# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Dr PARTHASARATHI DASTIDAR' _publ_contact_author_address ; Analytical Science CSMCRI G B Marg Bhavnagar Gujarat 364002 INDIA ; _publ_contact_author_email PARTHOD123@REDIFFMAIL.COM _publ_section_title ; Facile preparation and Structure-property Correlation of Low Molecular Mass Organic Gelators Derived from Simple Organic Salts ; loop_ _publ_author_name 'Parthasarathi Dastidar' 'Amar Ballabh' 'Darshak Trivedi' data_dt0942 _database_code_depnum_ccdc_archive 'CCDC 264768' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H31 N O2' _chemical_formula_weight 317.46 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 'P 2(1)2(1)2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.4009(7) _cell_length_b 15.0341(9) _cell_length_c 22.2413(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3812.2(4) _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 PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.59mm _exptl_crystal_size_mid 0.33mm _exptl_crystal_size_min 0.14mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.106 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type SADABS _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_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '<10 %' _diffrn_reflns_number 15480 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2826 _reflns_number_gt 2600 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics "PLATON, 'MERCURY 1.2" _computing_publication_material ? _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^)+(0.0671P)^2^+0.2211P] 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 -0.6(15) _refine_ls_number_reflns 2826 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 N2 N 0.93420(14) 0.87209(12) 0.87400(9) 0.0452(4) Uani 1 1 d . . . N2' N 0.05579(14) 0.14905(12) 0.87747(8) 0.0427(4) Uani 1 1 d . . . O1 O 0.08420(16) 0.05812(12) 0.77141(7) 0.0701(5) Uani 1 1 d . . . O2 O -0.07239(16) -0.03041(13) 0.77103(7) 0.0761(5) Uani 1 1 d . . . C1 C 0.0066(2) 0.01358(15) 0.74544(11) 0.0542(6) Uani 1 1 d . . . C2 C 0.00714(18) 0.01272(13) 0.67831(10) 0.0487(6) Uani 1 1 d . . . C3 C -0.0926(2) -0.00759(17) 0.64600(11) 0.0607(6) Uani 1 1 d . . . H3 H -0.1616 -0.0215 0.6662 0.073 Uiso 1 1 calc R . . C4 C -0.0910(3) -0.00739(18) 0.58400(11) 0.0708(7) Uani 1 1 d . . . H4 H -0.1598 -0.0194 0.5631 0.085 Uiso 1 1 calc R . . C5 C 0.0101(3) 0.01011(16) 0.55247(11) 0.0676(7) Uani 1 1 d . . . C6 C 0.0107(3) 0.0101(2) 0.48454(13) 0.1115(13) Uani 1 1 d . . . H6A H 0.0869 -0.0074 0.4704 0.167 Uiso 1 1 calc R . . H6B H -0.0071 0.0687 0.4701 0.167 Uiso 1 1 calc R . . H6C H -0.0471 -0.0311 0.4700 0.167 Uiso 1 1 calc R . . C7 C 0.1097(3) 0.02877(19) 0.58462(11) 0.0734(8) Uani 1 1 d . . . H7 H 0.1795 0.0399 0.5643 0.088 Uiso 1 1 calc R . . C8 C 0.1083(2) 0.03138(16) 0.64664(11) 0.0597(6) Uani 1 1 d . . . H8 H 0.1765 0.0459 0.6674 0.072 Uiso 1 1 calc R . . O1' O 0.91222(16) 0.96376(12) 0.97848(7) 0.0705(5) Uani 1 1 d . . . O2' O 1.05966(17) 1.05988(13) 0.98334(7) 0.0738(5) Uani 1 1 d . . . C1' C 0.98717(19) 1.00788(15) 1.00660(10) 0.0530(6) Uani 1 1 d . . . C2' C 0.98982(17) 0.99788(13) 1.07375(10) 0.0446(5) Uani 1 1 d . . . C3' C 0.9115(2) 0.94294(17) 1.10245(11) 0.0643(7) Uani 1 1 d . . . H3' H 0.8563 0.9119 1.0800 0.077 Uiso 1 1 calc R . . C4' C 0.9134(2) 0.9331(2) 1.16379(11) 0.0740(8) Uani 1 1 d . . . H4' H 0.8593 0.8955 1.1820 0.089 Uiso 1 1 calc R . . C5' C 0.9929(2) 0.97731(16) 1.19884(10) 0.0596(6) Uani 1 1 d . . . C6' C 0.9963(3) 0.9644(2) 1.26612(11) 0.0928(10) Uani 1 1 d . . . H6A' H 1.0159 0.9037 1.2751 0.139 Uiso 1 1 calc R . . H6B' H 0.9208 0.9782 1.2828 0.139 Uiso 1 1 calc R . . H6C' H 1.0543 1.0031 1.2833 0.139 Uiso 1 1 calc R . . C7' C 1.0708(2) 1.03214(18) 1.17020(10) 0.0668(7) Uani 1 1 d . . . H7' H 1.1259 1.0631 1.1929 0.080 Uiso 1 1 calc R . . C8' C 1.0698(2) 1.04268(17) 1.10879(10) 0.0605(6) Uani 1 1 d . . . H8' H 1.1238 1.0806 1.0907 0.073 Uiso 1 1 calc R . . C1A C 1.04737(18) 0.82186(15) 0.87850(11) 0.0530(6) Uani 1 1 d . . . H1A1 H 1.0536 0.7822 0.8437 0.064 Uiso 1 1 calc R . . C2A C 1.14704(19) 0.88909(17) 0.87554(12) 0.0621(6) Uani 1 1 d . . . H2A2 H 1.1436 0.9207 0.8376 0.075 Uiso 1 1 calc R . . H2A1 H 1.1381 0.9322 0.9077 0.075 Uiso 1 1 calc R . . C3A C 1.2652(2) 0.8432(2) 0.88144(15) 0.0811(9) Uani 1 1 d . . . H3A2 H 1.2778 0.8049 0.8469 0.097 Uiso 1 1 calc R . . H3A1 H 1.3270 0.8875 0.8819 0.097 Uiso 1 1 calc R . . C4A C 1.2714(2) 0.7886(2) 0.93807(16) 0.0901(9) Uani 1 1 d . . . H4A1 H 1.2664 0.8276 0.9727 0.108 Uiso 1 1 calc R . . H4A2 H 1.3460 0.7578 0.9397 0.108 Uiso 1 1 calc R . . C5A C 1.1727(2) 0.7216(2) 0.94032(16) 0.0892(9) Uani 1 1 d . . . H5A2 H 1.1766 0.6891 0.9780 0.107 Uiso 1 1 calc R . . H5A1 H 1.1822 0.6792 0.9078 0.107 Uiso 1 1 calc R . . C6A C 1.0535(2) 0.76630(17) 0.93493(13) 0.0721(7) Uani 1 1 d . . . H6A1 H 0.9925 0.7213 0.9340 0.087 Uiso 1 1 calc R . . H6A2 H 1.0402 0.8038 0.9697 0.087 Uiso 1 1 calc R . . C1B C 0.82337(18) 0.81940(15) 0.86871(10) 0.0501(5) Uani 1 1 d . . . H1B1 H 0.8183 0.7788 0.9031 0.060 Uiso 1 1 calc R . . C2B C 0.72112(18) 0.88372(17) 0.87165(12) 0.0591(6) Uani 1 1 d . . . H2B1 H 0.7293 0.9279 0.8402 0.071 Uiso 1 1 calc R . . H2B2 H 0.7221 0.9143 0.9100 0.071 Uiso 1 1 calc R . . C3B C 0.6046(2) 0.8356(2) 0.86421(12) 0.0720(8) Uani 1 1 d . . . H3B2 H 0.5925 0.7960 0.8981 0.086 Uiso 1 1 calc R . . H3B1 H 0.5413 0.8787 0.8639 0.086 Uiso 1 1 calc R . . C4B C 0.6016(2) 0.7826(2) 0.80670(13) 0.0819(8) Uani 1 1 d . . . H4B2 H 0.5280 0.7504 0.8040 0.098 Uiso 1 1 calc R . . H4B1 H 0.6065 0.8226 0.7726 0.098 Uiso 1 1 calc R . . C5B C 0.7022(2) 0.71778(19) 0.80478(15) 0.0825(9) Uani 1 1 d . . . H5B2 H 0.7006 0.6858 0.7669 0.099 Uiso 1 1 calc R . . H5B1 H 0.6933 0.6747 0.8369 0.099 Uiso 1 1 calc R . . C6B C 0.8200(2) 0.76493(17) 0.81142(12) 0.0665(7) Uani 1 1 d . . . H6B1 H 0.8825 0.7212 0.8122 0.080 Uiso 1 1 calc R . . H6B2 H 0.8327 0.8036 0.7771 0.080 Uiso 1 1 calc R . . C1A' C 0.16732(17) 0.20196(15) 0.88198(10) 0.0468(5) Uani 1 1 d . . . H1A3 H 0.1727 0.2411 0.8469 0.056 Uiso 1 1 calc R . . C2A' C 0.26902(18) 0.13732(17) 0.88021(11) 0.0558(6) Uani 1 1 d . . . H2A4 H 0.2670 0.1043 0.8428 0.067 Uiso 1 1 calc R . . H2A3 H 0.2615 0.0952 0.9130 0.067 Uiso 1 1 calc R . . C3A' C 0.3855(2) 0.1858(2) 0.88543(12) 0.0678(7) Uani 1 1 d . . . H3A3 H 0.3969 0.2232 0.8503 0.081 Uiso 1 1 calc R . . H3A4 H 0.4489 0.1428 0.8867 0.081 Uiso 1 1 calc R . . C4A' C 0.3894(2) 0.24309(19) 0.94192(12) 0.0750(8) Uani 1 1 d . . . H4A3 H 0.3864 0.2052 0.9772 0.090 Uiso 1 1 calc R . . H4A4 H 0.4624 0.2761 0.9430 0.090 Uiso 1 1 calc R . . C5A' C 0.2875(2) 0.30710(18) 0.94296(13) 0.0731(7) Uani 1 1 d . . . H5A3 H 0.2951 0.3487 0.9098 0.088 Uiso 1 1 calc R . . H5A4 H 0.2893 0.3409 0.9801 0.088 Uiso 1 1 calc R . . C6A' C 0.1702(2) 0.25854(16) 0.93797(11) 0.0607(6) Uani 1 1 d . . . H6A4 H 0.1589 0.2212 0.9731 0.073 Uiso 1 1 calc R . . H6A3 H 0.1069 0.3016 0.9367 0.073 Uiso 1 1 calc R . . C1B' C -0.05733(17) 0.19980(14) 0.87302(10) 0.0477(5) Uani 1 1 d . . . H1B3 H -0.0632 0.2395 0.9079 0.057 Uiso 1 1 calc R . . C2B' C -0.15790(18) 0.13372(16) 0.87567(11) 0.0565(6) Uani 1 1 d . . . H2B3 H -0.1495 0.0908 0.8434 0.068 Uiso 1 1 calc R . . H2B4 H -0.1550 0.1018 0.9135 0.068 Uiso 1 1 calc R . . C3B' C -0.2751(2) 0.1801(2) 0.86993(13) 0.0721(8) Uani 1 1 d . . . H3B3 H -0.3373 0.1361 0.8696 0.087 Uiso 1 1 calc R . . H3B4 H -0.2871 0.2185 0.9044 0.087 Uiso 1 1 calc R . . C4B' C -0.2813(2) 0.2347(2) 0.81323(14) 0.0797(8) Uani 1 1 d . . . H4B4 H -0.3556 0.2660 0.8117 0.096 Uiso 1 1 calc R . . H4B3 H -0.2769 0.1957 0.7786 0.096 Uiso 1 1 calc R . . C5B' C -0.1814(2) 0.30163(18) 0.81085(13) 0.0757(8) Uani 1 1 d . . . H5B3 H -0.1904 0.3442 0.8433 0.091 Uiso 1 1 calc R . . H5B4 H -0.1847 0.3339 0.7731 0.091 Uiso 1 1 calc R . . C6B' C -0.0624(2) 0.25581(15) 0.81649(11) 0.0624(6) Uani 1 1 d . . . H6B4 H -0.0492 0.2183 0.7817 0.075 Uiso 1 1 calc R . . H6B3 H -0.0008 0.3003 0.8176 0.075 Uiso 1 1 calc R . . H2N1 H 0.934(2) 0.9081(15) 0.8411(10) 0.056(7) Uiso 1 1 d . . . H2N2 H 0.927(2) 0.9073(15) 0.9090(10) 0.060(7) Uiso 1 1 d . . . H2N3 H 0.060(2) 0.1115(16) 0.8419(11) 0.068(7) Uiso 1 1 d . . . H2N4 H 0.053(2) 0.1140(16) 0.9117(10) 0.063(7) 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 N2 0.0374(10) 0.0451(10) 0.0530(11) -0.0026(10) 0.0007(10) -0.0012(8) N2' 0.0368(9) 0.0448(10) 0.0466(10) -0.0011(9) 0.0003(9) -0.0020(8) O1 0.0750(11) 0.0775(12) 0.0578(9) -0.0133(9) -0.0035(9) -0.0090(11) O2 0.0753(12) 0.0922(13) 0.0607(10) 0.0143(10) 0.0053(9) -0.0140(12) C1 0.0585(14) 0.0497(14) 0.0545(13) -0.0005(11) 0.0011(11) 0.0025(14) C2 0.0566(14) 0.0374(12) 0.0520(13) -0.0007(10) 0.0007(10) 0.0007(11) C3 0.0584(15) 0.0586(15) 0.0652(15) 0.0022(12) -0.0019(12) -0.0076(13) C4 0.084(2) 0.0619(16) 0.0664(16) -0.0016(13) -0.0232(15) -0.0055(16) C5 0.094(2) 0.0535(14) 0.0549(15) 0.0030(11) -0.0027(14) 0.0106(16) C6 0.163(4) 0.117(3) 0.0550(16) -0.0002(16) -0.0011(18) 0.030(3) C7 0.0784(19) 0.0773(19) 0.0645(16) 0.0137(14) 0.0179(14) 0.0066(16) C8 0.0575(15) 0.0588(15) 0.0629(14) 0.0031(12) -0.0006(12) -0.0050(13) O1' 0.0739(11) 0.0782(11) 0.0593(9) -0.0118(9) -0.0078(9) -0.0075(11) O2' 0.0770(12) 0.0877(12) 0.0567(9) 0.0183(9) 0.0027(9) -0.0154(12) C1' 0.0514(13) 0.0522(14) 0.0553(14) 0.0008(11) 0.0002(11) 0.0064(13) C2' 0.0407(12) 0.0419(11) 0.0512(12) 0.0021(9) 0.0001(9) 0.0015(11) C3' 0.0600(15) 0.0659(15) 0.0669(15) 0.0069(13) -0.0066(12) -0.0220(13) C4' 0.0684(17) 0.0845(19) 0.0691(15) 0.0248(14) 0.0072(14) -0.0196(16) C5' 0.0668(16) 0.0605(14) 0.0514(13) 0.0079(11) 0.0058(11) 0.0104(14) C6' 0.121(3) 0.099(2) 0.0588(16) 0.0083(16) 0.0035(16) 0.013(2) C7' 0.0722(17) 0.0705(16) 0.0578(14) -0.0034(13) -0.0121(13) -0.0110(16) C8' 0.0587(14) 0.0618(14) 0.0610(14) 0.0057(12) 0.0011(12) -0.0164(13) C1A 0.0396(11) 0.0494(12) 0.0699(15) -0.0107(11) -0.0007(12) 0.0032(10) C2A 0.0415(12) 0.0655(15) 0.0794(16) 0.0052(14) -0.0009(13) -0.0056(12) C3A 0.0407(14) 0.088(2) 0.114(2) -0.007(2) -0.0013(15) -0.0004(14) C4A 0.0541(16) 0.0810(19) 0.135(3) 0.000(2) -0.0277(18) 0.0092(16) C5A 0.0668(18) 0.0670(17) 0.134(3) 0.0149(18) -0.0195(19) 0.0112(16) C6A 0.0544(15) 0.0555(14) 0.106(2) 0.0145(15) -0.0074(15) -0.0005(13) C1B 0.0397(11) 0.0519(12) 0.0587(13) 0.0010(11) 0.0015(11) -0.0046(10) C2B 0.0414(12) 0.0668(15) 0.0690(15) -0.0136(13) 0.0024(12) 0.0027(12) C3B 0.0413(13) 0.0837(19) 0.0909(19) -0.0063(16) 0.0029(13) 0.0013(13) C4B 0.0524(15) 0.0869(19) 0.106(2) -0.0197(18) -0.0171(15) -0.0092(15) C5B 0.0594(16) 0.0746(18) 0.114(2) -0.0351(17) -0.0045(16) -0.0113(15) C6B 0.0530(15) 0.0612(15) 0.0853(17) -0.0254(14) 0.0052(13) -0.0090(12) C1A' 0.0380(11) 0.0508(12) 0.0515(12) 0.0021(11) 0.0012(10) -0.0071(10) C2A' 0.0432(12) 0.0646(14) 0.0598(13) -0.0106(13) -0.0002(11) 0.0016(11) C3A' 0.0401(12) 0.0848(18) 0.0785(16) -0.0025(15) -0.0022(12) -0.0025(13) C4A' 0.0513(15) 0.0834(18) 0.0904(18) -0.0095(16) -0.0156(14) -0.0150(14) C5A' 0.0577(15) 0.0669(16) 0.0945(19) -0.0190(15) -0.0083(15) -0.0155(14) C6A' 0.0519(14) 0.0554(14) 0.0747(15) -0.0148(13) -0.0006(12) -0.0057(12) C1B' 0.0383(11) 0.0475(12) 0.0572(13) -0.0077(10) 0.0013(11) 0.0011(10) C2B' 0.0408(12) 0.0598(14) 0.0689(15) 0.0052(13) 0.0020(12) -0.0037(11) C3B' 0.0419(13) 0.0759(17) 0.099(2) -0.0037(17) -0.0015(14) -0.0028(13) C4B' 0.0522(15) 0.0773(18) 0.110(2) 0.0011(18) -0.0237(16) 0.0074(15) C5B' 0.0621(16) 0.0622(16) 0.103(2) 0.0113(15) -0.0178(16) 0.0072(14) C6B' 0.0531(14) 0.0518(13) 0.0822(16) 0.0102(13) -0.0042(13) 0.0002(12) _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 N2 C1B 1.496(3) . ? N2 C1A 1.498(3) . ? N2 H2N1 0.91(2) . ? N2 H2N2 0.94(2) . ? N2' C1B' 1.502(3) . ? N2' C1A' 1.503(3) . ? N2' H2N3 0.97(2) . ? N2' H2N4 0.93(2) . ? O1 O1 0.000(6) 1 ? O1 C1 1.250(3) . ? O2 C1 1.254(3) . ? C1 O1 1.250(3) 1 ? C1 C2 1.493(3) . ? C2 C3 1.380(3) . ? C2 C8 1.381(3) . ? C3 C4 1.379(3) . ? C3 H3 0.9300 . ? C4 C5 1.374(4) . ? C4 H4 0.9300 . ? C5 C7 1.371(4) . ? C5 C6 1.511(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.380(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? O1' O1' 0.000(3) 1 ? O1' C1' 1.249(3) . ? O2' C1' 1.250(3) . ? C1' O1' 1.249(3) 1 ? C1' C2' 1.501(3) . ? C2' C3' 1.374(3) . ? C2' C8' 1.376(3) . ? C3' C4' 1.372(3) . ? C3' H3' 0.9300 . ? C4' C5' 1.368(3) . ? C4' H4' 0.9300 . ? C5' C7' 1.369(3) . ? C5' C6' 1.509(3) . ? C6' H6A' 0.9600 . ? C6' H6B' 0.9600 . ? C6' H6C' 0.9600 . ? C7' C8' 1.375(3) . ? C7' H7' 0.9300 . ? C8' H8' 0.9300 . ? C1A C6A 1.509(3) . ? C1A C2A 1.522(3) . ? C1A H1A1 0.9800 . ? C2A C3A 1.520(3) . ? C2A H2A2 0.9700 . ? C2A H2A1 0.9700 . ? C3A C4A 1.505(4) . ? C3A H3A2 0.9700 . ? C3A H3A1 0.9700 . ? C4A C5A 1.511(4) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A C6A 1.521(3) . ? C5A H5A2 0.9700 . ? C5A H5A1 0.9700 . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C1B C6B 1.515(3) . ? C1B C2B 1.516(3) . ? C1B H1B1 0.9800 . ? C2B C3B 1.522(3) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.507(4) . ? C3B H3B2 0.9700 . ? C3B H3B1 0.9700 . ? C4B C5B 1.505(4) . ? C4B H4B2 0.9700 . ? C4B H4B1 0.9700 . ? C5B C6B 1.526(3) . ? C5B H5B2 0.9700 . ? C5B H5B1 0.9700 . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C1A' C6A' 1.508(3) . ? C1A' C2A' 1.513(3) . ? C1A' H1A3 0.9800 . ? C2A' C3A' 1.520(3) . ? C2A' H2A4 0.9700 . ? C2A' H2A3 0.9700 . ? C3A' C4A' 1.524(4) . ? C3A' H3A3 0.9700 . ? C3A' H3A4 0.9700 . ? C4A' C5A' 1.509(4) . ? C4A' H4A3 0.9700 . ? C4A' H4A4 0.9700 . ? C5A' C6A' 1.527(3) . ? C5A' H5A3 0.9700 . ? C5A' H5A4 0.9700 . ? C6A' H6A4 0.9700 . ? C6A' H6A3 0.9700 . ? C1B' C6B' 1.514(3) . ? C1B' C2B' 1.518(3) . ? C1B' H1B3 0.9800 . ? C2B' C3B' 1.513(3) . ? C2B' H2B3 0.9700 . ? C2B' H2B4 0.9700 . ? C3B' C4B' 1.507(4) . ? C3B' H3B3 0.9700 . ? C3B' H3B4 0.9700 . ? C4B' C5B' 1.520(4) . ? C4B' H4B4 0.9700 . ? C4B' H4B3 0.9700 . ? C5B' C6B' 1.527(3) . ? C5B' H5B3 0.9700 . ? C5B' H5B4 0.9700 . ? C6B' H6B4 0.9700 . ? C6B' H6B3 0.9700 . ? 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 C1B N2 C1A 117.75(16) . . ? C1B N2 H2N1 104.4(15) . . ? C1A N2 H2N1 110.9(15) . . ? C1B N2 H2N2 106.7(14) . . ? C1A N2 H2N2 107.6(14) . . ? H2N1 N2 H2N2 109.1(19) . . ? C1B' N2' C1A' 117.52(15) . . ? C1B' N2' H2N3 106.7(14) . . ? C1A' N2' H2N3 108.4(14) . . ? C1B' N2' H2N4 108.5(15) . . ? C1A' N2' H2N4 105.8(15) . . ? H2N3 N2' H2N4 110(2) . . ? O1 O1 C1 0(10) 1 . ? O1 C1 O1 0.00(13) 1 . ? O1 C1 O2 125.5(2) 1 . ? O1 C1 O2 125.5(2) . . ? O1 C1 C2 117.6(2) 1 . ? O1 C1 C2 117.6(2) . . ? O2 C1 C2 116.9(2) . . ? C3 C2 C8 117.9(2) . . ? C3 C2 C1 121.3(2) . . ? C8 C2 C1 120.8(2) . . ? C4 C3 C2 120.6(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 121.5(2) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C7 C5 C4 117.9(2) . . ? C7 C5 C6 121.2(3) . . ? C4 C5 C6 121.0(3) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 C8 121.2(3) . . ? C5 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C7 C8 C2 120.9(2) . . ? C7 C8 H8 119.5 . . ? C2 C8 H8 119.5 . . ? O1' O1' C1' 0(10) 1 . ? O2' C1' O1' 125.2(2) . 1 ? O2' C1' O1' 125.2(2) . . ? O1' C1' O1' 0.00(19) 1 . ? O2' C1' C2' 117.5(2) . . ? O1' C1' C2' 117.3(2) 1 . ? O1' C1' C2' 117.3(2) . . ? C3' C2' C8' 117.5(2) . . ? C3' C2' C1' 120.6(2) . . ? C8' C2' C1' 121.9(2) . . ? C4' C3' C2' 121.1(2) . . ? C4' C3' H3' 119.5 . . ? C2' C3' H3' 119.5 . . ? C5' C4' C3' 121.7(2) . . ? C5' C4' H4' 119.2 . . ? C3' C4' H4' 119.2 . . ? C4' C5' C7' 117.2(2) . . ? C4' C5' C6' 121.3(2) . . ? C7' C5' C6' 121.5(3) . . ? C5' C6' H6A' 109.5 . . ? C5' C6' H6B' 109.5 . . ? H6A' C6' H6B' 109.5 . . ? C5' C6' H6C' 109.5 . . ? H6A' C6' H6C' 109.5 . . ? H6B' C6' H6C' 109.5 . . ? C5' C7' C8' 121.7(2) . . ? C5' C7' H7' 119.1 . . ? C8' C7' H7' 119.1 . . ? C7' C8' C2' 120.8(2) . . ? C7' C8' H8' 119.6 . . ? C2' C8' H8' 119.6 . . ? N2 C1A C6A 111.99(19) . . ? N2 C1A C2A 107.77(17) . . ? C6A C1A C2A 111.6(2) . . ? N2 C1A H1A1 108.4 . . ? C6A C1A H1A1 108.4 . . ? C2A C1A H1A1 108.4 . . ? C3A C2A C1A 110.9(2) . . ? C3A C2A H2A2 109.5 . . ? C1A C2A H2A2 109.5 . . ? C3A C2A H2A1 109.5 . . ? C1A C2A H2A1 109.5 . . ? H2A2 C2A H2A1 108.1 . . ? C4A C3A C2A 111.2(2) . . ? C4A C3A H3A2 109.4 . . ? C2A C3A H3A2 109.4 . . ? C4A C3A H3A1 109.4 . . ? C2A C3A H3A1 109.4 . . ? H3A2 C3A H3A1 108.0 . . ? C3A C4A C5A 110.9(2) . . ? C3A C4A H4A1 109.5 . . ? C5A C4A H4A1 109.5 . . ? C3A C4A H4A2 109.5 . . ? C5A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 108.0 . . ? C4A C5A C6A 111.5(2) . . ? C4A C5A H5A2 109.3 . . ? C6A C5A H5A2 109.3 . . ? C4A C5A H5A1 109.3 . . ? C6A C5A H5A1 109.3 . . ? H5A2 C5A H5A1 108.0 . . ? C1A C6A C5A 110.6(2) . . ? C1A C6A H6A1 109.5 . . ? C5A C6A H6A1 109.5 . . ? C1A C6A H6A2 109.5 . . ? C5A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 108.1 . . ? N2 C1B C6B 111.93(18) . . ? N2 C1B C2B 107.96(17) . . ? C6B C1B C2B 111.2(2) . . ? N2 C1B H1B1 108.6 . . ? C6B C1B H1B1 108.6 . . ? C2B C1B H1B1 108.6 . . ? C1B C2B C3B 111.29(19) . . ? C1B C2B H2B1 109.4 . . ? C3B C2B H2B1 109.4 . . ? C1B C2B H2B2 109.4 . . ? C3B C2B H2B2 109.4 . . ? H2B1 C2B H2B2 108.0 . . ? C4B C3B C2B 111.3(2) . . ? C4B C3B H3B2 109.4 . . ? C2B C3B H3B2 109.4 . . ? C4B C3B H3B1 109.4 . . ? C2B C3B H3B1 109.4 . . ? H3B2 C3B H3B1 108.0 . . ? C5B C4B C3B 110.4(2) . . ? C5B C4B H4B2 109.6 . . ? C3B C4B H4B2 109.6 . . ? C5B C4B H4B1 109.6 . . ? C3B C4B H4B1 109.6 . . ? H4B2 C4B H4B1 108.1 . . ? C4B C5B C6B 111.6(2) . . ? C4B C5B H5B2 109.3 . . ? C6B C5B H5B2 109.3 . . ? C4B C5B H5B1 109.3 . . ? C6B C5B H5B1 109.3 . . ? H5B2 C5B H5B1 108.0 . . ? C1B C6B C5B 110.8(2) . . ? C1B C6B H6B1 109.5 . . ? C5B C6B H6B1 109.5 . . ? C1B C6B H6B2 109.5 . . ? C5B C6B H6B2 109.5 . . ? H6B1 C6B H6B2 108.1 . . ? N2' C1A' C6A' 111.84(17) . . ? N2' C1A' C2A' 107.85(17) . . ? C6A' C1A' C2A' 111.51(19) . . ? N2' C1A' H1A3 108.5 . . ? C6A' C1A' H1A3 108.5 . . ? C2A' C1A' H1A3 108.5 . . ? C1A' C2A' C3A' 111.07(19) . . ? C1A' C2A' H2A4 109.4 . . ? C3A' C2A' H2A4 109.4 . . ? C1A' C2A' H2A3 109.4 . . ? C3A' C2A' H2A3 109.4 . . ? H2A4 C2A' H2A3 108.0 . . ? C2A' C3A' C4A' 111.1(2) . . ? C2A' C3A' H3A3 109.4 . . ? C4A' C3A' H3A3 109.4 . . ? C2A' C3A' H3A4 109.4 . . ? C4A' C3A' H3A4 109.4 . . ? H3A3 C3A' H3A4 108.0 . . ? C5A' C4A' C3A' 110.5(2) . . ? C5A' C4A' H4A3 109.5 . . ? C3A' C4A' H4A3 109.5 . . ? C5A' C4A' H4A4 109.5 . . ? C3A' C4A' H4A4 109.5 . . ? H4A3 C4A' H4A4 108.1 . . ? C4A' C5A' C6A' 111.6(2) . . ? C4A' C5A' H5A3 109.3 . . ? C6A' C5A' H5A3 109.3 . . ? C4A' C5A' H5A4 109.3 . . ? C6A' C5A' H5A4 109.3 . . ? H5A3 C5A' H5A4 108.0 . . ? C1A' C6A' C5A' 110.4(2) . . ? C1A' C6A' H6A4 109.6 . . ? C5A' C6A' H6A4 109.6 . . ? C1A' C6A' H6A3 109.6 . . ? C5A' C6A' H6A3 109.6 . . ? H6A4 C6A' H6A3 108.1 . . ? N2' C1B' C6B' 111.70(18) . . ? N2' C1B' C2B' 108.28(16) . . ? C6B' C1B' C2B' 111.56(18) . . ? N2' C1B' H1B3 108.4 . . ? C6B' C1B' H1B3 108.4 . . ? C2B' C1B' H1B3 108.4 . . ? C3B' C2B' C1B' 111.25(19) . . ? C3B' C2B' H2B3 109.4 . . ? C1B' C2B' H2B3 109.4 . . ? C3B' C2B' H2B4 109.4 . . ? C1B' C2B' H2B4 109.4 . . ? H2B3 C2B' H2B4 108.0 . . ? C4B' C3B' C2B' 111.3(2) . . ? C4B' C3B' H3B3 109.4 . . ? C2B' C3B' H3B3 109.4 . . ? C4B' C3B' H3B4 109.4 . . ? C2B' C3B' H3B4 109.4 . . ? H3B3 C3B' H3B4 108.0 . . ? C3B' C4B' C5B' 110.8(2) . . ? C3B' C4B' H4B4 109.5 . . ? C5B' C4B' H4B4 109.5 . . ? C3B' C4B' H4B3 109.5 . . ? C5B' C4B' H4B3 109.5 . . ? H4B4 C4B' H4B3 108.1 . . ? C4B' C5B' C6B' 111.4(2) . . ? C4B' C5B' H5B3 109.4 . . ? C6B' C5B' H5B3 109.4 . . ? C4B' C5B' H5B4 109.4 . . ? C6B' C5B' H5B4 109.4 . . ? H5B3 C5B' H5B4 108.0 . . ? C1B' C6B' C5B' 110.7(2) . . ? C1B' C6B' H6B4 109.5 . . ? C5B' C6B' H6B4 109.5 . . ? C1B' C6B' H6B3 109.5 . . ? C5B' C6B' H6B3 109.5 . . ? H6B4 C6B' H6B3 108.1 . . ? 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 N2 H2N1 O2 0.91(2) 1.81(2) 2.720(3) 174(2) 1_665 N2 H2N2 O1' 0.94(2) 1.77(2) 2.713(2) 174(2) 1 N2' H2N3 O1 0.97(2) 1.78(2) 2.746(2) 170(2) 1 N2' H2N4 O2' 0.93(2) 1.79(2) 2.710(2) 171(2) 1_445 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.145 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.035 data_dt0944 _database_code_depnum_ccdc_archive 'CCDC 264769' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H31 N O2' _chemical_formula_weight 317.46 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 9.2246(10) _cell_length_b 10.5910(12) _cell_length_c 10.7338(11) _cell_angle_alpha 101.767(2) _cell_angle_beta 113.837(2) _cell_angle_gamma 90.137(2) _cell_volume 934.84(18) _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 PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.358mm _exptl_crystal_size_mid 0.458mm _exptl_crystal_size_min 0.289mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.128 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '<10 %' _diffrn_reflns_number 3755 _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2422 _reflns_number_gt 2186 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.2' _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.1554P] 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 2422 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.12194(15) 0.95330(11) 0.36139(13) 0.0443(3) Uani 1 d . . . O1 O 0.27134(15) 0.13059(12) 0.60366(11) 0.0740(4) Uani 1 d . . . O2 O 0.20288(12) 0.08438(12) 0.76607(12) 0.0700(4) Uani 1 d . . . C1 C 0.29117(17) 0.14056(14) 0.72770(15) 0.0499(4) Uani 1 d . . . C2 C 0.43469(16) 0.22528(13) 0.83945(13) 0.0442(4) Uani 1 d . . . C3 C 0.49028(18) 0.34161(14) 0.82467(16) 0.0545(4) Uani 1 d . . . C4 C 0.4070(2) 0.39604(19) 0.6971(2) 0.0833(6) Uani 1 d . . . H4C H 0.4475 0.4847 0.7163 0.125 Uiso 1 calc R . . H4A H 0.2947 0.3915 0.6734 0.125 Uiso 1 calc R . . H4B H 0.4257 0.3466 0.6204 0.125 Uiso 1 calc R . . C5 C 0.6247(2) 0.41023(19) 0.9347(2) 0.0769(5) Uani 1 d . . . H5 H 0.6618 0.4892 0.9280 0.092 Uiso 1 calc R . . C6 C 0.7044(2) 0.3648(3) 1.0530(2) 0.0901(7) Uani 1 d . . . H6 H 0.7961 0.4118 1.1239 0.108 Uiso 1 calc R . . C7 C 0.6499(2) 0.2511(2) 1.06717(18) 0.0834(6) Uani 1 d . . . H7 H 0.7037 0.2199 1.1472 0.100 Uiso 1 calc R . . C8 C 0.51436(19) 0.18366(17) 0.96163(15) 0.0604(4) Uani 1 d . . . H8 H 0.4748 0.1077 0.9725 0.073 Uiso 1 calc R . . C1A C 0.17749(17) 0.82334(13) 0.38294(15) 0.0487(4) Uani 1 d . . . H1A1 H 0.2935 0.8294 0.4155 0.058 Uiso 1 calc R . . C2A C 0.1354(2) 0.79008(14) 0.49594(15) 0.0571(4) Uani 1 d . . . H2A2 H 0.0215 0.7912 0.4684 0.068 Uiso 1 calc R . . H2A1 H 0.1889 0.8550 0.5821 0.068 Uiso 1 calc R . . C3A C 0.1840(2) 0.65739(16) 0.52101(18) 0.0699(5) Uani 1 d . . . H3A1 H 0.2990 0.6587 0.5572 0.084 Uiso 1 calc R . . H3A2 H 0.1512 0.6370 0.5904 0.084 Uiso 1 calc R . . C4A C 0.1094(2) 0.55437(16) 0.38786(19) 0.0713(5) Uani 1 d . . . H4A2 H -0.0053 0.5468 0.3569 0.086 Uiso 1 calc R . . H4A1 H 0.1471 0.4716 0.4054 0.086 Uiso 1 calc R . . C5A C 0.1505(3) 0.58695(16) 0.2744(2) 0.0756(5) Uani 1 d . . . H5A1 H 0.0954 0.5222 0.1884 0.091 Uiso 1 calc R . . H5A2 H 0.2640 0.5841 0.3010 0.091 Uiso 1 calc R . . C6A C 0.1049(2) 0.71996(14) 0.24859(17) 0.0639(5) Uani 1 d . . . H6A2 H 0.1414 0.7399 0.1812 0.077 Uiso 1 calc R . . H6A1 H -0.0101 0.7196 0.2096 0.077 Uiso 1 calc R . . C1B C 0.16610(17) 1.01255(13) 0.26435(14) 0.0471(4) Uani 1 d . . . H1B1 H 0.1274 0.9514 0.1733 0.056 Uiso 1 calc R . . C2B C 0.08215(19) 1.13438(16) 0.24579(18) 0.0609(4) Uani 1 d . . . H2B1 H 0.1128 1.1932 0.3362 0.073 Uiso 1 calc R . . H2B2 H -0.0320 1.1125 0.2063 0.073 Uiso 1 calc R . . C3B C 0.1239(2) 1.20101(17) 0.15024(19) 0.0731(5) Uani 1 d . . . H3B1 H 0.0834 1.1455 0.0572 0.088 Uiso 1 calc R . . H3B2 H 0.0731 1.2809 0.1440 0.088 Uiso 1 calc R . . C4B C 0.3012(2) 1.23079(17) 0.2031(2) 0.0756(5) Uani 1 d . . . H4B1 H 0.3405 1.2936 0.2917 0.091 Uiso 1 calc R . . H4B2 H 0.3243 1.2683 0.1371 0.091 Uiso 1 calc R . . C5B C 0.3842(2) 1.10923(18) 0.2217(2) 0.0768(5) Uani 1 d . . . H5B1 H 0.4984 1.1312 0.2608 0.092 Uiso 1 calc R . . H5B2 H 0.3534 1.0507 0.1311 0.092 Uiso 1 calc R . . C6B C 0.34424(19) 1.04059(17) 0.31740(18) 0.0624(4) Uani 1 d . . . H6B2 H 0.3940 0.9600 0.3213 0.075 Uiso 1 calc R . . H6B1 H 0.3861 1.0947 0.4112 0.075 Uiso 1 calc R . . H2N1 H 0.006(2) 0.9423(15) 0.3211(16) 0.065(5) Uiso 1 d . . . H2N2 H 0.165(2) 1.0122(17) 0.4517(19) 0.065(5) Uiso 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 N2 0.0448(8) 0.0419(7) 0.0432(7) 0.0089(6) 0.0155(6) -0.0033(5) O1 0.0829(8) 0.0758(8) 0.0462(7) -0.0022(5) 0.0173(6) -0.0225(6) O2 0.0508(7) 0.0814(8) 0.0734(8) 0.0218(6) 0.0192(6) -0.0155(6) C1 0.0469(8) 0.0467(8) 0.0509(9) 0.0091(7) 0.0158(7) 0.0000(7) C2 0.0408(8) 0.0475(8) 0.0423(8) 0.0046(6) 0.0179(6) 0.0005(6) C3 0.0523(9) 0.0513(9) 0.0596(9) 0.0052(7) 0.0262(8) -0.0044(7) C4 0.0903(14) 0.0680(11) 0.0937(14) 0.0354(10) 0.0320(11) -0.0027(10) C5 0.0700(12) 0.0709(12) 0.0812(13) -0.0103(10) 0.0359(11) -0.0255(9) C6 0.0539(11) 0.1267(19) 0.0594(12) -0.0199(12) 0.0122(9) -0.0228(11) C7 0.0630(12) 0.1241(18) 0.0479(10) 0.0132(10) 0.0106(9) 0.0055(12) C8 0.0590(10) 0.0730(11) 0.0485(9) 0.0149(8) 0.0207(8) 0.0043(8) C1A 0.0468(8) 0.0437(8) 0.0551(9) 0.0152(6) 0.0187(7) 0.0006(6) C2A 0.0690(10) 0.0512(9) 0.0472(9) 0.0124(7) 0.0196(8) -0.0042(7) C3A 0.0829(12) 0.0581(10) 0.0651(11) 0.0251(8) 0.0217(9) -0.0042(9) C4A 0.0878(13) 0.0470(9) 0.0820(12) 0.0187(8) 0.0358(10) -0.0004(8) C5A 0.1038(14) 0.0468(9) 0.0862(13) 0.0113(9) 0.0509(11) 0.0053(9) C6A 0.0902(12) 0.0482(9) 0.0583(10) 0.0093(7) 0.0370(9) 0.0021(8) C1B 0.0545(9) 0.0443(8) 0.0393(7) 0.0085(6) 0.0167(6) -0.0049(6) C2B 0.0536(9) 0.0574(10) 0.0740(11) 0.0263(8) 0.0233(8) 0.0037(7) C3B 0.0873(13) 0.0576(10) 0.0770(12) 0.0314(9) 0.0289(10) 0.0062(9) C4B 0.0958(14) 0.0594(10) 0.0888(13) 0.0221(9) 0.0528(11) -0.0066(9) C5B 0.0801(13) 0.0776(12) 0.0989(14) 0.0339(10) 0.0568(11) 0.0067(10) C6B 0.0563(10) 0.0695(10) 0.0733(11) 0.0268(8) 0.0337(8) 0.0066(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 N2 C1A 1.4993(18) . ? N2 C1B 1.5010(17) . ? N2 H2N1 0.977(18) . ? N2 H2N2 0.963(18) . ? O1 C1 1.2501(18) . ? O2 C1 1.2472(18) . ? C1 C2 1.506(2) . ? C2 C8 1.383(2) . ? C2 C3 1.396(2) . ? C3 C5 1.386(2) . ? C3 C4 1.507(2) . ? C4 H4C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C5 C6 1.372(3) . ? C5 H5 0.9300 . ? C6 C7 1.364(3) . ? C6 H6 0.9300 . ? C7 C8 1.370(2) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C1A C6A 1.516(2) . ? C1A C2A 1.517(2) . ? C1A H1A1 0.9800 . ? C2A C3A 1.519(2) . ? C2A H2A2 0.9700 . ? C2A H2A1 0.9700 . ? C3A C4A 1.507(2) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C4A C5A 1.513(2) . ? C4A H4A2 0.9700 . ? C4A H4A1 0.9700 . ? C5A C6A 1.518(2) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A H6A2 0.9700 . ? C6A H6A1 0.9700 . ? C1B C6B 1.512(2) . ? C1B C2B 1.513(2) . ? C1B H1B1 0.9800 . ? C2B C3B 1.521(2) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.506(3) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4B C5B 1.507(3) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C5B C6B 1.526(2) . ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? C6B H6B2 0.9700 . ? C6B H6B1 0.9700 . ? 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 N2 C1B 117.51(11) . . ? C1A N2 H2N1 106.6(9) . . ? C1B N2 H2N1 106.1(9) . . ? C1A N2 H2N2 107.1(9) . . ? C1B N2 H2N2 107.7(10) . . ? H2N1 N2 H2N2 111.9(14) . . ? O2 C1 O1 125.14(14) . . ? O2 C1 C2 117.58(13) . . ? O1 C1 C2 117.27(13) . . ? C8 C2 C3 119.29(14) . . ? C8 C2 C1 117.46(13) . . ? C3 C2 C1 123.26(13) . . ? C5 C3 C2 117.75(15) . . ? C5 C3 C4 119.65(16) . . ? C2 C3 C4 122.57(14) . . ? C3 C4 H4C 109.5 . . ? C3 C4 H4A 109.5 . . ? H4C C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4C C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C6 C5 C3 121.81(18) . . ? C6 C5 H5 119.1 . . ? C3 C5 H5 119.1 . . ? C7 C6 C5 120.28(17) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 118.92(18) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C7 C8 C2 121.89(17) . . ? C7 C8 H8 119.1 . . ? C2 C8 H8 119.1 . . ? N2 C1A C6A 111.62(12) . . ? N2 C1A C2A 108.13(12) . . ? C6A C1A C2A 111.31(12) . . ? N2 C1A H1A1 108.6 . . ? C6A C1A H1A1 108.6 . . ? C2A C1A H1A1 108.6 . . ? C1A C2A C3A 111.25(13) . . ? C1A C2A H2A2 109.4 . . ? C3A C2A H2A2 109.4 . . ? C1A C2A H2A1 109.4 . . ? C3A C2A H2A1 109.4 . . ? H2A2 C2A H2A1 108.0 . . ? C4A C3A C2A 111.07(13) . . ? C4A C3A H3A1 109.4 . . ? C2A C3A H3A1 109.4 . . ? C4A C3A H3A2 109.4 . . ? C2A C3A H3A2 109.4 . . ? H3A1 C3A H3A2 108.0 . . ? C3A C4A C5A 110.92(14) . . ? C3A C4A H4A2 109.5 . . ? C5A C4A H4A2 109.5 . . ? C3A C4A H4A1 109.5 . . ? C5A C4A H4A1 109.5 . . ? H4A2 C4A H4A1 108.0 . . ? C4A C5A C6A 112.21(14) . . ? C4A C5A H5A1 109.2 . . ? C6A C5A H5A1 109.2 . . ? C4A C5A H5A2 109.2 . . ? C6A C5A H5A2 109.2 . . ? H5A1 C5A H5A2 107.9 . . ? C1A C6A C5A 111.07(14) . . ? C1A C6A H6A2 109.4 . . ? C5A C6A H6A2 109.4 . . ? C1A C6A H6A1 109.4 . . ? C5A C6A H6A1 109.4 . . ? H6A2 C6A H6A1 108.0 . . ? N2 C1B C6B 111.95(11) . . ? N2 C1B C2B 108.17(12) . . ? C6B C1B C2B 111.40(12) . . ? N2 C1B H1B1 108.4 . . ? C6B C1B H1B1 108.4 . . ? C2B C1B H1B1 108.4 . . ? C1B C2B C3B 111.02(14) . . ? C1B C2B H2B1 109.4 . . ? C3B C2B H2B1 109.4 . . ? C1B C2B H2B2 109.4 . . ? C3B C2B H2B2 109.4 . . ? H2B1 C2B H2B2 108.0 . . ? C4B C3B C2B 111.56(14) . . ? C4B C3B H3B1 109.3 . . ? C2B C3B H3B1 109.3 . . ? C4B C3B H3B2 109.3 . . ? C2B C3B H3B2 109.3 . . ? H3B1 C3B H3B2 108.0 . . ? C3B C4B C5B 110.44(15) . . ? C3B C4B H4B1 109.6 . . ? C5B C4B H4B1 109.6 . . ? C3B C4B H4B2 109.6 . . ? C5B C4B H4B2 109.6 . . ? H4B1 C4B H4B2 108.1 . . ? C4B C5B C6B 112.24(15) . . ? C4B C5B H5B1 109.2 . . ? C6B C5B H5B1 109.2 . . ? C4B C5B H5B2 109.2 . . ? C6B C5B H5B2 109.2 . . ? H5B1 C5B H5B2 107.9 . . ? C1B C6B C5B 110.54(13) . . ? C1B C6B H6B2 109.5 . . ? C5B C6B H6B2 109.5 . . ? C1B C6B H6B1 109.5 . . ? C5B C6B H6B1 109.5 . . ? H6B2 C6B H6B1 108.1 . . ? 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 N2 H2N1 O2 0.977(18) 1.759(18) 2.7326(17) 174.7(14) 2_566 N2 H2N2 O1 0.963(18) 1.750(19) 2.6994(16) 168.3(15) 1_565 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.115 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.025 data_dt0938 _database_code_depnum_ccdc_archive 'CCDC 264770' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H30 N2 O4' _chemical_formula_weight 374.47 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.352(2) _cell_length_b 8.2035(6) _cell_length_c 19.4855(14) _cell_angle_alpha 90.00 _cell_angle_beta 115.8200(10) _cell_angle_gamma 90.00 _cell_volume 3935.8(5) _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 PLATE _exptl_crystal_colour BROWN _exptl_crystal_size_max 0.35mm _exptl_crystal_size_mid 0.26mm _exptl_crystal_size_min 0.08mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '<10 %' _diffrn_reflns_number 7600 _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2573 _reflns_number_gt 2371 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics "PLATON'; 'MERCURY 1.2" _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+2.3125P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2573 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.49925(6) 0.30574(18) 0.53527(8) 0.0469(4) Uani 1 d . . . N2 N 0.19412(5) -0.05196(15) 0.47847(7) 0.0325(3) Uani 1 d . . . O1 O 0.34427(4) -0.13235(14) 0.52103(7) 0.0476(3) Uani 1 d . . . O2 O 0.27386(4) 0.00148(15) 0.43313(7) 0.0520(3) Uani 1 d . . . O3 O 0.46434(5) 0.31365(18) 0.55803(8) 0.0651(4) Uani 1 d . . . O4 O 0.54419(5) 0.3651(2) 0.57019(8) 0.0734(4) Uani 1 d . . . C1 C 0.32265(6) -0.04143(19) 0.46433(9) 0.0374(4) Uani 1 d . . . C2 C 0.35701(6) 0.0238(2) 0.42840(9) 0.0391(4) Uani 1 d . . . H2 H 0.3405 0.0414 0.3760 0.047 Uiso 1 calc R . . C3 C 0.40913(6) 0.05802(19) 0.46602(9) 0.0392(4) Uani 1 d . . . H3 H 0.4254 0.0444 0.5187 0.047 Uiso 1 calc R . . C4 C 0.44335(6) 0.11671(19) 0.42977(9) 0.0377(4) Uani 1 d . . . C5 C 0.48656(6) 0.22599(19) 0.46178(9) 0.0379(4) Uani 1 d . . . C6 C 0.51965(7) 0.2659(2) 0.42729(10) 0.0474(4) Uani 1 d . . . H6 H 0.5482 0.3387 0.4507 0.057 Uiso 1 calc R . . C7 C 0.51015(7) 0.1981(2) 0.35870(10) 0.0524(5) Uani 1 d . . . H7 H 0.5324 0.2238 0.3352 0.063 Uiso 1 calc R . . C8 C 0.46766(7) 0.0920(2) 0.32459(10) 0.0541(5) Uani 1 d . . . H8 H 0.4606 0.0473 0.2773 0.065 Uiso 1 calc R . . C9 C 0.43530(7) 0.0513(2) 0.35990(10) 0.0476(4) Uani 1 d . . . H9 H 0.4071 -0.0226 0.3361 0.057 Uiso 1 calc R . . C1A C 0.20987(6) 0.01374(19) 0.55772(8) 0.0347(4) Uani 1 d . . . H1A1 H 0.2198 0.1288 0.5588 0.042 Uiso 1 calc R . . C2A C 0.25944(6) -0.0803(2) 0.61208(8) 0.0414(4) Uani 1 d . . . H2A2 H 0.2892 -0.0614 0.5987 0.050 Uiso 1 calc R . . H2A1 H 0.2514 -0.1961 0.6069 0.050 Uiso 1 calc R . . C3A C 0.27648(7) -0.0293(3) 0.69435(9) 0.0528(5) Uani 1 d . . . H3A2 H 0.3065 -0.0969 0.7278 0.063 Uiso 1 calc R . . H3A1 H 0.2888 0.0830 0.7010 0.063 Uiso 1 calc R . . C4A C 0.22987(7) -0.0455(3) 0.71606(10) 0.0579(5) Uani 1 d . . . H4A2 H 0.2198 -0.1593 0.7142 0.069 Uiso 1 calc R . . H4A1 H 0.2412 -0.0069 0.7678 0.069 Uiso 1 calc R . . C5A C 0.18144(7) 0.0522(3) 0.66232(9) 0.0556(5) Uani 1 d . . . H5A2 H 0.1908 0.1671 0.6677 0.067 Uiso 1 calc R . . H5A1 H 0.1516 0.0371 0.6760 0.067 Uiso 1 calc R . . C6A C 0.16341(6) 0.0014(2) 0.57992(9) 0.0429(4) Uani 1 d . . . H6A1 H 0.1502 -0.1100 0.5731 0.052 Uiso 1 calc R . . H6A2 H 0.1338 0.0709 0.5469 0.052 Uiso 1 calc R . . C1B C 0.14667(6) 0.02593(19) 0.41384(8) 0.0346(4) Uani 1 d . . . H1B1 H 0.1150 0.0182 0.4246 0.042 Uiso 1 calc R . . C2B C 0.13463(6) -0.0680(2) 0.34123(9) 0.0423(4) Uani 1 d . . . H2B1 H 0.1269 -0.1809 0.3477 0.051 Uiso 1 calc R . . H2B2 H 0.1662 -0.0655 0.3307 0.051 Uiso 1 calc R . . C3B C 0.08611(7) 0.0065(2) 0.27460(10) 0.0535(5) Uani 1 d . . . H3B2 H 0.0800 -0.0514 0.2281 0.064 Uiso 1 calc R . . H3B1 H 0.0539 -0.0058 0.2831 0.064 Uiso 1 calc R . . C4B C 0.09518(7) 0.1857(2) 0.26508(10) 0.0550(5) Uani 1 d . . . H4B2 H 0.1244 0.1970 0.2500 0.066 Uiso 1 calc R . . H4B1 H 0.0626 0.2313 0.2249 0.066 Uiso 1 calc R . . C5B C 0.10925(7) 0.2797(2) 0.33814(10) 0.0529(5) Uani 1 d . . . H5B2 H 0.0779 0.2817 0.3492 0.064 Uiso 1 calc R . . H5B1 H 0.1180 0.3913 0.3314 0.064 Uiso 1 calc R . . C6B C 0.15707(7) 0.2042(2) 0.40503(9) 0.0463(4) Uani 1 d . . . H6B2 H 0.1895 0.2146 0.3970 0.056 Uiso 1 calc R . . H6B1 H 0.1631 0.2623 0.4514 0.056 Uiso 1 calc R . . H2N2 H 0.2238 -0.0412 0.4636 0.050(5) Uiso 1 d R . . H2N1 H 0.1862 -0.1645 0.4808 0.048(5) Uiso 1 d 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 N1 0.0422(8) 0.0488(9) 0.0512(9) -0.0015(7) 0.0216(7) -0.0062(7) N2 0.0300(7) 0.0367(8) 0.0321(7) 0.0016(5) 0.0147(5) -0.0013(5) O1 0.0489(7) 0.0452(7) 0.0532(7) 0.0074(6) 0.0265(6) -0.0058(5) O2 0.0348(7) 0.0696(9) 0.0571(7) 0.0054(6) 0.0252(6) -0.0016(6) O3 0.0610(8) 0.0779(10) 0.0722(9) -0.0211(7) 0.0436(7) -0.0137(7) O4 0.0512(8) 0.1028(12) 0.0622(8) -0.0241(8) 0.0211(7) -0.0314(8) C1 0.0378(10) 0.0341(9) 0.0441(9) -0.0066(8) 0.0213(8) -0.0071(7) C2 0.0358(9) 0.0437(10) 0.0404(9) 0.0022(7) 0.0191(7) -0.0030(7) C3 0.0389(9) 0.0393(9) 0.0426(9) 0.0037(7) 0.0208(7) 0.0000(7) C4 0.0307(8) 0.0402(9) 0.0432(9) 0.0043(7) 0.0170(7) 0.0021(7) C5 0.0335(8) 0.0394(9) 0.0408(9) 0.0029(7) 0.0162(7) 0.0015(7) C6 0.0387(9) 0.0486(11) 0.0585(11) 0.0026(9) 0.0245(8) -0.0067(8) C7 0.0529(11) 0.0602(12) 0.0579(11) 0.0024(9) 0.0370(9) -0.0078(9) C8 0.0595(11) 0.0623(12) 0.0508(10) -0.0055(9) 0.0336(9) -0.0090(10) C9 0.0437(10) 0.0517(11) 0.0508(10) -0.0067(8) 0.0237(8) -0.0099(8) C1A 0.0358(8) 0.0362(9) 0.0315(8) -0.0008(7) 0.0141(7) -0.0034(7) C2A 0.0339(8) 0.0509(10) 0.0376(9) 0.0020(8) 0.0137(7) 0.0006(7) C3A 0.0459(10) 0.0674(12) 0.0361(9) 0.0012(8) 0.0096(8) 0.0013(9) C4A 0.0617(12) 0.0761(13) 0.0366(9) 0.0069(9) 0.0221(9) 0.0060(10) C5A 0.0580(11) 0.0727(13) 0.0429(10) -0.0001(9) 0.0284(9) 0.0082(10) C6A 0.0374(9) 0.0535(11) 0.0398(9) 0.0019(8) 0.0185(7) 0.0051(8) C1B 0.0281(8) 0.0430(9) 0.0327(8) 0.0038(7) 0.0132(7) -0.0006(7) C2B 0.0424(9) 0.0416(10) 0.0386(9) -0.0013(7) 0.0138(7) -0.0071(7) C3B 0.0502(10) 0.0579(12) 0.0392(10) 0.0009(8) 0.0073(8) -0.0097(9) C4B 0.0541(11) 0.0599(12) 0.0410(10) 0.0114(9) 0.0115(8) -0.0007(9) C5B 0.0582(11) 0.0458(10) 0.0495(11) 0.0105(8) 0.0185(9) 0.0073(9) C6B 0.0527(10) 0.0390(10) 0.0398(9) -0.0005(7) 0.0133(8) 0.0001(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 N1 O3 1.2172(17) . ? N1 O4 1.2177(18) . ? N1 C5 1.472(2) . ? N2 C1B 1.5015(19) . ? N2 C1A 1.5104(18) . ? N2 H2N2 0.9778 . ? N2 H2N1 0.9538 . ? O1 C1 1.2479(19) . ? O2 C1 1.2521(19) . ? C1 O2 1.2521(19) 1 ? C1 C2 1.494(2) . ? C2 C3 1.318(2) . ? C2 H2 0.9300 . ? C3 C4 1.477(2) . ? C3 H3 0.9300 . ? C4 C9 1.389(2) . ? C4 C5 1.395(2) . ? C5 C6 1.381(2) . ? C6 C7 1.364(2) . ? C6 H6 0.9300 . ? C7 C8 1.370(3) . ? C7 H7 0.9300 . ? C8 C9 1.378(2) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C1A C6A 1.514(2) . ? C1A C2A 1.518(2) . ? C1A H1A1 0.9800 . ? C2A C3A 1.520(2) . ? C2A H2A2 0.9700 . ? C2A H2A1 0.9700 . ? C3A C4A 1.514(2) . ? C3A H3A2 0.9700 . ? C3A H3A1 0.9700 . ? C4A C5A 1.512(3) . ? C4A H4A2 0.9700 . ? C4A H4A1 0.9700 . ? C5A C6A 1.518(2) . ? C5A H5A2 0.9700 . ? C5A H5A1 0.9700 . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C1B C6B 1.514(2) . ? C1B C2B 1.516(2) . ? C1B H1B1 0.9800 . ? C2B C3B 1.523(2) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.516(3) . ? C3B H3B2 0.9700 . ? C3B H3B1 0.9700 . ? C4B C5B 1.514(3) . ? C4B H4B2 0.9700 . ? C4B H4B1 0.9700 . ? C5B C6B 1.519(2) . ? C5B H5B2 0.9700 . ? C5B H5B1 0.9700 . ? C6B H6B2 0.9700 . ? C6B H6B1 0.9700 . ? 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 O3 N1 O4 122.43(15) . . ? O3 N1 C5 119.22(13) . . ? O4 N1 C5 118.32(14) . . ? C1B N2 C1A 117.59(11) . . ? C1B N2 H2N2 103.9 . . ? C1A N2 H2N2 111.5 . . ? C1B N2 H2N1 108.7 . . ? C1A N2 H2N1 105.4 . . ? H2N2 N2 H2N1 109.7 . . ? O1 C1 O2 126.29(14) . 1 ? O1 C1 O2 126.29(14) . . ? O1 C1 C2 118.45(14) . . ? O2 C1 C2 115.26(15) 1 . ? O2 C1 C2 115.26(15) . . ? C3 C2 C1 124.34(15) . . ? C3 C2 H2 117.8 . . ? C1 C2 H2 117.8 . . ? C2 C3 C4 124.08(15) . . ? C2 C3 H3 118.0 . . ? C4 C3 H3 118.0 . . ? C9 C4 C5 115.36(14) . . ? C9 C4 C3 118.66(14) . . ? C5 C4 C3 125.83(14) . . ? C6 C5 C4 122.80(15) . . ? C6 C5 N1 116.18(14) . . ? C4 C5 N1 121.02(13) . . ? C7 C6 C5 119.63(16) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 119.59(15) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 120.37(17) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C4 122.24(16) . . ? C8 C9 H9 118.9 . . ? C4 C9 H9 118.9 . . ? N2 C1A C6A 111.54(12) . . ? N2 C1A C2A 107.60(12) . . ? C6A C1A C2A 111.86(13) . . ? N2 C1A H1A1 108.6 . . ? C6A C1A H1A1 108.6 . . ? C2A C1A H1A1 108.6 . . ? C1A C2A C3A 111.48(14) . . ? C1A C2A H2A2 109.3 . . ? C3A C2A H2A2 109.3 . . ? C1A C2A H2A1 109.3 . . ? C3A C2A H2A1 109.3 . . ? H2A2 C2A H2A1 108.0 . . ? C4A C3A C2A 111.21(14) . . ? C4A C3A H3A2 109.4 . . ? C2A C3A H3A2 109.4 . . ? C4A C3A H3A1 109.4 . . ? C2A C3A H3A1 109.4 . . ? H3A2 C3A H3A1 108.0 . . ? C5A C4A C3A 110.52(15) . . ? C5A C4A H4A2 109.5 . . ? C3A C4A H4A2 109.5 . . ? C5A C4A H4A1 109.5 . . ? C3A C4A H4A1 109.5 . . ? H4A2 C4A H4A1 108.1 . . ? C4A C5A C6A 111.72(15) . . ? C4A C5A H5A2 109.3 . . ? C6A C5A H5A2 109.3 . . ? C4A C5A H5A1 109.3 . . ? C6A C5A H5A1 109.3 . . ? H5A2 C5A H5A1 107.9 . . ? C1A C6A C5A 110.93(14) . . ? C1A C6A H6A1 109.5 . . ? C5A C6A H6A1 109.5 . . ? C1A C6A H6A2 109.5 . . ? C5A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 108.0 . . ? N2 C1B C6B 111.70(12) . . ? N2 C1B C2B 108.88(12) . . ? C6B C1B C2B 111.12(13) . . ? N2 C1B H1B1 108.3 . . ? C6B C1B H1B1 108.3 . . ? C2B C1B H1B1 108.3 . . ? C1B C2B C3B 110.25(14) . . ? C1B C2B H2B1 109.6 . . ? C3B C2B H2B1 109.6 . . ? C1B C2B H2B2 109.6 . . ? C3B C2B H2B2 109.6 . . ? H2B1 C2B H2B2 108.1 . . ? C4B C3B C2B 111.43(14) . . ? C4B C3B H3B2 109.3 . . ? C2B C3B H3B2 109.3 . . ? C4B C3B H3B1 109.3 . . ? C2B C3B H3B1 109.3 . . ? H3B2 C3B H3B1 108.0 . . ? C5B C4B C3B 111.52(15) . . ? C5B C4B H4B2 109.3 . . ? C3B C4B H4B2 109.3 . . ? C5B C4B H4B1 109.3 . . ? C3B C4B H4B1 109.3 . . ? H4B2 C4B H4B1 108.0 . . ? C4B C5B C6B 111.75(15) . . ? C4B C5B H5B2 109.3 . . ? C6B C5B H5B2 109.3 . . ? C4B C5B H5B1 109.3 . . ? C6B C5B H5B1 109.3 . . ? H5B2 C5B H5B1 107.9 . . ? C1B C6B C5B 110.91(14) . . ? C1B C6B H6B2 109.5 . . ? C5B C6B H6B2 109.5 . . ? C1B C6B H6B1 109.5 . . ? C5B C6B H6B1 109.5 . . ? H6B2 C6B H6B1 108.0 . . ? 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 N2 H2N2 O2 0.98 1.75 2.7218(15) 173.1 1 N2 H2N1 O1 0.95 1.86 2.7961(16) 167.7 7_546 _diffrn_measured_fraction_theta_max 0.461 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.461 _refine_diff_density_max 0.192 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.029 data_dt0939 _database_code_depnum_ccdc_archive 'CCDC 264771' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H28 N2 O4' _chemical_formula_weight 348.43 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 'P 2(1)/C' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.5764(13) _cell_length_b 12.8644(13) _cell_length_c 12.9625(13) _cell_angle_alpha 90.00 _cell_angle_beta 115.300(2) _cell_angle_gamma 90.00 _cell_volume 1896.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour 'LIGHT YELLOW' _exptl_crystal_size_max 0.58mm _exptl_crystal_size_mid 0.68mm _exptl_crystal_size_min 0.32mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '<10 %' _diffrn_reflns_number 7506 _diffrn_reflns_av_R_equivalents 0.0131 _diffrn_reflns_av_sigmaI/netI 0.0157 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 22.49 _reflns_number_total 2471 _reflns_number_gt 2265 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.2' _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.3835P] 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 2471 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0985 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.72552(10) 0.43670(10) 0.13809(9) 0.0679(4) Uani 1 d . . . O2 O 0.60018(10) 0.43228(9) 0.21783(9) 0.0637(3) Uani 1 d . . . O3 O 1.17585(12) 0.32802(13) 0.66291(12) 0.0955(5) Uani 1 d . . . O4 O 1.05105(14) 0.29659(16) 0.73069(12) 0.1120(6) Uani 1 d . . . C2 C 0.79938(12) 0.39419(11) 0.33361(12) 0.0449(4) Uani 1 d . . . N1 N 1.07560(14) 0.32138(13) 0.65315(12) 0.0697(4) Uani 1 d . . . N2 N 0.37752(11) 0.43484(9) 0.04665(10) 0.0372(3) Uani 1 d . . . C1 C 0.69985(14) 0.42364(12) 0.21990(13) 0.0498(4) Uani 1 d . . . C3 C 0.77621(14) 0.37051(14) 0.42569(13) 0.0590(5) Uani 1 d . . . H3 H 0.6991 0.3722 0.4175 0.071 Uiso 1 calc R . . C4 C 0.86596(15) 0.34431(15) 0.53023(14) 0.0641(5) Uani 1 d . . . H4 H 0.8498 0.3269 0.5917 0.077 Uiso 1 calc R . . C5 C 0.97885(13) 0.34472(12) 0.54093(12) 0.0518(4) Uani 1 d . . . C6 C 1.00487(14) 0.36657(14) 0.45094(14) 0.0618(5) Uani 1 d . . . H6 H 1.0823 0.3652 0.4598 0.074 Uiso 1 calc R . . C7 C 0.91424(14) 0.39068(14) 0.34682(14) 0.0581(4) Uani 1 d . . . H7 H 0.9307 0.4047 0.2848 0.070 Uiso 1 calc R . . C1A C 0.36361(12) 0.32975(10) -0.00815(11) 0.0382(3) Uani 1 d . . . H1A1 H 0.2819 0.3219 -0.0648 0.046 Uiso 1 calc R . . C2A C 0.39242(13) 0.24237(11) 0.07785(12) 0.0464(4) Uani 1 d . . . H2A1 H 0.3375 0.2435 0.1123 0.056 Uiso 1 calc R . . H2A2 H 0.4710 0.2523 0.1379 0.056 Uiso 1 calc R . . C3A C 0.38540(16) 0.13740(12) 0.02048(15) 0.0577(4) Uani 1 d . . . H3A2 H 0.4082 0.0829 0.0776 0.069 Uiso 1 calc R . . H3A1 H 0.3049 0.1245 -0.0341 0.069 Uiso 1 calc R . . C4A C 0.46476(15) 0.13429(12) -0.04015(13) 0.0551(4) Uani 1 d . . . H4A2 H 0.5461 0.1397 0.0154 0.066 Uiso 1 calc R . . H4A1 H 0.4550 0.0684 -0.0795 0.066 Uiso 1 calc R . . C5A C 0.43644(14) 0.22209(12) -0.12503(12) 0.0487(4) Uani 1 d . . . H5A2 H 0.3580 0.2122 -0.1852 0.058 Uiso 1 calc R . . H5A1 H 0.4914 0.2209 -0.1594 0.058 Uiso 1 calc R . . C6A C 0.44299(13) 0.32682(11) -0.06919(12) 0.0439(4) Uani 1 d . . . H6A1 H 0.4195 0.3809 -0.1269 0.053 Uiso 1 calc R . . H6A2 H 0.5235 0.3404 -0.0149 0.053 Uiso 1 calc R . . C1B C 0.31236(12) 0.45646(11) 0.11775(11) 0.0394(3) Uani 1 d . . . H1B1 H 0.3455 0.4121 0.1856 0.047 Uiso 1 calc R . . C2B C 0.18239(12) 0.43290(13) 0.05545(13) 0.0499(4) Uani 1 d . . . H2B1 H 0.1712 0.3599 0.0347 0.060 Uiso 1 calc R . . H2B2 H 0.1480 0.4737 -0.0140 0.060 Uiso 1 calc R . . C3B C 0.12197(14) 0.45878(15) 0.13199(15) 0.0629(5) Uani 1 d . . . H3B2 H 0.0385 0.4446 0.0913 0.075 Uiso 1 calc R . . H3B1 H 0.1534 0.4147 0.1991 0.075 Uiso 1 calc R . . C4B C 0.13957(16) 0.57138(16) 0.16858(15) 0.0710(5) Uani 1 d . . . H4B2 H 0.1020 0.5849 0.2188 0.085 Uiso 1 calc R . . H4B1 H 0.1031 0.6157 0.1021 0.085 Uiso 1 calc R . . C5B C 0.26915(15) 0.59647(14) 0.22976(14) 0.0621(5) Uani 1 d . . . H5B2 H 0.3035 0.5577 0.3007 0.075 Uiso 1 calc R . . H5B1 H 0.2789 0.6700 0.2482 0.075 Uiso 1 calc R . . C6B C 0.33350(14) 0.56939(12) 0.15673(13) 0.0511(4) Uani 1 d . . . H6B2 H 0.3063 0.6146 0.0905 0.061 Uiso 1 calc R . . H6B1 H 0.4172 0.5810 0.2005 0.061 Uiso 1 calc R . . H2N1 H 0.3539(13) 0.4821(13) -0.0113(14) 0.053(4) Uiso 1 d . . . H2N2 H 0.4578(15) 0.4428(12) 0.0964(14) 0.053(4) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0733(8) 0.0791(9) 0.0460(7) 0.0193(6) 0.0205(6) 0.0181(6) O2 0.0442(7) 0.0784(8) 0.0526(7) 0.0073(6) 0.0054(5) 0.0013(5) O3 0.0529(8) 0.1363(14) 0.0761(9) 0.0047(9) 0.0072(7) 0.0322(8) O4 0.0902(11) 0.1867(18) 0.0483(8) 0.0252(10) 0.0192(8) 0.0458(11) C2 0.0451(9) 0.0424(8) 0.0409(8) 0.0020(6) 0.0123(7) 0.0018(6) N1 0.0603(10) 0.0874(11) 0.0497(9) 0.0003(8) 0.0123(8) 0.0289(8) N2 0.0388(7) 0.0374(7) 0.0337(6) 0.0021(5) 0.0138(6) 0.0036(5) C1 0.0514(10) 0.0435(9) 0.0445(9) 0.0023(7) 0.0110(8) 0.0009(7) C3 0.0418(9) 0.0844(12) 0.0474(9) 0.0052(8) 0.0158(7) 0.0055(8) C4 0.0573(11) 0.0933(14) 0.0406(9) 0.0083(9) 0.0198(8) 0.0133(9) C5 0.0470(9) 0.0588(10) 0.0395(8) 0.0004(7) 0.0087(7) 0.0153(7) C6 0.0422(9) 0.0783(12) 0.0621(11) 0.0081(9) 0.0196(8) 0.0120(8) C7 0.0545(10) 0.0718(11) 0.0496(9) 0.0128(8) 0.0238(8) 0.0084(8) C1A 0.0388(8) 0.0382(8) 0.0348(7) -0.0022(6) 0.0130(6) 0.0015(6) C2A 0.0568(9) 0.0434(8) 0.0442(8) 0.0032(7) 0.0265(7) 0.0033(7) C3A 0.0781(11) 0.0393(9) 0.0598(10) 0.0034(7) 0.0334(9) 0.0030(8) C4A 0.0697(11) 0.0452(9) 0.0488(9) -0.0025(7) 0.0237(8) 0.0135(7) C5A 0.0552(9) 0.0535(9) 0.0375(8) -0.0019(7) 0.0199(7) 0.0099(7) C6A 0.0513(9) 0.0453(8) 0.0380(8) 0.0025(6) 0.0217(7) 0.0045(6) C1B 0.0422(8) 0.0424(8) 0.0336(7) 0.0031(6) 0.0164(6) 0.0073(6) C2B 0.0438(9) 0.0553(9) 0.0496(9) -0.0036(7) 0.0192(7) 0.0045(7) C3B 0.0465(9) 0.0845(13) 0.0613(10) -0.0026(9) 0.0265(8) 0.0080(8) C4B 0.0664(12) 0.0905(14) 0.0608(11) -0.0066(10) 0.0317(9) 0.0271(10) C5B 0.0716(11) 0.0616(10) 0.0519(10) -0.0108(8) 0.0251(9) 0.0142(8) C6B 0.0566(9) 0.0473(9) 0.0483(9) -0.0056(7) 0.0214(7) 0.0036(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2449(18) . ? O2 C1 1.2473(19) . ? O3 N1 1.215(2) . ? O4 N1 1.213(2) . ? C2 C3 1.378(2) . ? C2 C7 1.381(2) . ? C2 C1 1.519(2) . ? N1 C5 1.474(2) . ? N2 C1B 1.4979(17) . ? N2 C1A 1.5022(17) . ? N2 H2N1 0.912(17) . ? N2 H2N2 0.943(17) . ? C1 O2 1.2473(19) 1 ? C3 C4 1.384(2) . ? C3 H3 0.9300 . ? C4 C5 1.366(2) . ? C4 H4 0.9300 . ? C5 C6 1.369(2) . ? C6 C7 1.379(2) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C1A C2A 1.5141(19) . ? C1A C6A 1.5164(19) . ? C1A H1A1 0.9800 . ? C2A C3A 1.526(2) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C4A 1.512(2) . ? C3A H3A2 0.9700 . ? C3A H3A1 0.9700 . ? C4A C5A 1.509(2) . ? C4A H4A2 0.9700 . ? C4A H4A1 0.9700 . ? C5A C6A 1.515(2) . ? C5A H5A2 0.9700 . ? C5A H5A1 0.9700 . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C1B C2B 1.513(2) . ? C1B C6B 1.524(2) . ? C1B H1B1 0.9800 . ? C2B C3B 1.522(2) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.511(3) . ? C3B H3B2 0.9700 . ? C3B H3B1 0.9700 . ? C4B C5B 1.511(3) . ? C4B H4B2 0.9700 . ? C4B H4B1 0.9700 . ? C5B C6B 1.525(2) . ? C5B H5B2 0.9700 . ? C5B H5B1 0.9700 . ? C6B H6B2 0.9700 . ? C6B H6B1 0.9700 . ? 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 C3 C2 C7 118.85(14) . . ? C3 C2 C1 120.27(14) . . ? C7 C2 C1 120.88(14) . . ? O4 N1 O3 123.52(15) . . ? O4 N1 C5 118.41(16) . . ? O3 N1 C5 118.07(16) . . ? C1B N2 C1A 118.32(11) . . ? C1B N2 H2N1 108.1(9) . . ? C1A N2 H2N1 106.3(10) . . ? C1B N2 H2N2 105.4(9) . . ? C1A N2 H2N2 107.2(9) . . ? H2N1 N2 H2N2 111.6(13) . . ? O1 C1 O2 126.43(14) . 1 ? O1 C1 O2 126.43(14) . . ? O1 C1 C2 117.02(14) . . ? O2 C1 C2 116.55(14) 1 . ? O2 C1 C2 116.55(14) . . ? C2 C3 C4 121.05(15) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 118.40(15) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C4 C5 C6 122.06(14) . . ? C4 C5 N1 118.88(15) . . ? C6 C5 N1 119.05(14) . . ? C5 C6 C7 118.79(15) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C6 C7 C2 120.79(15) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? N2 C1A C2A 112.15(11) . . ? N2 C1A C6A 107.43(10) . . ? C2A C1A C6A 111.22(11) . . ? N2 C1A H1A1 108.6 . . ? C2A C1A H1A1 108.6 . . ? C6A C1A H1A1 108.6 . . ? C1A C2A C3A 110.63(12) . . ? C1A C2A H2A1 109.5 . . ? C3A C2A H2A1 109.5 . . ? C1A C2A H2A2 109.5 . . ? C3A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 108.1 . . ? C4A C3A C2A 111.30(13) . . ? C4A C3A H3A2 109.4 . . ? C2A C3A H3A2 109.4 . . ? C4A C3A H3A1 109.4 . . ? C2A C3A H3A1 109.4 . . ? H3A2 C3A H3A1 108.0 . . ? C5A C4A C3A 110.89(12) . . ? C5A C4A H4A2 109.5 . . ? C3A C4A H4A2 109.5 . . ? C5A C4A H4A1 109.5 . . ? C3A C4A H4A1 109.5 . . ? H4A2 C4A H4A1 108.0 . . ? C4A C5A C6A 111.68(11) . . ? C4A C5A H5A2 109.3 . . ? C6A C5A H5A2 109.3 . . ? C4A C5A H5A1 109.3 . . ? C6A C5A H5A1 109.3 . . ? H5A2 C5A H5A1 107.9 . . ? C5A C6A C1A 110.97(12) . . ? C5A C6A H6A1 109.4 . . ? C1A C6A H6A1 109.4 . . ? C5A C6A H6A2 109.4 . . ? C1A C6A H6A2 109.4 . . ? H6A1 C6A H6A2 108.0 . . ? N2 C1B C2B 112.63(11) . . ? N2 C1B C6B 108.50(11) . . ? C2B C1B C6B 111.33(12) . . ? N2 C1B H1B1 108.1 . . ? C2B C1B H1B1 108.1 . . ? C6B C1B H1B1 108.1 . . ? C1B C2B C3B 109.56(12) . . ? C1B C2B H2B1 109.8 . . ? C3B C2B H2B1 109.8 . . ? C1B C2B H2B2 109.8 . . ? C3B C2B H2B2 109.8 . . ? H2B1 C2B H2B2 108.2 . . ? C4B C3B C2B 111.56(15) . . ? C4B C3B H3B2 109.3 . . ? C2B C3B H3B2 109.3 . . ? C4B C3B H3B1 109.3 . . ? C2B C3B H3B1 109.3 . . ? H3B2 C3B H3B1 108.0 . . ? C3B C4B C5B 110.48(14) . . ? C3B C4B H4B2 109.6 . . ? C5B C4B H4B2 109.6 . . ? C3B C4B H4B1 109.6 . . ? C5B C4B H4B1 109.6 . . ? H4B2 C4B H4B1 108.1 . . ? C4B C5B C6B 111.39(13) . . ? C4B C5B H5B2 109.4 . . ? C6B C5B H5B2 109.4 . . ? C4B C5B H5B1 109.4 . . ? C6B C5B H5B1 109.4 . . ? H5B2 C5B H5B1 108.0 . . ? C1B C6B C5B 111.09(13) . . ? C1B C6B H6B2 109.4 . . ? C5B C6B H6B2 109.4 . . ? C1B C6B H6B1 109.4 . . ? C5B C6B H6B1 109.4 . . ? H6B2 C6B H6B1 108.0 . . ? 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 N2 H2N1 O1 0.912(17) 1.840(18) 2.7372(16) 167.3(14) 3_665 N2 H2N2 O2 0.943(17) 1.815(18) 2.7305(16) 163.0(14) 1 _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.195 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.026 data_dt0940 _database_code_depnum_ccdc_archive 'CCDC 264772' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H56 N4 O8' _chemical_formula_weight 696.87 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 'C 2/C' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.7738(15) _cell_length_b 10.2812(7) _cell_length_c 35.610(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.4810(10) _cell_angle_gamma 90.00 _cell_volume 7591.6(9) _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 PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.56mm _exptl_crystal_size_mid 0.35mm _exptl_crystal_size_min 0.13mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3008 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type SADABS _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_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '<10 %' _diffrn_reflns_number 14920 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 22.50 _reflns_number_total 4962 _reflns_number_gt 4333 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.2' _computing_publication_material ? _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^)+(0.0518P)^2^+5.2677P] 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 4962 _refine_ls_number_parameters 467 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 N1 N 0.42755(12) 0.4084(3) 0.29234(7) 0.1007(8) Uani 1 1 d . . . N2 N 0.41973(7) -0.04575(15) 0.15240(4) 0.0399(4) Uani 1 1 d . . . N2' N 0.27769(7) 0.72659(15) 0.09026(5) 0.0407(4) Uani 1 1 d . . . O1 O 0.37809(7) 0.74959(14) 0.19198(4) 0.0696(4) Uani 1 1 d . . . O2 O 0.28083(6) 0.69536(14) 0.16747(3) 0.0591(4) Uani 1 1 d . . . O3 O 0.42585(12) 0.3072(3) 0.30917(8) 0.1544(11) Uani 1 1 d . . . O4 O 0.47448(11) 0.4777(3) 0.29376(8) 0.1753(14) Uani 1 1 d . . . C1 C 0.32725(9) 0.68515(18) 0.19121(5) 0.0452(4) Uani 1 1 d . . . C2 C 0.32156(8) 0.58536(16) 0.22202(4) 0.0401(4) Uani 1 1 d . . . C3 C 0.26310(9) 0.5290(2) 0.22856(5) 0.0529(5) Uani 1 1 d . . . H3 H 0.2263 0.5545 0.2142 0.063 Uiso 1 1 calc R . . C4 C 0.25813(10) 0.4352(2) 0.25601(6) 0.0649(6) Uani 1 1 d . . . H4 H 0.2181 0.3995 0.2603 0.078 Uiso 1 1 calc R . . C5 C 0.31180(11) 0.3946(2) 0.27692(6) 0.0634(6) Uani 1 1 d . . . H5 H 0.3091 0.3302 0.2951 0.076 Uiso 1 1 calc R . . C6 C 0.36975(10) 0.4517(2) 0.27027(5) 0.0569(5) Uani 1 1 d . . . C7 C 0.37565(9) 0.54731(18) 0.24355(5) 0.0483(5) Uani 1 1 d . . . H7 H 0.4155 0.5854 0.2401 0.058 Uiso 1 1 calc R . . O1' O 0.41162(7) -0.04021(16) 0.07578(4) 0.0720(4) Uani 1 1 d . . . O2' O 0.31111(7) -0.05596(14) 0.05115(4) 0.0680(4) Uani 1 1 d . . . O3' O 0.24790(9) 0.22290(18) -0.05638(5) 0.0888(5) Uani 1 1 d . . . O4' O 0.31942(9) 0.33547(17) -0.08325(5) 0.0914(5) Uani 1 1 d . . . N1' N 0.30356(10) 0.25829(17) -0.05949(5) 0.0612(5) Uani 1 1 d . . . C1' C 0.36707(10) -0.01372(18) 0.05169(5) 0.0506(5) Uani 1 1 d . . . C2' C 0.38402(9) 0.07614(17) 0.02035(5) 0.0438(4) Uani 1 1 d . . . C3' C 0.44761(10) 0.1085(2) 0.01569(6) 0.0597(5) Uani 1 1 d . . . H3' H 0.4797 0.0778 0.0328 0.072 Uiso 1 1 calc R . . C4' C 0.46415(11) 0.1859(2) -0.01402(7) 0.0729(6) Uani 1 1 d . . . H4' H 0.5073 0.2040 -0.0173 0.087 Uiso 1 1 calc R . . C5' C 0.41732(11) 0.2359(2) -0.03854(6) 0.0633(6) Uani 1 1 d . . . H5' H 0.4280 0.2894 -0.0583 0.076 Uiso 1 1 calc R . . C6' C 0.35438(9) 0.20518(17) -0.03331(5) 0.0473(5) Uani 1 1 d . . . C7' C 0.33675(9) 0.12523(17) -0.00476(5) 0.0441(4) Uani 1 1 d . . . H7' H 0.2936 0.1044 -0.0024 0.053 Uiso 1 1 calc R . . C1A C 0.49169(8) -0.05118(18) 0.15964(5) 0.0433(4) Uani 1 1 d . . . H1A1 H 0.5107 0.0215 0.1464 0.052 Uiso 1 1 calc R . . C2A C 0.51117(9) -0.0393(2) 0.20102(5) 0.0604(6) Uani 1 1 d . . . H2A2 H 0.4905 -0.1073 0.2148 0.072 Uiso 1 1 calc R . . H2A1 H 0.4970 0.0440 0.2103 0.072 Uiso 1 1 calc R . . C3A C 0.58415(10) -0.0505(3) 0.20751(7) 0.0789(7) Uani 1 1 d . . . H3A1 H 0.6045 0.0222 0.1955 0.095 Uiso 1 1 calc R . . H3A2 H 0.5958 -0.0463 0.2343 0.095 Uiso 1 1 calc R . . C4A C 0.60855(11) -0.1760(3) 0.19187(7) 0.0774(7) Uani 1 1 d . . . H4A2 H 0.5915 -0.2485 0.2056 0.093 Uiso 1 1 calc R . . H4A1 H 0.6552 -0.1784 0.1953 0.093 Uiso 1 1 calc R . . C5A C 0.58875(10) -0.1896(2) 0.15059(6) 0.0692(6) Uani 1 1 d . . . H5A1 H 0.6024 -0.2738 0.1417 0.083 Uiso 1 1 calc R . . H5A2 H 0.6100 -0.1231 0.1365 0.083 Uiso 1 1 calc R . . C6A C 0.51590(9) -0.1766(2) 0.14354(6) 0.0567(5) Uani 1 1 d . . . H6A1 H 0.5049 -0.1790 0.1167 0.068 Uiso 1 1 calc R . . H6A2 H 0.4948 -0.2496 0.1550 0.068 Uiso 1 1 calc R . . C1B C 0.38456(8) 0.07051(17) 0.16609(5) 0.0437(4) Uani 1 1 d . . . H1B1 H 0.3887 0.0706 0.1936 0.052 Uiso 1 1 calc R . . C2B C 0.31375(8) 0.05609(19) 0.15385(6) 0.0523(5) Uani 1 1 d . . . H2B1 H 0.2973 -0.0238 0.1641 0.063 Uiso 1 1 calc R . . H2B2 H 0.3090 0.0504 0.1266 0.063 Uiso 1 1 calc R . . C3B C 0.27477(10) 0.1706(2) 0.16707(6) 0.0681(6) Uani 1 1 d . . . H3B1 H 0.2302 0.1617 0.1575 0.082 Uiso 1 1 calc R . . H3B2 H 0.2756 0.1707 0.1943 0.082 Uiso 1 1 calc R . . C4B C 0.30175(12) 0.2979(2) 0.15351(7) 0.0743(7) Uani 1 1 d . . . H4B1 H 0.2779 0.3698 0.1635 0.089 Uiso 1 1 calc R . . H4B2 H 0.2967 0.3017 0.1263 0.089 Uiso 1 1 calc R . . C5B C 0.37248(11) 0.3110(2) 0.16596(7) 0.0707(6) Uani 1 1 d . . . H5B1 H 0.3770 0.3150 0.1932 0.085 Uiso 1 1 calc R . . H5B2 H 0.3891 0.3915 0.1562 0.085 Uiso 1 1 calc R . . C6B C 0.41185(10) 0.19731(18) 0.15232(6) 0.0572(5) Uani 1 1 d . . . H6B1 H 0.4107 0.1974 0.1250 0.069 Uiso 1 1 calc R . . H6B2 H 0.4564 0.2062 0.1617 0.069 Uiso 1 1 calc R . . C1A' C 0.31555(8) 0.61531(18) 0.07551(5) 0.0464(4) Uani 1 1 d . . . H1A3 H 0.2969 0.5339 0.0842 0.056 Uiso 1 1 calc R . . C2A' C 0.31293(11) 0.6136(2) 0.03295(5) 0.0637(6) Uani 1 1 d . . . H2A4 H 0.3284 0.6960 0.0238 0.076 Uiso 1 1 calc R . . H2A3 H 0.2687 0.6023 0.0232 0.076 Uiso 1 1 calc R . . C3A' C 0.35406(13) 0.5038(2) 0.01903(7) 0.0809(7) Uani 1 1 d . . . H3A4 H 0.3356 0.4211 0.0259 0.097 Uiso 1 1 calc R . . H3A3 H 0.3538 0.5073 -0.0082 0.097 Uiso 1 1 calc R . . C4A' C 0.42294(13) 0.5120(3) 0.03541(9) 0.0957(9) Uani 1 1 d . . . H4A4 H 0.4471 0.4376 0.0272 0.115 Uiso 1 1 calc R . . H4A3 H 0.4430 0.5900 0.0262 0.115 Uiso 1 1 calc R . . C5A' C 0.42525(12) 0.5148(3) 0.07774(8) 0.0877(8) Uani 1 1 d . . . H5A3 H 0.4695 0.5260 0.0875 0.105 Uiso 1 1 calc R . . H5A4 H 0.4097 0.4326 0.0870 0.105 Uiso 1 1 calc R . . C6A' C 0.38419(9) 0.6251(2) 0.09195(6) 0.0622(5) Uani 1 1 d . . . H6A4 H 0.3845 0.6214 0.1192 0.075 Uiso 1 1 calc R . . H6A3 H 0.4024 0.7079 0.0850 0.075 Uiso 1 1 calc R . . C1B' C 0.20673(8) 0.73183(18) 0.07940(5) 0.0452(4) Uani 1 1 d . . . H1B3 H 0.2012 0.7446 0.0521 0.054 Uiso 1 1 calc R . . C2B' C 0.17201(9) 0.60882(19) 0.08917(6) 0.0564(5) Uani 1 1 d . . . H2B4 H 0.1773 0.5935 0.1161 0.068 Uiso 1 1 calc R . . H2B3 H 0.1903 0.5355 0.0764 0.068 Uiso 1 1 calc R . . C3B' C 0.10058(9) 0.6212(2) 0.07733(6) 0.0674(6) Uani 1 1 d . . . H3B3 H 0.0954 0.6296 0.0502 0.081 Uiso 1 1 calc R . . H3B4 H 0.0783 0.5428 0.0844 0.081 Uiso 1 1 calc R . . C4B' C 0.07053(10) 0.7368(2) 0.09526(6) 0.0677(6) Uani 1 1 d . . . H4B3 H 0.0707 0.7232 0.1222 0.081 Uiso 1 1 calc R . . H4B4 H 0.0260 0.7451 0.0856 0.081 Uiso 1 1 calc R . . C5B' C 0.10650(10) 0.8608(2) 0.08744(8) 0.0763(7) Uani 1 1 d . . . H5B3 H 0.0886 0.9318 0.1014 0.092 Uiso 1 1 calc R . . H5B4 H 0.1007 0.8815 0.0609 0.092 Uiso 1 1 calc R . . C6B' C 0.17840(9) 0.84829(19) 0.09845(7) 0.0602(5) Uani 1 1 d . . . H6B3 H 0.2005 0.9266 0.0912 0.072 Uiso 1 1 calc R . . H6B4 H 0.1847 0.8388 0.1255 0.072 Uiso 1 1 calc R . . H2N1 H 0.4124(8) -0.0497(17) 0.1276(6) 0.048(5) Uiso 1 1 d . . . H2N2 H 0.4014(9) -0.122(2) 0.1641(6) 0.067(6) Uiso 1 1 d . . . H2N3 H 0.2954(9) 0.802(2) 0.0814(5) 0.054(6) Uiso 1 1 d . . . H2N4 H 0.2822(9) 0.7236(18) 0.1168(6) 0.058(6) 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 N1 0.0760(15) 0.129(2) 0.0957(16) 0.0610(16) -0.0061(12) 0.0111(14) N2 0.0388(8) 0.0446(9) 0.0361(9) 0.0022(7) 0.0006(7) -0.0021(7) N2' 0.0414(9) 0.0404(9) 0.0402(9) 0.0025(7) 0.0014(7) -0.0029(7) O1 0.0611(9) 0.0693(10) 0.0780(10) 0.0315(8) -0.0003(7) -0.0136(8) O2 0.0595(8) 0.0735(10) 0.0440(7) 0.0125(7) -0.0004(7) 0.0055(7) O3 0.1317(19) 0.162(2) 0.166(2) 0.110(2) -0.0198(16) 0.0227(16) O4 0.0818(15) 0.241(3) 0.196(3) 0.126(2) -0.0507(16) -0.0231(19) C1 0.0488(11) 0.0463(11) 0.0411(10) 0.0021(8) 0.0074(9) 0.0052(9) C2 0.0457(10) 0.0395(10) 0.0352(9) -0.0024(8) 0.0034(8) 0.0001(8) C3 0.0478(11) 0.0633(13) 0.0474(11) 0.0044(10) 0.0017(9) -0.0063(10) C4 0.0629(13) 0.0726(15) 0.0597(13) 0.0126(11) 0.0080(11) -0.0189(11) C5 0.0798(15) 0.0597(13) 0.0512(12) 0.0164(10) 0.0070(11) -0.0068(12) C6 0.0609(13) 0.0611(13) 0.0479(11) 0.0116(10) -0.0027(9) 0.0055(10) C7 0.0488(11) 0.0499(11) 0.0460(10) 0.0038(9) 0.0024(8) -0.0033(9) O1' 0.0834(10) 0.0901(11) 0.0418(8) 0.0118(7) -0.0026(7) 0.0112(9) O2' 0.0702(10) 0.0638(9) 0.0705(9) 0.0231(7) 0.0085(7) -0.0133(8) O3' 0.0780(12) 0.1060(14) 0.0807(11) 0.0259(10) -0.0100(9) 0.0026(10) O4' 0.1300(15) 0.0736(11) 0.0709(10) 0.0323(9) 0.0096(10) 0.0089(10) N1' 0.0898(15) 0.0484(10) 0.0456(10) 0.0051(8) 0.0056(9) 0.0064(10) C1' 0.0653(13) 0.0465(11) 0.0403(11) -0.0007(9) 0.0062(10) 0.0026(10) C2' 0.0527(11) 0.0397(10) 0.0390(10) -0.0045(8) 0.0029(8) -0.0064(8) C3' 0.0561(13) 0.0598(13) 0.0624(13) 0.0023(11) -0.0038(10) -0.0084(10) C4' 0.0575(13) 0.0720(15) 0.0904(17) 0.0087(13) 0.0143(12) -0.0190(12) C5' 0.0793(16) 0.0506(12) 0.0618(13) 0.0085(10) 0.0203(12) -0.0113(11) C6' 0.0661(13) 0.0374(10) 0.0388(10) -0.0013(8) 0.0056(9) -0.0019(9) C7' 0.0512(11) 0.0402(10) 0.0411(10) -0.0048(8) 0.0049(8) -0.0052(8) C1A 0.0354(9) 0.0504(11) 0.0441(10) 0.0039(8) 0.0027(7) -0.0036(8) C2A 0.0450(11) 0.0872(15) 0.0480(11) -0.0106(11) -0.0046(9) 0.0048(10) C3A 0.0478(12) 0.121(2) 0.0662(14) -0.0210(14) -0.0111(10) 0.0082(13) C4A 0.0496(12) 0.1018(19) 0.0791(16) 0.0049(14) -0.0094(11) 0.0163(12) C5A 0.0522(12) 0.0836(16) 0.0717(14) -0.0072(12) 0.0031(10) 0.0177(11) C6A 0.0498(11) 0.0668(13) 0.0531(11) -0.0051(10) -0.0005(9) 0.0065(10) C1B 0.0451(10) 0.0486(11) 0.0375(9) -0.0025(8) 0.0025(8) 0.0018(8) C2B 0.0431(10) 0.0578(12) 0.0560(11) -0.0006(9) 0.0017(9) 0.0024(9) C3B 0.0565(13) 0.0789(16) 0.0687(14) -0.0057(12) 0.0029(10) 0.0187(11) C4B 0.0906(17) 0.0655(15) 0.0660(14) -0.0084(12) -0.0010(12) 0.0284(13) C5B 0.0920(17) 0.0492(13) 0.0708(14) -0.0084(11) 0.0052(12) 0.0041(11) C6B 0.0614(12) 0.0486(12) 0.0617(12) -0.0025(10) 0.0037(10) -0.0048(10) C1A' 0.0482(11) 0.0399(10) 0.0517(11) -0.0021(8) 0.0091(8) -0.0026(8) C2A' 0.0792(15) 0.0617(13) 0.0511(12) -0.0088(10) 0.0124(10) -0.0084(11) C3A' 0.104(2) 0.0691(16) 0.0740(15) -0.0197(12) 0.0413(14) -0.0154(14) C4A' 0.092(2) 0.0682(16) 0.134(3) -0.0219(16) 0.0652(18) -0.0064(14) C5A' 0.0631(15) 0.0808(17) 0.121(2) -0.0148(16) 0.0184(14) 0.0182(13) C6A' 0.0501(12) 0.0635(13) 0.0730(14) -0.0088(11) 0.0037(10) 0.0080(10) C1B' 0.0408(10) 0.0534(11) 0.0408(10) 0.0060(8) -0.0016(8) -0.0028(8) C2B' 0.0507(11) 0.0521(12) 0.0663(13) -0.0071(10) 0.0027(9) -0.0109(9) C3B' 0.0502(12) 0.0775(15) 0.0743(14) -0.0086(12) 0.0023(10) -0.0182(11) C4B' 0.0434(11) 0.0860(16) 0.0740(14) -0.0013(12) 0.0055(10) -0.0074(11) C5B' 0.0491(12) 0.0726(15) 0.1075(19) 0.0136(14) 0.0067(12) 0.0082(11) C6B' 0.0470(11) 0.0469(12) 0.0868(15) 0.0047(11) 0.0040(10) -0.0009(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 N1 O3 1.202(3) . ? N1 O4 1.206(3) . ? N1 C6 1.464(3) . ? N2 C1B 1.498(2) . ? N2 C1A 1.503(2) . ? N2 H2N1 0.887(19) . ? N2 H2N2 0.98(2) . ? N2' C1A' 1.501(2) . ? N2' C1B' 1.502(2) . ? N2' H2N3 0.92(2) . ? N2' H2N4 0.95(2) . ? O1 C1 1.246(2) . ? O2 C1 1.248(2) . ? C1 O2 1.248(2) 1 ? C1 C2 1.512(2) . ? C2 C7 1.378(2) . ? C2 C3 1.378(2) . ? C3 C4 1.382(3) . ? C3 H3 0.9300 . ? C4 C5 1.368(3) . ? C4 H4 0.9300 . ? C5 C6 1.373(3) . ? C5 H5 0.9300 . ? C6 C7 1.378(3) . ? C7 H7 0.9300 . ? O1' O1' 0.000(4) 1 ? O1' C1' 1.253(2) . ? O2' C1' 1.240(2) . ? O3' N1' 1.224(2) . ? O4' N1' 1.220(2) . ? N1' C6' 1.470(3) . ? C1' O1' 1.253(2) 1 ? C1' C2' 1.507(3) . ? C2' C3' 1.382(3) . ? C2' C7' 1.383(2) . ? C3' C4' 1.384(3) . ? C3' H3' 0.9300 . ? C4' C5' 1.367(3) . ? C4' H4' 0.9300 . ? C5' C6' 1.369(3) . ? C5' H5' 0.9300 . ? C6' C7' 1.374(2) . ? C7' H7' 0.9300 . ? C1A C2A 1.509(3) . ? C1A C6A 1.510(3) . ? C1A H1A1 0.9800 . ? C2A C3A 1.524(3) . ? C2A H2A2 0.9700 . ? C2A H2A1 0.9700 . ? C3A C4A 1.505(3) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C4A C5A 1.509(3) . ? C4A H4A2 0.9700 . ? C4A H4A1 0.9700 . ? C5A C6A 1.525(3) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C1B C6B 1.515(3) . ? C1B C2B 1.516(2) . ? C1B H1B1 0.9800 . ? C2B C3B 1.520(3) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.514(3) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4B C5B 1.515(3) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C5B C6B 1.522(3) . ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C1A' C6A' 1.511(3) . ? C1A' C2A' 1.514(3) . ? C1A' H1A3 0.9800 . ? C2A' C3A' 1.517(3) . ? C2A' H2A4 0.9700 . ? C2A' H2A3 0.9700 . ? C3A' C4A' 1.515(4) . ? C3A' H3A4 0.9700 . ? C3A' H3A3 0.9700 . ? C4A' C5A' 1.505(4) . ? C4A' H4A4 0.9700 . ? C4A' H4A3 0.9700 . ? C5A' C6A' 1.523(3) . ? C5A' H5A3 0.9700 . ? C5A' H5A4 0.9700 . ? C6A' H6A4 0.9700 . ? C6A' H6A3 0.9700 . ? C1B' C2B' 1.507(3) . ? C1B' C6B' 1.513(3) . ? C1B' H1B3 0.9800 . ? C2B' C3B' 1.523(3) . ? C2B' H2B4 0.9700 . ? C2B' H2B3 0.9700 . ? C3B' C4B' 1.503(3) . ? C3B' H3B3 0.9700 . ? C3B' H3B4 0.9700 . ? C4B' C5B' 1.513(3) . ? C4B' H4B3 0.9700 . ? C4B' H4B4 0.9700 . ? C5B' C6B' 1.527(3) . ? C5B' H5B3 0.9700 . ? C5B' H5B4 0.9700 . ? C6B' H6B3 0.9700 . ? C6B' H6B4 0.9700 . ? 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 O3 N1 O4 122.6(3) . . ? O3 N1 C6 118.9(3) . . ? O4 N1 C6 118.5(2) . . ? C1B N2 C1A 118.27(14) . . ? C1B N2 H2N1 107.6(12) . . ? C1A N2 H2N1 106.2(11) . . ? C1B N2 H2N2 106.8(12) . . ? C1A N2 H2N2 107.9(11) . . ? H2N1 N2 H2N2 109.9(17) . . ? C1A' N2' C1B' 117.66(14) . . ? C1A' N2' H2N3 106.9(12) . . ? C1B' N2' H2N3 106.8(11) . . ? C1A' N2' H2N4 107.7(12) . . ? C1B' N2' H2N4 107.1(11) . . ? H2N3 N2' H2N4 110.6(16) . . ? O1 C1 O2 126.14(17) . 1 ? O1 C1 O2 126.14(17) . . ? O1 C1 C2 116.65(16) . . ? O2 C1 C2 117.22(16) 1 . ? O2 C1 C2 117.22(16) . . ? C7 C2 C3 118.93(17) . . ? C7 C2 C1 119.94(16) . . ? C3 C2 C1 121.11(16) . . ? C2 C3 C4 121.18(18) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 120.31(19) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 118.02(19) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C5 C6 C7 122.67(18) . . ? C5 C6 N1 118.44(19) . . ? C7 C6 N1 118.89(19) . . ? C2 C7 C6 118.86(17) . . ? C2 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? O1' O1' C1' 0(10) 1 . ? O4' N1' O3' 123.57(19) . . ? O4' N1' C6' 117.88(19) . . ? O3' N1' C6' 118.55(17) . . ? O2' C1' O1' 125.97(18) . 1 ? O2' C1' O1' 125.97(18) . . ? O1' C1' O1' 0.00(19) 1 . ? O2' C1' C2' 117.65(17) . . ? O1' C1' C2' 116.37(18) 1 . ? O1' C1' C2' 116.37(18) . . ? C3' C2' C7' 118.74(17) . . ? C3' C2' C1' 120.31(17) . . ? C7' C2' C1' 120.93(16) . . ? C2' C3' C4' 120.9(2) . . ? C2' C3' H3' 119.5 . . ? C4' C3' H3' 119.5 . . ? C5' C4' C3' 120.3(2) . . ? C5' C4' H4' 119.9 . . ? C3' C4' H4' 119.9 . . ? C4' C5' C6' 118.36(19) . . ? C4' C5' H5' 120.8 . . ? C6' C5' H5' 120.8 . . ? C5' C6' C7' 122.56(19) . . ? C5' C6' N1' 118.88(18) . . ? C7' C6' N1' 118.55(17) . . ? C6' C7' C2' 119.08(17) . . ? C6' C7' H7' 120.5 . . ? C2' C7' H7' 120.5 . . ? N2 C1A C2A 111.68(14) . . ? N2 C1A C6A 108.51(14) . . ? C2A C1A C6A 111.37(16) . . ? N2 C1A H1A1 108.4 . . ? C2A C1A H1A1 108.4 . . ? C6A C1A H1A1 108.4 . . ? C1A C2A C3A 110.30(16) . . ? C1A C2A H2A2 109.6 . . ? C3A C2A H2A2 109.6 . . ? C1A C2A H2A1 109.6 . . ? C3A C2A H2A1 109.6 . . ? H2A2 C2A H2A1 108.1 . . ? C4A C3A C2A 111.30(19) . . ? C4A C3A H3A1 109.4 . . ? C2A C3A H3A1 109.4 . . ? C4A C3A H3A2 109.4 . . ? C2A C3A H3A2 109.4 . . ? H3A1 C3A H3A2 108.0 . . ? C3A C4A C5A 111.23(19) . . ? C3A C4A H4A2 109.4 . . ? C5A C4A H4A2 109.4 . . ? C3A C4A H4A1 109.4 . . ? C5A C4A H4A1 109.4 . . ? H4A2 C4A H4A1 108.0 . . ? C4A C5A C6A 111.18(17) . . ? C4A C5A H5A1 109.4 . . ? C6A C5A H5A1 109.4 . . ? C4A C5A H5A2 109.4 . . ? C6A C5A H5A2 109.4 . . ? H5A1 C5A H5A2 108.0 . . ? C1A C6A C5A 111.25(16) . . ? C1A C6A H6A1 109.4 . . ? C5A C6A H6A1 109.4 . . ? C1A C6A H6A2 109.4 . . ? C5A C6A H6A2 109.4 . . ? H6A1 C6A H6A2 108.0 . . ? N2 C1B C6B 112.45(14) . . ? N2 C1B C2B 108.19(14) . . ? C6B C1B C2B 111.51(15) . . ? N2 C1B H1B1 108.2 . . ? C6B C1B H1B1 108.2 . . ? C2B C1B H1B1 108.2 . . ? C1B C2B C3B 111.17(16) . . ? C1B C2B H2B1 109.4 . . ? C3B C2B H2B1 109.4 . . ? C1B C2B H2B2 109.4 . . ? C3B C2B H2B2 109.4 . . ? H2B1 C2B H2B2 108.0 . . ? C4B C3B C2B 110.87(17) . . ? C4B C3B H3B1 109.5 . . ? C2B C3B H3B1 109.5 . . ? C4B C3B H3B2 109.5 . . ? C2B C3B H3B2 109.5 . . ? H3B1 C3B H3B2 108.1 . . ? C3B C4B C5B 110.76(18) . . ? C3B C4B H4B1 109.5 . . ? C5B C4B H4B1 109.5 . . ? C3B C4B H4B2 109.5 . . ? C5B C4B H4B2 109.5 . . ? H4B1 C4B H4B2 108.1 . . ? C4B C5B C6B 111.66(17) . . ? C4B C5B H5B1 109.3 . . ? C6B C5B H5B1 109.3 . . ? C4B C5B H5B2 109.3 . . ? C6B C5B H5B2 109.3 . . ? H5B1 C5B H5B2 107.9 . . ? C1B C6B C5B 109.77(16) . . ? C1B C6B H6B1 109.7 . . ? C5B C6B H6B1 109.7 . . ? C1B C6B H6B2 109.7 . . ? C5B C6B H6B2 109.7 . . ? H6B1 C6B H6B2 108.2 . . ? N2' C1A' C6A' 108.43(14) . . ? N2' C1A' C2A' 111.79(15) . . ? C6A' C1A' C2A' 111.37(16) . . ? N2' C1A' H1A3 108.4 . . ? C6A' C1A' H1A3 108.4 . . ? C2A' C1A' H1A3 108.4 . . ? C1A' C2A' C3A' 110.42(18) . . ? C1A' C2A' H2A4 109.6 . . ? C3A' C2A' H2A4 109.6 . . ? C1A' C2A' H2A3 109.6 . . ? C3A' C2A' H2A3 109.6 . . ? H2A4 C2A' H2A3 108.1 . . ? C4A' C3A' C2A' 111.72(19) . . ? C4A' C3A' H3A4 109.3 . . ? C2A' C3A' H3A4 109.3 . . ? C4A' C3A' H3A3 109.3 . . ? C2A' C3A' H3A3 109.3 . . ? H3A4 C3A' H3A3 107.9 . . ? C5A' C4A' C3A' 111.03(19) . . ? C5A' C4A' H4A4 109.4 . . ? C3A' C4A' H4A4 109.4 . . ? C5A' C4A' H4A3 109.4 . . ? C3A' C4A' H4A3 109.4 . . ? H4A4 C4A' H4A3 108.0 . . ? C4A' C5A' C6A' 111.3(2) . . ? C4A' C5A' H5A3 109.4 . . ? C6A' C5A' H5A3 109.4 . . ? C4A' C5A' H5A4 109.4 . . ? C6A' C5A' H5A4 109.4 . . ? H5A3 C5A' H5A4 108.0 . . ? C1A' C6A' C5A' 110.88(18) . . ? C1A' C6A' H6A4 109.5 . . ? C5A' C6A' H6A4 109.5 . . ? C1A' C6A' H6A3 109.5 . . ? C5A' C6A' H6A3 109.5 . . ? H6A4 C6A' H6A3 108.1 . . ? N2' C1B' C2B' 112.73(15) . . ? N2' C1B' C6B' 108.38(14) . . ? C2B' C1B' C6B' 110.85(15) . . ? N2' C1B' H1B3 108.3 . . ? C2B' C1B' H1B3 108.3 . . ? C6B' C1B' H1B3 108.3 . . ? C1B' C2B' C3B' 109.74(17) . . ? C1B' C2B' H2B4 109.7 . . ? C3B' C2B' H2B4 109.7 . . ? C1B' C2B' H2B3 109.7 . . ? C3B' C2B' H2B3 109.7 . . ? H2B4 C2B' H2B3 108.2 . . ? C4B' C3B' C2B' 111.80(17) . . ? C4B' C3B' H3B3 109.3 . . ? C2B' C3B' H3B3 109.3 . . ? C4B' C3B' H3B4 109.3 . . ? C2B' C3B' H3B4 109.3 . . ? H3B3 C3B' H3B4 107.9 . . ? C3B' C4B' C5B' 111.46(17) . . ? C3B' C4B' H4B3 109.3 . . ? C5B' C4B' H4B3 109.3 . . ? C3B' C4B' H4B4 109.3 . . ? C5B' C4B' H4B4 109.3 . . ? H4B3 C4B' H4B4 108.0 . . ? C4B' C5B' C6B' 111.59(18) . . ? C4B' C5B' H5B3 109.3 . . ? C6B' C5B' H5B3 109.3 . . ? C4B' C5B' H5B4 109.3 . . ? C6B' C5B' H5B4 109.3 . . ? H5B3 C5B' H5B4 108.0 . . ? C1B' C6B' C5B' 110.67(17) . . ? C1B' C6B' H6B3 109.5 . . ? C5B' C6B' H6B3 109.5 . . ? C1B' C6B' H6B4 109.5 . . ? C5B' C6B' H6B4 109.5 . . ? H6B3 C6B' H6B4 108.1 . . ? 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 N2 H2N1 O1' 0.887(19) 1.85(2) 2.724(2) 169.0(17) 1 N2 H2N2 O1 0.98(2) 1.74(2) 2.704(2) 169.6(18) 1_545 N2' H2N3 O2' 0.92(2) 1.86(2) 2.745(2) 161.5(17) 1_565 N2' H2N4 O2 0.95(2) 1.83(2) 2.765(2) 170.2(17) 1 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.318 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.029 data_dt0941 _database_code_depnum_ccdc_archive 'CCDC 264773' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H56 N4 O8' _chemical_formula_weight 696.87 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 'P 2(1)/C' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.2474(14) _cell_length_b 9.7893(7) _cell_length_c 20.5900(14) _cell_angle_alpha 90.00 _cell_angle_beta 108.2100(10) _cell_angle_gamma 90.00 _cell_volume 3876.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.78mm _exptl_crystal_size_mid 0.48mm _exptl_crystal_size_min 0.35mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type SADABS _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_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '<10 %' _diffrn_reflns_number 15175 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 22.50 _reflns_number_total 5075 _reflns_number_gt 4370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.2' _computing_publication_material ? _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^)+(0.0602P)^2^+0.9466P] 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 5075 _refine_ls_number_parameters 675 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 O1 O 0.45163(7) 0.07071(13) 0.09793(6) 0.0604(4) Uani 1 1 d . . . O2 O 0.53470(7) 0.21277(15) 0.09043(7) 0.0665(4) Uani 1 1 d . . . O3 O 0.31580(12) 0.1203(3) 0.14662(12) 0.1345(9) Uani 1 1 d . . . O4 O 0.32450(9) 0.2209(2) 0.05698(10) 0.1047(6) Uani 1 1 d . . . N1 N 0.34200(10) 0.2028(2) 0.11839(11) 0.0746(5) Uani 1 1 d . . . C1 C 0.48511(10) 0.17934(19) 0.11080(8) 0.0463(4) Uani 1 1 d . . . C2 C 0.46445(9) 0.27932(17) 0.15665(8) 0.0428(4) Uani 1 1 d . . . C3 C 0.51399(11) 0.3657(2) 0.19880(9) 0.0544(5) Uani 1 1 d . . . C4 C 0.49759(14) 0.4553(2) 0.24276(11) 0.0676(6) Uani 1 1 d . . . C5 C 0.43151(14) 0.4623(2) 0.24582(11) 0.0725(6) Uani 1 1 d . . . C6 C 0.38104(13) 0.3784(2) 0.20560(11) 0.0667(6) Uani 1 1 d . . . C7 C 0.39836(9) 0.28799(19) 0.16198(9) 0.0493(4) Uani 1 1 d . . . O1' O 0.08472(7) 0.72018(16) 0.06037(7) 0.0692(4) Uani 1 1 d . . . O2' O 0.07563(6) 0.54301(14) 0.12490(6) 0.0586(4) Uani 1 1 d . . . O3' O 0.20891(9) 0.4124(2) 0.18379(14) 0.1221(8) Uani 1 1 d . . . O4' O 0.17375(14) 0.4311(2) 0.27188(10) 0.1313(9) Uani 1 1 d . . . N1' N 0.19396(9) 0.4784(2) 0.22609(12) 0.0780(6) Uani 1 1 d . . . N2' N 0.02756(8) 0.30722(16) 0.05367(8) 0.0445(4) Uani 1 1 d . . . C1' C 0.10250(9) 0.6511(2) 0.11365(9) 0.0475(4) Uani 1 1 d . . . C2' C 0.16249(9) 0.70641(19) 0.17167(9) 0.0493(5) Uani 1 1 d . . . C3' C 0.17817(14) 0.8441(3) 0.17528(13) 0.0766(7) Uani 1 1 d . . . C4' C 0.23136(19) 0.8974(4) 0.22983(16) 0.1080(11) Uani 1 1 d . . . C5' C 0.26894(17) 0.8132(4) 0.28092(15) 0.1069(11) Uani 1 1 d . . . C6' C 0.25535(13) 0.6775(3) 0.27892(12) 0.0804(7) Uani 1 1 d . . . C7' C 0.20274(9) 0.6267(2) 0.22472(9) 0.0552(5) Uani 1 1 d . . . N2 N 0.46405(7) -0.17557(16) 0.04145(8) 0.0422(3) Uani 1 1 d . . . C1A C 0.39729(9) -0.2488(2) 0.03623(9) 0.0465(4) Uani 1 1 d . . . C2A C 0.38389(11) -0.2583(3) 0.10434(11) 0.0622(6) Uani 1 1 d . . . C3A C 0.31446(12) -0.3298(3) 0.09521(15) 0.0814(7) Uani 1 1 d . . . C4A C 0.25542(12) -0.2585(4) 0.04250(14) 0.0859(8) Uani 1 1 d . . . C5A C 0.26964(12) -0.2474(4) -0.02515(13) 0.0777(7) Uani 1 1 d . . . C6A C 0.33872(10) -0.1756(3) -0.01629(11) 0.0589(5) Uani 1 1 d . . . C1B C 0.53111(8) -0.23341(18) 0.08750(9) 0.0440(4) Uani 1 1 d . . . C2B C 0.58960(9) -0.1416(2) 0.08142(11) 0.0509(5) Uani 1 1 d . . . C3B C 0.66063(10) -0.1954(2) 0.12346(13) 0.0640(6) Uani 1 1 d . . . C4B C 0.67099(12) -0.3416(3) 0.10518(14) 0.0715(6) Uani 1 1 d . . . C5B C 0.61267(11) -0.4317(3) 0.11244(14) 0.0691(6) Uani 1 1 d . . . C6B C 0.54156(11) -0.3796(2) 0.06973(11) 0.0564(5) Uani 1 1 d . . . H2N1 H 0.4597(10) -0.084(2) 0.0564(9) 0.058(5) Uiso 1 1 d . . . H2N2 H 0.4673(9) -0.1737(19) -0.0020(11) 0.057(5) Uiso 1 1 d . . . H1A1 H 0.4019(9) -0.3390(19) 0.0198(9) 0.048(5) Uiso 1 1 d . . . H2A1 H 0.4215(11) -0.309(2) 0.1367(11) 0.064(6) Uiso 1 1 d . . . H2A2 H 0.3831(11) -0.166(3) 0.1214(11) 0.075(7) Uiso 1 1 d . . . H3A1 H 0.3184(13) -0.427(3) 0.0779(13) 0.099(9) Uiso 1 1 d . . . H3A2 H 0.3081(13) -0.332(3) 0.1393(14) 0.099(8) Uiso 1 1 d . . . H4A1 H 0.2131(15) -0.305(3) 0.0366(13) 0.102(8) Uiso 1 1 d . . . H4A2 H 0.2503(12) -0.162(3) 0.0595(12) 0.085(8) Uiso 1 1 d . . . H5A1 H 0.2331(14) -0.199(2) -0.0598(13) 0.090(8) Uiso 1 1 d . . . H5A2 H 0.2716(12) -0.341(3) -0.0442(13) 0.092(8) Uiso 1 1 d . . . H6A1 H 0.3496(11) -0.173(2) -0.0589(12) 0.071(6) Uiso 1 1 d . . . H6A2 H 0.3372(11) -0.081(2) 0.0002(11) 0.070(6) Uiso 1 1 d . . . H1B1 H 0.5285(8) -0.2284(17) 0.1332(9) 0.045(5) Uiso 1 1 d . . . H2B1 H 0.5818(9) -0.050(2) 0.0934(9) 0.049(5) Uiso 1 1 d . . . H2B2 H 0.5870(9) -0.1389(19) 0.0327(11) 0.058(5) Uiso 1 1 d . . . H3B1 H 0.6652(11) -0.193(2) 0.1708(12) 0.072(6) Uiso 1 1 d . . . H3B2 H 0.6968(11) -0.133(2) 0.1172(10) 0.069(6) Uiso 1 1 d . . . H4B1 H 0.7168(13) -0.373(2) 0.1351(12) 0.080(7) Uiso 1 1 d . . . H4B2 H 0.6714(12) -0.343(2) 0.0578(13) 0.083(7) Uiso 1 1 d . . . H5B1 H 0.6165(11) -0.528(3) 0.1000(11) 0.077(7) Uiso 1 1 d . . . H5B2 H 0.6150(11) -0.430(2) 0.1618(12) 0.071(6) Uiso 1 1 d . . . H6B1 H 0.5382(10) -0.383(2) 0.0215(11) 0.062(6) Uiso 1 1 d . . . H6B2 H 0.5052(11) -0.437(2) 0.0769(9) 0.062(6) Uiso 1 1 d . . . C1A' C 0.08881(9) 0.26331(18) 0.03227(9) 0.0468(4) Uani 1 1 d . . . C2A' C 0.09859(11) 0.3682(2) -0.01826(11) 0.0572(5) Uani 1 1 d . . . C3A' C 0.15936(14) 0.3312(3) -0.04316(15) 0.0776(7) Uani 1 1 d . . . C4A' C 0.15176(16) 0.1881(3) -0.07205(17) 0.0947(9) Uani 1 1 d . . . C5A' C 0.14181(13) 0.0849(3) -0.02125(15) 0.0805(7) Uani 1 1 d . . . C6A' C 0.07954(11) 0.1208(2) 0.00191(12) 0.0602(5) Uani 1 1 d . . . C1B' C 0.00661(10) 0.2205(2) 0.10451(9) 0.0509(5) Uani 1 1 d . . . C2B' C -0.05241(12) 0.2927(3) 0.12123(12) 0.0657(6) Uani 1 1 d . . . C3B' C -0.07583(15) 0.2135(4) 0.17396(14) 0.0845(7) Uani 1 1 d . . . C4B' C -0.01548(16) 0.1856(4) 0.23747(13) 0.0914(8) Uani 1 1 d . . . C5B' C 0.04221(18) 0.1135(3) 0.22022(15) 0.0910(8) Uani 1 1 d . . . C6B' C 0.06658(13) 0.1940(3) 0.16816(11) 0.0666(6) Uani 1 1 d . . . H3 H 0.5619(11) 0.360(2) 0.1960(10) 0.064(6) Uiso 1 1 d . . . H4 H 0.5320(13) 0.514(3) 0.2704(13) 0.093(8) Uiso 1 1 d . . . H5 H 0.4221(12) 0.531(3) 0.2758(12) 0.090(7) Uiso 1 1 d . . . H6 H 0.3358(13) 0.378(2) 0.2041(11) 0.086(7) Uiso 1 1 d . . . H3' H 0.1505(12) 0.898(3) 0.1378(13) 0.087(8) Uiso 1 1 d . . . H4' H 0.2368(15) 0.986(3) 0.2282(14) 0.112(10) Uiso 1 1 d . . . H5' H 0.3077(16) 0.851(3) 0.3196(15) 0.123(9) Uiso 1 1 d . . . H6' H 0.2821(13) 0.613(3) 0.3142(13) 0.092(8) Uiso 1 1 d . . . H1A3 H 0.1289(9) 0.2648(16) 0.0740(9) 0.042(4) Uiso 1 1 d . . . H2A3 H 0.1056(10) 0.457(2) 0.0031(10) 0.068(6) Uiso 1 1 d . . . H2A4 H 0.0555(11) 0.370(2) -0.0572(11) 0.064(6) Uiso 1 1 d . . . H3A3 H 0.2001(13) 0.337(2) -0.0054(13) 0.080(7) Uiso 1 1 d . . . H3A4 H 0.1629(12) 0.405(3) -0.0777(13) 0.091(7) Uiso 1 1 d . . . H4A3 H 0.1903(15) 0.167(3) -0.0869(13) 0.104(8) Uiso 1 1 d . . . H4A4 H 0.1093(16) 0.189(3) -0.1138(15) 0.109(9) Uiso 1 1 d . . . H5A3 H 0.1343(12) -0.007(3) -0.0406(12) 0.090(7) Uiso 1 1 d . . . H5A4 H 0.1856(14) 0.084(2) 0.0214(13) 0.093(8) Uiso 1 1 d . . . H6A3 H 0.0373(11) 0.1213(19) -0.0375(10) 0.059(5) Uiso 1 1 d . . . H6A4 H 0.0736(11) 0.050(2) 0.0371(11) 0.076(6) Uiso 1 1 d . . . H1B3 H -0.0093(9) 0.135(2) 0.0821(9) 0.052(5) Uiso 1 1 d . . . H2B3 H -0.0892(12) 0.309(2) 0.0805(12) 0.079(7) Uiso 1 1 d . . . H2B4 H -0.0328(11) 0.390(2) 0.1415(11) 0.075(6) Uiso 1 1 d . . . H3B3 H -0.0926(13) 0.125(3) 0.1550(13) 0.091(8) Uiso 1 1 d . . . H3B4 H -0.1119(15) 0.272(3) 0.1858(14) 0.110(9) Uiso 1 1 d . . . H4B3 H -0.0304(15) 0.132(3) 0.2695(16) 0.121(10) Uiso 1 1 d . . . H4B4 H 0.0013(14) 0.272(3) 0.2599(13) 0.096(9) Uiso 1 1 d . . . H5B3 H 0.0269(15) 0.023(3) 0.1983(14) 0.115(10) Uiso 1 1 d . . . H5B4 H 0.0844(16) 0.099(3) 0.2595(16) 0.119(10) Uiso 1 1 d . . . H6B3 H 0.1029(12) 0.151(2) 0.1563(10) 0.069(6) Uiso 1 1 d . . . H6B4 H 0.0848(11) 0.281(3) 0.1845(11) 0.074(7) Uiso 1 1 d . . . H2N3 H 0.0376(10) 0.396(2) 0.0731(10) 0.062(6) Uiso 1 1 d . . . H2N4 H -0.0122(11) 0.3116(19) 0.0137(11) 0.059(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0745(9) 0.0483(8) 0.0617(8) -0.0090(6) 0.0260(7) -0.0014(7) O2 0.0691(9) 0.0797(10) 0.0635(8) -0.0136(7) 0.0389(8) -0.0081(7) O3 0.1314(18) 0.155(2) 0.1396(18) -0.0295(15) 0.0742(15) -0.0750(16) O4 0.0782(12) 0.1374(17) 0.0731(12) -0.0050(11) -0.0129(9) 0.0038(11) N1 0.0578(11) 0.0907(14) 0.0781(14) -0.0077(11) 0.0251(11) -0.0031(10) C1 0.0526(11) 0.0485(11) 0.0371(9) 0.0026(8) 0.0132(8) 0.0054(9) C2 0.0524(11) 0.0417(10) 0.0367(9) 0.0056(7) 0.0173(8) 0.0028(8) C3 0.0623(13) 0.0557(12) 0.0476(10) -0.0021(9) 0.0206(9) -0.0035(10) C4 0.0864(17) 0.0633(14) 0.0531(12) -0.0140(11) 0.0218(12) -0.0071(12) C5 0.0950(19) 0.0700(15) 0.0563(13) -0.0123(11) 0.0292(13) 0.0131(13) C6 0.0648(14) 0.0844(16) 0.0584(12) 0.0052(12) 0.0300(11) 0.0206(12) C7 0.0491(11) 0.0560(11) 0.0430(10) 0.0030(8) 0.0149(8) 0.0039(9) O1' 0.0537(8) 0.0887(11) 0.0553(8) 0.0103(8) 0.0028(7) -0.0107(7) O2' 0.0537(8) 0.0611(9) 0.0558(8) -0.0096(6) 0.0099(6) -0.0135(7) O3' 0.0601(11) 0.1035(15) 0.198(2) -0.0592(16) 0.0343(13) 0.0030(9) O4' 0.182(2) 0.1092(16) 0.0781(12) 0.0248(11) 0.0043(14) -0.0476(15) N1' 0.0550(11) 0.0793(14) 0.0808(14) -0.0057(12) -0.0062(10) -0.0033(10) N2' 0.0432(9) 0.0459(10) 0.0439(8) -0.0005(7) 0.0131(7) -0.0037(7) C1' 0.0388(10) 0.0600(12) 0.0445(11) -0.0067(9) 0.0140(8) -0.0004(9) C2' 0.0452(10) 0.0594(12) 0.0442(10) -0.0089(9) 0.0153(8) -0.0100(9) C3' 0.0901(17) 0.0679(16) 0.0660(14) -0.0068(12) 0.0158(13) -0.0213(13) C4' 0.143(3) 0.080(2) 0.090(2) -0.0226(17) 0.0200(19) -0.058(2) C5' 0.113(2) 0.122(3) 0.0655(16) -0.0170(17) -0.0007(16) -0.060(2) C6' 0.0684(15) 0.103(2) 0.0552(13) -0.0043(13) -0.0014(12) -0.0274(14) C7' 0.0447(10) 0.0669(13) 0.0507(11) -0.0096(10) 0.0099(9) -0.0131(9) N2 0.0408(8) 0.0440(9) 0.0431(9) 0.0005(7) 0.0150(7) 0.0002(6) C1A 0.0408(10) 0.0482(11) 0.0519(10) -0.0004(9) 0.0165(8) -0.0030(8) C2A 0.0533(12) 0.0808(17) 0.0552(12) 0.0174(12) 0.0207(10) 0.0005(11) C3A 0.0598(14) 0.109(2) 0.0836(17) 0.0270(16) 0.0341(13) -0.0072(13) C4A 0.0472(13) 0.125(3) 0.0911(18) 0.0219(17) 0.0296(13) -0.0034(14) C5A 0.0435(12) 0.113(2) 0.0733(15) 0.0075(16) 0.0135(11) -0.0044(13) C6A 0.0449(11) 0.0824(17) 0.0489(12) 0.0095(11) 0.0137(9) 0.0012(10) C1B 0.0402(10) 0.0504(11) 0.0404(10) 0.0025(8) 0.0112(8) 0.0009(8) C2B 0.0459(11) 0.0490(12) 0.0583(12) -0.0009(9) 0.0169(9) -0.0023(8) C3B 0.0435(11) 0.0796(16) 0.0677(15) 0.0046(11) 0.0157(10) -0.0035(10) C4B 0.0523(13) 0.0815(17) 0.0804(16) 0.0180(13) 0.0204(12) 0.0198(11) C5B 0.0635(14) 0.0586(15) 0.0815(16) 0.0149(12) 0.0175(12) 0.0149(11) C6B 0.0568(12) 0.0452(11) 0.0638(14) 0.0059(9) 0.0141(10) 0.0029(9) C1A' 0.0398(10) 0.0501(11) 0.0472(10) -0.0032(8) 0.0090(9) -0.0009(8) C2A' 0.0511(12) 0.0654(14) 0.0587(12) 0.0040(11) 0.0222(10) -0.0005(10) C3A' 0.0601(15) 0.096(2) 0.0862(17) 0.0025(15) 0.0372(14) 0.0013(13) C4A' 0.0712(17) 0.130(3) 0.097(2) -0.0246(19) 0.0479(17) 0.0076(16) C5A' 0.0638(15) 0.0765(17) 0.0999(19) -0.0289(15) 0.0239(15) 0.0065(12) C6A' 0.0522(12) 0.0577(13) 0.0673(13) -0.0123(11) 0.0136(11) -0.0002(9) C1B' 0.0581(12) 0.0470(11) 0.0471(10) -0.0013(9) 0.0159(9) -0.0114(9) C2B' 0.0594(13) 0.0826(17) 0.0597(13) 0.0064(12) 0.0254(11) -0.0020(12) C3B' 0.0865(18) 0.105(2) 0.0735(16) 0.0059(15) 0.0411(15) -0.0136(17) C4B' 0.113(2) 0.107(2) 0.0643(16) 0.0102(16) 0.0428(16) -0.0114(18) C5B' 0.108(2) 0.095(2) 0.0689(16) 0.0298(15) 0.0263(16) 0.0021(17) C6B' 0.0691(15) 0.0704(16) 0.0579(13) 0.0132(11) 0.0164(11) 0.0000(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 O1 0.000(4) 1 ? O1 C1 1.244(2) . ? O2 C1 1.247(2) . ? O3 N1 1.210(3) . ? O4 N1 1.215(2) . ? N1 C7 1.471(3) . ? C1 O1 1.244(2) 1 ? C1 C2 1.507(2) . ? C2 C7 1.379(2) . ? C2 C3 1.389(3) . ? C3 C4 1.373(3) . ? C3 H3 0.99(2) . ? C4 C5 1.361(3) . ? C4 H4 0.95(3) . ? C5 C6 1.369(3) . ? C5 H5 0.97(3) . ? C6 C7 1.382(3) . ? C6 H6 0.91(2) . ? O1' C1' 1.242(2) . ? O2' C1' 1.244(2) . ? O3' N1' 1.197(3) . ? O4' N1' 1.230(3) . ? N1' C7' 1.463(3) . ? N2' C1A' 1.503(2) . ? N2' C1B' 1.508(2) . ? N2' H2N3 0.95(2) . ? N2' H2N4 0.96(2) . ? C1' O2' 1.244(2) 1 ? C1' C2' 1.513(2) . ? C2' C3' 1.382(3) . ? C2' C7' 1.382(3) . ? C3' C4' 1.392(4) . ? C3' H3' 0.96(2) . ? C4' C5' 1.365(5) . ? C4' H4' 0.88(3) . ? C5' C6' 1.355(4) . ? C5' H5' 1.00(3) . ? C6' C7' 1.373(3) . ? C6' H6' 0.99(3) . ? N2 C1B 1.503(2) . ? N2 C1A 1.504(2) . ? N2 H2N1 0.96(2) . ? N2 H2N2 0.92(2) . ? C1A C2A 1.512(3) . ? C1A C6A 1.513(3) . ? C1A H1A1 0.960(19) . ? C2A C3A 1.528(3) . ? C2A H2A1 0.97(2) . ? C2A H2A2 0.97(2) . ? C3A C4A 1.511(4) . ? C3A H3A1 1.03(3) . ? C3A H3A2 0.96(3) . ? C4A C5A 1.512(4) . ? C4A H4A1 0.94(3) . ? C4A H4A2 1.02(3) . ? C5A C6A 1.524(3) . ? C5A H5A1 0.98(3) . ? C5A H5A2 1.01(3) . ? C6A H6A1 0.97(2) . ? C6A H6A2 0.99(2) . ? C1B C6B 1.508(3) . ? C1B C2B 1.523(3) . ? C1B H1B1 0.959(18) . ? C2B C3B 1.522(3) . ? C2B H2B1 0.961(19) . ? C2B H2B2 0.99(2) . ? C3B C4B 1.512(3) . ? C3B H3B1 0.95(2) . ? C3B H3B2 0.99(2) . ? C4B C5B 1.518(3) . ? C4B H4B1 0.99(2) . ? C4B H4B2 0.98(2) . ? C5B C6B 1.521(3) . ? C5B H5B1 0.99(2) . ? C5B H5B2 1.00(2) . ? C6B H6B1 0.97(2) . ? C6B H6B2 0.98(2) . ? C1A' C6A' 1.516(3) . ? C1A' C2A' 1.518(3) . ? C1A' H1A3 0.980(18) . ? C2A' C3A' 1.518(3) . ? C2A' H2A3 0.96(2) . ? C2A' H2A4 0.98(2) . ? C3A' C4A' 1.510(4) . ? C3A' H3A3 0.94(2) . ? C3A' H3A4 1.03(3) . ? C4A' C5A' 1.513(4) . ? C4A' H4A3 0.95(3) . ? C4A' H4A4 1.01(3) . ? C5A' C6A' 1.522(3) . ? C5A' H5A3 0.98(3) . ? C5A' H5A4 1.03(3) . ? C6A' H6A3 0.98(2) . ? C6A' H6A4 1.04(2) . ? C1B' C6B' 1.505(3) . ? C1B' C2B' 1.517(3) . ? C1B' H1B3 0.961(19) . ? C2B' C3B' 1.525(3) . ? C2B' H2B3 0.95(2) . ? C2B' H2B4 1.07(2) . ? C3B' C4B' 1.510(4) . ? C3B' H3B3 0.97(3) . ? C3B' H3B4 1.02(3) . ? C4B' C5B' 1.499(4) . ? C4B' H4B3 0.96(3) . ? C4B' H4B4 0.97(3) . ? C5B' C6B' 1.531(3) . ? C5B' H5B3 1.00(3) . ? C5B' H5B4 0.99(3) . ? C6B' H6B3 0.94(2) . ? C6B' H6B4 0.95(2) . ? 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 O1 O1 C1 0(10) 1 . ? O3 N1 O4 124.6(2) . . ? O3 N1 C7 117.3(2) . . ? O4 N1 C7 118.1(2) . . ? O1 C1 O1 0.0(2) 1 . ? O1 C1 O2 126.53(17) 1 . ? O1 C1 O2 126.53(17) . . ? O1 C1 C2 116.68(16) 1 . ? O1 C1 C2 116.68(16) . . ? O2 C1 C2 116.79(16) . . ? C7 C2 C3 116.23(16) . . ? C7 C2 C1 123.79(16) . . ? C3 C2 C1 119.93(16) . . ? C4 C3 C2 121.6(2) . . ? C4 C3 H3 121.2(12) . . ? C2 C3 H3 117.1(12) . . ? C5 C4 C3 120.4(2) . . ? C5 C4 H4 119.4(15) . . ? C3 C4 H4 120.2(15) . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 117.0(14) . . ? C6 C5 H5 122.9(14) . . ? C5 C6 C7 119.0(2) . . ? C5 C6 H6 125.2(15) . . ? C7 C6 H6 115.8(15) . . ? C2 C7 C6 122.73(19) . . ? C2 C7 N1 120.24(16) . . ? C6 C7 N1 116.99(18) . . ? O3' N1' O4' 125.1(3) . . ? O3' N1' C7' 117.5(2) . . ? O4' N1' C7' 117.4(2) . . ? C1A' N2' C1B' 118.66(14) . . ? C1A' N2' H2N3 107.3(11) . . ? C1B' N2' H2N3 106.9(11) . . ? C1A' N2' H2N4 108.1(11) . . ? C1B' N2' H2N4 106.2(11) . . ? H2N3 N2' H2N4 109.5(16) . . ? O1' C1' O2' 127.17(17) . 1 ? O1' C1' O2' 127.17(17) . . ? O1' C1' C2' 116.26(17) . . ? O2' C1' C2' 116.55(16) 1 . ? O2' C1' C2' 116.55(16) . . ? C3' C2' C7' 116.08(18) . . ? C3' C2' C1' 120.38(19) . . ? C7' C2' C1' 123.49(17) . . ? C2' C3' C4' 121.0(3) . . ? C2' C3' H3' 115.2(15) . . ? C4' C3' H3' 123.7(15) . . ? C5' C4' C3' 120.0(3) . . ? C5' C4' H4' 125(2) . . ? C3' C4' H4' 114(2) . . ? C6' C5' C4' 120.6(3) . . ? C6' C5' H5' 119.1(18) . . ? C4' C5' H5' 120.2(18) . . ? C5' C6' C7' 118.6(3) . . ? C5' C6' H6' 123.2(15) . . ? C7' C6' H6' 118.2(15) . . ? C6' C7' C2' 123.6(2) . . ? C6' C7' N1' 114.3(2) . . ? C2' C7' N1' 122.01(16) . . ? C1B N2 C1A 118.69(14) . . ? C1B N2 H2N1 107.7(11) . . ? C1A N2 H2N1 107.3(11) . . ? C1B N2 H2N2 107.3(12) . . ? C1A N2 H2N2 106.0(12) . . ? H2N1 N2 H2N2 109.6(17) . . ? N2 C1A C2A 112.39(16) . . ? N2 C1A C6A 108.16(15) . . ? C2A C1A C6A 111.36(17) . . ? N2 C1A H1A1 106.2(10) . . ? C2A C1A H1A1 109.6(10) . . ? C6A C1A H1A1 108.9(10) . . ? C1A C2A C3A 109.8(2) . . ? C1A C2A H2A1 109.7(12) . . ? C3A C2A H2A1 110.1(12) . . ? C1A C2A H2A2 107.8(13) . . ? C3A C2A H2A2 110.6(13) . . ? H2A1 C2A H2A2 108.7(18) . . ? C4A C3A C2A 111.6(2) . . ? C4A C3A H3A1 108.0(15) . . ? C2A C3A H3A1 107.4(15) . . ? C4A C3A H3A2 112.5(16) . . ? C2A C3A H3A2 106.6(16) . . ? H3A1 C3A H3A2 111(2) . . ? C3A C4A C5A 111.1(2) . . ? C3A C4A H4A1 110.8(16) . . ? C5A C4A H4A1 110.0(16) . . ? C3A C4A H4A2 108.8(14) . . ? C5A C4A H4A2 108.5(14) . . ? H4A1 C4A H4A2 108(2) . . ? C4A C5A C6A 110.8(2) . . ? C4A C5A H5A1 113.0(14) . . ? C6A C5A H5A1 108.6(15) . . ? C4A C5A H5A2 109.6(15) . . ? C6A C5A H5A2 108.8(14) . . ? H5A1 C5A H5A2 106(2) . . ? C1A C6A C5A 110.63(19) . . ? C1A C6A H6A1 108.1(12) . . ? C5A C6A H6A1 111.4(12) . . ? C1A C6A H6A2 107.4(12) . . ? C5A C6A H6A2 110.2(12) . . ? H6A1 C6A H6A2 108.9(18) . . ? N2 C1B C6B 111.84(15) . . ? N2 C1B C2B 107.36(14) . . ? C6B C1B C2B 111.62(16) . . ? N2 C1B H1B1 106.5(10) . . ? C6B C1B H1B1 110.0(10) . . ? C2B C1B H1B1 109.4(10) . . ? C3B C2B C1B 111.73(17) . . ? C3B C2B H2B1 112.4(10) . . ? C1B C2B H2B1 109.8(10) . . ? C3B C2B H2B2 109.1(11) . . ? C1B C2B H2B2 107.7(11) . . ? H2B1 C2B H2B2 106.0(15) . . ? C4B C3B C2B 111.46(19) . . ? C4B C3B H3B1 107.6(13) . . ? C2B C3B H3B1 110.2(13) . . ? C4B C3B H3B2 112.5(12) . . ? C2B C3B H3B2 108.6(12) . . ? H3B1 C3B H3B2 106.3(18) . . ? C3B C4B C5B 110.66(19) . . ? C3B C4B H4B1 108.2(13) . . ? C5B C4B H4B1 111.6(13) . . ? C3B C4B H4B2 107.7(14) . . ? C5B C4B H4B2 109.9(14) . . ? H4B1 C4B H4B2 108.7(19) . . ? C4B C5B C6B 111.92(19) . . ? C4B C5B H5B1 113.8(13) . . ? C6B C5B H5B1 107.9(13) . . ? C4B C5B H5B2 107.5(12) . . ? C6B C5B H5B2 108.5(12) . . ? H5B1 C5B H5B2 106.9(18) . . ? C1B C6B C5B 110.91(18) . . ? C1B C6B H6B1 107.9(12) . . ? C5B C6B H6B1 109.3(11) . . ? C1B C6B H6B2 110.1(11) . . ? C5B C6B H6B2 109.9(11) . . ? H6B1 C6B H6B2 108.7(16) . . ? N2' C1A' C6A' 112.14(15) . . ? N2' C1A' C2A' 107.68(15) . . ? C6A' C1A' C2A' 111.45(17) . . ? N2' C1A' H1A3 105.7(9) . . ? C6A' C1A' H1A3 109.7(9) . . ? C2A' C1A' H1A3 109.9(9) . . ? C3A' C2A' C1A' 111.27(19) . . ? C3A' C2A' H2A3 110.5(12) . . ? C1A' C2A' H2A3 109.2(12) . . ? C3A' C2A' H2A4 109.6(11) . . ? C1A' C2A' H2A4 107.3(12) . . ? H2A3 C2A' H2A4 109.0(17) . . ? C4A' C3A' C2A' 111.2(2) . . ? C4A' C3A' H3A3 109.5(15) . . ? C2A' C3A' H3A3 107.5(15) . . ? C4A' C3A' H3A4 113.5(13) . . ? C2A' C3A' H3A4 107.7(14) . . ? H3A3 C3A' H3A4 107(2) . . ? C3A' C4A' C5A' 111.5(2) . . ? C3A' C4A' H4A3 109.8(17) . . ? C5A' C4A' H4A3 112.2(17) . . ? C3A' C4A' H4A4 106.2(16) . . ? C5A' C4A' H4A4 109.7(16) . . ? H4A3 C4A' H4A4 107(2) . . ? C4A' C5A' C6A' 111.4(2) . . ? C4A' C5A' H5A3 111.8(14) . . ? C6A' C5A' H5A3 107.6(14) . . ? C4A' C5A' H5A4 109.4(13) . . ? C6A' C5A' H5A4 108.1(13) . . ? H5A3 C5A' H5A4 108.5(19) . . ? C1A' C6A' C5A' 109.52(18) . . ? C1A' C6A' H6A3 107.5(11) . . ? C5A' C6A' H6A3 109.6(11) . . ? C1A' C6A' H6A4 110.7(12) . . ? C5A' C6A' H6A4 110.6(12) . . ? H6A3 C6A' H6A4 108.8(16) . . ? C6B' C1B' N2' 112.11(16) . . ? C6B' C1B' C2B' 111.17(18) . . ? N2' C1B' C2B' 107.92(16) . . ? C6B' C1B' H1B3 109.0(11) . . ? N2' C1B' H1B3 106.4(10) . . ? C2B' C1B' H1B3 110.1(11) . . ? C1B' C2B' C3B' 111.5(2) . . ? C1B' C2B' H2B3 109.6(14) . . ? C3B' C2B' H2B3 112.6(14) . . ? C1B' C2B' H2B4 106.4(11) . . ? C3B' C2B' H2B4 109.7(11) . . ? H2B3 C2B' H2B4 106.6(18) . . ? C4B' C3B' C2B' 111.2(2) . . ? C4B' C3B' H3B3 105.8(15) . . ? C2B' C3B' H3B3 108.5(15) . . ? C4B' C3B' H3B4 110.0(16) . . ? C2B' C3B' H3B4 106.8(16) . . ? H3B3 C3B' H3B4 115(2) . . ? C5B' C4B' C3B' 111.1(2) . . ? C5B' C4B' H4B3 109.7(18) . . ? C3B' C4B' H4B3 110.5(18) . . ? C5B' C4B' H4B4 109.9(16) . . ? C3B' C4B' H4B4 108.7(16) . . ? H4B3 C4B' H4B4 107(2) . . ? C4B' C5B' C6B' 111.7(2) . . ? C4B' C5B' H5B3 111.8(17) . . ? C6B' C5B' H5B3 105.3(17) . . ? C4B' C5B' H5B4 114.4(17) . . ? C6B' C5B' H5B4 105.3(17) . . ? H5B3 C5B' H5B4 108(2) . . ? C1B' C6B' C5B' 110.5(2) . . ? C1B' C6B' H6B3 109.5(13) . . ? C5B' C6B' H6B3 113.5(13) . . ? C1B' C6B' H6B4 105.8(13) . . ? C5B' C6B' H6B4 112.9(13) . . ? H6B3 C6B' H6B4 104.2(19) . . ? 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 N2 H2N1 O1 0.96(2) 1.77(2) 2.722(2) 169.8(17) 1 N2 H2N2 O2 0.92(2) 1.85(2) 2.748(2) 165.9(18) 3_655 N2' H2N3 O2' 0.95(2) 1.82(2) 2.745(2) 165.5(17) 1 N2' H2N4 O1' 0.96(2) 1.78(2) 2.723(2) 167.3(17) 3_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.293 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.032 data_dt0960 _database_code_depnum_ccdc_archive 'CCDC 264775' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H30 N2 O4' _chemical_formula_weight 374.47 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 'P 2(1)2(1)2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.7589(8) _cell_length_b 18.080(3) _cell_length_c 20.055(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2088.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description FIBER _exptl_crystal_colour 'LIGHT YELLOW' _exptl_crystal_size_max 0.24mm _exptl_crystal_size_mid 0.17mm _exptl_crystal_size_min 0.05mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type SADABS _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_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '<10 %' _diffrn_reflns_number 8378 _diffrn_reflns_av_R_equivalents 0.0998 _diffrn_reflns_av_sigmaI/netI 0.0949 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 22.49 _reflns_number_total 1618 _reflns_number_gt 970 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.2' _computing_publication_material ? _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^)+(0.0463P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 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 0(3) _refine_ls_number_reflns 1618 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1238 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1102 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _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 N1 N 0.2241(16) 0.0333(4) -0.0207(5) 0.113(3) Uani 1 1 d . . . O1 O 1.0738(8) 0.3468(2) 0.17778(17) 0.0606(12) Uani 1 1 d . . . O2 O 0.7846(7) 0.3828(2) 0.2428(2) 0.0659(12) Uani 1 1 d . . . O3 O 0.0473(12) 0.0135(4) 0.0017(5) 0.187(4) Uani 1 1 d . . . O4 O 0.3132(13) 0.0060(3) -0.0717(3) 0.143(3) Uani 1 1 d . . . C1 C 0.8668(12) 0.3468(3) 0.1950(3) 0.0479(16) Uani 1 1 d . . . C2 C 0.6946(12) 0.2990(3) 0.1588(3) 0.0632(19) Uani 1 1 d . . . H2 H 0.5391 0.3008 0.1712 0.076 Uiso 1 1 calc R . . C3 C 0.7555(10) 0.2558(3) 0.1115(3) 0.0521(17) Uani 1 1 d . . . H3 H 0.9092 0.2592 0.0976 0.063 Uiso 1 1 calc R . . C4 C 0.6071(12) 0.2003(3) 0.0758(3) 0.0508(17) Uani 1 1 d . . . C5 C 0.3960(13) 0.1775(4) 0.1007(3) 0.0661(18) Uani 1 1 d . . . H5 H 0.3384 0.1995 0.1392 0.079 Uiso 1 1 calc R . . C6 C 0.2668(13) 0.1224(4) 0.0694(4) 0.076(2) Uani 1 1 d . . . H6 H 0.1243 0.1072 0.0863 0.091 Uiso 1 1 calc R . . C7 C 0.3591(14) 0.0909(4) 0.0116(4) 0.067(2) Uani 1 1 d . . . C8 C 0.5618(15) 0.1140(4) -0.0136(3) 0.069(2) Uani 1 1 d . . . H8 H 0.6176 0.0935 -0.0530 0.083 Uiso 1 1 calc R . . C9 C 0.6864(12) 0.1673(4) 0.0183(3) 0.067(2) Uani 1 1 d . . . H9 H 0.8288 0.1819 0.0007 0.081 Uiso 1 1 calc R . . N2 N 1.3393(9) 0.4241(3) 0.2684(2) 0.0437(13) Uani 1 1 d . . . C1A C 1.2859(10) 0.3954(3) 0.3368(2) 0.0514(16) Uani 1 1 d . . . H1A H 1.1299 0.4121 0.3493 0.062 Uiso 1 1 calc R . . C2A C 1.2852(12) 0.3125(3) 0.3344(3) 0.075(2) Uani 1 1 d . . . H2A1 H 1.4345 0.2951 0.3183 0.090 Uiso 1 1 calc R . . H2A2 H 1.1669 0.2959 0.3034 0.090 Uiso 1 1 calc R . . C3A C 1.2379(13) 0.2798(4) 0.4031(3) 0.092(2) Uani 1 1 d . . . H3A1 H 1.0817 0.2927 0.4170 0.111 Uiso 1 1 calc R . . H3A2 H 1.2482 0.2263 0.4008 0.111 Uiso 1 1 calc R . . C4A C 1.4086(14) 0.3082(4) 0.4534(3) 0.108(3) Uani 1 1 d . . . H4A1 H 1.3689 0.2891 0.4972 0.129 Uiso 1 1 calc R . . H4A2 H 1.5629 0.2906 0.4422 0.129 Uiso 1 1 calc R . . C5A C 1.4086(19) 0.3904(5) 0.4553(3) 0.138(4) Uani 1 1 d . . . H5A1 H 1.5267 0.4070 0.4864 0.165 Uiso 1 1 calc R . . H5A2 H 1.2594 0.4075 0.4716 0.165 Uiso 1 1 calc R . . C6A C 1.4549(14) 0.4247(4) 0.3871(3) 0.101(3) Uani 1 1 d . . . H6A1 H 1.4403 0.4781 0.3899 0.121 Uiso 1 1 calc R . . H6A2 H 1.6121 0.4132 0.3730 0.121 Uiso 1 1 calc R . . C1B C 1.3290(9) 0.5055(3) 0.2560(3) 0.0510(17) Uani 1 1 d . . . H1B H 1.4418 0.5297 0.2854 0.061 Uiso 1 1 calc R . . C2B C 1.4012(12) 0.5189(3) 0.1851(3) 0.080(2) Uani 1 1 d . . . H2B1 H 1.2972 0.4926 0.1554 0.096 Uiso 1 1 calc R . . H2B2 H 1.5568 0.4998 0.1783 0.096 Uiso 1 1 calc R . . C3B C 1.3966(15) 0.6016(4) 0.1682(4) 0.112(3) Uani 1 1 d . . . H3B1 H 1.5138 0.6271 0.1942 0.135 Uiso 1 1 calc R . . H3B2 H 1.4331 0.6084 0.1214 0.135 Uiso 1 1 calc R . . C4B C 1.1623(14) 0.6341(4) 0.1828(4) 0.099(3) Uani 1 1 d . . . H4B1 H 1.1665 0.6870 0.1747 0.118 Uiso 1 1 calc R . . H4B2 H 1.0482 0.6126 0.1530 0.118 Uiso 1 1 calc R . . C5B C 1.0914(14) 0.6202(4) 0.2534(4) 0.095(2) Uani 1 1 d . . . H5B1 H 0.9364 0.6396 0.2606 0.114 Uiso 1 1 calc R . . H5B2 H 1.1964 0.6461 0.2831 0.114 Uiso 1 1 calc R . . C6B C 1.0945(12) 0.5372(3) 0.2701(3) 0.077(2) Uani 1 1 d . . . H6B1 H 1.0566 0.5302 0.3168 0.092 Uiso 1 1 calc R . . H6B2 H 0.9785 0.5117 0.2437 0.092 Uiso 1 1 calc R . . H1N2 H 1.498(12) 0.400(3) 0.254(3) 0.09(2) Uiso 1 1 d . . . H2N2 H 1.208(9) 0.395(3) 0.236(2) 0.069(17) 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 N1 0.102(7) 0.070(6) 0.166(8) -0.035(5) -0.061(7) 0.003(6) O1 0.035(3) 0.079(3) 0.068(3) -0.012(2) 0.001(2) -0.008(3) O2 0.043(3) 0.071(3) 0.084(3) -0.024(2) 0.001(2) 0.006(3) O3 0.080(5) 0.143(7) 0.338(10) -0.091(6) -0.038(6) -0.042(5) O4 0.183(7) 0.105(5) 0.140(5) -0.042(4) -0.068(5) -0.004(5) C1 0.032(4) 0.042(4) 0.069(4) -0.002(3) -0.016(4) -0.007(4) C2 0.059(5) 0.063(5) 0.068(5) 0.006(4) 0.007(4) 0.011(4) C3 0.038(4) 0.059(5) 0.059(4) 0.015(3) 0.001(3) 0.011(4) C4 0.051(5) 0.039(4) 0.062(4) 0.013(3) -0.012(4) -0.005(4) C5 0.059(5) 0.073(5) 0.066(4) -0.001(4) -0.004(4) 0.001(5) C6 0.055(5) 0.065(6) 0.109(6) 0.002(4) -0.020(5) -0.006(5) C7 0.068(6) 0.047(5) 0.084(5) -0.003(4) -0.041(5) -0.001(5) C8 0.084(6) 0.066(6) 0.058(5) -0.005(4) -0.024(5) -0.001(5) C9 0.078(5) 0.069(5) 0.054(4) 0.003(3) -0.010(4) 0.002(5) N2 0.041(4) 0.035(4) 0.054(3) -0.007(2) -0.001(3) -0.005(3) C1A 0.045(4) 0.059(5) 0.051(4) 0.000(3) 0.004(3) -0.010(4) C2A 0.084(6) 0.066(5) 0.074(5) 0.009(4) -0.005(4) -0.019(5) C3A 0.102(7) 0.091(6) 0.084(5) 0.032(4) -0.013(5) -0.016(5) C4A 0.106(7) 0.134(8) 0.083(6) 0.040(5) -0.027(5) -0.041(7) C5A 0.223(11) 0.124(8) 0.067(5) 0.011(5) -0.035(6) -0.057(9) C6A 0.152(7) 0.089(6) 0.062(5) 0.012(4) -0.040(5) -0.058(6) C1B 0.040(4) 0.048(5) 0.065(4) -0.006(3) 0.002(3) -0.002(4) C2B 0.086(5) 0.068(5) 0.086(5) 0.024(4) 0.031(4) 0.022(5) C3B 0.111(7) 0.096(7) 0.130(6) 0.040(6) 0.019(6) 0.008(6) C4B 0.117(7) 0.065(6) 0.114(6) 0.016(4) -0.025(6) 0.009(6) C5B 0.104(6) 0.055(6) 0.126(7) -0.015(4) 0.000(5) 0.025(5) C6B 0.082(6) 0.053(5) 0.095(5) -0.008(4) 0.021(4) 0.008(4) _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 N1 O3 1.169(9) . ? N1 O4 1.245(8) . ? N1 C7 1.453(9) . ? O1 O1 0.000(10) 1 ? O1 C1 1.241(6) . ? O2 C1 1.251(7) . ? C1 O1 1.241(6) 1 ? C1 C2 1.503(8) . ? C2 C3 1.277(6) . ? C2 H2 0.9300 . ? C3 C4 1.500(7) . ? C3 H3 0.9300 . ? C4 C9 1.377(7) . ? C4 C5 1.377(8) . ? C5 C6 1.393(8) . ? C5 H5 0.9300 . ? C6 C7 1.396(8) . ? C6 H6 0.9300 . ? C7 C8 1.339(8) . ? C8 C9 1.362(8) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? N2 C1B 1.495(7) . ? N2 C1A 1.499(6) . ? N2 H1N2 1.05(7) . ? N2 H2N2 1.13(6) . ? C1A C6A 1.498(7) . ? C1A C2A 1.499(7) . ? C1A H1A 0.9800 . ? C2A C3A 1.525(7) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C4A 1.499(8) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C4A C5A 1.487(8) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A C6A 1.527(7) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C1B C6B 1.494(7) . ? C1B C2B 1.501(7) . ? C1B H1B 0.9800 . ? C2B C3B 1.532(8) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.501(9) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4B C5B 1.495(8) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C5B C6B 1.537(8) . ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? 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 O3 N1 O4 123.6(9) . . ? O3 N1 C7 120.9(10) . . ? O4 N1 C7 115.5(9) . . ? O1 O1 C1 0(10) 1 . ? O1 C1 O1 0.0(5) 1 . ? O1 C1 O2 125.2(6) 1 . ? O1 C1 O2 125.2(6) . . ? O1 C1 C2 120.0(6) 1 . ? O1 C1 C2 120.0(6) . . ? O2 C1 C2 114.8(6) . . ? C3 C2 C1 122.0(6) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C2 C3 C4 127.4(6) . . ? C2 C3 H3 116.3 . . ? C4 C3 H3 116.3 . . ? C9 C4 C5 117.8(7) . . ? C9 C4 C3 120.1(6) . . ? C5 C4 C3 122.0(6) . . ? C4 C5 C6 121.5(6) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C7 117.5(7) . . ? C5 C6 H6 121.2 . . ? C7 C6 H6 121.2 . . ? C8 C7 C6 121.2(7) . . ? C8 C7 N1 121.4(9) . . ? C6 C7 N1 117.4(8) . . ? C7 C8 C9 120.2(7) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C4 121.7(7) . . ? C8 C9 H9 119.2 . . ? C4 C9 H9 119.2 . . ? C1B N2 C1A 119.0(4) . . ? C1B N2 H1N2 113(3) . . ? C1A N2 H1N2 107(3) . . ? C1B N2 H2N2 110(3) . . ? C1A N2 H2N2 103(2) . . ? H1N2 N2 H2N2 103(4) . . ? C6A C1A C2A 112.2(5) . . ? C6A C1A N2 111.1(5) . . ? C2A C1A N2 108.5(4) . . ? C6A C1A H1A 108.3 . . ? C2A C1A H1A 108.3 . . ? N2 C1A H1A 108.3 . . ? C1A C2A C3A 111.0(5) . . ? C1A C2A H2A1 109.4 . . ? C3A C2A H2A1 109.4 . . ? C1A C2A H2A2 109.4 . . ? C3A C2A H2A2 109.4 . . ? H2A1 C2A H2A2 108.0 . . ? C4A C3A C2A 111.0(6) . . ? C4A C3A H3A1 109.4 . . ? C2A C3A H3A1 109.4 . . ? C4A C3A H3A2 109.4 . . ? C2A C3A H3A2 109.4 . . ? H3A1 C3A H3A2 108.0 . . ? C5A C4A C3A 111.1(7) . . ? C5A C4A H4A1 109.4 . . ? C3A C4A H4A1 109.4 . . ? C5A C4A H4A2 109.4 . . ? C3A C4A H4A2 109.4 . . ? H4A1 C4A H4A2 108.0 . . ? C4A C5A C6A 112.5(6) . . ? C4A C5A H5A1 109.1 . . ? C6A C5A H5A1 109.1 . . ? C4A C5A H5A2 109.1 . . ? C6A C5A H5A2 109.1 . . ? H5A1 C5A H5A2 107.8 . . ? C1A C6A C5A 110.2(6) . . ? C1A C6A H6A1 109.6 . . ? C5A C6A H6A1 109.6 . . ? C1A C6A H6A2 109.6 . . ? C5A C6A H6A2 109.6 . . ? H6A1 C6A H6A2 108.1 . . ? N2 C1B C6B 112.5(5) . . ? N2 C1B C2B 107.8(5) . . ? C6B C1B C2B 111.6(5) . . ? N2 C1B H1B 108.3 . . ? C6B C1B H1B 108.3 . . ? C2B C1B H1B 108.3 . . ? C1B C2B C3B 111.2(5) . . ? C1B C2B H2B1 109.4 . . ? C3B C2B H2B1 109.4 . . ? C1B C2B H2B2 109.4 . . ? C3B C2B H2B2 109.4 . . ? H2B1 C2B H2B2 108.0 . . ? C4B C3B C2B 110.8(7) . . ? C4B C3B H3B1 109.5 . . ? C2B C3B H3B1 109.5 . . ? C4B C3B H3B2 109.5 . . ? C2B C3B H3B2 109.5 . . ? H3B1 C3B H3B2 108.1 . . ? C5B C4B C3B 111.4(7) . . ? C5B C4B H4B1 109.4 . . ? C3B C4B H4B1 109.4 . . ? C5B C4B H4B2 109.4 . . ? C3B C4B H4B2 109.4 . . ? H4B1 C4B H4B2 108.0 . . ? C4B C5B C6B 111.6(5) . . ? C4B C5B H5B1 109.3 . . ? C6B C5B H5B1 109.3 . . ? C4B C5B H5B2 109.3 . . ? C6B C5B H5B2 109.3 . . ? H5B1 C5B H5B2 108.0 . . ? C1B C6B C5B 110.1(6) . . ? C1B C6B H6B1 109.6 . . ? C5B C6B H6B1 109.6 . . ? C1B C6B H6B2 109.6 . . ? C5B C6B H6B2 109.6 . . ? H6B1 C6B H6B2 108.2 . . ? 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 N2 H1N2 O2 1.05(7) 1.70(7) 2.720(6) 163(5) 1_655 N2 H2N2 O1 1.13(6) 1.65(6) 2.755(6) 166(4) 1 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.119 _refine_diff_density_min -0.107 _refine_diff_density_rms 0.028 data_ab0456m _database_code_depnum_ccdc_archive 'CCDC 268351' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H30 Br N O2' _chemical_formula_weight 408.37 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' Br Br -0.2901 2.4595 '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 5.698(2) _cell_length_b 12.825(5) _cell_length_c 15.492(6) _cell_angle_alpha 105.226(6) _cell_angle_beta 96.024(6) _cell_angle_gamma 96.465(6) _cell_volume 1074.7(7) _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 NEEDLE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.95 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 1.925 _exptl_absorpt_correction_type SADABS _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_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <10% _diffrn_reflns_number 5929 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 22.49 _reflns_number_total 2793 _reflns_number_gt 1822 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, MERCURY 1.3' _computing_publication_material ? _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^)+(0.0586P)^2^+0.6294P] 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 2793 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 Br1 Br 0.29412(13) 0.10933(6) -0.40811(4) 0.0967(4) Uani 1 1 d . . . N1 N 0.8286(7) 0.3560(3) 0.2284(2) 0.0491(10) Uani 1 1 d . . . H1A H 0.6752 0.3274 0.2072 0.059 Uiso 1 1 calc R . . H1B H 0.9188 0.3162 0.1921 0.059 Uiso 1 1 calc R . . O1 O 0.3581(6) 0.2752(3) 0.1842(2) 0.0650(10) Uani 1 1 d . . . O2 O 0.0179(6) 0.2205(3) 0.0885(2) 0.0765(12) Uani 1 1 d . . . C1A C 0.8837(9) 0.3405(4) 0.3217(3) 0.0520(13) Uani 1 1 d . . . H1A1 H 1.0414 0.3815 0.3491 0.062 Uiso 1 1 calc R . . C2A C 0.8937(10) 0.2189(4) 0.3124(4) 0.0684(16) Uani 1 1 d . . . H2A1 H 1.0161 0.1948 0.2759 0.082 Uiso 1 1 calc R . . H2A2 H 0.7418 0.1763 0.2821 0.082 Uiso 1 1 calc R . . C3A C 0.9495(11) 0.2001(5) 0.4066(4) 0.0828(18) Uani 1 1 d . . . H3A1 H 0.9497 0.1227 0.3996 0.099 Uiso 1 1 calc R . . H3A2 H 1.1072 0.2379 0.4345 0.099 Uiso 1 1 calc R . . C4A C 0.7666(11) 0.2410(5) 0.4680(4) 0.0820(18) Uani 1 1 d . . . H4A1 H 0.8125 0.2323 0.5276 0.098 Uiso 1 1 calc R . . H4A2 H 0.6116 0.1976 0.4437 0.098 Uiso 1 1 calc R . . C5A C 0.7495(12) 0.3627(5) 0.4760(4) 0.0850(19) Uani 1 1 d . . . H5A1 H 0.6224 0.3847 0.5107 0.102 Uiso 1 1 calc R . . H5A2 H 0.8977 0.4069 0.5085 0.102 Uiso 1 1 calc R . . C6A C 0.7008(10) 0.3839(5) 0.3829(3) 0.0678(16) Uani 1 1 d . . . H6A1 H 0.5418 0.3486 0.3541 0.081 Uiso 1 1 calc R . . H6A2 H 0.7071 0.4618 0.3907 0.081 Uiso 1 1 calc R . . C1B C 0.8657(8) 0.4717(4) 0.2188(3) 0.0506(13) Uani 1 1 d . . . H1B1 H 0.7652 0.5152 0.2570 0.061 Uiso 1 1 calc R . . C2B C 0.7842(10) 0.4680(4) 0.1199(4) 0.0656(15) Uani 1 1 d . . . H2B1 H 0.6164 0.4380 0.1038 0.079 Uiso 1 1 calc R . . H2B2 H 0.8730 0.4202 0.0806 0.079 Uiso 1 1 calc R . . C3B C 0.8233(10) 0.5839(5) 0.1051(4) 0.0777(17) Uani 1 1 d . . . H3B1 H 0.7799 0.5786 0.0417 0.093 Uiso 1 1 calc R . . H3B2 H 0.7217 0.6298 0.1395 0.093 Uiso 1 1 calc R . . C4B C 1.0873(11) 0.6361(5) 0.1357(4) 0.0778(17) Uani 1 1 d . . . H4B1 H 1.1872 0.5941 0.0972 0.093 Uiso 1 1 calc R . . H4B2 H 1.1075 0.7098 0.1294 0.093 Uiso 1 1 calc R . . C5B C 1.1657(10) 0.6396(4) 0.2341(4) 0.0749(17) Uani 1 1 d . . . H5B1 H 1.0762 0.6875 0.2730 0.090 Uiso 1 1 calc R . . H5B2 H 1.3334 0.6696 0.2507 0.090 Uiso 1 1 calc R . . C6B C 1.1266(9) 0.5254(4) 0.2498(4) 0.0631(15) Uani 1 1 d . . . H6B1 H 1.2302 0.4796 0.2165 0.076 Uiso 1 1 calc R . . H6B2 H 1.1682 0.5318 0.3135 0.076 Uiso 1 1 calc R . . C1 C 0.2423(10) 0.2274(4) 0.1059(3) 0.0514(13) Uani 1 1 d . . . C2 C 0.3804(9) 0.1786(4) 0.0308(3) 0.0521(13) Uani 1 1 d . . . H2 H 0.5364 0.1678 0.0458 0.062 Uiso 1 1 calc R . . C3 C 0.2883(9) 0.1510(4) -0.0550(3) 0.0531(13) Uani 1 1 d . . . H3 H 0.1293 0.1596 -0.0669 0.064 Uiso 1 1 calc R . . C4 C 0.4067(9) 0.1077(4) -0.1355(3) 0.0503(13) Uani 1 1 d . . . C5 C 0.3155(9) 0.1209(4) -0.2198(3) 0.0544(13) Uani 1 1 d . . . H5 H 0.1798 0.1543 -0.2246 0.065 Uiso 1 1 calc R . . C6 C 0.4262(11) 0.0847(4) -0.2958(3) 0.0617(15) Uani 1 1 d . . . C7 C 0.6271(11) 0.0319(5) -0.2922(4) 0.0724(17) Uani 1 1 d . . . H7 H 0.6994 0.0078 -0.3434 0.087 Uiso 1 1 calc R . . C8 C 0.7169(10) 0.0163(5) -0.2099(4) 0.0716(17) Uani 1 1 d . . . H8 H 0.8488 -0.0199 -0.2069 0.086 Uiso 1 1 calc R . . C9 C 0.6121(9) 0.0540(4) -0.1314(4) 0.0602(14) Uani 1 1 d . . . H9 H 0.6766 0.0441 -0.0770 0.072 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 Br1 0.1239(7) 0.1096(6) 0.0552(5) 0.0280(4) 0.0148(4) -0.0028(4) N1 0.045(2) 0.054(3) 0.046(3) 0.0100(19) 0.0098(18) 0.0032(19) O1 0.054(2) 0.083(3) 0.048(2) 0.0050(19) 0.0067(18) 0.0004(19) O2 0.044(2) 0.116(3) 0.057(2) 0.002(2) 0.0073(18) 0.014(2) C1A 0.052(3) 0.055(3) 0.047(3) 0.015(2) 0.002(2) 0.002(3) C2A 0.078(4) 0.062(4) 0.073(4) 0.024(3) 0.026(3) 0.016(3) C3A 0.092(5) 0.081(4) 0.089(5) 0.045(4) 0.018(4) 0.013(4) C4A 0.087(4) 0.098(5) 0.062(4) 0.035(3) 0.009(3) -0.009(4) C5A 0.105(5) 0.100(5) 0.046(4) 0.014(3) 0.016(3) 0.004(4) C6A 0.086(4) 0.078(4) 0.040(3) 0.008(3) 0.022(3) 0.021(3) C1B 0.059(3) 0.044(3) 0.048(3) 0.009(2) 0.013(2) 0.007(2) C2B 0.068(4) 0.065(4) 0.060(4) 0.019(3) 0.001(3) -0.001(3) C3B 0.092(5) 0.069(4) 0.077(4) 0.035(3) 0.001(3) 0.007(3) C4B 0.088(5) 0.061(4) 0.093(5) 0.034(3) 0.023(4) 0.006(3) C5B 0.079(4) 0.060(4) 0.085(5) 0.026(3) 0.005(3) -0.003(3) C6B 0.062(4) 0.060(4) 0.061(4) 0.018(3) -0.001(3) -0.009(3) C1 0.053(4) 0.056(3) 0.048(3) 0.016(3) 0.014(3) 0.010(3) C2 0.047(3) 0.057(3) 0.051(3) 0.011(3) 0.011(3) 0.009(2) C3 0.050(3) 0.058(3) 0.052(4) 0.013(3) 0.015(3) 0.010(3) C4 0.051(3) 0.046(3) 0.050(3) 0.009(2) 0.011(3) -0.001(3) C5 0.058(3) 0.057(3) 0.049(3) 0.014(3) 0.013(3) 0.005(3) C6 0.073(4) 0.061(4) 0.043(3) 0.005(3) 0.014(3) -0.010(3) C7 0.067(4) 0.069(4) 0.071(5) -0.001(3) 0.030(3) -0.002(3) C8 0.055(4) 0.069(4) 0.083(5) 0.005(3) 0.017(3) 0.009(3) C9 0.059(4) 0.057(3) 0.058(4) 0.009(3) 0.007(3) 0.001(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 Br1 C6 1.939(6) . ? N1 C1A 1.516(6) . ? N1 C1B 1.524(6) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? O1 O1 0.000(10) 1 ? O1 C1 1.278(6) . ? O2 C1 1.267(6) . ? C1A C6A 1.535(7) . ? C1A C2A 1.536(7) . ? C1A H1A1 0.9800 . ? C2A C3A 1.547(8) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C4A 1.529(8) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C4A C5A 1.548(8) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A C6A 1.541(7) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C1B C6B 1.536(7) . ? C1B C2B 1.540(7) . ? C1B H1B1 0.9800 . ? C2B C3B 1.558(7) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.547(7) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4B C5B 1.531(8) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C5B C6B 1.542(7) . ? C5B H5B1 0.9700 . ? C5B H5B2 0.9700 . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C1 O1 1.278(6) 1 ? C1 C2 1.511(7) . ? C2 C3 1.317(6) . ? C2 H2 0.9300 . ? C3 C4 1.488(7) . ? C3 H3 0.9300 . ? C4 C5 1.414(7) . ? C4 C9 1.427(7) . ? C5 C6 1.391(7) . ? C5 H5 0.9300 . ? C6 C7 1.398(8) . ? C7 C8 1.396(8) . ? C7 H7 0.9300 . ? C8 C9 1.405(7) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? 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 N1 C1B 118.1(3) . . ? C1A N1 H1A 107.8 . . ? C1B N1 H1A 107.8 . . ? C1A N1 H1B 107.8 . . ? C1B N1 H1B 107.8 . . ? H1A N1 H1B 107.1 . . ? O1 O1 C1 0(10) 1 . ? N1 C1A C6A 111.5(4) . . ? N1 C1A C2A 108.9(4) . . ? C6A C1A C2A 111.5(4) . . ? N1 C1A H1A1 108.3 . . ? C6A C1A H1A1 108.3 . . ? C2A C1A H1A1 108.3 . . ? C1A C2A C3A 110.3(4) . . ? C1A C2A H2A1 109.6 . . ? C3A C2A H2A1 109.6 . . ? C1A C2A H2A2 109.6 . . ? C3A C2A H2A2 109.6 . . ? H2A1 C2A H2A2 108.1 . . ? C4A C3A C2A 111.6(5) . . ? C4A C3A H3A1 109.3 . . ? C2A C3A H3A1 109.3 . . ? C4A C3A H3A2 109.3 . . ? C2A C3A H3A2 109.3 . . ? H3A1 C3A H3A2 108.0 . . ? C3A C4A C5A 110.9(5) . . ? C3A C4A H4A1 109.5 . . ? C5A C4A H4A1 109.5 . . ? C3A C4A H4A2 109.5 . . ? C5A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 108.1 . . ? C6A C5A C4A 112.1(5) . . ? C6A C5A H5A1 109.2 . . ? C4A C5A H5A1 109.2 . . ? C6A C5A H5A2 109.2 . . ? C4A C5A H5A2 109.2 . . ? H5A1 C5A H5A2 107.9 . . ? C1A C6A C5A 111.4(5) . . ? C1A C6A H6A1 109.3 . . ? C5A C6A H6A1 109.3 . . ? C1A C6A H6A2 109.3 . . ? C5A C6A H6A2 109.3 . . ? H6A1 C6A H6A2 108.0 . . ? N1 C1B C6B 111.3(4) . . ? N1 C1B C2B 108.9(4) . . ? C6B C1B C2B 111.6(4) . . ? N1 C1B H1B1 108.3 . . ? C6B C1B H1B1 108.3 . . ? C2B C1B H1B1 108.3 . . ? C1B C2B C3B 111.4(4) . . ? C1B C2B H2B1 109.4 . . ? C3B C2B H2B1 109.4 . . ? C1B C2B H2B2 109.4 . . ? C3B C2B H2B2 109.4 . . ? H2B1 C2B H2B2 108.0 . . ? C4B C3B C2B 110.2(5) . . ? C4B C3B H3B1 109.6 . . ? C2B C3B H3B1 109.6 . . ? C4B C3B H3B2 109.6 . . ? C2B C3B H3B2 109.6 . . ? H3B1 C3B H3B2 108.1 . . ? C5B C4B C3B 110.9(5) . . ? C5B C4B H4B1 109.5 . . ? C3B C4B H4B1 109.5 . . ? C5B C4B H4B2 109.5 . . ? C3B C4B H4B2 109.5 . . ? H4B1 C4B H4B2 108.0 . . ? C4B C5B C6B 112.1(4) . . ? C4B C5B H5B1 109.2 . . ? C6B C5B H5B1 109.2 . . ? C4B C5B H5B2 109.2 . . ? C6B C5B H5B2 109.2 . . ? H5B1 C5B H5B2 107.9 . . ? C1B C6B C5B 110.9(4) . . ? C1B C6B H6B1 109.5 . . ? C5B C6B H6B1 109.5 . . ? C1B C6B H6B2 109.5 . . ? C5B C6B H6B2 109.5 . . ? H6B1 C6B H6B2 108.0 . . ? O2 C1 O1 122.8(4) . 1 ? O2 C1 O1 122.8(4) . . ? O1 C1 O1 0.0(2) 1 . ? O2 C1 C2 118.9(5) . . ? O1 C1 C2 118.3(5) 1 . ? O1 C1 C2 118.3(5) . . ? C3 C2 C1 122.5(5) . . ? C3 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? C2 C3 C4 128.1(5) . . ? C2 C3 H3 115.9 . . ? C4 C3 H3 115.9 . . ? C5 C4 C9 117.9(5) . . ? C5 C4 C3 119.2(5) . . ? C9 C4 C3 122.8(5) . . ? C6 C5 C4 120.8(5) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 121.4(5) . . ? C5 C6 Br1 118.1(5) . . ? C7 C6 Br1 120.4(4) . . ? C8 C7 C6 118.5(5) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C7 C8 C9 121.4(6) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C4 119.9(5) . . ? C8 C9 H9 120.1 . . ? C4 C9 H9 120.1 . . ? 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 N1 H1A O1 0.90 1.82 2.710(5) 170.5 1 N1 H1B O2 0.90 1.93 2.796(5) 161.7 1_655 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.450 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.059