Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jeffery Davis' _publ_contact_author_email jdavis@umd.edu _publ_section_title ; Ceramide-Mediated Transport of Chloride and Bicarbonate Across Phospholipid Membranes ; _publ_author_name 'Jeffery Davis' # Attachment '1793.cif' data_1793 _database_code_depnum_ccdc_archive 'CCDC 762206' #TrackingRef '1793.cif' _audit_creation_method 'SHELXL-97 & ZCIF' _chemical_name_systematic ; Isopropylidine C2 Ceramide ; _chemical_name_common 'Isopropylidine C2 Ceramide' _chemical_formula_moiety 'C23 H43 N O3' _chemical_formula_sum 'C23 H43 N O3' _chemical_formula_weight 381.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.9474(16) _cell_length_b 9.1515(16) _cell_length_c 29.391(5) _cell_angle_alpha 87.563(2) _cell_angle_beta 82.486(2) _cell_angle_gamma 88.842(2) _cell_volume 2383.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11982 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.4 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.063 _exptl_crystal_density_method ? _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.873 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; Crystals are non-merohedraly twinned by 180 deg. rotation around 0 1 0 real axis with domains ratio 4:1. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'three-circle diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_decay_% 0 _diffrn_reflns_number 30116 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8310 _reflns_number_gt 6931 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement Apex2 _computing_data_reduction Apex2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker, 2004)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.02P)^2^+3.17P], P=(max(Fo^2^,0)+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_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 8310 # 8310 w/o Fiedel pairs _refine_ls_number_parameters 989 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.8466(4) 0.0326(4) 0.63129(13) 0.0411(9) Uani 1 1 d . . . O2A O 0.4896(4) 0.1344(4) 0.51912(12) 0.0349(8) Uani 1 1 d . . . O3A O 0.3684(3) 0.1599(3) 0.59438(10) 0.0272(7) Uani 1 1 d . . . N1A N 0.7736(4) 0.2357(4) 0.59284(14) 0.0308(9) Uani 1 1 d . . . H1A H 0.7990 0.3245 0.5824 0.037 Uiso 1 1 calc R . . C1A C 0.6240(6) 0.2016(6) 0.52923(17) 0.0341(12) Uani 1 1 d . . . H1A1 H 0.6189 0.3083 0.5224 0.041 Uiso 1 1 calc R . . H1A2 H 0.7129 0.1610 0.5100 0.041 Uiso 1 1 calc R . . C2A C 0.6388(5) 0.1721(5) 0.57973(17) 0.0299(11) Uani 1 1 d . . . H2A H 0.6455 0.0638 0.5854 0.036 Uiso 1 1 calc R . . C3A C 0.4981(5) 0.2286(5) 0.60920(17) 0.0282(11) Uani 1 1 d . . . H3A H 0.4895 0.3370 0.6042 0.034 Uiso 1 1 calc R . . C4A C 0.4979(5) 0.1921(5) 0.65956(16) 0.0267(10) Uani 1 1 d . . . H4A H 0.5188 0.0941 0.6690 0.032 Uiso 1 1 calc R . . C5A C 0.4697(6) 0.2908(5) 0.69133(18) 0.0329(11) Uani 1 1 d . . . H5A H 0.4469 0.3870 0.6806 0.039 Uiso 1 1 calc R . . C6A C 0.4695(7) 0.2693(5) 0.74200(17) 0.0368(12) Uani 1 1 d . . . H6A1 H 0.3658 0.2890 0.7569 0.044 Uiso 1 1 calc R . . H6A2 H 0.5349 0.3446 0.7519 0.044 Uiso 1 1 calc R . . C7A C 0.5205(6) 0.1204(5) 0.76084(17) 0.0311(11) Uani 1 1 d . . . H7A1 H 0.4514 0.0439 0.7537 0.037 Uiso 1 1 calc R . . H7A2 H 0.6229 0.0963 0.7457 0.037 Uiso 1 1 calc R . . C8A C 0.5219(6) 0.1215(5) 0.81274(17) 0.0328(12) Uani 1 1 d . . . H8A1 H 0.5914 0.1984 0.8193 0.039 Uiso 1 1 calc R . . H8A2 H 0.4196 0.1489 0.8273 0.039 Uiso 1 1 calc R . . C9A C 0.5685(6) -0.0222(5) 0.83534(17) 0.0334(12) Uani 1 1 d . . . H9A1 H 0.6722 -0.0487 0.8218 0.040 Uiso 1 1 calc R . . H9A2 H 0.5007 -0.1002 0.8286 0.040 Uiso 1 1 calc R . . C10A C 0.5636(6) -0.0150(5) 0.88760(18) 0.0340(12) Uani 1 1 d . . . H10A H 0.6292 0.0652 0.8942 0.041 Uiso 1 1 calc R . . H10B H 0.4593 0.0098 0.9010 0.041 Uiso 1 1 calc R . . C11A C 0.6128(5) -0.1549(5) 0.91135(17) 0.0292(11) Uani 1 1 d . . . H11A H 0.7179 -0.1790 0.8986 0.035 Uiso 1 1 calc R . . H11B H 0.5483 -0.2358 0.9046 0.035 Uiso 1 1 calc R . . C12A C 0.6038(6) -0.1446(5) 0.96356(17) 0.0309(11) Uani 1 1 d . . . H12A H 0.6684 -0.0637 0.9703 0.037 Uiso 1 1 calc R . . H12B H 0.4987 -0.1200 0.9762 0.037 Uiso 1 1 calc R . . C13A C 0.6526(5) -0.2845(5) 0.98790(17) 0.0292(11) Uani 1 1 d . . . H13A H 0.7578 -0.3089 0.9753 0.035 Uiso 1 1 calc R . . H13B H 0.5882 -0.3654 0.9811 0.035 Uiso 1 1 calc R . . C14A C 0.6433(5) -0.2747(5) 1.03988(17) 0.0301(11) Uani 1 1 d . . . H14A H 0.5381 -0.2505 1.0525 0.036 Uiso 1 1 calc R . . H14B H 0.7077 -0.1938 1.0467 0.036 Uiso 1 1 calc R . . C15A C 0.6925(6) -0.4153(5) 1.06392(17) 0.0311(11) Uani 1 1 d . . . H15A H 0.6283 -0.4960 1.0569 0.037 Uiso 1 1 calc R . . H15B H 0.7977 -0.4392 1.0512 0.037 Uiso 1 1 calc R . . C16A C 0.6838(6) -0.4078(5) 1.11562(18) 0.0327(12) Uani 1 1 d . . . H16A H 0.5785 -0.3849 1.1285 0.039 Uiso 1 1 calc R . . H16B H 0.7476 -0.3269 1.1228 0.039 Uiso 1 1 calc R . . C17A C 0.7346(6) -0.5496(6) 1.13895(18) 0.0379(12) Uani 1 1 d . . . H17A H 0.8402 -0.5717 1.1263 0.046 Uiso 1 1 calc R . . H17B H 0.6717 -0.6306 1.1313 0.046 Uiso 1 1 calc R . . C18A C 0.7243(7) -0.5444(7) 1.19137(19) 0.0485(15) Uani 1 1 d . . . H18A H 0.6192 -0.5277 1.2044 0.073 Uiso 1 1 calc R . . H18B H 0.7864 -0.4646 1.1993 0.073 Uiso 1 1 calc R . . H18C H 0.7609 -0.6375 1.2038 0.073 Uiso 1 1 calc R . . C19A C 0.8601(5) 0.1635(5) 0.62034(17) 0.0296(11) Uani 1 1 d . . . C20A C 0.9789(6) 0.2548(6) 0.6377(2) 0.0403(13) Uani 1 1 d . . . H20A H 1.0761 0.2024 0.6338 0.060 Uiso 1 1 calc R . . H20B H 0.9494 0.2724 0.6704 0.060 Uiso 1 1 calc R . . H20C H 0.9880 0.3486 0.6203 0.060 Uiso 1 1 calc R . . C21A C 0.3546(5) 0.1816(5) 0.54692(17) 0.0292(11) Uani 1 1 d . . . C22A C 0.2346(6) 0.0757(6) 0.53795(18) 0.0382(12) Uani 1 1 d . . . H22A H 0.1365 0.1075 0.5535 0.057 Uiso 1 1 calc R . . H22B H 0.2594 -0.0224 0.5497 0.057 Uiso 1 1 calc R . . H22C H 0.2305 0.0735 0.5048 0.057 Uiso 1 1 calc R . . C23A C 0.3126(6) 0.3393(5) 0.53466(18) 0.0378(12) Uani 1 1 d . . . H23A H 0.3943 0.4039 0.5399 0.057 Uiso 1 1 calc R . . H23B H 0.2197 0.3677 0.5539 0.057 Uiso 1 1 calc R . . H23C H 0.2969 0.3479 0.5023 0.057 Uiso 1 1 calc R . . O1B O 0.8400(4) 0.5421(4) 0.57399(12) 0.0361(8) Uani 1 1 d . . . O2B O 0.3313(4) 0.6755(4) 0.61302(12) 0.0365(8) Uani 1 1 d . . . O3B O 0.4063(3) 0.6539(3) 0.68685(11) 0.0289(7) Uani 1 1 d . . . N1B N 0.7409(4) 0.7514(4) 0.60402(14) 0.0288(9) Uani 1 1 d . . . H1B H 0.7561 0.8443 0.6081 0.035 Uiso 1 1 calc R . . C1B C 0.4713(5) 0.7422(6) 0.59451(18) 0.0370(12) Uani 1 1 d . . . H1B1 H 0.4610 0.8499 0.5958 0.044 Uiso 1 1 calc R . . H1B2 H 0.4978 0.7170 0.5620 0.044 Uiso 1 1 calc R . . C2B C 0.5952(5) 0.6878(5) 0.62227(17) 0.0309(11) Uani 1 1 d . . . H2B H 0.6046 0.5794 0.6197 0.037 Uiso 1 1 calc R . . C3B C 0.5511(5) 0.7192(5) 0.67251(17) 0.0280(11) Uani 1 1 d . . . H3B H 0.5441 0.8272 0.6765 0.034 Uiso 1 1 calc R . . C4B C 0.6590(6) 0.6514(6) 0.70225(19) 0.0382(13) Uani 1 1 d . . . H4B H 0.6889 0.5526 0.6971 0.046 Uiso 1 1 calc R . . C5B C 0.7157(6) 0.7158(6) 0.73463(19) 0.0430(13) Uani 1 1 d . . . H5B H 0.6879 0.8153 0.7393 0.052 Uiso 1 1 calc R . . C6B C 0.8221(7) 0.6455(8) 0.76540(19) 0.0513(16) Uani 1 1 d . . . H6B1 H 0.8924 0.7203 0.7729 0.062 Uiso 1 1 calc R . . H6B2 H 0.8827 0.5687 0.7484 0.062 Uiso 1 1 calc R . . C7B C 0.7421(6) 0.5778(6) 0.80976(18) 0.0370(12) Uani 1 1 d . . . H7B1 H 0.6711 0.6508 0.8248 0.044 Uiso 1 1 calc R . . H7B2 H 0.6826 0.4937 0.8025 0.044 Uiso 1 1 calc R . . C8B C 0.8502(6) 0.5263(6) 0.84267(19) 0.0402(13) Uani 1 1 d . . . H8B1 H 0.9000 0.6126 0.8528 0.048 Uiso 1 1 calc R . . H8B2 H 0.9295 0.4643 0.8260 0.048 Uiso 1 1 calc R . . C9B C 0.7780(6) 0.4404(5) 0.88481(18) 0.0350(12) Uani 1 1 d . . . H9B1 H 0.7339 0.3506 0.8749 0.042 Uiso 1 1 calc R . . H9B2 H 0.6947 0.4998 0.9005 0.042 Uiso 1 1 calc R . . C10B C 0.8869(6) 0.3975(6) 0.91873(18) 0.0355(12) Uani 1 1 d . . . H10C H 0.9286 0.4877 0.9292 0.043 Uiso 1 1 calc R . . H10D H 0.9719 0.3412 0.9026 0.043 Uiso 1 1 calc R . . C11B C 0.8184(6) 0.3067(5) 0.96075(19) 0.0349(12) Uani 1 1 d . . . H11C H 0.7322 0.3618 0.9768 0.042 Uiso 1 1 calc R . . H11D H 0.7792 0.2150 0.9505 0.042 Uiso 1 1 calc R . . C12B C 0.9302(5) 0.2688(5) 0.99447(17) 0.0313(11) Uani 1 1 d . . . H12C H 0.9689 0.3606 1.0049 0.038 Uiso 1 1 calc R . . H12D H 1.0168 0.2145 0.9783 0.038 Uiso 1 1 calc R . . C13B C 0.8630(6) 0.1770(5) 1.03645(18) 0.0334(12) Uani 1 1 d . . . H13C H 0.7750 0.2302 1.0522 0.040 Uiso 1 1 calc R . . H13D H 0.8264 0.0842 1.0261 0.040 Uiso 1 1 calc R . . C14B C 0.9739(6) 0.1419(5) 1.07061(17) 0.0320(11) Uani 1 1 d . . . H14C H 1.0608 0.0868 1.0550 0.038 Uiso 1 1 calc R . . H14D H 1.0122 0.2347 1.0804 0.038 Uiso 1 1 calc R . . C15B C 0.9064(6) 0.0532(6) 1.11294(18) 0.0338(12) Uani 1 1 d . . . H15C H 0.8685 -0.0396 1.1031 0.041 Uiso 1 1 calc R . . H15D H 0.8191 0.1082 1.1284 0.041 Uiso 1 1 calc R . . C16B C 1.0157(6) 0.0180(6) 1.14750(19) 0.0383(13) Uani 1 1 d . . . H16C H 1.1045 -0.0347 1.1319 0.046 Uiso 1 1 calc R . . H16D H 1.0515 0.1108 1.1581 0.046 Uiso 1 1 calc R . . C17B C 0.9486(6) -0.0742(6) 1.18911(18) 0.0397(13) Uani 1 1 d . . . H17C H 0.8614 -0.0203 1.2050 0.048 Uiso 1 1 calc R . . H17D H 0.9103 -0.1657 1.1784 0.048 Uiso 1 1 calc R . . C18B C 1.0571(8) -0.1138(7) 1.2234(2) 0.0552(16) Uani 1 1 d . . . H18D H 1.0844 -0.0250 1.2377 0.083 Uiso 1 1 calc R . . H18E H 1.1481 -0.1596 1.2075 0.083 Uiso 1 1 calc R . . H18F H 1.0088 -0.1822 1.2471 0.083 Uiso 1 1 calc R . . C19B C 0.8514(5) 0.6723(5) 0.58135(16) 0.0266(10) Uani 1 1 d . . . C20B C 0.9957(5) 0.7534(6) 0.56389(19) 0.0364(12) Uani 1 1 d . . . H20D H 1.0076 0.7617 0.5303 0.055 Uiso 1 1 calc R . . H20E H 1.0821 0.6993 0.5739 0.055 Uiso 1 1 calc R . . H20F H 0.9905 0.8514 0.5763 0.055 Uiso 1 1 calc R . . C21B C 0.2865(5) 0.6998(5) 0.66050(17) 0.0303(11) Uani 1 1 d . . . C22B C 0.2358(6) 0.8567(6) 0.6692(2) 0.0407(13) Uani 1 1 d . . . H22D H 0.3132 0.9235 0.6543 0.061 Uiso 1 1 calc R . . H22E H 0.2203 0.8713 0.7023 0.061 Uiso 1 1 calc R . . H22F H 0.1410 0.8764 0.6565 0.061 Uiso 1 1 calc R . . C23B C 0.1600(6) 0.5943(6) 0.6758(2) 0.0409(13) Uani 1 1 d . . . H23D H 0.1321 0.5981 0.7091 0.061 Uiso 1 1 calc R . . H23E H 0.1935 0.4949 0.6679 0.061 Uiso 1 1 calc R . . H23F H 0.0725 0.6217 0.6602 0.061 Uiso 1 1 calc R . . O1C O 0.1546(4) 0.5729(4) 0.36855(13) 0.0416(9) Uani 1 1 d . . . O2C O 0.5139(4) 0.6340(4) 0.47979(12) 0.0347(8) Uani 1 1 d . . . O3C O 0.6359(4) 0.6875(3) 0.40506(11) 0.0307(8) Uani 1 1 d . . . N1C N 0.2284(5) 0.7650(4) 0.40622(15) 0.0344(10) Uani 1 1 d . . . H1C H 0.2022 0.8516 0.4169 0.041 Uiso 1 1 calc R . . C1C C 0.3776(6) 0.7046(6) 0.46977(17) 0.0342(12) Uani 1 1 d . . . H1C1 H 0.3771 0.8084 0.4780 0.041 Uiso 1 1 calc R . . H1C2 H 0.2899 0.6566 0.4880 0.041 Uiso 1 1 calc R . . C2C C 0.3665(6) 0.6948(5) 0.41828(17) 0.0315(11) Uani 1 1 d . . . H2C H 0.3643 0.5891 0.4111 0.038 Uiso 1 1 calc R . . C3C C 0.5075(6) 0.7621(5) 0.39057(17) 0.0314(11) Uani 1 1 d . . . H3C H 0.5115 0.8686 0.3967 0.038 Uiso 1 1 calc R . . C4C C 0.5114(6) 0.7426(5) 0.34018(17) 0.0330(11) Uani 1 1 d . . . H4C H 0.4752 0.6526 0.3313 0.040 Uiso 1 1 calc R . . C5C C 0.5594(6) 0.8368(5) 0.30723(17) 0.0335(11) Uani 1 1 d . . . H5C H 0.5945 0.9274 0.3160 0.040 Uiso 1 1 calc R . . C6C C 0.5643(6) 0.8149(6) 0.25664(18) 0.0368(12) Uani 1 1 d . . . H6C1 H 0.5061 0.7270 0.2521 0.044 Uiso 1 1 calc R . . H6C2 H 0.6701 0.7976 0.2431 0.044 Uiso 1 1 calc R . . C7C C 0.5002(6) 0.9458(5) 0.23192(17) 0.0341(12) Uani 1 1 d . . . H7C1 H 0.5577 1.0333 0.2373 0.041 Uiso 1 1 calc R . . H7C2 H 0.3945 0.9620 0.2457 0.041 Uiso 1 1 calc R . . C8C C 0.5030(6) 0.9324(5) 0.18012(18) 0.0336(12) Uani 1 1 d . . . H8C1 H 0.6070 0.9081 0.1664 0.040 Uiso 1 1 calc R . . H8C2 H 0.4376 0.8507 0.1746 0.040 Uiso 1 1 calc R . . C9C C 0.4502(6) 1.0711(5) 0.15637(17) 0.0323(11) Uani 1 1 d . . . H9C1 H 0.5148 1.1528 0.1624 0.039 Uiso 1 1 calc R . . H9C2 H 0.3458 1.0945 0.1700 0.039 Uiso 1 1 calc R . . C10C C 0.4534(6) 1.0616(5) 0.10466(17) 0.0312(11) Uani 1 1 d . . . H10E H 0.5572 1.0360 0.0911 0.037 Uiso 1 1 calc R . . H10F H 0.3869 0.9814 0.0986 0.037 Uiso 1 1 calc R . . C11C C 0.4040(6) 1.2009(5) 0.08083(18) 0.0320(11) Uani 1 1 d . . . H11E H 0.4702 1.2812 0.0869 0.038 Uiso 1 1 calc R . . H11F H 0.3000 1.2263 0.0943 0.038 Uiso 1 1 calc R . . C12C C 0.4080(5) 1.1911(5) 0.02935(17) 0.0306(11) Uani 1 1 d . . . H12E H 0.3402 1.1121 0.0232 0.037 Uiso 1 1 calc R . . H12F H 0.5115 1.1637 0.0159 0.037 Uiso 1 1 calc R . . C13C C 0.3612(6) 1.3323(5) 0.00524(18) 0.0327(12) Uani 1 1 d . . . H13E H 0.4285 1.4113 0.0117 0.039 Uiso 1 1 calc R . . H13F H 0.2575 1.3592 0.0186 0.039 Uiso 1 1 calc R . . C14C C 0.3653(6) 1.3250(5) -0.04677(18) 0.0326(12) Uani 1 1 d . . . H14E H 0.4689 1.2987 -0.0604 0.039 Uiso 1 1 calc R . . H14F H 0.2977 1.2465 -0.0534 0.039 Uiso 1 1 calc R . . C15C C 0.3179(6) 1.4676(5) -0.06961(18) 0.0335(12) Uani 1 1 d . . . H15E H 0.3850 1.5460 -0.0626 0.040 Uiso 1 1 calc R . . H15F H 0.2142 1.4934 -0.0559 0.040 Uiso 1 1 calc R . . C16C C 0.3215(6) 1.4650(5) -0.12201(18) 0.0328(12) Uani 1 1 d . . . H16E H 0.4253 1.4410 -0.1360 0.039 Uiso 1 1 calc R . . H16F H 0.2547 1.3867 -0.1293 0.039 Uiso 1 1 calc R . . C17C C 0.2720(6) 1.6089(6) -0.14308(18) 0.0347(12) Uani 1 1 d . . . H17E H 0.3379 1.6869 -0.1351 0.042 Uiso 1 1 calc R . . H17F H 0.1679 1.6319 -0.1290 0.042 Uiso 1 1 calc R . . C18C C 0.2755(7) 1.6124(7) -0.19511(19) 0.0452(14) Uani 1 1 d . . . H18G H 0.2124 1.5342 -0.2036 0.068 Uiso 1 1 calc R . . H18H H 0.3795 1.5979 -0.2096 0.068 Uiso 1 1 calc R . . H18I H 0.2369 1.7072 -0.2056 0.068 Uiso 1 1 calc R . . C19C C 0.1394(6) 0.7012(5) 0.37915(17) 0.0323(11) Uani 1 1 d . . . C20C C 0.0195(6) 0.7990(6) 0.3625(2) 0.0419(13) Uani 1 1 d . . . H20G H -0.0767 0.7478 0.3667 0.063 Uiso 1 1 calc R . . H20H H 0.0476 0.8249 0.3298 0.063 Uiso 1 1 calc R . . H20I H 0.0095 0.8882 0.3800 0.063 Uiso 1 1 calc R . . C21C C 0.6478(6) 0.6904(5) 0.45303(17) 0.0326(11) Uani 1 1 d . . . C22C C 0.6819(6) 0.8440(6) 0.46730(19) 0.0413(13) Uani 1 1 d . . . H22G H 0.5927 0.9072 0.4662 0.062 Uiso 1 1 calc R . . H22H H 0.7663 0.8844 0.4462 0.062 Uiso 1 1 calc R . . H22I H 0.7085 0.8386 0.4986 0.062 Uiso 1 1 calc R . . C23C C 0.7717(6) 0.5821(6) 0.46129(18) 0.0388(12) Uani 1 1 d . . . H23G H 0.8680 0.6176 0.4453 0.058 Uiso 1 1 calc R . . H23H H 0.7497 0.4873 0.4496 0.058 Uiso 1 1 calc R . . H23I H 0.7779 0.5713 0.4943 0.058 Uiso 1 1 calc R . . O1D O 0.2022(4) 0.0660(4) 0.42178(13) 0.0428(9) Uani 1 1 d . . . O2D O 0.6869(4) 0.1829(4) 0.37405(12) 0.0388(9) Uani 1 1 d . . . O3D O 0.6147(4) 0.2428(4) 0.30153(12) 0.0336(8) Uani 1 1 d . . . N1D N 0.2785(5) 0.2822(4) 0.38790(15) 0.0322(10) Uani 1 1 d . . . H1D H 0.2575 0.3758 0.3837 0.039 Uiso 1 1 calc R . . C1D C 0.5460(6) 0.2357(6) 0.39707(18) 0.0362(12) Uani 1 1 d . . . H1D1 H 0.5558 0.3391 0.4047 0.043 Uiso 1 1 calc R . . H1D2 H 0.5190 0.1778 0.4261 0.043 Uiso 1 1 calc R . . C2D C 0.4220(5) 0.2235(5) 0.36648(17) 0.0301(11) Uani 1 1 d . . . H2D H 0.4094 0.1180 0.3604 0.036 Uiso 1 1 calc R . . C3D C 0.4707(6) 0.3068(5) 0.32059(17) 0.0312(11) Uani 1 1 d . . . H3D H 0.4851 0.4121 0.3265 0.037 Uiso 1 1 calc R . . C4D C 0.3644(6) 0.2964(5) 0.28528(17) 0.0341(12) Uani 1 1 d . . . H4D H 0.3464 0.2028 0.2745 0.041 Uiso 1 1 calc R . . C5D C 0.2955(6) 0.4103(6) 0.26866(17) 0.0325(11) Uani 1 1 d . . . H5D H 0.3117 0.5021 0.2810 0.039 Uiso 1 1 calc R . . C6D C 0.1941(6) 0.4100(6) 0.23228(18) 0.0374(12) Uani 1 1 d . . . H6D1 H 0.0961 0.4562 0.2437 0.045 Uiso 1 1 calc R . . H6D2 H 0.1752 0.3078 0.2251 0.045 Uiso 1 1 calc R . . C7D C 0.2642(6) 0.4934(6) 0.18841(17) 0.0330(11) Uani 1 1 d . . . H7D1 H 0.2999 0.5889 0.1970 0.040 Uiso 1 1 calc R . . H7D2 H 0.3533 0.4373 0.1746 0.040 Uiso 1 1 calc R . . C8D C 0.1574(6) 0.5205(6) 0.15221(17) 0.0321(11) Uani 1 1 d . . . H8D1 H 0.0660 0.5729 0.1662 0.039 Uiso 1 1 calc R . . H8D2 H 0.1256 0.4252 0.1423 0.039 Uiso 1 1 calc R . . C9D C 0.2293(6) 0.6100(5) 0.11008(18) 0.0320(11) Uani 1 1 d . . . H9D1 H 0.2679 0.7020 0.1203 0.038 Uiso 1 1 calc R . . H9D2 H 0.3163 0.5542 0.0949 0.038 Uiso 1 1 calc R . . C10D C 0.1209(5) 0.6471(5) 0.07531(17) 0.0313(11) Uani 1 1 d . . . H10G H 0.0857 0.5549 0.0641 0.038 Uiso 1 1 calc R . . H10H H 0.0317 0.6990 0.0909 0.038 Uiso 1 1 calc R . . C11D C 0.1891(6) 0.7412(5) 0.03436(18) 0.0307(11) Uani 1 1 d . . . H11G H 0.2773 0.6887 0.0184 0.037 Uiso 1 1 calc R . . H11H H 0.2256 0.8328 0.0456 0.037 Uiso 1 1 calc R . . C12D C 0.0792(5) 0.7801(5) -0.00014(17) 0.0301(11) Uani 1 1 d . . . H12G H 0.0421 0.6885 -0.0112 0.036 Uiso 1 1 calc R . . H12H H -0.0087 0.8332 0.0157 0.036 Uiso 1 1 calc R . . C13D C 0.1483(5) 0.8739(5) -0.04147(17) 0.0303(11) Uani 1 1 d . . . H13G H 0.2369 0.8212 -0.0571 0.036 Uiso 1 1 calc R . . H13H H 0.1844 0.9658 -0.0304 0.036 Uiso 1 1 calc R . . C14D C 0.0391(6) 0.9115(5) -0.07625(18) 0.0341(12) Uani 1 1 d . . . H14G H 0.0002 0.8195 -0.0865 0.041 Uiso 1 1 calc R . . H14H H -0.0477 0.9673 -0.0609 0.041 Uiso 1 1 calc R . . C15D C 0.1098(6) 1.0004(6) -0.11819(18) 0.0345(12) Uani 1 1 d . . . H15G H 0.1997 0.9465 -0.1325 0.041 Uiso 1 1 calc R . . H15H H 0.1446 1.0941 -0.1080 0.041 Uiso 1 1 calc R . . C16D C 0.0057(6) 1.0335(6) -0.15442(19) 0.0412(13) Uani 1 1 d . . . H16G H -0.0294 0.9400 -0.1647 0.049 Uiso 1 1 calc R . . H16H H -0.0840 1.0880 -0.1403 0.049 Uiso 1 1 calc R . . C17D C 0.0787(7) 1.1217(8) -0.1960(2) 0.0517(16) Uani 1 1 d . . . H17G H 0.1675 1.0664 -0.2103 0.062 Uiso 1 1 calc R . . H17H H 0.1152 1.2145 -0.1856 0.062 Uiso 1 1 calc R . . C18D C -0.0259(9) 1.1574(10) -0.2322(3) 0.083(3) Uani 1 1 d . . . H18J H -0.1174 1.2065 -0.2179 0.124 Uiso 1 1 calc R . . H18K H -0.0531 1.0666 -0.2455 0.124 Uiso 1 1 calc R . . H18L H 0.0258 1.2218 -0.2565 0.124 Uiso 1 1 calc R . . C19D C 0.1771(6) 0.1968(5) 0.41392(17) 0.0318(11) Uani 1 1 d . . . C20D C 0.0330(6) 0.2691(6) 0.4330(2) 0.0423(13) Uani 1 1 d . . . H20J H 0.0194 0.2571 0.4665 0.063 Uiso 1 1 calc R . . H20K H -0.0513 0.2243 0.4208 0.063 Uiso 1 1 calc R . . H20L H 0.0361 0.3735 0.4241 0.063 Uiso 1 1 calc R . . C21D C 0.7323(6) 0.2523(6) 0.33013(18) 0.0331(11) Uani 1 1 d . . . C22D C 0.7786(6) 0.4106(6) 0.33359(19) 0.0381(12) Uani 1 1 d . . . H22J H 0.7005 0.4622 0.3536 0.057 Uiso 1 1 calc R . . H22K H 0.7910 0.4588 0.3029 0.057 Uiso 1 1 calc R . . H22L H 0.8742 0.4125 0.3465 0.057 Uiso 1 1 calc R . . C23D C 0.8607(6) 0.1606(6) 0.3075(2) 0.0422(13) Uani 1 1 d . . . H23J H 0.8916 0.1996 0.2762 0.063 Uiso 1 1 calc R . . H23K H 0.8279 0.0594 0.3065 0.063 Uiso 1 1 calc R . . H23L H 0.9461 0.1632 0.3252 0.063 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 O1A 0.041(2) 0.031(2) 0.055(2) -0.0012(17) -0.0191(18) -0.0051(15) O2A 0.0276(19) 0.047(2) 0.0310(19) -0.0038(16) -0.0064(15) -0.0098(15) O3A 0.0266(18) 0.0345(18) 0.0219(18) 0.0040(14) -0.0085(14) -0.0092(14) N1A 0.025(2) 0.030(2) 0.038(3) 0.0002(18) -0.0050(19) -0.0113(17) C1A 0.029(3) 0.047(3) 0.027(3) 0.003(2) -0.006(2) -0.013(2) C2A 0.028(3) 0.026(2) 0.037(3) 0.000(2) -0.011(2) -0.0095(19) C3A 0.030(3) 0.020(2) 0.038(3) -0.001(2) -0.015(2) -0.0077(19) C4A 0.033(3) 0.022(2) 0.027(3) 0.0020(19) -0.008(2) -0.0068(19) C5A 0.035(3) 0.023(2) 0.041(3) -0.001(2) -0.006(2) -0.005(2) C6A 0.051(3) 0.030(3) 0.030(3) -0.001(2) -0.006(2) -0.003(2) C7A 0.033(3) 0.030(3) 0.030(3) 0.000(2) -0.003(2) -0.006(2) C8A 0.036(3) 0.031(3) 0.033(3) -0.002(2) -0.007(2) -0.004(2) C9A 0.035(3) 0.033(3) 0.033(3) 0.000(2) -0.008(2) -0.005(2) C10A 0.033(3) 0.030(3) 0.040(3) -0.002(2) -0.008(2) -0.003(2) C11A 0.025(3) 0.032(3) 0.032(3) 0.001(2) -0.011(2) -0.005(2) C12A 0.026(3) 0.033(3) 0.034(3) -0.001(2) -0.006(2) -0.004(2) C13A 0.024(3) 0.031(3) 0.032(3) -0.002(2) -0.004(2) -0.004(2) C14A 0.021(3) 0.032(3) 0.037(3) -0.002(2) -0.004(2) -0.003(2) C15A 0.028(3) 0.034(3) 0.032(3) 0.000(2) -0.006(2) -0.006(2) C16A 0.025(3) 0.035(3) 0.038(3) -0.002(2) -0.003(2) -0.005(2) C17A 0.037(3) 0.044(3) 0.034(3) 0.004(2) -0.010(2) -0.007(2) C18A 0.043(4) 0.063(4) 0.040(3) 0.005(3) -0.007(3) -0.007(3) C19A 0.021(3) 0.034(3) 0.035(3) -0.008(2) -0.005(2) -0.005(2) C20A 0.034(3) 0.042(3) 0.048(3) -0.006(3) -0.014(3) -0.008(2) C21A 0.023(3) 0.036(3) 0.028(3) -0.001(2) -0.004(2) -0.007(2) C22A 0.039(3) 0.045(3) 0.034(3) -0.006(2) -0.012(2) -0.008(2) C23A 0.043(3) 0.042(3) 0.031(3) 0.005(2) -0.014(2) -0.002(2) O1B 0.034(2) 0.0303(19) 0.045(2) -0.0023(16) -0.0062(16) -0.0056(14) O2B 0.0222(18) 0.058(2) 0.030(2) -0.0030(16) -0.0039(15) -0.0172(15) O3B 0.0215(17) 0.0332(18) 0.0317(19) 0.0065(14) -0.0043(14) -0.0070(13) N1B 0.024(2) 0.025(2) 0.038(2) -0.0040(17) -0.0016(18) -0.0081(16) C1B 0.023(3) 0.058(3) 0.030(3) 0.001(2) -0.005(2) -0.016(2) C2B 0.031(3) 0.025(2) 0.037(3) -0.001(2) -0.005(2) -0.0091(19) C3B 0.026(3) 0.026(2) 0.034(3) 0.004(2) -0.012(2) -0.0055(19) C4B 0.039(3) 0.036(3) 0.040(3) 0.012(2) -0.010(3) -0.006(2) C5B 0.045(3) 0.051(3) 0.035(3) -0.001(3) -0.014(3) 0.002(3) C6B 0.035(3) 0.089(5) 0.030(3) 0.013(3) -0.010(3) -0.001(3) C7B 0.039(3) 0.040(3) 0.034(3) -0.003(2) -0.013(2) 0.001(2) C8B 0.034(3) 0.048(3) 0.040(3) 0.000(3) -0.013(3) -0.002(2) C9B 0.034(3) 0.035(3) 0.038(3) -0.002(2) -0.014(2) 0.001(2) C10B 0.029(3) 0.040(3) 0.039(3) -0.001(2) -0.010(2) -0.003(2) C11B 0.036(3) 0.029(3) 0.041(3) 0.000(2) -0.010(2) -0.001(2) C12B 0.027(3) 0.034(3) 0.034(3) -0.003(2) -0.006(2) -0.003(2) C13B 0.029(3) 0.032(3) 0.040(3) -0.001(2) -0.007(2) -0.003(2) C14B 0.030(3) 0.037(3) 0.031(3) -0.002(2) -0.008(2) -0.001(2) C15B 0.032(3) 0.035(3) 0.035(3) 0.000(2) -0.006(2) -0.005(2) C16B 0.034(3) 0.040(3) 0.041(3) -0.003(2) -0.004(2) -0.004(2) C17B 0.040(3) 0.045(3) 0.035(3) 0.001(2) -0.008(3) -0.002(2) C18B 0.060(4) 0.065(4) 0.043(4) 0.001(3) -0.017(3) 0.004(3) C19B 0.020(2) 0.034(3) 0.027(3) 0.005(2) -0.009(2) 0.0005(19) C20B 0.020(3) 0.044(3) 0.045(3) 0.004(2) -0.008(2) -0.007(2) C21B 0.022(3) 0.038(3) 0.032(3) 0.002(2) -0.010(2) -0.006(2) C22B 0.025(3) 0.045(3) 0.054(4) 0.000(3) -0.014(3) 0.004(2) C23B 0.025(3) 0.053(3) 0.044(3) 0.005(3) -0.003(2) -0.013(2) O1C 0.042(2) 0.036(2) 0.049(2) -0.0040(17) -0.0130(18) 0.0021(16) O2C 0.034(2) 0.041(2) 0.0273(19) 0.0045(15) -0.0036(15) 0.0006(15) O3C 0.0326(19) 0.0354(18) 0.0232(18) 0.0004(14) -0.0022(15) 0.0043(14) N1C 0.038(3) 0.026(2) 0.040(3) -0.0037(18) -0.012(2) 0.0060(18) C1C 0.029(3) 0.039(3) 0.033(3) 0.002(2) -0.003(2) 0.002(2) C2C 0.034(3) 0.026(2) 0.034(3) 0.001(2) -0.004(2) 0.006(2) C3C 0.036(3) 0.026(3) 0.031(3) -0.004(2) -0.004(2) 0.003(2) C4C 0.039(3) 0.028(3) 0.033(3) -0.004(2) -0.004(2) -0.001(2) C5C 0.037(3) 0.033(3) 0.031(3) -0.001(2) -0.001(2) -0.005(2) C6C 0.037(3) 0.038(3) 0.034(3) -0.001(2) 0.003(2) -0.002(2) C7C 0.033(3) 0.032(3) 0.037(3) -0.006(2) -0.005(2) -0.002(2) C8C 0.037(3) 0.028(3) 0.037(3) -0.003(2) -0.006(2) -0.003(2) C9C 0.030(3) 0.030(3) 0.036(3) -0.001(2) -0.003(2) -0.002(2) C10C 0.030(3) 0.029(3) 0.034(3) 0.000(2) -0.004(2) -0.005(2) C11C 0.026(3) 0.030(3) 0.040(3) 0.000(2) -0.004(2) -0.003(2) C12C 0.022(3) 0.033(3) 0.037(3) 0.001(2) -0.005(2) -0.002(2) C13C 0.032(3) 0.030(3) 0.037(3) -0.002(2) -0.005(2) -0.005(2) C14C 0.025(3) 0.033(3) 0.039(3) -0.004(2) -0.004(2) -0.001(2) C15C 0.030(3) 0.033(3) 0.038(3) -0.003(2) -0.007(2) 0.000(2) C16C 0.024(3) 0.037(3) 0.037(3) -0.003(2) -0.004(2) -0.002(2) C17C 0.029(3) 0.042(3) 0.035(3) -0.001(2) -0.008(2) -0.004(2) C18C 0.043(3) 0.056(4) 0.037(3) 0.003(3) -0.009(3) 0.002(3) C19C 0.035(3) 0.033(3) 0.029(3) 0.002(2) -0.002(2) 0.000(2) C20C 0.040(3) 0.046(3) 0.040(3) 0.005(3) -0.008(3) 0.003(2) C21C 0.031(3) 0.039(3) 0.027(3) 0.004(2) -0.005(2) -0.001(2) C22C 0.050(4) 0.040(3) 0.036(3) -0.005(2) -0.010(3) -0.005(2) C23C 0.038(3) 0.049(3) 0.031(3) 0.003(2) -0.009(2) 0.001(2) O1D 0.055(2) 0.029(2) 0.043(2) 0.0016(16) -0.0021(18) -0.0024(16) O2D 0.033(2) 0.047(2) 0.037(2) 0.0031(17) -0.0099(17) 0.0073(16) O3D 0.0310(19) 0.0361(19) 0.035(2) -0.0091(15) -0.0070(16) 0.0007(14) N1D 0.035(2) 0.023(2) 0.040(3) 0.0010(18) -0.010(2) 0.0055(17) C1D 0.031(3) 0.046(3) 0.032(3) 0.001(2) -0.007(2) 0.006(2) C2D 0.030(3) 0.027(2) 0.034(3) 0.000(2) -0.006(2) 0.003(2) C3D 0.038(3) 0.027(2) 0.029(3) -0.002(2) -0.005(2) 0.001(2) C4D 0.043(3) 0.031(3) 0.031(3) -0.005(2) -0.011(2) -0.002(2) C5D 0.033(3) 0.037(3) 0.027(3) 0.003(2) -0.004(2) -0.004(2) C6D 0.040(3) 0.037(3) 0.036(3) 0.002(2) -0.007(2) -0.005(2) C7D 0.029(3) 0.036(3) 0.033(3) 0.006(2) -0.006(2) -0.005(2) C8D 0.024(3) 0.037(3) 0.036(3) 0.001(2) -0.007(2) -0.004(2) C9D 0.028(3) 0.033(3) 0.036(3) 0.002(2) -0.010(2) 0.001(2) C10D 0.025(3) 0.036(3) 0.033(3) 0.001(2) -0.006(2) -0.001(2) C11D 0.025(3) 0.035(3) 0.032(3) 0.000(2) -0.006(2) -0.003(2) C12D 0.024(3) 0.036(3) 0.031(3) -0.001(2) -0.006(2) 0.001(2) C13D 0.027(3) 0.034(3) 0.030(3) 0.000(2) -0.005(2) -0.003(2) C14D 0.035(3) 0.030(3) 0.037(3) -0.003(2) -0.005(2) -0.001(2) C15D 0.032(3) 0.037(3) 0.035(3) 0.002(2) -0.008(2) 0.000(2) C16D 0.037(3) 0.050(3) 0.037(3) 0.004(3) -0.008(3) -0.001(2) C17D 0.044(4) 0.077(4) 0.035(3) 0.014(3) -0.013(3) -0.008(3) C18D 0.068(5) 0.130(7) 0.052(5) 0.035(5) -0.028(4) -0.019(5) C19D 0.038(3) 0.033(3) 0.027(3) -0.004(2) -0.014(2) 0.000(2) C20D 0.035(3) 0.045(3) 0.047(4) 0.002(3) -0.006(3) 0.001(2) C21D 0.028(3) 0.040(3) 0.033(3) -0.003(2) -0.011(2) 0.003(2) C22D 0.028(3) 0.045(3) 0.043(3) -0.005(2) -0.009(2) -0.003(2) C23D 0.029(3) 0.049(3) 0.049(4) -0.005(3) -0.006(3) 0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C19A 1.231(6) . ? O2A C1A 1.433(6) . ? O2A C21A 1.437(6) . ? O3A C21A 1.422(6) . ? O3A C3A 1.455(5) . ? N1A C19A 1.337(6) . ? N1A C2A 1.452(6) . ? N1A H1A 0.8800 . ? C1A C2A 1.520(7) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2A C3A 1.526(7) . ? C2A H2A 1.0000 . ? C3A C4A 1.503(7) . ? C3A H3A 1.0000 . ? C4A C5A 1.324(7) . ? C4A H4A 0.9500 . ? C5A C6A 1.494(7) . ? C5A H5A 0.9500 . ? C6A C7A 1.532(7) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A C8A 1.527(7) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C8A C9A 1.523(7) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A C10A 1.535(7) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10A C11A 1.517(7) . ? C10A H10A 0.9900 . ? C10A H10B 0.9900 . ? C11A C12A 1.533(7) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A C13A 1.524(7) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A C14A 1.525(7) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C14A C15A 1.527(7) . ? C14A H14A 0.9900 . ? C14A H14B 0.9900 . ? C15A C16A 1.516(7) . ? C15A H15A 0.9900 . ? C15A H15B 0.9900 . ? C16A C17A 1.531(7) . ? C16A H16A 0.9900 . ? C16A H16B 0.9900 . ? C17A C18A 1.534(8) . ? C17A H17A 0.9900 . ? C17A H17B 0.9900 . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? C19A C20A 1.518(6) . ? C20A H20A 0.9800 . ? C20A H20B 0.9800 . ? C20A H20C 0.9800 . ? C21A C22A 1.516(6) . ? C21A C23A 1.524(7) . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C23A H23A 0.9800 . ? C23A H23B 0.9800 . ? C23A H23C 0.9800 . ? O1B C19B 1.229(6) . ? O2B C21B 1.426(6) . ? O2B C1B 1.435(6) . ? O3B C3B 1.442(5) . ? O3B C21B 1.448(6) . ? N1B C19B 1.336(6) . ? N1B C2B 1.465(6) . ? N1B H1B 0.8800 . ? C1B C2B 1.524(7) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? C2B C3B 1.516(7) . ? C2B H2B 1.0000 . ? C3B C4B 1.494(7) . ? C3B H3B 1.0000 . ? C4B C5B 1.303(7) . ? C4B H4B 0.9500 . ? C5B C6B 1.513(8) . ? C5B H5B 0.9500 . ? C6B C7B 1.517(8) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B C8B 1.510(7) . ? C7B H7B1 0.9900 . ? C7B H7B2 0.9900 . ? C8B C9B 1.516(7) . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9B C10B 1.517(7) . ? C9B H9B1 0.9900 . ? C9B H9B2 0.9900 . ? C10B C11B 1.525(7) . ? C10B H10C 0.9900 . ? C10B H10D 0.9900 . ? C11B C12B 1.523(7) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B C13B 1.526(7) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B C14B 1.522(7) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B C15B 1.519(7) . ? C14B H14C 0.9900 . ? C14B H14D 0.9900 . ? C15B C16B 1.520(7) . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C16B C17B 1.519(7) . ? C16B H16C 0.9900 . ? C16B H16D 0.9900 . ? C17B C18B 1.517(8) . ? C17B H17C 0.9900 . ? C17B H17D 0.9900 . ? C18B H18D 0.9800 . ? C18B H18E 0.9800 . ? C18B H18F 0.9800 . ? C19B C20B 1.522(7) . ? C20B H20D 0.9800 . ? C20B H20E 0.9800 . ? C20B H20F 0.9800 . ? C21B C23B 1.513(7) . ? C21B C22B 1.519(7) . ? C22B H22D 0.9800 . ? C22B H22E 0.9800 . ? C22B H22F 0.9800 . ? C23B H23D 0.9800 . ? C23B H23E 0.9800 . ? C23B H23F 0.9800 . ? O1C C19C 1.228(6) . ? O2C C1C 1.428(6) . ? O2C C21C 1.437(6) . ? O3C C3C 1.428(6) . ? O3C C21C 1.429(6) . ? N1C C19C 1.354(6) . ? N1C C2C 1.458(6) . ? N1C H1C 0.8800 . ? C1C C2C 1.536(7) . ? C1C H1C1 0.9900 . ? C1C H1C2 0.9900 . ? C2C C3C 1.535(7) . ? C2C H2C 1.0000 . ? C3C C4C 1.495(7) . ? C3C H3C 1.0000 . ? C4C C5C 1.304(7) . ? C4C H4C 0.9500 . ? C5C C6C 1.504(7) . ? C5C H5C 0.9500 . ? C6C C7C 1.516(7) . ? C6C H6C1 0.9900 . ? C6C H6C2 0.9900 . ? C7C C8C 1.530(7) . ? C7C H7C1 0.9900 . ? C7C H7C2 0.9900 . ? C8C C9C 1.520(7) . ? C8C H8C1 0.9900 . ? C8C H8C2 0.9900 . ? C9C C10C 1.522(7) . ? C9C H9C1 0.9900 . ? C9C H9C2 0.9900 . ? C10C C11C 1.514(7) . ? C10C H10E 0.9900 . ? C10C H10F 0.9900 . ? C11C C12C 1.515(7) . ? C11C H11E 0.9900 . ? C11C H11F 0.9900 . ? C12C C13C 1.525(7) . ? C12C H12E 0.9900 . ? C12C H12F 0.9900 . ? C13C C14C 1.528(7) . ? C13C H13E 0.9900 . ? C13C H13F 0.9900 . ? C14C C15C 1.520(7) . ? C14C H14E 0.9900 . ? C14C H14F 0.9900 . ? C15C C16C 1.537(7) . ? C15C H15E 0.9900 . ? C15C H15F 0.9900 . ? C16C C17C 1.514(7) . ? C16C H16E 0.9900 . ? C16C H16F 0.9900 . ? C17C C18C 1.525(7) . ? C17C H17E 0.9900 . ? C17C H17F 0.9900 . ? C18C H18G 0.9800 . ? C18C H18H 0.9800 . ? C18C H18I 0.9800 . ? C19C C20C 1.501(7) . ? C20C H20G 0.9800 . ? C20C H20H 0.9800 . ? C20C H20I 0.9800 . ? C21C C23C 1.508(7) . ? C21C C22C 1.532(7) . ? C22C H22G 0.9800 . ? C22C H22H 0.9800 . ? C22C H22I 0.9800 . ? C23C H23G 0.9800 . ? C23C H23H 0.9800 . ? C23C H23I 0.9800 . ? O1D C19D 1.231(6) . ? O2D C21D 1.428(6) . ? O2D C1D 1.436(6) . ? O3D C21D 1.436(6) . ? O3D C3D 1.458(6) . ? N1D C19D 1.347(6) . ? N1D C2D 1.458(6) . ? N1D H1D 0.8800 . ? C1D C2D 1.525(7) . ? C1D H1D1 0.9900 . ? C1D H1D2 0.9900 . ? C2D C3D 1.537(7) . ? C2D H2D 1.0000 . ? C3D C4D 1.503(7) . ? C3D H3D 1.0000 . ? C4D C5D 1.310(7) . ? C4D H4D 0.9500 . ? C5D C6D 1.490(7) . ? C5D H5D 0.9500 . ? C6D C7D 1.537(7) . ? C6D H6D1 0.9900 . ? C6D H6D2 0.9900 . ? C7D C8D 1.530(7) . ? C7D H7D1 0.9900 . ? C7D H7D2 0.9900 . ? C8D C9D 1.531(7) . ? C8D H8D1 0.9900 . ? C8D H8D2 0.9900 . ? C9D C10D 1.522(7) . ? C9D H9D1 0.9900 . ? C9D H9D2 0.9900 . ? C10D C11D 1.518(7) . ? C10D H10G 0.9900 . ? C10D H10H 0.9900 . ? C11D C12D 1.529(7) . ? C11D H11G 0.9900 . ? C11D H11H 0.9900 . ? C12D C13D 1.527(7) . ? C12D H12G 0.9900 . ? C12D H12H 0.9900 . ? C13D C14D 1.528(7) . ? C13D H13G 0.9900 . ? C13D H13H 0.9900 . ? C14D C15D 1.521(7) . ? C14D H14G 0.9900 . ? C14D H14H 0.9900 . ? C15D C16D 1.521(7) . ? C15D H15G 0.9900 . ? C15D H15H 0.9900 . ? C16D C17D 1.516(8) . ? C16D H16G 0.9900 . ? C16D H16H 0.9900 . ? C17D C18D 1.529(8) . ? C17D H17G 0.9900 . ? C17D H17H 0.9900 . ? C18D H18J 0.9800 . ? C18D H18K 0.9800 . ? C18D H18L 0.9800 . ? C19D C20D 1.491(7) . ? C20D H20J 0.9800 . ? C20D H20K 0.9800 . ? C20D H20L 0.9800 . ? C21D C23D 1.508(7) . ? C21D C22D 1.526(7) . ? C22D H22J 0.9800 . ? C22D H22K 0.9800 . ? C22D H22L 0.9800 . ? C23D H23J 0.9800 . ? C23D H23K 0.9800 . ? C23D H23L 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 C1A O2A C21A 114.1(4) . . ? C21A O3A C3A 115.0(3) . . ? C19A N1A C2A 122.0(4) . . ? C19A N1A H1A 119.0 . . ? C2A N1A H1A 119.0 . . ? O2A C1A C2A 108.8(4) . . ? O2A C1A H1A1 109.9 . . ? C2A C1A H1A1 109.9 . . ? O2A C1A H1A2 109.9 . . ? C2A C1A H1A2 109.9 . . ? H1A1 C1A H1A2 108.3 . . ? N1A C2A C1A 112.4(4) . . ? N1A C2A C3A 110.7(4) . . ? C1A C2A C3A 109.7(4) . . ? N1A C2A H2A 108.0 . . ? C1A C2A H2A 108.0 . . ? C3A C2A H2A 108.0 . . ? O3A C3A C4A 108.2(4) . . ? O3A C3A C2A 107.6(4) . . ? C4A C3A C2A 113.0(4) . . ? O3A C3A H3A 109.3 . . ? C4A C3A H3A 109.3 . . ? C2A C3A H3A 109.3 . . ? C5A C4A C3A 122.8(4) . . ? C5A C4A H4A 118.6 . . ? C3A C4A H4A 118.6 . . ? C4A C5A C6A 127.9(5) . . ? C4A C5A H5A 116.1 . . ? C6A C5A H5A 116.1 . . ? C5A C6A C7A 118.4(4) . . ? C5A C6A H6A1 107.7 . . ? C7A C6A H6A1 107.7 . . ? C5A C6A H6A2 107.7 . . ? C7A C6A H6A2 107.7 . . ? H6A1 C6A H6A2 107.1 . . ? C8A C7A C6A 111.1(4) . . ? C8A C7A H7A1 109.4 . . ? C6A C7A H7A1 109.4 . . ? C8A C7A H7A2 109.4 . . ? C6A C7A H7A2 109.4 . . ? H7A1 C7A H7A2 108.0 . . ? C9A C8A C7A 115.6(4) . . ? C9A C8A H8A1 108.4 . . ? C7A C8A H8A1 108.4 . . ? C9A C8A H8A2 108.4 . . ? C7A C8A H8A2 108.4 . . ? H8A1 C8A H8A2 107.4 . . ? C8A C9A C10A 113.0(4) . . ? C8A C9A H9A1 109.0 . . ? C10A C9A H9A1 109.0 . . ? C8A C9A H9A2 109.0 . . ? C10A C9A H9A2 109.0 . . ? H9A1 C9A H9A2 107.8 . . ? C11A C10A C9A 114.7(4) . . ? C11A C10A H10A 108.6 . . ? C9A C10A H10A 108.6 . . ? C11A C10A H10B 108.6 . . ? C9A C10A H10B 108.6 . . ? H10A C10A H10B 107.6 . . ? C10A C11A C12A 113.3(4) . . ? C10A C11A H11A 108.9 . . ? C12A C11A H11A 108.9 . . ? C10A C11A H11B 108.9 . . ? C12A C11A H11B 108.9 . . ? H11A C11A H11B 107.7 . . ? C13A C12A C11A 113.8(4) . . ? C13A C12A H12A 108.8 . . ? C11A C12A H12A 108.8 . . ? C13A C12A H12B 108.8 . . ? C11A C12A H12B 108.8 . . ? H12A C12A H12B 107.7 . . ? C12A C13A C14A 113.9(4) . . ? C12A C13A H13A 108.8 . . ? C14A C13A H13A 108.8 . . ? C12A C13A H13B 108.8 . . ? C14A C13A H13B 108.8 . . ? H13A C13A H13B 107.7 . . ? C13A C14A C15A 113.5(4) . . ? C13A C14A H14A 108.9 . . ? C15A C14A H14A 108.9 . . ? C13A C14A H14B 108.9 . . ? C15A C14A H14B 108.9 . . ? H14A C14A H14B 107.7 . . ? C16A C15A C14A 114.3(4) . . ? C16A C15A H15A 108.7 . . ? C14A C15A H15A 108.7 . . ? C16A C15A H15B 108.7 . . ? C14A C15A H15B 108.7 . . ? H15A C15A H15B 107.6 . . ? C15A C16A C17A 113.4(4) . . ? C15A C16A H16A 108.9 . . ? C17A C16A H16A 108.9 . . ? C15A C16A H16B 108.9 . . ? C17A C16A H16B 108.9 . . ? H16A C16A H16B 107.7 . . ? C16A C17A C18A 114.0(5) . . ? C16A C17A H17A 108.8 . . ? C18A C17A H17A 108.8 . . ? C16A C17A H17B 108.8 . . ? C18A C17A H17B 108.8 . . ? H17A C17A H17B 107.6 . . ? C17A C18A H18A 109.5 . . ? C17A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C17A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? O1A C19A N1A 123.6(4) . . ? O1A C19A C20A 121.3(5) . . ? N1A C19A C20A 115.1(4) . . ? C19A C20A H20A 109.5 . . ? C19A C20A H20B 109.5 . . ? H20A C20A H20B 109.5 . . ? C19A C20A H20C 109.5 . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? O3A C21A O2A 110.7(4) . . ? O3A C21A C22A 105.1(4) . . ? O2A C21A C22A 105.0(4) . . ? O3A C21A C23A 112.1(4) . . ? O2A C21A C23A 111.6(4) . . ? C22A C21A C23A 111.9(4) . . ? C21A C22A H22A 109.5 . . ? C21A C22A H22B 109.5 . . ? H22A C22A H22B 109.5 . . ? C21A C22A H22C 109.5 . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? C21A C23A H23A 109.5 . . ? C21A C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? C21A C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C21B O2B C1B 114.1(4) . . ? C3B O3B C21B 115.9(3) . . ? C19B N1B C2B 121.9(4) . . ? C19B N1B H1B 119.0 . . ? C2B N1B H1B 119.0 . . ? O2B C1B C2B 109.5(4) . . ? O2B C1B H1B1 109.8 . . ? C2B C1B H1B1 109.8 . . ? O2B C1B H1B2 109.8 . . ? C2B C1B H1B2 109.8 . . ? H1B1 C1B H1B2 108.2 . . ? N1B C2B C3B 111.8(4) . . ? N1B C2B C1B 111.3(4) . . ? C3B C2B C1B 109.9(4) . . ? N1B C2B H2B 107.9 . . ? C3B C2B H2B 107.9 . . ? C1B C2B H2B 107.9 . . ? O3B C3B C4B 107.1(4) . . ? O3B C3B C2B 107.4(4) . . ? C4B C3B C2B 112.2(4) . . ? O3B C3B H3B 110.0 . . ? C4B C3B H3B 110.0 . . ? C2B C3B H3B 110.0 . . ? C5B C4B C3B 125.7(5) . . ? C5B C4B H4B 117.2 . . ? C3B C4B H4B 117.2 . . ? C4B C5B C6B 125.5(6) . . ? C4B C5B H5B 117.3 . . ? C6B C5B H5B 117.3 . . ? C5B C6B C7B 113.4(5) . . ? C5B C6B H6B1 108.9 . . ? C7B C6B H6B1 108.9 . . ? C5B C6B H6B2 108.9 . . ? C7B C6B H6B2 108.9 . . ? H6B1 C6B H6B2 107.7 . . ? C8B C7B C6B 112.5(5) . . ? C8B C7B H7B1 109.1 . . ? C6B C7B H7B1 109.1 . . ? C8B C7B H7B2 109.1 . . ? C6B C7B H7B2 109.1 . . ? H7B1 C7B H7B2 107.8 . . ? C7B C8B C9B 114.6(4) . . ? C7B C8B H8B1 108.6 . . ? C9B C8B H8B1 108.6 . . ? C7B C8B H8B2 108.6 . . ? C9B C8B H8B2 108.6 . . ? H8B1 C8B H8B2 107.6 . . ? C8B C9B C10B 113.7(4) . . ? C8B C9B H9B1 108.8 . . ? C10B C9B H9B1 108.8 . . ? C8B C9B H9B2 108.8 . . ? C10B C9B H9B2 108.8 . . ? H9B1 C9B H9B2 107.7 . . ? C9B C10B C11B 114.8(4) . . ? C9B C10B H10C 108.6 . . ? C11B C10B H10C 108.6 . . ? C9B C10B H10D 108.6 . . ? C11B C10B H10D 108.6 . . ? H10C C10B H10D 107.5 . . ? C12B C11B C10B 113.2(4) . . ? C12B C11B H11C 108.9 . . ? C10B C11B H11C 108.9 . . ? C12B C11B H11D 108.9 . . ? C10B C11B H11D 108.9 . . ? H11C C11B H11D 107.7 . . ? C11B C12B C13B 113.6(4) . . ? C11B C12B H12C 108.8 . . ? C13B C12B H12C 108.8 . . ? C11B C12B H12D 108.8 . . ? C13B C12B H12D 108.8 . . ? H12C C12B H12D 107.7 . . ? C14B C13B C12B 113.5(4) . . ? C14B C13B H13C 108.9 . . ? C12B C13B H13C 108.9 . . ? C14B C13B H13D 108.9 . . ? C12B C13B H13D 108.9 . . ? H13C C13B H13D 107.7 . . ? C15B C14B C13B 113.7(4) . . ? C15B C14B H14C 108.8 . . ? C13B C14B H14C 108.8 . . ? C15B C14B H14D 108.8 . . ? C13B C14B H14D 108.8 . . ? H14C C14B H14D 107.7 . . ? C14B C15B C16B 114.3(4) . . ? C14B C15B H15C 108.7 . . ? C16B C15B H15C 108.7 . . ? C14B C15B H15D 108.7 . . ? C16B C15B H15D 108.7 . . ? H15C C15B H15D 107.6 . . ? C17B C16B C15B 113.9(4) . . ? C17B C16B H16C 108.8 . . ? C15B C16B H16C 108.8 . . ? C17B C16B H16D 108.8 . . ? C15B C16B H16D 108.8 . . ? H16C C16B H16D 107.7 . . ? C18B C17B C16B 114.7(5) . . ? C18B C17B H17C 108.6 . . ? C16B C17B H17C 108.6 . . ? C18B C17B H17D 108.6 . . ? C16B C17B H17D 108.6 . . ? H17C C17B H17D 107.6 . . ? C17B C18B H18D 109.5 . . ? C17B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C17B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? O1B C19B N1B 123.5(4) . . ? O1B C19B C20B 120.4(4) . . ? N1B C19B C20B 116.1(4) . . ? C19B C20B H20D 109.5 . . ? C19B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C19B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? O2B C21B O3B 109.9(4) . . ? O2B C21B C23B 105.7(4) . . ? O3B C21B C23B 104.9(4) . . ? O2B C21B C22B 112.7(4) . . ? O3B C21B C22B 112.0(4) . . ? C23B C21B C22B 111.1(4) . . ? C21B C22B H22D 109.5 . . ? C21B C22B H22E 109.5 . . ? H22D C22B H22E 109.5 . . ? C21B C22B H22F 109.5 . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? C21B C23B H23D 109.5 . . ? C21B C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C21B C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? C1C O2C C21C 114.2(4) . . ? C3C O3C C21C 115.6(4) . . ? C19C N1C C2C 122.0(4) . . ? C19C N1C H1C 119.0 . . ? C2C N1C H1C 119.0 . . ? O2C C1C C2C 109.0(4) . . ? O2C C1C H1C1 109.9 . . ? C2C C1C H1C1 109.9 . . ? O2C C1C H1C2 109.9 . . ? C2C C1C H1C2 109.9 . . ? H1C1 C1C H1C2 108.3 . . ? N1C C2C C3C 111.8(4) . . ? N1C C2C C1C 111.2(4) . . ? C3C C2C C1C 109.1(4) . . ? N1C C2C H2C 108.2 . . ? C3C C2C H2C 108.2 . . ? C1C C2C H2C 108.2 . . ? O3C C3C C4C 107.9(4) . . ? O3C C3C C2C 107.6(4) . . ? C4C C3C C2C 111.9(4) . . ? O3C C3C H3C 109.8 . . ? C4C C3C H3C 109.8 . . ? C2C C3C H3C 109.8 . . ? C5C C4C C3C 126.5(5) . . ? C5C C4C H4C 116.8 . . ? C3C C4C H4C 116.8 . . ? C4C C5C C6C 125.9(5) . . ? C4C C5C H5C 117.0 . . ? C6C C5C H5C 117.0 . . ? C5C C6C C7C 112.1(4) . . ? C5C C6C H6C1 109.2 . . ? C7C C6C H6C1 109.2 . . ? C5C C6C H6C2 109.2 . . ? C7C C6C H6C2 109.2 . . ? H6C1 C6C H6C2 107.9 . . ? C6C C7C C8C 115.1(4) . . ? C6C C7C H7C1 108.5 . . ? C8C C7C H7C1 108.5 . . ? C6C C7C H7C2 108.5 . . ? C8C C7C H7C2 108.5 . . ? H7C1 C7C H7C2 107.5 . . ? C9C C8C C7C 113.1(4) . . ? C9C C8C H8C1 109.0 . . ? C7C C8C H8C1 109.0 . . ? C9C C8C H8C2 109.0 . . ? C7C C8C H8C2 109.0 . . ? H8C1 C8C H8C2 107.8 . . ? C8C C9C C10C 114.3(4) . . ? C8C C9C H9C1 108.7 . . ? C10C C9C H9C1 108.7 . . ? C8C C9C H9C2 108.7 . . ? C10C C9C H9C2 108.7 . . ? H9C1 C9C H9C2 107.6 . . ? C11C C10C C9C 114.3(4) . . ? C11C C10C H10E 108.7 . . ? C9C C10C H10E 108.7 . . ? C11C C10C H10F 108.7 . . ? C9C C10C H10F 108.7 . . ? H10E C10C H10F 107.6 . . ? C10C C11C C12C 114.1(4) . . ? C10C C11C H11E 108.7 . . ? C12C C11C H11E 108.7 . . ? C10C C11C H11F 108.7 . . ? C12C C11C H11F 108.7 . . ? H11E C11C H11F 107.6 . . ? C11C C12C C13C 114.1(4) . . ? C11C C12C H12E 108.7 . . ? C13C C12C H12E 108.7 . . ? C11C C12C H12F 108.7 . . ? C13C C12C H12F 108.7 . . ? H12E C12C H12F 107.6 . . ? C12C C13C C14C 114.9(4) . . ? C12C C13C H13E 108.5 . . ? C14C C13C H13E 108.5 . . ? C12C C13C H13F 108.5 . . ? C14C C13C H13F 108.5 . . ? H13E C13C H13F 107.5 . . ? C15C C14C C13C 113.4(4) . . ? C15C C14C H14E 108.9 . . ? C13C C14C H14E 108.9 . . ? C15C C14C H14F 108.9 . . ? C13C C14C H14F 108.9 . . ? H14E C14C H14F 107.7 . . ? C14C C15C C16C 115.0(4) . . ? C14C C15C H15E 108.5 . . ? C16C C15C H15E 108.5 . . ? C14C C15C H15F 108.5 . . ? C16C C15C H15F 108.5 . . ? H15E C15C H15F 107.5 . . ? C17C C16C C15C 113.0(4) . . ? C17C C16C H16E 109.0 . . ? C15C C16C H16E 109.0 . . ? C17C C16C H16F 109.0 . . ? C15C C16C H16F 109.0 . . ? H16E C16C H16F 107.8 . . ? C16C C17C C18C 115.0(4) . . ? C16C C17C H17E 108.5 . . ? C18C C17C H17E 108.5 . . ? C16C C17C H17F 108.5 . . ? C18C C17C H17F 108.5 . . ? H17E C17C H17F 107.5 . . ? C17C C18C H18G 109.5 . . ? C17C C18C H18H 109.5 . . ? H18G C18C H18H 109.5 . . ? C17C C18C H18I 109.5 . . ? H18G C18C H18I 109.5 . . ? H18H C18C H18I 109.5 . . ? O1C C19C N1C 123.1(5) . . ? O1C C19C C20C 121.7(5) . . ? N1C C19C C20C 115.2(4) . . ? C19C C20C H20G 109.5 . . ? C19C C20C H20H 109.5 . . ? H20G C20C H20H 109.5 . . ? C19C C20C H20I 109.5 . . ? H20G C20C H20I 109.5 . . ? H20H C20C H20I 109.5 . . ? O3C C21C O2C 110.7(4) . . ? O3C C21C C23C 105.6(4) . . ? O2C C21C C23C 105.4(4) . . ? O3C C21C C22C 111.7(4) . . ? O2C C21C C22C 111.2(4) . . ? C23C C21C C22C 111.8(4) . . ? C21C C22C H22G 109.5 . . ? C21C C22C H22H 109.5 . . ? H22G C22C H22H 109.5 . . ? C21C C22C H22I 109.5 . . ? H22G C22C H22I 109.5 . . ? H22H C22C H22I 109.5 . . ? C21C C23C H23G 109.5 . . ? C21C C23C H23H 109.5 . . ? H23G C23C H23H 109.5 . . ? C21C C23C H23I 109.5 . . ? H23G C23C H23I 109.5 . . ? H23H C23C H23I 109.5 . . ? C21D O2D C1D 114.5(4) . . ? C21D O3D C3D 114.4(4) . . ? C19D N1D C2D 121.6(4) . . ? C19D N1D H1D 119.2 . . ? C2D N1D H1D 119.2 . . ? O2D C1D C2D 110.2(4) . . ? O2D C1D H1D1 109.6 . . ? C2D C1D H1D1 109.6 . . ? O2D C1D H1D2 109.6 . . ? C2D C1D H1D2 109.6 . . ? H1D1 C1D H1D2 108.1 . . ? N1D C2D C1D 111.8(4) . . ? N1D C2D C3D 109.9(4) . . ? C1D C2D C3D 108.6(4) . . ? N1D C2D H2D 108.8 . . ? C1D C2D H2D 108.8 . . ? C3D C2D H2D 108.8 . . ? O3D C3D C4D 107.4(4) . . ? O3D C3D C2D 106.6(4) . . ? C4D C3D C2D 115.1(4) . . ? O3D C3D H3D 109.2 . . ? C4D C3D H3D 109.2 . . ? C2D C3D H3D 109.2 . . ? C5D C4D C3D 123.1(5) . . ? C5D C4D H4D 118.4 . . ? C3D C4D H4D 118.4 . . ? C4D C5D C6D 126.3(5) . . ? C4D C5D H5D 116.8 . . ? C6D C5D H5D 116.8 . . ? C5D C6D C7D 111.1(4) . . ? C5D C6D H6D1 109.4 . . ? C7D C6D H6D1 109.4 . . ? C5D C6D H6D2 109.4 . . ? C7D C6D H6D2 109.4 . . ? H6D1 C6D H6D2 108.0 . . ? C8D C7D C6D 114.5(4) . . ? C8D C7D H7D1 108.6 . . ? C6D C7D H7D1 108.6 . . ? C8D C7D H7D2 108.6 . . ? C6D C7D H7D2 108.6 . . ? H7D1 C7D H7D2 107.6 . . ? C7D C8D C9D 112.8(4) . . ? C7D C8D H8D1 109.0 . . ? C9D C8D H8D1 109.0 . . ? C7D C8D H8D2 109.0 . . ? C9D C8D H8D2 109.0 . . ? H8D1 C8D H8D2 107.8 . . ? C10D C9D C8D 113.4(4) . . ? C10D C9D H9D1 108.9 . . ? C8D C9D H9D1 108.9 . . ? C10D C9D H9D2 108.9 . . ? C8D C9D H9D2 108.9 . . ? H9D1 C9D H9D2 107.7 . . ? C11D C10D C9D 113.8(4) . . ? C11D C10D H10G 108.8 . . ? C9D C10D H10G 108.8 . . ? C11D C10D H10H 108.8 . . ? C9D C10D H10H 108.8 . . ? H10G C10D H10H 107.7 . . ? C10D C11D C12D 113.7(4) . . ? C10D C11D H11G 108.8 . . ? C12D C11D H11G 108.8 . . ? C10D C11D H11H 108.8 . . ? C12D C11D H11H 108.8 . . ? H11G C11D H11H 107.7 . . ? C13D C12D C11D 113.6(4) . . ? C13D C12D H12G 108.8 . . ? C11D C12D H12G 108.8 . . ? C13D C12D H12H 108.8 . . ? C11D C12D H12H 108.8 . . ? H12G C12D H12H 107.7 . . ? C12D C13D C14D 113.7(4) . . ? C12D C13D H13G 108.8 . . ? C14D C13D H13G 108.8 . . ? C12D C13D H13H 108.8 . . ? C14D C13D H13H 108.8 . . ? H13G C13D H13H 107.7 . . ? C15D C14D C13D 113.6(4) . . ? C15D C14D H14G 108.8 . . ? C13D C14D H14G 108.8 . . ? C15D C14D H14H 108.8 . . ? C13D C14D H14H 108.8 . . ? H14G C14D H14H 107.7 . . ? C14D C15D C16D 114.7(4) . . ? C14D C15D H15G 108.6 . . ? C16D C15D H15G 108.6 . . ? C14D C15D H15H 108.6 . . ? C16D C15D H15H 108.6 . . ? H15G C15D H15H 107.6 . . ? C17D C16D C15D 113.8(5) . . ? C17D C16D H16G 108.8 . . ? C15D C16D H16G 108.8 . . ? C17D C16D H16H 108.8 . . ? C15D C16D H16H 108.8 . . ? H16G C16D H16H 107.7 . . ? C16D C17D C18D 114.1(5) . . ? C16D C17D H17G 108.7 . . ? C18D C17D H17G 108.7 . . ? C16D C17D H17H 108.7 . . ? C18D C17D H17H 108.7 . . ? H17G C17D H17H 107.6 . . ? C17D C18D H18J 109.5 . . ? C17D C18D H18K 109.5 . . ? H18J C18D H18K 109.5 . . ? C17D C18D H18L 109.5 . . ? H18J C18D H18L 109.5 . . ? H18K C18D H18L 109.5 . . ? O1D C19D N1D 121.9(5) . . ? O1D C19D C20D 121.6(5) . . ? N1D C19D C20D 116.5(4) . . ? C19D C20D H20J 109.5 . . ? C19D C20D H20K 109.5 . . ? H20J C20D H20K 109.5 . . ? C19D C20D H20L 109.5 . . ? H20J C20D H20L 109.5 . . ? H20K C20D H20L 109.5 . . ? O2D C21D O3D 110.1(4) . . ? O2D C21D C23D 106.1(4) . . ? O3D C21D C23D 105.1(4) . . ? O2D C21D C22D 112.5(4) . . ? O3D C21D C22D 111.2(4) . . ? C23D C21D C22D 111.5(4) . . ? C21D C22D H22J 109.5 . . ? C21D C22D H22K 109.5 . . ? H22J C22D H22K 109.5 . . ? C21D C22D H22L 109.5 . . ? H22J C22D H22L 109.5 . . ? H22K C22D H22L 109.5 . . ? C21D C23D H23J 109.5 . . ? C21D C23D H23K 109.5 . . ? H23J C23D H23K 109.5 . . ? C21D C23D H23L 109.5 . . ? H23J C23D H23L 109.5 . . ? H23K C23D H23L 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 C21A O2A C1A C2A 56.9(5) . . . . ? C19A N1A C2A C1A -137.7(5) . . . . ? C19A N1A C2A C3A 99.3(5) . . . . ? O2A C1A C2A N1A 179.5(4) . . . . ? O2A C1A C2A C3A -56.9(5) . . . . ? C21A O3A C3A C4A -178.6(4) . . . . ? C21A O3A C3A C2A -56.2(5) . . . . ? N1A C2A C3A O3A -179.7(4) . . . . ? C1A C2A C3A O3A 55.7(4) . . . . ? N1A C2A C3A C4A -60.3(5) . . . . ? C1A C2A C3A C4A 175.1(4) . . . . ? O3A C3A C4A C5A -110.7(5) . . . . ? C2A C3A C4A C5A 130.3(5) . . . . ? C3A C4A C5A C6A -178.5(5) . . . . ? C4A C5A C6A C7A 5.9(8) . . . . ? C5A C6A C7A C8A 176.6(4) . . . . ? C6A C7A C8A C9A 179.1(4) . . . . ? C7A C8A C9A C10A -178.5(4) . . . . ? C8A C9A C10A C11A -178.6(4) . . . . ? C9A C10A C11A C12A -179.0(4) . . . . ? C10A C11A C12A C13A 179.9(4) . . . . ? C11A C12A C13A C14A -179.8(4) . . . . ? C12A C13A C14A C15A -180.0(4) . . . . ? C13A C14A C15A C16A -179.9(4) . . . . ? C14A C15A C16A C17A -179.6(4) . . . . ? C15A C16A C17A C18A -179.2(4) . . . . ? C2A N1A C19A O1A 10.9(8) . . . . ? C2A N1A C19A C20A -169.1(4) . . . . ? C3A O3A C21A O2A 55.4(5) . . . . ? C3A O3A C21A C22A 168.2(4) . . . . ? C3A O3A C21A C23A -69.9(5) . . . . ? C1A O2A C21A O3A -55.3(5) . . . . ? C1A O2A C21A C22A -168.2(4) . . . . ? C1A O2A C21A C23A 70.3(5) . . . . ? C21B O2B C1B C2B 56.7(6) . . . . ? C19B N1B C2B C3B 128.8(5) . . . . ? C19B N1B C2B C1B -107.8(5) . . . . ? O2B C1B C2B N1B 179.0(4) . . . . ? O2B C1B C2B C3B -56.5(5) . . . . ? C21B O3B C3B C4B -177.0(4) . . . . ? C21B O3B C3B C2B -56.2(5) . . . . ? N1B C2B C3B O3B 179.3(4) . . . . ? C1B C2B C3B O3B 55.2(5) . . . . ? N1B C2B C3B C4B -63.2(5) . . . . ? C1B C2B C3B C4B 172.7(4) . . . . ? O3B C3B C4B C5B -108.1(6) . . . . ? C2B C3B C4B C5B 134.2(6) . . . . ? C3B C4B C5B C6B 178.5(5) . . . . ? C4B C5B C6B C7B -91.8(7) . . . . ? C5B C6B C7B C8B -172.3(5) . . . . ? C6B C7B C8B C9B -172.5(5) . . . . ? C7B C8B C9B C10B -176.6(4) . . . . ? C8B C9B C10B C11B -178.1(4) . . . . ? C9B C10B C11B C12B -178.7(4) . . . . ? C10B C11B C12B C13B -179.6(4) . . . . ? C11B C12B C13B C14B -178.7(4) . . . . ? C12B C13B C14B C15B 178.8(4) . . . . ? C13B C14B C15B C16B -179.7(4) . . . . ? C14B C15B C16B C17B -178.4(4) . . . . ? C15B C16B C17B C18B 178.5(5) . . . . ? C2B N1B C19B O1B 0.1(7) . . . . ? C2B N1B C19B C20B 179.3(4) . . . . ? C1B O2B C21B O3B -54.5(5) . . . . ? C1B O2B C21B C23B -167.2(4) . . . . ? C1B O2B C21B C22B 71.3(5) . . . . ? C3B O3B C21B O2B 55.3(5) . . . . ? C3B O3B C21B C23B 168.6(4) . . . . ? C3B O3B C21B C22B -70.8(5) . . . . ? C21C O2C C1C C2C 56.2(5) . . . . ? C19C N1C C2C C3C 103.4(5) . . . . ? C19C N1C C2C C1C -134.3(5) . . . . ? O2C C1C C2C N1C 179.8(4) . . . . ? O2C C1C C2C C3C -56.4(5) . . . . ? C21C O3C C3C C4C -177.9(4) . . . . ? C21C O3C C3C C2C -57.1(5) . . . . ? N1C C2C C3C O3C 179.5(4) . . . . ? C1C C2C C3C O3C 56.0(5) . . . . ? N1C C2C C3C C4C -62.3(5) . . . . ? C1C C2C C3C C4C 174.2(4) . . . . ? O3C C3C C4C C5C -99.4(6) . . . . ? C2C C3C C4C C5C 142.6(5) . . . . ? C3C C4C C5C C6C 179.2(5) . . . . ? C4C C5C C6C C7C 132.9(6) . . . . ? C5C C6C C7C C8C 179.3(4) . . . . ? C6C C7C C8C C9C -175.0(4) . . . . ? C7C C8C C9C C10C 179.3(4) . . . . ? C8C C9C C10C C11C -178.7(4) . . . . ? C9C C10C C11C C12C 179.8(4) . . . . ? C10C C11C C12C C13C -178.9(4) . . . . ? C11C C12C C13C C14C 179.6(4) . . . . ? C12C C13C C14C C15C 180.0(4) . . . . ? C13C C14C C15C C16C 179.6(4) . . . . ? C14C C15C C16C C17C 179.5(4) . . . . ? C15C C16C C17C C18C 179.3(4) . . . . ? C2C N1C C19C O1C 11.3(8) . . . . ? C2C N1C C19C C20C -168.4(4) . . . . ? C3C O3C C21C O2C 55.6(5) . . . . ? C3C O3C C21C C23C 169.3(4) . . . . ? C3C O3C C21C C22C -68.9(5) . . . . ? C1C O2C C21C O3C -54.4(5) . . . . ? C1C O2C C21C C23C -168.2(4) . . . . ? C1C O2C C21C C22C 70.5(5) . . . . ? C21D O2D C1D C2D 55.3(5) . . . . ? C19D N1D C2D C1D -91.6(5) . . . . ? C19D N1D C2D C3D 147.7(4) . . . . ? O2D C1D C2D N1D -177.4(4) . . . . ? O2D C1D C2D C3D -56.0(5) . . . . ? C21D O3D C3D C4D 176.3(4) . . . . ? C21D O3D C3D C2D -59.8(5) . . . . ? N1D C2D C3D O3D 179.7(4) . . . . ? C1D C2D C3D O3D 57.1(5) . . . . ? N1D C2D C3D C4D -61.4(5) . . . . ? C1D C2D C3D C4D 176.0(4) . . . . ? O3D C3D C4D C5D -123.2(5) . . . . ? C2D C3D C4D C5D 118.3(5) . . . . ? C3D C4D C5D C6D 177.2(5) . . . . ? C4D C5D C6D C7D -113.5(6) . . . . ? C5D C6D C7D C8D -170.3(4) . . . . ? C6D C7D C8D C9D 177.3(4) . . . . ? C7D C8D C9D C10D -175.9(4) . . . . ? C8D C9D C10D C11D 177.6(4) . . . . ? C9D C10D C11D C12D -179.2(4) . . . . ? C10D C11D C12D C13D -179.6(4) . . . . ? C11D C12D C13D C14D 179.4(4) . . . . ? C12D C13D C14D C15D -178.0(4) . . . . ? C13D C14D C15D C16D 177.3(4) . . . . ? C14D C15D C16D C17D -179.8(5) . . . . ? C15D C16D C17D C18D -179.2(6) . . . . ? C2D N1D C19D O1D 1.8(7) . . . . ? C2D N1D C19D C20D -178.5(4) . . . . ? C1D O2D C21D O3D -54.4(5) . . . . ? C1D O2D C21D C23D -167.6(4) . . . . ? C1D O2D C21D C22D 70.2(5) . . . . ? C3D O3D C21D O2D 57.8(5) . . . . ? C3D O3D C21D C23D 171.6(4) . . . . ? C3D O3D C21D C22D -67.6(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1A H1A O1B 0.88 2.03 2.893(5) 166 . N1B H1B O1A 0.88 2.09 2.938(5) 160 1_565 N1C H1C O1D 0.88 1.97 2.811(5) 159 1_565 N1D H1D O1C 0.88 2.07 2.924(5) 164 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.297 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.047 _chemical_absolute_configuration unk _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 -0.1118110 _diffrn_orient_matrix_UB_12 -0.0006371 _diffrn_orient_matrix_UB_13 0.0001449 _diffrn_orient_matrix_UB_21 0.0123522 _diffrn_orient_matrix_UB_22 0.0414089 _diffrn_orient_matrix_UB_23 -0.0322865 _diffrn_orient_matrix_UB_31 0.0075587 _diffrn_orient_matrix_UB_32 -0.1012400 _diffrn_orient_matrix_UB_33 -0.0117139 _symmetry_space_group_name_Hall 'P 1' _exptl_crystal_id 'Davis/Harrell isopropylidine C2 Ceramide 150K' _diffrn_measurement_frame_width-CCD -0.30 _diffrn_measurement_details 610,610,610,1200,1200 _diffrn_measurement_total_frames-CCD 4230 _diffrn_measurement_frame_time-CCD 40 _diffrn_measurement_total_time-CCD 54.0 _diffrn_source_voltage 50.00 _diffrn_source_current 30.00 _diffrn_detector_distance-CCD 6.000 _diffrn_measurement_frame_size-CCD 512 _diffrn_measurement_specimen_support 'glass capillary' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker Smart Apex II' _reflns_Friedel_coverage 0 #_______________________________________________________________________________ # _publ_section_references ; Bruker (2005). Apex2. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (1997). SHELXL-97. University of G\"ottingen, Germany. Spek, A. L. (1990). Acta Cryst., A46, C-34. ; # Attachment '1807.cif.txt' data_1807 _database_code_depnum_ccdc_archive 'CCDC 771168' #TrackingRef '1807.cif.txt' _audit_creation_method 'SHELXL-97 & ZCIF' _chemical_name_systematic ; pMBC2 ; _chemical_name_common pMBC2 _chemical_formula_moiety 'C28 H45 N O4' _chemical_formula_sum 'C28 H45 N O4' _chemical_formula_weight 459.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4304(5) _cell_length_b 4.9089(3) _cell_length_c 30.3484(16) _cell_angle_alpha 90.00 _cell_angle_beta 91.2750(10) _cell_angle_gamma 90.00 _cell_volume 1404.57(14) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4185 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 23.0 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.087 _exptl_crystal_density_method ? _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.949 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; One-dimensional incommensurate modulated at 150 K ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'three-circle diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11341 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2789 _reflns_number_gt 2125 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement Apex2 _computing_data_reduction Apex2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker, 2004)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.002P)^2^+0.267P], P=(max(Fo^2^,0)+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_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2789 # 2789 w/o Fiedel pairs _refine_ls_number_parameters 366 _refine_ls_number_restraints 238 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0668 _refine_ls_wR_factor_gt 0.0631 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.1822(4) 0.8354(9) 0.29586(9) 0.1474(16) Uani 1 1 d . . . H1A H 1.1014 0.8498 0.2762 0.221 Uiso 1 1 calc R . . H1B H 1.2533 0.7241 0.2826 0.221 Uiso 1 1 calc R . . H1C H 1.2202 1.0137 0.3016 0.221 Uiso 1 1 calc R . . C2 C 1.1392(3) 0.7117(8) 0.33725(10) 0.1244(12) Uani 1 1 d . . . H2A H 1.2227 0.6945 0.3563 0.149 Uiso 1 1 calc R . . H2B H 1.1052 0.5290 0.3309 0.149 Uiso 1 1 calc R . . C3 C 1.0273(3) 0.8586(7) 0.36227(8) 0.0908(8) Uani 1 1 d . . . H3A H 0.9434 0.8752 0.3434 0.109 Uiso 1 1 calc R . . H3B H 1.0610 1.0414 0.3687 0.109 Uiso 1 1 calc R . . C4 C 0.9850(3) 0.7283(7) 0.40474(8) 0.0926(8) Uani 1 1 d . . . H4A H 0.9497 0.5468 0.3982 0.111 Uiso 1 1 calc R . . H4B H 1.0694 0.7081 0.4233 0.111 Uiso 1 1 calc R . . C5 C 0.8753(3) 0.8755(6) 0.43055(7) 0.0813(7) Uani 1 1 d . . . H5A H 0.7910 0.8973 0.4120 0.098 Uiso 1 1 calc R . . H5B H 0.9108 1.0562 0.4375 0.098 Uiso 1 1 calc R . . C6 C 0.8337(2) 0.7392(7) 0.47263(8) 0.0839(8) Uani 1 1 d . . . H6A H 0.9182 0.7172 0.4911 0.101 Uiso 1 1 calc R . . H6B H 0.7983 0.5586 0.4656 0.101 Uiso 1 1 calc R . . C7 C 0.7237(3) 0.8857(6) 0.49881(7) 0.0804(7) Uani 1 1 d . . . H7A H 0.6393 0.9092 0.4803 0.096 Uiso 1 1 calc R . . H7B H 0.7594 1.0656 0.5062 0.096 Uiso 1 1 calc R . . C8 C 0.6821(2) 0.7442(6) 0.54081(7) 0.0807(7) Uani 1 1 d . . . H8A H 0.6461 0.5646 0.5333 0.097 Uiso 1 1 calc R . . H8B H 0.7667 0.7194 0.5591 0.097 Uiso 1 1 calc R . . C9 C 0.5726(3) 0.8897(6) 0.56751(7) 0.0824(7) Uani 1 1 d . . . H9A H 0.4874 0.9121 0.5494 0.099 Uiso 1 1 calc R . . H9B H 0.6080 1.0702 0.5747 0.099 Uiso 1 1 calc R . . C10 C 0.5333(3) 0.7483(6) 0.60977(7) 0.0839(8) Uani 1 1 d . B . H10A H 0.4956 0.5697 0.6024 0.101 Uiso 1 1 calc R . . H10B H 0.6190 0.7213 0.6275 0.101 Uiso 1 1 calc R . . C11 C 0.4271(3) 0.8947(7) 0.63729(7) 0.0914(9) Uani 1 1 d . . . H11A H 0.3395 0.9140 0.6202 0.110 Uiso 1 1 calc R A 1 H11B H 0.4626 1.0763 0.6437 0.110 Uiso 1 1 calc R A 1 C12 C 0.3947(3) 0.7552(7) 0.68027(8) 0.1019(10) Uani 0.663(8) 1 d PDU B 1 H12A H 0.4836 0.7117 0.6954 0.122 Uiso 0.663(8) 1 calc PR B 1 H12B H 0.3466 0.5848 0.6738 0.122 Uiso 0.663(8) 1 calc PR B 1 C13 C 0.3032(8) 0.9220(15) 0.71145(19) 0.095(3) Uani 0.663(8) 1 d PDU B 1 H13A H 0.3457 1.1006 0.7153 0.114 Uiso 0.663(8) 1 calc PR B 1 H13B H 0.2102 0.9473 0.6978 0.114 Uiso 0.663(8) 1 calc PR B 1 C14 C 0.2857(5) 0.7944(12) 0.75594(18) 0.0844(17) Uani 0.663(8) 1 d PDU B 1 H14 H 0.3657 0.7853 0.7744 0.101 Uiso 0.663(8) 1 calc PR B 1 C15 C 0.1701(7) 0.6970(18) 0.77071(17) 0.080(2) Uani 0.663(8) 1 d PDU B 1 H15 H 0.0884 0.6995 0.7530 0.096 Uiso 0.663(8) 1 calc PR B 1 C16 C 0.1644(3) 0.5769(6) 0.81709(7) 0.0789(7) Uani 0.663(8) 1 d PDU B 1 H16 H 0.1423 0.3828 0.8138 0.095 Uiso 0.663(8) 1 calc PR B 1 C12A C 0.3947(3) 0.7552(7) 0.68027(8) 0.1019(10) Uani 0.337(8) 1 d PDU B 2 H12C H 0.4722 0.7886 0.7011 0.122 Uiso 0.337(8) 1 calc PR B 2 H12D H 0.3893 0.5603 0.6753 0.122 Uiso 0.337(8) 1 calc PR B 2 C13A C 0.2558(11) 0.851(3) 0.7006(3) 0.083(4) Uani 0.337(8) 1 d PDU B 2 H13C H 0.2650 1.0421 0.7085 0.099 Uiso 0.337(8) 1 calc PR B 2 H13D H 0.1800 0.8364 0.6786 0.099 Uiso 0.337(8) 1 calc PR B 2 C14A C 0.2159(12) 0.693(2) 0.7405(2) 0.083(3) Uani 0.337(8) 1 d PDU B 2 H14A H 0.1865 0.5147 0.7353 0.100 Uiso 0.337(8) 1 calc PR B 2 C15A C 0.2166(17) 0.768(2) 0.7808(2) 0.072(4) Uani 0.337(8) 1 d PDU B 2 H15A H 0.2492 0.9408 0.7882 0.086 Uiso 0.337(8) 1 calc PR B 2 C16A C 0.1644(3) 0.5769(6) 0.81709(7) 0.0789(7) Uani 0.337(8) 1 d PDU B 2 H16A H 0.1429 0.3922 0.8066 0.095 Uiso 0.337(8) 1 calc PR B 2 O16 O 0.29515(17) 0.5954(4) 0.84226(5) 0.0826(5) Uani 1 1 d . . . C17 C 0.0460(3) 0.7034(6) 0.84366(7) 0.0763(7) Uani 1 1 d . . . H17 H 0.0631 0.8998 0.8461 0.092 Uiso 1 1 calc R B 1 N17 N -0.0918(2) 0.6606(4) 0.82314(6) 0.0779(6) Uani 1 1 d . B . H17A H -0.1157 0.4970 0.8161 0.094 Uiso 1 1 calc R . . C18 C -0.1843(3) 0.8605(7) 0.81453(8) 0.0817(8) Uani 1 1 d . . . O18 O -0.1531(3) 1.0993(4) 0.82006(8) 0.1196(8) Uani 1 1 d . B . C19 C -0.3288(3) 0.7750(7) 0.79777(9) 0.1008(9) Uani 1 1 d . B . H19A H -0.3983 0.8205 0.8192 0.151 Uiso 1 1 calc R . . H19B H -0.3296 0.5819 0.7928 0.151 Uiso 1 1 calc R . . H19C H -0.3507 0.8681 0.7706 0.151 Uiso 1 1 calc R . . C20 C 0.0475(3) 0.5815(8) 0.88964(7) 0.0968(10) Uani 1 1 d . B . H20A H -0.0196 0.6785 0.9077 0.116 Uiso 1 1 calc R . . H20B H 0.0180 0.3924 0.8880 0.116 Uiso 1 1 calc R . . O20 O 0.18523(19) 0.5977(5) 0.90960(5) 0.1017(7) Uani 1 1 d . . . C21 C 0.2857(3) 0.4674(7) 0.88386(8) 0.0858(8) Uani 1 1 d . B . H21 H 0.2574 0.2771 0.8795 0.103 Uiso 1 1 calc R C 1 C22 C 0.4280(3) 0.4753(7) 0.90702(8) 0.0835(8) Uani 0.540(18) 1 d PDU B 1 C23 C 0.5411(7) 0.344(2) 0.8908(3) 0.095(3) Uani 0.540(18) 1 d PDU B 1 H23 H 0.5306 0.2478 0.8645 0.114 Uiso 0.540(18) 1 calc PR B 1 C24 C 0.4439(7) 0.609(2) 0.9479(2) 0.085(2) Uani 0.540(18) 1 d PDU B 1 H24 H 0.3669 0.6978 0.9601 0.102 Uiso 0.540(18) 1 calc PR B 1 C25 C 0.6721(8) 0.350(2) 0.9120(3) 0.099(3) Uani 0.540(18) 1 d PDU B 1 H25 H 0.7488 0.2621 0.8994 0.118 Uiso 0.540(18) 1 calc PR B 1 C26 C 0.5753(7) 0.609(2) 0.9703(3) 0.090(2) Uani 0.540(18) 1 d PDU B 1 H26 H 0.5856 0.6933 0.9976 0.108 Uiso 0.540(18) 1 calc PR B 1 C27 C 0.6899(3) 0.4819(8) 0.95124(10) 0.0921(9) Uani 0.540(18) 1 d PDU B 1 C22A C 0.4280(3) 0.4753(7) 0.90702(8) 0.0835(8) Uani 0.460(18) 1 d PDU B 2 C23A C 0.5255(9) 0.273(2) 0.9004(4) 0.099(3) Uani 0.460(18) 1 d PDU B 2 H23A H 0.5037 0.1338 0.8807 0.118 Uiso 0.460(18) 1 calc PR B 2 C24A C 0.4670(10) 0.6909(19) 0.9333(5) 0.107(3) Uani 0.460(18) 1 d PDU B 2 H24A H 0.4063 0.8390 0.9360 0.128 Uiso 0.460(18) 1 calc PR B 2 C25A C 0.6560(10) 0.272(2) 0.9225(4) 0.101(3) Uani 0.460(18) 1 d PDU B 2 H25A H 0.7200 0.1312 0.9180 0.121 Uiso 0.460(18) 1 calc PR B 2 C26A C 0.5971(10) 0.690(2) 0.9559(5) 0.107(3) Uani 0.460(18) 1 d PDU B 2 H26A H 0.6206 0.8341 0.9746 0.128 Uiso 0.460(18) 1 calc PR B 2 C27A C 0.6899(3) 0.4819(8) 0.95124(10) 0.0921(9) Uani 0.460(18) 1 d PDU B 2 O27 O 0.8213(2) 0.4693(6) 0.97155(6) 0.1125(7) Uani 1 1 d . . . C28 C 0.8479(3) 0.6453(10) 1.00816(11) 0.1360(14) Uani 1 1 d . B . H28A H 0.8320 0.8308 0.9993 0.204 Uiso 1 1 calc R . . H28B H 0.9443 0.6240 1.0183 0.204 Uiso 1 1 calc R . . H28C H 0.7851 0.5997 1.0315 0.204 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 C1 0.189(3) 0.152(4) 0.103(2) 0.006(3) 0.054(2) 0.014(3) C2 0.138(3) 0.119(3) 0.119(2) 0.012(3) 0.054(2) 0.009(3) C3 0.110(2) 0.084(2) 0.0787(16) 0.0005(18) 0.0176(15) -0.0010(19) C4 0.0980(18) 0.087(2) 0.0937(18) 0.0080(18) 0.0256(15) 0.0008(19) C5 0.0946(17) 0.0743(17) 0.0754(15) 0.0013(16) 0.0117(13) -0.0035(16) C6 0.0885(17) 0.0799(19) 0.0840(17) 0.0098(16) 0.0160(14) 0.0021(16) C7 0.0984(18) 0.0733(17) 0.0699(14) 0.0038(15) 0.0099(13) -0.0023(17) C8 0.0875(16) 0.0767(18) 0.0783(16) 0.0114(15) 0.0129(13) -0.0013(16) C9 0.1014(18) 0.0757(18) 0.0708(15) 0.0078(15) 0.0135(13) -0.0003(17) C10 0.0927(17) 0.0827(19) 0.0768(16) 0.0134(16) 0.0128(14) -0.0007(17) C11 0.113(2) 0.089(2) 0.0731(15) 0.0168(17) 0.0217(14) 0.0057(19) C12 0.118(2) 0.102(2) 0.0870(18) 0.0272(19) 0.0359(16) 0.016(2) C13 0.109(5) 0.095(5) 0.081(4) 0.019(4) 0.022(3) -0.001(4) C14 0.084(3) 0.104(4) 0.065(3) 0.007(3) 0.012(2) -0.007(3) C15 0.082(4) 0.103(5) 0.055(4) 0.001(4) 0.005(3) -0.006(3) C16 0.1008(18) 0.0702(18) 0.0661(14) 0.0049(14) 0.0118(14) -0.0007(16) C12A 0.118(2) 0.102(2) 0.0870(18) 0.0272(19) 0.0359(16) 0.016(2) C13A 0.113(8) 0.078(8) 0.058(5) 0.011(5) 0.026(6) 0.002(7) C14A 0.089(8) 0.084(7) 0.076(6) 0.004(5) 0.015(5) 0.001(6) C15A 0.093(12) 0.073(7) 0.048(5) -0.007(5) -0.003(6) 0.019(7) C16A 0.1008(18) 0.0702(18) 0.0661(14) 0.0049(14) 0.0118(14) -0.0007(16) O16 0.0954(12) 0.0814(12) 0.0719(10) 0.0127(10) 0.0222(9) -0.0076(11) C17 0.0905(17) 0.0602(17) 0.0788(16) -0.0081(14) 0.0182(14) -0.0119(15) N17 0.0958(15) 0.0523(13) 0.0859(14) -0.0072(12) 0.0050(12) -0.0067(12) C18 0.114(2) 0.0591(18) 0.0725(16) -0.0024(15) 0.0112(15) 0.0002(18) O18 0.157(2) 0.0497(12) 0.151(2) -0.0094(14) -0.0116(15) -0.0032(14) C19 0.114(2) 0.086(2) 0.102(2) -0.0043(19) -0.0062(17) 0.009(2) C20 0.0891(18) 0.134(3) 0.0679(15) -0.002(2) 0.0123(13) -0.028(2) O20 0.0898(12) 0.148(2) 0.0678(10) -0.0088(13) 0.0146(9) -0.0269(15) C21 0.101(2) 0.0857(19) 0.0710(15) 0.0071(16) 0.0110(15) -0.0219(18) C22 0.0938(19) 0.089(2) 0.0684(16) 0.0093(16) 0.0111(14) -0.0195(18) C23 0.100(4) 0.128(6) 0.059(4) -0.011(5) 0.032(3) -0.023(4) C24 0.092(4) 0.082(5) 0.080(4) -0.002(4) 0.006(3) -0.004(4) C25 0.090(4) 0.133(6) 0.075(4) -0.002(5) 0.035(3) -0.013(4) C26 0.101(4) 0.092(5) 0.078(4) 0.000(4) 0.009(3) -0.017(4) C27 0.087(2) 0.108(2) 0.0814(18) 0.0121(19) 0.0176(16) -0.020(2) C22A 0.0938(19) 0.089(2) 0.0684(16) 0.0093(16) 0.0111(14) -0.0195(18) C23A 0.102(5) 0.127(6) 0.068(5) -0.006(5) 0.027(4) -0.020(5) C24A 0.111(5) 0.063(5) 0.146(7) 0.012(5) -0.027(5) -0.018(4) C25A 0.093(5) 0.133(6) 0.078(5) 0.005(5) 0.036(4) -0.002(5) C26A 0.113(5) 0.070(5) 0.136(7) 0.010(5) -0.029(5) -0.026(4) C27A 0.087(2) 0.108(2) 0.0814(18) 0.0121(19) 0.0176(16) -0.020(2) O27 0.0853(13) 0.156(2) 0.0968(13) -0.0017(16) 0.0115(11) -0.0115(15) C28 0.107(2) 0.163(4) 0.136(3) -0.013(3) -0.021(2) -0.020(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.461(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.499(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.501(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.497(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.501(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.504(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.511(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.507(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.511(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.501(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.510(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.532(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.501(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.280(6) . ? C14 H14 0.9300 . ? C15 C16 1.528(5) . ? C15 H15 0.9300 . ? C16 O16 1.438(3) . ? C16 C17 1.524(3) . ? C16 H16 0.9800 . ? O16 C21 1.415(3) . ? C17 N17 1.444(3) . ? C17 C20 1.518(3) . ? C17 H17 0.9800 . ? N17 C18 1.335(3) . ? N17 H17A 0.8600 . ? C18 O18 1.220(3) . ? C18 C19 1.503(4) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 O20 1.424(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? O20 C21 1.396(3) . ? C21 C22 1.501(3) . ? C21 H21 0.9800 . ? C22 C23 1.349(6) . ? C22 C24 1.410(6) . ? C23 C25 1.381(6) . ? C23 H23 0.9300 . ? C24 C26 1.399(6) . ? C24 H24 0.9300 . ? C25 C27 1.364(6) . ? C25 H25 0.9300 . ? C26 C27 1.385(6) . ? C26 H26 0.9300 . ? C27 O27 1.373(3) . ? O27 C28 1.425(4) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 116.6(3) . . ? C1 C2 H2A 108.1 . . ? C3 C2 H2A 108.1 . . ? C1 C2 H2B 108.1 . . ? C3 C2 H2B 108.1 . . ? H2A C2 H2B 107.3 . . ? C2 C3 C4 115.7(3) . . ? C2 C3 H3A 108.4 . . ? C4 C3 H3A 108.4 . . ? C2 C3 H3B 108.4 . . ? C4 C3 H3B 108.4 . . ? H3A C3 H3B 107.4 . . ? C5 C4 C3 116.3(3) . . ? C5 C4 H4A 108.2 . . ? C3 C4 H4A 108.2 . . ? C5 C4 H4B 108.2 . . ? C3 C4 H4B 108.2 . . ? H4A C4 H4B 107.4 . . ? C4 C5 C6 115.3(2) . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C5 C6 C7 115.6(2) . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? C5 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.4 . . ? C6 C7 C8 114.9(2) . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7A 108.5 . . ? C6 C7 H7B 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C7 115.4(2) . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8B 108.4 . . ? C7 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C8 C9 C10 115.0(2) . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C11 C10 C9 115.6(2) . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C9 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? C10 C11 C12 114.4(2) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C13 114.7(3) . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 114.0(5) . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? C12 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 125.6(5) . . ? C15 C14 H14 117.2 . . ? C13 C14 H14 117.2 . . ? C14 C15 C16 120.9(5) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? O16 C16 C17 108.81(19) . . ? O16 C16 C15 114.7(3) . . ? C17 C16 C15 111.8(4) . . ? O16 C16 H16 107.1 . . ? C17 C16 H16 107.1 . . ? C15 C16 H16 107.1 . . ? C21 O16 C16 112.06(18) . . ? N17 C17 C20 109.2(2) . . ? N17 C17 C16 112.1(2) . . ? C20 C17 C16 109.5(2) . . ? N17 C17 H17 108.7 . . ? C20 C17 H17 108.7 . . ? C16 C17 H17 108.7 . . ? C18 N17 C17 123.7(2) . . ? C18 N17 H17A 118.1 . . ? C17 N17 H17A 118.1 . . ? O18 C18 N17 121.7(3) . . ? O18 C18 C19 122.0(3) . . ? N17 C18 C19 116.4(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O20 C20 C17 111.0(2) . . ? O20 C20 H20A 109.4 . . ? C17 C20 H20A 109.4 . . ? O20 C20 H20B 109.4 . . ? C17 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C21 O20 C20 111.1(2) . . ? O20 C21 O16 110.7(2) . . ? O20 C21 C22 109.7(2) . . ? O16 C21 C22 109.4(2) . . ? O20 C21 H21 109.0 . . ? O16 C21 H21 109.0 . . ? C22 C21 H21 109.0 . . ? C23 C22 C24 118.3(4) . . ? C23 C22 C21 121.5(4) . . ? C24 C22 C21 120.1(4) . . ? C22 C23 C25 121.8(6) . . ? C22 C23 H23 119.1 . . ? C25 C23 H23 119.1 . . ? C26 C24 C22 120.2(5) . . ? C26 C24 H24 119.9 . . ? C22 C24 H24 119.9 . . ? C27 C25 C23 120.5(6) . . ? C27 C25 H25 119.7 . . ? C23 C25 H25 119.7 . . ? C27 C26 C24 119.3(5) . . ? C27 C26 H26 120.4 . . ? C24 C26 H26 120.4 . . ? C25 C27 O27 117.6(4) . . ? C25 C27 C26 119.8(5) . . ? O27 C27 C26 122.5(4) . . ? C27 O27 C28 117.6(3) . . ? O27 C28 H28A 109.5 . . ? O27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 C1 C2 C3 C4 -179.9(3) . . . . ? C2 C3 C4 C5 178.8(3) . . . . ? C3 C4 C5 C6 179.3(2) . . . . ? C4 C5 C6 C7 180.0(2) . . . . ? C5 C6 C7 C8 179.4(2) . . . . ? C6 C7 C8 C9 179.6(2) . . . . ? C7 C8 C9 C10 -179.2(2) . . . . ? C8 C9 C10 C11 178.4(2) . . . . ? C9 C10 C11 C12 -177.4(2) . . . . ? C10 C11 C12 C13 171.7(4) . . . . ? C11 C12 C13 C14 -173.5(4) . . . . ? C12 C13 C14 C15 -111.8(10) . . . . ? C13 C14 C15 C16 -178.7(6) . . . . ? C14 C15 C16 O16 2.8(11) . . . . ? C14 C15 C16 C17 127.2(8) . . . . ? C17 C16 O16 C21 57.3(3) . . . . ? C15 C16 O16 C21 -176.7(5) . . . . ? O16 C16 C17 N17 -172.4(2) . . . . ? C15 C16 C17 N17 60.0(4) . . . . ? O16 C16 C17 C20 -51.0(3) . . . . ? C15 C16 C17 C20 -178.7(4) . . . . ? C20 C17 N17 C18 110.9(3) . . . . ? C16 C17 N17 C18 -127.6(3) . . . . ? C17 N17 C18 O18 6.5(4) . . . . ? C17 N17 C18 C19 -173.3(2) . . . . ? N17 C17 C20 O20 174.8(2) . . . . ? C16 C17 C20 O20 51.8(3) . . . . ? C17 C20 O20 C21 -57.3(4) . . . . ? C20 O20 C21 O16 62.2(3) . . . . ? C20 O20 C21 C22 -177.0(3) . . . . ? C16 O16 C21 O20 -63.2(3) . . . . ? C16 O16 C21 C22 175.8(3) . . . . ? O20 C21 C22 C23 174.6(7) . . . . ? O16 C21 C22 C23 -63.8(8) . . . . ? O20 C21 C22 C24 -1.9(7) . . . . ? O16 C21 C22 C24 119.7(6) . . . . ? C24 C22 C23 C25 -3.1(12) . . . . ? C21 C22 C23 C25 -179.7(7) . . . . ? C23 C22 C24 C26 1.3(10) . . . . ? C21 C22 C24 C26 177.9(5) . . . . ? C22 C23 C25 C27 2.1(14) . . . . ? C22 C24 C26 C27 1.6(10) . . . . ? C23 C25 C27 O27 177.2(7) . . . . ? C23 C25 C27 C26 0.9(11) . . . . ? C24 C26 C27 C25 -2.7(10) . . . . ? C24 C26 C27 O27 -178.8(5) . . . . ? C25 C27 O27 C28 169.0(7) . . . . ? C26 C27 O27 C28 -14.7(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N17 H17A O18 0.86 1.99 2.816(3) 161 1_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.090 _refine_diff_density_min -0.081 _refine_diff_density_rms 0.017 _chemical_absolute_configuration unk _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 0.0078414 _diffrn_orient_matrix_UB_12 -0.0212015 _diffrn_orient_matrix_UB_13 -0.0326266 _diffrn_orient_matrix_UB_21 -0.1057712 _diffrn_orient_matrix_UB_22 0.0004436 _diffrn_orient_matrix_UB_23 -0.0031881 _diffrn_orient_matrix_UB_31 0.0010588 _diffrn_orient_matrix_UB_32 0.2026040 _diffrn_orient_matrix_UB_33 -0.0034097 _symmetry_space_group_name_Hall 'P 2yb' _exptl_crystal_id 'Davis/Harrell pMBC2 at 295K =1804 (same xtal)' _diffrn_measurement_frame_width-CCD -0.30 _diffrn_measurement_details 610,610,610,270 _diffrn_measurement_total_frames-CCD 2100 _diffrn_measurement_frame_time-CCD 60 _diffrn_measurement_total_time-CCD 38.5 _diffrn_source_voltage 50.00 _diffrn_source_current 30.00 _diffrn_detector_distance-CCD 6.000 _diffrn_measurement_frame_size-CCD 512 _diffrn_measurement_specimen_support 'glass capillary' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker Smart Apex II' #_______________________________________________________________________________ # _publ_section_references ; Bruker (2005). Apex2. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (1997). SHELXL-97. University of G\"ottingen, Germany. Spek, A. L. (1990). Acta Cryst., A46, C-34. ;