#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:11:35 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179779 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/75/7007534.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_7007534
loop_
_publ_author_name
'de Bettencourt-Dias, Ana'
'Viswanathan, Subha'
_publ_section_title
;
 Nitro-functionalization and luminescence quantum yield of Eu(III) and
 Tb(III) benzoic acid complexes.
;
_journal_issue                   34
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4093
_journal_page_last               4103
_journal_paper_doi               10.1039/b606970c
_journal_year                    2006
_chemical_formula_sum            'C24 H23 Eu N3 O15'
_chemical_formula_weight         745.41
_chemical_name_common            'Europium 3-Nitrobenzoate'
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.41(3)
_cell_angle_beta                 88.78(3)
_cell_angle_gamma                88.16(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7100(19)
_cell_length_b                   10.579(2)
_cell_length_c                   13.361(3)
_cell_measurement_reflns_used    7177
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      28.2415
_cell_measurement_theta_min      2.598
_cell_volume                     1338.6(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      99(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEX CCD detector'
_diffrn_measurement_method       'Phi and omega 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14194
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0.001
_exptl_absorpt_coefficient_mu    2.426
_exptl_absorpt_correction_T_max  0.8296
_exptl_absorpt_correction_T_min  0.4437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS SHELXL-97 (Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             742
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.130
_refine_diff_density_min         -1.188
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0407P)²+1.7318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                6137
_reflns_number_total             6584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b606970c.txt
_cod_data_source_block           pbar111102005a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1338.7(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7007534
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
C1 C -0.0051(3) 1.3196(3) 0.5978(2) 0.0130(5) Uani 1 1 d . . .
C2 C -0.1278(3) 1.3451(3) 0.6468(2) 0.0146(6) Uani 1 1 d . . .
H2A H -0.2029 1.2884 0.6533 0.018 Uiso 1 1 calc R . .
C3 C -0.1361(3) 1.4565(3) 0.6857(2) 0.0161(6) Uani 1 1 d . . .
C4 C -0.0299(3) 1.5431(3) 0.6772(2) 0.0180(6) Uani 1 1 d . . .
H4 H -0.0401 1.6193 0.7038 0.022 Uiso 1 1 calc R . .
C5 C 0.0909(3) 1.5153(3) 0.6290(3) 0.0186(6) Uani 1 1 d . . .
H5 H 0.1652 1.5730 0.6219 0.022 Uiso 1 1 calc R . .
C6 C 0.1043(3) 1.4028(3) 0.5906(2) 0.0164(6) Uani 1 1 d . . .
H6 H 0.1887 1.3830 0.5594 0.020 Uiso 1 1 calc R . .
C7 C 0.0081(3) 1.2024(3) 0.5512(2) 0.0135(5) Uani 1 1 d . . .
C8 C 0.5703(3) 0.8742(3) 0.2544(2) 0.0140(6) Uani 1 1 d . . .
C9 C 0.4893(3) 0.8660(3) 0.1719(2) 0.0156(6) Uani 1 1 d . . .
H9 H 0.3924 0.8812 0.1739 0.019 Uiso 1 1 calc R . .
C10 C 0.5534(3) 0.8352(3) 0.0864(2) 0.0176(6) Uani 1 1 d . . .
C11 C 0.6939(4) 0.8104(3) 0.0803(3) 0.0223(7) Uani 1 1 d . . .
H11A H 0.7345 0.7884 0.0208 0.027 Uiso 1 1 calc R . .
C12 C 0.7735(3) 0.8184(4) 0.1629(3) 0.0238(7) Uani 1 1 d . . .
H12 H 0.8700 0.8010 0.1609 0.029 Uiso 1 1 calc R . .
C13 C 0.7127(3) 0.8518(3) 0.2492(3) 0.0196(6) Uani 1 1 d . . .
H13 H 0.7684 0.8595 0.3050 0.024 Uiso 1 1 calc R . .
C14 C 0.5040(3) 0.9058(3) 0.3484(2) 0.0136(6) Uani 1 1 d . . .
C15 C 0.2662(3) 0.7160(3) 0.7642(2) 0.0139(6) Uani 1 1 d . . .
C16 C 0.3649(3) 0.6146(3) 0.7773(2) 0.0170(6) Uani 1 1 d . . .
H16 H 0.4268 0.6074 0.7227 0.020 Uiso 1 1 calc R . .
C17 C 0.3724(4) 0.5244(3) 0.8699(3) 0.0228(7) Uani 1 1 d . . .
H17 H 0.4415 0.4574 0.8791 0.027 Uiso 1 1 calc R . .
C18 C 0.2796(3) 0.5317(3) 0.9492(3) 0.0226(7) Uani 1 1 d . . .
H18 H 0.2825 0.4694 1.0122 0.027 Uiso 1 1 calc R . .
C19 C 0.1826(3) 0.6328(4) 0.9334(2) 0.0212(7) Uani 1 1 d . . .
C20 C 0.1751(3) 0.7260(3) 0.8439(2) 0.0181(6) Uani 1 1 d . . .
H20 H 0.1092 0.7956 0.8368 0.022 Uiso 1 1 calc R . .
C21 C 0.2576(3) 0.8148(3) 0.6647(2) 0.0141(6) Uani 1 1 d . . .
C22 C 0.1653(3) 1.1092(3) 0.2135(2) 0.0195(6) Uani 1 1 d . . .
H22A H 0.2671 1.1046 0.2076 0.023 Uiso 1 1 calc R . .
H22B H 0.1329 1.1921 0.1694 0.023 Uiso 1 1 calc R . .
C23 C 0.1066(4) 0.9989(3) 0.1755(3) 0.0249(7) Uani 1 1 d . . .
H23A H 0.1391 0.9165 0.2185 0.037 Uiso 1 1 calc R . .
H23B H 0.1367 1.0036 0.1044 0.037 Uiso 1 1 calc R . .
H23C H 0.0058 1.0047 0.1790 0.037 Uiso 1 1 calc R . .
C24 C 0.4035(5) 0.3921(6) 0.4643(4) 0.0530(13) Uani 1 1 d . . .
H24A H 0.3114 0.4115 0.4893 0.080 Uiso 1 1 calc R . .
H24B H 0.4140 0.2989 0.4675 0.080 Uiso 1 1 calc R . .
H24C H 0.4156 0.4396 0.3931 0.080 Uiso 1 1 calc R . .
Eu1 Eu 0.258433(13) 1.006394(13) 0.476627(11) 0.01061(5) Uani 1 1 d . . .
N1 N -0.2624(3) 1.4821(3) 0.7407(2) 0.0211(6) Uani 1 1 d . . .
N2 N 0.4670(3) 0.8267(3) -0.0012(2) 0.0253(6) Uani 1 1 d . . .
N3 N 0.0819(3) 0.6414(4) 1.0151(2) 0.0309(7) Uani 1 1 d . . .
O1 O 0.1251(2) 1.1741(2) 0.51992(18) 0.0188(5) Uani 1 1 d . . .
O2 O -0.2805(3) 1.5899(2) 0.76102(19) 0.0238(5) Uani 1 1 d . . .
O3 O -0.3441(3) 1.3960(3) 0.7655(3) 0.0429(8) Uani 1 1 d . . .
O4 O 0.3744(2) 0.9088(2) 0.35351(17) 0.0178(4) Uani 1 1 d . . .
O6 O 0.3453(3) 0.8578(3) 0.0019(2) 0.0349(6) Uani 1 1 d . . .
O7 O 0.5223(3) 0.7877(3) -0.0728(2) 0.0413(7) Uani 1 1 d . . .
O8 O 0.3445(2) 0.8077(2) 0.59420(16) 0.0147(4) Uani 1 1 d . . .
O9 O 0.1635(2) 0.9019(2) 0.65292(16) 0.0151(4) Uani 1 1 d . . .
O10 O 0.0085(3) 0.7400(4) 1.0048(2) 0.0476(9) Uani 1 1 d . . .
O11 O 0.0747(3) 0.5483(3) 1.0888(2) 0.0409(8) Uani 1 1 d . . .
O12 O 0.3836(2) 1.1825(2) 0.3728(2) 0.0247(5) Uani 1 1 d . . .
O13 O 0.0979(2) 0.8599(2) 0.45267(18) 0.0193(5) Uani 1 1 d . . .
O14 O 0.4214(2) 1.0708(2) 0.58229(18) 0.0194(5) Uani 1 1 d . . .
O15 O 0.1264(2) 1.1077(2) 0.31850(17) 0.0183(5) Uani 1 1 d . . .
O17 O 0.4988(6) 0.4282(5) 0.5229(4) 0.0835(14) 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'
Eu Eu -0.1578 3.6682 '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
C6 C1 C2 120.3(3) . . ?
C6 C1 C7 119.9(3) . . ?
C2 C1 C7 119.8(3) . . ?
C3 C2 C1 117.5(3) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C2 C3 C4 123.4(3) . . ?
C2 C3 N1 118.1(3) . . ?
C4 C3 N1 118.4(3) . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O13 C7 O1 124.8(3) 2_576 . ?
O13 C7 C1 117.7(3) 2_576 . ?
O1 C7 C1 117.5(3) . . ?
C9 C8 C13 119.7(3) . . ?
C9 C8 C14 119.5(3) . . ?
C13 C8 C14 120.8(3) . . ?
C10 C9 C8 118.2(3) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C9 C10 C11 123.0(3) . . ?
C9 C10 N2 118.1(3) . . ?
C11 C10 N2 118.9(3) . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H11A 120.9 . . ?
C10 C11 H11A 120.9 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
O4 C14 O14 123.0(3) . 2_676 ?
O4 C14 C8 117.6(3) . . ?
O14 C14 C8 119.4(3) 2_676 . ?
C20 C15 C16 119.8(3) . . ?
C20 C15 C21 119.4(3) . . ?
C16 C15 C21 120.8(3) . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 117.9(3) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
C20 C19 C18 123.2(3) . . ?
C20 C19 N3 117.8(3) . . ?
C18 C19 N3 119.0(3) . . ?
C19 C20 C15 118.4(3) . . ?
C19 C20 H20 120.8 . . ?
C15 C20 H20 120.8 . . ?
O9 C21 O8 121.6(3) . . ?
O9 C21 C15 119.6(3) . . ?
O8 C21 C15 118.8(3) . . ?
O15 C22 C23 112.6(3) . . ?
O15 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
O15 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O17 C24 H24A 109.5 . . ?
O17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O13 Eu1 O1 103.67(8) . . ?
O13 Eu1 O14 149.22(9) . . ?
O1 Eu1 O14 83.20(8) . . ?
O13 Eu1 O4 79.05(8) . . ?
O1 Eu1 O4 151.18(8) . . ?
O14 Eu1 O4 109.37(8) . . ?
O13 Eu1 O12 137.65(9) . . ?
O1 Eu1 O12 83.13(9) . . ?
O14 Eu1 O12 72.47(9) . . ?
O4 Eu1 O12 76.62(9) . . ?
O13 Eu1 O8 79.11(8) . . ?
O1 Eu1 O8 126.99(8) . . ?
O14 Eu1 O8 73.16(8) . . ?
O4 Eu1 O8 81.82(8) . . ?
O12 Eu1 O8 129.97(8) . . ?
O13 Eu1 O15 72.50(8) . . ?
O1 Eu1 O15 74.30(8) . . ?
O14 Eu1 O15 137.39(8) . . ?
O4 Eu1 O15 79.43(8) . . ?
O12 Eu1 O15 69.32(8) . . ?
O8 Eu1 O15 148.39(8) . . ?
O13 Eu1 O9 73.09(8) . . ?
O1 Eu1 O9 77.47(8) . . ?
O14 Eu1 O9 79.42(8) . . ?
O4 Eu1 O9 129.41(8) . . ?
O12 Eu1 O9 147.44(9) . . ?
O8 Eu1 O9 52.24(7) . . ?
O15 Eu1 O9 128.05(7) . . ?
O3 N1 O2 122.8(3) . . ?
O3 N1 C3 118.6(3) . . ?
O2 N1 C3 118.6(3) . . ?
O6 N2 O7 124.0(3) . . ?
O6 N2 C10 118.3(3) . . ?
O7 N2 C10 117.7(3) . . ?
O10 N3 O11 124.3(3) . . ?
O10 N3 C19 117.7(3) . . ?
O11 N3 C19 117.9(3) . . ?
C7 O1 Eu1 143.4(2) . . ?
C14 O4 Eu1 120.2(2) . . ?
C21 O8 Eu1 94.74(18) . . ?
C21 O9 Eu1 91.32(18) . . ?
C7 O13 Eu1 166.4(2) 2_576 . ?
C14 O14 Eu1 169.9(2) 2_676 . ?
C22 O15 Eu1 127.37(18) . . ?
C24 O17 O17 100.4(6) . 2_666 ?
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
C1 C6 1.390(4) . ?
C1 C2 1.394(4) . ?
C1 C7 1.504(4) . ?
C2 C3 1.387(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.388(4) . ?
C3 N1 1.465(4) . ?
C4 C5 1.381(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O13 1.249(4) 2_576 ?
C7 O1 1.252(4) . ?
C8 C9 1.388(4) . ?
C8 C13 1.397(4) . ?
C8 C14 1.496(4) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(5) . ?
C10 N2 1.475(4) . ?
C11 C12 1.379(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.392(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O4 1.258(4) . ?
C14 O14 1.259(4) 2_676 ?
C15 C20 1.390(4) . ?
C15 C16 1.399(4) . ?
C15 C21 1.504(4) . ?
C16 C17 1.390(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(5) . ?
C19 N3 1.466(4) . ?
C20 H20 0.9500 . ?
C21 O9 1.264(4) . ?
C21 O8 1.264(4) . ?
C22 O15 1.442(4) . ?
C22 C23 1.502(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O17 1.341(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
Eu1 O13 2.307(2) . ?
Eu1 O1 2.329(2) . ?
Eu1 O14 2.355(2) . ?
Eu1 O4 2.372(2) . ?
Eu1 O12 2.412(2) . ?
Eu1 O8 2.468(2) . ?
Eu1 O15 2.509(2) . ?
Eu1 O9 2.541(2) . ?
N1 O3 1.213(4) . ?
N1 O2 1.235(4) . ?
N2 O6 1.218(4) . ?
N2 O7 1.228(4) . ?
N3 O10 1.228(5) . ?
N3 O11 1.234(4) . ?
O13 C7 1.249(4) 2_576 ?
O14 C14 1.259(4) 2_676 ?
O17 O17 1.509(10) 2_666 ?
