# Supplementary Material (ESI) for Soft Matter # This journal is (C) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 777 loop_ _publ_author_name 'Ivan Lin' _publ_contact_author_name 'Ivan Lin' _publ_contact_author_email ijblin@mail.ndhu.edu.tw # Attachment '- crystal.txt' data_my52m _database_code_depnum_ccdc_archive 'CCDC 802278' #TrackingRef '- crystal.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H72 Br N O2' _chemical_formula_weight 642.87 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' 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 7.1010(5) _cell_length_b 8.7939(6) _cell_length_c 33.018(2) _cell_angle_alpha 82.386(1) _cell_angle_beta 88.279(2) _cell_angle_gamma 67.146(1) _cell_volume 1882.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5475 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 1.121 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.76252 _exptl_absorpt_correction_T_max 0.95251 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22009 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 0.62 _diffrn_reflns_theta_max 28.32 _reflns_number_total 9295 _reflns_number_gt 7911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0839P)^2^+0.2757P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9295 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1231 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 Br1 Br 0.34244(3) 0.15052(3) 0.423166(6) 0.02004(8) Uani 1 1 d . . . O1 O 0.2290(2) -0.39274(17) 0.57790(4) 0.0142(3) Uani 1 1 d . . . O2 O 0.2614(2) 0.13699(18) 0.52272(5) 0.0188(3) Uani 1 1 d . . . N1 N 0.2375(3) -0.3322(2) 0.45245(5) 0.0131(3) Uani 1 1 d . . . C1 C 0.2297(3) -0.2048(2) 0.47238(6) 0.0139(4) Uani 1 1 d . . . C2 C 0.2281(3) -0.2171(2) 0.51437(6) 0.0135(4) Uani 1 1 d . . . C3 C 0.2333(3) -0.3659(2) 0.53720(6) 0.0116(4) Uani 1 1 d . . . C4 C 0.2462(3) -0.4981(2) 0.51604(6) 0.0131(4) Uani 1 1 d . . . C5 C 0.2456(3) -0.4782(2) 0.47429(6) 0.0144(4) Uani 1 1 d . . . C6 C 0.1870(3) -0.2516(2) 0.60085(6) 0.0148(4) Uani 1 1 d . . . C7 C 0.1191(3) -0.2988(3) 0.64302(6) 0.0168(4) Uani 1 1 d . . . C8 C 0.2822(3) -0.4447(3) 0.66942(6) 0.0153(4) Uani 1 1 d . . . C9 C 0.4534(3) -0.4038(3) 0.68614(6) 0.0149(4) Uani 1 1 d . . . C10 C 0.5985(3) -0.5507(3) 0.71539(6) 0.0148(4) Uani 1 1 d . . . C11 C 0.7664(3) -0.5162(2) 0.73537(6) 0.0146(4) Uani 1 1 d . . . C12 C 0.9051(3) -0.6661(2) 0.76450(6) 0.0144(4) Uani 1 1 d . . . C13 C 1.0740(3) -0.6360(3) 0.78555(6) 0.0148(4) Uani 1 1 d . . . C14 C 1.2139(3) -0.7883(3) 0.81381(6) 0.0145(4) Uani 1 1 d . . . C15 C 1.3850(3) -0.7594(3) 0.83431(6) 0.0149(4) Uani 1 1 d . . . C16 C 1.5263(3) -0.9128(3) 0.86242(6) 0.0152(4) Uani 1 1 d . . . C17 C 1.6986(3) -0.8844(3) 0.88268(6) 0.0163(4) Uani 1 1 d . . . C18 C 1.8395(3) -1.0383(3) 0.91066(6) 0.0159(4) Uani 1 1 d . . . C19 C 2.0158(3) -1.0131(3) 0.93026(6) 0.0176(4) Uani 1 1 d . . . C20 C 2.1500(4) -1.1651(3) 0.95917(7) 0.0224(5) Uani 1 1 d . . . C21 C 2.3255(4) -1.1409(4) 0.97949(8) 0.0299(5) Uani 1 1 d . . . C22 C 0.2116(3) -0.3074(3) 0.40709(6) 0.0173(4) Uani 1 1 d . . . C23 C -0.0154(3) -0.2416(3) 0.39588(6) 0.0162(4) Uani 1 1 d . . . C24 C -0.0694(3) -0.2029(3) 0.35012(6) 0.0153(4) Uani 1 1 d . . . C25 C -0.3017(3) -0.1149(3) 0.34376(6) 0.0146(4) Uani 1 1 d . . . C26 C -0.3797(3) -0.0800(3) 0.29955(6) 0.0148(4) Uani 1 1 d . . . C27 C -0.6129(3) 0.0102(3) 0.29585(6) 0.0149(4) Uani 1 1 d . . . C28 C -0.6978(3) 0.0416(3) 0.25223(6) 0.0154(4) Uani 1 1 d . . . C29 C -0.9305(3) 0.1338(3) 0.24858(6) 0.0148(4) Uani 1 1 d . . . C30 C -1.0149(3) 0.1637(3) 0.20492(6) 0.0153(4) Uani 1 1 d . . . C31 C -1.2469(3) 0.2584(3) 0.20081(6) 0.0153(4) Uani 1 1 d . . . C32 C -1.3296(3) 0.2876(3) 0.15701(6) 0.0160(4) Uani 1 1 d . . . C33 C -1.5611(3) 0.3823(3) 0.15230(6) 0.0154(4) Uani 1 1 d . . . C34 C -1.6402(3) 0.4101(3) 0.10826(6) 0.0160(4) Uani 1 1 d . . . C35 C -1.8716(3) 0.5049(3) 0.10296(6) 0.0165(4) Uani 1 1 d . . . C36 C -1.9476(4) 0.5321(3) 0.05892(7) 0.0206(4) Uani 1 1 d . . . C37 C -2.1782(4) 0.6305(3) 0.05327(7) 0.0264(5) Uani 1 1 d . . . H1A H 0.2265 -0.1031 0.4553 0.080 Uiso 1 1 d . . . H2A H 0.2876 0.1417 0.4991 0.080 Uiso 1 1 d . . . H2B H 0.3585 0.0774 0.5328 0.080 Uiso 1 1 d . . . H2C H 0.2186 -0.1282 0.5271 0.080 Uiso 1 1 d . . . H4A H 0.2491 -0.5973 0.5295 0.080 Uiso 1 1 d . . . H5A H 0.2489 -0.5579 0.4594 0.080 Uiso 1 1 d . . . H6A H 0.3145 -0.2345 0.6002 0.080 Uiso 1 1 d . . . H6B H 0.0757 -0.1614 0.5865 0.080 Uiso 1 1 d . . . H7A H 0.0026 -0.3147 0.6386 0.080 Uiso 1 1 d . . . H7B H 0.0636 -0.2040 0.6574 0.080 Uiso 1 1 d . . . H8A H 0.2191 -0.4814 0.6930 0.080 Uiso 1 1 d . . . H8B H 0.3519 -0.5393 0.6528 0.080 Uiso 1 1 d . . . H9A H 0.5281 -0.3784 0.6656 0.080 Uiso 1 1 d . . . H9B H 0.3900 -0.3055 0.7011 0.080 Uiso 1 1 d . . . H10A H 0.5208 -0.5827 0.7365 0.080 Uiso 1 1 d . . . H10B H 0.6642 -0.6408 0.7005 0.080 Uiso 1 1 d . . . H11A H 0.8432 -0.4856 0.7142 0.080 Uiso 1 1 d . . . H11B H 0.7074 -0.4260 0.7501 0.080 Uiso 1 1 d . . . H12A H 0.8255 -0.6931 0.7857 0.080 Uiso 1 1 d . . . H12B H 0.9656 -0.7549 0.7504 0.080 Uiso 1 1 d . . . H13A H 1.1458 -0.6100 0.7676 0.080 Uiso 1 1 d . . . H13B H 1.0142 -0.5472 0.7994 0.080 Uiso 1 1 d . . . H14A H 1.1314 -0.8215 0.8343 0.080 Uiso 1 1 d . . . H14B H 1.2709 -0.8845 0.7989 0.080 Uiso 1 1 d . . . H15A H 1.4620 -0.7375 0.8150 0.080 Uiso 1 1 d . . . H15B H 1.3374 -0.6719 0.8504 0.080 Uiso 1 1 d . . . H16A H 1.4485 -0.9434 0.8824 0.080 Uiso 1 1 d . . . H16B H 1.5808 -1.0014 0.8464 0.080 Uiso 1 1 d . . . H17A H 1.6507 -0.8023 0.8973 0.080 Uiso 1 1 d . . . H17B H 1.7800 -0.8540 0.8617 0.080 Uiso 1 1 d . . . H18A H 1.7604 -1.0696 0.9305 0.080 Uiso 1 1 d . . . H18B H 1.8889 -1.1254 0.8954 0.080 Uiso 1 1 d . . . H19A H 2.0984 -0.9955 0.9092 0.080 Uiso 1 1 d . . . H19B H 1.9627 -0.9213 0.9461 0.080 Uiso 1 1 d . . . H20A H 2.0609 -1.1880 0.9796 0.080 Uiso 1 1 d . . . H20B H 2.2076 -1.2519 0.9457 0.080 Uiso 1 1 d . . . H21A H 2.2818 -1.0575 0.9946 0.080 Uiso 1 1 d . . . H21B H 2.4115 -1.1255 0.9591 0.080 Uiso 1 1 d . . . H21C H 2.4115 -1.2425 0.9997 0.080 Uiso 1 1 d . . . H22A H 0.2640 -0.2243 0.3970 0.080 Uiso 1 1 d . . . H22B H 0.2868 -0.3966 0.3970 0.080 Uiso 1 1 d . . . H23A H -0.0838 -0.1422 0.4093 0.080 Uiso 1 1 d . . . H23B H -0.0697 -0.3243 0.4074 0.080 Uiso 1 1 d . . . H24A H 0.0034 -0.1360 0.3356 0.080 Uiso 1 1 d . . . H24B H -0.0253 -0.2983 0.3357 0.080 Uiso 1 1 d . . . H25A H -0.3439 -0.0126 0.3555 0.080 Uiso 1 1 d . . . H25B H -0.3691 -0.1825 0.3609 0.080 Uiso 1 1 d . . . H26A H -0.3140 -0.0148 0.2823 0.080 Uiso 1 1 d . . . H26B H -0.3368 -0.1768 0.2869 0.080 Uiso 1 1 d . . . H27A H -0.6582 0.1184 0.3069 0.080 Uiso 1 1 d . . . H27B H -0.6752 -0.0541 0.3142 0.080 Uiso 1 1 d . . . H28A H -0.6285 0.1027 0.2337 0.080 Uiso 1 1 d . . . H28B H -0.6591 -0.0574 0.2399 0.080 Uiso 1 1 d . . . H29A H -0.9749 0.2414 0.2586 0.080 Uiso 1 1 d . . . H29B H -0.9959 0.0727 0.2663 0.080 Uiso 1 1 d . . . H30A H -0.9545 0.2338 0.1852 0.080 Uiso 1 1 d . . . H30B H -0.9752 0.0671 0.1955 0.080 Uiso 1 1 d . . . H31A H -1.3132 0.2051 0.2190 0.080 Uiso 1 1 d . . . H31B H -1.2984 0.3712 0.2109 0.080 Uiso 1 1 d . . . H32A H -1.2659 0.3403 0.1387 0.080 Uiso 1 1 d . . . H32B H -1.2838 0.1838 0.1472 0.080 Uiso 1 1 d . . . H33A H -1.6212 0.3267 0.1700 0.080 Uiso 1 1 d . . . H33B H -1.6059 0.4908 0.1637 0.080 Uiso 1 1 d . . . H34A H -1.5807 0.4669 0.0911 0.080 Uiso 1 1 d . . . H34B H -1.5978 0.3075 0.0990 0.080 Uiso 1 1 d . . . H35A H -1.9406 0.4460 0.1209 0.080 Uiso 1 1 d . . . H35B H -1.9213 0.6147 0.1142 0.080 Uiso 1 1 d . . . H36A H -1.8819 0.5829 0.0425 0.080 Uiso 1 1 d . . . H36B H -1.9052 0.4239 0.0482 0.080 Uiso 1 1 d . . . H37A H -2.2426 0.5806 0.0679 0.080 Uiso 1 1 d . . . H37B H -2.2203 0.7464 0.0634 0.080 Uiso 1 1 d . . . H37C H -2.2172 0.6475 0.0263 0.080 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 Br1 0.01863(12) 0.02067(12) 0.02215(12) -0.00308(8) 0.00004(8) -0.00893(9) O1 0.0190(8) 0.0111(6) 0.0132(7) -0.0017(5) -0.0009(5) -0.0064(6) O2 0.0213(8) 0.0134(7) 0.0212(7) -0.0039(6) 0.0044(6) -0.0059(6) N1 0.0112(8) 0.0144(8) 0.0128(8) -0.0001(6) -0.0011(6) -0.0046(7) C1 0.0113(9) 0.0122(9) 0.0187(9) 0.0013(7) -0.0029(7) -0.0059(8) C2 0.0123(9) 0.0102(8) 0.0191(10) -0.0015(7) -0.0021(7) -0.0055(7) C3 0.0071(9) 0.0110(8) 0.0162(9) -0.0006(7) -0.0016(7) -0.0032(7) C4 0.0101(9) 0.0091(8) 0.0194(10) -0.0013(7) -0.0008(7) -0.0030(7) C5 0.0119(9) 0.0111(9) 0.0203(10) -0.0027(7) -0.0006(7) -0.0044(8) C6 0.0154(10) 0.0130(9) 0.0158(9) -0.0039(7) -0.0011(7) -0.0045(8) C7 0.0110(9) 0.0214(10) 0.0156(9) -0.0023(8) -0.0022(7) -0.0035(8) C8 0.0148(10) 0.0189(10) 0.0134(9) -0.0014(7) -0.0020(7) -0.0078(8) C9 0.0132(10) 0.0154(9) 0.0155(9) -0.0013(7) -0.0035(7) -0.0048(8) C10 0.0137(10) 0.0140(9) 0.0162(9) -0.0011(7) -0.0030(7) -0.0050(8) C11 0.0152(10) 0.0130(9) 0.0147(9) -0.0011(7) -0.0022(7) -0.0047(8) C12 0.0140(10) 0.0141(9) 0.0150(9) -0.0015(7) -0.0022(7) -0.0053(8) C13 0.0137(10) 0.0142(9) 0.0163(9) -0.0011(7) -0.0016(7) -0.0054(8) C14 0.0132(10) 0.0151(9) 0.0162(9) -0.0007(7) -0.0026(7) -0.0067(8) C15 0.0133(10) 0.0151(9) 0.0169(9) -0.0005(8) -0.0027(7) -0.0063(8) C16 0.0137(10) 0.0152(9) 0.0172(9) -0.0003(8) -0.0028(7) -0.0067(8) C17 0.0147(10) 0.0148(9) 0.0192(10) -0.0006(8) -0.0036(8) -0.0058(8) C18 0.0142(10) 0.0160(9) 0.0175(10) -0.0006(8) -0.0029(8) -0.0061(8) C19 0.0160(10) 0.0208(10) 0.0161(10) -0.0013(8) -0.0027(8) -0.0074(8) C20 0.0178(11) 0.0248(11) 0.0220(11) 0.0010(9) -0.0047(9) -0.0063(9) C21 0.0201(12) 0.0418(14) 0.0251(12) -0.0042(11) -0.0074(9) -0.0087(11) C22 0.0146(10) 0.0234(10) 0.0118(9) -0.0011(8) -0.0015(7) -0.0054(8) C23 0.0124(10) 0.0228(10) 0.0130(9) -0.0016(8) -0.0009(7) -0.0067(8) C24 0.0136(10) 0.0179(10) 0.0131(9) -0.0017(7) -0.0011(7) -0.0048(8) C25 0.0117(9) 0.0169(9) 0.0141(9) -0.0028(7) -0.0011(7) -0.0042(8) C26 0.0141(10) 0.0153(9) 0.0141(9) -0.0019(7) -0.0014(7) -0.0045(8) C27 0.0115(9) 0.0164(9) 0.0164(9) -0.0014(8) -0.0016(7) -0.0052(8) C28 0.0125(10) 0.0163(9) 0.0168(9) -0.0023(8) -0.0009(7) -0.0049(8) C29 0.0121(9) 0.0168(9) 0.0160(9) -0.0015(8) -0.0014(7) -0.0063(8) C30 0.0137(10) 0.0157(9) 0.0159(9) -0.0023(8) -0.0008(7) -0.0046(8) C31 0.0129(10) 0.0167(9) 0.0166(9) -0.0018(8) 0.0000(7) -0.0062(8) C32 0.0136(10) 0.0173(10) 0.0166(10) -0.0016(8) -0.0009(8) -0.0055(8) C33 0.0126(10) 0.0163(9) 0.0169(9) -0.0019(8) -0.0014(7) -0.0051(8) C34 0.0136(10) 0.0168(10) 0.0168(9) -0.0016(8) -0.0009(8) -0.0053(8) C35 0.0150(10) 0.0168(9) 0.0172(10) -0.0015(8) -0.0016(8) -0.0057(8) C36 0.0187(11) 0.0236(11) 0.0186(10) -0.0005(8) -0.0031(8) -0.0076(9) C37 0.0195(12) 0.0309(13) 0.0255(11) -0.0013(10) -0.0079(9) -0.0064(10) _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 C3 1.335(2) . ? O1 C6 1.467(2) . ? N1 C1 1.355(3) . ? N1 C5 1.368(3) . ? N1 C22 1.491(2) . ? C1 C2 1.376(3) . ? C2 C3 1.409(3) . ? C3 C4 1.406(3) . ? C4 C5 1.366(3) . ? C6 C7 1.518(3) . ? C7 C8 1.535(3) . ? C8 C9 1.532(3) . ? C9 C10 1.536(3) . ? C10 C11 1.527(3) . ? C11 C12 1.531(3) . ? C12 C13 1.529(3) . ? C13 C14 1.530(3) . ? C14 C15 1.527(3) . ? C15 C16 1.537(3) . ? C16 C17 1.529(3) . ? C17 C18 1.535(3) . ? C18 C19 1.529(3) . ? C19 C20 1.528(3) . ? C20 C21 1.530(3) . ? C22 C23 1.525(3) . ? C23 C24 1.531(3) . ? C24 C25 1.533(3) . ? C25 C26 1.526(3) . ? C26 C27 1.534(3) . ? C27 C28 1.527(3) . ? C28 C29 1.532(3) . ? C29 C30 1.528(3) . ? C30 C31 1.531(3) . ? C31 C32 1.529(3) . ? C32 C33 1.529(3) . ? C33 C34 1.529(3) . ? C34 C35 1.530(3) . ? C35 C36 1.523(3) . ? C36 C37 1.529(3) . ? 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 O1 C6 118.42(15) . . ? C1 N1 C5 119.72(17) . . ? C1 N1 C22 120.35(17) . . ? C5 N1 C22 119.51(17) . . ? N1 C1 C2 121.84(18) . . ? C1 C2 C3 118.99(18) . . ? O1 C3 C4 116.69(17) . . ? O1 C3 C2 124.93(18) . . ? C4 C3 C2 118.38(18) . . ? C5 C4 C3 119.97(18) . . ? C4 C5 N1 121.07(18) . . ? O1 C6 C7 107.31(16) . . ? C6 C7 C8 115.19(17) . . ? C9 C8 C7 114.69(17) . . ? C8 C9 C10 111.38(17) . . ? C11 C10 C9 114.61(17) . . ? C10 C11 C12 112.41(17) . . ? C13 C12 C11 114.09(17) . . ? C12 C13 C14 113.37(17) . . ? C15 C14 C13 113.45(17) . . ? C14 C15 C16 113.39(17) . . ? C17 C16 C15 113.43(17) . . ? C16 C17 C18 113.16(17) . . ? C19 C18 C17 113.71(17) . . ? C20 C19 C18 113.04(18) . . ? C19 C20 C21 113.7(2) . . ? N1 C22 C23 109.20(16) . . ? C22 C23 C24 115.92(17) . . ? C23 C24 C25 109.75(17) . . ? C26 C25 C24 115.64(17) . . ? C25 C26 C27 112.27(17) . . ? C28 C27 C26 113.89(17) . . ? C27 C28 C29 113.74(17) . . ? C30 C29 C28 113.53(17) . . ? C29 C30 C31 113.95(17) . . ? C32 C31 C30 113.48(17) . . ? C31 C32 C33 114.21(17) . . ? C34 C33 C32 113.27(17) . . ? C33 C34 C35 113.99(17) . . ? C36 C35 C34 113.31(18) . . ? C35 C36 C37 113.55(19) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.078 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.124 data_41026am _database_code_depnum_ccdc_archive 'CCDC 802279' #TrackingRef '- crystal.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H38 Cl N O' _chemical_formula_weight 355.97 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' Cl Cl 0.1484 0.1585 '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 5.0633(2) _cell_length_b 7.8476(3) _cell_length_c 28.8648(9) _cell_angle_alpha 92.227(2) _cell_angle_beta 93.436(2) _cell_angle_gamma 102.045(2) _cell_volume 1118.12(7) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4394 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 27.52 _exptl_crystal_description ? _exptl_crystal_colour clear _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.090 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.057 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7172 _exptl_absorpt_correction_T_max 0.9163 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16173 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 0.71 _diffrn_reflns_theta_max 28.04 _reflns_number_total 5404 _reflns_number_gt 3348 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1152P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5404 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1997 _refine_ls_wR_factor_gt 0.1710 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 Cl1 Cl 0.05565(10) 0.86552(8) 0.399689(17) 0.0607(2) Uani 1 1 d . . . C5 C 0.5765(4) 1.2405(3) 0.35866(6) 0.0513(5) Uani 1 1 d . . . H5A H 0.5674 1.3554 0.3483 0.062 Uiso 1 1 calc R . . H5B H 0.3944 1.1810 0.3644 0.062 Uiso 1 1 calc R . . C6 C 0.6777(4) 1.1408(3) 0.32059(6) 0.0504(5) Uani 1 1 d . . . H6A H 0.6890 1.0259 0.3307 0.061 Uiso 1 1 calc R . . H6B H 0.8580 1.2012 0.3140 0.061 Uiso 1 1 calc R . . C4 C 0.8200(4) 1.1771(3) 0.47930(7) 0.0500(5) Uani 1 1 d . . . H4 H 0.7577 1.1099 0.5038 0.060 Uiso 1 1 calc R . . C3 C 0.6687(4) 1.1616(3) 0.43822(7) 0.0504(5) Uani 1 1 d . . . H3 H 0.5056 1.0802 0.4347 0.061 Uiso 1 1 calc R . . C1 C 1.1517(4) 1.3938(3) 0.44738(7) 0.0521(5) Uani 1 1 d . . . H1 H 1.3177 1.4724 0.4497 0.063 Uiso 1 1 calc R . . C2 C 0.9877(4) 1.3758(3) 0.40737(7) 0.0523(5) Uani 1 1 d . . . H2 H 1.0422 1.4447 0.3827 0.063 Uiso 1 1 calc R . . C10 C 0.4821(4) 0.9152(3) 0.15182(7) 0.0537(5) Uani 1 1 d . . . H10A H 0.4823 0.7970 0.1604 0.064 Uiso 1 1 calc R . . H10B H 0.6661 0.9700 0.1458 0.064 Uiso 1 1 calc R . . C7 C 0.4907(4) 1.1223(3) 0.27673(7) 0.0530(5) Uani 1 1 d . . . H7A H 0.3107 1.0633 0.2838 0.064 Uiso 1 1 calc R . . H7B H 0.4795 1.2379 0.2672 0.064 Uiso 1 1 calc R . . C11 C 0.3034(4) 0.9075(3) 0.10735(7) 0.0533(5) Uani 1 1 d . . . H11A H 0.1194 0.8529 0.1134 0.064 Uiso 1 1 calc R . . H11B H 0.3032 1.0258 0.0988 0.064 Uiso 1 1 calc R . . C8 C 0.5779(4) 1.0232(3) 0.23660(7) 0.0542(5) Uani 1 1 d . . . H8A H 0.5801 0.9057 0.2456 0.065 Uiso 1 1 calc R . . H8B H 0.7612 1.0788 0.2304 0.065 Uiso 1 1 calc R . . C9 C 0.3973(4) 1.0131(3) 0.19217(7) 0.0541(5) Uani 1 1 d . . . H9A H 0.2141 0.9573 0.1984 0.065 Uiso 1 1 calc R . . H9B H 0.3945 1.1308 0.1834 0.065 Uiso 1 1 calc R . . C16 C 0.1975(4) 0.5969(3) -0.10318(7) 0.0544(5) Uani 1 1 d . . . H16A H 0.1967 0.4787 -0.0945 0.065 Uiso 1 1 calc R . . H16B H 0.3820 0.6509 -0.1091 0.065 Uiso 1 1 calc R . . C14 C 0.2926(4) 0.7037(3) -0.01829(7) 0.0541(5) Uani 1 1 d . . . H14A H 0.4766 0.7585 -0.0243 0.065 Uiso 1 1 calc R . . H14B H 0.2933 0.5855 -0.0097 0.065 Uiso 1 1 calc R . . C12 C 0.3869(4) 0.8093(3) 0.06664(7) 0.0538(5) Uani 1 1 d . . . H12A H 0.3869 0.6909 0.0751 0.065 Uiso 1 1 calc R . . H12B H 0.5709 0.8638 0.0605 0.065 Uiso 1 1 calc R . . C13 C 0.2080(4) 0.8021(3) 0.02241(6) 0.0537(5) Uani 1 1 d . . . H13A H 0.2080 0.9205 0.0139 0.064 Uiso 1 1 calc R . . H13B H 0.0240 0.7475 0.0285 0.064 Uiso 1 1 calc R . . C15 C 0.1146(4) 0.6953(3) -0.06273(7) 0.0549(5) Uani 1 1 d . . . H15A H -0.0694 0.6409 -0.0566 0.066 Uiso 1 1 calc R . . H15B H 0.1146 0.8134 -0.0714 0.066 Uiso 1 1 calc R . . C17 C 0.0219(4) 0.5887(3) -0.14775(7) 0.0547(5) Uani 1 1 d . . . H17A H -0.1627 0.5345 -0.1419 0.066 Uiso 1 1 calc R . . H17B H 0.0227 0.7069 -0.1565 0.066 Uiso 1 1 calc R . . C18 C 0.1066(4) 0.4901(3) -0.18792(7) 0.0571(5) Uani 1 1 d . . . H18A H 0.1057 0.3720 -0.1791 0.068 Uiso 1 1 calc R . . H18B H 0.2915 0.5442 -0.1936 0.068 Uiso 1 1 calc R . . C20 C 0.0242(7) 0.3827(4) -0.27213(9) 0.0891(8) Uani 1 1 d . . . H20A H 0.2058 0.4374 -0.2782 0.134 Uiso 1 1 calc R . . H20B H -0.0941 0.3832 -0.2994 0.134 Uiso 1 1 calc R . . H20C H 0.0187 0.2645 -0.2641 0.134 Uiso 1 1 calc R . . C19 C -0.0663(5) 0.4812(3) -0.23254(7) 0.0675(6) Uani 1 1 d . . . H19A H -0.2511 0.4262 -0.2271 0.081 Uiso 1 1 calc R . . H19B H -0.0661 0.5991 -0.2415 0.081 Uiso 1 1 calc R . . N1 N 0.7483(3) 1.2603(2) 0.40277(5) 0.0450(4) Uani 1 1 d . . . C21 C 1.0688(4) 1.2942(3) 0.48439(6) 0.0445(4) Uani 1 1 d . . . O1 O 1.2304(3) 1.3145(2) 0.52307(5) 0.0614(4) Uani 1 1 d . . . H1A H 1.1499 1.2615 0.5437 0.092 Uiso 1 1 calc R . . O2 O 0.4785(5) 0.6487(3) 0.36453(10) 0.1146(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0537(3) 0.0764(4) 0.0486(3) 0.0066(2) 0.0035(2) 0.0059(2) C5 0.0517(11) 0.0667(13) 0.0368(10) 0.0039(9) 0.0023(8) 0.0153(9) C6 0.0550(11) 0.0593(12) 0.0391(10) 0.0021(9) 0.0000(8) 0.0179(9) C4 0.0497(11) 0.0581(12) 0.0378(10) 0.0084(8) 0.0079(8) -0.0012(9) C3 0.0428(10) 0.0613(13) 0.0419(10) 0.0051(9) 0.0071(8) -0.0026(9) C1 0.0480(11) 0.0549(12) 0.0471(11) -0.0004(9) 0.0096(8) -0.0048(9) C2 0.0579(12) 0.0532(12) 0.0423(10) 0.0046(9) 0.0131(9) 0.0005(9) C10 0.0568(12) 0.0647(13) 0.0410(11) 0.0014(9) -0.0032(9) 0.0181(10) C7 0.0549(11) 0.0630(13) 0.0419(10) 0.0005(9) -0.0006(8) 0.0159(9) C11 0.0578(12) 0.0645(13) 0.0390(10) -0.0005(9) -0.0013(9) 0.0180(10) C8 0.0583(12) 0.0654(14) 0.0400(10) -0.0016(9) -0.0032(9) 0.0184(10) C9 0.0567(12) 0.0649(13) 0.0418(10) -0.0001(9) -0.0032(9) 0.0175(10) C16 0.0567(12) 0.0656(13) 0.0430(11) 0.0016(10) 0.0021(9) 0.0182(10) C14 0.0569(12) 0.0657(14) 0.0420(11) 0.0019(9) 0.0022(9) 0.0182(10) C12 0.0561(12) 0.0652(13) 0.0421(11) -0.0001(9) -0.0003(9) 0.0190(10) C13 0.0576(12) 0.0650(14) 0.0404(10) 0.0005(9) 0.0002(9) 0.0189(10) C15 0.0575(12) 0.0678(14) 0.0414(11) 0.0033(9) 0.0010(9) 0.0180(10) C17 0.0569(12) 0.0661(14) 0.0426(11) 0.0035(9) 0.0004(9) 0.0173(10) C18 0.0628(13) 0.0651(14) 0.0445(11) 0.0023(10) 0.0021(9) 0.0166(10) C20 0.122(2) 0.096(2) 0.0468(14) -0.0051(13) 0.0033(14) 0.0185(17) C19 0.0823(16) 0.0756(16) 0.0443(12) 0.0029(11) -0.0044(11) 0.0181(13) N1 0.0466(9) 0.0521(9) 0.0361(8) 0.0012(7) 0.0078(6) 0.0091(7) C21 0.0422(10) 0.0514(11) 0.0388(9) -0.0019(8) 0.0057(7) 0.0073(8) O1 0.0500(8) 0.0825(11) 0.0431(8) 0.0010(7) 0.0002(6) -0.0039(7) O2 0.0930(15) 0.0910(15) 0.151(2) -0.0108(14) 0.0010(14) 0.0037(11) _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 C5 N1 1.482(2) . ? C5 C6 1.500(3) . ? C6 C7 1.518(3) . ? C4 C3 1.360(3) . ? C4 C21 1.392(3) . ? C3 N1 1.338(2) . ? C1 C2 1.366(3) . ? C1 C21 1.382(3) . ? C2 N1 1.349(2) . ? C10 C9 1.503(3) . ? C10 C11 1.517(3) . ? C7 C8 1.508(3) . ? C11 C12 1.509(3) . ? C8 C9 1.519(3) . ? C16 C15 1.503(3) . ? C16 C17 1.511(3) . ? C14 C15 1.514(3) . ? C14 C13 1.513(3) . ? C12 C13 1.513(3) . ? C17 C18 1.502(3) . ? C18 C19 1.504(3) . ? C20 C19 1.502(3) . ? C21 O1 1.328(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 N1 C5 C6 113.48(15) . . ? C5 C6 C7 110.89(16) . . ? C3 C4 C21 119.52(18) . . ? N1 C3 C4 121.74(18) . . ? C2 C1 C21 119.43(18) . . ? N1 C2 C1 121.49(18) . . ? C9 C10 C11 114.41(17) . . ? C8 C7 C6 114.34(16) . . ? C12 C11 C10 114.78(17) . . ? C7 C8 C9 113.97(17) . . ? C10 C9 C8 114.59(17) . . ? C15 C16 C17 115.30(17) . . ? C15 C14 C13 114.79(17) . . ? C11 C12 C13 114.51(17) . . ? C12 C13 C14 114.32(17) . . ? C16 C15 C14 114.93(17) . . ? C18 C17 C16 114.82(17) . . ? C17 C18 C19 115.34(18) . . ? C20 C19 C18 114.1(2) . . ? C3 N1 C2 119.37(16) . . ? C3 N1 C5 120.12(16) . . ? C2 N1 C5 120.50(16) . . ? O1 C21 C1 118.49(17) . . ? O1 C21 C4 123.10(18) . . ? C1 C21 C4 118.40(17) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.04 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.343 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.072 data_jn07_0m _database_code_depnum_ccdc_archive 'CCDC 802280' #TrackingRef '- crystal.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H39 N O2' _chemical_formula_weight 337.53 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 P2(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 20.7504(8) _cell_length_b 7.9455(3) _cell_length_c 13.4383(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.245(2) _cell_angle_gamma 90.00 _cell_volume 2180.28(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1820 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 21.41 _exptl_crystal_description Columnar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.028 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.85753 _exptl_absorpt_correction_T_max 0.96843 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17765 _diffrn_reflns_av_R_equivalents 0.0905 _diffrn_reflns_av_sigmaI/netI 0.1066 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.00 _diffrn_reflns_theta_max 25.06 _reflns_number_total 3846 _reflns_number_gt 1361 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0717P)^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_number_reflns 3846 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1555 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1543 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 0.767 _refine_ls_restrained_S_all 0.767 _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 0.45318(9) 0.6800(2) -0.18711(13) 0.0652(6) Uani 1 1 d . . . O2 O 0.45034(16) 0.4397(4) -0.34619(19) 0.0890(9) Uani 1 1 d . . . N1 N 0.39835(11) 0.5148(3) 0.07333(15) 0.0532(6) Uani 1 1 d . . . C1 C 0.39060(14) 0.4180(4) -0.0092(2) 0.0674(9) Uani 1 1 d . . . H1A H 0.3732 0.3107 -0.0061 0.081 Uiso 1 1 calc R . . C2 C 0.40710(15) 0.4705(4) -0.09699(19) 0.0680(9) Uani 1 1 d . . . H2A H 0.4004 0.3985 -0.1524 0.082 Uiso 1 1 calc R . . C3 C 0.43417(13) 0.6311(4) -0.10716(19) 0.0522(8) Uani 1 1 d . . . C4 C 0.43989(14) 0.7303(3) -0.0180(2) 0.0616(8) Uani 1 1 d . . . H4A H 0.4560 0.8395 -0.0185 0.074 Uiso 1 1 calc R . . C5 C 0.42256(14) 0.6700(4) 0.06761(19) 0.0625(9) Uani 1 1 d . . . H5A H 0.4276 0.7388 0.1245 0.075 Uiso 1 1 calc R . . C6 C 0.38560(14) 0.4492(4) 0.17101(17) 0.0623(8) Uani 1 1 d . . . H6A H 0.4257 0.4577 0.2205 0.075 Uiso 1 1 calc R . . H6B H 0.3747 0.3307 0.1628 0.075 Uiso 1 1 calc R . . C7 C 0.33193(13) 0.5365(4) 0.21240(17) 0.0597(8) Uani 1 1 d . . . H7A H 0.2907 0.5224 0.1662 0.072 Uiso 1 1 calc R . . H7B H 0.3413 0.6559 0.2192 0.072 Uiso 1 1 calc R . . C8 C 0.32658(13) 0.4625(4) 0.31512(17) 0.0600(8) Uani 1 1 d . . . H8A H 0.3122 0.3465 0.3054 0.072 Uiso 1 1 calc R . . H8B H 0.3699 0.4614 0.3566 0.072 Uiso 1 1 calc R . . C9 C 0.28085(13) 0.5525(4) 0.37260(16) 0.0617(8) Uani 1 1 d . . . H9A H 0.2367 0.5476 0.3340 0.074 Uiso 1 1 calc R . . H9B H 0.2935 0.6700 0.3802 0.074 Uiso 1 1 calc R . . C10 C 0.28139(13) 0.4765(4) 0.47671(17) 0.0616(8) Uani 1 1 d . . . H10A H 0.2690 0.3589 0.4681 0.074 Uiso 1 1 calc R . . H10B H 0.3259 0.4804 0.5141 0.074 Uiso 1 1 calc R . . C11 C 0.23719(14) 0.5594(4) 0.53960(17) 0.0651(9) Uani 1 1 d . . . H11A H 0.1923 0.5510 0.5043 0.078 Uiso 1 1 calc R . . H11B H 0.2482 0.6780 0.5467 0.078 Uiso 1 1 calc R . . C12 C 0.24204(14) 0.4826(4) 0.64387(17) 0.0669(9) Uani 1 1 d . . . H12A H 0.2346 0.3623 0.6363 0.080 Uiso 1 1 calc R . . H12B H 0.2863 0.4987 0.6805 0.080 Uiso 1 1 calc R . . C13 C 0.19490(14) 0.5529(4) 0.70657(18) 0.0670(9) Uani 1 1 d . . . H13A H 0.1506 0.5369 0.6699 0.080 Uiso 1 1 calc R . . H13B H 0.2023 0.6731 0.7143 0.080 Uiso 1 1 calc R . . C14 C 0.19981(14) 0.4757(4) 0.81043(17) 0.0681(9) Uani 1 1 d . . . H14A H 0.1939 0.3550 0.8028 0.082 Uiso 1 1 calc R . . H14B H 0.2437 0.4949 0.8478 0.082 Uiso 1 1 calc R . . C15 C 0.15136(14) 0.5415(4) 0.87218(17) 0.0695(9) Uani 1 1 d . . . H15A H 0.1580 0.6617 0.8813 0.083 Uiso 1 1 calc R . . H15B H 0.1075 0.5248 0.8341 0.083 Uiso 1 1 calc R . . C16 C 0.15526(14) 0.4615(4) 0.97452(17) 0.0701(9) Uani 1 1 d . . . H16A H 0.1479 0.3415 0.9651 0.084 Uiso 1 1 calc R . . H16B H 0.1994 0.4763 1.0119 0.084 Uiso 1 1 calc R . . C17 C 0.10831(14) 0.5273(4) 1.03759(19) 0.0768(10) Uani 1 1 d . . . H17A H 0.0642 0.5165 0.9994 0.092 Uiso 1 1 calc R . . H17B H 0.1168 0.6463 1.0496 0.092 Uiso 1 1 calc R . . C18 C 0.11117(15) 0.4414(4) 1.13781(18) 0.0756(10) Uani 1 1 d . . . H18A H 0.1560 0.4461 1.1740 0.091 Uiso 1 1 calc R . . H18B H 0.1002 0.3237 1.1254 0.091 Uiso 1 1 calc R . . C19 C 0.06718(15) 0.5119(4) 1.20541(18) 0.0811(10) Uani 1 1 d . . . H19A H 0.0779 0.6297 1.2178 0.097 Uiso 1 1 calc R . . H19B H 0.0223 0.5062 1.1697 0.097 Uiso 1 1 calc R . . C20 C 0.07111(17) 0.4258(5) 1.3045(2) 0.0997(12) Uani 1 1 d . . . H20A H 0.1163 0.4291 1.3392 0.120 Uiso 1 1 calc R . . H20B H 0.0595 0.3085 1.2918 0.120 Uiso 1 1 calc R . . C21 C 0.02866(17) 0.4963(5) 1.3744(2) 0.1250(16) Uani 1 1 d . . . H21A H 0.0344 0.4308 1.4354 0.187 Uiso 1 1 calc R . . H21B H -0.0164 0.4922 1.3418 0.187 Uiso 1 1 calc R . . H21C H 0.0409 0.6109 1.3906 0.187 Uiso 1 1 calc R . . H2B H 0.453(2) 0.511(6) -0.289(3) 0.19(2) Uiso 1 1 d . . . H2C H 0.4782(17) 0.375(5) -0.335(3) 0.103(18) 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 0.0922(16) 0.0594(14) 0.0510(11) 0.0044(10) 0.0316(10) -0.0002(12) O2 0.122(2) 0.070(2) 0.0735(16) -0.0032(14) 0.0143(15) 0.0199(18) N1 0.0675(17) 0.0493(17) 0.0478(14) -0.0014(12) 0.0243(11) -0.0025(13) C1 0.088(2) 0.060(2) 0.0617(19) -0.0151(17) 0.0343(17) -0.0213(18) C2 0.098(3) 0.061(2) 0.0511(18) -0.0148(15) 0.0289(17) -0.0228(19) C3 0.058(2) 0.051(2) 0.0487(16) 0.0002(15) 0.0141(14) 0.0083(16) C4 0.090(2) 0.0420(19) 0.0592(17) -0.0031(15) 0.0313(17) -0.0073(16) C5 0.088(2) 0.056(2) 0.0479(17) -0.0107(15) 0.0239(16) -0.0010(19) C6 0.081(2) 0.062(2) 0.0505(16) 0.0067(14) 0.0298(15) 0.0031(18) C7 0.062(2) 0.072(2) 0.0491(16) 0.0024(15) 0.0209(14) 0.0040(17) C8 0.069(2) 0.066(2) 0.0493(16) 0.0050(15) 0.0232(15) -0.0003(17) C9 0.068(2) 0.075(2) 0.0460(16) 0.0028(15) 0.0203(14) 0.0052(17) C10 0.070(2) 0.067(2) 0.0512(17) 0.0012(15) 0.0228(15) 0.0033(17) C11 0.070(2) 0.082(2) 0.0478(16) 0.0015(15) 0.0245(15) 0.0054(18) C12 0.075(2) 0.080(2) 0.0509(17) 0.0036(16) 0.0244(15) 0.0044(18) C13 0.077(2) 0.081(2) 0.0494(16) -0.0038(16) 0.0267(15) -0.0003(18) C14 0.075(2) 0.085(2) 0.0487(17) -0.0008(16) 0.0232(15) -0.0027(19) C15 0.075(2) 0.089(2) 0.0484(17) -0.0052(16) 0.0234(15) -0.0041(19) C16 0.081(2) 0.088(2) 0.0450(16) -0.0051(16) 0.0215(15) -0.0075(19) C17 0.080(2) 0.106(3) 0.0497(17) -0.0007(17) 0.0259(16) -0.001(2) C18 0.082(2) 0.098(3) 0.0511(17) -0.0035(17) 0.0256(16) -0.003(2) C19 0.081(2) 0.113(3) 0.0548(18) -0.0017(18) 0.0256(17) 0.000(2) C20 0.112(3) 0.135(3) 0.060(2) 0.004(2) 0.038(2) -0.003(3) C21 0.125(3) 0.188(4) 0.076(2) -0.009(2) 0.054(2) 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 O1 C3 1.270(3) . ? O2 H2B 0.95(4) . ? O2 H2C 0.77(3) . ? N1 C1 1.335(3) . ? N1 C5 1.339(3) . ? N1 C6 1.479(3) . ? C1 C2 1.352(3) . ? C1 H1A 0.9300 . ? C2 C3 1.411(4) . ? C2 H2A 0.9300 . ? C3 C4 1.422(3) . ? C4 C5 1.352(3) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.500(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.522(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.506(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.522(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.505(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.515(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.507(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.511(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.506(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.504(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.495(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.502(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.506(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.486(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.506(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H2B O2 H2C 108(4) . . ? C1 N1 C5 118.3(2) . . ? C1 N1 C6 121.3(3) . . ? C5 N1 C6 120.2(2) . . ? N1 C1 C2 122.4(3) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C1 C2 C3 122.0(3) . . ? C1 C2 H2A 119.0 . . ? C3 C2 H2A 119.0 . . ? O1 C3 C2 123.2(3) . . ? O1 C3 C4 123.5(3) . . ? C2 C3 C4 113.3(2) . . ? C5 C4 C3 121.7(3) . . ? C5 C4 H4A 119.2 . . ? C3 C4 H4A 119.2 . . ? N1 C5 C4 122.3(2) . . ? N1 C5 H5A 118.8 . . ? C4 C5 H5A 118.8 . . ? N1 C6 C7 115.3(2) . . ? N1 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? N1 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C6 C7 C8 109.7(2) . . ? C6 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? C6 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C9 C8 C7 115.8(2) . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8B 108.3 . . ? C7 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C8 C9 C10 112.4(2) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 115.9(2) . . ? C11 C10 H10A 108.3 . . ? C9 C10 H10A 108.3 . . ? C11 C10 H10B 108.3 . . ? C9 C10 H10B 108.3 . . ? H10A C10 H10B 107.4 . . ? C10 C11 C12 113.3(2) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 115.1(2) . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12B 108.5 . . ? C11 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C12 C13 C14 115.0(2) . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13B 108.5 . . ? C14 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C15 C14 C13 115.2(2) . . ? C15 C14 H14A 108.5 . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14B 108.5 . . ? C13 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C16 C15 C14 115.1(3) . . ? C16 C15 H15A 108.5 . . ? C14 C15 H15A 108.5 . . ? C16 C15 H15B 108.5 . . ? C14 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C17 C16 C15 115.9(3) . . ? C17 C16 H16A 108.3 . . ? C15 C16 H16A 108.3 . . ? C17 C16 H16B 108.3 . . ? C15 C16 H16B 108.3 . . ? H16A C16 H16B 107.4 . . ? C16 C17 C18 115.1(3) . . ? C16 C17 H17A 108.5 . . ? C18 C17 H17A 108.5 . . ? C16 C17 H17B 108.5 . . ? C18 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C17 C18 C19 116.1(3) . . ? C17 C18 H18A 108.3 . . ? C19 C18 H18A 108.3 . . ? C17 C18 H18B 108.3 . . ? C19 C18 H18B 108.3 . . ? H18A C18 H18B 107.4 . . ? C20 C19 C18 115.3(3) . . ? C20 C19 H19A 108.5 . . ? C18 C19 H19A 108.5 . . ? C20 C19 H19B 108.5 . . ? C18 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C19 C20 C21 116.3(3) . . ? C19 C20 H20A 108.2 . . ? C21 C20 H20A 108.2 . . ? C19 C20 H20B 108.2 . . ? C21 C20 H20B 108.2 . . ? H20A C20 H20B 107.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.200 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.057