#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:49:17 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178446 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/67/4026793.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_4026793
loop_
_publ_author_name
'Jinzhen Lu'
'Xiaohu Qu'
'Germanas Peleckis'
'John F Boas'
'Alan M Bond'
'Lisandra L Martin'
_publ_contact_author_address
' School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.'
_publ_contact_author_email       alan.bond@monash.edu,lisa.martin@monash.edu
_publ_contact_author_fax         ': 61399055142'
_publ_contact_author_name
'prof Alan M Bonda,a/prof Lisarandra L. Martina'
_publ_contact_author_phone       61399055142
_publ_section_title
;
 Synthesis and Structural Characterization of a TCNQ Based Organic
 Semi-Conducting Material with a 2:5 Stoichiometry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10078
_journal_page_last               10082
_journal_paper_doi               10.1021/jo2018334
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C47 H50 N11 O'
_chemical_formula_sum            'C47 H50 N11 O'
_chemical_formula_weight         784.98
_chemical_name_common            ÎTBA2TCNQ5â
_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                100.676(4)
_cell_angle_beta                 92.585(4)
_cell_angle_gamma                92.799(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7869(6)
_cell_length_b                   16.4712(12)
_cell_length_c                   17.3078(13)
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.12
_cell_volume                     2175.5(3)
_computing_cell_refinement       'Bruker Apex2 v2.0'
_computing_data_collection       'Bruker Apex2 v2.0'
_computing_data_reduction        'Bruker Apex2 v2.0'
_computing_molecular_graphics    Îx-seedâ
_computing_publication_material  ÎCIFTABâ
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker X8 APEX 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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27889
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_correction_T_min  0.9799
_exptl_absorpt_correction_type   \^Imulti-scan\^a
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       plate
_exptl_crystal_F_000             834
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         7499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1031P)²+0.1780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1713
_refine_ls_wR_factor_ref         0.2022
_reflns_number_gt                4540
_reflns_number_total             7499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2018334_si_002.cif
_cod_data_source_block
c:\data\docume~1\crysta1\lu9\work\workfo1\platon
_cod_database_code               4026793
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
N1 N 0.6492(2) 0.03508(11) 0.74561(11) 0.0281(5) Uani 1 1 d .
C12 C 0.7533(4) -0.06864(19) 0.45666(16) 0.0586(8) Uani 1 1 d .
H12B H 0.6384 -0.0949 0.4406 0.088 Uiso 1 1 calc R
H12C H 0.8389 -0.0982 0.4242 0.088 Uiso 1 1 calc R
H12A H 0.7560 -0.0109 0.4496 0.088 Uiso 1 1 calc R
C1 C 0.7250(3) 0.01779(15) 0.82295(14) 0.0326(6) Uani 1 1 d .
H1A H 0.6943 -0.0407 0.8253 0.039 Uiso 1 1 calc R
H1B H 0.8520 0.0239 0.8224 0.039 Uiso 1 1 calc R
C16 C 1.1028(4) 0.25968(17) 0.73028(17) 0.0533(8) Uani 1 1 d .
H16A H 1.1658 0.2442 0.7751 0.080 Uiso 1 1 calc R
H16C H 1.1197 0.3195 0.7328 0.080 Uiso 1 1 calc R
H16B H 1.1459 0.2303 0.6811 0.080 Uiso 1 1 calc R
C10 C 0.6752(3) -0.02187(16) 0.59772(14) 0.0387(6) Uani 1 1 d .
H10A H 0.6802 0.0364 0.5903 0.046 Uiso 1 1 calc R
H10B H 0.5551 -0.0449 0.5856 0.046 Uiso 1 1 calc R
C7 C 0.1887(3) -0.06811(16) 0.73541(17) 0.0437(7) Uani 1 1 d .
H7A H 0.1424 -0.0278 0.7780 0.052 Uiso 1 1 calc R
H7B H 0.1538 -0.0526 0.6846 0.052 Uiso 1 1 calc R
C5 C 0.4543(3) 0.02294(14) 0.74053(14) 0.0294(6) Uani 1 1 d .
H5A H 0.4088 0.0628 0.7837 0.035 Uiso 1 1 calc R
H5B H 0.4104 0.0367 0.6902 0.035 Uiso 1 1 calc R
C6 C 0.3828(3) -0.06288(15) 0.74529(15) 0.0350(6) Uani 1 1 d .
H6A H 0.4299 -0.1039 0.7036 0.042 Uiso 1 1 calc R
H6B H 0.4186 -0.0762 0.7969 0.042 Uiso 1 1 calc R
C15 C 0.9140(3) 0.23684(15) 0.73298(15) 0.0383(6) Uani 1 1 d .
H15A H 0.8682 0.2710 0.7800 0.046 Uiso 1 1 calc R
H15B H 0.8518 0.2492 0.6858 0.046 Uiso 1 1 calc R
C9 C 0.7284(3) -0.02530(14) 0.68145(14) 0.0327(6) Uani 1 1 d .
H9A H 0.8551 -0.0157 0.6881 0.039 Uiso 1 1 calc R
H9B H 0.7001 -0.0821 0.6901 0.039 Uiso 1 1 calc R
C14 C 0.8813(3) 0.14706(15) 0.73604(16) 0.0409(7) Uani 1 1 d .
H14A H 0.9423 0.1349 0.7836 0.049 Uiso 1 1 calc R
H14B H 0.9285 0.1130 0.6894 0.049 Uiso 1 1 calc R
C13 C 0.6922(3) 0.12358(13) 0.73770(14) 0.0305(6) Uani 1 1 d .
H13A H 0.6335 0.1334 0.6886 0.037 Uiso 1 1 calc R
H13B H 0.6446 0.1608 0.7822 0.037 Uiso 1 1 calc R
C11 C 0.7944(4) -0.07145(17) 0.54228(16) 0.0478(7) Uani 1 1 d .
H11A H 0.9146 -0.0496 0.5567 0.057 Uiso 1 1 calc R
H11B H 0.7862 -0.1298 0.5493 0.057 Uiso 1 1 calc R
C2 C 0.6711(4) 0.07062(17) 0.89674(14) 0.0454(7) Uani 1 1 d .
H2A H 0.5456 0.0618 0.9014 0.054 Uiso 1 1 calc R
H2B H 0.6968 0.1298 0.8953 0.054 Uiso 1 1 calc R
C8 C 0.1117(4) -0.15332(18) 0.73730(18) 0.0549(8) Uani 1 1 d .
H8B H 0.1541 -0.1932 0.6941 0.082 Uiso 1 1 calc R
H8C H -0.0140 -0.1535 0.7313 0.082 Uiso 1 1 calc R
H8A H 0.1450 -0.1688 0.7877 0.082 Uiso 1 1 calc R
C3 C 0.7694(4) 0.0472(2) 0.96729(17) 0.0620(9) Uani 1 1 d .
H3A H 0.7413 -0.0119 0.9681 0.074 Uiso 1 1 calc R
H3B H 0.8945 0.0538 0.9605 0.074 Uiso 1 1 calc R
C4 C 0.7299(6) 0.0968(3) 1.0428(2) 0.0999(14) Uani 1 1 d .
H4B H 0.7542 0.1556 1.0420 0.150 Uiso 1 1 calc R
H4C H 0.8012 0.0810 1.0852 0.150 Uiso 1 1 calc R
H4A H 0.6080 0.0872 1.0520 0.150 Uiso 1 1 calc R
N8 N 0.5244(3) 0.73165(14) 0.41172(14) 0.0511(6) Uani 1 1 d .
N9 N 0.9686(3) 0.58053(14) 0.39109(13) 0.0469(6) Uani 1 1 d .
N6 N -0.1020(3) 0.33286(13) 0.16320(13) 0.0432(6) Uani 1 1 d .
N7 N 0.3372(3) 0.18071(13) 0.14137(14) 0.0482(6) Uani 1 1 d .
C37 C 0.5408(3) 0.52494(14) 0.31629(13) 0.0266(5) Uani 1 1 d .
C33 C 0.2596(3) 0.46837(14) 0.26090(13) 0.0282(6) Uani 1 1 d .
H33 H 0.1409 0.4755 0.2510 0.034 Uiso 1 1 calc R
C40 C 0.8231(3) 0.58420(15) 0.37644(14) 0.0333(6) Uani 1 1 d .
C30 C 0.2230(3) 0.32339(14) 0.19278(13) 0.0275(5) Uani 1 1 d .
C31 C 0.2870(3) 0.24427(15) 0.16468(14) 0.0317(6) Uani 1 1 d .
C35 C 0.5088(3) 0.38240(14) 0.24804(13) 0.0271(5) Uani 1 1 d .
H35 H 0.5582 0.3313 0.2295 0.032 Uiso 1 1 calc R
C36 C 0.6096(3) 0.44671(14) 0.28780(13) 0.0273(6) Uani 1 1 d .
H36 H 0.7288 0.4400 0.2971 0.033 Uiso 1 1 calc R
C34 C 0.3613(3) 0.53254(14) 0.30088(13) 0.0263(5) Uani 1 1 d .
H34 H 0.3124 0.5838 0.3191 0.032 Uiso 1 1 calc R
C32 C 0.3277(3) 0.38967(14) 0.23318(13) 0.0259(5) Uani 1 1 d .
C29 C 0.0428(3) 0.32936(14) 0.17696(14) 0.0304(6) Uani 1 1 d .
C39 C 0.5774(3) 0.66901(16) 0.38760(14) 0.0343(6) Uani 1 1 d .
C38 C 0.6452(3) 0.59077(15) 0.35878(13) 0.0289(6) Uani 1 1 d .
N11 N 0.4066(3) 0.22680(13) 0.36398(14) 0.0491(6) Uani 1 1 d .
N10 N -0.0385(3) 0.37369(13) 0.38945(13) 0.0455(6) Uani 1 1 d .
C41 C 0.1070(3) 0.37239(14) 0.40223(14) 0.0306(6) Uani 1 1 d .
C42 C 0.2874(3) 0.36756(14) 0.41743(13) 0.0274(5) Uani 1 1 d .
C46 C 0.5735(3) 0.42492(14) 0.47255(12) 0.0243(5) Uani 1 1 d .
H46 H 0.6217 0.3737 0.4532 0.029 Uiso 1 1 calc R
C44 C 0.3928(3) 0.43310(13) 0.45832(12) 0.0237(5) Uani 1 1 d .
C43 C 0.3543(3) 0.28949(15) 0.38770(14) 0.0320(6) Uani 1 1 d .
C45 C 0.3238(3) 0.51174(13) 0.48733(13) 0.0255(5) Uani 1 1 d .
H45 H 0.2048 0.5190 0.4781 0.031 Uiso 1 1 calc R
N4 N 0.4836(3) 0.69205(13) 0.18763(13) 0.0421(6) Uani 1 1 d .
N5 N 0.9150(3) 0.53805(13) 0.15212(13) 0.0412(6) Uani 1 1 d .
N2 N -0.1728(3) 0.29860(15) -0.05084(13) 0.0516(6) Uani 1 1 d .
N3 N 0.2488(3) 0.14112(14) -0.09071(15) 0.0541(7) Uani 1 1 d .
C25 C 0.4802(3) 0.48281(14) 0.09341(12) 0.0243(5) Uani 1 1 d .
C28 C 0.7684(3) 0.54103(14) 0.14350(13) 0.0279(6) Uani 1 1 d .
C24 C 0.5460(3) 0.40366(13) 0.06324(13) 0.0256(5) Uani 1 1 d .
H24 H 0.6652 0.3960 0.0712 0.031 Uiso 1 1 calc R
C21 C 0.1946(3) 0.42798(14) 0.04224(13) 0.0267(5) Uani 1 1 d .
H21 H 0.0750 0.4353 0.0352 0.032 Uiso 1 1 calc R
C23 C 0.4419(3) 0.34026(14) 0.02391(13) 0.0281(6) Uani 1 1 d .
H23 H 0.4890 0.2889 0.0042 0.034 Uiso 1 1 calc R
C18 C 0.1524(3) 0.28502(14) -0.02925(13) 0.0290(6) Uani 1 1 d .
C27 C 0.5263(3) 0.62764(15) 0.16279(13) 0.0279(6) Uani 1 1 d .
C19 C 0.2105(3) 0.20566(16) -0.06263(15) 0.0360(6) Uani 1 1 d .
C22 C 0.2987(3) 0.49135(14) 0.08084(13) 0.0251(5) Uani 1 1 d .
H22 H 0.2516 0.5428 0.1002 0.030 Uiso 1 1 calc R
C17 C -0.0275(3) 0.29297(15) -0.04139(14) 0.0334(6) Uani 1 1 d .
C20 C 0.2609(3) 0.34920(14) 0.01136(12) 0.0256(5) Uani 1 1 d .
C26 C 0.5878(3) 0.54813(14) 0.13280(13) 0.0252(5) Uani 1 1 d .
O1 O 0.7281(5) 0.15823(16) 0.5198(2) 0.1173(11) Uani 1 1 d .
H1 H 0.7280 0.1131 0.4879 0.141 Uiso 1 1 calc R
C47 C 0.8365(5) 0.2167(3) 0.4951(3) 0.1033(15) Uani 1 1 d .
H47A H 0.8419 0.2684 0.5339 0.155 Uiso 1 1 calc R
H47B H 0.7921 0.2268 0.4441 0.155 Uiso 1 1 calc R
H47C H 0.9522 0.1961 0.4899 0.155 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'
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
C13 N1 C5 106.86(15) .
C13 N1 C1 111.02(17) .
C5 N1 C1 111.17(17) .
C13 N1 C9 110.99(17) .
C5 N1 C9 111.27(17) .
C1 N1 C9 105.61(16) .
C11 C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C11 C12 H12A 109.5 .
H12B C12 H12A 109.5 .
H12C C12 H12A 109.5 .
C2 C1 N1 116.84(19) .
C2 C1 H1A 108.1 .
N1 C1 H1A 108.1 .
C2 C1 H1B 108.1 .
N1 C1 H1B 108.1 .
H1A C1 H1B 107.3 .
C15 C16 H16A 109.5 .
C15 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
C15 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
H16C C16 H16B 109.5 .
C9 C10 C11 109.8(2) .
C9 C10 H10A 109.7 .
C11 C10 H10A 109.7 .
C9 C10 H10B 109.7 .
C11 C10 H10B 109.7 .
H10A C10 H10B 108.2 .
C8 C7 C6 112.5(2) .
C8 C7 H7A 109.1 .
C6 C7 H7A 109.1 .
C8 C7 H7B 109.1 .
C6 C7 H7B 109.1 .
H7A C7 H7B 107.8 .
C6 C5 N1 115.67(16) .
C6 C5 H5A 108.4 .
N1 C5 H5A 108.4 .
C6 C5 H5B 108.4 .
N1 C5 H5B 108.4 .
H5A C5 H5B 107.4 .
C7 C6 C5 110.53(18) .
C7 C6 H6A 109.5 .
C5 C6 H6A 109.5 .
C7 C6 H6B 109.5 .
C5 C6 H6B 109.5 .
H6A C6 H6B 108.1 .
C14 C15 C16 111.9(2) .
C14 C15 H15A 109.2 .
C16 C15 H15A 109.2 .
C14 C15 H15B 109.2 .
C16 C15 H15B 109.2 .
H15A C15 H15B 107.9 .
C10 C9 N1 117.08(18) .
C10 C9 H9A 108.0 .
N1 C9 H9A 108.0 .
C10 C9 H9B 108.0 .
N1 C9 H9B 108.0 .
H9A C9 H9B 107.3 .
C15 C14 C13 112.2(2) .
C15 C14 H14A 109.2 .
C13 C14 H14A 109.2 .
C15 C14 H14B 109.2 .
C13 C14 H14B 109.2 .
H14A C14 H14B 107.9 .
C14 C13 N1 115.38(18) .
C14 C13 H13A 108.4 .
N1 C13 H13A 108.4 .
C14 C13 H13B 108.4 .
N1 C13 H13B 108.4 .
H13A C13 H13B 107.5 .
C12 C11 C10 113.1(2) .
C12 C11 H11A 108.9 .
C10 C11 H11A 108.9 .
C12 C11 H11B 108.9 .
C10 C11 H11B 108.9 .
H11A C11 H11B 107.8 .
C1 C2 C3 108.7(2) .
C1 C2 H2A 109.9 .
C3 C2 H2A 109.9 .
C1 C2 H2B 109.9 .
C3 C2 H2B 109.9 .
H2A C2 H2B 108.3 .
C7 C8 H8B 109.5 .
C7 C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C7 C8 H8A 109.5 .
H8B C8 H8A 109.5 .
H8C C8 H8A 109.5 .
C4 C3 C2 113.4(3) .
C4 C3 H3A 108.9 .
C2 C3 H3A 108.9 .
C4 C3 H3B 108.9 .
C2 C3 H3B 108.9 .
H3A C3 H3B 107.7 .
C3 C4 H4B 109.5 .
C3 C4 H4C 109.5 .
H4B C4 H4C 109.5 .
C3 C4 H4A 109.5 .
H4B C4 H4A 109.5 .
H4C C4 H4A 109.5 .
C38 C37 C34 121.4(2) .
C38 C37 C36 121.0(2) .
C34 C37 C36 117.6(2) .
C34 C33 C32 121.1(2) .
C34 C33 H33 119.4 .
C32 C33 H33 119.4 .
N9 C40 C38 178.6(3) .
C32 C30 C31 122.4(2) .
C32 C30 C29 122.3(2) .
C31 C30 C29 115.2(2) .
N7 C31 C30 179.2(3) .
C36 C35 C32 121.2(2) .
C36 C35 H35 119.4 .
C32 C35 H35 119.4 .
C35 C36 C37 121.3(2) .
C35 C36 H36 119.4 .
C37 C36 H36 119.4 .
C33 C34 C37 121.4(2) .
C33 C34 H34 119.3 .
C37 C34 H34 119.3 .
C30 C32 C33 121.2(2) .
C30 C32 C35 121.4(2) .
C33 C32 C35 117.4(2) .
N6 C29 C30 178.7(3) .
N8 C39 C38 179.0(3) .
C37 C38 C40 122.5(2) .
C37 C38 C39 121.3(2) .
C40 C38 C39 116.2(2) .
N10 C41 C42 177.9(3) .
C44 C42 C41 123.3(2) .
C44 C42 C43 121.3(2) .
C41 C42 C43 115.3(2) .
C45 C46 C44 121.4(2) 2_666
C45 C46 H46 119.3 2_666
C44 C46 H46 119.3 .
C42 C44 C46 121.19(19) .
C42 C44 C45 120.7(2) .
C46 C44 C45 118.1(2) .
N11 C43 C42 179.5(3) .
C46 C45 C44 120.5(2) 2_666
C46 C45 H45 119.8 2_666
C44 C45 H45 119.8 .
C26 C25 C22 121.4(2) .
C26 C25 C24 121.2(2) .
C22 C25 C24 117.5(2) .
N5 C28 C26 177.7(2) .
C23 C24 C25 121.3(2) .
C23 C24 H24 119.4 .
C25 C24 H24 119.4 .
C22 C21 C20 121.2(2) .
C22 C21 H21 119.4 .
C20 C21 H21 119.4 .
C24 C23 C20 121.0(2) .
C24 C23 H23 119.5 .
C20 C23 H23 119.5 .
C20 C18 C17 122.2(2) .
C20 C18 C19 123.2(2) .
C17 C18 C19 114.5(2) .
N4 C27 C26 177.4(3) .
N3 C19 C18 176.6(3) .
C21 C22 C25 121.3(2) .
C21 C22 H22 119.4 .
C25 C22 H22 119.4 .
N2 C17 C18 179.2(3) .
C18 C20 C23 121.8(2) .
C18 C20 C21 120.4(2) .
C23 C20 C21 117.8(2) .
C25 C26 C28 121.8(2) .
C25 C26 C27 122.4(2) .
C28 C26 C27 115.8(2) .
C47 O1 H1 109.5 .
O1 C47 H47A 109.5 .
O1 C47 H47B 109.5 .
H47A C47 H47B 109.5 .
O1 C47 H47C 109.5 .
H47A C47 H47C 109.5 .
H47B C47 H47C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C13 1.512(3) .
N1 C5 1.518(3) .
N1 C1 1.519(3) .
N1 C9 1.521(3) .
C12 C11 1.512(4) .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C12 H12A 0.9800 .
C1 C2 1.496(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C16 C15 1.505(4) .
C16 H16A 0.9800 .
C16 H16C 0.9800 .
C16 H16B 0.9800 .
C10 C9 1.501(3) .
C10 C11 1.521(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C7 C8 1.506(4) .
C7 C6 1.510(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C5 C6 1.512(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C15 C14 1.499(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C14 C13 1.507(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C2 C3 1.532(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C8 H8A 0.9800 .
C3 C4 1.462(4) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C4 H4A 0.9800 .
N8 C39 1.143(3) .
N9 C40 1.156(3) .
N6 C29 1.148(3) .
N7 C31 1.144(3) .
C37 C38 1.394(3) .
C37 C34 1.427(3) .
C37 C36 1.431(3) .
C33 C34 1.349(3) .
C33 C32 1.432(3) .
C33 H33 0.9500 .
C40 C38 1.419(3) .
C30 C32 1.387(3) .
C30 C31 1.426(3) .
C30 C29 1.429(3) .
C35 C36 1.346(3) .
C35 C32 1.436(3) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C34 H34 0.9500 .
C39 C38 1.428(3) .
N11 C43 1.140(3) .
N10 C41 1.147(3) .
C41 C42 1.426(3) .
C42 C44 1.385(3) .
C42 C43 1.426(3) .
C46 C45 1.346(3) 2_666
C46 C44 1.435(3) .
C46 H46 0.9500 .
C44 C45 1.439(3) .
C45 C46 1.346(3) 2_666
C45 H45 0.9500 .
N4 C27 1.140(3) .
N5 C28 1.149(3) .
N2 C17 1.146(3) .
N3 C19 1.144(3) .
C25 C26 1.383(3) .
C25 C22 1.438(3) .
C25 C24 1.439(3) .
C28 C26 1.424(3) .
C24 C23 1.347(3) .
C24 H24 0.9500 .
C21 C22 1.343(3) .
C21 C20 1.438(3) .
C21 H21 0.9500 .
C23 C20 1.435(3) .
C23 H23 0.9500 .
C18 C20 1.382(3) .
C18 C17 1.423(3) .
C18 C19 1.431(3) .
C27 C26 1.430(3) .
C22 H22 0.9500 .
O1 C47 1.389(5) .
O1 H1 0.8400 .
C47 H47A 0.9800 .
C47 H47B 0.9800 .
C47 H47C 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
C13 N1 C1 C2 58.3(3) . .
C5 N1 C1 C2 -60.5(3) . .
C9 N1 C1 C2 178.7(2) . .
C13 N1 C5 C6 178.64(19) . .
C1 N1 C5 C6 -60.1(3) . .
C9 N1 C5 C6 57.3(2) . .
C8 C7 C6 C5 178.3(2) . .
N1 C5 C6 C7 -177.1(2) . .
C11 C10 C9 N1 167.3(2) . .
C13 N1 C9 C10 -59.7(3) . .
C5 N1 C9 C10 59.2(3) . .
C1 N1 C9 C10 179.9(2) . .
C16 C15 C14 C13 -179.3(2) . .
C15 C14 C13 N1 -176.6(2) . .
C5 N1 C13 C14 -176.3(2) . .
C1 N1 C13 C14 62.4(3) . .
C9 N1 C13 C14 -54.8(3) . .
C9 C10 C11 C12 -178.0(2) . .
N1 C1 C2 C3 -176.5(2) . .
C1 C2 C3 C4 178.4(3) . .
C32 C30 C31 N7 -140(23) . .
C29 C30 C31 N7 40(23) . .
C32 C35 C36 C37 -0.5(3) . .
C38 C37 C36 C35 178.7(2) . .
C34 C37 C36 C35 -0.2(3) . .
C32 C33 C34 C37 0.8(3) . .
C38 C37 C34 C33 -178.8(2) . .
C36 C37 C34 C33 0.0(3) . .
C31 C30 C32 C33 -179.8(2) . .
C29 C30 C32 C33 -0.4(3) . .
C31 C30 C32 C35 0.9(3) . .
C29 C30 C32 C35 -179.6(2) . .
C34 C33 C32 C30 179.3(2) . .
C34 C33 C32 C35 -1.4(3) . .
C36 C35 C32 C30 -179.5(2) . .
C36 C35 C32 C33 1.2(3) . .
C32 C30 C29 N6 163(13) . .
C31 C30 C29 N6 -18(13) . .
C34 C37 C38 C40 178.5(2) . .
C36 C37 C38 C40 -0.3(3) . .
C34 C37 C38 C39 -1.0(3) . .
C36 C37 C38 C39 -179.8(2) . .
N9 C40 C38 C37 160(11) . .
N9 C40 C38 C39 -20(11) . .
N8 C39 C38 C37 134(17) . .
N8 C39 C38 C40 -45(17) . .
N10 C41 C42 C44 -164(7) . .
N10 C41 C42 C43 15(7) . .
C41 C42 C44 C46 179.6(2) . .
C43 C42 C44 C46 -0.2(3) . .
C41 C42 C44 C45 -0.9(3) . .
C43 C42 C44 C45 179.4(2) . .
C45 C46 C44 C42 -179.6(2) 2_666 .
C45 C46 C44 C45 0.8(3) 2_666 .
C44 C42 C43 N11 154(100) . .
C41 C42 C43 N11 -26(28) . .
C42 C44 C45 C46 179.6(2) . 2_666
C46 C44 C45 C46 -0.8(3) . 2_666
C26 C25 C24 C23 -179.1(2) . .
C22 C25 C24 C23 0.8(3) . .
C25 C24 C23 C20 -0.6(3) . .
C20 C18 C19 N3 -178(100) . .
C17 C18 C19 N3 2(5) . .
C20 C21 C22 C25 -0.5(3) . .
C26 C25 C22 C21 179.7(2) . .
C24 C25 C22 C21 -0.2(3) . .
C20 C18 C17 N2 -127(25) . .
C19 C18 C17 N2 53(25) . .
C17 C18 C20 C23 179.4(2) . .
C19 C18 C20 C23 -0.8(4) . .
C17 C18 C20 C21 -0.9(3) . .
C19 C18 C20 C21 178.9(2) . .
C24 C23 C20 C18 179.6(2) . .
C24 C23 C20 C21 -0.1(3) . .
C22 C21 C20 C18 -179.0(2) . .
C22 C21 C20 C23 0.7(3) . .
C22 C25 C26 C28 -178.11(19) . .
C24 C25 C26 C28 1.7(3) . .
C22 C25 C26 C27 -0.4(3) . .
C24 C25 C26 C27 179.44(19) . .
N5 C28 C26 C25 150(6) . .
N5 C28 C26 C27 -28(6) . .
N4 C27 C26 C25 -178(100) . .
N4 C27 C26 C28 0(6) . .
