Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Claudio Jimenez' _publ_contact_author_address ; Quimica Organica Universidad de Concepcion Edmundo Larenas 129. Barrio Universitario Concepcion CHILE ; _publ_contact_author_email CJIMENEZ@UDEC.CL _publ_section_title ; Subtle Structural Changes in the Crystal Packing of Highly Hindered Symmetrical Vicinal Bis-Amides ; loop_ _publ_author_name 'Claudio Jimenez' 'Julio Belmar' 'Fernando S. Delgado' 'Miguel Julve' 'Catalina Ruiz-Perez' data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 629529' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H52 N2 O4' _chemical_formula_weight 552.78 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 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0092(6) _cell_length_b 11.2895(7) _cell_length_c 15.5109(8) _cell_angle_alpha 98.90(4) _cell_angle_beta 102.04(5) _cell_angle_gamma 104.00(5) _cell_volume 1623.85(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 0.19 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.131 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15426 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0661 _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 -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7124 _reflns_number_gt 3915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1d (Brandenburg &Putz GbR, 2000)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+0.4999P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7124 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1320 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1752 _refine_ls_wR_factor_gt 0.1470 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 C1 C -0.1309(2) 0.7835(2) 0.33297(14) 0.0321(5) Uani 1 1 d . . . C2 C -0.0112(2) 0.8833(2) 0.34139(15) 0.0349(5) Uani 1 1 d . . . C3 C -0.0243(2) 1.0040(2) 0.33919(14) 0.0334(5) Uani 1 1 d . . . C4 C -0.1603(2) 1.0169(2) 0.32479(15) 0.0360(5) Uani 1 1 d . . . C5 C -0.2838(2) 0.9189(2) 0.31142(14) 0.0330(5) Uani 1 1 d . . . C6 C -0.2662(2) 0.8036(2) 0.31643(15) 0.0336(5) Uani 1 1 d . . . C7 C -0.1109(2) 0.6605(2) 0.34491(15) 0.0348(5) Uani 1 1 d . . . C8 C -0.2109(3) 0.4478(2) 0.36348(19) 0.0462(6) Uani 1 1 d . . . C9 C -0.2117(3) 0.4233(3) 0.4571(2) 0.0514(7) Uani 1 1 d . . . C10 C -0.3524(3) 0.4111(3) 0.47926(19) 0.0508(7) Uani 1 1 d . . . C11 C -0.3647(3) 0.3526(2) 0.55997(16) 0.0441(6) Uani 1 1 d . . . C12 C -0.3329(2) 0.4879(2) 0.70689(15) 0.0347(5) Uani 1 1 d . . . C13 C -0.2376(2) 0.5642(2) 0.79415(15) 0.0332(5) Uani 1 1 d . . . C14 C -0.2922(2) 0.6346(2) 0.85344(15) 0.0365(5) Uani 1 1 d . . . C15 C -0.2034(2) 0.7124(2) 0.93484(15) 0.0389(5) Uani 1 1 d . . . C16 C -0.0624(2) 0.7134(2) 0.95365(17) 0.0402(6) Uani 1 1 d . . . C17 C -0.0033(2) 0.6423(2) 0.89881(15) 0.0345(5) Uani 1 1 d . . . C18 C -0.0932(2) 0.5696(2) 0.81950(16) 0.0347(5) Uani 1 1 d . . . C19 C -0.4288(2) 0.9460(2) 0.29590(17) 0.0415(6) Uani 1 1 d . . . C20 C -0.4464(3) 1.0213(4) 0.2252(3) 0.1127(16) Uani 1 1 d . . . H20A H -0.4374 0.9769 0.1697 0.169 Uiso 1 1 calc R . . H20B H -0.3742 1.1003 0.2446 0.169 Uiso 1 1 calc R . . H20C H -0.5388 1.0352 0.2160 0.169 Uiso 1 1 calc R . . C21 C -0.4405(4) 1.0137(4) 0.3843(2) 0.1154(16) Uani 1 1 d . . . H21A H -0.4286 0.9638 0.4286 0.173 Uiso 1 1 calc R . . H21B H -0.5325 1.0281 0.3766 0.173 Uiso 1 1 calc R . . H21C H -0.3678 1.0923 0.4042 0.173 Uiso 1 1 calc R . . C22 C -0.5516(3) 0.8268(3) 0.2635(3) 0.0810(10) Uani 1 1 d . . . H22A H -0.5460 0.7814 0.2073 0.121 Uiso 1 1 calc R . . H22B H -0.6403 0.8475 0.2550 0.121 Uiso 1 1 calc R . . H22C H -0.5461 0.7761 0.3077 0.121 Uiso 1 1 calc R . . C23 C 0.1059(2) 1.1162(2) 0.35208(16) 0.0420(6) Uani 1 1 d . . . C24 C 0.0653(3) 1.2387(2) 0.3567(2) 0.0715(9) Uani 1 1 d . . . H24A H -0.0040 1.2336 0.3021 0.107 Uiso 1 1 calc R . . H24B H 0.1485 1.3065 0.3636 0.107 Uiso 1 1 calc R . . H24C H 0.0257 1.2528 0.4074 0.107 Uiso 1 1 calc R . . C25 C 0.1725(3) 1.0990(3) 0.27236(19) 0.0629(8) Uani 1 1 d . . . H25A H 0.1028 1.0906 0.2172 0.094 Uiso 1 1 calc R . . H25B H 0.2043 1.0252 0.2703 0.094 Uiso 1 1 calc R . . H25C H 0.2521 1.1704 0.2796 0.094 Uiso 1 1 calc R . . C26 C 0.2157(3) 1.1291(3) 0.44024(19) 0.0641(8) Uani 1 1 d . . . H26A H 0.1732 1.1398 0.4899 0.096 Uiso 1 1 calc R . . H26B H 0.2956 1.2004 0.4480 0.096 Uiso 1 1 calc R . . H26C H 0.2472 1.0551 0.4383 0.096 Uiso 1 1 calc R . . C27 C -0.2609(2) 0.7912(2) 1.00041(17) 0.0490(6) Uani 1 1 d . . . C28 C -0.3248(3) 0.8813(3) 0.9519(2) 0.0692(9) Uani 1 1 d . . . H28A H -0.2529 0.9341 0.9313 0.104 Uiso 1 1 calc R . . H28B H -0.3588 0.9320 0.9929 0.104 Uiso 1 1 calc R . . H28C H -0.4024 0.8342 0.9011 0.104 Uiso 1 1 calc R . . C29 C -0.3739(3) 0.7066(3) 1.0334(2) 0.0679(8) Uani 1 1 d . . . H29A H -0.4092 0.7569 1.0739 0.102 Uiso 1 1 calc R . . H29B H -0.3327 0.6515 1.0644 0.102 Uiso 1 1 calc R . . H29C H -0.4509 0.6582 0.9827 0.102 Uiso 1 1 calc R . . C30 C -0.1437(3) 0.8692(3) 1.0829(2) 0.0776(10) Uani 1 1 d . . . H30A H -0.0711 0.9239 1.0641 0.116 Uiso 1 1 calc R . . H30B H -0.1029 0.8150 1.1151 0.116 Uiso 1 1 calc R . . H30C H -0.1830 0.9181 1.1217 0.116 Uiso 1 1 calc R . . C31 C 0.1555(2) 0.6518(2) 0.92634(16) 0.0430(6) Uani 1 1 d . . . C32 C 0.2064(3) 0.6604(5) 1.0257(2) 0.129(2) Uani 1 1 d . . . H32A H 0.1532 0.5879 1.0416 0.193 Uiso 1 1 calc R . . H32B H 0.1929 0.7341 1.0585 0.193 Uiso 1 1 calc R . . H32C H 0.3057 0.6648 1.0406 0.193 Uiso 1 1 calc R . . C33 C 0.1866(3) 0.5377(4) 0.8802(3) 0.1019(14) Uani 1 1 d . . . H33A H 0.1564 0.5281 0.8160 0.153 Uiso 1 1 calc R . . H33B H 0.1362 0.4651 0.8974 0.153 Uiso 1 1 calc R . . H33C H 0.2871 0.5473 0.8979 0.153 Uiso 1 1 calc R . . C34 C 0.2360(3) 0.7627(4) 0.8980(4) 0.1237(18) Uani 1 1 d . . . H34A H 0.2025 0.7534 0.8340 0.186 Uiso 1 1 calc R . . H34B H 0.3358 0.7684 0.9131 0.186 Uiso 1 1 calc R . . H34C H 0.2215 0.8373 0.9287 0.186 Uiso 1 1 calc R . . N1 N -0.2197(2) 0.57276(18) 0.35412(13) 0.0405(5) Uani 1 1 d . . . N2 N -0.2781(2) 0.43232(17) 0.64639(13) 0.0385(5) Uani 1 1 d . . . O1 O 0.11985(16) 0.86559(18) 0.35141(14) 0.0560(5) Uani 1 1 d . . . O2 O -0.43207(16) 0.63008(19) 0.83267(13) 0.0585(5) Uani 1 1 d . . . O3 O 0.00689(16) 0.63921(15) 0.34819(13) 0.0543(5) Uani 1 1 d . . . O4 O -0.46373(15) 0.47735(16) 0.68810(11) 0.0524(5) Uani 1 1 d . . . H18 H -0.061(2) 0.5188(19) 0.7790(14) 0.029(5) Uiso 1 1 d . . . H6 H -0.348(2) 0.732(2) 0.3057(14) 0.032(6) Uiso 1 1 d . . . H16 H -0.004(2) 0.762(2) 1.0089(16) 0.042(6) Uiso 1 1 d . . . H4 H -0.174(2) 1.096(2) 0.3213(14) 0.035(6) Uiso 1 1 d . . . H1N H -0.301(3) 0.589(2) 0.3518(15) 0.044(7) Uiso 1 1 d . . . H2N H -0.187(3) 0.435(2) 0.6625(15) 0.041(7) Uiso 1 1 d . . . H1O H 0.102(3) 0.780(3) 0.354(2) 0.077(10) Uiso 1 1 d . . . H111 H -0.467(3) 0.336(2) 0.5630(18) 0.066(8) Uiso 1 1 d . . . H101 H -0.370(3) 0.497(3) 0.489(2) 0.082(9) Uiso 1 1 d . . . H91 H -0.134(3) 0.494(2) 0.5065(17) 0.056(7) Uiso 1 1 d . . . H112 H -0.339(2) 0.272(2) 0.5530(15) 0.046(7) Uiso 1 1 d . . . H92 H -0.193(3) 0.339(3) 0.460(2) 0.082(9) Uiso 1 1 d . . . H82 H -0.115(3) 0.439(2) 0.3510(18) 0.067(8) Uiso 1 1 d . . . H102 H -0.425(4) 0.355(3) 0.420(3) 0.105(11) Uiso 1 1 d . . . H81 H -0.289(3) 0.394(3) 0.3201(19) 0.067(9) Uiso 1 1 d . . . H2O H -0.467(3) 0.573(3) 0.773(2) 0.099(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0309(11) 0.0347(12) 0.0331(12) 0.0070(10) 0.0105(9) 0.0115(9) C2 0.0257(11) 0.0428(13) 0.0377(13) 0.0076(11) 0.0088(9) 0.0127(10) C3 0.0336(11) 0.0336(12) 0.0320(12) 0.0056(10) 0.0077(9) 0.0093(9) C4 0.0367(12) 0.0357(13) 0.0396(14) 0.0114(11) 0.0105(10) 0.0150(10) C5 0.0315(11) 0.0427(13) 0.0305(12) 0.0134(10) 0.0100(9) 0.0157(10) C6 0.0283(11) 0.0387(13) 0.0359(13) 0.0116(10) 0.0107(9) 0.0093(10) C7 0.0324(11) 0.0365(13) 0.0379(13) 0.0065(10) 0.0104(9) 0.0137(10) C8 0.0521(16) 0.0372(14) 0.0561(18) 0.0148(13) 0.0214(14) 0.0158(13) C9 0.0499(15) 0.0495(17) 0.0583(18) 0.0188(15) 0.0160(13) 0.0143(13) C10 0.0491(15) 0.0593(18) 0.0451(17) 0.0108(14) 0.0121(12) 0.0173(14) C11 0.0436(14) 0.0431(15) 0.0380(15) 0.0014(12) 0.0096(11) 0.0038(12) C12 0.0294(11) 0.0358(12) 0.0380(13) 0.0093(10) 0.0075(10) 0.0075(9) C13 0.0286(11) 0.0345(12) 0.0358(13) 0.0079(10) 0.0077(9) 0.0080(9) C14 0.0267(11) 0.0425(13) 0.0401(14) 0.0066(11) 0.0082(10) 0.0110(10) C15 0.0363(12) 0.0421(13) 0.0385(14) 0.0059(11) 0.0100(10) 0.0131(10) C16 0.0344(12) 0.0470(14) 0.0327(14) 0.0024(12) 0.0028(10) 0.0084(11) C17 0.0271(11) 0.0408(13) 0.0354(13) 0.0105(11) 0.0077(9) 0.0080(9) C18 0.0301(11) 0.0395(13) 0.0363(13) 0.0088(11) 0.0108(10) 0.0108(10) C19 0.0312(12) 0.0501(15) 0.0550(16) 0.0247(13) 0.0168(11) 0.0198(11) C20 0.064(2) 0.166(4) 0.170(4) 0.134(3) 0.050(2) 0.067(2) C21 0.076(2) 0.188(4) 0.090(3) -0.017(3) 0.018(2) 0.084(3) C22 0.0345(15) 0.085(2) 0.125(3) 0.032(2) 0.0122(16) 0.0220(15) C23 0.0349(12) 0.0374(13) 0.0478(15) 0.0084(11) 0.0069(10) 0.0033(10) C24 0.0538(17) 0.0392(15) 0.115(3) 0.0204(17) 0.0170(17) 0.0028(13) C25 0.0501(16) 0.0707(19) 0.0608(19) 0.0138(15) 0.0203(14) -0.0007(14) C26 0.0512(16) 0.0624(18) 0.0565(19) 0.0020(15) -0.0059(13) -0.0011(13) C27 0.0434(13) 0.0580(16) 0.0434(15) -0.0026(13) 0.0092(11) 0.0206(12) C28 0.078(2) 0.0633(19) 0.072(2) 0.0036(17) 0.0193(16) 0.0382(16) C29 0.0638(18) 0.093(2) 0.0611(19) 0.0172(17) 0.0305(15) 0.0354(17) C30 0.0667(19) 0.102(3) 0.0516(19) -0.0239(18) 0.0074(15) 0.0323(18) C31 0.0281(11) 0.0574(16) 0.0413(14) 0.0090(12) 0.0064(10) 0.0109(11) C32 0.0512(19) 0.285(6) 0.055(2) 0.034(3) 0.0000(16) 0.068(3) C33 0.0461(17) 0.111(3) 0.133(3) -0.014(3) -0.0086(19) 0.0460(19) C34 0.0398(17) 0.104(3) 0.243(6) 0.094(3) 0.038(2) 0.0111(18) N1 0.0386(11) 0.0379(11) 0.0536(13) 0.0153(10) 0.0189(9) 0.0175(9) N2 0.0289(10) 0.0422(11) 0.0396(12) 0.0042(9) 0.0073(9) 0.0052(9) O1 0.0290(9) 0.0470(11) 0.0980(16) 0.0217(11) 0.0187(9) 0.0155(8) O2 0.0298(9) 0.0794(13) 0.0582(12) -0.0107(11) 0.0039(8) 0.0229(8) O3 0.0373(9) 0.0468(10) 0.0887(14) 0.0203(10) 0.0212(9) 0.0225(8) O4 0.0270(8) 0.0649(12) 0.0543(11) -0.0062(9) 0.0015(7) 0.0127(8) _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 1.399(3) . ? C1 C6 1.405(3) . ? C1 C7 1.483(3) . ? C2 O1 1.355(2) . ? C2 C3 1.405(3) . ? C3 C4 1.379(3) . ? C3 C23 1.535(3) . ? C4 C5 1.398(3) . ? C5 C6 1.367(3) . ? C5 C19 1.533(3) . ? C7 O3 1.251(2) . ? C7 N1 1.332(3) . ? C8 N1 1.462(3) . ? C8 C9 1.522(4) . ? C9 C10 1.497(4) . ? C10 C11 1.517(4) . ? C11 N2 1.457(3) . ? C12 O4 1.252(2) . ? C12 N2 1.332(3) . ? C12 C13 1.479(3) . ? C13 C18 1.400(3) . ? C13 C14 1.405(3) . ? C14 O2 1.355(2) . ? C14 C15 1.402(3) . ? C15 C16 1.377(3) . ? C15 C27 1.539(3) . ? C16 C17 1.395(3) . ? C17 C18 1.366(3) . ? C17 C31 1.530(3) . ? C19 C20 1.495(4) . ? C19 C21 1.504(4) . ? C19 C22 1.519(4) . ? C23 C26 1.527(3) . ? C23 C24 1.528(4) . ? C23 C25 1.531(3) . ? C27 C30 1.522(4) . ? C27 C29 1.524(4) . ? C27 C28 1.537(4) . ? C31 C34 1.497(4) . ? C31 C32 1.498(4) . ? C31 C33 1.506(4) . ? 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 C6 119.1(2) . . ? C2 C1 C7 119.07(18) . . ? C6 C1 C7 121.84(19) . . ? O1 C2 C1 120.8(2) . . ? O1 C2 C3 118.46(19) . . ? C1 C2 C3 120.78(18) . . ? C4 C3 C2 116.63(19) . . ? C4 C3 C23 121.5(2) . . ? C2 C3 C23 121.91(18) . . ? C3 C4 C5 124.7(2) . . ? C6 C5 C4 116.83(19) . . ? C6 C5 C19 123.68(19) . . ? C4 C5 C19 119.4(2) . . ? C5 C6 C1 121.9(2) . . ? O3 C7 N1 119.9(2) . . ? O3 C7 C1 121.04(19) . . ? N1 C7 C1 119.10(18) . . ? N1 C8 C9 113.9(2) . . ? C10 C9 C8 114.0(2) . . ? C9 C10 C11 113.4(2) . . ? N2 C11 C10 114.4(2) . . ? O4 C12 N2 119.5(2) . . ? O4 C12 C13 121.06(19) . . ? N2 C12 C13 119.42(19) . . ? C18 C13 C14 118.6(2) . . ? C18 C13 C12 122.03(19) . . ? C14 C13 C12 119.39(19) . . ? O2 C14 C15 118.47(19) . . ? O2 C14 C13 120.6(2) . . ? C15 C14 C13 120.88(19) . . ? C16 C15 C14 116.6(2) . . ? C16 C15 C27 121.7(2) . . ? C14 C15 C27 121.72(19) . . ? C15 C16 C17 125.0(2) . . ? C18 C17 C16 116.4(2) . . ? C18 C17 C31 123.11(19) . . ? C16 C17 C31 120.4(2) . . ? C17 C18 C13 122.5(2) . . ? C20 C19 C21 111.0(3) . . ? C20 C19 C22 106.5(3) . . ? C21 C19 C22 107.8(3) . . ? C20 C19 C5 111.31(19) . . ? C21 C19 C5 108.3(2) . . ? C22 C19 C5 112.0(2) . . ? C26 C23 C24 107.3(2) . . ? C26 C23 C25 109.9(2) . . ? C24 C23 C25 107.9(2) . . ? C26 C23 C3 110.4(2) . . ? C24 C23 C3 111.66(19) . . ? C25 C23 C3 109.60(19) . . ? C30 C27 C29 107.7(2) . . ? C30 C27 C28 107.7(2) . . ? C29 C27 C28 110.1(2) . . ? C30 C27 C15 111.8(2) . . ? C29 C27 C15 110.3(2) . . ? C28 C27 C15 109.1(2) . . ? C34 C31 C32 111.5(3) . . ? C34 C31 C33 107.8(3) . . ? C32 C31 C33 106.0(3) . . ? C34 C31 C17 108.4(2) . . ? C32 C31 C17 111.5(2) . . ? C33 C31 C17 111.5(2) . . ? C7 N1 C8 122.8(2) . . ? C12 N2 C11 123.0(2) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.297 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.041 # Attachment 'compound-2.cif' data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 629530' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H54 N2 O4' _chemical_formula_weight 566.80 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 orthorhombic _symmetry_space_group_name_H-M Iba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, z+1/2' 'x, -y, z+1/2' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1' 'x+1/2, -y+1/2, z+1' _cell_length_a 23.029(4) _cell_length_b 25.201(5) _cell_length_c 12.087(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7015(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.073 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2480 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15705 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 6.48 _diffrn_reflns_theta_max 24.50 _reflns_number_total 5432 _reflns_number_gt 3845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1d (Brandenburg &Putz GbR, 2000)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.9432P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.8(11) _refine_ls_number_reflns 5432 _refine_ls_number_parameters 386 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 C1 C 0.23407(11) 0.08079(9) -0.08666(18) 0.0373(6) Uani 1 1 d . . . C2 C 0.26893(11) 0.04284(10) -0.13888(19) 0.0436(6) Uani 1 1 d . . . C3 C 0.26180(11) -0.01116(9) -0.1156(2) 0.0428(6) Uani 1 1 d . . . C4 C 0.21572(11) -0.02479(10) -0.0478(2) 0.0468(7) Uani 1 1 d . . . H4 H 0.2098 -0.0606 -0.0334 0.056 Uiso 1 1 calc R . . C5 C 0.17757(10) 0.01132(9) 0.00026(19) 0.0410(6) Uani 1 1 d . . . C6 C 0.18877(11) 0.06431(9) -0.01912(19) 0.0399(6) Uani 1 1 d . . . H6 H 0.1653 0.0897 0.0141 0.048 Uiso 1 1 calc R . . C7 C 0.24852(11) 0.13746(9) -0.10189(19) 0.0385(6) Uani 1 1 d . . . C8 C 0.24757(11) 0.22732(9) -0.02265(18) 0.0407(6) Uani 1 1 d . . . H8A H 0.2126 0.2479 -0.0102 0.049 Uiso 1 1 calc R . . H8B H 0.2626 0.2370 -0.0949 0.049 Uiso 1 1 calc R . . C9 C 0.29241(11) 0.24245(9) 0.06504(19) 0.0385(6) Uani 1 1 d . . . C10 C 0.34952(12) 0.21325(12) 0.0460(2) 0.0594(8) Uani 1 1 d . . . H10A H 0.3431 0.1757 0.0512 0.089 Uiso 1 1 calc R . . H10B H 0.3772 0.2239 0.1011 0.089 Uiso 1 1 calc R . . H10C H 0.3642 0.2217 -0.0262 0.089 Uiso 1 1 calc R . . C11 C 0.30205(13) 0.30195(10) 0.0579(2) 0.0593(8) Uani 1 1 d . . . H11A H 0.3304 0.3125 0.1118 0.089 Uiso 1 1 calc R . . H11B H 0.2661 0.3201 0.0722 0.089 Uiso 1 1 calc R . . H11C H 0.3157 0.3110 -0.0148 0.089 Uiso 1 1 calc R . . C12 C 0.27016(10) 0.22729(10) 0.17981(18) 0.0401(6) Uani 1 1 d . . . H12A H 0.2703 0.1889 0.1861 0.048 Uiso 1 1 calc R . . H12B H 0.2969 0.2411 0.2348 0.048 Uiso 1 1 calc R . . C13 C 0.16575(11) 0.21512(10) 0.20870(18) 0.0402(6) Uani 1 1 d . . . C14 C 0.10971(10) 0.23933(9) 0.23987(17) 0.0367(6) Uani 1 1 d . . . C15 C 0.06808(11) 0.20823(10) 0.29280(19) 0.0448(6) Uani 1 1 d . . . C16 C 0.01549(11) 0.23067(11) 0.3284(2) 0.0471(7) Uani 1 1 d . . . C17 C 0.00645(11) 0.28304(11) 0.3015(2) 0.0503(7) Uani 1 1 d . . . H17 H -0.0281 0.2985 0.3249 0.060 Uiso 1 1 calc R . . C18 C 0.04511(11) 0.31505(10) 0.24160(19) 0.0440(6) Uani 1 1 d . . . C19 C 0.09701(10) 0.29194(10) 0.21355(18) 0.0404(6) Uani 1 1 d . . . H19 H 0.1246 0.3120 0.1758 0.048 Uiso 1 1 calc R . . C20 C 0.30409(12) -0.05271(10) -0.1622(2) 0.0551(8) Uani 1 1 d . . . C21 C 0.36598(14) -0.03800(14) -0.1272(3) 0.0850(10) Uani 1 1 d . . . H21A H 0.3927 -0.0638 -0.1560 0.127 Uiso 1 1 calc R . . H21B H 0.3684 -0.0375 -0.0479 0.127 Uiso 1 1 calc R . . H21C H 0.3756 -0.0036 -0.1558 0.127 Uiso 1 1 calc R . . C22 C 0.29870(16) -0.05586(13) -0.2884(3) 0.0841(10) Uani 1 1 d . . . H22A H 0.2597 -0.0656 -0.3079 0.126 Uiso 1 1 calc R . . H22B H 0.3253 -0.0820 -0.3163 0.126 Uiso 1 1 calc R . . H22C H 0.3077 -0.0219 -0.3200 0.126 Uiso 1 1 calc R . . C23 C 0.29173(15) -0.10790(11) -0.1158(3) 0.0789(10) Uani 1 1 d . . . H23A H 0.2533 -0.1188 -0.1370 0.118 Uiso 1 1 calc R . . H23B H 0.2945 -0.1070 -0.0366 0.118 Uiso 1 1 calc R . . H23C H 0.3196 -0.1326 -0.1447 0.118 Uiso 1 1 calc R . . C24 C 0.12635(12) -0.00785(10) 0.0694(2) 0.0527(7) Uani 1 1 d . . . C25 C 0.09495(19) 0.03657(15) 0.1272(4) 0.1114(15) Uani 1 1 d . . . H25A H 0.0810 0.0615 0.0733 0.167 Uiso 1 1 calc R . . H25B H 0.1211 0.0541 0.1771 0.167 Uiso 1 1 calc R . . H25C H 0.0627 0.0224 0.1679 0.167 Uiso 1 1 calc R . . C26 C 0.08422(18) -0.0362(2) -0.0055(4) 0.157(2) Uani 1 1 d . . . H26A H 0.1037 -0.0651 -0.0417 0.235 Uiso 1 1 calc R . . H26B H 0.0697 -0.0119 -0.0600 0.235 Uiso 1 1 calc R . . H26C H 0.0525 -0.0498 0.0375 0.235 Uiso 1 1 calc R . . C27 C 0.1472(2) -0.04590(19) 0.1584(4) 0.1342(18) Uani 1 1 d . . . H27A H 0.1671 -0.0751 0.1245 0.201 Uiso 1 1 calc R . . H27B H 0.1144 -0.0589 0.1994 0.201 Uiso 1 1 calc R . . H27C H 0.1732 -0.0277 0.2075 0.201 Uiso 1 1 calc R . . C28 C -0.02954(13) 0.19816(11) 0.3937(2) 0.0616(8) Uani 1 1 d . . . C29 C -0.04935(17) 0.15055(14) 0.3257(3) 0.0997(13) Uani 1 1 d . . . H29A H -0.0164 0.1288 0.3081 0.150 Uiso 1 1 calc R . . H29B H -0.0672 0.1627 0.2585 0.150 Uiso 1 1 calc R . . H29C H -0.0769 0.1302 0.3676 0.150 Uiso 1 1 calc R . . C30 C -0.00290(16) 0.18023(14) 0.5030(3) 0.0846(10) Uani 1 1 d . . . H30A H 0.0306 0.1587 0.4886 0.127 Uiso 1 1 calc R . . H30B H -0.0309 0.1600 0.5439 0.127 Uiso 1 1 calc R . . H30C H 0.0084 0.2108 0.5454 0.127 Uiso 1 1 calc R . . C31 C -0.08299(13) 0.23140(14) 0.4220(3) 0.0838(11) Uani 1 1 d . . . H31A H -0.0714 0.2618 0.4646 0.126 Uiso 1 1 calc R . . H31B H -0.1098 0.2104 0.4642 0.126 Uiso 1 1 calc R . . H31C H -0.1014 0.2430 0.3550 0.126 Uiso 1 1 calc R . . C32 C 0.02906(11) 0.37212(11) 0.2124(2) 0.0543(7) Uani 1 1 d . . . C33 C 0.07132(14) 0.39653(12) 0.1307(3) 0.0724(9) Uani 1 1 d . . . H33A H 0.0595 0.4322 0.1142 0.109 Uiso 1 1 calc R . . H33B H 0.0716 0.3760 0.0638 0.109 Uiso 1 1 calc R . . H33C H 0.1096 0.3968 0.1622 0.109 Uiso 1 1 calc R . . C34 C -0.03141(13) 0.37304(15) 0.1581(3) 0.0851(11) Uani 1 1 d . . . H34A H -0.0416 0.4089 0.1399 0.128 Uiso 1 1 calc R . . H34B H -0.0595 0.3588 0.2086 0.128 Uiso 1 1 calc R . . H34C H -0.0308 0.3520 0.0919 0.128 Uiso 1 1 calc R . . C35 C 0.02847(16) 0.40540(12) 0.3169(3) 0.0829(10) Uani 1 1 d . . . H35A H 0.0180 0.4413 0.2989 0.124 Uiso 1 1 calc R . . H35B H 0.0663 0.4050 0.3501 0.124 Uiso 1 1 calc R . . H35C H 0.0007 0.3911 0.3680 0.124 Uiso 1 1 calc R . . N1 N 0.23238(9) 0.17149(8) -0.02393(18) 0.0421(5) Uani 1 1 d . . . N2 N 0.21213(8) 0.24651(9) 0.20499(16) 0.0384(5) Uani 1 1 d . . . O1 O 0.31050(9) 0.05788(8) -0.21147(16) 0.0672(6) Uani 1 1 d . . . O2 O 0.07814(11) 0.15625(8) 0.31385(17) 0.0659(6) Uani 1 1 d . . . O3 O 0.27614(8) 0.15285(6) -0.18513(13) 0.0563(5) Uani 1 1 d . . . O4 O 0.16967(8) 0.16675(7) 0.18797(14) 0.0546(5) Uani 1 1 d . . . H1N H 0.2156(11) 0.1594(10) 0.035(2) 0.049(8) Uiso 1 1 d . . . H1O H 0.3054(15) 0.1012(16) -0.216(3) 0.110(12) Uiso 1 1 d . . . H2N H 0.2109(10) 0.2809(10) 0.2309(19) 0.047(7) Uiso 1 1 d . . . H2O H 0.1073(12) 0.1472(10) 0.282(2) 0.047(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0427(16) 0.0316(14) 0.0376(15) 0.0010(11) 0.0045(11) -0.0017(12) C2 0.0463(17) 0.0394(17) 0.0451(15) 0.0015(11) 0.0085(12) -0.0019(13) C3 0.0433(16) 0.0356(16) 0.0496(14) -0.0028(12) 0.0000(13) 0.0000(12) C4 0.0505(17) 0.0328(15) 0.0572(16) -0.0012(12) -0.0003(14) -0.0056(13) C5 0.0402(16) 0.0374(16) 0.0455(15) 0.0007(11) 0.0019(12) -0.0053(13) C6 0.0416(15) 0.0390(16) 0.0393(14) -0.0048(10) 0.0025(12) 0.0029(12) C7 0.0424(15) 0.0380(15) 0.0351(14) 0.0034(12) 0.0025(12) 0.0006(12) C8 0.0541(16) 0.0328(14) 0.0351(13) 0.0021(10) -0.0002(12) 0.0001(12) C9 0.0374(16) 0.0359(14) 0.0422(14) 0.0033(11) 0.0032(12) 0.0005(12) C10 0.0447(17) 0.0678(19) 0.0656(18) 0.0029(14) 0.0121(14) 0.0059(15) C11 0.065(2) 0.0448(17) 0.0682(18) 0.0038(13) -0.0020(15) -0.0125(14) C12 0.0366(15) 0.0447(15) 0.0391(14) -0.0008(11) -0.0036(11) 0.0031(12) C13 0.0434(16) 0.0412(16) 0.0362(13) -0.0065(11) 0.0048(12) -0.0035(14) C14 0.0341(15) 0.0410(15) 0.0350(13) -0.0096(10) 0.0033(11) -0.0039(12) C15 0.0494(17) 0.0415(17) 0.0433(14) -0.0068(12) 0.0057(13) -0.0071(14) C16 0.0414(17) 0.0570(18) 0.0429(14) -0.0084(13) 0.0085(13) -0.0078(14) C17 0.0374(16) 0.0602(19) 0.0532(16) -0.0058(14) 0.0089(13) 0.0003(14) C18 0.0331(15) 0.0526(17) 0.0463(15) -0.0046(12) 0.0014(12) -0.0004(14) C19 0.0348(15) 0.0461(16) 0.0402(14) -0.0030(11) 0.0037(12) -0.0091(12) C20 0.0524(19) 0.0416(17) 0.071(2) -0.0058(13) 0.0042(15) 0.0071(14) C21 0.058(2) 0.068(2) 0.128(3) -0.004(2) -0.001(2) 0.0123(17) C22 0.100(3) 0.077(2) 0.076(2) -0.0198(17) 0.011(2) 0.0237(19) C23 0.084(2) 0.0417(19) 0.111(3) -0.0052(17) 0.014(2) 0.0114(16) C24 0.0511(17) 0.0452(16) 0.0618(16) -0.0021(13) 0.0135(14) -0.0136(14) C25 0.115(3) 0.079(3) 0.140(3) -0.011(2) 0.081(3) -0.018(2) C26 0.084(3) 0.246(6) 0.140(4) -0.068(4) 0.038(3) -0.102(4) C27 0.118(4) 0.142(4) 0.143(4) 0.084(3) 0.058(3) 0.019(3) C28 0.0552(19) 0.071(2) 0.0591(17) -0.0029(15) 0.0192(15) -0.0166(15) C29 0.094(3) 0.105(3) 0.100(3) -0.021(2) 0.028(2) -0.058(2) C30 0.088(3) 0.094(3) 0.072(2) 0.0178(19) 0.0270(19) -0.012(2) C31 0.051(2) 0.104(3) 0.096(3) 0.0105(19) 0.0321(18) -0.0080(18) C32 0.0381(16) 0.0541(17) 0.0707(18) 0.0005(14) 0.0038(14) 0.0022(13) C33 0.062(2) 0.061(2) 0.095(2) 0.0186(16) 0.0019(18) 0.0047(17) C34 0.048(2) 0.084(3) 0.123(3) 0.017(2) -0.0125(19) 0.0081(18) C35 0.087(2) 0.065(2) 0.097(2) -0.0185(18) 0.013(2) 0.0049(18) N1 0.0554(15) 0.0338(13) 0.0370(14) -0.0021(10) 0.0067(11) -0.0032(10) N2 0.0352(13) 0.0380(13) 0.0420(11) -0.0098(10) 0.0027(9) -0.0008(11) O1 0.0728(14) 0.0480(13) 0.0808(14) 0.0015(10) 0.0411(11) 0.0021(10) O2 0.0681(16) 0.0469(14) 0.0828(14) 0.0006(10) 0.0309(13) -0.0038(11) O3 0.0808(14) 0.0400(10) 0.0480(11) 0.0041(8) 0.0260(10) -0.0018(9) O4 0.0549(12) 0.0411(11) 0.0678(12) -0.0123(8) 0.0195(9) -0.0037(9) _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 C6 1.388(3) . ? C1 C2 1.399(3) . ? C1 C7 1.478(3) . ? C2 O1 1.353(3) . ? C2 C3 1.399(3) . ? C3 C4 1.384(3) . ? C3 C20 1.537(3) . ? C4 C5 1.392(3) . ? C5 C6 1.380(3) . ? C5 C24 1.524(3) . ? C7 O3 1.252(3) . ? C7 N1 1.327(3) . ? C8 N1 1.450(3) . ? C8 C9 1.528(3) . ? C9 C11 1.518(3) . ? C9 C10 1.524(4) . ? C9 C12 1.527(3) . ? C12 N2 1.454(3) . ? C13 O4 1.248(3) . ? C13 N2 1.330(3) . ? C13 C14 1.476(3) . ? C14 C15 1.394(3) . ? C14 C19 1.395(3) . ? C15 O2 1.355(3) . ? C15 C16 1.404(3) . ? C16 C17 1.375(3) . ? C16 C28 1.539(4) . ? C17 C18 1.403(3) . ? C18 C19 1.372(3) . ? C18 C32 1.526(4) . ? C20 C23 1.526(4) . ? C20 C21 1.532(4) . ? C20 C22 1.533(4) . ? C24 C25 1.504(4) . ? C24 C26 1.508(5) . ? C24 C27 1.519(5) . ? C28 C29 1.524(4) . ? C28 C30 1.525(5) . ? C28 C31 1.528(4) . ? C32 C35 1.516(4) . ? C32 C33 1.517(4) . ? C32 C34 1.540(4) . ? 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 C6 C1 C2 119.5(2) . . ? C6 C1 C7 122.1(2) . . ? C2 C1 C7 118.4(2) . . ? O1 C2 C1 120.5(2) . . ? O1 C2 C3 119.1(2) . . ? C1 C2 C3 120.5(2) . . ? C4 C3 C2 116.8(2) . . ? C4 C3 C20 122.3(2) . . ? C2 C3 C20 121.0(2) . . ? C3 C4 C5 124.7(2) . . ? C6 C5 C4 116.3(2) . . ? C6 C5 C24 123.0(2) . . ? C4 C5 C24 120.7(2) . . ? C5 C6 C1 122.0(2) . . ? O3 C7 N1 120.8(2) . . ? O3 C7 C1 120.9(2) . . ? N1 C7 C1 118.2(2) . . ? N1 C8 C9 114.36(19) . . ? C11 C9 C10 110.0(2) . . ? C11 C9 C12 110.3(2) . . ? C10 C9 C12 107.79(19) . . ? C11 C9 C8 107.8(2) . . ? C10 C9 C8 111.0(2) . . ? C12 C9 C8 109.94(19) . . ? N2 C12 C9 114.53(18) . . ? O4 C13 N2 121.1(2) . . ? O4 C13 C14 121.2(2) . . ? N2 C13 C14 117.7(2) . . ? C15 C14 C19 119.7(2) . . ? C15 C14 C13 119.1(2) . . ? C19 C14 C13 121.2(2) . . ? O2 C15 C14 120.8(2) . . ? O2 C15 C16 118.6(2) . . ? C14 C15 C16 120.5(2) . . ? C17 C16 C15 116.4(2) . . ? C17 C16 C28 122.0(2) . . ? C15 C16 C28 121.6(2) . . ? C16 C17 C18 125.3(2) . . ? C19 C18 C17 115.9(2) . . ? C19 C18 C32 123.6(2) . . ? C17 C18 C32 120.5(2) . . ? C18 C19 C14 122.0(2) . . ? C23 C20 C21 107.0(3) . . ? C23 C20 C22 107.6(2) . . ? C21 C20 C22 111.2(3) . . ? C23 C20 C3 111.6(2) . . ? C21 C20 C3 108.9(2) . . ? C22 C20 C3 110.4(2) . . ? C25 C24 C26 108.8(3) . . ? C25 C24 C27 107.0(3) . . ? C26 C24 C27 109.2(4) . . ? C25 C24 C5 113.0(2) . . ? C26 C24 C5 108.6(3) . . ? C27 C24 C5 110.1(3) . . ? C29 C28 C30 110.8(3) . . ? C29 C28 C31 108.1(3) . . ? C30 C28 C31 107.0(2) . . ? C29 C28 C16 110.2(2) . . ? C30 C28 C16 109.3(2) . . ? C31 C28 C16 111.5(2) . . ? C35 C32 C33 108.9(2) . . ? C35 C32 C18 109.3(2) . . ? C33 C32 C18 112.2(2) . . ? C35 C32 C34 109.8(3) . . ? C33 C32 C34 107.3(3) . . ? C18 C32 C34 109.4(2) . . ? C7 N1 C8 124.5(2) . . ? C13 N2 C12 123.2(2) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 24.50 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.134 _refine_diff_density_min -0.116 _refine_diff_density_rms 0.028