#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:37:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180513 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/82/7218280.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_7218280
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 H40 Cl6 N4 O12 Tm2'
_chemical_formula_weight         1631.58
_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   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                111.320(2)
_cell_angle_beta                 96.529(3)
_cell_angle_gamma                101.207(2)
_cell_formula_units_Z            1
_cell_length_a                   10.1079(3)
_cell_length_b                   11.8190(3)
_cell_length_c                   14.2667(4)
_cell_measurement_reflns_used    22033
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.877
_cell_measurement_theta_min      4.700
_cell_volume                     1525.43(8)
_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 0.994
_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  0.0300
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22033
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.850
_diffrn_reflns_theta_min         1.564
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.220
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6555
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_description       Plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0273P)²+0.1724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0554
_refine_ls_wR_factor_ref         0.0586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6909
_reflns_number_total             7934
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce01806k2.cif
_cod_data_source_block           Compound_8
_cod_depositor_comments
'Adding full bibliography for 7218273--7218283.cif.'
_cod_database_code               7218280
#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
Tm1 Tm 0.12223(2) 0.37146(2) 0.93532(2) 0.02535(4) Uani 1 1 d . .
Cl1 Cl 0.36419(12) 0.18813(11) 0.34230(7) 0.0707(3) Uani 1 1 d . .
Cl2 Cl 0.68862(12) 1.07758(10) 1.40957(9) 0.0849(4) Uani 1 1 d . .
Cl3 Cl -0.28806(16) 0.41818(13) 0.40243(8) 0.1035(5) Uani 1 1 d . .
O2 O 0.0732(2) 0.2376(2) 0.75085(16) 0.0414(5) Uani 1 1 d . .
C23 C 0.5777(3) 0.8907(3) 1.2237(3) 0.0433(8) Uani 1 1 d . .
H23 H 0.6625 0.9117 1.2066 0.052 Uiso 1 1 calc R U
O5 O 0.0712(2) 0.4981(2) 0.85430(15) 0.0426(5) Uani 1 1 d . .
O3 O 0.2581(2) 0.56671(18) 1.04092(16) 0.0413(5) Uani 1 1 d . .
O1 O 0.2833(2) 0.3503(2) 0.83020(15) 0.0385(5) Uani 1 1 d . .
O6 O 0.0765(2) 0.3863(2) 1.09192(15) 0.0395(5) Uani 1 1 d . .
N2 N 0.0919(2) 0.1455(2) 0.91196(17) 0.0315(5) Uani 1 1 d . .
O4 O -0.1093(2) 0.3224(2) 0.90013(17) 0.0472(6) Uani 1 1 d . .
C20 C 0.2285(3) 0.6621(3) 1.0998(2) 0.0324(6) Uani 1 1 d . .
N1 N 0.3233(2) 0.3239(2) 1.03224(16) 0.0286(5) Uani 1 1 d . .
C14 C 0.2393(3) 0.2522(3) 0.6468(2) 0.0379(7) Uani 1 1 d . .
C13 C 0.1956(3) 0.2802(3) 0.7481(2) 0.0349(7) Uani 1 1 d . .
C12 C 0.3077(3) 0.2058(3) 1.0295(2) 0.0289(6) Uani 1 1 d . .
C21 C 0.3437(3) 0.7659(2) 1.1772(2) 0.0297(6) Uani 1 1 d . .
C11 C 0.1866(3) 0.1106(2) 0.9634(2) 0.0298(6) Uani 1 1 d . .
C27 C -0.0265(3) 0.5443(3) 0.8393(2) 0.0308(6) Uani 1 1 d . .
C28 C -0.0899(3) 0.5147(3) 0.7296(2) 0.0344(6) Uani 1 1 d . .
C1 C 0.4387(3) 0.4091(3) 1.0890(2) 0.0363(7) Uani 1 1 d . .
H1 H 0.4508 0.4903 1.0916 0.044 Uiso 1 1 calc R U
C4 C 0.4062(3) 0.1718(3) 1.0845(2) 0.0362(7) Uani 1 1 d . .
C3 C 0.5262(3) 0.2651(3) 1.1436(2) 0.0439(8) Uani 1 1 d . .
H3 H 0.5936 0.2465 1.1814 0.053 Uiso 1 1 calc R U
C7 C 0.1722(3) -0.0149(3) 0.9531(2) 0.0384(7) Uani 1 1 d . .
C5 C 0.3842(4) 0.0446(3) 1.0758(3) 0.0473(8) Uani 1 1 d . .
H5 H 0.4479 0.0234 1.1145 0.057 Uiso 1 1 calc R U
C17 C 0.3149(4) 0.2098(3) 0.4600(2) 0.0508(9) Uani 1 1 d . .
C16 C 0.1812(4) 0.1639(4) 0.4617(3) 0.0618(11) Uani 1 1 d . .
H16 H 0.1167 0.1189 0.4007 0.074 Uiso 1 1 calc R U
C26 C 0.3228(3) 0.8350(3) 1.2741(2) 0.0427(7) Uani 1 1 d . .
H26 H 0.2368 0.8178 1.2906 0.051 Uiso 1 1 calc R U
C22 C 0.4715(3) 0.7926(3) 1.1527(2) 0.0347(6) Uani 1 1 d . .
H22 H 0.4865 0.7449 1.0887 0.042 Uiso 1 1 calc R U
C10 C -0.0166(3) 0.0560(3) 0.8481(2) 0.0401(7) Uani 1 1 d . .
H10 H -0.0821 0.0788 0.8122 0.048 Uiso 1 1 calc R U
C18 C 0.4133(4) 0.2747(3) 0.5487(3) 0.0503(8) Uani 1 1 d . .
H18 H 0.5046 0.3037 0.5459 0.060 Uiso 1 1 calc R U
C19 C 0.3742(3) 0.2958(3) 0.6420(2) 0.0442(8) Uani 1 1 d . .
H19 H 0.4398 0.3401 0.7025 0.053 Uiso 1 1 calc R U
C33 C -0.2019(4) 0.5588(3) 0.7076(3) 0.0484(8) Uani 1 1 d . .
H33 H -0.2364 0.6092 0.7609 0.058 Uiso 1 1 calc R U
C29 C -0.0409(4) 0.4396(3) 0.6498(2) 0.0519(9) Uani 1 1 d . .
H29 H 0.0340 0.4093 0.6638 0.062 Uiso 1 1 calc R U
C8 C 0.0562(4) -0.1051(3) 0.8851(3) 0.0497(8) Uani 1 1 d . .
H8 H 0.0428 -0.1888 0.8761 0.060 Uiso 1 1 calc R U
C2 C 0.5432(3) 0.3831(3) 1.1452(2) 0.0445(8) Uani 1 1 d . .
H2 H 0.6229 0.4454 1.1830 0.053 Uiso 1 1 calc R U
C32 C -0.2629(4) 0.5277(4) 0.6063(3) 0.0629(11) Uani 1 1 d . .
H32 H -0.3384 0.5570 0.5915 0.076 Uiso 1 1 calc R U
C9 C -0.0368(4) -0.0701(3) 0.8323(3) 0.0503(9) Uani 1 1 d . .
H9 H -0.1134 -0.1297 0.7860 0.060 Uiso 1 1 calc R U
C24 C 0.5549(3) 0.9561(3) 1.3197(3) 0.0475(8) Uani 1 1 d . .
C6 C 0.2735(4) -0.0442(3) 1.0128(3) 0.0482(8) Uani 1 1 d . .
H6 H 0.2622 -0.1264 1.0078 0.058 Uiso 1 1 calc R U
C15 C 0.1421(4) 0.1851(3) 0.5557(2) 0.0517(9) Uani 1 1 d . .
H15 H 0.0509 0.1544 0.5578 0.062 Uiso 1 1 calc R U
C30 C -0.1021(5) 0.4086(4) 0.5483(3) 0.0661(11) Uani 1 1 d . .
H30 H -0.0689 0.3575 0.4945 0.079 Uiso 1 1 calc R U
C25 C 0.4297(4) 0.9289(3) 1.3456(3) 0.0546(9) Uani 1 1 d . .
H25 H 0.4169 0.9736 1.4111 0.065 Uiso 1 1 calc R U
C31 C -0.2116(4) 0.4541(4) 0.5286(3) 0.0596(10) 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tm Tm -0.3139 5.2483 '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
O4 Tm1 O6 79.26(8) . .
O4 Tm1 O3 124.05(8) . .
O6 Tm1 O3 78.35(8) . .
O4 Tm1 O5 76.16(8) . .
O6 Tm1 O5 124.92(7) . .
O3 Tm1 O5 76.20(8) . .
O4 Tm1 O1 132.18(8) . .
O6 Tm1 O1 146.34(7) . .
O3 Tm1 O1 89.07(8) . .
O5 Tm1 O1 80.74(7) . .
O4 Tm1 O2 79.04(8) . .
O6 Tm1 O2 145.23(8) . .
O3 Tm1 O2 136.42(8) . .
O5 Tm1 O2 74.96(7) . .
O1 Tm1 O2 54.58(7) . .
O4 Tm1 N2 84.73(8) . .
O6 Tm1 N2 80.51(7) . .
O3 Tm1 N2 139.48(7) . .
O5 Tm1 N2 143.25(8) . .
O1 Tm1 N2 89.80(7) . .
O2 Tm1 N2 70.73(7) . .
O4 Tm1 N1 140.14(8) . .
O6 Tm1 N1 71.76(7) . .
O3 Tm1 N1 76.39(7) . .
O5 Tm1 N1 143.36(8) . .
O1 Tm1 N1 74.99(7) . .
O2 Tm1 N1 110.59(7) . .
N2 Tm1 N1 64.27(7) . .
O4 Tm1 C13 105.09(9) . .
O6 Tm1 C13 160.57(8) . .
O3 Tm1 C13 112.63(9) . .
O5 Tm1 C13 74.24(8) . .
O1 Tm1 C13 27.52(8) . .
O2 Tm1 C13 27.20(8) . .
N2 Tm1 C13 81.05(8) . .
N1 Tm1 C13 94.64(8) . .
C13 O2 Tm1 89.07(17) . .
C24 C23 C22 118.8(3) . .
C24 C23 H23 120.6 . .
C22 C23 H23 120.6 . .
C27 O5 Tm1 137.59(19) . .
C20 O3 Tm1 131.19(19) . .
C13 O1 Tm1 94.83(17) . .
C27 O6 Tm1 137.38(18) 2_567 .
C10 N2 C11 117.6(2) . .
C10 N2 Tm1 121.36(19) . .
C11 N2 Tm1 121.03(17) . .
C20 O4 Tm1 158.7(2) 2_567 .
O3 C20 O4 125.0(3) . 2_567
O3 C20 C21 117.9(2) . .
O4 C20 C21 117.1(3) 2_567 .
C1 N1 C12 117.3(2) . .
C1 N1 Tm1 124.33(18) . .
C12 N1 Tm1 118.27(17) . .
C19 C14 C15 119.1(3) . .
C19 C14 C13 120.9(3) . .
C15 C14 C13 119.9(3) . .
O2 C13 O1 120.9(3) . .
O2 C13 C14 120.0(3) . .
O1 C13 C14 119.1(3) . .
O2 C13 Tm1 63.73(15) . .
O1 C13 Tm1 57.65(14) . .
C14 C13 Tm1 170.5(2) . .
N1 C12 C4 123.0(3) . .
N1 C12 C11 117.9(2) . .
C4 C12 C11 119.0(3) . .
C22 C21 C26 119.8(3) . .
C22 C21 C20 120.1(2) . .
C26 C21 C20 120.1(3) . .
N2 C11 C7 122.6(3) . .
N2 C11 C12 118.2(2) . .
C7 C11 C12 119.2(3) . .
O5 C27 O6 125.6(3) . 2_567
O5 C27 C28 117.5(3) . .
O6 C27 C28 116.9(2) 2_567 .
C29 C28 C33 119.0(3) . .
C29 C28 C27 120.6(3) . .
C33 C28 C27 120.4(3) . .
N1 C1 C2 123.5(3) . .
N1 C1 H1 118.2 . .
C2 C1 H1 118.2 . .
C3 C4 C12 117.6(3) . .
C3 C4 C5 122.5(3) . .
C12 C4 C5 119.9(3) . .
C2 C3 C4 119.5(3) . .
C2 C3 H3 120.2 . .
C4 C3 H3 120.2 . .
C8 C7 C11 117.4(3) . .
C8 C7 C6 123.1(3) . .
C11 C7 C6 119.5(3) . .
C6 C5 C4 121.1(3) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C16 C17 C18 121.9(3) . .
C16 C17 Cl1 119.6(3) . .
C18 C17 Cl1 118.4(3) . .
C17 C16 C15 119.2(3) . .
C17 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
C25 C26 C21 119.9(3) . .
C25 C26 H26 120.0 . .
C21 C26 H26 120.0 . .
C21 C22 C23 120.1(3) . .
C21 C22 H22 119.9 . .
C23 C22 H22 119.9 . .
N2 C10 C9 123.2(3) . .
N2 C10 H10 118.4 . .
C9 C10 H10 118.4 . .
C17 C18 C19 118.8(3) . .
C17 C18 H18 120.6 . .
C19 C18 H18 120.6 . .
C14 C19 C18 121.0(3) . .
C14 C19 H19 119.5 . .
C18 C19 H19 119.5 . .
C28 C33 C32 120.2(3) . .
C28 C33 H33 119.9 . .
C32 C33 H33 119.9 . .
C28 C29 C30 120.8(3) . .
C28 C29 H29 119.6 . .
C30 C29 H29 119.6 . .
C9 C8 C7 119.8(3) . .
C9 C8 H8 120.1 . .
C7 C8 H8 120.1 . .
C3 C2 C1 119.0(3) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C31 C32 C33 119.7(3) . .
C31 C32 H32 120.2 . .
C33 C32 H32 120.2 . .
C8 C9 C10 119.4(3) . .
C8 C9 H9 120.3 . .
C10 C9 H9 120.3 . .
C25 C24 C23 121.6(3) . .
C25 C24 Cl2 119.5(3) . .
C23 C24 Cl2 118.9(3) . .
C5 C6 C7 121.1(3) . .
C5 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C16 C15 C14 120.0(3) . .
C16 C15 H15 120.0 . .
C14 C15 H15 120.0 . .
C31 C30 C29 119.1(3) . .
C31 C30 H30 120.5 . .
C29 C30 H30 120.5 . .
C24 C25 C26 119.7(3) . .
C24 C25 H25 120.2 . .
C26 C25 H25 120.2 . .
C32 C31 C30 121.3(3) . .
C32 C31 Cl3 118.9(3) . .
C30 C31 Cl3 119.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Tm1 O4 2.249(2) .
Tm1 O6 2.2841(19) .
Tm1 O3 2.291(2) .
Tm1 O5 2.294(2) .
Tm1 O1 2.324(2) .
Tm1 O2 2.459(2) .
Tm1 N2 2.519(2) .
Tm1 N1 2.594(2) .
Tm1 C13 2.742(3) .
Cl1 C17 1.750(3) .
Cl2 C24 1.745(3) .
Cl3 C31 1.737(3) .
O2 C13 1.253(4) .
C23 C24 1.378(5) .
C23 C22 1.392(4) .
C23 H23 0.9300 .
O5 C27 1.251(3) .
O3 C20 1.251(3) .
O1 C13 1.272(4) .
O6 C27 1.256(3) 2_567
N2 C10 1.332(4) .
N2 C11 1.356(3) .
O4 C20 1.254(3) 2_567
C20 O4 1.254(3) 2_567
C20 C21 1.498(4) .
N1 C1 1.329(4) .
N1 C12 1.359(3) .
C14 C19 1.380(4) .
C14 C15 1.393(4) .
C14 C13 1.499(4) .
C12 C4 1.406(4) .
C12 C11 1.444(4) .
C21 C22 1.384(4) .
C21 C26 1.392(4) .
C11 C7 1.413(4) .
C27 O6 1.256(3) 2_567
C27 C28 1.506(4) .
C28 C29 1.377(4) .
C28 C33 1.386(4) .
C1 C2 1.401(4) .
C1 H1 0.9300 .
C4 C3 1.403(5) .
C4 C5 1.433(4) .
C3 C2 1.363(5) .
C3 H3 0.9300 .
C7 C8 1.399(5) .
C7 C6 1.431(5) .
C5 C6 1.338(5) .
C5 H5 0.9300 .
C17 C16 1.361(5) .
C17 C18 1.375(5) .
C16 C15 1.390(5) .
C16 H16 0.9300 .
C26 C25 1.378(5) .
C26 H26 0.9300 .
C22 H22 0.9300 .
C10 C9 1.394(4) .
C10 H10 0.9300 .
C18 C19 1.381(4) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C33 C32 1.389(5) .
C33 H33 0.9300 .
C29 C30 1.392(5) .
C29 H29 0.9300 .
C8 C9 1.356(5) .
C8 H8 0.9300 .
C2 H2 0.9300 .
C32 C31 1.364(5) .
C32 H32 0.9300 .
C9 H9 0.9300 .
C24 C25 1.370(5) .
C6 H6 0.9300 .
C15 H15 0.9300 .
C30 C31 1.366(5) .
C30 H30 0.9300 .
C25 H25 0.9300 .
