# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Paul D. Beer' 'Andrew Cowley' 'David Curiel' _publ_contact_author_name 'Prof Paul D. Beer' _publ_contact_author_address ; Chemistry University of Oxford South Parks Road Oxford OX1 3QR UNITED KINGDOM ; _publ_contact_author_email PAUL.BEER@CHEM.OX.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Indolocarbazoles: a new family of anion sensors ; data_arc873 _database_code_depnum_ccdc_archive 'CCDC 247741' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; Geometric restraints have been applied to the disordered fragments of the structure. For the disordered butyl group C109-C212 the C-C bond lengths were restrained to 1.54(2) \%A and N-C-C and C-C-C angles to 112(2) \%. For the disordered solvent molecules O1-C224 the O-C bond lengths were restrained to 1.43(2) \%A, the C-C bond lengths to 1.52(2) \% and all bond angles to 112(2) \%. Similarity restraints were applied to the thermal displacement parameters of directly-bonded pairs of atoms. The NH hydrogen atoms were located in a difference Fourier map and their coordinates and isotropic thermal parameters subsequently refined. All other hydrogen atoms were positioned geometrically, the preferred orientations of the aromatic methyl substituents having been previously identified by examination of the Fourier map. ; #============================================================= _cell_length_a 14.1678(2) _cell_angle_alpha 104.5255(8) _cell_length_b 14.5150(2) _cell_angle_beta 94.2109(8) _cell_length_c 28.0396(4) _cell_angle_gamma 92.3985(5) _cell_volume 5555.98(14) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'F ' 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C124 H164 F2 N10 O2 ' _chemical_formula_moiety '4(C20 H16 N2), 2(C16 H36 N), 2(C6 H14 O), 2F' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 1864.73 _cell_measurement_reflns_used 89631 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.38 _exptl_crystal_density_diffrn 1.115 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2024 _exptl_absorpt_coefficient_mu 0.068 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 89631 _reflns_number_total 24984 _diffrn_reflns_av_R_equivalents 0.078 _diffrn_reflns_theta_min 5.092 _diffrn_reflns_theta_max 27.423 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.775 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _reflns_limit_h_min -18 _reflns_limit_h_max 18 _reflns_limit_k_min -18 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 36 _refine_diff_density_min -0.51 _refine_diff_density_max 0.71 _refine_ls_number_reflns 11480 _refine_ls_number_restraints 88 _refine_ls_number_parameters 1262 #_refine_ls_R_factor_ref 0.0790 _refine_ls_wR_factor_ref 0.0839 _refine_ls_goodness_of_fit_ref 1.1383 #_reflns_number_all 24984 _refine_ls_R_factor_all 0.1841 _refine_ls_wR_factor_all 0.1094 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 11480 _refine_ls_R_factor_gt 0.0790 _refine_ls_wR_factor_gt 0.0839 _refine_ls_shift/su_max 0.025405 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.74 2.72 2.02 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_disorder_assembly _atom_site_refinement_disorder_group F1 F 0.29843(12) 0.37310(12) 0.30740(7) 0.0452 1.0000 Uani . . . . . F2 F 0.30190(13) 0.32055(13) 0.20036(7) 0.0472 1.0000 Uani . . . . . N1 N 0.2404(2) 0.5469(2) 0.32984(10) 0.0420 1.0000 Uani . . . . . C1 C 0.2510(2) 0.6178(2) 0.37356(12) 0.0407 1.0000 Uani . . . . . C2 C 0.3126(3) 0.6252(2) 0.41550(13) 0.0479 1.0000 Uani . . . . . C3 C 0.3116(3) 0.7061(3) 0.45372(13) 0.0514 1.0000 Uani . . . . . C4 C 0.2514(3) 0.7797(3) 0.45135(13) 0.0475 1.0000 Uani . . . . . C5 C 0.1887(3) 0.7698(2) 0.40981(13) 0.0451 1.0000 Uani . . . . . C6 C 0.1871(2) 0.6886(2) 0.37055(12) 0.0421 1.0000 Uani . . . . . C7 C 0.1340(2) 0.6571(2) 0.32244(12) 0.0396 1.0000 Uani . . . . . C8 C 0.0589(2) 0.6938(2) 0.29869(13) 0.0428 1.0000 Uani . . . . . C9 C 0.0207(2) 0.6448(2) 0.25201(13) 0.0434 1.0000 Uani . . . . . C10 C 0.0586(2) 0.5584(2) 0.22817(12) 0.0411 1.0000 Uani . . . . . C11 C 0.0370(2) 0.4923(2) 0.17993(12) 0.0433 1.0000 Uani . . . . . C12 C -0.0281(2) 0.4882(3) 0.13908(13) 0.0482 1.0000 Uani . . . . . C13 C -0.0269(3) 0.4159(3) 0.09622(13) 0.0538 1.0000 Uani . . . . . C14 C 0.0396(3) 0.3460(3) 0.09459(14) 0.0550 1.0000 Uani . . . . . C15 C 0.1042(3) 0.3463(2) 0.13390(13) 0.0495 1.0000 Uani . . . . . C16 C 0.1021(2) 0.4200(2) 0.17671(12) 0.0433 1.0000 Uani . . . . . N2 N 0.1588(2) 0.43766(19) 0.22047(10) 0.0412 1.0000 Uani . . . . . C17 C 0.1335(2) 0.5213(2) 0.25108(12) 0.0374 1.0000 Uani . . . . . C18 C 0.1706(2) 0.5699(2) 0.29911(12) 0.0370 1.0000 Uani . . . . . C19 C 0.2547(3) 0.8672(3) 0.49387(14) 0.0595 1.0000 Uani . . . . . C20 C -0.0929(4) 0.4138(4) 0.05112(16) 0.0758 1.0000 Uani . . . . . N3 N 0.4730(2) 0.4559(2) 0.31324(12) 0.0458 1.0000 Uani . . . . . C21 C 0.5208(2) 0.4744(2) 0.35962(13) 0.0439 1.0000 Uani . . . . . C22 C 0.5015(2) 0.4395(3) 0.40011(14) 0.0494 1.0000 Uani . . . . . C23 C 0.5634(3) 0.4668(3) 0.44171(14) 0.0500 1.0000 Uani . . . . . C24 C 0.6436(3) 0.5291(3) 0.44507(13) 0.0499 1.0000 Uani . . . . . C25 C 0.6616(2) 0.5648(2) 0.40499(14) 0.0459 1.0000 Uani . . . . . C26 C 0.6006(2) 0.5371(2) 0.36141(13) 0.0401 1.0000 Uani . . . . . C27 C 0.5983(2) 0.5586(2) 0.31378(13) 0.0411 1.0000 Uani . . . . . C28 C 0.6557(2) 0.6192(2) 0.29395(13) 0.0459 1.0000 Uani . . . . . C29 C 0.6314(3) 0.6299(2) 0.24750(13) 0.0486 1.0000 Uani . . . . . C30 C 0.5508(2) 0.5790(2) 0.21905(13) 0.0459 1.0000 Uani . . . . . C31 C 0.5078(3) 0.5735(2) 0.16997(13) 0.0472 1.0000 Uani . . . . . C32 C 0.5299(3) 0.6159(2) 0.13240(14) 0.0524 1.0000 Uani . . . . . C33 C 0.4759(3) 0.5923(3) 0.08735(15) 0.0579 1.0000 Uani . . . . . C34 C 0.3983(3) 0.5253(3) 0.08048(15) 0.0605 1.0000 Uani . . . . . C35 C 0.3728(3) 0.4816(3) 0.11658(15) 0.0559 1.0000 Uani . . . . . C36 C 0.4289(2) 0.5068(2) 0.16191(14) 0.0477 1.0000 Uani . . . . . N4 N 0.4208(2) 0.4739(2) 0.20336(12) 0.0498 1.0000 Uani . . . . . C37 C 0.4946(2) 0.5166(2) 0.23810(13) 0.0447 1.0000 Uani . . . . . C38 C 0.5177(2) 0.5068(2) 0.28575(13) 0.0417 1.0000 Uani . . . . . C39 C 0.7092(3) 0.5548(3) 0.49184(15) 0.0606 1.0000 Uani . . . . . C40 C 0.5007(4) 0.6350(3) 0.04568(16) 0.0747 1.0000 Uani . . . . . N5 N 0.3872(2) 0.2135(2) 0.30294(10) 0.0416 1.0000 Uani . . . . . C41 C 0.3912(2) 0.1921(2) 0.34826(12) 0.0402 1.0000 Uani . . . . . C42 C 0.3432(3) 0.2301(2) 0.38951(13) 0.0457 1.0000 Uani . . . . . C43 C 0.3611(3) 0.1965(3) 0.43051(13) 0.0510 1.0000 Uani . . . . . C44 C 0.4248(3) 0.1249(3) 0.43200(14) 0.0548 1.0000 Uani . . . . . C45 C 0.4714(3) 0.0864(2) 0.39032(13) 0.0478 1.0000 Uani . . . . . C46 C 0.4558(2) 0.1201(2) 0.34812(12) 0.0401 1.0000 Uani . . . . . C47 C 0.4943(2) 0.0997(2) 0.30081(12) 0.0397 1.0000 Uani . . . . . C48 C 0.5639(2) 0.0383(2) 0.27973(13) 0.0427 1.0000 Uani . . . . . C49 C 0.5895(2) 0.0383(2) 0.23350(13) 0.0456 1.0000 Uani . . . . . C50 C 0.5454(2) 0.0977(2) 0.20687(12) 0.0417 1.0000 Uani . . . . . C51 C 0.5526(2) 0.1110(2) 0.15779(13) 0.0453 1.0000 Uani . . . . . C52 C 0.6069(3) 0.0703(3) 0.11882(14) 0.0517 1.0000 Uani . . . . . C53 C 0.5938(3) 0.0954(3) 0.07425(15) 0.0575 1.0000 Uani . . . . . C54 C 0.5268(3) 0.1616(3) 0.06920(14) 0.0587 1.0000 Uani . . . . . C55 C 0.4740(3) 0.2042(3) 0.10692(14) 0.0522 1.0000 Uani . . . . . C56 C 0.4871(2) 0.1779(2) 0.15151(12) 0.0450 1.0000 Uani . . . . . N6 N 0.4425(2) 0.2071(2) 0.19399(10) 0.0422 1.0000 Uani . . . . . C57 C 0.4753(2) 0.1584(2) 0.22721(12) 0.0400 1.0000 Uani . . . . . C58 C 0.4506(2) 0.1596(2) 0.27456(12) 0.0391 1.0000 Uani . . . . . C59 C 0.4418(4) 0.0917(4) 0.47886(17) 0.0814 1.0000 Uani . . . . . C60 C 0.6501(3) 0.0511(4) 0.03169(16) 0.0755 1.0000 Uani . . . . . N7 N 0.1330(2) 0.29190(19) 0.31695(10) 0.0387 1.0000 Uani . . . . . C61 C 0.0894(2) 0.3106(2) 0.36057(12) 0.0370 1.0000 Uani . . . . . C62 C 0.1076(2) 0.3858(2) 0.40262(13) 0.0460 1.0000 Uani . . . . . C63 C 0.0527(2) 0.3883(3) 0.44158(12) 0.0464 1.0000 Uani . . . . . C64 C -0.0198(2) 0.3181(2) 0.43975(12) 0.0427 1.0000 Uani . . . . . C65 C -0.0362(2) 0.2433(2) 0.39792(12) 0.0392 1.0000 Uani . . . . . C66 C 0.0184(2) 0.2383(2) 0.35776(11) 0.0349 1.0000 Uani . . . . . C67 C 0.0210(2) 0.1720(2) 0.31041(11) 0.0339 1.0000 Uani . . . . . C68 C -0.0301(2) 0.0836(2) 0.28739(12) 0.0428 1.0000 Uani . . . . . C69 C -0.0068(2) 0.0317(2) 0.24231(13) 0.0448 1.0000 Uani . . . . . C70 C 0.0663(2) 0.0666(2) 0.21850(11) 0.0390 1.0000 Uani . . . . . C71 C 0.1044(2) 0.0316(2) 0.17135(11) 0.0410 1.0000 Uani . . . . . C72 C 0.0837(3) -0.0504(2) 0.13220(12) 0.0482 1.0000 Uani . . . . . C73 C 0.1298(3) -0.0603(3) 0.08960(13) 0.0534 1.0000 Uani . . . . . C74 C 0.1973(3) 0.0109(3) 0.08631(13) 0.0533 1.0000 Uani . . . . . C75 C 0.2205(3) 0.0908(3) 0.12458(13) 0.0477 1.0000 Uani . . . . . C76 C 0.1729(2) 0.1010(2) 0.16717(12) 0.0409 1.0000 Uani . . . . . N8 N 0.1802(2) 0.1744(2) 0.20958(10) 0.0398 1.0000 Uani . . . . . C77 C 0.1153(2) 0.1550(2) 0.24041(11) 0.0351 1.0000 Uani . . . . . C78 C 0.0941(2) 0.2070(2) 0.28703(11) 0.0346 1.0000 Uani . . . . . C79 C -0.0796(3) 0.3262(3) 0.48290(14) 0.0607 1.0000 Uani . . . . . C80 C 0.1067(4) -0.1469(3) 0.04602(14) 0.0731 1.0000 Uani . . . . . N9 N 0.3078(2) 0.8271(2) 0.23947(10) 0.0452 1.0000 Uani . . . . . C81 C 0.3434(3) 0.7637(2) 0.27175(13) 0.0463 1.0000 Uani . . . . . C82 C 0.4296(3) 0.8058(3) 0.30780(14) 0.0581 1.0000 Uani . . . . . C83 C 0.4442(3) 0.7519(3) 0.34655(15) 0.0537 1.0000 Uani . . . . . C84 C 0.5293(3) 0.7903(3) 0.38275(15) 0.0629 1.0000 Uani . . . . . C85 C 0.2180(3) 0.7784(3) 0.20793(13) 0.0494 1.0000 Uani . . . . . C86 C 0.2307(3) 0.6890(3) 0.16748(13) 0.0510 1.0000 Uani . . . . . C87 C 0.1421(3) 0.6720(3) 0.13080(13) 0.0515 1.0000 Uani . . . . . C88 C 0.1489(3) 0.5891(3) 0.08617(14) 0.0638 1.0000 Uani . . . . . C89 C 0.2827(3) 0.9232(2) 0.27030(12) 0.0459 1.0000 Uani . . . . . C90 C 0.2169(3) 0.9194(3) 0.31041(14) 0.0580 1.0000 Uani . . . . . C91 C 0.1989(3) 1.0176(2) 0.33904(13) 0.0489 1.0000 Uani . . . . . C92 C 0.1353(3) 1.0204(3) 0.38099(14) 0.0587 1.0000 Uani . . . . . C93 C 0.3868(3) 0.8419(3) 0.20749(13) 0.0513 1.0000 Uani . . . . . C94 C 0.3623(3) 0.8880(3) 0.16643(14) 0.0622 1.0000 Uani . . . . . C95 C 0.4408(3) 0.8694(3) 0.13074(14) 0.0658 1.0000 Uani . . . . . C96 C 0.4188(4) 0.8991(4) 0.08402(17) 0.0755 1.0000 Uani . . . . . N10 N 0.8027(2) 0.32872(19) 0.23871(10) 0.0451 1.0000 Uani D . . . . C97 C 0.8171(3) 0.2290(2) 0.20784(12) 0.0438 1.0000 Uani . . . . . C98 C 0.8858(3) 0.2220(3) 0.16810(12) 0.0486 1.0000 Uani . . . . . C99 C 0.8768(3) 0.1212(3) 0.13382(13) 0.0502 1.0000 Uani . . . . . C100 C 0.9357(3) 0.1112(3) 0.09031(15) 0.0641 1.0000 Uani . . . . . C101 C 0.7225(3) 0.3230(3) 0.27057(13) 0.0518 1.0000 Uani . . . . . C102 C 0.7388(3) 0.2637(3) 0.30805(13) 0.0511 1.0000 Uani . . . . . C103 C 0.6701(3) 0.2889(2) 0.34776(13) 0.0477 1.0000 Uani . . . . . C104 C 0.6842(3) 0.2359(3) 0.38765(13) 0.0522 1.0000 Uani . . . . . C105 C 0.7771(3) 0.3953(2) 0.20585(13) 0.0504 1.0000 Uani . . . . . C106 C 0.6992(3) 0.3611(3) 0.16462(14) 0.0562 1.0000 Uani . . . . . C107 C 0.7023(3) 0.4296(3) 0.13124(14) 0.0539 1.0000 Uani . . . . . C108 C 0.6344(3) 0.3979(3) 0.08438(15) 0.0645 1.0000 Uani . . . . . C109 C 0.8954(3) 0.3692(2) 0.26945(13) 0.0554 0.562(11) Uani D . P 1 1 C110 C 0.9133(5) 0.4664(4) 0.3033(2) 0.0414(18) 0.562(11) Uiso D . P 1 1 C111 C 0.8836(4) 0.4764(4) 0.3557(2) 0.040(2) 0.562(11) Uiso D . P 1 1 C112 C 0.9275(3) 0.5775(3) 0.38710(16) 0.0743 0.562(11) Uani D . P 1 1 C209 C 0.8954(3) 0.3692(2) 0.26945(13) 0.0554 0.438(11) Uani D . P 1 2 C210 C 0.8639(7) 0.4603(6) 0.3096(3) 0.054(3) 0.438(11) Uiso D . P 1 2 C211 C 0.9528(6) 0.4980(6) 0.3423(3) 0.056(3) 0.438(11) Uiso D . P 1 2 C212 C 0.9275(3) 0.5775(3) 0.38710(16) 0.0743 0.438(11) Uani D . P 1 2 O1 O 0.7577(5) 0.7651(5) 0.0769(2) 0.1054(19) 0.634(9) Uiso D U P 2 1 C113 C 0.8002(10) 0.7493(8) 0.0325(4) 0.106(2) 0.634(9) Uiso D U P 2 1 C114 C 0.7665(8) 0.6543(7) 0.0018(4) 0.108(2) 0.634(9) Uiso D U P 2 1 C115 C 0.8130(7) 0.8274(7) 0.0072(4) 0.107(2) 0.634(9) Uiso D U P 2 1 C116 C 0.8140(7) 0.8052(7) 0.1222(3) 0.0996(19) 0.634(9) Uiso D U P 2 1 C117 C 0.7484(7) 0.8518(7) 0.1583(4) 0.095(2) 0.634(9) Uiso D U P 2 1 C118 C 0.8792(8) 0.7449(8) 0.1412(4) 0.104(2) 0.634(9) Uiso D U P 2 1 O101 O 0.8197(10) 0.7990(9) 0.0798(4) 0.116(3) 0.366(9) Uiso D U P 2 2 C213 C 0.8015(18) 0.7474(13) 0.0281(6) 0.120(4) 0.366(9) Uiso D U P 2 2 C214 C 0.8265(16) 0.6453(13) 0.0162(7) 0.120(4) 0.366(9) Uiso D U P 2 2 C215 C 0.7254(14) 0.7661(14) -0.0088(7) 0.124(4) 0.366(9) Uiso D U P 2 2 C216 C 0.7805(11) 0.7591(12) 0.1176(5) 0.109(3) 0.366(9) Uiso D U P 2 2 C217 C 0.7168(13) 0.8330(14) 0.1454(7) 0.107(4) 0.366(9) Uiso D U P 2 2 C218 C 0.8570(14) 0.7432(15) 0.1579(7) 0.110(4) 0.366(9) Uiso D U P 2 2 O2 O 0.8238(4) 0.8369(4) 0.3879(2) 0.0655(17) 0.533(9) Uiso D U P 3 1 C119 C 0.8354(6) 0.8984(6) 0.3568(3) 0.0669(18) 0.533(9) Uiso D U P 3 1 C120 C 0.8222(8) 0.8450(8) 0.3036(4) 0.071(2) 0.533(9) Uiso D U P 3 1 C121 C 0.7856(7) 0.9862(7) 0.3688(4) 0.070(2) 0.533(9) Uiso D U P 3 1 C122 C 0.8550(6) 0.8734(7) 0.4393(3) 0.0707(19) 0.533(9) Uiso D U P 3 1 C123 C 0.8202(7) 0.8024(7) 0.4675(3) 0.071(2) 0.533(9) Uiso D U P 3 1 C124 C 0.9596(7) 0.8715(7) 0.4476(4) 0.082(2) 0.533(9) Uiso D U P 3 1 O102 O 0.8904(6) 0.8591(6) 0.3955(3) 0.088(2) 0.467(9) Uiso D U P 3 2 C219 C 0.8109(8) 0.8721(9) 0.3643(4) 0.090(2) 0.467(9) Uiso D U P 3 2 C220 C 0.8383(11) 0.8329(11) 0.3131(5) 0.090(3) 0.467(9) Uiso D U P 3 2 C221 C 0.7642(11) 0.9672(10) 0.3731(6) 0.093(3) 0.467(9) Uiso D U P 3 2 C222 C 0.8801(8) 0.8828(10) 0.4473(4) 0.092(2) 0.467(9) Uiso D U P 3 2 C223 C 0.7926(9) 0.8296(10) 0.4606(5) 0.092(3) 0.467(9) Uiso D U P 3 2 C224 C 0.9752(9) 0.8813(10) 0.4754(5) 0.099(3) 0.467(9) Uiso D U P 3 2 H1 H 0.265(3) 0.491(4) 0.3224(17) 0.080(15) 1.0000 Uiso . . . . . H2 H 0.206(3) 0.405(3) 0.2253(16) 0.070(14) 1.0000 Uiso . . . . . H3 H 0.423(3) 0.428(2) 0.3073(12) 0.036(9) 1.0000 Uiso . . . . . H4 H 0.385(3) 0.434(3) 0.2067(14) 0.052(12) 1.0000 Uiso . . . . . H5 H 0.357(3) 0.257(3) 0.2961(16) 0.066(13) 1.0000 Uiso . . . . . H6 H 0.398(2) 0.241(2) 0.1966(11) 0.026(8) 1.0000 Uiso . . . . . H7 H 0.183(3) 0.321(2) 0.3132(12) 0.035(9) 1.0000 Uiso . . . . . H8 H 0.212(3) 0.222(3) 0.2125(14) 0.046(11) 1.0000 Uiso . . . . . H21 H 0.3561 0.5737 0.4178 0.0585 1.0000 Uiso . . . . . H31 H 0.3552 0.7126 0.4843 0.0622 1.0000 Uiso . . . . . H51 H 0.1445 0.8210 0.4080 0.0549 1.0000 Uiso . . . . . H81 H 0.0331 0.7554 0.3157 0.0524 1.0000 Uiso . . . . . H91 H -0.0333 0.6702 0.2352 0.0529 1.0000 Uiso . . . . . H121 H -0.0756 0.5378 0.1409 0.0585 1.0000 Uiso . . . . . H141 H 0.0401 0.2939 0.0636 0.0647 1.0000 Uiso . . . . . H151 H 0.1507 0.2958 0.1318 0.0595 1.0000 Uiso . . . . . H191 H 0.2077 0.9119 0.4861 0.0696 1.0000 Uiso . . . . . H192 H 0.3198 0.8994 0.4994 0.0696 1.0000 Uiso . . . . . H193 H 0.2389 0.8483 0.5244 0.0696 1.0000 Uiso . . . . . H201 H -0.1351 0.4682 0.0588 0.0890 1.0000 Uiso . . . . . H202 H -0.0549 0.4195 0.0232 0.0890 1.0000 Uiso . . . . . H203 H -0.1325 0.3522 0.0414 0.0890 1.0000 Uiso . . . . . H221 H 0.4443 0.3958 0.3988 0.0594 1.0000 Uiso . . . . . H231 H 0.5509 0.4414 0.4708 0.0604 1.0000 Uiso . . . . . H251 H 0.7178 0.6101 0.4071 0.0542 1.0000 Uiso . . . . . H281 H 0.7139 0.6542 0.3137 0.0535 1.0000 Uiso . . . . . H291 H 0.6711 0.6740 0.2337 0.0568 1.0000 Uiso . . . . . H321 H 0.5852 0.6636 0.1380 0.0622 1.0000 Uiso . . . . . H341 H 0.3597 0.5083 0.0478 0.0707 1.0000 Uiso . . . . . H351 H 0.3171 0.4344 0.1107 0.0645 1.0000 Uiso . . . . . H391 H 0.7623 0.5994 0.4882 0.0717 1.0000 Uiso . . . . . H392 H 0.6732 0.5864 0.5202 0.0717 1.0000 Uiso . . . . . H393 H 0.7355 0.4956 0.4981 0.0717 1.0000 Uiso . . . . . H401 H 0.5573 0.6809 0.0569 0.0887 1.0000 Uiso . . . . . H402 H 0.4459 0.6692 0.0357 0.0887 1.0000 Uiso . . . . . H403 H 0.5155 0.5830 0.0168 0.0887 1.0000 Uiso . . . . . H421 H 0.2972 0.2804 0.3892 0.0544 1.0000 Uiso . . . . . H431 H 0.3277 0.2237 0.4606 0.0608 1.0000 Uiso . . . . . H451 H 0.5158 0.0348 0.3906 0.0576 1.0000 Uiso . . . . . H481 H 0.5941 -0.0047 0.2984 0.0505 1.0000 Uiso . . . . . H491 H 0.6394 -0.0039 0.2186 0.0532 1.0000 Uiso . . . . . H521 H 0.6547 0.0235 0.1231 0.0616 1.0000 Uiso . . . . . H541 H 0.5171 0.1785 0.0368 0.0719 1.0000 Uiso . . . . . H551 H 0.4277 0.2522 0.1026 0.0635 1.0000 Uiso . . . . . H591 H 0.4886 0.0411 0.4736 0.1028 1.0000 Uiso . . . . . H592 H 0.4674 0.1468 0.5066 0.1028 1.0000 Uiso . . . . . H593 H 0.3807 0.0652 0.4872 0.1028 1.0000 Uiso . . . . . H601 H 0.6941 0.0060 0.0419 0.0907 1.0000 Uiso . . . . . H602 H 0.6878 0.1023 0.0220 0.0907 1.0000 Uiso . . . . . H603 H 0.6059 0.0156 0.0029 0.0907 1.0000 Uiso . . . . . H621 H 0.1588 0.4365 0.4046 0.0525 1.0000 Uiso . . . . . H631 H 0.0650 0.4417 0.4721 0.0527 1.0000 Uiso . . . . . H651 H -0.0872 0.1926 0.3963 0.0469 1.0000 Uiso . . . . . H681 H -0.0825 0.0595 0.3040 0.0504 1.0000 Uiso . . . . . H691 H -0.0416 -0.0311 0.2262 0.0524 1.0000 Uiso . . . . . H721 H 0.0361 -0.1011 0.1351 0.0571 1.0000 Uiso . . . . . H741 H 0.2297 0.0033 0.0552 0.0646 1.0000 Uiso . . . . . H751 H 0.2699 0.1400 0.1219 0.0589 1.0000 Uiso . . . . . H791 H -0.1275 0.2708 0.4755 0.0694 1.0000 Uiso . . . . . H792 H -0.0380 0.3262 0.5133 0.0694 1.0000 Uiso . . . . . H793 H -0.1129 0.3869 0.4884 0.0694 1.0000 Uiso . . . . . H801 H 0.0575 -0.1902 0.0545 0.0848 1.0000 Uiso . . . . . H802 H 0.1654 -0.1817 0.0384 0.0848 1.0000 Uiso . . . . . H803 H 0.0819 -0.1255 0.0165 0.0848 1.0000 Uiso . . . . . H811 H 0.2907 0.7505 0.2914 0.0555 1.0000 Uiso . . . . . H812 H 0.3608 0.7025 0.2496 0.0555 1.0000 Uiso . . . . . H821 H 0.4196 0.8738 0.3242 0.0684 1.0000 Uiso . . . . . H822 H 0.4872 0.8027 0.2890 0.0684 1.0000 Uiso . . . . . H831 H 0.3865 0.7556 0.3653 0.0648 1.0000 Uiso . . . . . H832 H 0.4531 0.6837 0.3298 0.0648 1.0000 Uiso . . . . . H841 H 0.5355 0.7516 0.4076 0.0736 1.0000 Uiso . . . . . H842 H 0.5212 0.8583 0.4000 0.0736 1.0000 Uiso . . . . . H843 H 0.5878 0.7864 0.3646 0.0736 1.0000 Uiso . . . . . H851 H 0.1890 0.8258 0.1918 0.0579 1.0000 Uiso . . . . . H852 H 0.1734 0.7606 0.2307 0.0579 1.0000 Uiso . . . . . H861 H 0.2883 0.6983 0.1502 0.0589 1.0000 Uiso . . . . . H862 H 0.2376 0.6333 0.1821 0.0589 1.0000 Uiso . . . . . H871 H 0.1330 0.7310 0.1192 0.0608 1.0000 Uiso . . . . . H872 H 0.0860 0.6586 0.1482 0.0608 1.0000 Uiso . . . . . H881 H 0.0894 0.5813 0.0636 0.0737 1.0000 Uiso . . . . . H882 H 0.2044 0.6019 0.0682 0.0737 1.0000 Uiso . . . . . H883 H 0.1573 0.5294 0.0973 0.0737 1.0000 Uiso . . . . . H891 H 0.3429 0.9596 0.2866 0.0535 1.0000 Uiso . . . . . H892 H 0.2512 0.9580 0.2475 0.0535 1.0000 Uiso . . . . . H901 H 0.2469 0.8842 0.3334 0.0678 1.0000 Uiso . . . . . H902 H 0.1553 0.8852 0.2947 0.0678 1.0000 Uiso . . . . . H911 H 0.2612 1.0517 0.3535 0.0592 1.0000 Uiso . . . . . H912 H 0.1679 1.0515 0.3157 0.0592 1.0000 Uiso . . . . . H921 H 0.1265 1.0882 0.3984 0.0703 1.0000 Uiso . . . . . H922 H 0.1656 0.9874 0.4050 0.0703 1.0000 Uiso . . . . . H923 H 0.0722 0.9873 0.3671 0.0703 1.0000 Uiso . . . . . H931 H 0.4392 0.8825 0.2298 0.0603 1.0000 Uiso . . . . . H932 H 0.4099 0.7778 0.1924 0.0603 1.0000 Uiso . . . . . H941 H 0.3584 0.9582 0.1802 0.0746 1.0000 Uiso . . . . . H942 H 0.2999 0.8599 0.1486 0.0746 1.0000 Uiso . . . . . H951 H 0.5005 0.9055 0.1481 0.0782 1.0000 Uiso . . . . . H952 H 0.4507 0.7995 0.1219 0.0782 1.0000 Uiso . . . . . H961 H 0.4727 0.8850 0.0627 0.0912 1.0000 Uiso . . . . . H962 H 0.4094 0.9690 0.0921 0.0912 1.0000 Uiso . . . . . H963 H 0.3596 0.8631 0.0660 0.0912 1.0000 Uiso . . . . . H971 H 0.8412 0.1909 0.2308 0.0522 1.0000 Uiso . . . . . H972 H 0.7541 0.2003 0.1912 0.0522 1.0000 Uiso . . . . . H981 H 0.9521 0.2363 0.1840 0.0576 1.0000 Uiso . . . . . H982 H 0.8707 0.2691 0.1484 0.0576 1.0000 Uiso . . . . . H991 H 0.8980 0.0756 0.1533 0.0581 1.0000 Uiso . . . . . H992 H 0.8088 0.1051 0.1211 0.0581 1.0000 Uiso . . . . . H1001 H 0.9273 0.0443 0.0692 0.0753 1.0000 Uiso . . . . . H1002 H 1.0041 0.1266 0.1025 0.0753 1.0000 Uiso . . . . . H1003 H 0.9149 0.1561 0.0704 0.0753 1.0000 Uiso . . . . . H1011 H 0.7111 0.3894 0.2892 0.0629 1.0000 Uiso . . . . . H1012 H 0.6647 0.2946 0.2482 0.0629 1.0000 Uiso . . . . . H1021 H 0.8053 0.2771 0.3237 0.0610 1.0000 Uiso . . . . . H1022 H 0.7285 0.1944 0.2907 0.0610 1.0000 Uiso . . . . . H1031 H 0.6789 0.3589 0.3636 0.0562 1.0000 Uiso . . . . . H1032 H 0.6040 0.2731 0.3317 0.0562 1.0000 Uiso . . . . . H1041 H 0.6371 0.2555 0.4126 0.0628 1.0000 Uiso . . . . . H1042 H 0.7499 0.2515 0.4043 0.0628 1.0000 Uiso . . . . . H1043 H 0.6750 0.1657 0.3724 0.0628 1.0000 Uiso . . . . . H1051 H 0.8358 0.4090 0.1904 0.0608 1.0000 Uiso . . . . . H1052 H 0.7576 0.4557 0.2278 0.0608 1.0000 Uiso . . . . . H1061 H 0.7098 0.2950 0.1453 0.0681 1.0000 Uiso . . . . . H1062 H 0.6362 0.3615 0.1786 0.0681 1.0000 Uiso . . . . . H1071 H 0.7684 0.4345 0.1213 0.0663 1.0000 Uiso . . . . . H1072 H 0.6852 0.4937 0.1504 0.0663 1.0000 Uiso . . . . . H1081 H 0.6399 0.4454 0.0642 0.0782 1.0000 Uiso . . . . . H1082 H 0.6511 0.3341 0.0646 0.0782 1.0000 Uiso . . . . . H1083 H 0.5679 0.3933 0.0937 0.0782 1.0000 Uiso . . . . . H1091 H 0.9440 0.3645 0.2450 0.0651 0.562 Uiso . . . 1 1 H1092 H 0.9090 0.3243 0.2906 0.0651 0.562 Uiso . . . 1 1 H1101 H 0.9828 0.4840 0.3059 0.0497 0.562 Uiso . . . 1 1 H1102 H 0.8776 0.5118 0.2885 0.0497 0.562 Uiso . . . 1 1 H1111 H 0.9092 0.4246 0.3697 0.0481 0.562 Uiso . . . 1 1 H1112 H 0.8129 0.4734 0.3554 0.0481 0.562 Uiso . . . 1 1 H1121 H 0.9104 0.5884 0.4220 0.0827 0.562 Uiso . . . 1 1 H1122 H 0.9980 0.5796 0.3867 0.0827 0.562 Uiso . . . 1 1 H1123 H 0.9017 0.6284 0.3724 0.0827 0.562 Uiso . . . 1 1 H2091 H 0.9426 0.3887 0.2485 0.0651 0.438 Uiso . . . 1 2 H2092 H 0.9229 0.3216 0.2860 0.0651 0.438 Uiso . . . 1 2 H2101 H 0.8398 0.5093 0.2930 0.0642 0.438 Uiso . . . 1 2 H2102 H 0.8136 0.4410 0.3290 0.0642 0.438 Uiso . . . 1 2 H2111 H 0.9991 0.5249 0.3234 0.0668 0.438 Uiso . . . 1 2 H2112 H 0.9814 0.4453 0.3544 0.0668 0.438 Uiso . . . 1 2 H2121 H 0.9863 0.6032 0.4092 0.0827 0.438 Uiso . . . 1 2 H2122 H 0.8988 0.6301 0.3750 0.0827 0.438 Uiso . . . 1 2 H2123 H 0.8810 0.5505 0.4060 0.0827 0.438 Uiso . . . 1 2 H1131 H 0.8699 0.7510 0.0419 0.1278 0.634 Uiso . . . 2 1 H1141 H 0.7963 0.6417 -0.0302 0.1295 0.634 Uiso . . . 2 1 H1142 H 0.7843 0.6050 0.0196 0.1295 0.634 Uiso . . . 2 1 H1143 H 0.6960 0.6515 -0.0047 0.1295 0.634 Uiso . . . 2 1 H1151 H 0.8445 0.8029 -0.0239 0.1279 0.634 Uiso . . . 2 1 H1152 H 0.8533 0.8815 0.0296 0.1279 0.634 Uiso . . . 2 1 H1153 H 0.7497 0.8501 -0.0011 0.1279 0.634 Uiso . . . 2 1 H1161 H 0.8620 0.8516 0.1154 0.1195 0.634 Uiso . . . 2 1 H1171 H 0.7850 0.8811 0.1909 0.1136 0.634 Uiso . . . 2 1 H1172 H 0.7164 0.9025 0.1460 0.1136 0.634 Uiso . . . 2 1 H1173 H 0.6996 0.8032 0.1624 0.1136 0.634 Uiso . . . 2 1 H1181 H 0.9135 0.7826 0.1730 0.1254 0.634 Uiso . . . 2 1 H1182 H 0.9260 0.7220 0.1166 0.1254 0.634 Uiso . . . 2 1 H1183 H 0.8426 0.6890 0.1471 0.1254 0.634 Uiso . . . 2 1 H2131 H 0.8490 0.7936 0.0206 0.1444 0.366 Uiso . . . 2 2 H2141 H 0.8116 0.6159 -0.0200 0.1441 0.366 Uiso . . . 2 2 H2142 H 0.8957 0.6422 0.0252 0.1441 0.366 Uiso . . . 2 2 H2143 H 0.7888 0.6098 0.0354 0.1441 0.366 Uiso . . . 2 2 H2151 H 0.7290 0.7201 -0.0416 0.1492 0.366 Uiso . . . 2 2 H2152 H 0.7355 0.8328 -0.0121 0.1492 0.366 Uiso . . . 2 2 H2153 H 0.6615 0.7579 0.0031 0.1492 0.366 Uiso . . . 2 2 H2161 H 0.7479 0.6958 0.1003 0.1311 0.366 Uiso . . . 2 2 H2171 H 0.6882 0.8086 0.1718 0.1286 0.366 Uiso . . . 2 2 H2172 H 0.7553 0.8939 0.1608 0.1286 0.366 Uiso . . . 2 2 H2173 H 0.6651 0.8448 0.1218 0.1286 0.366 Uiso . . . 2 2 H2181 H 0.8251 0.7159 0.1823 0.1319 0.366 Uiso . . . 2 2 H2182 H 0.8912 0.8056 0.1753 0.1319 0.366 Uiso . . . 2 2 H2183 H 0.9034 0.6981 0.1416 0.1319 0.366 Uiso . . . 2 2 H1191 H 0.9030 0.9240 0.3639 0.0803 0.533 Uiso . . . 3 1 H1201 H 0.8309 0.8903 0.2824 0.0849 0.533 Uiso . . . 3 1 H1202 H 0.8701 0.7957 0.2968 0.0849 0.533 Uiso . . . 3 1 H1203 H 0.7569 0.8132 0.2960 0.0849 0.533 Uiso . . . 3 1 H1211 H 0.7985 1.0244 0.3446 0.0840 0.533 Uiso . . . 3 1 H1212 H 0.8081 1.0242 0.4029 0.0840 0.533 Uiso . . . 3 1 H1213 H 0.7158 0.9701 0.3670 0.0840 0.533 Uiso . . . 3 1 H1221 H 0.8316 0.9389 0.4500 0.0849 0.533 Uiso . . . 3 1 H1231 H 0.8415 0.8269 0.5034 0.0856 0.533 Uiso . . . 3 1 H1232 H 0.8472 0.7394 0.4543 0.0856 0.533 Uiso . . . 3 1 H1233 H 0.7494 0.7946 0.4631 0.0856 0.533 Uiso . . . 3 1 H1241 H 0.9797 0.8972 0.4836 0.0988 0.533 Uiso . . . 3 1 H1242 H 0.9910 0.9117 0.4283 0.0988 0.533 Uiso . . . 3 1 H1243 H 0.9785 0.8044 0.4364 0.0988 0.533 Uiso . . . 3 1 H2191 H 0.7546 0.8375 0.3728 0.1083 0.467 Uiso . . . 3 2 H2201 H 0.7856 0.8394 0.2886 0.1078 0.467 Uiso . . . 3 2 H2202 H 0.8969 0.8690 0.3080 0.1078 0.467 Uiso . . . 3 2 H2203 H 0.8509 0.7640 0.3082 0.1078 0.467 Uiso . . . 3 2 H2211 H 0.7099 0.9624 0.3475 0.1116 0.467 Uiso . . . 3 2 H2212 H 0.8117 1.0185 0.3708 0.1116 0.467 Uiso . . . 3 2 H2213 H 0.7404 0.9830 0.4067 0.1116 0.467 Uiso . . . 3 2 H2221 H 0.8625 0.9502 0.4592 0.1099 0.467 Uiso . . . 3 2 H2231 H 0.7887 0.8487 0.4972 0.1104 0.467 Uiso . . . 3 2 H2232 H 0.7337 0.8466 0.4436 0.1104 0.467 Uiso . . . 3 2 H2233 H 0.7988 0.7592 0.4495 0.1104 0.467 Uiso . . . 3 2 H2241 H 0.9677 0.8979 0.5117 0.1186 0.467 Uiso . . . 3 2 H2242 H 1.0212 0.9288 0.4680 0.1186 0.467 Uiso . . . 3 2 H2243 H 0.9994 0.8162 0.4652 0.1186 0.467 Uiso . . . 3 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0335(9) 0.0363(10) 0.0667(13) 0.0126(9) 0.0107(9) 0.0028(8) F2 0.0418(10) 0.0438(10) 0.0568(12) 0.0125(9) 0.0093(9) 0.0049(8) N1 0.0419(16) 0.0370(15) 0.0469(17) 0.0080(13) 0.0097(13) 0.0066(13) C1 0.0416(18) 0.0375(17) 0.0434(19) 0.0090(15) 0.0126(15) 0.0010(14) C2 0.051(2) 0.0441(19) 0.051(2) 0.0162(17) 0.0076(17) 0.0035(16) C3 0.059(2) 0.050(2) 0.046(2) 0.0145(17) 0.0078(17) 0.0015(18) C4 0.054(2) 0.047(2) 0.0409(19) 0.0107(16) 0.0098(17) -0.0034(17) C5 0.052(2) 0.0346(17) 0.050(2) 0.0097(15) 0.0199(17) 0.0019(15) C6 0.0462(19) 0.0367(17) 0.0461(19) 0.0119(15) 0.0163(15) 0.0030(15) C7 0.0414(17) 0.0332(16) 0.0446(19) 0.0084(14) 0.0133(15) 0.0017(14) C8 0.0457(19) 0.0356(17) 0.050(2) 0.0114(15) 0.0167(16) 0.0053(15) C9 0.0417(18) 0.0379(17) 0.053(2) 0.0126(16) 0.0101(16) 0.0088(14) C10 0.0392(17) 0.0398(17) 0.0451(19) 0.0097(15) 0.0116(15) 0.0037(14) C11 0.0453(19) 0.0412(18) 0.0431(19) 0.0084(15) 0.0121(16) -0.0013(15) C12 0.0439(19) 0.051(2) 0.052(2) 0.0154(17) 0.0067(17) 0.0014(16) C13 0.060(2) 0.056(2) 0.042(2) 0.0066(17) 0.0065(17) -0.0014(19) C14 0.071(3) 0.047(2) 0.044(2) 0.0033(16) 0.0136(19) 0.0006(19) C15 0.058(2) 0.0415(19) 0.049(2) 0.0079(16) 0.0188(18) 0.0053(16) C16 0.0492(19) 0.0374(17) 0.0440(19) 0.0104(15) 0.0118(16) -0.0006(15) N2 0.0420(16) 0.0337(14) 0.0475(17) 0.0068(13) 0.0104(13) 0.0068(13) C17 0.0329(16) 0.0341(16) 0.0461(19) 0.0093(14) 0.0128(14) 0.0010(13) C18 0.0342(16) 0.0329(16) 0.0444(18) 0.0073(14) 0.0147(14) 0.0035(13) C19 0.077(3) 0.046(2) 0.051(2) 0.0024(17) 0.012(2) 0.0011(19) C20 0.079(3) 0.090(3) 0.053(2) 0.009(2) 0.005(2) 0.008(3) N3 0.0286(15) 0.0435(16) 0.065(2) 0.0140(14) 0.0064(14) -0.0010(13) C21 0.0400(18) 0.0372(17) 0.054(2) 0.0070(15) 0.0123(16) 0.0087(14) C22 0.0413(19) 0.0449(19) 0.062(2) 0.0111(17) 0.0160(18) 0.0034(15) C23 0.050(2) 0.047(2) 0.054(2) 0.0106(17) 0.0163(18) 0.0062(17) C24 0.054(2) 0.0446(19) 0.047(2) 0.0015(16) 0.0084(17) 0.0111(17) C25 0.0403(18) 0.0364(17) 0.059(2) 0.0068(16) 0.0098(17) 0.0020(14) C26 0.0325(16) 0.0334(16) 0.053(2) 0.0075(15) 0.0094(15) 0.0034(13) C27 0.0337(16) 0.0313(16) 0.054(2) 0.0029(15) 0.0060(15) 0.0024(13) C28 0.0425(19) 0.0398(18) 0.051(2) 0.0057(16) 0.0034(16) -0.0037(15) C29 0.052(2) 0.0383(18) 0.051(2) 0.0051(16) 0.0075(17) -0.0072(16) C30 0.0437(19) 0.0382(18) 0.053(2) 0.0071(15) 0.0055(16) 0.0013(15) C31 0.052(2) 0.0375(18) 0.049(2) 0.0064(15) 0.0006(17) 0.0034(16) C32 0.057(2) 0.0386(18) 0.060(2) 0.0094(17) 0.0043(19) 0.0043(16) C33 0.071(3) 0.049(2) 0.052(2) 0.0101(18) 0.002(2) 0.015(2) C34 0.064(3) 0.061(2) 0.052(2) 0.0049(19) -0.0019(19) 0.020(2) C35 0.044(2) 0.054(2) 0.064(2) 0.0061(19) -0.0091(18) 0.0074(17) C36 0.0410(19) 0.0406(19) 0.058(2) 0.0059(17) 0.0017(17) 0.0072(15) N4 0.0407(17) 0.0417(17) 0.063(2) 0.0081(15) -0.0005(15) -0.0010(14) C37 0.0383(18) 0.0361(17) 0.055(2) 0.0022(15) 0.0019(16) 0.0044(14) C38 0.0331(17) 0.0338(16) 0.055(2) 0.0042(15) 0.0073(15) 0.0004(13) C39 0.069(3) 0.055(2) 0.055(2) 0.0091(19) 0.007(2) 0.003(2) C40 0.095(3) 0.072(3) 0.056(3) 0.010(2) 0.009(2) 0.012(3) N5 0.0460(16) 0.0354(15) 0.0428(16) 0.0068(13) 0.0065(13) 0.0104(13) C41 0.0418(18) 0.0331(16) 0.0445(19) 0.0085(14) 0.0038(15) -0.0010(14) C42 0.051(2) 0.0361(17) 0.049(2) 0.0076(15) 0.0084(16) 0.0025(15) C43 0.061(2) 0.048(2) 0.043(2) 0.0093(16) 0.0098(17) -0.0022(18) C44 0.067(2) 0.046(2) 0.052(2) 0.0174(17) -0.0016(19) -0.0028(18) C45 0.054(2) 0.0409(18) 0.049(2) 0.0138(16) 0.0013(17) 0.0024(16) C46 0.0397(17) 0.0322(16) 0.0457(19) 0.0063(14) -0.0009(15) 0.0009(14) C47 0.0404(17) 0.0311(16) 0.0433(18) 0.0042(14) -0.0029(15) -0.0013(14) C48 0.0396(18) 0.0351(17) 0.051(2) 0.0080(15) 0.0011(15) 0.0051(14) C49 0.0403(18) 0.0396(18) 0.053(2) 0.0046(16) 0.0026(16) 0.0077(15) C50 0.0354(17) 0.0416(18) 0.0442(19) 0.0034(15) 0.0041(14) 0.0016(14) C51 0.0410(18) 0.0432(18) 0.049(2) 0.0066(16) 0.0069(15) 0.0027(15) C52 0.046(2) 0.056(2) 0.052(2) 0.0095(18) 0.0121(17) 0.0023(17) C53 0.051(2) 0.064(2) 0.056(2) 0.0099(19) 0.0152(18) 0.0051(19) C54 0.061(2) 0.071(3) 0.048(2) 0.0198(19) 0.0131(19) 0.001(2) C55 0.048(2) 0.059(2) 0.052(2) 0.0175(18) 0.0062(17) 0.0048(17) C56 0.0438(19) 0.0463(19) 0.0429(19) 0.0063(16) 0.0094(16) 0.0005(15) N6 0.0386(16) 0.0440(16) 0.0470(17) 0.0141(13) 0.0087(13) 0.0118(14) C57 0.0349(16) 0.0353(17) 0.0467(19) 0.0060(15) 0.0007(14) -0.0025(14) C58 0.0410(18) 0.0298(15) 0.0420(18) 0.0013(14) 0.0023(15) 0.0016(14) C59 0.108(4) 0.088(3) 0.061(3) 0.036(2) 0.020(3) 0.025(3) C60 0.079(3) 0.094(3) 0.054(2) 0.012(2) 0.027(2) 0.014(3) N7 0.0342(14) 0.0368(14) 0.0429(16) 0.0064(12) 0.0074(12) -0.0052(12) C61 0.0313(16) 0.0383(17) 0.0409(18) 0.0089(14) 0.0029(14) 0.0037(13) C62 0.0381(18) 0.0440(19) 0.049(2) 0.0012(16) 0.0019(15) -0.0058(15) C63 0.0452(19) 0.052(2) 0.0350(18) -0.0017(15) 0.0016(15) 0.0001(16) C64 0.0371(17) 0.051(2) 0.0374(18) 0.0076(15) 0.0028(14) 0.0001(15) C65 0.0348(16) 0.0437(18) 0.0386(18) 0.0107(15) 0.0020(14) -0.0021(14) C66 0.0296(15) 0.0383(16) 0.0355(17) 0.0079(13) -0.0001(13) 0.0041(13) C67 0.0352(16) 0.0338(16) 0.0316(16) 0.0061(13) 0.0024(13) 0.0035(13) C68 0.0448(19) 0.0444(18) 0.0368(18) 0.0074(15) 0.0053(15) -0.0086(15) C69 0.0486(19) 0.0390(18) 0.0433(19) 0.0070(15) 0.0011(15) -0.0109(15) C70 0.0448(18) 0.0379(17) 0.0324(16) 0.0056(13) 0.0032(14) 0.0024(14) C71 0.0481(19) 0.0425(18) 0.0323(17) 0.0079(14) 0.0051(14) 0.0071(15) C72 0.063(2) 0.0423(19) 0.0372(19) 0.0069(15) 0.0057(17) 0.0007(17) C73 0.073(3) 0.052(2) 0.0352(19) 0.0078(16) 0.0071(17) 0.0148(19) C74 0.063(2) 0.061(2) 0.0372(19) 0.0119(18) 0.0117(17) 0.0121(19) C75 0.051(2) 0.053(2) 0.043(2) 0.0166(17) 0.0135(16) 0.0089(17) C76 0.0466(19) 0.0378(17) 0.0399(18) 0.0118(15) 0.0051(15) 0.0070(15) N8 0.0391(15) 0.0379(16) 0.0422(16) 0.0080(13) 0.0092(12) 0.0024(13) C77 0.0338(16) 0.0358(16) 0.0383(17) 0.0136(14) 0.0051(13) 0.0041(13) C78 0.0329(16) 0.0316(15) 0.0388(17) 0.0084(13) 0.0016(13) 0.0021(13) C79 0.060(2) 0.072(3) 0.041(2) -0.0025(19) 0.0144(18) -0.009(2) C80 0.106(4) 0.067(3) 0.038(2) -0.0014(19) 0.016(2) -0.001(2) N9 0.0475(16) 0.0483(16) 0.0367(15) 0.0056(13) 0.0083(12) -0.0084(13) C81 0.049(2) 0.0454(19) 0.0445(19) 0.0102(16) 0.0108(16) -0.0054(16) C82 0.062(2) 0.067(2) 0.042(2) 0.0121(18) -0.0008(18) -0.015(2) C83 0.059(2) 0.0412(19) 0.062(2) 0.0139(17) 0.0077(19) 0.0061(17) C84 0.075(3) 0.061(2) 0.048(2) 0.0063(19) 0.000(2) 0.009(2) C85 0.049(2) 0.052(2) 0.044(2) 0.0074(16) 0.0063(16) -0.0090(17) C86 0.054(2) 0.050(2) 0.043(2) 0.0019(16) 0.0066(17) -0.0043(17) C87 0.059(2) 0.051(2) 0.043(2) 0.0099(16) 0.0001(17) -0.0053(17) C88 0.062(2) 0.078(3) 0.044(2) 0.007(2) -0.0033(18) -0.009(2) C89 0.052(2) 0.0397(18) 0.0424(19) 0.0041(15) 0.0056(16) -0.0041(15) C90 0.072(3) 0.046(2) 0.052(2) 0.0016(17) 0.0209(19) -0.0074(18) C91 0.061(2) 0.0392(18) 0.048(2) 0.0115(16) 0.0096(17) 0.0061(16) C92 0.076(3) 0.053(2) 0.046(2) 0.0074(17) 0.0143(19) 0.015(2) C93 0.049(2) 0.057(2) 0.044(2) 0.0077(17) 0.0093(16) -0.0114(17) C94 0.059(2) 0.078(3) 0.049(2) 0.020(2) 0.0028(18) -0.018(2) C95 0.083(3) 0.070(3) 0.043(2) 0.0103(19) 0.015(2) -0.010(2) C96 0.085(3) 0.079(3) 0.064(3) 0.021(2) 0.009(2) 0.001(2) N10 0.0619(18) 0.0377(15) 0.0357(15) 0.0084(12) 0.0047(13) 0.0088(13) C97 0.056(2) 0.0371(17) 0.0377(18) 0.0065(14) 0.0031(15) 0.0105(15) C98 0.059(2) 0.0467(19) 0.0380(18) 0.0071(15) 0.0049(16) 0.0061(17) C99 0.055(2) 0.051(2) 0.0389(19) 0.0027(16) 0.0013(16) 0.0021(17) C100 0.075(3) 0.065(3) 0.047(2) 0.0043(19) 0.009(2) 0.014(2) C101 0.074(3) 0.0450(19) 0.0386(19) 0.0089(15) 0.0151(18) 0.0166(18) C102 0.066(2) 0.0428(19) 0.044(2) 0.0071(16) 0.0107(17) 0.0079(17) C103 0.053(2) 0.0428(19) 0.045(2) 0.0066(16) 0.0052(16) -0.0001(16) C104 0.054(2) 0.060(2) 0.043(2) 0.0135(17) 0.0053(17) 0.0008(18) C105 0.076(3) 0.0370(18) 0.0388(18) 0.0117(15) 0.0013(18) 0.0071(17) C106 0.067(2) 0.052(2) 0.051(2) 0.0153(18) 0.0048(19) 0.0110(19) C107 0.056(2) 0.060(2) 0.050(2) 0.0200(18) 0.0057(17) 0.0130(18) C108 0.068(3) 0.070(3) 0.058(2) 0.022(2) -0.005(2) 0.010(2) C109 0.082(3) 0.0424(19) 0.0380(19) 0.0094(15) -0.0090(19) -0.0060(19) C112 0.086(3) 0.066(3) 0.054(2) -0.009(2) -0.015(2) 0.006(2) C209 0.082(3) 0.0424(19) 0.0380(19) 0.0094(15) -0.0090(19) -0.0060(19) C212 0.086(3) 0.066(3) 0.054(2) -0.009(2) -0.015(2) 0.006(2) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . H1 . 0.88(5) no N1 . C18 . 1.370(4) yes N1 . C1 . 1.383(4) yes C1 . C6 . 1.412(5) yes C1 . C2 . 1.391(5) yes C2 . H21 . 1.000 no C2 . C3 . 1.378(5) yes C3 . H31 . 1.000 no C3 . C4 . 1.406(5) yes C4 . C19 . 1.504(5) yes C4 . C5 . 1.385(5) yes C5 . H51 . 1.000 no C5 . C6 . 1.395(5) yes C6 . C7 . 1.452(5) yes C7 . C18 . 1.411(4) yes C7 . C8 . 1.407(5) yes C8 . H81 . 1.000 no C8 . C9 . 1.382(5) yes C9 . H91 . 1.000 no C9 . C10 . 1.414(5) yes C10 . C17 . 1.396(5) yes C10 . C11 . 1.451(5) yes C11 . C16 . 1.416(5) yes C11 . C12 . 1.405(5) yes C12 . H121 . 1.000 no C12 . C13 . 1.385(5) yes C13 . C20 . 1.509(6) yes C13 . C14 . 1.408(6) yes C14 . H141 . 1.000 no C14 . C15 . 1.379(6) yes C15 . H151 . 1.000 no C15 . C16 . 1.396(5) yes C16 . N2 . 1.377(5) yes N2 . H2 . 0.85(5) no N2 . C17 . 1.378(4) yes C17 . C18 . 1.405(5) yes C19 . H193 . 1.000 no C19 . H192 . 1.000 no C19 . H191 . 1.000 no C20 . H203 . 1.000 no C20 . H202 . 1.000 no C20 . H201 . 1.000 no N3 . H3 . 0.79(4) no N3 . C38 . 1.363(4) yes N3 . C21 . 1.380(5) yes C21 . C26 . 1.410(5) yes C21 . C22 . 1.394(5) yes C22 . H221 . 1.000 no C22 . C23 . 1.369(5) yes C23 . H231 . 1.000 no C23 . C24 . 1.406(5) yes C24 . C39 . 1.506(6) yes C24 . C25 . 1.385(5) yes C25 . H251 . 1.000 no C25 . C26 . 1.404(5) yes C26 . C27 . 1.445(5) yes C27 . C38 . 1.409(5) yes C27 . C28 . 1.413(5) yes C28 . H281 . 1.000 no C28 . C29 . 1.370(5) yes C29 . H291 . 1.000 no C29 . C30 . 1.410(5) yes C30 . C37 . 1.408(5) yes C30 . C31 . 1.446(5) yes C31 . C36 . 1.414(5) yes C31 . C32 . 1.395(5) yes C32 . H321 . 1.000 no C32 . C33 . 1.385(6) yes C33 . C40 . 1.509(6) yes C33 . C34 . 1.406(6) yes C34 . H341 . 1.000 no C34 . C35 . 1.383(6) yes C35 . H351 . 1.000 no C35 . C36 . 1.405(5) yes C36 . N4 . 1.373(5) yes N4 . H4 . 0.78(4) no N4 . C37 . 1.386(5) yes C37 . C38 . 1.396(5) yes C39 . H393 . 1.000 no C39 . H392 . 1.000 no C39 . H391 . 1.000 no C40 . H403 . 1.000 no C40 . H402 . 1.000 no C40 . H401 . 1.000 no N5 . H5 . 0.84(5) no N5 . C58 . 1.380(4) yes N5 . C41 . 1.380(4) yes C41 . C46 . 1.417(5) yes C41 . C42 . 1.389(5) yes C42 . H421 . 1.000 no C42 . C43 . 1.369(5) yes C43 . H431 . 1.000 no C43 . C44 . 1.410(6) yes C44 . C59 . 1.516(6) yes C44 . C45 . 1.390(5) yes C45 . H451 . 1.000 no C45 . C46 . 1.396(5) yes C46 . C47 . 1.438(5) yes C47 . C58 . 1.407(5) yes C47 . C48 . 1.418(5) yes C48 . H481 . 1.000 no C48 . C49 . 1.371(5) yes C49 . H491 . 1.000 no C49 . C50 . 1.411(5) yes C50 . C57 . 1.411(5) yes C50 . C51 . 1.447(5) yes C51 . C56 . 1.405(5) yes C51 . C52 . 1.405(5) yes C52 . H521 . 1.000 no C52 . C53 . 1.389(5) yes C53 . C60 . 1.507(6) yes C53 . C54 . 1.404(6) yes C54 . H541 . 1.000 no C54 . C55 . 1.374(5) yes C55 . H551 . 1.000 no C55 . C56 . 1.397(5) yes C56 . N6 . 1.370(4) yes N6 . H6 . 0.81(3) no N6 . C57 . 1.370(4) yes C57 . C58 . 1.394(5) yes C59 . H593 . 1.000 no C59 . H592 . 1.000 no C59 . H591 . 1.000 no C60 . H603 . 1.000 no C60 . H602 . 1.000 no C60 . H601 . 1.000 no N7 . H7 . 0.84(4) no N7 . C78 . 1.372(4) yes N7 . C61 . 1.382(4) yes C61 . C66 . 1.407(4) yes C61 . C62 . 1.391(5) yes C62 . H621 . 1.000 no C62 . C63 . 1.381(5) yes C63 . H631 . 1.000 no C63 . C64 . 1.405(5) yes C64 . C79 . 1.511(5) yes C64 . C65 . 1.382(5) yes C65 . H651 . 1.000 no C65 . C66 . 1.402(4) yes C66 . C67 . 1.435(4) yes C67 . C78 . 1.409(4) yes C67 . C68 . 1.423(4) yes C68 . H681 . 1.000 no C68 . C69 . 1.370(5) yes C69 . H691 . 1.000 no C69 . C70 . 1.416(5) yes C70 . C77 . 1.404(4) yes C70 . C71 . 1.445(5) yes C71 . C76 . 1.402(5) yes C71 . C72 . 1.406(5) yes C72 . H721 . 1.000 no C72 . C73 . 1.382(5) yes C73 . C80 . 1.521(5) yes C73 . C74 . 1.404(6) yes C74 . H741 . 1.000 no C74 . C75 . 1.378(5) yes C75 . H751 . 1.000 no C75 . C76 . 1.393(5) yes C76 . N8 . 1.377(4) yes N8 . H8 . 0.79(4) no N8 . C77 . 1.375(4) yes C77 . C78 . 1.396(4) yes C79 . H793 . 1.000 no C79 . H792 . 1.000 no C79 . H791 . 1.000 no C80 . H803 . 1.000 no C80 . H802 . 1.000 no C80 . H801 . 1.000 no N9 . C93 . 1.525(4) yes N9 . C89 . 1.517(4) yes N9 . C85 . 1.531(4) yes N9 . C81 . 1.521(5) yes C81 . H812 . 1.000 no C81 . H811 . 1.000 no C81 . C82 . 1.527(5) yes C82 . H822 . 1.000 no C82 . H821 . 1.000 no C82 . C83 . 1.498(5) yes C83 . H832 . 1.000 no C83 . H831 . 1.000 no C83 . C84 . 1.509(6) yes C84 . H843 . 1.000 no C84 . H842 . 1.000 no C84 . H841 . 1.000 no C85 . H852 . 1.000 no C85 . H851 . 1.000 no C85 . C86 . 1.521(5) yes C86 . H862 . 1.000 no C86 . H861 . 1.000 no C86 . C87 . 1.533(5) yes C87 . H872 . 1.000 no C87 . H871 . 1.000 no C87 . C88 . 1.515(6) yes C88 . H883 . 1.000 no C88 . H882 . 1.000 no C88 . H881 . 1.000 no C89 . H892 . 1.000 no C89 . H891 . 1.000 no C89 . C90 . 1.523(5) yes C90 . H902 . 1.000 no C90 . H901 . 1.000 no C90 . C91 . 1.493(5) yes C91 . H912 . 1.000 no C91 . H911 . 1.000 no C91 . C92 . 1.527(5) yes C92 . H923 . 1.000 no C92 . H922 . 1.000 no C92 . H921 . 1.000 no C93 . H932 . 1.000 no C93 . H931 . 1.000 no C93 . C94 . 1.497(6) yes C94 . H942 . 1.000 no C94 . H941 . 1.000 no C94 . C95 . 1.538(6) yes C95 . H952 . 1.000 no C95 . H951 . 1.000 no C95 . C96 . 1.494(6) yes C96 . H963 . 1.000 no C96 . H962 . 1.000 no C96 . H961 . 1.000 no N10 . C109 . 1.525(5) yes N10 . C105 . 1.530(4) yes N10 . C101 . 1.508(5) yes N10 . C97 . 1.519(4) yes N10 . C209 . 1.525(5) yes N10 . C105 . 1.530(4) yes N10 . C101 . 1.508(5) yes N10 . C97 . 1.519(4) yes C97 . H972 . 1.000 no C97 . H971 . 1.000 no C97 . C98 . 1.520(5) yes C98 . H982 . 1.000 no C98 . H981 . 1.000 no C98 . C99 . 1.530(5) yes C99 . H992 . 1.000 no C99 . H991 . 1.000 no C99 . C100 . 1.509(5) yes C100 . H1003 . 1.000 no C100 . H1002 . 1.000 no C100 . H1001 . 1.000 no C101 . H1012 . 1.000 no C101 . H1011 . 1.000 no C101 . C102 . 1.528(5) yes C102 . H1022 . 1.000 no C102 . H1021 . 1.000 no C102 . C103 . 1.518(5) yes C103 . H1032 . 1.000 no C103 . H1031 . 1.000 no C103 . C104 . 1.515(5) yes C104 . H1043 . 1.000 no C104 . H1042 . 1.000 no C104 . H1041 . 1.000 no C105 . H1052 . 1.000 no C105 . H1051 . 1.000 no C105 . C106 . 1.510(5) yes C106 . H1062 . 1.000 no C106 . H1061 . 1.000 no C106 . C107 . 1.528(5) yes C107 . H1072 . 1.000 no C107 . H1071 . 1.000 no C107 . C108 . 1.529(6) yes C108 . H1083 . 1.000 no C108 . H1082 . 1.000 no C108 . H1081 . 1.000 no C109 . H1092 . 1.000 no C109 . H1091 . 1.000 no C109 . C110 . 1.490(7) yes C110 . H1102 . 1.000 no C110 . H1101 . 1.000 no C110 . C111 . 1.531(8) yes C111 . H1112 . 1.000 no C111 . H1111 . 1.000 no C111 . C112 . 1.585(7) yes C112 . H1123 . 1.000 no C112 . H1122 . 1.000 no C112 . H1121 . 1.000 no C209 . H2092 . 1.000 no C209 . H2091 . 1.000 no C209 . C210 . 1.610(9) yes C210 . H2102 . 1.000 no C210 . H2101 . 1.000 no C210 . C211 . 1.500(11) yes C211 . H2112 . 1.000 no C211 . H2111 . 1.000 no C211 . C212 . 1.552(9) yes C212 . H2123 . 1.000 no C212 . H2122 . 1.000 no C212 . H2121 . 1.000 no O1 . C116 . 1.425(10) yes O1 . C113 . 1.393(12) yes C113 . H1131 . 1.000 no C113 . C115 . 1.492(13) yes C113 . C114 . 1.470(12) yes C114 . H1143 . 1.000 no C114 . H1142 . 1.000 no C114 . H1141 . 1.000 no C115 . H1153 . 1.000 no C115 . H1152 . 1.000 no C115 . H1151 . 1.000 no C116 . H1161 . 1.000 no C116 . C118 . 1.459(11) yes C116 . C117 . 1.481(11) yes C117 . H1173 . 1.000 no C117 . H1172 . 1.000 no C117 . H1171 . 1.000 no C118 . H1183 . 1.000 no C118 . H1182 . 1.000 no C118 . H1181 . 1.000 no O101 . C216 . 1.460(15) yes O101 . C213 . 1.454(16) yes C213 . H2131 . 1.000 no C213 . C215 . 1.519(17) yes C213 . C214 . 1.499(17) yes C214 . H2143 . 1.000 no C214 . H2142 . 1.000 no C214 . H2141 . 1.000 no C215 . H2153 . 1.000 no C215 . H2152 . 1.000 no C215 . H2151 . 1.000 no C216 . H2161 . 1.000 no C216 . C218 . 1.573(16) yes C216 . C217 . 1.529(16) yes C217 . H2173 . 1.000 no C217 . H2172 . 1.000 no C217 . H2171 . 1.000 no C218 . H2183 . 1.000 no C218 . H2182 . 1.000 no C218 . H2181 . 1.000 no O2 . C122 . 1.435(10) yes O2 . C119 . 1.408(9) yes C119 . H1191 . 1.000 no C119 . C121 . 1.459(11) yes C119 . C120 . 1.492(11) yes C120 . H1203 . 1.000 no C120 . H1202 . 1.000 no C120 . H1201 . 1.000 no C121 . H1213 . 1.000 no C121 . H1212 . 1.000 no C121 . H1211 . 1.000 no C122 . H1221 . 1.000 no C122 . C124 . 1.486(12) yes C122 . C123 . 1.534(11) yes C123 . H1233 . 1.000 no C123 . H1232 . 1.000 no C123 . H1231 . 1.000 no C124 . H1243 . 1.000 no C124 . H1242 . 1.000 no C124 . H1241 . 1.000 no O102 . C222 . 1.425(12) yes O102 . C219 . 1.424(12) yes C219 . H2191 . 1.000 no C219 . C221 . 1.528(14) yes C219 . C220 . 1.492(14) yes C220 . H2203 . 1.000 no C220 . H2202 . 1.000 no C220 . H2201 . 1.000 no C221 . H2213 . 1.000 no C221 . H2212 . 1.000 no C221 . H2211 . 1.000 no C222 . H2221 . 1.000 no C222 . C224 . 1.514(14) yes C222 . C223 . 1.551(14) yes C223 . H2233 . 1.000 no C223 . H2232 . 1.000 no C223 . H2231 . 1.000 no C224 . H2243 . 1.000 no C224 . H2242 . 1.000 no C224 . H2241 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H1 . N1 . C18 . 121(3) no H1 . N1 . C1 . 130(3) no C18 . N1 . C1 . 108.5(3) yes C6 . C1 . C2 . 121.6(3) yes C6 . C1 . N1 . 109.1(3) yes C2 . C1 . N1 . 129.3(3) yes H21 . C2 . C3 . 121.184 no H21 . C2 . C1 . 121.184 no C3 . C2 . C1 . 117.6(3) yes H31 . C3 . C4 . 118.819 no H31 . C3 . C2 . 118.819 no C4 . C3 . C2 . 122.4(3) yes C19 . C4 . C5 . 120.9(3) yes C19 . C4 . C3 . 120.0(3) yes C5 . C4 . C3 . 119.1(3) yes H51 . C5 . C6 . 119.924 no H51 . C5 . C4 . 119.924 no C6 . C5 . C4 . 120.2(3) yes C7 . C6 . C5 . 134.3(3) yes C7 . C6 . C1 . 106.6(3) yes C5 . C6 . C1 . 119.0(3) yes C18 . C7 . C8 . 120.5(3) yes C18 . C7 . C6 . 105.6(3) yes C8 . C7 . C6 . 133.8(3) yes H81 . C8 . C9 . 119.908 no H81 . C8 . C7 . 119.908 no C9 . C8 . C7 . 120.2(3) yes H91 . C9 . C10 . 120.325 no H91 . C9 . C8 . 120.325 no C10 . C9 . C8 . 119.4(3) yes C17 . C10 . C11 . 105.8(3) yes C17 . C10 . C9 . 121.2(3) yes C11 . C10 . C9 . 133.0(3) yes C16 . C11 . C12 . 118.7(3) yes C16 . C11 . C10 . 106.4(3) yes C12 . C11 . C10 . 134.9(3) yes H121 . C12 . C13 . 119.813 no H121 . C12 . C11 . 119.813 no C13 . C12 . C11 . 120.4(3) yes C20 . C13 . C14 . 120.2(3) yes C20 . C13 . C12 . 120.8(4) yes C14 . C13 . C12 . 118.9(3) yes H141 . C14 . C15 . 118.568 no H141 . C14 . C13 . 118.567 no C15 . C14 . C13 . 122.9(3) yes H151 . C15 . C16 . 121.338 no H151 . C15 . C14 . 121.338 no C16 . C15 . C14 . 117.3(3) yes N2 . C16 . C15 . 129.1(3) yes N2 . C16 . C11 . 109.1(3) yes C15 . C16 . C11 . 121.8(3) yes H2 . N2 . C17 . 127(3) no H2 . N2 . C16 . 124(3) no C17 . N2 . C16 . 108.2(3) yes C18 . C17 . N2 . 130.1(3) yes C18 . C17 . C10 . 119.4(3) yes N2 . C17 . C10 . 110.5(3) yes N1 . C18 . C17 . 130.6(3) yes N1 . C18 . C7 . 110.1(3) yes C17 . C18 . C7 . 119.3(3) yes H193 . C19 . H192 . 109.476 no H193 . C19 . H191 . 109.476 no H192 . C19 . H191 . 109.475 no H193 . C19 . C4 . 109.467 no H192 . C19 . C4 . 109.467 no H191 . C19 . C4 . 109.467 no H203 . C20 . H202 . 109.476 no H203 . C20 . H201 . 109.476 no H202 . C20 . H201 . 109.476 no H203 . C20 . C13 . 109.466 no H202 . C20 . C13 . 109.466 no H201 . C20 . C13 . 109.467 no H3 . N3 . C38 . 129(2) no H3 . N3 . C21 . 121(2) no C38 . N3 . C21 . 109.0(3) yes C26 . C21 . C22 . 121.4(3) yes C26 . C21 . N3 . 108.8(3) yes C22 . C21 . N3 . 129.8(3) yes H221 . C22 . C23 . 121.083 no H221 . C22 . C21 . 121.083 no C23 . C22 . C21 . 117.8(3) yes H231 . C23 . C24 . 118.719 no H231 . C23 . C22 . 118.719 no C24 . C23 . C22 . 122.6(3) yes C39 . C24 . C25 . 121.2(3) yes C39 . C24 . C23 . 119.5(3) yes C25 . C24 . C23 . 119.3(3) yes H251 . C25 . C26 . 120.149 no H251 . C25 . C24 . 120.149 no C26 . C25 . C24 . 119.7(3) yes C27 . C26 . C25 . 134.3(3) yes C27 . C26 . C21 . 106.5(3) yes C25 . C26 . C21 . 119.1(3) yes C38 . C27 . C28 . 120.7(3) yes C38 . C27 . C26 . 106.0(3) yes C28 . C27 . C26 . 133.2(3) yes H281 . C28 . C29 . 120.151 no H281 . C28 . C27 . 120.151 no C29 . C28 . C27 . 119.7(3) yes H291 . C29 . C30 . 119.844 no H291 . C29 . C28 . 119.844 no C30 . C29 . C28 . 120.3(3) yes C37 . C30 . C31 . 106.0(3) yes C37 . C30 . C29 . 120.3(3) yes C31 . C30 . C29 . 133.7(3) yes C36 . C31 . C32 . 119.4(3) yes C36 . C31 . C30 . 106.5(3) yes C32 . C31 . C30 . 134.1(3) yes H321 . C32 . C33 . 119.788 no H321 . C32 . C31 . 119.789 no C33 . C32 . C31 . 120.4(4) yes C40 . C33 . C34 . 120.2(4) yes C40 . C33 . C32 . 121.2(4) yes C34 . C33 . C32 . 118.6(4) yes H341 . C34 . C35 . 118.343 no H341 . C34 . C33 . 118.343 no C35 . C34 . C33 . 123.3(4) yes H351 . C35 . C36 . 121.564 no H351 . C35 . C34 . 121.565 no C36 . C35 . C34 . 116.9(4) yes N4 . C36 . C35 . 129.1(3) yes N4 . C36 . C31 . 109.5(3) yes C35 . C36 . C31 . 121.3(4) yes H4 . N4 . C37 . 124(3) no H4 . N4 . C36 . 128(3) no C37 . N4 . C36 . 108.2(3) yes C38 . C37 . N4 . 130.4(3) yes C38 . C37 . C30 . 119.8(3) yes N4 . C37 . C30 . 109.7(3) yes N3 . C38 . C37 . 131.2(3) yes N3 . C38 . C27 . 109.7(3) yes C37 . C38 . C27 . 119.1(3) yes H393 . C39 . H392 . 109.476 no H393 . C39 . H391 . 109.476 no H392 . C39 . H391 . 109.476 no H393 . C39 . C24 . 109.466 no H392 . C39 . C24 . 109.467 no H391 . C39 . C24 . 109.466 no H403 . C40 . H402 . 109.476 no H403 . C40 . H401 . 109.475 no H402 . C40 . H401 . 109.476 no H403 . C40 . C33 . 109.467 no H402 . C40 . C33 . 109.467 no H401 . C40 . C33 . 109.466 no H5 . N5 . C58 . 127(3) no H5 . N5 . C41 . 124(3) no C58 . N5 . C41 . 108.3(3) yes C46 . C41 . C42 . 121.5(3) yes C46 . C41 . N5 . 108.9(3) yes C42 . C41 . N5 . 129.6(3) yes H421 . C42 . C43 . 121.095 no H421 . C42 . C41 . 121.095 no C43 . C42 . C41 . 117.8(3) yes H431 . C43 . C44 . 118.695 no H431 . C43 . C42 . 118.695 no C44 . C43 . C42 . 122.6(3) yes C59 . C44 . C45 . 121.1(4) yes C59 . C44 . C43 . 119.8(4) yes C45 . C44 . C43 . 119.1(3) yes H451 . C45 . C46 . 120.158 no H451 . C45 . C44 . 120.157 no C46 . C45 . C44 . 119.7(3) yes C47 . C46 . C45 . 133.9(3) yes C47 . C46 . C41 . 106.8(3) yes C45 . C46 . C41 . 119.3(3) yes C58 . C47 . C48 . 120.7(3) yes C58 . C47 . C46 . 106.0(3) yes C48 . C47 . C46 . 133.3(3) yes H481 . C48 . C49 . 120.269 no H481 . C48 . C47 . 120.269 no C49 . C48 . C47 . 119.5(3) yes H491 . C49 . C50 . 119.959 no H491 . C49 . C48 . 119.959 no C50 . C49 . C48 . 120.1(3) yes C57 . C50 . C51 . 105.4(3) yes C57 . C50 . C49 . 121.0(3) yes C51 . C50 . C49 . 133.6(3) yes C56 . C51 . C52 . 119.6(3) yes C56 . C51 . C50 . 106.9(3) yes C52 . C51 . C50 . 133.5(3) yes H521 . C52 . C53 . 120.245 no H521 . C52 . C51 . 120.245 no C53 . C52 . C51 . 119.5(3) yes C60 . C53 . C54 . 120.5(4) yes C60 . C53 . C52 . 120.3(4) yes C54 . C53 . C52 . 119.2(3) yes H541 . C54 . C55 . 118.650 no H541 . C54 . C53 . 118.650 no C55 . C54 . C53 . 122.7(3) yes H551 . C55 . C56 . 121.144 no H551 . C55 . C54 . 121.144 no C56 . C55 . C54 . 117.7(3) yes N6 . C56 . C55 . 129.6(3) yes N6 . C56 . C51 . 109.1(3) yes C55 . C56 . C51 . 121.3(3) yes H6 . N6 . C57 . 127(2) no H6 . N6 . C56 . 124(2) no C57 . N6 . C56 . 108.8(3) yes C58 . C57 . N6 . 131.3(3) yes C58 . C57 . C50 . 118.9(3) yes N6 . C57 . C50 . 109.8(3) yes N5 . C58 . C57 . 130.2(3) yes N5 . C58 . C47 . 110.0(3) yes C57 . C58 . C47 . 119.9(3) yes H593 . C59 . H592 . 109.476 no H593 . C59 . H591 . 109.475 no H592 . C59 . H591 . 109.476 no H593 . C59 . C44 . 109.467 no H592 . C59 . C44 . 109.467 no H591 . C59 . C44 . 109.467 no H603 . C60 . H602 . 109.476 no H603 . C60 . H601 . 109.476 no H602 . C60 . H601 . 109.475 no H603 . C60 . C53 . 109.467 no H602 . C60 . C53 . 109.467 no H601 . C60 . C53 . 109.467 no H7 . N7 . C78 . 126(2) no H7 . N7 . C61 . 124(2) no C78 . N7 . C61 . 108.4(3) yes C66 . C61 . C62 . 121.4(3) yes C66 . C61 . N7 . 109.2(3) yes C62 . C61 . N7 . 129.4(3) yes H621 . C62 . C63 . 121.067 no H621 . C62 . C61 . 121.067 no C63 . C62 . C61 . 117.9(3) yes H631 . C63 . C64 . 118.884 no H631 . C63 . C62 . 118.884 no C64 . C63 . C62 . 122.2(3) yes C79 . C64 . C65 . 121.0(3) yes C79 . C64 . C63 . 119.9(3) yes C65 . C64 . C63 . 119.1(3) yes H651 . C65 . C66 . 119.907 no H651 . C65 . C64 . 119.907 no C66 . C65 . C64 . 120.2(3) yes C67 . C66 . C65 . 134.4(3) yes C67 . C66 . C61 . 106.5(3) yes C65 . C66 . C61 . 119.1(3) yes C78 . C67 . C68 . 120.7(3) yes C78 . C67 . C66 . 106.5(3) yes C68 . C67 . C66 . 132.8(3) yes H681 . C68 . C69 . 120.280 no H681 . C68 . C67 . 120.280 no C69 . C68 . C67 . 119.4(3) yes H691 . C69 . C70 . 119.901 no H691 . C69 . C68 . 119.901 no C70 . C69 . C68 . 120.2(3) yes C77 . C70 . C71 . 106.0(3) yes C77 . C70 . C69 . 120.6(3) yes C71 . C70 . C69 . 133.3(3) yes C76 . C71 . C72 . 119.7(3) yes C76 . C71 . C70 . 106.7(3) yes C72 . C71 . C70 . 133.6(3) yes H721 . C72 . C73 . 120.317 no H721 . C72 . C71 . 120.317 no C73 . C72 . C71 . 119.4(3) yes C80 . C73 . C74 . 119.8(3) yes C80 . C73 . C72 . 120.5(4) yes C74 . C73 . C72 . 119.6(3) yes H741 . C74 . C75 . 118.920 no H741 . C74 . C73 . 118.920 no C75 . C74 . C73 . 122.2(3) yes H751 . C75 . C76 . 121.033 no H751 . C75 . C74 . 121.032 no C76 . C75 . C74 . 117.9(3) yes N8 . C76 . C75 . 129.6(3) yes N8 . C76 . C71 . 109.2(3) yes C75 . C76 . C71 . 121.2(3) yes H8 . N8 . C77 . 128(3) no H8 . N8 . C76 . 123(3) no C77 . N8 . C76 . 108.5(3) yes C78 . C77 . N8 . 130.8(3) yes C78 . C77 . C70 . 119.6(3) yes N8 . C77 . C70 . 109.6(3) yes N7 . C78 . C77 . 131.2(3) yes N7 . C78 . C67 . 109.4(3) yes C77 . C78 . C67 . 119.4(3) yes H793 . C79 . H792 . 109.476 no H793 . C79 . H791 . 109.476 no H792 . C79 . H791 . 109.476 no H793 . C79 . C64 . 109.466 no H792 . C79 . C64 . 109.466 no H791 . C79 . C64 . 109.467 no H803 . C80 . H802 . 109.476 no H803 . C80 . H801 . 109.476 no H802 . C80 . H801 . 109.475 no H803 . C80 . C73 . 109.467 no H802 . C80 . C73 . 109.466 no H801 . C80 . C73 . 109.467 no C93 . N9 . C89 . 109.3(3) yes C93 . N9 . C85 . 111.6(2) yes C89 . N9 . C85 . 107.9(3) yes C93 . N9 . C81 . 107.6(3) yes C89 . N9 . C81 . 111.6(2) yes C85 . N9 . C81 . 108.8(3) yes H812 . C81 . H811 . 109.467 no H812 . C81 . C82 . 108.083 no H811 . C81 . C82 . 108.083 no H812 . C81 . N9 . 108.083 no H811 . C81 . N9 . 108.083 no C82 . C81 . N9 . 115.0(3) yes H822 . C82 . H821 . 109.467 no H822 . C82 . C83 . 109.033 no H821 . C82 . C83 . 109.033 no H822 . C82 . C81 . 109.033 no H821 . C82 . C81 . 109.033 no C83 . C82 . C81 . 111.2(3) yes H832 . C83 . H831 . 109.467 no H832 . C83 . C84 . 108.552 no H831 . C83 . C84 . 108.552 no H832 . C83 . C82 . 108.551 no H831 . C83 . C82 . 108.551 no C84 . C83 . C82 . 113.1(3) yes H843 . C84 . H842 . 109.476 no H843 . C84 . H841 . 109.476 no H842 . C84 . H841 . 109.476 no H843 . C84 . C83 . 109.466 no H842 . C84 . C83 . 109.467 no H841 . C84 . C83 . 109.467 no H852 . C85 . H851 . 109.467 no H852 . C85 . C86 . 107.639 no H851 . C85 . C86 . 107.639 no H852 . C85 . N9 . 107.639 no H851 . C85 . N9 . 107.639 no C86 . C85 . N9 . 116.7(3) yes H862 . C86 . H861 . 109.467 no H862 . C86 . C87 . 109.967 no H861 . C86 . C87 . 109.967 no H862 . C86 . C85 . 109.967 no H861 . C86 . C85 . 109.967 no C87 . C86 . C85 . 107.5(3) yes H872 . C87 . H871 . 109.467 no H872 . C87 . C88 . 108.599 no H871 . C87 . C88 . 108.599 no H872 . C87 . C86 . 108.598 no H871 . C87 . C86 . 108.598 no C88 . C87 . C86 . 112.9(3) yes H883 . C88 . H882 . 109.476 no H883 . C88 . H881 . 109.476 no H882 . C88 . H881 . 109.476 no H883 . C88 . C87 . 109.466 no H882 . C88 . C87 . 109.467 no H881 . C88 . C87 . 109.467 no H892 . C89 . H891 . 109.467 no H892 . C89 . C90 . 108.009 no H891 . C89 . C90 . 108.009 no H892 . C89 . N9 . 108.009 no H891 . C89 . N9 . 108.009 no C90 . C89 . N9 . 115.2(3) yes H902 . C90 . H901 . 109.467 no H902 . C90 . C91 . 109.186 no H901 . C90 . C91 . 109.186 no H902 . C90 . C89 . 109.186 no H901 . C90 . C89 . 109.186 no C91 . C90 . C89 . 110.6(3) yes H912 . C91 . H911 . 109.467 no H912 . C91 . C92 . 108.297 no H911 . C91 . C92 . 108.297 no H912 . C91 . C90 . 108.298 no H911 . C91 . C90 . 108.297 no C92 . C91 . C90 . 114.1(3) yes H923 . C92 . H922 . 109.476 no H923 . C92 . H921 . 109.476 no H922 . C92 . H921 . 109.475 no H923 . C92 . C91 . 109.467 no H922 . C92 . C91 . 109.467 no H921 . C92 . C91 . 109.467 no H932 . C93 . H931 . 109.467 no H932 . C93 . C94 . 107.515 no H931 . C93 . C94 . 107.515 no H932 . C93 . N9 . 107.515 no H931 . C93 . N9 . 107.515 no C94 . C93 . N9 . 117.2(3) yes H942 . C94 . H941 . 109.467 no H942 . C94 . C95 . 109.858 no H941 . C94 . C95 . 109.858 no H942 . C94 . C93 . 109.858 no H941 . C94 . C93 . 109.858 no C95 . C94 . C93 . 107.9(4) yes H952 . C95 . H951 . 109.466 no H952 . C95 . C96 . 108.374 no H951 . C95 . C96 . 108.374 no H952 . C95 . C94 . 108.374 no H951 . C95 . C94 . 108.374 no C96 . C95 . C94 . 113.8(4) yes H963 . C96 . H962 . 109.476 no H963 . C96 . H961 . 109.476 no H962 . C96 . H961 . 109.476 no H963 . C96 . C95 . 109.466 no H962 . C96 . C95 . 109.466 no H961 . C96 . C95 . 109.467 no C109 . N10 . C105 . 107.7(3) yes C109 . N10 . C101 . 112.1(3) yes C105 . N10 . C101 . 108.6(3) yes C109 . N10 . C97 . 108.7(3) yes C105 . N10 . C97 . 111.2(2) yes C101 . N10 . C97 . 108.7(3) yes C209 . N10 . C105 . 107.7(3) yes C209 . N10 . C101 . 112.1(3) yes C105 . N10 . C101 . 108.6(3) yes C209 . N10 . C97 . 108.7(3) yes C105 . N10 . C97 . 111.2(2) yes C101 . N10 . C97 . 108.7(3) yes H972 . C97 . H971 . 109.467 no H972 . C97 . C98 . 107.743 no H971 . C97 . C98 . 107.742 no H972 . C97 . N10 . 107.743 no H971 . C97 . N10 . 107.743 no C98 . C97 . N10 . 116.3(3) yes H982 . C98 . H981 . 109.467 no H982 . C98 . C99 . 109.443 no H981 . C98 . C99 . 109.443 no H982 . C98 . C97 . 109.443 no H981 . C98 . C97 . 109.443 no C99 . C98 . C97 . 109.6(3) yes H992 . C99 . H991 . 109.467 no H992 . C99 . C100 . 108.636 no H991 . C99 . C100 . 108.635 no H992 . C99 . C98 . 108.636 no H991 . C99 . C98 . 108.636 no C100 . C99 . C98 . 112.8(3) yes H1003 . C100 . H1002 . 109.476 no H1003 . C100 . H1001 . 109.476 no H1002 . C100 . H1001 . 109.476 no H1003 . C100 . C99 . 109.466 no H1002 . C100 . C99 . 109.467 no H1001 . C100 . C99 . 109.467 no H1012 . C101 . H1011 . 109.467 no H1012 . C101 . C102 . 107.926 no H1011 . C101 . C102 . 107.926 no H1012 . C101 . N10 . 107.926 no H1011 . C101 . N10 . 107.926 no C102 . C101 . N10 . 115.6(3) yes H1022 . C102 . H1021 . 109.467 no H1022 . C102 . C103 . 109.355 no H1021 . C102 . C103 . 109.355 no H1022 . C102 . C101 . 109.355 no H1021 . C102 . C101 . 109.355 no C103 . C102 . C101 . 109.9(3) yes H1032 . C103 . H1031 . 109.467 no H1032 . C103 . C104 . 108.504 no H1031 . C103 . C104 . 108.504 no H1032 . C103 . C102 . 108.504 no H1031 . C103 . C102 . 108.504 no C104 . C103 . C102 . 113.3(3) yes H1043 . C104 . H1042 . 109.476 no H1043 . C104 . H1041 . 109.476 no H1042 . C104 . H1041 . 109.475 no H1043 . C104 . C103 . 109.467 no H1042 . C104 . C103 . 109.467 no H1041 . C104 . C103 . 109.467 no H1052 . C105 . H1051 . 109.467 no H1052 . C105 . C106 . 107.317 no H1051 . C105 . C106 . 107.317 no H1052 . C105 . N10 . 107.316 no H1051 . C105 . N10 . 107.317 no C106 . C105 . N10 . 117.9(3) yes H1062 . C106 . H1061 . 109.467 no H1062 . C106 . C107 . 110.020 no H1061 . C106 . C107 . 110.020 no H1062 . C106 . C105 . 110.019 no H1061 . C106 . C105 . 110.019 no C107 . C106 . C105 . 107.3(3) yes H1072 . C107 . H1071 . 109.466 no H1072 . C107 . C108 . 108.491 no H1071 . C107 . C108 . 108.492 no H1072 . C107 . C106 . 108.491 no H1071 . C107 . C106 . 108.491 no C108 . C107 . C106 . 113.4(3) yes H1083 . C108 . H1082 . 109.476 no H1083 . C108 . H1081 . 109.475 no H1082 . C108 . H1081 . 109.476 no H1083 . C108 . C107 . 109.467 no H1082 . C108 . C107 . 109.467 no H1081 . C108 . C107 . 109.467 no H1092 . C109 . H1091 . 109.466 no H1092 . C109 . C110 . 105.123 no H1091 . C109 . C110 . 105.123 no H1092 . C109 . N10 . 105.124 no H1091 . C109 . N10 . 105.124 no C110 . C109 . N10 . 126.3(4) yes H1102 . C110 . H1101 . 109.467 no H1102 . C110 . C111 . 108.072 no H1101 . C110 . C111 . 108.072 no H1102 . C110 . C109 . 108.072 no H1101 . C110 . C109 . 108.072 no C111 . C110 . C109 . 115.0(5) yes H1112 . C111 . H1111 . 109.467 no H1112 . C111 . C112 . 110.434 no H1111 . C111 . C112 . 110.433 no H1112 . C111 . C110 . 110.434 no H1111 . C111 . C110 . 110.433 no C112 . C111 . C110 . 105.6(4) yes H1123 . C112 . H1122 . 109.476 no H1123 . C112 . H1121 . 109.476 no H1122 . C112 . H1121 . 109.476 no H1123 . C112 . C111 . 109.466 no H1122 . C112 . C111 . 109.467 no H1121 . C112 . C111 . 109.466 no H2092 . C209 . H2091 . 109.467 no H2092 . C209 . C210 . 110.984 no H2091 . C209 . C210 . 110.984 no H2092 . C209 . N10 . 110.983 no H2091 . C209 . N10 . 110.983 no C210 . C209 . N10 . 103.3(4) yes H2102 . C210 . H2101 . 109.467 no H2102 . C210 . C211 . 110.709 no H2101 . C210 . C211 . 110.709 no H2102 . C210 . C209 . 110.709 no H2101 . C210 . C209 . 110.710 no C211 . C210 . C209 . 104.5(6) yes H2112 . C211 . H2111 . 109.467 no H2112 . C211 . C212 . 109.636 no H2111 . C211 . C212 . 109.636 no H2112 . C211 . C210 . 109.636 no H2111 . C211 . C210 . 109.636 no C212 . C211 . C210 . 108.8(6) yes H2123 . C212 . H2122 . 109.476 no H2123 . C212 . H2121 . 109.476 no H2122 . C212 . H2121 . 109.476 no H2123 . C212 . C211 . 109.467 no H2122 . C212 . C211 . 109.467 no H2121 . C212 . C211 . 109.467 no C116 . O1 . C113 . 119.2(8) yes H1131 . C113 . C115 . 91.923 no H1131 . C113 . C114 . 110.080 no C115 . C113 . C114 . 117.7(9) yes H1131 . C113 . O1 . 105.536 no C115 . C113 . O1 . 120.9(9) yes C114 . C113 . O1 . 108.3(9) yes H1143 . C114 . H1142 . 109.477 no H1143 . C114 . H1141 . 109.477 no H1142 . C114 . H1141 . 109.473 no H1143 . C114 . C113 . 109.483 no H1142 . C114 . C113 . 109.459 no H1141 . C114 . C113 . 109.458 no H1153 . C115 . H1152 . 109.476 no H1153 . C115 . H1151 . 109.478 no H1152 . C115 . H1151 . 109.475 no H1153 . C115 . C113 . 109.481 no H1152 . C115 . C113 . 109.457 no H1151 . C115 . C113 . 109.459 no H1161 . C116 . C118 . 98.363 no H1161 . C116 . C117 . 112.423 no C118 . C116 . C117 . 113.8(8) yes H1161 . C116 . O1 . 106.779 no C118 . C116 . O1 . 118.6(8) yes C117 . C116 . O1 . 106.6(7) yes H1173 . C117 . H1172 . 109.473 no H1173 . C117 . H1171 . 109.475 no H1172 . C117 . H1171 . 109.474 no H1173 . C117 . C116 . 109.469 no H1172 . C117 . C116 . 109.467 no H1171 . C117 . C116 . 109.469 no H1183 . C118 . H1182 . 109.478 no H1183 . C118 . H1181 . 109.475 no H1182 . C118 . H1181 . 109.476 no H1183 . C118 . C116 . 109.467 no H1182 . C118 . C116 . 109.467 no H1181 . C118 . C116 . 109.465 no C216 . O101 . C213 . 119.2(13) yes H2131 . C213 . C215 . 92.980 no H2131 . C213 . C214 . 115.797 no C215 . C213 . C214 . 112.5(13) yes H2131 . C213 . O101 . 87.371 no C215 . C213 . O101 . 126.5(14) yes C214 . C213 . O101 . 115.2(12) yes H2143 . C214 . H2142 . 109.469 no H2143 . C214 . H2141 . 109.483 no H2142 . C214 . H2141 . 109.471 no H2143 . C214 . C213 . 109.451 no H2142 . C214 . C213 . 109.484 no H2141 . C214 . C213 . 109.468 no H2153 . C215 . H2152 . 109.492 no H2153 . C215 . H2151 . 109.495 no H2152 . C215 . H2151 . 109.481 no H2153 . C215 . C213 . 109.440 no H2152 . C215 . C213 . 109.461 no H2151 . C215 . C213 . 109.459 no H2161 . C216 . C218 . 108.155 no H2161 . C216 . C217 . 115.398 no C218 . C216 . C217 . 105.6(12) yes H2161 . C216 . O101 . 107.217 no C218 . C216 . O101 . 114.0(12) yes C217 . C216 . O101 . 106.6(12) yes H2173 . C217 . H2172 . 109.483 no H2173 . C217 . H2171 . 109.476 no H2172 . C217 . H2171 . 109.485 no H2173 . C217 . C216 . 109.458 no H2172 . C217 . C216 . 109.464 no H2171 . C217 . C216 . 109.462 no H2183 . C218 . H2182 . 109.478 no H2183 . C218 . H2181 . 109.473 no H2182 . C218 . H2181 . 109.474 no H2183 . C218 . C216 . 109.472 no H2182 . C218 . C216 . 109.466 no H2181 . C218 . C216 . 109.465 no C122 . O2 . C119 . 117.3(6) yes H1191 . C119 . C121 . 101.297 no H1191 . C119 . C120 . 107.296 no C121 . C119 . C120 . 114.4(7) yes H1191 . C119 . O2 . 105.346 no C121 . C119 . O2 . 116.0(7) yes C120 . C119 . O2 . 111.2(7) yes H1203 . C120 . H1202 . 109.476 no H1203 . C120 . H1201 . 109.475 no H1202 . C120 . H1201 . 109.477 no H1203 . C120 . C119 . 109.466 no H1202 . C120 . C119 . 109.467 no H1201 . C120 . C119 . 109.466 no H1213 . C121 . H1212 . 109.476 no H1213 . C121 . H1211 . 109.477 no H1212 . C121 . H1211 . 109.475 no H1213 . C121 . C119 . 109.466 no H1212 . C121 . C119 . 109.466 no H1211 . C121 . C119 . 109.467 no H1221 . C122 . C124 . 113.258 no H1221 . C122 . C123 . 115.329 no C124 . C122 . C123 . 101.8(7) yes H1221 . C122 . O2 . 107.027 no C124 . C122 . O2 . 110.8(7) yes C123 . C122 . O2 . 108.6(7) yes H1233 . C123 . H1232 . 109.476 no H1233 . C123 . H1231 . 109.475 no H1232 . C123 . H1231 . 109.475 no H1233 . C123 . C122 . 109.467 no H1232 . C123 . C122 . 109.467 no H1231 . C123 . C122 . 109.467 no H1243 . C124 . H1242 . 109.477 no H1243 . C124 . H1241 . 109.476 no H1242 . C124 . H1241 . 109.475 no H1243 . C124 . C122 . 109.467 no H1242 . C124 . C122 . 109.466 no H1241 . C124 . C122 . 109.466 no C222 . O102 . C219 . 116.6(8) yes H2191 . C219 . C221 . 93.779 no H2191 . C219 . C220 . 114.338 no C221 . C219 . C220 . 115.5(10) yes H2191 . C219 . O102 . 107.308 no C221 . C219 . O102 . 121.3(9) yes C220 . C219 . O102 . 104.5(9) yes H2203 . C220 . H2202 . 109.476 no H2203 . C220 . H2201 . 109.475 no H2202 . C220 . H2201 . 109.475 no H2203 . C220 . C219 . 109.467 no H2202 . C220 . C219 . 109.467 no H2201 . C220 . C219 . 109.467 no H2213 . C221 . H2212 . 109.477 no H2213 . C221 . H2211 . 109.476 no H2212 . C221 . H2211 . 109.475 no H2213 . C221 . C219 . 109.467 no H2212 . C221 . C219 . 109.467 no H2211 . C221 . C219 . 109.466 no H2221 . C222 . C224 . 103.746 no H2221 . C222 . C223 . 99.947 no C224 . C222 . C223 . 118.7(10) yes H2221 . C222 . O102 . 111.012 no C224 . C222 . O102 . 109.7(10) yes C223 . C222 . O102 . 112.8(9) yes H2233 . C223 . H2232 . 109.476 no H2233 . C223 . H2231 . 109.475 no H2232 . C223 . H2231 . 109.476 no H2233 . C223 . C222 . 109.467 no H2232 . C223 . C222 . 109.467 no H2231 . C223 . C222 . 109.467 no H2243 . C224 . H2242 . 109.476 no H2243 . C224 . H2241 . 109.474 no H2242 . C224 . H2241 . 109.477 no H2243 . C224 . C222 . 109.465 no H2242 . C224 . C222 . 109.467 no H2241 . C224 . C222 . 109.467 no loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_atom_site_label_a _geom_hbond_distance_dh _geom_hbond_distance_ha _geom_hbond_distance_da _geom_hbond_angle_dha _geom_hbond_publ_flag N1 H1 F1 0.88(5) 1.75(5) 2.625(3) 173(5) yes N2 H2 F2 0.85(5) 1.92(5) 2.701(4) 151(4) yes N3 H3 F1 0.79(4) 1.90(4) 2.680(4) 168(3) yes N4 H4 F2 0.78(4) 1.95(4) 2.715(4) 168(4) yes N5 H5 F1 0.84(5) 1.87(5) 2.662(3) 158(4) yes N6 H6 F2 0.81(3) 1.81(3) 2.625(4) 177(3) yes N7 H7 F1 0.84(4) 1.81(4) 2.640(3) 174(3) yes N8 H8 F2 0.79(4) 1.98(4) 2.752(4) 163(4) yes data_arc888 _database_code_depnum_ccdc_archive 'CCDC 247742' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The NH hydrogen atoms were located in a difference Fourier map and their coordiantes and isotropic thermal parameters subsequently refined. Other hydrogen atoms were positioned geometrically, the preferred orientations of the methyl groups having been previously determined by examination of a Fourier map ; #============================================================= _cell_length_a 8.3402(2) _cell_angle_alpha 90 _cell_length_b 16.5722(5) _cell_angle_beta 90.7479(13) _cell_length_c 23.5914(7) _cell_angle_gamma 90 _cell_volume 3260.42(16) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'Cl ' 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C36 H52 Cl N3 ' _chemical_formula_moiety ' C16 H36 N, C20 H16 N2, Cl ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 562.28 _cell_measurement_reflns_used 31120 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.145 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.145 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 31120 _reflns_number_total 7149 #7394 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_theta_min 5.105 _diffrn_reflns_theta_max 27.485 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 30 _refine_diff_density_min -0.37 _refine_diff_density_max 0.38 _refine_ls_number_reflns 4418 _refine_ls_number_restraints 0 _refine_ls_number_parameters 369 #_refine_ls_R_factor_ref 0.0478 _refine_ls_wR_factor_ref 0.0566 _refine_ls_goodness_of_fit_ref 1.0934 #_reflns_number_all 7149 _refine_ls_R_factor_all 0.0905 _refine_ls_wR_factor_all 0.0645 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 4418 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_gt 0.0566 _refine_ls_shift/su_max 0.009681 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.85 1.05 1.44 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type N1 N 0.38213(19) 0.48492(11) 0.24237(7) 0.0271 1.0000 Uani C1 C 0.3268(2) 0.48241(12) 0.29742(8) 0.0256 1.0000 Uani C2 C 0.2701(2) 0.54436(12) 0.33153(9) 0.0298 1.0000 Uani C3 C 0.2211(2) 0.52453(14) 0.38562(9) 0.0337 1.0000 Uani C4 C 0.2280(3) 0.44574(14) 0.40692(9) 0.0343 1.0000 Uani C5 C 0.2860(2) 0.38430(12) 0.37244(9) 0.0305 1.0000 Uani C6 C 0.3354(2) 0.40212(12) 0.31727(8) 0.0271 1.0000 Uani C7 C 0.3967(2) 0.35334(12) 0.27155(8) 0.0270 1.0000 Uani C8 C 0.4289(2) 0.27026(12) 0.26585(8) 0.0297 1.0000 Uani C9 C 0.4782(2) 0.24062(12) 0.21445(9) 0.0304 1.0000 Uani C10 C 0.4996(2) 0.29387(13) 0.16827(8) 0.0283 1.0000 Uani C11 C 0.5431(2) 0.28207(12) 0.10962(8) 0.0288 1.0000 Uani C12 C 0.5723(2) 0.21314(13) 0.07681(9) 0.0332 1.0000 Uani C13 C 0.6121(3) 0.22207(15) 0.02001(9) 0.0384 1.0000 Uani C14 C 0.6219(3) 0.29947(15) -0.00351(9) 0.0408 1.0000 Uani C15 C 0.5890(3) 0.36853(14) 0.02756(9) 0.0372 1.0000 Uani C16 C 0.5477(2) 0.35892(13) 0.08429(8) 0.0298 1.0000 Uani N2 N 0.5073(2) 0.41668(11) 0.12407(7) 0.0304 1.0000 Uani C17 C 0.4764(2) 0.37720(12) 0.17464(8) 0.0259 1.0000 Uani C18 C 0.4227(2) 0.40741(12) 0.22649(8) 0.0259 1.0000 Uani C19 C 0.1738(3) 0.42732(16) 0.46642(10) 0.0470 1.0000 Uani C20 C 0.6438(3) 0.14861(17) -0.01648(10) 0.0494 1.0000 Uani Cl1 Cl 0.43809(6) 0.60168(3) 0.13776(2) 0.0334 1.0000 Uani N3 N 0.06563(18) 0.04758(10) 0.32511(7) 0.0269 1.0000 Uani C21 C -0.0462(2) 0.11648(12) 0.30745(9) 0.0302 1.0000 Uani C22 C 0.0357(3) 0.19695(14) 0.29782(10) 0.0372 1.0000 Uani C23 C -0.0879(3) 0.26417(14) 0.28901(10) 0.0417 1.0000 Uani C24 C -0.1728(3) 0.28806(15) 0.34295(12) 0.0483 1.0000 Uani C25 C 0.1969(2) 0.03587(13) 0.28163(8) 0.0294 1.0000 Uani C26 C 0.1385(2) 0.02569(14) 0.22048(9) 0.0346 1.0000 Uani C27 C 0.2821(2) 0.01538(13) 0.18180(9) 0.0331 1.0000 Uani C28 C 0.2349(3) 0.01345(15) 0.11929(10) 0.0418 1.0000 Uani C29 C 0.1481(2) 0.06615(13) 0.38152(8) 0.0299 1.0000 Uani C30 C 0.0355(3) 0.07921(14) 0.43111(9) 0.0376 1.0000 Uani C31 C 0.1292(3) 0.10952(14) 0.48351(9) 0.0403 1.0000 Uani C32 C 0.1911(4) 0.19465(16) 0.47750(11) 0.0510 1.0000 Uani C33 C -0.0382(2) -0.02775(12) 0.33001(8) 0.0288 1.0000 Uani C34 C 0.0465(2) -0.10357(13) 0.35105(9) 0.0315 1.0000 Uani C35 C -0.0748(3) -0.17215(13) 0.35594(9) 0.0350 1.0000 Uani C36 C 0.0024(3) -0.25003(15) 0.37673(12) 0.0482 1.0000 Uani H1 H 0.389(4) 0.5297(19) 0.2188(13) 0.057(8) 1.0000 Uiso H2 H 0.491(3) 0.4715(18) 0.1188(11) 0.044(7) 1.0000 Uiso H21 H 0.2649 0.6012 0.3175 0.0358 1.0000 Uiso H31 H 0.1790 0.5683 0.4105 0.0404 1.0000 Uiso H51 H 0.2923 0.3277 0.3870 0.0367 1.0000 Uiso H81 H 0.4160 0.2331 0.2989 0.0357 1.0000 Uiso H91 H 0.4990 0.1816 0.2097 0.0365 1.0000 Uiso H121 H 0.5647 0.1582 0.0940 0.0398 1.0000 Uiso H141 H 0.6536 0.3052 -0.0440 0.0490 1.0000 Uiso H151 H 0.5947 0.4233 0.0099 0.0447 1.0000 Uiso H191 H 0.1362 0.4781 0.4849 0.0565 1.0000 Uiso H192 H 0.2654 0.4043 0.4889 0.0565 1.0000 Uiso H193 H 0.0839 0.3874 0.4649 0.0565 1.0000 Uiso H201 H 0.6705 0.1663 -0.0558 0.0592 1.0000 Uiso H202 H 0.7358 0.1174 0.0000 0.0592 1.0000 Uiso H203 H 0.5460 0.1137 -0.0177 0.0592 1.0000 Uiso H211 H -0.1271 0.1238 0.3379 0.0363 1.0000 Uiso H212 H -0.1019 0.1005 0.2714 0.0363 1.0000 Uiso H221 H 0.1044 0.2101 0.3316 0.0447 1.0000 Uiso H222 H 0.1041 0.1931 0.2634 0.0447 1.0000 Uiso H231 H -0.0317 0.3127 0.2738 0.0501 1.0000 Uiso H232 H -0.1701 0.2453 0.2608 0.0501 1.0000 Uiso H241 H -0.2516 0.3320 0.3344 0.0581 1.0000 Uiso H242 H -0.0922 0.3077 0.3715 0.0581 1.0000 Uiso H243 H -0.2305 0.2402 0.3585 0.0581 1.0000 Uiso H251 H 0.2593 -0.0134 0.2924 0.0353 1.0000 Uiso H252 H 0.2689 0.0841 0.2833 0.0353 1.0000 Uiso H261 H 0.0683 -0.0231 0.2176 0.0415 1.0000 Uiso H262 H 0.0762 0.0745 0.2086 0.0415 1.0000 Uiso H271 H 0.3576 0.0615 0.1883 0.0397 1.0000 Uiso H272 H 0.3373 -0.0364 0.1917 0.0397 1.0000 Uiso H281 H 0.3331 0.0066 0.0959 0.0501 1.0000 Uiso H282 H 0.1804 0.0652 0.1088 0.0501 1.0000 Uiso H283 H 0.1601 -0.0327 0.1121 0.0501 1.0000 Uiso H291 H 0.2205 0.0200 0.3912 0.0358 1.0000 Uiso H292 H 0.2133 0.1163 0.3768 0.0358 1.0000 Uiso H301 H -0.0182 0.0270 0.4405 0.0452 1.0000 Uiso H302 H -0.0475 0.1201 0.4202 0.0452 1.0000 Uiso H311 H 0.0566 0.1075 0.5169 0.0483 1.0000 Uiso H312 H 0.2227 0.0728 0.4902 0.0483 1.0000 Uiso H321 H 0.2505 0.2105 0.5129 0.0612 1.0000 Uiso H322 H 0.0988 0.2323 0.4711 0.0612 1.0000 Uiso H323 H 0.2649 0.1976 0.4445 0.0612 1.0000 Uiso H331 H -0.1268 -0.0154 0.3568 0.0345 1.0000 Uiso H332 H -0.0846 -0.0396 0.2916 0.0345 1.0000 Uiso H341 H 0.0966 -0.0929 0.3891 0.0377 1.0000 Uiso H342 H 0.1316 -0.1192 0.3237 0.0377 1.0000 Uiso H351 H -0.1596 -0.1558 0.3832 0.0420 1.0000 Uiso H352 H -0.1248 -0.1820 0.3178 0.0420 1.0000 Uiso H361 H -0.0812 -0.2931 0.3793 0.0578 1.0000 Uiso H362 H 0.0521 -0.2410 0.4150 0.0578 1.0000 Uiso H363 H 0.0869 -0.2672 0.3496 0.0578 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0277(8) 0.0261(9) 0.0274(8) -0.0011(7) -0.0006(6) -0.0011(6) C1 0.0218(9) 0.0287(10) 0.0263(9) 0.0001(7) -0.0029(7) -0.0016(7) C2 0.0273(9) 0.0282(10) 0.0339(10) -0.0030(8) -0.0011(8) -0.0030(8) C3 0.0306(10) 0.0385(12) 0.0320(11) -0.0074(9) 0.0001(8) -0.0012(9) C4 0.0349(11) 0.0380(12) 0.0302(10) -0.0029(9) 0.0041(8) -0.0057(9) C5 0.0320(10) 0.0303(11) 0.0294(10) 0.0010(8) 0.0008(8) -0.0065(8) C6 0.0230(9) 0.0296(10) 0.0287(9) -0.0021(8) -0.0015(7) -0.0032(8) C7 0.0248(9) 0.0292(11) 0.0269(9) 0.0006(8) 0.0002(7) -0.0029(7) C8 0.0292(10) 0.0278(10) 0.0323(10) 0.0021(8) 0.0015(8) -0.0009(8) C9 0.0285(10) 0.0262(10) 0.0366(10) -0.0011(8) 0.0007(8) -0.0017(8) C10 0.0229(9) 0.0302(11) 0.0316(10) -0.0002(8) -0.0005(7) 0.0012(7) C11 0.0251(9) 0.0297(10) 0.0315(10) -0.0021(8) -0.0009(8) 0.0022(8) C12 0.0319(10) 0.0322(11) 0.0353(11) -0.0016(9) -0.0025(8) 0.0053(8) C13 0.0414(12) 0.0425(13) 0.0311(11) -0.0045(9) -0.0009(9) 0.0100(10) C14 0.0453(13) 0.0474(14) 0.0299(11) 0.0014(9) 0.0025(9) 0.0094(10) C15 0.0408(12) 0.0386(12) 0.0323(11) 0.0057(9) 0.0026(9) 0.0040(9) C16 0.0283(10) 0.0325(11) 0.0287(10) -0.0003(8) -0.0011(7) 0.0013(8) N2 0.0332(9) 0.0290(10) 0.0289(9) 0.0009(7) 0.0008(7) 0.0003(7) C17 0.0226(9) 0.0273(10) 0.0279(9) 0.0007(7) -0.0017(7) -0.0020(7) C18 0.0220(9) 0.0261(10) 0.0295(9) -0.0006(7) -0.0026(7) -0.0006(7) C19 0.0602(15) 0.0433(13) 0.0377(12) -0.0047(10) 0.0125(11) -0.0084(11) C20 0.0620(16) 0.0492(15) 0.0367(12) -0.0109(11) -0.0028(11) 0.0171(12) Cl1 0.0319(3) 0.0301(3) 0.0383(3) 0.0066(2) 0.00453(18) 0.0061(2) N3 0.0211(7) 0.0290(9) 0.0307(9) -0.0013(7) -0.0010(6) 0.0004(6) C21 0.0242(9) 0.0314(11) 0.0351(10) 0.0001(8) 0.0007(8) 0.0031(8) C22 0.0335(11) 0.0349(12) 0.0434(12) 0.0031(9) 0.0056(9) -0.0042(9) C23 0.0467(13) 0.0311(12) 0.0474(13) 0.0079(10) 0.0040(10) 0.0007(10) C24 0.0534(15) 0.0306(12) 0.0612(16) -0.0008(11) 0.0098(12) 0.0022(10) C25 0.0224(9) 0.0346(11) 0.0313(10) -0.0042(8) 0.0024(7) -0.0008(8) C26 0.0298(10) 0.0419(13) 0.0319(11) -0.0060(9) -0.0013(8) 0.0040(9) C27 0.0308(10) 0.0349(11) 0.0336(11) -0.0050(8) 0.0020(8) -0.0023(8) C28 0.0474(13) 0.0448(13) 0.0331(11) -0.0018(10) 0.0012(9) 0.0084(10) C29 0.0266(9) 0.0340(11) 0.0290(10) -0.0018(8) -0.0013(7) -0.0040(8) C30 0.0386(12) 0.0414(13) 0.0329(11) -0.0021(9) 0.0059(9) -0.0058(9) C31 0.0534(14) 0.0367(13) 0.0307(11) -0.0027(9) 0.0014(9) -0.0036(10) C32 0.0703(17) 0.0422(14) 0.0405(13) -0.0053(10) -0.0055(12) -0.0131(12) C33 0.0217(9) 0.0312(11) 0.0334(10) -0.0025(8) 0.0001(7) -0.0019(7) C34 0.0274(10) 0.0299(10) 0.0370(11) -0.0006(8) -0.0029(8) 0.0011(8) C35 0.0339(11) 0.0314(11) 0.0397(11) -0.0003(9) -0.0010(9) -0.0008(9) C36 0.0508(14) 0.0328(13) 0.0609(16) 0.0054(11) -0.0033(12) -0.0015(10) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.385(3) yes N1 . C18 . 1.381(3) yes N1 . H1 . 0.93(3) no C1 . C2 . 1.391(3) yes C1 . C6 . 1.412(3) yes C2 . C3 . 1.384(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.400(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.394(3) yes C4 . C19 . 1.512(3) yes C5 . C6 . 1.402(3) yes C5 . H51 . 1.000 no C6 . C7 . 1.447(3) yes C7 . C8 . 1.409(3) yes C7 . C18 . 1.409(3) yes C8 . C9 . 1.376(3) yes C8 . H81 . 1.000 no C9 . C10 . 1.415(3) yes C9 . H91 . 1.000 no C10 . C11 . 1.448(3) yes C10 . C17 . 1.403(3) yes C11 . C12 . 1.403(3) yes C11 . C16 . 1.407(3) yes C12 . C13 . 1.392(3) yes C12 . H121 . 1.000 no C13 . C14 . 1.400(3) yes C13 . C20 . 1.516(3) yes C14 . C15 . 1.388(3) yes C14 . H141 . 1.000 no C15 . C16 . 1.395(3) yes C15 . H151 . 1.000 no C16 . N2 . 1.385(3) yes N2 . C17 . 1.388(3) yes N2 . H2 . 0.93(3) no C17 . C18 . 1.401(3) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no N3 . C21 . 1.528(3) yes N3 . C25 . 1.523(2) yes N3 . C29 . 1.521(3) yes N3 . C33 . 1.525(3) yes C21 . C22 . 1.517(3) yes C21 . H211 . 1.000 no C21 . H212 . 1.000 no C22 . C23 . 1.530(3) yes C22 . H221 . 1.000 no C22 . H222 . 1.000 no C23 . C24 . 1.517(4) yes C23 . H231 . 1.000 no C23 . H232 . 1.000 no C24 . H241 . 1.000 no C24 . H242 . 1.000 no C24 . H243 . 1.000 no C25 . C26 . 1.526(3) yes C25 . H251 . 1.000 no C25 . H252 . 1.000 no C26 . C27 . 1.525(3) yes C26 . H261 . 1.000 no C26 . H262 . 1.000 no C27 . C28 . 1.522(3) yes C27 . H271 . 1.000 no C27 . H272 . 1.000 no C28 . H281 . 1.000 no C28 . H282 . 1.000 no C28 . H283 . 1.000 no C29 . C30 . 1.525(3) yes C29 . H291 . 1.000 no C29 . H292 . 1.000 no C30 . C31 . 1.538(3) yes C30 . H301 . 1.000 no C30 . H302 . 1.000 no C31 . C32 . 1.510(3) yes C31 . H311 . 1.000 no C31 . H312 . 1.000 no C32 . H321 . 1.000 no C32 . H322 . 1.000 no C32 . H323 . 1.000 no C33 . C34 . 1.521(3) yes C33 . H331 . 1.000 no C33 . H332 . 1.000 no C34 . C35 . 1.527(3) yes C34 . H341 . 1.000 no C34 . H342 . 1.000 no C35 . C36 . 1.520(3) yes C35 . H351 . 1.000 no C35 . H352 . 1.000 no C36 . H361 . 1.000 no C36 . H362 . 1.000 no C36 . H363 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C18 . 108.19(16) yes C1 . N1 . H1 . 127.6(18) no C18 . N1 . H1 . 124.2(18) no N1 . C1 . C2 . 129.82(18) yes N1 . C1 . C6 . 108.86(17) yes C2 . C1 . C6 . 121.32(18) yes C1 . C2 . C3 . 117.69(19) yes C1 . C2 . H21 . 121.154 no C3 . C2 . H21 . 121.154 no C2 . C3 . C4 . 122.74(19) yes C2 . C3 . H31 . 118.632 no C4 . C3 . H31 . 118.632 no C3 . C4 . C5 . 119.02(19) yes C3 . C4 . C19 . 120.7(2) yes C5 . C4 . C19 . 120.3(2) yes C4 . C5 . C6 . 119.75(19) yes C4 . C5 . H51 . 120.123 no C6 . C5 . H51 . 120.123 no C1 . C6 . C5 . 119.48(18) yes C1 . C6 . C7 . 107.24(16) yes C5 . C6 . C7 . 133.28(19) yes C6 . C7 . C8 . 133.36(18) yes C6 . C7 . C18 . 105.45(17) yes C8 . C7 . C18 . 121.19(18) yes C7 . C8 . C9 . 119.49(18) yes C7 . C8 . H81 . 120.256 no C9 . C8 . H81 . 120.256 no C8 . C9 . C10 . 119.85(19) yes C8 . C9 . H91 . 120.073 no C10 . C9 . H91 . 120.073 no C9 . C10 . C11 . 133.39(19) yes C9 . C10 . C17 . 120.83(18) yes C11 . C10 . C17 . 105.78(17) yes C10 . C11 . C12 . 133.2(2) yes C10 . C11 . C16 . 106.98(17) yes C12 . C11 . C16 . 119.77(18) yes C11 . C12 . C13 . 119.3(2) yes C11 . C12 . H121 . 120.343 no C13 . C12 . H121 . 120.343 no C12 . C13 . C14 . 119.6(2) yes C12 . C13 . C20 . 120.4(2) yes C14 . C13 . C20 . 119.9(2) yes C13 . C14 . C15 . 122.2(2) yes C13 . C14 . H141 . 118.892 no C15 . C14 . H141 . 118.892 no C14 . C15 . C16 . 117.7(2) yes C14 . C15 . H151 . 121.142 no C16 . C15 . H151 . 121.142 no C11 . C16 . C15 . 121.27(19) yes C11 . C16 . N2 . 109.22(17) yes C15 . C16 . N2 . 129.5(2) yes C16 . N2 . C17 . 107.84(17) yes C16 . N2 . H2 . 128.6(16) no C17 . N2 . H2 . 123.3(16) no C10 . C17 . N2 . 110.16(17) yes C10 . C17 . C18 . 119.45(17) yes N2 . C17 . C18 . 130.34(18) yes N1 . C18 . C7 . 110.25(17) yes N1 . C18 . C17 . 130.65(18) yes C7 . C18 . C17 . 119.05(18) yes C4 . C19 . H191 . 109.467 no C4 . C19 . H192 . 109.467 no H191 . C19 . H192 . 109.475 no C4 . C19 . H193 . 109.467 no H191 . C19 . H193 . 109.476 no H192 . C19 . H193 . 109.476 no C13 . C20 . H201 . 109.467 no C13 . C20 . H202 . 109.467 no H201 . C20 . H202 . 109.476 no C13 . C20 . H203 . 109.467 no H201 . C20 . H203 . 109.476 no H202 . C20 . H203 . 109.476 no C21 . N3 . C25 . 110.68(15) yes C21 . N3 . C29 . 110.76(15) yes C25 . N3 . C29 . 107.12(14) yes C21 . N3 . C33 . 106.69(14) yes C25 . N3 . C33 . 111.16(15) yes C29 . N3 . C33 . 110.48(15) yes N3 . C21 . C22 . 115.07(16) yes N3 . C21 . H211 . 108.055 no C22 . C21 . H211 . 108.055 no N3 . C21 . H212 . 108.055 no C22 . C21 . H212 . 108.055 no H211 . C21 . H212 . 109.467 no C21 . C22 . C23 . 110.93(18) yes C21 . C22 . H221 . 109.106 no C23 . C22 . H221 . 109.106 no C21 . C22 . H222 . 109.106 no C23 . C22 . H222 . 109.106 no H221 . C22 . H222 . 109.467 no C22 . C23 . C24 . 113.4(2) yes C22 . C23 . H231 . 108.483 no C24 . C23 . H231 . 108.484 no C22 . C23 . H232 . 108.483 no C24 . C23 . H232 . 108.484 no H231 . C23 . H232 . 109.466 no C23 . C24 . H241 . 109.467 no C23 . C24 . H242 . 109.467 no H241 . C24 . H242 . 109.476 no C23 . C24 . H243 . 109.467 no H241 . C24 . H243 . 109.476 no H242 . C24 . H243 . 109.476 no N3 . C25 . C26 . 115.30(15) yes N3 . C25 . H251 . 107.997 no C26 . C25 . H251 . 107.997 no N3 . C25 . H252 . 107.997 no C26 . C25 . H252 . 107.997 no H251 . C25 . H252 . 109.467 no C25 . C26 . C27 . 109.53(17) yes C25 . C26 . H261 . 109.457 no C27 . C26 . H261 . 109.457 no C25 . C26 . H262 . 109.457 no C27 . C26 . H262 . 109.457 no H261 . C26 . H262 . 109.467 no C26 . C27 . C28 . 112.74(18) yes C26 . C27 . H271 . 108.649 no C28 . C27 . H271 . 108.649 no C26 . C27 . H272 . 108.649 no C28 . C27 . H272 . 108.649 no H271 . C27 . H272 . 109.467 no C27 . C28 . H281 . 109.467 no C27 . C28 . H282 . 109.467 no H281 . C28 . H282 . 109.476 no C27 . C28 . H283 . 109.467 no H281 . C28 . H283 . 109.476 no H282 . C28 . H283 . 109.476 no N3 . C29 . C30 . 115.09(16) yes N3 . C29 . H291 . 108.050 no C30 . C29 . H291 . 108.050 no N3 . C29 . H292 . 108.050 no C30 . C29 . H292 . 108.050 no H291 . C29 . H292 . 109.467 no C29 . C30 . C31 . 110.58(18) yes C29 . C30 . H301 . 109.195 no C31 . C30 . H301 . 109.195 no C29 . C30 . H302 . 109.195 no C31 . C30 . H302 . 109.195 no H301 . C30 . H302 . 109.467 no C30 . C31 . C32 . 113.61(19) yes C30 . C31 . H311 . 108.428 no C32 . C31 . H311 . 108.428 no C30 . C31 . H312 . 108.428 no C32 . C31 . H312 . 108.428 no H311 . C31 . H312 . 109.467 no C31 . C32 . H321 . 109.467 no C31 . C32 . H322 . 109.467 no H321 . C32 . H322 . 109.476 no C31 . C32 . H323 . 109.467 no H321 . C32 . H323 . 109.476 no H322 . C32 . H323 . 109.476 no N3 . C33 . C34 . 116.05(15) yes N3 . C33 . H331 . 107.803 no C34 . C33 . H331 . 107.803 no N3 . C33 . H332 . 107.803 no C34 . C33 . H332 . 107.803 no H331 . C33 . H332 . 109.467 no C33 . C34 . C35 . 109.53(16) yes C33 . C34 . H341 . 109.458 no C35 . C34 . H341 . 109.458 no C33 . C34 . H342 . 109.458 no C35 . C34 . H342 . 109.458 no H341 . C34 . H342 . 109.467 no C34 . C35 . C36 . 112.23(19) yes C34 . C35 . H351 . 108.778 no C36 . C35 . H351 . 108.778 no C34 . C35 . H352 . 108.778 no C36 . C35 . H352 . 108.778 no H351 . C35 . H352 . 109.467 no C35 . C36 . H361 . 109.467 no C35 . C36 . H362 . 109.467 no H361 . C36 . H362 . 109.476 no C35 . C36 . H363 . 109.467 no H361 . C36 . H363 . 109.476 no H362 . C36 . H363 . 109.476 no loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_atom_site_label_a _geom_hbond_distance_dh _geom_hbond_distance_ha _geom_hbond_distance_da _geom_hbond_angle_dha _geom_hbond_publ_flag N1 H1 Cl1 0.93(3) 2.29(3) 3.1753(18) 158(2) yes N2 H2 Cl1 0.93(3) 2.25(3) 3.1375(19) 161(2) yes