# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'A. Nangia' 'Balakrishna R. Bhogala' _publ_contact_author_name 'A. Nangia' _publ_contact_author_address ; School of Chemistry University of Hyderabad P O Central University Hyderabad 500046 INDIA ; _publ_contact_author_email ASHWINI_NANGIA@REDIFFMAIL.COM _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Ternary and quaternary cocrystals of 1,3cis,5cis-cyclohexanetricarboxylic acid and 4,4'-bipyridines ; data_1 _database_code_depnum_ccdc_archive 'CCDC 264605' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 4,4'-bipyridine - 1,2-bis(4-pyridyl)ethane ; _chemical_melting_point 453 _chemical_formula_moiety C9H12O6,C10H8N2,0.5(C12H12N2) _chemical_formula_sum 'C25 H26 N3 O6' _chemical_formula_weight 464.49 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2 /c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.167(7) _cell_length_b 9.954(2) _cell_length_c 14.988(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.91(3) _cell_angle_gamma 90.00 _cell_volume 4622.0(16) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.1 _cell_measurement_theta_max 10.5 _exptl_crystal_description cubic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1960 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius MACH-3' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time 90 _diffrn_standards_decay_% 1 _diffrn_reflns_number 5383 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5302 _reflns_number_gt 3011 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 data collection software' _computing_cell_refinement 'CAD4 data collection software' _computing_data_reduction 'XTAL 3.5' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+3.5709P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5302 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1025 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O13 O 0.15205(6) 0.37431(19) 0.14927(15) 0.0639(5) Uani 1 1 d . . . O15 O 0.03723(6) 0.41266(18) 0.44208(14) 0.0615(5) Uani 1 1 d . . . C1 C 0.10986(7) 0.6751(2) 0.29308(15) 0.0396(5) Uani 1 1 d . . . H1A H 0.0805 0.7053 0.2560 0.048 Uiso 1 1 calc R . . C2 C 0.10779(7) 0.5965(2) 0.37938(15) 0.0410(5) Uani 1 1 d . . . H2A H 0.1363 0.5636 0.4171 0.049 Uiso 1 1 calc R . . H2B H 0.0982 0.6554 0.4193 0.049 Uiso 1 1 calc R . . O11 O 0.12303(6) 0.90663(18) 0.33135(16) 0.0750(6) Uani 1 1 d . . . C3 C 0.07680(7) 0.4789(2) 0.34583(15) 0.0416(5) Uani 1 1 d . . . H3A H 0.0481 0.5141 0.3088 0.050 Uiso 1 1 calc R . . C5 C 0.09604(7) 0.4609(2) 0.19670(15) 0.0398(5) Uani 1 1 d . . . H5A H 0.0673 0.4913 0.1554 0.048 Uiso 1 1 calc R . . C6 C 0.12452(7) 0.5840(2) 0.22896(16) 0.0434(5) Uani 1 1 d . . . H6A H 0.1242 0.6343 0.1733 0.052 Uiso 1 1 calc R . . H6B H 0.1540 0.5555 0.2633 0.052 Uiso 1 1 calc R . . C9 C 0.11163(7) 0.3599(2) 0.14152(16) 0.0460(5) Uani 1 1 d . . . O10 O 0.17888(6) 0.77610(19) 0.34888(16) 0.0764(6) Uani 1 1 d . . . C8 C 0.07381(7) 0.4000(2) 0.42983(16) 0.0457(5) Uani 1 1 d . . . C7 C 0.13747(7) 0.7981(2) 0.32523(17) 0.0458(5) Uani 1 1 d . . . O12 O 0.08983(6) 0.2698(2) 0.09711(15) 0.0790(6) Uani 1 1 d . . . C4 C 0.09107(7) 0.3864(2) 0.28183(16) 0.0451(5) Uani 1 1 d . . . H4A H 0.0700 0.3150 0.2582 0.054 Uiso 1 1 calc R . . H4B H 0.1184 0.3454 0.3192 0.054 Uiso 1 1 calc R . . O14 O 0.10265(6) 0.3295(2) 0.47899(14) 0.0803(7) Uani 1 1 d . . . N28 N 0.02677(6) 0.76363(19) 0.05913(13) 0.0470(5) Uani 1 1 d . . . C31 C 0.00200(7) 0.9774(2) 0.14774(14) 0.0401(5) Uani 1 1 d . . . C30 C -0.02151(7) 0.8603(2) 0.12546(16) 0.0477(6) Uani 1 1 d . . . H30A H -0.0464 0.8514 0.1401 0.057 Uiso 1 1 calc R . . C32 C 0.03869(8) 0.9830(2) 0.12456(17) 0.0506(6) Uani 1 1 d . . . H32A H 0.0559 1.0595 0.1387 0.061 Uiso 1 1 calc R . . C33 C 0.04961(8) 0.8754(3) 0.08055(17) 0.0519(6) Uani 1 1 d . . . H33A H 0.0743 0.8816 0.0651 0.062 Uiso 1 1 calc R . . C29 C -0.00858(8) 0.7570(2) 0.08190(16) 0.0495(6) Uani 1 1 d . . . H29A H -0.0251 0.6790 0.0675 0.059 Uiso 1 1 calc R . . C34 C -0.01138(8) 1.0929(2) 0.19543(16) 0.0507(6) Uani 1 1 d . . . H34A H -0.0423 1.0889 0.1803 0.061 Uiso 1 1 calc R . . H34B H -0.0050 1.1765 0.1699 0.061 Uiso 1 1 calc R . . N22 N 0.22487(7) 0.0042(2) 0.38199(17) 0.0623(6) Uani 1 1 d . . . C19 C 0.28191(7) 0.3938(2) 0.39152(17) 0.0468(5) Uani 1 1 d . . . C25 C 0.26275(7) 0.2583(2) 0.38834(17) 0.0476(6) Uani 1 1 d . . . N16 N 0.31716(7) 0.6500(2) 0.39807(17) 0.0613(6) Uani 1 1 d . . . C26 C 0.28705(8) 0.1423(3) 0.4135(2) 0.0647(7) Uani 1 1 d . . . H26A H 0.3170 0.1470 0.4331 0.078 Uiso 1 1 calc R . . C20 C 0.32561(8) 0.4157(3) 0.4300(2) 0.0675(8) Uani 1 1 d . . . H20A H 0.3444 0.3445 0.4548 0.081 Uiso 1 1 calc R . . C24 C 0.21838(8) 0.2413(3) 0.3605(2) 0.0624(7) Uani 1 1 d . . . H24A H 0.2003 0.3157 0.3436 0.075 Uiso 1 1 calc R . . C23 C 0.20120(8) 0.1156(3) 0.3576(2) 0.0657(7) Uani 1 1 d . . . H23A H 0.1713 0.1076 0.3376 0.079 Uiso 1 1 calc R . . C21 C 0.34145(9) 0.5444(3) 0.4318(2) 0.0693(8) Uani 1 1 d . . . H21A H 0.3712 0.5569 0.4585 0.083 Uiso 1 1 calc R . . C27 C 0.26744(8) 0.0208(3) 0.4099(2) 0.0694(8) Uani 1 1 d . . . H27A H 0.2849 -0.0550 0.4281 0.083 Uiso 1 1 calc R . . C17 C 0.27546(10) 0.6293(3) 0.3620(3) 0.0776(9) Uani 1 1 d . . . H17A H 0.2574 0.7026 0.3387 0.093 Uiso 1 1 calc R . . C18 C 0.25706(9) 0.5044(3) 0.3569(2) 0.0748(9) Uani 1 1 d . . . H18A H 0.2272 0.4954 0.3294 0.090 Uiso 1 1 calc R . . H13 H 0.1596(10) 0.294(3) 0.126(2) 0.095(11) Uiso 1 1 d . . . H10 H 0.1975(11) 0.871(4) 0.364(2) 0.110(11) Uiso 1 1 d . . . H15 H 0.0374(10) 0.350(3) 0.489(2) 0.103(11) Uiso 1 1 d . . . 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 O13 0.0588(11) 0.0496(11) 0.0950(14) -0.0165(10) 0.0417(10) -0.0031(9) O15 0.0717(12) 0.0563(11) 0.0772(13) 0.0224(10) 0.0518(10) 0.0126(9) C1 0.0380(11) 0.0386(12) 0.0435(12) 0.0023(9) 0.0161(9) 0.0009(9) C2 0.0426(11) 0.0406(12) 0.0422(12) 0.0014(9) 0.0181(9) 0.0017(10) O11 0.0576(11) 0.0438(10) 0.1207(17) -0.0142(11) 0.0284(11) -0.0030(9) C3 0.0377(11) 0.0486(13) 0.0415(12) 0.0086(10) 0.0179(9) 0.0023(10) C5 0.0399(11) 0.0410(12) 0.0394(11) 0.0029(9) 0.0155(9) 0.0013(9) C6 0.0478(12) 0.0408(12) 0.0479(13) 0.0012(10) 0.0246(10) -0.0045(10) C9 0.0486(13) 0.0488(14) 0.0409(12) -0.0002(11) 0.0164(10) -0.0034(11) O10 0.0437(10) 0.0497(11) 0.1331(19) -0.0166(11) 0.0283(11) -0.0052(9) C8 0.0485(13) 0.0461(13) 0.0451(13) 0.0007(11) 0.0200(11) -0.0083(11) C7 0.0446(12) 0.0387(13) 0.0559(14) -0.0002(11) 0.0200(11) -0.0018(10) O12 0.0669(12) 0.0802(14) 0.0926(15) -0.0431(12) 0.0317(11) -0.0190(11) C4 0.0483(12) 0.0426(12) 0.0478(13) -0.0006(10) 0.0210(10) -0.0080(10) O14 0.0561(11) 0.1122(17) 0.0742(13) 0.0516(12) 0.0252(10) 0.0177(11) N28 0.0545(11) 0.0483(11) 0.0433(10) -0.0029(9) 0.0236(9) 0.0028(9) C31 0.0511(12) 0.0395(12) 0.0317(10) 0.0045(9) 0.0170(9) 0.0012(10) C30 0.0487(13) 0.0500(14) 0.0522(14) -0.0044(11) 0.0276(11) -0.0050(11) C32 0.0555(14) 0.0447(13) 0.0548(14) -0.0018(11) 0.0237(12) -0.0114(11) C33 0.0509(13) 0.0566(15) 0.0569(15) -0.0023(12) 0.0301(12) -0.0046(12) C29 0.0546(13) 0.0458(13) 0.0533(14) -0.0089(11) 0.0255(11) -0.0119(11) C34 0.0708(16) 0.0365(12) 0.0482(13) 0.0061(10) 0.0255(12) 0.0066(11) N22 0.0540(12) 0.0500(13) 0.0857(16) -0.0082(11) 0.0286(11) -0.0098(10) C19 0.0435(12) 0.0468(13) 0.0519(13) 0.0028(11) 0.0192(10) -0.0032(11) C25 0.0441(12) 0.0488(14) 0.0513(13) -0.0012(11) 0.0186(10) -0.0050(11) N16 0.0604(13) 0.0513(13) 0.0789(15) 0.0090(11) 0.0328(12) -0.0020(11) C26 0.0449(14) 0.0518(16) 0.098(2) -0.0057(15) 0.0259(14) -0.0026(12) C20 0.0453(14) 0.0509(15) 0.100(2) 0.0107(15) 0.0176(14) -0.0018(12) C24 0.0433(13) 0.0524(16) 0.0858(19) 0.0078(14) 0.0159(13) -0.0004(12) C23 0.0448(14) 0.0619(18) 0.085(2) 0.0014(15) 0.0167(13) -0.0085(13) C21 0.0460(14) 0.0609(18) 0.095(2) 0.0040(16) 0.0174(14) -0.0117(13) C27 0.0512(15) 0.0475(15) 0.110(2) -0.0083(15) 0.0291(15) -0.0024(12) C17 0.0614(18) 0.0538(17) 0.122(3) 0.0193(17) 0.0375(18) 0.0058(14) C18 0.0444(14) 0.0595(18) 0.118(3) 0.0167(17) 0.0260(15) 0.0005(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O13 C9 1.312(3) . ? O13 H13 0.94(3) . ? O15 C8 1.297(3) . ? O15 H15 0.94(4) . ? C1 C7 1.501(3) . ? C1 C6 1.522(3) . ? C1 C2 1.534(3) . ? C1 H1A 0.9800 . ? C2 C3 1.520(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? O11 C7 1.198(3) . ? C3 C8 1.517(3) . ? C3 C4 1.522(3) . ? C3 H3A 0.9800 . ? C5 C9 1.506(3) . ? C5 C6 1.517(3) . ? C5 C4 1.535(3) . ? C5 H5A 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C9 O12 1.194(3) . ? O10 C7 1.308(3) . ? O10 H10 1.11(4) . ? C8 O14 1.203(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N28 C33 1.320(3) . ? N28 C29 1.334(3) . ? C31 C30 1.375(3) . ? C31 C32 1.381(3) . ? C31 C34 1.502(3) . ? C30 C29 1.366(3) . ? C30 H30A 0.9300 . ? C32 C33 1.373(3) . ? C32 H32A 0.9300 . ? C33 H33A 0.9300 . ? C29 H29A 0.9300 . ? C34 C34 1.538(4) 2 ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? N22 C27 1.332(3) . ? N22 C23 1.332(3) . ? C19 C18 1.363(3) . ? C19 C20 1.373(3) . ? C19 C25 1.484(3) . ? C25 C26 1.381(3) . ? C25 C24 1.389(3) . ? N16 C17 1.309(3) . ? N16 C21 1.310(3) . ? C26 C27 1.365(4) . ? C26 H26A 0.9300 . ? C20 C21 1.381(4) . ? C20 H20A 0.9300 . ? C24 C23 1.369(4) . ? C24 H24A 0.9300 . ? C23 H23A 0.9300 . ? C21 H21A 0.9300 . ? C27 H27A 0.9300 . ? C17 C18 1.374(4) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? 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 _geom_angle_publ_flag C9 O13 H13 105.7(19) . . ? C8 O15 H15 107(2) . . ? C7 C1 C6 113.12(18) . . ? C7 C1 C2 110.54(18) . . ? C6 C1 C2 110.44(18) . . ? C7 C1 H1A 107.5 . . ? C6 C1 H1A 107.5 . . ? C2 C1 H1A 107.5 . . ? C3 C2 C1 110.01(17) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C8 C3 C2 111.15(18) . . ? C8 C3 C4 109.69(19) . . ? C2 C3 C4 110.41(17) . . ? C8 C3 H3A 108.5 . . ? C2 C3 H3A 108.5 . . ? C4 C3 H3A 108.5 . . ? C9 C5 C6 114.67(18) . . ? C9 C5 C4 107.07(18) . . ? C6 C5 C4 111.40(17) . . ? C9 C5 H5A 107.8 . . ? C6 C5 H5A 107.8 . . ? C4 C5 H5A 107.8 . . ? C5 C6 C1 112.31(17) . . ? C5 C6 H6A 109.1 . . ? C1 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C1 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? O12 C9 O13 121.9(2) . . ? O12 C9 C5 123.3(2) . . ? O13 C9 C5 114.8(2) . . ? C7 O10 H10 111.6(17) . . ? O14 C8 O15 123.3(2) . . ? O14 C8 C3 122.5(2) . . ? O15 C8 C3 114.1(2) . . ? O11 C7 O10 122.6(2) . . ? O11 C7 C1 123.0(2) . . ? O10 C7 C1 114.3(2) . . ? C3 C4 C5 112.41(18) . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? C33 N28 C29 117.4(2) . . ? C30 C31 C32 116.6(2) . . ? C30 C31 C34 121.7(2) . . ? C32 C31 C34 121.7(2) . . ? C29 C30 C31 120.4(2) . . ? C29 C30 H30A 119.8 . . ? C31 C30 H30A 119.8 . . ? C33 C32 C31 119.8(2) . . ? C33 C32 H32A 120.1 . . ? C31 C32 H32A 120.1 . . ? N28 C33 C32 123.2(2) . . ? N28 C33 H33A 118.4 . . ? C32 C33 H33A 118.4 . . ? N28 C29 C30 122.6(2) . . ? N28 C29 H29A 118.7 . . ? C30 C29 H29A 118.7 . . ? C31 C34 C34 112.95(18) . 2 ? C31 C34 H34A 109.0 . . ? C34 C34 H34A 109.0 2 . ? C31 C34 H34B 109.0 . . ? C34 C34 H34B 109.0 2 . ? H34A C34 H34B 107.8 . . ? C27 N22 C23 115.9(2) . . ? C18 C19 C20 115.8(2) . . ? C18 C19 C25 121.9(2) . . ? C20 C19 C25 122.3(2) . . ? C26 C25 C24 115.7(2) . . ? C26 C25 C19 123.3(2) . . ? C24 C25 C19 121.0(2) . . ? C17 N16 C21 116.5(2) . . ? C27 C26 C25 120.4(2) . . ? C27 C26 H26A 119.8 . . ? C25 C26 H26A 119.8 . . ? C19 C20 C21 119.5(2) . . ? C19 C20 H20A 120.2 . . ? C21 C20 H20A 120.2 . . ? C23 C24 C25 120.3(2) . . ? C23 C24 H24A 119.8 . . ? C25 C24 H24A 119.8 . . ? N22 C23 C24 123.7(2) . . ? N22 C23 H23A 118.2 . . ? C24 C23 H23A 118.2 . . ? N16 C21 C20 124.0(2) . . ? N16 C21 H21A 118.0 . . ? C20 C21 H21A 118.0 . . ? N22 C27 C26 124.0(3) . . ? N22 C27 H27A 118.0 . . ? C26 C27 H27A 118.0 . . ? N16 C17 C18 123.2(3) . . ? N16 C17 H17A 118.4 . . ? C18 C17 H17A 118.4 . . ? C19 C18 C17 120.9(2) . . ? C19 C18 H18A 119.6 . . ? C17 C18 H18A 119.6 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.206 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.038 # Attachment 'cocrystal_2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 681085' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1,2-bis(4-pyridyl)ethylene - 1,2-bis(4-pyridyl)ethane ; _chemical_melting_point 481(2) _chemical_formula_moiety (C9H12O6),(C12H10N2),0.5(C12H12N2) _chemical_formula_sum 'C27 H28 N3 O6' _chemical_formula_weight 490.52 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5110(14) _cell_length_b 11.9877(15) _cell_length_c 19.720(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.511(2) _cell_angle_gamma 90.00 _cell_volume 2482.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2075 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 20.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1036 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9661 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18168 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4817 _reflns_number_gt 2753 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1320P)^2^+5.1763P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4817 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1775 _refine_ls_R_factor_gt 0.1154 _refine_ls_wR_factor_ref 0.3229 _refine_ls_wR_factor_gt 0.2787 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 3.617 _refine_ls_shift/su_mean 0.045 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N27 N 0.6112(4) 0.3385(3) 0.1168(2) 0.0540(11) Uani 1 1 d . . . C24 C 0.6522(5) 0.5572(4) 0.1571(2) 0.0517(13) Uani 1 1 d . . . O15 O 0.7024(6) 0.2753(4) 0.3382(2) 0.0861(16) Uani 1 1 d . . . O9 O 0.5085(5) 0.6490(4) 0.4040(2) 0.0707(12) Uani 1 1 d . . . O14 O 0.7367(4) 0.1843(3) 0.43375(19) 0.0712(12) Uani 1 1 d . . . C25 C 0.6596(5) 0.4694(4) 0.2015(2) 0.0557(14) Uani 1 1 d . . . H25 H 0.6805 0.4826 0.2481 0.067 Uiso 1 1 calc R . . O12 O 0.9247(5) 0.5678(5) 0.6384(2) 0.0862(17) Uani 1 1 d . . . N34 N 0.0025(5) 0.9616(5) 0.2668(2) 0.0692(14) Uani 1 1 d . . . N21 N 0.6695(5) 1.0593(4) 0.2937(3) 0.0682(13) Uani 1 1 d . . . C31 C 0.0409(5) 0.9953(5) 0.4062(2) 0.0557(14) Uani 1 1 d . . . C6 C 0.6638(6) 0.4643(4) 0.4236(3) 0.0603(15) Uani 1 1 d . . . H6A H 0.5798 0.4369 0.4371 0.072 Uiso 1 1 calc R . . H6B H 0.6572 0.4780 0.3741 0.072 Uiso 1 1 calc R . . C29 C 0.6279(5) 0.5332(4) 0.0890(2) 0.0510(13) Uani 1 1 d . . . H29 H 0.6255 0.5906 0.0558 0.061 Uiso 1 1 calc R . . C19 C 0.6364(5) 0.9281(4) 0.2118(2) 0.0544(13) Uani 1 1 d . . . H19 H 0.6129 0.9152 0.1654 0.065 Uiso 1 1 calc R . . C22 C 0.6960(5) 0.9850(5) 0.3387(3) 0.0601(15) Uani 1 1 d . . . H22 H 0.7176 1.0080 0.3838 0.072 Uiso 1 1 calc R . . C35 C -0.0047(6) 1.0628(6) 0.2939(3) 0.0710(17) Uani 1 1 d . . . H35 H -0.0241 1.1241 0.2647 0.085 Uiso 1 1 calc R . . C26 C 0.6377(5) 0.3649(5) 0.1797(3) 0.0577(14) Uani 1 1 d . . . H26 H 0.6417 0.3066 0.2124 0.069 Uiso 1 1 calc R . . C18 C 0.6634(5) 0.8373(4) 0.2533(2) 0.0489(12) Uani 1 1 d . . . C4 C 0.8183(5) 0.3704(4) 0.5038(2) 0.0544(13) Uani 1 1 d . . . H4A H 0.9027 0.3356 0.4988 0.065 Uiso 1 1 calc R . . H4B H 0.7683 0.3204 0.5324 0.065 Uiso 1 1 calc R . . C13 C 0.7287(6) 0.2698(4) 0.4021(3) 0.0586(14) Uani 1 1 d . . . C2 C 0.7465(7) 0.5611(5) 0.5295(3) 0.0718(18) Uani 1 1 d . . . H2A H 0.7846 0.6334 0.5437 0.086 Uiso 1 1 calc R . . H2B H 0.6764 0.5455 0.5600 0.086 Uiso 1 1 calc R . . C32 C 0.0470(5) 0.8913(5) 0.3775(3) 0.0635(15) Uani 1 1 d . . . H32 H 0.0638 0.8281 0.4055 0.076 Uiso 1 1 calc R . . C7 C 0.5941(6) 0.6616(4) 0.4535(3) 0.0598(15) Uani 1 1 d . . . C23 C 0.6939(5) 0.8644(6) 0.3226(3) 0.0694(18) Uani 1 1 d . . . H23 H 0.7117 0.8089 0.3561 0.083 Uiso 1 1 calc R . . C28 C 0.6069(5) 0.4211(5) 0.0706(2) 0.0575(15) Uani 1 1 d . . . H28 H 0.5891 0.4033 0.0242 0.069 Uiso 1 1 calc R . . O8 O 0.5969(6) 0.7385(4) 0.4892(2) 0.116(2) Uani 1 1 d . . . C10 C 0.9006(6) 0.4686(6) 0.6103(3) 0.0667(17) Uani 1 1 d . . . O11 O 0.9206(6) 0.3850(4) 0.6352(2) 0.115(2) Uani 1 1 d . . . C36 C 0.0149(6) 1.0828(6) 0.3631(3) 0.0673(16) Uani 1 1 d . . . H36 H 0.0103 1.1566 0.3804 0.081 Uiso 1 1 calc R . . C17 C 0.6607(7) 0.7178(6) 0.2354(4) 0.083(2) Uani 1 1 d . . . H17 H 0.6604 0.6655 0.2716 0.100 Uiso 1 1 calc R . . C20 C 0.6417(6) 1.0306(5) 0.2336(3) 0.0685(16) Uani 1 1 d . . . H20 H 0.6231 1.0881 0.2016 0.082 Uiso 1 1 calc R . . C30 C 0.0581(5) 1.0101(6) 0.4822(2) 0.0687(17) Uani 1 1 d . . . H30A H 0.1250 0.9582 0.4997 0.082 Uiso 1 1 calc R . . H30B H 0.0877 1.0871 0.4919 0.082 Uiso 1 1 calc R . . C16 C 0.6589(7) 0.6798(6) 0.1757(3) 0.083(2) Uani 1 1 d . . . H16 H 0.6618 0.7320 0.1396 0.100 Uiso 1 1 calc R . . C5 C 0.7528(12) 0.3787(6) 0.4358(4) 0.144(5) Uani 1 1 d . . . H5 H 0.824(11) 0.407(10) 0.409(5) 0.172 Uiso 1 1 calc . . . C33 C 0.0290(6) 0.8778(6) 0.3091(3) 0.0700(17) Uani 1 1 d . . . H33 H 0.0359 0.8048 0.2907 0.084 Uiso 1 1 calc R . . C3 C 0.8368(10) 0.4807(7) 0.5402(4) 0.116(3) Uani 1 1 d . . . H3 H 0.908(9) 0.513(8) 0.515(5) 0.139 Uiso 1 1 calc . . . C1 C 0.6887(10) 0.5753(7) 0.4585(4) 0.124(4) Uani 1 1 d . . . H1 H 0.761(10) 0.607(9) 0.433(5) 0.149 Uiso 1 1 calc . . . H9 H 0.466(10) 0.702(8) 0.402(5) 0.15(4) Uiso 1 1 d . . . H15 H 0.696(10) 0.212(9) 0.330(5) 0.16(4) Uiso 1 1 d . . . H12 H 0.943(9) 0.557(8) 0.671(5) 0.13(4) Uiso 1 1 d . . . 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 N27 0.055(3) 0.044(2) 0.062(3) 0.001(2) -0.004(2) -0.006(2) C24 0.069(3) 0.044(3) 0.043(3) -0.005(2) 0.003(2) 0.001(2) O15 0.155(5) 0.057(3) 0.042(2) -0.0027(18) -0.046(2) -0.003(3) O9 0.092(3) 0.048(2) 0.071(3) 0.0106(19) -0.017(2) 0.002(2) O14 0.112(3) 0.045(2) 0.058(2) 0.0114(18) 0.008(2) 0.009(2) C25 0.071(4) 0.057(3) 0.038(3) 0.005(2) -0.006(2) -0.001(3) O12 0.107(4) 0.113(4) 0.037(2) -0.011(2) -0.022(2) -0.034(3) N34 0.067(3) 0.098(4) 0.041(2) 0.007(3) -0.013(2) 0.026(3) N21 0.070(3) 0.060(3) 0.073(3) 0.008(3) -0.009(3) -0.002(2) C31 0.047(3) 0.081(4) 0.038(3) 0.012(3) -0.005(2) 0.015(3) C6 0.076(4) 0.059(3) 0.043(3) -0.005(2) -0.021(3) 0.004(3) C29 0.054(3) 0.056(3) 0.043(3) 0.018(2) -0.001(2) 0.002(2) C19 0.067(4) 0.058(3) 0.038(3) 0.007(2) 0.001(2) 0.002(3) C22 0.053(3) 0.090(4) 0.036(3) -0.025(3) -0.011(2) -0.008(3) C35 0.069(4) 0.095(5) 0.048(3) 0.022(3) -0.011(3) 0.027(3) C26 0.062(3) 0.053(3) 0.057(3) 0.013(3) -0.006(3) -0.003(3) C18 0.057(3) 0.040(3) 0.050(3) -0.002(2) 0.004(2) -0.011(2) C4 0.075(4) 0.053(3) 0.033(2) 0.005(2) -0.013(2) -0.004(3) C13 0.083(4) 0.047(3) 0.046(3) -0.007(2) -0.008(3) 0.004(3) C2 0.115(5) 0.058(4) 0.041(3) -0.007(2) -0.019(3) -0.010(4) C32 0.063(4) 0.083(4) 0.044(3) 0.017(3) -0.011(2) 0.014(3) C7 0.088(4) 0.049(3) 0.042(3) 0.013(2) -0.011(3) -0.006(3) C23 0.058(3) 0.096(5) 0.054(3) 0.040(3) -0.005(3) -0.010(3) C28 0.041(3) 0.097(4) 0.033(2) -0.021(3) -0.006(2) 0.000(3) O8 0.191(6) 0.070(3) 0.082(3) -0.033(3) -0.048(3) 0.043(3) C10 0.067(4) 0.097(5) 0.035(3) -0.004(3) -0.006(3) -0.018(4) O11 0.200(6) 0.077(3) 0.060(3) 0.003(2) -0.074(3) -0.013(3) C36 0.072(4) 0.084(4) 0.045(3) 0.016(3) -0.009(3) 0.025(3) C17 0.108(6) 0.070(4) 0.071(4) -0.005(3) 0.008(4) -0.015(4) C20 0.081(4) 0.053(4) 0.071(4) -0.002(3) -0.001(3) 0.001(3) C30 0.062(4) 0.106(5) 0.037(3) 0.012(3) -0.012(2) 0.022(3) C16 0.113(6) 0.080(4) 0.057(4) 0.009(3) 0.014(4) -0.017(4) C5 0.285(14) 0.057(4) 0.079(5) -0.022(4) -0.116(7) 0.049(6) C33 0.068(4) 0.084(4) 0.057(3) 0.009(3) -0.016(3) 0.019(3) C3 0.181(10) 0.100(6) 0.062(4) -0.025(4) -0.070(5) 0.026(6) C1 0.169(9) 0.078(5) 0.117(7) -0.055(5) -0.094(6) 0.067(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N27 C26 1.300(7) . ? N27 C28 1.345(7) . ? C24 C25 1.368(7) . ? C24 C29 1.387(7) . ? C24 C16 1.515(8) . ? O15 C13 1.281(6) . ? O15 H15 0.78(10) . ? O9 C7 1.308(7) . ? O9 H9 0.77(10) . ? O14 C13 1.201(6) . ? C25 C26 1.340(7) . ? C25 H25 0.9500 . ? O12 C10 1.331(8) . ? O12 H12 0.68(9) . ? N34 C33 1.328(7) . ? N34 C35 1.328(8) . ? N21 C20 1.255(7) . ? N21 C22 1.279(7) . ? C31 C36 1.369(7) . ? C31 C32 1.372(8) . ? C31 C30 1.512(7) . ? C6 C5 1.402(10) . ? C6 C1 1.516(9) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C29 C28 1.406(8) . ? C29 H29 0.9500 . ? C19 C20 1.302(8) . ? C19 C18 1.383(7) . ? C19 H19 0.9500 . ? C22 C23 1.480(9) . ? C22 H22 0.9500 . ? C35 C36 1.393(8) . ? C35 H35 0.9500 . ? C26 H26 0.9500 . ? C18 C23 1.429(7) . ? C18 C17 1.475(8) . ? C4 C5 1.484(7) . ? C4 C3 1.513(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C13 C5 1.481(9) . ? C2 C3 1.362(10) . ? C2 C1 1.511(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C32 C33 1.364(8) . ? C32 H32 0.9500 . ? C7 O8 1.160(6) . ? C7 C1 1.435(9) . ? C23 H23 0.9500 . ? C28 H28 0.9500 . ? C10 O11 1.131(7) . ? C10 C3 1.517(8) . ? C36 H36 0.9500 . ? C17 C16 1.262(8) . ? C17 H17 0.9500 . ? C20 H20 0.9500 . ? C30 C30 1.455(11) 3_576 ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C16 H16 0.9500 . ? C5 H5 0.79(11) . ? C33 H33 0.9500 . ? C3 H3 1.06(9) . ? C1 H1 1.19(9) . ? 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 _geom_angle_publ_flag C26 N27 C28 117.8(4) . . ? C25 C24 C29 117.5(5) . . ? C25 C24 C16 126.2(5) . . ? C29 C24 C16 116.1(5) . . ? C13 O15 H15 99(7) . . ? C7 O9 H9 108(8) . . ? C26 C25 C24 120.7(5) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C10 O12 H12 106(9) . . ? C33 N34 C35 116.9(5) . . ? C20 N21 C22 119.9(5) . . ? C36 C31 C32 116.9(5) . . ? C36 C31 C30 122.4(6) . . ? C32 C31 C30 120.6(5) . . ? C5 C6 C1 117.7(5) . . ? C5 C6 H6A 107.9 . . ? C1 C6 H6A 107.9 . . ? C5 C6 H6B 107.9 . . ? C1 C6 H6B 107.9 . . ? H6A C6 H6B 107.2 . . ? C24 C29 C28 117.9(4) . . ? C24 C29 H29 121.0 . . ? C28 C29 H29 121.0 . . ? C20 C19 C18 122.8(5) . . ? C20 C19 H19 118.6 . . ? C18 C19 H19 118.6 . . ? N21 C22 C23 122.0(5) . . ? N21 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? N34 C35 C36 122.9(5) . . ? N34 C35 H35 118.6 . . ? C36 C35 H35 118.6 . . ? N27 C26 C25 124.1(5) . . ? N27 C26 H26 118.0 . . ? C25 C26 H26 118.0 . . ? C19 C18 C23 114.8(5) . . ? C19 C18 C17 128.4(5) . . ? C23 C18 C17 116.8(5) . . ? C5 C4 C3 114.6(5) . . ? C5 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? O14 C13 O15 124.2(5) . . ? O14 C13 C5 120.9(5) . . ? O15 C13 C5 114.9(5) . . ? C3 C2 C1 118.2(6) . . ? C3 C2 H2A 107.8 . . ? C1 C2 H2A 107.8 . . ? C3 C2 H2B 107.8 . . ? C1 C2 H2B 107.8 . . ? H2A C2 H2B 107.1 . . ? C33 C32 C31 120.6(5) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? O8 C7 O9 122.9(6) . . ? O8 C7 C1 122.2(6) . . ? O9 C7 C1 114.9(5) . . ? C18 C23 C22 115.3(4) . . ? C18 C23 H23 122.4 . . ? C22 C23 H23 122.4 . . ? N27 C28 C29 122.0(4) . . ? N27 C28 H28 119.0 . . ? C29 C28 H28 119.0 . . ? O11 C10 O12 125.7(5) . . ? O11 C10 C3 123.1(6) . . ? O12 C10 C3 111.2(7) . . ? C31 C36 C35 119.5(6) . . ? C31 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C16 C17 C18 125.0(6) . . ? C16 C17 H17 117.5 . . ? C18 C17 H17 117.5 . . ? N21 C20 C19 125.2(6) . . ? N21 C20 H20 117.4 . . ? C19 C20 H20 117.4 . . ? C30 C30 C31 113.2(6) 3_576 . ? C30 C30 H30A 108.9 3_576 . ? C31 C30 H30A 108.9 . . ? C30 C30 H30B 108.9 3_576 . ? C31 C30 H30B 108.9 . . ? H30A C30 H30B 107.8 . . ? C17 C16 C24 125.1(6) . . ? C17 C16 H16 117.5 . . ? C24 C16 H16 117.5 . . ? C6 C5 C13 118.0(7) . . ? C6 C5 C4 118.9(6) . . ? C13 C5 C4 114.2(5) . . ? C6 C5 H5 72(9) . . ? C13 C5 H5 117(8) . . ? C4 C5 H5 109(8) . . ? N34 C33 C32 123.2(6) . . ? N34 C33 H33 118.4 . . ? C32 C33 H33 118.4 . . ? C2 C3 C4 118.0(6) . . ? C2 C3 C10 119.1(7) . . ? C4 C3 C10 113.0(6) . . ? C2 C3 H3 92(6) . . ? C4 C3 H3 101(5) . . ? C10 C3 H3 109(5) . . ? C7 C1 C2 113.2(6) . . ? C7 C1 C6 119.7(6) . . ? C2 C1 C6 112.1(6) . . ? C7 C1 H1 119(5) . . ? C2 C1 H1 99(5) . . ? C6 C1 H1 91(5) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.730 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.072 # Attachment 'cocrystal_3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 681086' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1-bromo-1,2-bis(4-pyridyl)ethylene - 1,2-dibromo-1,2-bis(4-pyridyl)ethane ; _chemical_melting_point ? _chemical_formula_moiety C9H12O6,C12H9BrN2,0.5(C12H10Br2N2) _chemical_formula_sum 'C27 H26 Br2 N3 O6' _chemical_formula_weight 648.33 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 /c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2591(16) _cell_length_b 11.8962(17) _cell_length_c 20.253(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.554(3) _cell_angle_gamma 90.00 _cell_volume 2700.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3154 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 23.86 _exptl_crystal_description irregular _exptl_crystal_colour pale-pink _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308 _exptl_absorpt_coefficient_mu 3.049 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4237 _exptl_absorpt_correction_T_max 0.6252 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14784 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.41 _reflns_number_total 5518 _reflns_number_gt 3475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+1.9067P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5518 _refine_ls_number_parameters 385 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C23A C 0.8080(6) 0.7273(4) 0.2549(3) 0.034(2) Uani 0.456(11) 1 d PD A 1 C22A C 0.8690(7) 0.6758(4) 0.3101(4) 0.040(3) Uani 0.462(11) 1 d PD A 1 H22A H 0.9227 0.7175 0.3381 0.048 Uiso 0.462(11) 1 calc PR A 1 Br30 Br 0.704(2) 0.6324(14) 0.1996(5) 0.102(5) Uani 0.121(13) 1 d P A 1 C23B C 0.8093(7) 0.6468(5) 0.2771(3) 0.060(3) Uani 0.544(11) 1 d PD A 2 C22B C 0.8719(7) 0.7475(5) 0.2868(4) 0.060(3) Uani 0.538(11) 1 d PD A 2 H22B H 0.9342 0.7525 0.3203 0.072 Uiso 0.538(11) 1 calc PR A 2 Br31 Br 0.68346(17) 0.64474(12) 0.20437(9) 0.0624(4) Uani 0.879(13) 1 d P A 2 Br39 Br 0.35478(5) 0.13736(4) -0.00133(2) 0.0744(2) Uani 1 1 d . . . O10 O 0.9933(4) -0.1522(3) 0.59255(18) 0.0809(12) Uani 1 1 d . . . C4 C 0.6812(4) 0.1181(3) 0.48924(18) 0.0481(9) Uani 1 1 d . . . H4A H 0.6071 0.1599 0.4885 0.058 Uiso 1 1 calc R . . H4B H 0.7349 0.1601 0.4638 0.058 Uiso 1 1 calc R . . O15 O 0.8168(3) 0.2212(3) 0.65020(14) 0.0782(11) Uani 1 1 d . . . O14 O 0.7496(3) 0.3095(2) 0.55849(14) 0.0729(9) Uani 1 1 d . . . N24 N 0.8521(3) 1.0701(3) 0.19978(17) 0.0581(9) Uani 1 1 d . . . C6 C 0.8461(3) 0.0315(3) 0.56678(18) 0.0438(9) Uani 1 1 d . . . H6A H 0.8729 0.0202 0.6133 0.053 Uiso 1 1 calc R . . H6B H 0.9102 0.0672 0.5458 0.053 Uiso 1 1 calc R . . C3 C 0.6562(3) 0.0046(3) 0.45667(18) 0.0471(9) Uani 1 1 d . . . H3 H 0.5955 -0.0334 0.4802 0.056 Uiso 1 1 calc R . . O13 O 0.6153(4) 0.1025(3) 0.35364(16) 0.1016(14) Uani 1 1 d . . . N32 N 0.5091(3) -0.0547(3) 0.22783(16) 0.0563(9) Uani 1 1 d . . . C7 C 0.9210(4) -0.1629(3) 0.5398(2) 0.0561(11) Uani 1 1 d . . . C1 C 0.8171(3) -0.0825(3) 0.53389(17) 0.0410(8) Uani 1 1 d . . . H1 H 0.7541 -0.1168 0.5573 0.049 Uiso 1 1 calc R . . O12 O 0.5622(3) -0.0749(3) 0.35837(17) 0.0826(11) Uani 1 1 d . . . C38 C 0.4443(4) -0.0042(3) 0.01756(19) 0.0545(10) Uani 1 1 d . . . H38 H 0.3961 -0.0672 -0.0013 0.065 Uiso 1 1 calc R . . C36 C 0.5207(4) 0.0608(4) 0.13261(19) 0.0594(11) Uani 1 1 d . . . H36 H 0.5439 0.1288 0.1153 0.071 Uiso 1 1 calc R . . C29 C 0.8246(4) 0.9854(4) 0.1584(2) 0.0552(11) Uani 1 1 d . . . H25 H 0.8085 1.0016 0.1135 0.066 Uiso 1 1 calc R . . C5 C 0.7364(3) 0.1081(3) 0.56074(18) 0.0431(9) Uani 1 1 d . . . H5 H 0.6766 0.0751 0.5870 0.052 Uiso 1 1 calc R . . C2 C 0.7673(3) -0.0683(3) 0.46232(17) 0.0452(9) Uani 1 1 d . . . H2A H 0.7480 -0.1415 0.4431 0.054 Uiso 1 1 calc R . . H2B H 0.8273 -0.0341 0.4375 0.054 Uiso 1 1 calc R . . C9 C 0.7672(4) 0.2235(3) 0.58835(19) 0.0506(10) Uani 1 1 d . . . C25 C 0.8768(5) 1.0441(4) 0.2635(2) 0.0771(14) Uani 1 1 d . . . H29 H 0.8982 1.1013 0.2936 0.093 Uiso 1 1 calc R . . C34 C 0.4324(4) -0.1181(3) 0.1208(2) 0.0560(11) Uani 1 1 d . . . H34 H 0.3948 -0.1747 0.0950 0.067 Uiso 1 1 calc R . . C33 C 0.4550(4) -0.1316(3) 0.1885(2) 0.0580(11) Uani 1 1 d . . . H33 H 0.4309 -0.1980 0.2074 0.070 Uiso 1 1 calc R . . C37 C 0.5407(4) 0.0392(4) 0.1995(2) 0.0584(11) Uani 1 1 d . . . H37 H 0.5787 0.0942 0.2264 0.070 Uiso 1 1 calc R . . O11 O 0.9357(3) -0.2344(3) 0.4995(2) 0.1011(13) Uani 1 1 d . . . C19 C 0.8489(5) 0.5542(3) 0.3248(3) 0.0756(15) Uani 1 1 d D . . C35 C 0.4661(4) -0.0200(3) 0.09196(18) 0.0494(10) Uani 1 1 d . . . N16 N 0.8843(4) 0.3437(3) 0.3804(3) 0.0770(12) Uani 1 1 d . A . C21 C 0.8934(4) 0.4321(6) 0.4188(3) 0.0811(15) Uani 1 1 d . . . H22 H 0.9118 0.4223 0.4642 0.097 Uiso 1 1 calc R A . C8 C 0.6075(4) 0.0168(4) 0.3844(2) 0.0571(11) Uani 1 1 d . . . C18 C 0.8418(5) 0.4579(4) 0.2893(3) 0.0834(16) Uani 1 1 d . A . H19 H 0.8244 0.4615 0.2436 0.100 Uiso 1 1 calc R . . C27 C 0.8404(5) 0.8481(3) 0.2439(3) 0.0739(15) Uani 1 1 d D . . C26 C 0.8720(5) 0.9349(4) 0.2867(2) 0.0844(17) Uani 1 1 d . A . H28 H 0.8903 0.9203 0.3317 0.101 Uiso 1 1 calc R . . C28 C 0.8188(4) 0.8761(3) 0.1780(2) 0.0641(12) Uani 1 1 d . A . H26 H 0.8002 0.8202 0.1466 0.077 Uiso 1 1 calc R . . C17 C 0.8591(5) 0.3577(4) 0.3182(3) 0.0881(17) Uani 1 1 d . . . H18 H 0.8524 0.2941 0.2914 0.106 Uiso 1 1 calc R A . C20 C 0.8759(5) 0.5438(5) 0.3931(3) 0.0873(17) Uani 1 1 d . A . H21 H 0.8822 0.6064 0.4207 0.105 Uiso 1 1 calc R . . H15 H 0.832(4) 0.298(5) 0.666(2) 0.086(15) Uiso 1 1 d . . . H12 H 0.548(6) -0.067(5) 0.314(3) 0.13(2) Uiso 1 1 d . . . H10 H 1.027(6) -0.202(6) 0.600(3) 0.12(3) Uiso 1 1 d . . . 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 C23A 0.038(5) 0.031(5) 0.034(5) -0.012(4) 0.003(4) -0.003(4) C22A 0.059(6) 0.016(4) 0.046(5) 0.001(4) 0.006(4) -0.002(4) Br30 0.125(10) 0.145(11) 0.038(4) -0.054(6) 0.009(5) -0.027(5) C23B 0.059(6) 0.062(6) 0.059(6) -0.019(5) 0.012(4) 0.002(5) C22B 0.061(6) 0.057(6) 0.060(6) 0.004(5) 0.000(4) -0.001(4) Br31 0.0630(7) 0.0514(6) 0.0693(9) 0.0098(6) -0.0118(5) -0.0117(4) Br39 0.0848(4) 0.0805(4) 0.0570(3) -0.0033(2) 0.0029(2) 0.0360(3) O10 0.096(3) 0.070(2) 0.071(2) -0.0002(18) -0.0212(19) 0.040(2) C4 0.060(2) 0.043(2) 0.039(2) -0.0061(17) -0.0080(18) 0.0154(18) O15 0.137(3) 0.0406(17) 0.0494(18) -0.0077(14) -0.0303(18) 0.0072(18) O14 0.120(3) 0.0384(16) 0.0548(18) -0.0024(14) -0.0183(17) 0.0173(17) N24 0.079(3) 0.0387(19) 0.054(2) 0.0092(16) -0.0042(18) -0.0010(17) C6 0.057(2) 0.0350(19) 0.037(2) 0.0001(15) -0.0078(17) 0.0017(17) C3 0.055(2) 0.046(2) 0.039(2) -0.0026(17) -0.0012(17) 0.0031(18) O13 0.185(4) 0.055(2) 0.054(2) -0.0004(16) -0.045(2) 0.006(2) N32 0.064(2) 0.062(2) 0.0410(19) -0.0068(18) -0.0030(16) 0.0079(18) C7 0.059(3) 0.040(2) 0.069(3) 0.010(2) 0.006(2) 0.0018(19) C1 0.053(2) 0.0288(18) 0.041(2) 0.0025(15) 0.0029(17) 0.0006(16) O12 0.123(3) 0.075(2) 0.0452(19) -0.0011(17) -0.0185(19) -0.029(2) C38 0.062(3) 0.055(2) 0.044(2) -0.0081(19) -0.0029(19) -0.004(2) C36 0.075(3) 0.062(3) 0.041(2) -0.008(2) 0.004(2) -0.019(2) C29 0.066(3) 0.047(2) 0.051(3) 0.009(2) -0.005(2) -0.003(2) C5 0.055(2) 0.0345(19) 0.039(2) -0.0016(16) -0.0028(17) 0.0048(17) C2 0.061(2) 0.0346(19) 0.039(2) -0.0034(16) 0.0037(18) 0.0011(18) C9 0.069(3) 0.040(2) 0.041(2) -0.0049(18) -0.0020(19) 0.011(2) C25 0.113(4) 0.064(3) 0.053(3) -0.004(2) -0.005(3) 0.010(3) C34 0.070(3) 0.049(2) 0.046(2) -0.0126(19) -0.007(2) -0.004(2) C33 0.075(3) 0.047(2) 0.050(3) 0.000(2) -0.001(2) 0.001(2) C37 0.060(3) 0.070(3) 0.043(2) -0.020(2) -0.0030(19) -0.013(2) O11 0.094(3) 0.078(2) 0.125(3) -0.046(2) -0.023(2) 0.043(2) C19 0.099(4) 0.043(3) 0.092(4) 0.019(3) 0.048(3) 0.024(2) C35 0.053(2) 0.056(2) 0.038(2) -0.0102(19) -0.0003(17) -0.003(2) N16 0.077(3) 0.052(2) 0.101(4) 0.012(2) 0.000(3) 0.013(2) C21 0.068(3) 0.111(5) 0.064(3) 0.020(3) 0.004(2) -0.006(3) C8 0.075(3) 0.050(3) 0.043(2) -0.004(2) -0.010(2) 0.011(2) C18 0.113(4) 0.060(3) 0.079(4) 0.008(3) 0.015(3) 0.039(3) C27 0.107(4) 0.044(3) 0.080(3) 0.023(2) 0.052(3) 0.030(3) C26 0.132(5) 0.071(3) 0.053(3) 0.023(3) 0.025(3) 0.042(3) C28 0.087(3) 0.040(2) 0.068(3) -0.001(2) 0.018(2) 0.000(2) C17 0.106(4) 0.052(3) 0.104(5) 0.003(3) -0.001(4) 0.028(3) C20 0.097(4) 0.067(3) 0.105(5) -0.022(3) 0.043(3) -0.011(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C23A C22A 1.397(2) . ? C23A C27 1.504(2) . ? C23A Br30 1.909(13) . ? C22A C19 1.499(2) . ? C22A H22A 0.9300 . ? C23B C22B 1.395(2) . ? C23B C19 1.504(2) . ? C23B Br31 1.942(6) . ? C22B C27 1.500(2) . ? C22B H22B 0.9300 . ? Br39 C38 1.981(4) . ? O10 C7 1.285(6) . ? O10 H10 0.72(6) . ? C4 C3 1.517(5) . ? C4 C5 1.524(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? O15 C9 1.321(4) . ? O15 H15 0.98(5) . ? O14 C9 1.196(4) . ? N24 C29 1.327(5) . ? N24 C25 1.330(5) . ? C6 C5 1.530(5) . ? C6 C1 1.532(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C3 C2 1.517(5) . ? C3 C8 1.520(5) . ? C3 H3 0.9800 . ? O13 C8 1.202(5) . ? N32 C37 1.321(5) . ? N32 C33 1.322(5) . ? C7 O11 1.203(5) . ? C7 C1 1.506(6) . ? C1 C2 1.512(5) . ? C1 H1 0.9800 . ? O12 C8 1.294(5) . ? O12 H12 0.90(6) . ? C38 C38 1.504(8) 3_655 ? C38 C35 1.515(5) . ? C38 H38 0.9800 . ? C36 C35 1.371(5) . ? C36 C37 1.376(6) . ? C36 H36 0.9300 . ? C29 C28 1.363(6) . ? C29 H25 0.9300 . ? C5 C9 1.509(5) . ? C5 H5 0.9800 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C25 C26 1.384(6) . ? C25 H29 0.9300 . ? C34 C35 1.375(6) . ? C34 C33 1.378(6) . ? C34 H34 0.9300 . ? C33 H33 0.9300 . ? C37 H37 0.9300 . ? C19 C18 1.351(7) . ? C19 C20 1.392(7) . ? N16 C17 1.275(7) . ? N16 C21 1.306(7) . ? C21 C20 1.435(7) . ? C21 H22 0.9300 . ? C18 C17 1.334(6) . ? C18 H19 0.9300 . ? C27 C26 1.373(7) . ? C27 C28 1.374(6) . ? C26 H28 0.9300 . ? C28 H26 0.9300 . ? C17 H18 0.9300 . ? C20 H21 0.9300 . ? 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 _geom_angle_publ_flag C22A C23A C27 115.4(4) . . ? C22A C23A Br30 115.9(6) . . ? C27 C23A Br30 128.5(6) . . ? C23A C22A C19 120.7(5) . . ? C23A C22A H22A 119.7 . . ? C19 C22A H22A 119.7 . . ? C22B C23B C19 115.1(4) . . ? C22B C23B Br31 116.0(4) . . ? C19 C23B Br31 128.9(5) . . ? C23B C22B C27 121.1(5) . . ? C23B C22B H22B 119.5 . . ? C27 C22B H22B 119.5 . . ? C7 O10 H10 112(5) . . ? C3 C4 C5 112.7(3) . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C9 O15 H15 110(3) . . ? C29 N24 C25 116.7(4) . . ? C5 C6 C1 110.9(3) . . ? C5 C6 H6A 109.5 . . ? C1 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? C4 C3 C2 111.0(3) . . ? C4 C3 C8 111.6(3) . . ? C2 C3 C8 110.2(3) . . ? C4 C3 H3 107.9 . . ? C2 C3 H3 107.9 . . ? C8 C3 H3 107.9 . . ? C37 N32 C33 116.8(3) . . ? O11 C7 O10 121.1(4) . . ? O11 C7 C1 123.5(4) . . ? O10 C7 C1 115.4(4) . . ? C7 C1 C2 111.1(3) . . ? C7 C1 C6 113.4(3) . . ? C2 C1 C6 111.2(3) . . ? C7 C1 H1 106.9 . . ? C2 C1 H1 106.9 . . ? C6 C1 H1 106.9 . . ? C8 O12 H12 110(4) . . ? C38 C38 C35 114.6(4) 3_655 . ? C38 C38 Br39 106.5(4) 3_655 . ? C35 C38 Br39 109.1(3) . . ? C38 C38 H38 108.8 3_655 . ? C35 C38 H38 108.8 . . ? Br39 C38 H38 108.8 . . ? C35 C36 C37 118.8(4) . . ? C35 C36 H36 120.6 . . ? C37 C36 H36 120.6 . . ? N24 C29 C28 123.7(4) . . ? N24 C29 H25 118.2 . . ? C28 C29 H25 118.2 . . ? C9 C5 C4 109.8(3) . . ? C9 C5 C6 111.0(3) . . ? C4 C5 C6 112.0(3) . . ? C9 C5 H5 108.0 . . ? C4 C5 H5 108.0 . . ? C6 C5 H5 108.0 . . ? C1 C2 C3 111.3(3) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? O14 C9 O15 122.1(4) . . ? O14 C9 C5 124.8(3) . . ? O15 C9 C5 113.2(3) . . ? N24 C25 C26 122.5(5) . . ? N24 C25 H29 118.8 . . ? C26 C25 H29 118.8 . . ? C35 C34 C33 119.3(4) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? N32 C33 C34 123.3(4) . . ? N32 C33 H33 118.4 . . ? C34 C33 H33 118.4 . . ? N32 C37 C36 124.1(4) . . ? N32 C37 H37 118.0 . . ? C36 C37 H37 118.0 . . ? C18 C19 C20 116.7(4) . . ? C18 C19 C22A 135.7(5) . . ? C20 C19 C22A 105.1(5) . . ? C18 C19 C23B 106.3(5) . . ? C20 C19 C23B 136.5(5) . . ? C22A C19 C23B 37.5(4) . . ? C36 C35 C34 117.7(4) . . ? C36 C35 C38 122.0(4) . . ? C34 C35 C38 120.2(3) . . ? C17 N16 C21 118.7(5) . . ? N16 C21 C20 122.0(5) . . ? N16 C21 H22 119.0 . . ? C20 C21 H22 119.0 . . ? O13 C8 O12 123.4(4) . . ? O13 C8 C3 122.8(4) . . ? O12 C8 C3 113.8(4) . . ? C17 C18 C19 121.7(5) . . ? C17 C18 H19 119.1 . . ? C19 C18 H19 119.1 . . ? C26 C27 C28 116.2(4) . . ? C26 C27 C22B 101.7(5) . . ? C28 C27 C22B 139.9(5) . . ? C26 C27 C23A 132.7(5) . . ? C28 C27 C23A 110.6(5) . . ? C22B C27 C23A 36.9(3) . . ? C27 C26 C25 120.5(4) . . ? C27 C26 H28 119.8 . . ? C25 C26 H28 119.8 . . ? C29 C28 C27 120.4(4) . . ? C29 C28 H26 119.8 . . ? C27 C28 H26 119.8 . . ? N16 C17 C18 124.0(5) . . ? N16 C17 H18 118.0 . . ? C18 C17 H18 118.0 . . ? C19 C20 C21 116.9(5) . . ? C19 C20 H21 121.6 . . ? C21 C20 H21 121.6 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.874 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.068 # Attachment 'cocrystal_4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 681087' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1,2-bis(4-pyridyl)ethane - 1-bromo-1,2-bis(4-pyridyl)ethylene - 1,2-dibromo-1,2-bis(4-pyridyl)ethane ; _chemical_melting_point ? _chemical_formula_moiety ; C9H12O6,0.82(C12H12N2),0.18(C12H9BrN2),0.5(C12H10Br2N2) ; _chemical_formula_sum 'C27 H29 Br1.18 N3 O6' _chemical_formula_weight 591.42 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 /c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.328(3) _cell_length_b 11.837(3) _cell_length_c 20.015(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.448(4) _cell_angle_gamma 90.00 _cell_volume 2675.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1714 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 19.04 _exptl_crystal_description rhombous _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1215 _exptl_absorpt_coefficient_mu 1.956 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5477 _exptl_absorpt_correction_T_max 0.7449 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_reflns_number 15837 _diffrn_reflns_av_R_equivalents 0.0771 _diffrn_reflns_av_sigmaI/netI 0.1012 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.04 _reflns_number_total 5281 _reflns_number_gt 2500 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0819P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5281 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1565 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.1816 _refine_ls_wR_factor_gt 0.1471 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 2.094 _refine_ls_shift/su_mean 0.037 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br38 Br 0.35741(6) 0.86010(5) -0.00125(3) 0.0768(3) Uani 1 1 d . . . O9 O 0.9861(4) 1.1485(3) 0.5977(2) 0.0788(13) Uani 1 1 d . . . H9 H 1.0411 1.1935 0.5974 0.118 Uiso 1 1 calc R . . O12 O 0.5681(4) 1.0781(3) 0.36151(18) 0.0799(13) Uani 1 1 d . . . H12 H 0.5429 1.0671 0.3225 0.120 Uiso 1 1 calc R . . C1 C 0.8135(5) 1.0780(4) 0.5379(2) 0.0481(13) Uani 1 1 d . . . H1 H 0.752(4) 1.113(4) 0.562(2) 0.058 Uiso 1 1 calc . . . C4 C 0.6763(5) 0.8786(4) 0.4926(2) 0.0538(14) Uani 1 1 d . . . H4A H 0.6028 0.8364 0.4918 0.065 Uiso 1 1 calc R . . H4B H 0.7302 0.8372 0.4662 0.065 Uiso 1 1 calc R . . C32 C 0.4625(5) 1.0181(4) 0.0930(2) 0.0467(13) Uani 1 1 d . . . C31 C 0.4451(5) 1.0020(4) 0.0182(2) 0.0546(15) Uani 1 1 d . . . H31 H 0.396(4) 1.065(4) 0.000(2) 0.066 Uiso 1 1 calc . . . C6 C 0.8399(5) 0.9611(4) 0.5705(2) 0.0506(13) Uani 1 1 d . . . H6A H 0.9031 0.9244 0.5488 0.061 Uiso 1 1 calc R . . H6B H 0.8658 0.9710 0.6175 0.061 Uiso 1 1 calc R . . O14 O 0.7452(4) 0.6850(3) 0.55982(19) 0.0801(13) Uani 1 1 d . . . C5 C 0.7295(5) 0.8872(4) 0.5642(2) 0.0487(13) Uani 1 1 d . . . H5 H 0.670(4) 0.922(4) 0.591(2) 0.058 Uiso 1 1 calc . . . O15 O 0.7935(5) 0.7710(3) 0.65622(18) 0.0985(17) Uani 1 1 d . . . H15 H 0.8066 0.7061 0.6690 0.148 Uiso 1 1 calc R . . C2 C 0.7645(5) 1.0662(4) 0.4653(2) 0.0509(14) Uani 1 1 d . . . H2A H 0.8235 1.0314 0.4393 0.061 Uiso 1 1 calc R . . H2B H 0.7465 1.1404 0.4467 0.061 Uiso 1 1 calc R . . N35 N 0.5053(4) 1.0546(4) 0.2303(2) 0.0644(13) Uani 1 1 d . . . C36 C 0.4598(6) 1.1338(4) 0.1896(3) 0.0713(17) Uani 1 1 d . . . H36 H 0.4415 1.2032 0.2079 0.086 Uiso 1 1 calc R . . C3 C 0.6521(5) 0.9937(4) 0.4610(2) 0.0482(13) Uani 1 1 d . . . H3 H 0.593(4) 1.032(4) 0.486(2) 0.058 Uiso 1 1 calc . . . C10 C 0.6037(5) 0.9833(5) 0.3886(3) 0.0602(16) Uani 1 1 d . . . O11 O 0.6051(6) 0.8961(4) 0.3571(2) 0.120(2) Uani 1 1 d . . . C13 C 0.7565(5) 0.7702(5) 0.5923(3) 0.0623(16) Uani 1 1 d . . . C33 C 0.5094(5) 0.9348(5) 0.1352(2) 0.0628(16) Uani 1 1 d . . . H33 H 0.5278 0.8642 0.1183 0.075 Uiso 1 1 calc R . . O8 O 0.9351(4) 1.2268(4) 0.5009(2) 0.0961(16) Uani 1 1 d . . . C37 C 0.4382(6) 1.1193(4) 0.1218(3) 0.0632(16) Uani 1 1 d . . . H37 H 0.4070 1.1784 0.0954 0.076 Uiso 1 1 calc R . . C34 C 0.5284(5) 0.9572(5) 0.2021(3) 0.0667(16) Uani 1 1 d . . . H34 H 0.5599 0.8998 0.2298 0.080 Uiso 1 1 calc R . . Br30 Br 0.6846(3) 0.3603(3) 0.20937(18) 0.0790(17) Uani 0.182(2) 1 d P . . N21 N 0.8302(4) -0.0629(3) 0.2035(2) 0.0648(13) Uani 1 1 d . . . C26 C 0.8992(6) 0.5789(6) 0.4199(3) 0.0783(18) Uani 1 1 d . . . H26 H 0.9237 0.5938 0.4644 0.094 Uiso 1 1 calc R . . C19 C 0.8227(6) 0.1328(4) 0.1796(3) 0.0758(19) Uani 1 1 d . . . H19 H 0.8089 0.1898 0.1480 0.091 Uiso 1 1 calc R . . C24 C 0.8365(6) 0.4471(5) 0.3348(3) 0.0778(19) Uani 1 1 d . . . C22 C 0.8597(6) -0.0359(5) 0.2671(3) 0.0766(19) Uani 1 1 d . . . H22 H 0.8724 -0.0940 0.2981 0.092 Uiso 1 1 calc R . . C20 C 0.8130(6) 0.0221(5) 0.1611(3) 0.0711(18) Uani 1 1 d . . . H20 H 0.7933 0.0056 0.1162 0.085 Uiso 1 1 calc R . . C28 C 0.8532(6) 0.6418(5) 0.3163(3) 0.0785(19) Uani 1 1 d . . . H28 H 0.8447 0.7018 0.2863 0.094 Uiso 1 1 calc R . . N27 N 0.8889(5) 0.6649(4) 0.3773(3) 0.0718(14) Uani 1 1 d . . . C23 C 0.8721(6) 0.0729(5) 0.2890(3) 0.0774(19) Uani 1 1 d . . . H23 H 0.8938 0.0878 0.3339 0.093 Uiso 1 1 calc R . . C25 C 0.8752(6) 0.4687(5) 0.4013(3) 0.085(2) Uani 1 1 d . . . H25 H 0.8847 0.4103 0.4323 0.101 Uiso 1 1 calc R . . C18 C 0.8529(6) 0.1585(5) 0.2452(3) 0.0759(19) Uani 1 1 d . . . C29 C 0.8269(6) 0.5370(5) 0.2921(3) 0.084(2) Uani 1 1 d . . . H29 H 0.8026 0.5266 0.2471 0.101 Uiso 1 1 calc R . . C7 C 0.9191(5) 1.1581(5) 0.5427(3) 0.0573(15) Uani 1 1 d . . . C16 C 0.8104(10) 0.3258(5) 0.3099(5) 0.147(4) Uani 1 1 d . . . H16A H 0.8140 0.2774 0.3491 0.177 Uiso 1 1 calc R . . H16B H 0.7291 0.3246 0.2908 0.177 Uiso 1 1 calc R . . C17 C 0.8708(10) 0.2815(6) 0.2693(4) 0.150(4) Uani 1 1 d . . . H17A H 0.9524 0.2875 0.2875 0.179 Uiso 1 1 calc R . . H17B H 0.8636 0.3285 0.2295 0.179 Uiso 1 1 calc R . . 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 Br38 0.0981(6) 0.0682(4) 0.0635(4) 0.0017(3) 0.0028(3) -0.0326(4) O9 0.104(3) 0.051(2) 0.077(3) 0.010(2) -0.024(3) -0.032(2) O12 0.122(4) 0.064(3) 0.050(2) 0.002(2) -0.018(2) 0.022(3) C1 0.068(4) 0.029(3) 0.046(3) 0.001(2) -0.002(3) -0.005(3) C4 0.072(4) 0.041(3) 0.045(3) 0.005(2) -0.016(3) -0.007(3) C32 0.057(4) 0.042(3) 0.040(3) 0.008(2) -0.002(2) 0.004(3) C31 0.069(4) 0.043(3) 0.050(3) 0.008(2) -0.005(3) 0.008(3) C6 0.071(4) 0.034(3) 0.045(3) -0.003(2) -0.010(3) 0.002(3) O14 0.140(4) 0.036(2) 0.061(2) 0.0014(19) -0.013(2) -0.020(2) C5 0.070(4) 0.029(3) 0.046(3) 0.002(2) 0.000(3) -0.006(3) O15 0.189(5) 0.039(2) 0.059(3) 0.0076(18) -0.036(3) -0.007(3) C2 0.070(4) 0.033(3) 0.050(3) 0.006(2) 0.008(3) -0.004(3) N35 0.095(4) 0.051(3) 0.046(3) 0.003(2) 0.000(3) 0.003(3) C36 0.111(5) 0.042(3) 0.059(4) -0.001(3) -0.004(4) 0.009(3) C3 0.065(4) 0.039(3) 0.041(3) 0.001(2) 0.004(3) -0.005(3) C10 0.081(4) 0.046(4) 0.051(3) 0.006(3) -0.009(3) -0.009(3) O11 0.237(7) 0.051(3) 0.061(3) 0.004(2) -0.058(3) -0.016(3) C13 0.090(5) 0.044(4) 0.049(3) 0.008(3) -0.013(3) -0.016(3) C33 0.085(4) 0.058(4) 0.044(3) 0.009(3) -0.005(3) 0.016(3) O8 0.113(4) 0.079(3) 0.093(3) 0.037(3) -0.016(3) -0.045(3) C37 0.098(5) 0.043(3) 0.046(3) 0.009(2) -0.007(3) 0.011(3) C34 0.088(5) 0.062(4) 0.049(3) 0.021(3) -0.004(3) 0.010(3) Br30 0.093(3) 0.062(2) 0.081(3) -0.0038(17) -0.006(2) 0.023(2) N21 0.094(4) 0.039(3) 0.059(3) -0.007(2) -0.009(3) 0.008(2) C26 0.095(5) 0.074(5) 0.065(4) -0.008(4) -0.004(4) -0.007(4) C19 0.120(6) 0.039(4) 0.069(4) 0.004(3) 0.012(4) -0.014(3) C24 0.109(6) 0.040(4) 0.088(5) -0.002(3) 0.029(4) -0.010(3) C22 0.116(6) 0.051(4) 0.060(4) 0.000(3) -0.008(4) 0.009(4) C20 0.098(5) 0.055(4) 0.057(4) -0.009(3) -0.016(3) -0.003(3) C28 0.107(6) 0.048(4) 0.079(4) 0.005(3) -0.007(4) -0.010(4) N27 0.083(4) 0.043(3) 0.088(4) 0.000(3) -0.004(3) -0.009(3) C23 0.119(6) 0.052(4) 0.063(4) -0.016(3) 0.016(4) -0.015(4) C25 0.109(6) 0.059(4) 0.088(5) 0.019(4) 0.019(4) 0.001(4) C18 0.111(6) 0.040(4) 0.080(4) -0.010(3) 0.034(4) -0.015(3) C29 0.132(6) 0.055(4) 0.065(4) -0.006(3) 0.001(4) -0.015(4) C7 0.067(4) 0.039(3) 0.066(4) -0.011(3) 0.001(3) 0.003(3) C16 0.260(13) 0.035(4) 0.160(8) -0.035(5) 0.098(8) -0.020(5) C17 0.272(12) 0.051(5) 0.141(7) -0.038(5) 0.114(8) -0.041(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br38 C31 1.975(5) . ? O9 C7 1.293(6) . ? O9 H9 0.8200 . ? O12 C10 1.298(6) . ? O12 H12 0.8200 . ? C1 C2 1.519(6) . ? C1 C7 1.523(8) . ? C1 C6 1.549(6) . ? C1 H1 0.95(5) . ? C4 C5 1.514(6) . ? C4 C3 1.518(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C32 C37 1.367(7) . ? C32 C33 1.378(6) . ? C32 C31 1.505(6) . ? C31 C31 1.491(11) 3_675 ? C31 H31 0.91(5) . ? C6 C5 1.523(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O14 C13 1.201(6) . ? C5 C13 1.517(7) . ? C5 H5 0.82(5) . ? O15 C13 1.315(6) . ? O15 H15 0.8200 . ? C2 C3 1.533(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N35 C34 1.318(7) . ? N35 C36 1.320(6) . ? C36 C37 1.370(7) . ? C36 H36 0.9300 . ? C3 C10 1.513(7) . ? C3 H3 1.01(5) . ? C10 O11 1.211(6) . ? C33 C34 1.367(7) . ? C33 H33 0.9300 . ? O8 C7 1.191(6) . ? C37 H37 0.9300 . ? C34 H34 0.9300 . ? N21 C20 1.322(7) . ? N21 C22 1.328(7) . ? C26 N27 1.326(7) . ? C26 C25 1.378(8) . ? C26 H26 0.9300 . ? C19 C20 1.363(7) . ? C19 C18 1.366(8) . ? C19 H19 0.9300 . ? C24 C29 1.363(8) . ? C24 C25 1.392(8) . ? C24 C16 1.540(8) . ? C22 C23 1.365(7) . ? C22 H22 0.9300 . ? C20 H20 0.9300 . ? C28 N27 1.285(7) . ? C28 C29 1.357(7) . ? C28 H28 0.9300 . ? C23 C18 1.347(8) . ? C23 H23 0.9300 . ? C25 H25 0.9300 . ? C18 C17 1.542(8) . ? C29 H29 0.9300 . ? C16 C17 1.220(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? 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 _geom_angle_publ_flag C7 O9 H9 109.5 . . ? C10 O12 H12 109.5 . . ? C2 C1 C7 110.2(4) . . ? C2 C1 C6 111.4(4) . . ? C7 C1 C6 113.9(5) . . ? C2 C1 H1 106(3) . . ? C7 C1 H1 110(3) . . ? C6 C1 H1 105(3) . . ? C5 C4 C3 112.3(4) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? C37 C32 C33 116.7(5) . . ? C37 C32 C31 121.0(4) . . ? C33 C32 C31 122.2(5) . . ? C31 C31 C32 116.2(6) 3_675 . ? C31 C31 Br38 107.6(5) 3_675 . ? C32 C31 Br38 109.2(3) . . ? C31 C31 H31 114(3) 3_675 . ? C32 C31 H31 106(3) . . ? Br38 C31 H31 103(3) . . ? C5 C6 C1 110.4(4) . . ? C5 C6 H6A 109.6 . . ? C1 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? C1 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C4 C5 C13 110.1(4) . . ? C4 C5 C6 112.4(4) . . ? C13 C5 C6 110.6(5) . . ? C4 C5 H5 108(3) . . ? C13 C5 H5 107(3) . . ? C6 C5 H5 109(3) . . ? C13 O15 H15 109.5 . . ? C1 C2 C3 110.3(4) . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C34 N35 C36 116.0(4) . . ? N35 C36 C37 123.6(5) . . ? N35 C36 H36 118.2 . . ? C37 C36 H36 118.2 . . ? C10 C3 C4 111.5(4) . . ? C10 C3 C2 109.7(4) . . ? C4 C3 C2 110.9(4) . . ? C10 C3 H3 107(3) . . ? C4 C3 H3 110(3) . . ? C2 C3 H3 108(3) . . ? O11 C10 O12 122.4(5) . . ? O11 C10 C3 123.4(5) . . ? O12 C10 C3 114.0(5) . . ? O14 C13 O15 123.0(5) . . ? O14 C13 C5 123.8(5) . . ? O15 C13 C5 113.2(5) . . ? C34 C33 C32 119.0(5) . . ? C34 C33 H33 120.5 . . ? C32 C33 H33 120.5 . . ? C32 C37 C36 120.1(5) . . ? C32 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? N35 C34 C33 124.6(5) . . ? N35 C34 H34 117.7 . . ? C33 C34 H34 117.7 . . ? C20 N21 C22 116.5(5) . . ? N27 C26 C25 123.2(6) . . ? N27 C26 H26 118.4 . . ? C25 C26 H26 118.4 . . ? C20 C19 C18 119.0(5) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C29 C24 C25 117.3(5) . . ? C29 C24 C16 121.4(7) . . ? C25 C24 C16 121.3(6) . . ? N21 C22 C23 123.2(5) . . ? N21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? N21 C20 C19 123.5(5) . . ? N21 C20 H20 118.2 . . ? C19 C20 H20 118.2 . . ? N27 C28 C29 125.3(6) . . ? N27 C28 H28 117.4 . . ? C29 C28 H28 117.4 . . ? C28 N27 C26 116.9(5) . . ? C18 C23 C22 119.6(6) . . ? C18 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C26 C25 C24 118.2(6) . . ? C26 C25 H25 120.9 . . ? C24 C25 H25 120.9 . . ? C23 C18 C19 118.3(5) . . ? C23 C18 C17 119.8(7) . . ? C19 C18 C17 121.9(6) . . ? C28 C29 C24 119.1(6) . . ? C28 C29 H29 120.4 . . ? C24 C29 H29 120.4 . . ? O8 C7 O9 123.2(6) . . ? O8 C7 C1 122.8(5) . . ? O9 C7 C1 113.9(5) . . ? C17 C16 C24 120.8(8) . . ? C17 C16 H16A 107.1 . . ? C24 C16 H16A 107.1 . . ? C17 C16 H16B 107.1 . . ? C24 C16 H16B 107.1 . . ? H16A C16 H16B 106.8 . . ? C16 C17 C18 123.1(8) . . ? C16 C17 H17A 106.5 . . ? C18 C17 H17A 106.5 . . ? C16 C17 H17B 106.5 . . ? C18 C17 H17B 106.5 . . ? H17A C17 H17B 106.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.794 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.067 # Attachment 'cocrystal_5h.cif' data_5h _database_code_depnum_ccdc_archive 'CCDC 681088' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1,2-bis(4-pyridyl)ethane - 1,4-bis(4-pyridyl)butane ; _chemical_melting_point ? _chemical_formula_moiety 2(C9H12O6),2(C12H12N2),1.5(C14H16N2) _chemical_formula_sum 'C63 H72 N7 O12' _chemical_formula_weight 1119.28 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.678(2) _cell_length_b 14.124(3) _cell_length_c 17.964(3) _cell_angle_alpha 83.231(2) _cell_angle_beta 83.523(2) _cell_angle_gamma 79.704(2) _cell_volume 2882.1(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9735 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1190 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9480 _exptl_absorpt_correction_T_max 0.9770 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25927 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.06 _reflns_number_total 11056 _reflns_number_gt 7843 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11056 _refine_ls_number_parameters 739 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1956 _refine_ls_R_factor_gt 0.1707 _refine_ls_wR_factor_ref 0.4621 _refine_ls_wR_factor_gt 0.4327 _refine_ls_goodness_of_fit_ref 1.856 _refine_ls_restrained_S_all 1.856 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O11 O 0.7754(3) 0.5260(2) 0.1235(2) 0.0298(9) Uani 1 1 d . . . O1 O 0.2752(3) 0.5389(2) 0.1245(2) 0.0347(10) Uani 1 1 d . . . O12 O 0.6673(3) 0.4158(3) 0.1090(2) 0.0306(9) Uani 1 1 d . . . N6 N 0.3966(3) 0.3392(3) 0.9254(2) 0.0186(9) Uani 1 1 d . . . N1 N 0.2414(5) 0.9160(3) 0.2354(3) 0.0373(12) Uani 1 1 d . . . C6 C 0.8868(5) 0.0864(4) 0.2176(4) 0.0381(15) Uani 1 1 d . . . O3 O 0.4858(3) 0.4044(3) 0.3639(2) 0.0355(10) Uani 1 1 d . . . O8 O 0.9022(4) 0.0342(3) 0.1632(2) 0.0501(13) Uani 1 1 d . . . O10 O 0.9992(3) 0.4106(2) 0.3564(2) 0.0273(9) Uani 1 1 d . . . C10 C 0.5632(4) 0.1944(3) 0.9897(2) 0.0133(9) Uani 1 1 d . . . N4 N 0.8030(4) 0.8754(3) 0.2093(3) 0.0360(11) Uani 1 1 d . . . O9 O 1.1333(3) 0.2780(3) 0.3460(2) 0.0362(10) Uani 1 1 d . . . C13 C 0.7555(4) 0.4363(3) 0.1274(3) 0.0170(10) Uani 1 1 d . . . C14 C 0.3591(3) 0.3753(3) 0.1532(3) 0.0150(9) Uani 1 1 d . . . O6 O 0.4663(4) 0.0285(3) 0.1690(3) 0.0526(13) Uani 1 1 d . . . C16 C 0.8957(3) 0.3896(3) 0.2284(2) 0.0139(9) Uani 1 1 d . . . C17 C 0.3299(4) 0.2738(3) 0.1559(3) 0.0215(11) Uani 1 1 d . . . C18 C 0.7103(4) 0.0402(3) 0.9741(3) 0.0171(10) Uani 1 1 d . . . C19 C 0.2555(4) 0.4486(3) 0.1261(3) 0.0182(10) Uani 1 1 d . . . C20 C 0.7884(4) -0.0419(3) 1.0152(3) 0.0160(10) Uani 1 1 d . . . O2 O 0.1679(3) 0.4286(3) 0.1085(2) 0.0349(10) Uani 1 1 d . . . C22 C 0.8221(4) 0.2605(3) 0.1694(3) 0.0239(11) Uani 1 1 d . . . O5 O 0.2940(4) 0.0915(3) 0.2154(3) 0.0541(13) Uani 1 1 d . . . N3 N 0.7911(3) 0.6788(3) 0.5346(2) 0.0226(9) Uani 1 1 d . . . C25 C 0.5328(4) 0.3402(3) 0.3273(3) 0.0193(10) Uani 1 1 d . . . C26 C 0.9376(4) -0.1930(3) 1.0008(3) 0.0155(9) Uani 1 1 d . . . C27 C 0.4599(4) 0.2180(3) 0.2624(3) 0.0181(10) Uani 1 1 d . . . C28 C 0.4009(5) 0.0959(4) 0.1890(3) 0.0294(12) Uani 1 1 d . . . C29 C 0.4302(4) 0.1972(3) 0.1849(3) 0.0185(10) Uani 1 1 d . . . C30 C 0.3915(4) 0.3956(3) 0.2292(3) 0.0147(9) Uani 1 1 d . . . C31 C 1.0413(4) 0.3407(3) 0.3242(3) 0.0171(10) Uani 1 1 d . . . N7 N 1.0994(3) -0.3338(3) 1.0725(2) 0.0206(9) Uani 1 1 d . . . C33 C 0.8558(4) 0.3624(3) 0.1562(3) 0.0160(10) Uani 1 1 d . . . O4 O 0.6290(4) 0.2800(3) 0.3457(2) 0.0410(11) Uani 1 1 d . . . C35 C 0.4878(4) 0.3609(3) 0.9539(3) 0.0195(10) Uani 1 1 d . . . C36 C 0.8530(4) -0.1143(3) 0.9619(3) 0.0231(11) Uani 1 1 d . . . C37 C 0.7019(4) 0.6174(3) 0.4129(3) 0.0213(10) Uani 1 1 d . . . C38 C 0.3872(4) 0.2451(3) 0.9275(3) 0.0210(10) Uani 1 1 d . . . C39 C 0.4925(4) 0.3197(3) 0.2550(3) 0.0156(10) Uani 1 1 d . . . C40 C 0.4686(4) 0.1715(3) 0.9584(3) 0.0200(10) Uani 1 1 d . . . C41 C 0.8496(4) 0.6059(3) 0.4968(3) 0.0255(11) Uani 1 1 d . . . C42 C 0.9253(4) 0.1852(3) 0.1986(3) 0.0244(11) Uani 1 1 d . . . O7 O 0.8541(5) 0.0538(3) 0.2843(3) 0.0696(16) Uani 1 1 d . . . C44 C 0.9969(4) 0.3149(3) 0.2552(3) 0.0161(10) Uani 1 1 d . . . C45 C 0.6492(4) 0.1152(3) 1.0272(3) 0.0192(10) Uani 1 1 d . . . C46 C 1.0086(4) -0.3583(3) 1.0457(3) 0.0224(11) Uani 1 1 d . . . C47 C 0.9639(4) 0.2137(3) 0.2705(3) 0.0206(10) Uani 1 1 d . . . C48 C 0.3126(6) 0.8345(6) 0.2168(3) 0.0485(18) Uani 1 1 d . . . C49 C 0.8436(5) 0.7834(4) 0.2010(3) 0.0367(13) Uani 1 1 d . . . C50 C 0.7019(6) 0.9007(4) 0.2429(4) 0.0442(17) Uani 1 1 d . . . C51 C 0.7822(5) 0.7129(4) 0.2278(3) 0.0314(12) Uani 1 1 d . . . C52 C 0.5718(4) 0.2910(3) 0.9870(3) 0.0187(10) Uani 1 1 d . . . C53 C 0.7745(5) -0.0243(4) 0.5119(4) 0.0383(14) Uani 1 1 d . . . C54 C 0.9242(4) -0.2894(3) 1.0093(3) 0.0195(10) Uani 1 1 d . . . C55 C 0.6408(4) 0.6952(4) 0.4514(3) 0.0286(12) Uani 1 1 d . . . C56 C 1.1109(4) -0.2413(3) 1.0652(3) 0.0251(11) Uani 1 1 d . . . C57 C 0.8096(5) 0.5741(3) 0.4375(3) 0.0276(11) Uani 1 1 d . . . N2 N 0.2899(4) 0.6781(3) 0.5347(2) 0.0267(10) Uani 1 1 d . . . C59 C 0.3524(4) 0.6144(4) 0.4905(3) 0.0312(12) Uani 1 1 d . . . C60 C 0.6589(5) 0.5798(4) 0.3494(3) 0.0322(13) Uani 1 1 d . . . C61 C 0.2730(6) 0.7417(4) 0.2323(3) 0.0430(15) Uani 1 1 d . . . C62 C 0.6703(4) 0.7346(3) 0.2641(3) 0.0231(11) Uani 1 1 d . . . N5 N 0.5623(5) 0.0881(4) 0.5634(3) 0.0571(16) Uani 1 1 d . . . C64 C 1.0327(4) -0.1691(3) 1.0300(3) 0.0226(11) Uani 1 1 d . . . C65 C 0.7273(6) -0.0373(5) 0.5849(4) 0.0521(17) Uani 1 1 d . . . C66 C 0.6227(6) 0.0198(4) 0.6087(4) 0.0506(17) Uani 1 1 d . . . C67 C 0.5967(5) 0.6564(4) 0.2936(3) 0.0335(13) Uani 1 1 d . . . C68 C 0.1355(6) 0.9140(5) 0.2681(4) 0.0484(16) Uani 1 1 d . . . C69 C 0.8889(5) -0.0831(4) 0.4834(4) 0.0469(17) Uani 1 1 d . . . C70 C 0.9851(5) -0.0215(5) 0.4645(4) 0.0537(18) Uani 1 1 d . . . C71 C 0.6874(4) 0.7224(4) 0.5109(3) 0.0296(12) Uani 1 1 d . . . C72 C 0.6260(5) 0.8278(4) 0.2725(3) 0.0374(14) Uani 1 1 d . . . C73 C 0.1330(4) 0.6903(4) 0.4569(3) 0.0336(13) Uani 1 1 d . . . C74 C 0.7128(5) 0.0447(5) 0.4662(4) 0.0476(17) Uani 1 1 d . . . C75 C 0.1816(5) 0.7141(4) 0.5171(3) 0.0317(12) Uani 1 1 d . . . C76 C 0.0948(6) 0.8293(5) 0.2830(4) 0.0523(18) Uani 1 1 d . . . C77 C 0.6073(5) 0.0998(5) 0.4949(4) 0.0504(17) Uani 1 1 d . . . C78 C 0.2013(6) 0.6220(4) 0.4115(3) 0.0368(14) Uani 1 1 d . . . C79 C 0.3127(6) 0.5858(4) 0.4313(4) 0.0405(15) Uani 1 1 d . . . C80 C 0.1604(6) 0.7440(4) 0.2675(3) 0.0375(15) Uani 1 1 d . . . C81 C 0.1624(9) 0.5859(5) 0.3454(4) 0.081(3) Uani 1 1 d . . . C82 C 0.1049(8) 0.6539(5) 0.2907(4) 0.067(3) Uani 1 1 d . . . 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 O11 0.0256(18) 0.0164(16) 0.049(3) -0.0002(16) -0.0210(17) -0.0006(13) O1 0.0274(19) 0.0178(17) 0.059(3) 0.0095(17) -0.0219(18) -0.0011(14) O12 0.0224(18) 0.032(2) 0.041(2) 0.0007(17) -0.0170(16) -0.0085(14) N6 0.0200(19) 0.0184(19) 0.015(2) 0.0020(16) -0.0048(15) 0.0015(15) N1 0.063(3) 0.026(2) 0.027(3) 0.0061(19) -0.021(2) -0.012(2) C6 0.037(3) 0.014(2) 0.062(4) -0.011(3) 0.002(3) -0.003(2) O3 0.033(2) 0.040(2) 0.036(2) -0.0167(18) -0.0144(17) 0.0014(17) O8 0.102(4) 0.027(2) 0.026(2) -0.0082(17) 0.001(2) -0.023(2) O10 0.0258(18) 0.0255(18) 0.032(2) -0.0120(16) -0.0140(15) 0.0038(14) C10 0.016(2) 0.013(2) 0.010(2) -0.0014(16) -0.0010(16) 0.0004(16) N4 0.040(3) 0.042(3) 0.032(3) -0.005(2) -0.009(2) -0.017(2) O9 0.037(2) 0.032(2) 0.035(2) -0.0077(17) -0.0194(17) 0.0167(16) C13 0.014(2) 0.023(2) 0.013(2) -0.0033(18) -0.0040(17) 0.0009(17) C14 0.014(2) 0.012(2) 0.018(2) -0.0026(17) -0.0058(17) 0.0057(15) O6 0.072(3) 0.0133(19) 0.071(3) -0.0066(19) 0.000(2) -0.0051(19) C16 0.015(2) 0.0109(19) 0.015(2) -0.0033(17) -0.0055(17) 0.0023(15) C17 0.024(2) 0.013(2) 0.030(3) -0.0041(19) -0.010(2) -0.0034(17) C18 0.018(2) 0.009(2) 0.025(3) -0.0008(18) -0.0099(19) -0.0004(16) C19 0.021(2) 0.012(2) 0.019(3) -0.0020(18) -0.0005(18) 0.0006(17) C20 0.020(2) 0.010(2) 0.017(2) 0.0051(17) -0.0090(18) 0.0012(16) O2 0.0241(18) 0.0291(19) 0.054(3) -0.0031(18) -0.0235(18) 0.0014(15) C22 0.017(2) 0.017(2) 0.041(3) -0.013(2) -0.007(2) -0.0037(17) O5 0.064(3) 0.034(2) 0.065(3) -0.011(2) 0.012(2) -0.018(2) N3 0.0170(19) 0.027(2) 0.022(2) 0.0029(17) -0.0040(16) -0.0020(16) C25 0.018(2) 0.018(2) 0.021(3) 0.0022(19) -0.0030(18) -0.0048(17) C26 0.015(2) 0.014(2) 0.015(2) 0.0012(17) -0.0008(17) 0.0029(16) C27 0.023(2) 0.008(2) 0.022(3) 0.0040(17) -0.0061(19) -0.0012(16) C28 0.033(3) 0.023(3) 0.031(3) 0.006(2) -0.006(2) -0.008(2) C29 0.021(2) 0.011(2) 0.023(3) -0.0041(18) -0.0016(18) 0.0016(16) C30 0.019(2) 0.0087(19) 0.015(2) -0.0010(16) -0.0028(17) 0.0027(16) C31 0.015(2) 0.014(2) 0.021(3) 0.0015(18) -0.0047(18) 0.0000(16) N7 0.0178(19) 0.021(2) 0.020(2) 0.0027(16) -0.0040(16) 0.0038(15) C33 0.014(2) 0.012(2) 0.023(3) -0.0068(18) -0.0058(18) -0.0015(16) O4 0.044(2) 0.045(2) 0.031(2) -0.0013(18) -0.0268(18) 0.0141(18) C35 0.016(2) 0.016(2) 0.027(3) -0.0014(19) -0.0036(18) -0.0019(17) C36 0.023(2) 0.017(2) 0.028(3) 0.0019(19) -0.014(2) 0.0057(18) C37 0.030(2) 0.016(2) 0.019(3) 0.0031(18) -0.002(2) -0.0098(18) C38 0.020(2) 0.020(2) 0.024(3) 0.0034(19) -0.0093(19) -0.0054(18) C39 0.014(2) 0.011(2) 0.022(3) 0.0031(17) -0.0082(17) -0.0006(16) C40 0.017(2) 0.017(2) 0.026(3) 0.0022(19) -0.0070(19) -0.0014(17) C41 0.019(2) 0.022(2) 0.033(3) 0.004(2) -0.002(2) -0.0023(18) C42 0.022(2) 0.012(2) 0.041(3) -0.014(2) 0.001(2) -0.0021(17) O7 0.113(4) 0.050(3) 0.051(3) -0.015(2) 0.022(3) -0.039(3) C44 0.016(2) 0.0082(19) 0.025(3) 0.0015(17) -0.0058(18) -0.0025(16) C45 0.023(2) 0.014(2) 0.020(3) -0.0020(18) -0.0115(19) 0.0054(17) C46 0.024(2) 0.016(2) 0.024(3) -0.0015(19) 0.004(2) 0.0001(18) C47 0.023(2) 0.0062(19) 0.031(3) -0.0002(18) 0.001(2) -0.0020(16) C48 0.049(4) 0.093(6) 0.008(3) 0.009(3) -0.015(2) -0.023(4) C49 0.038(3) 0.043(3) 0.032(3) 0.001(3) -0.011(2) -0.013(2) C50 0.075(5) 0.017(3) 0.037(4) -0.004(2) -0.024(3) 0.012(3) C51 0.034(3) 0.039(3) 0.019(3) -0.005(2) -0.002(2) 0.001(2) C52 0.016(2) 0.019(2) 0.021(3) -0.0044(19) -0.0039(18) -0.0010(17) C53 0.033(3) 0.038(3) 0.047(4) -0.013(3) 0.010(3) -0.015(2) C54 0.018(2) 0.018(2) 0.022(3) -0.0072(19) -0.0008(18) 0.0008(17) C55 0.019(2) 0.029(3) 0.038(3) -0.003(2) -0.011(2) 0.0004(19) C56 0.018(2) 0.025(2) 0.032(3) 0.008(2) -0.008(2) -0.0047(18) C57 0.032(3) 0.021(2) 0.027(3) 0.002(2) 0.002(2) -0.003(2) N2 0.026(2) 0.029(2) 0.025(2) 0.0031(18) -0.0076(18) -0.0042(17) C59 0.029(3) 0.026(3) 0.036(3) 0.005(2) 0.001(2) -0.004(2) C60 0.050(3) 0.024(3) 0.027(3) 0.006(2) -0.009(2) -0.022(2) C61 0.070(4) 0.045(3) 0.018(3) 0.005(3) -0.019(3) -0.014(3) C62 0.033(3) 0.025(2) 0.016(3) 0.0056(19) -0.013(2) -0.016(2) N5 0.046(3) 0.061(4) 0.053(4) 0.013(3) 0.002(3) 0.003(3) C64 0.014(2) 0.021(2) 0.034(3) 0.006(2) -0.0086(19) -0.0067(17) C65 0.048(4) 0.041(3) 0.065(5) -0.006(3) 0.005(3) -0.007(3) C66 0.056(4) 0.034(3) 0.054(4) -0.003(3) 0.001(3) 0.010(3) C67 0.046(3) 0.037(3) 0.024(3) 0.004(2) -0.008(2) -0.024(3) C68 0.059(4) 0.047(4) 0.039(4) 0.013(3) -0.015(3) -0.017(3) C69 0.032(3) 0.038(3) 0.072(5) -0.025(3) 0.004(3) -0.002(2) C70 0.046(4) 0.059(4) 0.052(4) -0.010(3) 0.009(3) -0.003(3) C71 0.022(2) 0.039(3) 0.027(3) -0.009(2) -0.007(2) 0.005(2) C72 0.034(3) 0.039(3) 0.037(4) -0.011(3) -0.005(2) 0.004(2) C73 0.027(3) 0.046(3) 0.028(3) 0.009(3) -0.013(2) -0.010(2) C74 0.029(3) 0.057(4) 0.058(4) -0.017(3) 0.003(3) -0.007(3) C75 0.032(3) 0.043(3) 0.018(3) -0.002(2) -0.005(2) 0.003(2) C76 0.076(5) 0.051(4) 0.039(4) 0.007(3) -0.033(3) -0.025(3) C77 0.032(3) 0.059(4) 0.055(5) -0.002(3) 0.007(3) -0.002(3) C78 0.077(4) 0.025(3) 0.017(3) 0.006(2) -0.010(3) -0.034(3) C79 0.066(4) 0.017(3) 0.034(4) 0.001(2) 0.006(3) -0.004(2) C80 0.074(4) 0.030(3) 0.019(3) 0.011(2) -0.025(3) -0.034(3) C81 0.179(9) 0.050(4) 0.038(4) 0.023(3) -0.052(5) -0.079(5) C82 0.124(7) 0.058(4) 0.042(4) 0.022(3) -0.047(4) -0.069(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O11 C13 1.321(5) . ? O1 C19 1.333(5) . ? O12 C13 1.208(5) . ? N6 C35 1.330(6) . ? N6 C38 1.349(6) . ? N1 C68 1.312(8) . ? N1 C48 1.346(9) . ? C6 O8 1.270(7) . ? C6 O7 1.275(8) . ? C6 C42 1.530(7) . ? O3 C25 1.198(6) . ? O10 C31 1.203(5) . ? C10 C52 1.380(6) . ? C10 C40 1.397(6) . ? C10 C45 1.512(5) . ? N4 C50 1.275(8) . ? N4 C49 1.321(7) . ? O9 C31 1.329(5) . ? C13 C33 1.516(5) . ? C14 C17 1.525(6) . ? C14 C30 1.529(6) . ? C14 C19 1.529(5) . ? O6 C28 1.173(7) . ? C16 C44 1.518(5) . ? C16 C33 1.537(6) . ? C17 C29 1.538(6) . ? C18 C20 1.514(6) . ? C18 C45 1.535(6) . ? C19 O2 1.193(6) . ? C20 C36 1.526(6) . ? C22 C33 1.545(6) . ? C22 C42 1.553(6) . ? O5 C28 1.293(7) . ? N3 C41 1.341(6) . ? N3 C71 1.347(6) . ? C25 O4 1.331(5) . ? C25 C39 1.506(6) . ? C26 C54 1.388(6) . ? C26 C64 1.389(6) . ? C26 C36 1.510(5) . ? C27 C39 1.538(6) . ? C27 C29 1.546(6) . ? C28 C29 1.521(6) . ? C30 C39 1.520(5) . ? C31 C44 1.502(6) . ? N7 C46 1.327(6) . ? N7 C56 1.327(6) . ? C35 C52 1.391(6) . ? C37 C57 1.393(7) . ? C37 C55 1.408(7) . ? C37 C60 1.484(7) . ? C38 C40 1.386(6) . ? C41 C57 1.361(7) . ? C42 C47 1.533(7) . ? C44 C47 1.534(5) . ? C46 C54 1.414(6) . ? C48 C61 1.452(9) . ? C49 C51 1.343(8) . ? C50 C72 1.489(9) . ? C51 C62 1.392(7) . ? C53 C74 1.355(10) . ? C53 C65 1.369(9) . ? C53 C69 1.512(8) . ? C55 C71 1.376(7) . ? C56 C64 1.385(6) . ? N2 C59 1.332(7) . ? N2 C75 1.334(6) . ? C59 C79 1.337(8) . ? C60 C67 1.526(8) . ? C61 C80 1.390(9) . ? C62 C72 1.345(8) . ? C62 C67 1.529(7) . ? N5 C77 1.286(9) . ? N5 C66 1.338(8) . ? C65 C66 1.391(8) . ? C68 C76 1.352(9) . ? C69 C70 1.526(9) . ? C70 C70 1.572(14) 2_756 ? C73 C75 1.376(7) . ? C73 C78 1.413(9) . ? C74 C77 1.414(8) . ? C76 C80 1.349(10) . ? C78 C79 1.381(9) . ? C78 C81 1.491(8) . ? C80 C82 1.523(7) . ? C81 C82 1.427(10) . ? 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 _geom_angle_publ_flag C35 N6 C38 118.1(4) . . ? C68 N1 C48 121.4(5) . . ? O8 C6 O7 121.6(5) . . ? O8 C6 C42 114.9(5) . . ? O7 C6 C42 123.1(5) . . ? C52 C10 C40 117.4(4) . . ? C52 C10 C45 122.3(4) . . ? C40 C10 C45 120.2(4) . . ? C50 N4 C49 120.5(5) . . ? O12 C13 O11 123.3(4) . . ? O12 C13 C33 124.0(4) . . ? O11 C13 C33 112.7(3) . . ? C17 C14 C30 111.9(4) . . ? C17 C14 C19 108.7(3) . . ? C30 C14 C19 112.0(3) . . ? C44 C16 C33 110.7(3) . . ? C14 C17 C29 110.8(3) . . ? C20 C18 C45 111.5(4) . . ? O2 C19 O1 123.7(4) . . ? O2 C19 C14 125.1(4) . . ? O1 C19 C14 111.2(4) . . ? C18 C20 C36 111.6(4) . . ? C33 C22 C42 110.4(3) . . ? C41 N3 C71 116.8(4) . . ? O3 C25 O4 123.2(4) . . ? O3 C25 C39 124.4(4) . . ? O4 C25 C39 112.3(4) . . ? C54 C26 C64 117.9(4) . . ? C54 C26 C36 122.6(4) . . ? C64 C26 C36 119.5(4) . . ? C39 C27 C29 108.8(4) . . ? O6 C28 O5 122.7(5) . . ? O6 C28 C29 124.4(5) . . ? O5 C28 C29 112.8(4) . . ? C28 C29 C17 111.2(4) . . ? C28 C29 C27 110.6(4) . . ? C17 C29 C27 111.0(3) . . ? C39 C30 C14 110.3(3) . . ? O10 C31 O9 123.2(4) . . ? O10 C31 C44 124.2(4) . . ? O9 C31 C44 112.6(4) . . ? C46 N7 C56 118.8(4) . . ? C13 C33 C16 112.0(3) . . ? C13 C33 C22 110.7(3) . . ? C16 C33 C22 110.4(4) . . ? N6 C35 C52 122.8(4) . . ? C26 C36 C20 112.3(4) . . ? C57 C37 C55 116.4(5) . . ? C57 C37 C60 119.2(5) . . ? C55 C37 C60 124.5(4) . . ? N6 C38 C40 122.2(4) . . ? C25 C39 C30 112.3(4) . . ? C25 C39 C27 110.9(4) . . ? C30 C39 C27 110.7(3) . . ? C38 C40 C10 119.7(4) . . ? N3 C41 C57 123.8(4) . . ? C6 C42 C47 107.7(4) . . ? C6 C42 C22 109.6(4) . . ? C47 C42 C22 111.1(4) . . ? C31 C44 C16 112.3(3) . . ? C31 C44 C47 109.6(4) . . ? C16 C44 C47 111.5(3) . . ? C10 C45 C18 113.2(4) . . ? N7 C46 C54 122.3(4) . . ? C42 C47 C44 109.5(4) . . ? N1 C48 C61 120.3(6) . . ? N4 C49 C51 122.2(5) . . ? N4 C50 C72 121.0(5) . . ? C49 C51 C62 120.8(5) . . ? C10 C52 C35 119.8(4) . . ? C74 C53 C65 116.2(6) . . ? C74 C53 C69 121.5(6) . . ? C65 C53 C69 122.3(6) . . ? C26 C54 C46 118.6(4) . . ? C71 C55 C37 119.6(4) . . ? N7 C56 C64 122.8(4) . . ? C41 C57 C37 120.2(5) . . ? C59 N2 C75 116.3(5) . . ? N2 C59 C79 124.0(5) . . ? C37 C60 C67 115.5(4) . . ? C80 C61 C48 115.7(6) . . ? C72 C62 C51 118.3(5) . . ? C72 C62 C67 119.5(5) . . ? C51 C62 C67 122.2(5) . . ? C77 N5 C66 116.0(6) . . ? C56 C64 C26 119.6(4) . . ? C53 C65 C66 120.1(6) . . ? N5 C66 C65 123.5(6) . . ? C60 C67 C62 111.9(4) . . ? N1 C68 C76 120.2(7) . . ? C53 C69 C70 111.8(5) . . ? C69 C70 C70 112.5(7) . 2_756 ? N3 C71 C55 123.2(5) . . ? C62 C72 C50 117.1(5) . . ? C75 C73 C78 118.1(5) . . ? C53 C74 C77 120.2(7) . . ? N2 C75 C73 124.3(5) . . ? C80 C76 C68 122.6(7) . . ? N5 C77 C74 124.0(7) . . ? C79 C78 C73 116.3(5) . . ? C79 C78 C81 118.2(7) . . ? C73 C78 C81 125.5(7) . . ? C59 C79 C78 121.1(5) . . ? C76 C80 C61 119.7(5) . . ? C76 C80 C82 116.7(7) . . ? C61 C80 C82 123.6(6) . . ? C82 C81 C78 118.9(6) . . ? C81 C82 C80 115.0(6) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 2.754 _refine_diff_density_min -0.585 _refine_diff_density_rms 0.266 # Attachment 'cocrystal_5a.cif' data_5a _database_code_depnum_ccdc_archive 'CCDC 264606' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1,2-bis(4-pyridyl)ethane - 1,4-bis(4-pyridyl)butane - p-xylene ; _chemical_melting_point 412 _chemical_formula_moiety (C9H12O6),(C12H12N2),0.5(C14H16N2),0.5(C8H10) _chemical_formula_sum 'C32 H37 N3 O6' _chemical_formula_weight 559.65 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7110(4) _cell_length_b 14.1003(10) _cell_length_c 18.3960(13) _cell_angle_alpha 86.1000(10) _cell_angle_beta 84.5600(10) _cell_angle_gamma 82.1230(10) _cell_volume 1458.51(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6091 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 27.84 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9571 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 373(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17524 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 26.05 _reflns_number_total 5730 _reflns_number_gt 5007 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0836P)^2^+1.2295P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5730 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1704 _refine_ls_wR_factor_gt 0.1637 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N30 N -0.2090(3) 0.32623(12) 0.42122(9) 0.0250(4) Uani 1 1 d . . . C34 C -0.0510(4) 0.16348(14) 0.45011(11) 0.0243(4) Uani 1 1 d . . . H34 H -0.0619 0.0987 0.4471 0.029 Uiso 1 1 calc R . . C35 C -0.2156(4) 0.23202(14) 0.42015(11) 0.0247(4) Uani 1 1 d . . . H35 H -0.3381 0.2116 0.3980 0.030 Uiso 1 1 calc R . . C31 C -0.0299(4) 0.35380(14) 0.45305(12) 0.0268(5) Uani 1 1 d . . . H31 H -0.0200 0.4190 0.4536 0.032 Uiso 1 1 calc R . . C36 C 0.3078(4) 0.11993(14) 0.52277(11) 0.0248(4) Uani 1 1 d . . . H36A H 0.2284 0.0951 0.5676 0.030 Uiso 1 1 calc R . . H36B H 0.4342 0.1529 0.5362 0.030 Uiso 1 1 calc R . . C37 C 0.4180(3) 0.03561(13) 0.47792(11) 0.0230(4) Uani 1 1 d . . . H37A H 0.2932 0.0034 0.4624 0.028 Uiso 1 1 calc R . . H37B H 0.5073 0.0591 0.4345 0.028 Uiso 1 1 calc R . . C33 C 0.1317(3) 0.19208(14) 0.48484(11) 0.0220(4) Uani 1 1 d . . . C32 C 0.1409(4) 0.28978(14) 0.48515(12) 0.0260(4) Uani 1 1 d . . . H32 H 0.2616 0.3122 0.5069 0.031 Uiso 1 1 calc R . . N22 N 0.4096(4) 0.32414(15) -0.03982(11) 0.0376(5) Uani 1 1 d . . . N16 N 0.5175(4) 0.08313(13) 0.27268(11) 0.0337(4) Uani 1 1 d . . . C25 C 0.6429(4) 0.36560(15) 0.07846(12) 0.0286(5) Uani 1 1 d . . . C19 C 0.5993(4) 0.27173(15) 0.23421(11) 0.0279(5) Uani 1 1 d . . . C17 C 0.3498(4) 0.15619(17) 0.28617(12) 0.0328(5) Uani 1 1 d . . . H17 H 0.2036 0.1434 0.3085 0.039 Uiso 1 1 calc R . . C18 C 0.3836(4) 0.25121(16) 0.26833(12) 0.0320(5) Uani 1 1 d . . . H18 H 0.2623 0.3006 0.2792 0.038 Uiso 1 1 calc R . . C26 C 0.7413(4) 0.29587(17) 0.03164(13) 0.0342(5) Uani 1 1 d . . . H26 H 0.8884 0.2611 0.0391 0.041 Uiso 1 1 calc R . . C20 C 0.7697(4) 0.19450(17) 0.22039(13) 0.0349(5) Uani 1 1 d . . . H20 H 0.9171 0.2045 0.1973 0.042 Uiso 1 1 calc R . . C28 C 0.7748(5) 0.39037(17) 0.14054(13) 0.0362(5) Uani 1 1 d . . . H28A H 0.8002 0.4571 0.1337 0.043 Uiso 1 1 calc R . . H28B H 0.9291 0.3517 0.1390 0.043 Uiso 1 1 calc R . . C29 C 0.6438(5) 0.37418(16) 0.21541(13) 0.0376(6) Uani 1 1 d . . . H29A H 0.7352 0.3937 0.2523 0.045 Uiso 1 1 calc R . . H29B H 0.4925 0.4151 0.2174 0.045 Uiso 1 1 calc R . . C24 C 0.4206(4) 0.41346(16) 0.06500(13) 0.0332(5) Uani 1 1 d . . . H24 H 0.3458 0.4605 0.0955 0.040 Uiso 1 1 calc R . . C23 C 0.3121(4) 0.39046(17) 0.00598(13) 0.0345(5) Uani 1 1 d . . . H23 H 0.1631 0.4229 -0.0023 0.041 Uiso 1 1 calc R . . C27 C 0.6210(4) 0.2779(2) -0.02609(13) 0.0410(6) Uani 1 1 d . . . H27 H 0.6913 0.2309 -0.0573 0.049 Uiso 1 1 calc R . . C21 C 0.7239(4) 0.10333(17) 0.24027(14) 0.0386(6) Uani 1 1 d . . . H21 H 0.8433 0.0528 0.2306 0.046 Uiso 1 1 calc R . . C39 C 0.1454(9) 0.0355(4) 0.0444(2) 0.0915(15) Uani 1 1 d . . . C38 C 0.1261(9) 0.0682(4) -0.0264(3) 0.0956(14) Uani 1 1 d . . . H38 H 0.2178 0.1156 -0.0446 0.115 Uiso 1 1 calc R . . C40 C 0.0225(12) -0.0360(4) 0.0746(3) 0.119(2) Uani 1 1 d . . . H40 H 0.0349 -0.0613 0.1223 0.142 Uiso 1 1 calc R . . C41 C 0.3082(10) 0.0804(6) 0.0877(4) 0.157(3) Uani 1 1 d . . . H41A H 0.2458 0.1463 0.0944 0.236 Uiso 1 1 calc R . . H41B H 0.4628 0.0770 0.0618 0.236 Uiso 1 1 calc R . . H41C H 0.3196 0.0465 0.1346 0.236 Uiso 1 1 calc R . . O6 O 0.4364(3) 0.45494(10) 0.38109(9) 0.0292(4) Uani 1 1 d . . . O1 O 0.0430(3) 0.58659(11) 0.14188(9) 0.0358(4) Uani 1 1 d . . . O4 O 0.4416(3) 0.90111(12) 0.29842(10) 0.0402(4) Uani 1 1 d . . . O3 O 0.0774(3) 0.96317(11) 0.33927(10) 0.0395(4) Uani 1 1 d . . . O5 O 0.6761(3) 0.56340(11) 0.39512(10) 0.0393(4) Uani 1 1 d . . . C15 C 0.4885(4) 0.54359(14) 0.37887(11) 0.0240(4) Uani 1 1 d . . . C10 C 0.3533(4) 0.71864(14) 0.35390(12) 0.0253(4) Uani 1 1 d . . . H10A H 0.3805 0.7316 0.4033 0.030 Uiso 1 1 calc R . . H10B H 0.4991 0.7237 0.3231 0.030 Uiso 1 1 calc R . . C11 C 0.2899(4) 0.61704(13) 0.35316(11) 0.0222(4) Uani 1 1 d . . . H11 H 0.1496 0.6123 0.3876 0.027 Uiso 1 1 calc R . . C14 C 0.2193(4) 0.89469(14) 0.32290(12) 0.0283(5) Uani 1 1 d . . . O2 O -0.2395(4) 0.70856(16) 0.16227(12) 0.0609(7) Uani 1 1 d . . . C12 C 0.2262(4) 0.59531(14) 0.27742(11) 0.0237(4) Uani 1 1 d . . . H12A H 0.3642 0.5965 0.2425 0.028 Uiso 1 1 calc R . . H12B H 0.1780 0.5318 0.2794 0.028 Uiso 1 1 calc R . . C9 C 0.1567(4) 0.79320(13) 0.32666(11) 0.0241(4) Uani 1 1 d . . . H9 H 0.0153 0.7906 0.3610 0.029 Uiso 1 1 calc R . . C7 C 0.0252(4) 0.66945(14) 0.25290(11) 0.0247(4) Uani 1 1 d . . . H7 H -0.1108 0.6662 0.2893 0.030 Uiso 1 1 calc R . . C8 C 0.0927(4) 0.77132(14) 0.25106(11) 0.0261(4) Uani 1 1 d . . . H8A H 0.2270 0.7771 0.2153 0.031 Uiso 1 1 calc R . . H8B H -0.0394 0.8173 0.2366 0.031 Uiso 1 1 calc R . . C13 C -0.0529(4) 0.64919(15) 0.17991(12) 0.0284(5) Uani 1 1 d . . . H6 H 0.566(6) 0.410(2) 0.3971(17) 0.057(9) Uiso 1 1 d . . . H4 H 0.465(6) 0.966(2) 0.2932(17) 0.062(9) Uiso 1 1 d . . . H2 H -0.284(6) 0.692(3) 0.125(2) 0.070(11) Uiso 1 1 d . . . 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 N30 0.0260(9) 0.0206(8) 0.0274(9) 0.0018(7) -0.0058(7) 0.0013(7) C34 0.0262(10) 0.0175(9) 0.0288(11) -0.0008(8) -0.0053(8) -0.0004(8) C35 0.0241(10) 0.0223(10) 0.0281(11) -0.0012(8) -0.0072(8) -0.0013(8) C31 0.0288(11) 0.0167(9) 0.0346(12) -0.0002(8) -0.0055(9) -0.0008(8) C36 0.0254(10) 0.0216(10) 0.0268(11) -0.0018(8) -0.0087(8) 0.0038(8) C37 0.0230(10) 0.0186(9) 0.0275(11) -0.0011(8) -0.0085(8) 0.0012(8) C33 0.0222(10) 0.0207(10) 0.0217(10) -0.0018(8) -0.0006(8) 0.0020(8) C32 0.0245(10) 0.0227(10) 0.0315(11) -0.0037(8) -0.0077(8) -0.0009(8) N22 0.0348(11) 0.0488(12) 0.0301(10) -0.0017(9) -0.0111(8) -0.0031(9) N16 0.0410(11) 0.0266(10) 0.0336(11) 0.0045(8) -0.0076(8) -0.0047(8) C25 0.0343(12) 0.0282(11) 0.0249(11) 0.0066(8) -0.0035(9) -0.0134(9) C19 0.0393(12) 0.0271(11) 0.0190(10) -0.0006(8) -0.0097(8) -0.0058(9) C17 0.0291(11) 0.0413(13) 0.0285(12) 0.0028(9) -0.0037(9) -0.0082(10) C18 0.0343(12) 0.0323(12) 0.0274(11) -0.0040(9) -0.0049(9) 0.0049(9) C26 0.0289(12) 0.0412(13) 0.0318(12) -0.0022(10) -0.0068(9) 0.0004(10) C20 0.0288(12) 0.0400(13) 0.0340(12) 0.0044(10) -0.0004(9) -0.0028(10) C28 0.0494(14) 0.0313(12) 0.0323(12) 0.0027(9) -0.0078(10) -0.0203(10) C29 0.0566(16) 0.0302(12) 0.0288(12) -0.0041(9) -0.0054(11) -0.0127(11) C24 0.0385(13) 0.0249(11) 0.0352(12) 0.0003(9) 0.0040(10) -0.0068(9) C23 0.0296(12) 0.0338(12) 0.0392(13) 0.0102(10) -0.0072(10) -0.0040(9) C27 0.0376(13) 0.0526(15) 0.0323(13) -0.0118(11) -0.0081(10) 0.0036(11) C21 0.0393(13) 0.0308(12) 0.0417(14) 0.0033(10) -0.0015(10) 0.0059(10) C39 0.101(3) 0.095(3) 0.064(3) -0.026(2) -0.010(2) 0.050(3) C38 0.099(3) 0.093(3) 0.082(3) -0.027(3) 0.012(3) 0.030(3) C40 0.148(5) 0.083(3) 0.099(4) -0.013(3) 0.016(4) 0.062(3) C41 0.099(4) 0.219(7) 0.151(6) -0.095(5) -0.042(4) 0.051(4) O6 0.0291(8) 0.0175(7) 0.0414(9) 0.0034(6) -0.0136(7) 0.0007(6) O1 0.0417(9) 0.0326(8) 0.0345(9) -0.0124(7) -0.0122(7) 0.0011(7) O4 0.0430(10) 0.0221(8) 0.0539(11) 0.0009(7) 0.0034(8) -0.0051(7) O3 0.0401(9) 0.0202(8) 0.0574(11) -0.0058(7) -0.0081(8) 0.0034(7) O5 0.0317(9) 0.0242(8) 0.0642(12) 0.0041(7) -0.0226(8) -0.0020(6) C15 0.0269(11) 0.0198(9) 0.0246(10) 0.0006(8) -0.0056(8) 0.0001(8) C10 0.0289(11) 0.0184(10) 0.0292(11) -0.0022(8) -0.0103(8) 0.0005(8) C11 0.0231(10) 0.0179(9) 0.0252(10) -0.0012(8) -0.0050(8) 0.0011(7) C14 0.0367(12) 0.0198(10) 0.0282(11) 0.0001(8) -0.0103(9) 0.0016(9) O2 0.0576(13) 0.0739(15) 0.0497(12) -0.0291(11) -0.0368(10) 0.0317(11) C12 0.0248(10) 0.0183(9) 0.0279(11) -0.0039(8) -0.0065(8) 0.0019(8) C9 0.0279(11) 0.0169(9) 0.0268(11) -0.0012(8) -0.0055(8) 0.0021(8) C7 0.0250(10) 0.0225(10) 0.0263(11) -0.0041(8) -0.0063(8) 0.0020(8) C8 0.0298(11) 0.0209(10) 0.0267(11) -0.0010(8) -0.0074(8) 0.0035(8) C13 0.0283(11) 0.0273(11) 0.0305(11) -0.0018(9) -0.0094(9) -0.0020(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N30 C35 1.336(3) . ? N30 C31 1.339(3) . ? C34 C35 1.378(3) . ? C34 C33 1.391(3) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C31 C32 1.382(3) . ? C31 H31 0.9300 . ? C36 C33 1.513(3) . ? C36 C37 1.523(3) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C37 1.523(4) 2_656 ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C33 C32 1.386(3) . ? C32 H32 0.9300 . ? N22 C27 1.329(3) . ? N22 C23 1.330(3) . ? N16 C17 1.326(3) . ? N16 C21 1.327(3) . ? C25 C26 1.377(3) . ? C25 C24 1.389(3) . ? C25 C28 1.511(3) . ? C19 C20 1.377(3) . ? C19 C18 1.386(3) . ? C19 C29 1.512(3) . ? C17 C18 1.392(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C26 C27 1.374(3) . ? C26 H26 0.9300 . ? C20 C21 1.366(3) . ? C20 H20 0.9300 . ? C28 C29 1.522(3) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C24 C23 1.378(3) . ? C24 H24 0.9300 . ? C23 H23 0.9300 . ? C27 H27 0.9300 . ? C21 H21 0.9300 . ? C39 C38 1.361(6) . ? C39 C40 1.364(7) . ? C39 C41 1.507(7) . ? C38 C40 1.420(8) 2 ? C38 H38 0.9300 . ? C40 C38 1.420(8) 2 ? C40 H40 0.9300 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? O6 C15 1.321(2) . ? O6 H6 0.96(3) . ? O1 C13 1.203(3) . ? O4 C14 1.319(3) . ? O4 H4 0.93(3) . ? O3 C14 1.208(3) . ? O5 C15 1.212(3) . ? C15 C11 1.515(3) . ? C10 C9 1.526(3) . ? C10 C11 1.526(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.534(3) . ? C11 H11 0.9800 . ? C14 C9 1.517(3) . ? O2 C13 1.314(3) . ? O2 H2 0.81(4) . ? C12 C7 1.523(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C9 C8 1.533(3) . ? C9 H9 0.9800 . ? C7 C13 1.511(3) . ? C7 C8 1.535(3) . ? C7 H7 0.9800 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 _geom_angle_publ_flag C35 N30 C31 117.02(17) . . ? C35 C34 C33 119.42(18) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? N30 C35 C34 123.61(19) . . ? N30 C35 H35 118.2 . . ? C34 C35 H35 118.2 . . ? N30 C31 C32 123.03(18) . . ? N30 C31 H31 118.5 . . ? C32 C31 H31 118.5 . . ? C33 C36 C37 115.14(17) . . ? C33 C36 H36A 108.5 . . ? C37 C36 H36A 108.5 . . ? C33 C36 H36B 108.5 . . ? C37 C36 H36B 108.5 . . ? H36A C36 H36B 107.5 . . ? C37 C37 C36 111.2(2) 2_656 . ? C37 C37 H37A 109.4 2_656 . ? C36 C37 H37A 109.4 . . ? C37 C37 H37B 109.4 2_656 . ? C36 C37 H37B 109.4 . . ? H37A C37 H37B 108.0 . . ? C32 C33 C34 117.06(18) . . ? C32 C33 C36 121.42(18) . . ? C34 C33 C36 121.49(17) . . ? C31 C32 C33 119.83(19) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C27 N22 C23 117.0(2) . . ? C17 N16 C21 117.37(19) . . ? C26 C25 C24 117.2(2) . . ? C26 C25 C28 121.1(2) . . ? C24 C25 C28 121.7(2) . . ? C20 C19 C18 116.5(2) . . ? C20 C19 C29 122.5(2) . . ? C18 C19 C29 120.9(2) . . ? N16 C17 C18 122.8(2) . . ? N16 C17 H17 118.6 . . ? C18 C17 H17 118.6 . . ? C19 C18 C17 119.5(2) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C27 C26 C25 119.6(2) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C21 C20 C19 120.5(2) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C25 C28 C29 113.11(19) . . ? C25 C28 H28A 109.0 . . ? C29 C28 H28A 109.0 . . ? C25 C28 H28B 109.0 . . ? C29 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C19 C29 C28 114.47(19) . . ? C19 C29 H29A 108.6 . . ? C28 C29 H29A 108.6 . . ? C19 C29 H29B 108.6 . . ? C28 C29 H29B 108.6 . . ? H29A C29 H29B 107.6 . . ? C23 C24 C25 119.3(2) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? N22 C23 C24 123.3(2) . . ? N22 C23 H23 118.3 . . ? C24 C23 H23 118.3 . . ? N22 C27 C26 123.6(2) . . ? N22 C27 H27 118.2 . . ? C26 C27 H27 118.2 . . ? N16 C21 C20 123.3(2) . . ? N16 C21 H21 118.3 . . ? C20 C21 H21 118.3 . . ? C38 C39 C40 120.9(5) . . ? C38 C39 C41 117.7(6) . . ? C40 C39 C41 121.5(6) . . ? C39 C38 C40 125.4(5) . 2 ? C39 C38 H38 117.3 . . ? C40 C38 H38 117.3 2 . ? C39 C40 C38 113.7(5) . 2 ? C39 C40 H40 123.1 . . ? C38 C40 H40 123.1 2 . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C15 O6 H6 111.1(18) . . ? C14 O4 H4 109.4(19) . . ? O5 C15 O6 123.31(18) . . ? O5 C15 C11 123.99(18) . . ? O6 C15 C11 112.70(17) . . ? C9 C10 C11 111.62(16) . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C15 C11 C10 111.11(16) . . ? C15 C11 C12 110.87(16) . . ? C10 C11 C12 111.57(16) . . ? C15 C11 H11 107.7 . . ? C10 C11 H11 107.7 . . ? C12 C11 H11 107.7 . . ? O3 C14 O4 123.4(2) . . ? O3 C14 C9 123.1(2) . . ? O4 C14 C9 113.55(18) . . ? C13 O2 H2 109(3) . . ? C7 C12 C11 110.01(16) . . ? C7 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? C7 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C14 C9 C10 113.03(17) . . ? C14 C9 C8 108.59(16) . . ? C10 C9 C8 111.43(16) . . ? C14 C9 H9 107.9 . . ? C10 C9 H9 107.9 . . ? C8 C9 H9 107.9 . . ? C13 C7 C12 112.43(17) . . ? C13 C7 C8 110.64(17) . . ? C12 C7 C8 111.18(16) . . ? C13 C7 H7 107.4 . . ? C12 C7 H7 107.4 . . ? C8 C7 H7 107.4 . . ? C9 C8 C7 110.14(16) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? O1 C13 O2 123.4(2) . . ? O1 C13 C7 124.67(19) . . ? O2 C13 C7 111.93(19) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.057 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.059 # Attachment 'cocrystal_5b.cif' data_5b _database_code_depnum_ccdc_archive 'CCDC 264604' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1,2-bis(4-pyridyl)ethane - 1,4-bis(4-pyridyl)butane - 1,4-dichlorobenzene ; _chemical_melting_point 435 _chemical_formula_moiety (C9H12O6),(C12H12N2),0.5(C14H16N2),0.5(C6H4Cl2) _chemical_formula_sum 'C31 H34 Cl N3 O6' _chemical_formula_weight 580.06 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6882(7) _cell_length_b 14.0309(18) _cell_length_c 18.390(2) _cell_angle_alpha 85.767(2) _cell_angle_beta 84.034(2) _cell_angle_gamma 81.877(2) _cell_volume 1442.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4144 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 28.17 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9492 _exptl_absorpt_correction_T_max 0.9785 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14907 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.12 _diffrn_reflns_theta_max 25.73 _reflns_number_total 5470 _reflns_number_gt 4327 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.7404P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5470 _refine_ls_number_parameters 386 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl41 Cl 0.28458(15) 0.02796(13) 0.13066(7) 0.0601(4) Uani 0.811(3) 1 d P A 1 Cl42 Cl 0.2976(8) 0.0803(6) 0.1050(3) 0.0601(4) Uani 0.189(3) 1 d P A 2 C39 C 0.1244(4) 0.01537(18) 0.05579(13) 0.0401(6) Uani 1 1 d . . . C38 C 0.1772(4) 0.05785(16) -0.01227(14) 0.0407(6) Uani 1 1 d . . . H38 H 0.2997 0.0980 -0.0201 0.049 Uiso 1 1 calc R . . C40 C -0.0519(4) -0.04190(17) 0.06899(13) 0.0414(6) Uani 1 1 d . . . H40 H -0.0872 -0.0703 0.1167 0.050 Uiso 1 1 calc R . . O6 O 0.4370(2) 0.45806(9) 0.37780(8) 0.0264(3) Uani 1 1 d . . . O3 O 0.0821(2) 0.96929(9) 0.34012(8) 0.0310(4) Uani 1 1 d . . . O1 O 0.0420(3) 0.59206(10) 0.13891(8) 0.0322(4) Uani 1 1 d . . . O4 O 0.4527(3) 0.90736(10) 0.30151(8) 0.0306(3) Uani 1 1 d . . . O5 O 0.6851(3) 0.56464(10) 0.38729(10) 0.0421(4) Uani 1 1 d . . . C33 C 0.1281(3) 0.19316(13) 0.48574(10) 0.0186(4) Uani 1 1 d . . . C35 C -0.2173(3) 0.23372(13) 0.42005(11) 0.0221(4) Uani 1 1 d . . . H35 H -0.3413 0.2127 0.3970 0.027 Uiso 1 1 calc R . . C34 C -0.0539(3) 0.16487(13) 0.45071(10) 0.0209(4) Uani 1 1 d . . . H34 H -0.0652 0.0983 0.4480 0.025 Uiso 1 1 calc R . . O2 O -0.2033(3) 0.72962(11) 0.15144(9) 0.0375(4) Uani 1 1 d . . . C10 C 0.3594(4) 0.72257(13) 0.35147(11) 0.0243(4) Uani 1 1 d . . . H10A H 0.5104 0.7282 0.3204 0.029 Uiso 1 1 calc R . . H10B H 0.3852 0.7336 0.4024 0.029 Uiso 1 1 calc R . . N30 N -0.2114(3) 0.32852(11) 0.42086(9) 0.0231(4) Uani 1 1 d . . . C11 C 0.2944(3) 0.62114(13) 0.34854(11) 0.0226(4) Uani 1 1 d . . . H11 H 0.1487 0.6152 0.3831 0.027 Uiso 1 1 calc R . . C25 C 0.6455(3) 0.36360(13) 0.07564(11) 0.0227(4) Uani 1 1 d . . . C18 C 0.3881(3) 0.25856(14) 0.26775(11) 0.0253(4) Uani 1 1 d . . . H18 H 0.2620 0.3093 0.2777 0.030 Uiso 1 1 calc R . . C15 C 0.4934(3) 0.54635(13) 0.37314(11) 0.0231(4) Uani 1 1 d . . . N22 N 0.3994(3) 0.31013(12) -0.03543(9) 0.0292(4) Uani 1 1 d . . . C36 C 0.3048(3) 0.12025(13) 0.52342(11) 0.0212(4) Uani 1 1 d . . . H36A H 0.2225 0.0941 0.5691 0.025 Uiso 1 1 calc R . . H36B H 0.4333 0.1540 0.5375 0.025 Uiso 1 1 calc R . . C14 C 0.2271(4) 0.90091(13) 0.32387(11) 0.0239(4) Uani 1 1 d . . . C19 C 0.6051(3) 0.27921(13) 0.23340(10) 0.0214(4) Uani 1 1 d . . . C24 C 0.4219(4) 0.41180(14) 0.06148(11) 0.0261(4) Uani 1 1 d . . . H24 H 0.3491 0.4640 0.0897 0.031 Uiso 1 1 calc R . . C9 C 0.1639(3) 0.79942(13) 0.32505(11) 0.0220(4) Uani 1 1 d . . . H9 H 0.0164 0.7957 0.3593 0.026 Uiso 1 1 calc R . . N16 N 0.5265(3) 0.08969(11) 0.27590(9) 0.0248(4) Uani 1 1 d . . . C13 C -0.0368(3) 0.66149(13) 0.17339(11) 0.0238(4) Uani 1 1 d . . . C21 C 0.7357(4) 0.10936(14) 0.24356(11) 0.0272(5) Uani 1 1 d . . . H21 H 0.8600 0.0574 0.2355 0.033 Uiso 1 1 calc R . . C31 C -0.0337(3) 0.35596(13) 0.45309(11) 0.0254(4) Uani 1 1 d . . . H31 H -0.0240 0.4230 0.4535 0.031 Uiso 1 1 calc R . . C37 C 0.4182(3) 0.03624(12) 0.47806(10) 0.0202(4) Uani 1 1 d . . . H37A H 0.2912 0.0036 0.4617 0.024 Uiso 1 1 calc R . . H37B H 0.5111 0.0611 0.4339 0.024 Uiso 1 1 calc R . . C7 C 0.0378(3) 0.67946(13) 0.24723(11) 0.0217(4) Uani 1 1 d . . . H7 H -0.1038 0.6754 0.2838 0.026 Uiso 1 1 calc R . . C20 C 0.7809(3) 0.20120(14) 0.22126(11) 0.0259(4) Uani 1 1 d . . . H20 H 0.9326 0.2113 0.1975 0.031 Uiso 1 1 calc R . . C17 C 0.3549(3) 0.16392(14) 0.28756(11) 0.0254(4) Uani 1 1 d . . . H17 H 0.2040 0.1512 0.3104 0.030 Uiso 1 1 calc R . . C8 C 0.1063(4) 0.78119(13) 0.24800(11) 0.0237(4) Uani 1 1 d . . . H8A H -0.0273 0.8295 0.2332 0.028 Uiso 1 1 calc R . . H8B H 0.2471 0.7880 0.2125 0.028 Uiso 1 1 calc R . . C28 C 0.7783(4) 0.39376(14) 0.13478(11) 0.0274(5) Uani 1 1 d . . . H28A H 0.8010 0.4623 0.1247 0.033 Uiso 1 1 calc R . . H28B H 0.9382 0.3550 0.1335 0.033 Uiso 1 1 calc R . . C12 C 0.2367(3) 0.60298(13) 0.27141(11) 0.0229(4) Uani 1 1 d . . . H12A H 0.3811 0.6050 0.2366 0.028 Uiso 1 1 calc R . . H12B H 0.1865 0.5382 0.2715 0.028 Uiso 1 1 calc R . . C32 C 0.1362(3) 0.29157(13) 0.48576(11) 0.0239(4) Uani 1 1 d . . . H32 H 0.2585 0.3146 0.5082 0.029 Uiso 1 1 calc R . . C23 C 0.3077(4) 0.38281(14) 0.00613(12) 0.0278(5) Uani 1 1 d . . . H23 H 0.1555 0.4164 -0.0029 0.033 Uiso 1 1 calc R . . C29 C 0.6485(4) 0.38113(14) 0.21152(11) 0.0283(5) Uani 1 1 d . . . H29A H 0.7439 0.4029 0.2476 0.034 Uiso 1 1 calc R . . H29B H 0.4932 0.4233 0.2135 0.034 Uiso 1 1 calc R . . C26 C 0.7393(4) 0.28788(14) 0.03284(11) 0.0270(5) Uani 1 1 d . . . H26 H 0.8904 0.2524 0.0409 0.032 Uiso 1 1 calc R . . C27 C 0.6128(4) 0.26401(15) -0.02153(12) 0.0312(5) Uani 1 1 d . . . H27 H 0.6812 0.2120 -0.0506 0.037 Uiso 1 1 calc R . . H4 H 0.477(5) 0.975(2) 0.2936(15) 0.065(9) Uiso 1 1 d . . . H6 H 0.573(5) 0.411(2) 0.3925(16) 0.076(9) Uiso 1 1 d . . . H2 H -0.262(5) 0.715(2) 0.1084(17) 0.075(10) Uiso 1 1 d . . . 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 Cl41 0.0335(4) 0.1168(12) 0.0304(6) -0.0245(7) -0.0041(4) -0.0004(5) Cl42 0.0335(4) 0.1168(12) 0.0304(6) -0.0245(7) -0.0041(4) -0.0004(5) C39 0.0286(12) 0.0565(15) 0.0335(13) -0.0211(12) -0.0035(10) 0.0102(11) C38 0.0381(13) 0.0339(13) 0.0493(16) -0.0103(11) 0.0086(11) -0.0072(10) C40 0.0410(14) 0.0439(14) 0.0317(13) 0.0077(11) 0.0052(11) 0.0091(11) O6 0.0273(7) 0.0142(7) 0.0383(9) 0.0024(6) -0.0103(6) -0.0015(5) O3 0.0340(8) 0.0173(7) 0.0407(9) -0.0024(6) -0.0057(7) 0.0016(6) O1 0.0379(8) 0.0264(8) 0.0339(9) -0.0115(7) -0.0077(7) -0.0013(6) O4 0.0333(8) 0.0180(7) 0.0406(9) -0.0019(6) -0.0030(7) -0.0045(6) O5 0.0323(9) 0.0223(8) 0.0749(12) 0.0068(8) -0.0251(8) -0.0048(6) C33 0.0187(9) 0.0172(9) 0.0182(10) -0.0028(7) 0.0016(7) 0.0022(7) C35 0.0231(10) 0.0186(10) 0.0251(11) -0.0030(8) -0.0051(8) -0.0015(7) C34 0.0232(10) 0.0142(9) 0.0256(11) -0.0021(8) -0.0042(8) -0.0012(7) O2 0.0473(10) 0.0316(8) 0.0351(9) -0.0090(7) -0.0230(8) 0.0074(7) C10 0.0282(10) 0.0179(9) 0.0281(11) -0.0024(8) -0.0094(9) -0.0018(8) N30 0.0224(8) 0.0190(8) 0.0272(9) 0.0002(7) -0.0038(7) 0.0002(6) C11 0.0255(10) 0.0168(9) 0.0256(11) -0.0012(8) -0.0060(8) -0.0007(8) C25 0.0281(10) 0.0193(9) 0.0217(10) 0.0044(8) -0.0021(8) -0.0098(8) C18 0.0256(10) 0.0264(11) 0.0228(11) -0.0037(8) -0.0028(8) 0.0014(8) C15 0.0269(11) 0.0177(10) 0.0246(11) 0.0011(8) -0.0055(8) -0.0013(8) N22 0.0325(10) 0.0307(10) 0.0258(10) -0.0004(8) -0.0060(8) -0.0076(8) C36 0.0220(10) 0.0187(9) 0.0226(10) -0.0023(8) -0.0051(8) 0.0015(7) C14 0.0305(11) 0.0199(10) 0.0221(11) 0.0013(8) -0.0097(9) -0.0025(8) C19 0.0290(11) 0.0202(9) 0.0169(10) -0.0025(8) -0.0066(8) -0.0057(8) C24 0.0305(11) 0.0197(10) 0.0277(11) 0.0000(8) 0.0015(9) -0.0064(8) C9 0.0254(10) 0.0169(9) 0.0237(11) -0.0022(8) -0.0042(8) -0.0015(7) N16 0.0297(9) 0.0220(8) 0.0235(9) 0.0005(7) -0.0061(7) -0.0051(7) C13 0.0256(10) 0.0197(10) 0.0272(11) -0.0008(8) -0.0045(9) -0.0060(8) C21 0.0270(11) 0.0261(10) 0.0269(11) -0.0007(9) -0.0038(9) 0.0023(8) C31 0.0277(11) 0.0156(9) 0.0333(12) -0.0013(8) -0.0054(9) -0.0021(8) C37 0.0210(10) 0.0161(9) 0.0235(10) -0.0008(8) -0.0047(8) -0.0007(7) C7 0.0232(10) 0.0181(9) 0.0234(10) -0.0030(8) -0.0036(8) 0.0002(7) C20 0.0228(10) 0.0290(11) 0.0252(11) 0.0009(9) -0.0006(8) -0.0036(8) C17 0.0233(10) 0.0305(11) 0.0231(11) -0.0008(9) -0.0032(8) -0.0063(8) C8 0.0285(11) 0.0177(9) 0.0245(11) 0.0001(8) -0.0063(8) 0.0005(8) C28 0.0349(11) 0.0236(10) 0.0265(11) 0.0009(9) -0.0051(9) -0.0131(9) C12 0.0256(10) 0.0158(9) 0.0278(11) -0.0040(8) -0.0048(8) -0.0009(7) C32 0.0237(10) 0.0203(10) 0.0289(11) -0.0047(8) -0.0071(8) -0.0017(8) C23 0.0241(10) 0.0265(11) 0.0322(12) 0.0056(9) -0.0039(9) -0.0047(8) C29 0.0388(12) 0.0227(10) 0.0249(11) -0.0040(9) -0.0046(9) -0.0067(9) C26 0.0256(10) 0.0256(10) 0.0300(12) -0.0013(9) -0.0037(9) -0.0029(8) C27 0.0350(12) 0.0297(11) 0.0295(12) -0.0078(9) -0.0029(9) -0.0030(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl41 C39 1.761(2) . ? Cl42 C39 1.784(6) . ? C39 C40 1.363(4) . ? C39 C38 1.369(3) . ? C38 C40 1.371(3) 2 ? C38 H38 0.9500 . ? C40 C38 1.371(3) 2 ? C40 H40 0.9500 . ? O6 C15 1.318(2) . ? O6 H6 0.99(3) . ? O3 C14 1.207(2) . ? O1 C13 1.209(2) . ? O4 C14 1.319(2) . ? O4 H4 0.97(3) . ? O5 C15 1.212(2) . ? C33 C32 1.388(3) . ? C33 C34 1.392(3) . ? C33 C36 1.512(2) . ? C35 N30 1.336(2) . ? C35 C34 1.375(2) . ? C35 H35 0.9500 . ? C34 H34 0.9500 . ? O2 C13 1.319(2) . ? O2 H2 0.94(3) . ? C10 C11 1.526(3) . ? C10 C9 1.527(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? N30 C31 1.338(2) . ? C11 C15 1.513(2) . ? C11 C12 1.536(3) . ? C11 H11 1.0000 . ? C25 C26 1.382(3) . ? C25 C24 1.394(3) . ? C25 C28 1.504(3) . ? C18 C17 1.384(3) . ? C18 C19 1.385(3) . ? C18 H18 0.9500 . ? N22 C27 1.333(3) . ? N22 C23 1.333(3) . ? C36 C37 1.523(2) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C14 C9 1.515(3) . ? C19 C20 1.389(3) . ? C19 C29 1.504(3) . ? C24 C23 1.377(3) . ? C24 H24 0.9500 . ? C9 C8 1.534(3) . ? C9 H9 1.0000 . ? N16 C21 1.329(3) . ? N16 C17 1.336(2) . ? C13 C7 1.513(3) . ? C21 C20 1.374(3) . ? C21 H21 0.9500 . ? C31 C32 1.380(3) . ? C31 H31 0.9500 . ? C37 C37 1.523(3) 2_656 ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C7 C12 1.523(2) . ? C7 C8 1.533(3) . ? C7 H7 1.0000 . ? C20 H20 0.9500 . ? C17 H17 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C28 C29 1.534(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C32 H32 0.9500 . ? C23 H23 0.9500 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C26 C27 1.377(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? 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 _geom_angle_publ_flag C40 C39 C38 121.7(2) . . ? C40 C39 Cl41 115.9(2) . . ? C38 C39 Cl41 122.4(2) . . ? C40 C39 Cl42 139.5(3) . . ? C38 C39 Cl42 97.4(3) . . ? Cl41 C39 Cl42 27.8(2) . . ? C39 C38 C40 119.5(2) . 2 ? C39 C38 H38 120.3 . . ? C40 C38 H38 120.3 2 . ? C39 C40 C38 118.9(2) . 2 ? C39 C40 H40 120.6 . . ? C38 C40 H40 120.6 2 . ? C15 O6 H6 110.9(17) . . ? C14 O4 H4 110.0(16) . . ? C32 C33 C34 116.74(16) . . ? C32 C33 C36 121.70(17) . . ? C34 C33 C36 121.54(16) . . ? N30 C35 C34 123.64(18) . . ? N30 C35 H35 118.2 . . ? C34 C35 H35 118.2 . . ? C35 C34 C33 119.64(17) . . ? C35 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? C13 O2 H2 111.8(18) . . ? C11 C10 C9 111.60(15) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C35 N30 C31 116.89(16) . . ? C15 C11 C10 110.55(15) . . ? C15 C11 C12 110.64(15) . . ? C10 C11 C12 111.16(16) . . ? C15 C11 H11 108.1 . . ? C10 C11 H11 108.1 . . ? C12 C11 H11 108.1 . . ? C26 C25 C24 117.19(18) . . ? C26 C25 C28 121.81(18) . . ? C24 C25 C28 121.01(18) . . ? C17 C18 C19 119.97(18) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? O5 C15 O6 122.97(17) . . ? O5 C15 C11 124.26(17) . . ? O6 C15 C11 112.78(16) . . ? C27 N22 C23 117.11(18) . . ? C33 C36 C37 115.12(15) . . ? C33 C36 H36A 108.5 . . ? C37 C36 H36A 108.5 . . ? C33 C36 H36B 108.5 . . ? C37 C36 H36B 108.5 . . ? H36A C36 H36B 107.5 . . ? O3 C14 O4 123.66(18) . . ? O3 C14 C9 122.72(18) . . ? O4 C14 C9 113.60(16) . . ? C18 C19 C20 116.57(17) . . ? C18 C19 C29 121.54(17) . . ? C20 C19 C29 121.89(18) . . ? C23 C24 C25 119.18(18) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C14 C9 C10 113.12(16) . . ? C14 C9 C8 108.33(15) . . ? C10 C9 C8 111.11(15) . . ? C14 C9 H9 108.0 . . ? C10 C9 H9 108.0 . . ? C8 C9 H9 108.0 . . ? C21 N16 C17 117.44(17) . . ? O1 C13 O2 123.54(18) . . ? O1 C13 C7 124.40(17) . . ? O2 C13 C7 112.04(16) . . ? N16 C21 C20 123.22(18) . . ? N16 C21 H21 118.4 . . ? C20 C21 H21 118.4 . . ? N30 C31 C32 123.12(17) . . ? N30 C31 H31 118.4 . . ? C32 C31 H31 118.4 . . ? C37 C37 C36 111.34(19) 2_656 . ? C37 C37 H37A 109.4 2_656 . ? C36 C37 H37A 109.4 . . ? C37 C37 H37B 109.4 2_656 . ? C36 C37 H37B 109.4 . . ? H37A C37 H37B 108.0 . . ? C13 C7 C12 112.17(15) . . ? C13 C7 C8 111.31(16) . . ? C12 C7 C8 111.35(15) . . ? C13 C7 H7 107.2 . . ? C12 C7 H7 107.2 . . ? C8 C7 H7 107.2 . . ? C21 C20 C19 120.07(18) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? N16 C17 C18 122.73(18) . . ? N16 C17 H17 118.6 . . ? C18 C17 H17 118.6 . . ? C7 C8 C9 109.89(15) . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C25 C28 C29 112.85(16) . . ? C25 C28 H28A 109.0 . . ? C29 C28 H28A 109.0 . . ? C25 C28 H28B 109.0 . . ? C29 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C7 C12 C11 109.93(15) . . ? C7 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? C7 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C31 C32 C33 119.94(18) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? N22 C23 C24 123.51(19) . . ? N22 C23 H23 118.2 . . ? C24 C23 H23 118.2 . . ? C19 C29 C28 113.99(16) . . ? C19 C29 H29A 108.8 . . ? C28 C29 H29A 108.8 . . ? C19 C29 H29B 108.8 . . ? C28 C29 H29B 108.8 . . ? H29A C29 H29B 107.6 . . ? C27 C26 C25 119.71(18) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? N22 C27 C26 123.30(19) . . ? N22 C27 H27 118.4 . . ? C26 C27 H27 118.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.73 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.372 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.047 # Attachment 'cocrystal_5c.cif' data_5c _database_code_depnum_ccdc_archive 'CCDC 681089' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1,2-bis(4-pyridyl)ethane - 1,4-bis(4-pyridyl)butane - o-xylene ; _chemical_melting_point ? _chemical_formula_moiety (C14H16N2),2(C9H12O6),2(C12H12N2),(C8H10) _chemical_formula_sum 'C64 H74 N6 O12' _chemical_formula_weight 1119.29 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7049(6) _cell_length_b 14.0883(16) _cell_length_c 18.287(2) _cell_angle_alpha 85.834(2) _cell_angle_beta 82.960(2) _cell_angle_gamma 82.027(2) _cell_volume 1442.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6187 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.97 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9609 _exptl_absorpt_correction_T_max 0.9815 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20436 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.76 _reflns_number_total 5491 _reflns_number_gt 4462 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.8627P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5491 _refine_ls_number_parameters 418 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0602 _refine_ls_wR_factor_ref 0.1476 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C41 C 0.3580(13) 1.0041(6) 1.1150(4) 0.0552(18) Uani 0.50 1 d P A -1 H41 H 0.2820 1.0165 1.1632 0.066 Uiso 0.50 1 calc PR A -1 C40 C 0.5819(11) 0.9547(4) 1.1064(3) 0.0446(13) Uani 0.50 1 d P A -1 H40 H 0.6620 0.9320 1.1482 0.053 Uiso 0.50 1 calc PR A -1 C38 C 0.5758(14) 0.9661(6) 0.9739(4) 0.0600(18) Uani 0.50 1 d P A -1 C42 C 0.2424(14) 1.0357(5) 1.0553(5) 0.0676(19) Uani 0.50 1 d P A -1 H42 H 0.0844 1.0681 1.0615 0.081 Uiso 0.50 1 calc PR A -1 C39 C 0.6910(15) 0.9380(7) 1.0351(5) 0.061(2) Uani 0.50 1 d P A -1 H39 H 0.8498 0.9064 1.0287 0.074 Uiso 0.50 1 calc PR A -1 C43 C 0.3628(15) 1.0193(5) 0.9827(5) 0.054(2) Uani 0.50 1 d P A -1 C44 C 0.686(3) 0.9363(11) 0.8996(6) 0.134(6) Uani 0.50 1 d P A -1 H44A H 0.5812 0.9630 0.8625 0.201 Uiso 0.50 1 calc PR A -1 H44B H 0.7092 0.8661 0.8993 0.201 Uiso 0.50 1 calc PR A -1 H44C H 0.8405 0.9602 0.8881 0.201 Uiso 0.50 1 calc PR A -1 C45 C 0.223(2) 1.0531(6) 0.9180(6) 0.107(4) Uani 0.50 1 d P A -1 H45A H 0.3236 1.0387 0.8717 0.161 Uiso 0.50 1 calc PR A -1 H45B H 0.1736 1.1225 0.9191 0.161 Uiso 0.50 1 calc PR A -1 H45C H 0.0818 1.0199 0.9215 0.161 Uiso 0.50 1 calc PR A -1 O6 O 0.4472(3) 0.45556(10) 0.37782(9) 0.0274(4) Uani 1 1 d . . . O1 O 0.0486(3) 0.58607(11) 0.14040(9) 0.0348(4) Uani 1 1 d . . . O4 O 0.4689(3) 0.90217(11) 0.29960(9) 0.0310(4) Uani 1 1 d . . . O3 O 0.0982(3) 0.96482(10) 0.33757(9) 0.0332(4) Uani 1 1 d . . . O5 O 0.6898(3) 0.56266(11) 0.38993(11) 0.0403(5) Uani 1 1 d . . . C10 C 0.3707(4) 0.71912(14) 0.35091(12) 0.0238(5) Uani 1 1 d . . . H10A H 0.3946 0.7314 0.4019 0.029 Uiso 1 1 calc R . . H10B H 0.5226 0.7241 0.3192 0.029 Uiso 1 1 calc R . . C11 C 0.3052(4) 0.61776(14) 0.34950(11) 0.0216(4) Uani 1 1 d . . . H11 H 0.1592 0.6128 0.3851 0.026 Uiso 1 1 calc R . . O2 O -0.2020(3) 0.71989(13) 0.15672(11) 0.0471(5) Uani 1 1 d . . . C14 C 0.2422(4) 0.89631(15) 0.32205(11) 0.0233(5) Uani 1 1 d . . . C15 C 0.5022(4) 0.54382(14) 0.37447(12) 0.0232(4) Uani 1 1 d . . . C7 C 0.0494(4) 0.67384(14) 0.24861(11) 0.0224(4) Uani 1 1 d . . . H7 H -0.0909 0.6715 0.2870 0.027 Uiso 1 1 calc R . . C12 C 0.2468(4) 0.59801(14) 0.27280(12) 0.0218(4) Uani 1 1 d . . . H12A H 0.3911 0.5990 0.2368 0.026 Uiso 1 1 calc R . . H12B H 0.1952 0.5336 0.2742 0.026 Uiso 1 1 calc R . . C9 C 0.1775(4) 0.79499(14) 0.32397(11) 0.0215(4) Uani 1 1 d . . . H9 H 0.0291 0.7919 0.3589 0.026 Uiso 1 1 calc R . . C13 C -0.0310(4) 0.65411(15) 0.17612(12) 0.0254(5) Uani 1 1 d . . . C8 C 0.1222(4) 0.77505(14) 0.24711(11) 0.0225(4) Uani 1 1 d . . . H8A H 0.2646 0.7800 0.2109 0.027 Uiso 1 1 calc R . . H8B H -0.0088 0.8232 0.2318 0.027 Uiso 1 1 calc R . . H6 H 0.570(5) 0.4128(19) 0.3886(14) 0.040(7) Uiso 1 1 d . . . H2 H -0.248(5) 0.707(2) 0.1157(17) 0.050(8) Uiso 1 1 d . . . H4 H 0.488(6) 0.968(3) 0.2953(18) 0.070(10) Uiso 1 1 d . . . N30 N -0.2031(3) 0.32660(12) 0.42042(10) 0.0244(4) Uani 1 1 d . . . C34 C -0.0494(4) 0.16375(15) 0.45079(11) 0.0234(4) Uani 1 1 d . . . H34 H -0.0614 0.0975 0.4483 0.028 Uiso 1 1 calc R . . C37 C 0.4198(4) 0.03619(14) 0.47783(11) 0.0219(4) Uani 1 1 d . . . H37A H 0.5156 0.0610 0.4335 0.026 Uiso 1 1 calc R . . H37B H 0.2944 0.0037 0.4611 0.026 Uiso 1 1 calc R . . C35 C -0.2106(4) 0.23203(15) 0.42013(12) 0.0237(4) Uani 1 1 d . . . H35 H -0.3342 0.2110 0.3975 0.028 Uiso 1 1 calc R . . C33 C 0.1310(3) 0.19175(14) 0.48544(11) 0.0202(4) Uani 1 1 d . . . C36 C 0.3042(4) 0.11959(14) 0.52368(11) 0.0232(5) Uani 1 1 d . . . H36A H 0.2189 0.0935 0.5696 0.028 Uiso 1 1 calc R . . H36B H 0.4312 0.1534 0.5380 0.028 Uiso 1 1 calc R . . C32 C 0.1399(4) 0.28998(15) 0.48530(12) 0.0259(5) Uani 1 1 d . . . H32 H 0.2611 0.3130 0.5077 0.031 Uiso 1 1 calc R . . C31 C -0.0268(4) 0.35386(15) 0.45264(12) 0.0276(5) Uani 1 1 d . . . H31 H -0.0162 0.4205 0.4530 0.033 Uiso 1 1 calc R . . N16 N 0.5462(3) 0.08461(13) 0.27583(10) 0.0266(4) Uani 1 1 d . . . C25 C 0.6455(4) 0.36100(15) 0.07287(12) 0.0254(5) Uani 1 1 d . . . N22 N 0.3967(3) 0.31283(15) -0.03862(11) 0.0343(5) Uani 1 1 d . . . C18 C 0.3995(4) 0.25184(16) 0.26642(12) 0.0274(5) Uani 1 1 d . . . H18 H 0.2701 0.3012 0.2758 0.033 Uiso 1 1 calc R . . C28 C 0.7825(4) 0.38916(16) 0.13172(12) 0.0310(5) Uani 1 1 d . . . H28A H 0.8080 0.4572 0.1219 0.037 Uiso 1 1 calc R . . H28B H 0.9408 0.3498 0.1287 0.037 Uiso 1 1 calc R . . C17 C 0.3721(4) 0.15671(16) 0.28674(12) 0.0259(5) Uani 1 1 d . . . H17 H 0.2211 0.1426 0.3096 0.031 Uiso 1 1 calc R . . C19 C 0.6178(4) 0.27414(15) 0.23225(11) 0.0234(5) Uani 1 1 d . . . C23 C 0.3092(4) 0.38453(16) 0.00438(13) 0.0298(5) Uani 1 1 d . . . H23 H 0.1591 0.4196 -0.0038 0.036 Uiso 1 1 calc R . . C29 C 0.6554(4) 0.37623(16) 0.20976(12) 0.0309(5) Uani 1 1 d . . . H29A H 0.7502 0.3992 0.2451 0.037 Uiso 1 1 calc R . . H29B H 0.4986 0.4168 0.2129 0.037 Uiso 1 1 calc R . . C26 C 0.7346(4) 0.28617(17) 0.02869(13) 0.0325(5) Uani 1 1 d . . . H26 H 0.8844 0.2500 0.0355 0.039 Uiso 1 1 calc R . . C20 C 0.7976(4) 0.19847(16) 0.22104(12) 0.0282(5) Uani 1 1 d . . . H20 H 0.9499 0.2101 0.1977 0.034 Uiso 1 1 calc R . . C21 C 0.7567(4) 0.10608(16) 0.24357(12) 0.0290(5) Uani 1 1 d . . . H21 H 0.8840 0.0554 0.2358 0.035 Uiso 1 1 calc R . . C24 C 0.4248(4) 0.41065(16) 0.06022(13) 0.0292(5) Uani 1 1 d . . . H24 H 0.3542 0.4621 0.0898 0.035 Uiso 1 1 calc R . . C27 C 0.6062(4) 0.26381(19) -0.02554(13) 0.0388(6) Uani 1 1 d . . . H27 H 0.6698 0.2112 -0.0548 0.047 Uiso 1 1 calc R . . 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 C41 0.055(4) 0.073(5) 0.040(4) -0.017(4) -0.009(3) -0.005(4) C40 0.049(3) 0.050(3) 0.037(3) -0.011(3) -0.008(3) -0.010(3) C38 0.068(5) 0.083(5) 0.032(3) -0.006(3) -0.005(3) -0.019(4) C42 0.061(5) 0.060(4) 0.081(6) -0.017(4) -0.015(4) 0.009(4) C39 0.059(4) 0.063(6) 0.060(5) -0.021(5) -0.026(4) 0.023(4) C43 0.072(6) 0.029(4) 0.059(5) -0.008(4) -0.027(4) 0.018(4) C44 0.155(11) 0.190(14) 0.041(5) -0.030(8) -0.012(6) 0.050(11) C45 0.177(11) 0.066(6) 0.080(6) -0.010(5) -0.061(8) 0.021(7) O6 0.0260(8) 0.0141(7) 0.0442(9) 0.0035(6) -0.0153(7) -0.0022(6) O1 0.0387(9) 0.0275(9) 0.0413(10) -0.0118(7) -0.0154(7) -0.0011(7) O4 0.0294(8) 0.0181(8) 0.0460(10) -0.0012(7) -0.0018(7) -0.0068(6) O3 0.0307(8) 0.0152(8) 0.0538(10) -0.0028(7) -0.0080(7) -0.0006(7) O5 0.0291(9) 0.0217(8) 0.0750(13) 0.0079(8) -0.0277(8) -0.0065(7) C10 0.0246(10) 0.0156(10) 0.0335(12) -0.0011(9) -0.0106(9) -0.0039(8) C11 0.0204(10) 0.0164(10) 0.0288(11) -0.0008(8) -0.0048(8) -0.0042(8) O2 0.0527(11) 0.0459(11) 0.0454(11) -0.0159(9) -0.0332(9) 0.0161(9) C14 0.0258(11) 0.0192(11) 0.0264(11) 0.0017(8) -0.0097(9) -0.0043(9) C15 0.0248(11) 0.0161(10) 0.0295(11) 0.0011(8) -0.0065(9) -0.0036(8) C7 0.0206(10) 0.0185(10) 0.0289(11) -0.0025(9) -0.0061(8) -0.0020(8) C12 0.0206(10) 0.0143(10) 0.0319(11) -0.0024(8) -0.0072(8) -0.0025(8) C9 0.0225(10) 0.0140(10) 0.0290(11) -0.0018(8) -0.0055(8) -0.0032(8) C13 0.0219(10) 0.0233(11) 0.0326(12) -0.0032(9) -0.0068(9) -0.0044(9) C8 0.0244(10) 0.0152(10) 0.0281(11) -0.0001(8) -0.0075(8) 0.0002(8) N30 0.0241(9) 0.0194(9) 0.0307(10) 0.0014(7) -0.0082(7) -0.0027(7) C34 0.0241(10) 0.0179(10) 0.0288(11) -0.0009(8) -0.0053(8) -0.0034(8) C37 0.0224(10) 0.0167(10) 0.0283(11) 0.0003(8) -0.0100(8) -0.0026(8) C35 0.0212(10) 0.0212(11) 0.0303(11) -0.0023(9) -0.0062(8) -0.0047(8) C33 0.0193(10) 0.0182(10) 0.0223(10) -0.0025(8) -0.0001(8) -0.0014(8) C36 0.0236(10) 0.0199(11) 0.0267(11) -0.0001(9) -0.0086(8) -0.0004(8) C32 0.0226(10) 0.0212(11) 0.0361(12) -0.0040(9) -0.0093(9) -0.0048(8) C31 0.0283(11) 0.0179(11) 0.0373(12) -0.0012(9) -0.0065(9) -0.0039(9) N16 0.0303(10) 0.0231(10) 0.0282(10) 0.0023(8) -0.0072(8) -0.0078(8) C25 0.0272(11) 0.0234(11) 0.0270(11) 0.0057(9) -0.0028(9) -0.0125(9) N22 0.0310(10) 0.0409(12) 0.0328(11) -0.0001(9) -0.0103(8) -0.0062(9) C18 0.0273(11) 0.0251(11) 0.0297(12) -0.0032(9) -0.0059(9) -0.0001(9) C28 0.0373(13) 0.0245(12) 0.0353(13) 0.0029(10) -0.0092(10) -0.0169(10) C17 0.0228(11) 0.0297(12) 0.0267(11) 0.0012(9) -0.0040(8) -0.0092(9) C19 0.0310(11) 0.0223(11) 0.0203(10) -0.0008(8) -0.0095(8) -0.0091(9) C23 0.0242(11) 0.0289(12) 0.0367(13) 0.0092(10) -0.0083(9) -0.0067(9) C29 0.0420(13) 0.0220(11) 0.0322(12) -0.0035(9) -0.0078(10) -0.0125(10) C26 0.0291(12) 0.0361(13) 0.0329(12) -0.0014(10) -0.0110(10) 0.0002(10) C20 0.0239(11) 0.0300(12) 0.0315(12) 0.0029(9) -0.0034(9) -0.0084(9) C21 0.0273(11) 0.0248(12) 0.0334(12) 0.0013(9) -0.0047(9) 0.0017(9) C24 0.0325(12) 0.0207(11) 0.0340(12) 0.0026(9) -0.0004(9) -0.0073(9) C27 0.0384(14) 0.0450(15) 0.0338(13) -0.0125(11) -0.0106(11) 0.0027(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C41 C42 1.360(11) . ? C41 C40 1.364(10) . ? C41 H41 0.9500 . ? C40 C39 1.396(10) . ? C40 H40 0.9500 . ? C38 C43 1.335(11) . ? C38 C39 1.372(10) . ? C38 C44 1.490(12) . ? C42 C43 1.437(12) . ? C42 H42 0.9500 . ? C39 H39 0.9500 . ? C43 C45 1.518(11) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? O6 C15 1.319(2) . ? O6 H6 0.89(3) . ? O1 C13 1.204(3) . ? O4 C14 1.320(3) . ? O4 H4 0.95(4) . ? O3 C14 1.204(3) . ? O5 C15 1.208(3) . ? C10 C9 1.526(3) . ? C10 C11 1.528(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C15 1.513(3) . ? C11 C12 1.534(3) . ? C11 H11 1.0000 . ? O2 C13 1.312(3) . ? O2 H2 0.87(3) . ? C14 C9 1.520(3) . ? C7 C13 1.511(3) . ? C7 C12 1.525(3) . ? C7 C8 1.537(3) . ? C7 H7 1.0000 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C9 C8 1.531(3) . ? C9 H9 1.0000 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? N30 C31 1.338(3) . ? N30 C35 1.340(3) . ? C34 C35 1.374(3) . ? C34 C33 1.387(3) . ? C34 H34 0.9500 . ? C37 C36 1.520(3) . ? C37 C37 1.529(4) 2_656 ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C35 H35 0.9500 . ? C33 C32 1.392(3) . ? C33 C36 1.512(3) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C32 C31 1.377(3) . ? C32 H32 0.9500 . ? C31 H31 0.9500 . ? N16 C17 1.326(3) . ? N16 C21 1.335(3) . ? C25 C26 1.377(3) . ? C25 C24 1.390(3) . ? C25 C28 1.510(3) . ? N22 C23 1.329(3) . ? N22 C27 1.334(3) . ? C18 C19 1.389(3) . ? C18 C17 1.389(3) . ? C18 H18 0.9500 . ? C28 C29 1.530(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C17 H17 0.9500 . ? C19 C20 1.381(3) . ? C19 C29 1.504(3) . ? C23 C24 1.378(3) . ? C23 H23 0.9500 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C26 C27 1.381(3) . ? C26 H26 0.9500 . ? C20 C21 1.379(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C24 H24 0.9500 . ? C27 H27 0.9500 . ? 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 _geom_angle_publ_flag C42 C41 C40 120.7(7) . . ? C42 C41 H41 119.7 . . ? C40 C41 H41 119.7 . . ? C41 C40 C39 118.6(7) . . ? C41 C40 H40 120.7 . . ? C39 C40 H40 120.7 . . ? C43 C38 C39 118.7(9) . . ? C43 C38 C44 121.0(9) . . ? C39 C38 C44 120.3(9) . . ? C41 C42 C43 119.0(8) . . ? C41 C42 H42 120.5 . . ? C43 C42 H42 120.5 . . ? C38 C39 C40 122.0(8) . . ? C38 C39 H39 119.0 . . ? C40 C39 H39 119.0 . . ? C38 C43 C42 120.5(9) . . ? C38 C43 C45 122.0(9) . . ? C42 C43 C45 116.9(8) . . ? C38 C44 H44A 109.5 . . ? C38 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C38 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 H45A 109.5 . . ? C43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C15 O6 H6 111.1(17) . . ? C14 O4 H4 107(2) . . ? C9 C10 C11 111.75(16) . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C15 C11 C10 110.72(16) . . ? C15 C11 C12 111.10(16) . . ? C10 C11 C12 111.25(16) . . ? C15 C11 H11 107.9 . . ? C10 C11 H11 107.9 . . ? C12 C11 H11 107.9 . . ? C13 O2 H2 110.5(19) . . ? O3 C14 O4 123.48(19) . . ? O3 C14 C9 122.90(19) . . ? O4 C14 C9 113.59(18) . . ? O5 C15 O6 123.15(18) . . ? O5 C15 C11 124.24(18) . . ? O6 C15 C11 112.62(17) . . ? C13 C7 C12 112.88(17) . . ? C13 C7 C8 111.74(17) . . ? C12 C7 C8 110.99(16) . . ? C13 C7 H7 107.0 . . ? C12 C7 H7 107.0 . . ? C8 C7 H7 107.0 . . ? C7 C12 C11 110.12(16) . . ? C7 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? C7 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.2 . . ? C14 C9 C10 112.87(16) . . ? C14 C9 C8 108.86(16) . . ? C10 C9 C8 111.21(16) . . ? C14 C9 H9 107.9 . . ? C10 C9 H9 107.9 . . ? C8 C9 H9 107.9 . . ? O1 C13 O2 123.5(2) . . ? O1 C13 C7 124.70(19) . . ? O2 C13 C7 111.77(18) . . ? C9 C8 C7 109.54(16) . . ? C9 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? C9 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C31 N30 C35 116.77(17) . . ? C35 C34 C33 119.86(19) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C36 C37 C37 111.3(2) . 2_656 ? C36 C37 H37A 109.4 . . ? C37 C37 H37A 109.4 2_656 . ? C36 C37 H37B 109.4 . . ? C37 C37 H37B 109.4 2_656 . ? H37A C37 H37B 108.0 . . ? N30 C35 C34 123.55(19) . . ? N30 C35 H35 118.2 . . ? C34 C35 H35 118.2 . . ? C34 C33 C32 116.60(18) . . ? C34 C33 C36 121.81(18) . . ? C32 C33 C36 121.56(18) . . ? C33 C36 C37 114.78(16) . . ? C33 C36 H36A 108.6 . . ? C37 C36 H36A 108.6 . . ? C33 C36 H36B 108.6 . . ? C37 C36 H36B 108.6 . . ? H36A C36 H36B 107.5 . . ? C31 C32 C33 120.02(19) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? N30 C31 C32 123.2(2) . . ? N30 C31 H31 118.4 . . ? C32 C31 H31 118.4 . . ? C17 N16 C21 117.35(19) . . ? C26 C25 C24 117.1(2) . . ? C26 C25 C28 121.7(2) . . ? C24 C25 C28 121.3(2) . . ? C23 N22 C27 117.2(2) . . ? C19 C18 C17 119.4(2) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C25 C28 C29 113.07(18) . . ? C25 C28 H28A 109.0 . . ? C29 C28 H28A 109.0 . . ? C25 C28 H28B 109.0 . . ? C29 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? N16 C17 C18 123.2(2) . . ? N16 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C20 C19 C18 116.79(19) . . ? C20 C19 C29 122.1(2) . . ? C18 C19 C29 121.1(2) . . ? N22 C23 C24 123.4(2) . . ? N22 C23 H23 118.3 . . ? C24 C23 H23 118.3 . . ? C19 C29 C28 113.72(18) . . ? C19 C29 H29A 108.8 . . ? C28 C29 H29A 108.8 . . ? C19 C29 H29B 108.8 . . ? C28 C29 H29B 108.8 . . ? H29A C29 H29B 107.7 . . ? C25 C26 C27 120.0(2) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C21 C20 C19 120.2(2) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? N16 C21 C20 122.9(2) . . ? N16 C21 H21 118.5 . . ? C20 C21 H21 118.5 . . ? C23 C24 C25 119.4(2) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? N22 C27 C26 122.9(2) . . ? N22 C27 H27 118.6 . . ? C26 C27 H27 118.6 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.76 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.380 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.059 # Attachment 'cocrystal_5d.cif' data_5d _database_code_depnum_ccdc_archive 'CCDC 681090' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1,2-bis(4-pyridyl)ethane - 1,4-bis(4-pyridyl)butane - o-chlorotoluene ; _chemical_melting_point ? _chemical_formula_moiety (C14H16N2),2(C9H12O6),2(C12H12N2),(C7H7Cl) _chemical_formula_sum 'C63 H71 Cl N6 O12' _chemical_formula_weight 1139.71 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7053(5) _cell_length_b 14.1098(13) _cell_length_c 18.2660(16) _cell_angle_alpha 86.0620(10) _cell_angle_beta 83.1300(10) _cell_angle_gamma 81.9200(10) _cell_volume 1443.4(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8110 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.16 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9292 _exptl_absorpt_correction_T_max 0.9721 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20347 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.71 _reflns_number_total 5474 _reflns_number_gt 4431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+0.8262P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5474 _refine_ls_number_parameters 427 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_gt 0.1283 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O6 O 0.4446(2) 0.45565(9) 0.37872(8) 0.0269(3) Uani 1 1 d . . . O4 O 0.4665(2) 0.90153(10) 0.29940(8) 0.0312(3) Uani 1 1 d . . . O3 O 0.0957(2) 0.96439(9) 0.33769(8) 0.0324(3) Uani 1 1 d . . . O1 O 0.0471(3) 0.58545(10) 0.14026(8) 0.0362(4) Uani 1 1 d . . . N30 N -0.2047(3) 0.32637(11) 0.42055(8) 0.0232(3) Uani 1 1 d . . . N16 N 0.5434(3) 0.08337(11) 0.27493(9) 0.0266(4) Uani 1 1 d . . . C15 C 0.5000(3) 0.54361(13) 0.37488(10) 0.0222(4) Uani 1 1 d . . . O5 O 0.6899(2) 0.56237(10) 0.38975(9) 0.0387(4) Uani 1 1 d . . . C10 C 0.3695(3) 0.71883(12) 0.35097(10) 0.0224(4) Uani 1 1 d . . . H10A H 0.3946 0.7314 0.4019 0.027 Uiso 1 1 calc R . . H10B H 0.5208 0.7234 0.3190 0.027 Uiso 1 1 calc R . . C14 C 0.2404(3) 0.89547(13) 0.32204(10) 0.0226(4) Uani 1 1 d . . . C35 C -0.2122(3) 0.23219(13) 0.42007(10) 0.0229(4) Uani 1 1 d . . . H35 H -0.3360 0.2114 0.3973 0.028 Uiso 1 1 calc R . . C34 C -0.0508(3) 0.16355(13) 0.45069(10) 0.0220(4) Uani 1 1 d . . . H34 H -0.0626 0.0974 0.4481 0.026 Uiso 1 1 calc R . . C11 C 0.3033(3) 0.61774(12) 0.34975(10) 0.0206(4) Uani 1 1 d . . . H11 H 0.1574 0.6133 0.3854 0.025 Uiso 1 1 calc R . . O2 O -0.2087(3) 0.71834(12) 0.15722(9) 0.0455(4) Uani 1 1 d . . . C36 C 0.3039(3) 0.11978(12) 0.52377(10) 0.0219(4) Uani 1 1 d . . . H36A H 0.2187 0.0940 0.5696 0.026 Uiso 1 1 calc R . . H36B H 0.4310 0.1534 0.5382 0.026 Uiso 1 1 calc R . . N22 N 0.4029(3) 0.31510(14) -0.03928(10) 0.0366(4) Uani 1 1 d . . . C17 C 0.3697(3) 0.15604(14) 0.28653(10) 0.0266(4) Uani 1 1 d . . . H17 H 0.2188 0.1424 0.3094 0.032 Uiso 1 1 calc R . . C18 C 0.3983(3) 0.25045(14) 0.26690(10) 0.0266(4) Uani 1 1 d . . . H18 H 0.2694 0.3000 0.2767 0.032 Uiso 1 1 calc R . . C12 C 0.2443(3) 0.59735(12) 0.27301(10) 0.0214(4) Uani 1 1 d . . . H12A H 0.3882 0.5980 0.2369 0.026 Uiso 1 1 calc R . . H12B H 0.1926 0.5331 0.2745 0.026 Uiso 1 1 calc R . . C37 C 0.4198(3) 0.03596(12) 0.47778(10) 0.0207(4) Uani 1 1 d . . . H37A H 0.5154 0.0604 0.4335 0.025 Uiso 1 1 calc R . . H37B H 0.2944 0.0034 0.4610 0.025 Uiso 1 1 calc R . . C13 C -0.0344(3) 0.65295(13) 0.17638(11) 0.0251(4) Uani 1 1 d . . . C25 C 0.6497(3) 0.36119(14) 0.07391(10) 0.0258(4) Uani 1 1 d . . . C33 C 0.1305(3) 0.19210(12) 0.48561(9) 0.0197(4) Uani 1 1 d . . . C9 C 0.1755(3) 0.79469(12) 0.32417(10) 0.0207(4) Uani 1 1 d . . . H9 H 0.0276 0.7920 0.3592 0.025 Uiso 1 1 calc R . . C7 C 0.0463(3) 0.67328(12) 0.24895(10) 0.0218(4) Uani 1 1 d . . . H7 H -0.0937 0.6712 0.2873 0.026 Uiso 1 1 calc R . . C32 C 0.1402(3) 0.28968(13) 0.48545(10) 0.0242(4) Uani 1 1 d . . . H32 H 0.2622 0.3125 0.5077 0.029 Uiso 1 1 calc R . . C31 C -0.0279(3) 0.35385(13) 0.45284(11) 0.0254(4) Uani 1 1 d . . . H31 H -0.0176 0.4204 0.4533 0.030 Uiso 1 1 calc R . . C28 C 0.7852(4) 0.38818(14) 0.13362(11) 0.0302(4) Uani 1 1 d . . . H28A H 0.8111 0.4561 0.1247 0.036 Uiso 1 1 calc R . . H28B H 0.9434 0.3486 0.1307 0.036 Uiso 1 1 calc R . . C19 C 0.6166(3) 0.27253(13) 0.23277(10) 0.0234(4) Uani 1 1 d . . . C23 C 0.3139(4) 0.38571(15) 0.00473(12) 0.0316(5) Uani 1 1 d . . . H23 H 0.1636 0.4208 -0.0034 0.038 Uiso 1 1 calc R . . C8 C 0.1189(3) 0.77416(12) 0.24728(10) 0.0226(4) Uani 1 1 d . . . H8A H 0.2608 0.7788 0.2109 0.027 Uiso 1 1 calc R . . H8B H -0.0124 0.8222 0.2320 0.027 Uiso 1 1 calc R . . C29 C 0.6568(4) 0.37458(14) 0.21137(11) 0.0306(4) Uani 1 1 d . . . H29A H 0.7516 0.3965 0.2474 0.037 Uiso 1 1 calc R . . H29B H 0.5007 0.4157 0.2146 0.037 Uiso 1 1 calc R . . C21 C 0.7537(3) 0.10432(14) 0.24244(11) 0.0299(4) Uani 1 1 d . . . H21 H 0.8802 0.0534 0.2341 0.036 Uiso 1 1 calc R . . C20 C 0.7955(3) 0.19622(14) 0.22057(11) 0.0286(4) Uani 1 1 d . . . H20 H 0.9475 0.2074 0.1970 0.034 Uiso 1 1 calc R . . C24 C 0.4284(4) 0.41090(14) 0.06167(11) 0.0297(4) Uani 1 1 d . . . H24 H 0.3568 0.4615 0.0920 0.036 Uiso 1 1 calc R . . C26 C 0.7406(4) 0.28722(17) 0.02850(12) 0.0357(5) Uani 1 1 d . . . H26 H 0.8907 0.2510 0.0352 0.043 Uiso 1 1 calc R . . C27 C 0.6135(4) 0.26600(19) -0.02651(13) 0.0441(6) Uani 1 1 d . . . H27 H 0.6784 0.2143 -0.0566 0.053 Uiso 1 1 calc R . . Cl45 Cl 0.7452(19) 0.9702(8) -0.1049(5) 0.143(4) Uani 0.25 1 d P A -1 Cl46 Cl 0.6886(9) 0.8957(6) -0.1003(2) 0.124(2) Uani 0.25 1 d P A -1 C38 C 0.5675(9) 0.9610(6) -0.0239(3) 0.097(4) Uani 0.50 1 d PD A -1 C44 C 0.214(3) 1.0553(6) -0.0786(5) 0.126(4) Uani 0.50 1 d P A -1 H44A H 0.3169 1.0431 -0.1248 0.189 Uiso 0.50 1 calc PR A -1 H44B H 0.1599 1.1242 -0.0763 0.189 Uiso 0.50 1 calc PR A -1 H44C H 0.0760 1.0207 -0.0766 0.189 Uiso 0.50 1 calc PR A -1 C39 C 0.6694(14) 0.9334(7) 0.0410(4) 0.092(3) Uani 0.50 1 d PD A -1 H39A H 0.8265 0.8998 0.0358 0.110 Uiso 0.50 1 calc PR A -1 C42 C 0.2339(19) 1.0316(7) 0.0571(4) 0.103(3) Uani 0.50 1 d PD A -1 H42A H 0.0673 1.0522 0.0641 0.123 Uiso 0.50 1 calc PR A -1 C40 C 0.5712(9) 0.9488(4) 0.1092(3) 0.0498(13) Uani 0.50 1 d PD A -1 H40A H 0.6396 0.9189 0.1513 0.060 Uiso 0.50 1 calc PR A -1 C43 C 0.3532(16) 1.0211(5) -0.0135(5) 0.103(4) Uani 0.50 1 d PD A -1 C41 C 0.3604(15) 1.0120(11) 0.1148(6) 0.086(5) Uani 0.50 1 d PD A -1 H41A H 0.3054 1.0415 0.1600 0.104 Uiso 0.50 1 calc PR A -1 H6 H 0.568(5) 0.410(2) 0.3931(15) 0.059(8) Uiso 1 1 d . . . H4 H 0.485(5) 0.965(2) 0.2942(15) 0.060(8) Uiso 1 1 d . . . H2 H -0.264(6) 0.701(2) 0.1128(19) 0.079(10) Uiso 1 1 d . . . 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 O6 0.0240(7) 0.0162(6) 0.0421(8) 0.0040(6) -0.0140(6) -0.0018(5) O4 0.0275(7) 0.0202(7) 0.0459(9) 0.0004(6) -0.0010(6) -0.0065(6) O3 0.0292(7) 0.0181(7) 0.0498(9) -0.0039(6) -0.0067(6) 0.0003(6) O1 0.0422(9) 0.0298(8) 0.0402(8) -0.0116(7) -0.0173(7) -0.0020(6) N30 0.0198(8) 0.0215(8) 0.0280(8) 0.0015(6) -0.0057(6) -0.0007(6) N16 0.0281(8) 0.0251(8) 0.0281(8) 0.0025(7) -0.0077(7) -0.0067(7) C15 0.0212(9) 0.0187(9) 0.0270(9) 0.0010(7) -0.0060(7) -0.0014(7) O5 0.0263(7) 0.0241(7) 0.0695(11) 0.0073(7) -0.0243(7) -0.0053(6) C10 0.0220(9) 0.0173(9) 0.0297(10) -0.0008(7) -0.0106(7) -0.0025(7) C14 0.0257(9) 0.0200(9) 0.0232(9) 0.0003(7) -0.0089(7) -0.0023(7) C35 0.0208(9) 0.0220(9) 0.0270(9) -0.0008(7) -0.0071(7) -0.0030(7) C34 0.0207(9) 0.0173(9) 0.0285(9) -0.0007(7) -0.0052(7) -0.0024(7) C11 0.0182(8) 0.0182(9) 0.0257(9) -0.0003(7) -0.0055(7) -0.0017(7) O2 0.0443(9) 0.0508(10) 0.0426(9) -0.0137(8) -0.0289(8) 0.0150(8) C36 0.0214(9) 0.0203(9) 0.0244(9) -0.0006(7) -0.0078(7) 0.0000(7) N22 0.0293(9) 0.0520(11) 0.0306(9) 0.0013(8) -0.0111(7) -0.0081(8) C17 0.0219(9) 0.0326(10) 0.0261(9) 0.0010(8) -0.0026(7) -0.0076(8) C18 0.0267(10) 0.0260(10) 0.0270(10) -0.0032(8) -0.0051(8) 0.0000(8) C12 0.0201(9) 0.0169(8) 0.0282(9) -0.0020(7) -0.0071(7) -0.0018(7) C37 0.0180(9) 0.0199(9) 0.0249(9) -0.0001(7) -0.0074(7) -0.0009(7) C13 0.0220(9) 0.0249(10) 0.0306(10) -0.0006(8) -0.0077(7) -0.0071(7) C25 0.0264(10) 0.0279(10) 0.0251(9) 0.0066(8) -0.0036(7) -0.0135(8) C33 0.0169(8) 0.0208(9) 0.0206(8) -0.0021(7) -0.0005(7) -0.0004(7) C9 0.0189(9) 0.0177(9) 0.0254(9) -0.0009(7) -0.0038(7) -0.0013(7) C7 0.0180(9) 0.0215(9) 0.0267(9) -0.0013(7) -0.0070(7) -0.0014(7) C32 0.0207(9) 0.0228(9) 0.0310(10) -0.0037(8) -0.0086(7) -0.0035(7) C31 0.0241(9) 0.0189(9) 0.0338(10) -0.0005(8) -0.0064(8) -0.0032(7) C28 0.0372(11) 0.0276(10) 0.0298(10) 0.0028(8) -0.0087(8) -0.0164(8) C19 0.0297(10) 0.0243(9) 0.0183(8) -0.0005(7) -0.0078(7) -0.0072(8) C23 0.0254(10) 0.0322(11) 0.0380(11) 0.0105(9) -0.0085(8) -0.0087(8) C8 0.0226(9) 0.0182(9) 0.0270(9) -0.0001(7) -0.0073(7) 0.0001(7) C29 0.0407(12) 0.0249(10) 0.0290(10) -0.0019(8) -0.0075(9) -0.0110(8) C21 0.0260(10) 0.0281(10) 0.0343(11) 0.0029(8) -0.0054(8) 0.0005(8) C20 0.0208(9) 0.0332(11) 0.0321(10) 0.0024(8) -0.0035(8) -0.0061(8) C24 0.0303(10) 0.0242(10) 0.0349(11) 0.0034(8) -0.0019(8) -0.0082(8) C26 0.0252(10) 0.0495(13) 0.0330(11) -0.0063(10) -0.0097(8) 0.0004(9) C27 0.0333(12) 0.0630(16) 0.0370(12) -0.0179(11) -0.0102(9) 0.0023(11) Cl45 0.179(8) 0.140(6) 0.099(6) -0.049(5) 0.087(7) -0.055(6) Cl46 0.063(2) 0.257(8) 0.052(2) -0.061(4) -0.0061(19) 0.001(4) C38 0.067(4) 0.218(11) 0.028(3) -0.035(5) 0.006(3) -0.094(6) C44 0.259(15) 0.060(5) 0.072(5) 0.009(4) -0.085(8) -0.017(7) C39 0.062(4) 0.132(9) 0.078(6) -0.040(6) -0.022(4) 0.024(5) C42 0.137(8) 0.115(7) 0.048(4) -0.038(5) 0.004(6) 0.016(6) C40 0.055(3) 0.066(4) 0.035(3) -0.009(2) -0.012(2) -0.022(3) C43 0.193(11) 0.036(4) 0.089(6) 0.002(4) -0.071(8) 0.003(5) C41 0.044(4) 0.174(13) 0.037(4) -0.038(5) -0.023(4) 0.030(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O6 C15 1.319(2) . ? O6 H6 0.93(3) . ? O4 C14 1.319(2) . ? O4 H4 0.92(3) . ? O3 C14 1.210(2) . ? O1 C13 1.203(2) . ? N30 C35 1.336(2) . ? N30 C31 1.342(2) . ? N16 C17 1.331(2) . ? N16 C21 1.336(3) . ? C15 O5 1.216(2) . ? C15 C11 1.514(2) . ? C10 C9 1.528(2) . ? C10 C11 1.528(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C14 C9 1.516(2) . ? C35 C34 1.378(2) . ? C35 H35 0.9500 . ? C34 C33 1.396(2) . ? C34 H34 0.9500 . ? C11 C12 1.535(2) . ? C11 H11 1.0000 . ? O2 C13 1.321(2) . ? O2 H2 0.96(3) . ? C36 C33 1.513(2) . ? C36 C37 1.525(2) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? N22 C23 1.329(3) . ? N22 C27 1.338(3) . ? C17 C18 1.382(3) . ? C17 H17 0.9500 . ? C18 C19 1.391(3) . ? C18 H18 0.9500 . ? C12 C7 1.527(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C37 C37 1.526(3) 2_656 ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C13 C7 1.512(2) . ? C25 C26 1.382(3) . ? C25 C24 1.390(3) . ? C25 C28 1.508(3) . ? C33 C32 1.385(3) . ? C9 C8 1.533(2) . ? C9 H9 1.0000 . ? C7 C8 1.535(2) . ? C7 H7 1.0000 . ? C32 C31 1.383(3) . ? C32 H32 0.9500 . ? C31 H31 0.9500 . ? C28 C29 1.531(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C19 C20 1.386(3) . ? C19 C29 1.508(3) . ? C23 C24 1.383(3) . ? C23 H23 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C21 C20 1.375(3) . ? C21 H21 0.9500 . ? C20 H20 0.9500 . ? C24 H24 0.9500 . ? C26 C27 1.379(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? Cl45 C38 1.699(8) . ? Cl46 C38 1.743(8) . ? C38 C43 1.387(2) . ? C38 C39 1.391(2) . ? C44 C43 1.521(11) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C39 C40 1.322(9) . ? C39 H39A 0.9500 . ? C42 C41 1.340(14) . ? C42 C43 1.391(2) . ? C42 H42A 0.9500 . ? C40 C41 1.390(2) . ? C40 H40A 0.9500 . ? C41 H41A 0.9500 . ? 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 _geom_angle_publ_flag C15 O6 H6 112.3(17) . . ? C14 O4 H4 107.8(17) . . ? C35 N30 C31 116.95(15) . . ? C17 N16 C21 117.34(16) . . ? O5 C15 O6 123.13(16) . . ? O5 C15 C11 124.06(16) . . ? O6 C15 C11 112.81(15) . . ? C9 C10 C11 111.65(14) . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? O3 C14 O4 123.21(17) . . ? O3 C14 C9 122.79(16) . . ? O4 C14 C9 113.96(15) . . ? N30 C35 C34 123.74(16) . . ? N30 C35 H35 118.1 . . ? C34 C35 H35 118.1 . . ? C35 C34 C33 119.37(16) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? C15 C11 C10 110.79(14) . . ? C15 C11 C12 110.97(14) . . ? C10 C11 C12 111.33(14) . . ? C15 C11 H11 107.9 . . ? C10 C11 H11 107.9 . . ? C12 C11 H11 107.9 . . ? C13 O2 H2 109.8(19) . . ? C33 C36 C37 114.98(14) . . ? C33 C36 H36A 108.5 . . ? C37 C36 H36A 108.5 . . ? C33 C36 H36B 108.5 . . ? C37 C36 H36B 108.5 . . ? H36A C36 H36B 107.5 . . ? C23 N22 C27 117.30(18) . . ? N16 C17 C18 123.18(17) . . ? N16 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C17 C18 C19 119.67(17) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C7 C12 C11 109.86(14) . . ? C7 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? C7 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C36 C37 C37 111.20(18) . 2_656 ? C36 C37 H37A 109.4 . . ? C37 C37 H37A 109.4 2_656 . ? C36 C37 H37B 109.4 . . ? C37 C37 H37B 109.4 2_656 . ? H37A C37 H37B 108.0 . . ? O1 C13 O2 123.51(18) . . ? O1 C13 C7 124.81(17) . . ? O2 C13 C7 111.68(16) . . ? C26 C25 C24 117.18(18) . . ? C26 C25 C28 121.73(18) . . ? C24 C25 C28 121.09(18) . . ? C32 C33 C34 116.96(16) . . ? C32 C33 C36 121.62(16) . . ? C34 C33 C36 121.39(16) . . ? C14 C9 C10 112.83(14) . . ? C14 C9 C8 108.91(14) . . ? C10 C9 C8 111.08(14) . . ? C14 C9 H9 108.0 . . ? C10 C9 H9 108.0 . . ? C8 C9 H9 108.0 . . ? C13 C7 C12 112.58(15) . . ? C13 C7 C8 111.76(15) . . ? C12 C7 C8 111.10(14) . . ? C13 C7 H7 107.0 . . ? C12 C7 H7 107.0 . . ? C8 C7 H7 107.0 . . ? C31 C32 C33 119.97(17) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? N30 C31 C32 122.99(17) . . ? N30 C31 H31 118.5 . . ? C32 C31 H31 118.5 . . ? C25 C28 C29 113.17(16) . . ? C25 C28 H28A 108.9 . . ? C29 C28 H28A 108.9 . . ? C25 C28 H28B 108.9 . . ? C29 C28 H28B 108.9 . . ? H28A C28 H28B 107.8 . . ? C20 C19 C18 116.61(17) . . ? C20 C19 C29 121.90(17) . . ? C18 C19 C29 121.48(17) . . ? N22 C23 C24 123.52(19) . . ? N22 C23 H23 118.2 . . ? C24 C23 H23 118.2 . . ? C9 C8 C7 109.60(14) . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C19 C29 C28 113.90(16) . . ? C19 C29 H29A 108.8 . . ? C28 C29 H29A 108.8 . . ? C19 C29 H29B 108.8 . . ? C28 C29 H29B 108.8 . . ? H29A C29 H29B 107.7 . . ? N16 C21 C20 122.96(18) . . ? N16 C21 H21 118.5 . . ? C20 C21 H21 118.5 . . ? C21 C20 C19 120.23(17) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C23 C24 C25 119.15(19) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C27 C26 C25 120.01(19) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? N22 C27 C26 122.8(2) . . ? N22 C27 H27 118.6 . . ? C26 C27 H27 118.6 . . ? C43 C38 C39 113.8(8) . . ? C43 C38 Cl45 119.4(7) . . ? C39 C38 Cl45 119.7(6) . . ? C43 C38 Cl46 129.0(6) . . ? C39 C38 Cl46 115.5(6) . . ? Cl45 C38 Cl46 38.5(3) . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C40 C39 C38 127.0(7) . . ? C40 C39 H39A 116.5 . . ? C38 C39 H39A 116.5 . . ? C41 C42 C43 118.2(9) . . ? C41 C42 H42A 120.9 . . ? C43 C42 H42A 120.9 . . ? C39 C40 C41 115.1(7) . . ? C39 C40 H40A 122.4 . . ? C41 C40 H40A 122.4 . . ? C38 C43 C42 120.1(8) . . ? C38 C43 C44 120.5(8) . . ? C42 C43 C44 117.5(8) . . ? C42 C41 C40 120.7(8) . . ? C42 C41 H41A 119.7 . . ? C40 C41 H41A 119.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.71 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.541 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.055 # Attachment 'cocrystal_5e.cif' data_5e _database_code_depnum_ccdc_archive 'CCDC 681091' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1,2-bis(4-pyridyl)ethane - 1,4-bis(4-pyridyl)butane - o-dichlorobenzene ; _chemical_melting_point ? _chemical_formula_moiety (C9H12O6),(C12H12N2),0.5(C14H16N2),0.5(C6H4Cl2) _chemical_formula_sum 'C31 H34 Cl N3 O6' _chemical_formula_weight 580.06 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6867(3) _cell_length_b 14.0676(8) _cell_length_c 18.3545(10) _cell_angle_alpha 88.4000(10) _cell_angle_beta 86.0400(10) _cell_angle_gamma 81.1640(10) _cell_volume 1447.21(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8831 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 28.20 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9166 _exptl_absorpt_correction_T_max 0.9664 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19187 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 26.36 _reflns_number_total 5886 _reflns_number_gt 5179 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+1.1083P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5886 _refine_ls_number_parameters 475 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1454 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O4 O 0.9216(2) 0.45751(9) 0.38426(8) 0.0318(3) Uani 1 1 d . . . H4 H 1.0401 0.4186 0.3965 0.048 Uiso 1 1 calc R . . O5 O 1.1758(3) 0.56281(10) 0.38761(9) 0.0437(4) Uani 1 1 d . . . O8 O 0.5444(3) 0.57658(10) 0.13195(8) 0.0390(3) Uani 1 1 d . . . N1 N 0.2772(3) 0.32797(11) 0.42839(8) 0.0284(3) Uani 1 1 d . . . C36 C 0.4379(3) 0.63829(13) 0.17143(10) 0.0290(4) Uani 1 1 d . . . C16 C 0.9157(3) 0.03660(12) 0.47897(10) 0.0271(4) Uani 1 1 d . . . H16A H 1.0049 0.0614 0.4362 0.033 Uiso 1 1 calc R . . H16B H 0.7882 0.0047 0.4608 0.033 Uiso 1 1 calc R . . C35 C 0.9817(3) 0.54427(12) 0.37506(10) 0.0265(4) Uani 1 1 d . . . C29 C 0.7824(3) 0.61664(12) 0.34693(9) 0.0241(4) Uani 1 1 d . . . H29 H 0.6377 0.6152 0.3809 0.029 Uiso 1 1 calc R . . C31 C 0.5161(3) 0.66275(12) 0.24488(9) 0.0252(4) Uani 1 1 d . . . H31 H 0.3773 0.6623 0.2813 0.030 Uiso 1 1 calc R . . C12 C 0.6235(3) 0.19291(12) 0.49073(10) 0.0268(4) Uani 1 1 d . . . C10 C 0.2652(3) 0.23343(13) 0.42832(11) 0.0310(4) Uani 1 1 d . . . H10 H 0.1347 0.2129 0.4068 0.037 Uiso 1 1 calc R . . C11 C 0.4332(3) 0.16451(13) 0.45797(11) 0.0301(4) Uani 1 1 d . . . H11 H 0.4188 0.0983 0.4560 0.036 Uiso 1 1 calc R . . C13 C 0.6370(3) 0.29045(13) 0.49022(11) 0.0313(4) Uani 1 1 d . . . H13 H 0.7650 0.3130 0.5116 0.038 Uiso 1 1 calc R . . C30 C 0.7208(3) 0.58975(12) 0.27074(10) 0.0247(4) Uani 1 1 d . . . H30A H 0.8622 0.5889 0.2360 0.030 Uiso 1 1 calc R . . H30B H 0.6744 0.5247 0.2727 0.030 Uiso 1 1 calc R . . C15 C 0.8042(4) 0.11990(14) 0.52705(11) 0.0336(4) Uani 1 1 d . . . H15A H 0.7255 0.0938 0.5713 0.040 Uiso 1 1 calc R . . H15B H 0.9328 0.1531 0.5429 0.040 Uiso 1 1 calc R . . C32 C 0.5821(4) 0.76464(12) 0.24214(10) 0.0311(4) Uani 1 1 d . . . H32A H 0.7197 0.7674 0.2064 0.037 Uiso 1 1 calc R . . H32B H 0.4459 0.8111 0.2260 0.037 Uiso 1 1 calc R . . N2 N -0.0606(3) 0.33300(13) -0.03105(9) 0.0388(4) Uani 1 1 d . B . C22 C 0.2144(4) 0.35712(14) 0.22633(11) 0.0345(4) Uani 1 1 d . . . H22A H 0.0779 0.4101 0.2288 0.041 Uiso 1 1 calc R A 1 H22B H 0.3197 0.3671 0.2653 0.041 Uiso 1 1 calc R A 1 O9 O 0.2382(3) 0.69282(12) 0.15548(9) 0.0496(4) Uani 1 1 d . . . H9 H 0.1946 0.6753 0.1158 0.074 Uiso 1 1 calc R . . C34 C 0.8450(4) 0.71812(13) 0.34661(11) 0.0322(4) Uani 1 1 d . . . H34A H 0.9938 0.7203 0.3157 0.039 Uiso 1 1 calc R . . H34B H 0.8740 0.7349 0.3969 0.039 Uiso 1 1 calc R . . C14 C 0.4628(3) 0.35496(13) 0.45838(10) 0.0304(4) Uani 1 1 d . . . H14 H 0.4763 0.4215 0.4579 0.036 Uiso 1 1 calc R . . C28 C -0.1405(4) 0.39698(15) 0.02074(12) 0.0383(5) Uani 1 1 d . . . H28 H -0.2907 0.4361 0.0162 0.046 Uiso 1 1 calc R . . C26 C 0.2056(3) 0.35234(13) 0.08847(10) 0.0297(4) Uani 1 1 d . . . C25 C 0.2871(4) 0.28641(15) 0.03464(11) 0.0361(4) Uani 1 1 d . B . H25 H 0.4368 0.2463 0.0376 0.043 Uiso 1 1 calc R . . C23 C 0.3527(4) 0.36286(15) 0.15236(11) 0.0364(5) Uani 1 1 d . B . H23A H 0.4118 0.4255 0.1478 0.044 Uiso 1 1 calc R . . H23B H 0.4932 0.3116 0.1505 0.044 Uiso 1 1 calc R . . C27 C -0.0140(4) 0.40863(14) 0.08051(11) 0.0348(4) Uani 1 1 d . B . H27 H -0.0772 0.4551 0.1161 0.042 Uiso 1 1 calc R . . C33 C 0.6458(4) 0.79211(13) 0.31779(11) 0.0372(5) Uani 1 1 d . . . H33 H 0.5011 0.7918 0.3520 0.045 Uiso 1 1 calc R . . C24 C 0.1502(4) 0.27915(16) -0.02338(12) 0.0414(5) Uani 1 1 d . . . H24 H 0.2093 0.2333 -0.0598 0.050 Uiso 1 1 calc R B . O7 O 0.5802(5) 0.96223(12) 0.33551(16) 0.0995(10) Uani 1 1 d . . . N3 N -0.0257(14) 0.0810(5) 0.2675(2) 0.0369(14) Uani 0.606(12) 1 d PU B 1 C17 C -0.1639(15) 0.1607(7) 0.2885(3) 0.0352(19) Uani 0.606(12) 1 d PU B 1 H17 H -0.3142 0.1564 0.3133 0.042 Uiso 0.606(12) 1 calc PR B 1 C18 C -0.0975(14) 0.2506(5) 0.2757(4) 0.0340(14) Uani 0.606(12) 1 d PU B 1 H18 H -0.2045 0.3063 0.2907 0.041 Uiso 0.606(12) 1 calc PR B 1 C19 C 0.119(3) 0.2610(14) 0.2417(8) 0.026(2) Uani 0.606(12) 1 d PU B 1 C20 C 0.2602(19) 0.1739(9) 0.2161(6) 0.0322(16) Uani 0.606(12) 1 d PU B 1 H20 H 0.4064 0.1757 0.1881 0.039 Uiso 0.606(12) 1 calc PR B 1 C21 C 0.1830(14) 0.0886(4) 0.2320(3) 0.0396(13) Uani 0.606(12) 1 d PU B 1 H21 H 0.2833 0.0312 0.2170 0.048 Uiso 0.606(12) 1 calc PR B 1 N3A N -0.135(2) 0.1186(8) 0.2824(6) 0.034(2) Uani 0.394(12) 1 d PU B 2 C17A C -0.2403(15) 0.2087(8) 0.2939(4) 0.0299(19) Uani 0.394(12) 1 d PU B 2 H17A H -0.3983 0.2194 0.3158 0.036 Uiso 0.394(12) 1 calc PR B 2 C18A C -0.1286(18) 0.2870(7) 0.2754(6) 0.0252(17) Uani 0.394(12) 1 d PU B 2 H18A H -0.2056 0.3502 0.2866 0.030 Uiso 0.394(12) 1 calc PR B 2 C19A C 0.106(5) 0.272(2) 0.2388(12) 0.033(5) Uani 0.394(12) 1 d PU B 2 C20A C 0.209(3) 0.1818(15) 0.2327(9) 0.036(3) Uani 0.394(12) 1 d PU B 2 H20A H 0.3705 0.1685 0.2146 0.044 Uiso 0.394(12) 1 calc PR B 2 C21A C 0.084(2) 0.1031(6) 0.2527(5) 0.0340(19) Uani 0.394(12) 1 d PU B 2 H21A H 0.1597 0.0390 0.2443 0.041 Uiso 0.394(12) 1 calc PR B 2 C37 C 0.7046(8) 0.89111(18) 0.31497(18) 0.0737(11) Uani 1 1 d . . . O6 O 0.9149(6) 0.89725(14) 0.28381(15) 0.0980(9) Uani 1 1 d . . . H6 H 0.9254 0.9552 0.2739 0.147 Uiso 1 1 calc R . . Cl1 Cl 0.7190(3) 1.10666(11) -0.07964(7) 0.0536(3) Uani 0.50 1 d P C -1 Cl2 Cl 0.2869(3) 1.00560(13) -0.11846(8) 0.0512(6) Uani 0.379(2) 1 d P C -1 Cl3 Cl 0.8408(12) 1.1024(5) 0.0809(4) 0.077(2) Uani 0.121(2) 1 d P C -1 C38 C 0.3909(18) 0.9905(7) -0.0348(5) 0.0467(19) Uani 0.50 1 d P C -1 C39 C 0.5842(10) 1.0361(4) -0.0155(4) 0.0451(11) Uani 0.50 1 d P C -1 C40 C 0.662(2) 1.0256(10) 0.0569(7) 0.067(3) Uani 0.50 1 d P C -1 C41 C 0.5563(13) 0.9714(4) 0.1048(3) 0.0674(16) Uani 0.50 1 d P C -1 H41A H 0.6097 0.9631 0.1528 0.081 Uiso 0.50 1 calc PR C -1 C42 C 0.3768(14) 0.9286(5) 0.0872(5) 0.080(2) Uani 0.50 1 d P C -1 H42A H 0.3050 0.8908 0.1235 0.096 Uiso 0.50 1 calc PR C -1 C43 C 0.2888(13) 0.9361(4) 0.0185(4) 0.0591(15) Uani 0.50 1 d P C -1 H43A H 0.1596 0.9041 0.0082 0.071 Uiso 0.50 1 calc PR C -1 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 O4 0.0302(7) 0.0210(6) 0.0440(8) 0.0069(5) -0.0112(6) -0.0005(5) O5 0.0331(8) 0.0345(8) 0.0661(10) 0.0109(7) -0.0204(7) -0.0074(6) O8 0.0485(9) 0.0339(7) 0.0344(7) -0.0074(6) -0.0106(6) -0.0013(6) N1 0.0282(8) 0.0246(7) 0.0311(8) 0.0034(6) -0.0043(6) 0.0007(6) C36 0.0335(10) 0.0235(9) 0.0312(9) 0.0038(7) -0.0085(8) -0.0067(7) C16 0.0246(9) 0.0226(8) 0.0337(9) 0.0003(7) -0.0085(7) 0.0003(7) C35 0.0298(9) 0.0238(8) 0.0256(9) 0.0007(7) -0.0045(7) -0.0019(7) C29 0.0253(9) 0.0200(8) 0.0263(9) -0.0004(6) -0.0033(7) -0.0006(6) C31 0.0273(9) 0.0213(8) 0.0263(9) 0.0012(6) -0.0038(7) -0.0007(7) C12 0.0267(9) 0.0247(9) 0.0271(9) -0.0024(7) -0.0022(7) 0.0026(7) C10 0.0266(9) 0.0259(9) 0.0408(11) 0.0028(8) -0.0087(8) -0.0028(7) C11 0.0291(9) 0.0224(8) 0.0386(10) 0.0027(7) -0.0054(8) -0.0025(7) C13 0.0287(9) 0.0275(9) 0.0375(10) -0.0073(8) -0.0085(8) -0.0003(7) C30 0.0286(9) 0.0170(8) 0.0282(9) -0.0011(6) -0.0059(7) -0.0009(6) C15 0.0346(10) 0.0282(9) 0.0360(10) -0.0040(8) -0.0128(8) 0.0063(8) C32 0.0436(11) 0.0182(8) 0.0311(9) 0.0014(7) -0.0099(8) -0.0006(7) N2 0.0380(9) 0.0444(10) 0.0363(9) 0.0052(8) -0.0116(7) -0.0109(8) C22 0.0475(12) 0.0272(9) 0.0301(10) -0.0032(7) -0.0043(8) -0.0086(8) O9 0.0512(10) 0.0512(9) 0.0443(9) -0.0088(7) -0.0260(7) 0.0104(7) C34 0.0404(11) 0.0212(9) 0.0368(10) -0.0019(7) -0.0144(8) -0.0042(8) C14 0.0327(10) 0.0219(8) 0.0361(10) -0.0012(7) -0.0036(8) -0.0021(7) C28 0.0307(10) 0.0379(11) 0.0459(12) 0.0081(9) -0.0037(9) -0.0051(8) C26 0.0321(10) 0.0311(9) 0.0287(9) 0.0036(7) -0.0003(7) -0.0152(8) C25 0.0325(10) 0.0413(11) 0.0338(10) -0.0018(8) -0.0051(8) -0.0020(8) C23 0.0404(11) 0.0405(11) 0.0336(10) 0.0003(8) -0.0059(8) -0.0220(9) C27 0.0388(11) 0.0310(10) 0.0351(10) -0.0013(8) 0.0026(8) -0.0090(8) C33 0.0551(13) 0.0185(9) 0.0376(11) -0.0031(7) -0.0161(9) 0.0023(8) C24 0.0450(12) 0.0467(12) 0.0320(10) -0.0065(9) -0.0062(9) -0.0030(10) O7 0.136(2) 0.0177(9) 0.149(2) -0.0203(11) -0.0824(19) 0.0120(10) N3 0.042(3) 0.034(3) 0.037(2) 0.0050(16) -0.001(2) -0.013(2) C17 0.026(3) 0.047(6) 0.032(2) 0.000(4) -0.001(2) -0.006(4) C18 0.037(3) 0.030(4) 0.033(2) -0.003(3) -0.0046(17) 0.003(3) C19 0.028(4) 0.025(4) 0.031(4) 0.009(2) -0.013(3) -0.016(4) C20 0.034(4) 0.023(3) 0.039(5) -0.004(3) 0.007(2) -0.003(3) C21 0.044(3) 0.028(2) 0.046(3) 0.0017(17) 0.003(2) -0.004(2) N3A 0.030(4) 0.029(6) 0.042(4) 0.001(4) -0.001(3) 0.001(5) C17A 0.024(4) 0.031(5) 0.036(3) 0.001(3) -0.002(3) -0.008(3) C18A 0.024(3) 0.020(4) 0.031(3) 0.002(4) -0.009(2) -0.002(3) C19A 0.043(7) 0.037(9) 0.017(5) 0.004(5) -0.008(4) 0.007(4) C20A 0.031(7) 0.040(5) 0.037(7) -0.007(5) 0.001(4) -0.001(5) C21A 0.029(5) 0.028(4) 0.044(4) -0.002(3) 0.003(4) -0.002(3) C37 0.133(3) 0.0299(14) 0.0700(19) 0.0147(12) -0.062(2) -0.0287(16) O6 0.175(3) 0.0306(10) 0.0967(18) 0.0028(10) -0.0123(18) -0.0422(14) Cl1 0.0534(8) 0.0600(8) 0.0464(7) 0.0047(6) -0.0010(6) -0.0077(6) Cl2 0.0427(10) 0.0740(11) 0.0364(9) -0.0092(7) 0.0029(6) -0.0085(8) Cl3 0.066(4) 0.091(5) 0.063(4) 0.006(3) -0.012(3) 0.025(3) C38 0.058(5) 0.037(4) 0.035(5) 0.003(3) 0.007(3) 0.020(3) C39 0.041(3) 0.034(3) 0.055(4) -0.001(3) 0.006(3) 0.007(2) C40 0.081(7) 0.053(6) 0.058(7) -0.003(4) -0.010(4) 0.020(4) C41 0.073(4) 0.063(4) 0.063(4) 0.021(3) -0.019(3) 0.003(3) C42 0.070(5) 0.066(4) 0.105(6) 0.045(4) -0.024(4) -0.013(4) C43 0.048(3) 0.045(3) 0.079(4) 0.010(3) 0.000(3) 0.007(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O4 C35 1.321(2) . ? O4 H4 0.8400 . ? O5 C35 1.211(2) . ? O8 C36 1.208(2) . ? N1 C14 1.333(2) . ? N1 C10 1.342(2) . ? C36 O9 1.315(2) . ? C36 C31 1.513(2) . ? C16 C15 1.519(3) . ? C16 C16 1.527(3) 2_756 ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C35 C29 1.511(2) . ? C29 C34 1.523(2) . ? C29 C30 1.536(2) . ? C29 H29 1.0000 . ? C31 C30 1.522(2) . ? C31 C32 1.535(2) . ? C31 H31 1.0000 . ? C12 C13 1.386(3) . ? C12 C11 1.389(3) . ? C12 C15 1.512(2) . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C13 C14 1.386(3) . ? C13 H13 0.9500 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C32 C33 1.533(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? N2 C24 1.330(3) . ? N2 C28 1.335(3) . ? C22 C19A 1.43(2) . ? C22 C23 1.528(3) . ? C22 C19 1.544(14) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? O9 H9 0.8400 . ? C34 C33 1.528(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C14 H14 0.9500 . ? C28 C27 1.379(3) . ? C28 H28 0.9500 . ? C26 C25 1.381(3) . ? C26 C27 1.387(3) . ? C26 C23 1.510(3) . ? C25 C24 1.377(3) . ? C25 H25 0.9500 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C27 H27 0.9500 . ? C33 C37 1.480(3) . ? C33 H33 1.0000 . ? C24 H24 0.9500 . ? O7 C37 1.188(4) . ? N3 C17 1.318(8) . ? N3 C21 1.332(6) . ? C17 C18 1.384(8) . ? C17 H17 0.9500 . ? C18 C19 1.370(16) . ? C18 H18 0.9500 . ? C19 C20 1.43(2) . ? C20 C21 1.357(14) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? N3A C21A 1.310(14) . ? N3A C17A 1.334(9) . ? C17A C18A 1.377(12) . ? C17A H17A 0.9500 . ? C18A C19A 1.44(3) . ? C18A H18A 0.9500 . ? C19A C20A 1.32(4) . ? C20A C21A 1.43(2) . ? C20A H20A 0.9500 . ? C21A H21A 0.9500 . ? C37 O6 1.304(5) . ? O6 H6 0.8400 . ? Cl1 C39 1.733(7) . ? Cl2 C38 1.679(9) . ? Cl3 C40 1.678(15) . ? C38 C43 1.377(13) . ? C38 C39 1.425(12) . ? C39 C40 1.427(11) . ? C40 C41 1.323(17) . ? C41 C42 1.325(11) . ? C41 H41A 0.9500 . ? C42 C43 1.385(10) . ? C42 H42A 0.9500 . ? C43 H43A 0.9500 . ? 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 _geom_angle_publ_flag C35 O4 H4 109.5 . . ? C14 N1 C10 117.30(15) . . ? O8 C36 O9 123.74(17) . . ? O8 C36 C31 124.66(17) . . ? O9 C36 C31 111.59(16) . . ? C15 C16 C16 111.13(19) . 2_756 ? C15 C16 H16A 109.4 . . ? C16 C16 H16A 109.4 2_756 . ? C15 C16 H16B 109.4 . . ? C16 C16 H16B 109.4 2_756 . ? H16A C16 H16B 108.0 . . ? O5 C35 O4 123.24(16) . . ? O5 C35 C29 124.32(16) . . ? O4 C35 C29 112.44(15) . . ? C35 C29 C34 111.05(15) . . ? C35 C29 C30 111.01(14) . . ? C34 C29 C30 111.15(14) . . ? C35 C29 H29 107.8 . . ? C34 C29 H29 107.8 . . ? C30 C29 H29 107.8 . . ? C36 C31 C30 112.58(14) . . ? C36 C31 C32 110.07(14) . . ? C30 C31 C32 110.91(15) . . ? C36 C31 H31 107.7 . . ? C30 C31 H31 107.7 . . ? C32 C31 H31 107.7 . . ? C13 C12 C11 117.34(16) . . ? C13 C12 C15 121.78(17) . . ? C11 C12 C15 120.86(16) . . ? N1 C10 C11 123.24(17) . . ? N1 C10 H10 118.4 . . ? C11 C10 H10 118.4 . . ? C10 C11 C12 119.40(17) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C12 C13 C14 119.71(17) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C31 C30 C29 109.59(14) . . ? C31 C30 H30A 109.8 . . ? C29 C30 H30A 109.8 . . ? C31 C30 H30B 109.8 . . ? C29 C30 H30B 109.8 . . ? H30A C30 H30B 108.2 . . ? C12 C15 C16 114.47(15) . . ? C12 C15 H15A 108.6 . . ? C16 C15 H15A 108.6 . . ? C12 C15 H15B 108.6 . . ? C16 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C33 C32 C31 110.18(15) . . ? C33 C32 H32A 109.6 . . ? C31 C32 H32A 109.6 . . ? C33 C32 H32B 109.6 . . ? C31 C32 H32B 109.6 . . ? H32A C32 H32B 108.1 . . ? C24 N2 C28 117.35(18) . . ? C19A C22 C23 115.1(9) . . ? C19A C22 C19 5.1(19) . . ? C23 C22 C19 114.2(6) . . ? C19A C22 H22A 103.9 . . ? C23 C22 H22A 108.7 . . ? C19 C22 H22A 108.7 . . ? C19A C22 H22B 112.4 . . ? C23 C22 H22B 108.7 . . ? C19 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C36 O9 H9 109.5 . . ? C29 C34 C33 111.69(16) . . ? C29 C34 H34A 109.3 . . ? C33 C34 H34A 109.3 . . ? C29 C34 H34B 109.3 . . ? C33 C34 H34B 109.3 . . ? H34A C34 H34B 107.9 . . ? N1 C14 C13 122.99(17) . . ? N1 C14 H14 118.5 . . ? C13 C14 H14 118.5 . . ? N2 C28 C27 122.77(19) . . ? N2 C28 H28 118.6 . . ? C27 C28 H28 118.6 . . ? C25 C26 C27 117.09(18) . . ? C25 C26 C23 120.90(18) . . ? C27 C26 C23 122.01(18) . . ? C24 C25 C26 119.59(19) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C26 C23 C22 113.28(16) . . ? C26 C23 H23A 108.9 . . ? C22 C23 H23A 108.9 . . ? C26 C23 H23B 108.9 . . ? C22 C23 H23B 108.9 . . ? H23A C23 H23B 107.7 . . ? C28 C27 C26 119.81(19) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C37 C33 C34 112.9(2) . . ? C37 C33 C32 109.81(18) . . ? C34 C33 C32 110.99(15) . . ? C37 C33 H33 107.7 . . ? C34 C33 H33 107.7 . . ? C32 C33 H33 107.7 . . ? N2 C24 C25 123.4(2) . . ? N2 C24 H24 118.3 . . ? C25 C24 H24 118.3 . . ? C17 N3 C21 118.0(4) . . ? N3 C17 C18 122.2(5) . . ? N3 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C19 C18 C17 121.3(10) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 115.2(11) . . ? C18 C19 C22 125.7(15) . . ? C20 C19 C22 119.0(10) . . ? C21 C20 C19 119.4(8) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? N3 C21 C20 123.5(5) . . ? N3 C21 H21 118.2 . . ? C20 C21 H21 118.2 . . ? C21A N3A C17A 119.3(9) . . ? N3A C17A C18A 122.4(8) . . ? N3A C17A H17A 118.8 . . ? C18A C17A H17A 118.8 . . ? C17A C18A C19A 119.4(13) . . ? C17A C18A H18A 120.3 . . ? C19A C18A H18A 120.3 . . ? C20A C19A C22 128(2) . . ? C20A C19A C18A 115.7(18) . . ? C22 C19A C18A 115(2) . . ? C19A C20A C21A 122.1(14) . . ? C19A C20A H20A 118.9 . . ? C21A C20A H20A 118.9 . . ? N3A C21A C20A 120.6(9) . . ? N3A C21A H21A 119.7 . . ? C20A C21A H21A 119.7 . . ? O7 C37 O6 119.3(3) . . ? O7 C37 C33 127.2(4) . . ? O6 C37 C33 113.5(3) . . ? C37 O6 H6 109.5 . . ? C43 C38 C39 117.3(9) . . ? C43 C38 Cl2 121.6(8) . . ? C39 C38 Cl2 121.2(7) . . ? C38 C39 C40 120.1(10) . . ? C38 C39 Cl1 119.7(6) . . ? C40 C39 Cl1 120.2(8) . . ? C41 C40 C39 119.0(10) . . ? C41 C40 Cl3 122.9(8) . . ? C39 C40 Cl3 116.6(11) . . ? C40 C41 C42 121.3(7) . . ? C40 C41 H41A 119.4 . . ? C42 C41 H41A 119.4 . . ? C41 C42 C43 123.2(7) . . ? C41 C42 H42A 118.4 . . ? C43 C42 H42A 118.4 . . ? C38 C43 C42 119.2(9) . . ? C38 C43 H43A 120.4 . . ? C42 C43 H43A 120.4 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.557 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.051 # Attachment 'cocrystal_5f.cif' data_5f _database_code_depnum_ccdc_archive 'CCDC 681092' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1,2-bis(4-pyridyl)ethane - 1,4-bis(4-pyridyl)butane - anisole ; _chemical_melting_point ? _chemical_formula_moiety 2(C9H12O6),(C14H16N2),2(C12H12N2),(C7H8O) _chemical_formula_sum 'C63 H72 N6 O13' _chemical_formula_weight 1121.27 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7484(5) _cell_length_b 14.1360(12) _cell_length_c 18.1188(15) _cell_angle_alpha 85.7580(10) _cell_angle_beta 83.8170(10) _cell_angle_gamma 81.5740(10) _cell_volume 1445.4(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3745 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.08 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9707 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details 'SADABS -Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9842 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.67 _reflns_number_total 5434 _reflns_number_gt 4473 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.5509P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5434 _refine_ls_number_parameters 418 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O6 O 0.4400(2) 0.45762(8) 0.38114(7) 0.0296(3) Uani 1 1 d . . . O1 O 0.0424(2) 0.58582(9) 0.13878(7) 0.0349(3) Uani 1 1 d . . . O3 O 0.0867(2) 0.96506(9) 0.33816(8) 0.0413(3) Uani 1 1 d . . . O4 O 0.4480(2) 0.90306(10) 0.29452(8) 0.0424(4) Uani 1 1 d . . . O5 O 0.6853(2) 0.56381(9) 0.38927(8) 0.0409(4) Uani 1 1 d . . . O2 O -0.2153(3) 0.71841(10) 0.15442(8) 0.0442(4) Uani 1 1 d . . . N30 N -0.2065(2) 0.32757(10) 0.42187(8) 0.0260(3) Uani 1 1 d . . . C15 C 0.4959(3) 0.54540(11) 0.37550(9) 0.0248(4) Uani 1 1 d . . . C10 C 0.3624(3) 0.72046(11) 0.35021(10) 0.0268(4) Uani 1 1 d . . . H10A H 0.5104 0.7252 0.3176 0.032 Uiso 1 1 calc R . . H10B H 0.3905 0.7331 0.4013 0.032 Uiso 1 1 calc R . . C34 C -0.0518(3) 0.16462(12) 0.45254(9) 0.0256(4) Uani 1 1 d . . . H34 H -0.0641 0.0986 0.4505 0.031 Uiso 1 1 calc R . . C35 C -0.2155(3) 0.23337(12) 0.42210(9) 0.0263(4) Uani 1 1 d . . . H35 H -0.3411 0.2129 0.4002 0.032 Uiso 1 1 calc R . . C11 C 0.2986(3) 0.61945(11) 0.34971(9) 0.0232(4) Uani 1 1 d . . . H11 H 0.1553 0.6151 0.3856 0.028 Uiso 1 1 calc R . . C37 C 0.4205(3) 0.03674(11) 0.47761(9) 0.0235(4) Uani 1 1 d . . . H37A H 0.5152 0.0618 0.4335 0.028 Uiso 1 1 calc R . . H37B H 0.2957 0.0053 0.4599 0.028 Uiso 1 1 calc R . . C31 C -0.0269(3) 0.35436(12) 0.45267(9) 0.0272(4) Uani 1 1 d . . . H31 H -0.0153 0.4208 0.4521 0.033 Uiso 1 1 calc R . . C7 C 0.0381(3) 0.67378(11) 0.24811(9) 0.0241(4) Uani 1 1 d . . . H7 H -0.1000 0.6710 0.2864 0.029 Uiso 1 1 calc R . . C36 C 0.3062(3) 0.11962(12) 0.52444(9) 0.0257(4) Uani 1 1 d . . . H36A H 0.2239 0.0931 0.5705 0.031 Uiso 1 1 calc R . . H36B H 0.4325 0.1529 0.5392 0.031 Uiso 1 1 calc R . . C14 C 0.2279(3) 0.89666(12) 0.32024(10) 0.0294(4) Uani 1 1 d . . . C33 C 0.1319(3) 0.19233(11) 0.48635(9) 0.0223(3) Uani 1 1 d . . . C12 C 0.2371(3) 0.59885(11) 0.27274(9) 0.0236(4) Uani 1 1 d . . . H12A H 0.3782 0.5998 0.2363 0.028 Uiso 1 1 calc R . . H12B H 0.1879 0.5344 0.2747 0.028 Uiso 1 1 calc R . . C8 C 0.1060(3) 0.77510(11) 0.24624(9) 0.0259(4) Uani 1 1 d . . . H8A H 0.2441 0.7806 0.2093 0.031 Uiso 1 1 calc R . . H8B H -0.0271 0.8227 0.2311 0.031 Uiso 1 1 calc R . . C13 C -0.0412(3) 0.65356(12) 0.17469(10) 0.0269(4) Uani 1 1 d . . . C9 C 0.1661(3) 0.79587(11) 0.32339(9) 0.0256(4) Uani 1 1 d . . . H9 H 0.0216 0.7929 0.3591 0.031 Uiso 1 1 calc R . . C32 C 0.1425(3) 0.28987(12) 0.48522(9) 0.0264(4) Uani 1 1 d . . . H32 H 0.2661 0.3123 0.5068 0.032 Uiso 1 1 calc R . . H6 H 0.581(5) 0.4108(18) 0.3930(14) 0.073(8) Uiso 1 1 d . . . H2 H -0.264(5) 0.7033(19) 0.1122(15) 0.072(8) Uiso 1 1 d . . . H4 H 0.461(5) 0.970(2) 0.2884(16) 0.091(9) Uiso 1 1 d . . . N22 N 0.4022(3) 0.31895(11) -0.03633(8) 0.0335(4) Uani 1 1 d . . . N16 N 0.5241(3) 0.08441(11) 0.27094(9) 0.0349(4) Uani 1 1 d . . . C25 C 0.6517(3) 0.36350(12) 0.07752(9) 0.0284(4) Uani 1 1 d . . . C18 C 0.3950(3) 0.25305(13) 0.26850(10) 0.0325(4) Uani 1 1 d . . . H18 H 0.2725 0.3041 0.2802 0.039 Uiso 1 1 calc R . . C17 C 0.3585(3) 0.15790(14) 0.28526(10) 0.0330(4) Uani 1 1 d . . . H17 H 0.2082 0.1455 0.3079 0.040 Uiso 1 1 calc R . . C19 C 0.6129(3) 0.27193(12) 0.23449(9) 0.0270(4) Uani 1 1 d . . . C26 C 0.7419(3) 0.29037(13) 0.03141(10) 0.0318(4) Uani 1 1 d . . . H26 H 0.8916 0.2539 0.0379 0.038 Uiso 1 1 calc R . . C23 C 0.3141(3) 0.38913(13) 0.00845(10) 0.0333(4) Uani 1 1 d . . . H23 H 0.1638 0.4242 0.0007 0.040 Uiso 1 1 calc R . . C28 C 0.7884(4) 0.38855(13) 0.13812(10) 0.0347(4) Uani 1 1 d . . . H28A H 0.8138 0.4564 0.1298 0.042 Uiso 1 1 calc R . . H28B H 0.9453 0.3486 0.1351 0.042 Uiso 1 1 calc R . . C20 C 0.7813(3) 0.19375(14) 0.21998(10) 0.0349(4) Uani 1 1 d . . . H20 H 0.9329 0.2031 0.1966 0.042 Uiso 1 1 calc R . . C27 C 0.6127(3) 0.27073(14) -0.02424(10) 0.0364(4) Uani 1 1 d . . . H27 H 0.6774 0.2203 -0.0554 0.044 Uiso 1 1 calc R . . C24 C 0.4305(3) 0.41317(12) 0.06531(10) 0.0321(4) Uani 1 1 d . . . H24 H 0.3604 0.4634 0.0960 0.039 Uiso 1 1 calc R . . C29 C 0.6625(4) 0.37339(13) 0.21587(10) 0.0364(4) Uani 1 1 d . . . H29A H 0.7610 0.3908 0.2529 0.044 Uiso 1 1 calc R . . H29B H 0.5111 0.4171 0.2199 0.044 Uiso 1 1 calc R . . C21 C 0.7318(4) 0.10265(14) 0.23895(11) 0.0385(5) Uani 1 1 d . . . H21 H 0.8520 0.0503 0.2287 0.046 Uiso 1 1 calc R . . C41 C -0.247(3) -0.0599(12) -0.0413(6) 0.150(8) Uani 0.50 1 d PD A -1 H41A H -0.3689 -0.0918 -0.0548 0.180 Uiso 0.50 1 calc PR A -1 C39 C 0.011(3) -0.0340(10) 0.0522(5) 0.052(3) Uani 0.50 1 d PD A -1 H39A H 0.0684 -0.0492 0.0995 0.062 Uiso 0.50 1 calc PR A -1 C42 C -0.1472(8) 0.0093(4) -0.0921(3) 0.0488(11) Uani 0.50 1 d PD A -1 H42A H -0.1985 0.0240 -0.1403 0.059 Uiso 0.50 1 calc PR A -1 C40 C -0.1633(10) -0.0797(4) 0.0280(4) 0.0551(14) Uani 0.50 1 d PD A -1 H40A H -0.2283 -0.1270 0.0606 0.066 Uiso 0.50 1 calc PR A -1 O44 O 0.2488(12) 0.0852(6) 0.0259(3) 0.0635(17) Uani 0.50 1 d PD A -1 C43 C 0.027(3) 0.0538(12) -0.0678(7) 0.060(3) Uani 0.50 1 d PD A -1 H43A H 0.1020 0.0982 -0.1007 0.072 Uiso 0.50 1 calc PR A -1 C38 C 0.0940(8) 0.0351(4) 0.0022(3) 0.0519(12) Uani 0.50 1 d PD A -1 C45 C 0.3504(11) 0.0670(5) 0.0954(3) 0.086(2) Uani 0.50 1 d PD A -1 H45A H 0.4586 0.1135 0.0994 0.129 Uiso 0.50 1 calc PR A -1 H45B H 0.4376 0.0021 0.0977 0.129 Uiso 0.50 1 calc PR A -1 H45C H 0.2245 0.0732 0.1364 0.129 Uiso 0.50 1 calc PR A -1 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 O6 0.0302(7) 0.0188(6) 0.0406(7) 0.0040(5) -0.0137(5) -0.0013(5) O1 0.0408(7) 0.0291(7) 0.0368(7) -0.0084(6) -0.0135(6) -0.0018(6) O3 0.0437(8) 0.0207(6) 0.0602(9) -0.0063(6) -0.0120(7) 0.0001(6) O4 0.0458(8) 0.0238(7) 0.0569(9) -0.0012(6) 0.0018(7) -0.0086(6) O5 0.0328(7) 0.0275(7) 0.0653(10) 0.0070(6) -0.0226(7) -0.0058(6) O2 0.0525(9) 0.0394(8) 0.0418(8) -0.0086(6) -0.0295(7) 0.0113(7) N30 0.0269(7) 0.0224(7) 0.0284(8) 0.0021(6) -0.0072(6) -0.0007(6) C15 0.0284(9) 0.0214(8) 0.0250(8) 0.0015(7) -0.0070(7) -0.0027(7) C10 0.0309(9) 0.0199(8) 0.0311(9) -0.0017(7) -0.0117(7) -0.0022(7) C34 0.0270(9) 0.0198(8) 0.0306(9) -0.0001(7) -0.0060(7) -0.0034(7) C35 0.0258(9) 0.0237(8) 0.0304(9) -0.0001(7) -0.0084(7) -0.0029(7) C11 0.0242(8) 0.0193(8) 0.0262(9) -0.0001(7) -0.0055(7) -0.0019(6) C37 0.0238(8) 0.0201(8) 0.0275(9) -0.0003(7) -0.0094(7) -0.0009(7) C31 0.0301(9) 0.0195(8) 0.0323(9) -0.0003(7) -0.0065(7) -0.0027(7) C7 0.0260(8) 0.0197(8) 0.0267(9) -0.0004(7) -0.0063(7) -0.0014(7) C36 0.0273(9) 0.0225(8) 0.0276(9) -0.0007(7) -0.0096(7) -0.0002(7) C14 0.0364(10) 0.0222(9) 0.0309(9) -0.0007(7) -0.0123(8) -0.0025(8) C33 0.0227(8) 0.0220(8) 0.0214(8) -0.0025(6) -0.0025(6) 0.0004(7) C12 0.0262(8) 0.0171(8) 0.0281(9) -0.0009(6) -0.0069(7) -0.0021(6) C8 0.0310(9) 0.0185(8) 0.0281(9) 0.0013(7) -0.0079(7) -0.0005(7) C13 0.0274(9) 0.0227(8) 0.0318(9) 0.0018(7) -0.0065(7) -0.0065(7) C9 0.0302(9) 0.0186(8) 0.0286(9) -0.0011(7) -0.0065(7) -0.0029(7) C32 0.0259(9) 0.0252(9) 0.0296(9) -0.0028(7) -0.0086(7) -0.0033(7) N22 0.0367(9) 0.0347(8) 0.0301(8) 0.0035(7) -0.0106(7) -0.0061(7) N16 0.0426(9) 0.0297(8) 0.0336(8) 0.0026(7) -0.0090(7) -0.0077(7) C25 0.0345(9) 0.0267(9) 0.0258(9) 0.0058(7) -0.0025(7) -0.0145(7) C18 0.0335(10) 0.0357(10) 0.0271(9) -0.0037(8) -0.0064(7) 0.0022(8) C17 0.0290(9) 0.0448(11) 0.0271(9) 0.0037(8) -0.0045(7) -0.0126(8) C19 0.0374(10) 0.0265(9) 0.0198(8) -0.0005(7) -0.0103(7) -0.0078(7) C26 0.0311(9) 0.0346(10) 0.0299(9) 0.0010(8) -0.0078(7) -0.0028(8) C23 0.0306(9) 0.0301(10) 0.0379(10) 0.0085(8) -0.0045(8) -0.0040(8) C28 0.0472(11) 0.0322(10) 0.0299(10) 0.0004(8) -0.0076(8) -0.0206(9) C20 0.0297(9) 0.0384(10) 0.0354(10) 0.0041(8) -0.0029(8) -0.0050(8) C27 0.0418(11) 0.0369(10) 0.0306(10) -0.0065(8) -0.0095(8) 0.0005(8) C24 0.0387(10) 0.0236(9) 0.0335(10) 0.0003(7) 0.0022(8) -0.0077(8) C29 0.0523(12) 0.0297(10) 0.0306(10) -0.0046(8) -0.0073(9) -0.0137(9) C21 0.0400(11) 0.0327(10) 0.0400(11) 0.0033(8) -0.0029(9) 0.0008(8) C41 0.110(11) 0.095(10) 0.247(19) -0.091(11) -0.079(13) 0.068(7) C39 0.050(6) 0.049(7) 0.052(4) -0.011(4) -0.001(5) 0.012(3) C42 0.046(3) 0.049(3) 0.047(3) -0.011(2) -0.005(2) 0.012(2) C40 0.047(3) 0.046(3) 0.068(4) 0.002(3) 0.003(3) -0.001(2) O44 0.055(4) 0.068(4) 0.068(3) -0.018(2) -0.007(3) -0.001(3) C43 0.046(5) 0.042(5) 0.083(7) 0.003(4) 0.016(5) 0.001(3) C38 0.039(3) 0.037(3) 0.078(4) -0.014(3) -0.006(3) 0.005(2) C45 0.068(4) 0.127(6) 0.063(4) -0.034(4) -0.023(3) 0.011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O6 C15 1.321(2) . ? O6 H6 1.00(3) . ? O1 C13 1.209(2) . ? O3 C14 1.208(2) . ? O4 C14 1.314(2) . ? O4 H4 0.96(3) . ? O5 C15 1.211(2) . ? O2 C13 1.318(2) . ? O2 H2 0.89(3) . ? N30 C31 1.338(2) . ? N30 C35 1.340(2) . ? C15 C11 1.515(2) . ? C10 C11 1.526(2) . ? C10 C9 1.528(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C34 C35 1.378(2) . ? C34 C33 1.393(2) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C11 C12 1.533(2) . ? C11 H11 1.0000 . ? C37 C36 1.525(2) . ? C37 C37 1.526(3) 2_656 ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C31 C32 1.383(2) . ? C31 H31 0.9500 . ? C7 C13 1.511(2) . ? C7 C12 1.521(2) . ? C7 C8 1.536(2) . ? C7 H7 1.0000 . ? C36 C33 1.510(2) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C14 C9 1.514(2) . ? C33 C32 1.388(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C8 C9 1.534(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9 1.0000 . ? C32 H32 0.9500 . ? N22 C27 1.331(2) . ? N22 C23 1.335(2) . ? N16 C21 1.322(3) . ? N16 C17 1.323(2) . ? C25 C26 1.383(2) . ? C25 C24 1.391(3) . ? C25 C28 1.508(2) . ? C18 C19 1.388(3) . ? C18 C17 1.398(3) . ? C18 H18 0.9500 . ? C17 H17 0.9500 . ? C19 C20 1.379(3) . ? C19 C29 1.510(2) . ? C26 C27 1.382(2) . ? C26 H26 0.9500 . ? C23 C24 1.375(3) . ? C23 H23 0.9500 . ? C28 C29 1.528(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C20 C21 1.370(3) . ? C20 H20 0.9500 . ? C27 H27 0.9500 . ? C24 H24 0.9500 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C21 H21 0.9500 . ? C41 C40 1.386(2) . ? C41 C42 1.432(15) . ? C41 H41A 0.9500 . ? C39 C38 1.385(2) . ? C39 C40 1.392(10) . ? C39 H39A 0.9500 . ? C42 C43 1.384(2) . ? C42 H42A 0.9500 . ? C40 H40A 0.9500 . ? O44 C38 1.338(2) . ? O44 C45 1.435(2) . ? C43 C38 1.359(11) . ? C43 H43A 0.9500 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? 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 _geom_angle_publ_flag C15 O6 H6 109.5(15) . . ? C14 O4 H4 106.4(18) . . ? C13 O2 H2 110.1(17) . . ? C31 N30 C35 117.12(14) . . ? O5 C15 O6 123.17(15) . . ? O5 C15 C11 124.17(15) . . ? O6 C15 C11 112.65(13) . . ? C11 C10 C9 111.48(13) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C35 C34 C33 119.71(15) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? N30 C35 C34 123.32(15) . . ? N30 C35 H35 118.3 . . ? C34 C35 H35 118.3 . . ? C15 C11 C10 110.90(13) . . ? C15 C11 C12 111.00(13) . . ? C10 C11 C12 111.32(13) . . ? C15 C11 H11 107.8 . . ? C10 C11 H11 107.8 . . ? C12 C11 H11 107.8 . . ? C36 C37 C37 111.18(16) . 2_656 ? C36 C37 H37A 109.4 . . ? C37 C37 H37A 109.4 2_656 . ? C36 C37 H37B 109.4 . . ? C37 C37 H37B 109.4 2_656 . ? H37A C37 H37B 108.0 . . ? N30 C31 C32 123.03(15) . . ? N30 C31 H31 118.5 . . ? C32 C31 H31 118.5 . . ? C13 C7 C12 112.51(13) . . ? C13 C7 C8 111.44(13) . . ? C12 C7 C8 111.12(13) . . ? C13 C7 H7 107.2 . . ? C12 C7 H7 107.2 . . ? C8 C7 H7 107.2 . . ? C33 C36 C37 114.86(13) . . ? C33 C36 H36A 108.6 . . ? C37 C36 H36A 108.6 . . ? C33 C36 H36B 108.6 . . ? C37 C36 H36B 108.6 . . ? H36A C36 H36B 107.5 . . ? O3 C14 O4 123.17(16) . . ? O3 C14 C9 123.14(17) . . ? O4 C14 C9 113.67(15) . . ? C32 C33 C34 116.84(14) . . ? C32 C33 C36 121.76(14) . . ? C34 C33 C36 121.37(14) . . ? C7 C12 C11 110.09(13) . . ? C7 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? C7 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.2 . . ? C9 C8 C7 109.90(13) . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O1 C13 O2 123.60(16) . . ? O1 C13 C7 124.52(15) . . ? O2 C13 C7 111.88(14) . . ? C14 C9 C10 112.86(14) . . ? C14 C9 C8 108.74(13) . . ? C10 C9 C8 110.98(13) . . ? C14 C9 H9 108.0 . . ? C10 C9 H9 108.0 . . ? C8 C9 H9 108.0 . . ? C31 C32 C33 119.94(15) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C27 N22 C23 117.34(16) . . ? C21 N16 C17 117.97(16) . . ? C26 C25 C24 117.19(16) . . ? C26 C25 C28 121.29(16) . . ? C24 C25 C28 121.51(16) . . ? C19 C18 C17 119.05(16) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? N16 C17 C18 122.83(17) . . ? N16 C17 H17 118.6 . . ? C18 C17 H17 118.6 . . ? C20 C19 C18 116.68(16) . . ? C20 C19 C29 122.10(17) . . ? C18 C19 C29 121.21(16) . . ? C27 C26 C25 119.47(17) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? N22 C23 C24 123.16(17) . . ? N22 C23 H23 118.4 . . ? C24 C23 H23 118.4 . . ? C25 C28 C29 112.81(15) . . ? C25 C28 H28A 109.0 . . ? C29 C28 H28A 109.0 . . ? C25 C28 H28B 109.0 . . ? C29 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C21 C20 C19 120.59(18) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? N22 C27 C26 123.26(17) . . ? N22 C27 H27 118.4 . . ? C26 C27 H27 118.4 . . ? C23 C24 C25 119.56(17) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C19 C29 C28 113.66(15) . . ? C19 C29 H29A 108.8 . . ? C28 C29 H29A 108.8 . . ? C19 C29 H29B 108.8 . . ? C28 C29 H29B 108.8 . . ? H29A C29 H29B 107.7 . . ? N16 C21 C20 122.87(18) . . ? N16 C21 H21 118.6 . . ? C20 C21 H21 118.6 . . ? C40 C41 C42 119.3(12) . . ? C40 C41 H41A 120.4 . . ? C42 C41 H41A 120.4 . . ? C38 C39 C40 115.0(7) . . ? C38 C39 H39A 122.5 . . ? C40 C39 H39A 122.5 . . ? C43 C42 C41 116.9(8) . . ? C43 C42 H42A 121.6 . . ? C41 C42 H42A 121.6 . . ? C41 C40 C39 123.4(11) . . ? C41 C40 H40A 118.3 . . ? C39 C40 H40A 118.3 . . ? C38 O44 C45 125.4(6) . . ? C38 C43 C42 121.4(8) . . ? C38 C43 H43A 119.3 . . ? C42 C43 H43A 119.3 . . ? O44 C38 C43 119.7(6) . . ? O44 C38 C39 116.4(6) . . ? C43 C38 C39 123.9(6) . . ? O44 C45 H45A 109.5 . . ? O44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? O44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.67 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.309 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.044 # Attachment 'cocrystal_5g.cif' data_5g _database_code_depnum_ccdc_archive 'CCDC 681093' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis,cis-1,3,5-cyclohexanetricarboxylic acid - 1,2-bis(4-pyridyl)ethane - 1,4-bis(4-pyridyl)butane - benzylalcohol ; _chemical_melting_point ? _chemical_formula_moiety 2(C9H12O6),2(C12H12N2),(C14H16N2),(C7H8O) _chemical_formula_sum 'C63 H72 N6 O13' _chemical_formula_weight 1121.27 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7311(6) _cell_length_b 18.4298(18) _cell_length_c 27.577(3) _cell_angle_alpha 94.300(2) _cell_angle_beta 91.509(2) _cell_angle_gamma 94.623(2) _cell_volume 2893.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3377 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 24.03 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9673 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22418 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.11 _diffrn_reflns_theta_max 26.05 _reflns_number_total 11350 _reflns_number_gt 6965 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1648P)^2^+5.3660P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11350 _refine_ls_number_parameters 812 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1612 _refine_ls_R_factor_gt 0.1128 _refine_ls_wR_factor_ref 0.3377 _refine_ls_wR_factor_gt 0.2937 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 2.010 _refine_ls_shift/su_mean 0.023 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0831(5) 0.88038(17) 1.01640(10) 0.0387(7) Uani 1 1 d . . . H1AA H -0.0150 0.8957 1.0359 0.058 Uiso 1 1 calc R . . O2 O -0.1940(5) 0.89833(19) 0.96150(12) 0.0470(8) Uani 1 1 d . . . O6 O 0.4361(6) 0.64505(17) 0.95167(12) 0.0503(9) Uani 1 1 d . . . N2 N 0.7913(6) 0.92440(19) 0.08361(13) 0.0343(8) Uani 1 1 d . . . N1 N -0.3211(6) 1.0665(2) 0.42236(14) 0.0395(9) Uani 1 1 d . . . C1 C -0.0028(7) 0.8796(2) 0.97142(15) 0.0297(9) Uani 1 1 d . . . O5 O 0.6715(7) 0.66128(18) 0.88993(15) 0.0691(13) Uani 1 1 d . . . H5AA H 0.7166 0.6212 0.8974 0.104 Uiso 1 1 calc R . . C24 C 0.0783(7) 0.9613(2) 0.31161(17) 0.0369(10) Uani 1 1 d . . . H24A H -0.0236 0.9202 0.2953 0.044 Uiso 1 1 calc R . . H24B H 0.2142 0.9406 0.3267 0.044 Uiso 1 1 calc R . . C7 C 0.4171(7) 0.7525(2) 0.90815(14) 0.0301(9) Uani 1 1 d . . . H7 H 0.554(8) 0.790(2) 0.9098(15) 0.036 Uiso 1 1 calc . . . C21 C -0.0560(7) 0.9986(2) 0.35093(17) 0.0351(10) Uani 1 1 d . . . C27 C 0.3755(8) 1.0223(2) 0.19487(16) 0.0398(11) Uani 1 1 d . . . H27A H 0.2365 1.0410 0.1796 0.048 Uiso 1 1 calc R . . H27B H 0.4722 1.0646 0.2110 0.048 Uiso 1 1 calc R . . C29 C 0.4542(7) 0.9854(2) 0.10668(16) 0.0368(10) Uani 1 1 d . . . H29 H 0.3163 1.0064 0.0967 0.044 Uiso 1 1 calc R . . C9 C 0.2460(7) 0.7779(2) 0.94574(13) 0.0272(8) Uani 1 1 d . . . H9A H 0.3223 0.7818 0.9786 0.033 Uiso 1 1 calc R . . H9B H 0.1083 0.7418 0.9455 0.033 Uiso 1 1 calc R . . C8 C 0.5067(8) 0.6810(2) 0.91950(17) 0.0400(11) Uani 1 1 d . . . C20 C 0.0112(7) 1.0038(2) 0.39961(16) 0.0368(10) Uani 1 1 d . . . H20 H 0.1507 0.9837 0.4096 0.044 Uiso 1 1 calc R . . C2 C 0.1664(7) 0.8525(2) 0.93436(14) 0.0300(9) Uani 1 1 d . . . H2 H 0.308(8) 0.888(2) 0.9366(15) 0.036 Uiso 1 1 calc . . . C32 C 0.7214(8) 0.9551(3) 0.16745(17) 0.0424(11) Uani 1 1 d . . . H32 H 0.7710 0.9541 0.2005 0.051 Uiso 1 1 calc R . . C19 C -0.1231(7) 1.0378(2) 0.43387(17) 0.0396(10) Uani 1 1 d . . . H19 H -0.0720 1.0409 0.4671 0.048 Uiso 1 1 calc R . . C30 C 0.5920(7) 0.9538(2) 0.07213(17) 0.0369(10) Uani 1 1 d . . . H30 H 0.5440 0.9527 0.0388 0.044 Uiso 1 1 calc R . . C28 C 0.5151(7) 0.9870(2) 0.15573(16) 0.0372(10) Uani 1 1 d . . . C31 C 0.8514(7) 0.9255(2) 0.13117(17) 0.0396(10) Uani 1 1 d . . . H31 H 0.9912 0.9047 0.1401 0.047 Uiso 1 1 calc R . . C25 C 0.1659(6) 1.0118(2) 0.27350(15) 0.0296(9) Uani 1 1 d . . . H25A H 0.0310 1.0337 0.2590 0.035 Uiso 1 1 calc R . . H25B H 0.2728 1.0519 0.2895 0.035 Uiso 1 1 calc R . . C23 C -0.3854(7) 1.0627(3) 0.37549(18) 0.0436(11) Uani 1 1 d . . . H23 H -0.5250 1.0837 0.3666 0.052 Uiso 1 1 calc R . . C26 C 0.2940(7) 0.9718(2) 0.23333(16) 0.0332(9) Uani 1 1 d . . . H26A H 0.4313 0.9509 0.2477 0.040 Uiso 1 1 calc R . . H26B H 0.1884 0.9310 0.2178 0.040 Uiso 1 1 calc R . . C22 C -0.2608(8) 1.0302(3) 0.33917(19) 0.0463(12) Uani 1 1 d . . . H22 H -0.3142 1.0292 0.3062 0.056 Uiso 1 1 calc R . . C6 C 0.3098(8) 0.7484(3) 0.85671(15) 0.0436(11) Uani 1 1 d . . . H6A H 0.1739 0.7114 0.8537 0.052 Uiso 1 1 calc R . . H6B H 0.4267 0.7332 0.8330 0.052 Uiso 1 1 calc R . . C3 C 0.0633(8) 0.8507(3) 0.88320(16) 0.0476(13) Uani 1 1 d . . . H3A H 0.0263 0.9006 0.8763 0.057 Uiso 1 1 calc R . . H3B H -0.0848 0.8189 0.8807 0.057 Uiso 1 1 calc R . . C4 C 0.2308(9) 0.8226(3) 0.84530(16) 0.0498(13) Uani 1 1 d . . . H4 H 0.373(10) 0.858(3) 0.8462(19) 0.060 Uiso 1 1 calc . . . C5 C 0.1177(12) 0.8185(5) 0.7942(2) 0.087(3) Uani 1 1 d . . . O11 O 0.3926(5) 0.11627(17) 0.48968(11) 0.0416(8) Uani 1 1 d . . . H11A H 0.4875 0.0982 0.4705 0.062 Uiso 1 1 calc R . . O10 O 0.0744(6) 0.37233(17) 0.54329(13) 0.0496(9) Uani 1 1 d . . . C15 C 0.2593(7) 0.2371(2) 0.55384(13) 0.0281(8) Uani 1 1 d . . . H15A H 0.3985 0.2720 0.5514 0.034 Uiso 1 1 calc R . . H15B H 0.1786 0.2295 0.5215 0.034 Uiso 1 1 calc R . . C16 C 0.3364(7) 0.1641(2) 0.56938(15) 0.0345(10) Uani 1 1 d . . . H16 H 0.193(8) 0.130(2) 0.5704(16) 0.041 Uiso 1 1 calc . . . O12 O 0.6963(6) 0.1199(2) 0.54222(16) 0.0639(11) Uani 1 1 d . . . O7 O 0.3952(7) 0.1814(2) 0.73546(14) 0.0613(17) Uani 1.000(15) 1 d . . . H7AA H 0.4688 0.1966 0.7615 0.092 Uiso 0.70(12) 1 calc PR . . C17 C 0.4957(7) 0.1314(2) 0.53297(17) 0.0378(10) Uani 1 1 d . . . C14 C 0.0049(9) 0.3384(2) 0.57638(19) 0.0516(13) Uani 1 1 d . . . C13 C 0.0950(8) 0.2686(2) 0.59078(15) 0.0392(11) Uani 1 1 d . . . H13 H -0.043(8) 0.232(3) 0.5925(17) 0.047 Uiso 1 1 calc . . . O9 O -0.1632(10) 0.3591(2) 0.6046(2) 0.108(2) Uani 1 1 d . . . H9AA H -0.2097 0.3982 0.5956 0.162 Uiso 1 1 calc R . . C18 C 0.4492(9) 0.1744(4) 0.62058(19) 0.0629(17) Uani 1 1 d . . . H18A H 0.5984 0.2053 0.6198 0.075 Uiso 1 1 calc R . . H18B H 0.4858 0.1263 0.6311 0.075 Uiso 1 1 calc R . . C12 C 0.2098(11) 0.2806(3) 0.64103(17) 0.0649(17) Uani 1 1 d . . . H12A H 0.0970 0.2999 0.6643 0.078 Uiso 1 1 calc R . . H12B H 0.3459 0.3172 0.6406 0.078 Uiso 1 1 calc R . . C11 C 0.2904(11) 0.2100(4) 0.65760(18) 0.070(2) Uani 1 1 d . . . H11 H 0.149(11) 0.175(3) 0.661(2) 0.084 Uiso 1 1 calc . . . O8 O 0.4756(12) 0.2972(3) 0.72328(19) 0.042(2) Uani 0.531(12) 1 d P . . C10 C 0.4123(16) 0.2271(6) 0.7074(2) 0.116(4) Uani 1 1 d . . . N3 N 0.3083(7) 0.7807(2) 0.18765(16) 0.0484(10) Uani 1 1 d . . . N4 N 0.1621(7) 0.4611(2) 0.08816(16) 0.0508(11) Uani 1 1 d . . . C43 C 0.2638(9) 0.5006(3) 0.05483(19) 0.0523(13) Uani 1 1 d . . . H43 H 0.4039 0.4849 0.0414 0.063 Uiso 1 1 calc R . . C35 C -0.0228(8) 0.7338(2) 0.11462(16) 0.0372(10) Uani 1 1 d . . . C34 C -0.0697(9) 0.7215(3) 0.1621(2) 0.0520(13) Uani 1 1 d . . . H34 H -0.2133 0.6968 0.1705 0.062 Uiso 1 1 calc R . . C40 C -0.0197(10) 0.5863(2) 0.05747(18) 0.0512(13) Uani 1 1 d . . . C36 C 0.1907(8) 0.7693(2) 0.10586(18) 0.0445(11) Uani 1 1 d . . . H36 H 0.2288 0.7784 0.0734 0.053 Uiso 1 1 calc R . . C37 C 0.3465(8) 0.7913(3) 0.14247(19) 0.0470(12) Uani 1 1 d . . . H37 H 0.4915 0.8159 0.1348 0.056 Uiso 1 1 calc R . . C44 C 0.1812(10) 0.5610(3) 0.03902(19) 0.0551(14) Uani 1 1 d . . . H44 H 0.2621 0.5863 0.0149 0.066 Uiso 1 1 calc R . . C42 C -0.0337(9) 0.4849(3) 0.1070(2) 0.0565(15) Uani 1 1 d . . . H42 H -0.1102 0.4579 0.1309 0.068 Uiso 1 1 calc R . . C41 C -0.1283(10) 0.5466(3) 0.0931(2) 0.0596(15) Uani 1 1 d . . . H41 H -0.2662 0.5622 0.1076 0.071 Uiso 1 1 calc R . . C38 C -0.1991(10) 0.7065(3) 0.0743(2) 0.0610(15) Uani 1 1 d . . . H38A H -0.3414 0.6849 0.0891 0.073 Uiso 1 1 calc R . . H38B H -0.2443 0.7488 0.0572 0.073 Uiso 1 1 calc R . . C33 C 0.1069(11) 0.7475(3) 0.19853(17) 0.0581(15) Uani 1 1 d . . . H33 H 0.0772 0.7405 0.2317 0.070 Uiso 1 1 calc R . . C39 C -0.1177(12) 0.6523(3) 0.0385(2) 0.0650(16) Uani 1 1 d . . . H39A H 0.0045 0.6772 0.0194 0.078 Uiso 1 1 calc R . . H39B H -0.2505 0.6353 0.0157 0.078 Uiso 1 1 calc R . . C51 C 0.4847(8) 0.2522(2) 0.38896(15) 0.0351(10) Uani 1 1 d . . . N6A N 0.2337(17) 0.2163(4) 0.3016(3) 0.115(4) Uani 1.000(18) 1 d . . . N5 N 0.3526(9) 0.5222(2) 0.4144(2) 0.0749(16) Uani 1 1 d . . . C50 C 0.6261(8) 0.2708(3) 0.43561(17) 0.0466(12) Uani 1 1 d . . . H50A H 0.5181 0.2701 0.4630 0.056 Uiso 1 1 calc R . . H50B H 0.7341 0.2323 0.4396 0.056 Uiso 1 1 calc R . . C52 C 0.2631(9) 0.2170(3) 0.3884(2) 0.0532(13) Uani 1 1 d . . . H52 H 0.1923 0.2047 0.4178 0.064 Uiso 1 1 calc R . . C55 C 0.5709(10) 0.2688(3) 0.34456(18) 0.0536(13) Uani 1 1 d . . . H55 H 0.7221 0.2934 0.3427 0.064 Uiso 1 1 calc R . . C46 C 0.4254(10) 0.4192(3) 0.4567(2) 0.0624(16) Uani 1 1 d . . . H46 H 0.3789 0.3876 0.4810 0.075 Uiso 1 1 calc R . . C47 C 0.6210(9) 0.4063(3) 0.4304(2) 0.0555(14) Uani 1 1 d . . . C48 C 0.6729(11) 0.4535(3) 0.3947(2) 0.0707(19) Uani 1 1 d . . . H48 H 0.8018 0.4462 0.3744 0.085 Uiso 1 1 calc R . . C53 C 0.1451(11) 0.1998(3) 0.3434(4) 0.080(2) Uani 1 1 d . . . H53 H -0.0068 0.1749 0.3429 0.095 Uiso 1 1 calc R . . C45 C 0.2971(10) 0.4766(3) 0.4484(2) 0.0692(19) Uani 1 1 d . . . H45 H 0.1644 0.4843 0.4675 0.083 Uiso 1 1 calc R . . C49 C 0.7666(9) 0.3432(3) 0.4389(2) 0.0633(16) Uani 1 1 d . . . H49A H 0.8904 0.3418 0.4146 0.076 Uiso 1 1 calc R . . H49B H 0.8445 0.3517 0.4715 0.076 Uiso 1 1 calc R . . C54 C 0.439(2) 0.2497(5) 0.3041(2) 0.103(3) Uani 1 1 d . . . H54 H 0.5045 0.2622 0.2742 0.123 Uiso 1 1 calc R . . C56 C 0.5407(11) 0.5100(3) 0.3884(3) 0.077(2) Uani 1 1 d . . . H56 H 0.5840 0.5425 0.3644 0.093 Uiso 1 1 calc R . . O13 O 0.4701(12) 0.4028(4) 0.8048(2) 0.127(2) Uani 1 1 d . . . H13A H 0.5213 0.3743 0.7831 0.190 Uiso 1 1 calc R . . C58 C 0.1669(16) 0.4547(4) 0.7333(3) 0.085(2) Uani 1 1 d . . . C62 C -0.0574(17) 0.5535(5) 0.7133(3) 0.097(3) Uani 1 1 d . . . C57 C 0.517(2) 0.4710(6) 0.7941(3) 0.103(3) Uani 1 1 d . . . C64 C 0.285(2) 0.5701(6) 0.7724(3) 0.103(3) Uani 1 1 d . . . C63 C 0.279(2) 0.5061(5) 0.7614(4) 0.151(6) Uani 1 1 d . . . C59 C -0.022(2) 0.4824(7) 0.7071(4) 0.133(4) Uani 1 1 d . . . O16 O 0.035(3) 0.6171(10) 0.7016(6) 0.322(8) Uani 1 1 d . . . C65 C 0.083(4) 0.6019(7) 0.7462(5) 0.172(7) Uani 1 1 d . . . O15 O 0.669(3) 0.2132(6) 0.7025(3) 0.103(6) Uani 0.470(15) 1 d P . . C67 C 0.512(5) 0.5304(17) 0.8007(12) 0.387(19) Uani 1 1 d . . . C68 C 0.348(7) 0.4104(12) 0.7521(7) 0.39(2) Uani 1 1 d . . . O1A O 0.1920(12) 0.8471(3) 0.76227(15) 0.105(3) Uani 0.980(15) 1 d P . . O2A O -0.0906(10) 0.7989(3) 0.79173(18) 0.058(2) Uani 0.693(14) 1 d P . . H2AA H -0.1401 0.7981 0.7627 0.086 Uiso 0.55(11) 1 calc PR . . O3A O 0.024(3) 0.7239(6) 0.7795(4) 0.071(6) Uani 0.326(14) 1 d P . . H3AA H 0.0429 0.7132 0.7497 0.106 Uiso 0.19(13) 1 calc PR . . 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 O1 0.0364(16) 0.0541(19) 0.0294(16) 0.0041(13) 0.0076(12) 0.0237(14) O2 0.0367(17) 0.061(2) 0.049(2) 0.0137(16) 0.0058(14) 0.0249(15) O6 0.060(2) 0.0402(18) 0.057(2) 0.0182(16) 0.0252(17) 0.0226(16) N2 0.0284(18) 0.0357(19) 0.041(2) 0.0056(15) 0.0093(15) 0.0123(15) N1 0.0320(19) 0.040(2) 0.052(2) 0.0162(17) 0.0156(17) 0.0146(16) C1 0.033(2) 0.026(2) 0.033(2) 0.0116(16) 0.0067(17) 0.0087(16) O5 0.096(3) 0.0388(19) 0.082(3) 0.0187(18) 0.061(2) 0.0353(19) C24 0.028(2) 0.034(2) 0.051(3) 0.0085(19) 0.0084(19) 0.0122(17) C7 0.036(2) 0.029(2) 0.026(2) 0.0010(16) 0.0072(17) 0.0035(17) C21 0.027(2) 0.031(2) 0.051(3) 0.0150(19) 0.0100(18) 0.0109(17) C27 0.040(2) 0.040(2) 0.044(3) 0.010(2) 0.014(2) 0.0212(19) C29 0.031(2) 0.037(2) 0.047(3) 0.0190(19) 0.0096(19) 0.0167(18) C9 0.032(2) 0.029(2) 0.0226(19) 0.0063(15) 0.0034(16) 0.0093(16) C8 0.047(3) 0.033(2) 0.042(3) 0.0034(19) 0.019(2) 0.0076(19) C20 0.028(2) 0.038(2) 0.051(3) 0.026(2) 0.0119(19) 0.0141(17) C2 0.030(2) 0.037(2) 0.025(2) 0.0110(17) 0.0022(16) 0.0083(17) C32 0.037(2) 0.052(3) 0.041(3) 0.002(2) 0.0081(19) 0.021(2) C19 0.038(2) 0.039(2) 0.047(3) 0.019(2) 0.013(2) 0.0128(19) C30 0.035(2) 0.035(2) 0.044(3) 0.0126(19) 0.0093(19) 0.0123(18) C28 0.033(2) 0.039(2) 0.043(3) 0.0099(19) 0.0122(19) 0.0169(18) C31 0.028(2) 0.048(3) 0.045(3) 0.003(2) 0.0073(19) 0.0167(19) C25 0.0226(19) 0.0255(19) 0.042(2) 0.0046(17) 0.0046(17) 0.0104(15) C23 0.028(2) 0.050(3) 0.057(3) 0.013(2) 0.011(2) 0.019(2) C26 0.0238(19) 0.030(2) 0.048(3) 0.0029(18) 0.0045(18) 0.0115(16) C22 0.032(2) 0.058(3) 0.052(3) 0.007(2) 0.003(2) 0.019(2) C6 0.043(2) 0.061(3) 0.024(2) -0.007(2) 0.0082(18) -0.007(2) C3 0.033(2) 0.086(4) 0.030(2) 0.028(2) 0.0074(18) 0.020(2) C4 0.040(3) 0.090(4) 0.024(2) 0.023(2) 0.0040(19) 0.015(3) C5 0.055(4) 0.181(8) 0.029(3) 0.012(4) 0.015(3) 0.037(5) O11 0.0342(16) 0.0470(18) 0.0467(19) 0.0094(15) 0.0084(14) 0.0145(14) O10 0.054(2) 0.0402(18) 0.057(2) 0.0093(16) 0.0198(17) 0.0098(15) C15 0.033(2) 0.034(2) 0.0180(19) 0.0054(15) 0.0014(15) 0.0035(16) C16 0.029(2) 0.041(2) 0.035(2) 0.0196(19) -0.0013(17) 0.0000(18) O12 0.0339(19) 0.063(2) 0.098(3) 0.012(2) -0.0077(19) 0.0199(17) O7 0.091(3) 0.057(3) 0.037(2) 0.0179(17) -0.0154(19) 0.009(2) C17 0.030(2) 0.031(2) 0.055(3) 0.019(2) -0.002(2) 0.0069(17) C14 0.064(3) 0.030(2) 0.060(3) -0.008(2) 0.032(3) -0.001(2) C13 0.052(3) 0.038(2) 0.026(2) -0.0026(17) 0.0175(19) -0.010(2) O9 0.149(4) 0.045(2) 0.139(4) 0.006(2) 0.116(4) 0.023(3) C18 0.045(3) 0.098(4) 0.048(3) 0.049(3) -0.015(2) -0.018(3) C12 0.093(4) 0.070(4) 0.024(2) -0.004(2) 0.014(3) -0.040(3) C11 0.074(4) 0.106(5) 0.024(3) 0.026(3) -0.007(2) -0.048(4) O8 0.080(5) 0.013(3) 0.028(3) -0.003(2) -0.022(3) -0.004(3) C10 0.099(6) 0.204(11) 0.038(4) 0.056(5) -0.025(4) -0.057(6) N3 0.053(2) 0.043(2) 0.052(3) 0.0056(19) -0.001(2) 0.0155(19) N4 0.060(3) 0.031(2) 0.064(3) 0.0023(18) 0.030(2) 0.0142(18) C43 0.064(3) 0.035(3) 0.059(3) 0.000(2) 0.026(3) 0.006(2) C35 0.045(3) 0.024(2) 0.044(3) 0.0040(18) -0.004(2) 0.0184(18) C34 0.056(3) 0.037(3) 0.065(4) 0.008(2) 0.022(3) 0.011(2) C40 0.090(4) 0.024(2) 0.039(3) -0.0012(19) -0.004(3) 0.006(2) C36 0.051(3) 0.039(3) 0.048(3) 0.014(2) 0.009(2) 0.022(2) C37 0.040(3) 0.047(3) 0.058(3) 0.015(2) 0.001(2) 0.016(2) C44 0.083(4) 0.038(3) 0.043(3) -0.002(2) 0.020(3) 0.002(3) C42 0.064(3) 0.041(3) 0.070(4) 0.012(2) 0.037(3) 0.018(2) C41 0.064(3) 0.048(3) 0.070(4) -0.006(3) 0.017(3) 0.026(3) C38 0.075(4) 0.044(3) 0.065(4) -0.003(3) -0.024(3) 0.025(3) C33 0.103(5) 0.052(3) 0.025(2) 0.010(2) 0.020(3) 0.030(3) C39 0.099(5) 0.045(3) 0.051(3) -0.001(2) -0.014(3) 0.018(3) C51 0.045(2) 0.027(2) 0.034(2) 0.0055(17) -0.0109(19) 0.0075(18) N6A 0.182(9) 0.077(5) 0.085(5) -0.053(4) -0.093(6) 0.086(5) N5 0.066(3) 0.045(3) 0.110(4) -0.022(3) 0.047(3) -0.004(2) C50 0.044(3) 0.058(3) 0.038(3) 0.013(2) -0.007(2) -0.006(2) C52 0.043(3) 0.041(3) 0.076(4) 0.012(2) -0.015(3) 0.007(2) C55 0.076(4) 0.049(3) 0.038(3) 0.004(2) 0.000(2) 0.025(3) C46 0.060(3) 0.055(3) 0.064(4) -0.024(3) 0.018(3) -0.024(3) C47 0.047(3) 0.045(3) 0.070(4) -0.019(3) 0.016(3) -0.014(2) C48 0.071(4) 0.044(3) 0.095(5) -0.009(3) 0.048(3) -0.009(3) C53 0.056(4) 0.033(3) 0.145(7) -0.019(4) -0.056(4) 0.018(2) C45 0.055(3) 0.063(4) 0.081(4) -0.032(3) 0.040(3) -0.020(3) C49 0.049(3) 0.071(4) 0.064(4) -0.009(3) 0.000(3) -0.016(3) C54 0.197(10) 0.090(5) 0.028(3) -0.020(3) -0.028(5) 0.088(6) C56 0.086(4) 0.037(3) 0.111(5) 0.001(3) 0.058(4) 0.003(3) O13 0.158(6) 0.108(5) 0.109(5) -0.005(4) 0.041(4) -0.017(4) C58 0.119(6) 0.070(5) 0.066(5) 0.005(4) 0.017(4) 0.003(4) C62 0.138(7) 0.069(5) 0.083(5) 0.006(4) 0.054(5) -0.004(5) C57 0.128(7) 0.110(7) 0.064(5) 0.024(5) 0.005(5) -0.045(6) C64 0.138(8) 0.101(7) 0.066(5) 0.000(5) 0.029(5) -0.021(6) C63 0.237(14) 0.068(5) 0.136(9) -0.048(6) 0.138(10) -0.054(7) C59 0.146(9) 0.131(9) 0.128(9) 0.012(7) 0.029(7) 0.042(7) O16 0.334(19) 0.34(2) 0.291(19) 0.067(16) 0.088(16) -0.022(16) C65 0.31(2) 0.108(9) 0.104(9) 0.018(8) 0.096(12) 0.006(11) O15 0.170(14) 0.096(8) 0.042(6) 0.008(5) -0.029(6) 0.013(8) C67 0.33(3) 0.32(4) 0.47(4) -0.11(3) -0.08(3) -0.05(3) C68 0.80(6) 0.21(2) 0.158(18) -0.009(15) 0.18(3) 0.02(3) O1A 0.208(7) 0.091(4) 0.024(3) 0.011(2) -0.014(3) 0.064(4) O2A 0.076(5) 0.064(4) 0.029(3) 0.005(2) -0.010(2) -0.018(3) O3A 0.122(12) 0.044(7) 0.040(8) -0.007(5) -0.034(7) -0.009(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.321(5) . ? O1 H1AA 0.8400 . ? O2 C1 1.206(5) . ? O6 C8 1.206(5) . ? N2 C30 1.343(5) . ? N2 C31 1.346(6) . ? N1 C23 1.330(6) . ? N1 C19 1.330(5) . ? C1 C2 1.513(5) . ? O5 C8 1.319(5) . ? O5 H5AA 0.8400 . ? C24 C21 1.503(6) . ? C24 C25 1.523(6) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C7 C8 1.503(6) . ? C7 C9 1.520(5) . ? C7 C6 1.525(6) . ? C7 H7 0.92(5) . ? C21 C20 1.381(6) . ? C21 C22 1.393(6) . ? C27 C28 1.500(6) . ? C27 C26 1.520(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C29 C30 1.380(6) . ? C29 C28 1.386(6) . ? C29 H29 0.9500 . ? C9 C2 1.533(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C20 C19 1.381(6) . ? C20 H20 0.9500 . ? C2 C3 1.512(6) . ? C2 H2 0.96(5) . ? C32 C31 1.370(6) . ? C32 C28 1.403(6) . ? C32 H32 0.9500 . ? C19 H19 0.9500 . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C25 C26 1.521(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C23 C22 1.374(6) . ? C23 H23 0.9500 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C22 H22 0.9500 . ? C6 C4 1.526(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C3 C4 1.528(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.530(8) . ? C4 H4 1.02(6) . ? C5 O1A 1.134(8) . ? C5 O2A 1.218(8) . ? C5 O3A 1.795(14) . ? O11 C17 1.319(5) . ? O11 H11A 0.8400 . ? O10 C14 1.203(6) . ? C15 C13 1.519(5) . ? C15 C16 1.538(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.499(6) . ? C16 C18 1.530(6) . ? C16 H16 1.01(5) . ? O12 C17 1.210(5) . ? O7 C10 1.185(8) . ? O7 H7AA 0.8400 . ? C14 O9 1.316(6) . ? C14 C13 1.501(7) . ? C13 C12 1.511(7) . ? C13 H13 0.88(5) . ? O9 H9AA 0.8400 . ? C18 C11 1.531(9) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C12 C11 1.514(9) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C11 C10 1.525(8) . ? C11 H11 0.91(7) . ? O8 C10 1.350(11) . ? C10 O15 1.523(15) . ? N3 C37 1.297(6) . ? N3 C33 1.315(7) . ? N4 C43 1.332(6) . ? N4 C42 1.340(6) . ? C43 C44 1.342(7) . ? C43 H43 0.9500 . ? C35 C36 1.376(7) . ? C35 C34 1.376(7) . ? C35 C38 1.512(7) . ? C34 C33 1.434(8) . ? C34 H34 0.9500 . ? C40 C44 1.373(7) . ? C40 C41 1.398(7) . ? C40 C39 1.504(7) . ? C36 C37 1.347(7) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C44 H44 0.9500 . ? C42 C41 1.374(7) . ? C42 H42 0.9500 . ? C41 H41 0.9500 . ? C38 C39 1.465(7) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C33 H33 0.9500 . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C51 C52 1.378(7) . ? C51 C55 1.378(7) . ? C51 C50 1.504(6) . ? N6A C54 1.282(13) . ? N6A C53 1.317(11) . ? N5 C45 1.333(8) . ? N5 C56 1.334(7) . ? C50 C49 1.497(7) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C52 C53 1.402(9) . ? C52 H52 0.9500 . ? C55 C54 1.339(9) . ? C55 H55 0.9500 . ? C46 C45 1.366(9) . ? C46 C47 1.377(7) . ? C46 H46 0.9500 . ? C47 C48 1.386(8) . ? C47 C49 1.513(8) . ? C48 C56 1.354(8) . ? C48 H48 0.9500 . ? C53 H53 0.9500 . ? C45 H45 0.9500 . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C54 H54 0.9500 . ? C56 H56 0.9500 . ? O13 C57 1.321(10) . ? O13 H13A 0.8400 . ? C58 C63 1.296(13) . ? C58 C59 1.434(13) . ? C58 C68 1.48(4) . ? C62 O16 1.313(17) . ? C62 C59 1.342(13) . ? C62 C65 1.411(19) . ? C57 C67 1.10(3) . ? C57 C68 1.76(3) . ? C57 C63 1.807(18) . ? C64 C63 1.191(12) . ? C64 C65 1.526(19) . ? C64 C67 1.74(3) . ? C63 C67 1.71(3) . ? C63 C68 1.84(3) . ? O2A H2AA 0.8400 . ? O3A H3AA 0.8400 . ? 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 _geom_angle_publ_flag C1 O1 H1AA 109.5 . . ? C30 N2 C31 117.0(4) . . ? C23 N1 C19 117.2(4) . . ? O2 C1 O1 123.5(4) . . ? O2 C1 C2 124.5(4) . . ? O1 C1 C2 112.0(3) . . ? C8 O5 H5AA 109.5 . . ? C21 C24 C25 113.5(3) . . ? C21 C24 H24A 108.9 . . ? C25 C24 H24A 108.9 . . ? C21 C24 H24B 108.9 . . ? C25 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C8 C7 C9 111.4(3) . . ? C8 C7 C6 111.4(4) . . ? C9 C7 C6 111.5(3) . . ? C8 C7 H7 105(3) . . ? C9 C7 H7 106(3) . . ? C6 C7 H7 111(3) . . ? C20 C21 C22 116.3(4) . . ? C20 C21 C24 123.6(4) . . ? C22 C21 C24 120.1(4) . . ? C28 C27 C26 114.3(3) . . ? C28 C27 H27A 108.7 . . ? C26 C27 H27A 108.7 . . ? C28 C27 H27B 108.7 . . ? C26 C27 H27B 108.7 . . ? H27A C27 H27B 107.6 . . ? C30 C29 C28 120.6(4) . . ? C30 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C7 C9 C2 110.1(3) . . ? C7 C9 H9A 109.6 . . ? C2 C9 H9A 109.6 . . ? C7 C9 H9B 109.6 . . ? C2 C9 H9B 109.6 . . ? H9A C9 H9B 108.2 . . ? O6 C8 O5 123.3(4) . . ? O6 C8 C7 124.3(4) . . ? O5 C8 C7 112.4(4) . . ? C19 C20 C21 120.4(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C3 C2 C1 111.2(3) . . ? C3 C2 C9 111.7(4) . . ? C1 C2 C9 111.4(3) . . ? C3 C2 H2 107(3) . . ? C1 C2 H2 109(3) . . ? C9 C2 H2 107(3) . . ? C31 C32 C28 120.0(4) . . ? C31 C32 H32 120.0 . . ? C28 C32 H32 120.0 . . ? N1 C19 C20 122.8(4) . . ? N1 C19 H19 118.6 . . ? C20 C19 H19 118.6 . . ? N2 C30 C29 122.7(4) . . ? N2 C30 H30 118.6 . . ? C29 C30 H30 118.6 . . ? C29 C28 C32 116.3(4) . . ? C29 C28 C27 123.0(4) . . ? C32 C28 C27 120.7(4) . . ? N2 C31 C32 123.4(4) . . ? N2 C31 H31 118.3 . . ? C32 C31 H31 118.3 . . ? C26 C25 C24 112.2(3) . . ? C26 C25 H25A 109.2 . . ? C24 C25 H25A 109.2 . . ? C26 C25 H25B 109.2 . . ? C24 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? N1 C23 C22 123.6(4) . . ? N1 C23 H23 118.2 . . ? C22 C23 H23 118.2 . . ? C27 C26 C25 111.8(3) . . ? C27 C26 H26A 109.2 . . ? C25 C26 H26A 109.2 . . ? C27 C26 H26B 109.3 . . ? C25 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C23 C22 C21 119.7(5) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C7 C6 C4 110.3(4) . . ? C7 C6 H6A 109.6 . . ? C4 C6 H6A 109.6 . . ? C7 C6 H6B 109.6 . . ? C4 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C2 C3 C4 111.9(4) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C6 C4 C3 111.4(4) . . ? C6 C4 C5 110.6(5) . . ? C3 C4 C5 110.7(4) . . ? C6 C4 H4 105(3) . . ? C3 C4 H4 112(3) . . ? C5 C4 H4 107(3) . . ? O1A C5 O2A 116.9(7) . . ? O1A C5 C4 125.4(8) . . ? O2A C5 C4 114.9(6) . . ? O1A C5 O3A 113.6(7) . . ? O2A C5 O3A 60.5(7) . . ? C4 C5 O3A 105.7(7) . . ? C17 O11 H11A 109.5 . . ? C13 C15 C16 110.0(3) . . ? C13 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? C13 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C17 C16 C18 112.1(4) . . ? C17 C16 C15 110.9(3) . . ? C18 C16 C15 110.1(4) . . ? C17 C16 H16 110(3) . . ? C18 C16 H16 110(3) . . ? C15 C16 H16 104(3) . . ? C10 O7 H7AA 109.5 . . ? O12 C17 O11 123.6(5) . . ? O12 C17 C16 123.9(5) . . ? O11 C17 C16 112.5(3) . . ? O10 C14 O9 122.9(5) . . ? O10 C14 C13 125.3(4) . . ? O9 C14 C13 111.8(4) . . ? C14 C13 C12 109.7(4) . . ? C14 C13 C15 112.5(3) . . ? C12 C13 C15 111.6(4) . . ? C14 C13 H13 106(3) . . ? C12 C13 H13 109(3) . . ? C15 C13 H13 108(3) . . ? C14 O9 H9AA 109.5 . . ? C16 C18 C11 112.4(4) . . ? C16 C18 H18A 109.1 . . ? C11 C18 H18A 109.1 . . ? C16 C18 H18B 109.1 . . ? C11 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C13 C12 C11 110.8(4) . . ? C13 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C12 C11 C10 107.6(7) . . ? C12 C11 C18 111.5(4) . . ? C10 C11 C18 112.2(6) . . ? C12 C11 H11 114(4) . . ? C10 C11 H11 110(4) . . ? C18 C11 H11 102(4) . . ? O7 C10 O8 120.1(7) . . ? O7 C10 O15 88.7(8) . . ? O8 C10 O15 89.9(7) . . ? O7 C10 C11 117.5(8) . . ? O8 C10 C11 119.6(7) . . ? O15 C10 C11 108.0(8) . . ? C37 N3 C33 118.7(5) . . ? C43 N4 C42 116.7(4) . . ? N4 C43 C44 124.2(5) . . ? N4 C43 H43 117.9 . . ? C44 C43 H43 117.9 . . ? C36 C35 C34 117.3(5) . . ? C36 C35 C38 122.6(5) . . ? C34 C35 C38 120.1(5) . . ? C35 C34 C33 117.3(5) . . ? C35 C34 H34 121.4 . . ? C33 C34 H34 121.4 . . ? C44 C40 C41 116.7(4) . . ? C44 C40 C39 120.4(5) . . ? C41 C40 C39 122.9(5) . . ? C37 C36 C35 121.1(5) . . ? C37 C36 H36 119.4 . . ? C35 C36 H36 119.4 . . ? N3 C37 C36 123.2(5) . . ? N3 C37 H37 118.4 . . ? C36 C37 H37 118.4 . . ? C43 C44 C40 120.3(5) . . ? C43 C44 H44 119.8 . . ? C40 C44 H44 119.8 . . ? N4 C42 C41 122.7(5) . . ? N4 C42 H42 118.6 . . ? C41 C42 H42 118.6 . . ? C42 C41 C40 119.3(5) . . ? C42 C41 H41 120.3 . . ? C40 C41 H41 120.3 . . ? C39 C38 C35 115.0(5) . . ? C39 C38 H38A 108.5 . . ? C35 C38 H38A 108.5 . . ? C39 C38 H38B 108.5 . . ? C35 C38 H38B 108.5 . . ? H38A C38 H38B 107.5 . . ? N3 C33 C34 122.3(4) . . ? N3 C33 H33 118.8 . . ? C34 C33 H33 118.8 . . ? C38 C39 C40 117.2(5) . . ? C38 C39 H39A 108.0 . . ? C40 C39 H39A 108.0 . . ? C38 C39 H39B 108.0 . . ? C40 C39 H39B 108.0 . . ? H39A C39 H39B 107.2 . . ? C52 C51 C55 116.6(5) . . ? C52 C51 C50 121.6(4) . . ? C55 C51 C50 121.8(4) . . ? C54 N6A C53 116.0(6) . . ? C45 N5 C56 117.5(6) . . ? C49 C50 C51 115.2(4) . . ? C49 C50 H50A 108.5 . . ? C51 C50 H50A 108.5 . . ? C49 C50 H50B 108.5 . . ? C51 C50 H50B 108.5 . . ? H50A C50 H50B 107.5 . . ? C51 C52 C53 118.2(6) . . ? C51 C52 H52 120.9 . . ? C53 C52 H52 120.9 . . ? C54 C55 C51 119.3(7) . . ? C54 C55 H55 120.4 . . ? C51 C55 H55 120.4 . . ? C45 C46 C47 121.2(6) . . ? C45 C46 H46 119.4 . . ? C47 C46 H46 119.4 . . ? C46 C47 C48 115.9(6) . . ? C46 C47 C49 122.3(5) . . ? C48 C47 C49 121.8(5) . . ? C56 C48 C47 120.3(5) . . ? C56 C48 H48 119.8 . . ? C47 C48 H48 119.8 . . ? N6A C53 C52 123.4(7) . . ? N6A C53 H53 118.3 . . ? C52 C53 H53 118.3 . . ? N5 C45 C46 122.0(5) . . ? N5 C45 H45 119.0 . . ? C46 C45 H45 119.0 . . ? C50 C49 C47 113.2(4) . . ? C50 C49 H49A 108.9 . . ? C47 C49 H49A 108.9 . . ? C50 C49 H49B 108.9 . . ? C47 C49 H49B 108.9 . . ? H49A C49 H49B 107.7 . . ? N6A C54 C55 126.5(9) . . ? N6A C54 H54 116.8 . . ? C55 C54 H54 116.8 . . ? N5 C56 C48 123.2(6) . . ? N5 C56 H56 118.4 . . ? C48 C56 H56 118.4 . . ? C57 O13 H13A 109.5 . . ? C63 C58 C59 110.8(11) . . ? C63 C58 C68 82.8(13) . . ? C59 C58 C68 166.2(13) . . ? O16 C62 C59 139.9(12) . . ? O16 C62 C65 57.4(9) . . ? C59 C62 C65 121.5(12) . . ? C67 C57 O13 153(2) . . ? C67 C57 C68 128(2) . . ? O13 C57 C68 61.3(9) . . ? C67 C57 C63 66.8(19) . . ? O13 C57 C63 112.9(8) . . ? C68 C57 C63 62.1(11) . . ? C63 C64 C65 109.4(13) . . ? C63 C64 C67 68.3(12) . . ? C65 C64 C67 177.6(13) . . ? C64 C63 C58 141.8(17) . . ? C64 C63 C67 71.2(13) . . ? C58 C63 C67 146.7(17) . . ? C64 C63 C57 107.6(12) . . ? C58 C63 C57 110.5(9) . . ? C67 C63 C57 36.4(12) . . ? C64 C63 C68 165(2) . . ? C58 C63 C68 52.8(12) . . ? C67 C63 C68 93.9(19) . . ? C57 C63 C68 57.7(13) . . ? C62 C59 C58 119.7(11) . . ? C62 C65 C64 116.7(11) . . ? C57 C67 C63 76.8(16) . . ? C57 C67 C64 117(2) . . ? C63 C67 C64 40.5(9) . . ? C58 C68 C57 104.5(14) . . ? C58 C68 C63 44.4(9) . . ? C57 C68 C63 60.2(9) . . ? C5 O2A H2AA 109.5 . . ? C5 O3A H3AA 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.853 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.089