# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_famon _database_code_depnum_ccdc_archive 'CCDC 809334' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-hydroxy-N,N,N-trimethylethanaminium 4,4'-dioxo-4H, 4'H-2,2'-spirobi[benzo[d][1,3,2]dioxaborinin]-2-uide ; _chemical_name_common 'Choline BScB' _chemical_melting_point ? _chemical_formula_moiety '2(C14 H8 B O6), C5 H14 N O, C5 N O' _chemical_formula_sum 'C38 H30 B2 N2 O14' _chemical_formula_weight 760.26 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' B B 0.0013 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 Pc _symmetry_space_group_name_Hall ' P -2yc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 9.759(4) _cell_length_b 16.442(7) _cell_length_c 12.446(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.435(11) _cell_angle_gamma 90.00 _cell_volume 1871.5(13) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 722 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 17.47 _exptl_crystal_description Cut _exptl_crystal_colour Translucent _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9797 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details 'sadabs (Bruker Apex II V 1.0, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 APEX KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13750 _diffrn_reflns_av_R_equivalents 0.1011 _diffrn_reflns_av_sigmaI/netI 0.1582 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4301 _reflns_number_gt 2002 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II V 1.0 (Bruker AXS, 2005)' _computing_cell_refinement 'Bruker Apex II V 1.0' _computing_data_reduction 'Bruker Apex II V 1.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Pov-ray for windows, version 3.1' _computing_publication_material 'Microsoft Office' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1131P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.004(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 4301 _refine_ls_number_parameters 563 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1708 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.2325 _refine_ls_wR_factor_gt 0.1780 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.064 _refine_ls_shift/su_mean 0.013 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 O9A O 0.2127(6) 0.3033(3) 0.2572(4) 0.0442(14) Uani 1 1 d . . . O11A O 0.0436(6) 0.3963(3) -0.1023(4) 0.0455(14) Uani 1 1 d . . . O8A O 0.1521(5) 0.3701(3) 0.0800(4) 0.0440(15) Uani 1 1 d . . . O10A O 0.3719(6) 0.4079(4) 0.2252(4) 0.0506(15) Uani 1 1 d . . . C16A C 0.2559(8) 0.3140(4) -0.0504(6) 0.0312(17) Uani 1 1 d . . . C23A C 0.3103(7) 0.4093(4) 0.3944(6) 0.0320(17) Uani 1 1 d . . . C28A C 0.2285(8) 0.3393(4) 0.3588(6) 0.0322(17) Uani 1 1 d . . . C27A C 0.1566(9) 0.3030(5) 0.4249(6) 0.0366(18) Uani 1 1 d . . . H27A H 0.0978 0.2560 0.3989 0.044 Uiso 1 1 calc R . . C21A C 0.3601(7) 0.2726(4) 0.0416(6) 0.0299(17) Uani 1 1 d . . . C24A C 0.3209(8) 0.4446(5) 0.4979(6) 0.0373(19) Uani 1 1 d . . . H24A H 0.3723 0.4944 0.5207 0.045 Uiso 1 1 calc R . . C15A C 0.1438(8) 0.3635(5) -0.0276(6) 0.0356(18) Uani 1 1 d . . . C22A C 0.3828(9) 0.4466(6) 0.3224(7) 0.047(2) Uani 1 1 d . . . C19A C 0.4723(9) 0.2208(5) -0.0852(7) 0.043(2) Uani 1 1 d . . . H19A H 0.5453 0.1885 -0.0987 0.052 Uiso 1 1 calc R . . O12A O 0.4582(6) 0.5068(4) 0.3499(5) 0.0578(17) Uani 1 1 d . . . O7A O 0.3559(6) 0.2757(4) 0.1477(4) 0.0598(18) Uani 1 1 d . . . C20A C 0.4659(8) 0.2257(5) 0.0219(6) 0.0379(18) Uani 1 1 d . . . H20A H 0.5346 0.1968 0.0833 0.046 Uiso 1 1 calc R . . C26A C 0.1736(9) 0.3378(5) 0.5296(7) 0.044(2) Uani 1 1 d . . . H26A H 0.1272 0.3136 0.5773 0.053 Uiso 1 1 calc R . . C25A C 0.2579(9) 0.4081(5) 0.5670(7) 0.045(2) Uani 1 1 d . . . H25A H 0.2711 0.4302 0.6405 0.055 Uiso 1 1 calc R . . B2A B 0.2753(11) 0.3396(8) 0.1783(8) 0.052(3) Uani 1 1 d . . . C18A C 0.3697(13) 0.2640(6) -0.1767(8) 0.067(3) Uani 1 1 d . . . H18A H 0.3753 0.2616 -0.2513 0.080 Uiso 1 1 calc R . . C17A C 0.2622(11) 0.3093(6) -0.1574(7) 0.057(3) Uani 1 1 d . . . H17A H 0.1922 0.3373 -0.2190 0.068 Uiso 1 1 calc R . . O2A O 0.8608(9) 0.1872(3) 0.2210(5) 0.071(2) Uani 1 1 d . . . C9A C 0.8438(8) 0.1892(5) 0.5194(6) 0.0333(18) Uani 1 1 d . . . O1A O 0.7369(9) 0.0618(4) 0.2387(6) 0.077(2) Uani 1 1 d . . . C2A C 0.7911(9) 0.0898(5) 0.0722(6) 0.0361(18) Uani 1 1 d . . . O4A O 0.9349(8) 0.1145(4) 0.3960(6) 0.073(2) Uani 1 1 d . . . C7A C 0.8540(9) 0.1630(4) 0.1174(6) 0.0370(19) Uani 1 1 d . . . O6A O 1.0677(7) 0.1161(4) 0.5777(6) 0.074(2) Uani 1 1 d . . . C13A C 0.6120(9) 0.2551(4) 0.4479(7) 0.041(2) Uani 1 1 d . . . H13A H 0.5258 0.2690 0.3858 0.050 Uiso 1 1 calc R . . C3A C 0.7817(9) 0.0679(5) -0.0373(7) 0.0392(19) Uani 1 1 d . . . H3A H 0.7367 0.0179 -0.0688 0.047 Uiso 1 1 calc R . . C6A C 0.9080(8) 0.2125(5) 0.0540(6) 0.0372(19) Uani 1 1 d . . . H6A H 0.9519 0.2627 0.0858 0.045 Uiso 1 1 calc R . . O3A O 0.6996(8) 0.1813(4) 0.3236(4) 0.072(2) Uani 1 1 d . . . C12A C 0.6321(11) 0.2816(5) 0.5573(7) 0.050(2) Uani 1 1 d . . . H12A H 0.5574 0.3125 0.5706 0.060 Uiso 1 1 calc R . . C5A C 0.9007(8) 0.1917(5) -0.0551(6) 0.0396(19) Uani 1 1 d . . . H5A H 0.9387 0.2273 -0.0979 0.048 Uiso 1 1 calc R . . O5A O 0.6665(10) -0.0290(4) 0.1004(7) 0.093(3) Uani 1 1 d . . . C8A C 0.9541(9) 0.1381(6) 0.5005(8) 0.048(2) Uani 1 1 d . . . C14A C 0.7194(9) 0.2080(5) 0.4300(6) 0.0403(19) Uani 1 1 d . . . C4A C 0.8374(10) 0.1185(5) -0.1017(7) 0.046(2) Uani 1 1 d . . . H4A H 0.8322 0.1031 -0.1766 0.055 Uiso 1 1 calc R . . C11A C 0.7546(13) 0.2649(6) 0.6451(8) 0.065(3) Uani 1 1 d . . . H11A H 0.7674 0.2858 0.7192 0.078 Uiso 1 1 calc R . . C1A C 0.7239(13) 0.0369(6) 0.1359(9) 0.061(3) Uani 1 1 d . . . C10A C 0.8591(12) 0.2190(5) 0.6295(7) 0.058(3) Uani 1 1 d . . . H10A H 0.9445 0.2063 0.6930 0.070 Uiso 1 1 calc R . . B1A B 0.8089(16) 0.1374(7) 0.2926(9) 0.066(4) Uani 1 1 d . . . N1 N 0.7627(7) 0.4392(4) 0.1983(6) 0.0438(17) Uani 1 1 d . . . N2 N 0.3075(7) 0.0475(5) 0.3071(7) 0.062(2) Uani 1 1 d . . . C2 C 0.7002(9) 0.5211(5) 0.2188(7) 0.048(2) Uani 1 1 d . . . H2A H 0.6836 0.5562 0.1519 0.072 Uiso 1 1 calc R . . H2B H 0.7698 0.5473 0.2867 0.072 Uiso 1 1 calc R . . H2C H 0.6075 0.5120 0.2310 0.072 Uiso 1 1 calc R . . C3 C 0.6715(9) 0.4060(5) 0.0875(8) 0.057(2) Uani 1 1 d . . . H3B H 0.7139 0.3548 0.0735 0.085 Uiso 1 1 calc R . . H3C H 0.6667 0.4449 0.0267 0.085 Uiso 1 1 calc R . . H3D H 0.5728 0.3959 0.0880 0.085 Uiso 1 1 calc R . . C4 C 0.9236(9) 0.4481(5) 0.2115(8) 0.050(2) Uani 1 1 d . . . H4B H 0.9802 0.4594 0.2931 0.060 Uiso 1 1 calc R . . H4C H 0.9581 0.3953 0.1922 0.060 Uiso 1 1 calc R . . C1 C 0.7556(11) 0.3806(5) 0.2891(8) 0.060(2) Uani 1 1 d . . . H1A H 0.6535 0.3736 0.2834 0.089 Uiso 1 1 calc R . . H1B H 0.8127 0.4021 0.3650 0.089 Uiso 1 1 calc R . . H1C H 0.7958 0.3280 0.2780 0.089 Uiso 1 1 calc R . . O1 O 0.9015(6) 0.4973(4) 0.0206(5) 0.0629(18) Uani 1 1 d . . . H1 H 0.9373 0.4540 0.0062 0.075 Uiso 1 1 calc R . . C5 C 0.9585(9) 0.5124(6) 0.1407(7) 0.051(2) Uani 1 1 d . . . H5B H 0.9192 0.5649 0.1562 0.061 Uiso 1 1 calc R . . H5C H 1.0660 0.5179 0.1650 0.061 Uiso 1 1 calc R . . O2 O 0.2838(17) 0.0428(8) 0.5494(13) 0.074(4) Uani 0.50 1 d P A 1 C9 C 0.4235(19) 0.0439(13) 0.4206(14) 0.059(5) Uani 0.50 1 d P A 1 C7B C 0.1686(17) 0.0811(16) 0.215(2) 0.065(8) Uani 0.50 1 d P A 2 C6B C 0.4400(19) 0.0712(11) 0.2815(15) 0.053(4) Uani 0.50 1 d P A 2 C10 C 0.367(2) 0.0914(11) 0.5011(16) 0.057(5) Uani 0.50 1 d P A 1 O2B O 0.1730(13) -0.0326(8) 0.4790(10) 0.062(4) Uani 0.50 1 d P A 2 C9B C 0.2931(17) -0.0304(9) 0.3428(10) 0.030(3) Uani 0.50 1 d P A 2 C10B C 0.1695(19) -0.0549(11) 0.3710(14) 0.046(5) Uani 0.50 1 d P A 2 C8BA C 0.3815(19) -0.0188(9) 0.2347(14) 0.047(4) Uani 0.50 1 d P A 1 C7BA C 0.175(2) -0.0070(16) 0.308(2) 0.072(7) Uani 0.50 1 d P A 1 C8B C 0.3260(19) 0.1130(10) 0.4190(15) 0.044(4) Uani 0.50 1 d P A 2 C6BA C 0.256(5) 0.1063(15) 0.2381(18) 0.124(16) Uani 0.50 1 d P A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O9A 0.050(3) 0.049(4) 0.037(3) -0.010(3) 0.019(3) -0.003(3) O11A 0.039(3) 0.048(3) 0.045(3) 0.011(3) 0.009(3) 0.012(3) O8A 0.035(3) 0.063(4) 0.032(3) -0.006(3) 0.010(2) 0.006(3) O10A 0.046(3) 0.078(4) 0.032(3) 0.000(3) 0.018(3) -0.010(3) C16A 0.042(4) 0.019(4) 0.035(4) -0.001(3) 0.016(4) -0.003(3) C23A 0.021(3) 0.034(4) 0.040(4) -0.001(3) 0.009(3) -0.001(3) C28A 0.036(4) 0.029(4) 0.030(4) 0.002(3) 0.009(3) 0.007(3) C27A 0.040(4) 0.033(4) 0.035(4) -0.001(3) 0.010(3) -0.001(4) C21A 0.029(4) 0.037(4) 0.024(3) 0.001(3) 0.009(3) 0.005(3) C24A 0.042(5) 0.026(4) 0.047(5) -0.013(3) 0.019(4) -0.004(3) C15A 0.034(4) 0.029(4) 0.039(4) -0.002(3) 0.006(4) -0.008(4) C22A 0.030(4) 0.067(6) 0.041(5) 0.011(5) 0.008(4) 0.001(4) C19A 0.042(5) 0.031(4) 0.059(5) -0.004(4) 0.022(4) 0.004(4) O12A 0.052(4) 0.058(4) 0.061(4) 0.008(3) 0.017(3) -0.022(3) O7A 0.055(4) 0.096(5) 0.027(3) -0.003(3) 0.012(3) 0.030(4) C20A 0.035(4) 0.042(5) 0.034(4) -0.004(3) 0.009(3) 0.000(4) C26A 0.049(5) 0.053(5) 0.036(4) 0.006(4) 0.020(4) -0.004(4) C25A 0.055(5) 0.047(5) 0.038(4) -0.009(4) 0.022(4) -0.007(4) B2A 0.043(6) 0.082(9) 0.033(5) -0.006(5) 0.014(4) 0.012(6) C18A 0.104(8) 0.072(7) 0.045(5) 0.012(5) 0.051(5) 0.037(6) C17A 0.072(6) 0.063(6) 0.036(5) 0.008(4) 0.020(4) 0.031(5) O2A 0.152(7) 0.031(3) 0.039(3) -0.004(3) 0.044(4) -0.008(4) C9A 0.028(4) 0.037(4) 0.034(4) 0.011(3) 0.009(3) 0.003(3) O1A 0.144(7) 0.048(4) 0.069(4) 0.010(3) 0.075(5) 0.012(4) C2A 0.051(5) 0.030(4) 0.035(4) 0.004(3) 0.025(4) 0.010(4) O4A 0.094(5) 0.073(5) 0.079(5) 0.043(4) 0.064(4) 0.048(4) C7A 0.059(5) 0.023(4) 0.032(4) -0.004(3) 0.020(4) 0.002(4) O6A 0.046(4) 0.079(5) 0.097(5) 0.037(4) 0.027(4) 0.018(4) C13A 0.044(5) 0.029(4) 0.056(5) 0.002(4) 0.024(4) 0.008(4) C3A 0.044(4) 0.030(4) 0.046(4) -0.010(4) 0.019(4) 0.001(4) C6A 0.040(4) 0.032(4) 0.031(4) 0.002(3) 0.003(3) -0.009(4) O3A 0.096(5) 0.076(5) 0.032(3) -0.006(3) 0.008(3) 0.049(4) C12A 0.083(7) 0.023(4) 0.059(6) 0.001(4) 0.045(5) 0.004(4) C5A 0.043(5) 0.044(5) 0.038(4) -0.005(4) 0.021(4) -0.017(4) O5A 0.165(8) 0.030(4) 0.137(7) -0.015(4) 0.118(6) -0.023(4) C8A 0.045(5) 0.057(6) 0.053(6) 0.029(5) 0.029(5) 0.005(5) C14A 0.051(5) 0.037(4) 0.034(4) 0.002(3) 0.016(4) -0.001(4) C4A 0.057(5) 0.047(5) 0.040(4) -0.007(4) 0.023(4) 0.001(4) C11A 0.106(9) 0.049(6) 0.040(5) 0.002(4) 0.026(5) 0.033(6) C1A 0.098(8) 0.040(6) 0.066(6) 0.002(5) 0.054(6) 0.010(6) C10A 0.075(7) 0.039(5) 0.042(5) 0.010(4) -0.002(4) -0.010(5) B1A 0.108(10) 0.055(7) 0.044(6) 0.015(5) 0.039(7) 0.029(7) N1 0.030(3) 0.028(4) 0.068(4) -0.005(3) 0.009(3) 0.003(3) N2 0.028(4) 0.084(6) 0.068(5) 0.011(5) 0.010(4) -0.003(4) C2 0.043(5) 0.046(5) 0.056(5) 0.007(4) 0.018(4) 0.011(4) C3 0.042(5) 0.042(5) 0.075(6) -0.015(5) 0.007(4) -0.003(4) C4 0.033(4) 0.045(5) 0.070(6) -0.013(4) 0.015(4) 0.005(4) C1 0.078(6) 0.029(5) 0.075(6) 0.021(4) 0.032(5) 0.011(5) O1 0.056(4) 0.066(4) 0.077(4) -0.001(3) 0.038(4) 0.013(3) C5 0.042(5) 0.052(6) 0.067(6) -0.015(5) 0.029(4) -0.012(4) O2 0.092(10) 0.050(8) 0.101(11) 0.014(8) 0.062(9) 0.013(8) C9 0.046(10) 0.088(15) 0.036(9) -0.021(9) 0.008(8) 0.014(10) C7B 0.014(8) 0.09(2) 0.073(16) 0.000(13) -0.011(8) -0.014(9) C6B 0.052(10) 0.050(11) 0.053(10) -0.010(8) 0.012(8) 0.011(9) C10 0.064(12) 0.047(11) 0.050(11) 0.017(9) 0.009(9) 0.010(10) O2B 0.055(8) 0.071(9) 0.052(7) -0.006(6) 0.009(6) 0.007(7) C9B 0.040(9) 0.024(7) 0.023(7) 0.002(6) 0.009(6) 0.002(7) C10B 0.052(11) 0.043(11) 0.041(9) 0.002(8) 0.014(8) -0.018(9) C8BA 0.056(10) 0.030(9) 0.056(10) -0.008(8) 0.022(8) 0.032(8) C7BA 0.044(12) 0.084(17) 0.094(17) -0.039(14) 0.031(12) 0.004(12) C8B 0.050(10) 0.030(9) 0.044(9) -0.004(8) 0.007(8) -0.006(8) C6BA 0.27(5) 0.050(15) 0.027(11) -0.002(10) 0.02(2) 0.07(2) _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 O9A C28A 1.355(9) . ? O9A B2A 1.454(12) . ? O11A C15A 1.215(8) . ? O8A C15A 1.318(9) . ? O8A B2A 1.472(11) . ? O10A C22A 1.337(10) . ? O10A B2A 1.451(13) . ? C16A C17A 1.357(11) . ? C16A C21A 1.413(10) . ? C16A C15A 1.468(11) . ? C23A C28A 1.382(10) . ? C23A C24A 1.383(10) . ? C23A C22A 1.457(11) . ? C28A C27A 1.389(11) . ? C27A C26A 1.379(11) . ? C21A O7A 1.336(8) . ? C21A C20A 1.377(11) . ? C24A C25A 1.360(11) . ? C22A O12A 1.209(10) . ? C19A C20A 1.358(11) . ? C19A C18A 1.416(12) . ? O7A B2A 1.441(12) . ? C26A C25A 1.401(12) . ? C18A C17A 1.374(13) . ? O2A C7A 1.329(9) . ? O2A B1A 1.427(13) . ? C9A C14A 1.365(10) . ? C9A C10A 1.413(12) . ? C9A C8A 1.448(12) . ? O1A C1A 1.307(11) . ? O1A B1A 1.470(15) . ? C2A C7A 1.379(10) . ? C2A C3A 1.381(10) . ? C2A C1A 1.476(12) . ? O4A C8A 1.306(11) . ? O4A B1A 1.485(14) . ? C7A C6A 1.361(10) . ? O6A C8A 1.240(10) . ? C13A C12A 1.376(11) . ? C13A C14A 1.383(11) . ? C3A C4A 1.392(12) . ? C6A C5A 1.377(11) . ? O3A C14A 1.344(9) . ? O3A B1A 1.447(14) . ? C12A C11A 1.337(13) . ? C5A C4A 1.384(11) . ? O5A C1A 1.228(11) . ? C11A C10A 1.337(14) . ? N1 C3 1.461(10) . ? N1 C1 1.505(10) . ? N1 C4 1.528(10) . ? N1 C2 1.536(10) . ? N2 C6BA 1.27(2) . ? N2 C9B 1.379(16) . ? N2 C9 1.471(17) . ? N2 C6B 1.49(2) . ? N2 C7B 1.54(2) . ? N2 C7BA 1.57(3) . ? N2 C8B 1.718(18) . ? N2 C8BA 1.726(16) . ? C4 C5 1.490(12) . ? O1 C5 1.423(10) . ? O2 C10 1.42(2) . ? C9 C10 1.52(3) . ? O2B C10B 1.381(19) . ? C9B C10B 1.43(2) . ? 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 C28A O9A B2A 120.8(7) . . ? C15A O8A B2A 124.0(6) . . ? C22A O10A B2A 124.6(7) . . ? C17A C16A C21A 120.1(7) . . ? C17A C16A C15A 120.9(7) . . ? C21A C16A C15A 119.0(6) . . ? C28A C23A C24A 119.7(7) . . ? C28A C23A C22A 120.2(7) . . ? C24A C23A C22A 120.1(7) . . ? O9A C28A C23A 121.9(7) . . ? O9A C28A C27A 116.6(6) . . ? C23A C28A C27A 121.5(7) . . ? C26A C27A C28A 117.6(7) . . ? O7A C21A C20A 118.8(6) . . ? O7A C21A C16A 121.4(7) . . ? C20A C21A C16A 119.8(6) . . ? C25A C24A C23A 120.1(7) . . ? O11A C15A O8A 119.3(7) . . ? O11A C15A C16A 123.6(7) . . ? O8A C15A C16A 117.1(6) . . ? O12A C22A O10A 119.6(8) . . ? O12A C22A C23A 123.3(8) . . ? O10A C22A C23A 117.0(8) . . ? C20A C19A C18A 119.8(8) . . ? C21A O7A B2A 119.8(6) . . ? C19A C20A C21A 120.2(7) . . ? C27A C26A C25A 121.2(8) . . ? C24A C25A C26A 119.8(7) . . ? O7A B2A O10A 109.4(8) . . ? O7A B2A O9A 106.0(9) . . ? O10A B2A O9A 114.4(7) . . ? O7A B2A O8A 113.1(7) . . ? O10A B2A O8A 107.3(9) . . ? O9A B2A O8A 106.7(7) . . ? C17A C18A C19A 119.9(8) . . ? C16A C17A C18A 120.1(8) . . ? C7A O2A B1A 121.8(7) . . ? C14A C9A C10A 118.3(8) . . ? C14A C9A C8A 120.0(7) . . ? C10A C9A C8A 121.7(8) . . ? C1A O1A B1A 125.4(8) . . ? C7A C2A C3A 119.8(7) . . ? C7A C2A C1A 120.9(7) . . ? C3A C2A C1A 119.2(8) . . ? C8A O4A B1A 125.1(7) . . ? O2A C7A C6A 119.0(7) . . ? O2A C7A C2A 121.4(7) . . ? C6A C7A C2A 119.6(6) . . ? C12A C13A C14A 118.8(8) . . ? C2A C3A C4A 120.6(7) . . ? C7A C6A C5A 121.7(7) . . ? C14A O3A B1A 124.0(8) . . ? C11A C12A C13A 121.5(9) . . ? C6A C5A C4A 119.5(8) . . ? O6A C8A O4A 117.6(9) . . ? O6A C8A C9A 123.9(9) . . ? O4A C8A C9A 118.5(7) . . ? O3A C14A C9A 120.7(8) . . ? O3A C14A C13A 119.0(7) . . ? C9A C14A C13A 120.3(7) . . ? C5A C4A C3A 119.0(8) . . ? C10A C11A C12A 120.5(9) . . ? O5A C1A O1A 120.3(9) . . ? O5A C1A C2A 123.9(9) . . ? O1A C1A C2A 115.6(8) . . ? C11A C10A C9A 120.6(8) . . ? O2A B1A O3A 109.7(8) . . ? O2A B1A O1A 114.7(8) . . ? O3A B1A O1A 105.3(10) . . ? O2A B1A O4A 108.6(10) . . ? O3A B1A O4A 111.1(8) . . ? O1A B1A O4A 107.4(8) . . ? C3 N1 C1 107.3(7) . . ? C3 N1 C4 113.7(7) . . ? C1 N1 C4 107.2(6) . . ? C3 N1 C2 109.8(6) . . ? C1 N1 C2 108.1(6) . . ? C4 N1 C2 110.5(6) . . ? C6BA N2 C9B 150(2) . . ? C6BA N2 C9 131.9(19) . . ? C9B N2 C9 77.5(11) . . ? C6BA N2 C6B 80(2) . . ? C9B N2 C6B 120.4(11) . . ? C9 N2 C6B 77.3(11) . . ? C6BA N2 C7B 36(2) . . ? C9B N2 C7B 114.3(12) . . ? C9 N2 C7B 155.8(14) . . ? C6B N2 C7B 110.6(13) . . ? C6BA N2 C7BA 108(2) . . ? C9B N2 C7BA 45.0(11) . . ? C9 N2 C7BA 109.3(14) . . ? C6B N2 C7BA 157.7(12) . . ? C7B N2 C7BA 72.4(13) . . ? C6BA N2 C8B 88.7(12) . . ? C9B N2 C8B 108.3(9) . . ? C9 N2 C8B 54.5(10) . . ? C6B N2 C8B 99.0(10) . . ? C7B N2 C8B 101.3(13) . . ? C7BA N2 C8B 102.0(10) . . ? C6BA N2 C8BA 105.4(15) . . ? C9B N2 C8BA 71.9(9) . . ? C9 N2 C8BA 98.8(10) . . ? C6B N2 C8BA 60.0(9) . . ? C7B N2 C8BA 105.0(12) . . ? C7BA N2 C8BA 97.8(10) . . ? C8B N2 C8BA 150.9(9) . . ? C5 C4 N1 116.3(7) . . ? O1 C5 C4 114.3(7) . . ? N2 C9 C10 106.1(13) . . ? O2 C10 C9 112.6(16) . . ? N2 C9B C10B 122.1(14) . . ? O2B C10B C9B 115.4(13) . . ? 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 B2A O9A C28A C23A -3.4(10) . . . . ? B2A O9A C28A C27A 175.8(7) . . . . ? C24A C23A C28A O9A 178.9(6) . . . . ? C22A C23A C28A O9A 0.0(11) . . . . ? C24A C23A C28A C27A -0.2(11) . . . . ? C22A C23A C28A C27A -179.1(7) . . . . ? O9A C28A C27A C26A 178.7(7) . . . . ? C23A C28A C27A C26A -2.1(11) . . . . ? C17A C16A C21A O7A -179.6(8) . . . . ? C15A C16A C21A O7A 1.9(11) . . . . ? C17A C16A C21A C20A -1.6(12) . . . . ? C15A C16A C21A C20A 179.9(7) . . . . ? C28A C23A C24A C25A 3.6(11) . . . . ? C22A C23A C24A C25A -177.5(7) . . . . ? B2A O8A C15A O11A -174.1(8) . . . . ? B2A O8A C15A C16A 7.7(11) . . . . ? C17A C16A C15A O11A 7.1(12) . . . . ? C21A C16A C15A O11A -174.4(7) . . . . ? C17A C16A C15A O8A -174.7(8) . . . . ? C21A C16A C15A O8A 3.8(10) . . . . ? B2A O10A C22A O12A -174.4(8) . . . . ? B2A O10A C22A C23A 10.2(11) . . . . ? C28A C23A C22A O12A -178.4(8) . . . . ? C24A C23A C22A O12A 2.7(11) . . . . ? C28A C23A C22A O10A -3.2(10) . . . . ? C24A C23A C22A O10A 177.9(7) . . . . ? C20A C21A O7A B2A 163.2(8) . . . . ? C16A C21A O7A B2A -18.9(12) . . . . ? C18A C19A C20A C21A 0.0(13) . . . . ? O7A C21A C20A C19A 179.5(7) . . . . ? C16A C21A C20A C19A 1.5(12) . . . . ? C28A C27A C26A C25A 1.2(12) . . . . ? C23A C24A C25A C26A -4.5(12) . . . . ? C27A C26A C25A C24A 2.1(13) . . . . ? C21A O7A B2A O10A -91.6(8) . . . . ? C21A O7A B2A O9A 144.5(7) . . . . ? C21A O7A B2A O8A 28.0(12) . . . . ? C22A O10A B2A O7A -131.9(7) . . . . ? C22A O10A B2A O9A -13.1(12) . . . . ? C22A O10A B2A O8A 105.1(8) . . . . ? C28A O9A B2A O7A 129.9(7) . . . . ? C28A O9A B2A O10A 9.2(11) . . . . ? C28A O9A B2A O8A -109.4(8) . . . . ? C15A O8A B2A O7A -23.0(13) . . . . ? C15A O8A B2A O10A 97.8(9) . . . . ? C15A O8A B2A O9A -139.1(7) . . . . ? C20A C19A C18A C17A -1.4(15) . . . . ? C21A C16A C17A C18A 0.2(14) . . . . ? C15A C16A C17A C18A 178.7(9) . . . . ? C19A C18A C17A C16A 1.3(17) . . . . ? B1A O2A C7A C6A -178.7(9) . . . . ? B1A O2A C7A C2A 2.5(13) . . . . ? C3A C2A C7A O2A 177.8(8) . . . . ? C1A C2A C7A O2A 2.3(12) . . . . ? C3A C2A C7A C6A -0.9(12) . . . . ? C1A C2A C7A C6A -176.4(8) . . . . ? C7A C2A C3A C4A 1.2(11) . . . . ? C1A C2A C3A C4A 176.7(8) . . . . ? O2A C7A C6A C5A -178.3(8) . . . . ? C2A C7A C6A C5A 0.5(12) . . . . ? C14A C13A C12A C11A 2.1(13) . . . . ? C7A C6A C5A C4A -0.3(12) . . . . ? B1A O4A C8A O6A -177.6(9) . . . . ? B1A O4A C8A C9A 1.4(13) . . . . ? C14A C9A C8A O6A -177.5(8) . . . . ? C10A C9A C8A O6A 0.8(13) . . . . ? C14A C9A C8A O4A 3.6(12) . . . . ? C10A C9A C8A O4A -178.1(8) . . . . ? B1A O3A C14A C9A -5.2(13) . . . . ? B1A O3A C14A C13A 174.6(9) . . . . ? C10A C9A C14A O3A 179.9(8) . . . . ? C8A C9A C14A O3A -1.8(12) . . . . ? C10A C9A C14A C13A 0.1(12) . . . . ? C8A C9A C14A C13A 178.4(7) . . . . ? C12A C13A C14A O3A 179.3(7) . . . . ? C12A C13A C14A C9A -0.9(12) . . . . ? C6A C5A C4A C3A 0.5(13) . . . . ? C2A C3A C4A C5A -0.9(12) . . . . ? C13A C12A C11A C10A -2.5(15) . . . . ? B1A O1A C1A O5A 177.2(11) . . . . ? B1A O1A C1A C2A 1.4(15) . . . . ? C7A C2A C1A O5A -179.9(10) . . . . ? C3A C2A C1A O5A 4.6(15) . . . . ? C7A C2A C1A O1A -4.2(13) . . . . ? C3A C2A C1A O1A -179.7(8) . . . . ? C12A C11A C10A C9A 1.7(15) . . . . ? C14A C9A C10A C11A -0.5(13) . . . . ? C8A C9A C10A C11A -178.8(9) . . . . ? C7A O2A B1A O3A -123.3(10) . . . . ? C7A O2A B1A O1A -5.1(14) . . . . ? C7A O2A B1A O4A 115.2(10) . . . . ? C14A O3A B1A O2A -111.0(10) . . . . ? C14A O3A B1A O1A 125.1(9) . . . . ? C14A O3A B1A O4A 9.1(14) . . . . ? C1A O1A B1A O2A 3.0(15) . . . . ? C1A O1A B1A O3A 123.6(10) . . . . ? C1A O1A B1A O4A -117.9(10) . . . . ? C8A O4A B1A O2A 113.5(9) . . . . ? C8A O4A B1A O3A -7.2(15) . . . . ? C8A O4A B1A O1A -121.9(9) . . . . ? C3 N1 C4 C5 70.0(9) . . . . ? C1 N1 C4 C5 -171.6(7) . . . . ? C2 N1 C4 C5 -54.0(9) . . . . ? N1 C4 C5 O1 -66.8(10) . . . . ? C6BA N2 C9 C10 67(3) . . . . ? C9B N2 C9 C10 -103.9(16) . . . . ? C6B N2 C9 C10 130.7(17) . . . . ? C7B N2 C9 C10 18(4) . . . . ? C7BA N2 C9 C10 -71.5(18) . . . . ? C8B N2 C9 C10 19.7(12) . . . . ? C8BA N2 C9 C10 -173.0(14) . . . . ? N2 C9 C10 O2 87.4(18) . . . . ? C6BA N2 C9B C10B -55(4) . . . . ? C9 N2 C9B C10B 111.3(14) . . . . ? C6B N2 C9B C10B 178.3(12) . . . . ? C7B N2 C9B C10B -46.3(19) . . . . ? C7BA N2 C9B C10B -23.1(14) . . . . ? C8B N2 C9B C10B 65.7(15) . . . . ? C8BA N2 C9B C10B -145.0(14) . . . . ? N2 C9B C10B O2B -80.1(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.395 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.064 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 _geom_hbond_publ_flag O1 H1 O8A 0.84 2.41 3.105(8) 141 1_655 y O1 H1 O11A 0.84 2.19 2.916(8) 145 1_655 y C1 H1B O1 0.98 2.46 3.390(11) 158 2_565 y C1 H1C O2A 0.98 2.57 3.534(11) 170 ? y C2 H2C O12A 0.98 2.41 3.315(11) 153 ? y C3* H3C O1 0.98 2.47 3.048(11) 117 ? y C3 H3C O12A 0.98 2.55 3.292(11) 133 2_564 y loop_ _geom_extra_tableA_col_1 _geom_extra_tableA_col_2 _geom_extra_tableA_col_3 _geom_extra_tableA_col_4 _geom_extra_tableA_col_5 _geom_extra_tableA_col_6 X--H/X CgJ H..Cg X-H..Cg X..Cg 'Symmetry position of CgJ' C19A--H19A Cg1 2.87 141 3.660(10) x,y,z _geom_extra_table_head_A ; Geometrical parameters (\%A, \%) of selected inter-ring C-H...\p interactions. The CgJ refer to the Ring Centre-of-Gravity ; _geom_table_footnote_A ; Notes: Cg1 is the centroid of ring C2A/C3A/C4A/C5A/C6A/C7A. ;