 0.3017 0.0434 0.9661 0.035 Uiso 1 1 calc R
C2 C 0.34947(9) 0.05127(18) 0.8674(2) 0.0294(5) Uani 1 1 d .
H2B H 0.3584 -0.0225 0.8737 0.035 Uiso 1 1 calc R
C3 C 0.36961(8) 0.12233(18) 0.8013(2) 0.0280(5) Uani 1 1 d .
C4 C 0.35665(10) 0.23233(19) 0.7974(3) 0.0372(6) Uani 1 1 d .
H4B H 0.3699 0.2821 0.7542 0.045 Uiso 1 1 calc R
C5 C 0.32369(10) 0.26663(19) 0.8589(2) 0.0357(5) Uani 1 1 d .
H5B H 0.3156 0.3408 0.8577 0.043 Uiso 1 1 calc R
C6 C 0.40276(9) 0.08100(18) 0.7335(2) 0.0313(5) Uani 1 1 d .
C7 C 0.43764(9) -0.0383(2) 0.6523(2) 0.0291(5) Uani 1 1 d .
C8 C 0.45081(8) -0.14705(19) 0.6180(2) 0.0276(5) Uani 1 1 d .
C9 C 0.42808(11) -0.2419(2) 0.6415(3) 0.0409(6) Uani 1 1 d .
H9A H 0.4032 -0.2388 0.6804 0.049 Uiso 1 1 calc R
C10 C 0.44283(11) -0.3408(2) 0.6066(3) 0.0426(6) Uani 1 1 d .
H10A H 0.4268 -0.4041 0.6213 0.051 Uiso 1 1 calc R
C11 C 0.50102(10) -0.2590(2) 0.5307(3) 0.0374(6) Uani 1 1 d .
H11A H 0.5263 -0.2644 0.4933 0.045 Uiso 1 1 calc R
C12 C 0.48798(10) -0.1564(2) 0.5612(2) 0.0364(6) Uani 1 1 d .
H12A H 0.5040 -0.0942 0.5437 0.044 Uiso 1 1 calc R
C13 C 0.10743(10) 0.01416(18) 0.6851(2) 0.0331(5) Uani 1 1 d .
C14 C 0.17715(8) 0.08162(19) 0.8309(2) 0.0318(5) Uani 1 1 d .
O1W O 0.28038(8) 0.11928(16) 1.15290(17) 0.0500(5) Uani 1 1 d D
H1WA H 0.2920 0.1419 1.2251 0.075 Uiso 1 1 d RD
H1WB H 0.2728 0.0520 1.1395 0.075 Uiso 1 1 d RD
O2W O 0.24141(11) 0.4048(2) 0.4267(3) 0.0865(8) Uani 1 1 d D
H2WA H 0.2723 0.3853 0.4396 0.130 Uiso 1 1 d RD
H2WB H 0.2218 0.3642 0.4531 0.130 Uiso 1 1 d RD
O3W O 0.04634(11) 0.1010(3) 0.3646(2) 0.0876(9) Uani 1 1 d D
H3WA H 0.0479 0.1552 0.3223 0.131 Uiso 1 1 d RD
H3WB H 0.0739 0.0713 0.4098 0.131 Uiso 1 1 d RD
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N7 Cu1 N7 180.0 . 7_557
N7 Cu1 N1 88.81(8) . .
N7 Cu1 N1 91.19(8) 7_557 .
N7 Cu1 N1 91.19(8) . 7_557
N7 Cu1 N1 88.81(8) 7_557 7_557
N1 Cu1 N1 180.0 . 7_557
N7 Cu1 O1W 90.15(8) . 7_557
N7 Cu1 O1W 89.85(8) 7_557 7_557
N1 Cu1 O1W 90.14(7) . 7_557
N1 Cu1 O1W 89.86(7) 7_557 7_557
N7 Cu1 O1W 89.85(8) . .
N7 Cu1 O1W 90.15(8) 7_557 .
N1 Cu1 O1W 89.86(7) . .
N1 Cu1 O1W 90.14(7) 7_557 .
O1W Cu1 O1W 180.0 7_557 .
N6 Cu2 N6 180.00(9) . 5_556
N6 Cu2 N4 88.73(8) . 7_546
N6 Cu2 N4 91.27(8) 5_556 7_546
N6 Cu2 N4 91.27(8) . 3_455
N6 Cu2 N4 88.73(8) 5_556 3_455
N4 Cu2 N4 180.00(10) 7_546 3_455
C7 O1 C6 102.48(17) . .
C5 N1 C1 118.05(19) . .
C5 N1 Cu1 121.62(15) . .
C1 N1 Cu1 120.27(15) . .
C6 N2 N3 105.99(19) . .
C7 N3 N2 106.47(19) . .
C11 N4 C10 117.4(2) . .
C11 N4 Cu2 120.42(15) . 3_545
C10 N4 Cu2 122.21(16) . 3_545
C13 N5 C14 123.7(2) . .
C13 N6 Cu2 174.2(2) . .
C14 N7 Cu1 167.9(2) . .
O3 N8 O2 117.9(3) . .
O3 N8 O4 121.9(3) . .
O2 N8 O4 120.2(3) . .
N1 C1 C2 122.8(2) . .
N1 C1 H1A 118.6 . .
C2 C1 H1A 118.6 . .
C1 C2 C3 118.8(2) . .
C1 C2 H2B 120.6 . .
C3 C2 H2B 120.6 . .
C2 C3 C4 118.8(2) . .
C2 C3 C6 120.4(2) . .
C4 C3 C6 120.7(2) . .
C5 C4 C3 118.6(2) . .
C5 C4 H4B 120.7 . .
C3 C4 H4B 120.7 . .
N1 C5 C4 122.8(2) . .
N1 C5 H5B 118.6 . .
C4 C5 H5B 118.6 . .
N2 C6 O1 112.56(19) . .
N2 C6 C3 129.5(2) . .
O1 C6 C3 117.96(19) . .
N3 C7 O1 112.5(2) . .
N3 C7 C8 128.1(2) . .
O1 C7 C8 119.4(2) . .
C9 C8 C12 118.2(2) . .
C9 C8 C7 122.7(2) . .
C12 C8 C7 119.1(2) . .
C10 C9 C8 118.9(2) . .
C10 C9 H9A 120.5 . .
C8 C9 H9A 120.5 . .
N4 C10 C9 123.2(2) . .
N4 C10 H10A 118.4 . .
C9 C10 H10A 118.4 . .
N4 C11 C12 123.2(2) . .
N4 C11 H11A 118.4 . .
C12 C11 H11A 118.4 . .
C11 C12 C8 119.1(2) . .
C11 C12 H12A 120.4 . .
C8 C12 H12A 120.4 . .
N6 C13 N5 172.3(3) . .
N7 C14 N5 173.6(3) . .
Cu1 O1W H1WA 117.9 . .
Cu1 O1W H1WB 120.7 . .
H1WA O1W H1WB 119.5 . .
H2WA O2W H2WB 118.7 . .
H3WA O3W H3WB 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N7 1.9864(19) .
Cu1 N7 1.9864(19) 7_557
Cu1 N1 2.0544(17) .
Cu1 N1 2.0544(17) 7_557
Cu1 O1W 2.3413(19) 7_557
Cu1 O1W 2.3413(19) .
Cu2 N6 1.938(2) .
Cu2 N6 1.938(2) 5_556
Cu2 N4 2.0577(18) 7_546
Cu2 N4 2.0577(18) 3_455
O1 C7 1.356(3) .
O1 C6 1.360(3) .
O2 N8 1.240(4) .
O3 N8 1.211(3) .
O4 N8 1.248(3) .
N1 C5 1.338(3) .
N1 C1 1.338(3) .
N2 C6 1.283(3) .
N2 N3 1.402(3) .
N3 C7 1.280(3) .
N4 C11 1.327(3) .
N4 C10 1.342(3) .
N4 Cu2 2.0577(18) 3_545
N5 C13 1.288(3) .
N5 C14 1.299(3) .
N6 C13 1.135(3) .
N7 C14 1.135(3) .
C1 C2 1.377(3) .
C1 H1A 0.9300 .
C2 C3 1.383(3) .
C2 H2B 0.9300 .
C3 C4 1.385(3) .
C3 C6 1.467(3) .
C4 C5 1.381(3) .
C4 H4B 0.9300 .
C5 H5B 0.9300 .
C7 C8 1.463(3) .
C8 C9 1.381(3) .
C8 C12 1.382(3) .
C9 C10 1.374(4) .
C9 H9A 0.9300 .
C10 H10A 0.9300 .
C11 C12 1.378(3) .
C11 H11A 0.9300 .
C12 H12A 0.9300 .
O1W H1WA 0.8469 .
O1W H1WB 0.8489 .
O2W H2WA 0.8486 .
O2W H2WB 0.8553 .
O3W H3WA 0.8331 .
O3W H3WB 0.8553 .
