#------------------------------------------------------------------------------
#$Date: 2018-10-05 14:19:55 +0200 (vie 05 de oct de 2018) $
#$Revision: 211332 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/05/7050560.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_7050560
loop_
_publ_author_name
'José Carranza'
'Conor Brennan'
'Jorunn Sletten'
'Brita Vangdal'
'Paul Rillema'
'Francesc Lloret'
'Miguel Julve'
_publ_section_title
;
 Syntheses, crystal structures and magnetic properties of new oxalato-,
 croconato- and squarato-containing copper(II) complexes
;
_journal_issue                   12
_journal_name_full               'New J. Chem.'
_journal_page_first              1775
_journal_page_last               1783
_journal_paper_doi               10.1039/b301212n
_journal_volume                  27
_journal_year                    2003
_chemical_formula_sum            'C13 H8 Cu N4 O6'
_chemical_formula_weight         379.77
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   'geom if bound to C, difmap if bound to O'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.3160(10)
_cell_angle_beta                 97.9950(10)
_cell_angle_gamma                107.8400(10)
_cell_formula_units_Z            2
_cell_length_a                   6.7113(4)
_cell_length_b                   9.2977(5)
_cell_length_c                   11.8250(6)
_cell_measurement_reflns_used    4899
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.9
_cell_measurement_theta_min      2.5
_cell_volume                     653.32(6)
_computing_cell_refinement       'SAINT, version 6.02a'
_computing_data_collection       'SMART, version 5.054'
_computing_data_reduction        'SAINT, version 6.02a'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.888
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  '2K SMART CCD'
_diffrn_measurement_method       'omega scan'
_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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6057
_diffrn_reflns_theta_full        32.09
_diffrn_reflns_theta_max         32.09
_diffrn_reflns_theta_min         2.45
_diffrn_standards_decay_%        0
_diffrn_standards_number
'50 first frames remeasured at end of experiment'
_exptl_absorpt_coefficient_mu    1.717
_exptl_absorpt_correction_T_max  'see above'
_exptl_absorpt_correction_T_min  'Tmin/Tmax ratio 0.768846'
_exptl_absorpt_correction_type   'empirical, SADABS'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             382
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0296
_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)+(0.0418P)²+0.2473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                3684
_reflns_number_total             4055
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b301212n.txt
_cod_data_source_block           13jc
_cod_original_cell_volume        653.31(6)
_cod_database_code               7050560
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.28156(3) 0.33018(2) 0.128467(16) 0.01612(7) Uani 1 1 d . . .
O1 O 0.2735(2) 0.31781(14) -0.04131(10) 0.0209(2) Uani 1 1 d . . .
O2 O 0.25147(19) 0.10108(13) 0.07398(10) 0.0178(2) Uani 1 1 d . . .
O3 O 0.1892(2) -0.22139(14) -0.10683(11) 0.0227(2) Uani 1 1 d . . .
O4 O 0.2568(2) -0.16268(16) -0.33368(11) 0.0274(3) Uani 1 1 d . . .
O5 O 0.2829(2) 0.16962(16) -0.30445(11) 0.0261(3) Uani 1 1 d . . .
O6 O 0.6384(2) 0.44450(15) 0.19363(11) 0.0239(2) Uani 1 1 d . . .
H61 H 0.6985 0.5194 0.2681 0.029 Uiso 1 1 d R . .
H62 H 0.7003 0.3822 0.1798 0.029 Uiso 1 1 d R . .
N1 N 0.2412(2) 0.53992(15) 0.18235(12) 0.0157(2) Uani 1 1 d . . .
N2 N 0.2537(2) 0.33825(15) 0.29494(11) 0.0152(2) Uani 1 1 d . . .
N3 N 0.2135(2) 0.83872(17) 0.28714(14) 0.0225(3) Uani 1 1 d . . .
N4 N 0.2339(2) 0.38872(17) 0.53513(12) 0.0199(3) Uani 1 1 d . . .
C1 C 0.2342(3) 0.63532(19) 0.11715(15) 0.0185(3) Uani 1 1 d . . .
H1 H 0.2394 0.6017 0.0343 0.022 Uiso 1 1 calc R . .
C2 C 0.2194(3) 0.78480(19) 0.17105(16) 0.0213(3) Uani 1 1 d . . .
H2 H 0.2132 0.8506 0.1231 0.026 Uiso 1 1 calc R . .
C3 C 0.2201(3) 0.74117(19) 0.35153(15) 0.0205(3) Uani 1 1 d . . .
H3 H 0.2164 0.7757 0.4346 0.025 Uiso 1 1 calc R . .
C4 C 0.2324(2) 0.59103(17) 0.29977(14) 0.0159(3) Uani 1 1 d . . .
C5 C 0.2383(2) 0.47533(17) 0.36322(13) 0.0150(3) Uani 1 1 d . . .
C6 C 0.2322(2) 0.50059(18) 0.48435(14) 0.0176(3) Uani 1 1 d . . .
H6 H 0.2266 0.5996 0.5322 0.021 Uiso 1 1 calc R . .
C7 C 0.2444(3) 0.25164(19) 0.46501(14) 0.0197(3) Uani 1 1 d . . .
H7 H 0.2422 0.1692 0.4980 0.024 Uiso 1 1 calc R . .
C8 C 0.2583(3) 0.22645(18) 0.34490(14) 0.0174(3) Uani 1 1 d . . .
H8 H 0.2712 0.1296 0.2984 0.021 Uiso 1 1 calc R . .
C9 C 0.2640(2) 0.17741(18) -0.09911(14) 0.0165(3) Uani 1 1 d . . .
C10 C 0.2493(2) 0.06235(17) -0.03930(13) 0.0152(3) Uani 1 1 d . . .
C11 C 0.2266(2) -0.09125(18) -0.12466(14) 0.0169(3) Uani 1 1 d . . .
C12 C 0.2528(2) -0.06316(19) -0.24124(14) 0.0187(3) Uani 1 1 d . . .
C13 C 0.2680(3) 0.10684(19) -0.22641(14) 0.0181(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
O1 Cu1 O2 86.71(4) . . ?
O1 Cu1 N2 173.43(5) . . ?
O2 Cu1 N2 94.04(5) . . ?
O1 Cu1 N1 96.10(5) . . ?
O2 Cu1 N1 166.99(5) . . ?
N2 Cu1 N1 81.73(5) . . ?
O1 Cu1 O6 95.21(5) . . ?
O2 Cu1 O6 99.51(5) . . ?
N2 Cu1 O6 91.10(5) . . ?
N1 Cu1 O6 92.90(5) . . ?
O1 Cu1 O3 97.80(4) . 2 ?
O2 Cu1 O3 87.98(4) . 2 ?
N2 Cu1 O3 75.72(4) . 2 ?
N1 Cu1 O3 79.06(4) . 2 ?
O6 Cu1 O3 165.34(4) . 2 ?
C9 O1 Cu1 106.75(10) . . ?
C10 O2 Cu1 105.89(9) . . ?
Cu1 O6 H61 119.8 . . ?
Cu1 O6 H62 114.0 . . ?
H61 O6 H62 111.3 . . ?
C1 N1 C4 118.61(13) . . ?
C1 N1 Cu1 126.80(11) . . ?
C4 N1 Cu1 114.48(10) . . ?
C8 N2 C5 118.76(13) . . ?
C8 N2 Cu1 126.71(10) . . ?
C5 N2 Cu1 114.46(10) . . ?
C2 N3 C3 116.83(14) . . ?
C7 N4 C6 117.29(13) . . ?
N1 C1 C2 119.84(15) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
N3 C2 C1 122.63(14) . . ?
N3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
N3 C3 C4 121.73(15) . . ?
N3 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
N1 C4 C3 120.35(14) . . ?
N1 C4 C5 114.22(13) . . ?
C3 C4 C5 125.43(14) . . ?
N2 C5 C6 120.16(14) . . ?
N2 C5 C4 114.83(13) . . ?
C6 C5 C4 125.00(13) . . ?
N4 C6 C5 121.68(14) . . ?
N4 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
N4 C7 C8 121.86(14) . . ?
N4 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
N2 C8 C7 120.19(14) . . ?
N2 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
O1 C9 C10 120.17(13) . . ?
O1 C9 C13 129.71(14) . . ?
C10 C9 C13 110.12(13) . . ?
O2 C10 C9 120.36(13) . . ?
O2 C10 C11 129.29(14) . . ?
C9 C10 C11 110.33(13) . . ?
O3 C11 C10 127.62(14) . . ?
O3 C11 C12 126.37(14) . . ?
C10 C11 C12 106.00(13) . . ?
O4 C12 C11 125.66(15) . . ?
O4 C12 C13 126.01(15) . . ?
C11 C12 C13 108.32(12) . . ?
O5 C13 C9 128.72(15) . . ?
O5 C13 C12 126.42(15) . . ?
C9 C13 C12 104.85(13) . . ?
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 1.9705(11) . ?
Cu1 O2 1.9805(11) . ?
Cu1 N2 1.9858(13) . ?
Cu1 N1 1.9891(13) . ?
Cu1 O6 2.2192(13) . ?
Cu1 O3 2.9568(13) 2 ?
O1 C9 1.2692(19) . ?
O2 C10 1.2825(18) . ?
O3 C11 1.2425(19) . ?
O4 C12 1.2276(19) . ?
O5 C13 1.223(2) . ?
O6 H61 0.8993 . ?
O6 H62 0.8048 . ?
N1 C1 1.3352(19) . ?
N1 C4 1.3515(19) . ?
N2 C8 1.3379(19) . ?
N2 C5 1.3465(19) . ?
N3 C2 1.333(2) . ?
N3 C3 1.345(2) . ?
N4 C7 1.339(2) . ?
N4 C6 1.341(2) . ?
C1 C2 1.397(2) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.481(2) . ?
C5 C6 1.393(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.426(2) . ?
C9 C13 1.471(2) . ?
C10 C11 1.448(2) . ?
C11 C12 1.497(2) . ?
C12 C13 1.510(2) . ?
