# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12jo0017s _audit_creation_date 2012-12-05 _audit_creation_method ; Olex2 1.2 (compiled Nov 5 2012 18:22:26, GUI svn.r4372) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'F, 2(C13 H13 N O3), C16 H36 N' _chemical_formula_sum 'C42 H62 F N3 O6' _chemical_formula_weight 723.95 _chemical_absolute_configuration unk _chemical_melting_point ? _chemical_oxdiff_formula 'C42 H62 N3 O6 F' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 8.4365(4) _cell_length_b 19.7096(17) _cell_length_c 11.9702(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.556(3) _cell_angle_gamma 90.00 _cell_volume 1989.7(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 15305 _cell_measurement_temperature 100(1) _cell_measurement_theta_max 29.3225 _cell_measurement_theta_min 2.4095 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.2723 _exptl_crystal_size_mid 0.2115 _exptl_crystal_size_min 0.083 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_unetI/netI 0.0361 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 21857 _diffrn_reflns_theta_full 29.42 _diffrn_reflns_theta_max 29.42 _diffrn_reflns_theta_min 2.42 _diffrn_ambient_temperature 100(1) _diffrn_detector_area_resol_mean 10.3590 _diffrn_measured_fraction_theta_full 0.9991 _diffrn_measured_fraction_theta_max 0.9905 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -57.00 16.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 10.5301 -77.0000 150.0000 73 #__ type_ start__ end____ width___ exp.time_ 2 omega -93.00 -36.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -11.9364 -19.0000 150.0000 57 #__ type_ start__ end____ width___ exp.time_ 3 omega -23.00 21.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -11.9364 -19.0000 150.0000 44 #__ type_ start__ end____ width___ exp.time_ 4 omega -1.00 25.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -11.9364 -99.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega -20.00 5.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 10.5301 -99.0000 -150.0000 25 #__ type_ start__ end____ width___ exp.time_ 6 omega -42.00 62.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -11.9364 57.0000 -60.0000 104 #__ type_ start__ end____ width___ exp.time_ 7 omega -1.00 36.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 10.6864 -57.0000 -180.0000 37 #__ type_ start__ end____ width___ exp.time_ 8 omega 47.00 90.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 10.6864 -178.0000 120.0000 43 #__ type_ start__ end____ width___ exp.time_ 9 omega -65.00 -19.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -11.9364 -38.0000 120.0000 46 #__ type_ start__ end____ width___ exp.time_ 10 omega -20.00 5.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -11.9364 -99.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 11 omega -88.00 -63.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -11.9364 -38.0000 -150.0000 25 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0539242000 _diffrn_orient_matrix_UB_12 -0.0142650000 _diffrn_orient_matrix_UB_13 -0.0399245000 _diffrn_orient_matrix_UB_21 -0.0482009000 _diffrn_orient_matrix_UB_22 -0.0115773000 _diffrn_orient_matrix_UB_23 0.0437726000 _diffrn_orient_matrix_UB_31 -0.0428807000 _diffrn_orient_matrix_UB_32 0.0308952000 _diffrn_orient_matrix_UB_33 -0.0020380000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_special_details ? _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 8558 _reflns_number_total 9275 _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.205 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.038 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(4) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 485 _refine_ls_number_reflns 9275 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0357 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.2795P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0798 _refine_ls_wR_factor_ref 0.0830 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H30 of C30, H18 of C18, H16 of C16, H11 of C11, H22 of C22, H27 of C27, H19 of C19, H26 of C26, H25 of C25, H38 of C38, H35 of C35, {H49A,H49B} of C49, {H24A,H24B} of C24, {H33A,H33B} of C33, {H45A,H45B} of C45, {H51A,H51B} of C51, H41 of C41, {H32A,H32B} of C32, {H28A,H28B} of C28, {H37A,H37B} of C37, {H31A,H31B} of C31, {H52A,H52B} of C52, {H29A,H29B} of C29, {H50A,H50B} of C50 At 1.5 times of: {H36A,H36B,H36C} of C36, {H42A,H42B,H42C} of C42, {H39A,H39B,H39C} of C39, {H48A,H48B,H48C} of C48, {H47A,H47B,H47C} of C47, {H46A,H46B,H46C} of C46, {H44A,H44B,H44C} of C44, {H43A,H43B,H43C} of C43 2.a Secondary CH2 refined with riding coordinates: C24(H24A,H24B), C28(H28A,H28B), C29(H29A,H29B), C31(H31A,H31B), C32(H32A, H32B), C33(H33A,H33B), C37(H37A,H37B), C45(H45A,H45B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B) 2.b Aromatic/amide H refined with riding coordinates: C11(H11), C16(H16), C18(H18), C19(H19), C22(H22), C25(H25), C26(H26), C27(H27), C30(H30), C35(H35), C38(H38), C41(H41) 2.c Idealised Me refined as rotating group: C36(H36A,H36B,H36C), C39(H39A,H39B,H39C), C42(H42A,H42B,H42C), C44(H44A,H44B, H44C), C43(H43A,H43B,H43C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A, H48B,H48C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 F1 F 0.22516(10) 0.48420(4) 0.09951(7) 0.02020(18) Uani 1 1 d . . . O2 O -0.12888(13) 0.28105(6) -0.49381(9) 0.0275(3) Uani 1 1 d . . . O3 O 0.29713(12) 0.53951(6) -0.07870(9) 0.0231(2) Uani 1 1 d . . . O4 O 0.34999(12) 0.61517(5) -0.42972(8) 0.0205(2) Uani 1 1 d . . . O5 O 0.57409(13) 0.77198(6) -0.32723(9) 0.0254(2) Uani 1 1 d . . . C6 C 0.07213(16) 0.44754(7) -0.51750(12) 0.0184(3) Uani 1 1 d . . . O7 O 0.43261(13) 0.79511(5) 0.30899(9) 0.0255(2) Uani 1 1 d . . . O8 O 0.21039(12) 0.59821(5) 0.18596(8) 0.0183(2) Uani 1 1 d . . . C9 C 0.11695(16) 0.45899(7) -0.40326(12) 0.0156(3) Uani 1 1 d . . . C11 C -0.01441(17) 0.38852(8) -0.54915(13) 0.0197(3) Uani 1 1 d . . . H11 H -0.0444 0.3819 -0.6237 0.024 Uiso 1 1 calc R . . C12 C 0.25717(17) 0.56054(7) -0.46014(12) 0.0175(3) Uani 1 1 d . . . N13 N 0.32072(13) 0.63892(6) 0.13326(10) 0.0169(2) Uani 1 1 d . . . C14 C 0.21175(16) 0.51723(7) -0.37441(12) 0.0158(3) Uani 1 1 d . . . C15 C 0.55273(16) 0.81356(7) -0.02559(13) 0.0170(3) Uani 1 1 d . . . C16 C 0.06655(17) 0.40998(8) -0.32432(12) 0.0191(3) Uani 1 1 d . . . H16 H 0.0899 0.4168 -0.2488 0.023 Uiso 1 1 calc R . . C17 C 0.41880(16) 0.75367(7) 0.12588(12) 0.0165(3) Uani 1 1 d . . . C18 C 0.26672(16) 0.53521(8) -0.26096(12) 0.0187(3) Uani 1 1 d . . . H18 H 0.3412 0.5699 -0.2546 0.022 Uiso 1 1 calc R . . C19 C 0.59435(17) 0.81965(8) -0.13963(13) 0.0199(3) Uani 1 1 d . . . H19 H 0.6576 0.8554 -0.1625 0.024 Uiso 1 1 calc R . . C20 C 0.54047(17) 0.77237(8) -0.21545(12) 0.0195(3) Uani 1 1 d . . . C21 C 0.45645(16) 0.75875(7) 0.01039(12) 0.0160(3) Uani 1 1 d . . . C22 C 0.44094(17) 0.71916(8) -0.18167(12) 0.0188(3) Uani 1 1 d . . . H22 H 0.4023 0.6884 -0.2346 0.023 Uiso 1 1 calc R . . N23 N 0.22283(13) 0.50819(6) -0.17026(10) 0.0165(2) Uani 1 1 d . . . C25 C 0.56614(17) 0.85798(8) 0.16321(13) 0.0206(3) Uani 1 1 d . . . H25 H 0.6002 0.8911 0.2137 0.025 Uiso 1 1 calc R . . C26 C 0.31824(16) 0.69966(7) 0.17129(12) 0.0164(3) Uani 1 1 d . . . H26 H 0.2510 0.7100 0.2292 0.020 Uiso 1 1 calc R . . C27 C -0.01523(17) 0.35315(8) -0.35665(13) 0.0222(3) Uani 1 1 d . . . H27 H -0.0457 0.3219 -0.3032 0.027 Uiso 1 1 calc R . . C30 C 0.11808(17) 0.49459(8) -0.59896(13) 0.0216(3) Uani 1 1 d . . . H30 H 0.0867 0.4877 -0.6732 0.026 Uiso 1 1 calc R . . C34 C -0.05399(17) 0.34145(8) -0.47103(13) 0.0211(3) Uani 1 1 d . . . C35 C 0.40032(16) 0.71203(7) -0.07275(12) 0.0171(3) Uani 1 1 d . . . H35 H 0.3352 0.6763 -0.0524 0.020 Uiso 1 1 calc R . . C36 C 0.4655(2) 0.84909(9) 0.38499(14) 0.0318(4) Uani 1 1 d . . . H36A H 0.4291 0.8371 0.4577 0.048 Uiso 1 1 calc R . . H36B H 0.4119 0.8894 0.3595 0.048 Uiso 1 1 calc R . . H36C H 0.5777 0.8572 0.3891 0.048 Uiso 1 1 calc R . . C38 C 0.60640(16) 0.86215(7) 0.05382(13) 0.0190(3) Uani 1 1 d . . . H38 H 0.6704 0.8977 0.0310 0.023 Uiso 1 1 calc R . . C39 C 0.70086(19) 0.81483(9) -0.36032(14) 0.0297(4) Uani 1 1 d . . . H39A H 0.7916 0.8075 -0.3117 0.044 Uiso 1 1 calc R . . H39B H 0.6684 0.8614 -0.3558 0.044 Uiso 1 1 calc R . . H39C H 0.7279 0.8044 -0.4358 0.044 Uiso 1 1 calc R . . C40 C 0.47287(17) 0.80340(7) 0.19962(12) 0.0189(3) Uani 1 1 d . . . C41 C 0.20765(17) 0.54997(8) -0.57140(12) 0.0208(3) Uani 1 1 d . . . H41 H 0.2358 0.5807 -0.6264 0.025 Uiso 1 1 calc R . . C42 C 0.41569(19) 0.65531(8) -0.51735(13) 0.0246(3) Uani 1 1 d . . . H42A H 0.4844 0.6893 -0.4853 0.037 Uiso 1 1 calc R . . H42B H 0.3315 0.6768 -0.5597 0.037 Uiso 1 1 calc R . . H42C H 0.4751 0.6266 -0.5657 0.037 Uiso 1 1 calc R . . C44 C -0.16089(19) 0.26622(9) -0.60906(14) 0.0285(4) Uani 1 1 d . . . H44A H -0.2036 0.2212 -0.6160 0.043 Uiso 1 1 calc R . . H44B H -0.0644 0.2691 -0.6495 0.043 Uiso 1 1 calc R . . H44C H -0.2362 0.2983 -0.6392 0.043 Uiso 1 1 calc R . . N10 N 0.23073(13) 0.02978(6) -0.00258(10) 0.0164(2) Uani 1 1 d . . . C24 C 0.30559(16) 0.04738(8) 0.11064(12) 0.0199(3) Uani 1 1 d . . . H24A H 0.3626 0.0079 0.1387 0.024 Uiso 1 1 calc R . . H24B H 0.3827 0.0832 0.1003 0.024 Uiso 1 1 calc R . . C28 C 0.11341(15) -0.02852(7) 0.00583(13) 0.0174(3) Uani 1 1 d . . . H28A H 0.0281 -0.0143 0.0533 0.021 Uiso 1 1 calc R . . H28B H 0.0676 -0.0371 -0.0680 0.021 Uiso 1 1 calc R . . C29 C 0.2784(2) 0.08234(10) 0.30975(14) 0.0325(4) Uani 1 1 d . . . H29A H 0.3245 0.0399 0.3356 0.039 Uiso 1 1 calc R . . H29B H 0.3646 0.1139 0.2980 0.039 Uiso 1 1 calc R . . C31 C 0.18130(16) -0.09442(8) 0.05136(13) 0.0204(3) Uani 1 1 d . . . H31A H 0.2080 -0.0892 0.1302 0.024 Uiso 1 1 calc R . . H31B H 0.2776 -0.1055 0.0128 0.024 Uiso 1 1 calc R . . C32 C 0.45101(17) -0.00722(8) -0.27543(12) 0.0213(3) Uani 1 1 d . . . H32A H 0.4768 0.0405 -0.2823 0.026 Uiso 1 1 calc R . . H32B H 0.5444 -0.0305 -0.2458 0.026 Uiso 1 1 calc R . . C33 C 0.13653(16) 0.08943(7) -0.05023(13) 0.0191(3) Uani 1 1 d . . . H33A H 0.0464 0.0972 -0.0033 0.023 Uiso 1 1 calc R . . H33B H 0.0954 0.0770 -0.1239 0.023 Uiso 1 1 calc R . . C37 C 0.36629(16) 0.01118(7) -0.07883(12) 0.0171(3) Uani 1 1 d . . . H37A H 0.4319 0.0510 -0.0886 0.020 Uiso 1 1 calc R . . H37B H 0.4314 -0.0230 -0.0417 0.020 Uiso 1 1 calc R . . C43 C 0.1737(2) 0.11032(10) 0.39993(15) 0.0355(4) Uani 1 1 d . . . H43A H 0.2349 0.1152 0.4683 0.053 Uiso 1 1 calc R . . H43B H 0.0873 0.0797 0.4115 0.053 Uiso 1 1 calc R . . H43C H 0.1329 0.1538 0.3771 0.053 Uiso 1 1 calc R . . C45 C 0.06076(17) -0.15196(8) 0.03536(13) 0.0224(3) Uani 1 1 d . . . H45A H 0.0975 -0.1911 0.0777 0.027 Uiso 1 1 calc R . . H45B H -0.0395 -0.1378 0.0656 0.027 Uiso 1 1 calc R . . C46 C 0.0334(2) -0.17282(9) -0.08609(15) 0.0296(4) Uani 1 1 d . . . H46A H -0.0418 -0.2094 -0.0901 0.044 Uiso 1 1 calc R . . H46B H 0.1318 -0.1874 -0.1166 0.044 Uiso 1 1 calc R . . H46C H -0.0072 -0.1349 -0.1282 0.044 Uiso 1 1 calc R . . C47 C 0.4074(2) -0.03568(9) -0.39029(14) 0.0303(4) Uani 1 1 d . . . H47A H 0.3842 -0.0832 -0.3840 0.045 Uiso 1 1 calc R . . H47B H 0.4946 -0.0295 -0.4392 0.045 Uiso 1 1 calc R . . H47C H 0.3158 -0.0123 -0.4202 0.045 Uiso 1 1 calc R . . C48 C 0.1785(3) 0.17875(10) -0.26761(16) 0.0406(4) Uani 1 1 d . . . H48A H 0.2904 0.1783 -0.2801 0.061 Uiso 1 1 calc R . . H48B H 0.1272 0.2095 -0.3192 0.061 Uiso 1 1 calc R . . H48C H 0.1363 0.1339 -0.2787 0.061 Uiso 1 1 calc R . . C49 C 0.19092(18) 0.07013(9) 0.19878(14) 0.0256(3) Uani 1 1 d . . . H49A H 0.1104 0.0356 0.2082 0.031 Uiso 1 1 calc R . . H49B H 0.1385 0.1116 0.1745 0.031 Uiso 1 1 calc R . . C50 C 0.31573(16) -0.01544(8) -0.19404(12) 0.0201(3) Uani 1 1 d . . . H50A H 0.2234 0.0094 -0.2216 0.024 Uiso 1 1 calc R . . H50B H 0.2871 -0.0630 -0.1887 0.024 Uiso 1 1 calc R . . C51 C 0.22792(18) 0.15577(8) -0.06020(14) 0.0241(3) Uani 1 1 d . . . H51A H 0.3363 0.1462 -0.0803 0.029 Uiso 1 1 calc R . . H51B H 0.2306 0.1789 0.0113 0.029 Uiso 1 1 calc R . . C52 C 0.14947(19) 0.20154(8) -0.14899(15) 0.0275(4) Uani 1 1 d . . . H52A H 0.0361 0.2026 -0.1375 0.033 Uiso 1 1 calc R . . H52B H 0.1894 0.2474 -0.1393 0.033 Uiso 1 1 calc R . . H8 H 0.221(2) 0.5556(11) 0.1535(18) 0.043(6) Uiso 1 1 d . . . H3 H 0.266(3) 0.5160(11) -0.0132(19) 0.046(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 F1 0.0240(4) 0.0186(4) 0.0179(4) 0.0006(3) -0.0014(3) -0.0031(3) O2 0.0308(6) 0.0270(6) 0.0248(6) -0.0062(5) 0.0001(4) -0.0108(5) O3 0.0299(6) 0.0259(5) 0.0133(5) -0.0004(5) -0.0023(4) -0.0105(5) O4 0.0263(6) 0.0183(5) 0.0169(5) 0.0029(4) 0.0010(4) -0.0034(4) O5 0.0245(6) 0.0326(6) 0.0193(6) 0.0041(5) 0.0039(4) -0.0062(5) C6 0.0166(7) 0.0216(7) 0.0170(7) -0.0009(6) 0.0000(5) 0.0044(6) O7 0.0331(6) 0.0240(6) 0.0193(6) -0.0066(5) 0.0021(4) -0.0068(5) O8 0.0223(5) 0.0170(5) 0.0158(5) 0.0018(4) 0.0031(4) -0.0035(4) C9 0.0139(6) 0.0161(7) 0.0168(7) -0.0017(5) -0.0009(5) 0.0033(5) C11 0.0168(7) 0.0248(8) 0.0172(7) -0.0062(6) -0.0022(5) 0.0015(6) C12 0.0167(6) 0.0158(7) 0.0199(8) -0.0009(6) 0.0017(5) 0.0031(5) N13 0.0176(6) 0.0181(6) 0.0149(6) 0.0025(5) 0.0001(4) -0.0026(5) C14 0.0145(6) 0.0172(7) 0.0157(7) 0.0002(5) 0.0001(5) 0.0032(5) C15 0.0126(6) 0.0140(6) 0.0242(8) 0.0028(6) -0.0022(5) 0.0025(5) C16 0.0200(7) 0.0215(7) 0.0157(7) -0.0012(6) -0.0004(5) 0.0004(6) C17 0.0150(7) 0.0137(6) 0.0208(7) 0.0008(5) 0.0004(5) 0.0020(5) C18 0.0207(7) 0.0170(6) 0.0182(7) 0.0007(6) -0.0011(5) -0.0042(6) C19 0.0153(7) 0.0188(7) 0.0256(8) 0.0063(6) 0.0008(6) -0.0004(6) C20 0.0170(7) 0.0226(7) 0.0189(7) 0.0043(6) 0.0009(5) 0.0015(6) C21 0.0150(6) 0.0143(6) 0.0186(7) 0.0007(5) -0.0003(5) 0.0032(5) C22 0.0198(7) 0.0187(7) 0.0179(7) -0.0005(6) -0.0014(5) 0.0007(6) N23 0.0164(5) 0.0191(6) 0.0140(6) -0.0013(5) -0.0025(4) -0.0003(5) C25 0.0185(7) 0.0161(7) 0.0269(8) -0.0038(6) -0.0042(6) 0.0007(6) C26 0.0160(6) 0.0187(7) 0.0144(7) 0.0011(5) -0.0003(5) 0.0010(5) C27 0.0234(7) 0.0216(8) 0.0218(8) 0.0017(6) 0.0018(6) -0.0029(6) C30 0.0235(7) 0.0260(8) 0.0151(7) -0.0009(6) -0.0033(5) 0.0024(6) C34 0.0165(7) 0.0219(7) 0.0247(8) -0.0053(6) -0.0002(6) -0.0014(6) C35 0.0169(7) 0.0143(7) 0.0200(7) 0.0020(6) -0.0005(5) 0.0003(5) C36 0.0380(9) 0.0329(9) 0.0246(9) -0.0107(7) 0.0014(7) -0.0094(8) C38 0.0134(6) 0.0134(6) 0.0302(8) 0.0017(6) -0.0021(6) -0.0006(5) C39 0.0223(8) 0.0404(10) 0.0265(9) 0.0081(7) 0.0047(6) -0.0065(7) C40 0.0177(7) 0.0186(7) 0.0204(8) -0.0009(6) -0.0008(5) 0.0015(6) C41 0.0241(7) 0.0221(8) 0.0162(7) 0.0029(6) 0.0021(5) 0.0025(6) C42 0.0324(8) 0.0220(8) 0.0198(8) 0.0022(6) 0.0064(6) -0.0038(6) C44 0.0274(8) 0.0300(9) 0.0281(9) -0.0092(7) 0.0004(6) -0.0096(7) N10 0.0131(5) 0.0174(6) 0.0185(6) -0.0013(5) -0.0010(4) -0.0005(5) C24 0.0158(6) 0.0238(8) 0.0200(7) -0.0031(6) -0.0021(5) -0.0016(6) C28 0.0114(6) 0.0177(7) 0.0230(8) -0.0022(6) -0.0002(5) -0.0026(5) C29 0.0257(8) 0.0472(11) 0.0247(9) -0.0091(8) 0.0015(7) -0.0057(8) C31 0.0152(7) 0.0220(7) 0.0239(8) 0.0026(6) -0.0012(5) -0.0009(6) C32 0.0210(7) 0.0226(7) 0.0203(8) -0.0017(6) 0.0004(5) -0.0043(6) C33 0.0151(6) 0.0165(7) 0.0257(8) -0.0010(6) -0.0010(5) 0.0013(5) C37 0.0126(6) 0.0185(7) 0.0201(7) -0.0011(6) 0.0012(5) -0.0004(5) C43 0.0335(9) 0.0459(11) 0.0275(9) -0.0143(8) 0.0068(7) -0.0110(8) C45 0.0190(7) 0.0198(7) 0.0285(8) 0.0032(6) 0.0006(6) -0.0018(6) C46 0.0298(8) 0.0231(8) 0.0358(10) -0.0039(7) -0.0036(7) -0.0041(7) C47 0.0275(8) 0.0398(10) 0.0237(9) -0.0089(7) 0.0044(6) -0.0082(7) C48 0.0585(12) 0.0274(9) 0.0358(11) 0.0067(8) 0.0014(9) 0.0025(9) C49 0.0196(7) 0.0339(9) 0.0234(8) -0.0073(7) 0.0020(6) -0.0028(6) C50 0.0175(7) 0.0208(7) 0.0220(8) -0.0031(6) -0.0005(5) -0.0016(6) C51 0.0203(7) 0.0188(7) 0.0330(9) -0.0029(7) -0.0023(6) -0.0019(6) C52 0.0241(8) 0.0156(7) 0.0428(10) 0.0017(7) 0.0001(7) -0.0002(6) _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 O2 C34 1.3717(18) . ? O2 C44 1.4288(19) . ? O3 N23 1.3921(15) . ? O4 C12 1.3747(17) . ? O4 C42 1.4369(17) . ? O5 C20 1.3753(18) . ? O5 C39 1.4271(18) . ? C6 C9 1.4268(19) . ? C6 C11 1.419(2) . ? C6 C30 1.408(2) . ? O7 C36 1.4222(19) . ? O7 C40 1.3712(18) . ? O8 N13 1.3928(15) . ? C9 C14 1.4359(19) . ? C9 C16 1.424(2) . ? C11 C34 1.365(2) . ? C12 C14 1.3964(19) . ? C12 C41 1.400(2) . ? N13 C26 1.2812(19) . ? C14 C18 1.4665(19) . ? C15 C19 1.424(2) . ? C15 C21 1.4251(19) . ? C15 C38 1.415(2) . ? C16 C27 1.366(2) . ? C17 C21 1.430(2) . ? C17 C26 1.4743(19) . ? C17 C40 1.388(2) . ? C18 N23 1.2732(18) . ? C19 C20 1.370(2) . ? C20 C22 1.410(2) . ? C21 C35 1.427(2) . ? C22 C35 1.364(2) . ? C25 C38 1.364(2) . ? C25 C40 1.409(2) . ? C27 C34 1.418(2) . ? C30 C41 1.363(2) . ? N10 C24 1.5197(18) . ? N10 C28 1.5217(17) . ? N10 C33 1.5213(18) . ? N10 C37 1.5271(17) . ? C24 C49 1.518(2) . ? C28 C31 1.515(2) . ? C29 C43 1.517(2) . ? C29 C49 1.521(2) . ? C31 C45 1.532(2) . ? C32 C47 1.521(2) . ? C32 C50 1.529(2) . ? C33 C51 1.524(2) . ? C37 C50 1.526(2) . ? C45 C46 1.522(2) . ? C48 C52 1.516(3) . ? C51 C52 1.531(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 C34 O2 C44 116.33(12) . . ? C12 O4 C42 117.78(11) . . ? C20 O5 C39 116.28(12) . . ? C11 C6 C9 120.43(13) . . ? C30 C6 C9 119.27(13) . . ? C30 C6 C11 120.28(14) . . ? C40 O7 C36 118.20(12) . . ? C6 C9 C14 119.22(13) . . ? C16 C9 C6 116.91(13) . . ? C16 C9 C14 123.85(13) . . ? C34 C11 C6 120.51(14) . . ? O4 C12 C14 116.74(12) . . ? O4 C12 C41 121.43(13) . . ? C14 C12 C41 121.82(13) . . ? C26 N13 O8 111.09(11) . . ? C9 C14 C18 125.16(13) . . ? C12 C14 C9 118.31(12) . . ? C12 C14 C18 116.53(12) . . ? C19 C15 C21 120.74(13) . . ? C38 C15 C19 120.28(13) . . ? C38 C15 C21 118.98(13) . . ? C27 C16 C9 121.72(13) . . ? C21 C17 C26 123.51(13) . . ? C40 C17 C21 119.17(13) . . ? C40 C17 C26 117.25(13) . . ? N23 C18 C14 126.63(13) . . ? C20 C19 C15 119.46(13) . . ? O5 C20 C22 114.53(13) . . ? C19 C20 O5 125.09(13) . . ? C19 C20 C22 120.38(14) . . ? C15 C21 C17 119.24(13) . . ? C15 C21 C35 117.34(13) . . ? C35 C21 C17 123.40(13) . . ? C35 C22 C20 121.18(14) . . ? C18 N23 O3 110.54(11) . . ? C38 C25 C40 119.91(14) . . ? N13 C26 C17 121.91(13) . . ? C16 C27 C34 120.55(14) . . ? C41 C30 C6 121.41(14) . . ? O2 C34 C27 115.21(13) . . ? C11 C34 O2 125.00(14) . . ? C11 C34 C27 119.79(13) . . ? C22 C35 C21 120.85(13) . . ? C25 C38 C15 121.37(13) . . ? O7 C40 C17 115.94(13) . . ? O7 C40 C25 122.77(13) . . ? C17 C40 C25 121.28(14) . . ? C30 C41 C12 119.89(14) . . ? C24 N10 C28 111.63(11) . . ? C24 N10 C33 110.99(11) . . ? C24 N10 C37 106.74(10) . . ? C28 N10 C37 110.93(11) . . ? C33 N10 C28 105.92(10) . . ? C33 N10 C37 110.71(11) . . ? C49 C24 N10 115.46(12) . . ? C31 C28 N10 115.53(10) . . ? C43 C29 C49 113.62(14) . . ? C28 C31 C45 110.27(11) . . ? C47 C32 C50 111.75(12) . . ? N10 C33 C51 115.60(11) . . ? C50 C37 N10 115.30(11) . . ? C46 C45 C31 113.73(13) . . ? C24 C49 C29 110.50(13) . . ? C37 C50 C32 110.14(11) . . ? C33 C51 C52 110.47(12) . . ? C48 C52 C51 113.46(14) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 0 -1 0.0148 -0.0006 -0.0016 -0.9995 0.0400 -0.0437 0.0020 0 0 1 0.0682 0.0006 0.0016 0.9995 -0.0400 0.0437 -0.0020 -1 0 0 0.1169 -0.9988 0.0180 -0.0004 0.0536 0.0479 0.0434 1 0 0 0.0946 0.9988 -0.0180 0.0004 -0.0536 -0.0479 -0.0434 0 1 0 0.0996 0.0023 0.9992 -0.0011 -0.0143 -0.0117 0.0308 0 -1 0 0.1723 -0.0023 -0.9992 0.0011 0.0143 0.0117 -0.0308 _database_code_depnum_ccdc_archive 'CCDC 932310' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12jo0011a_01 _audit_creation_date 2012-09-06 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H36 N, 2(C11 H9 N O), F' _chemical_formula_sum 'C38 H54 F N3 O2' _chemical_formula_weight 603.84 _chemical_melting_point ? 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 17.2054(17) _cell_length_b 8.3014(9) _cell_length_c 23.741(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.687(4) _cell_angle_gamma 90.00 _cell_volume 3367.8(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1238 _cell_measurement_temperature 100 _cell_measurement_theta_max 21.96 _cell_measurement_theta_min 2.73 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8882 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0724 before and 0.0576 after correction. The Ratio of minimum to maximum transmission is 0.8882. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1312 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_unetI/netI 0.1101 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 12793 _diffrn_reflns_theta_full 22.02 _diffrn_reflns_theta_max 22.02 _diffrn_reflns_theta_min 1.73 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\f scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 2355 _reflns_number_total 4105 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.210 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.054 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 406 _refine_ls_number_reflns 4105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1256 _refine_ls_R_factor_gt 0.0568 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1167 _refine_ls_wR_factor_ref 0.1418 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 F1 F 0.24977(13) 0.0732(3) 0.49337(9) 0.0305(6) Uani 1 1 d . . . O2 O 0.11407(16) 0.0596(4) 0.51507(11) 0.0346(8) Uani 1 1 d . . . H2 H 0.1611 0.0623 0.5087 0.052 Uiso 1 1 calc R . . C5 C -0.0804(2) 0.2395(5) 0.70076(16) 0.0219(10) Uani 1 1 d . . . C6 C -0.0613(2) 0.1661(4) 0.64950(17) 0.0224(11) Uani 1 1 d . . . C12 C 0.0157(2) 0.1863(4) 0.63332(16) 0.0232(11) Uani 1 1 d . . . C17 C -0.1571(2) 0.2206(5) 0.71620(16) 0.0249(11) Uani 1 1 d . . . H17 H -0.1702 0.2702 0.7499 0.030 Uiso 1 1 calc R . . C18 C -0.1210(2) 0.0755(4) 0.61678(16) 0.0222(10) Uani 1 1 d . . . H18 H -0.1098 0.0245 0.5828 0.027 Uiso 1 1 calc R . . C21 C -0.1940(2) 0.0608(5) 0.63346(17) 0.0245(11) Uani 1 1 d . . . H21 H -0.2330 0.0009 0.6107 0.029 Uiso 1 1 calc R . . C26 C -0.0231(3) 0.3324(5) 0.73399(17) 0.0291(11) Uani 1 1 d . . . H26 H -0.0362 0.3850 0.7671 0.035 Uiso 1 1 calc R . . N29 N 0.1070(2) 0.1315(4) 0.56728(14) 0.0263(9) Uani 1 1 d . . . C37 C -0.2124(2) 0.1334(5) 0.68402(17) 0.0275(11) Uani 1 1 d . . . H37 H -0.2631 0.1214 0.6955 0.033 Uiso 1 1 calc R . . C39 C 0.0697(2) 0.2740(5) 0.66870(17) 0.0284(11) Uani 1 1 d . . . H39 H 0.1214 0.2852 0.6588 0.034 Uiso 1 1 calc R . . C42 C 0.0508(3) 0.3470(5) 0.71883(18) 0.0305(12) Uani 1 1 d . . . H42 H 0.0894 0.4064 0.7421 0.037 Uiso 1 1 calc R . . C43 C 0.0376(3) 0.1194(5) 0.58038(17) 0.0266(11) Uani 1 1 d . . . H43 H -0.0009 0.0658 0.5552 0.032 Uiso 1 1 calc R . . O3 O 0.38819(19) 0.1234(3) 0.48175(12) 0.0317(8) Uani 1 1 d . . . N4 N 0.3969(2) 0.1483(4) 0.42475(14) 0.0255(9) Uani 1 1 d . . . C8 C 0.4928(2) 0.1667(4) 0.35978(16) 0.0222(11) Uani 1 1 d . . . C9 C 0.5690(2) 0.1171(4) 0.34731(17) 0.0205(10) Uani 1 1 d . . . C10 C 0.5379(2) 0.2318(5) 0.25167(17) 0.0258(11) Uani 1 1 d . . . H10 H 0.5525 0.2547 0.2151 0.031 Uiso 1 1 calc R . . C11 C 0.6240(2) 0.0366(4) 0.38675(17) 0.0255(11) Uani 1 1 d . . . H11 H 0.6103 0.0121 0.4234 0.031 Uiso 1 1 calc R . . C13 C 0.6961(2) -0.0066(5) 0.37340(17) 0.0270(11) Uani 1 1 d . . . H13 H 0.7315 -0.0611 0.4006 0.032 Uiso 1 1 calc R . . C14 C 0.7184(2) 0.0291(5) 0.31947(17) 0.0272(11) Uani 1 1 d . . . H14 H 0.7687 -0.0010 0.3105 0.033 Uiso 1 1 calc R . . C16 C 0.5921(2) 0.1544(4) 0.29279(17) 0.0236(11) Uani 1 1 d . . . C19 C 0.4650(2) 0.2736(5) 0.26415(18) 0.0283(11) Uani 1 1 d . . . H19 H 0.4291 0.3237 0.2361 0.034 Uiso 1 1 calc R . . C22 C 0.6677(2) 0.1065(5) 0.28037(17) 0.0261(11) Uani 1 1 d . . . H22 H 0.6830 0.1291 0.2440 0.031 Uiso 1 1 calc R . . C24 C 0.4431(2) 0.2430(5) 0.31782(17) 0.0259(11) Uani 1 1 d . . . H24 H 0.3926 0.2753 0.3259 0.031 Uiso 1 1 calc R . . C32 C 0.4688(2) 0.1394(5) 0.41648(17) 0.0260(11) Uani 1 1 d . . . H32 H 0.5072 0.1148 0.4473 0.031 Uiso 1 1 calc R . . N7 N 0.23905(18) 0.5491(3) 0.50299(13) 0.0199(8) Uani 1 1 d . . . C15 C 0.3279(2) 0.5512(4) 0.59840(15) 0.0245(11) Uani 1 1 d . . . H15A H 0.2960 0.6439 0.6083 0.029 Uiso 1 1 calc R . . H15B H 0.3757 0.5936 0.5841 0.029 Uiso 1 1 calc R . . C20 C 0.2816(2) 0.4519(4) 0.55221(15) 0.0229(10) Uani 1 1 d . . . H20A H 0.2423 0.3873 0.5697 0.028 Uiso 1 1 calc R . . H20B H 0.3178 0.3756 0.5366 0.028 Uiso 1 1 calc R . . C23 C 0.1432(2) 0.3729(4) 0.35966(16) 0.0256(11) Uani 1 1 d . . . H23A H 0.0997 0.4111 0.3319 0.031 Uiso 1 1 calc R . . H23B H 0.1259 0.2722 0.3768 0.031 Uiso 1 1 calc R . . C25 C 0.1735(2) 0.6493(4) 0.52293(16) 0.0208(10) Uani 1 1 d . . . H25A H 0.1962 0.7206 0.5540 0.025 Uiso 1 1 calc R . . H25B H 0.1515 0.7192 0.4912 0.025 Uiso 1 1 calc R . . C27 C 0.1070(2) 0.5547(5) 0.54370(16) 0.0264(11) Uani 1 1 d . . . H27A H 0.1285 0.4770 0.5731 0.032 Uiso 1 1 calc R . . H27B H 0.0794 0.4929 0.5118 0.032 Uiso 1 1 calc R . . C28 C 0.1601(2) 0.4995(4) 0.40604(15) 0.0221(11) Uani 1 1 d . . . H28A H 0.1895 0.5901 0.3914 0.027 Uiso 1 1 calc R . . H28B H 0.1102 0.5423 0.4167 0.027 Uiso 1 1 calc R . . C30 C 0.0803(2) 0.7380(5) 0.62516(16) 0.0327(12) Uani 1 1 d . . . H30A H 0.1267 0.8035 0.6209 0.049 Uiso 1 1 calc R . . H30B H 0.0944 0.6512 0.6524 0.049 Uiso 1 1 calc R . . H30C H 0.0399 0.8059 0.6389 0.049 Uiso 1 1 calc R . . C31 C 0.2944(2) 0.6682(4) 0.47972(16) 0.0218(11) Uani 1 1 d . . . H31A H 0.2644 0.7310 0.4490 0.026 Uiso 1 1 calc R . . H31B H 0.3132 0.7446 0.5103 0.026 Uiso 1 1 calc R . . C33 C 0.3508(2) 0.4496(5) 0.65120(16) 0.0252(11) Uani 1 1 d . . . H33A H 0.3683 0.3424 0.6395 0.030 Uiso 1 1 calc R . . H33B H 0.3954 0.5016 0.6743 0.030 Uiso 1 1 calc R . . C34 C 0.2844(2) 0.4276(5) 0.68737(17) 0.0393(13) Uani 1 1 d . . . H34A H 0.2421 0.3658 0.6661 0.059 Uiso 1 1 calc R . . H34B H 0.2645 0.5333 0.6972 0.059 Uiso 1 1 calc R . . H34C H 0.3036 0.3694 0.7221 0.059 Uiso 1 1 calc R . . C35 C 0.2074(2) 0.4285(4) 0.45781(15) 0.0219(10) Uani 1 1 d . . . H35A H 0.2521 0.3686 0.4453 0.026 Uiso 1 1 calc R . . H35B H 0.1742 0.3498 0.4753 0.026 Uiso 1 1 calc R . . C36 C 0.4089(2) 0.7278(5) 0.42925(16) 0.0264(11) Uani 1 1 d . . . H36A H 0.3749 0.7715 0.3963 0.032 Uiso 1 1 calc R . . H36B H 0.4203 0.8164 0.4569 0.032 Uiso 1 1 calc R . . C38 C 0.0494(2) 0.6663(5) 0.56828(17) 0.0348(12) Uani 1 1 d . . . H38A H 0.0354 0.7549 0.5411 0.042 Uiso 1 1 calc R . . H38B H 0.0009 0.6053 0.5726 0.042 Uiso 1 1 calc R . . C40 C 0.2141(2) 0.3365(5) 0.32865(17) 0.0322(12) Uani 1 1 d . . . H40A H 0.1993 0.2593 0.2981 0.048 Uiso 1 1 calc R . . H40B H 0.2559 0.2906 0.3554 0.048 Uiso 1 1 calc R . . H40C H 0.2325 0.4363 0.3126 0.048 Uiso 1 1 calc R . . C41 C 0.3648(2) 0.5950(5) 0.45663(17) 0.0262(11) Uani 1 1 d . . . H41A H 0.3477 0.5112 0.4282 0.031 Uiso 1 1 calc R . . H41B H 0.3996 0.5440 0.4878 0.031 Uiso 1 1 calc R . . C44 C 0.4851(2) 0.6697(5) 0.40971(17) 0.0335(12) Uani 1 1 d . . . H44A H 0.4746 0.5780 0.3840 0.050 Uiso 1 1 calc R . . H44B H 0.5211 0.6365 0.4427 0.050 Uiso 1 1 calc R . . H44C H 0.5088 0.7573 0.3899 0.050 Uiso 1 1 calc R . . H3 H 0.334(3) 0.114(6) 0.484(2) 0.074(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 F1 0.0262(14) 0.0317(14) 0.0355(14) 0.0037(12) 0.0109(11) 0.0011(12) O2 0.0275(19) 0.0442(19) 0.0337(19) -0.0103(16) 0.0103(15) -0.0012(17) C5 0.031(3) 0.015(2) 0.019(2) 0.008(2) 0.000(2) 0.002(2) C6 0.028(3) 0.013(2) 0.026(3) 0.005(2) 0.003(2) 0.003(2) C12 0.027(3) 0.018(2) 0.023(3) 0.001(2) -0.001(2) -0.003(2) C17 0.029(3) 0.027(3) 0.020(3) 0.007(2) 0.009(2) 0.011(2) C18 0.027(3) 0.015(2) 0.026(3) 0.005(2) 0.006(2) 0.005(2) C21 0.021(3) 0.020(2) 0.032(3) 0.007(2) 0.001(2) -0.001(2) C26 0.046(3) 0.021(3) 0.020(3) 0.003(2) 0.005(2) 0.006(2) N29 0.032(3) 0.024(2) 0.024(2) -0.0024(17) 0.0090(18) 0.0029(18) C37 0.027(3) 0.031(3) 0.025(3) 0.009(2) 0.005(2) -0.001(2) C39 0.023(3) 0.029(3) 0.034(3) 0.007(2) 0.005(2) -0.002(2) C42 0.035(3) 0.028(3) 0.028(3) 0.000(2) 0.000(2) -0.005(2) C43 0.027(3) 0.025(3) 0.028(3) -0.003(2) 0.003(2) -0.003(2) O3 0.029(2) 0.045(2) 0.0224(19) 0.0003(15) 0.0094(15) -0.0019(16) N4 0.030(3) 0.025(2) 0.022(2) 0.0011(17) 0.0047(18) 0.0009(18) C8 0.030(3) 0.019(2) 0.018(3) -0.003(2) 0.007(2) -0.006(2) C9 0.023(3) 0.012(2) 0.027(3) -0.001(2) 0.003(2) -0.0055(19) C10 0.034(3) 0.025(3) 0.019(2) 0.001(2) 0.006(2) -0.008(2) C11 0.032(3) 0.021(3) 0.023(3) -0.002(2) 0.002(2) -0.005(2) C13 0.030(3) 0.018(2) 0.032(3) 0.001(2) -0.001(2) 0.000(2) C14 0.022(3) 0.025(3) 0.036(3) -0.003(2) 0.007(2) -0.001(2) C16 0.030(3) 0.014(2) 0.027(3) -0.003(2) 0.004(2) -0.005(2) C19 0.027(3) 0.024(3) 0.032(3) -0.002(2) 0.000(2) -0.002(2) C22 0.029(3) 0.027(3) 0.024(3) -0.004(2) 0.009(2) -0.003(2) C24 0.023(3) 0.029(3) 0.026(3) 0.001(2) 0.005(2) -0.001(2) C32 0.018(3) 0.028(3) 0.031(3) -0.002(2) -0.002(2) 0.000(2) N7 0.021(2) 0.0139(19) 0.0251(19) 0.0010(17) 0.0042(16) -0.0009(16) C15 0.025(3) 0.018(2) 0.031(3) -0.004(2) 0.003(2) 0.000(2) C20 0.026(3) 0.018(2) 0.025(2) 0.004(2) 0.003(2) 0.000(2) C23 0.025(3) 0.019(2) 0.032(3) 0.002(2) 0.001(2) 0.001(2) C25 0.018(2) 0.022(2) 0.023(2) -0.003(2) 0.007(2) 0.003(2) C27 0.028(3) 0.028(3) 0.023(2) -0.003(2) 0.002(2) -0.005(2) C28 0.026(3) 0.016(2) 0.024(2) 0.003(2) 0.002(2) 0.000(2) C30 0.038(3) 0.034(3) 0.027(3) -0.002(2) 0.008(2) 0.003(2) C31 0.028(3) 0.015(2) 0.022(2) 0.001(2) 0.003(2) -0.005(2) C33 0.026(3) 0.020(2) 0.030(3) -0.002(2) 0.003(2) 0.002(2) C34 0.033(3) 0.056(3) 0.029(3) 0.005(2) 0.006(2) 0.009(3) C35 0.025(3) 0.014(2) 0.027(2) -0.001(2) 0.002(2) -0.002(2) C36 0.022(3) 0.031(3) 0.027(3) 0.002(2) 0.005(2) -0.002(2) C38 0.030(3) 0.044(3) 0.032(3) -0.005(2) 0.007(2) -0.006(2) C40 0.037(3) 0.026(3) 0.035(3) 0.001(2) 0.011(2) -0.003(2) C41 0.029(3) 0.019(2) 0.031(3) 0.002(2) 0.008(2) -0.001(2) C44 0.032(3) 0.036(3) 0.032(3) -0.001(2) 0.005(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 N29 1.394(4) . ? C5 C6 1.433(5) . ? C5 C17 1.420(5) . ? C5 C26 1.417(5) . ? C6 C12 1.432(5) . ? C6 C18 1.428(5) . ? C12 C39 1.385(5) . ? C12 C43 1.463(5) . ? C17 C37 1.357(5) . ? C18 C21 1.366(5) . ? C21 C37 1.411(5) . ? C26 C42 1.367(6) . ? N29 C43 1.273(5) . ? C39 C42 1.407(5) . ? O3 N4 1.394(4) . ? N4 C32 1.276(5) . ? C8 C9 1.438(5) . ? C8 C24 1.388(5) . ? C8 C32 1.471(5) . ? C9 C11 1.419(5) . ? C9 C16 1.431(5) . ? C10 C16 1.423(5) . ? C10 C19 1.366(5) . ? C11 C13 1.362(5) . ? C13 C14 1.410(5) . ? C14 C22 1.359(5) . ? C16 C22 1.423(5) . ? C19 C24 1.394(5) . ? N7 C20 1.534(4) . ? N7 C25 1.521(4) . ? N7 C31 1.520(5) . ? N7 C35 1.521(4) . ? C15 C20 1.521(5) . ? C15 C33 1.524(5) . ? C23 C28 1.526(5) . ? C23 C40 1.527(5) . ? C25 C27 1.516(5) . ? C27 C38 1.522(5) . ? C28 C35 1.512(5) . ? C30 C38 1.515(5) . ? C31 C41 1.515(5) . ? C33 C34 1.518(5) . ? C36 C41 1.525(5) . ? C36 C44 1.520(5) . ? 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 C17 C5 C6 119.0(4) . . ? C26 C5 C6 119.4(4) . . ? C26 C5 C17 121.6(4) . . ? C12 C6 C5 119.3(4) . . ? C18 C6 C5 117.7(4) . . ? C18 C6 C12 123.1(4) . . ? C6 C12 C43 121.6(4) . . ? C39 C12 C6 118.4(4) . . ? C39 C12 C43 120.0(4) . . ? C37 C17 C5 121.7(4) . . ? C21 C18 C6 121.1(4) . . ? C18 C21 C37 120.8(4) . . ? C42 C26 C5 120.7(4) . . ? C43 N29 O2 111.4(3) . . ? C17 C37 C21 119.7(4) . . ? C12 C39 C42 122.3(4) . . ? C26 C42 C39 119.9(4) . . ? N29 C43 C12 121.5(4) . . ? C32 N4 O3 110.9(3) . . ? C9 C8 C32 120.3(4) . . ? C24 C8 C9 118.9(4) . . ? C24 C8 C32 120.8(4) . . ? C11 C9 C8 123.6(4) . . ? C11 C9 C16 117.7(4) . . ? C16 C9 C8 118.7(4) . . ? C19 C10 C16 120.7(4) . . ? C13 C11 C9 121.7(4) . . ? C11 C13 C14 120.5(4) . . ? C22 C14 C13 119.9(4) . . ? C10 C16 C9 119.3(4) . . ? C10 C16 C22 121.7(4) . . ? C22 C16 C9 118.9(4) . . ? C10 C19 C24 120.3(4) . . ? C14 C22 C16 121.3(4) . . ? C8 C24 C19 122.0(4) . . ? N4 C32 C8 120.8(4) . . ? C25 N7 C20 110.9(3) . . ? C31 N7 C20 110.9(3) . . ? C31 N7 C25 106.0(3) . . ? C31 N7 C35 111.1(3) . . ? C35 N7 C20 106.9(3) . . ? C35 N7 C25 111.2(3) . . ? C20 C15 C33 110.9(3) . . ? C15 C20 N7 115.3(3) . . ? C28 C23 C40 112.8(3) . . ? C27 C25 N7 115.6(3) . . ? C25 C27 C38 111.1(3) . . ? C35 C28 C23 111.0(3) . . ? C41 C31 N7 115.6(3) . . ? C34 C33 C15 113.1(3) . . ? C28 C35 N7 115.5(3) . . ? C44 C36 C41 112.9(3) . . ? C30 C38 C27 113.8(3) . . ? C31 C41 C36 108.8(3) . . ? _database_code_depnum_ccdc_archive 'CCDC 932311'