#------------------------------------------------------------------------------
#$Date: 2015-12-09 13:11:40 +0200 (Wed, 09 Dec 2015) $
#$Revision: 170937 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/91/1529195.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_1529195
loop_
_publ_author_name
'Shibata, Yu'
'Nagae, Haruki'
'Sumiya, Shiki'
'Rochat, Raphaël'
'Tsurugi, Hayato'
'Mashima, Kazushi'
_publ_section_title
;
 2,2′-Bipyridyl formation from 2-arylpyridines through bimetallic
 diyttrium intermediate
;
_journal_issue                   10
_journal_name_full               'Chem. Sci.'
_journal_page_first              5394
_journal_paper_doi               10.1039/C5SC01599E
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C98 H128 N6 O2 Y2'
_chemical_formula_sum            'C98 H128 N6 O2 Y2'
_chemical_formula_weight         1599.94
_chemical_melting_point          118(2)
_chemical_name_systematic
; 
 ? 
;
_chemical_properties_physical
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-10 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.350(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.324(6)
_cell_length_b                   16.849(7)
_cell_length_c                   19.590(8)
_cell_measurement_reflns_used    7506
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.07
_cell_volume                     4261(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_sigmaI/netI    0.0764
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40751
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.408
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1704
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.446
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         9727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0661
_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)+(0.0580P)²+7.0358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1626
_reflns_number_gt                6791
_reflns_number_total             9727
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc01599e2.cif
_cod_data_source_block           4b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '116-120' was changed to '118(2)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1529194--1529200.cif.
;
_cod_database_code               1529195
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Y1 Y 0.47377(3) 0.04499(2) 0.363507(18) 0.02234(11) Uani 1 1 d .
O1 O 0.3657(2) -0.06441(16) 0.32991(15) 0.0327(6) Uani 1 1 d .
N1 N 0.4870(2) 0.10634(17) 0.47229(16) 0.0233(7) Uani 1 1 d .
N2 N 0.3924(2) 0.11607(18) 0.27192(16) 0.0247(7) Uani 1 1 d .
N3 N 0.6038(2) 0.07411(18) 0.31734(15) 0.0227(7) Uani 1 1 d .
C1 C 0.4684(3) 0.0331(2) 0.50283(19) 0.0237(8) Uani 1 1 d .
C2 C 0.6168(3) -0.0296(2) 0.46225(19) 0.0255(8) Uani 1 1 d .
H2 H 0.6750 0.0056 0.4868 0.031 Uiso 1 1 calc R
C3 C 0.6492(3) -0.0994(2) 0.4394(2) 0.0290(9) Uani 1 1 d .
H3 H 0.7012 -0.0986 0.4138 0.035 Uiso 1 1 calc R
C4 C 0.3937(3) 0.1731(2) 0.54676(19) 0.0261(8) Uani 1 1 d .
H4 H 0.3816 0.2203 0.5700 0.031 Uiso 1 1 calc R
C5 C 0.4539(3) 0.1738(2) 0.49809(19) 0.0245(8) Uani 1 1 d .
C6 C 0.4833(3) 0.2501(2) 0.46964(19) 0.0250(8) Uani 1 1 d .
C7 C 0.4279(3) 0.3205(2) 0.4717(2) 0.0292(9) Uani 1 1 d .
H7 H 0.3705 0.3201 0.4924 0.035 Uiso 1 1 calc R
C8 C 0.4555(3) 0.3910(2) 0.4441(2) 0.0305(9) Uani 1 1 d .
H8 H 0.4166 0.4378 0.4463 0.037 Uiso 1 1 calc R
C9 C 0.5381(3) 0.3944(2) 0.4137(2) 0.0304(9) Uani 1 1 d .
C10 C 0.5942(3) 0.3247(2) 0.4120(2) 0.0296(9) Uani 1 1 d .
H10 H 0.6519 0.3258 0.3916 0.035 Uiso 1 1 calc R
C11 C 0.5678(3) 0.2538(2) 0.4394(2) 0.0277(8) Uani 1 1 d .
H11 H 0.6076 0.2074 0.4375 0.033 Uiso 1 1 calc R
C12 C 0.5662(4) 0.4708(2) 0.3832(2) 0.0391(10) Uani 1 1 d .
H12A H 0.5471 0.5157 0.4091 0.047 Uiso 1 1 calc R
H12B H 0.5289 0.4744 0.3334 0.047 Uiso 1 1 calc R
H12C H 0.6410 0.4720 0.3872 0.047 Uiso 1 1 calc R
C13 C 0.4710(3) 0.1733(2) 0.2596(2) 0.0266(8) Uani 1 1 d .
H13A H 0.4833 0.2144 0.2969 0.032 Uiso 1 1 calc R
H13B H 0.4437 0.2001 0.2137 0.032 Uiso 1 1 calc R
C14 C 0.5740(3) 0.1325(2) 0.25945(19) 0.0250(8) Uani 1 1 d .
H14A H 0.5674 0.1052 0.2138 0.030 Uiso 1 1 calc R
H14B H 0.6290 0.1731 0.2645 0.030 Uiso 1 1 calc R
C15 C 0.2905(3) 0.1306(2) 0.2315(2) 0.0277(8) Uani 1 1 d .
C16 C 0.2108(3) 0.1494(3) 0.2657(2) 0.0341(10) Uani 1 1 d .
C17 C 0.1114(3) 0.1656(3) 0.2257(2) 0.0436(12) Uani 1 1 d .
H17 H 0.0588 0.1780 0.2490 0.052 Uiso 1 1 calc R
C18 C 0.0867(3) 0.1641(3) 0.1529(2) 0.0399(11) Uani 1 1 d .
H18 H 0.0188 0.1771 0.1265 0.048 Uiso 1 1 calc R
C19 C 0.1627(3) 0.1433(3) 0.1190(2) 0.0341(9) Uani 1 1 d .
H19 H 0.1455 0.1406 0.0690 0.041 Uiso 1 1 calc R
C20 C 0.2640(3) 0.1261(2) 0.1565(2) 0.0281(8) Uani 1 1 d .
C21 C 0.2320(3) 0.1547(3) 0.3452(2) 0.0382(11) Uani 1 1 d .
H21 H 0.3085 0.1493 0.3648 0.046 Uiso 1 1 calc R
C22 C 0.1805(6) 0.0876(3) 0.3746(3) 0.075(2) Uani 1 1 d .
H22A H 0.2061 0.0368 0.3614 0.091 Uiso 1 1 calc R
H22B H 0.1053 0.0907 0.3554 0.091 Uiso 1 1 calc R
H22C H 0.1966 0.0919 0.4261 0.091 Uiso 1 1 calc R
C23 C 0.1993(5) 0.2322(3) 0.3712(3) 0.0608(16) Uani 1 1 d .
H23A H 0.1245 0.2392 0.3527 0.073 Uiso 1 1 calc R
H23B H 0.2361 0.2759 0.3550 0.073 Uiso 1 1 calc R
H23C H 0.2161 0.2319 0.4228 0.073 Uiso 1 1 calc R
C24 C 0.3404(3) 0.0989(2) 0.1154(2) 0.0323(9) Uani 1 1 d .
H24 H 0.4064 0.0842 0.1501 0.039 Uiso 1 1 calc R
C25 C 0.3008(4) 0.0251(3) 0.0704(2) 0.0418(11) Uani 1 1 d .
H25A H 0.2388 0.0391 0.0337 0.050 Uiso 1 1 calc R
H25B H 0.2837 -0.0166 0.1005 0.050 Uiso 1 1 calc R
H25C H 0.3548 0.0060 0.0484 0.050 Uiso 1 1 calc R
C26 C 0.3649(4) 0.1642(3) 0.0676(2) 0.0430(11) Uani 1 1 d .
H26A H 0.3938 0.2104 0.0963 0.052 Uiso 1 1 calc R
H26B H 0.3012 0.1798 0.0332 0.052 Uiso 1 1 calc R
H26C H 0.4154 0.1444 0.0429 0.052 Uiso 1 1 calc R
C27 C 0.6962(3) 0.0330(2) 0.31469(19) 0.0243(8) Uani 1 1 d .
C28 C 0.7926(3) 0.0525(2) 0.3622(2) 0.0260(8) Uani 1 1 d .
C29 C 0.8822(3) 0.0129(2) 0.3568(2) 0.0336(9) Uani 1 1 d .
H29 H 0.9464 0.0267 0.3881 0.040 Uiso 1 1 calc R
C30 C 0.8803(3) -0.0459(3) 0.3074(2) 0.0351(10) Uani 1 1 d .
H30 H 0.9423 -0.0722 0.3049 0.042 Uiso 1 1 calc R
C31 C 0.7864(3) -0.0662(3) 0.2615(2) 0.0343(10) Uani 1 1 d .
H31 H 0.7850 -0.1064 0.2272 0.041 Uiso 1 1 calc R
C32 C 0.6939(3) -0.0284(2) 0.2646(2) 0.0284(9) Uani 1 1 d .
C33 C 0.7993(3) 0.1186(2) 0.4157(2) 0.0294(9) Uani 1 1 d .
H33 H 0.7279 0.1270 0.4221 0.035 Uiso 1 1 calc R
C34 C 0.8332(4) 0.1967(3) 0.3878(2) 0.0398(10) Uani 1 1 d .
H34A H 0.7780 0.2159 0.3484 0.048 Uiso 1 1 calc R
H34B H 0.8962 0.1877 0.3717 0.048 Uiso 1 1 calc R
H34C H 0.8470 0.2363 0.4256 0.048 Uiso 1 1 calc R
C35 C 0.8696(3) 0.0992(3) 0.4881(2) 0.0391(10) Uani 1 1 d .
H35A H 0.8570 0.1373 0.5228 0.047 Uiso 1 1 calc R
H35B H 0.9422 0.1025 0.4860 0.047 Uiso 1 1 calc R
H35C H 0.8547 0.0454 0.5018 0.047 Uiso 1 1 calc R
C36 C 0.5943(3) -0.0562(2) 0.2146(2) 0.0306(9) Uani 1 1 d .
H36 H 0.5370 -0.0224 0.2232 0.037 Uiso 1 1 calc R
C37 C 0.5952(4) -0.0460(3) 0.1367(2) 0.0422(11) Uani 1 1 d .
H37A H 0.6524 -0.0768 0.1269 0.051 Uiso 1 1 calc R
H37B H 0.6044 0.0102 0.1270 0.051 Uiso 1 1 calc R
H37C H 0.5294 -0.0649 0.1067 0.051 Uiso 1 1 calc R
C38 C 0.5698(4) -0.1420(3) 0.2295(3) 0.0427(11) Uani 1 1 d .
H38A H 0.6250 -0.1768 0.2220 0.051 Uiso 1 1 calc R
H38B H 0.5037 -0.1576 0.1977 0.051 Uiso 1 1 calc R
H38C H 0.5649 -0.1467 0.2785 0.051 Uiso 1 1 calc R
C39 C 0.3214(4) -0.1186(3) 0.3728(2) 0.0430(11) Uani 1 1 d .
H39A H 0.3112 -0.0911 0.4153 0.052 Uiso 1 1 calc R
H39B H 0.3676 -0.1647 0.3879 0.052 Uiso 1 1 calc R
C40 C 0.2175(4) -0.1454(3) 0.3260(3) 0.0500(13) Uani 1 1 d .
H40A H 0.2173 -0.2035 0.3182 0.060 Uiso 1 1 calc R
H40B H 0.1602 -0.1318 0.3477 0.060 Uiso 1 1 calc R
C41 C 0.2062(4) -0.1010(3) 0.2566(2) 0.0436(11) Uani 1 1 d .
H41A H 0.1734 -0.1349 0.2159 0.052 Uiso 1 1 calc R
H41B H 0.1645 -0.0522 0.2554 0.052 Uiso 1 1 calc R
C42 C 0.3155(4) -0.0816(3) 0.2566(2) 0.0441(12) Uani 1 1 d .
H42A H 0.3492 -0.1272 0.2393 0.053 Uiso 1 1 calc R
H42B H 0.3183 -0.0350 0.2263 0.053 Uiso 1 1 calc R
C43 C 0.5909(4) 0.2405(3) 0.0192(3) 0.0483(12) Uani 1 1 d .
H43 H 0.5397 0.2619 -0.0191 0.058 Uiso 1 1 calc R
C44 C 0.6198(4) 0.2809(3) 0.0817(3) 0.0445(11) Uani 1 1 d .
H44 H 0.5886 0.3304 0.0871 0.053 Uiso 1 1 calc R
C45 C 0.6948(4) 0.2493(3) 0.1369(3) 0.0410(11) Uani 1 1 d .
H45 H 0.7144 0.2779 0.1800 0.049 Uiso 1 1 calc R
C46 C 0.7422(3) 0.1774(2) 0.1313(2) 0.0340(10) Uani 1 1 d .
C47 C 0.7108(4) 0.1372(3) 0.0668(2) 0.0388(10) Uani 1 1 d .
H47 H 0.7413 0.0874 0.0612 0.047 Uiso 1 1 calc R
C48 C 0.6371(4) 0.1681(3) 0.0121(3) 0.0473(12) Uani 1 1 d .
H48 H 0.6173 0.1399 -0.0311 0.057 Uiso 1 1 calc R
C49 C 0.8220(3) 0.1435(3) 0.1910(2) 0.0411(11) Uani 1 1 d .
H49A H 0.7919 0.1350 0.2313 0.049 Uiso 1 1 calc R
H49B H 0.8804 0.1804 0.2045 0.049 Uiso 1 1 calc R
H49C H 0.8464 0.0927 0.1767 0.049 Uiso 1 1 calc 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'
Y Y -2.7962 3.5667 '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
N3 Y1 N2 79.80(11) . .
N3 Y1 O1 123.70(11) . .
N2 Y1 O1 93.15(11) . .
N3 Y1 N1 112.79(11) . .
N2 Y1 N1 114.37(11) . .
O1 Y1 N1 120.61(10) . .
N3 Y1 C2 84.79(12) . .
N2 Y1 C2 164.54(11) . .
O1 Y1 C2 96.46(11) . .
N1 Y1 C2 70.63(11) . .
N3 Y1 C1 129.79(11) . .
N2 Y1 C1 135.82(11) . .
O1 Y1 C1 93.22(10) . .
N1 Y1 C1 31.02(10) . .
C2 Y1 C1 55.74(11) . .
N3 Y1 C1 114.71(11) . 3_656
N2 Y1 C1 163.96(11) . 3_656
O1 Y1 C1 84.39(10) . 3_656
N1 Y1 C1 54.97(11) . 3_656
C2 Y1 C1 30.47(10) . 3_656
C1 Y1 C1 29.18(14) . 3_656
N3 Y1 C13 55.39(11) . .
N2 Y1 C13 28.96(11) . .
O1 Y1 C13 118.76(10) . .
N1 Y1 C13 106.81(11) . .
C2 Y1 C13 136.59(11) . .
C1 Y1 C13 137.27(11) . .
C1 Y1 C13 156.80(11) 3_656 .
C42 O1 C39 106.9(3) . .
C42 O1 Y1 122.5(2) . .
C39 O1 Y1 129.9(2) . .
C5 N1 C1 117.6(3) . .
C5 N1 Y1 138.6(2) . .
C1 N1 Y1 91.0(2) . .
C15 N2 C13 114.5(3) . .
C15 N2 Y1 139.4(2) . .
C13 N2 Y1 105.1(2) . .
C27 N3 C14 111.5(3) . .
C27 N3 Y1 133.1(2) . .
C14 N3 Y1 111.9(2) . .
C1 C1 N1 118.8(4) 3_656 .
C1 C1 C2 123.3(4) 3_656 3_656
N1 C1 C2 117.9(3) . 3_656
C1 C1 Y1 79.5(3) 3_656 .
N1 C1 Y1 57.95(17) . .
C2 C1 Y1 132.8(3) 3_656 .
C1 C1 Y1 71.3(3) 3_656 3_656
N1 C1 Y1 138.6(2) . 3_656
C2 C1 Y1 67.54(19) 3_656 3_656
Y1 C1 Y1 150.82(14) . 3_656
C3 C2 C1 117.6(3) . 3_656
C3 C2 Y1 113.2(3) . .
C1 C2 Y1 82.0(2) 3_656 .
C3 C2 H2 113.5 . .
C1 C2 H2 113.5 3_656 .
Y1 C2 H2 113.5 . .
C2 C3 C4 121.0(4) . 3_656
C2 C3 H3 119.5 . .
C4 C3 H3 119.5 3_656 .
C5 C4 C3 117.8(3) . 3_656
C5 C4 H4 121.1 . .
C3 C4 H4 121.1 3_656 .
N1 C5 C4 122.9(3) . .
N1 C5 C6 116.2(3) . .
C4 C5 C6 120.9(3) . .
C11 C6 C7 117.3(4) . .
C11 C6 C5 120.7(3) . .
C7 C6 C5 121.9(3) . .
C8 C7 C6 121.2(4) . .
C8 C7 H7 119.4 . .
C6 C7 H7 119.4 . .
C9 C8 C7 121.3(4) . .
C9 C8 H8 119.3 . .
C7 C8 H8 119.3 . .
C8 C9 C10 117.8(4) . .
C8 C9 C12 120.7(4) . .
C10 C9 C12 121.5(4) . .
C11 C10 C9 121.6(4) . .
C11 C10 H10 119.2 . .
C9 C10 H10 119.2 . .
C10 C11 C6 120.7(4) . .
C10 C11 H11 119.7 . .
C6 C11 H11 119.7 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N2 C13 C14 112.0(3) . .
N2 C13 Y1 45.92(16) . .
C14 C13 Y1 79.4(2) . .
N2 C13 H13A 109.2 . .
C14 C13 H13A 109.2 . .
Y1 C13 H13A 91.8 . .
N2 C13 H13B 109.2 . .
C14 C13 H13B 109.2 . .
Y1 C13 H13B 153.5 . .
H13A C13 H13B 107.9 . .
N3 C14 C13 111.5(3) . .
N3 C14 H14A 109.3 . .
C13 C14 H14A 109.3 . .
N3 C14 H14B 109.3 . .
C13 C14 H14B 109.3 . .
H14A C14 H14B 108.0 . .
N2 C15 C16 120.1(3) . .
N2 C15 C20 121.8(3) . .
C16 C15 C20 118.2(4) . .
C17 C16 C15 119.8(4) . .
C17 C16 C21 118.5(4) . .
C15 C16 C21 121.6(4) . .
C18 C17 C16 121.9(4) . .
C18 C17 H17 119.0 . .
C16 C17 H17 119.0 . .
C17 C18 C19 118.9(4) . .
C17 C18 H18 120.5 . .
C19 C18 H18 120.5 . .
C18 C19 C20 121.7(4) . .
C18 C19 H19 119.2 . .
C20 C19 H19 119.2 . .
C19 C20 C15 119.4(4) . .
C19 C20 C24 118.1(4) . .
C15 C20 C24 122.4(4) . .
C23 C21 C22 108.9(4) . .
C23 C21 C16 113.7(4) . .
C22 C21 C16 111.2(4) . .
C23 C21 H21 107.6 . .
C22 C21 H21 107.6 . .
C16 C21 H21 107.6 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C21 C23 H23A 109.5 . .
C21 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C21 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C20 C24 C26 112.3(3) . .
C20 C24 C25 111.6(3) . .
C26 C24 C25 109.0(3) . .
C20 C24 H24 107.9 . .
C26 C24 H24 107.9 . .
C25 C24 H24 107.9 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C32 C27 N3 120.5(3) . .
C32 C27 C28 118.7(3) . .
N3 C27 C28 120.8(3) . .
C29 C28 C27 119.4(4) . .
C29 C28 C33 119.9(4) . .
C27 C28 C33 120.6(3) . .
C30 C29 C28 121.9(4) . .
C30 C29 H29 119.0 . .
C28 C29 H29 119.0 . .
C29 C30 C31 119.2(4) . .
C29 C30 H30 120.4 . .
C31 C30 H30 120.4 . .
C30 C31 C32 121.3(4) . .
C30 C31 H31 119.3 . .
C32 C31 H31 119.3 . .
C31 C32 C27 119.5(4) . .
C31 C32 C36 118.0(4) . .
C27 C32 C36 122.5(3) . .
C28 C33 C35 113.7(3) . .
C28 C33 C34 110.9(3) . .
C35 C33 C34 110.3(3) . .
C28 C33 H33 107.2 . .
C35 C33 H33 107.2 . .
C34 C33 H33 107.2 . .
C33 C34 H34A 109.5 . .
C33 C34 H34B 109.5 . .
H34A C34 H34B 109.5 . .
C33 C34 H34C 109.5 . .
H34A C34 H34C 109.5 . .
H34B C34 H34C 109.5 . .
C33 C35 H35A 109.5 . .
C33 C35 H35B 109.5 . .
H35A C35 H35B 109.5 . .
C33 C35 H35C 109.5 . .
H35A C35 H35C 109.5 . .
H35B C35 H35C 109.5 . .
C32 C36 C38 111.3(3) . .
C32 C36 C37 112.7(3) . .
C38 C36 C37 110.6(4) . .
C32 C36 H36 107.3 . .
C38 C36 H36 107.3 . .
C37 C36 H36 107.3 . .
C36 C37 H37A 109.5 . .
C36 C37 H37B 109.5 . .
H37A C37 H37B 109.5 . .
C36 C37 H37C 109.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
C36 C38 H38A 109.5 . .
C36 C38 H38B 109.5 . .
H38A C38 H38B 109.5 . .
C36 C38 H38C 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
O1 C39 C40 105.9(3) . .
O1 C39 H39A 110.5 . .
C40 C39 H39A 110.5 . .
O1 C39 H39B 110.5 . .
C40 C39 H39B 110.5 . .
H39A C39 H39B 108.7 . .
C41 C40 C39 105.4(4) . .
C41 C40 H40A 110.7 . .
C39 C40 H40A 110.7 . .
C41 C40 H40B 110.7 . .
C39 C40 H40B 110.7 . .
H40A C40 H40B 108.8 . .
C42 C41 C40 103.1(4) . .
C42 C41 H41A 111.1 . .
C40 C41 H41A 111.1 . .
C42 C41 H41B 111.1 . .
C40 C41 H41B 111.1 . .
H41A C41 H41B 109.1 . .
O1 C42 C41 104.6(3) . .
O1 C42 H42A 110.8 . .
C41 C42 H42A 110.8 . .
O1 C42 H42B 110.8 . .
C41 C42 H42B 110.8 . .
H42A C42 H42B 108.9 . .
C44 C43 C48 119.5(5) . .
C44 C43 H43 120.3 . .
C48 C43 H43 120.3 . .
C43 C44 C45 119.7(5) . .
C43 C44 H44 120.1 . .
C45 C44 H44 120.1 . .
C46 C45 C44 122.0(5) . .
C46 C45 H45 119.0 . .
C44 C45 H45 119.0 . .
C45 C46 C47 117.0(4) . .
C45 C46 C49 121.8(4) . .
C47 C46 C49 121.2(4) . .
C48 C47 C46 121.2(4) . .
C48 C47 H47 119.4 . .
C46 C47 H47 119.4 . .
C47 C48 C43 120.5(5) . .
C47 C48 H48 119.7 . .
C43 C48 H48 119.7 . .
C46 C49 H49A 109.5 . .
C46 C49 H49B 109.5 . .
H49A C49 H49B 109.5 . .
C46 C49 H49C 109.5 . .
H49A C49 H49C 109.5 . .
H49B C49 H49C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Y1 N3 2.200(3) .
Y1 N2 2.205(3) .
Y1 O1 2.331(3) .
Y1 N1 2.335(3) .
Y1 C2 2.669(4) .
Y1 C1 2.755(4) .
Y1 C1 2.860(4) 3_656
Y1 C13 2.964(4) .
O1 C42 1.456(5) .
O1 C39 1.460(5) .
N1 C5 1.361(5) .
N1 C1 1.420(4) .
N2 C15 1.413(5) .
N2 C13 1.486(5) .
N3 C27 1.424(5) .
N3 C14 1.479(5) .
C1 C1 1.418(7) 3_656
C1 C2 1.465(5) 3_656
C1 Y1 2.860(4) 3_656
C2 C3 1.366(5) .
C2 C1 1.465(5) 3_656
C2 H2 1.0000 .
C3 C4 1.422(5) 3_656
C3 H3 0.9500 .
C4 C5 1.390(5) .
C4 C3 1.422(5) 3_656
C4 H4 0.9500 .
C5 C6 1.492(5) .
C6 C11 1.397(5) .
C6 C7 1.404(5) .
C7 C8 1.392(5) .
C7 H7 0.9500 .
C8 C9 1.377(6) .
C8 H8 0.9500 .
C9 C10 1.396(6) .
C9 C12 1.505(5) .
C10 C11 1.391(5) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.536(5) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.425(5) .
C15 C20 1.426(5) .
C16 C17 1.388(6) .
C16 C21 1.515(5) .
C17 C18 1.382(6) .
C17 H17 0.9500 .
C18 C19 1.386(6) .
C18 H18 0.9500 .
C19 C20 1.398(6) .
C19 H19 0.9500 .
C20 C24 1.518(5) .
C21 C23 1.505(7) .
C21 C22 1.508(7) .
C21 H21 1.0000 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 C26 1.532(6) .
C24 C25 1.539(6) .
C24 H24 1.0000 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 C32 1.421(5) .
C27 C28 1.425(5) .
C28 C29 1.393(5) .
C28 C33 1.517(5) .
C29 C30 1.381(6) .
C29 H29 0.9500 .
C30 C31 1.390(6) .
C30 H30 0.9500 .
C31 C32 1.402(5) .
C31 H31 0.9500 .
C32 C36 1.516(6) .
C33 C35 1.529(6) .
C33 C34 1.533(6) .
C33 H33 1.0000 .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
C35 H35A 0.9800 .
C35 H35B 0.9800 .
C35 H35C 0.9800 .
C36 C38 1.527(6) .
C36 C37 1.538(6) .
C36 H36 1.0000 .
C37 H37A 0.9800 .
C37 H37B 0.9800 .
C37 H37C 0.9800 .
C38 H38A 0.9800 .
C38 H38B 0.9800 .
C38 H38C 0.9800 .
C39 C40 1.527(6) .
C39 H39A 0.9900 .
C39 H39B 0.9900 .
C40 C41 1.525(6) .
C40 H40A 0.9900 .
C40 H40B 0.9900 .
C41 C42 1.493(6) .
C41 H41A 0.9900 .
C41 H41B 0.9900 .
C42 H42A 0.9900 .
C42 H42B 0.9900 .
C43 C44 1.370(7) .
C43 C48 1.389(7) .
C43 H43 0.9500 .
C44 C45 1.385(6) .
C44 H44 0.9500 .
C45 C46 1.382(6) .
C45 H45 0.9500 .
C46 C47 1.403(6) .
C46 C49 1.486(6) .
C47 C48 1.364(7) .
C47 H47 0.9500 .
C48 H48 0.9500 .
C49 H49A 0.9800 .
C49 H49B 0.9800 .
C49 H49C 0.9800 .
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_4
N3 Y1 O1 C42 -50.8(3) . .
N2 Y1 O1 C42 29.0(3) . .
N1 Y1 O1 C42 149.8(3) . .
C2 Y1 O1 C42 -138.9(3) . .
C1 Y1 O1 C42 165.3(3) . .
C1 Y1 O1 C42 -166.9(3) 3_656 .
C13 Y1 O1 C42 14.8(3) . .
N3 Y1 O1 C39 140.4(3) . .
N2 Y1 O1 C39 -139.7(3) . .
N1 Y1 O1 C39 -18.9(4) . .
C2 Y1 O1 C39 52.4(3) . .
C1 Y1 O1 C39 -3.5(3) . .
C1 Y1 O1 C39 24.4(3) 3_656 .
C13 Y1 O1 C39 -154.0(3) . .
N3 Y1 N1 C5 93.5(4) . .
N2 Y1 N1 C5 4.6(4) . .
O1 Y1 N1 C5 -105.1(4) . .
C2 Y1 N1 C5 168.8(4) . .
C1 Y1 N1 C5 -136.1(5) . .
C1 Y1 N1 C5 -161.5(4) 3_656 .
C13 Y1 N1 C5 34.6(4) . .
N3 Y1 N1 C1 -130.4(2) . .
N2 Y1 N1 C1 140.8(2) . .
O1 Y1 N1 C1 31.0(2) . .
C2 Y1 N1 C1 -55.0(2) . .
C1 Y1 N1 C1 -25.4(2) 3_656 .
C13 Y1 N1 C1 170.7(2) . .
N3 Y1 N2 C15 162.8(4) . .
O1 Y1 N2 C15 39.1(4) . .
N1 Y1 N2 C15 -86.7(4) . .
C2 Y1 N2 C15 167.6(4) . .
C1 Y1 N2 C15 -58.8(4) . .
C1 Y1 N2 C15 -41.5(7) 3_656 .
C13 Y1 N2 C15 -167.3(5) . .
N3 Y1 N2 C13 -29.9(2) . .
O1 Y1 N2 C13 -153.6(2) . .
N1 Y1 N2 C13 80.6(2) . .
C2 Y1 N2 C13 -25.2(6) . .
C1 Y1 N2 C13 108.5(2) . .
C1 Y1 N2 C13 125.8(4) 3_656 .
N2 Y1 N3 C27 -148.0(3) . .
O1 Y1 N3 C27 -61.1(4) . .
N1 Y1 N3 C27 99.7(3) . .
C2 Y1 N3 C27 33.2(3) . .
C1 Y1 N3 C27 69.0(4) . .
C1 Y1 N3 C27 39.2(3) 3_656 .
C13 Y1 N3 C27 -165.1(4) . .
N2 Y1 N3 C14 8.4(2) . .
O1 Y1 N3 C14 95.3(2) . .
N1 Y1 N3 C14 -103.9(2) . .
C2 Y1 N3 C14 -170.4(2) . .
C1 Y1 N3 C14 -134.6(2) . .
C1 Y1 N3 C14 -164.4(2) 3_656 .
C13 Y1 N3 C14 -8.7(2) . .
C5 N1 C1 C1 -157.2(4) . 3_656
Y1 N1 C1 C1 53.9(4) . 3_656
C5 N1 C1 C2 23.8(5) . 3_656
Y1 N1 C1 C2 -125.1(3) . 3_656
C5 N1 C1 Y1 148.9(3) . .
C5 N1 C1 Y1 -63.2(5) . 3_656
Y1 N1 C1 Y1 147.9(3) . 3_656
N3 Y1 C1 C1 -67.9(3) . 3_656
N2 Y1 C1 C1 170.3(2) . 3_656
O1 Y1 C1 C1 72.4(3) . 3_656
N1 Y1 C1 C1 -133.9(4) . 3_656
C2 Y1 C1 C1 -23.2(3) . 3_656
C13 Y1 C1 C1 -147.1(3) . 3_656
N3 Y1 C1 N1 66.0(2) . .
N2 Y1 C1 N1 -55.8(3) . .
O1 Y1 C1 N1 -153.6(2) . .
C2 Y1 C1 N1 110.7(2) . .
C1 Y1 C1 N1 133.9(4) 3_656 .
C13 Y1 C1 N1 -13.2(3) . .
N3 Y1 C1 C2 166.0(3) . 3_656
N2 Y1 C1 C2 44.2(4) . 3_656
O1 Y1 C1 C2 -53.7(3) . 3_656
N1 Y1 C1 C2 100.0(4) . 3_656
C2 Y1 C1 C2 -149.3(3) . 3_656
C1 Y1 C1 C2 -126.1(5) 3_656 3_656
C13 Y1 C1 C2 86.8(4) . 3_656
N3 Y1 C1 Y1 -67.9(3) . 3_656
N2 Y1 C1 Y1 170.3(2) . 3_656
O1 Y1 C1 Y1 72.4(3) . 3_656
N1 Y1 C1 Y1 -133.9(4) . 3_656
C2 Y1 C1 Y1 -23.2(3) . 3_656
C1 Y1 C1 Y1 -0.002(1) 3_656 3_656
C13 Y1 C1 Y1 -147.1(3) . 3_656
N3 Y1 C2 C3 -74.0(3) . .
N2 Y1 C2 C3 -78.7(5) . .
O1 Y1 C2 C3 49.4(3) . .
N1 Y1 C2 C3 169.6(3) . .
C1 Y1 C2 C3 138.9(3) . .
C1 Y1 C2 C3 116.7(4) 3_656 .
C13 Y1 C2 C3 -96.1(3) . .
N3 Y1 C2 C1 169.4(2) . 3_656
N2 Y1 C2 C1 164.7(4) . 3_656
O1 Y1 C2 C1 -67.3(2) . 3_656
N1 Y1 C2 C1 53.0(2) . 3_656
C1 Y1 C2 C1 22.2(3) . 3_656
C13 Y1 C2 C1 147.2(2) . 3_656
C1 C2 C3 C4 -4.1(5) 3_656 3_656
Y1 C2 C3 C4 -97.2(4) . 3_656
C1 N1 C5 C4 -7.2(5) . .
Y1 N1 C5 C4 121.4(4) . .
C1 N1 C5 C6 174.4(3) . .
Y1 N1 C5 C6 -57.0(5) . .
C3 C4 C5 N1 -11.0(6) 3_656 .
C3 C4 C5 C6 167.3(3) 3_656 .
N1 C5 C6 C11 -22.0(5) . .
C4 C5 C6 C11 159.6(4) . .
N1 C5 C6 C7 157.7(4) . .
C4 C5 C6 C7 -20.7(6) . .
C11 C6 C7 C8 0.6(6) . .
C5 C6 C7 C8 -179.1(4) . .
C6 C7 C8 C9 0.1(6) . .
C7 C8 C9 C10 -0.7(6) . .
C7 C8 C9 C12 179.2(4) . .
C8 C9 C10 C11 0.6(6) . .
C12 C9 C10 C11 -179.3(4) . .
C9 C10 C11 C6 0.1(6) . .
C7 C6 C11 C10 -0.7(6) . .
C5 C6 C11 C10 179.1(3) . .
C15 N2 C13 C14 -141.1(3) . .
Y1 N2 C13 C14 48.0(3) . .
C15 N2 C13 Y1 170.9(4) . .
N3 Y1 C13 N2 143.4(3) . .
O1 Y1 C13 N2 30.4(3) . .
N1 Y1 C13 N2 -110.1(2) . .
C2 Y1 C13 N2 170.5(2) . .
C1 Y1 C13 N2 -103.1(3) . .
C1 Y1 C13 N2 -145.3(3) 3_656 .
N3 Y1 C13 C14 7.89(19) . .
N2 Y1 C13 C14 -135.5(3) . .
O1 Y1 C13 C14 -105.1(2) . .
N1 Y1 C13 C14 114.3(2) . .
C2 Y1 C13 C14 35.0(3) . .
C1 Y1 C13 C14 121.4(2) . .
C1 Y1 C13 C14 79.2(3) 3_656 .
C27 N3 C14 C13 176.6(3) . .
Y1 N3 C14 C13 14.9(4) . .
N2 C13 C14 N3 -43.3(4) . .
Y1 C13 C14 N3 -10.4(3) . .
C13 N2 C15 C16 -117.3(4) . .
Y1 N2 C15 C16 49.2(6) . .
C13 N2 C15 C20 63.4(5) . .
Y1 N2 C15 C20 -130.1(4) . .
N2 C15 C16 C17 178.4(4) . .
C20 C15 C16 C17 -2.3(6) . .
N2 C15 C16 C21 0.1(6) . .
C20 C15 C16 C21 179.5(4) . .
C15 C16 C17 C18 -0.1(7) . .
C21 C16 C17 C18 178.3(5) . .
C16 C17 C18 C19 2.2(8) . .
C17 C18 C19 C20 -1.9(7) . .
C18 C19 C20 C15 -0.4(6) . .
C18 C19 C20 C24 176.3(4) . .
N2 C15 C20 C19 -178.2(4) . .
C16 C15 C20 C19 2.5(6) . .
N2 C15 C20 C24 5.3(6) . .
C16 C15 C20 C24 -174.0(4) . .
C17 C16 C21 C23 -52.7(6) . .
C15 C16 C21 C23 125.6(5) . .
C17 C16 C21 C22 70.6(6) . .
C15 C16 C21 C22 -111.1(5) . .
C19 C20 C24 C26 66.6(5) . .
C15 C20 C24 C26 -116.8(4) . .
C19 C20 C24 C25 -56.2(5) . .
C15 C20 C24 C25 120.4(4) . .
C14 N3 C27 C32 -76.6(4) . .
Y1 N3 C27 C32 79.9(4) . .
C14 N3 C27 C28 103.6(4) . .
Y1 N3 C27 C28 -99.9(4) . .
C32 C27 C28 C29 2.1(5) . .
N3 C27 C28 C29 -178.1(3) . .
C32 C27 C28 C33 178.9(3) . .
N3 C27 C28 C33 -1.3(5) . .
C27 C28 C29 C30 -1.1(6) . .
C33 C28 C29 C30 -177.9(4) . .
C28 C29 C30 C31 0.2(6) . .
C29 C30 C31 C32 -0.4(6) . .
C30 C31 C32 C27 1.5(6) . .
C30 C31 C32 C36 -177.6(4) . .
N3 C27 C32 C31 177.9(3) . .
C28 C27 C32 C31 -2.3(5) . .
N3 C27 C32 C36 -3.1(5) . .
C28 C27 C32 C36 176.7(3) . .
C29 C28 C33 C35 -43.9(5) . .
C27 C28 C33 C35 139.3(4) . .
C29 C28 C33 C34 81.0(5) . .
C27 C28 C33 C34 -95.8(4) . .
C31 C32 C36 C38 64.1(5) . .
C27 C32 C36 C38 -115.0(4) . .
C31 C32 C36 C37 -60.8(5) . .
C27 C32 C36 C37 120.2(4) . .
C42 O1 C39 C40 -21.1(5) . .
Y1 O1 C39 C40 149.0(3) . .
O1 C39 C40 C41 -1.9(5) . .
C39 C40 C41 C42 23.2(5) . .
C39 O1 C42 C41 36.5(5) . .
Y1 O1 C42 C41 -134.4(3) . .
C40 C41 C42 O1 -36.5(5) . .
C48 C43 C44 C45 0.2(7) . .
C43 C44 C45 C46 -0.1(7) . .
C44 C45 C46 C47 -0.1(6) . .
C44 C45 C46 C49 -179.5(4) . .
C45 C46 C47 C48 0.3(6) . .
C49 C46 C47 C48 179.7(4) . .
C46 C47 C48 C43 -0.3(7) . .
C44 C43 C48 C47 0.0(7) . .
