#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:14:00 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179959 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/53/7025385.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_7025385
loop_
_publ_author_name
'Keene, Tony D.'
'Zimmermann, Iwan'
'Neels, Antonia'
'Sereda, Olha'
'Hauser, Jürg'
'Bonin, Michel'
'Hursthouse, Michael B.'
'Price, Daniel J.'
'Decurtins, Silvio'
_publ_section_title
;
 Heterocyclic amine directed synthesis of metal(II)-oxalates:
 investigating the magnetic properties of two complete series of chains
 with S = 5/2 to S = 1/2.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4937
_journal_page_last               4950
_journal_paper_doi               10.1039/b927522c
_journal_volume                  39
_journal_year                    2010
_chemical_formula_moiety         'C14 H10 Cu N6 O4'
_chemical_formula_sum            'C14 H10 Cu N6 O4'
_chemical_formula_weight         389.82
_chemical_melting_point          ?
_chemical_name_common            '[Cu(ox)(btz)2]n'
_chemical_name_systematic
;
catena-[(μ₂-oxalato)-bis(benzotriazole)-manganese(II)]
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 108.7210(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2379(2)
_cell_length_b                   12.28010(10)
_cell_length_c                   9.38300(10)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      34.062
_cell_measurement_theta_min      2.243
_cell_volume                     1553.75(3)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'DIAMOND 2.1a (Brandenberg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type
'BRUKER APEXII CCD area-detector diffractometer'
_diffrn_measurement_method       'rotation method'
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35225
_diffrn_reflns_theta_full        36.09
_diffrn_reflns_theta_max         36.09
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    1.440
_exptl_absorpt_correction_T_max  0.9110
_exptl_absorpt_correction_T_min  0.8067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008-1 (Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.603(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         6553
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                5830
_reflns_number_total             6553
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b927522c.txt
_cod_data_source_block           compound10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'N/A' was changed to '?' - the value
is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7025385
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'
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
C16 C 0.24790(18) 0.2502(2) 0.4328(2) 0.0395(5) Uani 1 1 d .
H16 H 0.1899 0.2098 0.3955 0.047 Uiso 1 1 calc R
Cu1 Cu 0.16841(2) 0.124191(13) 0.73839(3) 0.01896(5) Uani 1 1 d .
O4 O 0.24995(13) -0.11099(13) 0.4988(2) 0.0305(4) Uani 1 1 d .
O1 O 0.07518(11) 0.08895(14) 0.49139(18) 0.0251(3) Uani 1 1 d .
O2 O 0.08508(11) -0.01950(13) 0.30768(17) 0.0245(3) Uani 1 1 d .
O3 O 0.23962(12) -0.00190(13) 0.68333(18) 0.0265(3) Uani 1 1 d .
N12 N 0.34287(14) 0.25663(16) 0.8344(2) 0.0283(4) Uani 1 1 d .
N22 N -0.01265(13) 0.24506(15) 0.6538(2) 0.0287(4) Uani 1 1 d .
C1 C 0.11479(13) 0.01505(14) 0.4402(2) 0.0190(3) Uani 1 1 d .
C2 C 0.20985(14) -0.03697(15) 0.5506(2) 0.0214(3) Uani 1 1 d .
N13 N 0.27439(12) 0.22352(14) 0.71130(19) 0.0243(3) Uani 1 1 d .
N21 N -0.05944(14) 0.33458(16) 0.6733(2) 0.0307(4) Uani 1 1 d .
H21 H -0.1200 0.3498 0.6234 0.037 Uiso 1 1 calc R
N23 N 0.07836(12) 0.24831(14) 0.74735(19) 0.0239(3) Uani 1 1 d .
N11 N 0.40702(13) 0.31720(17) 0.7930(2) 0.0297(4) Uani 1 1 d .
H11 H 0.4580 0.3483 0.8549 0.036 Uiso 1 1 calc R
C25 C 0.1607(2) 0.4847(2) 1.0006(4) 0.0475(7) Uani 1 1 d .
H25 H 0.2137 0.5164 1.0743 0.057 Uiso 1 1 calc R
C13 C 0.4240(2) 0.3780(2) 0.5448(3) 0.0456(6) Uani 1 1 d .
H13 H 0.4804 0.4212 0.5814 0.055 Uiso 1 1 calc R
C21 C 0.09082(13) 0.34173(15) 0.8303(2) 0.0250(3) Uani 1 1 d .
C26 C 0.17367(18) 0.38488(18) 0.9428(3) 0.0353(5) Uani 1 1 d .
H26 H 0.2338 0.3480 0.9761 0.042 Uiso 1 1 calc R
C23 C -0.01177(19) 0.5002(2) 0.8422(3) 0.0430(6) Uani 1 1 d .
H23 H -0.0715 0.5379 0.8097 0.052 Uiso 1 1 calc R
C22 C 0.00093(16) 0.39891(18) 0.7825(2) 0.0305(4) Uani 1 1 d .
C12 C 0.38211(15) 0.32386(17) 0.6409(2) 0.0303(4) Uani 1 1 d .
C15 C 0.2908(2) 0.3006(2) 0.3391(3) 0.0526(7) Uani 1 1 d .
H15 H 0.2619 0.2930 0.2356 0.063 Uiso 1 1 calc R
C14 C 0.3781(3) 0.3641(3) 0.3958(3) 0.0551(8) Uani 1 1 d .
H14 H 0.4045 0.3972 0.3281 0.066 Uiso 1 1 calc R
C24 C 0.0696(2) 0.5399(2) 0.9514(3) 0.0522(7) Uani 1 1 d .
H24 H 0.0644 0.6066 0.9952 0.063 Uiso 1 1 calc R
C11 C 0.29561(14) 0.26235(16) 0.5878(2) 0.0270(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
C15 C16 C11 116.8(2) . .
C15 C16 H16 121.6 . .
C11 C16 H16 121.6 . .
O2 Cu1 O3 89.38(7) 2 .
O2 Cu1 N23 91.20(7) 2 .
O3 Cu1 N23 167.71(7) . .
O2 Cu1 N13 167.78(7) 2 .
O3 Cu1 N13 88.51(7) . .
N23 Cu1 N13 93.42(8) . .
O2 Cu1 O1 89.76(6) 2 .
O3 Cu1 O1 76.85(6) . .
N23 Cu1 O1 90.87(6) . .
N13 Cu1 O1 101.46(7) . .
O2 Cu1 O4 76.33(6) 2 2
O3 Cu1 O4 95.31(6) . 2
N23 Cu1 O4 96.75(7) . 2
N13 Cu1 O4 91.88(6) . 2
O1 Cu1 O4 164.22(5) . 2
C2 O4 Cu1 108.61(13) . 2_554
C1 O1 Cu1 109.75(12) . .
C1 O2 Cu1 119.70(13) . 2_554
C2 O3 Cu1 118.82(14) . .
N13 N12 N11 107.55(18) . .
N23 N22 N21 108.28(17) . .
O1 C1 O2 125.47(17) . .
O1 C1 C2 116.68(15) . .
O2 C1 C2 117.84(15) . .
O4 C2 O3 125.67(18) . .
O4 C2 C1 116.64(15) . .
O3 C2 C1 117.69(15) . .
N12 N13 C11 109.40(16) . .
N12 N13 Cu1 116.73(14) . .
C11 N13 Cu1 133.77(13) . .
N22 N21 C22 111.19(18) . .
N22 N21 H21 124.4 . .
C22 N21 H21 124.4 . .
N22 N23 C21 109.07(16) . .
N22 N23 Cu1 117.06(13) . .
C21 N23 Cu1 133.85(12) . .
N12 N11 C12 111.64(16) . .
N12 N11 H11 124.2 . .
C12 N11 H11 124.2 . .
C26 C25 C24 121.8(3) . .
C26 C25 H25 119.1 . .
C24 C25 H25 119.1 . .
C14 C13 C12 116.2(2) . .
C14 C13 H13 121.9 . .
C12 C13 H13 121.9 . .
N23 C21 C22 107.48(15) . .
N23 C21 C26 131.83(17) . .
C22 C21 C26 120.68(18) . .
C25 C26 C21 116.3(2) . .
C25 C26 H26 121.8 . .
C21 C26 H26 121.8 . .
C24 C23 C22 115.5(2) . .
C24 C23 H23 122.3 . .
C22 C23 H23 122.3 . .
N21 C22 C23 133.4(2) . .
N21 C22 C21 103.98(17) . .
C23 C22 C21 122.64(19) . .
N11 C12 C11 104.24(17) . .
N11 C12 C13 133.20(19) . .
C11 C12 C13 122.5(2) . .
C16 C15 C14 121.7(2) . .
C16 C15 H15 119.1 . .
C14 C15 H15 119.1 . .
C13 C14 C15 122.2(2) . .
C13 C14 H14 118.9 . .
C15 C14 H14 118.9 . .
C23 C24 C25 123.0(2) . .
C23 C24 H24 118.5 . .
C25 C24 H24 118.5 . .
N13 C11 C12 107.16(16) . .
N13 C11 C16 132.35(17) . .
C12 C11 C16 120.49(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C16 C15 1.369(3) .
C16 C11 1.402(3) .
C16 H16 0.9300 .
Cu1 O2 1.9946(15) 2
Cu1 O3 2.0072(16) .
Cu1 N23 2.0108(17) .
Cu1 N13 2.0187(17) .
Cu1 O1 2.3121(16) .
Cu1 O4 2.3503(17) 2
O4 C2 1.252(3) .
O4 Cu1 2.3503(17) 2_554
O1 C1 1.243(2) .
O2 C1 1.252(2) .
O2 Cu1 1.9946(15) 2_554
O3 C2 1.256(3) .
N12 N13 1.314(3) .
N12 N11 1.329(3) .
N22 N23 1.312(2) .
N22 N21 1.328(3) .
C1 C2 1.553(2) .
N13 C11 1.373(3) .
N21 C22 1.359(3) .
N21 H21 0.8600 .
N23 C21 1.366(3) .
N11 C12 1.358(3) .
N11 H11 0.8600 .
C25 C26 1.377(3) .
C25 C24 1.404(4) .
C25 H25 0.9300 .
C13 C14 1.351(4) .
C13 C12 1.399(3) .
C13 H13 0.9300 .
C21 C22 1.401(3) .
C21 C26 1.410(3) .
C26 H26 0.9300 .
C23 C24 1.367(4) .
C23 C22 1.399(3) .
C23 H23 0.9300 .
C12 C11 1.393(3) .
C15 C14 1.418(4) .
C15 H15 0.9300 .
C14 H14 0.9300 .
C24 H24 0.9300 .
