# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '9893_web_deposit_cif_file_0_MichaelHaindl_1330528584.h237_2.cif' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Nov 10 09:02:39 2008' _audit_creation_method 'PLATON option' _audit_update_record ; ; #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondence 'Ruth M. Gschwind' _publ_contact_author_address # address of author for correspondence ; ; _publ_contact_author_email ruth.gschwind@chemie.uni-regensburg.de _publ_contact_author_fax ? _publ_contact_author_phone ? # Publication choise FI, CI or EI for Inorganic # FM, CM or EM for Metal-organic # FO, CO or EO for Organic _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter # Include date of submission ; Date of submission ? Please consider this CIF submission for publication as a Regular Structural Paper in Acta Crystallographica C. ; #=============================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ; _journal_techeditor_code ? _journal_techeditor_notes ; ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; ; _publ_section_title_footnote ; ; # The loop structure below should contain the names and adresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_footnote _publ_author_address # author name 'Michael H. Haindl' ; # author related footnote ; ; # Address of this author ; 'Markus B. Schmid' '' '' 'Kirsten Zeitler' '' '' 'Ruth M.Gschwind' '' '' #=============================================================================== # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; # Insert blank lines between paragraphs _publ_section_comment ; ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; The data were collected at 123K using an Oxford Diffraction Cryojet Cooler. The structure was solved by direct methods (SIR-97) and refined by full-matrix anisotropic least squares (SHELXL97). Most of the H-atoms were calculated geometrically and a riding model was used during refinement process; the remaining ones were located by difference Fourier syntheses and refined isotropically. ; # Insert blank lines between references _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Cosier, J. & Glazer, A.M. (1986). J. Appl. Cryst. 19, 105-107. Flack, H.D. (1983). Acta Cryst. A39, 876-881. L. J. Farrugia, J. Appl. Cryst (1997), 30, 565. Sheldrick, G.M. SHELXL97 (1997). Program for crystal structure refinement. University of G\\"ottingen, Germany. Sheldrick, G.M. SHELXS97 (1997). Program for Crystal Structure solution. University of G\\"ottingen, Germany. Sluis, P. van der & Spek, A.L. (1990). Acta Cryst. A46, 194-201. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_acknowledgements ; ; _publ_section_figure_captions ; View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. ; #=============================================================================== data_h237 _database_code_depnum_ccdc_archive 'CCDC 869742' #TrackingRef '9893_web_deposit_cif_file_0_MichaelHaindl_1330528584.h237_2.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H20 N O, C7 H5 O2' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C24 H25 N O3' _chemical_formula_iupac ? _chemical_formula_weight 375.45 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z _cell_length_a 5.9196(3) _cell_length_b 19.4951(9) _cell_length_c 9.1303(5) _cell_angle_alpha 90 _cell_angle_beta 107.906(5) _cell_angle_gamma 90 _cell_volume 1002.63(9) _cell_formula_units_Z 2 _cell_measurement_temperature 123 _cell_measurement_reflns_used 3543 _cell_measurement_theta_min 5.0794 _cell_measurement_theta_max 66.4670 _cell_special_details ; ; _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.457 _exptl_crystal_size_mid 0.068 _exptl_crystal_size_min 0.048 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.650 _exptl_crystal_density_meas_temp ? # Permitted for # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.30 (release 18-06-2008 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.79562 _exptl_absorpt_correction_T_max 1.00000 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Gemini Ultra' _diffrn_measurement_method omega-scan _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 10.00 63.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -11.6137 45.0000 30.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 2 omega -58.00 -13.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 11.6137 -45.0000 0.0000 0.0000 0.0000 45 #__ type_ start__ end____ width___ exp.time_ 3 omega 14.00 61.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -11.6137 45.0000 90.0000 0.0000 0.0000 47 #__ type_ start__ end____ width___ exp.time_ 4 omega -123.00 -70.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -90.0000 128.0000 38.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 5 omega -118.00 -65.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -90.0000 45.0000 120.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 6 omega -148.00 -122.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -90.0000 -142.0000 153.0000 0.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 7 omega -165.00 -112.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -90.0000 -45.0000 0.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 8 omega 66.00 119.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 45.0000 240.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 9 omega 80.00 133.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -92.0000 296.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 10 omega 124.00 168.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 45.0000 210.0000 0.0000 0.0000 44 #__ type_ start__ end____ width___ exp.time_ 11 omega 21.00 71.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -45.0000 300.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 12 omega 117.00 162.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 130.0000 306.0000 0.0000 0.0000 45 #__ type_ start__ end____ width___ exp.time_ 13 omega 15.00 73.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -77.0000 120.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 14 omega 21.00 54.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -139.0000 238.0000 0.0000 0.0000 33 #__ type_ start__ end____ width___ exp.time_ 15 omega 117.00 167.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 45.0000 60.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 16 omega 84.00 113.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -93.0000 133.0000 0.0000 0.0000 29 #__ type_ start__ end____ width___ exp.time_ 17 omega 69.00 110.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 77.0000 60.0000 0.0000 0.0000 41 #__ type_ start__ end____ width___ exp.time_ 18 omega 76.00 119.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -37.0000 220.0000 0.0000 0.0000 43 #__ type_ start__ end____ width___ exp.time_ 19 omega 70.00 96.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -63.0000 176.0000 0.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 20 omega 67.00 93.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -34.0000 257.0000 0.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 21 omega 74.00 101.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -89.0000 255.0000 0.0000 0.0000 27 #__ type_ start__ end____ width___ exp.time_ 22 omega 81.00 108.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -92.0000 174.0000 0.0000 0.0000 27 #__ type_ start__ end____ width___ exp.time_ 23 omega 19.00 45.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 93.5000 -128.0000 321.0000 0.0000 0.0000 26 ; _diffrn_detector_area_resol_mean 10.5431 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 5354 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.09 _diffrn_reflns_theta_max 66.65 _diffrn_reflns_theta_full 66.65 _diffrn_measured_fraction_theta_max 0.964 _diffrn_measured_fraction_theta_full 0.964 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2855 # number of observed reflections (> n sig(I)) _reflns_number_gt 2584 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.30 (release 18-06-2008 CrysAlis171 .NET) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.30 (release 18-06-2008 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.30 (release 18-06-2008 CrysAlis171 .NET) ; _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0841P)^2^+0.1355P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method shelxl _refine_ls_extinction_coef 0.0121(17) _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 -0.2(3) # Permitted for _chemical_absolute_configuration: # Absolute configuration details # rm = Det. by chiral ref. mol. with known abs.conf # ad = Det. by anomalous dispersion # rmad = Det. by 'rm' and 'ad' # syn = Det. with reference to synthesis # unk = Unknown/Arbitrary _chemical_absolute_configuration ? _refine_ls_number_reflns 2855 _refine_ls_number_parameters 263 _refine_ls_number_restraints 1 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.186 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.051 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani -0.3482(3) -0.52550(10) -0.9661(2) 1.000 0.0274(6) . . N1 N Uani 0.0922(4) -0.60690(13) -0.9110(3) 1.000 0.0261(6) . . C1 C Uani -0.1231(4) -0.49154(14) -0.9265(3) 1.000 0.0243(7) . . C2 C Uani 0.0499(4) -0.53591(14) -0.9824(3) 1.000 0.0258(8) . . C3 C Uani -0.0373(6) -0.55012(16) -1.1550(3) 1.000 0.0334(9) . . C4 C Uani 0.0814(5) -0.61719(16) -1.1712(4) 1.000 0.0351(9) . . C5 C Uani 0.0567(6) -0.65839(16) -1.0380(4) 1.000 0.0397(10) . . C6 C Uani -0.0415(4) -0.47442(14) -0.7553(3) 1.000 0.0239(7) . . C7 C Uani 0.1839(5) -0.48768(14) -0.6561(3) 1.000 0.0275(8) . . C8 C Uani 0.2450(5) -0.46833(17) -0.5024(4) 1.000 0.0337(8) . . C9 C Uani 0.0835(5) -0.43512(16) -0.4466(3) 1.000 0.0329(8) . . C10 C Uani -0.1448(5) -0.42112(16) -0.5439(3) 1.000 0.0320(8) . . C11 C Uani -0.2039(5) -0.44102(15) -0.6966(3) 1.000 0.0294(8) . . C12 C Uani -0.1517(4) -0.42511(14) -1.0193(3) 1.000 0.0246(7) . . C13 C Uani 0.0478(5) -0.38403(15) -1.0080(3) 1.000 0.0283(8) . . C14 C Uani 0.0292(5) -0.32654(15) -1.0986(3) 1.000 0.0319(8) . . C15 C Uani -0.1883(5) -0.30763(16) -1.2014(4) 1.000 0.0342(9) . . C16 C Uani -0.3864(5) -0.34644(17) -1.2096(4) 1.000 0.0369(9) . . C17 C Uani -0.3687(5) -0.40515(15) -1.1198(3) 1.000 0.0300(8) . . O2 O Uani -0.4374(3) -0.60621(11) -0.7529(2) 1.000 0.0320(6) . . O3 O Uani -0.1092(4) -0.66709(12) -0.7237(3) 1.000 0.0426(7) . . C18 C Uani -0.3335(4) -0.69168(14) -0.5561(3) 1.000 0.0247(7) . . C19 C Uani -0.5140(5) -0.67290(16) -0.4968(3) 1.000 0.0305(8) . . C20 C Uani -0.5508(5) -0.71017(18) -0.3770(4) 1.000 0.0354(9) . . C21 C Uani -0.4081(5) -0.76572(17) -0.3138(4) 1.000 0.0349(9) . . C22 C Uani -0.2254(5) -0.78431(15) -0.3719(4) 1.000 0.0327(8) . . C23 C Uani -0.1887(5) -0.74729(15) -0.4927(3) 1.000 0.0276(8) . . C24 C Uani -0.2902(4) -0.65272(14) -0.6863(3) 1.000 0.0275(8) . . H1M H Uiso 0.002(7) -0.615(2) -0.862(4) 1.000 0.0310 . . H1N H Uiso 0.241(7) -0.6098(19) -0.841(4) 1.000 0.0310 . . H1O H Uiso -0.356(6) -0.551(2) -0.889(4) 1.000 0.0330 . . H2 H Uiso 0.20570 -0.51150 -0.95750 1.000 0.0310 calc R H3A H Uiso -0.21230 -0.55460 -1.19250 1.000 0.0400 calc R H3B H Uiso 0.01140 -0.51300 -1.21300 1.000 0.0400 calc R H4A H Uiso -0.00040 -0.63980 -1.27050 1.000 0.0420 calc R H4B H Uiso 0.25040 -0.61020 -1.16320 1.000 0.0420 calc R H5A H Uiso -0.10260 -0.67960 -1.06330 1.000 0.0480 calc R H5B H Uiso 0.17850 -0.69490 -1.00900 1.000 0.0480 calc R H7 H Uiso 0.29750 -0.51020 -0.69360 1.000 0.0330 calc R H8 H Uiso 0.39940 -0.47810 -0.43540 1.000 0.0400 calc R H9 H Uiso 0.12740 -0.42170 -0.34160 1.000 0.0390 calc R H10 H Uiso -0.25740 -0.39840 -0.50600 1.000 0.0380 calc R H11 H Uiso -0.35900 -0.43170 -0.76330 1.000 0.0350 calc R H13 H Uiso 0.19710 -0.39600 -0.93720 1.000 0.0340 calc R H14 H Uiso 0.16610 -0.29960 -1.09070 1.000 0.0380 calc R H15 H Uiso -0.20030 -0.26840 -1.26520 1.000 0.0410 calc R H16 H Uiso -0.53660 -0.33300 -1.27720 1.000 0.0440 calc R H17 H Uiso -0.50650 -0.43170 -1.12760 1.000 0.0360 calc R H19 H Uiso -0.61210 -0.63460 -0.53830 1.000 0.0370 calc R H20 H Uiso -0.67570 -0.69740 -0.33760 1.000 0.0420 calc R H21 H Uiso -0.43480 -0.79090 -0.23160 1.000 0.0420 calc R H22 H Uiso -0.12600 -0.82220 -0.32910 1.000 0.0390 calc R H23 H Uiso -0.06380 -0.76000 -0.53230 1.000 0.0330 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0174(8) 0.0284(10) 0.0318(11) 0.0024(9) 0.0010(7) -0.0051(7) N1 0.0213(10) 0.0244(11) 0.0316(12) 0.0024(10) 0.0069(10) 0.0010(9) C1 0.0192(11) 0.0251(13) 0.0261(14) 0.0006(11) 0.0033(10) -0.0024(10) C2 0.0260(13) 0.0228(14) 0.0273(14) 0.0021(11) 0.0063(10) 0.0007(10) C3 0.0403(15) 0.0306(16) 0.0277(15) -0.0003(12) 0.0081(12) 0.0038(12) C4 0.0373(14) 0.0325(16) 0.0334(15) -0.0069(13) 0.0079(12) 0.0021(12) C5 0.0475(17) 0.0267(15) 0.0421(18) -0.0039(14) 0.0098(14) 0.0012(13) C6 0.0243(12) 0.0227(12) 0.0242(13) 0.0014(11) 0.0068(11) -0.0036(10) C7 0.0250(12) 0.0261(14) 0.0283(14) -0.0006(11) 0.0037(11) 0.0009(10) C8 0.0325(14) 0.0338(15) 0.0276(15) 0.0015(12) -0.0012(12) -0.0022(12) C9 0.0389(14) 0.0343(16) 0.0246(14) 0.0002(12) 0.0084(12) -0.0067(12) C10 0.0313(13) 0.0335(15) 0.0340(16) -0.0049(13) 0.0143(11) -0.0049(12) C11 0.0218(11) 0.0313(15) 0.0329(15) 0.0007(12) 0.0051(10) -0.0006(11) C12 0.0244(12) 0.0238(13) 0.0238(13) -0.0035(11) 0.0048(10) 0.0010(10) C13 0.0225(13) 0.0250(13) 0.0348(15) -0.0014(12) 0.0048(11) -0.0016(10) C14 0.0330(14) 0.0278(14) 0.0351(15) -0.0017(12) 0.0107(11) -0.0013(12) C15 0.0447(16) 0.0248(14) 0.0322(16) 0.0018(12) 0.0106(12) -0.0007(12) C16 0.0339(14) 0.0349(17) 0.0341(16) 0.0033(14) -0.0008(12) 0.0003(12) C17 0.0252(12) 0.0310(15) 0.0293(15) 0.0000(12) 0.0018(11) -0.0006(11) O2 0.0228(8) 0.0324(10) 0.0384(11) 0.0078(10) 0.0058(7) 0.0026(8) O3 0.0350(11) 0.0429(13) 0.0568(14) 0.0203(11) 0.0245(10) 0.0122(9) C18 0.0204(12) 0.0230(13) 0.0285(13) -0.0033(11) 0.0043(10) -0.0024(9) C19 0.0254(12) 0.0308(14) 0.0328(15) -0.0016(12) 0.0053(11) 0.0024(11) C20 0.0313(14) 0.0428(18) 0.0322(15) -0.0036(13) 0.0100(12) 0.0010(13) C21 0.0384(14) 0.0350(16) 0.0314(16) 0.0014(13) 0.0111(12) -0.0036(13) C22 0.0360(14) 0.0267(14) 0.0323(16) 0.0004(12) 0.0060(12) 0.0003(12) C23 0.0243(12) 0.0269(14) 0.0292(14) -0.0034(12) 0.0047(10) 0.0008(10) C24 0.0225(12) 0.0238(13) 0.0325(14) 0.0025(11) 0.0029(11) 0.0016(10) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.431(3) . . yes O1 H1O 0.88(4) . . no O2 C24 1.275(3) . . yes O3 C24 1.252(4) . . yes N1 C5 1.499(4) . . yes N1 C2 1.517(4) . . yes N1 H1N 0.92(4) . . no N1 H1M 0.81(4) . . no C1 C12 1.528(4) . . no C1 C2 1.542(4) . . no C1 C6 1.524(4) . . no C2 C3 1.525(4) . . no C3 C4 1.513(5) . . no C4 C5 1.502(5) . . no C6 C7 1.387(4) . . no C6 C11 1.397(4) . . no C7 C8 1.389(4) . . no C8 C9 1.376(4) . . no C9 C10 1.397(4) . . no C10 C11 1.385(4) . . no C12 C17 1.385(4) . . no C12 C13 1.404(4) . . no C13 C14 1.377(4) . . no C14 C15 1.390(4) . . no C15 C16 1.378(5) . . no C16 C17 1.393(4) . . no C2 H2 1.0000 . . no C3 H3A 0.9900 . . no C3 H3B 0.9900 . . no C4 H4A 0.9900 . . no C4 H4B 0.9900 . . no C5 H5B 0.9900 . . no C5 H5A 0.9900 . . no C7 H7 0.9500 . . no C8 H8 0.9500 . . no C9 H9 0.9500 . . no C10 H10 0.9500 . . no C11 H11 0.9500 . . no C13 H13 0.9500 . . no C14 H14 0.9500 . . no C15 H15 0.9500 . . no C16 H16 0.9500 . . no C17 H17 0.9500 . . no C18 C19 1.387(4) . . no C18 C23 1.393(4) . . no C18 C24 1.498(4) . . no C19 C20 1.385(4) . . no C20 C21 1.386(5) . . no C21 C22 1.391(5) . . no C22 C23 1.390(4) . . no C19 H19 0.9500 . . no C20 H20 0.9500 . . no C21 H21 0.9500 . . no C22 H22 0.9500 . . no C23 H23 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1O 110(2) . . . no C2 N1 C5 108.3(2) . . . yes C5 N1 H1N 112(2) . . . no H1M N1 H1N 105(4) . . . no C5 N1 H1M 110(3) . . . no C2 N1 H1M 111(3) . . . no C2 N1 H1N 111(2) . . . no C2 C1 C6 115.4(2) . . . no C2 C1 C12 105.3(2) . . . no C6 C1 C12 109.2(2) . . . no O1 C1 C2 108.6(2) . . . yes O1 C1 C6 109.7(2) . . . yes O1 C1 C12 108.4(2) . . . yes C1 C2 C3 113.3(2) . . . no N1 C2 C1 114.1(2) . . . yes N1 C2 C3 103.7(2) . . . yes C2 C3 C4 103.8(2) . . . no C3 C4 C5 102.7(3) . . . no N1 C5 C4 104.1(2) . . . yes C1 C6 C7 124.5(2) . . . no C7 C6 C11 118.3(2) . . . no C1 C6 C11 117.2(2) . . . no C6 C7 C8 120.6(3) . . . no C7 C8 C9 120.5(3) . . . no C8 C9 C10 120.2(3) . . . no C9 C10 C11 118.8(3) . . . no C6 C11 C10 121.8(3) . . . no C1 C12 C13 119.7(2) . . . no C1 C12 C17 121.8(2) . . . no C13 C12 C17 118.4(3) . . . no C12 C13 C14 120.7(3) . . . no C13 C14 C15 120.5(3) . . . no C14 C15 C16 119.2(3) . . . no C15 C16 C17 120.7(3) . . . no C12 C17 C16 120.5(3) . . . no N1 C2 H2 109.00 . . . no C1 C2 H2 109.00 . . . no C3 C2 H2 108.00 . . . no C2 C3 H3A 111.00 . . . no C2 C3 H3B 111.00 . . . no C4 C3 H3A 111.00 . . . no C4 C3 H3B 111.00 . . . no H3A C3 H3B 109.00 . . . no C3 C4 H4A 111.00 . . . no C3 C4 H4B 111.00 . . . no C5 C4 H4A 111.00 . . . no C5 C4 H4B 111.00 . . . no H4A C4 H4B 109.00 . . . no N1 C5 H5A 111.00 . . . no N1 C5 H5B 111.00 . . . no C4 C5 H5A 111.00 . . . no C4 C5 H5B 111.00 . . . no H5A C5 H5B 109.00 . . . no C6 C7 H7 120.00 . . . no C8 C7 H7 120.00 . . . no C7 C8 H8 120.00 . . . no C9 C8 H8 120.00 . . . no C8 C9 H9 120.00 . . . no C10 C9 H9 120.00 . . . no C9 C10 H10 121.00 . . . no C11 C10 H10 121.00 . . . no C6 C11 H11 119.00 . . . no C10 C11 H11 119.00 . . . no C12 C13 H13 120.00 . . . no C14 C13 H13 120.00 . . . no C13 C14 H14 120.00 . . . no C15 C14 H14 120.00 . . . no C14 C15 H15 120.00 . . . no C16 C15 H15 120.00 . . . no C15 C16 H16 120.00 . . . no C17 C16 H16 120.00 . . . no C12 C17 H17 120.00 . . . no C16 C17 H17 120.00 . . . no C19 C18 C23 119.5(3) . . . no C19 C18 C24 121.1(2) . . . no C23 C18 C24 119.4(2) . . . no C18 C19 C20 119.8(3) . . . no C19 C20 C21 121.0(3) . . . no C20 C21 C22 119.4(3) . . . no C21 C22 C23 119.8(3) . . . no C18 C23 C22 120.5(3) . . . no O2 C24 O3 123.1(3) . . . yes O2 C24 C18 118.7(2) . . . yes O3 C24 C18 118.2(2) . . . yes C18 C19 H19 120.00 . . . no C20 C19 H19 120.00 . . . no C19 C20 H20 119.00 . . . no C21 C20 H20 120.00 . . . no C20 C21 H21 120.00 . . . no C22 C21 H21 120.00 . . . no C21 C22 H22 120.00 . . . no C23 C22 H22 120.00 . . . no C18 C23 H23 120.00 . . . no C22 C23 H23 120.00 . . . no 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 C2 C1 129.8(3) . . . . no C5 N1 C2 C3 6.0(3) . . . . no C2 N1 C5 C4 19.7(3) . . . . no O1 C1 C2 N1 -60.6(3) . . . . no O1 C1 C2 C3 57.8(3) . . . . no C12 C1 C2 C3 -58.1(3) . . . . no O1 C1 C6 C7 132.3(3) . . . . no O1 C1 C6 C11 -50.0(3) . . . . no C2 C1 C6 C7 9.3(4) . . . . no C6 C1 C2 N1 63.0(3) . . . . no C12 C1 C6 C7 -109.0(3) . . . . no C12 C1 C6 C11 68.7(3) . . . . no O1 C1 C12 C13 -176.3(2) . . . . no O1 C1 C12 C17 1.1(3) . . . . no C2 C1 C12 C13 -60.3(3) . . . . no C2 C1 C12 C17 117.2(3) . . . . no C6 C1 C12 C13 64.2(3) . . . . no C6 C1 C12 C17 -118.4(3) . . . . no C6 C1 C2 C3 -178.6(2) . . . . no C12 C1 C2 N1 -176.5(2) . . . . no C2 C1 C6 C11 -173.0(2) . . . . no N1 C2 C3 C4 -29.3(3) . . . . no C1 C2 C3 C4 -153.5(2) . . . . no C2 C3 C4 C5 41.9(3) . . . . no C3 C4 C5 N1 -37.7(3) . . . . no C1 C6 C7 C8 178.0(3) . . . . no C11 C6 C7 C8 0.2(4) . . . . no C1 C6 C11 C10 -177.8(3) . . . . no C7 C6 C11 C10 0.1(4) . . . . no C6 C7 C8 C9 -0.6(5) . . . . no C7 C8 C9 C10 0.6(5) . . . . no C8 C9 C10 C11 -0.3(5) . . . . no C9 C10 C11 C6 -0.1(5) . . . . no C1 C12 C13 C14 175.4(3) . . . . no C17 C12 C13 C14 -2.2(4) . . . . no C1 C12 C17 C16 -176.2(3) . . . . no C13 C12 C17 C16 1.3(4) . . . . no C12 C13 C14 C15 0.9(4) . . . . no C13 C14 C15 C16 1.2(5) . . . . no C14 C15 C16 C17 -2.0(5) . . . . no C15 C16 C17 C12 0.7(5) . . . . no C23 C18 C19 C20 -1.0(4) . . . . no C24 C18 C19 C20 179.6(3) . . . . no C19 C18 C23 C22 0.6(4) . . . . no C24 C18 C23 C22 -179.9(3) . . . . no C19 C18 C24 O2 -7.2(4) . . . . no C19 C18 C24 O3 172.2(3) . . . . no C23 C18 C24 O2 173.4(2) . . . . no C23 C18 C24 O3 -7.2(4) . . . . no C18 C19 C20 C21 0.7(5) . . . . no C19 C20 C21 C22 -0.1(5) . . . . no C20 C21 C22 C23 -0.3(5) . . . . no C21 C22 C23 C18 0.0(5) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O2 2.679(3) . . no O1 N1 2.960(3) . . no O2 N1 2.714(3) . 1_455 no O2 C2 3.401(3) . 1_455 no O2 O1 2.679(3) . . no O3 C5 3.311(4) . . no O3 N1 2.641(4) . . no O1 H17 2.3600 . . no O1 H1M 2.65(4) . . no O1 H11 2.6200 . . no O1 H3A 2.5000 . . no O1 H2 2.6800 . 1_455 no O2 H1O 1.82(4) . . no O2 H1N 1.83(4) . 1_455 no O2 H7 2.6000 . 1_455 no O2 H19 2.5400 . . no O3 H1O 2.86(4) . . no O3 H1M 1.89(4) . . no O3 H23 2.4700 . . no O3 H15 2.7200 . 2_543 no O3 H1N 2.84(4) . . no N1 C7 3.215(4) . . no N1 O1 2.960(3) . . no N1 O2 2.714(3) . 1_655 no N1 O3 2.641(4) . . no N1 H7 2.7400 . . no N1 H1O 2.93(4) . . no C2 O2 3.401(3) . 1_655 no C3 C13 3.482(4) . . no C3 C17 3.511(4) . . no C5 C15 3.578(5) . 2_543 no C5 O3 3.311(4) . . no C5 C14 3.599(4) . 2_543 no C7 N1 3.215(4) . . no C9 C22 3.599(4) . 2_554 no C13 C3 3.482(4) . . no C14 C5 3.599(4) . 2_553 no C15 C5 3.578(5) . 2_553 no C17 C3 3.511(4) . . no C22 C9 3.599(4) . 2_544 no C2 H13 2.8500 . . no C2 H7 2.6400 . . no C4 H20 2.8600 . 1_654 no C6 H13 2.9200 . . no C6 H1M 2.95(4) . . no C7 H2 2.8300 . . no C7 H1M 3.10(4) . . no C7 H1N 3.00(4) . . no C9 H16 3.0500 . 1_656 no C9 H3B 2.7600 . 1_556 no C9 H22 3.0700 . 2_554 no C10 H22 2.9600 . 2_554 no C11 H22 2.9900 . 2_554 no C11 H1O 2.74(4) . . no C12 H3A 2.9400 . . no C12 H11 2.9600 . . no C12 H3B 2.8400 . . no C13 H2 2.6500 . . no C14 H9 3.0800 . 1_554 no C15 H5B 2.9100 . 2_553 no C17 H9 3.0600 . 1_454 no C18 H4A 2.9200 . 1_556 no C19 H15 2.9600 . 2_443 no C20 H23 3.0900 . 1_455 no C21 H5A 2.9600 . 1_556 no C23 H16 2.7800 . 2_443 no C23 H4A 2.8900 . 1_556 no C23 H20 3.0900 . 1_655 no C24 H1N 2.83(4) . 1_455 no C24 H1O 2.66(4) . . no C24 H1M 2.80(4) . . no H1M O1 2.65(4) . . no H1M O3 1.89(4) . . no H1M C6 2.95(4) . . no H1M C24 2.80(4) . . no H1M H1O 2.41(6) . . no H1M C7 3.10(4) . . no H1N O2 1.83(4) . 1_655 no H1N O3 2.84(4) . . no H1N C24 2.83(4) . 1_655 no H1N H7 2.3300 . . no H1N C7 3.00(4) . . no H1O O2 1.82(4) . . no H1O O3 2.86(4) . . no H1O N1 2.93(4) . . no H1O C11 2.74(4) . . no H1O C24 2.66(4) . . no H1O H1M 2.41(6) . . no H1O H2 2.5900 . 1_455 no H1O H11 2.6000 . . no H2 H1O 2.5900 . 1_655 no H2 H7 2.3000 . . no H2 H13 2.2600 . . no H2 C13 2.6500 . . no H2 O1 2.6800 . 1_655 no H2 C7 2.8300 . . no H3A O1 2.5000 . . no H3A C12 2.9400 . . no H3B C9 2.7600 . 1_554 no H3B H9 2.3500 . 1_554 no H3B C12 2.8400 . . no H4A C18 2.9200 . 1_554 no H4A C23 2.8900 . 1_554 no H4A H20 2.4600 . 1_654 no H4B H20 2.4600 . 1_654 no H5A C21 2.9600 . 1_554 no H5B C15 2.9100 . 2_543 no H7 C2 2.6400 . . no H7 H1N 2.3300 . . no H7 N1 2.7400 . . no H7 O2 2.6000 . 1_655 no H7 H2 2.3000 . . no H9 C17 3.0600 . 1_656 no H9 C14 3.0800 . 1_556 no H9 H16 2.5600 . 1_656 no H9 H17 2.4400 . 1_656 no H9 H3B 2.3500 . 1_556 no H11 O1 2.6200 . . no H11 H1O 2.6000 . . no H11 C12 2.9600 . . no H13 C2 2.8500 . . no H13 H2 2.2600 . . no H13 C6 2.9200 . . no H15 O3 2.7200 . 2_553 no H15 C19 2.9600 . 2_453 no H16 H9 2.5600 . 1_454 no H16 C9 3.0500 . 1_454 no H16 C23 2.7800 . 2_453 no H17 O1 2.3600 . . no H17 H9 2.4400 . 1_454 no H19 O2 2.5400 . . no H20 C4 2.8600 . 1_456 no H20 C23 3.0900 . 1_455 no H20 H4A 2.4600 . 1_456 no H20 H4B 2.4600 . 1_456 no H22 C9 3.0700 . 2_544 no H22 C10 2.9600 . 2_544 no H22 C11 2.9900 . 2_544 no H23 O3 2.4700 . . no H23 C20 3.0900 . 1_655 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1M O3 0.81(4) 1.89(4) 2.641(4) 154(4) . yes N1 H1N O2 0.92(4) 1.83(4) 2.714(3) 162(3) 1_655 yes O1 H1O O2 0.88(4) 1.82(4) 2.679(3) 168(4) . yes C3 H3A O1 0.9900 2.5000 2.923(4) 105.00 . yes C17 H17 O1 0.9500 2.3600 2.717(3) 102.00 . yes #===END