#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:44:31 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179202 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/37/4313745.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_4313745
loop_
_publ_author_name
'Jamie L. Manson'
'Jiyeong Gu'
'John A. Schlueter'
'H.-Hau Wang'
_publ_section_title
;
 Structures and Magnetic Behavior of 1-, 2-, and 3D Coordination Polymers
 in the Cu(II)-Dicyanamide-Pyrimidine Family
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3950
_journal_page_last               3955
_journal_paper_doi               10.1021/ic026164t
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C6 H6 Cu N6 O4'
_chemical_formula_weight         289.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.585(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6475(3)
_cell_length_b                   12.2422(5)
_cell_length_c                   11.0286(4)
_cell_measurement_temperature    301(2)
_cell_volume                     989.57(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_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  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6673
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    2.223
_exptl_crystal_density_diffrn    1.945
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0236(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0230
_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)+(0.0266P)²+0.4280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0637
_reflns_number_gt                2196
_reflns_number_total             2336
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic026164tsi20021108_021441_2.cif
_cod_data_source_block           cudcapym_nitrate2
_cod_database_code               4313745
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.04251(2) 0.760541(16) 0.244735(16) 0.01950(9) Uani 1 1 d . . .
N5 N 0.18763(18) 0.84528(11) 0.39810(12) 0.0209(3) Uani 1 1 d . . .
N1 N 0.1297(2) 0.85526(12) 0.12690(13) 0.0274(3) Uani 1 1 d . . .
C1 C 0.2064(2) 0.88714(13) 0.05884(16) 0.0261(3) Uani 1 1 d . . .
C6 C 0.3025(2) 0.79137(14) 0.49267(14) 0.0219(3) Uani 1 1 d . . .
H6A H 0.3140 0.7165 0.4832 0.026 Uiso 1 1 calc R . .
O4 O -0.2018(2) 0.87948(13) 0.21654(15) 0.0350(3) Uani 1 1 d . . .
N2 N 0.2889(3) 0.93367(13) -0.01634(17) 0.0420(5) Uani 1 1 d . . .
C3 C 0.1708(2) 0.95310(14) 0.41027(15) 0.0259(3) Uani 1 1 d . . .
H3A H 0.0905 0.9923 0.3457 0.031 Uiso 1 1 calc R . .
N4 N 0.4532(2) 0.71032(14) 0.24151(15) 0.0302(3) Uani 1 1 d . . .
O2 O 0.5328(2) 0.78316(14) 0.31590(17) 0.0504(4) Uani 1 1 d . . .
O3 O 0.4943(2) 0.69508(16) 0.14238(16) 0.0551(4) Uani 1 1 d . . .
O1 O 0.3289(2) 0.65468(11) 0.26591(14) 0.0368(3) Uani 1 1 d . . .
C4 C 0.2716(3) 1.00698(14) 0.51792(17) 0.0305(4) Uani 1 1 d . . .
H4A H 0.2619 1.0821 0.5265 0.037 Uiso 1 1 calc R . .
N6 N 0.40184(18) 0.83664(11) 0.59961(12) 0.0211(3) Uani 1 1 d . . .
C5 C 0.3863(2) 0.94557(13) 0.61158(15) 0.0262(3) Uani 1 1 d . . .
H5A H 0.4550 0.9799 0.6850 0.031 Uiso 1 1 calc R . .
H4B H -0.290(4) 0.845(2) 0.221(2) 0.049(7) Uiso 1 1 d . . .
H4C H -0.220(4) 0.910(2) 0.158(3) 0.056(9) Uiso 1 1 d . . .
C2 C 0.3770(2) 0.87501(13) -0.07804(15) 0.0250(3) Uani 1 1 d . . .
N3 N 0.4596(2) 0.83513(12) -0.13785(13) 0.0281(3) Uani 1 1 d . . .
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
_geom_angle_publ_flag
N3 Cu1 N1 179.03(6) 4_576 . ?
N3 Cu1 N5 87.61(6) 4_576 . ?
N1 Cu1 N5 92.35(6) . . ?
N3 Cu1 N6 88.42(6) 4_576 4_575 ?
N1 Cu1 N6 91.57(5) . 4_575 ?
N5 Cu1 N6 175.06(5) . 4_575 ?
N3 Cu1 O4 93.60(6) 4_576 . ?
N1 Cu1 O4 87.36(6) . . ?
N5 Cu1 O4 91.08(5) . . ?
N6 Cu1 O4 92.11(5) 4_575 . ?
N3 Cu1 O1 93.90(6) 4_576 . ?
N1 Cu1 O1 85.13(5) . . ?
N5 Cu1 O1 86.03(5) . . ?
N6 Cu1 O1 91.30(5) 4_575 . ?
O4 Cu1 O1 171.84(5) . . ?
C6 N5 C3 118.16(14) . . ?
C6 N5 Cu1 118.84(11) . . ?
C3 N5 Cu1 122.98(11) . . ?
C1 N1 Cu1 162.75(14) . . ?
N1 C1 N2 174.07(18) . . ?
N6 C6 N5 124.84(15) . . ?
C2 N2 C1 120.44(16) . . ?
N5 C3 C4 120.70(15) . . ?
O3 N4 O2 119.39(17) . . ?
O3 N4 O1 120.40(17) . . ?
O2 N4 O1 120.19(15) . . ?
N4 O1 Cu1 113.24(11) . . ?
C5 C4 C3 117.66(16) . . ?
C6 N6 C5 117.09(14) . . ?
C6 N6 Cu1 119.60(11) . 4_676 ?
C5 N6 Cu1 122.82(11) . 4_676 ?
N6 C5 C4 121.54(16) . . ?
N3 C2 N2 171.73(18) . . ?
C2 N3 Cu1 164.10(15) . 4_675 ?
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 N3 1.9799(14) 4_576 ?
Cu1 N1 1.9932(14) . ?
Cu1 N5 2.0242(13) . ?
Cu1 N6 2.0375(13) 4_575 ?
Cu1 O4 2.3185(14) . ?
Cu1 O1 2.4978(14) . ?
N5 C6 1.331(2) . ?
N5 C3 1.337(2) . ?
N1 C1 1.145(2) . ?
C1 N2 1.307(2) . ?
C6 N6 1.328(2) . ?
N2 C2 1.301(2) . ?
C3 C4 1.384(2) . ?
N4 O3 1.235(2) . ?
N4 O2 1.246(2) . ?
N4 O1 1.259(2) . ?
C4 C5 1.373(3) . ?
N6 C5 1.349(2) . ?
N6 Cu1 2.0375(13) 4_676 ?
C2 N3 1.145(2) . ?
N3 Cu1 1.9799(14) 4_675 ?
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
N3 Cu1 N5 C6 53.33(12) 4_576 . . . ?
N1 Cu1 N5 C6 -125.71(11) . . . . ?
N6 Cu1 N5 C6 16.7(6) 4_575 . . . ?
O4 Cu1 N5 C6 146.89(11) . . . . ?
O1 Cu1 N5 C6 -40.75(11) . . . . ?
N3 Cu1 N5 C3 -125.20(13) 4_576 . . . ?
N1 Cu1 N5 C3 55.77(13) . . . . ?
N6 Cu1 N5 C3 -161.8(5) 4_575 . . . ?
O4 Cu1 N5 C3 -31.64(13) . . . . ?
O1 Cu1 N5 C3 140.72(13) . . . . ?
N3 Cu1 N1 C1 17(4) 4_576 . . . ?
N5 Cu1 N1 C1 104.2(5) . . . . ?
N6 Cu1 N1 C1 -72.8(5) 4_575 . . . ?
O4 Cu1 N1 C1 -164.8(5) . . . . ?
O1 Cu1 N1 C1 18.4(5) . . . . ?
Cu1 N1 C1 N2 -161.6(17) . . . . ?
C3 N5 C6 N6 0.4(2) . . . . ?
Cu1 N5 C6 N6 -178.16(12) . . . . ?
N1 C1 N2 C2 180(100) . . . . ?
C6 N5 C3 C4 0.6(2) . . . . ?
Cu1 N5 C3 C4 179.14(13) . . . . ?
O3 N4 O1 Cu1 -107.18(17) . . . . ?
O2 N4 O1 Cu1 71.1(2) . . . . ?
N3 Cu1 O1 N4 -155.65(12) 4_576 . . . ?
N1 Cu1 O1 N4 24.38(12) . . . . ?
N5 Cu1 O1 N4 -68.32(12) . . . . ?
N6 Cu1 O1 N4 115.85(12) 4_575 . . . ?
O4 Cu1 O1 N4 1.2(4) . . . . ?
N5 C3 C4 C5 -1.0(3) . . . . ?
N5 C6 N6 C5 -1.0(2) . . . . ?
N5 C6 N6 Cu1 171.17(12) . . . 4_676 ?
C6 N6 C5 C4 0.6(2) . . . . ?
Cu1 N6 C5 C4 -171.33(13) 4_676 . . . ?
C3 C4 C5 N6 0.3(3) . . . . ?
C1 N2 C2 N3 -178.7(13) . . . . ?
N2 C2 N3 Cu1 -132.9(12) . . . 4_675 ?
