#------------------------------------------------------------------------------
#$Date: 2021-01-07 07:20:33 +0100 (jue 07 de ene de 2021) $
#$Revision: 260760 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/57/7705758.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_7705758
loop_
_publ_author_name
'de Bettencourt-Dias, Ana'
'Rossini, Jeffrey S. K.'
'Sobrinho, Josiane A.'
_publ_section_title
;
 Effect of the aromatic substituent on the para-position of
 pyridine-bis(oxazoline) sensitizers on the emission efficiency of their
 EuIII and TbIII complexes.
;
_journal_issue                   48
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17699
_journal_page_last               17708
_journal_paper_doi               10.1039/d0dt03135f
_journal_volume                  49
_journal_year                    2020
_chemical_formula_sum            'C17 H17 Eu N6 O12'
_chemical_formula_weight         649.33
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-07-06 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                98.419(1)
_cell_angle_beta                 108.109(1)
_cell_angle_gamma                91.791(1)
_cell_formula_units_Z            2
_cell_length_a                   9.1845(2)
_cell_length_b                   10.3327(2)
_cell_length_c                   11.9654(2)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.34
_cell_volume                     1064.08(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2001)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX CCD'
_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  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22516
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    3.029
_exptl_absorpt_correction_T_max  0.7722
_exptl_absorpt_correction_T_min  0.2325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS (Bruker 2005)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0208
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0235P)²+1.3510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0502
_refine_ls_wR_factor_ref         0.0525
_reflns_number_gt                3492
_reflns_number_total             3740
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0dt03135f2.cif
_cod_data_source_block           abd204_0m
_cod_depositor_comments
'Adding full bibliography for 7705758--7705761.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7705758
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
Eu1 Eu -0.155458(17) 0.696373(15) 0.197174(13) 0.01237(6) Uani 1 1 d . . .
O1 O 0.3538(2) 0.6437(2) 0.4089(2) 0.0181(5) Uani 1 1 d . . .
O2 O -0.0821(3) 1.1133(2) 0.1073(2) 0.0252(6) Uani 1 1 d . . .
O3 O -0.1551(3) 0.4609(2) 0.1291(2) 0.0191(5) Uani 1 1 d . . .
H3A H -0.090(6) 0.434(4) 0.122(4) 0.037(16) Uiso 1 1 d . . .
H3B H -0.228(6) 0.436(5) 0.069(5) 0.059(17) Uiso 1 1 d . . .
O4 O -0.0227(2) 0.6679(2) 0.04112(19) 0.0186(5) Uani 1 1 d . . .
O5 O -0.2707(2) 0.6714(2) -0.0252(2) 0.0184(5) Uani 1 1 d . . .
O6 O -0.1418(3) 0.6308(2) -0.1496(2) 0.0229(5) Uani 1 1 d . . .
O7 O -0.4172(2) 0.7715(2) 0.1793(2) 0.0192(5) Uani 1 1 d . . .
O8 O -0.6348(2) 0.6503(2) 0.1067(2) 0.0219(5) Uani 1 1 d . . .
O9 O -0.4161(2) 0.5625(2) 0.1303(2) 0.0189(5) Uani 1 1 d . . .
O10 O -0.1245(3) 0.8319(2) 0.3911(2) 0.0185(5) Uani 1 1 d . . .
O11 O -0.1943(3) 0.7674(3) 0.5335(2) 0.0330(6) Uani 1 1 d . . .
O12 O -0.2103(3) 0.6299(2) 0.3726(2) 0.0192(5) Uani 1 1 d . . .
N1 N 0.0954(3) 0.8551(3) 0.2534(2) 0.0157(6) Uani 1 1 d . . .
N2 N 0.0956(3) 0.6221(3) 0.3247(2) 0.0155(6) Uani 1 1 d . . .
N3 N -0.1802(3) 0.9217(3) 0.1335(2) 0.0166(6) Uani 1 1 d . . .
N4 N -0.1455(3) 0.6558(3) -0.0467(2) 0.0166(6) Uani 1 1 d . . .
N5 N -0.4933(3) 0.6598(3) 0.1376(2) 0.0175(6) Uani 1 1 d . . .
N6 N -0.1769(3) 0.7438(3) 0.4361(2) 0.0189(6) Uani 1 1 d . . .
C1 C 0.2323(4) 0.8192(3) 0.3112(3) 0.0153(7) Uani 1 1 d . . .
C2 C 0.3695(4) 0.8949(3) 0.3346(3) 0.0164(7) Uani 1 1 d . . .
H2 H 0.4645 0.8638 0.3754 0.020 Uiso 1 1 calc R . .
C3 C 0.3661(4) 1.0179(3) 0.2975(3) 0.0129(5) Uani 1 1 d . . .
C4 C 0.2216(4) 1.0560(3) 0.2387(3) 0.0165(7) Uani 1 1 d . . .
H4 H 0.2122 1.1392 0.2133 0.020 Uiso 1 1 calc R . .
C5 C 0.0921(4) 0.9722(3) 0.2176(3) 0.0161(7) Uani 1 1 d . . .
C6 C 0.2239(4) 0.6896(3) 0.3474(3) 0.0155(7) Uani 1 1 d . . .
C7 C 0.1328(4) 0.5069(3) 0.3858(3) 0.0171(7) Uani 1 1 d . . .
H7A H 0.0866 0.4244 0.3307 0.020 Uiso 1 1 calc R . .
H7B H 0.0950 0.5135 0.4553 0.020 Uiso 1 1 calc R . .
C8 C 0.3088(4) 0.5121(3) 0.4256(3) 0.0192(7) Uani 1 1 d . . .
H8A H 0.3514 0.5010 0.5102 0.023 Uiso 1 1 calc R . .
H8B H 0.3443 0.4432 0.3758 0.023 Uiso 1 1 calc R . .
C9 C -0.0644(4) 1.0009(3) 0.1513(3) 0.0161(7) Uani 1 1 d . . .
C10 C -0.2474(4) 1.1131(3) 0.0461(3) 0.0230(8) Uani 1 1 d . . .
H10A H -0.2683 1.1172 -0.0395 0.028 Uiso 1 1 calc R . .
H10B H -0.2908 1.1883 0.0825 0.028 Uiso 1 1 calc R . .
C11 C -0.3149(4) 0.9822(3) 0.0632(3) 0.0214(8) Uani 1 1 d . . .
H11A H -0.3900 0.9971 0.1069 0.026 Uiso 1 1 calc R . .
H11B H -0.3663 0.9258 -0.0146 0.026 Uiso 1 1 calc R . .
C12 C 0.5198(4) 1.1047(3) 0.3200(3) 0.0129(5) Uani 1 1 d . . .
C13 C 0.6483(4) 1.0635(3) 0.3721(3) 0.0246(8) Uani 1 1 d . . .
H13 H 0.6513 0.9826 0.4014 0.030 Uiso 1 1 calc R . .
C14 C 0.7866(4) 1.1376(3) 0.3867(3) 0.0239(8) Uani 1 1 d . . .
H14 H 0.8831 1.1076 0.4257 0.029 Uiso 1 1 calc R . .
C15 C 0.7787(4) 1.2553(4) 0.3430(3) 0.0257(8) Uani 1 1 d . . .
H15 H 0.8702 1.3068 0.3516 0.031 Uiso 1 1 calc R . .
C16 C 0.6360(4) 1.2971(3) 0.2866(3) 0.0248(8) Uani 1 1 d . . .
H16 H 0.6296 1.3780 0.2572 0.030 Uiso 1 1 calc R . .
C17 C 0.5034(4) 1.2208(3) 0.2733(3) 0.0230(8) Uani 1 1 d . . .
H17 H 0.4048 1.2468 0.2337 0.028 Uiso 1 1 calc R . .
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'
Eu Eu -0.1578 3.6682 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Eu1 O10 134.35(8) . . ?
O3 Eu1 O12 85.68(8) . . ?
O10 Eu1 O12 51.87(7) . . ?
O3 Eu1 O7 114.00(9) . . ?
O10 Eu1 O7 75.52(7) . . ?
O12 Eu1 O7 76.40(7) . . ?
O3 Eu1 O5 76.20(8) . . ?
O10 Eu1 O5 146.74(7) . . ?
O12 Eu1 O5 140.48(7) . . ?
O7 Eu1 O5 79.43(7) . . ?
O3 Eu1 O4 71.65(8) . . ?
O10 Eu1 O4 139.17(7) . . ?
O12 Eu1 O4 151.34(7) . . ?
O7 Eu1 O4 128.49(7) . . ?
O5 Eu1 O4 51.14(7) . . ?
O3 Eu1 N3 144.95(8) . . ?
O10 Eu1 N3 80.70(8) . . ?
O12 Eu1 N3 126.99(8) . . ?
O7 Eu1 N3 69.16(8) . . ?
O5 Eu1 N3 70.06(8) . . ?
O4 Eu1 N3 79.85(8) . . ?
O3 Eu1 N2 72.85(9) . . ?
O10 Eu1 N2 79.17(8) . . ?
O12 Eu1 N2 74.17(8) . . ?
O7 Eu1 N2 149.15(8) . . ?
O5 Eu1 N2 130.32(8) . . ?
O4 Eu1 N2 82.35(8) . . ?
N3 Eu1 N2 123.63(8) . . ?
O3 Eu1 O9 63.77(9) . . ?
O10 Eu1 O9 107.82(7) . . ?
O12 Eu1 O9 69.97(7) . . ?
O7 Eu1 O9 50.32(7) . . ?
O5 Eu1 O9 70.52(7) . . ?
O4 Eu1 O9 112.66(7) . . ?
N3 Eu1 O9 111.63(8) . . ?
N2 Eu1 O9 124.60(8) . . ?
O3 Eu1 N1 121.18(9) . . ?
O10 Eu1 N1 72.17(8) . . ?
O12 Eu1 N1 113.72(8) . . ?
O7 Eu1 N1 124.27(8) . . ?
O5 Eu1 N1 105.70(8) . . ?
O4 Eu1 N1 67.00(8) . . ?
N3 Eu1 N1 61.77(8) . . ?
N2 Eu1 N1 62.00(8) . . ?
O9 Eu1 N1 173.40(7) . . ?
O3 Eu1 N6 110.71(8) . . ?
O10 Eu1 N6 25.91(7) . . ?
O12 Eu1 N6 26.00(7) . . ?
O7 Eu1 N6 73.19(7) . . ?
O5 Eu1 N6 152.22(7) . . ?
O4 Eu1 N6 156.38(7) . . ?
N3 Eu1 N6 103.61(8) . . ?
N2 Eu1 N6 76.32(8) . . ?
O9 Eu1 N6 88.10(8) . . ?
N1 Eu1 N6 93.70(8) . . ?
O3 Eu1 N4 70.90(8) . . ?
O10 Eu1 N4 153.23(7) . . ?
O12 Eu1 N4 154.85(7) . . ?
O7 Eu1 N4 104.37(8) . . ?
O5 Eu1 N4 25.55(7) . . ?
O4 Eu1 N4 25.64(7) . . ?
N3 Eu1 N4 74.56(8) . . ?
N2 Eu1 N4 106.18(8) . . ?
O9 Eu1 N4 90.92(7) . . ?
N1 Eu1 N4 87.02(8) . . ?
N6 Eu1 N4 177.43(7) . . ?
C6 O1 C8 105.6(2) . . ?
C9 O2 C10 105.5(2) . . ?
Eu1 O3 H3A 121(4) . . ?
Eu1 O3 H3B 111(4) . . ?
H3A O3 H3B 110(5) . . ?
N4 O4 Eu1 95.09(17) . . ?
N4 O5 Eu1 95.55(17) . . ?
N5 O7 Eu1 97.58(17) . . ?
N5 O9 Eu1 95.44(17) . . ?
N6 O10 Eu1 96.69(17) . . ?
N6 O12 Eu1 95.21(17) . . ?
C1 N1 C5 116.9(3) . . ?
C1 N1 Eu1 121.6(2) . . ?
C5 N1 Eu1 121.4(2) . . ?
C6 N2 C7 105.8(3) . . ?
C6 N2 Eu1 121.2(2) . . ?
C7 N2 Eu1 132.96(19) . . ?
C9 N3 C11 106.5(3) . . ?
C9 N3 Eu1 122.1(2) . . ?
C11 N3 Eu1 131.1(2) . . ?
O6 N4 O5 121.3(3) . . ?
O6 N4 O4 120.7(3) . . ?
O5 N4 O4 118.0(3) . . ?
O6 N4 Eu1 176.2(2) . . ?
O5 N4 Eu1 58.90(14) . . ?
O4 N4 Eu1 59.26(14) . . ?
O8 N5 O9 122.8(3) . . ?
O8 N5 O7 120.8(3) . . ?
O9 N5 O7 116.4(3) . . ?
O8 N5 Eu1 175.4(2) . . ?
O9 N5 Eu1 59.53(15) . . ?
O7 N5 Eu1 57.07(14) . . ?
O11 N6 O10 121.9(3) . . ?
O11 N6 O12 122.1(3) . . ?
O10 N6 O12 116.0(3) . . ?
O11 N6 Eu1 175.9(2) . . ?
O10 N6 Eu1 57.40(14) . . ?
O12 N6 Eu1 58.79(14) . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 C6 112.8(3) . . ?
C2 C1 C6 123.3(3) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 116.5(3) . . ?
C4 C3 C12 122.8(3) . . ?
C2 C3 C12 120.6(3) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 123.8(3) . . ?
N1 C5 C9 112.6(3) . . ?
C4 C5 C9 123.6(3) . . ?
N2 C6 O1 119.4(3) . . ?
N2 C6 C1 121.9(3) . . ?
O1 C6 C1 118.6(3) . . ?
N2 C7 C8 104.2(2) . . ?
N2 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
N2 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O1 C8 C7 103.4(2) . . ?
O1 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
O1 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
N3 C9 O2 119.9(3) . . ?
N3 C9 C5 121.9(3) . . ?
O2 C9 C5 118.2(3) . . ?
O2 C10 C11 103.9(2) . . ?
O2 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
O2 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
N3 C11 C10 104.3(3) . . ?
N3 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
N3 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C13 C12 C17 124.2(3) . . ?
C13 C12 C3 120.0(3) . . ?
C17 C12 C3 115.7(3) . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 117.5(3) . . ?
C16 C17 H17 121.3 . . ?
C12 C17 H17 121.3 . . ?
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
Eu1 O3 2.450(3) . ?
Eu1 O10 2.458(2) . ?
Eu1 O12 2.488(2) . ?
Eu1 O7 2.505(2) . ?
Eu1 O5 2.509(2) . ?
Eu1 O4 2.517(2) . ?
Eu1 N3 2.549(3) . ?
Eu1 N2 2.549(3) . ?
Eu1 O9 2.561(2) . ?
Eu1 N1 2.632(3) . ?
Eu1 N6 2.897(3) . ?
Eu1 N4 2.917(3) . ?
O1 C6 1.335(4) . ?
O1 C8 1.469(4) . ?
O2 C9 1.338(4) . ?
O2 C10 1.467(4) . ?
O3 H3A 0.69(5) . ?
O3 H3B 0.82(6) . ?
O4 N4 1.267(3) . ?
O5 N4 1.264(3) . ?
O6 N4 1.232(3) . ?
O7 N5 1.278(3) . ?
O8 N5 1.232(3) . ?
O9 N5 1.257(3) . ?
O10 N6 1.275(3) . ?
O11 N6 1.216(4) . ?
O12 N6 1.275(4) . ?
N1 C1 1.326(4) . ?
N1 C5 1.339(4) . ?
N2 C6 1.282(4) . ?
N2 C7 1.481(4) . ?
N3 C9 1.265(4) . ?
N3 C11 1.477(4) . ?
C1 C2 1.390(4) . ?
C1 C6 1.473(4) . ?
C2 C3 1.404(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(5) . ?
C3 C12 1.576(4) . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C9 1.473(5) . ?
C7 C8 1.534(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.537(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.271(5) . ?
C12 C17 1.389(5) . ?
C13 C14 1.411(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
