#------------------------------------------------------------------------------
#$Date: 2018-10-05 14:19:55 +0200 (vie 05 de oct de 2018) $
#$Revision: 211332 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/05/7050558.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_7050558
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            'C12 H15 Cu N3 O8'
_chemical_formula_weight         392.81
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens
'geom if bound to C or N, difmap if bound to O'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.533(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4848(4)
_cell_length_b                   21.1731(12)
_cell_length_c                   9.3035(5)
_cell_measurement_reflns_used    8132
_cell_measurement_temperature    153(2)
_cell_volume                     1554.72(14)
_computing_cell_refinement       'SAINT, version 6.02a'
_computing_data_collection       'SMART, version 5.054'
_computing_data_reduction        'SAINT, version 6.02a'
_computing_molecular_graphics    'XP, version 5.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13985
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        0
_diffrn_standards_number
'50 first frames remeasured at end of data collection'
_exptl_absorpt_coefficient_mu    1.453
_exptl_absorpt_correction_T_max  'see above'
_exptl_absorpt_correction_T_min  'Tmin/Tmax ratio 0.830281'
_exptl_absorpt_correction_type   'empirical, SADABS'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0263
_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)+(0.0476P)²+0.1883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0845
_reflns_number_gt                4093
_reflns_number_total             4716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b301212n.txt
_cod_data_source_block           2jc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7050558
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.41859(2) 0.656775(7) 0.10438(2) 0.01757(6) Uani 1 1 d . . .
O1 O 0.27046(14) 0.68661(5) 0.20983(13) 0.0230(2) Uani 1 1 d . . .
O2 O 0.15639(14) 0.54149(5) 0.24602(14) 0.0272(2) Uani 1 1 d . . .
O3 O -0.09049(14) 0.59630(5) 0.41600(13) 0.0268(2) Uani 1 1 d . . .
O4 O 0.00869(14) 0.73912(5) 0.35671(14) 0.0267(2) Uani 1 1 d . . .
O5 O 0.39177(14) 0.56533(5) 0.13103(14) 0.0243(2) Uani 1 1 d . . .
H51 H 0.3250 0.5555 0.1624 0.036 Uiso 1 1 d R . .
H52 H 0.4827 0.5446 0.1841 0.036 Uiso 1 1 d R . .
O6 O 0.22067(14) 0.66133(5) -0.12892(13) 0.0238(2) Uani 1 1 d . . .
H61 H 0.1554 0.6906 -0.1381 0.036 Uiso 1 1 d R . .
H62 H 0.1663 0.6285 -0.1581 0.036 Uiso 1 1 d R . .
O7 O 0.67565(15) 0.50371(6) 0.29203(16) 0.0328(3) Uani 1 1 d . . .
H71 H 0.7236 0.4814 0.2578 0.049 Uiso 1 1 d R . .
H72 H 0.7416 0.5334 0.3180 0.051 Uiso 1 1 d R . .
O8 O -0.03299(15) 0.44125(5) 0.27464(14) 0.0275(2) Uani 1 1 d . . .
H81 H 0.0034 0.4326 0.3587 0.041 Uiso 1 1 d R . .
H82 H 0.0329 0.4711 0.2795 0.041 Uiso 1 1 d R . .
N1 N 0.48949(15) 0.74886(5) 0.09709(14) 0.0182(2) Uani 1 1 d . . .
N2 N 0.61251(15) 0.64215(6) 0.03615(14) 0.0192(2) Uani 1 1 d . . .
N3 N 0.79984(15) 0.68466(6) -0.04875(14) 0.0207(2) Uani 1 1 d . . .
H31 H 0.8598 0.7132 -0.0750 0.031 Uiso 1 1 calc R . .
C1 C 0.41851(18) 0.80084(7) 0.13126(17) 0.0210(3) Uani 1 1 d . . .
H1 H 0.3314 0.7960 0.1717 0.031 Uiso 1 1 calc R . .
C2 C 0.4691(2) 0.86138(7) 0.10895(17) 0.0241(3) Uani 1 1 d . . .
H2 H 0.4168 0.8973 0.1337 0.036 Uiso 1 1 calc R . .
C3 C 0.5961(2) 0.86888(7) 0.05044(19) 0.0262(3) Uani 1 1 d . . .
H3 H 0.6315 0.9099 0.0340 0.039 Uiso 1 1 calc R . .
C4 C 0.67140(19) 0.81553(7) 0.01594(18) 0.0235(3) Uani 1 1 d . . .
H4 H 0.7597 0.8194 -0.0234 0.035 Uiso 1 1 calc R . .
C5 C 0.61436(17) 0.75651(6) 0.04036(16) 0.0181(2) Uani 1 1 d . . .
C6 C 0.67846(17) 0.69611(6) 0.00911(16) 0.0183(2) Uani 1 1 d . . .
C7 C 0.69622(18) 0.59401(7) -0.00651(17) 0.0217(3) Uani 1 1 d . . .
H7 H 0.6764 0.5501 -0.0003 0.032 Uiso 1 1 calc R . .
C8 C 0.81271(19) 0.62009(7) -0.05926(17) 0.0227(3) Uani 1 1 d . . .
H8 H 0.8878 0.5979 -0.0960 0.034 Uiso 1 1 calc R . .
C9 C 0.16843(17) 0.65991(6) 0.26105(16) 0.0175(2) Uani 1 1 d . . .
C10 C 0.11805(17) 0.59538(7) 0.28053(16) 0.0194(2) Uani 1 1 d . . .
C11 C 0.00474(17) 0.61996(7) 0.35463(16) 0.0195(3) Uani 1 1 d . . .
C12 C 0.05145(17) 0.68490(7) 0.33018(16) 0.0191(2) 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 O5 97.37(4) . . ?
O1 Cu1 N2 164.76(5) . . ?
O5 Cu1 N2 91.97(5) . . ?
O1 Cu1 N1 87.70(4) . . ?
O5 Cu1 N1 170.22(5) . . ?
N2 Cu1 N1 81.40(5) . . ?
O1 Cu1 O6 94.70(4) . . ?
O5 Cu1 O6 94.89(4) . . ?
N2 Cu1 O6 96.47(5) . . ?
N1 Cu1 O6 93.01(4) . . ?
C9 O1 Cu1 134.24(9) . . ?
Cu1 O5 H51 117.0 . . ?
Cu1 O5 H52 116.6 . . ?
H51 O5 H52 106.2 . . ?
Cu1 O6 H61 112.3 . . ?
Cu1 O6 H62 114.8 . . ?
H61 O6 H62 109.3 . . ?
H71 O7 H72 100.9 . . ?
H81 O8 H82 96.7 . . ?
C1 N1 C5 118.37(12) . . ?
C1 N1 Cu1 127.40(9) . . ?
C5 N1 Cu1 114.05(9) . . ?
C6 N2 C7 106.37(12) . . ?
C6 N2 Cu1 112.27(9) . . ?
C7 N2 Cu1 141.05(10) . . ?
C6 N3 C8 107.40(11) . . ?
C6 N3 H31 126.3 . . ?
C8 N3 H31 126.3 . . ?
N1 C1 C2 121.89(13) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.47(14) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.16(14) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.40(13) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 122.71(12) . . ?
N1 C5 C6 111.98(11) . . ?
C4 C5 C6 125.31(12) . . ?
N2 C6 N3 110.83(12) . . ?
N2 C6 C5 119.94(12) . . ?
N3 C6 C5 129.22(12) . . ?
C8 C7 N2 108.66(13) . . ?
C8 C7 H7 125.7 . . ?
N2 C7 H7 125.7 . . ?
C7 C8 N3 106.74(12) . . ?
C7 C8 H8 126.6 . . ?
N3 C8 H8 126.6 . . ?
O1 C9 C10 137.39(12) . . ?
O1 C9 C12 132.19(12) . . ?
C10 C9 C12 90.41(10) . . ?
O2 C10 C9 134.42(12) . . ?
O2 C10 C11 135.66(13) . . ?
C9 C10 C11 89.92(11) . . ?
O3 C11 C10 135.67(14) . . ?
O3 C11 C12 134.39(13) . . ?
C10 C11 C12 89.93(10) . . ?
O4 C12 C9 135.05(13) . . ?
O4 C12 C11 135.26(12) . . ?
C9 C12 C11 89.69(11) . . ?
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 1.9612(10) . ?
Cu1 O5 1.9758(10) . ?
Cu1 N2 1.9932(12) . ?
Cu1 N1 2.0489(11) . ?
Cu1 O6 2.2057(11) . ?
O1 C9 1.2645(16) . ?
O2 C10 1.2600(17) . ?
O3 C11 1.2524(17) . ?
O4 C12 1.2553(17) . ?
O5 H51 0.7552 . ?
O5 H52 0.8665 . ?
O6 H61 0.8141 . ?
O6 H62 0.8236 . ?
O7 H71 0.7647 . ?
O7 H72 0.8164 . ?
O8 H81 0.7510 . ?
O8 H82 0.8337 . ?
N1 C1 1.3473(17) . ?
N1 C5 1.3557(17) . ?
N2 C6 1.3360(17) . ?
N2 C7 1.3814(18) . ?
N3 C6 1.3476(16) . ?
N3 C8 1.378(2) . ?
N3 H31 0.8800 . ?
C1 C2 1.391(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3885(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4601(19) . ?
C7 C8 1.371(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.4626(18) . ?
C9 C12 1.4654(18) . ?
C10 C11 1.4687(19) . ?
C11 C12 1.472(2) . ?
