#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:05:22 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179230 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/50/4315062.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_4315062
loop_
_publ_author_name
'Hai-Ying Wang'
'Jun-Yan Cheng'
'Jian-Ping Ma'
'Yu-Bin Dong'
'Ru-Qi Huang'
_publ_section_title
;
 Synthesis and Characterization of New Coordination Polymers with Tunable
 Luminescent Properties Generated from Bent 1,2,4-Triazole-Bridged
 N,N'-Dioxides and Ln(III) Salts
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2416
_journal_page_last               2426
_journal_paper_doi               10.1021/ic902311g
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C24 H28 Cl3 N12 O20 Tm'
_chemical_formula_weight         1079.86
_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                91.927(2)
_cell_angle_beta                 94.929(2)
_cell_angle_gamma                90.397(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2035(13)
_cell_length_b                   11.7560(16)
_cell_length_c                   17.331(2)
_cell_measurement_reflns_used    3616
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.291
_cell_measurement_theta_min      2.361
_cell_volume                     1867.1(4)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area 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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9827
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.18
_exptl_absorpt_coefficient_mu    2.690
_exptl_absorpt_correction_T_max  0.8553
_exptl_absorpt_correction_T_min  0.4615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.496
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0516P)²+4.8392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                6021
_reflns_number_total             6792
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic902311g_si_001_11.cif
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1867.0(4)
_cod_database_code               4315062
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 1.1671(7) -0.1158(5) 0.8295(4) 0.0373(14) Uani 1 1 d . . .
H1 H 1.1937 -0.1856 0.8084 0.045 Uiso 1 1 calc R . .
C2 C 1.2498(7) -0.0676(6) 0.8911(4) 0.0420(15) Uani 1 1 d . . .
H2 H 1.3322 -0.1047 0.9120 0.050 Uiso 1 1 calc R . .
C3 C 1.2114(7) 0.0361(5) 0.9226(4) 0.0390(15) Uani 1 1 d . . .
H3 H 1.2682 0.0702 0.9641 0.047 Uiso 1 1 calc R . .
C4 C 1.0863(7) 0.0885(5) 0.8912(3) 0.0332(13) Uani 1 1 d . . .
C5 C 1.0051(7) 0.0365(5) 0.8291(3) 0.0338(13) Uani 1 1 d . . .
H5 H 0.9205 0.0705 0.8081 0.041 Uiso 1 1 calc R . .
C6 C 1.0317(7) 0.1911(5) 0.9287(3) 0.0319(13) Uani 1 1 d . . .
C7 C 0.9137(6) 0.3470(5) 0.9528(3) 0.0298(13) Uani 1 1 d . . .
C8 C 0.8199(7) 0.4470(5) 0.9458(3) 0.0329(13) Uani 1 1 d . . .
C9 C 0.7638(7) 0.4916(6) 1.0126(3) 0.0393(15) Uani 1 1 d . . .
H9 H 0.7886 0.4596 1.0602 0.047 Uiso 1 1 calc R . .
C10 C 0.6714(8) 0.5834(6) 1.0076(4) 0.0437(16) Uani 1 1 d . . .
H10 H 0.6343 0.6140 1.0519 0.052 Uiso 1 1 calc R . .
C11 C 0.6348(8) 0.6292(6) 0.9373(4) 0.0434(16) Uani 1 1 d . . .
H11 H 0.5720 0.6908 0.9336 0.052 Uiso 1 1 calc R . .
C12 C 0.7789(7) 0.4957(5) 0.8768(3) 0.0332(13) Uani 1 1 d . . .
H12 H 0.8136 0.4662 0.8314 0.040 Uiso 1 1 calc R . .
C13 C 0.3705(8) 0.8807(6) 0.6852(4) 0.0439(16) Uani 1 1 d . . .
H13 H 0.3494 0.8135 0.7090 0.053 Uiso 1 1 calc R . .
C14 C 0.2722(8) 0.9239(6) 0.6303(4) 0.0498(18) Uani 1 1 d . . .
H14 H 0.1851 0.8850 0.6160 0.060 Uiso 1 1 calc R . .
C15 C 0.3013(7) 1.0240(6) 0.5964(4) 0.0430(16) Uani 1 1 d . . .
H15 H 0.2334 1.0539 0.5599 0.052 Uiso 1 1 calc R . .
C16 C 0.4311(7) 1.0803(5) 0.6164(3) 0.0340(14) Uani 1 1 d . . .
C17 C 0.5308(7) 1.0335(5) 0.6712(3) 0.0355(14) Uani 1 1 d . . .
H17 H 0.6201 1.0695 0.6847 0.043 Uiso 1 1 calc R . .
C18 C 0.4745(7) 1.1813(5) 0.5758(4) 0.0345(14) Uani 1 1 d . . .
C19 C 0.5846(7) 1.3358(5) 0.5468(3) 0.0326(13) Uani 1 1 d . . .
C20 C 0.6824(7) 1.4363(5) 0.5465(3) 0.0337(13) Uani 1 1 d . . .
C21 C 0.7191(8) 1.4742(6) 0.4765(4) 0.0445(16) Uani 1 1 d . . .
H21 H 0.6796 1.4389 0.4305 0.053 Uiso 1 1 calc R . .
C22 C 0.8143(9) 1.5645(6) 0.4746(4) 0.0496(18) Uani 1 1 d . . .
H22 H 0.8403 1.5894 0.4272 0.060 Uiso 1 1 calc R . .
C23 C 0.8716(8) 1.6183(6) 0.5425(4) 0.0430(16) Uani 1 1 d . . .
H23 H 0.9345 1.6803 0.5415 0.052 Uiso 1 1 calc R . .
C24 C 0.7423(7) 1.4912(5) 0.6139(3) 0.0335(13) Uani 1 1 d . . .
H24 H 0.7186 1.4670 0.6618 0.040 Uiso 1 1 calc R . .
Cl1 Cl 0.58376(19) 0.14702(15) 0.88476(11) 0.0478(4) Uani 1 1 d . . .
Cl2 Cl 0.2930(2) 0.5094(2) 0.76496(13) 0.0677(6) Uani 1 1 d . . .
Cl3 Cl 0.93145(3) 0.15346(2) 0.606304(13) 0.0605(5) Uani 1 1 d . . .
H8B H 0.6960 0.8617 0.5889 0.073 Uiso 1 1 d R . .
H8A H 0.8262 0.9069 0.6179 0.073 Uiso 1 1 d R . .
H6B H 0.8344 0.8473 0.9121 0.073 Uiso 1 1 d R . .
H5B H 1.0154 0.6329 0.7919 0.073 Uiso 1 1 d R . .
H6A H 0.7169 0.9011 0.8726 0.073 Uiso 1 1 d R . .
H5A H 0.9935 0.6745 0.8684 0.073 Uiso 1 1 d R . .
H7A H 0.5138 0.6419 0.6883 0.073 Uiso 1 1 d R . .
H7B H 0.5441 0.6946 0.6214 0.073 Uiso 1 1 d R . .
H5C H 1.0334 0.3209 0.7998 0.073 Uiso 1 1 d R . .
H5D H 0.8990 0.2471 0.7891 0.073 Uiso 1 1 d R . .
H12A H 0.5029 1.3130 0.7048 0.073 Uiso 1 1 d R . .
H12B H 0.6573 1.2547 0.7045 0.073 Uiso 1 1 d R . .
Tm1 Tm 0.77445(3) 0.76563(2) 0.744786(13) 0.02846(10) Uani 1 1 d R . .
N1 N 0.68967(3) 0.58511(2) 0.873534(13) 0.0333(11) Uani 1 1 d R . .
N2 N 0.95845(3) 0.30363(2) 1.019531(13) 0.0384(12) Uani 1 1 d R . .
N3 N 1.03260(3) 0.20476(2) 1.003896(13) 0.0369(12) Uani 1 1 d R . .
N4 N 0.96043(3) 0.27944(2) 0.894169(13) 0.0311(11) Uani 1 1 d R . .
N5 N 0.94535(3) 0.30519(2) 0.815845(13) 0.0417(13) Uani 1 1 d R . .
N6 N 0.49734(3) 0.93546(2) 0.704674(13) 0.0376(12) Uani 1 1 d R . .
N7 N 1.04774(3) -0.06342(2) 0.798951(13) 0.0323(11) Uani 1 1 d R . .
N8 N 0.83428(3) 1.57915(2) 0.610102(13) 0.0361(12) Uani 1 1 d R . .
N9 N 0.51992(3) 1.28953(2) 0.483121(13) 0.0404(13) Uani 1 1 d R . .
N10 N 0.44966(3) 1.19188(2) 0.501136(13) 0.0410(13) Uani 1 1 d R . .
N11 N 0.55461(3) 1.27235(2) 0.607714(13) 0.0322(11) Uani 1 1 d R . .
N12 N 0.59045(3) 1.30424(2) 0.685912(13) 0.0438(13) Uani 1 1 d R . .
O1 O 0.88872(3) 1.63130(2) 0.675266(13) 0.0407(11) Uani 1 1 d R . .
O2 O 0.59365(3) 0.89496(2) 0.757691(13) 0.0450(12) Uani 1 1 d R . .
O3 O 0.96663(3) -0.11182(2) 0.738954(13) 0.0404(11) Uani 1 1 d R . .
O4 O 0.65458(3) 0.63096(2) 0.805314(13) 0.0411(11) Uani 1 1 d R . .
O5 O 0.96660(3) 0.67527(2) 0.820420(13) 0.0368(10) Uani 1 1 d R . .
O6 O 0.78412(3) 0.85309(2) 0.868907(13) 0.0400(10) Uani 1 1 d R . .
O7 O 0.57536(3) 0.68216(2) 0.667714(13) 0.0366(10) Uani 1 1 d R . .
O8 O 0.76605(3) 0.85318(2) 0.623435(13) 0.0432(11) Uani 1 1 d R . .
O9 O 0.15374(3) 0.48634(2) 0.770470(13) 0.159(5) Uani 1 1 d R . .
O10 O 0.39028(3) 0.45317(2) 0.817968(13) 0.147(4) Uani 1 1 d R . .
O11 O 0.30267(3) 0.62286(2) 0.787436(13) 0.252(9) Uani 1 1 d R . .
O12 O 0.36048(3) 0.50510(2) 0.700380(13) 0.165(5) Uani 1 1 d R . .
O13 O 0.44670(3) 0.14682(2) 0.839253(13) 0.109(3) Uani 1 1 d R . .
O14 O 0.60086(3) 0.03800(2) 0.917131(13) 0.089(2) Uani 1 1 d R . .
O15 O 0.58795(3) 0.23058(2) 0.944369(13) 0.108(3) Uani 1 1 d R . .
O16 O 0.68959(3) 0.16677(2) 0.832029(13) 0.087(2) Uani 1 1 d R . .
O17 O 0.84687(3) 0.16111(2) 0.670844(13) 0.0814(19) Uani 1 1 d R . .
O18 O 0.94744(3) 0.03860(2) 0.582782(13) 0.0775(18) Uani 1 1 d R . .
O19 O 1.06990(3) 0.19692(2) 0.630697(13) 0.217(8) Uani 1 1 d R . .
O20 O 0.87051(3) 0.21649(2) 0.547246(13) 0.189(6) Uani 1 1 d 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'
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
_geom_angle_publ_flag
N7 C1 C2 120.6(5) . . ?
N7 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 120.1(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 118.8(6) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.3(6) . . ?
C5 C4 C6 119.9(6) . . ?
C3 C4 C6 120.5(5) . . ?
N7 C5 C4 120.2(5) . . ?
N7 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N3 C6 N4 109.3(4) . . ?
N3 C6 C4 122.8(5) . . ?
N4 C6 C4 127.6(5) . . ?
N2 C7 N4 108.9(4) . . ?
N2 C7 C8 123.3(5) . . ?
N4 C7 C8 127.6(5) . . ?
C12 C8 C9 118.3(6) . . ?
C12 C8 C7 123.5(6) . . ?
C9 C8 C7 118.2(5) . . ?
C10 C9 C8 119.6(6) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 119.8(6) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 119.8(6) . . ?
N1 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N1 C12 C8 120.9(5) . . ?
N1 C12 H12 119.5 . . ?
C8 C12 H12 119.5 . . ?
N6 C13 C14 119.9(6) . . ?
N6 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.3(7) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 119.8(6) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 118.8(6) . . ?
C15 C16 C18 121.9(6) . . ?
C17 C16 C18 118.9(6) . . ?
N6 C17 C16 119.8(6) . . ?
N6 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
N10 C18 N11 110.1(4) . . ?
N10 C18 C16 123.3(5) . . ?
N11 C18 C16 126.4(5) . . ?
N9 C19 N11 109.1(4) . . ?
N9 C19 C20 122.3(5) . . ?
N11 C19 C20 128.5(5) . . ?
C21 C20 C24 118.7(6) . . ?
C21 C20 C19 118.6(5) . . ?
C24 C20 C19 122.6(5) . . ?
C22 C21 C20 119.8(6) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.4(6) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
N8 C23 C22 118.5(6) . . ?
N8 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
N8 C24 C20 120.0(5) . . ?
N8 C24 H24 120.0 . . ?
C20 C24 H24 120.0 . . ?
O15 Cl1 O16 112.15(12) . . ?
O15 Cl1 O14 109.51(12) . . ?
O16 Cl1 O14 111.20(12) . . ?
O15 Cl1 O13 110.99(12) . . ?
O16 Cl1 O13 105.30(12) . . ?
O14 Cl1 O13 107.54(12) . . ?
O9 Cl2 O12 125.93(19) . . ?
O9 Cl2 O11 102.26(14) . . ?
O12 Cl2 O11 103.16(14) . . ?
O9 Cl2 O10 114.76(14) . . ?
O12 Cl2 O10 103.01(14) . . ?
O11 Cl2 O10 105.57(17) . . ?
O20 Cl3 O19 109.4 . . ?
O20 Cl3 O18 111.8 . . ?
O19 Cl3 O18 107.7 . . ?
O20 Cl3 O17 110.4 . . ?
O19 Cl3 O17 107.2 . . ?
O18 Cl3 O17 110.2 . . ?
O4 Tm1 O1 91.6 . 1_545 ?
O4 Tm1 O2 92.4 . . ?
O1 Tm1 O2 151.8 1_545 . ?
O4 Tm1 O3 151.4 . 1_565 ?
O1 Tm1 O3 90.4 1_545 1_565 ?
O2 Tm1 O3 99.2 . 1_565 ?
O4 Tm1 O6 81.2 . . ?
O1 Tm1 O6 141.2 1_545 . ?
O2 Tm1 O6 67.0 . . ?
O3 Tm1 O6 79.5 1_565 . ?
O4 Tm1 O7 66.3 . . ?
O1 Tm1 O7 78.8 1_545 . ?
O2 Tm1 O7 77.3 . . ?
O3 Tm1 O7 141.9 1_565 . ?
O6 Tm1 O7 130.1 . . ?
O4 Tm1 O8 139.7 . . ?
O1 Tm1 O8 80.0 1_545 . ?
O2 Tm1 O8 78.9 . . ?
O3 Tm1 O8 68.6 1_565 . ?
O6 Tm1 O8 128.3 . . ?
O7 Tm1 O8 73.5 . . ?
O4 Tm1 O5 77.3 . . ?
O1 Tm1 O5 67.5 1_545 . ?
O2 Tm1 O5 140.5 . . ?
O3 Tm1 O5 77.2 1_565 . ?
O6 Tm1 O5 73.7 . . ?
O7 Tm1 O5 129.0 . . ?
O8 Tm1 O5 132.1 . . ?
O4 N1 C12 118.9(2) . . ?
O4 N1 C11 119.5(3) . . ?
C12 N1 C11 121.6(4) . . ?
C7 N2 N3 107.6(3) . . ?
C6 N3 N2 108.0(3) . . ?
C6 N4 C7 106.2(3) . . ?
C6 N4 N5 128.8(2) . . ?
C7 N4 N5 124.8(2) . . ?
N4 N5 H5C 109.6 . . ?
N4 N5 H5D 108.6 . . ?
H5C N5 H5D 113.4 . . ?
O2 N6 C13 120.7(3) . . ?
O2 N6 C17 118.0(3) . . ?
C13 N6 C17 121.3(4) . . ?
O3 N7 C1 120.1(3) . . ?
O3 N7 C5 118.8(3) . . ?
C1 N7 C5 121.1(4) . . ?
O1 N8 C24 119.0(3) . . ?
O1 N8 C23 118.5(3) . . ?
C24 N8 C23 122.5(4) . . ?
C19 N9 N10 108.7(3) . . ?
C18 N10 N9 106.8(3) . . ?
C19 N11 C18 105.3(4) . . ?
C19 N11 N12 124.6(3) . . ?
C18 N11 N12 129.9(3) . . ?
N11 N12 H12A 103.4 . . ?
N11 N12 H12B 106.7 . . ?
H12A N12 H12B 123.3 . . ?
N8 O1 Tm1 125.9 . 1_565 ?
N6 O2 Tm1 129.9 . . ?
N7 O3 Tm1 126.6 . 1_545 ?
N1 O4 Tm1 129.2 . . ?
Tm1 O5 H5B 110.7 . . ?
Tm1 O5 H5A 134.4 . . ?
H5B O5 H5A 114.9 . . ?
Tm1 O6 H6B 137.2 . . ?
Tm1 O6 H6A 111.8 . . ?
H6B O6 H6A 110.8 . . ?
Tm1 O7 H7A 120.0 . . ?
Tm1 O7 H7B 129.7 . . ?
H7A O7 H7B 109.4 . . ?
Tm1 O8 H8B 131.2 . . ?
Tm1 O8 H8A 118.2 . . ?
H8B O8 H8A 105.8 . . ?
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 N7 1.340(6) . ?
C1 C2 1.361(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(8) . ?
C4 C6 1.463(8) . ?
C5 N7 1.344(6) . ?
C5 H5 0.9300 . ?
C6 N3 1.307(6) . ?
C6 N4 1.360(6) . ?
C7 N2 1.314(6) . ?
C7 N4 1.369(6) . ?
C7 C8 1.466(8) . ?
C8 C12 1.369(8) . ?
C8 C9 1.395(9) . ?
C9 C10 1.379(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(9) . ?
C10 H10 0.9300 . ?
C11 N1 1.345(7) . ?
C11 H11 0.9300 . ?
C12 N1 1.338(6) . ?
C12 H12 0.9300 . ?
C13 N6 1.341(7) . ?
C13 C14 1.368(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.392(8) . ?
C16 C18 1.471(9) . ?
C17 N6 1.353(6) . ?
C17 H17 0.9300 . ?
C18 N10 1.304(6) . ?
C18 N11 1.369(6) . ?
C19 N9 1.308(6) . ?
C19 N11 1.359(6) . ?
C19 C20 1.481(9) . ?
C20 C21 1.375(9) . ?
C20 C24 1.386(8) . ?
C21 C22 1.374(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(9) . ?
C22 H22 0.9300 . ?
C23 N8 1.344(7) . ?
C23 H23 0.9300 . ?
C24 N8 1.339(6) . ?
C24 H24 0.9300 . ?
Cl1 O15 1.3993(18) . ?
Cl1 O16 1.4148(18) . ?
Cl1 O14 1.4206(18) . ?
Cl1 O13 1.4290(18) . ?
Cl2 O9 1.320(2) . ?
Cl2 O12 1.326(2) . ?
Cl2 O11 1.377(3) . ?
Cl2 O10 1.411(2) . ?
Cl3 O20 1.3673 . ?
Cl3 O19 1.3955 . ?
Cl3 O18 1.4096 . ?
Cl3 O17 1.4174 . ?
Tm1 O4 2.2606 . ?
Tm1 O1 2.2725 1_545 ?
Tm1 O2 2.2818 . ?
Tm1 O3 2.2846 1_565 ?
Tm1 O6 2.3472 . ?
Tm1 O7 2.3602 . ?
Tm1 O8 2.3679 . ?
Tm1 O5 2.3866 . ?
N1 O4 1.3313 . ?
N2 N3 1.3827 . ?
N4 N5 1.3962 . ?
N5 H5C 0.8988 . ?
N5 H5D 0.8968 . ?
N6 O2 1.3236 . ?
N7 O3 1.3354 . ?
N8 O1 1.3245 . ?
N9 N10 1.3719 . ?
N11 N12 1.4048 . ?
N12 H12A 0.9006 . ?
N12 H12B 0.8981 . ?
O1 Tm1 2.2725 1_565 ?
O3 Tm1 2.2846 1_545 ?
O5 H5B 0.8482 . ?
O5 H5A 0.8479 . ?
O6 H6B 0.8497 . ?
O6 H6A 0.8450 . ?
O7 H7A 0.8455 . ?
O7 H7B 0.8474 . ?
O8 H8B 0.8503 . ?
O8 H8A 0.8505 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8B N10 0.85 2.05 2.838 154.4 2_676
O6 H6B N3 0.85 1.94 2.765 163.8 2_767
O5 H5B O9 0.85 2.19 2.971 153.2 1_655
O5 H5B O11 0.85 2.65 3.253 128.7 1_655
O5 H5B Cl2 0.85 3.01 3.768(2) 149.9 1_655
O6 H6A O14 0.85 2.10 2.905 159.1 1_565
O5 H5A N2 0.85 1.96 2.802 171.0 2_767
O5 H5A N3 0.85 2.62 3.312 139.9 2_767
O7 H7A O12 0.85 2.16 2.963 158.7 .
O7 H7B N9 0.85 1.87 2.717 175.4 2_676
O7 H7B N10 0.85 2.55 3.315 150.7 2_676
N5 H5C O9 0.90 2.32 3.024 134.7 1_655
N5 H5D O16 0.90 2.33 2.891 120.6 .
N5 H5D O17 0.90 2.27 3.051 145.9 .
N12 H12A O12 0.90 2.62 3.200 123.0 1_565
N12 H12A O10 0.90 2.79 3.492 135.6 1_565
N12 H12B O17 0.90 2.18 2.933 141.0 1_565
N12 H12B O16 0.90 2.47 3.123 130.3 1_565
O8 H8A O18 0.85 2.04 2.879 168.2 1_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N7 C1 C2 C3 -0.2(10) . . . . ?
C1 C2 C3 C4 1.2(10) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C2 C3 C4 C6 172.3(6) . . . . ?
C3 C4 C5 N7 -0.8(9) . . . . ?
C6 C4 C5 N7 -173.8(5) . . . . ?
C5 C4 C6 N3 133.3(6) . . . . ?
C3 C4 C6 N3 -39.6(9) . . . . ?
C5 C4 C6 N4 -39.3(9) . . . . ?
C3 C4 C6 N4 147.7(6) . . . . ?
N2 C7 C8 C12 176.7(5) . . . . ?
N4 C7 C8 C12 -8.2(9) . . . . ?
N2 C7 C8 C9 -6.5(9) . . . . ?
N4 C7 C8 C9 168.7(5) . . . . ?
C12 C8 C9 C10 -0.9(10) . . . . ?
C7 C8 C9 C10 -177.9(6) . . . . ?
C8 C9 C10 C11 0.5(11) . . . . ?
C9 C10 C11 N1 -0.4(10) . . . . ?
C9 C8 C12 N1 1.3(9) . . . . ?
C7 C8 C12 N1 178.1(5) . . . . ?
N6 C13 C14 C15 -1.4(10) . . . . ?
C13 C14 C15 C16 1.3(11) . . . . ?
C14 C15 C16 C17 0.0(10) . . . . ?
C14 C15 C16 C18 173.3(6) . . . . ?
C15 C16 C17 N6 -1.3(9) . . . . ?
C18 C16 C17 N6 -174.8(5) . . . . ?
C15 C16 C18 N10 -38.7(9) . . . . ?
C17 C16 C18 N10 134.6(6) . . . . ?
C15 C16 C18 N11 146.8(6) . . . . ?
C17 C16 C18 N11 -39.9(9) . . . . ?
N9 C19 C20 C21 -7.4(9) . . . . ?
N11 C19 C20 C21 167.4(6) . . . . ?
N9 C19 C20 C24 174.8(5) . . . . ?
N11 C19 C20 C24 -10.3(10) . . . . ?
C24 C20 C21 C22 0.5(10) . . . . ?
C19 C20 C21 C22 -177.4(6) . . . . ?
C20 C21 C22 C23 -1.0(12) . . . . ?
C21 C22 C23 N8 1.3(11) . . . . ?
C21 C20 C24 N8 -0.2(9) . . . . ?
C19 C20 C24 N8 177.5(5) . . . . ?
C8 C12 N1 O4 178.9(4) . . . . ?
C8 C12 N1 C11 -1.2(8) . . . . ?
C10 C11 N1 O4 -179.3(5) . . . . ?
C10 C11 N1 C12 0.8(8) . . . . ?
N4 C7 N2 N3 -1.4(4) . . . . ?
C8 C7 N2 N3 174.5(4) . . . . ?
N4 C6 N3 N2 0.8(4) . . . . ?
C4 C6 N3 N2 -173.0(5) . . . . ?
C7 N2 N3 C6 0.4(4) . . . . ?
N3 C6 N4 C7 -1.7(5) . . . . ?
C4 C6 N4 C7 171.8(6) . . . . ?
N3 C6 N4 N5 173.40(17) . . . . ?
C4 C6 N4 N5 -13.1(7) . . . . ?
N2 C7 N4 C6 1.9(5) . . . . ?
C8 C7 N4 C6 -173.8(6) . . . . ?
N2 C7 N4 N5 -173.42(18) . . . . ?
C8 C7 N4 N5 10.9(7) . . . . ?
C14 C13 N6 O2 179.9(5) . . . . ?
C14 C13 N6 C17 0.1(8) . . . . ?
C16 C17 N6 O2 -178.6(4) . . . . ?
C16 C17 N6 C13 1.2(7) . . . . ?
C2 C1 N7 O3 -179.4(5) . . . . ?
C2 C1 N7 C5 -1.3(8) . . . . ?
C4 C5 N7 O3 179.9(4) . . . . ?
C4 C5 N7 C1 1.8(7) . . . . ?
C20 C24 N8 O1 179.1(4) . . . . ?
C20 C24 N8 C23 0.5(8) . . . . ?
C22 C23 N8 O1 -179.7(5) . . . . ?
C22 C23 N8 C24 -1.0(8) . . . . ?
N11 C19 N9 N10 -2.0(4) . . . . ?
C20 C19 N9 N10 173.8(4) . . . . ?
N11 C18 N10 N9 2.4(4) . . . . ?
C16 C18 N10 N9 -172.9(5) . . . . ?
C19 N9 N10 C18 -0.3(4) . . . . ?
N9 C19 N11 C18 3.4(5) . . . . ?
C20 C19 N11 C18 -172.0(6) . . . . ?
N9 C19 N11 N12 -171.54(19) . . . . ?
C20 C19 N11 N12 13.1(7) . . . . ?
N10 C18 N11 C19 -3.6(5) . . . . ?
C16 C18 N11 C19 171.6(6) . . . . ?
N10 C18 N11 N12 170.93(17) . . . . ?
C16 C18 N11 N12 -13.9(7) . . . . ?
C24 N8 O1 Tm1 -81.0(3) . . . 1_565 ?
C23 N8 O1 Tm1 97.7(3) . . . 1_565 ?
C13 N6 O2 Tm1 86.8(3) . . . . ?
C17 N6 O2 Tm1 -93.4(3) . . . . ?
O4 Tm1 O2 N6 -108.8 . . . . ?
O1 Tm1 O2 N6 -11.0 1_545 . . . ?
O3 Tm1 O2 N6 97.5 1_565 . . . ?
O6 Tm1 O2 N6 171.8 . . . . ?
O7 Tm1 O2 N6 -43.8 . . . . ?
O8 Tm1 O2 N6 31.5 . . . . ?
O5 Tm1 O2 N6 178.4 . . . . ?
C1 N7 O3 Tm1 89.6(3) . . . 1_545 ?
C5 N7 O3 Tm1 -88.6(3) . . . 1_545 ?
C12 N1 O4 Tm1 -86.2(3) . . . . ?
C11 N1 O4 Tm1 93.9(3) . . . . ?
O1 Tm1 O4 N1 95.0 1_545 . . . ?
O2 Tm1 O4 N1 -112.9 . . . . ?
O3 Tm1 O4 N1 1.2 1_565 . . . ?
O6 Tm1 O4 N1 -46.7 . . . . ?
O7 Tm1 O4 N1 172.1 . . . . ?
O8 Tm1 O4 N1 171.4 . . . . ?
O5 Tm1 O4 N1 28.5 . . . . ?
