# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Luiz Fernando de Oliveira'
_publ_contact_author_email       LUIZ.OLIVEIRA@UFJF.EDU.BR

_publ_section_title              
;
An Intriguing Hydrogen Bond Arrangement of Polymeric
1D Chains of 4,4'-Bipyridine Coordinated to Co2+, Ni2+, Cu2+ and Zn2+
Ions Having Barbiturate as Counterions in a 3D Network
;
loop_
_publ_author_name
'Luiz Fernando de Oliveira'
'Renata Diniz'
'Humberto C. Garcia'
'Maria I. Yoshida'

# Attachment 'hbcobi-ccdc2.cif'

#----------------------------------------------------------------------------#
# Global data block identification for start of deposition

data_HBCOBI
_database_code_depnum_ccdc_archive 'CCDC 702329'

_audit_creation_date             'Dec 16 14:05:31 2008'
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
'tetraaquacobalt(II)-4,4'-bipyridine barbiturate hexahydrate'
;
_chemical_name_common            
"'tetraaquacobalt(ii)-4,4'-bipyridine barbiturate hexahydrate'"
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 Co N2 O4, 2(C4 H3 N2 O3), 6(H2 O)'
_chemical_formula_sum            'C18 H34 Co N6 O16'
_chemical_formula_weight         649.44

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+2/3'
'y, -x+y, z+1/3'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'y, x, -z+1/3'
'-y, -x, -z+1/3'
'x, x-y, -z+2/3'
'-x+y, y, -z'

_cell_length_a                   11.641(1)
_cell_length_b                   11.641(1)
_cell_length_c                   18.756(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2201.2(4)
_cell_formula_units_Z            3
_cell_measurement_temperature    298(2)
_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_Hall  'P 64 2c (0 0 -1)'
_symmetry_space_group_name_H-M   'P 64 2 2'
_symmetry_Int_Tables_number      181

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'light pink'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1005

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0900
-1 1 1 0.1150
0 -1 1 0.1400
-1 0 1 0.1440
0 1 1 0.0860
1 -1 1 0.1100
0 0 -1 0.1580
0 -1 -1 0.2580
0 1 -2 0.1940
2 0 -3 0.2030
-1 0 -1 0.2470

_exptl_absorpt_coefficient_mu    0.6600
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
a grid of 8 x 8 x 8 = 512 sampling points was used
;
_exptl_absorpt_correction_T_min  0.8358
_exptl_absorpt_correction_T_max  0.8713
_exptl_absorpt_correction_T_ave  0.8558

_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_number            17763
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         5.20
_diffrn_reflns_theta_max         27.56
_reflns_number_total             1674
_reflns_number_gt                1365
_reflns_threshold_expression     >2sigma(I)
_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.979

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'COLLECT (Enraf-Nonius, 1997-2000)'
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_reduction        'EVALCCD (Duisenber et al., 2003)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 3 FOR WINDOWS (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 1990)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0250P)²+0.9641P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_number_reflns         1674
_refine_ls_number_parameters     102
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0714
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Co1 Co 1.0000 1.0000 0.8333 0.03001(14) Uani 1 4 d S . .
N1 N 1.0000 0.80817(19) 0.8333 0.0331(5) Uani 1 2 d S . .
O1 O 0.85739(18) 0.91841(19) 0.91165(10) 0.0593(5) Uani 1 1 d . . .
H1B H 0.8665 0.8671 0.9411 0.089 Uiso 1 1 d R . .
H1A H 0.8001 0.9265 0.9163 0.089 Uiso 1 1 d R . .
C3 C 1.0000 0.5643(2) 0.8333 0.0310(6) Uani 1 2 d S . .
C2 C 1.1144(2) 0.6847(2) 0.84707(13) 0.0403(6) Uani 1 1 d . . .
H2 H 1.1937 0.6868 0.8569 0.048 Uiso 1 1 calc R . .
C1 C 1.1098(2) 0.8016(2) 0.84612(13) 0.0408(6) Uani 1 1 d . . .
H1 H 1.1881 0.8805 0.8549 0.049 Uiso 1 1 calc R . .
O2 O 0.86626(10) 0.73252(19) 1.0000 0.0421(5) Uani 1 2 d S . .
C6 C 0.66562(16) 0.3312(3) 1.0000 0.0447(7) Uani 1 2 d S . .
H6 H 0.6195 0.2390 1.0000 0.054 Uiso 1 2 calc SR . .
C4 C 0.80479(14) 0.6096(3) 1.0000 0.0326(6) Uani 1 2 d S . .
N2 N 0.67522(19) 0.53729(19) 0.98042(10) 0.0371(4) Uani 1 1 d . . .
O3 O 0.48286(17) 0.34632(17) 0.95692(12) 0.0592(5) Uani 1 1 d . . .
C5 C 0.6016(2) 0.3991(2) 0.97844(12) 0.0403(5) Uani 1 1 d . . .
O4 O 0.6346(2) 0.9218(2) 0.94027(17) 0.0991(10) Uani 1 1 d . . .
H4A H 0.5716 0.9308 0.9163 0.149 Uiso 1 1 d R . .
H4B H 0.6057 0.8425 0.9550 0.149 Uiso 1 1 d R . .
O5 O 1.5000 1.0000 0.8541(2) 0.165(2) Uani 1 2 d SD . .
H5A H 1.4337 0.9724 0.8316 0.247 Uiso 1 1 d RD . .
H2N H 0.636(3) 0.578(2) 0.9696(13) 0.041(7) Uiso 1 1 d . . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.0586(16) 11_566 ?
Co1 O1 2.0586(16) 8_766 ?
Co1 O1 2.0586(16) 2_775 ?
Co1 O1 2.0586(16) . ?
Co1 N1 2.234(2) . ?
Co1 N1 2.234(2) 2_775 ?
N1 C1 1.340(3) 8_766 ?
N1 C1 1.340(3) . ?
C3 C2 1.391(3) 8_766 ?
C3 C2 1.391(3) . ?
C3 C3 1.498(5) 2_765 ?
C2 C1 1.388(3) . ?
O2 C4 1.238(3) . ?
C6 C5 1.390(3) 12_657 ?
C6 C5 1.390(3) . ?
C4 N2 1.361(3) . ?
C4 N2 1.361(2) 12_657 ?
N2 C5 1.393(3) . ?
O3 C5 1.265(3) . ?

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
_geom_angle_publ_flag
O1 Co1 O1 88.92(11) 11_566 8_766 ?
O1 Co1 O1 173.34(10) 11_566 2_775 ?
O1 Co1 O1 91.46(11) 8_766 2_775 ?
O1 Co1 O1 91.46(11) 11_566 . ?
O1 Co1 O1 173.34(10) 8_766 . ?
O1 Co1 O1 88.92(11) 2_775 . ?
O1 Co1 N1 93.33(5) 11_566 . ?
O1 Co1 N1 86.67(5) 8_766 . ?
O1 Co1 N1 93.33(5) 2_775 . ?
O1 Co1 N1 86.67(5) . . ?
O1 Co1 N1 86.67(5) 11_566 2_775 ?
O1 Co1 N1 93.33(5) 8_766 2_775 ?
O1 Co1 N1 86.67(5) 2_775 2_775 ?
O1 Co1 N1 93.33(5) . 2_775 ?
N1 Co1 N1 180.000(1) . 2_775 ?
C1 N1 C1 115.5(2) 8_766 . ?
C1 N1 Co1 122.26(12) 8_766 . ?
C1 N1 Co1 122.26(12) . . ?
C2 C3 C2 116.2(2) 8_766 . ?
C2 C3 C3 121.89(13) 8_766 2_765 ?
C2 C3 C3 121.89(12) . 2_765 ?
C1 C2 C3 119.9(2) . . ?
N1 C1 C2 124.2(2) . . ?
C5 C6 C5 121.1(3) 12_657 . ?
O2 C4 N2 122.46(13) . . ?
O2 C4 N2 122.46(13) . 12_657 ?
N2 C4 N2 115.1(3) . 12_657 ?
C4 N2 C5 125.00(19) . . ?
O3 C5 C6 125.6(2) . . ?
O3 C5 N2 117.48(19) . . ?
C6 C5 N2 116.9(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Co1 N1 C1 -122.07(15) . . . . no
O1 Co1 N1 C1 57.92(15) . . . 8_766 no
O1 Co1 N1 C1 -33.35(15) 2_775 . . . no
O1 Co1 N1 C1 146.65(15) 11_566 . . . no
Co1 N1 C1 C2 179.68(17) . . . . no
C1 N1 C1 C2 -0.3(3) . . 8_766 8_766 no
C5 N2 C4 O2 179.04(16) . . . . no
C5 N2 C4 N2 -1.0(3) . . . 12_657 no
C4 N2 C5 O3 -177.9(2) . . . . no
C4 N2 C5 C6 1.8(3) . . . . no
N1 C1 C2 C3 0.6(3) . . . . no
C1 C2 C3 C3 179.71(16) . . . 2_765 no
C1 C2 C3 C2 -0.3(3) . . . 8_766 no
O3 C5 C6 C5 178.9(2) . . . 12_657 no
N2 C5 C6 C5 -0.8(3) . . . 12_657 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_site_symmetry_A
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
O1 H1A O4 0.7200 1.9500 2.670(5) 170.00 . yes
O1 H1B O2 0.8600 1.9200 2.769(3) 172.00 . yes
N2 H2N O3 0.84(4) 1.98(4) 2.813(4) 171(3) 2_665 yes
O4 H4A O5 0.9100 1.8500 2.706(4) 159.00 1_455 yes
O4 H4B O3 0.8500 1.9100 2.728(3) 161.00 2_665 yes

#
#END
#

# Attachment 'hbnibi-ccdc2.cif'

#----------------------------------------------------------------------------#
# Global data block identification for start of deposition

data_HBNIBI
_database_code_depnum_ccdc_archive 'CCDC 702330'

_audit_creation_date             'Dec 17 16:01:44 2008'
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
'tetraaquanickel(II)-4,4'-bipyridine barbiturate hexahydrate'
;
_chemical_name_common            
"'tetraaquanickel(ii)-4,4'-bipyridine barbiturate hexahydrate'"
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 N2 Ni O4, 2(C4 H3 N2 O3), 6(H2 O)'
_chemical_formula_sum            'C18 H34 N6 Ni O16'
_chemical_formula_weight         649.22

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, -x, -z+1/6'
'y, x, -z+2/3'
'x-y, -y, -z'
'-x+y, y, -z+1/2'
'x, x-y, -z+5/6'
'-x, -x+y, -z+1/3'
'-y, x-y, z+2/3'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'
'-x+y, -x, z+1/3'

_cell_length_a                   11.453(2)
_cell_length_b                   11.453(2)
_cell_length_c                   36.912(4)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                120.000
_cell_volume                     4193(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    298(2)
_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_Hall  'P 65 2 ( 0 0 1)'
_symmetry_space_group_name_H-M   'P 65 2 2'
_symmetry_Int_Tables_number      179

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2040

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.7800
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
a grid of 8 x 8 x 8 = 512 sampling points was used
;
_exptl_absorpt_correction_T_min  0.7903
_exptl_absorpt_correction_T_max  0.9007
_exptl_absorpt_correction_T_ave  0.8516
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -3 0.1490
0 2 -3 0.1540
0 0 1 0.0600
0 0 -1 0.0910
-1 2 -3 0.1760
-2 2 -3 0.1690
-1 0 -1 0.1820
0 -1 2 0.1080
1 -1 1 0.1650

_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_number            16434
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         5.25
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3137
_reflns_number_gt                2401
_reflns_threshold_expression     >2sigma(I)
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        0.50
_diffrn_measured_fraction_theta_full 0.000

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'COLLECT (Enraf-Nonius, 1997-2000)'
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_reduction        'EVALCCD (Duisenber et al., 2003)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 3 FOR WINDOWS (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 1990)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0614P)²+2.7232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_number_reflns         3137
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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'
Ni Ni 0.3393 1.1124 '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_
_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
Ni Ni 0.06979(5) 0.0000 0.0000 0.03197(19) Uani 1 2 d S . .
N1 N -0.1183(3) 0.0000 0.0000 0.0338(9) Uani 1 2 d S . .
N2 N -0.7432(3) 0.0000 0.0000 0.0358(10) Uani 1 2 d S . .
N3 N 0.3574(3) 0.8275(4) 0.09500(9) 0.0444(8) Uani 1 1 d . . .
H3N H 0.3964 0.9101 0.1020 0.053 Uiso 1 1 calc R . .
N4 N 0.7065(3) 0.1046(3) 0.09379(9) 0.0432(8) Uani 1 1 d . . .
H4N H 0.6668 0.0217 0.1006 0.052 Uiso 1 1 calc R . .
O1 O -0.0139(3) -0.1691(3) 0.03206(7) 0.0446(7) Uani 1 1 d . . .
H1A H 0.0365 -0.1673 0.0493 0.067 Uiso 1 1 d R . .
H1B H -0.0373 -0.2386 0.0205 0.067 Uiso 1 1 d R . .
O2 O 0.1229(3) 0.1183(3) 0.04612(6) 0.0501(7) Uani 1 1 d . . .
H2A H 0.2021 0.1716 0.0527 0.075 Uiso 1 1 d R . .
H2B H 0.0609 0.1236 0.0559 0.075 Uiso 1 1 d R . .
O3 O 0.1662(2) 0.8338(2) 0.0833 0.0489(12) Uani 1 2 d S . .
O4 O 0.5496(3) 0.8268(4) 0.10971(12) 0.0849(13) Uani 1 1 d . . .
O5 O 0.90033(18) 0.09967(18) 0.0833 0.0375(9) Uani 1 2 d S . .
O6 O 0.5112(4) 0.1073(4) 0.10459(14) 0.0959(14) Uani 1 1 d . . .
O7 O 0.3680(4) 0.2562(6) 0.08002(12) 0.1202(19) Uani 1 1 d . . .
H7A H 0.4028 0.2189 0.0864 0.180 Uiso 1 1 d R . .
H7B H 0.4197 0.3208 0.0665 0.180 Uiso 1 1 d R . .
O8 O 0.9186(7) 0.5978(5) -0.00422(15) 0.066(3) Uani 0.601(13) 1 d P . .
H8A H 0.9145 0.5710 0.0120 0.099 Uiso 1 1 d R . .
H8B H 0.8719 0.5862 -0.0178 0.099 Uiso 1 1 d R . .
O8A O 0.7966(18) 0.5884(13) 0.0087(5) 0.139(9) Uani 0.399(13) 1 d P . .
O9 O 0.5812(8) 0.5114(9) 0.02498(18) 0.197(3) Uani 1 1 d . . .
H9A H 0.4998 0.4772 0.0183 0.296 Uiso 1 1 d R . .
H9B H 0.6359 0.5628 0.0432 0.296 Uiso 1 1 d R . .
C1 C -0.2334(4) -0.1061(4) 0.01192(10) 0.0408(10) Uani 1 1 d . . .
H1 H -0.2306 -0.1812 0.0204 0.049 Uiso 1 1 calc R . .
C2 C -0.3561(4) -0.1094(4) 0.01227(10) 0.0411(10) Uani 1 1 d . . .
H2 H -0.4327 -0.1858 0.0208 0.049 Uiso 1 1 calc R . .
C3 C -0.3658(4) 0.0000 0.0000 0.0344(11) Uani 1 2 d S . .
C4 C -0.7386(4) -0.1141(4) -0.00420(11) 0.0413(9) Uani 1 1 d . . .
H4 H -0.8195 -0.1945 -0.0072 0.050 Uiso 1 1 calc R . .
C5 C -0.6193(4) -0.1183(4) -0.00428(10) 0.0410(9) Uani 1 1 d . . .
H5 H -0.6217 -0.2000 -0.0072 0.049 Uiso 1 1 calc R . .
C6 C -0.4963(4) 0.0000 0.0000 0.0360(12) Uani 1 2 d S . .
C7 C 0.2288(3) 0.7712(3) 0.0833 0.0352(13) Uani 1 2 d S . .
C8 C 0.4317(5) 0.7616(5) 0.09660(13) 0.0569(12) Uani 1 1 d . . .
C9 C 0.3694(3) 0.6306(3) 0.0833 0.068(2) Uani 1 2 d S . .
H9 H 0.4163 0.5838 0.0833 0.082 Uiso 1 2 calc SR . .
C10 C 0.8380(3) 0.1620(3) 0.0833 0.0328(13) Uani 1 2 d S . .
C11 C 0.6307(5) 0.1703(5) 0.09424(15) 0.0635(14) Uani 1 1 d . . .
C12 C 0.6963(4) 0.3037(4) 0.0833 0.082(3) Uani 1 2 d S . .
H12 H 0.6493 0.3505 0.0833 0.098 Uiso 1 2 calc SR . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni O1 2.051(3) 5 ?
Ni O1 2.051(3) . ?
Ni O2 2.071(2) . ?
Ni O2 2.071(2) 5 ?
Ni N2 2.140(4) 1_655 ?
Ni N1 2.152(4) . ?
N1 C1 1.343(4) . ?
N1 C1 1.344(4) 5 ?
N2 C4 1.343(4) 5 ?
N2 C4 1.344(4) . ?
N2 Ni 2.140(4) 1_455 ?
N3 C7 1.350(4) . ?
N3 C8 1.392(6) . ?
N4 C10 1.362(4) . ?
N4 C11 1.406(6) . ?
O3 C7 1.241(7) . ?
O4 C8 1.268(6) . ?
O5 C10 1.236(6) . ?
O6 C11 1.244(6) . ?
O8 O8A 1.427(19) . ?
C1 C2 1.386(5) . ?
C2 C3 1.389(5) . ?
C3 C2 1.388(5) 5 ?
C3 C6 1.493(7) . ?
C4 C5 1.390(5) . ?
C5 C6 1.392(5) . ?
C6 C5 1.393(5) 5 ?
C7 N3 1.351(4) 3_665 ?
C8 C9 1.390(6) . ?
C9 C8 1.389(6) 3_665 ?
C10 N4 1.364(4) 3_665 ?
C11 C12 1.383(6) . ?
C12 C11 1.381(6) 3_665 ?

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
_geom_angle_publ_flag
O1 Ni O1 179.46(15) 5 . ?
O1 Ni O2 90.55(11) 5 . ?
O1 Ni O2 89.46(11) . . ?
O1 Ni O2 89.46(11) 5 5 ?
O1 Ni O2 90.56(11) . 5 ?
O2 Ni O2 176.18(16) . 5 ?
O1 Ni N2 89.83(7) 5 1_655 ?
O1 Ni N2 89.64(7) . 1_655 ?
O2 Ni N2 91.87(8) . 1_655 ?
O2 Ni N2 91.94(8) 5 1_655 ?
O1 Ni N1 90.17(7) 5 . ?
O1 Ni N1 90.36(7) . . ?
O2 Ni N1 88.13(8) . . ?
O2 Ni N1 88.06(8) 5 . ?
N2 Ni N1 180.0 1_655 . ?
C1 N1 C1 116.2(4) . 5 ?
C1 N1 Ni 121.9(2) . . ?
C1 N1 Ni 122.0(2) 5 . ?
C4 N2 C4 116.6(4) 5 . ?
C4 N2 Ni 121.6(2) 5 1_455 ?
C4 N2 Ni 121.7(2) . 1_455 ?
C7 N3 C8 124.8(4) . . ?
C10 N4 C11 125.0(4) . . ?
N1 C1 C2 123.3(4) . . ?
C1 C2 C3 120.7(4) . . ?
C2 C3 C2 115.8(5) 5 . ?
C2 C3 C6 122.1(2) 5 . ?
C2 C3 C6 122.2(2) . . ?
N2 C4 C5 123.4(4) . . ?
C4 C5 C6 120.0(4) . . ?
C5 C6 C5 116.6(5) . 5 ?
C5 C6 C3 121.7(2) . . ?
C5 C6 C3 121.7(2) 5 . ?
O3 C7 N3 122.1(3) . . ?
O3 C7 N3 122.2(3) . 3_665 ?
N3 C7 N3 115.8(5) . 3_665 ?
O4 C8 C9 126.3(5) . . ?
O4 C8 N3 117.1(4) . . ?
C9 C8 N3 116.6(4) . . ?
C8 C9 C8 121.3(6) 3_665 . ?
O5 C10 N4 122.6(2) . . ?
O5 C10 N4 122.7(2) . 3_665 ?
N4 C10 N4 114.7(5) . 3_665 ?
O6 C11 C12 124.1(5) . . ?
O6 C11 N4 119.1(5) . . ?
C12 C11 N4 116.7(5) . . ?
C11 C12 C11 121.8(6) 3_665 . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Ni N1 C1 -12.5(2) . . . . no
O1 Ni N1 C1 167.5(2) . . . 5_555 no
O2 Ni N1 C1 -101.9(2) . . . . no
O2 Ni N1 C1 78.1(2) . . . 5_555 no
O1 Ni N1 C1 167.5(2) 5_555 . . . no
O1 Ni N2 C4 137.0(2) . . . 5_555 no
O1 Ni N2 C4 -43.0(2) . . . . no
O2 Ni N2 C4 47.6(2) . . . 5_555 no
O2 Ni N2 C4 -132.4(2) . . . . no
Ni N1 C1 C2 -179.9(3) . . . . no
C1 N1 C1 C2 0.2(5) 5_555 . . . no
C8 N3 C7 N3 -1.8(5) . . . 3_665 no
C7 N3 C8 O4 -177.0(4) . . . . no
C7 N3 C8 C9 3.5(6) . . . . no
C8 N3 C7 O3 178.2(3) . . . . no
C10 N4 C11 C12 -0.4(6) . . . . no
C11 N4 C10 O5 -179.8(3) . . . . no
C11 N4 C10 N4 0.2(5) . . . 3_665 no
C10 N4 C11 O6 -179.6(4) . . . . no
N1 C1 C2 C3 -0.1(6) . . . . no
C1 C2 C3 C2 0.1(5) . . . 5_555 no
C1 C2 C3 C6 -180.0(3) . . . 1_455 no
O4 C8 C9 C8 179.0(5) . . . 3_665 no
N3 C8 C9 C8 -1.6(6) . . . 3_665 no
O6 C11 C12 C11 179.3(5) . . . 3_665 no
N4 C11 C12 C11 0.2(6) . . . 3_665 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_site_symmetry_A
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
O1 H1A O3 0.8500 1.9400 2.787(3) 172.00 3_655 yes
O1 H1B O8 0.8200 1.9100 2.730(9) 175.00 1_445 yes
O2 H2A O7 0.8400 1.9300 2.740(5) 162.00 . yes
O2 H2B O5 0.8200 2.0000 2.808(3) 168.00 3_565 yes
N3 H3N O6 0.8600 1.9700 2.802(7) 164.00 1_565 yes
O7 H7A O6 0.7500 2.2800 3.036(7) 179.00 . yes
O7 H7B O9 0.8400 2.5500 3.391(10) 178.00 . yes
O8 H8B O4 0.6900 2.1100 2.807(10) 177.00 11_654 yes
O9 H9A O8 0.8500 1.8600 2.706(14) 179.00 5_565 yes
C1 H1 O1 0.9300 2.4500 3.034(6) 121.00 . yes

#
#END
#


#
#END
#

# Attachment 'hbcubi-ccdc2.cif'

#----------------------------------------------------------------------------#
# Global data block identification for start of deposition

data_HBCUBI
_database_code_depnum_ccdc_archive 'CCDC 702331'
_audit_creation_date             'Dec 17 16:02:39 2008'
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
'tetraaquacopper(II)-4,4'-bipyridine barbiturate hexahydrate'
;
_chemical_name_common            
"'tetraaquacopper(ii)-4,4'-bipyridine barbiturate hexahydrate'"
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 Cu N2 O4, 2(C4 H3 N2 O3), 6(H2 O)'
_chemical_formula_sum            'C18 H34 Cu N6 O16'
_chemical_formula_weight         654.05

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, -x, -z+1/6'
'y, x, -z+2/3'
'x-y, -y, -z'
'-x+y, y, -z+1/2'
'x, x-y, -z+5/6'
'-x, -x+y, -z+1/3'
'-y, x-y, z+2/3'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'
'-x+y, -x, z+1/3'

_cell_length_a                   11.467(2)
_cell_length_b                   11.467(2)
_cell_length_c                   36.974(3)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                120.000
_cell_volume                     4210.1(11)
_cell_formula_units_Z            6
_cell_measurement_temperature    298(2)
_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_Hall  'P 65 2 ( 0 0 1)'
_symmetry_space_group_name_H-M   'P 65 2 2'
_symmetry_Int_Tables_number      179

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prismatic
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2046

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.8600
_exptl_absorpt_correction_type   gaussian

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.1190
-1 1 -1 0.1530
1 1 -1 0.1940
0 0 1 0.2400
3 -2 0 0.1060
0 0 -1 0.1390
-1 1 4 0.1470
0 1 2 0.1350
2 -5 -1 0.1700
1 -2 6 0.2070

_exptl_absorpt_process_details   
;
a grid of 8 x 8 x 8 = 512 sampling points was used
;
_exptl_absorpt_correction_T_min  0.8044
_exptl_absorpt_correction_T_max  0.8464
_exptl_absorpt_correction_T_ave  0.8274

_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_number            26411
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         5.25
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3141
_reflns_number_gt                2494
_reflns_threshold_expression     >2sigma(I)
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.982

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'COLLECT (Enraf-Nonius, 1997-2000)'
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_reduction        'EVALCCD (Duisenber et al., 2003)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 3 FOR WINDOWS (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 1990)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0742P)²+3.5657P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_number_reflns         3141
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#
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_
_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 0.07071(5) 0.0000 0.0000 0.0334(2) Uani 1 2 d S . .
N1 N -0.1174(4) 0.0000 0.0000 0.0323(10) Uani 1 2 d S . .
N2 N -0.7420(4) 0.0000 0.0000 0.0342(10) Uani 1 2 d S . .
N3 N 0.3580(4) 0.8275(4) 0.09502(10) 0.0420(9) Uani 1 1 d . . .
H3N H 0.3969 0.9101 0.1020 0.050 Uiso 1 1 calc R . .
N4 N 0.7067(4) 0.1041(3) 0.09369(10) 0.0402(8) Uani 1 1 d . . .
H4N H 0.6667 0.0212 0.1004 0.048 Uiso 1 1 calc R . .
O1 O -0.0133(3) -0.1697(3) 0.03203(7) 0.0408(7) Uani 1 1 d . . .
H1A H 0.0372 -0.1679 0.0493 0.061 Uiso 1 1 d R . .
H1B H -0.0366 -0.2391 0.0204 0.061 Uiso 1 1 d R . .
O2 O 0.1240(3) 0.1186(3) 0.04616(7) 0.0471(7) Uani 1 1 d . . .
H2A H 0.2032 0.1719 0.0527 0.071 Uiso 1 1 d R . .
H2B H 0.0620 0.1239 0.0559 0.071 Uiso 1 1 d R . .
O3 O 0.1664(2) 0.8336(2) 0.0833 0.0445(11) Uani 1 2 d S . .
O4 O 0.5497(3) 0.8262(4) 0.10961(13) 0.0811(14) Uani 1 1 d . . .
O5 O 0.90066(18) 0.09934(18) 0.0833 0.0358(9) Uani 1 2 d S . .
O6 O 0.5114(4) 0.1063(4) 0.10448(15) 0.0902(15) Uani 1 1 d . . .
O7 O 0.3697(5) 0.2549(6) 0.08017(14) 0.1055(17) Uani 1 1 d . . .
H7A H 0.4045 0.2175 0.0865 0.158 Uiso 1 1 d R . .
H7B H 0.4214 0.3194 0.0666 0.158 Uiso 1 1 d R . .
O8 O 0.9200(7) 0.5979(6) -0.00429(17) 0.062(2) Uani 0.638(15) 1 d P . .
H8A H 0.9160 0.5711 0.0119 0.093 Uiso 1 1 d R . .
H8B H 0.8734 0.5863 -0.0179 0.093 Uiso 1 1 d R . .
O8A O 0.802(2) 0.5889(15) 0.0083(5) 0.130(11) Uani 0.362(15) 1 d P . .
O9 O 0.5837(9) 0.5139(10) 0.0248(2) 0.187(4) Uani 1 1 d . . .
H9A H 0.5022 0.4797 0.0181 0.281 Uiso 1 1 d R . .
H9B H 0.6384 0.5653 0.0430 0.281 Uiso 1 1 d R . .
C1 C -0.2327(4) -0.1065(4) 0.01185(12) 0.0403(10) Uani 1 1 d . . .
H1 H -0.2298 -0.1815 0.0202 0.048 Uiso 1 1 calc R . .
C2 C -0.3555(4) -0.1100(4) 0.01223(12) 0.0397(10) Uani 1 1 d . . .
H2 H -0.4320 -0.1863 0.0207 0.048 Uiso 1 1 calc R . .
C3 C -0.3649(4) 0.0000 0.0000 0.0312(11) Uani 1 2 d S . .
C4 C -0.6230(4) 0.1147(4) 0.00415(12) 0.0380(9) Uani 1 1 d . . .
H4 H -0.6235 0.1950 0.0071 0.046 Uiso 1 1 calc R . .
C5 C -0.4991(4) 0.1189(4) 0.00426(11) 0.0390(9) Uani 1 1 d . . .
H5 H -0.4195 0.2003 0.0071 0.047 Uiso 1 1 calc R . .
C6 C -0.4959(4) 0.0000 0.0000 0.0325(12) Uani 1 2 d S . .
C7 C 0.2292(3) 0.7708(3) 0.0833 0.0343(13) Uani 1 2 d S . .
C8 C 0.4324(5) 0.7613(5) 0.09659(15) 0.0549(13) Uani 1 1 d . . .
C9 C 0.3696(3) 0.6304(3) 0.0833 0.066(2) Uani 1 2 d S . .
H9 H 0.4164 0.5836 0.0833 0.080 Uiso 1 2 calc SR . .
C10 C 0.8386(3) 0.1614(3) 0.0833 0.0308(12) Uani 1 2 d S . .
C11 C 0.6317(5) 0.1705(5) 0.09418(16) 0.0608(15) Uani 1 1 d . . .
C12 C 0.6965(4) 0.3035(4) 0.0833 0.077(3) Uani 1 2 d S . .
H12 H 0.6496 0.3503 0.0833 0.093 Uiso 1 2 calc SR . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.060(3) 5 ?
Cu1 O1 2.060(3) . ?
Cu1 O2 2.075(3) 5 ?
Cu1 O2 2.075(3) . ?
Cu1 N2 2.147(4) 1_655 ?
Cu1 N1 2.156(4) . ?
N1 C1 1.348(5) . ?
N1 C1 1.348(5) 5 ?
N2 C4 1.349(5) . ?
N2 C4 1.350(5) 5 ?
N2 Cu1 2.147(4) 1_455 ?
N3 C7 1.352(5) . ?
N3 C8 1.398(6) . ?
N4 C10 1.367(5) . ?
N4 C11 1.405(6) . ?
O3 C7 1.248(7) . ?
O4 C8 1.262(6) . ?
O5 C10 1.233(6) . ?
O6 C11 1.254(6) . ?
O8 O8A 1.38(2) . ?
C1 C2 1.388(6) . ?
C2 C3 1.395(5) . ?
C3 C2 1.394(5) 5 ?
C3 C6 1.501(7) . ?
C4 C5 1.398(5) . ?
C5 C6 1.391(5) . ?
C6 C5 1.391(5) 5 ?
C7 N3 1.353(5) 3_665 ?
C8 C9 1.389(6) . ?
C9 C8 1.389(6) 3_665 ?
C10 N4 1.368(5) 3_665 ?
C11 C12 1.381(6) . ?
C12 C11 1.380(6) 3_665 ?

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
_geom_angle_publ_flag
O1 Cu1 O1 179.45(16) 5 . ?
O1 Cu1 O2 89.53(12) 5 5 ?
O1 Cu1 O2 90.49(12) . 5 ?
O1 Cu1 O2 90.49(12) 5 . ?
O1 Cu1 O2 89.53(12) . . ?
O2 Cu1 O2 176.20(16) 5 . ?
O1 Cu1 N2 89.74(8) 5 1_655 ?
O1 Cu1 N2 89.71(8) . 1_655 ?
O2 Cu1 N2 91.89(8) 5 1_655 ?
O2 Cu1 N2 91.91(8) . 1_655 ?
O1 Cu1 N1 90.26(8) 5 . ?
O1 Cu1 N1 90.29(8) . . ?
O2 Cu1 N1 88.11(8) 5 . ?
O2 Cu1 N1 88.09(8) . . ?
N2 Cu1 N1 180.0 1_655 . ?
C1 N1 C1 116.4(5) . 5 ?
C1 N1 Cu1 121.8(2) . . ?
C1 N1 Cu1 121.8(2) 5 . ?
C4 N2 C4 116.9(4) . 5 ?
C4 N2 Cu1 121.5(2) . 1_455 ?
C4 N2 Cu1 121.6(2) 5 1_455 ?
C7 N3 C8 124.6(4) . . ?
C10 N4 C11 124.9(4) . . ?
N1 C1 C2 123.4(4) . . ?
C1 C2 C3 120.4(4) . . ?
C2 C3 C2 116.0(5) 5 . ?
C2 C3 C6 122.0(2) 5 . ?
C2 C3 C6 122.0(2) . . ?
N2 C4 C5 123.2(4) . . ?
C6 C5 C4 119.4(4) . . ?
C5 C6 C5 117.8(5) 5 . ?
C5 C6 C3 121.1(2) 5 . ?
C5 C6 C3 121.1(2) . . ?
O3 C7 N3 121.9(3) . . ?
O3 C7 N3 121.9(3) . 3_665 ?
N3 C7 N3 116.2(5) . 3_665 ?
O4 C8 C9 126.5(5) . . ?
O4 C8 N3 117.0(5) . . ?
C9 C8 N3 116.4(5) . . ?
C8 C9 C8 121.8(6) 3_665 . ?
O5 C10 N4 122.7(2) . . ?
O5 C10 N4 122.8(2) . 3_665 ?
N4 C10 N4 114.5(5) . 3_665 ?
O6 C11 C12 124.3(5) . . ?
O6 C11 N4 118.5(5) . . ?
C12 C11 N4 117.2(5) . . ?
C11 C12 C11 121.3(6) 3_665 . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 N1 C1 -12.6(2) . . . . no
O1 Cu1 N1 C1 167.4(2) . . . 5_555 no
O2 Cu1 N1 C1 -102.1(2) . . . . no
O2 Cu1 N1 C1 77.9(2) . . . 5_555 no
O1 Cu1 N1 C1 167.4(2) 5_555 . . . no
O1 Cu1 N2 C4 137.2(2) . . . . no
O1 Cu1 N2 C4 -42.8(2) . . . 5_555 no
O2 Cu1 N2 C4 47.7(2) . . . . no
O2 Cu1 N2 C4 -132.3(2) . . . 5_555 no
O1 Cu1 N2 C4 -42.8(2) 5_555 . . . no
Cu1 N1 C1 C2 -180.0(3) . . . . no
C1 N1 C1 C2 0.0(5) 5_555 . . . no
C8 N3 C7 N3 -1.8(5) . . . 3_665 no
C7 N3 C8 O4 -177.0(4) . . . . no
C7 N3 C8 C9 3.4(7) . . . . no
C8 N3 C7 O3 178.2(3) . . . . no
C10 N4 C11 C12 0.1(7) . . . . no
C11 N4 C10 O5 180.0(4) . . . . no
C11 N4 C10 N4 0.0(5) . . . 3_665 no
C10 N4 C11 O6 -179.6(4) . . . . no
N1 C1 C2 C3 0.0(6) . . . . no
C1 C2 C3 C2 0.0(5) . . . 5_555 no
C1 C2 C3 C6 -180.0(3) . . . 1_455 no
O4 C8 C9 C8 179.0(5) . . . 3_665 no
N3 C8 C9 C8 -1.6(6) . . . 3_665 no
O6 C11 C12 C11 179.6(5) . . . 3_665 no
N4 C11 C12 C11 0.0(6) . . . 3_665 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_site_symmetry_A
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
O1 H1A O3 0.8600 1.9400 2.788(4) 172.00 3_655 yes
O1 H1B O8 0.8200 1.9100 2.731(7) 175.00 1_445 yes
O2 H2A O7 0.8400 1.9400 2.749(7) 162.00 . yes
O2 H2B O5 0.8300 2.0000 2.816(4) 168.00 3_565 yes
N3 H3N O6 0.8600 1.9600 2.795(7) 164.00 1_565 yes
O7 H7A O6 0.7500 2.2700 3.020(8) 179.00 . yes
O7 H7B O9 0.8400 2.5800 3.427(11) 178.00 . yes
O8 H8B O4 0.7000 2.1200 2.819(10) 177.00 11_654 yes
O9 H9A O8 0.8500 1.8700 2.715(15) 179.00 5_565 yes
C1 H1 O1 0.9300 2.4600 3.038(6) 121.00 . yes

