#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/25/4302540.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_4302540
loop_
_publ_author_name
'Jean-Claude G. Bünzli'
'Nail M. Shavaleev'
'Rosario Scopelliti'
'Frédéric Gumy'
_publ_contact_author_address
;Ecole polytechnique fédérale de Lausanne
Institut des sciences et ingénierie chimiques
EPFL SB ISIC LCSL
BCH 1402 (Bât. BCH)
CH-1015 Lausanne
Switzerland
;
_publ_contact_author_email       jean-claude.bunzli@epfl.ch
_publ_contact_author_fax         '+41 21 693 98 25'
_publ_contact_author_name        'Jean-Claude Bünzli'
_publ_contact_author_phone       '+41 21 693 98 21'
_publ_section_title
;
Benzothiazole- and Benzoxazole-Substituted Pyridine-2-Carboxylates as
Efficient Sensitizers of Europium Luminescence
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6178
_journal_page_last               6191
_journal_paper_doi               10.1021/ic9005136
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C39 H22 Br3 N6 O11 Yb, C2 H3 N'
_chemical_formula_sum            'C41 H25 Br3 N7 O11 Yb'
_chemical_formula_weight         1204.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.266(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0118(19)
_cell_length_b                   14.560(2)
_cell_length_c                   18.4450(15)
_cell_measurement_reflns_used    99
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.606
_cell_measurement_theta_min      3.183
_cell_volume                     4007.5(8)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II 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  0.0879
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            87172
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    5.398
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10, G.M.Sheldrick, 2003'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2332
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.913
_refine_diff_density_min         -1.049
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         9191
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0504
_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)+(0.0120P)²+31.6424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                7071
_reflns_number_total             9191
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9005136_si_001_09.cif
_cod_data_source_block           '[Yb(LBr)3(H2O)2)]'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        4007.6(9)
_cod_database_code               4302540
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Yb1 Yb 0.249901(17) 0.390457(19) 0.486854(14) 0.01322(7) Uani 1 1 d D . .
Br1 Br 0.53002(5) 0.04781(5) 0.66844(4) 0.02960(17) Uani 1 1 d . . .
Br2 Br -0.05910(5) 0.14266(5) 0.24859(4) 0.03002(17) Uani 1 1 d . . .
Br3 Br -0.45047(5) 0.13629(5) 0.46242(4) 0.02818(17) Uani 1 1 d . . .
O1 O 0.1528(3) 0.5085(3) 0.4465(2) 0.0181(9) Uani 1 1 d . . .
O2 O 0.0408(3) 0.6065(3) 0.4597(2) 0.0183(9) Uani 1 1 d . . .
O3 O 0.2911(3) 0.3548(3) 0.7397(2) 0.0193(10) Uani 1 1 d . . .
O4 O 0.3465(3) 0.4940(3) 0.5503(2) 0.0171(9) Uani 1 1 d . . .
O5 O 0.4555(3) 0.5994(3) 0.5598(2) 0.0190(9) Uani 1 1 d . . .
O6 O 0.2334(3) 0.4163(3) 0.2324(2) 0.0196(10) Uani 1 1 d . . .
O7 O 0.2425(3) 0.2352(3) 0.4761(3) 0.0247(10) Uani 1 1 d . . .
O8 O 0.3502(3) 0.1442(3) 0.4436(2) 0.0241(10) Uani 1 1 d . . .
O9 O -0.0520(3) 0.1623(3) 0.4698(2) 0.0251(11) Uani 1 1 d . . .
O10 O 0.1052(3) 0.3261(3) 0.4891(2) 0.0192(9) Uani 1 1 d D . .
H10A H 0.058(2) 0.354(4) 0.502(4) 0.029 Uiso 1 1 d D . .
H10B H 0.097(3) 0.263(2) 0.488(4) 0.029 Uiso 1 1 d D . .
O11 O 0.3905(3) 0.3280(3) 0.4717(2) 0.0172(9) Uani 1 1 d D . .
H11A H 0.436(2) 0.356(3) 0.453(4) 0.026 Uiso 1 1 d D . .
H11B H 0.400(3) 0.264(2) 0.468(4) 0.026 Uiso 1 1 d D . .
N1 N 0.1734(3) 0.4673(4) 0.5843(3) 0.0164(11) Uani 1 1 d . . .
N2 N 0.2926(3) 0.3260(4) 0.6189(3) 0.0148(10) Uani 1 1 d . . .
N3 N 0.3309(3) 0.4957(4) 0.4077(3) 0.0139(10) Uani 1 1 d . . .
N4 N 0.2101(3) 0.3715(4) 0.3459(3) 0.0159(11) Uani 1 1 d . . .
N5 N 0.1150(4) 0.1131(4) 0.4429(3) 0.0222(12) Uani 1 1 d . . .
N6 N -0.1165(4) 0.0390(4) 0.4103(3) 0.0226(12) Uani 1 1 d . . .
C1 C 0.0998(4) 0.5514(5) 0.4840(3) 0.0172(13) Uani 1 1 d . . .
C2 C 0.1144(4) 0.5326(4) 0.5660(3) 0.0160(13) Uani 1 1 d . . .
C3 C 0.0687(4) 0.5797(5) 0.6167(3) 0.0215(14) Uani 1 1 d . . .
H3 H 0.0265 0.6264 0.6018 0.026 Uiso 1 1 calc R . .
C4 C 0.0873(5) 0.5556(5) 0.6900(4) 0.0286(16) Uani 1 1 d . . .
H4 H 0.0569 0.5854 0.7260 0.034 Uiso 1 1 calc R . .
C5 C 0.1498(5) 0.4887(5) 0.7098(3) 0.0245(15) Uani 1 1 d . . .
H5 H 0.1637 0.4720 0.7596 0.029 Uiso 1 1 calc R . .
C6 C 0.1917(4) 0.4464(4) 0.6559(3) 0.0168(13) Uani 1 1 d . . .
C7 C 0.2591(4) 0.3746(4) 0.6689(3) 0.0164(13) Uani 1 1 d . . .
C8 C 0.3523(4) 0.2852(4) 0.7328(3) 0.0166(13) Uani 1 1 d . . .
C9 C 0.4045(4) 0.2398(5) 0.7890(3) 0.0197(14) Uani 1 1 d . . .
H9 H 0.4037 0.2560 0.8389 0.024 Uiso 1 1 calc R . .
C10 C 0.4575(4) 0.1698(5) 0.7672(3) 0.0197(14) Uani 1 1 d . . .
H10 H 0.4947 0.1361 0.8027 0.024 Uiso 1 1 calc R . .
C11 C 0.4568(4) 0.1478(5) 0.6924(3) 0.0214(14) Uani 1 1 d . . .
C12 C 0.4063(4) 0.1950(5) 0.6371(3) 0.0188(13) Uani 1 1 d . . .
H12 H 0.4080 0.1799 0.5872 0.023 Uiso 1 1 calc R . .
C13 C 0.3531(4) 0.2656(4) 0.6589(3) 0.0141(12) Uani 1 1 d . . .
C14 C 0.3994(4) 0.5497(4) 0.5238(3) 0.0155(12) Uani 1 1 d . . .
C15 C 0.3909(4) 0.5543(4) 0.4403(3) 0.0135(12) Uani 1 1 d . . .
C16 C 0.4390(4) 0.6151(5) 0.4014(3) 0.0192(13) Uani 1 1 d . . .
H16 H 0.4802 0.6571 0.4261 0.023 Uiso 1 1 calc R . .
C17 C 0.4256(4) 0.6133(5) 0.3257(3) 0.0212(13) Uani 1 1 d . . .
H17 H 0.4576 0.6543 0.2980 0.025 Uiso 1 1 calc R . .
C18 C 0.3650(4) 0.5509(5) 0.2908(3) 0.0195(14) Uani 1 1 d . . .
H18 H 0.3552 0.5477 0.2391 0.023 Uiso 1 1 calc R . .
C19 C 0.3195(4) 0.4936(4) 0.3342(3) 0.0156(13) Uani 1 1 d . . .
C20 C 0.2535(4) 0.4254(4) 0.3060(3) 0.0170(13) Uani 1 1 d . . .
C21 C 0.1676(4) 0.3497(4) 0.2255(3) 0.0170(13) Uani 1 1 d . . .
C22 C 0.1233(4) 0.3138(5) 0.1614(3) 0.0212(14) Uani 1 1 d . . .
H22 H 0.1379 0.3315 0.1146 0.025 Uiso 1 1 calc R . .
C23 C 0.0563(4) 0.2504(5) 0.1708(3) 0.0210(14) Uani 1 1 d . . .
H23 H 0.0229 0.2241 0.1292 0.025 Uiso 1 1 calc R . .
C24 C 0.0372(4) 0.2248(5) 0.2405(3) 0.0194(13) Uani 1 1 d . . .
C25 C 0.0843(4) 0.2586(4) 0.3045(3) 0.0184(13) Uani 1 1 d . . .
H25 H 0.0714 0.2392 0.3514 0.022 Uiso 1 1 calc R . .
C26 C 0.1512(4) 0.3222(4) 0.2952(3) 0.0173(13) Uani 1 1 d . . .
C27 C 0.2710(4) 0.1611(4) 0.4522(3) 0.0167(13) Uani 1 1 d . . .
C28 C 0.1998(4) 0.0889(4) 0.4326(3) 0.0175(13) Uani 1 1 d . . .
C29 C 0.2209(4) 0.0051(4) 0.4038(3) 0.0187(13) Uani 1 1 d . . .
H29 H 0.2812 -0.0100 0.3980 0.022 Uiso 1 1 calc R . .
C30 C 0.1513(5) -0.0571(5) 0.3833(3) 0.0230(14) Uani 1 1 d . . .
H30 H 0.1639 -0.1156 0.3640 0.028 Uiso 1 1 calc R . .
C31 C 0.0639(5) -0.0320(5) 0.3916(3) 0.0247(15) Uani 1 1 d . . .
H31 H 0.0153 -0.0720 0.3769 0.030 Uiso 1 1 calc R . .
C32 C 0.0491(4) 0.0536(5) 0.4221(3) 0.0199(14) Uani 1 1 d . . .
C33 C -0.0433(5) 0.0828(5) 0.4330(3) 0.0217(14) Uani 1 1 d . . .
C34 C -0.1839(4) 0.0952(5) 0.4346(3) 0.0237(15) Uani 1 1 d . . .
C35 C -0.2773(4) 0.0817(5) 0.4303(3) 0.0213(14) Uani 1 1 d . . .
H35 H -0.3062 0.0314 0.4049 0.026 Uiso 1 1 calc R . .
C36 C -0.3242(5) 0.1469(5) 0.4657(4) 0.0235(14) Uani 1 1 d . . .
C37 C -0.2820(5) 0.2195(5) 0.5066(4) 0.0272(16) Uani 1 1 d . . .
H37 H -0.3169 0.2606 0.5318 0.033 Uiso 1 1 calc R . .
C38 C -0.1902(5) 0.2317(5) 0.5103(4) 0.0287(16) Uani 1 1 d . . .
H38 H -0.1608 0.2806 0.5373 0.034 Uiso 1 1 calc R . .
C39 C -0.1434(5) 0.1690(5) 0.4729(4) 0.0248(15) Uani 1 1 d . . .
C40 C 0.3035(6) 0.6792(7) 0.6686(4) 0.043(2) Uani 1 1 d . . .
H40A H 0.2501 0.6944 0.6354 0.064 Uiso 1 1 calc R . .
H40B H 0.3181 0.6141 0.6635 0.064 Uiso 1 1 calc R . .
H40C H 0.3540 0.7169 0.6566 0.064 Uiso 1 1 calc R . .
C41 C 0.2863(6) 0.6976(6) 0.7435(4) 0.0368(19) Uani 1 1 d . . .
N7 N 0.2727(6) 0.7143(6) 0.8020(4) 0.059(2) 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 '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
O7 Yb1 O4 135.51(16) . . ?
O7 Yb1 O1 133.29(16) . . ?
O4 Yb1 O1 90.94(15) . . ?
O7 Yb1 O11 68.86(16) . . ?
O4 Yb1 O11 77.92(15) . . ?
O1 Yb1 O11 142.29(15) . . ?
O7 Yb1 O10 64.62(16) . . ?
O4 Yb1 O10 140.55(15) . . ?
O1 Yb1 O10 75.78(16) . . ?
O11 Yb1 O10 133.44(15) . . ?
O7 Yb1 N1 119.09(17) . . ?
O4 Yb1 N1 69.96(16) . . ?
O1 Yb1 N1 65.01(15) . . ?
O11 Yb1 N1 138.59(15) . . ?
O10 Yb1 N1 70.77(16) . . ?
O7 Yb1 N3 125.26(16) . . ?
O4 Yb1 N3 65.30(15) . . ?
O1 Yb1 N3 71.93(15) . . ?
O11 Yb1 N3 70.68(15) . . ?
O10 Yb1 N3 138.77(15) . . ?
N1 Yb1 N3 115.66(17) . . ?
O7 Yb1 N4 78.76(16) . . ?
O4 Yb1 N4 129.20(15) . . ?
O1 Yb1 N4 72.10(15) . . ?
O11 Yb1 N4 87.23(15) . . ?
O10 Yb1 N4 82.29(15) . . ?
N1 Yb1 N4 133.47(16) . . ?
N3 Yb1 N4 63.94(16) . . ?
O7 Yb1 N2 74.31(16) . . ?
O4 Yb1 N2 71.82(15) . . ?
O1 Yb1 N2 130.02(15) . . ?
O11 Yb1 N2 80.79(15) . . ?
O10 Yb1 N2 88.48(15) . . ?
N1 Yb1 N2 65.01(16) . . ?
N3 Yb1 N2 132.16(15) . . ?
N4 Yb1 N2 152.95(17) . . ?
C1 O1 Yb1 126.6(4) . . ?
C7 O3 C8 103.5(5) . . ?
C14 O4 Yb1 127.2(4) . . ?
C20 O6 C21 103.8(5) . . ?
C27 O7 Yb1 150.3(4) . . ?
C33 O9 C39 103.4(5) . . ?
Yb1 O10 H10A 127(3) . . ?
Yb1 O10 H10B 121(3) . . ?
H10A O10 H10B 111(5) . . ?
Yb1 O11 H11A 127(3) . . ?
Yb1 O11 H11B 122(3) . . ?
H11A O11 H11B 107(5) . . ?
C2 N1 C6 118.2(5) . . ?
C2 N1 Yb1 119.2(4) . . ?
C6 N1 Yb1 122.7(4) . . ?
C7 N2 C13 104.1(5) . . ?
C7 N2 Yb1 112.9(4) . . ?
C13 N2 Yb1 141.8(4) . . ?
C15 N3 C19 118.2(5) . . ?
C15 N3 Yb1 118.2(4) . . ?
C19 N3 Yb1 123.6(4) . . ?
C20 N4 C26 104.3(5) . . ?
C20 N4 Yb1 115.2(4) . . ?
C26 N4 Yb1 140.4(4) . . ?
C32 N5 C28 117.9(6) . . ?
C33 N6 C34 102.9(6) . . ?
O2 C1 O1 125.7(6) . . ?
O2 C1 C2 119.5(5) . . ?
O1 C1 C2 114.7(5) . . ?
N1 C2 C3 123.1(6) . . ?
N1 C2 C1 113.7(5) . . ?
C3 C2 C1 123.1(6) . . ?
C4 C3 C2 117.7(6) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C5 C4 C3 119.7(6) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 118.4(6) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 122.9(6) . . ?
N1 C6 C7 112.7(5) . . ?
C5 C6 C7 124.4(6) . . ?
N2 C7 O3 115.9(5) . . ?
N2 C7 C6 125.9(5) . . ?
O3 C7 C6 118.2(5) . . ?
O3 C8 C13 108.5(5) . . ?
O3 C8 C9 127.1(6) . . ?
C13 C8 C9 124.4(6) . . ?
C10 C9 C8 115.3(6) . . ?
C10 C9 H9 122.3 . . ?
C8 C9 H9 122.3 . . ?
C9 C10 C11 120.6(6) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 123.4(6) . . ?
C12 C11 Br1 119.5(5) . . ?
C10 C11 Br1 117.2(5) . . ?
C11 C12 C13 116.1(6) . . ?
C11 C12 H12 121.9 . . ?
C13 C12 H12 121.9 . . ?
C12 C13 C8 120.1(6) . . ?
C12 C13 N2 131.8(5) . . ?
C8 C13 N2 108.1(5) . . ?
O5 C14 O4 125.6(5) . . ?
O5 C14 C15 119.2(5) . . ?
O4 C14 C15 115.3(5) . . ?
N3 C15 C16 122.5(5) . . ?
N3 C15 C14 113.8(5) . . ?
C16 C15 C14 123.7(5) . . ?
C17 C16 C15 118.7(6) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 119.5(6) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 117.7(5) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
N3 C19 C18 123.4(6) . . ?
N3 C19 C20 112.3(5) . . ?
C18 C19 C20 124.3(5) . . ?
N4 C20 O6 115.8(5) . . ?
N4 C20 C19 125.0(5) . . ?
O6 C20 C19 119.2(5) . . ?
O6 C21 C22 127.9(6) . . ?
O6 C21 C26 108.2(5) . . ?
C22 C21 C26 123.9(6) . . ?
C23 C22 C21 115.4(6) . . ?
C23 C22 H22 122.3 . . ?
C21 C22 H22 122.3 . . ?
C22 C23 C24 121.0(6) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 123.2(6) . . ?
C25 C24 Br2 118.4(5) . . ?
C23 C24 Br2 118.3(5) . . ?
C26 C25 C24 115.8(6) . . ?
C26 C25 H25 122.1 . . ?
C24 C25 H25 122.1 . . ?
C25 C26 C21 120.5(6) . . ?
C25 C26 N4 131.7(6) . . ?
C21 C26 N4 107.7(6) . . ?
O8 C27 O7 125.6(6) . . ?
O8 C27 C28 119.5(6) . . ?
O7 C27 C28 114.9(5) . . ?
N5 C28 C29 122.8(6) . . ?
N5 C28 C27 115.8(6) . . ?
C29 C28 C27 121.3(6) . . ?
C28 C29 C30 118.6(6) . . ?
C28 C29 H29 120.7 . . ?
C30 C29 H29 120.7 . . ?
C31 C30 C29 119.0(6) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C30 C31 C32 118.3(6) . . ?
C30 C31 H31 120.8 . . ?
C32 C31 H31 120.8 . . ?
N5 C32 C31 123.3(6) . . ?
N5 C32 C33 116.6(6) . . ?
C31 C32 C33 120.1(6) . . ?
N6 C33 O9 117.1(6) . . ?
N6 C33 C32 125.9(6) . . ?
O9 C33 C32 117.0(6) . . ?
C39 C34 C35 120.9(6) . . ?
C39 C34 N6 108.7(6) . . ?
C35 C34 N6 130.1(6) . . ?
C36 C35 C34 115.6(6) . . ?
C36 C35 H35 122.2 . . ?
C34 C35 H35 122.2 . . ?
C35 C36 C37 122.9(6) . . ?
C35 C36 Br3 119.1(5) . . ?
C37 C36 Br3 118.0(5) . . ?
C38 C37 C36 120.7(7) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C39 C38 C37 116.7(7) . . ?
C39 C38 H38 121.7 . . ?
C37 C38 H38 121.7 . . ?
C38 C39 O9 128.9(7) . . ?
C38 C39 C34 123.1(7) . . ?
O9 C39 C34 107.8(6) . . ?
C41 C40 H40A 109.5 . . ?
C41 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C41 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N7 C41 C40 178.3(10) . . ?
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
Yb1 O7 2.270(5) . ?
Yb1 O4 2.318(4) . ?
Yb1 O1 2.323(4) . ?
Yb1 O11 2.342(4) . ?
Yb1 O10 2.371(4) . ?
Yb1 N1 2.500(5) . ?
Yb1 N3 2.520(5) . ?
Yb1 N4 2.617(5) . ?
Yb1 N2 2.623(5) . ?
Br1 C11 1.905(7) . ?
Br2 C24 1.895(7) . ?
Br3 C36 1.896(7) . ?
O1 C1 1.274(7) . ?
O2 C1 1.242(7) . ?
O3 C7 1.372(7) . ?
O3 C8 1.383(7) . ?
O4 C14 1.270(7) . ?
O5 C14 1.246(7) . ?
O6 C20 1.364(7) . ?
O6 C21 1.379(8) . ?
O7 C27 1.259(8) . ?
O8 C27 1.241(7) . ?
O9 C33 1.355(8) . ?
O9 C39 1.383(8) . ?
O10 H10A 0.87(3) . ?
O10 H10B 0.93(3) . ?
O11 H11A 0.90(3) . ?
O11 H11B 0.95(3) . ?
N1 C2 1.318(8) . ?
N1 C6 1.354(8) . ?
N2 C7 1.306(8) . ?
N2 C13 1.414(8) . ?
N3 C15 1.334(7) . ?
N3 C19 1.348(7) . ?
N4 C20 1.298(8) . ?
N4 C26 1.411(8) . ?
N5 C32 1.338(8) . ?
N5 C28 1.355(8) . ?
N6 C33 1.301(8) . ?
N6 C34 1.412(8) . ?
C1 C2 1.528(8) . ?
C2 C3 1.398(9) . ?
C3 C4 1.394(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.456(9) . ?
C8 C13 1.394(8) . ?
C8 C9 1.396(8) . ?
C9 C10 1.379(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.415(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(9) . ?
C12 C13 1.388(9) . ?
C12 H12 0.9500 . ?
C14 C15 1.534(8) . ?
C15 C16 1.390(9) . ?
C16 C17 1.388(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.459(9) . ?
C21 C22 1.392(8) . ?
C21 C26 1.395(8) . ?
C22 C23 1.390(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.396(8) . ?
C25 C26 1.392(9) . ?
C25 H25 0.9500 . ?
C27 C28 1.515(9) . ?
C28 C29 1.380(9) . ?
C29 C30 1.404(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.386(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.395(9) . ?
C31 H31 0.9500 . ?
C32 C33 1.485(9) . ?
C34 C39 1.389(10) . ?
C34 C35 1.409(9) . ?
C35 C36 1.387(9) . ?
C35 H35 0.9500 . ?
C36 C37 1.408(10) . ?
C37 C38 1.383(10) . ?
C37 H37 0.9500 . ?
C38 C39 1.381(10) . ?
C38 H38 0.9500 . ?
C40 C41 1.457(11) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 N7 1.147(10) . ?
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
O10 H10A O2 0.87(3) 1.80(3) 2.666(6) 169(6) 3_566
O10 H10B N5 0.93(3) 2.36(4) 3.224(8) 154(5) .
O10 H10B O9 0.93(3) 2.66(3) 3.346(7) 131(4) .
O11 H11A O5 0.90(3) 1.79(3) 2.664(6) 162(6) 3_666
O11 H11B O8 0.95(3) 1.93(4) 2.779(7) 148(4) .
O11 H11B Br3 0.95(3) 2.93(3) 3.689(5) 138(4) 1_655
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
O7 Yb1 O1 C1 99.7(5) . . . . ?
O4 Yb1 O1 C1 -74.9(5) . . . . ?
O11 Yb1 O1 C1 -146.2(5) . . . . ?
O10 Yb1 O1 C1 67.5(5) . . . . ?
N1 Yb1 O1 C1 -7.6(5) . . . . ?
N3 Yb1 O1 C1 -138.5(5) . . . . ?
N4 Yb1 O1 C1 153.8(5) . . . . ?
N2 Yb1 O1 C1 -8.1(6) . . . . ?
O7 Yb1 O4 C14 110.8(5) . . . . ?
O1 Yb1 O4 C14 -74.8(5) . . . . ?
O11 Yb1 O4 C14 68.9(5) . . . . ?
O10 Yb1 O4 C14 -143.3(5) . . . . ?
N1 Yb1 O4 C14 -137.7(5) . . . . ?
N3 Yb1 O4 C14 -5.2(5) . . . . ?
N4 Yb1 O4 C14 -7.3(6) . . . . ?
N2 Yb1 O4 C14 153.0(5) . . . . ?
O4 Yb1 O7 C27 -72.7(9) . . . . ?
O1 Yb1 O7 C27 115.0(8) . . . . ?
O11 Yb1 O7 C27 -28.2(8) . . . . ?
O10 Yb1 O7 C27 149.9(9) . . . . ?
N1 Yb1 O7 C27 -163.0(8) . . . . ?
N3 Yb1 O7 C27 16.7(9) . . . . ?
N4 Yb1 O7 C27 63.2(9) . . . . ?
N2 Yb1 O7 C27 -114.2(9) . . . . ?
O7 Yb1 N1 C2 -124.6(5) . . . . ?
O4 Yb1 N1 C2 103.6(5) . . . . ?
O1 Yb1 N1 C2 2.7(4) . . . . ?
O11 Yb1 N1 C2 145.0(4) . . . . ?
O10 Yb1 N1 C2 -80.1(5) . . . . ?
N3 Yb1 N1 C2 55.6(5) . . . . ?
N4 Yb1 N1 C2 -21.9(6) . . . . ?
N2 Yb1 N1 C2 -177.7(5) . . . . ?
O7 Yb1 N1 C6 57.2(5) . . . . ?
O4 Yb1 N1 C6 -74.6(5) . . . . ?
O1 Yb1 N1 C6 -175.5(5) . . . . ?
O11 Yb1 N1 C6 -33.2(6) . . . . ?
O10 Yb1 N1 C6 101.6(5) . . . . ?
N3 Yb1 N1 C6 -122.6(5) . . . . ?
N4 Yb1 N1 C6 159.9(4) . . . . ?
N2 Yb1 N1 C6 4.1(4) . . . . ?
O7 Yb1 N2 C7 -140.7(4) . . . . ?
O4 Yb1 N2 C7 68.6(4) . . . . ?
O1 Yb1 N2 C7 -6.8(5) . . . . ?
O11 Yb1 N2 C7 148.8(4) . . . . ?
O10 Yb1 N2 C7 -76.7(4) . . . . ?
N1 Yb1 N2 C7 -7.3(4) . . . . ?
N3 Yb1 N2 C7 95.6(4) . . . . ?
N4 Yb1 N2 C7 -146.4(4) . . . . ?
O7 Yb1 N2 C13 55.3(6) . . . . ?
O4 Yb1 N2 C13 -95.4(6) . . . . ?
O1 Yb1 N2 C13 -170.8(6) . . . . ?
O11 Yb1 N2 C13 -15.2(6) . . . . ?
O10 Yb1 N2 C13 119.3(6) . . . . ?
N1 Yb1 N2 C13 -171.2(7) . . . . ?
N3 Yb1 N2 C13 -68.4(7) . . . . ?
N4 Yb1 N2 C13 49.6(8) . . . . ?
O7 Yb1 N3 C15 -126.4(4) . . . . ?
O4 Yb1 N3 C15 3.1(4) . . . . ?
O1 Yb1 N3 C15 102.8(4) . . . . ?
O11 Yb1 N3 C15 -82.1(4) . . . . ?
O10 Yb1 N3 C15 143.0(4) . . . . ?
N1 Yb1 N3 C15 53.4(5) . . . . ?
N4 Yb1 N3 C15 -178.7(5) . . . . ?
N2 Yb1 N3 C15 -25.3(5) . . . . ?
O7 Yb1 N3 C19 50.9(5) . . . . ?
O4 Yb1 N3 C19 -179.6(5) . . . . ?
O1 Yb1 N3 C19 -79.8(5) . . . . ?
O11 Yb1 N3 C19 95.2(5) . . . . ?
O10 Yb1 N3 C19 -39.7(6) . . . . ?
N1 Yb1 N3 C19 -129.3(4) . . . . ?
N4 Yb1 N3 C19 -1.4(4) . . . . ?
N2 Yb1 N3 C19 152.1(4) . . . . ?
O7 Yb1 N4 C20 -137.8(5) . . . . ?
O4 Yb1 N4 C20 3.1(5) . . . . ?
O1 Yb1 N4 C20 79.2(4) . . . . ?
O11 Yb1 N4 C20 -68.8(4) . . . . ?
O10 Yb1 N4 C20 156.7(5) . . . . ?
N1 Yb1 N4 C20 102.6(5) . . . . ?
N3 Yb1 N4 C20 1.0(4) . . . . ?
N2 Yb1 N4 C20 -132.3(5) . . . . ?
O7 Yb1 N4 C26 45.8(6) . . . . ?
O4 Yb1 N4 C26 -173.2(6) . . . . ?
O1 Yb1 N4 C26 -97.2(6) . . . . ?
O11 Yb1 N4 C26 114.8(6) . . . . ?
O10 Yb1 N4 C26 -19.7(6) . . . . ?
N1 Yb1 N4 C26 -73.8(7) . . . . ?
N3 Yb1 N4 C26 -175.4(7) . . . . ?
N2 Yb1 N4 C26 51.4(8) . . . . ?
Yb1 O1 C1 O2 -170.8(5) . . . . ?
Yb1 O1 C1 C2 10.8(8) . . . . ?
C6 N1 C2 C3 -1.3(9) . . . . ?
Yb1 N1 C2 C3 -179.7(5) . . . . ?
C6 N1 C2 C1 179.3(5) . . . . ?
Yb1 N1 C2 C1 0.9(7) . . . . ?
O2 C1 C2 N1 174.6(6) . . . . ?
O1 C1 C2 N1 -6.9(8) . . . . ?
O2 C1 C2 C3 -4.8(10) . . . . ?
O1 C1 C2 C3 173.7(6) . . . . ?
N1 C2 C3 C4 0.0(10) . . . . ?
C1 C2 C3 C4 179.4(6) . . . . ?
C2 C3 C4 C5 1.0(11) . . . . ?
C3 C4 C5 C6 -0.7(11) . . . . ?
C2 N1 C6 C5 1.7(9) . . . . ?
Yb1 N1 C6 C5 179.9(5) . . . . ?
C2 N1 C6 C7 -178.9(5) . . . . ?
Yb1 N1 C6 C7 -0.6(7) . . . . ?
C4 C5 C6 N1 -0.6(11) . . . . ?
C4 C5 C6 C7 179.9(7) . . . . ?
C13 N2 C7 O3 0.8(7) . . . . ?
Yb1 N2 C7 O3 -169.1(4) . . . . ?
C13 N2 C7 C6 -178.9(6) . . . . ?
Yb1 N2 C7 C6 11.2(8) . . . . ?
C8 O3 C7 N2 0.1(7) . . . . ?
C8 O3 C7 C6 179.8(5) . . . . ?
N1 C6 C7 N2 -7.8(9) . . . . ?
C5 C6 C7 N2 171.7(7) . . . . ?
N1 C6 C7 O3 172.5(5) . . . . ?
C5 C6 C7 O3 -8.0(10) . . . . ?
C7 O3 C8 C13 -1.0(6) . . . . ?
C7 O3 C8 C9 179.9(6) . . . . ?
O3 C8 C9 C10 177.2(6) . . . . ?
C13 C8 C9 C10 -1.8(10) . . . . ?
C8 C9 C10 C11 0.0(9) . . . . ?
C9 C10 C11 C12 1.7(10) . . . . ?
C9 C10 C11 Br1 -178.4(5) . . . . ?
C10 C11 C12 C13 -1.5(10) . . . . ?
Br1 C11 C12 C13 178.5(5) . . . . ?
C11 C12 C13 C8 -0.3(9) . . . . ?
C11 C12 C13 N2 -178.6(6) . . . . ?
O3 C8 C13 C12 -177.2(6) . . . . ?
C9 C8 C13 C12 2.1(10) . . . . ?
O3 C8 C13 N2 1.5(7) . . . . ?
C9 C8 C13 N2 -179.3(6) . . . . ?
C7 N2 C13 C12 177.1(7) . . . . ?
Yb1 N2 C13 C12 -18.1(11) . . . . ?
C7 N2 C13 C8 -1.3(7) . . . . ?
Yb1 N2 C13 C8 163.5(5) . . . . ?
Yb1 O4 C14 O5 -174.1(4) . . . . ?
Yb1 O4 C14 C15 6.3(7) . . . . ?
C19 N3 C15 C16 2.5(9) . . . . ?
Yb1 N3 C15 C16 -180.0(5) . . . . ?
C19 N3 C15 C14 -179.0(5) . . . . ?
Yb1 N3 C15 C14 -1.5(6) . . . . ?
O5 C14 C15 N3 177.8(5) . . . . ?
O4 C14 C15 N3 -2.6(8) . . . . ?
O5 C14 C15 C16 -3.7(9) . . . . ?
O4 C14 C15 C16 175.9(6) . . . . ?
N3 C15 C16 C17 -1.6(10) . . . . ?
C14 C15 C16 C17 -179.9(6) . . . . ?
C15 C16 C17 C18 -0.2(10) . . . . ?
C16 C17 C18 C19 0.8(10) . . . . ?
C15 N3 C19 C18 -1.9(9) . . . . ?
Yb1 N3 C19 C18 -179.2(5) . . . . ?
C15 N3 C19 C20 178.9(5) . . . . ?
Yb1 N3 C19 C20 1.5(7) . . . . ?
C17 C18 C19 N3 0.2(10) . . . . ?
C17 C18 C19 C20 179.4(6) . . . . ?
C26 N4 C20 O6 -2.4(7) . . . . ?
Yb1 N4 C20 O6 -180.0(4) . . . . ?
C26 N4 C20 C19 176.9(6) . . . . ?
Yb1 N4 C20 C19 -0.7(8) . . . . ?
C21 O6 C20 N4 1.4(7) . . . . ?
C21 O6 C20 C19 -177.8(5) . . . . ?
N3 C19 C20 N4 -0.4(9) . . . . ?
C18 C19 C20 N4 -179.7(6) . . . . ?
N3 C19 C20 O6 178.8(5) . . . . ?
C18 C19 C20 O6 -0.5(10) . . . . ?
C20 O6 C21 C22 -179.8(6) . . . . ?
C20 O6 C21 C26 0.2(7) . . . . ?
O6 C21 C22 C23 -176.7(6) . . . . ?
C26 C21 C22 C23 3.3(10) . . . . ?
C21 C22 C23 C24 -0.9(10) . . . . ?
C22 C23 C24 C25 -1.5(10) . . . . ?
C22 C23 C24 Br2 176.9(5) . . . . ?
C23 C24 C25 C26 1.6(10) . . . . ?
Br2 C24 C25 C26 -176.8(5) . . . . ?
C24 C25 C26 C21 0.7(9) . . . . ?
C24 C25 C26 N4 178.5(6) . . . . ?
O6 C21 C26 C25 176.7(6) . . . . ?
C22 C21 C26 C25 -3.3(10) . . . . ?
O6 C21 C26 N4 -1.5(7) . . . . ?
C22 C21 C26 N4 178.4(6) . . . . ?
C20 N4 C26 C25 -175.7(7) . . . . ?
Yb1 N4 C26 C25 0.9(11) . . . . ?
C20 N4 C26 C21 2.3(7) . . . . ?
Yb1 N4 C26 C21 178.9(5) . . . . ?
Yb1 O7 C27 O8 33.5(12) . . . . ?
Yb1 O7 C27 C28 -146.2(7) . . . . ?
C32 N5 C28 C29 -2.0(9) . . . . ?
C32 N5 C28 C27 175.9(5) . . . . ?
O8 C27 C28 N5 -179.4(5) . . . . ?
O7 C27 C28 N5 0.3(8) . . . . ?
O8 C27 C28 C29 -1.5(9) . . . . ?
O7 C27 C28 C29 178.2(5) . . . . ?
N5 C28 C29 C30 1.0(9) . . . . ?
C27 C28 C29 C30 -176.8(5) . . . . ?
C28 C29 C30 C31 1.0(9) . . . . ?
C29 C30 C31 C32 -1.8(9) . . . . ?
C28 N5 C32 C31 1.0(9) . . . . ?
C28 N5 C32 C33 -179.0(5) . . . . ?
C30 C31 C32 N5 0.8(10) . . . . ?
C30 C31 C32 C33 -179.2(6) . . . . ?
C34 N6 C33 O9 0.0(7) . . . . ?
C34 N6 C33 C32 179.9(6) . . . . ?
C39 O9 C33 N6 1.8(7) . . . . ?
C39 O9 C33 C32 -178.1(5) . . . . ?
N5 C32 C33 N6 173.3(6) . . . . ?
C31 C32 C33 N6 -6.8(10) . . . . ?
N5 C32 C33 O9 -6.8(8) . . . . ?
C31 C32 C33 O9 173.2(6) . . . . ?
C33 N6 C34 C39 -1.8(7) . . . . ?
C33 N6 C34 C35 -176.0(7) . . . . ?
C39 C34 C35 C36 0.7(9) . . . . ?
N6 C34 C35 C36 174.3(6) . . . . ?
C34 C35 C36 C37 -3.1(10) . . . . ?
C34 C35 C36 Br3 179.2(5) . . . . ?
C35 C36 C37 C38 3.2(11) . . . . ?
Br3 C36 C37 C38 -179.1(5) . . . . ?
C36 C37 C38 C39 -0.6(10) . . . . ?
C37 C38 C39 O9 -176.9(6) . . . . ?
C37 C38 C39 C34 -1.8(10) . . . . ?
C33 O9 C39 C38 172.9(7) . . . . ?
C33 O9 C39 C34 -2.8(7) . . . . ?
C35 C34 C39 C38 1.8(10) . . . . ?
N6 C34 C39 C38 -173.0(6) . . . . ?
C35 C34 C39 O9 177.8(6) . . . . ?
N6 C34 C39 O9 3.0(7) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336773
