Electronic Supplementary Information for Dalton Transactions This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ;Department of Chemistry The Ohio State University 100 West 18th Avenue Columbus, OH 43210 U.S.A. ; _publ_contact_author_name 'Malcolm H. Chisholm' _publ_section_title ;18-Membered Cyclic Esters Derived from Glycolide and Lactide: Preparations, Structures and Coordination to Sodium Ions ; _publ_requested_category FM _publ_contact_author_email P.G.STEEL@DURHAM.AC.UK loop_ _publ_author_name M.Chisholm J.Gallucci 'Hongfeng Yin' #===END # CIF produced by WinGX routine CIF_UPDATE # Created on 2005-05-05 at 17:32:59 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : c:\wingx\files\archive.dat # CIF files read : shelxl dreduc import struct data_Chisholm1368 _database_code_depnum_ccdc_archive 'CCDC 271310' _audit_creation_date 2005-05-05T17:32:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Chisholm 1368' _chemical_formula_moiety 'C16 H18 N2 Na O12, C24 H20 B' _chemical_formula_sum 'C40 H38 B N2 Na O12' _chemical_formula_weight 772.52 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.9205(10) _cell_length_b 13.4728(10) _cell_length_c 13.977(2) _cell_angle_alpha 80.972(4) _cell_angle_beta 64.021(4) _cell_angle_gamma 63.137(5) _cell_volume 1948.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6775 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a hemisphere of reciprocal space with a redundancy factor of 3.4. Phi and omega scans with a frame width of 1.0 degree was used for data collection. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. The asymmetric unit consists of a Na+ ion coordinated by two CH3CN groups, three carbonyl groups of one cyclic ester, and one carbonyl group of a second cyclic ester. There is also a B(Ph)4 anion present. There are two different types of cyclic esters present and each contains a crystallographic inversion center. Both esters have the same formula, but have different conformations. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.183466E-1 _diffrn_orient_matrix_ub_12 -0.306832E-1 _diffrn_orient_matrix_ub_13 0.884913E-1 _diffrn_orient_matrix_ub_21 0.659954E-1 _diffrn_orient_matrix_ub_22 0.55082E-2 _diffrn_orient_matrix_ub_23 -0.505469E-1 _diffrn_orient_matrix_ub_31 -0.68036E-2 _diffrn_orient_matrix_ub_32 0.790958E-1 _diffrn_orient_matrix_ub_33 -0.69812E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 44653 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 24.95 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 6794 _reflns_number_gt 4646 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;For the methyl groups, the hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5*Ueq(bonded atom). The torsion angle, which defines the orientation of the methyl group about the C-C bond, was refined. The remaining hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq (bonded atom). 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 'w=1/[\s^2^(Fo^2^)+(0.0857P)^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 none _refine_ls_number_reflns 6794 _refine_ls_number_parameters 507 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1223 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.271 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 Na Na 0.90888(7) 0.02920(6) 0.19986(6) 0.0341(2) Uani 1 1 d . . . O1 O 0.83957(15) 0.18897(13) 0.30105(12) 0.0475(4) Uani 1 1 d . . . O2 O 0.45796(17) 0.21609(15) 0.56363(17) 0.0717(6) Uani 1 1 d . . . O3 O 0.64964(15) 0.49652(13) 0.35509(12) 0.0442(4) Uani 1 1 d . . . O4 O 0.79601(14) 0.42339(11) 0.42459(11) 0.0392(4) Uani 1 1 d . . . O5 O 0.74075(14) 0.25329(12) 0.47152(11) 0.0396(4) Uani 1 1 d . . . O6 O 0.51404(15) 0.35048(12) 0.47639(12) 0.0456(4) Uani 1 1 d . . . O7 O 0.82674(13) 0.14790(11) 0.08324(11) 0.0351(4) Uani 1 1 d . . . O8 O 0.80063(13) 0.27787(11) -0.03723(11) 0.0365(4) Uani 1 1 d . . . O9 O 1.11113(13) 0.02678(12) 0.07882(11) 0.0358(4) Uani 1 1 d . . . O10 O 1.31031(13) -0.06549(11) -0.04456(11) 0.0348(4) Uani 1 1 d . . . O11 O 0.94733(13) -0.13070(12) 0.11694(11) 0.0357(4) Uani 1 1 d . . . O12 O 0.90822(13) -0.22004(11) 0.02362(11) 0.0352(4) Uani 1 1 d . . . N1 N 1.0289(2) -0.1027(2) 0.29899(16) 0.0529(5) Uani 1 1 d . . . N2 N 0.6936(2) 0.03040(18) 0.31347(16) 0.0528(5) Uani 1 1 d . . . C1 C 0.35675(19) 0.36908(16) 0.18373(15) 0.0301(5) Uani 1 1 d . . . C2 C 0.4386(2) 0.30267(18) 0.23159(16) 0.0351(5) Uani 1 1 d . . . H2 H 0.4311 0.2372 0.2636 0.042 Uiso 1 1 calc R . . C3 C 0.5309(2) 0.32710(19) 0.23500(17) 0.0397(5) Uani 1 1 d . . . H3 H 0.5851 0.2785 0.2679 0.048 Uiso 1 1 calc R . . C4 C 0.5431(2) 0.4223(2) 0.19033(17) 0.0415(6) Uani 1 1 d . . . H4 H 0.6044 0.4408 0.1934 0.05 Uiso 1 1 calc R . . C5 C 0.4652(2) 0.49009(19) 0.14115(18) 0.0420(6) Uani 1 1 d . . . H5 H 0.4736 0.5552 0.1092 0.05 Uiso 1 1 calc R . . C6 C 0.3745(2) 0.46374(17) 0.13810(17) 0.0362(5) Uani 1 1 d . . . H6 H 0.3222 0.5119 0.1036 0.043 Uiso 1 1 calc R . . C7 C 0.21942(18) 0.24596(17) 0.25417(15) 0.0304(5) Uani 1 1 d . . . C8 C 0.20426(19) 0.15843(17) 0.22919(17) 0.0337(5) Uani 1 1 d . . . H8 H 0.224 0.1457 0.157 0.04 Uiso 1 1 calc R . . C9 C 0.1619(2) 0.08901(18) 0.30419(18) 0.0426(6) Uani 1 1 d . . . H9 H 0.1537 0.0304 0.2828 0.051 Uiso 1 1 calc R . . C10 C 0.1315(2) 0.1054(2) 0.41038(18) 0.0450(6) Uani 1 1 d . . . H10 H 0.1033 0.0579 0.4624 0.054 Uiso 1 1 calc R . . C11 C 0.1431(2) 0.1925(2) 0.43909(17) 0.0452(6) Uani 1 1 d . . . H11 H 0.1218 0.2055 0.5116 0.054 Uiso 1 1 calc R . . C12 C 0.1854(2) 0.26063(18) 0.36283(16) 0.0371(5) Uani 1 1 d . . . H12 H 0.1917 0.32 0.385 0.045 Uiso 1 1 calc R . . C13 C 0.12130(19) 0.44303(16) 0.18778(15) 0.0307(5) Uani 1 1 d . . . C14 C 0.0446(2) 0.45208(17) 0.13712(16) 0.0343(5) Uani 1 1 d . . . H14 H 0.0766 0.3963 0.0845 0.041 Uiso 1 1 calc R . . C15 C -0.0758(2) 0.53892(18) 0.16071(18) 0.0396(5) Uani 1 1 d . . . H15 H -0.1238 0.5421 0.1237 0.047 Uiso 1 1 calc R . . C16 C -0.1263(2) 0.62087(19) 0.23772(19) 0.0453(6) Uani 1 1 d . . . H16 H -0.2086 0.6806 0.2541 0.054 Uiso 1 1 calc R . . C17 C -0.0549(2) 0.61428(19) 0.29020(19) 0.0465(6) Uani 1 1 d . . . H17 H -0.0884 0.6696 0.3437 0.056 Uiso 1 1 calc R . . C18 C 0.0656(2) 0.52733(18) 0.26541(17) 0.0389(5) Uani 1 1 d . . . H18 H 0.1126 0.525 0.303 0.047 Uiso 1 1 calc R . . C19 C 0.33811(18) 0.28248(16) 0.04360(15) 0.0285(5) Uani 1 1 d . . . C20 C 0.3301(2) 0.34630(17) -0.04438(16) 0.0325(5) Uani 1 1 d . . . H20 H 0.2701 0.4224 -0.032 0.039 Uiso 1 1 calc R . . C21 C 0.4062(2) 0.30338(19) -0.14921(17) 0.0392(5) Uani 1 1 d . . . H21 H 0.3968 0.3496 -0.2064 0.047 Uiso 1 1 calc R . . C22 C 0.4957(2) 0.19297(19) -0.16980(17) 0.0383(5) Uani 1 1 d . . . H22 H 0.5476 0.1627 -0.241 0.046 Uiso 1 1 calc R . . C23 C 0.50869(19) 0.12756(18) -0.08577(16) 0.0350(5) Uani 1 1 d . . . H23 H 0.5705 0.0521 -0.0991 0.042 Uiso 1 1 calc R . . C24 C 0.43157(18) 0.17165(17) 0.01846(16) 0.0305(5) Uani 1 1 d . . . H24 H 0.4425 0.1249 0.075 0.037 Uiso 1 1 calc R . . C25 C 1.1027(2) -0.1848(2) 0.31111(18) 0.0425(6) Uani 1 1 d . . . C26 C 1.1972(3) -0.2897(2) 0.3257(2) 0.0700(8) Uani 1 1 d . . . H26A H 1.217 -0.3477 0.2777 0.105 Uiso 1 1 calc R . . H26B H 1.1636 -0.3103 0.3997 0.105 Uiso 1 1 calc R . . H26C H 1.275 -0.282 0.3096 0.105 Uiso 1 1 calc R . . C27 C 0.5991(3) 0.0311(2) 0.3337(2) 0.0541(7) Uani 1 1 d . . . C28 C 0.4765(3) 0.0321(3) 0.3603(4) 0.132(2) Uani 1 1 d . . . H28A H 0.4089 0.0921 0.4142 0.197 Uiso 1 1 calc R . . H28B H 0.4776 -0.0396 0.3884 0.197 Uiso 1 1 calc R . . H28C H 0.4603 0.0445 0.2962 0.197 Uiso 1 1 calc R . . C29 C 0.5361(2) 0.25159(18) 0.51868(18) 0.0421(6) Uani 1 1 d . . . C30 C 0.6730(2) 0.18536(18) 0.50159(18) 0.0423(6) Uani 1 1 d . . . H30A H 0.6764 0.1488 0.568 0.051 Uiso 1 1 calc R . . H30B H 0.7157 0.1263 0.4451 0.051 Uiso 1 1 calc R . . C31 C 0.8156(2) 0.25158(18) 0.36752(17) 0.0347(5) Uani 1 1 d . . . C32 C 0.8709(2) 0.33345(18) 0.34523(17) 0.0410(6) Uani 1 1 d . . . H32A H 0.9583 0.2944 0.342 0.049 Uiso 1 1 calc R . . H32B H 0.8771 0.3641 0.2748 0.049 Uiso 1 1 calc R . . C33 C 0.6852(2) 0.49793(18) 0.42115(18) 0.0369(5) Uani 1 1 d . . . C34 C 0.6132(2) 0.5802(2) 0.5140(2) 0.0501(6) Uani 1 1 d . . . H34A H 0.6101 0.54 0.5802 0.06 Uiso 1 1 calc R . . H34B H 0.6577 0.627 0.5042 0.06 Uiso 1 1 calc R . . C35 C 0.78059(19) 0.19384(17) 0.02115(17) 0.0327(5) Uani 1 1 d . . . C36 C 0.6931(2) 0.16757(17) -0.00295(17) 0.0338(5) Uani 1 1 d . . . H36A H 0.6061 0.2292 0.0256 0.041 Uiso 1 1 calc R . . H36B H 0.7234 0.1598 -0.0811 0.041 Uiso 1 1 calc R . . C37 C 1.2034(2) 0.02653(17) 0.00159(16) 0.0313(5) Uani 1 1 d . . . C38 C 1.2153(2) 0.12841(17) -0.05388(17) 0.0350(5) Uani 1 1 d . . . H38A H 1.2697 0.147 -0.0344 0.042 Uiso 1 1 calc R . . H38B H 1.2561 0.1135 -0.132 0.042 Uiso 1 1 calc R . . C39 C 0.9827(2) -0.20898(17) 0.06031(16) 0.0320(5) Uani 1 1 d . . . C40 C 1.1116(2) -0.30572(17) 0.02273(18) 0.0378(5) Uani 1 1 d . . . H40A H 1.106 -0.3715 0.0636 0.045 Uiso 1 1 calc R . . H40B H 1.1427 -0.3245 -0.0536 0.045 Uiso 1 1 calc R . . B B 0.2578(2) 0.33504(19) 0.16783(18) 0.0300(5) 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 Na 0.0341(5) 0.0355(5) 0.0324(4) 0.0003(4) -0.0114(4) -0.0167(4) O1 0.0484(10) 0.0480(10) 0.0420(9) -0.0118(8) -0.0079(8) -0.0235(8) O2 0.0422(11) 0.0517(11) 0.1052(15) 0.0172(10) -0.0157(10) -0.0260(10) O3 0.0452(9) 0.0469(10) 0.0459(9) 0.0056(7) -0.0216(8) -0.0228(8) O4 0.0351(9) 0.0341(8) 0.0484(9) -0.0030(7) -0.0175(7) -0.0133(8) O5 0.0394(9) 0.0407(9) 0.0348(9) -0.0001(7) -0.0086(7) -0.0202(8) O6 0.0412(10) 0.0345(9) 0.0529(10) 0.0030(7) -0.0158(8) -0.0138(8) O7 0.0332(8) 0.0358(8) 0.0381(8) 0.0036(7) -0.0172(7) -0.0146(7) O8 0.0309(8) 0.0327(8) 0.0464(9) 0.0075(7) -0.0168(7) -0.0151(7) O9 0.0309(8) 0.0408(9) 0.0341(8) 0.0007(7) -0.0094(7) -0.0177(7) O10 0.0278(8) 0.0359(8) 0.0391(8) 0.0059(7) -0.0118(7) -0.0159(7) O11 0.0344(8) 0.0337(8) 0.0415(8) -0.0020(7) -0.0147(7) -0.0165(7) O12 0.0338(8) 0.0320(8) 0.0456(9) 0.0005(7) -0.0180(7) -0.0168(7) N1 0.0630(15) 0.0616(15) 0.0477(12) 0.0167(11) -0.0282(11) -0.0373(13) N2 0.0473(14) 0.0591(14) 0.0516(13) -0.0024(10) -0.0138(11) -0.0275(12) C1 0.0257(11) 0.0318(12) 0.0277(11) -0.0056(9) -0.0065(9) -0.0106(10) C2 0.0352(12) 0.0380(12) 0.0343(12) 0.0020(10) -0.0139(10) -0.0182(11) C3 0.0325(13) 0.0527(15) 0.0353(12) -0.0046(11) -0.0145(10) -0.0169(12) C4 0.0346(13) 0.0540(15) 0.0410(13) -0.0090(11) -0.0103(11) -0.0248(12) C5 0.0408(14) 0.0411(13) 0.0485(14) -0.0010(11) -0.0135(11) -0.0250(12) C6 0.0323(12) 0.0355(12) 0.0433(13) 0.0032(10) -0.0158(10) -0.0168(11) C7 0.0220(11) 0.0327(11) 0.0347(12) 0.0001(9) -0.0107(9) -0.0109(10) C8 0.0280(12) 0.0337(12) 0.0346(12) -0.0006(9) -0.0074(9) -0.0143(10) C9 0.0358(13) 0.0337(12) 0.0522(15) -0.0006(11) -0.0097(11) -0.0175(11) C10 0.0397(14) 0.0444(14) 0.0429(14) 0.0117(11) -0.0102(11) -0.0216(12) C11 0.0438(14) 0.0595(16) 0.0327(12) 0.0047(11) -0.0105(11) -0.0285(13) C12 0.0356(13) 0.0422(13) 0.0340(12) -0.0013(10) -0.0108(10) -0.0196(11) C13 0.0291(11) 0.0315(11) 0.0324(11) 0.0003(9) -0.0095(9) -0.0166(10) C14 0.0310(12) 0.0334(12) 0.0369(12) 0.0044(9) -0.0129(10) -0.0145(10) C15 0.0311(13) 0.0406(13) 0.0480(13) 0.0125(11) -0.0177(11) -0.0183(11) C16 0.0288(13) 0.0366(13) 0.0582(15) 0.0043(12) -0.0110(12) -0.0117(11) C17 0.0380(14) 0.0369(13) 0.0506(14) -0.0101(11) -0.0081(12) -0.0110(12) C18 0.0341(13) 0.0388(13) 0.0425(13) -0.0026(10) -0.0131(10) -0.0158(11) C19 0.0233(11) 0.0312(11) 0.0360(11) 0.0005(9) -0.0127(9) -0.0152(10) C20 0.0295(11) 0.0305(11) 0.0378(12) 0.0027(10) -0.0121(10) -0.0152(10) C21 0.0428(14) 0.0438(14) 0.0336(12) 0.0054(10) -0.0149(11) -0.0229(12) C22 0.0348(13) 0.0488(14) 0.0307(12) -0.0047(10) -0.0065(10) -0.0224(12) C23 0.0263(12) 0.0368(12) 0.0412(13) -0.0033(10) -0.0099(10) -0.0155(10) C24 0.0249(11) 0.0349(12) 0.0342(12) 0.0016(9) -0.0120(9) -0.0151(10) C25 0.0497(15) 0.0528(16) 0.0355(13) 0.0034(12) -0.0193(12) -0.0295(14) C26 0.076(2) 0.0563(18) 0.081(2) -0.0062(15) -0.0439(17) -0.0173(17) C27 0.0466(17) 0.0397(14) 0.0756(19) 0.0108(13) -0.0234(14) -0.0227(13) C28 0.073(2) 0.079(2) 0.271(6) 0.088(3) -0.097(3) -0.056(2) C29 0.0420(14) 0.0336(13) 0.0430(13) -0.0005(11) -0.0096(11) -0.0171(12) C30 0.0409(14) 0.0341(12) 0.0412(13) 0.0036(10) -0.0083(11) -0.0166(11) C31 0.0272(12) 0.0343(12) 0.0356(12) -0.0007(10) -0.0110(10) -0.0087(10) C32 0.0332(13) 0.0397(13) 0.0425(13) -0.0052(10) -0.0070(10) -0.0159(11) C33 0.0361(13) 0.0341(12) 0.0429(13) 0.0066(10) -0.0148(11) -0.0202(11) C34 0.0451(15) 0.0425(14) 0.0548(15) -0.0056(12) -0.0237(12) -0.0074(12) C35 0.0250(11) 0.0313(12) 0.0339(12) -0.0010(10) -0.0072(10) -0.0098(10) C36 0.0301(12) 0.0321(12) 0.0383(12) 0.0057(10) -0.0143(10) -0.0140(10) C37 0.0280(12) 0.0376(12) 0.0326(12) -0.0012(10) -0.0147(10) -0.0147(11) C38 0.0292(12) 0.0378(12) 0.0419(12) 0.0027(10) -0.0158(10) -0.0169(11) C39 0.0335(12) 0.0324(12) 0.0344(11) 0.0064(10) -0.0123(10) -0.0209(11) C40 0.0333(13) 0.0297(12) 0.0523(14) 0.0016(10) -0.0169(11) -0.0158(11) B 0.0296(13) 0.0307(13) 0.0313(13) -0.0003(10) -0.0114(11) -0.0150(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Na O7 2.3461(17) . ? Na O1 2.3535(17) . ? Na O11 2.3544(15) . ? Na O9 2.3998(16) . ? Na N1 2.470(2) . ? Na N2 2.521(2) . ? O1 C31 1.195(2) . ? O2 C29 1.196(3) . ? O3 C33 1.203(3) . ? O4 C33 1.344(3) . ? O4 C32 1.434(2) . ? O5 C31 1.344(2) . ? O5 C30 1.436(2) . ? O6 C29 1.328(3) . ? O6 C34 1.432(3) 2_666 ? O7 C35 1.201(2) . ? O8 C35 1.343(2) . ? O8 C40 1.442(2) 2_755 ? O9 C37 1.207(2) . ? O10 C37 1.336(2) . ? O10 C36 1.441(2) 2_755 ? O11 C39 1.207(2) . ? O12 C39 1.340(2) . ? O12 C38 1.429(3) 2_755 ? N1 C25 1.136(3) . ? N2 C27 1.123(3) . ? C1 C2 1.394(3) . ? C1 C6 1.402(3) . ? C1 B 1.645(3) . ? C2 C3 1.393(3) . ? C2 H2 0.95 . ? C3 C4 1.380(3) . ? C3 H3 0.95 . ? C4 C5 1.378(3) . ? C4 H4 0.95 . ? C5 C6 1.387(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.396(3) . ? C7 C12 1.403(3) . ? C7 B 1.643(3) . ? C8 C9 1.388(3) . ? C8 H8 0.95 . ? C9 C10 1.385(3) . ? C9 H9 0.95 . ? C10 C11 1.386(3) . ? C10 H10 0.95 . ? C11 C12 1.383(3) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 C18 1.396(3) . ? C13 C14 1.406(3) . ? C13 B 1.638(3) . ? C14 C15 1.387(3) . ? C14 H14 0.95 . ? C15 C16 1.382(3) . ? C15 H15 0.95 . ? C16 C17 1.376(3) . ? C16 H16 0.95 . ? C17 C18 1.387(3) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? C19 C20 1.400(3) . ? C19 C24 1.405(3) . ? C19 B 1.654(3) . ? C20 C21 1.392(3) . ? C20 H20 0.95 . ? C21 C22 1.386(3) . ? C21 H21 0.95 . ? C22 C23 1.378(3) . ? C22 H22 0.95 . ? C23 C24 1.390(3) . ? C23 H23 0.95 . ? C24 H24 0.95 . ? C25 C26 1.448(4) . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C27 C28 1.454(4) . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? C29 C30 1.500(3) . ? C30 H30A 0.99 . ? C30 H30B 0.99 . ? C31 C32 1.495(3) . ? C32 H32A 0.99 . ? C32 H32B 0.99 . ? C33 C34 1.497(3) . ? C34 O6 1.432(3) 2_666 ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? C35 C36 1.500(3) . ? C36 O10 1.441(2) 2_755 ? C36 H36A 0.99 . ? C36 H36B 0.99 . ? C37 C38 1.504(3) . ? C38 O12 1.429(3) 2_755 ? C38 H38A 0.99 . ? C38 H38B 0.99 . ? C39 C40 1.495(3) . ? C40 O8 1.442(2) 2_755 ? C40 H40A 0.99 . ? C40 H40B 0.99 . ? 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 O7 Na O1 87.98(6) . . ? O7 Na O11 92.56(5) . . ? O1 Na O11 171.03(6) . . ? O7 Na O9 86.54(5) . . ? O1 Na O9 95.53(6) . . ? O11 Na O9 93.44(5) . . ? O7 Na N1 170.91(7) . . ? O1 Na N1 95.29(7) . . ? O11 Na N1 85.53(7) . . ? O9 Na N1 84.71(6) . . ? O7 Na N2 89.86(7) . . ? O1 Na N2 87.55(6) . . ? O11 Na N2 83.50(6) . . ? O9 Na N2 175.17(7) . . ? N1 Na N2 98.73(7) . . ? C31 O1 Na 164.39(16) . . ? C33 O4 C32 115.05(17) . . ? C31 O5 C30 117.27(16) . . ? C29 O6 C34 117.40(18) . 2_666 ? C35 O7 Na 168.60(13) . . ? C35 O8 C40 113.84(16) . 2_755 ? C37 O9 Na 165.74(13) . . ? C37 O10 C36 114.77(15) . 2_755 ? C39 O11 Na 169.02(13) . . ? C39 O12 C38 113.90(15) . 2_755 ? C25 N1 Na 155.02(19) . . ? C27 N2 Na 158.6(2) . . ? C2 C1 C6 114.57(18) . . ? C2 C1 B 124.17(17) . . ? C6 C1 B 120.90(18) . . ? C3 C2 C1 123.5(2) . . ? C3 C2 H2 118.2 . . ? C1 C2 H2 118.2 . . ? C4 C3 C2 119.6(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 119.1(2) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 120.4(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 122.9(2) . . ? C5 C6 H6 118.6 . . ? C1 C6 H6 118.6 . . ? C8 C7 C12 114.59(18) . . ? C8 C7 B 123.79(18) . . ? C12 C7 B 121.27(17) . . ? C9 C8 C7 123.5(2) . . ? C9 C8 H8 118.2 . . ? C7 C8 H8 118.2 . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C11 C10 C9 118.6(2) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C7 122.97(19) . . ? C11 C12 H12 118.5 . . ? C7 C12 H12 118.5 . . ? C18 C13 C14 114.64(19) . . ? C18 C13 B 122.15(18) . . ? C14 C13 B 122.83(17) . . ? C15 C14 C13 122.8(2) . . ? C15 C14 H14 118.6 . . ? C13 C14 H14 118.6 . . ? C16 C15 C14 120.3(2) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 118.7(2) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? C16 C17 C18 120.4(2) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C13 123.1(2) . . ? C17 C18 H18 118.4 . . ? C13 C18 H18 118.4 . . ? C20 C19 C24 114.99(18) . . ? C20 C19 B 123.46(18) . . ? C24 C19 B 121.14(18) . . ? C21 C20 C19 123.0(2) . . ? C21 C20 H20 118.5 . . ? C19 C20 H20 118.5 . . ? C22 C21 C20 119.8(2) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C23 C22 C21 119.2(2) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 120.2(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C19 122.7(2) . . ? C23 C24 H24 118.6 . . ? C19 C24 H24 118.6 . . ? N1 C25 C26 179.6(2) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N2 C27 C28 179.7(4) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O2 C29 O6 124.9(2) . . ? O2 C29 C30 122.4(2) . . ? O6 C29 C30 112.67(18) . . ? O5 C30 C29 112.30(17) . . ? O5 C30 H30A 109.1 . . ? C29 C30 H30A 109.1 . . ? O5 C30 H30B 109.1 . . ? C29 C30 H30B 109.1 . . ? H30A C30 H30B 107.9 . . ? O1 C31 O5 124.18(19) . . ? O1 C31 C32 123.67(19) . . ? O5 C31 C32 112.09(18) . . ? O4 C32 C31 112.51(17) . . ? O4 C32 H32A 109.1 . . ? C31 C32 H32A 109.1 . . ? O4 C32 H32B 109.1 . . ? C31 C32 H32B 109.1 . . ? H32A C32 H32B 107.8 . . ? O3 C33 O4 125.1(2) . . ? O3 C33 C34 126.2(2) . . ? O4 C33 C34 108.70(19) . . ? O6 C34 C33 110.39(19) 2_666 . ? O6 C34 H34A 109.6 2_666 . ? C33 C34 H34A 109.6 . . ? O6 C34 H34B 109.6 2_666 . ? C33 C34 H34B 109.6 . . ? H34A C34 H34B 108.1 . . ? O7 C35 O8 124.03(18) . . ? O7 C35 C36 126.03(18) . . ? O8 C35 C36 109.94(18) . . ? O10 C36 C35 109.89(16) 2_755 . ? O10 C36 H36A 109.7 2_755 . ? C35 C36 H36A 109.7 . . ? O10 C36 H36B 109.7 2_755 . ? C35 C36 H36B 109.7 . . ? H36A C36 H36B 108.2 . . ? O9 C37 O10 123.84(18) . . ? O9 C37 C38 125.17(19) . . ? O10 C37 C38 110.97(17) . . ? O12 C38 C37 109.82(16) 2_755 . ? O12 C38 H38A 109.7 2_755 . ? C37 C38 H38A 109.7 . . ? O12 C38 H38B 109.7 2_755 . ? C37 C38 H38B 109.7 . . ? H38A C38 H38B 108.2 . . ? O11 C39 O12 123.18(19) . . ? O11 C39 C40 125.77(18) . . ? O12 C39 C40 111.05(17) . . ? O8 C40 C39 109.58(16) 2_755 . ? O8 C40 H40A 109.8 2_755 . ? C39 C40 H40A 109.8 . . ? O8 C40 H40B 109.8 2_755 . ? C39 C40 H40B 109.8 . . ? H40A C40 H40B 108.2 . . ? C13 B C7 104.53(16) . . ? C13 B C1 111.68(16) . . ? C7 B C1 112.61(17) . . ? C13 B C19 112.98(17) . . ? C7 B C19 112.62(16) . . ? C1 B C19 102.70(15) . . ? 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 O7 Na O1 C31 177.9(6) . . . . ? O9 Na O1 C31 -95.8(6) . . . . ? N1 Na O1 C31 -10.6(6) . . . . ? N2 Na O1 C31 87.9(6) . . . . ? O1 Na O7 C35 -147.9(7) . . . . ? O11 Na O7 C35 23.1(7) . . . . ? O9 Na O7 C35 116.4(7) . . . . ? N2 Na O7 C35 -60.4(7) . . . . ? O7 Na O9 C37 -35.4(6) . . . . ? O1 Na O9 C37 -123.0(6) . . . . ? O11 Na O9 C37 57.0(6) . . . . ? N1 Na O9 C37 142.2(6) . . . . ? O7 Na O11 C39 69.2(8) . . . . ? O9 Na O11 C39 -17.5(8) . . . . ? N1 Na O11 C39 -101.9(8) . . . . ? N2 Na O11 C39 158.8(8) . . . . ? O1 Na N1 C25 -160.8(4) . . . . ? O11 Na N1 C25 28.2(4) . . . . ? O9 Na N1 C25 -65.7(4) . . . . ? N2 Na N1 C25 110.9(4) . . . . ? O7 Na N2 C27 37.1(6) . . . . ? O1 Na N2 C27 125.1(6) . . . . ? O11 Na N2 C27 -55.5(6) . . . . ? N1 Na N2 C27 -139.9(6) . . . . ? C6 C1 C2 C3 0.2(3) . . . . ? B C1 C2 C3 173.30(19) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? C3 C4 C5 C6 1.0(3) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C2 C1 C6 C5 -0.6(3) . . . . ? B C1 C6 C5 -173.99(19) . . . . ? C12 C7 C8 C9 -1.4(3) . . . . ? B C7 C8 C9 -174.6(2) . . . . ? C7 C8 C9 C10 0.3(3) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? C10 C11 C12 C7 -0.5(3) . . . . ? C8 C7 C12 C11 1.5(3) . . . . ? B C7 C12 C11 174.9(2) . . . . ? C18 C13 C14 C15 1.2(3) . . . . ? B C13 C14 C15 174.38(18) . . . . ? C13 C14 C15 C16 -0.8(3) . . . . ? C14 C15 C16 C17 -0.1(3) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C16 C17 C18 C13 0.0(3) . . . . ? C14 C13 C18 C17 -0.8(3) . . . . ? B C13 C18 C17 -174.06(19) . . . . ? C24 C19 C20 C21 1.6(3) . . . . ? B C19 C20 C21 174.27(18) . . . . ? C19 C20 C21 C22 -0.7(3) . . . . ? C20 C21 C22 C23 -0.6(3) . . . . ? C21 C22 C23 C24 0.8(3) . . . . ? C22 C23 C24 C19 0.2(3) . . . . ? C20 C19 C24 C23 -1.4(3) . . . . ? B C19 C24 C23 -174.19(17) . . . . ? C34 O6 C29 O2 0.3(3) 2_666 . . . ? C34 O6 C29 C30 178.66(18) 2_666 . . . ? C31 O5 C30 C29 -100.3(2) . . . . ? O2 C29 C30 O5 -164.9(2) . . . . ? O6 C29 C30 O5 16.7(3) . . . . ? Na O1 C31 O5 -58.9(6) . . . . ? Na O1 C31 C32 117.9(5) . . . . ? C30 O5 C31 O1 -8.3(3) . . . . ? C30 O5 C31 C32 174.60(18) . . . . ? C33 O4 C32 C31 -73.0(2) . . . . ? O1 C31 C32 O4 158.9(2) . . . . ? O5 C31 C32 O4 -24.0(3) . . . . ? C32 O4 C33 O3 -3.6(3) . . . . ? C32 O4 C33 C34 174.99(17) . . . . ? O3 C33 C34 O6 8.3(3) . . . 2_666 ? O4 C33 C34 O6 -170.28(17) . . . 2_666 ? Na O7 C35 O8 -158.6(6) . . . . ? Na O7 C35 C36 21.6(8) . . . . ? C40 O8 C35 O7 2.7(3) 2_755 . . . ? C40 O8 C35 C36 -177.42(16) 2_755 . . . ? O7 C35 C36 O10 -10.4(3) . . . 2_755 ? O8 C35 C36 O10 169.74(15) . . . 2_755 ? Na O9 C37 O10 -98.6(6) . . . . ? Na O9 C37 C38 83.0(6) . . . . ? C36 O10 C37 O9 2.0(3) 2_755 . . . ? C36 O10 C37 C38 -179.42(16) 2_755 . . . ? O9 C37 C38 O12 -17.3(3) . . . 2_755 ? O10 C37 C38 O12 164.08(15) . . . 2_755 ? Na O11 C39 O12 -116.2(7) . . . . ? Na O11 C39 C40 64.4(8) . . . . ? C38 O12 C39 O11 2.5(3) 2_755 . . . ? C38 O12 C39 C40 -178.10(15) 2_755 . . . ? O11 C39 C40 O8 -16.6(3) . . . 2_755 ? O12 C39 C40 O8 163.99(16) . . . 2_755 ? C18 C13 B C7 85.7(2) . . . . ? C14 C13 B C7 -86.9(2) . . . . ? C18 C13 B C1 -36.3(3) . . . . ? C14 C13 B C1 151.05(18) . . . . ? C18 C13 B C19 -151.48(18) . . . . ? C14 C13 B C19 35.9(2) . . . . ? C8 C7 B C13 97.0(2) . . . . ? C12 C7 B C13 -75.8(2) . . . . ? C8 C7 B C1 -141.60(19) . . . . ? C12 C7 B C1 45.7(3) . . . . ? C8 C7 B C19 -26.0(3) . . . . ? C12 C7 B C19 161.22(18) . . . . ? C2 C1 B C13 141.42(19) . . . . ? C6 C1 B C13 -45.9(2) . . . . ? C2 C1 B C7 24.2(3) . . . . ? C6 C1 B C7 -163.16(18) . . . . ? C2 C1 B C19 -97.2(2) . . . . ? C6 C1 B C19 75.4(2) . . . . ? C20 C19 B C13 30.1(2) . . . . ? C24 C19 B C13 -157.74(17) . . . . ? C20 C19 B C7 148.22(18) . . . . ? C24 C19 B C7 -39.6(2) . . . . ? C20 C19 B C1 -90.4(2) . . . . ? C24 C19 B C1 81.8(2) . . . . ? #===END # CIF produced by WinGX routine CIF_UPDATE # Created on 2005-05-05 at 17:21:50 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : c:\wingx\files\archive.dat # CIF files read : shelxl dreduc import struct data_Chisholm1371 _database_code_depnum_ccdc_archive 'CCDC 271311' _audit_creation_date 2005-05-05T17:21:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Chisholm 1371' _chemical_formula_moiety 'C12 H12 O12' _chemical_formula_sum 'C12 H12 O12' _chemical_formula_weight 348.22 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 14 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 7.6685(10) _cell_length_b 5.9013(10) _cell_length_c 16.004(3) _cell_angle_alpha 90 _cell_angle_beta 102.408(9) _cell_angle_gamma 90 _cell_volume 707.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1776 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 4.5. Phi and omega scans with a frame width of 2.0 degrees were used for data collection. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. The molecule contains a crystallographic inversion center. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.599418E-1 _diffrn_orient_matrix_ub_12 0.119235 _diffrn_orient_matrix_ub_13 -0.42693E-2 _diffrn_orient_matrix_ub_21 -0.149834 _diffrn_orient_matrix_ub_22 -0.743527E-1 _diffrn_orient_matrix_ub_23 0.271337E-1 _diffrn_orient_matrix_ub_31 0.18864E-2 _diffrn_orient_matrix_ub_32 0.185341E-1 _diffrn_orient_matrix_ub_33 0.612047E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 17673 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 1618 _reflns_number_gt 1313 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;The hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2*Ueq(bonded atom). 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 'w=1/[\s^2^(Fo^2^)+(0.0698P)^2^+0.0716P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1618 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.041 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.291 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 -0.04622(12) 0.18680(16) -0.08323(6) 0.0273(3) Uani 1 1 d . . . O2 O 0.30843(13) 0.44434(17) -0.05034(6) 0.0275(3) Uani 1 1 d . . . O3 O 0.46726(13) 0.05313(17) 0.20358(6) 0.0302(3) Uani 1 1 d . . . O4 O 0.00000(13) -0.01309(16) -0.19657(6) 0.0251(3) Uani 1 1 d . . . O5 O 0.29048(12) 0.09873(16) 0.00640(6) 0.0237(3) Uani 1 1 d . . . O6 O 0.23341(12) 0.28090(16) 0.14912(6) 0.0240(3) Uani 1 1 d . . . C1 C 0.04915(18) 0.0744(2) -0.11701(8) 0.0219(3) Uani 1 1 d . . . C2 C 0.23778(19) 0.0046(2) -0.07773(9) 0.0243(3) Uani 1 1 d . . . H2A H 0.2458 -0.1627 -0.0746 0.029 Uiso 1 1 calc R . . H2B H 0.3191 0.0589 -0.1138 0.029 Uiso 1 1 calc R . . C3 C 0.31003(16) 0.3241(2) 0.01065(8) 0.0214(3) Uani 1 1 d . . . C4 C 0.33891(19) 0.4085(2) 0.10159(8) 0.0242(3) Uani 1 1 d . . . H4A H 0.4668 0.3945 0.1295 0.029 Uiso 1 1 calc R . . H4B H 0.3058 0.5706 0.1015 0.029 Uiso 1 1 calc R . . C5 C 0.31283(19) 0.1033(2) 0.19432(8) 0.0235(3) Uani 1 1 d . . . C6 C 0.18441(18) -0.0246(3) 0.23645(9) 0.0265(3) Uani 1 1 d . . . H6A H 0.2103 -0.1887 0.2348 0.032 Uiso 1 1 calc R . . H6B H 0.2044 0.0214 0.2972 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0249(5) 0.0297(6) 0.0281(5) -0.0045(4) 0.0072(4) 0.0015(4) O2 0.0302(6) 0.0293(6) 0.0223(5) 0.0047(4) 0.0038(4) -0.0033(4) O3 0.0239(6) 0.0367(6) 0.0295(6) 0.0056(4) 0.0047(4) 0.0043(4) O4 0.0232(5) 0.0328(6) 0.0193(5) -0.0018(4) 0.0050(4) -0.0004(4) O5 0.0281(5) 0.0224(5) 0.0197(5) -0.0001(4) 0.0027(4) 0.0000(4) O6 0.0240(5) 0.0273(5) 0.0207(5) 0.0023(4) 0.0052(4) 0.0014(4) C1 0.0245(7) 0.0215(7) 0.0202(6) 0.0013(5) 0.0061(5) -0.0031(5) C2 0.0258(7) 0.0243(7) 0.0226(7) -0.0019(6) 0.0047(6) 0.0010(6) C3 0.0167(6) 0.0229(7) 0.0239(7) 0.0021(5) 0.0026(5) 0.0004(5) C4 0.0260(7) 0.0241(7) 0.0219(7) 0.0015(6) 0.0040(6) -0.0022(6) C5 0.0264(7) 0.0253(7) 0.0177(6) -0.0017(5) 0.0025(5) 0.0001(6) C6 0.0239(8) 0.0349(8) 0.0193(7) 0.0018(6) 0.0013(5) -0.0008(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.1990(16) . ? O2 C3 1.2048(16) . ? O3 C5 1.1986(17) . ? O4 C1 1.3503(16) . ? O4 C6 1.4383(17) 3 ? O5 C3 1.3383(17) . ? O5 C2 1.4321(16) . ? O6 C5 1.3431(17) . ? O6 C4 1.4367(16) . ? C1 C2 1.505(2) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.5089(19) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.510(2) . ? C6 O4 1.4383(17) 3 ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O4 C6 114.07(11) . 3 ? C3 O5 C2 116.04(10) . . ? C5 O6 C4 116.89(11) . . ? O1 C1 O4 124.27(13) . . ? O1 C1 C2 125.97(12) . . ? O4 C1 C2 109.74(11) . . ? O5 C2 C1 109.77(11) . . ? O5 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? O5 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? O2 C3 O5 124.24(12) . . ? O2 C3 C4 124.11(13) . . ? O5 C3 C4 111.63(11) . . ? O6 C4 C3 110.80(11) . . ? O6 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? O6 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? O3 C5 O6 125.51(13) . . ? O3 C5 C6 122.91(13) . . ? O6 C5 C6 111.53(12) . . ? O4 C6 C5 113.45(11) 3 . ? O4 C6 H6A 108.9 3 . ? C5 C6 H6A 108.9 . . ? O4 C6 H6B 108.9 3 . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? 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 C6 O4 C1 O1 -4.69(18) 3 . . . ? C6 O4 C1 C2 174.04(11) 3 . . . ? C3 O5 C2 C1 -68.36(14) . . . . ? O1 C1 C2 O5 -1.73(19) . . . . ? O4 C1 C2 O5 179.57(10) . . . . ? C2 O5 C3 O2 -9.77(18) . . . . ? C2 O5 C3 C4 171.64(10) . . . . ? C5 O6 C4 C3 93.91(13) . . . . ? O2 C3 C4 O6 144.43(13) . . . . ? O5 C3 C4 O6 -36.98(14) . . . . ? C4 O6 C5 O3 6.10(19) . . . . ? C4 O6 C5 C6 -176.31(11) . . . . ? O3 C5 C6 O4 -160.94(13) . . . 3 ? O6 C5 C6 O4 21.39(16) . . . 3 ? data_Chisholm_CMC0438 _database_code_depnum_ccdc_archive 'CCDC 651113' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H25 B N2' _chemical_formula_sum 'C25 H25 B N2' _chemical_formula_weight 364.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0007 0.0007 '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 0.0018 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0003 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.2297(11) _cell_length_b 11.7129(8) _cell_length_c 22.5154(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4016.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 95(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.015 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;Because of the small size of the crystal a synchrotron data set was collected at The Advanced Photon Source at the beamline ChemMatCARS Sector 15. All work was done at 95 K using a Bruker Smart6000 diffractometer. The data collection strategy was set up to measure a hemisphere of reciprocal space. Omega and phi scans with a frame width of 0.5 degree and an exposure time of one second were used. Data integration was done with SAINT and scaling of the data was done with SADABS. The crystal was too small to be accurately measured with the available microscope. While the maximum dimension was measurable at 0.08 mm, the other two dimensions were smaller than 0.08 mm. ChemMatCARS Sector 15 is principally supported by the National Science Foundation/Department of Energy under grant number CHE0087817 and by the Illinois Board of Higher Education. The Advanced Photon Source is supported by the U.S. Department of Energy, Basic Energy Sciences, Office of Science, under Contract No. W-31-109-Eng-38. Dr. Maren Pink of Indiana University collected the synchrotron data set. ; _diffrn_ambient_temperature 95(2) _diffrn_radiation_wavelength 0.49594 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator 'diamond 1 1 1' _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48843 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 17.51 _reflns_number_total 3750 _reflns_number_gt 3200 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'SAINT, Bruker AXS, 2003' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ;For the methyl groups, the hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle, which defines the orientation of the methyl group about the N-C bond, was refined. The remaining hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2 * Ueq (attached atom). 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 'w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+2.6670P] 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 0.0060(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3750 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.002 _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 B B 0.32810(11) 0.21363(14) 0.62902(7) 0.0131(3) Uani 1 1 d . . . C1 C 0.26956(9) 0.20211(12) 0.56834(6) 0.0142(3) Uani 1 1 d . . . C2 C 0.28576(10) 0.12031(13) 0.52451(7) 0.0180(3) Uani 1 1 d . . . H2 H 0.3322 0.0672 0.5302 0.022 Uiso 1 1 calc R . . C3 C 0.23573(11) 0.11434(15) 0.47259(7) 0.0242(4) Uani 1 1 d . . . H3 H 0.2479 0.0568 0.4440 0.029 Uiso 1 1 calc R . . C4 C 0.16879(11) 0.19142(15) 0.46261(7) 0.0260(4) Uani 1 1 d . . . H4 H 0.1356 0.1886 0.4269 0.031 Uiso 1 1 calc R . . C5 C 0.15057(11) 0.27334(14) 0.50562(7) 0.0235(4) Uani 1 1 d . . . H5 H 0.1048 0.3271 0.4993 0.028 Uiso 1 1 calc R . . C6 C 0.19910(10) 0.27683(13) 0.55778(7) 0.0180(3) Uani 1 1 d . . . H6 H 0.1842 0.3315 0.5873 0.022 Uiso 1 1 calc R . . C7 C 0.26480(9) 0.22355(13) 0.68724(6) 0.0136(3) Uani 1 1 d . . . C8 C 0.19923(10) 0.14093(13) 0.69612(7) 0.0179(3) Uani 1 1 d . . . H8 H 0.1901 0.0849 0.6663 0.022 Uiso 1 1 calc R . . C9 C 0.14713(10) 0.13775(14) 0.74677(7) 0.0203(3) Uani 1 1 d . . . H9 H 0.1040 0.0798 0.7513 0.024 Uiso 1 1 calc R . . C10 C 0.15818(10) 0.21924(14) 0.79058(7) 0.0204(4) Uani 1 1 d . . . H10 H 0.1239 0.2165 0.8258 0.024 Uiso 1 1 calc R . . C11 C 0.21972(10) 0.30492(14) 0.78252(7) 0.0194(3) Uani 1 1 d . . . H11 H 0.2263 0.3627 0.8118 0.023 Uiso 1 1 calc R . . C12 C 0.27210(9) 0.30670(13) 0.73159(6) 0.0158(3) Uani 1 1 d . . . H12 H 0.3139 0.3662 0.7269 0.019 Uiso 1 1 calc R . . C13 C 0.39938(10) 0.10985(12) 0.63535(6) 0.0135(3) Uani 1 1 d . . . C14 C 0.38882(10) 0.01645(13) 0.67368(6) 0.0171(3) Uani 1 1 d . . . H14 H 0.3377 0.0125 0.6977 0.021 Uiso 1 1 calc R . . C15 C 0.45068(11) -0.07064(14) 0.67770(7) 0.0223(4) Uani 1 1 d . . . H15 H 0.4405 -0.1333 0.7036 0.027 Uiso 1 1 calc R . . C16 C 0.52680(11) -0.06668(14) 0.64430(7) 0.0232(4) Uani 1 1 d . . . H16 H 0.5700 -0.1247 0.6481 0.028 Uiso 1 1 calc R . . C17 C 0.53901(11) 0.02349(14) 0.60517(8) 0.0239(4) Uani 1 1 d . . . H17 H 0.5905 0.0268 0.5814 0.029 Uiso 1 1 calc R . . C18 C 0.47612(10) 0.10870(14) 0.60074(7) 0.0204(3) Uani 1 1 d . . . H18 H 0.4853 0.1689 0.5731 0.024 Uiso 1 1 calc R . . C19 C 0.45365(10) 0.34601(13) 0.66404(7) 0.0163(3) Uani 1 1 d . . . H19 H 0.4605 0.2916 0.6950 0.020 Uiso 1 1 calc R . . C20 C 0.51066(10) 0.43549(13) 0.66225(7) 0.0189(3) Uani 1 1 d . . . H20 H 0.5546 0.4428 0.6919 0.023 Uiso 1 1 calc R . . C21 C 0.50466(10) 0.51747(12) 0.61636(7) 0.0160(3) Uani 1 1 d . . . C22 C 0.43332(10) 0.50328(13) 0.57699(7) 0.0163(3) Uani 1 1 d . . . H22 H 0.4232 0.5579 0.5466 0.020 Uiso 1 1 calc R . . C23 C 0.37871(10) 0.41095(12) 0.58254(6) 0.0140(3) Uani 1 1 d . . . H23 H 0.3316 0.4039 0.5552 0.017 Uiso 1 1 calc R . . C24 C 0.55768(13) 0.68298(15) 0.56165(8) 0.0296(4) Uani 1 1 d . . . H24A H 0.5432 0.6420 0.5250 0.044 Uiso 1 1 calc R . . H24B H 0.6140 0.7223 0.5568 0.044 Uiso 1 1 calc R . . H24C H 0.5116 0.7391 0.5702 0.044 Uiso 1 1 calc R . . C25 C 0.63303(13) 0.61843(16) 0.65401(10) 0.0399(5) Uani 1 1 d . . . H25A H 0.6069 0.6354 0.6928 0.060 Uiso 1 1 calc R . . H25B H 0.6706 0.6822 0.6418 0.060 Uiso 1 1 calc R . . H25C H 0.6683 0.5487 0.6568 0.060 Uiso 1 1 calc R . . N1 N 0.38765(8) 0.32957(10) 0.62437(5) 0.0125(3) Uani 1 1 d . . . N2 N 0.56379(9) 0.60222(11) 0.61049(6) 0.0225(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 B 0.0141(8) 0.0116(7) 0.0136(8) 0.0021(6) 0.0000(6) -0.0014(6) C1 0.0143(7) 0.0144(7) 0.0137(7) 0.0038(6) 0.0012(5) -0.0048(6) C2 0.0191(8) 0.0187(8) 0.0161(7) 0.0013(6) 0.0017(6) -0.0033(6) C3 0.0289(9) 0.0284(9) 0.0154(8) -0.0039(7) 0.0010(7) -0.0071(7) C4 0.0283(9) 0.0344(10) 0.0154(8) 0.0055(7) -0.0073(7) -0.0109(8) C5 0.0206(8) 0.0247(9) 0.0253(8) 0.0092(7) -0.0069(7) -0.0039(7) C6 0.0175(8) 0.0184(8) 0.0182(8) 0.0022(6) -0.0014(6) -0.0035(6) C7 0.0121(7) 0.0160(7) 0.0126(7) 0.0032(6) -0.0025(5) 0.0040(6) C8 0.0169(8) 0.0204(8) 0.0165(7) -0.0018(6) -0.0007(6) -0.0011(6) C9 0.0152(8) 0.0236(8) 0.0222(8) 0.0031(7) 0.0028(6) -0.0012(6) C10 0.0163(7) 0.0283(9) 0.0166(8) 0.0039(6) 0.0049(6) 0.0076(7) C11 0.0214(8) 0.0206(8) 0.0163(8) -0.0043(6) -0.0012(6) 0.0081(6) C12 0.0144(7) 0.0151(7) 0.0178(7) 0.0015(6) -0.0022(6) 0.0042(6) C13 0.0158(7) 0.0135(7) 0.0111(7) -0.0006(6) -0.0026(6) -0.0018(6) C14 0.0210(8) 0.0153(7) 0.0150(7) 0.0005(6) 0.0006(6) -0.0019(6) C15 0.0342(9) 0.0153(8) 0.0173(7) 0.0028(6) -0.0025(7) 0.0019(7) C16 0.0276(9) 0.0175(8) 0.0246(8) -0.0040(7) -0.0060(7) 0.0091(7) C17 0.0210(8) 0.0230(8) 0.0278(9) -0.0013(7) 0.0050(7) 0.0056(7) C18 0.0215(8) 0.0189(8) 0.0208(8) 0.0043(6) 0.0040(6) 0.0017(6) C19 0.0156(7) 0.0160(8) 0.0174(7) 0.0012(6) -0.0034(6) 0.0031(6) C20 0.0148(7) 0.0184(8) 0.0235(8) -0.0020(6) -0.0066(6) 0.0027(6) C21 0.0133(7) 0.0127(7) 0.0221(8) -0.0049(6) 0.0028(6) 0.0011(6) C22 0.0197(8) 0.0132(7) 0.0160(7) 0.0008(6) 0.0019(6) -0.0005(6) C23 0.0139(7) 0.0161(7) 0.0121(7) 0.0004(6) 0.0001(5) 0.0010(6) C24 0.0394(10) 0.0238(9) 0.0257(9) -0.0032(7) 0.0057(8) -0.0169(8) C25 0.0312(10) 0.0226(9) 0.0659(14) 0.0029(9) -0.0224(10) -0.0107(8) N1 0.0112(6) 0.0122(6) 0.0142(6) 0.0004(5) 0.0006(5) 0.0013(5) N2 0.0191(7) 0.0150(7) 0.0335(8) -0.0022(6) -0.0020(6) -0.0042(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 B C7 1.631(2) . ? B C13 1.636(2) . ? B N1 1.636(2) . ? B C1 1.637(2) . ? C1 C2 1.398(2) . ? C1 C6 1.405(2) . ? C2 C3 1.397(2) . ? C2 H2 0.9500 . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 C6 1.388(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.399(2) . ? C7 C8 1.405(2) . ? C8 C9 1.390(2) . ? C8 H8 0.9500 . ? C9 C10 1.383(2) . ? C9 H9 0.9500 . ? C10 C11 1.385(2) . ? C10 H10 0.9500 . ? C11 C12 1.397(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.403(2) . ? C13 C18 1.405(2) . ? C14 C15 1.392(2) . ? C14 H14 0.9500 . ? C15 C16 1.383(2) . ? C15 H15 0.9500 . ? C16 C17 1.388(2) . ? C16 H16 0.9500 . ? C17 C18 1.387(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 N1 1.3584(19) . ? C19 C20 1.362(2) . ? C19 H19 0.9500 . ? C20 C21 1.413(2) . ? C20 H20 0.9500 . ? C21 N2 1.347(2) . ? C21 C22 1.412(2) . ? C22 C23 1.370(2) . ? C22 H22 0.9500 . ? C23 N1 1.3470(18) . ? C23 H23 0.9500 . ? C24 N2 1.454(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 N2 1.452(2) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 C7 B C13 112.03(12) . . ? C7 B N1 108.65(11) . . ? C13 B N1 104.74(11) . . ? C7 B C1 110.77(12) . . ? C13 B C1 111.89(12) . . ? N1 B C1 108.47(11) . . ? C2 C1 C6 116.25(14) . . ? C2 C1 B 123.36(13) . . ? C6 C1 B 120.39(13) . . ? C3 C2 C1 121.94(15) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C4 C3 C2 120.42(15) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.02(15) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 120.20(16) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 122.11(15) . . ? C5 C6 H6 118.9 . . ? C1 C6 H6 118.9 . . ? C12 C7 C8 115.75(13) . . ? C12 C7 B 125.17(13) . . ? C8 C7 B 119.04(13) . . ? C9 C8 C7 122.76(14) . . ? C9 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? C10 C9 C8 119.82(15) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 119.28(14) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C10 C11 C12 120.31(14) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 122.00(14) . . ? C11 C12 H12 119.0 . . ? C7 C12 H12 119.0 . . ? C14 C13 C18 115.41(14) . . ? C14 C13 B 123.86(13) . . ? C18 C13 B 120.73(13) . . ? C15 C14 C13 122.30(14) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C16 C15 C14 120.50(14) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 118.89(15) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? C18 C17 C16 120.05(15) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C13 122.80(15) . . ? C17 C18 H18 118.6 . . ? C13 C18 H18 118.6 . . ? N1 C19 C20 124.16(14) . . ? N1 C19 H19 117.9 . . ? C20 C19 H19 117.9 . . ? C19 C20 C21 120.22(14) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? N2 C21 C22 122.66(14) . . ? N2 C21 C20 121.96(14) . . ? C22 C21 C20 115.38(13) . . ? C23 C22 C21 120.18(14) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? N1 C23 C22 124.13(14) . . ? N1 C23 H23 117.9 . . ? C22 C23 H23 117.9 . . ? N2 C24 H24A 109.5 . . ? N2 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N2 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 C25 H25A 109.5 . . ? N2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 N1 C19 115.74(13) . . ? C23 N1 B 125.17(12) . . ? C19 N1 B 119.06(12) . . ? C21 N2 C25 121.05(14) . . ? C21 N2 C24 120.74(14) . . ? C25 N2 C24 118.16(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 C7 B C1 C2 -132.31(14) . . . . ? C13 B C1 C2 -6.52(19) . . . . ? N1 B C1 C2 108.52(15) . . . . ? C7 B C1 C6 48.05(18) . . . . ? C13 B C1 C6 173.84(13) . . . . ? N1 B C1 C6 -71.12(16) . . . . ? C6 C1 C2 C3 1.1(2) . . . . ? B C1 C2 C3 -178.58(14) . . . . ? C1 C2 C3 C4 1.0(2) . . . . ? C2 C3 C4 C5 -1.5(2) . . . . ? C3 C4 C5 C6 -0.2(2) . . . . ? C4 C5 C6 C1 2.4(2) . . . . ? C2 C1 C6 C5 -2.8(2) . . . . ? B C1 C6 C5 176.86(14) . . . . ? C13 B C7 C12 104.22(16) . . . . ? N1 B C7 C12 -11.01(19) . . . . ? C1 B C7 C12 -130.07(14) . . . . ? C13 B C7 C8 -73.17(16) . . . . ? N1 B C7 C8 171.60(12) . . . . ? C1 B C7 C8 52.54(17) . . . . ? C12 C7 C8 C9 -2.8(2) . . . . ? B C7 C8 C9 174.79(14) . . . . ? C7 C8 C9 C10 0.9(2) . . . . ? C8 C9 C10 C11 1.7(2) . . . . ? C9 C10 C11 C12 -2.2(2) . . . . ? C10 C11 C12 C7 0.0(2) . . . . ? C8 C7 C12 C11 2.4(2) . . . . ? B C7 C12 C11 -175.10(13) . . . . ? C7 B C13 C14 21.66(19) . . . . ? N1 B C13 C14 139.25(14) . . . . ? C1 B C13 C14 -103.44(15) . . . . ? C7 B C13 C18 -159.50(13) . . . . ? N1 B C13 C18 -41.91(17) . . . . ? C1 B C13 C18 75.40(17) . . . . ? C18 C13 C14 C15 0.8(2) . . . . ? B C13 C14 C15 179.69(14) . . . . ? C13 C14 C15 C16 1.3(2) . . . . ? C14 C15 C16 C17 -2.3(2) . . . . ? C15 C16 C17 C18 1.1(2) . . . . ? C16 C17 C18 C13 1.2(3) . . . . ? C14 C13 C18 C17 -2.0(2) . . . . ? B C13 C18 C17 179.04(15) . . . . ? N1 C19 C20 C21 -1.4(2) . . . . ? C19 C20 C21 N2 -174.89(14) . . . . ? C19 C20 C21 C22 4.3(2) . . . . ? N2 C21 C22 C23 175.39(14) . . . . ? C20 C21 C22 C23 -3.8(2) . . . . ? C21 C22 C23 N1 0.3(2) . . . . ? C22 C23 N1 C19 2.8(2) . . . . ? C22 C23 N1 B -175.15(13) . . . . ? C20 C19 N1 C23 -2.2(2) . . . . ? C20 C19 N1 B 175.83(14) . . . . ? C7 B N1 C23 -110.20(15) . . . . ? C13 B N1 C23 129.92(14) . . . . ? C1 B N1 C23 10.29(18) . . . . ? C7 B N1 C19 71.96(15) . . . . ? C13 B N1 C19 -47.92(16) . . . . ? C1 B N1 C19 -167.55(12) . . . . ? C22 C21 N2 C25 176.04(16) . . . . ? C20 C21 N2 C25 -4.8(2) . . . . ? C22 C21 N2 C24 -1.3(2) . . . . ? C20 C21 N2 C24 177.86(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 17.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.321 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.046 #===END # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-01-31 at 13:00:45 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : shelxl dreduc import struct data_Chisholm1498 _database_code_depnum_ccdc_archive 'CCDC 651114' _audit_creation_date 2007-01-31T13:00:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Chisholm 1498' _chemical_formula_moiety 'C18 H24 O12' _chemical_formula_sum 'C18 H24 O12' _chemical_formula_weight 432.37 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4322(10) _cell_length_b 16.513(2) _cell_length_c 14.964(2) _cell_angle_alpha 90 _cell_angle_beta 93.048(5) _cell_angle_gamma 90 _cell_volume 2080.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4911 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'wedge-shaped fragment' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.38 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_special_details ;The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 3.7, which means that 90% of the data were measured at least 3.7 times. Phi and omega scans with a frame width of 1.0 degree were used for data collection. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.105626 _diffrn_orient_matrix_ub_12 -0.539368E-1 _diffrn_orient_matrix_ub_13 0.61782E-2 _diffrn_orient_matrix_ub_21 -0.76003E-2 _diffrn_orient_matrix_ub_22 0.80641E-2 _diffrn_orient_matrix_ub_23 -0.59537E-1 _diffrn_orient_matrix_ub_31 0.262092E-1 _diffrn_orient_matrix_ub_32 -0.604833E-1 _diffrn_orient_matrix_ub_33 -0.115381E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 34054 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 4751 _reflns_number_gt 3455 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;The methyl group hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle, which defines the orientation of the methyl group about the C-C bond, was refined. The other hydrogen atoms were added to the model at calculated positions using a riding model with U(H) = 1.2 * Ueq(attached atom). 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 'w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.2267P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4751 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0905 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.19 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.48085(10) 0.11097(5) 0.17942(6) 0.0316(2) Uani 1 1 d . . . O2 O 0.35295(9) 0.23013(5) 0.18801(5) 0.0285(2) Uani 1 1 d . . . O3 O 0.57546(11) 0.27738(6) 0.08016(6) 0.0387(2) Uani 1 1 d . . . O4 O 0.45644(9) 0.21419(5) -0.03745(5) 0.0248(2) Uani 1 1 d . . . O5 O 0.87213(10) 0.18253(6) -0.05541(6) 0.0402(3) Uani 1 1 d . . . O6 O 0.67952(9) 0.11003(5) 0.00539(5) 0.0257(2) Uani 1 1 d . . . O7 O 0.86594(10) 0.15118(5) 0.15590(6) 0.0335(2) Uani 1 1 d . . . O8 O 0.98151(9) 0.02802(5) 0.15755(6) 0.0300(2) Uani 1 1 d . . . O9 O 1.00592(12) 0.08945(7) 0.38668(7) 0.0491(3) Uani 1 1 d . . . O10 O 0.83269(9) 0.00957(5) 0.30835(6) 0.0279(2) Uani 1 1 d . . . O11 O 0.46812(10) 0.06348(6) 0.39366(6) 0.0389(2) Uani 1 1 d . . . O12 O 0.65567(9) 0.13791(5) 0.33124(5) 0.0282(2) Uani 1 1 d . . . C1 C 0.45739(13) 0.17289(8) 0.21852(8) 0.0247(3) Uani 1 1 d . . . C2 C 0.31092(14) 0.22552(8) 0.09324(8) 0.0273(3) Uani 1 1 d . . . H2 H 0.2707 0.1701 0.0772 0.033 Uiso 1 1 calc R . . C3 C 0.18366(16) 0.28793(9) 0.07228(9) 0.0390(3) Uani 1 1 d . . . H3A H 0.0903 0.2756 0.1061 0.059 Uiso 1 1 calc R . . H3B H 0.1541 0.2869 0.0081 0.059 Uiso 1 1 calc R . . H3C H 0.224 0.3418 0.089 0.059 Uiso 1 1 calc R . . C4 C 0.46293(14) 0.24308(7) 0.04622(8) 0.0257(3) Uani 1 1 d . . . C5 C 0.60281(13) 0.22436(8) -0.08326(8) 0.0275(3) Uani 1 1 d . . . H5 H 0.6361 0.2825 -0.0803 0.033 Uiso 1 1 calc R . . C6 C 0.56669(16) 0.20065(9) -0.17948(9) 0.0366(3) Uani 1 1 d . . . H6A H 0.523 0.1457 -0.182 0.055 Uiso 1 1 calc R . . H6B H 0.6645 0.2024 -0.212 0.055 Uiso 1 1 calc R . . H6C H 0.489 0.2385 -0.2071 0.055 Uiso 1 1 calc R . . C7 C 0.73450(14) 0.17187(7) -0.04188(8) 0.0262(3) Uani 1 1 d . . . C8 C 0.79497(14) 0.05216(7) 0.04027(8) 0.0274(3) Uani 1 1 d . . . H8 H 0.8737 0.0412 -0.0059 0.033 Uiso 1 1 calc R . . C9 C 0.70456(17) -0.02484(8) 0.05835(10) 0.0394(3) Uani 1 1 d . . . H9A H 0.6298 -0.0147 0.105 0.059 Uiso 1 1 calc R . . H9B H 0.7795 -0.0673 0.0783 0.059 Uiso 1 1 calc R . . H9C H 0.646 -0.0423 0.0034 0.059 Uiso 1 1 calc R . . C10 C 0.88097(13) 0.08554(8) 0.12379(8) 0.0260(3) Uani 1 1 d . . . C11 C 1.06977(14) 0.04801(8) 0.24010(9) 0.0313(3) Uani 1 1 d . . . H11 H 1.1251 0.101 0.2329 0.038 Uiso 1 1 calc R . . C12 C 1.19272(15) -0.01837(9) 0.25452(10) 0.0405(4) Uani 1 1 d . . . H12A H 1.1391 -0.0707 0.2594 0.061 Uiso 1 1 calc R . . H12B H 1.2571 -0.0077 0.3097 0.061 Uiso 1 1 calc R . . H12C H 1.2615 -0.0196 0.2038 0.061 Uiso 1 1 calc R . . C13 C 0.96532(15) 0.05315(8) 0.31971(9) 0.0316(3) Uani 1 1 d . . . C14 C 0.72805(14) 0.00650(8) 0.38279(8) 0.0295(3) Uani 1 1 d . . . H14 H 0.7914 0.0168 0.4401 0.035 Uiso 1 1 calc R . . C15 C 0.65611(18) -0.07682(9) 0.38522(11) 0.0447(4) Uani 1 1 d . . . H15A H 0.5932 -0.0868 0.3293 0.067 Uiso 1 1 calc R . . H15B H 0.5874 -0.0807 0.4358 0.067 Uiso 1 1 calc R . . H15C H 0.7409 -0.1173 0.3921 0.067 Uiso 1 1 calc R . . C16 C 0.60139(14) 0.07115(8) 0.36976(8) 0.0258(3) Uani 1 1 d . . . C17 C 0.54001(14) 0.19918(8) 0.30594(8) 0.0263(3) Uani 1 1 d . . . H17 H 0.4611 0.2045 0.3531 0.032 Uiso 1 1 calc R . . C18 C 0.62993(15) 0.27768(8) 0.29689(9) 0.0321(3) Uani 1 1 d . . . H18A H 0.6889 0.2899 0.3535 0.048 Uiso 1 1 calc R . . H18B H 0.5548 0.3216 0.2822 0.048 Uiso 1 1 calc R . . H18C H 0.7044 0.2724 0.2491 0.048 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0386(5) 0.0256(5) 0.0308(5) -0.0031(4) 0.0027(4) 0.0034(4) O2 0.0281(4) 0.0352(5) 0.0220(5) -0.0045(4) 0.0000(3) 0.0106(4) O3 0.0397(5) 0.0416(6) 0.0346(6) -0.0043(4) -0.0004(4) -0.0127(5) O4 0.0247(4) 0.0273(5) 0.0226(5) 0.0000(4) 0.0033(3) 0.0023(3) O5 0.0263(5) 0.0490(6) 0.0462(6) 0.0173(5) 0.0094(4) -0.0002(4) O6 0.0246(4) 0.0232(5) 0.0295(5) 0.0059(4) 0.0041(3) 0.0028(3) O7 0.0382(5) 0.0237(5) 0.0384(5) -0.0008(4) 0.0002(4) 0.0026(4) O8 0.0254(4) 0.0268(5) 0.0374(5) -0.0006(4) -0.0024(4) 0.0045(4) O9 0.0489(6) 0.0507(7) 0.0467(6) -0.0139(5) -0.0049(5) -0.0134(5) O10 0.0247(4) 0.0254(5) 0.0332(5) -0.0031(4) -0.0002(4) -0.0006(4) O11 0.0317(5) 0.0418(6) 0.0440(6) 0.0061(5) 0.0081(4) 0.0015(4) O12 0.0254(4) 0.0275(5) 0.0319(5) 0.0038(4) 0.0014(3) 0.0060(4) C1 0.0232(6) 0.0266(7) 0.0250(7) 0.0018(5) 0.0072(5) 0.0015(5) C2 0.0274(6) 0.0332(7) 0.0210(6) -0.0044(5) -0.0005(5) 0.0040(5) C3 0.0357(7) 0.0511(9) 0.0296(7) -0.0045(7) -0.0045(6) 0.0152(7) C4 0.0301(7) 0.0217(6) 0.0249(7) -0.0004(5) -0.0012(5) 0.0036(5) C5 0.0258(6) 0.0292(7) 0.0282(7) 0.0072(6) 0.0072(5) -0.0001(5) C6 0.0320(7) 0.0505(9) 0.0278(7) 0.0079(6) 0.0066(5) 0.0021(6) C7 0.0277(7) 0.0280(7) 0.0234(6) 0.0021(5) 0.0056(5) -0.0022(5) C8 0.0268(6) 0.0239(7) 0.0316(7) 0.0015(5) 0.0026(5) 0.0067(5) C9 0.0424(8) 0.0225(7) 0.0518(9) 0.0022(6) -0.0121(7) -0.0003(6) C10 0.0227(6) 0.0226(7) 0.0332(7) 0.0049(6) 0.0065(5) -0.0005(5) C11 0.0246(6) 0.0285(7) 0.0403(8) -0.0009(6) -0.0040(5) -0.0023(5) C12 0.0277(7) 0.0382(8) 0.0546(9) 0.0008(7) -0.0063(6) 0.0043(6) C13 0.0288(7) 0.0252(7) 0.0398(8) -0.0014(6) -0.0085(5) 0.0009(5) C14 0.0307(7) 0.0308(7) 0.0270(7) 0.0014(6) 0.0016(5) 0.0035(6) C15 0.0503(9) 0.0308(8) 0.0545(10) 0.0063(7) 0.0158(7) 0.0025(7) C16 0.0294(7) 0.0286(7) 0.0192(6) -0.0030(5) -0.0014(5) -0.0010(5) C17 0.0245(6) 0.0278(7) 0.0267(7) -0.0008(5) 0.0013(5) 0.0088(5) C18 0.0336(7) 0.0283(7) 0.0336(7) -0.0028(6) -0.0054(5) 0.0045(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.1997(14) . ? O2 C1 1.3545(14) . ? O2 C2 1.4454(14) . ? O3 C4 1.1949(14) . ? O4 C4 1.3383(15) . ? O4 C5 1.4530(13) . ? O5 C7 1.2016(14) . ? O6 C7 1.3390(14) . ? O6 C8 1.4419(14) . ? O7 C10 1.1950(15) . ? O8 C10 1.3530(14) . ? O8 C11 1.4462(15) . ? O9 C13 1.2018(16) . ? O10 C13 1.3331(15) . ? O10 C14 1.4582(15) . ? O11 C16 1.2039(14) . ? O12 C16 1.3361(15) . ? O12 C17 1.4418(14) . ? C1 C17 1.5127(17) . ? C2 C3 1.5088(17) . ? C2 C4 1.5225(17) . ? C2 H2 1 . ? C3 H3A 0.98 . ? C3 H3B 0.98 . ? C3 H3C 0.98 . ? C5 C6 1.5075(18) . ? C5 C7 1.5148(17) . ? C5 H5 1 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C8 C9 1.5143(18) . ? C8 C10 1.5150(17) . ? C8 H8 1 . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C11 C12 1.5163(18) . ? C11 C13 1.521(2) . ? C11 H11 1 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C14 C15 1.5049(19) . ? C14 C16 1.5153(17) . ? C14 H14 1 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C17 C18 1.5115(18) . ? C17 H17 1 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C2 114.52(9) . . ? C4 O4 C5 114.00(9) . . ? C7 O6 C8 116.78(9) . . ? C10 O8 C11 116.26(10) . . ? C13 O10 C14 117.32(10) . . ? C16 O12 C17 116.73(9) . . ? O1 C1 O2 123.47(11) . . ? O1 C1 C17 125.88(11) . . ? O2 C1 C17 110.64(10) . . ? O2 C2 C3 107.61(10) . . ? O2 C2 C4 105.96(9) . . ? C3 C2 C4 112.38(11) . . ? O2 C2 H2 110.3 . . ? C3 C2 H2 110.3 . . ? C4 C2 H2 110.3 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O3 C4 O4 123.96(11) . . ? O3 C4 C2 124.26(11) . . ? O4 C4 C2 111.77(10) . . ? O4 C5 C6 106.68(9) . . ? O4 C5 C7 111.32(9) . . ? C6 C5 C7 110.38(11) . . ? O4 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? C7 C5 H5 109.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O5 C7 O6 124.43(11) . . ? O5 C7 C5 122.74(11) . . ? O6 C7 C5 112.67(10) . . ? O6 C8 C9 106.53(10) . . ? O6 C8 C10 110.00(10) . . ? C9 C8 C10 112.43(11) . . ? O6 C8 H8 109.3 . . ? C9 C8 H8 109.3 . . ? C10 C8 H8 109.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O7 C10 O8 124.36(12) . . ? O7 C10 C8 127.24(11) . . ? O8 C10 C8 108.39(10) . . ? O8 C11 C12 105.86(10) . . ? O8 C11 C13 112.87(10) . . ? C12 C11 C13 110.42(11) . . ? O8 C11 H11 109.2 . . ? C12 C11 H11 109.2 . . ? C13 C11 H11 109.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O9 C13 O10 125.12(13) . . ? O9 C13 C11 121.99(12) . . ? O10 C13 C11 112.76(11) . . ? O10 C14 C15 108.13(11) . . ? O10 C14 C16 109.16(10) . . ? C15 C14 C16 111.40(11) . . ? O10 C14 H14 109.4 . . ? C15 C14 H14 109.4 . . ? C16 C14 H14 109.4 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O11 C16 O12 124.16(11) . . ? O11 C16 C14 123.39(12) . . ? O12 C16 C14 112.43(10) . . ? O12 C17 C18 106.85(9) . . ? O12 C17 C1 107.44(10) . . ? C18 C17 C1 112.26(10) . . ? O12 C17 H17 110.1 . . ? C18 C17 H17 110.1 . . ? C1 C17 H17 110.1 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 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 C2 O2 C1 O1 -19.80(16) . . . . ? C2 O2 C1 C17 159.02(9) . . . . ? C1 O2 C2 C3 174.88(10) . . . . ? C1 O2 C2 C4 -64.71(13) . . . . ? C5 O4 C4 O3 3.00(17) . . . . ? C5 O4 C4 C2 -175.93(9) . . . . ? O2 C2 C4 O3 -20.48(16) . . . . ? C3 C2 C4 O3 96.78(14) . . . . ? O2 C2 C4 O4 158.45(9) . . . . ? C3 C2 C4 O4 -84.29(13) . . . . ? C4 O4 C5 C6 -171.53(10) . . . . ? C4 O4 C5 C7 67.99(13) . . . . ? C8 O6 C7 O5 -1.29(17) . . . . ? C8 O6 C7 C5 174.25(10) . . . . ? O4 C5 C7 O5 -163.68(12) . . . . ? C6 C5 C7 O5 78.04(16) . . . . ? O4 C5 C7 O6 20.69(14) . . . . ? C6 C5 C7 O6 -97.59(12) . . . . ? C7 O6 C8 C9 -158.87(10) . . . . ? C7 O6 C8 C10 79.02(12) . . . . ? C11 O8 C10 O7 2.77(17) . . . . ? C11 O8 C10 C8 -177.53(9) . . . . ? O6 C8 C10 O7 -3.81(17) . . . . ? C9 C8 C10 O7 -122.34(14) . . . . ? O6 C8 C10 O8 176.51(9) . . . . ? C9 C8 C10 O8 57.97(13) . . . . ? C10 O8 C11 C12 -170.10(10) . . . . ? C10 O8 C11 C13 69.00(14) . . . . ? C14 O10 C13 O9 0.68(18) . . . . ? C14 O10 C13 C11 176.61(10) . . . . ? O8 C11 C13 O9 -159.33(12) . . . . ? C12 C11 C13 O9 82.40(16) . . . . ? O8 C11 C13 O10 24.59(15) . . . . ? C12 C11 C13 O10 -93.68(13) . . . . ? C13 O10 C14 C15 -144.12(11) . . . . ? C13 O10 C14 C16 94.53(12) . . . . ? C17 O12 C16 O11 -9.08(17) . . . . ? C17 O12 C16 C14 172.67(9) . . . . ? O10 C14 C16 O11 147.10(11) . . . . ? C15 C14 C16 O11 27.76(17) . . . . ? O10 C14 C16 O12 -34.63(14) . . . . ? C15 C14 C16 O12 -153.97(11) . . . . ? C16 O12 C17 C18 159.55(10) . . . . ? C16 O12 C17 C1 -79.79(12) . . . . ? O1 C1 C17 O12 2.27(16) . . . . ? O2 C1 C17 O12 -176.50(9) . . . . ? O1 C1 C17 C18 119.46(13) . . . . ? O2 C1 C17 C18 -59.32(13) . . . . ? #===END # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-01-31 at 12:41:48 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : shelxl dreduc import struct data_Chisholm1477 _database_code_depnum_ccdc_archive 'CCDC 651115' _audit_creation_date 2007-01-31T12:41:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Chisholm 1477' _chemical_formula_moiety 'C18 H24 O12' _chemical_formula_sum 'C18 H24 O12' _chemical_formula_weight 432.37 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.663(2) _cell_length_b 11.967(3) _cell_length_c 16.489(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2104.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2138 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure an octant of reciprocal space with a redundancy factor of 3.7. Phi and omega scans with a frame width of 1.0 degree were used for data collection. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. The correct enantiomer was chosen based on the known chiral centers. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.101686E-1 _diffrn_orient_matrix_ub_12 0.932246E-1 _diffrn_orient_matrix_ub_13 -0.6235E-3 _diffrn_orient_matrix_ub_21 0.18532E-1 _diffrn_orient_matrix_ub_22 -0.25661E-2 _diffrn_orient_matrix_ub_23 -0.81444E-1 _diffrn_orient_matrix_ub_31 -0.587682E-1 _diffrn_orient_matrix_ub_32 0.63194E-2 _diffrn_orient_matrix_ub_33 -0.135714E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 16936 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.1 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2124 _reflns_number_gt 1925 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; The methyl group hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle, which defines the orientation of the methyl group about the C-C bond, was refined. The other hydrogen atoms were added to the model at calculated positions using a riding model with U(H) = 1.2 * Ueq(attached atom). 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 'w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.3605P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2124 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0846 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_diff_density_max 0.308 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.64995(17) 0.50510(16) 0.28006(11) 0.0396(5) Uani 1 1 d . . . O2 O 0.78742(16) 0.39050(15) 0.34148(10) 0.0346(4) Uani 1 1 d . . . O3 O 0.7448(2) 0.26272(17) 0.14802(12) 0.0504(5) Uani 1 1 d . . . O4 O 0.87582(16) 0.39576(14) 0.19470(10) 0.0316(4) Uani 1 1 d . . . O5 O 0.74508(17) 0.52905(17) 0.08275(12) 0.0440(5) Uani 1 1 d . . . O6 O 0.93601(15) 0.59983(14) 0.05748(10) 0.0311(4) Uani 1 1 d . . . O7 O 0.87058(18) 0.73774(16) 0.18146(11) 0.0397(5) Uani 1 1 d . . . O8 O 0.75494(17) 0.84299(15) 0.09809(10) 0.0375(4) Uani 1 1 d . . . O9 O 0.57043(16) 0.75818(16) 0.20145(11) 0.0373(4) Uani 1 1 d . . . O10 O 0.64679(17) 0.87030(15) 0.29962(11) 0.0365(4) Uani 1 1 d . . . O11 O 0.58298(17) 0.64450(18) 0.43580(11) 0.0469(5) Uani 1 1 d . . . O12 O 0.74560(16) 0.68660(14) 0.35490(10) 0.0339(4) Uani 1 1 d . . . C1 C 0.7351(2) 0.4909(2) 0.32591(15) 0.0324(6) Uani 1 1 d . . . C2 C 0.7440(2) 0.3016(2) 0.28937(16) 0.0345(6) Uani 1 1 d . . . H2 H 0.6522 0.299 0.2909 0.041 Uiso 1 1 calc R . . C3 C 0.7959(3) 0.1935(2) 0.32274(18) 0.0427(7) Uani 1 1 d . . . H3A H 0.8859 0.1961 0.322 0.064 Uiso 1 1 calc R . . H3B H 0.7674 0.1322 0.29 0.064 Uiso 1 1 calc R . . H3C H 0.7673 0.1835 0.3775 0.064 Uiso 1 1 calc R . . C4 C 0.7870(2) 0.3181(2) 0.20240(16) 0.0335(6) Uani 1 1 d . . . C5 C 0.9242(2) 0.4162(2) 0.11344(15) 0.0311(6) Uani 1 1 d . . . H5 H 0.9023 0.353 0.0785 0.037 Uiso 1 1 calc R . . C6 C 1.0655(2) 0.4243(2) 0.11975(18) 0.0399(7) Uani 1 1 d . . . H6A H 1.0875 0.4853 0.1547 0.06 Uiso 1 1 calc R . . H6B H 1.1004 0.4367 0.0668 0.06 Uiso 1 1 calc R . . H6C H 1.0982 0.3559 0.1417 0.06 Uiso 1 1 calc R . . C7 C 0.8570(2) 0.5200(2) 0.08337(14) 0.0306(6) Uani 1 1 d . . . C8 C 0.8771(2) 0.7046(2) 0.03659(14) 0.0327(6) Uani 1 1 d . . . H8 H 0.8054 0.6918 0.0006 0.039 Uiso 1 1 calc R . . C9 C 0.9744(3) 0.7764(2) -0.00516(16) 0.0449(7) Uani 1 1 d . . . H9A H 1.046 0.7849 0.0297 0.067 Uiso 1 1 calc R . . H9B H 0.9393 0.8485 -0.0168 0.067 Uiso 1 1 calc R . . H9C H 0.9998 0.7412 -0.0549 0.067 Uiso 1 1 calc R . . C10 C 0.8343(2) 0.7601(2) 0.11465(16) 0.0313(6) Uani 1 1 d . . . C11 C 0.7161(3) 0.9077(2) 0.16803(16) 0.0371(6) Uani 1 1 d . . . H11 H 0.7895 0.9357 0.1974 0.044 Uiso 1 1 calc R . . C12 C 0.6389(3) 1.0038(2) 0.13624(19) 0.0475(7) Uani 1 1 d . . . H12A H 0.6908 1.0514 0.1036 0.071 Uiso 1 1 calc R . . H12B H 0.6057 1.0458 0.181 0.071 Uiso 1 1 calc R . . H12C H 0.5711 0.9754 0.104 0.071 Uiso 1 1 calc R . . C13 C 0.6366(2) 0.8337(2) 0.22306(15) 0.0322(6) Uani 1 1 d . . . C14 C 0.5714(2) 0.8125(2) 0.35874(15) 0.0385(6) Uani 1 1 d . . . H14 H 0.4903 0.794 0.3341 0.046 Uiso 1 1 calc R . . C15 C 0.5494(3) 0.8935(3) 0.4284(2) 0.0632(9) Uani 1 1 d . . . H15A H 0.6284 0.9136 0.4522 0.095 Uiso 1 1 calc R . . H15B H 0.4974 0.8586 0.4686 0.095 Uiso 1 1 calc R . . H15C H 0.5085 0.9594 0.4083 0.095 Uiso 1 1 calc R . . C16 C 0.6329(2) 0.7053(2) 0.38750(15) 0.0345(6) Uani 1 1 d . . . C17 C 0.8031(2) 0.5810(2) 0.37367(16) 0.0343(6) Uani 1 1 d . . . H17 H 0.796 0.5659 0.4319 0.041 Uiso 1 1 calc R . . C18 C 0.9398(2) 0.5899(2) 0.35004(17) 0.0399(6) Uani 1 1 d . . . H18A H 0.9461 0.6046 0.2929 0.06 Uiso 1 1 calc R . . H18B H 0.9817 0.521 0.3624 0.06 Uiso 1 1 calc R . . H18C H 0.9783 0.6497 0.3797 0.06 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0369(10) 0.0421(11) 0.0397(10) -0.0022(8) -0.0050(9) 0.0068(9) O2 0.0385(10) 0.0322(9) 0.0332(9) 0.0015(8) -0.0021(8) 0.0021(9) O3 0.0587(12) 0.0496(12) 0.0429(10) -0.0090(10) -0.0029(10) -0.0207(11) O4 0.0337(9) 0.0310(9) 0.0300(9) -0.0016(7) -0.0020(8) -0.0043(8) O5 0.0280(10) 0.0489(12) 0.0552(12) 0.0077(10) -0.0006(9) 0.0025(9) O6 0.0310(9) 0.0316(9) 0.0306(8) 0.0025(8) 0.0041(8) 0.0037(8) O7 0.0460(10) 0.0463(11) 0.0269(9) 0.0022(8) 0.0002(8) 0.0091(9) O8 0.0429(10) 0.0364(10) 0.0333(9) 0.0048(8) 0.0053(8) 0.0112(9) O9 0.0365(10) 0.0430(11) 0.0323(9) -0.0038(9) -0.0020(8) 0.0027(9) O10 0.0372(10) 0.0391(10) 0.0331(9) -0.0076(8) 0.0019(8) 0.0046(9) O11 0.0410(10) 0.0653(13) 0.0345(10) 0.0037(10) 0.0083(9) -0.0052(11) O12 0.0326(9) 0.0360(9) 0.0332(9) -0.0031(7) 0.0061(8) 0.0024(8) C1 0.0330(14) 0.0366(15) 0.0275(12) 0.0037(11) 0.0040(12) 0.0037(12) C2 0.0319(12) 0.0332(14) 0.0383(14) 0.0025(11) -0.0016(11) -0.0029(12) C3 0.0486(16) 0.0361(15) 0.0435(15) 0.0060(13) -0.0031(13) 0.0031(14) C4 0.0324(12) 0.0291(13) 0.0390(14) 0.0008(12) -0.0057(12) -0.0012(12) C5 0.0343(13) 0.0301(13) 0.0289(12) -0.0033(11) 0.0006(11) 0.0002(11) C6 0.0323(14) 0.0364(15) 0.0510(16) 0.0038(13) 0.0012(13) 0.0063(12) C7 0.0301(14) 0.0365(14) 0.0253(12) -0.0024(11) 0.0000(10) -0.0019(12) C8 0.0367(13) 0.0343(13) 0.0271(12) 0.0028(11) 0.0006(11) 0.0080(12) C9 0.0528(17) 0.0466(18) 0.0354(14) 0.0096(13) 0.0143(13) 0.0063(15) C10 0.0297(13) 0.0299(13) 0.0343(13) 0.0045(11) 0.0049(11) 0.0013(12) C11 0.0378(14) 0.0367(15) 0.0367(14) -0.0033(12) 0.0024(12) 0.0043(13) C12 0.0518(17) 0.0382(16) 0.0526(17) -0.0007(14) 0.0005(15) 0.0077(15) C13 0.0309(12) 0.0333(14) 0.0322(13) -0.0048(11) -0.0033(11) 0.0098(13) C14 0.0314(13) 0.0542(17) 0.0299(13) -0.0068(13) 0.0049(11) 0.0028(14) C15 0.067(2) 0.074(2) 0.0487(17) -0.0205(18) 0.0097(17) 0.020(2) C16 0.0336(13) 0.0474(15) 0.0224(11) -0.0083(12) 0.0038(11) -0.0045(13) C17 0.0380(14) 0.0350(14) 0.0299(13) 0.0024(11) 0.0015(11) -0.0006(12) C18 0.0353(14) 0.0432(16) 0.0412(14) 0.0028(13) -0.0010(12) 0.0014(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.194(3) . ? O2 C1 1.350(3) . ? O2 C2 1.444(3) . ? O3 C4 1.202(3) . ? O4 C4 1.333(3) . ? O4 C5 1.457(3) . ? O5 C7 1.198(3) . ? O6 C7 1.343(3) . ? O6 C8 1.444(3) . ? O7 C10 1.198(3) . ? O8 C10 1.332(3) . ? O8 C11 1.450(3) . ? O9 C13 1.201(3) . ? O10 C13 1.341(3) . ? O10 C14 1.441(3) . ? O11 C16 1.203(3) . ? O12 C16 1.335(3) . ? O12 C17 1.438(3) . ? C1 C17 1.519(4) . ? C2 C3 1.511(4) . ? C2 C4 1.518(4) . ? C2 H2 0.98 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C5 C6 1.513(4) . ? C5 C7 1.517(4) . ? C5 H5 0.98 . ? C6 H6A 0.96 . ? C6 H6B 0.96 . ? C6 H6C 0.96 . ? C8 C9 1.513(4) . ? C8 C10 1.519(4) . ? C8 H8 0.98 . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C11 C12 1.508(4) . ? C11 C13 1.525(4) . ? C11 H11 0.98 . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C14 C16 1.517(4) . ? C14 C15 1.521(4) . ? C14 H14 0.98 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C17 C18 1.512(4) . ? C17 H17 0.98 . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C2 114.24(19) . . ? C4 O4 C5 117.17(19) . . ? C7 O6 C8 114.85(19) . . ? C10 O8 C11 114.60(19) . . ? C13 O10 C14 115.8(2) . . ? C16 O12 C17 116.4(2) . . ? O1 C1 O2 124.1(3) . . ? O1 C1 C17 126.2(2) . . ? O2 C1 C17 109.6(2) . . ? O2 C2 C3 107.3(2) . . ? O2 C2 C4 111.7(2) . . ? C3 C2 C4 110.2(2) . . ? O2 C2 H2 109.2 . . ? C3 C2 H2 109.2 . . ? C4 C2 H2 109.2 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O3 C4 O4 125.4(2) . . ? O3 C4 C2 121.3(2) . . ? O4 C4 C2 113.3(2) . . ? O4 C5 C6 107.5(2) . . ? O4 C5 C7 105.7(2) . . ? C6 C5 C7 116.2(2) . . ? O4 C5 H5 109.1 . . ? C6 C5 H5 109.1 . . ? C7 C5 H5 109.1 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O5 C7 O6 123.9(2) . . ? O5 C7 C5 123.2(2) . . ? O6 C7 C5 112.9(2) . . ? O6 C8 C9 107.6(2) . . ? O6 C8 C10 107.97(19) . . ? C9 C8 C10 110.1(2) . . ? O6 C8 H8 110.4 . . ? C9 C8 H8 110.4 . . ? C10 C8 H8 110.4 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O7 C10 O8 124.1(2) . . ? O7 C10 C8 125.7(2) . . ? O8 C10 C8 110.1(2) . . ? O8 C11 C12 106.7(2) . . ? O8 C11 C13 108.8(2) . . ? C12 C11 C13 110.3(2) . . ? O8 C11 H11 110.3 . . ? C12 C11 H11 110.3 . . ? C13 C11 H11 110.3 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O9 C13 O10 124.9(2) . . ? O9 C13 C11 125.9(2) . . ? O10 C13 C11 109.0(2) . . ? O10 C14 C16 112.1(2) . . ? O10 C14 C15 106.9(2) . . ? C16 C14 C15 111.7(2) . . ? O10 C14 H14 108.7 . . ? C16 C14 H14 108.7 . . ? C15 C14 H14 108.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O11 C16 O12 124.3(3) . . ? O11 C16 C14 121.8(2) . . ? O12 C16 C14 113.9(2) . . ? O12 C17 C18 107.1(2) . . ? O12 C17 C1 107.9(2) . . ? C18 C17 C1 112.1(2) . . ? O12 C17 H17 109.9 . . ? C18 C17 H17 109.9 . . ? C1 C17 H17 109.9 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 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 C2 O2 C1 O1 8.4(3) . . . . ? C2 O2 C1 C17 -170.3(2) . . . . ? C1 O2 C2 C3 -171.6(2) . . . . ? C1 O2 C2 C4 67.6(3) . . . . ? C5 O4 C4 O3 1.0(4) . . . . ? C5 O4 C4 C2 179.2(2) . . . . ? O2 C2 C4 O3 -168.5(2) . . . . ? C3 C2 C4 O3 72.4(3) . . . . ? O2 C2 C4 O4 13.3(3) . . . . ? C3 C2 C4 O4 -105.9(2) . . . . ? C4 O4 C5 C6 -135.8(2) . . . . ? C4 O4 C5 C7 99.6(2) . . . . ? C8 O6 C7 O5 6.6(3) . . . . ? C8 O6 C7 C5 -173.56(19) . . . . ? O4 C5 C7 O5 -53.6(3) . . . . ? C6 C5 C7 O5 -172.7(3) . . . . ? O4 C5 C7 O6 126.6(2) . . . . ? C6 C5 C7 O6 7.5(3) . . . . ? C7 O6 C8 C9 -169.9(2) . . . . ? C7 O6 C8 C10 71.3(3) . . . . ? C11 O8 C10 O7 1.2(4) . . . . ? C11 O8 C10 C8 -175.2(2) . . . . ? O6 C8 C10 O7 17.9(4) . . . . ? C9 C8 C10 O7 -99.3(3) . . . . ? O6 C8 C10 O8 -165.73(18) . . . . ? C9 C8 C10 O8 77.1(3) . . . . ? C10 O8 C11 C12 174.0(2) . . . . ? C10 O8 C11 C13 -67.1(3) . . . . ? C14 O10 C13 O9 0.1(4) . . . . ? C14 O10 C13 C11 176.8(2) . . . . ? O8 C11 C13 O9 -30.7(3) . . . . ? C12 C11 C13 O9 86.0(3) . . . . ? O8 C11 C13 O10 152.7(2) . . . . ? C12 C11 C13 O10 -90.6(3) . . . . ? C13 O10 C14 C16 82.4(3) . . . . ? C13 O10 C14 C15 -154.9(2) . . . . ? C17 O12 C16 O11 6.4(3) . . . . ? C17 O12 C16 C14 -174.09(19) . . . . ? O10 C14 C16 O11 -178.6(2) . . . . ? C15 C14 C16 O11 61.5(3) . . . . ? O10 C14 C16 O12 1.9(3) . . . . ? C15 C14 C16 O12 -118.0(3) . . . . ? C16 O12 C17 C18 -165.4(2) . . . . ? C16 O12 C17 C1 73.7(3) . . . . ? O1 C1 C17 O12 0.9(3) . . . . ? O2 C1 C17 O12 179.48(19) . . . . ? O1 C1 C17 C18 -116.9(3) . . . . ? O2 C1 C17 C18 61.8(3) . . . . ? #===END # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-09-05 at 11:36:50 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : shelxl dreduc import struct data_Chisholm1497 _database_code_depnum_ccdc_archive 'CCDC 651116' _audit_creation_date 2006-09-05T11:36:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Chisholm 1497' _chemical_formula_moiety 'C18 H24 Na1 O12, C24 H20 B, C2 H3 N1' _chemical_formula_sum 'C44 H47 B1 N1 Na1 O12' _chemical_formula_weight 815.62 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.986(2) _cell_length_b 19.900(3) _cell_length_c 21.545(4) _cell_angle_alpha 90 _cell_angle_beta 90.376(6) _cell_angle_gamma 90 _cell_volume 4281.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7744 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 2.8. Phi and omega scans with a frame width of 1 degree were used for data collection. Data integration was done with Denzo, and scaling and merging of the data was done with Scalepack. The asymmetric unit contains two half molecules of the cyclic C18 H24 O12 compound. Each half molecule is situated about an inversion center, which generates the other half of each molecule. These half molecules are labeled as A and B. A Na+ ion is bonded to three oxygen atoms of the A molecule and three oxygen atoms of the B molecule, with the result that an infinite chain of ring-Na-ring-Na... is formed. The asymmetric unit also contains a [B(Phenyl)4]- ion and a molecule of CH3CN. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.95631E-2 _diffrn_orient_matrix_ub_12 0.197614E-1 _diffrn_orient_matrix_ub_13 -0.424732E-1 _diffrn_orient_matrix_ub_21 0.884503E-1 _diffrn_orient_matrix_ub_22 -0.196116E-1 _diffrn_orient_matrix_ub_23 -0.118016E-1 _diffrn_orient_matrix_ub_31 -0.459825E-1 _diffrn_orient_matrix_ub_32 -0.41834E-1 _diffrn_orient_matrix_ub_33 -0.145308E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 41693 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 7541 _reflns_number_gt 4755 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;The methyl group hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle, which defines the orientation of the methyl group about the C-C bond, was refined. The other hydrogen atoms were added to the model at calculated positions using a riding model with U(H) = 1.2 * Ueq(attached atom). 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 'w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+0.0970P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7541 _refine_ls_number_parameters 539 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.081 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.188 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Na Na 0.74884(5) -0.00257(3) -0.00458(3) 0.02251(18) Uani 1 1 d . . . O1A O 1.11322(11) -0.01633(6) 0.09032(6) 0.0286(3) Uani 1 1 d . . . O2A O 0.95403(11) -0.05912(6) 0.15168(5) 0.0246(3) Uani 1 1 d . . . O3A O 0.87361(11) -0.09561(6) 0.03254(5) 0.0261(3) Uani 1 1 d . . . O4A O 1.04088(10) -0.17102(6) 0.03128(5) 0.0237(3) Uani 1 1 d . . . O5A O 1.11991(11) -0.07222(6) -0.05143(5) 0.0261(3) Uani 1 1 d . . . O6A O 0.97354(11) -0.11258(6) -0.12124(5) 0.0262(3) Uani 1 1 d . . . C1A C 1.02804(17) -0.00843(10) 0.12893(8) 0.0230(5) Uani 1 1 d . . . C2A C 0.98807(17) -0.12484(9) 0.12810(8) 0.0248(5) Uani 1 1 d . . . H2A H 1.0852 -0.1339 0.136 0.03 Uiso 1 1 calc R . . C3A C 0.90432(19) -0.17570(10) 0.16253(8) 0.0363(5) Uani 1 1 d . . . H3A1 H 0.9216 -0.1717 0.2072 0.055 Uiso 1 1 calc R . . H3A2 H 0.9278 -0.2211 0.1487 0.055 Uiso 1 1 calc R . . H3A3 H 0.8092 -0.1673 0.154 0.055 Uiso 1 1 calc R . . C4A C 0.96014(17) -0.12696(9) 0.05918(8) 0.0219(5) Uani 1 1 d . . . C5A C 1.01811(16) -0.18053(9) -0.03450(8) 0.0224(5) Uani 1 1 d . . . H5A H 0.9242 -0.1961 -0.0423 0.027 Uiso 1 1 calc R . . C6A C 1.11680(18) -0.23375(10) -0.05532(9) 0.0330(5) Uani 1 1 d . . . H6A1 H 1.2083 -0.2184 -0.0468 0.049 Uiso 1 1 calc R . . H6A2 H 1.1058 -0.2417 -0.1 0.049 Uiso 1 1 calc R . . H6A3 H 1.1001 -0.2756 -0.0327 0.049 Uiso 1 1 calc R . . C7A C 1.04313(16) -0.11530(10) -0.06784(8) 0.0213(4) Uani 1 1 d . . . C8A C 1.00556(17) -0.05608(9) -0.16134(8) 0.0258(5) Uani 1 1 d . . . H8A H 1.1027 -0.0569 -0.1724 0.031 Uiso 1 1 calc R . . C9A C 0.9199(2) -0.06368(11) -0.21932(9) 0.0425(6) Uani 1 1 d . . . H9A1 H 0.9392 -0.107 -0.239 0.064 Uiso 1 1 calc R . . H9A2 H 0.9401 -0.0272 -0.2483 0.064 Uiso 1 1 calc R . . H9A3 H 0.825 -0.0618 -0.2081 0.064 Uiso 1 1 calc R . . O1B O 0.61463(11) 0.07778(6) -0.05604(5) 0.0266(3) Uani 1 1 d . . . O2B O 0.45356(11) 0.11525(6) -0.12071(5) 0.0239(3) Uani 1 1 d . . . O3B O 0.37398(11) -0.01120(6) -0.08661(6) 0.0266(3) Uani 1 1 d . . . O4B O 0.51118(11) -0.05693(6) -0.15698(5) 0.0258(3) Uani 1 1 d . . . O5B O 0.61591(11) -0.08924(6) -0.04255(5) 0.0275(3) Uani 1 1 d . . . O6B O 0.46167(11) -0.17047(6) -0.03214(5) 0.0239(3) Uani 1 1 d . . . C1B C 0.52837(17) 0.11785(10) -0.06886(8) 0.0219(4) Uani 1 1 d . . . C2B C 0.48177(16) 0.05980(9) -0.16212(8) 0.0219(4) Uani 1 1 d . . . H2B H 0.5785 0.0603 -0.1739 0.026 Uiso 1 1 calc R . . C3B C 0.39484(17) 0.06947(10) -0.21937(8) 0.0304(5) Uani 1 1 d . . . H3B1 H 0.3005 0.0711 -0.2072 0.046 Uiso 1 1 calc R . . H3B2 H 0.4087 0.0319 -0.248 0.046 Uiso 1 1 calc R . . H3B3 H 0.4192 0.1117 -0.2399 0.046 Uiso 1 1 calc R . . C4B C 0.44880(17) -0.00518(10) -0.12977(8) 0.0224(5) Uani 1 1 d . . . C5B C 0.48183(18) -0.12245(9) -0.13104(8) 0.0261(5) Uani 1 1 d . . . H5B H 0.3833 -0.1313 -0.1334 0.031 Uiso 1 1 calc R . . C6B C 0.5563(2) -0.17398(10) -0.16900(9) 0.0449(6) Uani 1 1 d . . . H6B1 H 0.524 -0.1726 -0.212 0.067 Uiso 1 1 calc R . . H6B2 H 0.5408 -0.2188 -0.1517 0.067 Uiso 1 1 calc R . . H6B3 H 0.6523 -0.1639 -0.1679 0.067 Uiso 1 1 calc R . . C7B C 0.52799(17) -0.12344(9) -0.06443(8) 0.0213(4) Uani 1 1 d . . . C8B C 0.50674(17) -0.17957(9) 0.03119(8) 0.0234(5) Uani 1 1 d . . . H8B H 0.6058 -0.1868 0.0321 0.028 Uiso 1 1 calc R . . C9B C 0.4362(2) -0.24132(10) 0.05588(9) 0.0386(6) Uani 1 1 d . . . H9B1 H 0.3399 -0.2325 0.0585 0.058 Uiso 1 1 calc R . . H9B2 H 0.4713 -0.2521 0.0973 0.058 Uiso 1 1 calc R . . H9B3 H 0.4518 -0.2793 0.0279 0.058 Uiso 1 1 calc R . . C1C C 0.23136(16) 0.35245(9) 0.17108(8) 0.0221(5) Uani 1 1 d . . . C2C C 0.25823(16) 0.36233(10) 0.23449(8) 0.0272(5) Uani 1 1 d . . . H2C H 0.3147 0.3986 0.2462 0.033 Uiso 1 1 calc R . . C3C C 0.20648(16) 0.32176(10) 0.28079(9) 0.0290(5) Uani 1 1 d . . . H3C H 0.2291 0.3303 0.323 0.035 Uiso 1 1 calc R . . C4C C 0.12257(19) 0.26911(10) 0.26613(9) 0.0329(5) Uani 1 1 d . . . H4C H 0.0874 0.2409 0.2977 0.039 Uiso 1 1 calc R . . C5C C 0.0910(2) 0.25833(10) 0.20458(9) 0.0414(6) Uani 1 1 d . . . H5C H 0.0316 0.223 0.1934 0.05 Uiso 1 1 calc R . . C6C C 0.14534(19) 0.29883(10) 0.15896(9) 0.0331(5) Uani 1 1 d . . . H6C H 0.1227 0.2895 0.1169 0.04 Uiso 1 1 calc R . . C7C C 0.21925(16) 0.38172(9) 0.05018(8) 0.0226(5) Uani 1 1 d . . . C8C C 0.26073(16) 0.32607(10) 0.01510(8) 0.0276(5) Uani 1 1 d . . . H8C H 0.337 0.3015 0.0287 0.033 Uiso 1 1 calc R . . C9C C 0.19525(17) 0.30555(10) -0.03848(9) 0.0304(5) Uani 1 1 d . . . H9C H 0.2269 0.2677 -0.0608 0.037 Uiso 1 1 calc R . . C10C C 0.08394(17) 0.34016(10) -0.05943(9) 0.0304(5) Uani 1 1 d . . . H10C H 0.0382 0.3261 -0.096 0.036 Uiso 1 1 calc R . . C11C C 0.04016(18) 0.39525(10) -0.02669(9) 0.0288(5) Uani 1 1 d . . . H11C H -0.036 0.4196 -0.0408 0.035 Uiso 1 1 calc R . . C12C C 0.10699(16) 0.41531(9) 0.02689(8) 0.0254(5) Uani 1 1 d . . . H12C H 0.0749 0.4535 0.0486 0.03 Uiso 1 1 calc R . . C13C C 0.45650(16) 0.39070(9) 0.10939(8) 0.0234(5) Uani 1 1 d . . . C14C C 0.53857(17) 0.36216(10) 0.15525(8) 0.0287(5) Uani 1 1 d . . . H14C H 0.4976 0.3448 0.1916 0.034 Uiso 1 1 calc R . . C15C C 0.67701(18) 0.35791(10) 0.15024(9) 0.0351(5) Uani 1 1 d . . . H15C H 0.7283 0.3382 0.1827 0.042 Uiso 1 1 calc R . . C16C C 0.73985(18) 0.38236(10) 0.09806(10) 0.0355(5) Uani 1 1 d . . . H16C H 0.8346 0.3804 0.0946 0.043 Uiso 1 1 calc R . . C17C C 0.66321(18) 0.40973(10) 0.05098(9) 0.0343(5) Uani 1 1 d . . . H17C H 0.7051 0.4264 0.0146 0.041 Uiso 1 1 calc R . . C18C C 0.52554(17) 0.41298(10) 0.05662(8) 0.0293(5) Uani 1 1 d . . . H18C H 0.475 0.4312 0.0231 0.035 Uiso 1 1 calc R . . C19C C 0.26087(16) 0.47994(10) 0.13368(8) 0.0219(5) Uani 1 1 d . . . C20C C 0.14639(17) 0.49819(10) 0.16723(8) 0.0282(5) Uani 1 1 d . . . H20C H 0.0875 0.4636 0.1805 0.034 Uiso 1 1 calc R . . C21C C 0.11494(18) 0.56391(11) 0.18201(9) 0.0317(5) Uani 1 1 d . . . H21C H 0.0365 0.5734 0.2051 0.038 Uiso 1 1 calc R . . C22C C 0.19729(19) 0.61583(10) 0.16331(9) 0.0322(5) Uani 1 1 d . . . H22C H 0.1771 0.6611 0.1737 0.039 Uiso 1 1 calc R . . C23C C 0.30935(19) 0.60018(10) 0.12928(9) 0.0347(5) Uani 1 1 d . . . H23C H 0.3662 0.6352 0.1152 0.042 Uiso 1 1 calc R . . C24C C 0.34025(18) 0.53393(10) 0.11529(8) 0.0284(5) Uani 1 1 d . . . H24C H 0.4189 0.525 0.0922 0.034 Uiso 1 1 calc R . . B B 0.29322(19) 0.40098(11) 0.11636(9) 0.0232(5) Uani 1 1 d . . . N1D N 1.2553(2) -0.11831(13) -0.25335(11) 0.0796(8) Uani 1 1 d . . . C1D C 1.2092(2) -0.05211(13) -0.35418(11) 0.0630(7) Uani 1 1 d . . . H1D1 H 1.1474 -0.0152 -0.3452 0.094 Uiso 1 1 calc R . . H1D2 H 1.1693 -0.0817 -0.3856 0.094 Uiso 1 1 calc R . . H1D3 H 1.2937 -0.0338 -0.3698 0.094 Uiso 1 1 calc R . . C2D C 1.2347(2) -0.08990(14) -0.29805(13) 0.0513(7) 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 Na 0.0161(3) 0.0244(4) 0.0270(4) -0.0016(4) -0.0009(3) -0.0005(3) O1A 0.0213(7) 0.0343(9) 0.0302(8) -0.0033(7) 0.0040(6) 0.0007(6) O2A 0.0256(7) 0.0226(8) 0.0256(8) -0.0032(6) 0.0018(5) -0.0005(6) O3A 0.0212(7) 0.0296(9) 0.0275(8) 0.0001(7) -0.0041(6) 0.0056(6) O4A 0.0240(6) 0.0243(8) 0.0228(8) -0.0031(6) -0.0010(5) 0.0051(6) O5A 0.0216(7) 0.0279(9) 0.0287(8) -0.0038(7) -0.0029(5) -0.0068(6) O6A 0.0304(7) 0.0251(8) 0.0230(7) -0.0023(6) -0.0072(6) -0.0044(6) C1A 0.0194(10) 0.0282(13) 0.0214(11) -0.0017(10) -0.0064(9) -0.0024(9) C2A 0.0288(10) 0.0214(13) 0.0240(11) -0.0024(10) -0.0041(8) 0.0051(9) C3A 0.0591(13) 0.0259(13) 0.0241(12) 0.0004(10) -0.0012(10) -0.0029(11) C4A 0.0167(10) 0.0217(12) 0.0272(12) 0.0004(10) 0.0005(9) -0.0036(9) C5A 0.0218(10) 0.0234(13) 0.0219(11) -0.0057(9) -0.0025(8) -0.0021(9) C6A 0.0377(11) 0.0287(13) 0.0326(13) -0.0054(10) 0.0039(9) 0.0056(10) C7A 0.0158(9) 0.0252(13) 0.0230(11) -0.0056(10) 0.0009(8) 0.0022(9) C8A 0.0327(11) 0.0247(13) 0.0200(11) -0.0017(10) -0.0013(8) -0.0014(9) C9A 0.0654(14) 0.0349(14) 0.0268(12) -0.0052(11) -0.0162(10) -0.0022(12) O1B 0.0232(7) 0.0280(9) 0.0284(8) 0.0017(7) -0.0027(6) 0.0047(6) O2B 0.0284(7) 0.0223(8) 0.0210(7) -0.0009(6) -0.0037(6) 0.0032(6) O3B 0.0232(7) 0.0302(9) 0.0264(8) 0.0014(7) 0.0050(6) -0.0025(6) O4B 0.0349(7) 0.0204(8) 0.0221(7) 0.0006(7) 0.0057(6) 0.0007(6) O5B 0.0219(7) 0.0262(8) 0.0344(8) -0.0006(7) -0.0035(6) -0.0067(6) O6B 0.0274(7) 0.0227(8) 0.0216(7) 0.0035(6) 0.0000(6) -0.0056(6) C1B 0.0211(10) 0.0224(12) 0.0222(11) 0.0042(10) 0.0021(8) -0.0047(9) C2B 0.0251(10) 0.0207(12) 0.0199(11) -0.0012(9) 0.0018(8) 0.0028(9) C3B 0.0355(11) 0.0315(13) 0.0241(11) 0.0006(10) -0.0038(9) 0.0014(9) C4B 0.0200(10) 0.0257(13) 0.0215(11) -0.0012(10) -0.0043(9) -0.0003(9) C5B 0.0378(11) 0.0178(12) 0.0226(11) 0.0025(9) -0.0005(9) -0.0052(9) C6B 0.0813(16) 0.0238(14) 0.0297(13) -0.0021(11) 0.0092(11) 0.0066(12) C7B 0.0188(10) 0.0197(12) 0.0255(11) 0.0010(10) 0.0025(8) 0.0034(9) C8B 0.0288(10) 0.0221(13) 0.0193(11) 0.0023(9) -0.0017(8) 0.0018(9) C9B 0.0630(14) 0.0236(13) 0.0292(13) 0.0027(10) 0.0063(10) -0.0062(11) C1C 0.0200(9) 0.0220(12) 0.0242(11) -0.0042(9) -0.0020(8) 0.0032(9) C2C 0.0243(10) 0.0310(13) 0.0262(12) -0.0017(10) -0.0020(9) -0.0053(9) C3C 0.0272(10) 0.0373(14) 0.0226(12) -0.0006(10) -0.0015(8) -0.0001(10) C4C 0.0473(12) 0.0253(13) 0.0261(13) 0.0046(10) 0.0066(10) -0.0022(10) C5C 0.0677(15) 0.0280(14) 0.0286(13) -0.0023(11) 0.0022(11) -0.0202(11) C6C 0.0507(13) 0.0282(13) 0.0203(11) -0.0025(10) -0.0020(9) -0.0093(11) C7C 0.0239(10) 0.0224(12) 0.0214(11) 0.0022(9) 0.0029(8) -0.0034(9) C8C 0.0285(10) 0.0289(13) 0.0253(12) -0.0032(10) -0.0041(9) 0.0056(9) C9C 0.0371(11) 0.0264(13) 0.0277(12) -0.0074(10) -0.0053(9) 0.0064(10) C10C 0.0382(12) 0.0285(14) 0.0244(12) -0.0029(10) -0.0103(9) 0.0008(10) C11C 0.0284(10) 0.0263(13) 0.0317(12) 0.0014(10) -0.0061(9) 0.0053(9) C12C 0.0283(10) 0.0233(12) 0.0246(11) -0.0040(10) -0.0001(8) 0.0017(9) C13C 0.0275(10) 0.0216(12) 0.0210(11) -0.0042(9) 0.0005(8) -0.0015(9) C14C 0.0274(11) 0.0334(13) 0.0254(12) -0.0008(10) 0.0012(9) -0.0015(9) C15C 0.0297(12) 0.0384(14) 0.0372(13) -0.0018(11) -0.0057(10) 0.0044(10) C16C 0.0228(11) 0.0377(14) 0.0462(14) -0.0113(12) 0.0048(10) 0.0012(10) C17C 0.0323(12) 0.0399(15) 0.0308(13) -0.0043(11) 0.0091(10) -0.0025(10) C18C 0.0295(11) 0.0335(13) 0.0249(12) -0.0018(10) 0.0003(9) 0.0003(9) C19C 0.0241(10) 0.0254(12) 0.0160(10) -0.0013(9) -0.0031(8) -0.0025(9) C20C 0.0307(11) 0.0237(13) 0.0301(12) -0.0016(10) 0.0011(9) -0.0028(9) C21C 0.0316(11) 0.0318(14) 0.0318(13) -0.0069(11) -0.0022(9) 0.0034(10) C22C 0.0424(12) 0.0216(13) 0.0323(13) -0.0046(10) -0.0103(10) 0.0049(10) C23C 0.0449(12) 0.0241(14) 0.0351(13) 0.0045(11) -0.0033(10) -0.0092(10) C24C 0.0313(11) 0.0296(14) 0.0242(12) 0.0006(10) 0.0026(9) -0.0019(10) B 0.0248(11) 0.0237(14) 0.0210(13) 0.0010(11) -0.0002(9) -0.0022(10) N1D 0.0663(14) 0.105(2) 0.0674(17) 0.0165(16) 0.0061(13) 0.0215(14) C1D 0.0633(16) 0.064(2) 0.0618(18) 0.0107(15) 0.0010(13) 0.0201(14) C2D 0.0380(13) 0.0585(19) 0.0573(18) 0.0006(15) 0.0039(13) 0.0079(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Na O5A 2.3169(14) 3_755 ? Na O5B 2.3221(14) . ? Na O3B 2.3389(14) 3_655 ? Na O1A 2.3419(14) 3_755 ? Na O1B 2.3585(14) . ? Na O3A 2.3679(14) . ? O1A C1A 1.204(2) . ? O1A Na 2.3419(14) 3_755 ? O2A C1A 1.345(2) . ? O2A C2A 1.444(2) . ? O3A C4A 1.2078(19) . ? O4A C4A 1.337(2) . ? O4A C5A 1.4463(19) . ? O5A C7A 1.202(2) . ? O5A Na 2.3169(14) 3_755 ? O6A C7A 1.341(2) . ? O6A C8A 1.455(2) . ? C1A C8A 1.500(2) 3_755 ? C2A C4A 1.510(2) . ? C2A C3A 1.511(2) . ? C2A H2A 1 . ? C3A H3A1 0.98 . ? C3A H3A2 0.98 . ? C3A H3A3 0.98 . ? C5A C7A 1.505(2) . ? C5A C6A 1.517(2) . ? C5A H5A 1 . ? C6A H6A1 0.98 . ? C6A H6A2 0.98 . ? C6A H6A3 0.98 . ? C8A C1A 1.500(2) 3_755 ? C8A C9A 1.517(2) . ? C8A H8A 1 . ? C9A H9A1 0.98 . ? C9A H9A2 0.98 . ? C9A H9A3 0.98 . ? O1B C1B 1.205(2) . ? O2B C1B 1.341(2) . ? O2B C2B 1.448(2) . ? O3B C4B 1.2026(19) . ? O3B Na 2.3389(14) 3_655 ? O4B C4B 1.341(2) . ? O4B C5B 1.449(2) . ? O5B C7B 1.204(2) . ? O6B C7B 1.343(2) . ? O6B C8B 1.4454(19) . ? C1B C8B 1.515(2) 3_655 ? C2B C4B 1.506(2) . ? C2B C3B 1.516(2) . ? C2B H2B 1 . ? C3B H3B1 0.98 . ? C3B H3B2 0.98 . ? C3B H3B3 0.98 . ? C5B C7B 1.505(2) . ? C5B C6B 1.510(2) . ? C5B H5B 1 . ? C6B H6B1 0.98 . ? C6B H6B2 0.98 . ? C6B H6B3 0.98 . ? C8B C1B 1.515(2) 3_655 ? C8B C9B 1.515(2) . ? C8B H8B 1 . ? C9B H9B1 0.98 . ? C9B H9B2 0.98 . ? C9B H9B3 0.98 . ? C1C C6C 1.393(2) . ? C1C C2C 1.404(2) . ? C1C B 1.647(3) . ? C2C C3C 1.386(2) . ? C2C H2C 0.95 . ? C3C C4C 1.377(3) . ? C3C H3C 0.95 . ? C4C C5C 1.378(2) . ? C4C H4C 0.95 . ? C5C C6C 1.385(3) . ? C5C H5C 0.95 . ? C6C H6C 0.95 . ? C7C C12C 1.396(2) . ? C7C C8C 1.405(2) . ? C7C B 1.647(3) . ? C8C C9C 1.385(2) . ? C8C H8C 0.95 . ? C9C C10C 1.381(2) . ? C9C H9C 0.95 . ? C10C C11C 1.376(2) . ? C10C H10C 0.95 . ? C11C C12C 1.388(2) . ? C11C H11C 0.95 . ? C12C H12C 0.95 . ? C13C C14C 1.400(2) . ? C13C C18C 1.405(2) . ? C13C B 1.651(3) . ? C14C C15C 1.390(2) . ? C14C H14C 0.95 . ? C15C C16C 1.380(3) . ? C15C H15C 0.95 . ? C16C C17C 1.379(2) . ? C16C H16C 0.95 . ? C17C C18C 1.382(2) . ? C17C H17C 0.95 . ? C18C H18C 0.95 . ? C19C C24C 1.394(2) . ? C19C C20C 1.404(2) . ? C19C B 1.648(3) . ? C20C C21C 1.383(2) . ? C20C H20C 0.95 . ? C21C C22C 1.382(3) . ? C21C H21C 0.95 . ? C22C C23C 1.378(3) . ? C22C H22C 0.95 . ? C23C C24C 1.387(3) . ? C23C H23C 0.95 . ? C24C H24C 0.95 . ? N1D C2D 1.134(3) . ? C1D C2D 1.445(3) . ? C1D H1D1 0.98 . ? C1D H1D2 0.98 . ? C1D H1D3 0.98 . ? 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 O5A Na O5B 168.74(5) 3_755 . ? O5A Na O3B 77.60(5) 3_755 3_655 ? O5B Na O3B 94.66(5) . 3_655 ? O5A Na O1A 88.51(5) 3_755 3_755 ? O5B Na O1A 100.32(5) . 3_755 ? O3B Na O1A 163.36(5) 3_655 3_755 ? O5A Na O1B 97.30(5) 3_755 . ? O5B Na O1B 90.93(5) . . ? O3B Na O1B 90.92(5) 3_655 . ? O1A Na O1B 81.70(5) 3_755 . ? O5A Na O3A 91.82(5) 3_755 . ? O5B Na O3A 80.59(5) . . ? O3B Na O3A 94.91(5) 3_655 . ? O1A Na O3A 94.64(5) 3_755 . ? O1B Na O3A 170.05(5) . . ? C1A O1A Na 161.07(13) . 3_755 ? C1A O2A C2A 114.82(13) . . ? C4A O3A Na 159.65(12) . . ? C4A O4A C5A 115.79(13) . . ? C7A O5A Na 165.71(12) . 3_755 ? C7A O6A C8A 115.22(13) . . ? O1A C1A O2A 123.11(17) . . ? O1A C1A C8A 126.47(17) . 3_755 ? O2A C1A C8A 110.31(15) . 3_755 ? O2A C2A C4A 109.21(14) . . ? O2A C2A C3A 107.56(14) . . ? C4A C2A C3A 111.40(15) . . ? O2A C2A H2A 109.5 . . ? C4A C2A H2A 109.5 . . ? C3A C2A H2A 109.5 . . ? C2A C3A H3A1 109.5 . . ? C2A C3A H3A2 109.5 . . ? H3A1 C3A H3A2 109.5 . . ? C2A C3A H3A3 109.5 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 109.5 . . ? O3A C4A O4A 123.83(17) . . ? O3A C4A C2A 125.45(17) . . ? O4A C4A C2A 110.65(15) . . ? O4A C5A C7A 109.22(14) . . ? O4A C5A C6A 106.43(14) . . ? C7A C5A C6A 110.54(15) . . ? O4A C5A H5A 110.2 . . ? C7A C5A H5A 110.2 . . ? C6A C5A H5A 110.2 . . ? C5A C6A H6A1 109.5 . . ? C5A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 109.5 . . ? C5A C6A H6A3 109.5 . . ? H6A1 C6A H6A3 109.5 . . ? H6A2 C6A H6A3 109.5 . . ? O5A C7A O6A 123.32(17) . . ? O5A C7A C5A 125.63(16) . . ? O6A C7A C5A 110.95(15) . . ? O6A C8A C1A 109.52(14) . 3_755 ? O6A C8A C9A 106.68(14) . . ? C1A C8A C9A 110.00(15) 3_755 . ? O6A C8A H8A 110.2 . . ? C1A C8A H8A 110.2 3_755 . ? C9A C8A H8A 110.2 . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C1B O1B Na 163.71(12) . . ? C1B O2B C2B 115.66(13) . . ? C4B O3B Na 165.84(13) . 3_655 ? C4B O4B C5B 115.26(13) . . ? C7B O5B Na 166.19(12) . . ? C7B O6B C8B 115.13(13) . . ? O1B C1B O2B 124.01(17) . . ? O1B C1B C8B 125.56(16) . 3_655 ? O2B C1B C8B 110.37(15) . 3_655 ? O2B C2B C4B 108.97(14) . . ? O2B C2B C3B 106.97(14) . . ? C4B C2B C3B 111.09(14) . . ? O2B C2B H2B 109.9 . . ? C4B C2B H2B 109.9 . . ? C3B C2B H2B 109.9 . . ? C2B C3B H3B1 109.5 . . ? C2B C3B H3B2 109.5 . . ? H3B1 C3B H3B2 109.5 . . ? C2B C3B H3B3 109.5 . . ? H3B1 C3B H3B3 109.5 . . ? H3B2 C3B H3B3 109.5 . . ? O3B C4B O4B 123.67(17) . . ? O3B C4B C2B 125.60(17) . . ? O4B C4B C2B 110.69(15) . . ? O4B C5B C7B 108.55(14) . . ? O4B C5B C6B 107.49(14) . . ? C7B C5B C6B 111.03(16) . . ? O4B C5B H5B 109.9 . . ? C7B C5B H5B 109.9 . . ? C6B C5B H5B 109.9 . . ? C5B C6B H6B1 109.5 . . ? C5B C6B H6B2 109.5 . . ? H6B1 C6B H6B2 109.5 . . ? C5B C6B H6B3 109.5 . . ? H6B1 C6B H6B3 109.5 . . ? H6B2 C6B H6B3 109.5 . . ? O5B C7B O6B 123.48(16) . . ? O5B C7B C5B 125.72(17) . . ? O6B C7B C5B 110.74(16) . . ? O6B C8B C1B 109.42(14) . 3_655 ? O6B C8B C9B 106.89(14) . . ? C1B C8B C9B 111.10(15) 3_655 . ? O6B C8B H8B 109.8 . . ? C1B C8B H8B 109.8 3_655 . ? C9B C8B H8B 109.8 . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? C6C C1C C2C 113.77(17) . . ? C6C C1C B 123.26(16) . . ? C2C C1C B 122.95(16) . . ? C3C C2C C1C 123.30(18) . . ? C3C C2C H2C 118.4 . . ? C1C C2C H2C 118.4 . . ? C4C C3C C2C 120.49(18) . . ? C4C C3C H3C 119.8 . . ? C2C C3C H3C 119.8 . . ? C3C C4C C5C 118.32(18) . . ? C3C C4C H4C 120.8 . . ? C5C C4C H4C 120.8 . . ? C4C C5C C6C 120.28(19) . . ? C4C C5C H5C 119.9 . . ? C6C C5C H5C 119.9 . . ? C5C C6C C1C 123.83(18) . . ? C5C C6C H6C 118.1 . . ? C1C C6C H6C 118.1 . . ? C12C C7C C8C 115.04(16) . . ? C12C C7C B 123.67(16) . . ? C8C C7C B 121.14(16) . . ? C9C C8C C7C 122.80(17) . . ? C9C C8C H8C 118.6 . . ? C7C C8C H8C 118.6 . . ? C10C C9C C8C 120.00(18) . . ? C10C C9C H9C 120 . . ? C8C C9C H9C 120 . . ? C11C C10C C9C 119.18(17) . . ? C11C C10C H10C 120.4 . . ? C9C C10C H10C 120.4 . . ? C10C C11C C12C 120.17(17) . . ? C10C C11C H11C 119.9 . . ? C12C C11C H11C 119.9 . . ? C11C C12C C7C 122.80(18) . . ? C11C C12C H12C 118.6 . . ? C7C C12C H12C 118.6 . . ? C14C C13C C18C 114.26(16) . . ? C14C C13C B 124.06(16) . . ? C18C C13C B 121.63(16) . . ? C15C C14C C13C 123.23(17) . . ? C15C C14C H14C 118.4 . . ? C13C C14C H14C 118.4 . . ? C16C C15C C14C 119.98(18) . . ? C16C C15C H15C 120 . . ? C14C C15C H15C 120 . . ? C17C C16C C15C 119.04(17) . . ? C17C C16C H16C 120.5 . . ? C15C C16C H16C 120.5 . . ? C16C C17C C18C 120.09(18) . . ? C16C C17C H17C 120 . . ? C18C C17C H17C 120 . . ? C17C C18C C13C 123.35(18) . . ? C17C C18C H18C 118.3 . . ? C13C C18C H18C 118.3 . . ? C24C C19C C20C 114.41(17) . . ? C24C C19C B 123.92(15) . . ? C20C C19C B 121.64(16) . . ? C21C C20C C19C 123.37(18) . . ? C21C C20C H20C 118.3 . . ? C19C C20C H20C 118.3 . . ? C22C C21C C20C 120.22(18) . . ? C22C C21C H21C 119.9 . . ? C20C C21C H21C 119.9 . . ? C23C C22C C21C 118.24(19) . . ? C23C C22C H22C 120.9 . . ? C21C C22C H22C 120.9 . . ? C22C C23C C24C 120.86(19) . . ? C22C C23C H23C 119.6 . . ? C24C C23C H23C 119.6 . . ? C23C C24C C19C 122.88(18) . . ? C23C C24C H24C 118.6 . . ? C19C C24C H24C 118.6 . . ? C7C B C1C 108.37(14) . . ? C7C B C19C 109.30(15) . . ? C1C B C19C 108.79(14) . . ? C7C B C13C 109.27(14) . . ? C1C B C13C 111.57(15) . . ? C19C B C13C 109.51(15) . . ? C2D C1D H1D1 109.5 . . ? C2D C1D H1D2 109.5 . . ? H1D1 C1D H1D2 109.5 . . ? C2D C1D H1D3 109.5 . . ? H1D1 C1D H1D3 109.5 . . ? H1D2 C1D H1D3 109.5 . . ? N1D C2D C1D 178.5(3) . . ? 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 O5A Na O3A C4A -5.4(3) 3_755 . . . ? O5B Na O3A C4A -177.0(3) . . . . ? O3B Na O3A C4A -83.1(3) 3_655 . . . ? O1A Na O3A C4A 83.3(3) 3_755 . . . ? Na O1A C1A O2A 143.6(3) 3_755 . . . ? Na O1A C1A C8A -40.6(5) 3_755 . . 3_755 ? C2A O2A C1A O1A 2.4(2) . . . . ? C2A O2A C1A C8A -174.00(13) . . . 3_755 ? C1A O2A C2A C4A -63.89(18) . . . . ? C1A O2A C2A C3A 175.07(14) . . . . ? Na O3A C4A O4A -122.8(3) . . . . ? Na O3A C4A C2A 60.3(4) . . . . ? C5A O4A C4A O3A -0.8(2) . . . . ? C5A O4A C4A C2A 176.42(14) . . . . ? O2A C2A C4A O3A -30.8(2) . . . . ? C3A C2A C4A O3A 87.8(2) . . . . ? O2A C2A C4A O4A 151.99(13) . . . . ? C3A C2A C4A O4A -89.34(17) . . . . ? C4A O4A C5A C7A 62.55(17) . . . . ? C4A O4A C5A C6A -178.09(14) . . . . ? Na O5A C7A O6A 148.8(4) 3_755 . . . ? Na O5A C7A C5A -35.2(6) 3_755 . . . ? C8A O6A C7A O5A 5.1(2) . . . . ? C8A O6A C7A C5A -171.38(13) . . . . ? O4A C5A C7A O5A 29.3(2) . . . . ? C6A C5A C7A O5A -87.5(2) . . . . ? O4A C5A C7A O6A -154.33(13) . . . . ? C6A C5A C7A O6A 88.89(17) . . . . ? C7A O6A C8A C1A -62.72(18) . . . 3_755 ? C7A O6A C8A C9A 178.27(14) . . . . ? O5A Na O1B C1B -84.5(4) 3_755 . . . ? O5B Na O1B C1B 87.8(4) . . . . ? O3B Na O1B C1B -6.9(4) 3_655 . . . ? O1A Na O1B C1B -171.9(4) 3_755 . . . ? O5A Na O5B C7B 119.2(5) 3_755 . . . ? O3B Na O5B C7B 73.1(5) 3_655 . . . ? O1A Na O5B C7B -99.6(5) 3_755 . . . ? O1B Na O5B C7B -17.9(5) . . . . ? O3A Na O5B C7B 167.3(5) . . . . ? Na O1B C1B O2B -127.2(4) . . . . ? Na O1B C1B C8B 56.0(5) . . . 3_655 ? C2B O2B C1B O1B 0.3(2) . . . . ? C2B O2B C1B C8B 177.50(13) . . . 3_655 ? C1B O2B C2B C4B 64.20(17) . . . . ? C1B O2B C2B C3B -175.63(14) . . . . ? Na O3B C4B O4B 145.4(4) 3_655 . . . ? Na O3B C4B C2B -37.0(6) 3_655 . . . ? C5B O4B C4B O3B 0.4(2) . . . . ? C5B O4B C4B C2B -177.52(13) . . . . ? O2B C2B C4B O3B 21.8(2) . . . . ? C3B C2B C4B O3B -95.8(2) . . . . ? O2B C2B C4B O4B -160.32(13) . . . . ? C3B C2B C4B O4B 82.08(17) . . . . ? C4B O4B C5B C7B -61.99(18) . . . . ? C4B O4B C5B C6B 177.83(15) . . . . ? Na O5B C7B O6B -114.3(5) . . . . ? Na O5B C7B C5B 68.9(6) . . . . ? C8B O6B C7B O5B -2.4(2) . . . . ? C8B O6B C7B C5B 174.85(14) . . . . ? O4B C5B C7B O5B -26.0(2) . . . . ? C6B C5B C7B O5B 92.0(2) . . . . ? O4B C5B C7B O6B 156.89(13) . . . . ? C6B C5B C7B O6B -85.16(18) . . . . ? C7B O6B C8B C1B 68.56(17) . . . 3_655 ? C7B O6B C8B C9B -171.04(14) . . . . ? C6C C1C C2C C3C 1.3(3) . . . . ? B C1C C2C C3C 179.94(16) . . . . ? C1C C2C C3C C4C -0.9(3) . . . . ? C2C C3C C4C C5C -0.5(3) . . . . ? C3C C4C C5C C6C 1.5(3) . . . . ? C4C C5C C6C C1C -1.1(3) . . . . ? C2C C1C C6C C5C -0.3(3) . . . . ? B C1C C6C C5C -178.92(18) . . . . ? C12C C7C C8C C9C -0.3(3) . . . . ? B C7C C8C C9C 175.40(17) . . . . ? C7C C8C C9C C10C -0.2(3) . . . . ? C8C C9C C10C C11C 0.5(3) . . . . ? C9C C10C C11C C12C -0.4(3) . . . . ? C10C C11C C12C C7C -0.1(3) . . . . ? C8C C7C C12C C11C 0.4(3) . . . . ? B C7C C12C C11C -175.15(16) . . . . ? C18C C13C C14C C15C 1.9(3) . . . . ? B C13C C14C C15C -175.65(18) . . . . ? C13C C14C C15C C16C -0.2(3) . . . . ? C14C C15C C16C C17C -1.1(3) . . . . ? C15C C16C C17C C18C 0.6(3) . . . . ? C16C C17C C18C C13C 1.3(3) . . . . ? C14C C13C C18C C17C -2.5(3) . . . . ? B C13C C18C C17C 175.14(18) . . . . ? C24C C19C C20C C21C -1.0(3) . . . . ? B C19C C20C C21C -179.19(17) . . . . ? C19C C20C C21C C22C 0.5(3) . . . . ? C20C C21C C22C C23C 0.8(3) . . . . ? C21C C22C C23C C24C -1.4(3) . . . . ? C22C C23C C24C C19C 0.8(3) . . . . ? C20C C19C C24C C23C 0.4(3) . . . . ? B C19C C24C C23C 178.53(17) . . . . ? C12C C7C B C1C 94.3(2) . . . . ? C8C C7C B C1C -81.01(19) . . . . ? C12C C7C B C19C -24.1(2) . . . . ? C8C C7C B C19C 160.57(15) . . . . ? C12C C7C B C13C -143.94(17) . . . . ? C8C C7C B C13C 40.7(2) . . . . ? C6C C1C B C7C 8.1(2) . . . . ? C2C C1C B C7C -170.43(16) . . . . ? C6C C1C B C19C 126.84(17) . . . . ? C2C C1C B C19C -51.7(2) . . . . ? C6C C1C B C13C -112.24(19) . . . . ? C2C C1C B C13C 69.2(2) . . . . ? C24C C19C B C7C -90.10(19) . . . . ? C20C C19C B C7C 87.90(19) . . . . ? C24C C19C B C1C 151.74(16) . . . . ? C20C C19C B C1C -30.3(2) . . . . ? C24C C19C B C13C 29.6(2) . . . . ? C20C C19C B C13C -152.43(16) . . . . ? C14C C13C B C7C -138.87(18) . . . . ? C18C C13C B C7C 43.7(2) . . . . ? C14C C13C B C1C -19.1(2) . . . . ? C18C C13C B C1C 163.55(17) . . . . ? C14C C13C B C19C 101.4(2) . . . . ? C18C C13C B C19C -75.9(2) . . . . ? #END OF CIF