#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:48:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178445 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/66/4026664.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_4026664
loop_
_publ_author_name
'Bret R. Van Ausdall'
'Nils F. Poth'
'Virginia A. Kincaid'
'Atta M. Arif'
'Janis Louie'
_publ_section_title
;
 Imidazolidene Carboxylate Bound MBPh4 Complexes (M = Li, Na) and Their
 Relevance in Transcarboxylation Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8413
_journal_page_last               8420
_journal_paper_doi               10.1021/jo201647b
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C68 H98 N6 Na2 O6,2(C24 H20 B),C4 H10 O'
_chemical_formula_sum            'C120 H148 B2 N6 Na2 O7'
_chemical_formula_weight         1854.04
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.1820(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   17.5568(4)
_cell_length_b                   14.9417(2)
_cell_length_c                   21.8429(5)
_cell_measurement_reflns_used    40044
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1.018
_cell_volume                     5579.0(2)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'WinGx, Ortep3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD Diffractometer'
_diffrn_measurement_method       'Phi and Omega scan'
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23129
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_correction_T_min  0.9746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Monor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_description       prism
_exptl_crystal_F_000             1996
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         12715
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0834P)²+2.8635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1944
_reflns_number_gt                7509
_reflns_number_total             12715
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201647b_si_003.cif
_cod_data_source_block           jl020
_cod_database_code               4026664
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.41627(5) 0.57504(6) 1.04676(4) 0.0352(2) Uani 1 1 d . . .
B1 B 0.97755(15) 0.51601(17) 0.79181(12) 0.0302(6) Uani 1 1 d . . .
O1 O 0.46403(10) 0.63961(11) 0.97063(8) 0.0407(4) Uani 1 1 d . . .
O2 O 0.56020(10) 0.57101(11) 0.93617(9) 0.0427(4) Uani 1 1 d . . .
O3 O 0.28592(11) 0.62048(13) 1.04369(9) 0.0509(5) Uani 1 1 d . . .
N1 N 0.59885(10) 0.74612(12) 0.89532(8) 0.0280(4) Uani 1 1 d . . .
N2 N 0.49506(18) 0.64050(18) 1.14097(13) 0.0673(8) Uani 1 1 d . . .
N3 N 0.47834(10) 0.78451(11) 0.88701(8) 0.0262(4) Uani 1 1 d . . .
C2 C 0.53096(12) 0.71997(14) 0.90828(10) 0.0261(5) Uani 1 1 d . . .
C4 C 0.51359(13) 0.85224(15) 0.85990(10) 0.0307(5) Uani 1 1 d . . .
H4 H 0.4893 0.9052 0.8408 0.037 Uiso 1 1 calc R . .
C5 C 0.58903(14) 0.82838(15) 0.86587(11) 0.0320(5) Uani 1 1 d . . .
H5 H 0.6281 0.8620 0.8523 0.038 Uiso 1 1 calc R . .
C6 C 0.51704(13) 0.63441(15) 0.94222(10) 0.0294(5) Uani 1 1 d . . .
C7 C 0.67217(13) 0.69632(15) 0.90796(11) 0.0311(5) Uani 1 1 d . . .
C8 C 0.72210(13) 0.70412(16) 0.96716(12) 0.0366(6) Uani 1 1 d . . .
C9 C 0.79166(15) 0.65541(19) 0.97672(14) 0.0475(7) Uani 1 1 d . . .
H9 H 0.8278 0.6585 1.0163 0.057 Uiso 1 1 calc R . .
C10 C 0.80880(16) 0.6030(2) 0.92995(14) 0.0528(7) Uani 1 1 d . . .
H10 H 0.8566 0.5706 0.9377 0.063 Uiso 1 1 calc R . .
C11 C 0.75774(16) 0.5968(2) 0.87190(13) 0.0496(7) Uani 1 1 d . . .
H11 H 0.7705 0.5596 0.8404 0.059 Uiso 1 1 calc R . .
C12 C 0.68762(14) 0.64426(17) 0.85893(12) 0.0376(6) Uani 1 1 d . . .
C13 C 0.70396(15) 0.76179(18) 1.01910(12) 0.0441(6) Uani 1 1 d . . .
H13 H 0.6532 0.7931 1.0019 0.053 Uiso 1 1 calc R . .
C14 C 0.6942(2) 0.7060(2) 1.07502(14) 0.0628(9) Uani 1 1 d . . .
H14A H 0.6523 0.6621 1.0612 0.094 Uiso 1 1 calc R . .
H14B H 0.6808 0.7452 1.1070 0.094 Uiso 1 1 calc R . .
H14C H 0.7433 0.6746 1.0930 0.094 Uiso 1 1 calc R . .
C15 C 0.7669(2) 0.8334(2) 1.03989(18) 0.0717(10) Uani 1 1 d . . .
H15A H 0.8168 0.8046 1.0587 0.107 Uiso 1 1 calc R . .
H15B H 0.7516 0.8728 1.0709 0.107 Uiso 1 1 calc R . .
H15C H 0.7724 0.8687 1.0033 0.107 Uiso 1 1 calc R . .
C16 C 0.63306(16) 0.63925(18) 0.79408(12) 0.0438(6) Uani 1 1 d . . .
H16 H 0.5893 0.6824 0.7933 0.053 Uiso 1 1 calc R . .
C17 C 0.5972(2) 0.5465(2) 0.78098(16) 0.0652(9) Uani 1 1 d . . .
H17A H 0.6388 0.5026 0.7810 0.098 Uiso 1 1 calc R . .
H17B H 0.5604 0.5462 0.7398 0.098 Uiso 1 1 calc R . .
H17C H 0.5695 0.5308 0.8136 0.098 Uiso 1 1 calc R . .
C18 C 0.67425(17) 0.66731(19) 0.74308(13) 0.0484(7) Uani 1 1 d . . .
H18A H 0.6964 0.7273 0.7524 0.073 Uiso 1 1 calc R . .
H18B H 0.6366 0.6679 0.7023 0.073 Uiso 1 1 calc R . .
H18C H 0.7163 0.6248 0.7416 0.073 Uiso 1 1 calc R . .
C19 C 0.39474(13) 0.78056(15) 0.88351(10) 0.0305(5) Uani 1 1 d . . .
C20 C 0.36482(14) 0.83207(16) 0.92581(11) 0.0363(5) Uani 1 1 d . . .
C21 C 0.28407(15) 0.82784(19) 0.91988(13) 0.0456(7) Uani 1 1 d . . .
H21 H 0.2609 0.8620 0.9475 0.055 Uiso 1 1 calc R . .
C22 C 0.23733(15) 0.7753(2) 0.87480(13) 0.0478(7) Uani 1 1 d . . .
H22 H 0.1826 0.7732 0.8720 0.057 Uiso 1 1 calc R . .
C23 C 0.26914(14) 0.72549(19) 0.83352(13) 0.0448(6) Uani 1 1 d . . .
H23 H 0.2359 0.6894 0.8028 0.054 Uiso 1 1 calc R . .
C24 C 0.34915(13) 0.72748(16) 0.83622(11) 0.0352(5) Uani 1 1 d . . .
C25 C 0.41635(16) 0.88740(19) 0.97727(13) 0.0468(7) Uani 1 1 d . . .
H25 H 0.4676 0.8963 0.9654 0.056 Uiso 1 1 calc R . .
C26 C 0.3830(2) 0.9795(2) 0.98513(15) 0.0612(8) Uani 1 1 d . . .
H26A H 0.3742 1.0120 0.9451 0.092 Uiso 1 1 calc R . .
H26B H 0.4200 1.0130 1.0174 0.092 Uiso 1 1 calc R . .
H26C H 0.3332 0.9730 0.9979 0.092 Uiso 1 1 calc R . .
C27 C 0.4326(3) 0.8374(2) 1.03964(15) 0.0810(12) Uani 1 1 d . . .
H27A H 0.3832 0.8269 1.0523 0.121 Uiso 1 1 calc R . .
H27B H 0.4675 0.8732 1.0719 0.121 Uiso 1 1 calc R . .
H27C H 0.4575 0.7799 1.0349 0.121 Uiso 1 1 calc R . .
C28 C 0.38294(15) 0.67314(18) 0.79018(12) 0.0422(6) Uani 1 1 d . . .
H28 H 0.4395 0.6893 0.7965 0.051 Uiso 1 1 calc R . .
C29 C 0.37812(18) 0.57267(19) 0.80248(14) 0.0547(7) Uani 1 1 d . . .
H29A H 0.3232 0.5550 0.7965 0.082 Uiso 1 1 calc R . .
H29B H 0.4060 0.5593 0.8457 0.082 Uiso 1 1 calc R . .
H29C H 0.4021 0.5394 0.7731 0.082 Uiso 1 1 calc R . .
C30 C 0.34270(18) 0.6957(2) 0.72231(13) 0.0530(7) Uani 1 1 d . . .
H30A H 0.2870 0.6806 0.7149 0.079 Uiso 1 1 calc R . .
H30B H 0.3668 0.6612 0.6936 0.079 Uiso 1 1 calc R . .
H30C H 0.3484 0.7598 0.7149 0.079 Uiso 1 1 calc R . .
C31 C 0.5262(2) 0.65738(19) 1.19040(15) 0.0567(8) Uani 1 1 d . . .
C32 C 0.5654(3) 0.6785(3) 1.25455(17) 0.0939(14) Uani 1 1 d . . .
H32A H 0.5343 0.7222 1.2718 0.141 Uiso 1 1 calc R . .
H32B H 0.6171 0.7038 1.2553 0.141 Uiso 1 1 calc R . .
H32C H 0.5714 0.6239 1.2800 0.141 Uiso 1 1 calc R . .
C33 C 0.3027(3) 0.6966(3) 1.1410(2) 0.1115(17) Uani 1 1 d . . .
H33A H 0.3206 0.6429 1.1660 0.167 Uiso 1 1 calc R . .
H33B H 0.2776 0.7374 1.1655 0.167 Uiso 1 1 calc R . .
H33C H 0.3476 0.7266 1.1303 0.167 Uiso 1 1 calc R . .
C34 C 0.2487(3) 0.6721(4) 1.0855(2) 0.1026(15) Uani 1 1 d . . .
H34A H 0.2249 0.7267 1.0635 0.123 Uiso 1 1 calc R . .
H34B H 0.2063 0.6360 1.0964 0.123 Uiso 1 1 calc R . .
C35 C 0.22960(17) 0.5970(2) 0.98780(15) 0.0565(8) Uani 1 1 d . . .
H35A H 0.2064 0.6519 0.9658 0.068 Uiso 1 1 calc R . .
H35B H 0.1871 0.5612 0.9987 0.068 Uiso 1 1 calc R . .
C36 C 0.26898(19) 0.5441(2) 0.94621(15) 0.0618(8) Uani 1 1 d . . .
H36A H 0.3087 0.5812 0.9334 0.093 Uiso 1 1 calc R . .
H36B H 0.2302 0.5248 0.9088 0.093 Uiso 1 1 calc R . .
H36C H 0.2940 0.4914 0.9690 0.093 Uiso 1 1 calc R . .
C37 C 1.05233(13) 0.51883(15) 0.75730(11) 0.0317(5) Uani 1 1 d . . .
C38 C 1.11572(14) 0.45916(17) 0.77080(12) 0.0390(6) Uani 1 1 d . . .
H38 H 1.1175 0.4159 0.8029 0.047 Uiso 1 1 calc R . .
C39 C 1.17611(16) 0.46060(19) 0.73917(14) 0.0489(7) Uani 1 1 d . . .
H39 H 1.2171 0.4178 0.7494 0.059 Uiso 1 1 calc R . .
C40 C 1.17701(17) 0.5231(2) 0.69350(14) 0.0535(8) Uani 1 1 d . . .
H40 H 1.2176 0.5233 0.6712 0.064 Uiso 1 1 calc R . .
C41 C 1.11816(17) 0.5854(2) 0.68062(13) 0.0521(7) Uani 1 1 d . . .
H41 H 1.1186 0.6300 0.6497 0.063 Uiso 1 1 calc R . .
C42 C 1.05775(15) 0.58380(18) 0.71242(12) 0.0414(6) Uani 1 1 d . . .
H42 H 1.0186 0.6288 0.7032 0.050 Uiso 1 1 calc R . .
C43 C 0.97429(13) 0.61452(14) 0.82491(11) 0.0298(5) Uani 1 1 d . . .
C44 C 1.03753(13) 0.64538(15) 0.87099(11) 0.0321(5) Uani 1 1 d . . .
H44 H 1.0837 0.6100 0.8806 0.039 Uiso 1 1 calc R . .
C45 C 1.03652(14) 0.72498(16) 0.90349(11) 0.0365(6) Uani 1 1 d . . .
H45 H 1.0811 0.7429 0.9346 0.044 Uiso 1 1 calc R . .
C46 C 0.97027(17) 0.77800(17) 0.89037(14) 0.0485(7) Uani 1 1 d . . .
H46 H 0.9684 0.8322 0.9127 0.058 Uiso 1 1 calc R . .
C47 C 0.90733(17) 0.75105(19) 0.84451(15) 0.0569(8) Uani 1 1 d . . .
H47 H 0.8616 0.7872 0.8348 0.068 Uiso 1 1 calc R . .
C48 C 0.90987(15) 0.67131(17) 0.81216(13) 0.0440(6) Uani 1 1 d . . .
H48 H 0.8658 0.6550 0.7800 0.053 Uiso 1 1 calc R . .
C49 C 0.89329(13) 0.49667(14) 0.74091(11) 0.0300(5) Uani 1 1 d . . .
C50 C 0.87016(15) 0.53699(17) 0.68156(11) 0.0384(6) Uani 1 1 d . . .
H50 H 0.9057 0.5765 0.6684 0.046 Uiso 1 1 calc R . .
C51 C 0.79789(15) 0.52215(18) 0.64099(12) 0.0435(6) Uani 1 1 d . . .
H51 H 0.7853 0.5511 0.6012 0.052 Uiso 1 1 calc R . .
C52 C 0.74414(15) 0.46541(18) 0.65832(13) 0.0437(6) Uani 1 1 d . . .
H52 H 0.6948 0.4546 0.6307 0.052 Uiso 1 1 calc R . .
C53 C 0.76368(14) 0.42508(17) 0.71640(13) 0.0409(6) Uani 1 1 d . . .
H53 H 0.7274 0.3862 0.7292 0.049 Uiso 1 1 calc R . .
C54 C 0.83637(14) 0.44082(15) 0.75653(12) 0.0346(5) Uani 1 1 d . . .
H54 H 0.8479 0.4123 0.7965 0.042 Uiso 1 1 calc R . .
C55 C 0.98965(13) 0.43555(15) 0.84440(11) 0.0301(5) Uani 1 1 d . . .
C56 C 0.98915(14) 0.44686(16) 0.90757(11) 0.0355(5) Uani 1 1 d . . .
H56 H 0.9848 0.5059 0.9226 0.043 Uiso 1 1 calc R . .
C57 C 0.99465(16) 0.37583(18) 0.95001(12) 0.0435(6) Uani 1 1 d . . .
H57 H 0.9933 0.3871 0.9925 0.052 Uiso 1 1 calc R . .
C58 C 1.00209(16) 0.28939(18) 0.93009(13) 0.0451(6) Uani 1 1 d . . .
H58 H 1.0069 0.2408 0.9588 0.054 Uiso 1 1 calc R . .
C59 C 1.00244(15) 0.27446(17) 0.86773(13) 0.0419(6) Uani 1 1 d . . .
H59 H 1.0071 0.2152 0.8532 0.050 Uiso 1 1 calc R . .
C60 C 0.99599(14) 0.34575(15) 0.82642(12) 0.0370(6) Uani 1 1 d . . .
H60 H 0.9958 0.3335 0.7837 0.044 Uiso 1 1 calc R . .
O4 O 0.5195(9) 0.5105(13) 0.5026(7) 0.230(8) Uani 0.50 1 d PD . .
C61 C 0.5940(8) 0.5310(11) 0.4834(6) 0.157(6) Uiso 0.50 1 d PD A 1
H61A H 0.6385 0.4977 0.5094 0.189 Uiso 0.50 1 calc PR A 1
H61B H 0.6057 0.5959 0.4865 0.189 Uiso 0.50 1 calc PR A 1
C62 C 0.5761(6) 0.4991(7) 0.4148(4) 0.236(4) Uiso 1 1 d D . .
H62A H 0.6220 0.5089 0.3972 0.354 Uiso 0.50 1 calc PR A 1
H62B H 0.5316 0.5330 0.3903 0.354 Uiso 0.50 1 calc PR A 1
H62C H 0.5632 0.4353 0.4131 0.354 Uiso 0.50 1 calc PR A 1
H62D H 0.5673 0.4745 0.3722 0.354 Uiso 0.50 1 calc PR A 2
H62E H 0.6225 0.4713 0.4415 0.354 Uiso 0.50 1 calc PR A 2
H62F H 0.5840 0.5640 0.4134 0.354 Uiso 0.50 1 calc PR A 2
C61A C 0.5011(9) 0.4789(11) 0.4435(6) 0.167(6) Uiso 0.50 1 d PD . 2
H61C H 0.4582 0.5091 0.4132 0.201 Uiso 0.50 1 calc PR . 2
H61D H 0.4923 0.4141 0.4351 0.201 Uiso 0.50 1 calc PR . 2
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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
O2 Na1 O1 117.20(7) 3_667 .
O2 Na1 O3 115.09(8) 3_667 .
O1 Na1 O3 112.14(7) . .
O2 Na1 N2 101.85(9) 3_667 .
O1 Na1 N2 102.69(9) . .
O3 Na1 N2 105.67(10) . .
C55 B1 C43 111.04(18) . .
C55 B1 C37 110.32(19) . .
C43 B1 C37 106.71(18) . .
C55 B1 C49 107.11(18) . .
C43 B1 C49 109.55(18) . .
C37 B1 C49 112.16(19) . .
C6 O1 Na1 142.96(15) . .
C6 O2 Na1 145.34(15) . 3_667
C35 O3 C34 110.1(3) . .
C35 O3 Na1 115.40(16) . .
C34 O3 Na1 134.5(2) . .
C2 N1 C5 109.54(18) . .
C2 N1 C7 126.78(18) . .
C5 N1 C7 123.66(18) . .
C31 N2 Na1 166.4(3) . .
C2 N3 C4 109.43(18) . .
C2 N3 C19 126.57(18) . .
C4 N3 C19 123.41(17) . .
N3 C2 N1 106.95(18) . .
N3 C2 C6 126.59(19) . .
N1 C2 C6 126.44(19) . .
C5 C4 N3 106.85(19) . .
C5 C4 H4 126.6 . .
N3 C4 H4 126.6 . .
C4 C5 N1 107.22(19) . .
C4 C5 H5 126.4 . .
N1 C5 H5 126.4 . .
O1 C6 O2 130.7(2) . .
O1 C6 C2 114.51(19) . .
O2 C6 C2 114.79(19) . .
C8 C7 C12 124.5(2) . .
C8 C7 N1 118.4(2) . .
C12 C7 N1 117.1(2) . .
C7 C8 C9 116.1(2) . .
C7 C8 C13 123.2(2) . .
C9 C8 C13 120.7(2) . .
C10 C9 C8 121.2(3) . .
C10 C9 H9 119.4 . .
C8 C9 H9 119.4 . .
C9 C10 C11 121.1(2) . .
C9 C10 H10 119.5 . .
C11 C10 H10 119.5 . .
C10 C11 C12 120.7(3) . .
C10 C11 H11 119.6 . .
C12 C11 H11 119.6 . .
C11 C12 C7 116.4(2) . .
C11 C12 C16 120.3(2) . .
C7 C12 C16 123.3(2) . .
C8 C13 C14 111.8(2) . .
C8 C13 C15 111.1(2) . .
C14 C13 C15 110.6(3) . .
C8 C13 H13 107.8 . .
C14 C13 H13 107.8 . .
C15 C13 H13 107.8 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C18 C16 C12 111.4(2) . .
C18 C16 C17 111.0(2) . .
C12 C16 C17 111.4(2) . .
C18 C16 H16 107.6 . .
C12 C16 H16 107.6 . .
C17 C16 H16 107.6 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C18 H18A 109.5 . .
C16 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C16 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C20 C19 C24 124.3(2) . .
C20 C19 N3 118.1(2) . .
C24 C19 N3 117.5(2) . .
C19 C20 C21 116.2(2) . .
C19 C20 C25 122.7(2) . .
C21 C20 C25 121.0(2) . .
C22 C21 C20 121.3(3) . .
C22 C21 H21 119.3 . .
C20 C21 H21 119.3 . .
C21 C22 C23 120.7(2) . .
C21 C22 H22 119.6 . .
C23 C22 H22 119.6 . .
C22 C23 C24 121.0(2) . .
C22 C23 H23 119.5 . .
C24 C23 H23 119.5 . .
C23 C24 C19 116.4(2) . .
C23 C24 C28 120.3(2) . .
C19 C24 C28 123.3(2) . .
C20 C25 C26 113.4(2) . .
C20 C25 C27 110.7(2) . .
C26 C25 C27 110.0(2) . .
C20 C25 H25 107.5 . .
C26 C25 H25 107.5 . .
C27 C25 H25 107.5 . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C25 C27 H27A 109.5 . .
C25 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C25 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C24 C28 C30 111.2(2) . .
C24 C28 C29 111.3(2) . .
C30 C28 C29 110.8(2) . .
C24 C28 H28 107.8 . .
C30 C28 H28 107.8 . .
C29 C28 H28 107.8 . .
C28 C29 H29A 109.5 . .
C28 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C28 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C28 C30 H30A 109.5 . .
C28 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C28 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
N2 C31 C32 179.1(4) . .
C31 C32 H32A 109.5 . .
C31 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C31 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
C34 C33 H33A 109.5 . .
C34 C33 H33B 109.5 . .
H33A C33 H33B 109.5 . .
C34 C33 H33C 109.5 . .
H33A C33 H33C 109.5 . .
H33B C33 H33C 109.5 . .
C33 C34 O3 111.5(4) . .
C33 C34 H34A 109.3 . .
O3 C34 H34A 109.3 . .
C33 C34 H34B 109.3 . .
O3 C34 H34B 109.3 . .
H34A C34 H34B 108.0 . .
O3 C35 C36 109.0(2) . .
O3 C35 H35A 109.9 . .
C36 C35 H35A 109.9 . .
O3 C35 H35B 109.9 . .
C36 C35 H35B 109.9 . .
H35A C35 H35B 108.3 . .
C35 C36 H36A 109.5 . .
C35 C36 H36B 109.5 . .
H36A C36 H36B 109.5 . .
C35 C36 H36C 109.5 . .
H36A C36 H36C 109.5 . .
H36B C36 H36C 109.5 . .
C42 C37 C38 114.3(2) . .
C42 C37 B1 121.6(2) . .
C38 C37 B1 124.1(2) . .
C39 C38 C37 122.9(3) . .
C39 C38 H38 118.5 . .
C37 C38 H38 118.5 . .
C40 C39 C38 120.6(3) . .
C40 C39 H39 119.7 . .
C38 C39 H39 119.7 . .
C39 C40 C41 118.6(3) . .
C39 C40 H40 120.7 . .
C41 C40 H40 120.7 . .
C40 C41 C42 120.6(3) . .
C40 C41 H41 119.7 . .
C42 C41 H41 119.7 . .
C41 C42 C37 122.8(3) . .
C41 C42 H42 118.6 . .
C37 C42 H42 118.6 . .
C48 C43 C44 114.8(2) . .
C48 C43 B1 124.4(2) . .
C44 C43 B1 120.7(2) . .
C45 C44 C43 123.4(2) . .
C45 C44 H44 118.3 . .
C43 C44 H44 118.3 . .
C46 C45 C44 119.6(2) . .
C46 C45 H45 120.2 . .
C44 C45 H45 120.2 . .
C47 C46 C45 118.9(2) . .
C47 C46 H46 120.6 . .
C45 C46 H46 120.6 . .
C46 C47 C48 120.6(3) . .
C46 C47 H47 119.7 . .
C48 C47 H47 119.7 . .
C43 C48 C47 122.7(2) . .
C43 C48 H48 118.7 . .
C47 C48 H48 118.7 . .
C54 C49 C50 114.1(2) . .
C54 C49 B1 121.1(2) . .
C50 C49 B1 124.7(2) . .
C51 C50 C49 123.4(2) . .
C51 C50 H50 118.3 . .
C49 C50 H50 118.3 . .
C52 C51 C50 120.2(2) . .
C52 C51 H51 119.9 . .
C50 C51 H51 119.9 . .
C53 C52 C51 118.6(2) . .
C53 C52 H52 120.7 . .
C51 C52 H52 120.7 . .
C52 C53 C54 120.4(2) . .
C52 C53 H53 119.8 . .
C54 C53 H53 119.8 . .
C53 C54 C49 123.3(2) . .
C53 C54 H54 118.4 . .
C49 C54 H54 118.4 . .
C56 C55 C60 114.2(2) . .
C56 C55 B1 125.1(2) . .
C60 C55 B1 120.5(2) . .
C55 C56 C57 123.4(2) . .
C55 C56 H56 118.3 . .
C57 C56 H56 118.3 . .
C58 C57 C56 119.9(2) . .
C58 C57 H57 120.0 . .
C56 C57 H57 120.0 . .
C57 C58 C59 119.0(2) . .
C57 C58 H58 120.5 . .
C59 C58 H58 120.5 . .
C58 C59 C60 120.0(2) . .
C58 C59 H59 120.0 . .
C60 C59 H59 120.0 . .
C59 C60 C55 123.4(2) . .
C59 C60 H60 118.3 . .
C55 C60 H60 118.3 . .
O4 O4 C61A 76(2) 3_666 3_666
O4 O4 C61 152(3) 3_666 .
C61A O4 C61 131.5(11) 3_666 .
O4 C61 C62 102.3(10) . .
O4 C61 H61A 111.3 . .
C62 C61 H61A 111.3 . .
O4 C61 H61B 111.3 . .
C62 C61 H61B 111.3 . .
H61A C61 H61B 109.2 . .
C61 C62 C61A 71.5(7) . .
C61 C62 H62A 109.5 . .
C61A C62 H62A 177.7 . .
C61 C62 H62B 109.5 . .
C61A C62 H62B 71.9 . .
H62A C62 H62B 109.5 . .
C61 C62 H62C 109.5 . .
C61A C62 H62C 68.2 . .
H62A C62 H62C 109.5 . .
H62B C62 H62C 109.5 . .
C61 C62 H62D 175.3 . .
C61A C62 H62D 109.5 . .
H62A C62 H62D 69.4 . .
H62B C62 H62D 75.1 . .
H62C C62 H62D 67.2 . .
C61 C62 H62E 66.1 . .
C61A C62 H62E 109.5 . .
H62A C62 H62E 69.3 . .
H62B C62 H62E 173.9 . .
H62C C62 H62E 76.3 . .
H62D C62 H62E 109.5 . .
C61 C62 H62F 74.1 . .
C61A C62 H62F 109.5 . .
H62A C62 H62F 72.9 . .
H62B C62 H62F 64.8 . .
H62C C62 H62F 174.2 . .
H62D C62 H62F 109.5 . .
H62E C62 H62F 109.5 . .
O4 C61A C62 137.8(13) 3_666 .
O4 C61A H61C 102.7 3_666 .
C62 C61A H61C 102.7 . .
O4 C61A H61D 102.7 3_666 .
C62 C61A H61D 102.7 . .
H61C C61A H61D 105.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 O2 2.2364(18) 3_667
Na1 O1 2.2439(18) .
Na1 O3 2.373(2) .
Na1 N2 2.410(3) .
B1 C55 1.643(3) .
B1 C43 1.647(3) .
B1 C37 1.657(3) .
B1 C49 1.661(3) .
O1 C6 1.233(3) .
O2 C6 1.239(3) .
O2 Na1 2.2364(18) 3_667
O3 C35 1.428(4) .
O3 C34 1.459(4) .
N1 C2 1.344(3) .
N1 C5 1.380(3) .
N1 C7 1.458(3) .
N2 C31 1.122(4) .
N3 C2 1.343(3) .
N3 C4 1.387(3) .
N3 C19 1.453(3) .
C2 C6 1.525(3) .
C4 C5 1.349(3) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C7 C8 1.392(3) .
C7 C12 1.399(3) .
C8 C9 1.396(3) .
C8 C13 1.515(4) .
C9 C10 1.374(4) .
C9 H9 0.9500 .
C10 C11 1.379(4) .
C10 H10 0.9500 .
C11 C12 1.393(4) .
C11 H11 0.9500 .
C12 C16 1.520(4) .
C13 C14 1.521(4) .
C13 C15 1.531(4) .
C13 H13 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C18 1.519(4) .
C16 C17 1.522(4) .
C16 H16 1.0000 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 C20 1.394(3) .
C19 C24 1.400(3) .
C20 C21 1.395(3) .
C20 C25 1.517(4) .
C21 C22 1.375(4) .
C21 H21 0.9500 .
C22 C23 1.381(4) .
C22 H22 0.9500 .
C23 C24 1.393(3) .
C23 H23 0.9500 .
C24 C28 1.515(4) .
C25 C26 1.521(4) .
C25 C27 1.523(4) .
C25 H25 1.0000 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C28 C30 1.527(4) .
C28 C29 1.531(4) .
C28 H28 1.0000 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C31 C32 1.448(5) .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C33 C34 1.408(6) .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 C36 1.488(4) .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C36 H36A 0.9800 .
C36 H36B 0.9800 .
C36 H36C 0.9800 .
C37 C42 1.398(3) .
C37 C38 1.404(3) .
C38 C39 1.391(4) .
C38 H38 0.9500 .
C39 C40 1.369(4) .
C39 H39 0.9500 .
C40 C41 1.371(4) .
C40 H40 0.9500 .
C41 C42 1.394(4) .
C41 H41 0.9500 .
C42 H42 0.9500 .
C43 C48 1.390(3) .
C43 C44 1.396(3) .
C44 C45 1.387(3) .
C44 H44 0.9500 .
C45 C46 1.382(4) .
C45 H45 0.9500 .
C46 C47 1.372(4) .
C46 H46 0.9500 .
C47 C48 1.391(4) .
C47 H47 0.9500 .
C48 H48 0.9500 .
C49 C54 1.402(3) .
C49 C50 1.403(3) .
C50 C51 1.390(4) .
C50 H50 0.9500 .
C51 C52 1.384(4) .
C51 H51 0.9500 .
C52 C53 1.375(4) .
C52 H52 0.9500 .
C53 C54 1.394(3) .
C53 H53 0.9500 .
C54 H54 0.9500 .
C55 C56 1.392(3) .
C55 C60 1.409(3) .
C56 C57 1.398(3) .
C56 H56 0.9500 .
C57 C58 1.379(4) .
C57 H57 0.9500 .
C58 C59 1.382(4) .
C58 H58 0.9500 .
C59 C60 1.384(3) .
C59 H59 0.9500 .
C60 H60 0.9500 .
O4 O4 0.74(2) 3_666
O4 C61A 1.32(2) 3_666
O4 C61 1.492(16) .
C61 C62 1.535(12) .
C61 H61A 0.9900 .
C61 H61B 0.9900 .
C62 C61A 1.609(13) .
C62 H62A 0.9800 .
C62 H62B 0.9800 .
C62 H62C 0.9800 .
C62 H62D 0.9800 .
C62 H62E 0.9800 .
C62 H62F 0.9800 .
C61A O4 1.32(2) 3_666
C61A H61C 0.9900 .
C61A H61D 0.9900 .
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
O2 Na1 O1 C6 -27.7(3) 3_667 .
O3 Na1 O1 C6 -164.1(3) . .
N2 Na1 O1 C6 83.0(3) . .
O2 Na1 O3 C35 -74.9(2) 3_667 .
O1 Na1 O3 C35 62.5(2) . .
N2 Na1 O3 C35 173.60(18) . .
O2 Na1 O3 C34 108.6(3) 3_667 .
O1 Na1 O3 C34 -114.1(3) . .
N2 Na1 O3 C34 -2.9(4) . .
O2 Na1 N2 C31 -41.7(12) 3_667 .
O1 Na1 N2 C31 -163.5(12) . .
O3 Na1 N2 C31 78.9(12) . .
C4 N3 C2 N1 0.3(2) . .
C19 N3 C2 N1 171.73(19) . .
C4 N3 C2 C6 178.9(2) . .
C19 N3 C2 C6 -9.7(3) . .
C5 N1 C2 N3 0.4(2) . .
C7 N1 C2 N3 -178.0(2) . .
C5 N1 C2 C6 -178.2(2) . .
C7 N1 C2 C6 3.4(3) . .
C2 N3 C4 C5 -0.9(2) . .
C19 N3 C4 C5 -172.6(2) . .
N3 C4 C5 N1 1.1(2) . .
C2 N1 C5 C4 -0.9(3) . .
C7 N1 C5 C4 177.5(2) . .
Na1 O1 C6 O2 20.0(5) . .
Na1 O1 C6 C2 -160.91(19) . .
Na1 O2 C6 O1 8.1(5) 3_667 .
Na1 O2 C6 C2 -171.1(2) 3_667 .
N3 C2 C6 O1 -25.9(3) . .
N1 C2 C6 O1 152.3(2) . .
N3 C2 C6 O2 153.4(2) . .
N1 C2 C6 O2 -28.4(3) . .
C2 N1 C7 C8 -85.5(3) . .
C5 N1 C7 C8 96.3(3) . .
C2 N1 C7 C12 95.0(3) . .
C5 N1 C7 C12 -83.1(3) . .
C12 C7 C8 C9 -0.3(4) . .
N1 C7 C8 C9 -179.7(2) . .
C12 C7 C8 C13 179.4(2) . .
N1 C7 C8 C13 0.0(3) . .
C7 C8 C9 C10 -0.1(4) . .
C13 C8 C9 C10 -179.9(3) . .
C8 C9 C10 C11 0.0(5) . .
C9 C10 C11 C12 0.7(5) . .
C10 C11 C12 C7 -1.1(4) . .
C10 C11 C12 C16 178.0(3) . .
C8 C7 C12 C11 0.9(4) . .
N1 C7 C12 C11 -179.7(2) . .
C8 C7 C12 C16 -178.1(2) . .
N1 C7 C12 C16 1.3(3) . .
C7 C8 C13 C14 115.5(3) . .
C9 C8 C13 C14 -64.8(3) . .
C7 C8 C13 C15 -120.5(3) . .
C9 C8 C13 C15 59.2(3) . .
C11 C12 C16 C18 -56.7(3) . .
C7 C12 C16 C18 122.2(3) . .
C11 C12 C16 C17 67.9(3) . .
C7 C12 C16 C17 -113.1(3) . .
C2 N3 C19 C20 108.1(3) . .
C4 N3 C19 C20 -81.6(3) . .
C2 N3 C19 C24 -74.1(3) . .
C4 N3 C19 C24 96.2(3) . .
C24 C19 C20 C21 1.0(3) . .
N3 C19 C20 C21 178.6(2) . .
C24 C19 C20 C25 178.8(2) . .
N3 C19 C20 C25 -3.6(3) . .
C19 C20 C21 C22 0.3(4) . .
C25 C20 C21 C22 -177.6(3) . .
C20 C21 C22 C23 -0.6(4) . .
C21 C22 C23 C24 -0.3(4) . .
C22 C23 C24 C19 1.4(4) . .
C22 C23 C24 C28 -179.4(2) . .
C20 C19 C24 C23 -1.8(3) . .
N3 C19 C24 C23 -179.4(2) . .
C20 C19 C24 C28 179.1(2) . .
N3 C19 C24 C28 1.4(3) . .
C19 C20 C25 C26 137.9(3) . .
C21 C20 C25 C26 -44.4(3) . .
C19 C20 C25 C27 -98.0(3) . .
C21 C20 C25 C27 79.8(3) . .
C23 C24 C28 C30 55.3(3) . .
C19 C24 C28 C30 -125.5(2) . .
C23 C24 C28 C29 -68.7(3) . .
C19 C24 C28 C29 110.4(3) . .
Na1 N2 C31 C32 -31(26) . .
C35 O3 C34 C33 -179.8(4) . .
Na1 O3 C34 C33 -3.1(6) . .
C34 O3 C35 C36 -179.7(3) . .
Na1 O3 C35 C36 2.9(3) . .
C55 B1 C37 C42 -177.3(2) . .
C43 B1 C37 C42 -56.6(3) . .
C49 B1 C37 C42 63.4(3) . .
C55 B1 C37 C38 1.2(3) . .
C43 B1 C37 C38 121.9(2) . .
C49 B1 C37 C38 -118.1(2) . .
C42 C37 C38 C39 -4.2(3) . .
B1 C37 C38 C39 177.1(2) . .
C37 C38 C39 C40 1.5(4) . .
C38 C39 C40 C41 1.5(4) . .
C39 C40 C41 C42 -1.4(4) . .
C40 C41 C42 C37 -1.6(4) . .
C38 C37 C42 C41 4.3(3) . .
B1 C37 C42 C41 -177.1(2) . .
C55 B1 C43 C48 -117.3(3) . .
C37 B1 C43 C48 122.4(2) . .
C49 B1 C43 C48 0.8(3) . .
C55 B1 C43 C44 60.1(3) . .
C37 B1 C43 C44 -60.2(3) . .
C49 B1 C43 C44 178.2(2) . .
C48 C43 C44 C45 1.9(3) . .
B1 C43 C44 C45 -175.7(2) . .
C43 C44 C45 C46 -0.2(4) . .
C44 C45 C46 C47 -1.1(4) . .
C45 C46 C47 C48 0.6(5) . .
C44 C43 C48 C47 -2.4(4) . .
B1 C43 C48 C47 175.1(3) . .
C46 C47 C48 C43 1.3(5) . .
C55 B1 C49 C54 19.5(3) . .
C43 B1 C49 C54 -101.0(2) . .
C37 B1 C49 C54 140.7(2) . .
C55 B1 C49 C50 -164.5(2) . .
C43 B1 C49 C50 75.0(3) . .
C37 B1 C49 C50 -43.3(3) . .
C54 C49 C50 C51 -1.1(4) . .
B1 C49 C50 C51 -177.3(2) . .
C49 C50 C51 C52 0.3(4) . .
C50 C51 C52 C53 0.5(4) . .
C51 C52 C53 C54 -0.4(4) . .
C52 C53 C54 C49 -0.5(4) . .
C50 C49 C54 C53 1.2(3) . .
B1 C49 C54 C53 177.6(2) . .
C43 B1 C55 C56 6.3(3) . .
C37 B1 C55 C56 124.4(2) . .
C49 B1 C55 C56 -113.3(2) . .
C43 B1 C55 C60 -178.4(2) . .
C37 B1 C55 C60 -60.3(3) . .
C49 B1 C55 C60 62.0(3) . .
C60 C55 C56 C57 0.2(3) . .
B1 C55 C56 C57 175.8(2) . .
C55 C56 C57 C58 0.9(4) . .
C56 C57 C58 C59 -1.2(4) . .
C57 C58 C59 C60 0.5(4) . .
C58 C59 C60 C55 0.7(4) . .
C56 C55 C60 C59 -1.0(3) . .
B1 C55 C60 C59 -176.8(2) . .
O4 O4 C61 C62 11(9) 3_666 .
C61A O4 C61 C62 179(2) 3_666 .
O4 C61 C62 C61A -1.6(12) . .
C61 C62 C61A O4 0(3) . 3_666
