# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Nizar Issa' ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; 'Sarah A. Barnett' ; Light Source Diamond House Harwell Science and Innovation Campus Didcot Oxfordshire OX11 0DE United Kingdom ; 'Sharmarke Mohamed' ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; 'Doris E. Braun' ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; 'Royston C. B. Copley' ; GlaxoSmithKline Gunnels Wood Road Stevenage Herts SG1 2NY United Kingdom ; ; D.A.Tocher ; ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; 'Sarah L. Price' ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; _publ_contact_author_address ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ United Kingdom ; _publ_contact_author_email s.l.price@ucl.ac.uk _publ_contact_author_fax '+44 (0)20 7679 7463' _publ_contact_author_phone '+44 (0)20 7679 4622' #TrackingRef '- 4ABAAP_III.cif' # SUBMISSION DETAILS _publ_contact_author_name 'Sarah L. Price' # TITLE AND AUTHOR LIST _publ_section_title ; Screening for pharmaceutical cocrystals of succinic acid and 4-aminobenzoic acid ; data_4-AminobenzoicAcid_Antipyrine _database_code_depnum_ccdc_archive 'CCDC 847627' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Antipyrine 4-Aminobenzoic acid (1/1) ; _chemical_name_common '(Antipyrine)(4-Aminobenzoic acid)' _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N2 O, C7 H7 N O2' _chemical_formula_sum 'C18 H19 N3 O3' _chemical_formula_weight 325.36 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.5767(12) _cell_length_b 12.7646(17) _cell_length_c 13.9388(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.758(2) _cell_angle_gamma 90.00 _cell_volume 1703.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2519 _cell_measurement_theta_min 2.6590 _cell_measurement_theta_max 22.2314 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.867080 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS v2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14769 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 28.39 _reflns_number_total 4240 _reflns_number_gt 3175 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; SHELXTL (Bruker, 2000) and Mercury (Macrae et al., 2006) ; _computing_publication_material 'Bruker SHELXTL and local programs' _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. All the H atoms bonded to carbon atoms were generated by a riding model in idealized geometries and refined with Uiso(H) = 1.2 Ueq(C) for phenyl C-H and Uiso(H) = 1.5 Ueq(C) for -CH3 groups. The amino and carboxylic acid H atoms were identified from difference maps and their Uiso parameters were refined freely. The position of H1 was refined using the SHELXL97 DFIX 0.84 (0.01) command. ; _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^)+(0.0645P)^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_number_reflns 4240 _refine_ls_number_parameters 461 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 C1 C 0.9899(3) 0.0851(3) 0.7004(2) 0.0420(8) Uani 1 1 d . . . C2 C 0.8836(3) 0.1220(2) 0.7668(2) 0.0327(7) Uani 1 1 d . . . C3 C 0.8221(3) 0.2205(3) 0.7531(2) 0.0369(7) Uani 1 1 d . . . H2 H 0.8518 0.2627 0.7011 0.044 Uiso 1 1 calc R . . C4 C 0.7201(3) 0.2580(3) 0.8124(2) 0.0381(8) Uani 1 1 d . . . H3A H 0.6793 0.3246 0.8004 0.046 Uiso 1 1 calc R . . C5 C 0.6763(3) 0.1981(2) 0.8904(2) 0.0319(7) Uani 1 1 d . . . C6 C 0.7370(3) 0.0998(3) 0.9048(2) 0.0368(7) Uani 1 1 d . . . H6 H 0.7081 0.0578 0.9572 0.044 Uiso 1 1 calc R . . C7 C 0.8383(3) 0.0627(2) 0.8439(2) 0.0350(7) Uani 1 1 d . . . H7 H 0.8777 -0.0046 0.8550 0.042 Uiso 1 1 calc R . . C8 C 0.5914(3) 0.5925(3) 0.8059(2) 0.0331(7) Uani 1 1 d . . . C9 C 0.6760(3) 0.6414(2) 0.7305(2) 0.0295(6) Uani 1 1 d . . . C10 C 0.6759(3) 0.6047(3) 0.6367(2) 0.0355(7) Uani 1 1 d . . . H9 H 0.6197 0.5459 0.6200 0.043 Uiso 1 1 calc R . . C11 C 0.7562(3) 0.6520(3) 0.5674(2) 0.0372(7) Uani 1 1 d . . . H10 H 0.7542 0.6260 0.5036 0.045 Uiso 1 1 calc R . . C12 C 0.8402(3) 0.7377(2) 0.59051(19) 0.0284(6) Uani 1 1 d . . . C13 C 0.8402(3) 0.7755(2) 0.6836(2) 0.0364(7) Uani 1 1 d . . . H13 H 0.8963 0.8342 0.7004 0.044 Uiso 1 1 calc R . . C14 C 0.7593(3) 0.7281(3) 0.7519(2) 0.0374(7) Uani 1 1 d . . . H14 H 0.7603 0.7552 0.8154 0.045 Uiso 1 1 calc R . . C15 C -0.0957(3) 0.4902(3) 0.9342(3) 0.0501(9) Uani 1 1 d . . . H16 H -0.1804 0.4529 0.9532 0.075 Uiso 1 1 calc R . . H17 H -0.1116 0.5240 0.8719 0.075 Uiso 1 1 calc R . . H15 H -0.0725 0.5435 0.9825 0.075 Uiso 1 1 calc R . . C16 C -0.0548(4) 0.2985(3) 1.0583(2) 0.0491(9) Uani 1 1 d . . . H19 H -0.0805 0.3527 1.1047 0.074 Uiso 1 1 calc R . . H20 H -0.0167 0.2376 1.0926 0.074 Uiso 1 1 calc R . . H18 H -0.1377 0.2775 1.0211 0.074 Uiso 1 1 calc R . . C17 C 0.0528(3) 0.3410(2) 0.9921(2) 0.0341(7) Uani 1 1 d . . . C18 C 0.1922(3) 0.3184(2) 0.9871(2) 0.0312(7) Uani 1 1 d . . . H21 H 0.2401 0.2656 1.0225 0.037 Uiso 1 1 calc R . . C19 C 0.2524(3) 0.3877(2) 0.91992(19) 0.0292(6) Uani 1 1 d . . . C20 C 0.1449(3) 0.5089(2) 0.7997(2) 0.0334(7) Uani 1 1 d . . . C21 C 0.2181(3) 0.6017(3) 0.7953(2) 0.0407(8) Uani 1 1 d . . . H22 H 0.2660 0.6281 0.8503 0.049 Uiso 1 1 calc R . . C22 C 0.2205(4) 0.6557(3) 0.7091(3) 0.0567(11) Uani 1 1 d . . . H23 H 0.2718 0.7192 0.7049 0.068 Uiso 1 1 calc R . . C23 C 0.1503(4) 0.6190(3) 0.6302(3) 0.0580(11) Uani 1 1 d . . . H24 H 0.1535 0.6570 0.5717 0.070 Uiso 1 1 calc R . . C24 C 0.0755(5) 0.5279(4) 0.6348(3) 0.0616(11) Uani 1 1 d . . . H25 H 0.0257 0.5033 0.5799 0.074 Uiso 1 1 calc R . . C25 C 0.0725(4) 0.4716(3) 0.7200(2) 0.0492(9) Uani 1 1 d . . . H26 H 0.0213 0.4080 0.7236 0.059 Uiso 1 1 calc R . . C26 C 0.6497(3) 0.9936(3) 0.5615(3) 0.0466(9) Uani 1 1 d . . . H28 H 0.7319 0.9617 0.5322 0.070 Uiso 1 1 calc R . . H27 H 0.6683 1.0051 0.6300 0.070 Uiso 1 1 calc R . . H29 H 0.6294 1.0607 0.5303 0.070 Uiso 1 1 calc R . . C27 C 0.5991(4) 0.8448(4) 0.3949(2) 0.0528(10) Uani 1 1 d . . . H32 H 0.6257 0.9096 0.3622 0.079 Uiso 1 1 calc R . . H31 H 0.5583 0.7958 0.3483 0.079 Uiso 1 1 calc R . . H30 H 0.6820 0.8131 0.4250 0.079 Uiso 1 1 calc R . . C28 C 0.4944(3) 0.8691(3) 0.4702(2) 0.0354(7) Uani 1 1 d . . . C29 C 0.3551(3) 0.8483(3) 0.4706(2) 0.0372(7) Uani 1 1 d . . . H33 H 0.3056 0.8079 0.4242 0.045 Uiso 1 1 calc R . . C30 C 0.2963(3) 0.8971(2) 0.5518(2) 0.0312(6) Uani 1 1 d . . . C31 C 0.4100(3) 0.9708(2) 0.6972(2) 0.0306(6) Uani 1 1 d . . . C32 C 0.3511(4) 1.0607(3) 0.7314(3) 0.0476(9) Uani 1 1 d . . . H34 H 0.3136 1.1116 0.6885 0.057 Uiso 1 1 calc R . . C33 C 0.3471(4) 1.0764(4) 0.8298(3) 0.0728(15) Uani 1 1 d . . . H35 H 0.3048 1.1378 0.8547 0.087 Uiso 1 1 calc R . . C34 C 0.4039(5) 1.0036(6) 0.8913(3) 0.0814(18) Uani 1 1 d . . . H36 H 0.4018 1.0150 0.9586 0.098 Uiso 1 1 calc R . . C35 C 0.4635(5) 0.9147(4) 0.8559(3) 0.0734(14) Uani 1 1 d . . . H37 H 0.5032 0.8647 0.8987 0.088 Uiso 1 1 calc R . . C36 C 0.4664(4) 0.8973(3) 0.7593(2) 0.0486(9) Uani 1 1 d . . . H38 H 0.5069 0.8350 0.7349 0.058 Uiso 1 1 calc R . . H4 H 0.532(4) 0.284(3) 0.933(2) 0.043(11) Uiso 1 1 d . . . H5 H 0.550(4) 0.195(3) 1.003(3) 0.044(11) Uiso 1 1 d . . . H11 H 0.935(3) 0.749(2) 0.472(2) 0.021(8) Uiso 1 1 d . . . H12 H 0.990(3) 0.825(3) 0.540(2) 0.030(8) Uiso 1 1 d . . . N1 N 0.5808(3) 0.2367(3) 0.9534(2) 0.0439(7) Uani 1 1 d . . . N2 N 0.9181(3) 0.7864(2) 0.5206(2) 0.0350(6) Uani 1 1 d . . . N3 N 0.1452(2) 0.4511(2) 0.88751(17) 0.0323(6) Uani 1 1 d . . . N4 N 0.0200(3) 0.4158(2) 0.92697(18) 0.0366(6) Uani 1 1 d . . . N5 N 0.4059(2) 0.9497(2) 0.59673(17) 0.0312(6) Uani 1 1 d . . . N6 N 0.5295(3) 0.9235(2) 0.54974(17) 0.0344(6) Uani 1 1 d . . . O1 O 1.0357(2) -0.01050(18) 0.71891(17) 0.0421(5) Uani 1 1 d D . . H1 H 1.087(3) -0.036(3) 0.6753(19) 0.051(11) Uiso 1 1 d D . . O2 O 1.0332(3) 0.1362(3) 0.6337(2) 0.0759(10) Uani 1 1 d . . . O3 O 0.5788(3) 0.6274(2) 0.88587(15) 0.0522(7) Uani 1 1 d . . . O4 O 0.5297(2) 0.50490(17) 0.77685(16) 0.0381(5) Uani 1 1 d . . . H8 H 0.479(3) 0.480(3) 0.820(2) 0.038(10) Uiso 1 1 d . . . O5 O 0.3753(2) 0.39525(19) 0.89114(15) 0.0398(5) Uani 1 1 d . . . O6 O 0.1752(2) 0.8986(2) 0.58371(15) 0.0437(6) 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 C1 0.0360(18) 0.051(2) 0.0396(19) 0.0069(17) 0.0026(14) 0.0014(16) C2 0.0285(15) 0.0358(17) 0.0338(16) 0.0034(13) -0.0003(12) -0.0039(13) C3 0.0331(17) 0.0418(18) 0.0357(17) 0.0137(14) -0.0006(13) -0.0042(14) C4 0.0372(18) 0.0295(16) 0.0473(19) 0.0053(14) -0.0083(15) 0.0029(13) C5 0.0303(16) 0.0369(17) 0.0283(15) -0.0010(13) -0.0048(12) 0.0024(13) C6 0.0406(18) 0.0392(17) 0.0308(16) 0.0088(14) 0.0051(13) 0.0004(15) C7 0.0331(17) 0.0324(16) 0.0394(18) 0.0044(13) -0.0002(13) 0.0022(13) C8 0.0326(16) 0.0360(17) 0.0307(17) 0.0016(14) 0.0030(12) 0.0041(14) C9 0.0296(15) 0.0323(15) 0.0266(15) 0.0014(12) 0.0038(12) 0.0022(13) C10 0.0398(17) 0.0366(17) 0.0302(16) -0.0037(14) 0.0051(13) -0.0072(14) C11 0.0471(19) 0.0412(17) 0.0235(15) -0.0071(13) 0.0045(13) -0.0101(15) C12 0.0257(14) 0.0343(15) 0.0252(14) 0.0036(12) 0.0032(11) 0.0020(12) C13 0.0416(18) 0.0355(17) 0.0321(16) -0.0059(14) 0.0007(13) -0.0117(14) C14 0.0446(19) 0.0432(18) 0.0243(15) -0.0079(14) -0.0001(13) -0.0050(16) C15 0.0320(18) 0.062(2) 0.056(2) 0.0083(19) 0.0100(15) 0.0081(17) C16 0.0382(19) 0.061(2) 0.048(2) 0.0061(18) 0.0022(15) -0.0169(17) C17 0.0357(17) 0.0371(17) 0.0296(16) -0.0023(14) 0.0022(13) -0.0113(14) C18 0.0344(16) 0.0317(15) 0.0276(15) 0.0028(13) 0.0012(12) -0.0046(13) C19 0.0270(15) 0.0321(15) 0.0285(14) -0.0017(13) 0.0010(11) -0.0004(13) C20 0.0306(16) 0.0374(17) 0.0323(16) 0.0039(14) 0.0078(12) 0.0093(13) C21 0.0376(18) 0.0360(17) 0.0488(19) 0.0052(16) 0.0083(14) 0.0075(15) C22 0.052(2) 0.050(2) 0.068(3) 0.024(2) 0.020(2) 0.0148(19) C23 0.071(3) 0.060(3) 0.044(2) 0.0214(19) 0.0162(19) 0.034(2) C24 0.072(3) 0.076(3) 0.037(2) -0.003(2) 0.0016(19) 0.028(2) C25 0.059(2) 0.048(2) 0.0407(19) -0.0012(17) -0.0038(17) 0.0039(18) C26 0.0328(18) 0.059(2) 0.048(2) -0.0031(18) 0.0088(15) -0.0086(16) C27 0.050(2) 0.073(3) 0.0359(18) -0.0037(18) 0.0031(16) 0.028(2) C28 0.0389(17) 0.0396(18) 0.0277(15) 0.0004(13) 0.0008(13) 0.0129(14) C29 0.0403(18) 0.0401(18) 0.0310(16) -0.0065(14) -0.0029(13) 0.0041(15) C30 0.0294(16) 0.0304(15) 0.0338(16) -0.0029(13) -0.0026(12) 0.0001(13) C31 0.0251(14) 0.0365(16) 0.0303(15) -0.0030(13) 0.0056(11) -0.0070(13) C32 0.0383(19) 0.049(2) 0.055(2) -0.0190(18) 0.0017(16) -0.0014(16) C33 0.038(2) 0.104(4) 0.077(3) -0.058(3) 0.004(2) -0.005(2) C34 0.053(3) 0.158(6) 0.034(2) -0.020(3) 0.0097(19) -0.042(3) C35 0.085(3) 0.098(4) 0.038(2) 0.018(2) -0.003(2) -0.031(3) C36 0.055(2) 0.048(2) 0.0426(19) 0.0072(17) -0.0066(16) -0.0148(18) N1 0.0468(18) 0.0477(18) 0.0372(17) 0.0022(15) 0.0013(14) 0.0141(16) N2 0.0341(15) 0.0400(16) 0.0309(15) -0.0014(13) 0.0033(12) -0.0072(13) N3 0.0300(13) 0.0351(13) 0.0321(13) 0.0034(11) 0.0053(10) -0.0035(11) N4 0.0262(14) 0.0450(16) 0.0386(14) 0.0040(12) 0.0023(11) -0.0028(12) N5 0.0284(13) 0.0357(14) 0.0297(13) -0.0024(11) 0.0023(10) 0.0040(11) N6 0.0321(14) 0.0430(15) 0.0282(13) -0.0019(11) 0.0043(10) 0.0037(11) O1 0.0388(13) 0.0391(13) 0.0487(14) -0.0049(11) 0.0144(10) -0.0041(11) O2 0.076(2) 0.089(2) 0.0643(18) 0.0415(17) 0.0378(16) 0.0317(18) O3 0.0667(16) 0.0638(17) 0.0264(12) -0.0090(11) 0.0148(11) -0.0181(13) O4 0.0421(13) 0.0352(12) 0.0372(12) 0.0033(10) 0.0136(10) -0.0036(10) O5 0.0306(11) 0.0457(13) 0.0432(12) 0.0162(11) 0.0083(9) 0.0030(10) O6 0.0302(12) 0.0573(15) 0.0435(13) -0.0114(12) 0.0023(9) -0.0032(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 C1 O2 1.213(4) . ? C1 O1 1.321(4) . ? C1 C2 1.463(4) . ? C2 C7 1.389(4) . ? C2 C3 1.400(4) . ? C3 C4 1.375(5) . ? C3 H2 0.9500 . ? C4 C5 1.397(4) . ? C4 H3A 0.9500 . ? C5 N1 1.367(4) . ? C5 C6 1.396(4) . ? C6 C7 1.381(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 O3 1.208(4) . ? C8 O4 1.325(4) . ? C8 C9 1.473(4) . ? C9 C10 1.389(4) . ? C9 C14 1.394(4) . ? C10 C11 1.382(4) . ? C10 H9 0.9500 . ? C11 C12 1.393(4) . ? C11 H10 0.9500 . ? C12 N2 1.383(4) . ? C12 C13 1.384(4) . ? C13 C14 1.375(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N4 1.464(4) . ? C15 H16 0.9800 . ? C15 H17 0.9800 . ? C15 H15 0.9800 . ? C16 C17 1.494(4) . ? C16 H19 0.9800 . ? C16 H20 0.9800 . ? C16 H18 0.9800 . ? C17 N4 1.352(4) . ? C17 C18 1.367(4) . ? C18 C19 1.417(4) . ? C18 H21 0.9500 . ? C19 O5 1.252(3) 1 ? C19 O5 1.252(3) 1 ? C19 O5 1.252(3) . ? C19 N3 1.378(4) . ? C20 C21 1.379(5) . ? C20 C25 1.386(5) . ? C20 N3 1.429(4) . ? C21 C22 1.386(5) . ? C21 H22 0.9500 . ? C22 C23 1.364(6) . ? C22 H23 0.9500 . ? C23 C24 1.368(7) . ? C23 H24 0.9500 . ? C24 C25 1.389(6) . ? C24 H25 0.9500 . ? C25 H26 0.9500 . ? C26 N6 1.466(4) . ? C26 H28 0.9800 . ? C26 H27 0.9800 . ? C26 H29 0.9800 . ? C27 C28 1.492(4) . ? C27 H32 0.9800 . ? C27 H31 0.9800 . ? C27 H30 0.9800 . ? C28 N6 1.348(4) . ? C28 C29 1.360(5) . ? C29 C30 1.415(4) . ? C29 H33 0.9500 . ? C30 O6 1.248(4) . ? C30 N5 1.388(4) . ? C31 C32 1.368(5) . ? C31 C36 1.381(5) . ? C31 N5 1.426(4) . ? C32 C33 1.386(6) . ? C32 H34 0.9500 . ? C33 C34 1.373(8) . ? C33 H35 0.9500 . ? C34 C35 1.365(8) . ? C34 H36 0.9500 . ? C35 C36 1.365(5) . ? C35 H37 0.9500 . ? C36 H38 0.9500 . ? N1 H4 0.81(4) . ? N1 H5 0.92(4) . ? N2 H11 0.85(3) . ? N2 H12 0.89(4) . ? N3 N4 1.401(3) . ? N5 N6 1.402(3) . ? O1 H1 0.852(10) . ? O4 H8 0.84(3) . ? O5 O5 0.0000 1 ? O5 O5 0.0000 1 ? 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 O2 C1 O1 122.0(3) . . ? O2 C1 C2 124.0(3) . . ? O1 C1 C2 114.0(3) . . ? C7 C2 C3 117.4(3) . . ? C7 C2 C1 122.8(3) . . ? C3 C2 C1 119.8(3) . . ? C4 C3 C2 122.1(3) . . ? C4 C3 H2 119.0 . . ? C2 C3 H2 119.0 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H3A 120.0 . . ? C5 C4 H3A 120.0 . . ? N1 C5 C6 120.8(3) . . ? N1 C5 C4 120.8(3) . . ? C6 C5 C4 118.3(3) . . ? C7 C6 C5 121.0(3) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C2 121.1(3) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? O3 C8 O4 122.9(3) . . ? O3 C8 C9 124.3(3) . . ? O4 C8 C9 112.8(2) . . ? C10 C9 C14 117.5(3) . . ? C10 C9 C8 122.3(3) . . ? C14 C9 C8 120.2(3) . . ? C11 C10 C9 121.1(3) . . ? C11 C10 H9 119.4 . . ? C9 C10 H9 119.4 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H10 119.8 . . ? C12 C11 H10 119.8 . . ? N2 C12 C13 120.8(3) . . ? N2 C12 C11 120.3(3) . . ? C13 C12 C11 118.9(3) . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 121.8(3) . . ? C13 C14 H14 119.1 . . ? C9 C14 H14 119.1 . . ? N4 C15 H16 109.5 . . ? N4 C15 H17 109.5 . . ? H16 C15 H17 109.5 . . ? N4 C15 H15 109.5 . . ? H16 C15 H15 109.5 . . ? H17 C15 H15 109.5 . . ? C17 C16 H19 109.5 . . ? C17 C16 H20 109.5 . . ? H19 C16 H20 109.5 . . ? C17 C16 H18 109.5 . . ? H19 C16 H18 109.5 . . ? H20 C16 H18 109.5 . . ? N4 C17 C18 109.4(3) . . ? N4 C17 C16 121.0(3) . . ? C18 C17 C16 129.5(3) . . ? C17 C18 C19 108.0(3) . . ? C17 C18 H21 126.0 . . ? C19 C18 H21 126.0 . . ? O5 C19 O5 0.00(18) 1 1 ? O5 C19 O5 0.00(18) 1 . ? O5 C19 O5 0.00(18) 1 . ? O5 C19 N3 123.3(3) 1 . ? O5 C19 N3 123.3(3) 1 . ? O5 C19 N3 123.3(3) . . ? O5 C19 C18 130.7(3) 1 . ? O5 C19 C18 130.7(3) 1 . ? O5 C19 C18 130.7(3) . . ? N3 C19 C18 106.0(2) . . ? C21 C20 C25 120.6(3) . . ? C21 C20 N3 119.1(3) . . ? C25 C20 N3 120.3(3) . . ? C20 C21 C22 118.7(3) . . ? C20 C21 H22 120.6 . . ? C22 C21 H22 120.6 . . ? C23 C22 C21 121.0(4) . . ? C23 C22 H23 119.5 . . ? C21 C22 H23 119.5 . . ? C22 C23 C24 120.4(4) . . ? C22 C23 H24 119.8 . . ? C24 C23 H24 119.8 . . ? C23 C24 C25 119.8(4) . . ? C23 C24 H25 120.1 . . ? C25 C24 H25 120.1 . . ? C20 C25 C24 119.5(4) . . ? C20 C25 H26 120.3 . . ? C24 C25 H26 120.3 . . ? N6 C26 H28 109.5 . . ? N6 C26 H27 109.5 . . ? H28 C26 H27 109.5 . . ? N6 C26 H29 109.5 . . ? H28 C26 H29 109.5 . . ? H27 C26 H29 109.5 . . ? C28 C27 H32 109.5 . . ? C28 C27 H31 109.5 . . ? H32 C27 H31 109.5 . . ? C28 C27 H30 109.5 . . ? H32 C27 H30 109.5 . . ? H31 C27 H30 109.5 . . ? N6 C28 C29 109.3(3) . . ? N6 C28 C27 121.5(3) . . ? C29 C28 C27 129.1(3) . . ? C28 C29 C30 108.6(3) . . ? C28 C29 H33 125.7 . . ? C30 C29 H33 125.7 . . ? O6 C30 N5 122.1(3) . . ? O6 C30 C29 132.4(3) . . ? N5 C30 C29 105.5(3) . . ? C32 C31 C36 120.7(3) . . ? C32 C31 N5 119.6(3) . . ? C36 C31 N5 119.5(3) . . ? C31 C32 C33 118.9(4) . . ? C31 C32 H34 120.5 . . ? C33 C32 H34 120.5 . . ? C34 C33 C32 120.2(4) . . ? C34 C33 H35 119.9 . . ? C32 C33 H35 119.9 . . ? C35 C34 C33 120.1(4) . . ? C35 C34 H36 120.0 . . ? C33 C34 H36 120.0 . . ? C36 C35 C34 120.4(5) . . ? C36 C35 H37 119.8 . . ? C34 C35 H37 119.8 . . ? C35 C36 C31 119.7(4) . . ? C35 C36 H38 120.2 . . ? C31 C36 H38 120.2 . . ? C5 N1 H4 115(2) . . ? C5 N1 H5 120(2) . . ? H4 N1 H5 120(3) . . ? C12 N2 H11 115(2) . . ? C12 N2 H12 117.3(19) . . ? H11 N2 H12 114(3) . . ? C19 N3 N4 108.7(2) . . ? C19 N3 C20 125.2(2) . . ? N4 N3 C20 120.7(2) . . ? C17 N4 N3 107.3(2) . . ? C17 N4 C15 125.6(3) . . ? N3 N4 C15 118.1(3) . . ? C30 N5 N6 108.1(2) . . ? C30 N5 C31 123.0(2) . . ? N6 N5 C31 119.4(2) . . ? C28 N6 N5 107.8(2) . . ? C28 N6 C26 126.4(3) . . ? N5 N6 C26 117.9(3) . . ? C1 O1 H1 114(3) . . ? C8 O4 H8 111(2) . . ? O5 O5 O5 0(10) 1 1 ? O5 O5 C19 0(10) 1 . ? O5 O5 C19 0(10) 1 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C7 -178.4(4) . . . . ? O1 C1 C2 C7 1.7(4) . . . . ? O2 C1 C2 C3 2.4(5) . . . . ? O1 C1 C2 C3 -177.5(3) . . . . ? C7 C2 C3 C4 -0.4(5) . . . . ? C1 C2 C3 C4 178.8(3) . . . . ? C2 C3 C4 C5 1.1(5) . . . . ? C3 C4 C5 N1 176.2(3) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? N1 C5 C6 C7 -176.9(3) . . . . ? C4 C5 C6 C7 0.4(5) . . . . ? C5 C6 C7 C2 0.3(5) . . . . ? C3 C2 C7 C6 -0.3(4) . . . . ? C1 C2 C7 C6 -179.5(3) . . . . ? O3 C8 C9 C10 -173.1(3) . . . . ? O4 C8 C9 C10 7.0(4) . . . . ? O3 C8 C9 C14 6.5(5) . . . . ? O4 C8 C9 C14 -173.4(3) . . . . ? C14 C9 C10 C11 0.3(5) . . . . ? C8 C9 C10 C11 180.0(3) . . . . ? C9 C10 C11 C12 0.5(5) . . . . ? C10 C11 C12 N2 -178.6(3) . . . . ? C10 C11 C12 C13 -0.9(5) . . . . ? N2 C12 C13 C14 178.3(3) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? C12 C13 C14 C9 0.3(5) . . . . ? C10 C9 C14 C13 -0.7(5) . . . . ? C8 C9 C14 C13 179.6(3) . . . . ? N4 C17 C18 C19 4.2(3) . . . . ? C16 C17 C18 C19 -173.3(3) . . . . ? C17 C18 C19 O5 -178.9(3) . . . 1 ? C17 C18 C19 O5 -178.9(3) . . . 1 ? C17 C18 C19 O5 -178.9(3) . . . . ? C17 C18 C19 N3 0.7(3) . . . . ? C25 C20 C21 C22 -1.4(5) . . . . ? N3 C20 C21 C22 178.2(3) . . . . ? C20 C21 C22 C23 1.0(5) . . . . ? C21 C22 C23 C24 0.2(6) . . . . ? C22 C23 C24 C25 -1.0(6) . . . . ? C21 C20 C25 C24 0.8(5) . . . . ? N3 C20 C25 C24 -178.9(3) . . . . ? C23 C24 C25 C20 0.5(6) . . . . ? N6 C28 C29 C30 3.5(4) . . . . ? C27 C28 C29 C30 -173.0(3) . . . . ? C28 C29 C30 O6 -178.2(3) . . . . ? C28 C29 C30 N5 1.9(3) . . . . ? C36 C31 C32 C33 -0.9(5) . . . . ? N5 C31 C32 C33 175.4(3) . . . . ? C31 C32 C33 C34 1.3(6) . . . . ? C32 C33 C34 C35 -0.7(7) . . . . ? C33 C34 C35 C36 -0.3(7) . . . . ? C34 C35 C36 C31 0.7(6) . . . . ? C32 C31 C36 C35 -0.1(5) . . . . ? N5 C31 C36 C35 -176.4(3) . . . . ? O5 C19 N3 N4 174.5(3) 1 . . . ? O5 C19 N3 N4 174.5(3) 1 . . . ? O5 C19 N3 N4 174.5(3) . . . . ? C18 C19 N3 N4 -5.2(3) . . . . ? O5 C19 N3 C20 20.5(5) 1 . . . ? O5 C19 N3 C20 20.5(5) 1 . . . ? O5 C19 N3 C20 20.5(5) . . . . ? C18 C19 N3 C20 -159.1(3) . . . . ? C21 C20 N3 C19 -78.8(4) . . . . ? C25 C20 N3 C19 100.8(4) . . . . ? C21 C20 N3 N4 130.2(3) . . . . ? C25 C20 N3 N4 -50.2(4) . . . . ? C18 C17 N4 N3 -7.3(3) . . . . ? C16 C17 N4 N3 170.4(3) . . . . ? C18 C17 N4 C15 -153.4(3) . . . . ? C16 C17 N4 C15 24.3(5) . . . . ? C19 N3 N4 C17 7.8(3) . . . . ? C20 N3 N4 C17 163.1(3) . . . . ? C19 N3 N4 C15 156.8(3) . . . . ? C20 N3 N4 C15 -47.8(4) . . . . ? O6 C30 N5 N6 173.7(3) . . . . ? C29 C30 N5 N6 -6.4(3) . . . . ? O6 C30 N5 C31 27.6(4) . . . . ? C29 C30 N5 C31 -152.5(3) . . . . ? C32 C31 N5 C30 -88.6(4) . . . . ? C36 C31 N5 C30 87.8(4) . . . . ? C32 C31 N5 N6 128.9(3) . . . . ? C36 C31 N5 N6 -54.7(4) . . . . ? C29 C28 N6 N5 -7.5(3) . . . . ? C27 C28 N6 N5 169.4(3) . . . . ? C29 C28 N6 C26 -155.5(3) . . . . ? C27 C28 N6 C26 21.4(5) . . . . ? C30 N5 N6 C28 8.7(3) . . . . ? C31 N5 N6 C28 156.2(3) . . . . ? C30 N5 N6 C26 159.9(3) . . . . ? C31 N5 N6 C26 -52.6(4) . . . . ? O5 C19 O5 O5 0.0(7) 1 . . 1 ? N3 C19 O5 O5 0.0(7) . . . 1 ? C18 C19 O5 O5 0.0(7) . . . 1 ? O5 C19 O5 O5 0.0(7) 1 . . 1 ? N3 C19 O5 O5 0.0(7) . . . 1 ? C18 C19 O5 O5 0.0(7) . . . 1 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H4 O5 0.81(4) 2.14(4) 2.946(4) 170(3) 1 N1 H5 O3 0.92(4) 2.18(4) 3.065(4) 163(3) 2_647 N2 H11 O2 0.85(3) 2.08(3) 2.923(4) 171(3) 2_756 N2 H12 O6 0.89(4) 2.09(4) 2.971(4) 173(3) 1_655 O1 H1 O6 0.852(10) 1.752(12) 2.598(3) 172(4) 1_645 O4 H8 O5 0.84(3) 1.78(4) 2.597(3) 164(4) 1 _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.179 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.041 # Attachment '- 4ABAPHE_IV.cif' data_4-AminobenzoicAcid_Phenazine _database_code_depnum_ccdc_archive 'CCDC 847628' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Phenazine 4-Aminobenzoic acid (2/1) ; _chemical_name_common '2(Phenazine)(4-Aminobenzoic acid)' _chemical_melting_point ? _chemical_formula_moiety '2(C12 H8 N2), C7 H7 N O2' _chemical_formula_sum 'C31 H23 N5 O2' _chemical_formula_weight 497.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0029 0.0015 '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 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0101 0.0057 '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 15.557(2) _cell_length_b 17.056(3) _cell_length_c 19.782(3) _cell_angle_alpha 80.658(5) _cell_angle_beta 78.559(7) _cell_angle_gamma 77.168(6) _cell_volume 4977.6(13) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8556 _cell_measurement_theta_min 1.4763 _cell_measurement_theta_max 31.7057 _exptl_crystal_description 'Hexagonal Block' _exptl_crystal_colour Orange _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7039 _exptl_absorpt_process_details 'REQAB within d*TREK' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Diamond Light Source Beamline I19' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Crystal Logic goniometer Rigaku Saturn724+ (2x2 bin mode)' _diffrn_measurement_method '\w rotation with 1 degree frames' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 76255 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.03 _diffrn_reflns_theta_max 29.48 _reflns_number_total 29699 _reflns_number_gt 22369 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM 2.0.0 b4 1998-2008 Rigaku, Inc.' _computing_cell_refinement 'd*TREK version 9.9 Rigaku 2007' _computing_data_reduction 'd*TREK version 9.9 Rigaku 2007' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXH-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. All the H atoms were identified from the Fourier difference map and refined isotropically. ; _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^)+(0.1164P)^2^+1.1086P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 29699 _refine_ls_number_parameters 1737 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.2304 _refine_ls_wR_factor_gt 0.1999 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 C1 C 0.53276(10) 0.22598(9) 0.27251(7) 0.0199(3) Uani 1 1 d . . . C7 C 0.46522(10) 0.18427(9) 0.31718(7) 0.0212(3) Uani 1 1 d . . . O1 O 0.39165(8) 0.18657(8) 0.30294(6) 0.0287(3) Uani 1 1 d . . . O2 O 0.49105(8) 0.14410(8) 0.37541(6) 0.0298(3) Uani 1 1 d . . . H2A H 0.4453(17) 0.1173(15) 0.4024(13) 0.050(7) Uiso 1 1 d . . . C2 C 0.50993(10) 0.28074(9) 0.21497(8) 0.0209(3) Uani 1 1 d . . . H2 H 0.4485(14) 0.2913(12) 0.2054(10) 0.028(5) Uiso 1 1 d . . . C3 C 0.57182(10) 0.32136(10) 0.17245(8) 0.0215(3) Uani 1 1 d . . . H3 H 0.5531(13) 0.3608(12) 0.1323(10) 0.028(5) Uiso 1 1 d . . . C4 C 0.66013(10) 0.30782(9) 0.18571(7) 0.0212(3) Uani 1 1 d . . . N1 N 0.72169(10) 0.34598(10) 0.14240(8) 0.0295(3) Uani 1 1 d . . . H1A H 0.7032(15) 0.3768(14) 0.1075(12) 0.037(6) Uiso 1 1 d . . . H1B H 0.7796(16) 0.3372(14) 0.1524(12) 0.041(6) Uiso 1 1 d . . . C5 C 0.68279(10) 0.25307(9) 0.24377(8) 0.0217(3) Uani 1 1 d . . . H5 H 0.7445(15) 0.2407(13) 0.2527(11) 0.035(6) Uiso 1 1 d . . . C6 C 0.62015(10) 0.21317(9) 0.28643(7) 0.0201(3) Uani 1 1 d . . . H6 H 0.6354(14) 0.1757(13) 0.3260(11) 0.030(5) Uiso 1 1 d . . . C11 C 0.96821(10) 0.72861(9) 0.77275(8) 0.0204(3) Uani 1 1 d . . . C17 C 1.03453(11) 0.68634(9) 0.81646(8) 0.0221(3) Uani 1 1 d . . . O11 O 1.11440(8) 0.68706(8) 0.80084(6) 0.0304(3) Uani 1 1 d . . . O12 O 1.00001(8) 0.64652(8) 0.87576(6) 0.0299(3) Uani 1 1 d . . . H12A H 1.050(2) 0.6114(18) 0.8979(15) 0.078(9) Uiso 1 1 d . . . C12 C 0.87900(10) 0.71863(9) 0.78907(8) 0.0216(3) Uani 1 1 d . . . H12 H 0.8579(12) 0.6855(11) 0.8319(9) 0.019(4) Uiso 1 1 d . . . C13 C 0.81840(11) 0.75758(10) 0.74610(8) 0.0228(3) Uani 1 1 d . . . H13 H 0.7571(14) 0.7530(12) 0.7585(10) 0.024(5) Uiso 1 1 d . . . C14 C 0.84507(11) 0.80819(10) 0.68559(8) 0.0244(3) Uani 1 1 d . . . N11 N 0.78725(11) 0.84561(11) 0.64169(9) 0.0354(4) Uani 1 1 d . . . H11A H 0.7309(16) 0.8394(14) 0.6538(12) 0.040(6) Uiso 1 1 d . . . H11B H 0.8066(15) 0.8822(14) 0.6069(12) 0.042(6) Uiso 1 1 d . . . C15 C 0.93485(11) 0.81826(10) 0.66979(8) 0.0243(3) Uani 1 1 d . . . H15 H 0.9539(14) 0.8545(13) 0.6285(11) 0.032(5) Uiso 1 1 d . . . C16 C 0.99488(10) 0.77872(9) 0.71268(8) 0.0217(3) Uani 1 1 d . . . H16 H 1.0582(12) 0.7865(10) 0.7009(9) 0.013(4) Uiso 1 1 d . . . C21 C 0.03167(10) 0.27419(9) 0.73553(7) 0.0197(3) Uani 1 1 d . . . C27 C -0.03878(10) 0.32144(9) 0.69782(8) 0.0212(3) Uani 1 1 d . . . O21 O -0.11252(8) 0.30562(8) 0.70371(6) 0.0293(3) Uani 1 1 d . . . O22 O -0.01560(9) 0.38590(8) 0.65684(7) 0.0378(3) Uani 1 1 d . . . H22A H -0.063(2) 0.4154(19) 0.6270(17) 0.089(10) Uiso 1 1 d . . . C22 C 0.11891(10) 0.28924(9) 0.72087(8) 0.0214(3) Uani 1 1 d . . . H22 H 0.1343(12) 0.3326(11) 0.6838(9) 0.020(4) Uiso 1 1 d . . . C23 C 0.18382(10) 0.24296(10) 0.75698(8) 0.0218(3) Uani 1 1 d . . . H23 H 0.2432(15) 0.2483(13) 0.7448(11) 0.033(6) Uiso 1 1 d . . . C24 C 0.16323(10) 0.18051(9) 0.80994(8) 0.0216(3) Uani 1 1 d . . . N21 N 0.22659(10) 0.13422(10) 0.84591(8) 0.0310(3) Uani 1 1 d . . . H21A H 0.2823(15) 0.1448(12) 0.8367(10) 0.030(5) Uiso 1 1 d . . . H21B H 0.2089(16) 0.0961(14) 0.8818(12) 0.044(6) Uiso 1 1 d . . . C25 C 0.07519(10) 0.16657(9) 0.82478(8) 0.0222(3) Uani 1 1 d . . . H25 H 0.0609(12) 0.1235(11) 0.8613(9) 0.020(4) Uiso 1 1 d . . . C26 C 0.01109(10) 0.21230(9) 0.78779(8) 0.0209(3) Uani 1 1 d . . . H26 H -0.0484(13) 0.1991(11) 0.7990(10) 0.023(5) Uiso 1 1 d . . . C31 C 0.46410(10) 0.77418(9) 0.22868(7) 0.0197(3) Uani 1 1 d . . . C37 C 0.53115(10) 0.81775(9) 0.18576(8) 0.0216(3) Uani 1 1 d . . . O31 O 0.60502(8) 0.81354(8) 0.19978(6) 0.0305(3) Uani 1 1 d . . . O32 O 0.50492(9) 0.86173(8) 0.12913(7) 0.0335(3) Uani 1 1 d . . . H32A H 0.551(2) 0.8900(18) 0.1013(15) 0.070(9) Uiso 1 1 d . . . C32 C 0.48767(11) 0.71711(9) 0.28463(8) 0.0212(3) Uani 1 1 d . . . H32 H 0.5476(16) 0.7080(14) 0.2958(12) 0.043(6) Uiso 1 1 d . . . C33 C 0.42641(11) 0.67470(10) 0.32516(8) 0.0228(3) Uani 1 1 d . . . H33 H 0.4439(12) 0.6322(11) 0.3639(9) 0.016(4) Uiso 1 1 d . . . C34 C 0.33822(10) 0.68841(9) 0.31222(8) 0.0216(3) Uani 1 1 d . . . N31 N 0.27741(10) 0.64739(10) 0.35309(8) 0.0312(3) Uani 1 1 d . . . H31A H 0.2935(18) 0.6156(16) 0.3890(14) 0.053(7) Uiso 1 1 d . . . H31B H 0.2204(16) 0.6595(14) 0.3430(12) 0.041(6) Uiso 1 1 d . . . C35 C 0.31450(10) 0.74613(10) 0.25582(8) 0.0217(3) Uani 1 1 d . . . H35 H 0.2539(14) 0.7571(12) 0.2466(10) 0.027(5) Uiso 1 1 d . . . C36 C 0.37675(10) 0.78773(9) 0.21468(7) 0.0201(3) Uani 1 1 d . . . H36 H 0.3611(13) 0.8296(12) 0.1759(10) 0.026(5) Uiso 1 1 d . . . C101 C 0.14542(13) 1.11991(11) 0.03553(9) 0.0296(3) Uani 1 1 d . . . H101 H 0.1601(17) 1.1569(16) -0.0057(13) 0.057(7) Uiso 1 1 d . . . C102 C 0.14030(13) 1.13987(12) 0.10003(10) 0.0354(4) Uani 1 1 d . . . H102 H 0.1494(17) 1.1949(16) 0.1036(13) 0.057(7) Uiso 1 1 d . . . C103 C 0.11854(13) 1.08532(13) 0.16036(10) 0.0351(4) Uani 1 1 d . . . H103 H 0.1105(15) 1.1045(14) 0.2078(12) 0.044(6) Uiso 1 1 d . . . C104 C 0.10273(12) 1.01160(12) 0.15490(9) 0.0319(4) Uani 1 1 d . . . H104 H 0.0888(14) 0.9733(13) 0.1990(11) 0.034(6) Uiso 1 1 d . . . N105 N 0.09456(9) 0.91446(9) 0.08313(7) 0.0263(3) Uani 1 1 d . . . C106 C 0.08852(12) 0.81754(11) 0.01021(10) 0.0303(4) Uani 1 1 d . . . H106 H 0.0729(16) 0.7773(15) 0.0526(13) 0.051(7) Uiso 1 1 d . . . C107 C 0.09639(13) 0.79711(11) -0.05466(10) 0.0330(4) Uani 1 1 d . . . H107 H 0.0878(16) 0.7455(15) -0.0601(12) 0.046(7) Uiso 1 1 d . . . C108 C 0.11554(13) 0.85281(11) -0.11473(9) 0.0313(4) Uani 1 1 d . . . H108 H 0.1173(13) 0.8383(12) -0.1621(10) 0.026(5) Uiso 1 1 d . . . C109 C 0.12762(12) 0.92776(11) -0.10888(9) 0.0282(3) Uani 1 1 d . . . H109 H 0.1412(16) 0.9679(14) -0.1510(12) 0.045(6) Uiso 1 1 d . . . N110 N 0.13599(9) 1.02452(8) -0.03664(7) 0.0232(3) Uani 1 1 d . . . C111 C 0.10813(11) 0.98762(10) 0.08809(8) 0.0242(3) Uani 1 1 d . . . C112 C 0.10076(11) 0.89583(10) 0.01873(8) 0.0237(3) Uani 1 1 d . . . C113 C 0.12119(10) 0.95117(9) -0.04190(8) 0.0219(3) Uani 1 1 d . . . C114 C 0.12960(11) 1.04346(10) 0.02761(8) 0.0230(3) Uani 1 1 d . . . C121 C 0.67986(11) 0.14832(10) 0.99811(9) 0.0261(3) Uani 1 1 d . . . H121 H 0.7045(16) 0.1857(15) 0.9576(12) 0.046(7) Uiso 1 1 d . . . C122 C 0.66869(12) 0.16645(11) 1.06396(10) 0.0296(3) Uani 1 1 d . . . H122 H 0.6858(14) 0.2178(13) 1.0715(10) 0.030(5) Uiso 1 1 d . . . C123 C 0.63765(12) 0.11278(11) 1.12156(9) 0.0302(4) Uani 1 1 d . . . H123 H 0.6310(15) 0.1292(13) 1.1683(11) 0.035(6) Uiso 1 1 d . . . C124 C 0.61815(12) 0.04149(11) 1.11301(9) 0.0281(3) Uani 1 1 d . . . H124 H 0.5950(15) 0.0018(14) 1.1510(12) 0.038(6) Uiso 1 1 d . . . N125 N 0.60864(9) -0.04951(8) 1.03561(7) 0.0248(3) Uani 1 1 d . . . C126 C 0.59811(13) -0.13943(11) 0.95748(11) 0.0332(4) Uani 1 1 d . . . H126 H 0.5735(16) -0.1752(15) 0.9964(12) 0.047(7) Uiso 1 1 d . . . C127 C 0.60679(15) -0.15533(13) 0.89095(12) 0.0409(5) Uani 1 1 d . . . H127 H 0.595(2) -0.202(2) 0.8829(16) 0.081(10) Uiso 1 1 d . . . C128 C 0.63624(15) -0.10044(13) 0.83334(11) 0.0398(5) Uani 1 1 d . . . H128 H 0.6422(16) -0.1180(15) 0.7877(13) 0.049(7) Uiso 1 1 d . . . C129 C 0.65717(13) -0.03045(12) 0.84347(9) 0.0333(4) Uani 1 1 d . . . H129 H 0.6785(16) 0.0077(14) 0.8044(12) 0.042(6) Uiso 1 1 d . . . N130 N 0.67077(9) 0.05780(8) 0.92076(7) 0.0242(3) Uani 1 1 d . . . C131 C 0.62840(10) 0.02042(9) 1.04467(8) 0.0223(3) Uani 1 1 d . . . C132 C 0.61829(11) -0.06622(10) 0.96986(9) 0.0241(3) Uani 1 1 d . . . C133 C 0.64966(11) -0.01114(10) 0.91202(8) 0.0257(3) Uani 1 1 d . . . C134 C 0.65998(10) 0.07439(9) 0.98616(8) 0.0215(3) Uani 1 1 d . . . C141 C 0.98438(12) 0.38133(10) 0.95040(9) 0.0282(3) Uani 1 1 d . . . C142 C 1.01104(13) 0.37463(11) 0.88128(10) 0.0317(4) Uani 1 1 d . . . H142 H 1.0569(15) 0.3299(14) 0.8661(11) 0.041(6) Uiso 1 1 d . . . C143 C 0.97419(14) 0.43523(11) 0.83052(9) 0.0347(4) Uani 1 1 d . . . H143 H 0.9984(15) 0.4282(14) 0.7810(12) 0.043(6) Uiso 1 1 d . . . C144 C 0.91198(14) 0.50032(11) 0.85001(9) 0.0311(4) Uani 1 1 d . . . H144 H 0.8885(13) 0.5436(12) 0.8156(10) 0.030(5) Uiso 1 1 d . . . N145 N 0.82547(10) 0.57732(8) 0.93931(7) 0.0259(3) Uani 1 1 d . . . C146 C 0.74676(13) 0.65851(11) 1.02834(11) 0.0357(4) Uani 1 1 d . . . H146 H 0.7278(16) 0.7033(15) 0.9912(12) 0.045(6) Uiso 1 1 d . . . C147 C 0.72487(15) 0.66799(13) 1.09688(13) 0.0445(5) Uani 1 1 d . . . H147 H 0.6892(17) 0.7166(16) 1.1128(13) 0.054(7) Uiso 1 1 d . . . C148 C 0.75537(14) 0.60511(13) 1.14808(11) 0.0413(5) Uani 1 1 d . . . H148 H 0.7362(15) 0.6148(14) 1.1977(12) 0.043(6) Uiso 1 1 d . . . C149 C 0.80884(13) 0.53422(12) 1.13054(9) 0.0330(4) Uani 1 1 d . . . H149 H 0.8337(16) 0.4884(15) 1.1676(12) 0.050(7) Uiso 1 1 d . . . N150 N 0.89353(9) 0.45560(8) 1.04111(7) 0.0237(3) Uani 1 1 d . . . C151 C 0.88303(11) 0.51041(9) 0.92163(8) 0.0235(3) Uani 1 1 d . . . C152 C 0.80322(11) 0.58533(10) 1.00716(9) 0.0256(3) Uani 1 1 d . . . C153 C 0.83599(11) 0.52325(10) 1.05908(8) 0.0249(3) Uani 1 1 d . . . C154 C 0.91900(10) 0.44902(9) 0.97295(8) 0.0227(3) Uani 1 1 d . . . H154 H 1.0104(13) 0.3409(12) 0.9874(10) 0.027(5) Uiso 1 1 d . . . C161 C 0.49176(12) 0.33540(10) -0.00265(10) 0.0294(3) Uani 1 1 d . . . H161 H 0.5131(14) 0.2883(13) 0.0373(11) 0.035(6) Uiso 1 1 d . . . C162 C 0.52011(12) 0.32469(11) -0.07087(10) 0.0310(4) Uani 1 1 d . . . H162 H 0.5598(14) 0.2731(13) -0.0834(11) 0.032(5) Uiso 1 1 d . . . C163 C 0.49252(13) 0.38638(11) -0.12449(9) 0.0310(4) Uani 1 1 d . . . H163 H 0.5171(14) 0.3750(13) -0.1745(11) 0.030(5) Uiso 1 1 d . . . C164 C 0.43669(12) 0.45677(11) -0.10879(9) 0.0278(3) Uani 1 1 d . . . H164 H 0.4183(15) 0.5008(14) -0.1436(12) 0.039(6) Uiso 1 1 d . . . N165 N 0.34989(9) 0.53970(8) -0.02299(7) 0.0236(3) Uani 1 1 d . . . C166 C 0.26572(12) 0.62328(11) 0.06315(9) 0.0290(3) Uani 1 1 d . . . H166 H 0.2462(16) 0.6645(14) 0.0257(12) 0.042(6) Uiso 1 1 d . . . C167 C 0.23992(13) 0.63451(12) 0.13139(10) 0.0333(4) Uani 1 1 d . . . H167 H 0.2029(14) 0.6838(13) 0.1459(11) 0.032(5) Uiso 1 1 d . . . C168 C 0.27047(13) 0.57438(13) 0.18467(10) 0.0357(4) Uani 1 1 d . . . H168 H 0.2510(15) 0.5852(13) 0.2327(11) 0.036(6) Uiso 1 1 d . . . C169 C 0.32441(13) 0.50351(12) 0.16888(9) 0.0315(4) Uani 1 1 d . . . H169 H 0.3484(15) 0.4601(14) 0.2038(12) 0.038(6) Uiso 1 1 d . . . N170 N 0.40694(10) 0.41824(9) 0.08333(7) 0.0266(3) Uani 1 1 d . . . C171 C 0.40513(11) 0.46987(9) -0.03802(8) 0.0218(3) Uani 1 1 d . . . C172 C 0.32372(11) 0.55003(10) 0.04440(8) 0.0229(3) Uani 1 1 d . . . C173 C 0.35309(11) 0.48831(10) 0.09799(8) 0.0241(3) Uani 1 1 d . . . C174 C 0.43346(11) 0.40833(10) 0.01589(8) 0.0231(3) Uani 1 1 d . . . C181 C 0.50731(12) 0.66439(11) 0.49847(10) 0.0301(3) Uani 1 1 d . . . H181 H 0.4863(15) 0.7058(14) 0.4598(11) 0.036(6) Uiso 1 1 d . . . C182 C 0.47890(12) 0.67771(11) 0.56611(10) 0.0314(4) Uani 1 1 d . . . H182 H 0.4406(15) 0.7321(13) 0.5767(11) 0.034(6) Uiso 1 1 d . . . C183 C 0.50651(12) 0.61912(11) 0.62124(9) 0.0314(4) Uani 1 1 d . . . H183 H 0.4828(14) 0.6299(13) 0.6720(11) 0.030(5) Uiso 1 1 d . . . C184 C 0.56319(12) 0.54799(11) 0.60798(8) 0.0278(3) Uani 1 1 d . . . H184 H 0.5813(15) 0.5076(14) 0.6469(12) 0.038(6) Uiso 1 1 d . . . N185 N 0.64990(9) 0.46098(8) 0.52573(7) 0.0233(3) Uani 1 1 d . . . C186 C 0.73391(12) 0.37247(11) 0.44339(10) 0.0302(4) Uani 1 1 d . . . H186 H 0.7544(14) 0.3300(13) 0.4843(11) 0.032(5) Uiso 1 1 d . . . C187 C 0.76004(13) 0.35794(13) 0.37579(11) 0.0379(4) Uani 1 1 d . . . H187 H 0.7978(15) 0.3065(14) 0.3637(11) 0.036(6) Uiso 1 1 d . . . C188 C 0.73042(14) 0.41587(14) 0.32073(10) 0.0402(5) Uani 1 1 d . . . H188 H 0.7508(17) 0.4061(16) 0.2728(14) 0.054(7) Uiso 1 1 d . . . C189 C 0.67613(14) 0.48744(13) 0.33373(9) 0.0349(4) Uani 1 1 d . . . H189 H 0.6497(17) 0.5323(15) 0.2961(13) 0.051(7) Uiso 1 1 d . . . N190 N 0.59298(10) 0.57704(9) 0.41548(7) 0.0272(3) Uani 1 1 d . . . C191 C 0.59447(10) 0.53130(9) 0.53814(8) 0.0217(3) Uani 1 1 d . . . C192 C 0.67603(11) 0.44711(10) 0.45918(8) 0.0238(3) Uani 1 1 d . . . C193 C 0.64679(11) 0.50599(10) 0.40356(8) 0.0258(3) Uani 1 1 d . . . C194 C 0.56605(11) 0.59011(10) 0.48236(8) 0.0232(3) Uani 1 1 d . . . C201 C 0.25407(12) 0.33600(11) 0.49347(10) 0.0312(4) Uani 1 1 d . . . H201 H 0.2675(15) 0.3004(14) 0.5374(11) 0.038(6) Uiso 1 1 d . . . C202 C 0.28517(13) 0.31043(12) 0.43028(11) 0.0367(4) Uani 1 1 d . . . H202 H 0.3247(16) 0.2558(15) 0.4287(12) 0.048(7) Uiso 1 1 d . . . C203 C 0.26270(13) 0.35953(13) 0.36871(10) 0.0362(4) Uani 1 1 d . . . H203 H 0.2869(16) 0.3418(15) 0.3239(13) 0.052(7) Uiso 1 1 d . . . C204 C 0.20793(12) 0.43411(12) 0.37144(9) 0.0314(4) Uani 1 1 d . . . H204 H 0.1888(14) 0.4673(13) 0.3273(11) 0.036(6) Uiso 1 1 d . . . N205 N 0.11434(9) 0.53353(8) 0.44038(7) 0.0252(3) Uani 1 1 d . . . C206 C 0.01426(13) 0.62951(11) 0.50921(11) 0.0342(4) Uani 1 1 d . . . H206 H -0.0064(14) 0.6632(13) 0.4652(11) 0.035(5) Uiso 1 1 d . . . C207 C -0.02174(14) 0.65282(13) 0.57299(12) 0.0406(5) Uani 1 1 d . . . H207 H -0.0708(16) 0.7039(15) 0.5773(12) 0.051(7) Uiso 1 1 d . . . C208 C 0.00527(15) 0.60686(13) 0.63339(11) 0.0418(5) Uani 1 1 d . . . H208 H -0.0197(15) 0.6225(14) 0.6789(13) 0.048(7) Uiso 1 1 d . . . C209 C 0.06821(14) 0.53643(13) 0.63036(10) 0.0354(4) Uani 1 1 d . . . H209 H 0.0917(12) 0.5005(11) 0.6669(10) 0.019(4) Uiso 1 1 d . . . N210 N 0.16505(10) 0.43704(9) 0.56201(7) 0.0261(3) Uani 1 1 d . . . C211 C 0.17196(11) 0.46263(10) 0.43702(8) 0.0234(3) Uani 1 1 d . . . C212 C 0.08002(11) 0.55665(10) 0.50371(9) 0.0261(3) Uani 1 1 d . . . C213 C 0.10728(11) 0.50797(10) 0.56491(8) 0.0267(3) Uani 1 1 d . . . C214 C 0.19653(11) 0.41323(10) 0.49889(8) 0.0235(3) Uani 1 1 d . . . C221 C 0.32158(12) 0.85422(11) 0.49415(10) 0.0303(4) Uani 1 1 d . . . H221 H 0.2992(16) 0.8119(14) 0.5350(12) 0.043(6) Uiso 1 1 d . . . C222 C 0.33160(13) 0.84074(12) 0.42714(11) 0.0369(4) Uani 1 1 d . . . H222 H 0.3157(16) 0.7893(15) 0.4160(12) 0.045(6) Uiso 1 1 d . . . C223 C 0.36045(13) 0.89837(13) 0.37180(10) 0.0374(4) Uani 1 1 d . . . H223 H 0.3658(16) 0.8857(14) 0.3232(12) 0.046(7) Uiso 1 1 d . . . C224 C 0.37904(12) 0.96898(12) 0.38410(9) 0.0311(4) Uani 1 1 d . . . H224 H 0.4016(15) 1.0093(14) 0.3475(12) 0.041(6) Uiso 1 1 d . . . N225 N 0.38997(9) 1.05266(8) 0.46683(7) 0.0241(3) Uani 1 1 d . . . C226 C 0.40346(13) 1.13488(11) 0.55004(10) 0.0310(4) Uani 1 1 d . . . H226 H 0.4273(17) 1.1729(15) 0.5131(13) 0.050(7) Uiso 1 1 d . . . C227 C 0.39532(14) 1.14643(12) 0.61784(11) 0.0362(4) Uani 1 1 d . . . H227 H 0.411(2) 1.1942(18) 0.6298(15) 0.068(9) Uiso 1 1 d . . . C228 C 0.36560(14) 1.08861(13) 0.67283(10) 0.0387(4) Uani 1 1 d . . . H228 H 0.3594(18) 1.0995(16) 0.7207(14) 0.059(8) Uiso 1 1 d . . . C229 C 0.34478(13) 1.02031(12) 0.65913(9) 0.0311(4) Uani 1 1 d . . . H229 H 0.3217(16) 0.9759(14) 0.6961(12) 0.046(7) Uiso 1 1 d . . . N230 N 0.33103(9) 0.93837(8) 0.57647(7) 0.0245(3) Uani 1 1 d . . . C231 C 0.37024(10) 0.98437(10) 0.45409(8) 0.0235(3) Uani 1 1 d . . . C232 C 0.38194(11) 1.06423(10) 0.53384(8) 0.0231(3) Uani 1 1 d . . . C233 C 0.35188(11) 1.00592(10) 0.58898(8) 0.0237(3) Uani 1 1 d . . . C234 C 0.34091(11) 0.92649(10) 0.50980(8) 0.0234(3) Uani 1 1 d . . . C241 C 0.90601(13) 0.17661(12) 0.51039(12) 0.0378(4) Uani 1 1 d . . . H241 H 0.9172(16) 0.2228(15) 0.4710(12) 0.048(7) Uiso 1 1 d . . . C242 C 0.90011(14) 0.18496(14) 0.57826(13) 0.0450(5) Uani 1 1 d . . . H242 H 0.904(2) 0.2392(19) 0.5910(15) 0.080(10) Uiso 1 1 d . . . C243 C 0.88437(14) 0.12026(15) 0.63103(12) 0.0442(5) Uani 1 1 d . . . H243 H 0.8811(16) 0.1277(15) 0.6801(13) 0.053(7) Uiso 1 1 d . . . C244 C 0.87459(14) 0.04831(13) 0.61511(10) 0.0363(4) Uani 1 1 d . . . H244 H 0.8629(16) 0.0034(15) 0.6498(12) 0.047(7) Uiso 1 1 d . . . N245 N 0.86757(10) -0.03285(9) 0.52958(8) 0.0281(3) Uani 1 1 d . . . C246 C 0.86043(14) -0.11137(13) 0.44159(14) 0.0447(5) Uani 1 1 d . . . H246 H 0.8490(14) -0.1519(13) 0.4755(11) 0.031(6) Uiso 1 1 d . . . C247 C 0.86528(17) -0.1175(2) 0.37289(18) 0.0672(10) Uani 1 1 d . . . H247 H 0.857(2) -0.162(2) 0.3599(17) 0.087(10) Uiso 1 1 d . . . C248 C 0.88287(17) -0.0526(2) 0.32074(14) 0.0606(8) Uani 1 1 d . . . H248 H 0.889(2) -0.066(2) 0.2717(17) 0.091(11) Uiso 1 1 d . . . C249 C 0.89519(15) 0.01641(18) 0.33777(11) 0.0498(6) Uani 1 1 d . . . H249 H 0.908(2) 0.0650(18) 0.2979(16) 0.078(9) Uiso 1 1 d . . . N250 N 0.90097(10) 0.09625(10) 0.42404(8) 0.0315(3) Uani 1 1 d . . . C251 C 0.87972(11) 0.03756(10) 0.54456(8) 0.0246(3) Uani 1 1 d . . . C252 C 0.87293(11) -0.03930(11) 0.46183(9) 0.0292(3) Uani 1 1 d . . . C253 C 0.89011(12) 0.02590(12) 0.40892(9) 0.0309(4) Uani 1 1 d . . . C254 C 0.89594(11) 0.10222(10) 0.49118(9) 0.0264(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 C1 0.0162(7) 0.0219(7) 0.0211(6) -0.0017(5) -0.0035(5) -0.0028(6) C7 0.0190(7) 0.0219(7) 0.0217(6) -0.0020(5) -0.0024(5) -0.0030(6) O1 0.0204(6) 0.0360(7) 0.0311(6) 0.0005(5) -0.0062(4) -0.0100(5) O2 0.0237(6) 0.0357(7) 0.0286(6) 0.0086(5) -0.0066(5) -0.0097(5) C2 0.0175(7) 0.0222(7) 0.0237(6) -0.0024(5) -0.0066(5) -0.0029(6) C3 0.0203(7) 0.0230(7) 0.0209(6) 0.0014(5) -0.0078(5) -0.0030(6) C4 0.0204(7) 0.0226(7) 0.0215(6) -0.0011(5) -0.0064(5) -0.0045(6) N1 0.0217(7) 0.0366(8) 0.0293(7) 0.0107(6) -0.0090(5) -0.0100(6) C5 0.0176(7) 0.0236(7) 0.0238(6) 0.0004(5) -0.0068(5) -0.0031(6) C6 0.0194(7) 0.0215(7) 0.0189(6) 0.0006(5) -0.0050(5) -0.0033(6) C11 0.0179(7) 0.0197(7) 0.0234(6) -0.0033(5) -0.0032(5) -0.0031(6) C17 0.0216(7) 0.0212(7) 0.0245(7) -0.0039(5) -0.0041(5) -0.0052(6) O11 0.0195(6) 0.0401(7) 0.0304(6) 0.0031(5) -0.0068(4) -0.0063(5) O12 0.0257(6) 0.0337(7) 0.0296(6) 0.0066(5) -0.0084(5) -0.0088(5) C12 0.0185(7) 0.0221(7) 0.0244(7) -0.0032(5) -0.0028(5) -0.0052(6) C13 0.0180(7) 0.0231(7) 0.0267(7) -0.0017(6) -0.0027(5) -0.0050(6) C14 0.0217(8) 0.0235(7) 0.0272(7) 0.0009(6) -0.0059(6) -0.0042(6) N11 0.0249(8) 0.0414(9) 0.0399(8) 0.0146(7) -0.0141(6) -0.0130(7) C15 0.0196(7) 0.0247(7) 0.0275(7) 0.0022(6) -0.0046(6) -0.0052(6) C16 0.0169(7) 0.0223(7) 0.0259(7) -0.0034(5) -0.0025(5) -0.0049(6) C21 0.0181(7) 0.0175(6) 0.0233(6) -0.0013(5) -0.0039(5) -0.0038(5) C27 0.0196(7) 0.0201(7) 0.0234(6) -0.0009(5) -0.0050(5) -0.0028(6) O21 0.0206(6) 0.0331(6) 0.0347(6) 0.0054(5) -0.0105(5) -0.0082(5) O22 0.0290(7) 0.0370(7) 0.0466(8) 0.0205(6) -0.0173(6) -0.0137(6) C22 0.0194(7) 0.0223(7) 0.0220(6) 0.0012(5) -0.0039(5) -0.0056(6) C23 0.0165(7) 0.0243(7) 0.0238(7) 0.0002(5) -0.0028(5) -0.0048(6) C24 0.0177(7) 0.0215(7) 0.0244(7) 0.0004(5) -0.0041(5) -0.0030(6) N21 0.0185(7) 0.0349(8) 0.0360(7) 0.0129(6) -0.0088(5) -0.0061(6) C25 0.0194(7) 0.0207(7) 0.0249(7) 0.0023(5) -0.0032(5) -0.0045(6) C26 0.0173(7) 0.0207(7) 0.0243(6) -0.0014(5) -0.0025(5) -0.0046(6) C31 0.0159(7) 0.0199(7) 0.0234(6) -0.0038(5) -0.0043(5) -0.0023(5) C37 0.0176(7) 0.0202(7) 0.0263(7) -0.0038(5) -0.0020(5) -0.0032(6) O31 0.0195(6) 0.0402(7) 0.0339(6) -0.0011(5) -0.0062(4) -0.0114(5) O32 0.0238(6) 0.0365(7) 0.0391(7) 0.0134(5) -0.0102(5) -0.0121(5) C32 0.0185(7) 0.0212(7) 0.0249(7) -0.0037(5) -0.0067(5) -0.0027(6) C33 0.0195(7) 0.0261(7) 0.0226(6) 0.0008(6) -0.0071(5) -0.0039(6) C34 0.0203(7) 0.0232(7) 0.0218(6) -0.0008(5) -0.0049(5) -0.0055(6) N31 0.0209(7) 0.0411(9) 0.0292(7) 0.0125(6) -0.0088(5) -0.0095(6) C35 0.0161(7) 0.0244(7) 0.0241(7) 0.0017(5) -0.0064(5) -0.0037(6) C36 0.0187(7) 0.0200(7) 0.0220(6) -0.0014(5) -0.0055(5) -0.0035(6) C101 0.0308(9) 0.0244(8) 0.0344(8) -0.0059(6) -0.0075(7) -0.0036(7) C102 0.0337(10) 0.0328(9) 0.0419(10) -0.0146(8) -0.0073(8) -0.0033(8) C103 0.0320(10) 0.0444(11) 0.0313(8) -0.0168(8) -0.0048(7) -0.0042(8) C104 0.0284(9) 0.0426(10) 0.0251(7) -0.0063(7) -0.0048(6) -0.0062(8) N105 0.0215(7) 0.0308(7) 0.0257(6) 0.0005(5) -0.0012(5) -0.0083(6) C106 0.0279(9) 0.0237(8) 0.0388(9) -0.0029(7) -0.0008(7) -0.0087(7) C107 0.0303(9) 0.0288(9) 0.0421(9) -0.0110(7) -0.0016(7) -0.0094(7) C108 0.0305(9) 0.0338(9) 0.0330(8) -0.0116(7) -0.0075(7) -0.0059(7) C109 0.0314(9) 0.0268(8) 0.0264(7) -0.0036(6) -0.0088(6) -0.0019(7) N110 0.0243(7) 0.0197(6) 0.0246(6) -0.0002(5) -0.0067(5) -0.0019(5) C111 0.0195(7) 0.0283(8) 0.0242(7) -0.0038(6) -0.0032(5) -0.0037(6) C112 0.0194(7) 0.0228(7) 0.0280(7) -0.0015(6) -0.0031(6) -0.0045(6) C113 0.0193(7) 0.0212(7) 0.0246(7) -0.0013(5) -0.0058(5) -0.0022(6) C114 0.0208(7) 0.0214(7) 0.0259(7) -0.0029(6) -0.0053(5) -0.0009(6) C121 0.0217(8) 0.0191(7) 0.0372(8) -0.0006(6) -0.0085(6) -0.0021(6) C122 0.0250(8) 0.0233(8) 0.0415(9) -0.0091(7) -0.0096(7) 0.0003(7) C123 0.0253(8) 0.0332(9) 0.0321(8) -0.0099(7) -0.0061(6) -0.0002(7) C124 0.0247(8) 0.0300(8) 0.0270(7) -0.0032(6) -0.0040(6) -0.0006(7) N125 0.0210(7) 0.0227(6) 0.0297(6) -0.0004(5) -0.0044(5) -0.0042(5) C126 0.0325(10) 0.0225(8) 0.0469(10) -0.0071(7) -0.0097(8) -0.0054(7) C127 0.0375(11) 0.0330(10) 0.0587(13) -0.0182(9) -0.0165(9) -0.0041(8) C128 0.0394(11) 0.0411(11) 0.0432(10) -0.0186(9) -0.0171(8) 0.0020(9) C129 0.0335(10) 0.0360(9) 0.0301(8) -0.0053(7) -0.0126(7) 0.0014(8) N130 0.0230(7) 0.0223(6) 0.0262(6) 0.0016(5) -0.0078(5) -0.0020(5) C131 0.0190(7) 0.0195(7) 0.0269(7) -0.0016(5) -0.0052(5) -0.0006(6) C132 0.0205(7) 0.0195(7) 0.0320(8) -0.0024(6) -0.0078(6) -0.0009(6) C133 0.0228(8) 0.0253(8) 0.0277(7) -0.0022(6) -0.0096(6) 0.0019(6) C134 0.0165(7) 0.0196(7) 0.0267(7) 0.0004(5) -0.0056(5) -0.0004(6) C141 0.0261(8) 0.0232(7) 0.0354(8) -0.0029(6) -0.0056(6) -0.0056(7) C142 0.0305(9) 0.0239(8) 0.0407(9) -0.0099(7) 0.0008(7) -0.0072(7) C143 0.0472(11) 0.0286(9) 0.0296(8) -0.0084(7) 0.0020(7) -0.0143(8) C144 0.0423(10) 0.0259(8) 0.0270(7) -0.0005(6) -0.0057(7) -0.0126(8) N145 0.0247(7) 0.0208(6) 0.0316(7) 0.0022(5) -0.0060(5) -0.0063(5) C146 0.0272(9) 0.0230(8) 0.0533(11) -0.0056(8) 0.0018(8) -0.0046(7) C147 0.0349(11) 0.0323(10) 0.0622(13) -0.0206(10) 0.0151(9) -0.0084(9) C148 0.0383(11) 0.0457(11) 0.0416(10) -0.0184(9) 0.0090(8) -0.0166(9) C149 0.0342(10) 0.0377(10) 0.0290(8) -0.0060(7) 0.0017(7) -0.0163(8) N150 0.0227(7) 0.0225(6) 0.0265(6) -0.0002(5) -0.0045(5) -0.0073(5) C151 0.0238(8) 0.0192(7) 0.0281(7) -0.0003(5) -0.0040(6) -0.0076(6) C152 0.0209(8) 0.0214(7) 0.0340(8) -0.0026(6) -0.0014(6) -0.0064(6) C153 0.0225(8) 0.0242(7) 0.0295(7) -0.0027(6) -0.0020(6) -0.0104(6) C154 0.0200(7) 0.0200(7) 0.0293(7) -0.0018(6) -0.0040(5) -0.0072(6) C161 0.0277(9) 0.0233(8) 0.0393(9) -0.0052(7) -0.0144(7) -0.0009(7) C162 0.0277(9) 0.0256(8) 0.0416(9) -0.0115(7) -0.0092(7) -0.0011(7) C163 0.0319(9) 0.0320(9) 0.0322(8) -0.0113(7) -0.0039(7) -0.0087(7) C164 0.0323(9) 0.0263(8) 0.0257(7) -0.0033(6) -0.0035(6) -0.0091(7) N165 0.0253(7) 0.0207(6) 0.0251(6) -0.0015(5) -0.0061(5) -0.0045(5) C166 0.0267(9) 0.0238(8) 0.0356(8) -0.0016(6) -0.0049(7) -0.0050(7) C167 0.0295(9) 0.0307(9) 0.0389(9) -0.0105(7) 0.0004(7) -0.0054(8) C168 0.0330(10) 0.0431(11) 0.0308(8) -0.0105(8) 0.0013(7) -0.0085(8) C169 0.0323(9) 0.0360(9) 0.0268(8) -0.0035(7) -0.0074(7) -0.0060(8) N170 0.0251(7) 0.0271(7) 0.0270(6) -0.0004(5) -0.0100(5) -0.0013(6) C171 0.0211(7) 0.0192(7) 0.0268(7) -0.0015(5) -0.0064(5) -0.0062(6) C172 0.0213(7) 0.0218(7) 0.0264(7) -0.0018(6) -0.0056(5) -0.0054(6) C173 0.0225(8) 0.0250(7) 0.0257(7) -0.0023(6) -0.0072(6) -0.0045(6) C174 0.0210(7) 0.0215(7) 0.0287(7) -0.0024(6) -0.0092(6) -0.0042(6) C181 0.0267(9) 0.0243(8) 0.0404(9) -0.0035(7) -0.0141(7) -0.0001(7) C182 0.0236(8) 0.0275(8) 0.0447(10) -0.0097(7) -0.0090(7) -0.0020(7) C183 0.0295(9) 0.0333(9) 0.0341(8) -0.0107(7) -0.0032(7) -0.0090(7) C184 0.0318(9) 0.0267(8) 0.0255(7) -0.0022(6) -0.0048(6) -0.0080(7) N185 0.0237(7) 0.0206(6) 0.0259(6) -0.0016(5) -0.0055(5) -0.0045(5) C186 0.0245(8) 0.0263(8) 0.0403(9) -0.0072(7) -0.0020(7) -0.0067(7) C187 0.0293(10) 0.0361(10) 0.0481(11) -0.0168(8) 0.0060(8) -0.0090(8) C188 0.0391(11) 0.0503(12) 0.0329(9) -0.0141(8) 0.0077(8) -0.0182(9) C189 0.0381(10) 0.0445(11) 0.0247(7) -0.0054(7) -0.0023(7) -0.0155(9) N190 0.0270(7) 0.0294(7) 0.0265(6) -0.0005(5) -0.0088(5) -0.0065(6) C191 0.0208(7) 0.0203(7) 0.0253(7) -0.0018(5) -0.0053(5) -0.0062(6) C192 0.0204(7) 0.0252(7) 0.0270(7) -0.0027(6) -0.0039(6) -0.0075(6) C193 0.0248(8) 0.0291(8) 0.0246(7) -0.0019(6) -0.0054(6) -0.0075(7) C194 0.0213(7) 0.0219(7) 0.0285(7) -0.0016(6) -0.0086(6) -0.0055(6) C201 0.0256(9) 0.0245(8) 0.0422(9) 0.0024(7) -0.0108(7) -0.0025(7) C202 0.0259(9) 0.0311(9) 0.0521(11) -0.0085(8) -0.0065(8) -0.0010(8) C203 0.0287(9) 0.0438(11) 0.0377(9) -0.0142(8) -0.0010(7) -0.0076(8) C204 0.0282(9) 0.0394(10) 0.0268(7) -0.0011(7) -0.0049(6) -0.0090(8) N205 0.0219(7) 0.0225(6) 0.0305(6) 0.0033(5) -0.0057(5) -0.0064(5) C206 0.0290(9) 0.0244(8) 0.0501(11) -0.0058(7) -0.0059(8) -0.0069(7) C207 0.0331(10) 0.0323(10) 0.0578(12) -0.0162(9) 0.0012(9) -0.0095(8) C208 0.0401(11) 0.0438(11) 0.0466(11) -0.0226(9) 0.0071(9) -0.0198(9) C209 0.0380(10) 0.0428(11) 0.0302(8) -0.0076(8) -0.0003(7) -0.0205(9) N210 0.0279(7) 0.0268(7) 0.0253(6) 0.0027(5) -0.0070(5) -0.0111(6) C211 0.0209(7) 0.0259(7) 0.0241(7) 0.0017(6) -0.0048(5) -0.0084(6) C212 0.0226(8) 0.0230(7) 0.0337(8) -0.0023(6) -0.0023(6) -0.0097(6) C213 0.0274(8) 0.0269(8) 0.0288(7) -0.0031(6) -0.0028(6) -0.0135(7) C214 0.0208(7) 0.0221(7) 0.0284(7) 0.0002(6) -0.0074(6) -0.0052(6) C221 0.0248(8) 0.0224(8) 0.0454(10) -0.0047(7) -0.0135(7) -0.0008(7) C222 0.0297(10) 0.0307(9) 0.0532(11) -0.0162(8) -0.0147(8) 0.0030(8) C223 0.0286(9) 0.0466(11) 0.0389(9) -0.0224(9) -0.0093(7) 0.0040(8) C224 0.0262(9) 0.0374(9) 0.0284(8) -0.0080(7) -0.0053(6) 0.0000(7) N225 0.0217(7) 0.0241(6) 0.0254(6) -0.0003(5) -0.0041(5) -0.0041(5) C226 0.0309(9) 0.0236(8) 0.0406(9) -0.0040(7) -0.0105(7) -0.0058(7) C227 0.0376(10) 0.0313(9) 0.0446(10) -0.0132(8) -0.0157(8) -0.0030(8) C228 0.0388(11) 0.0436(11) 0.0354(9) -0.0150(8) -0.0151(8) 0.0033(9) C229 0.0313(9) 0.0356(9) 0.0251(7) -0.0036(7) -0.0088(6) -0.0001(8) N230 0.0239(7) 0.0214(6) 0.0265(6) 0.0030(5) -0.0077(5) -0.0020(5) C231 0.0180(7) 0.0258(7) 0.0256(7) -0.0036(6) -0.0043(5) -0.0012(6) C232 0.0209(7) 0.0219(7) 0.0262(7) -0.0023(6) -0.0050(5) -0.0032(6) C233 0.0214(7) 0.0253(7) 0.0228(7) -0.0001(6) -0.0068(5) -0.0006(6) C234 0.0192(7) 0.0222(7) 0.0280(7) -0.0015(6) -0.0080(6) 0.0000(6) C241 0.0284(9) 0.0290(9) 0.0576(12) -0.0076(8) -0.0084(8) -0.0066(8) C242 0.0299(10) 0.0432(12) 0.0679(14) -0.0294(11) -0.0115(9) -0.0004(9) C243 0.0350(11) 0.0561(13) 0.0454(11) -0.0273(10) -0.0143(8) 0.0048(10) C244 0.0344(10) 0.0435(11) 0.0278(8) -0.0059(8) -0.0092(7) 0.0034(8) N245 0.0240(7) 0.0257(7) 0.0330(7) -0.0011(5) -0.0075(5) -0.0010(6) C246 0.0322(11) 0.0329(10) 0.0762(16) -0.0246(11) -0.0200(10) 0.0010(8) C247 0.0388(13) 0.0719(18) 0.106(2) -0.0679(19) -0.0319(14) 0.0159(13) C248 0.0477(14) 0.087(2) 0.0540(14) -0.0438(15) -0.0151(11) 0.0045(14) C249 0.0355(11) 0.0827(18) 0.0324(10) -0.0206(11) -0.0052(8) -0.0046(11) N250 0.0247(7) 0.0395(8) 0.0292(7) -0.0004(6) -0.0015(5) -0.0093(6) C251 0.0208(7) 0.0261(8) 0.0266(7) -0.0046(6) -0.0066(6) -0.0005(6) C252 0.0198(8) 0.0303(8) 0.0395(9) -0.0115(7) -0.0077(6) -0.0014(7) C253 0.0205(8) 0.0453(10) 0.0277(8) -0.0109(7) -0.0029(6) -0.0046(7) C254 0.0188(7) 0.0275(8) 0.0329(8) -0.0042(6) -0.0036(6) -0.0047(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 C1 C2 1.401(2) . ? C1 C6 1.403(2) . ? C1 C7 1.466(2) . ? C7 O1 1.2228(19) . ? C7 O2 1.3278(19) . ? O2 H2A 0.96(3) . ? C2 C3 1.379(2) . ? C2 H2 0.98(2) . ? C3 C4 1.411(2) . ? C3 H3 1.00(2) . ? C4 N1 1.358(2) . ? C4 C5 1.408(2) . ? N1 H1A 0.85(2) . ? N1 H1B 0.94(2) . ? C5 C6 1.381(2) . ? C5 H5 0.98(2) . ? C6 H6 0.96(2) . ? C11 C16 1.395(2) . ? C11 C12 1.403(2) . ? C11 C17 1.467(2) . ? C17 O11 1.2218(19) . ? C17 O12 1.3338(18) . ? O12 H12A 0.99(3) . ? C12 C13 1.382(2) . ? C12 H12 0.980(18) . ? C13 C14 1.406(2) . ? C13 H13 0.95(2) . ? C14 N11 1.359(2) . ? C14 C15 1.412(2) . ? N11 H11A 0.89(2) . ? N11 H11B 0.90(2) . ? C15 C16 1.377(2) . ? C15 H15 0.98(2) . ? C16 H16 1.000(17) . ? C21 C26 1.396(2) . ? C21 C22 1.402(2) . ? C21 C27 1.464(2) . ? C27 O21 1.2151(19) . ? C27 O22 1.3293(19) . ? O22 H22A 1.02(3) . ? C22 C23 1.379(2) . ? C22 H22 0.987(19) . ? C23 C24 1.411(2) . ? C23 H23 0.93(2) . ? C24 N21 1.361(2) . ? C24 C25 1.408(2) . ? N21 H21A 0.90(2) . ? N21 H21B 0.93(2) . ? C25 C26 1.377(2) . ? C25 H25 0.974(18) . ? C26 H26 0.98(2) . ? C31 C32 1.400(2) . ? C31 C36 1.402(2) . ? C31 C37 1.466(2) . ? C37 O31 1.2189(19) . ? C37 O32 1.325(2) . ? O32 H32A 0.97(3) . ? C32 C33 1.374(2) . ? C32 H32 0.97(2) . ? C33 C34 1.407(2) . ? C33 H33 1.001(18) . ? C34 N31 1.358(2) . ? C34 C35 1.413(2) . ? N31 H31A 0.86(3) . ? N31 H31B 0.92(2) . ? C35 C36 1.382(2) . ? C35 H35 0.97(2) . ? C36 H36 0.99(2) . ? C101 C102 1.356(2) . ? C101 C114 1.418(2) . ? C101 H101 0.97(3) . ? C102 C103 1.423(3) . ? C102 H102 1.00(3) . ? C103 C104 1.358(3) . ? C103 H103 1.02(2) . ? C104 C111 1.427(2) . ? C104 H104 1.02(2) . ? N105 C111 1.333(2) . ? N105 C112 1.342(2) . ? C106 C107 1.359(3) . ? C106 C112 1.431(2) . ? C106 H106 1.02(2) . ? C107 C108 1.422(3) . ? C107 H107 0.95(2) . ? C108 C109 1.359(2) . ? C108 H108 1.001(19) . ? C109 C113 1.424(2) . ? C109 H109 1.01(2) . ? N110 C114 1.3412(19) . ? N110 C113 1.345(2) . ? C111 C114 1.436(2) . ? C112 C113 1.430(2) . ? C121 C122 1.356(2) . ? C121 C134 1.429(2) . ? C121 H121 1.01(2) . ? C122 C123 1.417(3) . ? C122 H122 1.01(2) . ? C123 C124 1.360(3) . ? C123 H123 0.99(2) . ? C124 C131 1.424(2) . ? C124 H124 0.99(2) . ? N125 C131 1.343(2) . ? N125 C132 1.349(2) . ? C126 C127 1.361(3) . ? C126 C132 1.422(2) . ? C126 H126 0.97(2) . ? C127 C128 1.422(3) . ? C127 H127 0.90(3) . ? C128 C129 1.359(3) . ? C128 H128 0.98(2) . ? C129 C133 1.424(2) . ? C129 H129 0.98(2) . ? N130 C133 1.334(2) . ? N130 C134 1.339(2) . ? C131 C134 1.434(2) . ? C132 C133 1.436(2) . ? C141 C142 1.364(2) . ? C141 C154 1.426(2) . ? C141 H154 1.00(2) . ? C142 C143 1.426(3) . ? C142 H142 0.96(2) . ? C143 C144 1.353(3) . ? C143 H143 0.99(2) . ? C144 C151 1.425(2) . ? C144 H144 0.98(2) . ? N145 C151 1.333(2) . ? N145 C152 1.339(2) . ? C146 C147 1.358(3) . ? C146 C152 1.429(2) . ? C146 H146 1.01(2) . ? C147 C148 1.419(3) . ? C147 H147 0.95(3) . ? C148 C149 1.360(3) . ? C148 H148 1.00(2) . ? C149 C153 1.423(2) . ? C149 H149 1.04(2) . ? N150 C154 1.343(2) . ? N150 C153 1.344(2) . ? C151 C154 1.435(2) . ? C152 C153 1.432(2) . ? C161 C162 1.363(3) . ? C161 C174 1.421(2) . ? C161 H161 1.08(2) . ? C162 C163 1.426(3) . ? C162 H162 0.99(2) . ? C163 C164 1.358(3) . ? C163 H163 1.02(2) . ? C164 C171 1.425(2) . ? C164 H164 0.97(2) . ? N165 C172 1.3427(19) . ? N165 C171 1.343(2) . ? C166 C167 1.362(2) . ? C166 C172 1.425(2) . ? C166 H166 0.98(2) . ? C167 C168 1.421(3) . ? C167 H167 0.96(2) . ? C168 C169 1.353(3) . ? C168 H168 0.97(2) . ? C169 C173 1.432(2) . ? C169 H169 0.99(2) . ? N170 C173 1.336(2) . ? N170 C174 1.342(2) . ? C171 C174 1.432(2) . ? C172 C173 1.434(2) . ? C181 C182 1.363(3) . ? C181 C194 1.429(2) . ? C181 H181 1.01(2) . ? C182 C183 1.419(3) . ? C182 H182 1.01(2) . ? C183 C184 1.362(3) . ? C183 H183 1.03(2) . ? C184 C191 1.423(2) . ? C184 H184 0.99(2) . ? N185 C191 1.340(2) . ? N185 C192 1.342(2) . ? C186 C187 1.365(3) . ? C186 C192 1.427(2) . ? C186 H186 1.04(2) . ? C187 C188 1.422(3) . ? C187 H187 0.98(2) . ? C188 C189 1.352(3) . ? C188 H188 0.97(3) . ? C189 C193 1.430(2) . ? C189 H189 1.05(3) . ? N190 C193 1.337(2) . ? N190 C194 1.345(2) . ? C191 C194 1.434(2) . ? C192 C193 1.436(2) . ? C201 C202 1.353(3) . ? C201 C214 1.426(2) . ? C201 H201 1.01(2) . ? C202 C203 1.419(3) . ? C202 H202 1.00(2) . ? C203 C204 1.367(3) . ? C203 H203 0.96(2) . ? C204 C211 1.424(2) . ? C204 H204 1.02(2) . ? N205 C211 1.338(2) . ? N205 C212 1.346(2) . ? C206 C207 1.359(3) . ? C206 C212 1.427(3) . ? C206 H206 1.03(2) . ? C207 C208 1.403(3) . ? C207 H207 1.03(2) . ? C208 C209 1.372(3) . ? C208 H208 0.96(2) . ? C209 C213 1.429(2) . ? C209 H209 0.946(19) . ? N210 C213 1.339(2) . ? N210 C214 1.341(2) . ? C211 C214 1.436(2) . ? C212 C213 1.434(2) . ? C221 C222 1.355(3) . ? C221 C234 1.425(2) . ? C221 H221 1.05(2) . ? C222 C223 1.420(3) . ? C222 H222 1.03(2) . ? C223 C224 1.368(3) . ? C223 H223 1.00(2) . ? C224 C231 1.425(2) . ? C224 H224 0.98(2) . ? N225 C231 1.341(2) . ? N225 C232 1.349(2) . ? C226 C227 1.364(3) . ? C226 C232 1.419(2) . ? C226 H226 0.97(3) . ? C227 C228 1.423(3) . ? C227 H227 0.97(3) . ? C228 C229 1.357(3) . ? C228 H228 0.98(3) . ? C229 C233 1.427(2) . ? C229 H229 1.04(2) . ? N230 C233 1.336(2) . ? N230 C234 1.340(2) . ? C231 C234 1.430(2) . ? C232 C233 1.432(2) . ? C241 C242 1.356(3) . ? C241 C254 1.431(2) . ? C241 H241 1.03(2) . ? C242 C243 1.419(4) . ? C242 H242 1.01(3) . ? C243 C244 1.362(3) . ? C243 H243 0.99(2) . ? C244 C251 1.421(2) . ? C244 H244 0.97(2) . ? N245 C251 1.343(2) . ? N245 C252 1.347(2) . ? C246 C247 1.366(4) . ? C246 C252 1.416(3) . ? C246 H246 0.90(2) . ? C247 C248 1.420(5) . ? C247 H247 0.89(3) . ? C248 C249 1.338(4) . ? C248 H248 1.01(3) . ? C249 C253 1.427(2) . ? C249 H249 1.07(3) . ? N250 C254 1.334(2) . ? N250 C253 1.336(2) . ? C251 C254 1.427(2) . ? C252 C253 1.431(3) . ? 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 C2 C1 C6 118.75(13) . . ? C2 C1 C7 119.72(14) . . ? C6 C1 C7 121.52(13) . . ? O1 C7 O2 122.78(14) . . ? O1 C7 C1 123.65(14) . . ? O2 C7 C1 113.56(14) . . ? C7 O2 H2A 110.5(15) . . ? C3 C2 C1 120.98(14) . . ? C3 C2 H2 119.6(12) . . ? C1 C2 H2 119.4(12) . . ? C2 C3 C4 120.45(14) . . ? C2 C3 H3 119.0(12) . . ? C4 C3 H3 120.6(12) . . ? N1 C4 C5 121.27(14) . . ? N1 C4 C3 120.26(14) . . ? C5 C4 C3 118.46(14) . . ? C4 N1 H1A 115.6(16) . . ? C4 N1 H1B 119.3(14) . . ? H1A N1 H1B 125(2) . . ? C6 C5 C4 120.70(14) . . ? C6 C5 H5 119.3(13) . . ? C4 C5 H5 119.9(13) . . ? C5 C6 C1 120.65(14) . . ? C5 C6 H6 121.0(13) . . ? C1 C6 H6 118.4(13) . . ? C16 C11 C12 119.12(14) . . ? C16 C11 C17 119.21(14) . . ? C12 C11 C17 121.66(14) . . ? O11 C17 O12 122.21(15) . . ? O11 C17 C11 123.81(14) . . ? O12 C17 C11 113.98(14) . . ? C17 O12 H12A 109.0(17) . . ? C13 C12 C11 120.49(14) . . ? C13 C12 H12 118.7(11) . . ? C11 C12 H12 120.8(11) . . ? C12 C13 C14 120.50(15) . . ? C12 C13 H13 120.3(12) . . ? C14 C13 H13 119.1(12) . . ? N11 C14 C13 121.57(15) . . ? N11 C14 C15 119.79(15) . . ? C13 C14 C15 118.63(15) . . ? C14 N11 H11A 117.6(15) . . ? C14 N11 H11B 116.9(15) . . ? H11A N11 H11B 124(2) . . ? C16 C15 C14 120.43(14) . . ? C16 C15 H15 120.1(12) . . ? C14 C15 H15 119.4(12) . . ? C15 C16 C11 120.83(14) . . ? C15 C16 H16 119.5(10) . . ? C11 C16 H16 119.6(10) . . ? C26 C21 C22 119.09(14) . . ? C26 C21 C27 118.82(13) . . ? C22 C21 C27 122.09(13) . . ? O21 C27 O22 122.06(14) . . ? O21 C27 C21 124.42(14) . . ? O22 C27 C21 113.50(13) . . ? C27 O22 H22A 113.0(19) . . ? C23 C22 C21 120.50(14) . . ? C23 C22 H22 119.7(11) . . ? C21 C22 H22 119.8(11) . . ? C22 C23 C24 120.57(14) . . ? C22 C23 H23 121.6(13) . . ? C24 C23 H23 117.6(13) . . ? N21 C24 C25 120.30(14) . . ? N21 C24 C23 121.26(14) . . ? C25 C24 C23 118.44(14) . . ? C24 N21 H21A 119.3(13) . . ? C24 N21 H21B 117.9(15) . . ? H21A N21 H21B 123(2) . . ? C26 C25 C24 120.61(14) . . ? C26 C25 H25 120.8(11) . . ? C24 C25 H25 118.5(11) . . ? C25 C26 C21 120.77(14) . . ? C25 C26 H26 117.5(11) . . ? C21 C26 H26 121.7(11) . . ? C32 C31 C36 118.96(14) . . ? C32 C31 C37 119.50(14) . . ? C36 C31 C37 121.54(14) . . ? O31 C37 O32 122.44(14) . . ? O31 C37 C31 123.64(15) . . ? O32 C37 C31 113.92(14) . . ? C37 O32 H32A 112.5(18) . . ? C33 C32 C31 120.67(14) . . ? C33 C32 H32 119.3(14) . . ? C31 C32 H32 120.0(14) . . ? C32 C33 C34 120.96(14) . . ? C32 C33 H33 120.8(10) . . ? C34 C33 H33 118.3(10) . . ? N31 C34 C33 120.82(14) . . ? N31 C34 C35 120.89(15) . . ? C33 C34 C35 118.29(14) . . ? C34 N31 H31A 117.7(18) . . ? C34 N31 H31B 117.3(15) . . ? H31A N31 H31B 125(2) . . ? C36 C35 C34 120.47(14) . . ? C36 C35 H35 120.0(12) . . ? C34 C35 H35 119.6(12) . . ? C35 C36 C31 120.64(14) . . ? C35 C36 H36 121.8(12) . . ? C31 C36 H36 117.5(12) . . ? C102 C101 C114 119.90(17) . . ? C102 C101 H101 121.2(15) . . ? C114 C101 H101 118.9(15) . . ? C101 C102 C103 120.97(18) . . ? C101 C102 H102 117.7(15) . . ? C103 C102 H102 121.3(15) . . ? C104 C103 C102 120.86(16) . . ? C104 C103 H103 120.6(13) . . ? C102 C103 H103 118.3(13) . . ? C103 C104 C111 120.19(17) . . ? C103 C104 H104 119.1(12) . . ? C111 C104 H104 120.7(12) . . ? C111 N105 C112 116.70(14) . . ? C107 C106 C112 119.88(16) . . ? C107 C106 H106 119.9(14) . . ? C112 C106 H106 120.3(14) . . ? C106 C107 C108 121.08(16) . . ? C106 C107 H107 119.6(14) . . ? C108 C107 H107 119.3(14) . . ? C109 C108 C107 120.86(16) . . ? C109 C108 H108 118.8(11) . . ? C107 C108 H108 120.2(11) . . ? C108 C109 C113 119.85(16) . . ? C108 C109 H109 121.8(13) . . ? C113 C109 H109 118.4(13) . . ? C114 N110 C113 117.11(13) . . ? N105 C111 C104 119.82(15) . . ? N105 C111 C114 121.78(14) . . ? C104 C111 C114 118.39(15) . . ? N105 C112 C113 122.09(14) . . ? N105 C112 C106 119.14(15) . . ? C113 C112 C106 118.75(15) . . ? N110 C113 C109 119.44(14) . . ? N110 C113 C112 120.98(14) . . ? C109 C113 C112 119.56(15) . . ? N110 C114 C101 118.97(15) . . ? N110 C114 C111 121.34(14) . . ? C101 C114 C111 119.69(14) . . ? C122 C121 C134 119.93(16) . . ? C122 C121 H121 120.4(14) . . ? C134 C121 H121 119.7(14) . . ? C121 C122 C123 120.89(16) . . ? C121 C122 H122 118.8(12) . . ? C123 C122 H122 120.3(12) . . ? C124 C123 C122 121.48(16) . . ? C124 C123 H123 121.3(13) . . ? C122 C123 H123 117.2(13) . . ? C123 C124 C131 119.40(16) . . ? C123 C124 H124 125.5(13) . . ? C131 C124 H124 115.1(13) . . ? C131 N125 C132 117.66(14) . . ? C127 C126 C132 119.49(18) . . ? C127 C126 H126 120.8(15) . . ? C132 C126 H126 119.6(14) . . ? C126 C127 C128 121.40(18) . . ? C126 C127 H127 120(2) . . ? C128 C127 H127 119(2) . . ? C129 C128 C127 120.52(18) . . ? C129 C128 H128 124.1(15) . . ? C127 C128 H128 115.4(15) . . ? C128 C129 C133 120.30(19) . . ? C128 C129 H129 121.7(13) . . ? C133 C129 H129 118.0(14) . . ? C133 N130 C134 117.01(14) . . ? N125 C131 C124 119.89(14) . . ? N125 C131 C134 120.72(14) . . ? C124 C131 C134 119.39(15) . . ? N125 C132 C126 119.83(15) . . ? N125 C132 C133 120.68(14) . . ? C126 C132 C133 119.48(16) . . ? N130 C133 C129 119.29(16) . . ? N130 C133 C132 121.92(14) . . ? C129 C133 C132 118.78(16) . . ? N130 C134 C121 119.10(14) . . ? N130 C134 C131 122.00(14) . . ? C121 C134 C131 118.90(14) . . ? C142 C141 C154 120.39(16) . . ? C142 C141 H154 122.7(11) . . ? C154 C141 H154 116.8(11) . . ? C141 C142 C143 120.58(17) . . ? C141 C142 H142 120.2(13) . . ? C143 C142 H142 119.2(13) . . ? C144 C143 C142 120.67(16) . . ? C144 C143 H143 122.6(13) . . ? C142 C143 H143 116.7(13) . . ? C143 C144 C151 120.70(17) . . ? C143 C144 H144 121.3(11) . . ? C151 C144 H144 117.9(12) . . ? C151 N145 C152 117.13(14) . . ? C147 C146 C152 119.80(19) . . ? C147 C146 H146 121.8(13) . . ? C152 C146 H146 118.2(13) . . ? C146 C147 C148 120.79(18) . . ? C146 C147 H147 122.2(16) . . ? C148 C147 H147 117.0(15) . . ? C149 C148 C147 121.58(18) . . ? C149 C148 H148 120.9(13) . . ? C147 C148 H148 117.5(13) . . ? C148 C149 C153 119.25(19) . . ? C148 C149 H149 122.3(13) . . ? C153 C149 H149 118.4(13) . . ? C154 N150 C153 117.41(14) . . ? N145 C151 C144 119.52(15) . . ? N145 C151 C154 121.62(14) . . ? C144 C151 C154 118.83(15) . . ? N145 C152 C146 119.17(16) . . ? N145 C152 C153 121.83(15) . . ? C146 C152 C153 118.98(16) . . ? N150 C153 C149 119.63(16) . . ? N150 C153 C152 120.84(14) . . ? C149 C153 C152 119.52(16) . . ? N150 C154 C141 120.11(15) . . ? N150 C154 C151 121.06(14) . . ? C141 C154 C151 118.81(15) . . ? C162 C161 C174 120.13(16) . . ? C162 C161 H161 119.9(11) . . ? C174 C161 H161 119.9(11) . . ? C161 C162 C163 120.74(16) . . ? C161 C162 H162 119.7(12) . . ? C163 C162 H162 119.6(12) . . ? C164 C163 C162 120.81(16) . . ? C164 C163 H163 122.4(12) . . ? C162 C163 H163 116.8(12) . . ? C163 C164 C171 120.03(16) . . ? C163 C164 H164 123.2(13) . . ? C171 C164 H164 116.7(13) . . ? C172 N165 C171 117.40(14) . . ? C167 C166 C172 119.87(17) . . ? C167 C166 H166 122.2(13) . . ? C172 C166 H166 117.9(13) . . ? C166 C167 C168 121.06(17) . . ? C166 C167 H167 122.2(13) . . ? C168 C167 H167 116.7(13) . . ? C169 C168 C167 120.70(17) . . ? C169 C168 H168 121.0(13) . . ? C167 C168 H168 118.3(13) . . ? C168 C169 C173 120.55(17) . . ? C168 C169 H169 124.0(13) . . ? C173 C169 H169 115.4(13) . . ? C173 N170 C174 117.02(14) . . ? N165 C171 C164 119.61(14) . . ? N165 C171 C174 121.14(14) . . ? C164 C171 C174 119.25(15) . . ? N165 C172 C166 119.64(15) . . ? N165 C172 C173 121.02(14) . . ? C166 C172 C173 119.34(15) . . ? N170 C173 C169 119.74(15) . . ? N170 C173 C172 121.80(14) . . ? C169 C173 C172 118.46(15) . . ? N170 C174 C161 119.35(15) . . ? N170 C174 C171 121.61(14) . . ? C161 C174 C171 119.04(15) . . ? C182 C181 C194 119.67(16) . . ? C182 C181 H181 120.7(12) . . ? C194 C181 H181 119.6(12) . . ? C181 C182 C183 121.27(17) . . ? C181 C182 H182 118.8(12) . . ? C183 C182 H182 119.8(12) . . ? C184 C183 C182 120.81(16) . . ? C184 C183 H183 119.3(12) . . ? C182 C183 H183 119.9(12) . . ? C183 C184 C191 119.93(16) . . ? C183 C184 H184 119.8(13) . . ? C191 C184 H184 120.2(13) . . ? C191 N185 C192 117.31(14) . . ? C187 C186 C192 119.52(18) . . ? C187 C186 H186 121.8(11) . . ? C192 C186 H186 118.7(11) . . ? C186 C187 C188 121.10(18) . . ? C186 C187 H187 121.1(13) . . ? C188 C187 H187 117.8(13) . . ? C189 C188 C187 120.97(17) . . ? C189 C188 H188 118.2(16) . . ? C187 C188 H188 120.8(16) . . ? C188 C189 C193 120.34(18) . . ? C188 C189 H189 125.3(13) . . ? C193 C189 H189 114.3(13) . . ? C193 N190 C194 116.68(14) . . ? N185 C191 C184 119.41(14) . . ? N185 C191 C194 121.23(14) . . ? C184 C191 C194 119.36(15) . . ? N185 C192 C186 119.39(15) . . ? N185 C192 C193 121.19(15) . . ? C186 C192 C193 119.41(15) . . ? N190 C193 C189 119.54(16) . . ? N190 C193 C192 121.82(14) . . ? C189 C193 C192 118.65(16) . . ? N190 C194 C181 119.30(15) . . ? N190 C194 C191 121.74(15) . . ? C181 C194 C191 118.96(15) . . ? C202 C201 C214 119.72(17) . . ? C202 C201 H201 121.6(12) . . ? C214 C201 H201 118.5(12) . . ? C201 C202 C203 121.32(18) . . ? C201 C202 H202 117.3(14) . . ? C203 C202 H202 121.4(14) . . ? C204 C203 C202 120.94(17) . . ? C204 C203 H203 118.2(15) . . ? C202 C203 H203 120.8(15) . . ? C203 C204 C211 119.62(16) . . ? C203 C204 H204 120.3(12) . . ? C211 C204 H204 119.9(12) . . ? C211 N205 C212 117.69(14) . . ? C207 C206 C212 119.42(19) . . ? C207 C206 H206 120.6(12) . . ? C212 C206 H206 119.9(12) . . ? C206 C207 C208 121.1(2) . . ? C206 C207 H207 119.7(14) . . ? C208 C207 H207 119.2(13) . . ? C209 C208 C207 121.33(18) . . ? C209 C208 H208 116.6(15) . . ? C207 C208 H208 122.0(15) . . ? C208 C209 C213 120.20(19) . . ? C208 C209 H209 129.2(11) . . ? C213 C209 H209 110.5(11) . . ? C213 N210 C214 116.86(14) . . ? N205 C211 C204 119.92(15) . . ? N205 C211 C214 121.05(14) . . ? C204 C211 C214 119.01(15) . . ? N205 C212 C206 118.93(16) . . ? N205 C212 C213 120.67(15) . . ? C206 C212 C213 120.38(16) . . ? N210 C213 C209 120.40(16) . . ? N210 C213 C212 121.99(15) . . ? C209 C213 C212 117.57(17) . . ? N210 C214 C201 118.95(15) . . ? N210 C214 C211 121.67(15) . . ? C201 C214 C211 119.36(15) . . ? C222 C221 C234 120.02(18) . . ? C222 C221 H221 120.6(13) . . ? C234 C221 H221 119.4(13) . . ? C221 C222 C223 120.74(18) . . ? C221 C222 H222 119.8(13) . . ? C223 C222 H222 119.4(13) . . ? C224 C223 C222 121.46(17) . . ? C224 C223 H223 121.1(14) . . ? C222 C223 H223 117.4(14) . . ? C223 C224 C231 119.08(18) . . ? C223 C224 H224 124.1(13) . . ? C231 C224 H224 116.7(13) . . ? C231 N225 C232 117.66(13) . . ? C227 C226 C232 119.69(17) . . ? C227 C226 H226 120.4(15) . . ? C232 C226 H226 119.8(15) . . ? C226 C227 C228 121.04(18) . . ? C226 C227 H227 120.7(17) . . ? C228 C227 H227 118.3(17) . . ? C229 C228 C227 120.74(17) . . ? C229 C228 H228 120.5(16) . . ? C227 C228 H228 118.7(16) . . ? C228 C229 C233 120.14(18) . . ? C228 C229 H229 125.4(13) . . ? C233 C229 H229 114.4(13) . . ? C233 N230 C234 117.16(14) . . ? N225 C231 C224 119.63(15) . . ? N225 C231 C234 120.90(14) . . ? C224 C231 C234 119.46(15) . . ? N225 C232 C226 119.81(15) . . ? N225 C232 C233 120.70(14) . . ? C226 C232 C233 119.49(15) . . ? N230 C233 C229 119.31(15) . . ? N230 C233 C232 121.80(14) . . ? C229 C233 C232 118.89(15) . . ? N230 C234 C221 119.02(15) . . ? N230 C234 C231 121.76(15) . . ? C221 C234 C231 119.23(15) . . ? C242 C241 C254 120.2(2) . . ? C242 C241 H241 122.2(14) . . ? C254 C241 H241 117.6(14) . . ? C241 C242 C243 120.67(19) . . ? C241 C242 H242 119.0(18) . . ? C243 C242 H242 120.2(17) . . ? C244 C243 C242 121.13(19) . . ? C244 C243 H243 119.8(15) . . ? C242 C243 H243 119.1(15) . . ? C243 C244 C251 119.8(2) . . ? C243 C244 H244 123.2(14) . . ? C251 C244 H244 117.0(14) . . ? C251 N245 C252 116.52(15) . . ? C247 C246 C252 120.0(3) . . ? C247 C246 H246 122.4(14) . . ? C252 C246 H246 117.6(14) . . ? C246 C247 C248 121.1(2) . . ? C246 C247 H247 120(2) . . ? C248 C247 H247 118(2) . . ? C249 C248 C247 120.7(2) . . ? C249 C248 H248 125(2) . . ? C247 C248 H248 114.0(19) . . ? C248 C249 C253 120.2(3) . . ? C248 C249 H249 119.8(16) . . ? C253 C249 H249 120.0(16) . . ? C254 N250 C253 116.41(15) . . ? N245 C251 C244 119.28(16) . . ? N245 C251 C254 121.29(15) . . ? C244 C251 C254 119.42(16) . . ? N245 C252 C246 120.11(19) . . ? N245 C252 C253 121.44(16) . . ? C246 C252 C253 118.44(18) . . ? N250 C253 C249 118.6(2) . . ? N250 C253 C252 121.91(15) . . ? C249 C253 C252 119.53(19) . . ? N250 C254 C251 122.42(16) . . ? N250 C254 C241 118.76(17) . . ? C251 C254 C241 118.82(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B O11 0.94(2) 1.98(2) 2.894(2) 165(2) 2_766 N1 H1A N165 0.85(2) 2.18(2) 3.034(2) 176(2) 2_665 N11 H11A O1 0.89(2) 2.04(2) 2.919(2) 170(2) 2_666 N11 H11B N245 0.90(2) 2.16(2) 3.055(2) 173(2) 1_565 N21 H21A O31 0.90(2) 2.00(2) 2.8827(19) 167.4(19) 2_666 N21 H21B N110 0.93(2) 2.15(2) 3.057(2) 166(2) 1_546 N31 H31A N185 0.86(3) 2.17(3) 3.025(2) 173(2) 2_666 N31 H31B O21 0.92(2) 2.00(2) 2.902(2) 165(2) 2_566 O2 H2A N225 0.96(3) 1.76(3) 2.6873(18) 161(2) 1_545 O12 H12A N150 0.99(3) 1.75(3) 2.7112(19) 161(3) 2_767 O22 H22A N205 1.02(3) 1.71(3) 2.7061(19) 163(3) 2_566 O32 H32A N125 0.97(3) 1.76(3) 2.7036(18) 163(3) 1_564 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.624 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.067 # Attachment '- SABP_I.cif' data_SuccinicAcid_2,2-bipyridine _database_code_depnum_ccdc_archive 'CCDC 847629' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-Bipyridine Succinic acid (1/1) ; _chemical_name_common "(2,2'-Bipyridine)(Succinic acid)" _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 N2, C4 H6 O4' _chemical_formula_sum 'C14 H14 N2 O4' _chemical_formula_weight 274.27 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 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 8.958(3) _cell_length_b 5.1788(14) _cell_length_c 14.357(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.109(4) _cell_angle_gamma 90.00 _cell_volume 639.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3531 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 28.33 _exptl_crystal_description Needle-like _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7480 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5107 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 28.33 _reflns_number_total 1523 _reflns_number_gt 1316 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; SHELXTL (Bruker, 2000) and Mercury (Macrae et al., 2006) ; _computing_publication_material 'Bruker SHELXTL and local programs' _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. All the H atoms were identified from the Fourier difference map and refined isotropically. ; _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^)+(0.0526P)^2^+0.1387P] 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 1523 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 O2 O 0.75702(10) -0.41419(17) -0.02628(6) 0.0273(2) Uani 1 1 d . . . O1 O 0.93813(10) -0.32357(18) 0.11154(7) 0.0340(3) Uani 1 1 d . . . N1 N 0.65570(11) 0.19736(18) 0.07493(7) 0.0195(2) Uani 1 1 d . . . C1 C 0.54790(12) 0.0080(2) 0.05152(8) 0.0170(2) Uani 1 1 d . . . C2 C 0.52830(14) -0.1661(2) 0.12124(8) 0.0223(3) Uani 1 1 d . . . H2 H 0.4533(19) -0.297(3) 0.1036(11) 0.033(4) Uiso 1 1 d . . . C3 C 0.62005(14) -0.1458(2) 0.21591(8) 0.0238(3) Uani 1 1 d . . . H3 H 0.6051(17) -0.265(3) 0.2637(11) 0.032(4) Uiso 1 1 d . . . C4 C 0.73021(14) 0.0468(2) 0.23972(8) 0.0224(3) Uani 1 1 d . . . H4 H 0.7963(16) 0.069(3) 0.3031(11) 0.024(3) Uiso 1 1 d . . . C5 C 0.74362(14) 0.2127(2) 0.16707(9) 0.0223(3) Uani 1 1 d . . . H5 H 0.8170(18) 0.347(3) 0.1786(11) 0.028(4) Uiso 1 1 d . . . C6 C 0.87875(13) -0.2821(2) 0.02707(8) 0.0194(3) Uani 1 1 d . . . C7 C 0.93174(13) -0.0765(2) -0.03077(9) 0.0213(3) Uani 1 1 d . . . H7A H 0.8437(17) 0.034(3) -0.0573(10) 0.029(4) Uiso 1 1 d . . . H7B H 0.9582(17) -0.163(3) -0.0831(11) 0.030(4) Uiso 1 1 d . . . H1 H 0.726(2) -0.539(4) 0.0088(16) 0.068(6) 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 O2 0.0330(5) 0.0273(5) 0.0217(4) -0.0025(3) 0.0080(4) -0.0147(4) O1 0.0278(5) 0.0355(6) 0.0317(5) 0.0134(4) -0.0034(4) -0.0116(4) N1 0.0210(5) 0.0187(5) 0.0189(5) -0.0008(4) 0.0057(4) -0.0027(4) C1 0.0177(5) 0.0155(5) 0.0185(6) -0.0015(4) 0.0061(4) 0.0005(4) C2 0.0227(6) 0.0210(6) 0.0223(6) 0.0009(4) 0.0047(5) -0.0059(4) C3 0.0261(6) 0.0249(6) 0.0200(6) 0.0048(4) 0.0058(5) -0.0021(5) C4 0.0218(5) 0.0268(6) 0.0175(6) -0.0007(4) 0.0034(4) -0.0006(4) C5 0.0225(6) 0.0226(6) 0.0213(6) -0.0029(4) 0.0053(4) -0.0057(4) C6 0.0182(5) 0.0159(5) 0.0254(6) -0.0008(4) 0.0082(4) 0.0003(4) C7 0.0231(6) 0.0177(6) 0.0241(6) -0.0004(4) 0.0081(5) -0.0040(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 O2 C6 1.3342(14) . ? O2 H1 0.91(2) . ? O1 C6 1.2008(14) . ? N1 C5 1.3411(15) . ? N1 C1 1.3517(14) . ? C1 C2 1.3941(16) . ? C1 C1 1.492(2) 3_655 ? C2 C3 1.3835(16) . ? C2 H2 0.940(16) . ? C3 C4 1.3778(17) . ? C3 H3 0.962(16) . ? C4 C5 1.3821(17) . ? C4 H4 0.945(14) . ? C5 H5 0.939(16) . ? C6 C7 1.5058(15) . ? C7 C7 1.518(2) 3_755 ? C7 H7A 0.964(15) . ? C7 H7B 0.959(16) . ? 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 C6 O2 H1 112.1(13) . . ? C5 N1 C1 118.16(10) . . ? N1 C1 C2 120.95(10) . . ? N1 C1 C1 117.48(12) . 3_655 ? C2 C1 C1 121.56(12) . 3_655 ? C3 C2 C1 119.82(11) . . ? C3 C2 H2 120.3(9) . . ? C1 C2 H2 119.8(9) . . ? C4 C3 C2 119.23(11) . . ? C4 C3 H3 121.4(9) . . ? C2 C3 H3 119.3(9) . . ? C3 C4 C5 117.97(11) . . ? C3 C4 H4 122.8(9) . . ? C5 C4 H4 119.2(9) . . ? N1 C5 C4 123.87(11) . . ? N1 C5 H5 114.1(9) . . ? C4 C5 H5 122.0(9) . . ? O1 C6 O2 123.40(11) . . ? O1 C6 C7 124.36(10) . . ? O2 C6 C7 112.24(10) . . ? C6 C7 C7 111.99(12) . 3_755 ? C6 C7 H7A 106.9(9) . . ? C7 C7 H7A 111.0(9) 3_755 . ? C6 C7 H7B 106.6(9) . . ? C7 C7 H7B 111.4(9) 3_755 . ? H7A C7 H7B 108.8(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.17(16) . . . . ? C5 N1 C1 C1 -179.42(11) . . . 3_655 ? N1 C1 C2 C3 0.05(17) . . . . ? C1 C1 C2 C3 179.62(13) 3_655 . . . ? C1 C2 C3 C4 -0.21(18) . . . . ? C2 C3 C4 C5 0.15(18) . . . . ? C1 N1 C5 C4 -0.24(17) . . . . ? C3 C4 C5 N1 0.07(18) . . . . ? O1 C6 C7 C7 -0.92(19) . . . 3_755 ? O2 C6 C7 C7 178.91(12) . . . 3_755 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1 N1 0.91(2) 1.87(2) 2.7774(14) 177(2) 1_545 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.284 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.081 # Attachment '- SADCPR_II.cif' data_SuccinicAcid_diphenylcyclopropenone _database_code_depnum_ccdc_archive 'CCDC 847630' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Diphenylcyclopropenone Succinic acid (2/1) ; _chemical_name_common '2(Diphenylcyclopropenone)(Succinic Acid)' _chemical_melting_point ? _chemical_formula_moiety 'C15 H10 O, 0.5(C4 H6 O4)' _chemical_formula_sum 'C17 H13 O3' _chemical_formula_weight 265.27 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' 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 14.654(4) _cell_length_b 5.5540(14) _cell_length_c 16.288(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.471(4) _cell_angle_gamma 90.00 _cell_volume 1325.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4236 _cell_measurement_theta_min 2.5011 _cell_measurement_theta_max 28.2575 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8442 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10750 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3179 _reflns_number_gt 2638 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; SHELXTL (Bruker, 2000) and Mercury (Macrae et al., 2006) ; _computing_publication_material 'Bruker SHELXTL and local programs' _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. All the H atoms were identified from the Fourier difference map and refined isotropically. ; _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^)+(0.0782P)^2^+0.2534P] 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 3179 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1261 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 O1 O 0.30165(6) 1.02278(18) 0.43259(7) 0.0399(3) Uani 1 1 d . . . C6 C 0.46878(8) 0.5467(2) 0.37606(7) 0.0231(3) Uani 1 1 d . . . C5 C 0.53612(9) 0.6634(2) 0.42245(8) 0.0257(3) Uani 1 1 d . . . C15 C 0.24017(9) 0.3504(2) 0.23722(8) 0.0283(3) Uani 1 1 d . . . C9 C 0.29192(8) 0.6533(2) 0.34021(8) 0.0249(3) Uani 1 1 d . . . C10 C 0.22375(8) 0.5558(2) 0.28423(7) 0.0244(3) Uani 1 1 d . . . C1 C 0.48946(9) 0.3306(2) 0.33626(8) 0.0260(3) Uani 1 1 d . . . C12 C 0.07719(9) 0.6017(3) 0.21802(8) 0.0319(3) Uani 1 1 d . . . C8 C 0.31809(8) 0.8365(2) 0.39469(8) 0.0277(3) Uani 1 1 d . . . C3 C 0.64261(9) 0.3500(2) 0.39048(8) 0.0295(3) Uani 1 1 d . . . C11 C 0.14106(9) 0.6796(2) 0.27497(8) 0.0280(3) Uani 1 1 d . . . C2 C 0.57633(9) 0.2332(2) 0.34391(8) 0.0297(3) Uani 1 1 d . . . C4 C 0.62297(9) 0.5654(3) 0.42946(8) 0.0294(3) Uani 1 1 d . . . C7 C 0.37861(8) 0.6530(2) 0.37155(7) 0.0246(3) Uani 1 1 d . . . C14 C 0.17592(10) 0.2740(3) 0.18002(8) 0.0321(3) Uani 1 1 d . . . C13 C 0.09518(10) 0.4008(3) 0.17016(8) 0.0330(3) Uani 1 1 d . . . O3 O 0.16956(6) 0.02726(18) 0.99206(6) 0.0347(3) Uani 1 1 d . . . O2 O 0.12665(7) 0.36814(19) 0.93026(7) 0.0389(3) Uani 1 1 d . . . C16 C 0.11022(8) 0.1600(2) 0.96652(7) 0.0236(3) Uani 1 1 d . . . C17 C 0.00964(8) 0.1067(2) 0.97251(8) 0.0269(3) Uani 1 1 d . . . H2 H 0.5894(11) 0.079(3) 0.3156(10) 0.034(4) Uiso 1 1 d . . . H5 H 0.5202(11) 0.813(3) 0.4516(10) 0.036(4) Uiso 1 1 d . . . H4 H 0.6711(14) 0.647(3) 0.4622(12) 0.055(5) Uiso 1 1 d . . . H1 H 0.4430(11) 0.244(3) 0.3034(10) 0.034(4) Uiso 1 1 d . . . H3 H 0.7020(11) 0.278(3) 0.3971(10) 0.036(4) Uiso 1 1 d . . . H7 H 0.0201(12) 0.688(3) 0.2114(10) 0.040(4) Uiso 1 1 d . . . H6 H 0.1295(11) 0.822(3) 0.3079(10) 0.034(4) Uiso 1 1 d . . . H8 H 0.0486(13) 0.349(3) 0.1323(11) 0.046(5) Uiso 1 1 d . . . H10 H 0.2974(11) 0.259(3) 0.2430(10) 0.037(4) Uiso 1 1 d . . . H9 H 0.1865(11) 0.129(3) 0.1458(10) 0.034(4) Uiso 1 1 d . . . H12 H -0.0223(11) 0.256(3) 0.9920(11) 0.040(4) Uiso 1 1 d . . . H13 H -0.0133(12) 0.072(3) 0.9146(12) 0.050(5) Uiso 1 1 d . . . H11 H 0.1915(17) 0.392(4) 0.9343(15) 0.084(7) 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 O1 0.0281(5) 0.0380(6) 0.0534(7) -0.0214(5) -0.0032(4) 0.0092(4) C6 0.0222(6) 0.0250(6) 0.0222(6) 0.0010(5) 0.0026(4) 0.0027(5) C5 0.0252(6) 0.0271(6) 0.0248(6) -0.0019(5) 0.0020(5) 0.0007(5) C15 0.0244(6) 0.0293(7) 0.0313(7) -0.0024(5) 0.0017(5) -0.0002(5) C9 0.0224(6) 0.0269(6) 0.0255(6) -0.0010(5) 0.0016(4) 0.0024(5) C10 0.0223(6) 0.0275(6) 0.0233(6) 0.0015(5) 0.0008(4) -0.0024(5) C1 0.0237(6) 0.0260(6) 0.0283(6) -0.0015(5) 0.0002(5) 0.0011(5) C12 0.0257(7) 0.0388(7) 0.0311(7) 0.0010(6) -0.0039(5) 0.0041(6) C8 0.0209(6) 0.0319(7) 0.0302(6) -0.0044(5) 0.0001(5) 0.0032(5) C3 0.0209(6) 0.0351(7) 0.0325(7) 0.0055(5) 0.0025(5) 0.0059(5) C11 0.0276(6) 0.0286(6) 0.0277(6) -0.0013(5) 0.0006(5) 0.0025(5) C2 0.0301(7) 0.0262(6) 0.0331(7) -0.0002(5) 0.0044(5) 0.0054(5) C4 0.0228(6) 0.0363(7) 0.0290(6) 0.0011(5) -0.0010(5) -0.0022(5) C7 0.0239(6) 0.0258(6) 0.0242(6) -0.0024(5) 0.0012(4) 0.0006(5) C14 0.0319(7) 0.0333(7) 0.0312(7) -0.0069(6) 0.0012(5) -0.0034(6) C13 0.0289(7) 0.0418(8) 0.0284(7) -0.0043(6) -0.0037(5) -0.0047(6) O3 0.0222(5) 0.0381(5) 0.0439(6) 0.0068(4) -0.0033(4) -0.0012(4) O2 0.0267(5) 0.0368(6) 0.0532(7) 0.0164(5) -0.0004(4) -0.0072(4) C16 0.0214(6) 0.0268(6) 0.0225(6) -0.0002(5) -0.0002(4) -0.0045(5) C17 0.0209(6) 0.0300(7) 0.0298(7) 0.0034(5) -0.0028(5) -0.0041(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 O1 C8 1.2298(16) . ? C6 C5 1.3974(17) . ? C6 C1 1.3982(17) . ? C6 C7 1.4485(17) . ? C5 C4 1.3881(18) . ? C5 H5 0.987(17) . ? C15 C14 1.3857(19) . ? C15 C10 1.3955(18) . ? C15 H10 0.985(17) . ? C9 C7 1.3652(18) . ? C9 C8 1.4012(18) . ? C9 C10 1.4519(17) . ? C10 C11 1.4006(18) . ? C1 C2 1.3879(18) . ? C1 H1 0.988(16) . ? C12 C11 1.3818(19) . ? C12 C13 1.387(2) . ? C12 H7 0.970(17) . ? C8 C7 1.4047(17) . ? C3 C4 1.386(2) . ? C3 C2 1.3884(19) . ? C3 H3 0.963(17) . ? C11 H6 0.971(16) . ? C2 H2 0.990(16) . ? C4 H4 0.99(2) . ? C14 C13 1.385(2) . ? C14 H9 0.994(16) . ? C13 H8 0.960(18) . ? O3 C16 1.2112(15) . ? O2 C16 1.3210(15) . ? O2 H11 0.96(3) . ? C16 C17 1.5073(17) . ? C17 C17 1.514(3) 3_557 ? C17 H12 1.004(18) . ? C17 H13 1.018(19) . ? 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 C5 C6 C1 119.61(11) . . ? C5 C6 C7 118.56(11) . . ? C1 C6 C7 121.83(11) . . ? C4 C5 C6 120.37(12) . . ? C4 C5 H5 120.7(9) . . ? C6 C5 H5 118.9(9) . . ? C14 C15 C10 119.99(12) . . ? C14 C15 H10 118.6(9) . . ? C10 C15 H10 121.4(10) . . ? C7 C9 C8 61.01(9) . . ? C7 C9 C10 150.18(12) . . ? C8 C9 C10 148.42(12) . . ? C15 C10 C11 119.68(12) . . ? C15 C10 C9 121.92(11) . . ? C11 C10 C9 118.33(12) . . ? C2 C1 C6 119.67(12) . . ? C2 C1 H1 119.0(9) . . ? C6 C1 H1 121.3(9) . . ? C11 C12 C13 119.89(13) . . ? C11 C12 H7 120.0(10) . . ? C13 C12 H7 120.2(10) . . ? O1 C8 C9 151.05(13) . . ? O1 C8 C7 150.69(13) . . ? C9 C8 C7 58.23(9) . . ? C4 C3 C2 120.45(12) . . ? C4 C3 H3 119.9(10) . . ? C2 C3 H3 119.6(10) . . ? C12 C11 C10 119.94(12) . . ? C12 C11 H6 120.3(9) . . ? C10 C11 H6 119.7(9) . . ? C1 C2 C3 120.26(12) . . ? C1 C2 H2 118.4(9) . . ? C3 C2 H2 121.4(9) . . ? C3 C4 C5 119.64(12) . . ? C3 C4 H4 119.5(11) . . ? C5 C4 H4 120.9(11) . . ? C9 C7 C8 60.76(9) . . ? C9 C7 C6 149.91(12) . . ? C8 C7 C6 149.30(12) . . ? C13 C14 C15 119.82(13) . . ? C13 C14 H9 119.0(9) . . ? C15 C14 H9 121.2(9) . . ? C14 C13 C12 120.64(13) . . ? C14 C13 H8 121.5(11) . . ? C12 C13 H8 117.8(11) . . ? C16 O2 H11 106.0(14) . . ? O3 C16 O2 123.60(12) . . ? O3 C16 C17 123.90(11) . . ? O2 C16 C17 112.50(11) . . ? C16 C17 C17 112.31(13) . 3_557 ? C16 C17 H12 108.5(10) . . ? C17 C17 H12 111.6(10) 3_557 . ? C16 C17 H13 107.0(10) . . ? C17 C17 H13 109.7(11) 3_557 . ? H12 C17 H13 107.5(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C6 C5 C4 -0.31(19) . . . . ? C7 C6 C5 C4 178.94(11) . . . . ? C14 C15 C10 C11 1.85(19) . . . . ? C14 C15 C10 C9 -175.09(12) . . . . ? C7 C9 C10 C15 7.1(3) . . . . ? C8 C9 C10 C15 174.80(19) . . . . ? C7 C9 C10 C11 -169.9(2) . . . . ? C8 C9 C10 C11 -2.2(3) . . . . ? C5 C6 C1 C2 0.64(18) . . . . ? C7 C6 C1 C2 -178.58(12) . . . . ? C7 C9 C8 O1 177.7(3) . . . . ? C10 C9 C8 O1 4.6(4) . . . . ? C10 C9 C8 C7 -173.1(2) . . . . ? C13 C12 C11 C10 0.0(2) . . . . ? C15 C10 C11 C12 -1.60(19) . . . . ? C9 C10 C11 C12 175.46(12) . . . . ? C6 C1 C2 C3 -0.3(2) . . . . ? C4 C3 C2 C1 -0.3(2) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C6 C5 C4 C3 -0.3(2) . . . . ? C10 C9 C7 C8 172.7(3) . . . . ? C8 C9 C7 C6 -178.0(3) . . . . ? C10 C9 C7 C6 -5.3(4) . . . . ? O1 C8 C7 C9 -177.7(3) . . . . ? O1 C8 C7 C6 0.3(4) . . . . ? C9 C8 C7 C6 178.0(2) . . . . ? C5 C6 C7 C9 174.9(2) . . . . ? C1 C6 C7 C9 -5.9(3) . . . . ? C5 C6 C7 C8 -1.7(3) . . . . ? C1 C6 C7 C8 177.56(19) . . . . ? C10 C15 C14 C13 -0.5(2) . . . . ? C15 C14 C13 C12 -1.1(2) . . . . ? C11 C12 C13 C14 1.4(2) . . . . ? O3 C16 C17 C17 10.6(2) . . . 3_557 ? O2 C16 C17 C17 -169.37(14) . . . 3_557 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H11 O1 0.96(3) 1.68(3) 2.6351(15) 170(2) 4_576 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.471 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.051