# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_5a _database_code_depnum_ccdc_archive 'CCDC 893518' #TrackingRef 'APA7_5a.cif' _audit_creation_date 2012-07-06 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ; ? ; _chemical_name_systematic ; (Benzene-1,2-diolato)(methanolato)(2-(morpholinomethyl)phenyl)boron methanol solvate ; _chemical_formula_moiety 'C18 H22 B N O4, C H4 O' _chemical_formula_sum 'C19 H26 B N O5' _chemical_formula_weight 359.22 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.1083(3) _cell_length_b 9.45522(19) _cell_length_c 15.1358(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.016(2) _cell_angle_gamma 90.00 _cell_volume 1852.80(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 12845 _cell_measurement_temperature 100.15 _cell_measurement_theta_max 67.0887 _cell_measurement_theta_min 3.4137 _exptl_absorpt_coefficient_mu 0.747 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 768 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_special_details ? _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_unetI/netI 0.0173 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 23639 _diffrn_reflns_theta_full 67.20 _diffrn_reflns_theta_max 67.20 _diffrn_reflns_theta_min 4.15 _diffrn_ambient_temperature 100.15 _diffrn_detector_area_resol_mean 10.3347 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -53.00 -25.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -41.0113 125.0000 -30.0000 28 #__ type_ start__ end____ width___ exp.time_ 2 omega -58.00 -20.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -41.0113 125.0000 -119.0000 38 #__ type_ start__ end____ width___ exp.time_ 3 omega 8.00 120.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 41.0113 77.0000 90.0000 112 #__ type_ start__ end____ width___ exp.time_ 4 omega 42.00 96.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 41.0113 -125.0000 -150.0000 54 #__ type_ start__ end____ width___ exp.time_ 5 omega 19.00 112.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 41.0113 37.0000 -30.0000 93 #__ type_ start__ end____ width___ exp.time_ 6 omega -121.00 -62.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 125.0000 60.0000 59 #__ type_ start__ end____ width___ exp.time_ 7 omega -120.00 -91.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 125.0000 -90.0000 29 #__ type_ start__ end____ width___ exp.time_ 8 omega 87.00 126.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -90.0000 -34.0000 39 #__ type_ start__ end____ width___ exp.time_ 9 omega 15.00 41.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -90.0000 -34.0000 26 #__ type_ start__ end____ width___ exp.time_ 10 omega 104.00 131.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -90.0000 123.0000 27 #__ type_ start__ end____ width___ exp.time_ 11 omega 93.00 119.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -83.0000 59.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 62.00 88.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 15.0000 -60.0000 26 #__ type_ start__ end____ width___ exp.time_ 13 omega 110.00 145.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 15.0000 -60.0000 35 #__ type_ start__ end____ width___ exp.time_ 14 omega 71.00 97.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 45.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 15 omega 89.00 115.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -71.0000 -54.0000 26 #__ type_ start__ end____ width___ exp.time_ 16 omega 90.00 116.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -71.0000 44.0000 26 #__ type_ start__ end____ width___ exp.time_ 17 omega 81.00 119.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -92.0000 76.0000 38 #__ type_ start__ end____ width___ exp.time_ 18 omega 20.00 76.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -45.0000 -150.0000 56 #__ type_ start__ end____ width___ exp.time_ 19 omega 20.00 76.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -45.0000 -60.0000 56 #__ type_ start__ end____ width___ exp.time_ 20 omega 20.00 76.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -45.0000 90.0000 56 #__ type_ start__ end____ width___ exp.time_ 21 omega 98.00 124.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 125.0000 90.0000 26 #__ type_ start__ end____ width___ exp.time_ 22 omega 20.00 76.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -45.0000 30.0000 56 #__ type_ start__ end____ width___ exp.time_ 23 omega 69.00 135.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 77.0000 120.0000 66 #__ type_ start__ end____ width___ exp.time_ 24 omega 144.00 169.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 77.0000 120.0000 25 #__ type_ start__ end____ width___ exp.time_ 25 omega 29.00 62.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -146.0000 -46.0000 33 #__ type_ start__ end____ width___ exp.time_ 26 omega 68.00 98.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 45.0000 -30.0000 30 #__ type_ start__ end____ width___ exp.time_ 27 omega 20.00 105.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -146.0000 -4.0000 85 #__ type_ start__ end____ width___ exp.time_ 28 omega 61.00 119.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 77.0000 -60.0000 58 #__ type_ start__ end____ width___ exp.time_ 29 omega 33.00 74.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -15.0000 30.0000 41 #__ type_ start__ end____ width___ exp.time_ 30 omega 96.00 154.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -15.0000 30.0000 58 #__ type_ start__ end____ width___ exp.time_ 31 omega 20.00 62.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -71.0000 44.0000 42 #__ type_ start__ end____ width___ exp.time_ 32 omega 83.00 140.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 45.0000 60.0000 57 #__ type_ start__ end____ width___ exp.time_ 33 omega 77.00 116.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 125.0000 -180.0000 39 #__ type_ start__ end____ width___ exp.time_ 34 omega 96.00 122.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -89.0000 -129.0000 26 #__ type_ start__ end____ width___ exp.time_ 35 omega 29.00 57.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -89.0000 -129.0000 28 #__ type_ start__ end____ width___ exp.time_ 36 omega 131.00 157.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 45.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 37 omega 112.00 138.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 45.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 38 omega 69.00 94.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 77.0000 -180.0000 25 #__ type_ start__ end____ width___ exp.time_ 39 omega 44.00 74.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -77.0000 -120.0000 30 #__ type_ start__ end____ width___ exp.time_ 40 omega 95.00 121.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -77.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 41 omega 24.00 62.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -77.0000 150.0000 38 #__ type_ start__ end____ width___ exp.time_ 42 omega 141.00 166.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 125.0000 -150.0000 25 #__ type_ start__ end____ width___ exp.time_ 43 omega 33.00 123.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -67.0000 -64.0000 90 #__ type_ start__ end____ width___ exp.time_ 44 omega 9.00 35.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -92.0000 76.0000 26 #__ type_ start__ end____ width___ exp.time_ 45 omega 48.00 75.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -90.0000 123.0000 27 #__ type_ start__ end____ width___ exp.time_ 46 omega 83.00 108.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 77.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 47 omega 119.00 155.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -15.0000 -180.0000 36 #__ type_ start__ end____ width___ exp.time_ 48 omega 39.00 109.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -92.0000 -172.0000 70 ; _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2894 _reflns_number_total 3316 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.341 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 243 _refine_ls_number_reflns 3316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0335 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.5541P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0862 _refine_ls_wR_factor_ref 0.0894 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.31794(6) 0.85941(9) 0.58390(5) 0.0188(2) Uani 1 1 d . . . O3 O 0.53775(7) 1.15661(9) 0.94301(6) 0.0223(2) Uani 1 1 d . . . O4 O 0.38531(6) 1.08447(9) 0.65107(5) 0.0188(2) Uani 1 1 d . . . O2 O 0.27009(6) 1.07482(8) 0.50844(5) 0.01793(19) Uani 1 1 d . . . N1 N 0.38339(7) 1.01592(10) 0.81886(7) 0.0163(2) Uani 1 1 d . . . C6 C 0.10478(9) 1.07978(12) 0.61558(8) 0.0182(3) Uani 1 1 d . . . H6 H 0.0997 1.1179 0.5570 0.022 Uiso 1 1 calc R . . C1 C 0.19928(9) 1.02409(12) 0.65660(8) 0.0162(2) Uani 1 1 d . . . C14 C 0.24638(9) 0.97212(15) 0.35741(8) 0.0230(3) Uani 1 1 d . . . H14 H 0.2296 1.0591 0.3271 0.028 Uiso 1 1 calc R . . C2 C 0.20352(9) 0.96973(12) 0.74393(8) 0.0179(3) Uani 1 1 d . . . C5 C 0.01819(9) 1.08104(13) 0.65777(9) 0.0217(3) Uani 1 1 d . . . H5 H -0.0450 1.1190 0.6279 0.026 Uiso 1 1 calc R . . C12 C 0.29649(9) 0.83946(13) 0.49432(8) 0.0185(3) Uani 1 1 d . . . C13 C 0.26958(8) 0.96649(13) 0.44954(8) 0.0177(3) Uani 1 1 d . . . C3 C 0.11672(10) 0.97197(14) 0.78665(9) 0.0227(3) Uani 1 1 d . . . H3 H 0.1211 0.9357 0.8457 0.027 Uiso 1 1 calc R . . C11 C 0.35568(9) 1.11285(13) 0.88935(8) 0.0197(3) Uani 1 1 d . . . H11A H 0.3468 1.0576 0.9432 0.024 Uiso 1 1 calc R . . H11B H 0.2896 1.1610 0.8671 0.024 Uiso 1 1 calc R . . C4 C 0.02384(10) 1.02695(14) 0.74342(9) 0.0251(3) Uani 1 1 d . . . H4 H -0.0354 1.0274 0.7724 0.030 Uiso 1 1 calc R . . C17 C 0.29752(10) 0.71366(14) 0.44816(9) 0.0239(3) Uani 1 1 d . . . H17 H 0.3146 0.6269 0.4786 0.029 Uiso 1 1 calc R . . C10 C 0.44030(10) 1.22178(13) 0.91335(8) 0.0223(3) Uani 1 1 d . . . H10A H 0.4453 1.2812 0.8604 0.027 Uiso 1 1 calc R . . H10B H 0.4223 1.2841 0.9612 0.027 Uiso 1 1 calc R . . C16 C 0.27248(10) 0.71870(15) 0.35469(9) 0.0278(3) Uani 1 1 d . . . H16 H 0.2720 0.6336 0.3213 0.033 Uiso 1 1 calc R . . C15 C 0.24848(10) 0.84480(16) 0.31012(9) 0.0279(3) Uani 1 1 d . . . H15 H 0.2332 0.8453 0.2467 0.033 Uiso 1 1 calc R . . B1 B 0.29558(10) 1.01325(14) 0.60135(9) 0.0162(3) Uani 1 1 d . . . C7 C 0.30194(9) 0.90442(13) 0.79235(8) 0.0186(3) Uani 1 1 d . . . H7A H 0.2872 0.8547 0.8465 0.022 Uiso 1 1 calc R . . H7B H 0.3281 0.8339 0.7530 0.022 Uiso 1 1 calc R . . C8 C 0.48775(9) 0.95279(13) 0.84907(8) 0.0201(3) Uani 1 1 d . . . H8A H 0.5083 0.8942 0.8006 0.024 Uiso 1 1 calc R . . H8B H 0.4855 0.8913 0.9017 0.024 Uiso 1 1 calc R . . C9 C 0.56578(10) 1.07035(14) 0.87349(8) 0.0224(3) Uani 1 1 d . . . H9A H 0.6349 1.0288 0.8933 0.027 Uiso 1 1 calc R . . H9B H 0.5697 1.1293 0.8201 0.027 Uiso 1 1 calc R . . C19 C 0.40665(12) 0.35130(16) 0.44934(11) 0.0363(3) Uani 1 1 d . . . H19A H 0.4131 0.2755 0.4064 0.054 Uiso 1 1 calc R . . H19B H 0.4535 0.3326 0.5052 0.054 Uiso 1 1 calc R . . H19C H 0.4247 0.4420 0.4245 0.054 Uiso 1 1 calc R . . O5 O 0.30477(8) 0.35673(12) 0.46644(9) 0.0425(3) Uani 1 1 d . . . C18 C 0.48036(10) 1.06947(16) 0.61669(9) 0.0267(3) Uani 1 1 d . . . H18A H 0.5300 1.1401 0.6445 0.040 Uiso 1 1 calc R . . H18B H 0.4679 1.0836 0.5517 0.040 Uiso 1 1 calc R . . H18C H 0.5083 0.9744 0.6303 0.040 Uiso 1 1 calc R . . H1 H 0.3872(12) 1.0636(18) 0.7662(12) 0.032 Uiso 1 1 d . . . H5A H 0.2875(14) 0.275(2) 0.4791(12) 0.040 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 0.0242(4) 0.0172(4) 0.0154(4) 0.0001(3) 0.0045(3) 0.0019(3) O3 0.0235(5) 0.0218(4) 0.0198(4) -0.0026(3) -0.0029(3) 0.0021(3) O4 0.0165(4) 0.0236(4) 0.0164(4) -0.0001(3) 0.0036(3) -0.0031(3) O2 0.0208(4) 0.0172(4) 0.0158(4) 0.0010(3) 0.0027(3) -0.0007(3) N1 0.0185(5) 0.0160(5) 0.0140(5) 0.0004(4) 0.0015(4) 0.0017(4) C6 0.0205(6) 0.0137(6) 0.0200(6) -0.0008(4) 0.0019(5) -0.0018(4) C1 0.0185(6) 0.0112(5) 0.0186(6) -0.0021(4) 0.0022(5) -0.0028(4) C14 0.0160(6) 0.0351(7) 0.0178(6) 0.0021(5) 0.0024(5) -0.0032(5) C2 0.0195(6) 0.0151(6) 0.0187(6) -0.0026(5) 0.0021(5) -0.0021(5) C5 0.0179(6) 0.0189(6) 0.0276(7) -0.0018(5) 0.0013(5) 0.0003(5) C12 0.0154(6) 0.0232(6) 0.0180(6) -0.0011(5) 0.0058(5) -0.0024(5) C13 0.0128(5) 0.0228(6) 0.0181(6) -0.0017(5) 0.0041(4) -0.0035(4) C3 0.0246(6) 0.0259(7) 0.0184(6) -0.0013(5) 0.0058(5) -0.0037(5) C11 0.0222(6) 0.0198(6) 0.0168(6) -0.0019(5) 0.0024(5) 0.0045(5) C4 0.0190(6) 0.0295(7) 0.0285(7) -0.0037(5) 0.0093(5) -0.0020(5) C17 0.0245(6) 0.0221(6) 0.0277(7) -0.0041(5) 0.0121(5) -0.0038(5) C10 0.0250(6) 0.0180(6) 0.0224(6) -0.0023(5) -0.0006(5) 0.0040(5) C16 0.0252(7) 0.0334(7) 0.0274(7) -0.0138(6) 0.0120(5) -0.0088(6) C15 0.0188(6) 0.0472(8) 0.0182(6) -0.0074(6) 0.0047(5) -0.0072(6) B1 0.0188(6) 0.0151(6) 0.0145(6) 0.0008(5) 0.0018(5) -0.0001(5) C7 0.0216(6) 0.0167(6) 0.0172(6) 0.0003(5) 0.0023(5) -0.0019(5) C8 0.0200(6) 0.0205(6) 0.0191(6) -0.0011(5) 0.0011(5) 0.0052(5) C9 0.0200(6) 0.0260(6) 0.0206(6) -0.0008(5) 0.0013(5) 0.0027(5) C19 0.0402(8) 0.0270(7) 0.0433(9) 0.0032(6) 0.0115(7) -0.0010(6) O5 0.0340(6) 0.0208(5) 0.0724(8) 0.0125(5) 0.0074(5) -0.0009(4) C18 0.0180(6) 0.0407(8) 0.0221(6) 0.0008(5) 0.0055(5) -0.0039(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 C12 1.3541(15) . ? O1 B1 1.5152(15) . y O3 C10 1.4259(15) . ? O3 C9 1.4243(15) . ? O4 B1 1.4580(15) . y O4 C18 1.4306(15) . ? O2 C13 1.3572(15) . ? O2 B1 1.5102(15) . y N1 C11 1.4940(15) . ? N1 C7 1.5094(15) . ? N1 C8 1.4969(15) . ? N1 H1 0.924(18) . ? C6 H6 0.9500 . ? C6 C1 1.3986(17) . ? C6 C5 1.3868(18) . ? C1 C2 1.4111(17) . ? C1 B1 1.6230(17) . ? C14 H14 0.9500 . ? C14 C13 1.3809(17) . ? C14 C15 1.403(2) . ? C2 C3 1.3941(18) . ? C2 C7 1.5122(17) . ? C5 H5 0.9500 . ? C5 C4 1.3848(19) . ? C12 C13 1.3969(18) . ? C12 C17 1.3806(18) . ? C3 H3 0.9500 . ? C3 C4 1.3896(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C10 1.5155(18) . ? C4 H4 0.9500 . ? C17 H17 0.9500 . ? C17 C16 1.4020(19) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C16 H16 0.9500 . ? C16 C15 1.382(2) . ? C15 H15 0.9500 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.5165(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C19 O5 1.4006(19) . ? O5 H5A 0.84(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O1 B1 107.03(9) . . ? C9 O3 C10 109.69(9) . . ? C18 O4 B1 116.40(9) . . ? C13 O2 B1 107.36(9) . . ? C11 N1 C7 112.16(9) . . ? C11 N1 C8 109.83(9) . . ? C11 N1 H1 111.6(10) . . ? C7 N1 H1 104.1(10) . . ? C8 N1 C7 112.16(9) . . ? C8 N1 H1 106.7(10) . . ? C1 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C5 C6 C1 122.05(11) . . ? C6 C1 C2 117.07(11) . . ? C6 C1 B1 120.08(10) . . ? C2 C1 B1 122.68(10) . . ? C13 C14 H14 121.2 . . ? C13 C14 C15 117.60(12) . . ? C15 C14 H14 121.2 . . ? C1 C2 C7 120.54(10) . . ? C3 C2 C1 120.91(11) . . ? C3 C2 C7 118.54(11) . . ? C6 C5 H5 120.0 . . ? C4 C5 C6 120.02(11) . . ? C4 C5 H5 120.0 . . ? O1 C12 C13 111.29(10) . . ? O1 C12 C17 127.57(11) . . ? C17 C12 C13 121.13(11) . . ? O2 C13 C14 127.72(12) . . ? O2 C13 C12 110.82(10) . . ? C14 C13 C12 121.46(12) . . ? C2 C3 H3 119.8 . . ? C4 C3 C2 120.39(12) . . ? C4 C3 H3 119.8 . . ? N1 C11 H11A 109.7 . . ? N1 C11 H11B 109.7 . . ? N1 C11 C10 109.71(10) . . ? H11A C11 H11B 108.2 . . ? C10 C11 H11A 109.7 . . ? C10 C11 H11B 109.7 . . ? C5 C4 C3 119.56(12) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C12 C17 H17 121.2 . . ? C12 C17 C16 117.52(12) . . ? C16 C17 H17 121.2 . . ? O3 C10 C11 111.58(10) . . ? O3 C10 H10A 109.3 . . ? O3 C10 H10B 109.3 . . ? C11 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C17 C16 H16 119.3 . . ? C15 C16 C17 121.42(12) . . ? C15 C16 H16 119.3 . . ? C14 C15 H15 119.6 . . ? C16 C15 C14 120.83(12) . . ? C16 C15 H15 119.6 . . ? O1 B1 C1 109.74(9) . . y O4 B1 O1 111.77(10) . . y O4 B1 O2 110.21(9) . . y O4 B1 C1 109.55(9) . . y O2 B1 O1 103.20(9) . . y O2 B1 C1 112.27(9) . . y N1 C7 C2 110.97(9) . . ? N1 C7 H7A 109.4 . . ? N1 C7 H7B 109.4 . . ? C2 C7 H7A 109.4 . . ? C2 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? N1 C8 H8A 109.8 . . ? N1 C8 H8B 109.8 . . ? N1 C8 C9 109.35(10) . . ? H8A C8 H8B 108.3 . . ? C9 C8 H8A 109.8 . . ? C9 C8 H8B 109.8 . . ? O3 C9 C8 110.95(10) . . ? O3 C9 H9A 109.4 . . ? O3 C9 H9B 109.4 . . ? C8 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O5 C19 H19A 109.5 . . ? O5 C19 H19B 109.5 . . ? O5 C19 H19C 109.5 . . ? C19 O5 H5A 108.0(12) . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 O1 C12 C13 O2 -1.36(13) . . . . ? O1 C12 C13 C14 178.78(10) . . . . ? O1 C12 C17 C16 -179.98(11) . . . . ? N1 C11 C10 O3 -57.50(13) . . . . ? N1 C8 C9 O3 59.27(13) . . . . ? C6 C1 C2 C3 0.05(17) . . . . ? C6 C1 C2 C7 178.56(10) . . . . ? C6 C1 B1 O1 -111.37(11) . . . . ? C6 C1 B1 O4 125.57(11) . . . . ? C6 C1 B1 O2 2.78(15) . . . . ? C6 C5 C4 C3 0.17(19) . . . . ? C1 C6 C5 C4 0.46(18) . . . . ? C1 C2 C3 C4 0.57(18) . . . . ? C1 C2 C7 N1 70.77(13) . . . . ? C2 C1 B1 O1 63.85(14) . . . . ? C2 C1 B1 O4 -59.21(14) . . . . ? C2 C1 B1 O2 178.00(10) . . . . ? C2 C3 C4 C5 -0.67(19) . . . . ? C5 C6 C1 C2 -0.56(17) . . . . ? C5 C6 C1 B1 174.92(11) . . . . ? C12 O1 B1 O4 -124.01(10) . . . . ? C12 O1 B1 O2 -5.60(11) . . . . ? C12 O1 B1 C1 114.25(10) . . . . ? C12 C17 C16 C15 0.55(19) . . . . ? C13 O2 B1 O1 4.83(11) . . . . ? C13 O2 B1 O4 124.32(10) . . . . ? C13 O2 B1 C1 -113.27(10) . . . . ? C13 C14 C15 C16 0.31(18) . . . . ? C13 C12 C17 C16 1.18(18) . . . . ? C3 C2 C7 N1 -110.69(12) . . . . ? C11 N1 C7 C2 68.01(12) . . . . ? C11 N1 C8 C9 -55.25(13) . . . . ? C17 C12 C13 O2 177.66(10) . . . . ? C17 C12 C13 C14 -2.21(18) . . . . ? C17 C16 C15 C14 -1.31(19) . . . . ? C10 O3 C9 C8 -61.68(13) . . . . ? C15 C14 C13 O2 -178.42(11) . . . . ? C15 C14 C13 C12 1.41(17) . . . . ? B1 O1 C12 C13 4.50(13) . . . . ? B1 O1 C12 C17 -174.44(12) . . . . ? B1 O2 C13 C14 177.41(11) . . . . ? B1 O2 C13 C12 -2.44(12) . . . . ? B1 C1 C2 C3 -175.31(11) . . . . ? B1 C1 C2 C7 3.20(16) . . . . ? C7 N1 C11 C10 179.79(9) . . . . ? C7 N1 C8 C9 179.30(9) . . . . ? C7 C2 C3 C4 -177.97(11) . . . . ? C8 N1 C11 C10 54.34(12) . . . . ? C8 N1 C7 C2 -167.83(10) . . . . ? C9 O3 C10 C11 60.87(13) . . . . ? C18 O4 B1 O1 50.70(13) . . . . ? C18 O4 B1 O2 -63.44(13) . . . . ? C18 O4 B1 C1 172.56(10) . . . . ? #===========end of cif