#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006594.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006594
loop_
_publ_author_name
'Leban, I.'
'Kozlevcar, B.'
'Sieler, J.'
'Segedin, P.'
_publ_section_title
;
Bis(nicotinamide-N)bis(salicylato-O,O')copper(II),
the Monoclinic Form
;
_journal_issue 10
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first 1420
_journal_page_last 1422
_journal_volume 53
_journal_year 1997
_chemical_formula_iupac '[Cu (C7 H5 O3)2 (C6 H6 N2 O)2]'
_chemical_formula_moiety '(Cu1 2+), (C7 H5 O3 1-)2, (C6 H6 N2 O)2'
_chemical_formula_sum 'C26 H22 Cu N4 O8'
_chemical_formula_weight 582.02
_chemical_name_systematic
;
bis(salicylato)bis(nicotinamide)copper(II)
;
_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'
_audit_creation_method SHELXL
_cell_angle_alpha 90.00
_cell_angle_beta 99.000(10)
_cell_angle_gamma 90.00
_cell_formula_units_Z 2
_cell_length_a 10.8340(10)
_cell_length_b 9.7500(10)
_cell_length_c 12.3810(10)
_cell_measurement_reflns_used 25
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 12
_cell_measurement_theta_min 10
_cell_volume 1291.7(2)
_computing_cell_refinement 'CAD-4 Software'
_computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'NRCVAX (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1971) and PLUTON (Spek, 1991)'
_computing_publication_material SHELXL93
_computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution 'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature 293(2)
_diffrn_measurement_device 'Nonius CAD-4 diffractometer'
_diffrn_measurement_method 'variable rate \q/2\q scans'
_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 0.0231
_diffrn_reflns_av_sigmaI/netI 0.0289
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 5720
_diffrn_reflns_theta_max 26.25
_diffrn_reflns_theta_min 2.32
_diffrn_standards_decay_% 2.0
_diffrn_standards_interval_time 180
_diffrn_standards_number 3
_exptl_absorpt_coefficient_mu 0.903
_exptl_absorpt_correction_type none
_exptl_crystal_colour red-violet
_exptl_crystal_density_diffrn 1.496
_exptl_crystal_density_meas 1.49(5)
_exptl_crystal_density_method 'flotation in hexane/CCl~4~'
_exptl_crystal_description plate
_exptl_crystal_F_000 598
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.12
_refine_diff_density_max 0.272
_refine_diff_density_min -0.244
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_all 1.088
_refine_ls_goodness_of_fit_obs 1.106
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 222
_refine_ls_number_reflns 2337
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.088
_refine_ls_restrained_S_obs 1.106
_refine_ls_R_factor_all 0.0460
_refine_ls_R_factor_obs 0.0365
_refine_ls_shift/esd_max 0.002
_refine_ls_shift/esd_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0183P)^2^+1.2159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all 0.0811
_refine_ls_wR_factor_obs 0.0757
_reflns_number_observed 2003
_reflns_number_total 2337
_reflns_observed_criterion >2sigma(I)
_[local]_cod_data_source_file ka1233.cif
_[local]_cod_data_source_block cryV32
_[local]_cod_chemical_formula_sum_orig 'C26 H22 Cu1 N4 O8'
_cod_database_code 2006594
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cu 0.0252(2) 0.0316(2) 0.0498(3) -0.0076(2) 0.0031(2) -0.0085(2)
O1 0.0320(9) 0.0376(10) 0.0668(12) -0.0084(7) 0.0087(9) -0.0067(9)
O2 0.0293(10) 0.0732(14) 0.0633(13) -0.0015(9) -0.0062(9) -0.0132(11)
O3 0.0565(15) 0.084(2) 0.0627(14) 0.0121(13) 0.0018(12) 0.0187(13)
C1 0.0300(13) 0.0416(15) 0.051(2) -0.0024(11) 0.0051(12) -0.0174(13)
C2 0.0299(13) 0.0392(14) 0.0448(14) -0.0043(11) 0.0035(11) -0.0034(11)
C3 0.0418(15) 0.051(2) 0.0439(15) 0.0054(13) 0.0076(12) -0.0005(13)
C4 0.065(2) 0.060(2) 0.067(2) -0.013(2) 0.021(2) 0.015(2)
C5 0.047(2) 0.093(3) 0.081(2) -0.032(2) 0.010(2) 0.012(2)
C6 0.039(2) 0.112(3) 0.071(2) -0.026(2) -0.011(2) 0.023(2)
C7 0.0342(15) 0.070(2) 0.059(2) -0.0124(14) -0.0018(13) 0.018(2)
O4 0.0664(15) 0.0285(11) 0.103(2) -0.0101(9) -0.0182(13) -0.0089(11)
N1 0.0282(11) 0.0343(11) 0.0491(12) -0.0046(9) 0.0018(9) -0.0049(10)
N2 0.0390(14) 0.0353(14) 0.084(2) -0.0071(11) -0.0165(13) -0.0090(13)
C8 0.0313(13) 0.0278(13) 0.0451(14) -0.0019(10) 0.0011(11) -0.0030(11)
C9 0.0362(14) 0.0285(12) 0.0460(14) -0.0031(10) 0.0012(11) -0.0024(11)
C10 0.046(2) 0.0342(15) 0.084(2) 0.0028(13) 0.004(2) -0.017(2)
C11 0.036(2) 0.047(2) 0.098(3) 0.0117(13) 0.001(2) -0.014(2)
C12 0.0266(14) 0.046(2) 0.072(2) -0.0031(12) 0.0005(13) -0.0125(14)
C13 0.046(2) 0.0318(14) 0.055(2) -0.0080(12) -0.0027(13) -0.0084(12)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cu 0 0 0.5 0.03582(14) Uani d S 1 Cu
O1 -0.1718(2) -0.0327(2) 0.5160(2) 0.0454(5) Uani d . 1 O
O2 -0.0870(2) -0.1477(2) 0.6634(2) 0.0567(5) Uani d . 1 O
O3 -0.2191(2) -0.3281(3) 0.7476(2) 0.0686(7) Uani d . 1 O
C1 -0.1792(2) -0.1181(3) 0.5926(2) 0.0410(6) Uani d . 1 C
C2 -0.3009(2) -0.1887(3) 0.5925(2) 0.0382(6) Uani d . 1 C
C3 -0.3136(3) -0.2918(3) 0.6677(2) 0.0455(6) Uani d . 1 C
C4 -0.4260(3) -0.3623(4) 0.6614(3) 0.0629(9) Uani d . 1 C
C5 -0.5240(3) -0.3293(4) 0.5827(3) 0.0741(11) Uani d . 1 C
C6 -0.5141(3) -0.2266(5) 0.5084(3) 0.0761(12) Uani d . 1 C
C7 -0.4025(3) -0.1582(4) 0.5129(3) 0.0556(8) Uani d . 1 C
O4 -0.2272(2) -0.5680(2) 0.2826(2) 0.0694(7) Uani d . 1 O
N1 0.0096(2) -0.1893(2) 0.4352(2) 0.0376(5) Uani d . 1 N
N2 -0.3092(2) -0.3592(3) 0.2452(2) 0.0556(7) Uani d . 1 N
C8 -0.0945(2) -0.2486(2) 0.3817(2) 0.0353(6) Uani d . 1 C
C9 -0.0969(2) -0.3783(2) 0.3381(2) 0.0375(6) Uani d . 1 C
C10 0.0139(3) -0.4515(3) 0.3506(3) 0.0554(8) Uani d . 1 C
C11 0.1216(3) -0.3913(3) 0.4036(3) 0.0615(9) Uani d . 1 C
C12 0.1156(3) -0.2616(3) 0.4449(3) 0.0488(7) Uani d . 1 C
C13 -0.2169(3) -0.4432(3) 0.2852(2) 0.0457(7) Uani d . 1 C
H1 -0.392(3) -0.093(3) 0.459(2) 0.059(9) Uiso d . 1 H
H2 -0.580(4) -0.207(4) 0.452(3) 0.092(12) Uiso d . 1 H
H3 -0.604(3) -0.373(3) 0.583(3) 0.075(10) Uiso d . 1 H
H4 -0.432(3) -0.427(3) 0.712(3) 0.067(10) Uiso d . 1 H
H5 -0.159(3) -0.271(4) 0.741(3) 0.071(12) Uiso d . 1 H
H6 -0.168(2) -0.195(2) 0.3787(18) 0.031(6) Uiso d . 1 H
H7 0.016(3) -0.538(3) 0.324(3) 0.069(10) Uiso d . 1 H
H8 0.198(3) -0.438(3) 0.413(3) 0.072(10) Uiso d . 1 H
H9 0.184(3) -0.223(3) 0.482(2) 0.049(8) Uiso d . 1 H
H10 -0.296(3) -0.276(3) 0.243(2) 0.057(9) Uiso d . 1 H
H11 -0.378(3) -0.389(3) 0.223(3) 0.067(11) Uiso d . 1 H
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu O1 . 3_556 180.0 ?
O1 Cu N1 . 3_556 89.99(8) ?
O1 Cu N1 3_556 3_556 90.01(8) ?
O1 Cu N1 . . 90.01(8) yes
O1 Cu N1 3_556 . 89.99(8) ?
N1 Cu N1 3_556 . 180.0 ?
O1 Cu O2 . 3_556 127.28(7) ?
O1 Cu O2 3_556 3_556 52.72(7) ?
N1 Cu O2 3_556 3_556 81.91(7) ?
N1 Cu O2 . 3_556 98.09(7) ?
O1 Cu O2 . . 52.72(7) yes
O1 Cu O2 3_556 . 127.28(7) ?
N1 Cu O2 3_556 . 98.09(7) ?
N1 Cu O2 . . 81.91(7) yes
O2 Cu O2 3_556 . 180.0 ?
C1 O1 Cu . . 111.0(2) ?
C1 O2 Cu . . 72.2(2) ?
O2 C1 O1 . . 122.3(2) yes
O2 C1 C2 . . 120.2(3) yes
O1 C1 C2 . . 117.4(2) yes
C7 C2 C3 . . 118.7(2) ?
C7 C2 C1 . . 120.3(2) yes
C3 C2 C1 . . 120.9(2) yes
O3 C3 C4 . . 117.8(3) yes
O3 C3 C2 . . 122.4(3) yes
C4 C3 C2 . . 119.8(3) ?
C5 C4 C3 . . 120.1(3) ?
C4 C5 C6 . . 121.1(3) ?
C7 C6 C5 . . 119.1(3) ?
C6 C7 C2 . . 121.3(3) ?
C12 N1 C8 . . 117.4(2) ?
C12 N1 Cu . . 122.9(2) ?
C8 N1 Cu . . 119.7(2) ?
N1 C8 C9 . . 123.5(2) ?
C8 C9 C10 . . 117.9(2) ?
C8 C9 C13 . . 121.4(2) yes
C10 C9 C13 . . 120.6(2) yes
C11 C10 C9 . . 119.3(3) ?
C12 C11 C10 . . 119.0(3) ?
N1 C12 C11 . . 122.9(3) ?
O4 C13 N2 . . 122.9(3) yes
O4 C13 C9 . . 120.1(3) yes
N2 C13 C9 . . 117.0(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu O1 . 1.928(2) yes
Cu O1 3_556 1.928(2) ?
Cu N1 3_556 2.022(2) ?
Cu N1 . 2.022(2) yes
Cu O2 3_556 2.766(2) ?
Cu O2 . 2.766(2) yes
O1 C1 . 1.275(3) yes
O2 C1 . 1.255(3) yes
O3 C3 . 1.354(3) yes
C1 C2 . 1.487(3) yes
C2 C7 . 1.390(4) ?
C2 C3 . 1.391(4) ?
C3 C4 . 1.390(4) ?
C4 C5 . 1.363(5) ?
C5 C6 . 1.376(5) ?
C6 C7 . 1.374(4) ?
O4 C13 . 1.222(3) yes
N1 C12 . 1.337(3) ?
N1 C8 . 1.346(3) ?
N2 C13 . 1.327(4) yes
C8 C9 . 1.374(3) ?
C9 C10 . 1.384(4) ?
C9 C13 . 1.500(3) yes
C10 C11 . 1.378(4) ?
C11 C12 . 1.369(4) ?
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_site_symmetry_1
_geom_torsion
O1 Cu O1 C1 3_556 -50.0(18)
N1 Cu O1 C1 3_556 -108.0(2)
N1 Cu O1 C1 . 72.0(2)
O2 Cu O1 C1 3_556 172.21(15)
O2 Cu O1 C1 . -7.79(15)
O1 Cu O2 C1 . 7.76(15)
O1 Cu O2 C1 3_556 -172.24(15)
N1 Cu O2 C1 3_556 91.5(2)
N1 Cu O2 C1 . -88.5(2)
O2 Cu O2 C1 3_556 135.40(10)
Cu O2 C1 O1 . -11.1(2)
Cu O2 C1 C2 . 165.6(2)
Cu O1 C1 O2 . 16.3(3)
Cu O1 C1 C2 . -160.5(2)
O2 C1 C2 C7 . -178.7(3)
O1 C1 C2 C7 . -1.8(4)
O2 C1 C2 C3 . -2.4(4)
O1 C1 C2 C3 . 174.5(2)
C7 C2 C3 O3 . 179.8(3)
C1 C2 C3 O3 . 3.5(4)
C7 C2 C3 C4 . 0.5(4)
C1 C2 C3 C4 . -175.8(3)
O3 C3 C4 C5 . 179.8(3)
C2 C3 C4 C5 . -0.9(5)
C3 C4 C5 C6 . 0.0(6)
C4 C5 C6 C7 . 1.2(7)
C5 C6 C7 C2 . -1.5(6)
C3 C2 C7 C6 . 0.7(5)
C1 C2 C7 C6 . 177.1(3)
O1 Cu N1 C12 . -150.7(2)
O1 Cu N1 C12 3_556 29.3(2)
N1 Cu N1 C12 3_556 -53.1(2)
O2 Cu N1 C12 3_556 81.5(2)
O2 Cu N1 C12 . -98.5(2)
O1 Cu N1 C8 . 27.8(2)
O1 Cu N1 C8 3_556 -152.2(2)
N1 Cu N1 C8 3_556 125.4(3)
O2 Cu N1 C8 3_556 -100.0(2)
O2 Cu N1 C8 . 80.0(2)
C12 N1 C8 C9 . 0.6(4)
Cu N1 C8 C9 . -178.0(2)
N1 C8 C9 C10 . 0.2(4)
N1 C8 C9 C13 . 176.2(2)
C8 C9 C10 C11 . -1.3(5)
C13 C9 C10 C11 . -177.3(3)
C9 C10 C11 C12 . 1.6(5)
C8 N1 C12 C11 . -0.3(4)
Cu N1 C12 C11 . 178.2(3)
C10 C11 C12 N1 . -0.7(5)
C8 C9 C13 O4 . -153.7(3)
C10 C9 C13 O4 . 22.1(4)
C8 C9 C13 N2 . 24.6(4)
C10 C9 C13 N2 . -159.5(3)
O1 Cu N1 C12 . -150.7(2)
O1 Cu N1 C8 . 27.8(2)
O2 Cu N1 C12 . -98.5(2)
O2 Cu N1 C8 . 80.0(2)
O1 C1 C2 C7 . -1.8(4)
O2 C1 C2 C3 . -2.4(4)
C1 C2 C3 O3 . 3.5(4)