#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/19/4111920.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_4111920
loop_
_publ_author_name
'Christel Dolain'
'Hua Jiang'
'Jean-Michel Léger'
'Philippe Guionneau'
'Ivan Huc'
_publ_section_title
;
 Chiral Induction in Quinoline-Derived Oligoamide Foldamers: Assignment of
 Helical Handedness and Role of Steric Effects
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12943
_journal_page_last               12951
_journal_paper_doi               10.1021/ja0527828
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C70.5 H76 N9 O10'
_chemical_formula_weight         1209.40
_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                90.150(10)
_cell_angle_beta                 104.040(10)
_cell_angle_gamma                117.100(10)
_cell_formula_units_Z            2
_cell_length_a                   13.2710(10)
_cell_length_b                   14.1310(10)
_cell_length_c                   20.6520(10)
_cell_measurement_temperature    296(2)
_cell_volume                     3315.9(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20134
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_type   'semi-empirical method scalepack'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       prism
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     813
_refine_ls_number_reflns         11531
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0837
_refine_ls_shift/su_max          3.981
_refine_ls_shift/su_mean         0.120
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1735P)²+0.5700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2367
_refine_ls_wR_factor_ref         0.2883
_reflns_number_gt                6658
_reflns_number_total             11531
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0527828si20050429_045704.cif
_cod_data_source_block           compound9
_cod_original_cell_volume        3315.9(4)
_cod_original_formula_sum        'C70.50 H76 N9 O10'
_cod_database_code               4111920
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
C1 C 0.2608(4) 0.5661(4) 0.1991(2) 0.0822(11) Uani 1 1 d .
C2 C 0.3577(5) 0.6619(4) 0.2209(3) 0.1033(14) Uani 1 1 d .
H2 H 0.4087 0.6722 0.2632 0.124 Uiso 1 1 calc R
C3 C 0.3834(7) 0.7450(6) 0.1824(4) 0.144(2) Uani 1 1 d .
H3 H 0.4505 0.8103 0.1993 0.172 Uiso 1 1 calc R
C4 C 0.3132(10) 0.7326(8) 0.1214(5) 0.171(3) Uani 1 1 d .
H4 H 0.3314 0.7890 0.0956 0.205 Uiso 1 1 calc R
C5 C 0.2152(10) 0.6381(9) 0.0968(4) 0.173(3) Uani 1 1 d .
H5 H 0.1664 0.6294 0.0540 0.208 Uiso 1 1 calc R
C6 C 0.1859(6) 0.5498(6) 0.1372(2) 0.1280(19) Uani 1 1 d .
H6 H 0.1183 0.4845 0.1212 0.154 Uiso 1 1 calc R
C7 C 0.2290(3) 0.4760(3) 0.24254(19) 0.0774(10) Uani 1 1 d .
H7 H 0.1707 0.4095 0.2130 0.093 Uiso 1 1 calc R
C8 C 0.1754(3) 0.4924(4) 0.2951(2) 0.0892(12) Uani 1 1 d .
H8A H 0.1556 0.4330 0.3207 0.134 Uiso 1 1 calc R
H8B H 0.1054 0.4973 0.2736 0.134 Uiso 1 1 calc R
H8C H 0.2307 0.5575 0.3247 0.134 Uiso 1 1 calc R
N9 N 0.3318(2) 0.4625(2) 0.27494(15) 0.0726(8) Uani 1 1 d .
H9 H 0.3589 0.4754 0.3181 0.087 Uiso 1 1 calc R
C10 C 0.3841(3) 0.4304(3) 0.23888(18) 0.0636(8) Uani 1 1 d .
O11 O 0.3504(2) 0.4106(2) 0.17749(13) 0.0805(7) Uani 1 1 d .
C12 C 0.4901(3) 0.4221(2) 0.27848(17) 0.0618(8) Uani 1 1 d .
C13 C 0.5709(3) 0.4255(3) 0.24438(18) 0.0693(9) Uani 1 1 d .
H13 H 0.5554 0.4260 0.1980 0.083 Uiso 1 1 calc R
C14 C 0.6735(3) 0.4279(3) 0.2811(2) 0.0722(10) Uani 1 1 d .
C15 C 0.6952(3) 0.4272(3) 0.35181(19) 0.0660(9) Uani 1 1 d .
C16 C 0.6055(3) 0.4181(2) 0.38011(17) 0.0588(8) Uani 1 1 d .
N17 N 0.5037(2) 0.41686(19) 0.34363(13) 0.0581(7) Uani 1 1 d .
O18 O 0.7594(2) 0.4317(2) 0.25501(14) 0.0902(8) Uani 1 1 d .
C19 C 0.7383(4) 0.4220(4) 0.1830(2) 0.0955(13) Uani 1 1 d .
H19A H 0.7388 0.4864 0.1665 0.115 Uiso 1 1 calc R
H19B H 0.6622 0.3614 0.1619 0.115 Uiso 1 1 calc R
C20 C 0.8349(4) 0.4061(5) 0.1667(3) 0.1157(17) Uani 1 1 d .
H20 H 0.9108 0.4678 0.1892 0.139 Uiso 1 1 calc R
C21 C 0.8186(6) 0.4012(8) 0.0909(3) 0.177(3) Uani 1 1 d .
H21A H 0.8178 0.4652 0.0762 0.266 Uiso 1 1 calc R
H21B H 0.7455 0.3399 0.0683 0.266 Uiso 1 1 calc R
H21C H 0.8823 0.3952 0.0805 0.266 Uiso 1 1 calc R
C22 C 0.8343(7) 0.3078(7) 0.1919(4) 0.181(3) Uani 1 1 d .
H22A H 0.8969 0.2993 0.1819 0.272 Uiso 1 1 calc R
H22B H 0.7603 0.2467 0.1704 0.272 Uiso 1 1 calc R
H22C H 0.8454 0.3139 0.2397 0.272 Uiso 1 1 calc R
C23 C 0.8006(3) 0.4350(3) 0.3945(2) 0.0792(11) Uani 1 1 d .
H23 H 0.8607 0.4410 0.3765 0.095 Uiso 1 1 calc R
C24 C 0.8137(3) 0.4336(3) 0.4611(2) 0.0800(11) Uani 1 1 d .
H24 H 0.8842 0.4406 0.4886 0.096 Uiso 1 1 calc R
C25 C 0.7237(3) 0.4220(3) 0.49026(19) 0.0716(9) Uani 1 1 d .
H25 H 0.7352 0.4218 0.5365 0.086 Uiso 1 1 calc R
C26 C 0.6198(3) 0.4108(2) 0.45018(17) 0.0595(8) Uani 1 1 d .
N27 N 0.5203(2) 0.3892(2) 0.47142(14) 0.0626(7) Uani 1 1 d .
H27 H 0.4619 0.3862 0.4405 0.075 Uiso 1 1 calc R
C28 C 0.5006(3) 0.3722(2) 0.53219(17) 0.0632(8) Uani 1 1 d .
O29 O 0.5774(2) 0.3877(2) 0.58452(12) 0.0858(8) Uani 1 1 d .
C30 C 0.3759(3) 0.3355(2) 0.53212(16) 0.0599(8) Uani 1 1 d .
C31 C 0.3472(3) 0.3258(2) 0.59286(17) 0.0669(9) Uani 1 1 d .
H31 H 0.4035 0.3369 0.6331 0.080 Uiso 1 1 calc R
C32 C 0.2330(3) 0.2991(3) 0.59229(17) 0.0714(10) Uani 1 1 d .
C33 C 0.1500(3) 0.2852(2) 0.53035(18) 0.0658(9) Uani 1 1 d .
C34 C 0.1862(3) 0.2866(2) 0.47132(16) 0.0603(8) Uani 1 1 d .
N35 N 0.2986(2) 0.31261(19) 0.47233(13) 0.0602(7) Uani 1 1 d .
O36 O 0.1938(2) 0.2850(2) 0.64748(13) 0.0935(9) Uani 1 1 d .
C37 C 0.2744(4) 0.2826(4) 0.7112(2) 0.1172(19) Uani 1 1 d .
H37A H 0.3116 0.2410 0.7015 0.141 Uiso 1 1 calc R
H37B H 0.3358 0.3551 0.7289 0.141 Uiso 1 1 calc R
C38 C 0.2170(5) 0.2390(5) 0.7595(3) 0.132(2) Uani 1 1 d .
H38 H 0.1786 0.2817 0.7666 0.159 Uiso 1 1 calc R
C39 C 0.1213(4) 0.1259(4) 0.7387(3) 0.1160(16) Uani 1 1 d .
H39A H 0.0825 0.1024 0.7736 0.174 Uiso 1 1 calc R
H39B H 0.1546 0.0805 0.7311 0.174 Uiso 1 1 calc R
H39C H 0.0654 0.1221 0.6980 0.174 Uiso 1 1 calc R
C40 C 0.3082(6) 0.2573(7) 0.8251(3) 0.172(3) Uani 1 1 d .
H40A H 0.2698 0.2298 0.8598 0.259 Uiso 1 1 calc R
H40B H 0.3606 0.3327 0.8374 0.259 Uiso 1 1 calc R
H40C H 0.3523 0.2209 0.8199 0.259 Uiso 1 1 calc R
C41 C 0.1009(3) 0.2555(3) 0.40675(17) 0.0629(8) Uani 1 1 d .
C42 C -0.0094(3) 0.2410(3) 0.4026(2) 0.0754(10) Uani 1 1 d .
H42 H -0.0636 0.2262 0.3609 0.090 Uiso 1 1 calc R
C43 C -0.0404(3) 0.2487(3) 0.4622(2) 0.0824(11) Uani 1 1 d .
H43 H -0.1150 0.2411 0.4589 0.099 Uiso 1 1 calc R
C44 C 0.0345(3) 0.2668(3) 0.5245(2) 0.0791(10) Uani 1 1 d .
H44 H 0.0095 0.2670 0.5629 0.095 Uiso 1 1 calc R
N45 N 0.1403(2) 0.2393(2) 0.35326(13) 0.0677(7) Uani 1 1 d .
H45 H 0.2145 0.2595 0.3627 0.081 Uiso 1 1 calc R
C46 C 0.0794(3) 0.1966(3) 0.28890(17) 0.0719(9) Uani 1 1 d .
O47 O -0.0228(2) 0.1764(3) 0.26408(15) 0.1026(9) Uani 1 1 d .
C48 C 0.1488(3) 0.1776(3) 0.24747(17) 0.0699(9) Uani 1 1 d .
N49 N 0.2435(2) 0.1703(2) 0.28014(13) 0.0655(7) Uani 1 1 d .
C50 C 0.3088(3) 0.1567(3) 0.24208(17) 0.0699(9) Uani 1 1 d .
C51 C 0.2815(4) 0.1543(3) 0.17173(19) 0.0823(11) Uani 1 1 d .
C52 C 0.1806(4) 0.1651(3) 0.14026(19) 0.0899(13) Uani 1 1 d .
C53 C 0.1120(4) 0.1733(3) 0.17762(19) 0.0863(12) Uani 1 1 d .
H53 H 0.0430 0.1760 0.1571 0.104 Uiso 1 1 calc R
O54 O 0.1599(3) 0.1669(3) 0.07255(14) 0.1202(12) Uani 1 1 d .
C55 C 0.0770(8) 0.2033(7) 0.0411(3) 0.169(3) Uani 1 1 d .
H55A H 0.0944 0.2697 0.0660 0.202 Uiso 1 1 calc R
H55B H -0.0024 0.1501 0.0399 0.202 Uiso 1 1 calc R
C56 C 0.0882(9) 0.2207(7) -0.0306(3) 0.193(4) Uani 1 1 d .
H56 H 0.1706 0.2659 -0.0299 0.231 Uiso 1 1 calc R
C57 C 0.0414(9) 0.1157(7) -0.0692(4) 0.205(4) Uani 1 1 d .
H57A H 0.0889 0.0825 -0.0502 0.308 Uiso 1 1 calc R
H57B H 0.0426 0.1243 -0.1151 0.308 Uiso 1 1 calc R
H57C H -0.0381 0.0713 -0.0676 0.308 Uiso 1 1 calc R
C58 C 0.0190(19) 0.2728(13) -0.0570(5) 0.428(14) Uani 1 1 d .
H58A H 0.0228 0.2859 -0.1022 0.643 Uiso 1 1 calc R
H58B H 0.0491 0.3397 -0.0294 0.643 Uiso 1 1 calc R
H58C H -0.0613 0.2277 -0.0572 0.643 Uiso 1 1 calc R
C59 C 0.4097(3) 0.1473(3) 0.27697(19) 0.0708(9) Uani 1 1 d .
C60 C 0.4817(4) 0.1393(3) 0.2421(2) 0.0881(12) Uani 1 1 d .
H60 H 0.5484 0.1344 0.2647 0.106 Uiso 1 1 calc R
C61 C 0.4545(5) 0.1387(4) 0.1724(3) 0.1060(15) Uani 1 1 d .
H61 H 0.5040 0.1334 0.1492 0.127 Uiso 1 1 calc R
C62 C 0.3572(5) 0.1457(4) 0.1373(2) 0.1050(15) Uani 1 1 d .
H62 H 0.3409 0.1449 0.0908 0.126 Uiso 1 1 calc R
N63 N 0.4256(2) 0.1439(2) 0.34575(15) 0.0709(8) Uani 1 1 d .
H63 H 0.3682 0.1394 0.3602 0.085 Uiso 1 1 calc R
C64 C 0.5173(3) 0.1466(2) 0.39350(18) 0.0641(9) Uani 1 1 d .
O65 O 0.6107(2) 0.1612(2) 0.38470(14) 0.0840(8) Uani 1 1 d .
C66 C 0.4919(3) 0.1289(2) 0.46065(18) 0.0624(8) Uani 1 1 d .
N67 N 0.3812(2) 0.0947(2) 0.46057(14) 0.0619(7) Uani 1 1 d .
C68 C 0.3562(3) 0.0745(2) 0.52075(18) 0.0603(8) Uani 1 1 d .
C69 C 0.4415(3) 0.0938(2) 0.58176(18) 0.0634(8) Uani 1 1 d .
C70 C 0.5600(3) 0.1346(3) 0.57864(19) 0.0673(9) Uani 1 1 d .
C71 C 0.5842(3) 0.1491(2) 0.51798(19) 0.0660(9) Uani 1 1 d .
H71 H 0.6603 0.1718 0.5147 0.079 Uiso 1 1 calc R
C72 C 0.2382(3) 0.0350(2) 0.52376(19) 0.0646(9) Uani 1 1 d .
C73 C 0.2072(3) 0.0181(3) 0.5821(2) 0.0761(10) Uani 1 1 d .
H73 H 0.1298 -0.0041 0.5824 0.091 Uiso 1 1 calc R
C74 C 0.2927(3) 0.0343(3) 0.6416(2) 0.0818(11) Uani 1 1 d .
H74 H 0.2714 0.0195 0.6816 0.098 Uiso 1 1 calc R
C75 C 0.4070(3) 0.0714(3) 0.6420(2) 0.0775(10) Uani 1 1 d .
H75 H 0.4631 0.0823 0.6822 0.093 Uiso 1 1 calc R
N76 N 0.1456(2) 0.0092(2) 0.46067(18) 0.0743(8) Uani 1 1 d .
O77 O 0.0801(3) 0.0479(2) 0.45780(17) 0.1044(10) Uani 1 1 d .
O78 O 0.1364(3) -0.0529(3) 0.41615(18) 0.1211(12) Uani 1 1 d .
O79 O 0.6391(2) 0.1556(2) 0.63873(13) 0.0824(7) Uani 1 1 d .
C80 C 0.7603(3) 0.2070(3) 0.6406(2) 0.0829(11) Uani 1 1 d .
H80A H 0.7799 0.2727 0.6202 0.099 Uiso 1 1 calc R
H80B H 0.7774 0.1605 0.6156 0.099 Uiso 1 1 calc R
C81 C 0.8317(3) 0.2319(3) 0.7134(2) 0.0866(11) Uani 1 1 d .
H81 H 0.8079 0.2738 0.7382 0.104 Uiso 1 1 calc R
C82 C 0.8081(5) 0.1285(4) 0.7445(3) 0.1243(19) Uani 1 1 d .
H82A H 0.7260 0.0888 0.7420 0.186 Uiso 1 1 calc R
H82B H 0.8536 0.1457 0.7908 0.186 Uiso 1 1 calc R
H82C H 0.8300 0.0860 0.7203 0.186 Uiso 1 1 calc R
C83 C 0.9589(4) 0.2981(4) 0.7174(3) 0.1174(17) Uani 1 1 d .
H83A H 0.9709 0.3634 0.6989 0.176 Uiso 1 1 calc R
H83B H 0.9832 0.2588 0.6924 0.176 Uiso 1 1 calc R
H83C H 1.0045 0.3147 0.7636 0.176 Uiso 1 1 calc R
C84 C 0.4511(11) 0.4194(12) 0.0370(6) 0.330(11) Uani 1 1 d D
H84 H 0.4127 0.3704 0.0638 0.396 Uiso 1 1 calc R
C85 C 0.4485(8) 0.5166(13) 0.0410(5) 0.255(8) Uani 1 1 d D
H85 H 0.4120 0.5240 0.0724 0.306 Uiso 1 1 calc R
C86 C 0.4953(7) 0.6140(10) 0.0028(5) 0.302(9) Uani 1 1 d D
C87 C 0.5076(7) 0.7047(5) 0.0021(4) 0.0531(17) Uani 0.50 1 d PD
H87A H 0.5816 0.7536 0.0328 0.080 Uiso 0.50 1 calc PR
H87B H 0.4448 0.7080 0.0155 0.080 Uiso 0.50 1 calc PR
H87C H 0.5061 0.7239 -0.0426 0.080 Uiso 0.50 1 calc PR
C88 C 0.5549(11) 0.0062(14) 0.0129(9) 0.283(7) Uani 1 1 d .
H88A H 0.5988 0.0765 0.0003 0.340 Uiso 1 1 calc R
H88B H 0.5536 -0.0425 -0.0209 0.340 Uiso 1 1 calc R
C89 C 0.6417(17) 0.0069(18) 0.0634(13) 0.404(16) Uani 1 1 d .
H89A H 0.6443 0.0527 0.0995 0.485 Uiso 1 1 calc R
H89B H 0.6040 -0.0650 0.0753 0.485 Uiso 1 1 calc R
C90 C 0.7452(16) 0.0255(17) 0.0764(12) 0.400(13) Uani 1 1 d .
H90A H 0.7690 0.0103 0.1211 0.599 Uiso 1 1 calc R
H90B H 0.7940 0.0997 0.0734 0.599 Uiso 1 1 calc R
H90C H 0.7530 -0.0188 0.0447 0.599 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
_geom_angle_site_symmetry_3
C2 C1 C6 119.6(5) . .
C2 C1 C7 122.2(4) . .
C6 C1 C7 118.1(5) . .
C1 C2 C3 122.0(6) . .
C4 C3 C2 120.6(8) . .
C3 C4 C5 119.9(8) . .
C4 C5 C6 120.2(7) . .
C1 C6 C5 117.7(7) . .
N9 C7 C8 109.6(3) . .
N9 C7 C1 111.1(3) . .
C8 C7 C1 112.7(3) . .
C10 N9 C7 121.2(3) . .
O11 C10 N9 123.0(3) . .
O11 C10 C12 121.4(3) . .
N9 C10 C12 115.6(3) . .
N17 C12 C13 124.3(3) . .
N17 C12 C10 117.9(3) . .
C13 C12 C10 117.8(3) . .
C14 C13 C12 118.4(3) . .
O18 C14 C13 124.8(4) . .
O18 C14 C15 115.5(3) . .
C13 C14 C15 119.8(3) . .
C16 C15 C14 116.9(3) . .
C16 C15 C23 119.0(3) . .
C14 C15 C23 124.0(3) . .
N17 C16 C15 123.3(3) . .
N17 C16 C26 117.4(3) . .
C15 C16 C26 119.3(3) . .
C12 N17 C16 117.2(3) . .
C14 O18 C19 118.4(3) . .
O18 C19 C20 107.8(4) . .
C22 C20 C19 110.3(5) . .
C22 C20 C21 111.7(6) . .
C19 C20 C21 109.1(4) . .
C24 C23 C15 120.1(4) . .
C23 C24 C25 121.8(3) . .
C26 C25 C24 119.5(4) . .
C25 C26 N27 125.4(3) . .
C25 C26 C16 120.0(3) . .
N27 C26 C16 114.6(3) . .
C28 N27 C26 130.6(3) . .
O29 C28 N27 124.4(3) . .
O29 C28 C30 121.5(3) . .
N27 C28 C30 114.1(3) . .
N35 C30 C31 124.3(3) . .
N35 C30 C28 116.5(3) . .
C31 C30 C28 119.3(3) . .
C30 C31 C32 118.5(3) . .
O36 C32 C31 124.2(3) . .
O36 C32 C33 116.5(4) . .
C31 C32 C33 119.3(3) . .
C44 C33 C34 119.0(3) . .
C44 C33 C32 124.1(3) . .
C34 C33 C32 116.8(3) . .
N35 C34 C33 123.0(3) . .
N35 C34 C41 117.4(3) . .
C33 C34 C41 119.5(3) . .
C30 N35 C34 117.4(3) . .
C32 O36 C37 117.0(3) . .
C38 C37 O36 112.7(4) . .
C37 C38 C39 114.1(5) . .
C37 C38 C40 108.4(5) . .
C39 C38 C40 115.0(5) . .
C42 C41 N45 125.9(3) . .
C42 C41 C34 119.5(3) . .
N45 C41 C34 114.6(3) . .
C41 C42 C43 119.3(4) . .
C44 C43 C42 122.6(4) . .
C43 C44 C33 119.3(4) . .
C46 N45 C41 129.5(3) . .
O47 C46 N45 124.6(4) . .
O47 C46 C48 121.1(3) . .
N45 C46 C48 114.3(3) . .
N49 C48 C53 124.5(4) . .
N49 C48 C46 117.4(3) . .
C53 C48 C46 118.0(3) . .
C48 N49 C50 117.1(3) . .
N49 C50 C51 123.0(4) . .
N49 C50 C59 117.2(3) . .
C51 C50 C59 119.7(4) . .
C50 C51 C62 119.0(4) . .
C50 C51 C52 116.8(4) . .
C62 C51 C52 124.1(4) . .
O54 C52 C53 124.6(4) . .
O54 C52 C51 115.1(4) . .
C53 C52 C51 120.3(4) . .
C52 C53 C48 118.1(4) . .
C52 O54 C55 116.9(4) . .
O54 C55 C56 107.0(6) . .
C58 C56 C57 111.2(9) . .
C58 C56 C55 105.8(10) . .
C57 C56 C55 108.0(7) . .
C60 C59 N63 124.5(4) . .
C60 C59 C50 119.8(4) . .
N63 C59 C50 115.7(3) . .
C59 C60 C61 119.8(5) . .
C62 C61 C60 121.9(5) . .
C61 C62 C51 119.7(4) . .
C64 N63 C59 130.0(3) . .
O65 C64 N63 125.5(3) . .
O65 C64 C66 122.4(3) . .
N63 C64 C66 112.1(3) . .
N67 C66 C71 124.8(3) . .
N67 C66 C64 116.0(3) . .
C71 C66 C64 119.2(3) . .
C66 N67 C68 116.6(3) . .
N67 C68 C69 123.8(3) . .
N67 C68 C72 119.3(3) . .
C69 C68 C72 116.8(3) . .
C68 C69 C75 119.6(3) . .
C68 C69 C70 116.7(3) . .
C75 C69 C70 123.7(3) . .
O79 C70 C71 125.9(3) . .
O79 C70 C69 114.5(3) . .
C71 C70 C69 119.6(3) . .
C70 C71 C66 118.4(3) . .
C73 C72 C68 122.9(3) . .
C73 C72 N76 118.6(3) . .
C68 C72 N76 118.6(3) . .
C72 C73 C74 119.2(3) . .
C75 C74 C73 120.7(4) . .
C74 C75 C69 120.7(4) . .
O77 N76 O78 124.4(4) . .
O77 N76 C72 117.4(3) . .
O78 N76 C72 118.1(3) . .
C70 O79 C80 117.7(3) . .
O79 C80 C81 108.1(3) . .
C83 C81 C80 109.2(4) . .
C83 C81 C82 111.7(4) . .
C80 C81 C82 110.5(3) . .
C85 C84 C86 128.1(14) . 2_665
C84 C85 C86 131.5(11) . .
C87 C86 C84 118.5(14) . 2_665
C87 C86 C85 140.7(13) . .
C84 C86 C85 100.4(10) 2_665 .
C88 C88 C89 152(3) 2_655 .
C90 C89 C88 141(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.349(6) .
C1 C6 1.359(6) .
C1 C7 1.517(6) .
C2 C3 1.378(7) .
C3 C4 1.330(10) .
C4 C5 1.351(11) .
C5 C6 1.459(10) .
C7 N9 1.463(4) .
C7 C8 1.505(5) .
N9 C10 1.334(4) .
C10 O11 1.223(4) .
C10 C12 1.501(5) .
C12 N17 1.320(4) .
C12 C13 1.403(5) .
C13 C14 1.373(5) .
C14 O18 1.356(4) .
C14 C15 1.418(5) .
C15 C16 1.405(5) .
C15 C23 1.416(5) .
C16 N17 1.370(4) .
C16 C26 1.423(5) .
O18 C19 1.438(5) .
C19 C20 1.510(6) .
C20 C22 1.481(9) .
C20 C21 1.524(8) .
C23 C24 1.344(6) .
C24 C25 1.410(5) .
C25 C26 1.364(5) .
C26 N27 1.394(4) .
N27 C28 1.343(4) .
C28 O29 1.231(4) .
C28 C30 1.493(5) .
C30 N35 1.327(4) .
C30 C31 1.386(5) .
C31 C32 1.382(5) .
C32 O36 1.343(4) .
C32 C33 1.416(5) .
C33 C44 1.407(5) .
C33 C34 1.411(5) .
C34 N35 1.360(4) .
C34 C41 1.437(4) .
O36 C37 1.493(5) .
C37 C38 1.378(7) .
C38 C39 1.495(7) .
C38 C40 1.512(7) .
C41 C42 1.363(5) .
C41 N45 1.391(4) .
C42 C43 1.407(5) .
C43 C44 1.363(6) .
N45 C46 1.347(4) .
C46 O47 1.221(4) .
C46 C48 1.503(5) .
C48 N49 1.324(4) .
C48 C53 1.398(5) .
N49 C50 1.373(5) .
C50 C51 1.406(5) .
C50 C59 1.424(5) .
C51 C62 1.409(6) .
C51 C52 1.416(6) .
C52 O54 1.361(5) .
C52 C53 1.368(6) .
O54 C55 1.438(8) .
C55 C56 1.532(9) .
C56 C58 1.434(15) .
C56 C57 1.462(10) .
C59 C60 1.369(5) .
C59 N63 1.389(5) .
C60 C61 1.394(6) .
C61 C62 1.366(7) .
N63 C64 1.353(4) .
C64 O65 1.221(4) .
C64 C66 1.500(5) .
C66 N67 1.320(4) .
C66 C71 1.401(5) .
N67 C68 1.361(4) .
C68 C69 1.403(5) .
C68 C72 1.420(4) .
C69 C75 1.415(5) .
C69 C70 1.426(5) .
C70 O79 1.346(4) .
C70 C71 1.361(5) .
C72 C73 1.353(5) .
C72 N76 1.468(5) .
C73 C74 1.392(5) .
C74 C75 1.358(5) .
N76 O77 1.211(4) .
N76 O78 1.214(4) .
O79 C80 1.422(4) .
C80 C81 1.512(5) .
C81 C83 1.491(6) .
C81 C82 1.527(6) .
C84 C85 1.392(15) .
C84 C86 1.410(18) 2_665
C85 C86 1.539(14) .
C86 C87 1.216(13) .
C86 C84 1.410(18) 2_665
C88 C88 1.35(2) 2_655
C88 C89 1.35(2) .
C89 C90 1.232(17) .
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
C6 C1 C2 C3 0.4(8) . .
C7 C1 C2 C3 -177.1(5) . .
C1 C2 C3 C4 -0.8(10) . .
C2 C3 C4 C5 0.4(13) . .
C3 C4 C5 C6 0.4(14) . .
C2 C1 C6 C5 0.4(8) . .
C7 C1 C6 C5 178.0(5) . .
C4 C5 C6 C1 -0.8(12) . .
C2 C1 C7 N9 -45.9(5) . .
C6 C1 C7 N9 136.6(4) . .
C2 C1 C7 C8 77.5(5) . .
C6 C1 C7 C8 -100.0(5) . .
C8 C7 N9 C10 169.5(3) . .
C1 C7 N9 C10 -65.3(4) . .
C7 N9 C10 O11 0.0(5) . .
C7 N9 C10 C12 178.8(3) . .
O11 C10 C12 N17 -162.6(3) . .
N9 C10 C12 N17 18.6(4) . .
O11 C10 C12 C13 20.3(5) . .
N9 C10 C12 C13 -158.5(3) . .
N17 C12 C13 C14 -2.8(5) . .
C10 C12 C13 C14 174.1(3) . .
C12 C13 C14 O18 -179.7(3) . .
C12 C13 C14 C15 -0.1(5) . .
O18 C14 C15 C16 -177.1(3) . .
C13 C14 C15 C16 3.3(5) . .
O18 C14 C15 C23 3.0(5) . .
C13 C14 C15 C23 -176.7(3) . .
C14 C15 C16 N17 -4.2(5) . .
C23 C15 C16 N17 175.8(3) . .
C14 C15 C16 C26 176.5(3) . .
C23 C15 C16 C26 -3.6(5) . .
C13 C12 N17 C16 2.1(5) . .
C10 C12 N17 C16 -174.8(3) . .
C15 C16 N17 C12 1.5(4) . .
C26 C16 N17 C12 -179.1(3) . .
C13 C14 O18 C19 -6.4(6) . .
C15 C14 O18 C19 174.0(3) . .
C14 O18 C19 C20 -168.7(4) . .
O18 C19 C20 C22 59.9(6) . .
O18 C19 C20 C21 -177.2(5) . .
C16 C15 C23 C24 0.0(5) . .
C14 C15 C23 C24 180.0(3) . .
C15 C23 C24 C25 1.6(6) . .
C23 C24 C25 C26 0.5(5) . .
C24 C25 C26 N27 174.0(3) . .
C24 C25 C26 C16 -4.1(5) . .
N17 C16 C26 C25 -173.8(3) . .
C15 C16 C26 C25 5.7(4) . .
N17 C16 C26 N27 8.0(4) . .
C15 C16 C26 N27 -172.6(3) . .
C25 C26 N27 C28 -1.7(5) . .
C16 C26 N27 C28 176.5(3) . .
C26 N27 C28 O29 10.6(5) . .
C26 N27 C28 C30 -171.4(3) . .
O29 C28 C30 N35 -174.5(3) . .
N27 C28 C30 N35 7.5(4) . .
O29 C28 C30 C31 4.5(5) . .
N27 C28 C30 C31 -173.5(3) . .
N35 C30 C31 C32 -5.6(5) . .
C28 C30 C31 C32 175.5(3) . .
C30 C31 C32 O36 178.5(3) . .
C30 C31 C32 C33 -1.5(5) . .
O36 C32 C33 C44 5.4(5) . .
C31 C32 C33 C44 -174.5(3) . .
O36 C32 C33 C34 -172.4(3) . .
C31 C32 C33 C34 7.7(5) . .
C44 C33 C34 N35 174.3(3) . .
C32 C33 C34 N35 -7.8(5) . .
C44 C33 C34 C41 -8.2(5) . .
C32 C33 C34 C41 169.7(3) . .
C31 C30 N35 C34 5.8(4) . .
C28 C30 N35 C34 -175.3(3) . .
C33 C34 N35 C30 1.2(4) . .
C41 C34 N35 C30 -176.3(3) . .
C31 C32 O36 C37 -9.3(5) . .
C33 C32 O36 C37 170.8(3) . .
C32 O36 C37 C38 -163.0(5) . .
O36 C37 C38 C39 59.9(7) . .
O36 C37 C38 C40 -170.5(5) . .
N35 C34 C41 C42 -172.3(3) . .
C33 C34 C41 C42 10.1(5) . .
N35 C34 C41 N45 9.7(4) . .
C33 C34 C41 N45 -167.8(3) . .
N45 C41 C42 C43 172.8(3) . .
C34 C41 C42 C43 -5.0(5) . .
C41 C42 C43 C44 -2.1(6) . .
C42 C43 C44 C33 4.0(6) . .
C34 C33 C44 C43 1.3(5) . .
C32 C33 C44 C43 -176.4(3) . .
C42 C41 N45 C46 -7.6(6) . .
C34 C41 N45 C46 170.2(3) . .
C41 N45 C46 O47 9.9(6) . .
C41 N45 C46 C48 -171.7(3) . .
O47 C46 C48 N49 -160.3(3) . .
N45 C46 C48 N49 21.3(5) . .
O47 C46 C48 C53 22.3(5) . .
N45 C46 C48 C53 -156.1(3) . .
C53 C48 N49 C50 -0.6(5) . .
C46 C48 N49 C50 -177.7(3) . .
C48 N49 C50 C51 2.3(5) . .
C48 N49 C50 C59 -179.2(3) . .
N49 C50 C51 C62 176.6(3) . .
C59 C50 C51 C62 -1.9(5) . .
N49 C50 C51 C52 -0.9(5) . .
C59 C50 C51 C52 -179.4(3) . .
C50 C51 C52 O54 177.3(3) . .
C62 C51 C52 O54 -0.1(6) . .
C50 C51 C52 C53 -2.3(6) . .
C62 C51 C52 C53 -179.7(4) . .
O54 C52 C53 C48 -175.6(4) . .
C51 C52 C53 C48 4.0(6) . .
N49 C48 C53 C52 -2.6(6) . .
C46 C48 C53 C52 174.6(3) . .
C53 C52 O54 C55 14.2(7) . .
C51 C52 O54 C55 -165.4(5) . .
C52 O54 C55 C56 168.3(5) . .
O54 C55 C56 C58 -171.0(10) . .
O54 C55 C56 C57 69.7(9) . .
N49 C50 C59 C60 -176.6(3) . .
C51 C50 C59 C60 2.0(5) . .
N49 C50 C59 N63 5.2(4) . .
C51 C50 C59 N63 -176.2(3) . .
N63 C59 C60 C61 177.0(4) . .
C50 C59 C60 C61 -1.0(6) . .
C59 C60 C61 C62 -0.1(7) . .
C60 C61 C62 C51 0.2(8) . .
C50 C51 C62 C61 0.8(7) . .
C52 C51 C62 C61 178.1(4) . .
C60 C59 N63 C64 9.6(6) . .
C50 C59 N63 C64 -172.3(3) . .
C59 N63 C64 O65 6.0(6) . .
C59 N63 C64 C66 -173.8(3) . .
O65 C64 C66 N67 -167.9(3) . .
N63 C64 C66 N67 11.9(4) . .
O65 C64 C66 C71 12.1(5) . .
N63 C64 C66 C71 -168.1(3) . .
C71 C66 N67 C68 -2.3(5) . .
C64 C66 N67 C68 177.6(3) . .
C66 N67 C68 C69 3.8(4) . .
C66 N67 C68 C72 -178.5(3) . .
N67 C68 C69 C75 179.2(3) . .
C72 C68 C69 C75 1.4(4) . .
N67 C68 C69 C70 -1.5(5) . .
C72 C68 C69 C70 -179.4(3) . .
C68 C69 C70 O79 177.7(3) . .
C75 C69 C70 O79 -3.1(5) . .
C68 C69 C70 C71 -2.2(5) . .
C75 C69 C70 C71 177.0(3) . .
O79 C70 C71 C66 -176.3(3) . .
C69 C70 C71 C66 3.6(5) . .
N67 C66 C71 C70 -1.3(5) . .
C64 C66 C71 C70 178.8(3) . .
N67 C68 C72 C73 -176.6(3) . .
C69 C68 C72 C73 1.4(5) . .
N67 C68 C72 N76 4.7(4) . .
C69 C68 C72 N76 -177.4(3) . .
C68 C72 C73 C74 -3.6(5) . .
N76 C72 C73 C74 175.1(3) . .
C72 C73 C74 C75 3.1(6) . .
C73 C74 C75 C69 -0.4(6) . .
C68 C69 C75 C74 -1.9(5) . .
C70 C69 C75 C74 179.0(3) . .
C73 C72 N76 O77 52.8(4) . .
C68 C72 N76 O77 -128.4(3) . .
C73 C72 N76 O78 -123.9(4) . .
C68 C72 N76 O78 54.9(4) . .
C71 C70 O79 C80 6.4(5) . .
C69 C70 O79 C80 -173.4(3) . .
C70 O79 C80 C81 174.5(3) . .
O79 C80 C81 C83 -172.9(4) . .
O79 C80 C81 C82 63.8(5) . .
C86 C84 C85 C86 3(2) 2_665 .
C84 C85 C86 C87 -174.0(14) . .
C84 C85 C86 C84 -2.8(18) . 2_665
C88 C88 C89 C90 -176(4) 2_655 .
