#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:37:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180513 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/82/7218278.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_7218278
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 Ho2 N4 O12'
_chemical_formula_weight         1623.58
_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                111.041(2)
_cell_angle_beta                 96.4820(10)
_cell_angle_gamma                101.4680(10)
_cell_formula_units_Z            1
_cell_length_a                   10.0939(3)
_cell_length_b                   11.8412(4)
_cell_length_c                   14.2899(5)
_cell_measurement_reflns_used    22815
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.753
_cell_measurement_theta_min      4.702
_cell_volume                     1530.25(9)
_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    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.932
_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  0.0286
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22815
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         30.122
_diffrn_reflns_theta_min         1.559
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.896
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Bruker-AXS (2008)'
_exptl_crystal_colour            Pink
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       Plate
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         8415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0258
_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)+(0.0239P)²+0.1125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7359
_reflns_number_total             8415
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce01806k2.cif
_cod_data_source_block           Compound_6
_cod_depositor_comments
'Adding full bibliography for 7218273--7218283.cif.'
_cod_original_cell_volume        1530.24(9)
_cod_database_code               7218278
#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
Ho1 Ho 0.87697(2) 0.12789(2) 0.06470(2) 0.02550(4) Uani 1 1 d . .
Cl1 Cl 0.63753(10) 0.31295(10) 0.65843(6) 0.0720(3) Uani 1 1 d . .
Cl3 Cl 0.31103(11) -0.57849(9) -0.41061(8) 0.0881(3) Uani 1 1 d . .
Cl2 Cl 0.71054(14) -0.08141(12) -0.59689(7) 0.1045(4) Uani 1 1 d . .
N1 N 0.67510(19) 0.17669(17) -0.03292(14) 0.0281(4) Uani 1 1 d . .
N2 N 0.9069(2) 0.35502(18) 0.08760(15) 0.0321(4) Uani 1 1 d . .
O1 O 0.71501(18) 0.15047(17) 0.17146(13) 0.0379(4) Uani 1 1 d . .
O2 O 0.92701(19) 0.26239(16) 0.24962(13) 0.0410(4) Uani 1 1 d . .
O3 O 0.92394(19) 0.11352(17) -0.09320(13) 0.0410(4) Uani 1 1 d . .
O6 O 0.73826(18) -0.06816(15) -0.04132(14) 0.0413(4) Uani 1 1 d . .
O5 O 0.9274(2) -0.00015(17) 0.14619(14) 0.0434(4) Uani 1 1 d . .
C20 C 0.9742(3) 0.0450(2) -0.16185(19) 0.0315(5) Uani 1 1 d . .
C12 C 0.6913(2) 0.2950(2) -0.02977(18) 0.0298(5) Uani 1 1 d . .
O4 O 1.11114(18) 0.17572(19) 0.09954(15) 0.0487(5) Uani 1 1 d . .
C11 C 0.8123(3) 0.3897(2) 0.03612(18) 0.0308(5) Uani 1 1 d . .
C28 C 0.6546(2) -0.2663(2) -0.17736(18) 0.0300(5) Uani 1 1 d . .
C27 C 0.7688(2) -0.1622(2) -0.10011(18) 0.0320(5) Uani 1 1 d . .
C29 C 0.5260(3) -0.2943(2) -0.1544(2) 0.0351(5) Uani 1 1 d . .
H29 H 0.5100 -0.2474 -0.0908 0.042 Uiso 1 1 calc R U
C31 C 0.4443(3) -0.4572(3) -0.3205(2) 0.0491(7) Uani 1 1 d . .
C13 C 0.8041(3) 0.2199(2) 0.25276(19) 0.0346(6) Uani 1 1 d . .
C17 C 0.6866(3) 0.2912(3) 0.5412(2) 0.0514(8) Uani 1 1 d . .
C21 C 0.9095(3) 0.0151(2) -0.27092(19) 0.0343(5) Uani 1 1 d . .
C4 C 0.5924(3) 0.3287(3) -0.08517(19) 0.0371(6) Uani 1 1 d . .
C14 C 0.7607(3) 0.2477(2) 0.35440(19) 0.0366(6) Uani 1 1 d . .
C7 C 0.8266(3) 0.5152(2) 0.0461(2) 0.0398(6) Uani 1 1 d . .
C10 C 1.0151(3) 0.4445(2) 0.1518(2) 0.0415(6) Uani 1 1 d . .
H10 H 1.0800 0.4219 0.1882 0.050 Uiso 1 1 calc R U
C1 C 0.5597(3) 0.0921(2) -0.08964(19) 0.0359(6) Uani 1 1 d . .
H1 H 0.5472 0.0111 -0.0921 0.043 Uiso 1 1 calc R U
C6 C 0.7259(3) 0.5443(3) -0.0133(2) 0.0492(7) Uani 1 1 d . .
H6 H 0.7372 0.6265 -0.0079 0.059 Uiso 1 1 calc R U
C3 C 0.4728(3) 0.2359(3) -0.1446(2) 0.0457(7) Uani 1 1 d . .
H3 H 0.4056 0.2542 -0.1827 0.055 Uiso 1 1 calc R U
C33 C 0.6772(3) -0.3346(3) -0.2733(2) 0.0453(7) Uani 1 1 d . .
H33 H 0.7640 -0.3170 -0.2889 0.054 Uiso 1 1 calc R U
C2 C 0.4559(3) 0.1177(3) -0.1459(2) 0.0450(7) Uani 1 1 d . .
H2 H 0.3762 0.0553 -0.1838 0.054 Uiso 1 1 calc R U
C22 C 0.7976(3) 0.0592(3) -0.2930(2) 0.0487(7) Uani 1 1 d . .
H22 H 0.7636 0.1099 -0.2400 0.058 Uiso 1 1 calc R U
C5 C 0.6156(3) 0.4560(3) -0.0766(2) 0.0494(7) Uani 1 1 d . .
H5 H 0.5527 0.4772 -0.1158 0.059 Uiso 1 1 calc R U
C18 C 0.8208(4) 0.3363(4) 0.5387(2) 0.0653(9) Uani 1 1 d . .
H18 H 0.8862 0.3805 0.5991 0.078 Uiso 1 1 calc R U
C32 C 0.5701(3) -0.4292(3) -0.3456(2) 0.0562(8) Uani 1 1 d . .
H32 H 0.5838 -0.4732 -0.4107 0.067 Uiso 1 1 calc R U
C30 C 0.4201(3) -0.3921(2) -0.2255(2) 0.0429(6) Uani 1 1 d . .
H30 H 0.3345 -0.4132 -0.2091 0.051 Uiso 1 1 calc R U
C19 C 0.8587(3) 0.3153(3) 0.4444(2) 0.0524(8) Uani 1 1 d . .
H19 H 0.9496 0.3465 0.4417 0.063 Uiso 1 1 calc R U
C15 C 0.6260(3) 0.2045(3) 0.3592(2) 0.0454(7) Uani 1 1 d . .
H15 H 0.5602 0.1604 0.2990 0.055 Uiso 1 1 calc R U
C9 C 1.0361(3) 0.5699(3) 0.1671(2) 0.0518(7) Uani 1 1 d . .
H9 H 1.1132 0.6292 0.2130 0.062 Uiso 1 1 calc R U
C26 C 0.9581(3) -0.0599(3) -0.3505(2) 0.0536(8) Uani 1 1 d . .
H26 H 1.0329 -0.0902 -0.3364 0.064 Uiso 1 1 calc R U
C16 C 0.5868(3) 0.2261(3) 0.4528(2) 0.0522(8) Uani 1 1 d . .
H16 H 0.4954 0.1973 0.4560 0.063 Uiso 1 1 calc R U
C24 C 0.7872(4) -0.0454(3) -0.4708(2) 0.0594(9) Uani 1 1 d . .
C8 C 0.9429(3) 0.6052(3) 0.1143(2) 0.0522(8) Uani 1 1 d . .
H8 H 0.9564 0.6888 0.1235 0.063 Uiso 1 1 calc R U
C23 C 0.7361(4) 0.0278(3) -0.3937(3) 0.0625(9) Uani 1 1 d . .
H23 H 0.6603 0.0567 -0.4086 0.075 Uiso 1 1 calc R U
C25 C 0.8969(4) -0.0910(3) -0.4514(2) 0.0672(10) Uani 1 1 d . .
H25 H 0.9298 -0.1420 -0.5049 0.081 Uiso 1 1 calc R U
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'
Ho Ho -0.2175 4.6783 '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 Ho1 O3 79.10(7) . .
O4 Ho1 O6 123.84(7) . .
O3 Ho1 O6 78.43(7) . .
O4 Ho1 O5 75.96(7) . .
O3 Ho1 O5 124.86(6) . .
O6 Ho1 O5 76.24(6) . .
O4 Ho1 O1 132.00(6) . .
O3 Ho1 O1 146.59(6) . .
O6 Ho1 O1 89.42(7) . .
O5 Ho1 O1 80.84(6) . .
O4 Ho1 O2 79.23(7) . .
O3 Ho1 O2 144.99(6) . .
O6 Ho1 O2 136.57(6) . .
O5 Ho1 O2 75.19(6) . .
O1 Ho1 O2 54.26(6) . .
O4 Ho1 N2 85.51(7) . .
O3 Ho1 N2 80.57(6) . .
O6 Ho1 N2 139.02(6) . .
O5 Ho1 N2 143.55(6) . .
O1 Ho1 N2 89.17(6) . .
O2 Ho1 N2 70.62(6) . .
O4 Ho1 N1 140.16(7) . .
O3 Ho1 N1 71.69(6) . .
O6 Ho1 N1 76.34(6) . .
O5 Ho1 N1 143.50(7) . .
O1 Ho1 N1 75.24(6) . .
O2 Ho1 N1 110.53(6) . .
N2 Ho1 N1 63.75(6) . .
O4 Ho1 C13 105.08(8) . .
O3 Ho1 C13 160.44(7) . .
O6 Ho1 C13 112.84(7) . .
O5 Ho1 C13 74.38(7) . .
O1 Ho1 C13 27.37(7) . .
O2 Ho1 C13 27.05(7) . .
N2 Ho1 C13 80.73(7) . .
N1 Ho1 C13 94.80(7) . .
C1 N1 C12 117.3(2) . .
C1 N1 Ho1 124.24(16) . .
C12 N1 Ho1 118.36(15) . .
C10 N2 C11 117.6(2) . .
C10 N2 Ho1 121.19(17) . .
C11 N2 Ho1 121.21(15) . .
C13 O1 Ho1 94.59(15) . .
C13 O2 Ho1 89.14(15) . .
C20 O3 Ho1 137.68(16) . .
C27 O6 Ho1 130.35(16) . .
C20 O5 Ho1 137.26(17) 2_755 .
O5 C20 O3 125.1(2) 2_755 .
O5 C20 C21 118.1(2) 2_755 .
O3 C20 C21 116.8(2) . .
N1 C12 C4 122.7(2) . .
N1 C12 C11 118.0(2) . .
C4 C12 C11 119.2(2) . .
C27 O4 Ho1 159.99(19) 2_755 .
N2 C11 C7 122.7(2) . .
N2 C11 C12 118.3(2) . .
C7 C11 C12 119.0(2) . .
C29 C28 C33 119.6(2) . .
C29 C28 C27 120.3(2) . .
C33 C28 C27 120.0(2) . .
O6 C27 O4 124.7(2) . 2_755
O6 C27 C28 118.1(2) . .
O4 C27 C28 117.2(2) 2_755 .
C28 C29 C30 120.5(2) . .
C28 C29 H29 119.8 . .
C30 C29 H29 119.8 . .
C32 C31 C30 121.6(3) . .
C32 C31 Cl3 119.4(2) . .
C30 C31 Cl3 119.0(2) . .
O2 C13 O1 121.3(2) . .
O2 C13 C14 119.9(2) . .
O1 C13 C14 118.7(2) . .
O2 C13 Ho1 63.81(13) . .
O1 C13 Ho1 58.04(12) . .
C14 C13 Ho1 170.22(17) . .
C18 C17 C16 121.9(3) . .
C18 C17 Cl1 119.9(2) . .
C16 C17 Cl1 118.2(2) . .
C26 C21 C22 119.0(3) . .
C26 C21 C20 120.3(2) . .
C22 C21 C20 120.6(2) . .
C3 C4 C12 117.8(2) . .
C3 C4 C5 122.7(2) . .
C12 C4 C5 119.5(3) . .
C15 C14 C19 119.6(3) . .
C15 C14 C13 120.7(2) . .
C19 C14 C13 119.7(2) . .
C8 C7 C11 117.1(2) . .
C8 C7 C6 123.1(3) . .
C11 C7 C6 119.7(3) . .
N2 C10 C9 123.4(3) . .
N2 C10 H10 118.3 . .
C9 C10 H10 118.3 . .
N1 C1 C2 123.7(2) . .
N1 C1 H1 118.1 . .
C2 C1 H1 118.1 . .
C5 C6 C7 121.2(3) . .
C5 C6 H6 119.4 . .
C7 C6 H6 119.4 . .
C2 C3 C4 119.2(2) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
C32 C33 C28 119.9(3) . .
C32 C33 H33 120.1 . .
C28 C33 H33 120.1 . .
C3 C2 C1 119.2(3) . .
C3 C2 H2 120.4 . .
C1 C2 H2 120.4 . .
C23 C22 C21 120.2(3) . .
C23 C22 H22 119.9 . .
C21 C22 H22 119.9 . .
C6 C5 C4 121.2(3) . .
C6 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
C17 C18 C19 119.1(3) . .
C17 C18 H18 120.5 . .
C19 C18 H18 120.5 . .
C31 C32 C33 119.5(3) . .
C31 C32 H32 120.2 . .
C33 C32 H32 120.2 . .
C31 C30 C29 118.8(3) . .
C31 C30 H30 120.6 . .
C29 C30 H30 120.6 . .
C14 C19 C18 120.1(3) . .
C14 C19 H19 120.0 . .
C18 C19 H19 120.0 . .
C14 C15 C16 120.8(3) . .
C14 C15 H15 119.6 . .
C16 C15 H15 119.6 . .
C8 C9 C10 119.3(3) . .
C8 C9 H9 120.3 . .
C10 C9 H9 120.3 . .
C21 C26 C25 120.9(3) . .
C21 C26 H26 119.5 . .
C25 C26 H26 119.5 . .
C17 C16 C15 118.5(3) . .
C17 C16 H16 120.7 . .
C15 C16 H16 120.7 . .
C23 C24 C25 121.6(3) . .
C23 C24 Cl2 118.9(3) . .
C25 C24 Cl2 119.5(3) . .
C9 C8 C7 119.8(3) . .
C9 C8 H8 120.1 . .
C7 C8 H8 120.1 . .
C24 C23 C22 119.6(3) . .
C24 C23 H23 120.2 . .
C22 C23 H23 120.2 . .
C24 C25 C26 118.8(3) . .
C24 C25 H25 120.6 . .
C26 C25 H25 120.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ho1 O4 2.2705(17) .
Ho1 O3 2.3115(17) .
Ho1 O6 2.3125(16) .
Ho1 O5 2.3141(17) .
Ho1 O1 2.3484(17) .
Ho1 O2 2.4761(17) .
Ho1 N2 2.5405(19) .
Ho1 N1 2.6148(18) .
Ho1 C13 2.759(2) .
Cl1 C17 1.745(3) .
Cl3 C31 1.745(3) .
Cl2 C24 1.740(3) .
N1 C1 1.325(3) .
N1 C12 1.362(3) .
N2 C10 1.331(3) .
N2 C11 1.356(3) .
O1 C13 1.272(3) .
O2 C13 1.255(3) .
O3 C20 1.258(3) .
O6 C27 1.251(3) .
O5 C20 1.250(3) 2_755
C20 O5 1.250(3) 2_755
C20 C21 1.504(3) .
C12 C4 1.410(3) .
C12 C11 1.440(3) .
O4 C27 1.253(3) 2_755
C11 C7 1.416(3) .
C28 C29 1.381(3) .
C28 C33 1.390(3) .
C28 C27 1.496(3) .
C27 O4 1.253(3) 2_755
C29 C30 1.390(4) .
C29 H29 0.9300 .
C31 C32 1.368(4) .
C31 C30 1.377(4) .
C13 C14 1.506(3) .
C17 C18 1.364(5) .
C17 C16 1.382(4) .
C21 C26 1.378(4) .
C21 C22 1.386(4) .
C4 C3 1.399(4) .
C4 C5 1.435(4) .
C14 C15 1.373(4) .
C14 C19 1.390(4) .
C7 C8 1.401(4) .
C7 C6 1.424(4) .
C10 C9 1.389(4) .
C10 H10 0.9300 .
C1 C2 1.395(4) .
C1 H1 0.9300 .
C6 C5 1.335(4) .
C6 H6 0.9300 .
C3 C2 1.368(4) .
C3 H3 0.9300 .
C33 C32 1.388(4) .
C33 H33 0.9300 .
C2 H2 0.9300 .
C22 C23 1.385(4) .
C22 H22 0.9300 .
C5 H5 0.9300 .
C18 C19 1.391(4) .
C18 H18 0.9300 .
C32 H32 0.9300 .
C30 H30 0.9300 .
C19 H19 0.9300 .
C15 C16 1.388(4) .
C15 H15 0.9300 .
C9 C8 1.360(4) .
C9 H9 0.9300 .
C26 C25 1.386(4) .
C26 H26 0.9300 .
C16 H16 0.9300 .
C24 C23 1.361(5) .
C24 C25 1.368(5) .
C8 H8 0.9300 .
C23 H23 0.9300 .
C25 H25 0.9300 .
