#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:37:38 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180513 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/82/7218274.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_7218274
loop_
_publ_author_name
'Carter, Korey P.'
'Zulato, Cecília H. F.'
'Cahill, Christopher L.'
_publ_section_title
;
 Exploring supramolecular assembly and luminescent behavior in a series of
 RE-p-chlorobenzoic acid-1,10-phenanthroline complexes
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              10189
_journal_paper_doi               10.1039/C4CE01806K
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C66 H44 Ce2 Cl6 N4 O14'
_chemical_formula_weight         1609.99
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                98.995(6)
_cell_angle_beta                 100.654(7)
_cell_angle_gamma                100.680(6)
_cell_formula_units_Z            1
_cell_length_a                   8.4595(5)
_cell_length_b                   12.9231(8)
_cell_length_c                   15.4404(9)
_cell_measurement_reflns_used    21251
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.862
_cell_measurement_theta_min      4.663
_cell_volume                     1598.09(18)
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_collection       'APEX, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_molecular_graphics    'Crystal Maker (Palmer, 2009)'
_computing_publication_material  'WINGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21250
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         27.608
_diffrn_reflns_theta_min         1.369
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.726
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_description       Plate
_exptl_crystal_F_000             798
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         7386
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0304P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0755
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5896
_reflns_number_total             7386
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce01806k2.cif
_cod_data_source_block           Compound_2
_cod_depositor_comments
'Adding full bibliography for 7218273--7218283.cif.'
_cod_original_cell_volume        1598.09(17)
_cod_database_code               7218274
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Ce1 Ce 0.79554(2) 0.36922(2) 0.48194(2) 0.02544(7) Uani 1 1 d . .
Cl1 Cl 0.83023(18) 0.28179(13) -0.05942(8) 0.0881(5) Uani 1 1 d . .
Cl3 Cl 0.2016(2) 0.00987(17) -0.06788(10) 0.1207(7) Uani 1 1 d . .
Cl2 Cl 0.5678(2) 0.6553(2) 0.01650(11) 0.1336(8) Uani 1 1 d . .
OW1 O 0.5129(3) 0.3720(2) 0.50943(19) 0.0393(6) Uani 1 1 d D .
O3 O 0.7118(3) 0.52069(19) 0.41953(16) 0.0351(6) Uani 1 1 d . .
O5 O 0.5904(3) 0.2664(2) 0.34861(17) 0.0411(6) Uani 1 1 d . .
O1 O 0.9889(3) 0.42897(19) 0.39049(16) 0.0362(6) Uani 1 1 d . .
O4 O 1.0627(3) 0.35254(19) 0.56719(17) 0.0388(6) Uani 1 1 d . .
N1 N 0.8683(4) 0.1804(2) 0.4184(2) 0.0348(7) Uani 1 1 d . .
O6 O 0.3440(3) 0.3065(3) 0.34274(19) 0.0619(9) Uani 1 1 d . .
N2 N 0.7220(4) 0.2024(2) 0.5628(2) 0.0388(8) Uani 1 1 d . .
C3 C 0.9013(6) -0.0196(4) 0.3365(3) 0.0648(14) Uani 1 1 d . .
H3 H 0.9092 -0.0865 0.3073 0.078 Uiso 1 1 calc R U
C1 C 0.9429(5) 0.1692(3) 0.3510(3) 0.0450(10) Uani 1 1 d . .
H1 H 0.9867 0.2307 0.3316 0.054 Uiso 1 1 calc R U
C14 C 0.9996(4) 0.4230(3) 0.2364(2) 0.0310(8) Uani 1 1 d . .
C11 C 0.7413(4) 0.1029(3) 0.5273(3) 0.0392(9) Uani 1 1 d . .
C28 C 0.3853(5) 0.1994(3) 0.2152(3) 0.0372(9) Uani 1 1 d . .
C16 C 0.8010(5) 0.3031(3) 0.1128(3) 0.0517(11) Uani 1 1 d . .
H16 H 0.7040 0.2508 0.0913 0.062 Uiso 1 1 calc R U
C15 C 0.8542(5) 0.3464(3) 0.2041(3) 0.0395(9) Uani 1 1 d . .
H15 H 0.7914 0.3236 0.2438 0.047 Uiso 1 1 calc R U
C12 C 0.8129(4) 0.0909(3) 0.4502(3) 0.0374(9) Uani 1 1 d . .
O2 O 0.8133(3) 0.4552(2) 0.64094(17) 0.0428(7) Uani 1 1 d . .
C21 C 0.7371(4) 0.6101(3) 0.2986(2) 0.0334(8) Uani 1 1 d . .
C2 C 0.9604(6) 0.0696(4) 0.3065(3) 0.0591(13) Uani 1 1 d . .
H2 H 1.0112 0.0652 0.2580 0.071 Uiso 1 1 calc R U
C26 C 0.8416(5) 0.6725(3) 0.2576(3) 0.0458(10) Uani 1 1 d . .
H26 H 0.9486 0.7050 0.2891 0.055 Uiso 1 1 calc R U
C13 C 1.0632(4) 0.4685(3) 0.3349(2) 0.0320(8) Uani 1 1 d . .
C27 C 0.4435(5) 0.2634(3) 0.3093(3) 0.0377(9) Uani 1 1 d . .
C33 C 0.2416(5) 0.2105(4) 0.1617(3) 0.0534(11) Uani 1 1 d . .
H33 H 0.1816 0.2573 0.1848 0.064 Uiso 1 1 calc R U
C10 C 0.6621(5) 0.2136(4) 0.6360(3) 0.0519(11) Uani 1 1 d . .
H10 H 0.6500 0.2813 0.6607 0.062 Uiso 1 1 calc R U
C19 C 1.0890(5) 0.4584(3) 0.1756(3) 0.0434(10) Uani 1 1 d . .
H19 H 1.1853 0.5115 0.1961 0.052 Uiso 1 1 calc R U
C4 C 0.8289(5) -0.0125(3) 0.4103(3) 0.0517(12) Uani 1 1 d . .
C30 C 0.4097(6) 0.0644(4) 0.0951(3) 0.0644(13) Uani 1 1 d . .
H30 H 0.4634 0.0125 0.0736 0.077 Uiso 1 1 calc R U
C20 C 0.8002(4) 0.5913(3) 0.3904(2) 0.0302(8) Uani 1 1 d . .
C29 C 0.4673(5) 0.1256(3) 0.1810(3) 0.0486(11) Uani 1 1 d . .
H29 H 0.5635 0.1166 0.2165 0.058 Uiso 1 1 calc R U
C7 C 0.6932(5) 0.0118(3) 0.5639(3) 0.0536(12) Uani 1 1 d . .
C24 C 0.6328(6) 0.6396(5) 0.1263(3) 0.0739(16) Uani 1 1 d . .
C23 C 0.5269(6) 0.5773(5) 0.1649(3) 0.092(2) Uani 1 1 d . .
H23 H 0.4200 0.5452 0.1329 0.110 Uiso 1 1 calc R U
C18 C 1.0359(5) 0.4153(4) 0.0851(3) 0.0535(11) Uani 1 1 d . .
H18 H 1.0969 0.4386 0.0448 0.064 Uiso 1 1 calc R U
C31 C 0.2716(6) 0.0819(4) 0.0422(3) 0.0678(14) Uani 1 1 d . .
C9 C 0.6154(6) 0.1271(4) 0.6785(3) 0.0683(14) Uani 1 1 d . .
H9 H 0.5754 0.1376 0.7307 0.082 Uiso 1 1 calc R U
C25 C 0.7896(6) 0.6870(4) 0.1716(3) 0.0592(12) Uani 1 1 d . .
H25 H 0.8607 0.7285 0.1447 0.071 Uiso 1 1 calc R U
C22 C 0.5796(5) 0.5625(4) 0.2511(3) 0.0585(13) Uani 1 1 d . .
H22 H 0.5081 0.5200 0.2772 0.070 Uiso 1 1 calc R U
C17 C 0.8935(5) 0.3385(4) 0.0549(3) 0.0508(11) Uani 1 1 d . .
C8 C 0.6308(6) 0.0280(4) 0.6409(4) 0.0710(16) Uani 1 1 d . .
H8 H 0.5988 -0.0301 0.6673 0.085 Uiso 1 1 calc R U
C6 C 0.7113(6) -0.0912(4) 0.5216(4) 0.0684(15) Uani 1 1 d . .
H6 H 0.6775 -0.1514 0.5452 0.082 Uiso 1 1 calc R U
C32 C 0.1856(6) 0.1532(4) 0.0744(3) 0.0696(14) Uani 1 1 d . .
H32 H 0.0908 0.1630 0.0382 0.083 Uiso 1 1 calc R U
C5 C 0.7752(6) -0.1018(3) 0.4494(4) 0.0710(15) Uani 1 1 d . .
H5 H 0.7854 -0.1696 0.4236 0.085 Uiso 1 1 calc R U
HW1 H 0.433(5) 0.354(4) 0.453(2) 0.091(18) Uiso 1 1 d D .
HW2 H 0.477(5) 0.424(3) 0.547(2) 0.072(15) Uiso 1 1 d 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.2486 2.6331 '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
O5 Ce1 O1 91.74(8) .
O5 Ce1 O4 136.55(8) .
O1 Ce1 O4 76.57(8) .
O5 Ce1 O3 81.28(8) .
O1 Ce1 O3 71.94(8) .
O4 Ce1 O3 131.10(8) .
O5 Ce1 O2 140.10(8) .
O1 Ce1 O2 124.66(8) .
O4 Ce1 O2 74.28(8) .
O3 Ce1 O2 94.11(8) .
O5 Ce1 OW1 71.23(9) .
O1 Ce1 OW1 143.62(9) .
O4 Ce1 OW1 137.47(9) .
O3 Ce1 OW1 73.78(8) .
O2 Ce1 OW1 69.45(9) .
O5 Ce1 N2 87.75(9) .
O1 Ce1 N2 137.73(9) .
O4 Ce1 N2 75.15(9) .
O3 Ce1 N2 148.95(9) .
O2 Ce1 N2 76.00(9) .
OW1 Ce1 N2 75.19(9) .
O5 Ce1 N1 67.89(8) .
O1 Ce1 N1 79.60(9) .
O4 Ce1 N1 68.87(8) .
O3 Ce1 N1 137.04(9) .
O2 Ce1 N1 128.75(9) .
OW1 Ce1 N1 119.79(9) .
N2 Ce1 N1 61.17(9) .
C20 O3 Ce1 127.2(2) .
C27 O5 Ce1 138.7(2) .
C13 O1 Ce1 167.2(2) .
C20 O4 Ce1 140.9(2) 2_766
C1 N1 C12 117.9(3) .
C1 N1 Ce1 121.8(2) .
C12 N1 Ce1 120.0(2) .
C10 N2 C11 118.4(3) .
C10 N2 Ce1 121.0(3) .
C11 N2 Ce1 120.5(2) .
C2 C3 C4 120.8(4) .
N1 C1 C2 123.9(4) .
C15 C14 C19 118.8(3) .
C15 C14 C13 121.9(3) .
C19 C14 C13 119.3(3) .
N2 C11 C7 122.3(4) .
N2 C11 C12 118.8(3) .
C7 C11 C12 118.8(4) .
C29 C28 C33 118.3(4) .
C29 C28 C27 121.8(3) .
C33 C28 C27 119.9(4) .
C17 C16 C15 119.1(4) .
C14 C15 C16 120.6(4) .
N1 C12 C4 121.7(4) .
N1 C12 C11 118.5(3) .
C4 C12 C11 119.8(4) .
C13 O2 Ce1 108.7(2) 2_766
C22 C21 C26 118.6(4) .
C22 C21 C20 121.5(3) .
C26 C21 C20 119.8(3) .
C3 C2 C1 118.1(4) .
C25 C26 C21 121.2(4) .
O2 C13 O1 122.4(3) 2_766
O2 C13 C14 118.7(3) 2_766
O1 C13 C14 118.9(3) .
O6 C27 O5 125.6(4) .
O6 C27 C28 117.6(3) .
O5 C27 C28 116.7(3) .
C32 C33 C28 121.2(4) .
N2 C10 C9 122.9(4) .
C18 C19 C14 120.4(4) .
C3 C4 C12 117.6(4) .
C3 C4 C5 123.7(4) .
C12 C4 C5 118.7(5) .
C31 C30 C29 118.6(4) .
O4 C20 O3 124.8(3) 2_766
O4 C20 C21 117.0(3) 2_766
O3 C20 C21 118.1(3) .
C28 C29 C30 121.4(4) .
C8 C7 C11 116.9(4) .
C8 C7 C6 123.5(4) .
C11 C7 C6 119.7(5) .
C25 C24 C23 121.2(4) .
C25 C24 Cl2 119.2(4) .
C23 C24 Cl2 119.6(4) .
C24 C23 C22 119.7(4) .
C17 C18 C19 119.8(4) .
C32 C31 C30 121.5(4) .
C32 C31 Cl3 119.0(4) .
C30 C31 Cl3 119.5(4) .
C8 C9 C10 118.0(5) .
C24 C25 C26 119.0(4) .
C21 C22 C23 120.3(4) .
C18 C17 C16 121.3(4) .
C18 C17 Cl1 119.4(3) .
C16 C17 Cl1 119.2(3) .
C9 C8 C7 121.5(4) .
C5 C6 C7 121.1(4) .
C31 C32 C33 118.9(4) .
C6 C5 C4 121.9(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ce1 O5 2.446(2) .
Ce1 O1 2.448(2) .
Ce1 O4 2.461(2) .
Ce1 O3 2.472(2) .
Ce1 O2 2.497(2) .
Ce1 OW1 2.511(3) .
Ce1 N2 2.688(3) .
Ce1 N1 2.706(3) .
Cl1 C17 1.743(4) .
Cl3 C31 1.742(5) .
Cl2 C24 1.739(5) .
O3 C20 1.263(4) .
O5 C27 1.269(4) .
O1 C13 1.269(4) .
O4 C20 1.249(4) 2_766
N1 C1 1.317(5) .
N1 C12 1.363(4) .
O6 C27 1.237(4) .
N2 C10 1.320(5) .
N2 C11 1.368(5) .
C3 C2 1.353(6) .
C3 C4 1.388(6) .
C1 C2 1.408(5) .
C14 C15 1.381(5) .
C14 C19 1.391(5) .
C14 C13 1.499(5) .
C11 C7 1.410(5) .
C11 C12 1.433(5) .
C28 C29 1.377(5) .
C28 C33 1.382(5) .
C28 C27 1.499(5) .
C16 C17 1.370(6) .
C16 C15 1.389(5) .
C12 C4 1.423(5) .
O2 C13 1.250(4) 2_766
C21 C22 1.374(5) .
C21 C26 1.390(5) .
C21 C20 1.493(5) .
C26 C25 1.373(5) .
C13 O2 1.250(4) 2_766
C33 C32 1.383(6) .
C10 C9 1.413(6) .
C19 C18 1.377(5) .
C4 C5 1.425(6) .
C30 C31 1.373(6) .
C30 C29 1.383(6) .
C20 O4 1.249(4) 2_766
C7 C8 1.390(7) .
C7 C6 1.436(7) .
C24 C25 1.359(6) .
C24 C23 1.373(7) .
C23 C22 1.378(6) .
C18 C17 1.363(6) .
C31 C32 1.366(7) .
C9 C8 1.361(7) .
C6 C5 1.325(7) .
