# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Sam Thompson' 'Andrew D. Hamilton' _publ_contact_author_name 'Sam Thompson' _publ_contact_author_email sam.thompson@chem.ox.ac.uk data_RS116 _database_code_depnum_ccdc_archive 'CCDC 861447' #TrackingRef '8944_web_deposit_cif_file_0_SamThompson_1325966967.rs116.cif' _chemical_name_systematic ; tert-butyl 3-(3-(3-(but-3-en-1-yl)-3-(3-(2-(tert-butoxy)-2-oxoethoxy) -5-isopropoxybenzoyl)ureido)-4-isopropoxyphenyl)propanoate ; _publ_section_exptl_refinement ; H2 was located from Fourier difference maps and positionally and isotropically refined. Other Hydrogens were placed in calculated positions with reference to Fourier difference maps and refined in a riding model. The smaller than ideal data to parameter ratio was as a result of a weakly diffracting crystal ; _cell_length_a 17.8976(4) _cell_length_b 11.2875(3) _cell_length_c 18.4543(5) _cell_angle_alpha 90 _cell_angle_beta 95.4952(12) _cell_angle_gamma 90 _cell_volume 3710.99(16) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ' -P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C37 H52 N2 O9 # Dc = 1.20 Fooo = 1440.00 Mu = 0.85 M = 668.83 # Found Formula = C37 H52 N2 O9 # Dc = 1.20 FOOO = 1440.00 Mu = 0.85 M = 668.83 _chemical_formula_sum 'C37 H52 N2 O9' _chemical_formula_moiety 'C37 H52 N2 O9' _chemical_compound_source ? _chemical_formula_weight 668.83 _cell_measurement_reflns_used 7600 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.150 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_max 0.150 _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.085 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 14356 _reflns_number_total 7733 _diffrn_reflns_av_R_equivalents 0.057 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 7733 # Theoretical number of reflections is about 15646 _diffrn_reflns_theta_min 5.116 _diffrn_reflns_theta_max 26.675 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.075 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -22 _reflns_limit_h_max 22 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 2.52 _oxford_diffrn_Wilson_scale 17.31 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.29 _refine_diff_density_max 0.66 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 3964 _refine_ls_number_restraints 0 _refine_ls_number_parameters 437 _oxford_refine_ls_R_factor_ref 0.0505 _refine_ls_wR_factor_ref 0.0478 _refine_ls_goodness_of_fit_ref 1.1257 _refine_ls_shift/su_max 0.0002865 _refine_ls_shift/su_mean 0.0000214 # The values computed from all data _oxford_reflns_number_all 7733 _refine_ls_R_factor_all 0.1212 _refine_ls_wR_factor_all 0.0788 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4605 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_gt 0.0524 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.08 1.05 1.13 0.403 0.297 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Oxford Diffraction, (2010). CrysAlisPro. Oxford Diffraction, (2010). Supernova User Manual. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N3 N 0.57637(12) 0.14035(19) 0.35020(12) 0.0254 1.0000 Uani . . . . . . N23 N 0.64590(11) 0.31356(18) 0.37958(11) 0.0244 1.0000 Uani . . . . . . O1 O 0.54033(10) 0.26932(16) 0.43544(9) 0.0310 1.0000 Uani . . . . . . O6 O 0.57585(11) -0.01811(18) 0.25018(10) 0.0400 1.0000 Uani . . . . . . O17 O 0.20240(10) 0.07173(17) 0.51651(9) 0.0338 1.0000 Uani . . . . . . O22 O 0.24193(12) -0.11497(19) 0.54031(11) 0.0484 1.0000 Uani . . . . . . O29 O 0.69341(10) 0.20849(16) 0.28750(9) 0.0310 1.0000 Uani . . . . . . O33 O 0.79950(10) 0.62459(17) 0.20859(10) 0.0356 1.0000 Uani . . . . . . O40 O 0.94777(10) 0.45492(17) 0.41053(9) 0.0312 1.0000 Uani . . . . . . O43 O 0.87646(11) 0.48784(17) 0.53449(10) 0.0362 1.0000 Uani . . . . . . O44 O 0.91629(10) 0.30748(17) 0.57564(10) 0.0339 1.0000 Uani . . . . . . C2 C 0.58283(14) 0.2392(2) 0.39129(13) 0.0241 1.0000 Uani . . . . . . C4 C 0.52136(14) 0.0508(2) 0.35200(13) 0.0250 1.0000 Uani . . . . . . C5 C 0.52258(14) -0.0363(2) 0.29763(14) 0.0291 1.0000 Uani . . . . . . C7 C 0.58416(17) -0.1017(3) 0.19243(15) 0.0387 1.0000 Uani . . . . . . C8 C 0.6247(2) -0.0343(3) 0.13773(17) 0.0543 1.0000 Uani . . . . . . C9 C 0.62533(18) -0.2102(3) 0.22135(18) 0.0509 1.0000 Uani . . . . . . C10 C 0.47244(15) -0.1298(3) 0.29542(15) 0.0338 1.0000 Uani . . . . . . C11 C 0.42166(15) -0.1382(3) 0.34769(14) 0.0321 1.0000 Uani . . . . . . C12 C 0.42032(13) -0.0549(2) 0.40218(13) 0.0272 1.0000 Uani . . . . . . C13 C 0.46999(13) 0.0409(2) 0.40376(13) 0.0256 1.0000 Uani . . . . . . C14 C 0.36732(14) -0.0680(3) 0.46087(14) 0.0312 1.0000 Uani . . . . . . C15 C 0.29302(15) -0.0054(3) 0.44498(15) 0.0346 1.0000 Uani . . . . . . C16 C 0.24391(14) -0.0240(3) 0.50572(14) 0.0310 1.0000 Uani . . . . . . C18 C 0.15417(16) 0.0778(3) 0.57673(15) 0.0362 1.0000 Uani . . . . . . C19 C 0.2022(2) 0.0744(4) 0.64817(16) 0.0587 1.0000 Uani . . . . . . C20 C 0.09702(19) -0.0217(3) 0.5709(2) 0.0609 1.0000 Uani . . . . . . C21 C 0.1158(2) 0.1959(3) 0.5634(2) 0.0651 1.0000 Uani . . . . . . C24 C 0.65202(15) 0.4227(2) 0.42454(14) 0.0296 1.0000 Uani . . . . . . C25 C 0.60856(18) 0.5268(2) 0.38928(16) 0.0402 1.0000 Uani . . . . . . C26 C 0.6374(3) 0.6417(3) 0.4210(2) 0.0736 1.0000 Uani . . . . . . C27 C 0.6015(3) 0.7230(4) 0.4478(2) 0.0844 1.0000 Uani . . . . . . C28 C 0.69650(13) 0.2931(2) 0.32940(13) 0.0238 1.0000 Uani . . . . . . C30 C 0.75873(14) 0.3824(2) 0.32535(13) 0.0253 1.0000 Uani . . . . . . C31 C 0.75161(14) 0.4669(2) 0.27151(13) 0.0264 1.0000 Uani . . . . . . C32 C 0.81093(15) 0.5464(2) 0.26494(13) 0.0273 1.0000 Uani . . . . . . C34 C 0.85931(16) 0.7020(2) 0.19081(14) 0.0341 1.0000 Uani . . . . . . C35 C 0.92039(17) 0.6345(3) 0.15742(15) 0.0408 1.0000 Uani . . . . . . C36 C 0.82148(19) 0.7911(3) 0.13830(17) 0.0491 1.0000 Uani . . . . . . C37 C 0.87443(14) 0.5406(2) 0.31359(13) 0.0267 1.0000 Uani . . . . . . C38 C 0.88060(14) 0.4535(2) 0.36700(13) 0.0264 1.0000 Uani . . . . . . C39 C 0.82354(14) 0.3723(2) 0.37372(13) 0.0268 1.0000 Uani . . . . . . C41 C 0.95801(15) 0.3703(2) 0.46725(13) 0.0286 1.0000 Uani . . . . . . C42 C 0.91128(15) 0.3977(2) 0.52906(14) 0.0271 1.0000 Uani . . . . . . C45 C 0.87382(16) 0.3058(3) 0.64113(15) 0.0360 1.0000 Uani . . . . . . C46 C 0.8924(2) 0.1852(3) 0.6722(2) 0.0702 1.0000 Uani . . . . . . C47 C 0.79047(16) 0.3179(3) 0.61818(18) 0.0518 1.0000 Uani . . . . . . C48 C 0.9022(2) 0.4021(3) 0.69304(16) 0.0549 1.0000 Uani . . . . . . H71 H 0.5359 -0.1241 0.1708 0.0496 1.0000 Uiso R . . . . . H81 H 0.6323 -0.0835 0.0973 0.0683 1.0000 Uiso R . . . . . H82 H 0.6719 -0.0087 0.1603 0.0683 1.0000 Uiso R . . . . . H83 H 0.5955 0.0326 0.1216 0.0683 1.0000 Uiso R . . . . . H91 H 0.6302 -0.2646 0.1828 0.0612 1.0000 Uiso R . . . . . H92 H 0.6738 -0.1876 0.2423 0.0612 1.0000 Uiso R . . . . . H93 H 0.5985 -0.2466 0.2574 0.0612 1.0000 Uiso R . . . . . H101 H 0.4730 -0.1877 0.2581 0.0412 1.0000 Uiso R . . . . . H111 H 0.3871 -0.2023 0.3460 0.0393 1.0000 Uiso R . . . . . H131 H 0.4689 0.0996 0.4405 0.0330 1.0000 Uiso R . . . . . H141 H 0.3911 -0.0367 0.5050 0.0407 1.0000 Uiso R . . . . . H142 H 0.3574 -0.1499 0.4670 0.0407 1.0000 Uiso R . . . . . H151 H 0.3020 0.0769 0.4394 0.0463 1.0000 Uiso R . . . . . H152 H 0.2685 -0.0361 0.4010 0.0463 1.0000 Uiso R . . . . . H191 H 0.1713 0.0779 0.6872 0.0707 1.0000 Uiso R . . . . . H192 H 0.2352 0.1406 0.6508 0.0707 1.0000 Uiso R . . . . . H193 H 0.2307 0.0033 0.6515 0.0707 1.0000 Uiso R . . . . . H201 H 0.0665 -0.0170 0.6102 0.0760 1.0000 Uiso R . . . . . H202 H 0.1221 -0.0960 0.5723 0.0760 1.0000 Uiso R . . . . . H203 H 0.0665 -0.0142 0.5261 0.0760 1.0000 Uiso R . . . . . H211 H 0.0826 0.2093 0.5997 0.0804 1.0000 Uiso R . . . . . H212 H 0.1524 0.2570 0.5653 0.0804 1.0000 Uiso R . . . . . H213 H 0.0881 0.1957 0.5168 0.0804 1.0000 Uiso R . . . . . H241 H 0.7033 0.4448 0.4329 0.0389 1.0000 Uiso R . . . . . H242 H 0.6329 0.4062 0.4697 0.0389 1.0000 Uiso R . . . . . H251 H 0.6135 0.5259 0.3385 0.0526 1.0000 Uiso R . . . . . H252 H 0.5571 0.5195 0.3971 0.0526 1.0000 Uiso R . . . . . H261 H 0.6899 0.6542 0.4211 0.0972 1.0000 Uiso R . . . . . H271 H 0.6262 0.7923 0.4670 0.1071 1.0000 Uiso R . . . . . H272 H 0.5488 0.7148 0.4490 0.1071 1.0000 Uiso R . . . . . H311 H 0.7070 0.4718 0.2393 0.0322 1.0000 Uiso R . . . . . H341 H 0.8798 0.7419 0.2335 0.0439 1.0000 Uiso R . . . . . H351 H 0.9594 0.6872 0.1471 0.0514 1.0000 Uiso R . . . . . H352 H 0.9403 0.5750 0.1902 0.0514 1.0000 Uiso R . . . . . H353 H 0.8994 0.5986 0.1135 0.0514 1.0000 Uiso R . . . . . H361 H 0.8569 0.8470 0.1239 0.0615 1.0000 Uiso R . . . . . H362 H 0.7831 0.8313 0.1607 0.0615 1.0000 Uiso R . . . . . H363 H 0.7999 0.7494 0.0967 0.0615 1.0000 Uiso R . . . . . H371 H 0.9135 0.5967 0.3104 0.0340 1.0000 Uiso R . . . . . H391 H 0.8279 0.3124 0.4100 0.0334 1.0000 Uiso R . . . . . H411 H 1.0095 0.3700 0.4854 0.0367 1.0000 Uiso R . . . . . H412 H 0.9444 0.2944 0.4482 0.0367 1.0000 Uiso R . . . . . H461 H 0.8680 0.1734 0.7151 0.0877 1.0000 Uiso R . . . . . H462 H 0.9452 0.1793 0.6836 0.0877 1.0000 Uiso R . . . . . H463 H 0.8763 0.1265 0.6373 0.0877 1.0000 Uiso R . . . . . H471 H 0.7632 0.3168 0.6599 0.0644 1.0000 Uiso R . . . . . H472 H 0.7816 0.3906 0.5929 0.0644 1.0000 Uiso R . . . . . H473 H 0.7745 0.2539 0.5870 0.0644 1.0000 Uiso R . . . . . H481 H 0.8751 0.4011 0.7348 0.0700 1.0000 Uiso R . . . . . H482 H 0.9540 0.3896 0.7074 0.0700 1.0000 Uiso R . . . . . H483 H 0.8957 0.4767 0.6694 0.0700 1.0000 Uiso R . . . . . H2 H 0.6093(17) 0.135(3) 0.3191(16) 0.043(9) 1.0000 Uiso . . . . . . 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 N3 0.0243(11) 0.0263(12) 0.0267(11) -0.0021(9) 0.0085(10) -0.0067(10) N23 0.0265(11) 0.0222(11) 0.0246(11) -0.0015(9) 0.0039(9) -0.0032(9) O1 0.0317(10) 0.0296(10) 0.0335(10) -0.0013(8) 0.0119(8) -0.0003(8) O6 0.0427(11) 0.0412(12) 0.0390(11) -0.0148(9) 0.0188(9) -0.0182(10) O17 0.0369(11) 0.0345(11) 0.0311(10) 0.0022(8) 0.0085(8) 0.0051(9) O22 0.0572(14) 0.0411(13) 0.0514(13) 0.0150(11) 0.0290(11) 0.0143(11) O29 0.0347(10) 0.0290(10) 0.0307(10) -0.0063(8) 0.0107(8) -0.0090(8) O33 0.0372(11) 0.0359(11) 0.0338(10) 0.0139(9) 0.0027(8) -0.0099(9) O40 0.0292(10) 0.0369(11) 0.0271(9) 0.0040(8) 0.0003(8) -0.0084(9) O43 0.0484(12) 0.0279(11) 0.0324(10) -0.0009(8) 0.0047(9) 0.0062(10) O44 0.0349(10) 0.0300(10) 0.0391(11) 0.0076(9) 0.0153(8) 0.0030(9) C2 0.0238(13) 0.0235(13) 0.0251(13) 0.0041(11) 0.0024(11) -0.0007(11) C4 0.0243(13) 0.0247(14) 0.0255(12) 0.0022(11) 0.0001(10) -0.0010(11) C5 0.0254(14) 0.0327(15) 0.0301(14) -0.0017(12) 0.0069(11) -0.0073(12) C7 0.0433(17) 0.0411(17) 0.0328(15) -0.0145(13) 0.0090(13) -0.0128(14) C8 0.060(2) 0.064(2) 0.0416(18) -0.0095(17) 0.0188(16) -0.0115(19) C9 0.0474(19) 0.053(2) 0.054(2) -0.0102(17) 0.0139(16) -0.0040(17) C10 0.0335(15) 0.0330(16) 0.0353(15) -0.0066(12) 0.0046(12) -0.0069(13) C11 0.0263(14) 0.0344(16) 0.0354(15) 0.0043(12) 0.0013(12) -0.0098(12) C12 0.0211(13) 0.0322(15) 0.0278(13) 0.0081(12) 0.0002(10) -0.0002(11) C13 0.0249(13) 0.0267(14) 0.0253(13) 0.0021(11) 0.0029(11) -0.0003(11) C14 0.0232(13) 0.0394(16) 0.0313(14) 0.0079(12) 0.0035(11) -0.0029(12) C15 0.0316(14) 0.0390(16) 0.0342(15) 0.0087(13) 0.0084(12) 0.0038(13) C16 0.0278(14) 0.0320(16) 0.0337(15) 0.0040(13) 0.0058(12) 0.0038(13) C18 0.0380(16) 0.0401(17) 0.0324(15) -0.0032(13) 0.0144(12) 0.0029(14) C19 0.064(2) 0.080(3) 0.0323(16) -0.0067(17) 0.0094(16) 0.001(2) C20 0.0410(18) 0.072(3) 0.074(2) -0.017(2) 0.0286(17) -0.0060(18) C21 0.080(3) 0.062(2) 0.057(2) -0.0011(19) 0.028(2) 0.026(2) C24 0.0347(15) 0.0278(14) 0.0271(13) -0.0075(11) 0.0064(11) -0.0069(12) C25 0.0520(18) 0.0281(15) 0.0413(16) -0.0061(13) 0.0086(14) 0.0012(14) C26 0.101(3) 0.042(2) 0.076(3) -0.010(2) 0.002(2) 0.006(2) C27 0.121(4) 0.052(3) 0.079(3) -0.022(2) 0.006(3) 0.012(3) C28 0.0261(13) 0.0238(13) 0.0216(12) 0.0025(11) 0.0029(10) -0.0019(11) C30 0.0305(14) 0.0238(13) 0.0225(12) -0.0026(11) 0.0066(11) -0.0052(11) C31 0.0258(13) 0.0265(14) 0.0275(13) -0.0013(11) 0.0054(11) -0.0050(11) C32 0.0362(15) 0.0243(14) 0.0220(12) 0.0003(11) 0.0064(11) -0.0033(12) C34 0.0429(16) 0.0303(15) 0.0296(14) 0.0028(12) 0.0062(12) -0.0121(13) C35 0.0476(18) 0.0452(18) 0.0314(15) 0.0001(13) 0.0138(13) -0.0057(15) C36 0.061(2) 0.0388(18) 0.0489(19) 0.0146(15) 0.0130(16) -0.0061(16) C37 0.0329(14) 0.0228(13) 0.0254(13) -0.0032(11) 0.0085(11) -0.0103(12) C38 0.0263(13) 0.0319(15) 0.0217(12) -0.0051(11) 0.0050(10) -0.0035(12) C39 0.0294(14) 0.0255(14) 0.0257(13) 0.0009(11) 0.0038(11) -0.0025(12) C41 0.0311(14) 0.0263(14) 0.0281(13) 0.0012(11) 0.0004(11) -0.0037(12) C42 0.0307(14) 0.0223(14) 0.0281(13) 0.0009(11) 0.0013(11) -0.0058(12) C45 0.0362(15) 0.0366(16) 0.0381(15) 0.0093(13) 0.0180(13) -0.0018(13) C46 0.079(3) 0.057(2) 0.080(3) 0.037(2) 0.040(2) 0.015(2) C47 0.0372(17) 0.069(2) 0.0509(19) -0.0016(18) 0.0149(15) -0.0096(17) C48 0.063(2) 0.071(2) 0.0311(16) 0.0049(16) 0.0057(15) -0.0086(19) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2500(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N3 . C2 . 1.348(3) yes N3 . C4 . 1.413(3) yes N3 . H2 . 0.86(3) no N23 . C2 . 1.439(3) yes N23 . C24 . 1.483(3) yes N23 . C28 . 1.375(3) yes O1 . C2 . 1.215(3) yes O6 . C5 . 1.370(3) yes O6 . C7 . 1.442(3) yes O17 . C16 . 1.337(3) yes O17 . C18 . 1.473(3) yes O22 . C16 . 1.211(3) yes O29 . C28 . 1.226(3) yes O33 . C32 . 1.365(3) yes O33 . C34 . 1.444(3) yes O40 . C38 . 1.381(3) yes O40 . C41 . 1.416(3) yes O43 . C42 . 1.202(3) yes O44 . C42 . 1.330(3) yes O44 . C45 . 1.488(3) yes C4 . C5 . 1.407(4) yes C4 . C13 . 1.392(3) yes C5 . C10 . 1.383(4) yes C7 . C8 . 1.504(4) yes C7 . C9 . 1.501(4) yes C7 . H71 . 0.950 no C8 . H81 . 0.950 no C8 . H82 . 0.950 no C8 . H83 . 0.950 no C9 . H91 . 0.950 no C9 . H92 . 0.950 no C9 . H93 . 0.950 no C10 . C11 . 1.390(4) yes C10 . H101 . 0.950 no C11 . C12 . 1.379(4) yes C11 . H111 . 0.950 no C12 . C13 . 1.398(4) yes C12 . C14 . 1.514(3) yes C13 . H131 . 0.950 no C14 . C15 . 1.510(4) yes C14 . H141 . 0.950 no C14 . H142 . 0.950 no C15 . C16 . 1.504(4) yes C15 . H151 . 0.950 no C15 . H152 . 0.950 no C18 . C19 . 1.504(4) yes C18 . C20 . 1.516(4) yes C18 . C21 . 1.509(5) yes C19 . H191 . 0.950 no C19 . H192 . 0.950 no C19 . H193 . 0.950 no C20 . H201 . 0.950 no C20 . H202 . 0.950 no C20 . H203 . 0.950 no C21 . H211 . 0.950 no C21 . H212 . 0.950 no C21 . H213 . 0.950 no C24 . C25 . 1.521(4) yes C24 . H241 . 0.950 no C24 . H242 . 0.950 no C25 . C26 . 1.494(5) yes C25 . H251 . 0.950 no C25 . H252 . 0.950 no C26 . C27 . 1.249(5) yes C26 . H261 . 0.950 no C27 . H271 . 0.950 no C27 . H272 . 0.950 no C28 . C30 . 1.510(3) yes C30 . C31 . 1.375(4) yes C30 . C39 . 1.399(3) yes C31 . C32 . 1.404(4) yes C31 . H311 . 0.950 no C32 . C37 . 1.381(4) yes C34 . C35 . 1.511(4) yes C34 . C36 . 1.511(4) yes C34 . H341 . 0.950 no C35 . H351 . 0.950 no C35 . H352 . 0.950 no C35 . H353 . 0.950 no C36 . H361 . 0.950 no C36 . H362 . 0.950 no C36 . H363 . 0.950 no C37 . C38 . 1.389(4) yes C37 . H371 . 0.950 no C38 . C39 . 1.387(4) yes C39 . H391 . 0.950 no C41 . C42 . 1.509(4) yes C41 . H411 . 0.950 no C41 . H412 . 0.950 no C45 . C46 . 1.502(4) yes C45 . C47 . 1.517(4) yes C45 . C48 . 1.506(4) yes C46 . H461 . 0.950 no C46 . H462 . 0.950 no C46 . H463 . 0.950 no C47 . H471 . 0.950 no C47 . H472 . 0.950 no C47 . H473 . 0.950 no C48 . H481 . 0.950 no C48 . H482 . 0.950 no C48 . H483 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N3 . C4 . 126.9(2) yes C2 . N3 . H2 . 114(2) no C4 . N3 . H2 . 119(2) no C2 . N23 . C24 . 114.7(2) yes C2 . N23 . C28 . 125.4(2) yes C24 . N23 . C28 . 119.9(2) yes C5 . O6 . C7 . 120.1(2) yes C16 . O17 . C18 . 121.6(2) yes C32 . O33 . C34 . 120.3(2) yes C38 . O40 . C41 . 117.80(19) yes C42 . O44 . C45 . 121.8(2) yes N23 . C2 . N3 . 115.1(2) yes N23 . C2 . O1 . 119.2(2) yes N3 . C2 . O1 . 125.7(2) yes N3 . C4 . C5 . 115.1(2) yes N3 . C4 . C13 . 125.5(2) yes C5 . C4 . C13 . 119.3(2) yes C4 . C5 . O6 . 114.2(2) yes C4 . C5 . C10 . 120.0(2) yes O6 . C5 . C10 . 125.8(2) yes O6 . C7 . C8 . 104.8(2) yes O6 . C7 . C9 . 110.7(2) yes C8 . C7 . C9 . 113.5(3) yes O6 . C7 . H71 . 109.3 no C8 . C7 . H71 . 109.2 no C9 . C7 . H71 . 109.1 no C7 . C8 . H81 . 110.3 no C7 . C8 . H82 . 109.0 no H81 . C8 . H82 . 109.5 no C7 . C8 . H83 . 109.1 no H81 . C8 . H83 . 109.5 no H82 . C8 . H83 . 109.5 no C7 . C9 . H91 . 109.7 no C7 . C9 . H92 . 108.9 no H91 . C9 . H92 . 109.5 no C7 . C9 . H93 . 109.8 no H91 . C9 . H93 . 109.5 no H92 . C9 . H93 . 109.5 no C5 . C10 . C11 . 119.8(3) yes C5 . C10 . H101 . 119.6 no C11 . C10 . H101 . 120.6 no C10 . C11 . C12 . 121.2(2) yes C10 . C11 . H111 . 119.7 no C12 . C11 . H111 . 119.1 no C11 . C12 . C13 . 119.2(2) yes C11 . C12 . C14 . 120.7(2) yes C13 . C12 . C14 . 120.1(2) yes C12 . C13 . C4 . 120.6(2) yes C12 . C13 . H131 . 119.8 no C4 . C13 . H131 . 119.6 no C12 . C14 . C15 . 114.6(2) yes C12 . C14 . H141 . 108.5 no C15 . C14 . H141 . 107.8 no C12 . C14 . H142 . 108.5 no C15 . C14 . H142 . 107.9 no H141 . C14 . H142 . 109.5 no C14 . C15 . C16 . 110.9(2) yes C14 . C15 . H151 . 108.9 no C16 . C15 . H151 . 109.5 no C14 . C15 . H152 . 108.8 no C16 . C15 . H152 . 109.3 no H151 . C15 . H152 . 109.5 no C15 . C16 . O17 . 111.8(2) yes C15 . C16 . O22 . 124.0(2) yes O17 . C16 . O22 . 124.2(2) yes O17 . C18 . C19 . 109.5(2) yes O17 . C18 . C20 . 110.7(2) yes C19 . C18 . C20 . 111.6(3) yes O17 . C18 . C21 . 102.0(2) yes C19 . C18 . C21 . 112.2(3) yes C20 . C18 . C21 . 110.4(3) yes C18 . C19 . H191 . 109.8 no C18 . C19 . H192 . 108.9 no H191 . C19 . H192 . 109.5 no C18 . C19 . H193 . 109.7 no H191 . C19 . H193 . 109.5 no H192 . C19 . H193 . 109.5 no C18 . C20 . H201 . 109.7 no C18 . C20 . H202 . 109.7 no H201 . C20 . H202 . 109.5 no C18 . C20 . H203 . 108.9 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no C18 . C21 . H211 . 109.3 no C18 . C21 . H212 . 109.5 no H211 . C21 . H212 . 109.5 no C18 . C21 . H213 . 109.6 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no N23 . C24 . C25 . 113.3(2) yes N23 . C24 . H241 . 109.1 no C25 . C24 . H241 . 108.3 no N23 . C24 . H242 . 108.3 no C25 . C24 . H242 . 108.4 no H241 . C24 . H242 . 109.5 no C24 . C25 . C26 . 111.1(3) yes C24 . C25 . H251 . 108.8 no C26 . C25 . H251 . 109.6 no C24 . C25 . H252 . 109.4 no C26 . C25 . H252 . 108.6 no H251 . C25 . H252 . 109.5 no C25 . C26 . C27 . 128.5(5) yes C25 . C26 . H261 . 115.7 no C27 . C26 . H261 . 115.8 no C26 . C27 . H271 . 120.9 no C26 . C27 . H272 . 119.1 no H271 . C27 . H272 . 120.0 no N23 . C28 . O29 . 124.2(2) yes N23 . C28 . C30 . 117.2(2) yes O29 . C28 . C30 . 118.5(2) yes C28 . C30 . C31 . 118.8(2) yes C28 . C30 . C39 . 119.0(2) yes C31 . C30 . C39 . 122.1(2) yes C30 . C31 . C32 . 119.2(2) yes C30 . C31 . H311 . 120.4 no C32 . C31 . H311 . 120.4 no C31 . C32 . O33 . 114.8(2) yes C31 . C32 . C37 . 119.7(2) yes O33 . C32 . C37 . 125.5(2) yes O33 . C34 . C35 . 111.6(2) yes O33 . C34 . C36 . 104.6(2) yes C35 . C34 . C36 . 111.8(2) yes O33 . C34 . H341 . 109.6 no C35 . C34 . H341 . 109.8 no C36 . C34 . H341 . 109.3 no C34 . C35 . H351 . 109.9 no C34 . C35 . H352 . 109.8 no H351 . C35 . H352 . 109.5 no C34 . C35 . H353 . 108.7 no H351 . C35 . H353 . 109.5 no H352 . C35 . H353 . 109.5 no C34 . C36 . H361 . 110.6 no C34 . C36 . H362 . 109.7 no H361 . C36 . H362 . 109.5 no C34 . C36 . H363 . 108.1 no H361 . C36 . H363 . 109.5 no H362 . C36 . H363 . 109.5 no C32 . C37 . C38 . 120.0(2) yes C32 . C37 . H371 . 119.6 no C38 . C37 . H371 . 120.5 no C37 . C38 . O40 . 114.2(2) yes C37 . C38 . C39 . 121.5(2) yes O40 . C38 . C39 . 124.3(2) yes C30 . C39 . C38 . 117.5(2) yes C30 . C39 . H391 . 121.0 no C38 . C39 . H391 . 121.5 no O40 . C41 . C42 . 112.3(2) yes O40 . C41 . H411 . 108.4 no C42 . C41 . H411 . 108.8 no O40 . C41 . H412 . 108.9 no C42 . C41 . H412 . 108.9 no H411 . C41 . H412 . 109.5 no C41 . C42 . O44 . 108.9(2) yes C41 . C42 . O43 . 124.4(2) yes O44 . C42 . O43 . 126.7(2) yes O44 . C45 . C46 . 102.1(2) yes O44 . C45 . C47 . 109.7(2) yes C46 . C45 . C47 . 111.4(3) yes O44 . C45 . C48 . 109.8(2) yes C46 . C45 . C48 . 111.3(3) yes C47 . C45 . C48 . 112.1(3) yes C45 . C46 . H461 . 110.0 no C45 . C46 . H462 . 109.1 no H461 . C46 . H462 . 109.5 no C45 . C46 . H463 . 109.3 no H461 . C46 . H463 . 109.5 no H462 . C46 . H463 . 109.5 no C45 . C47 . H471 . 109.9 no C45 . C47 . H472 . 109.2 no H471 . C47 . H472 . 109.5 no C45 . C47 . H473 . 109.3 no H471 . C47 . H473 . 109.5 no H472 . C47 . H473 . 109.5 no C45 . C48 . H481 . 109.8 no C45 . C48 . H482 . 109.4 no H481 . C48 . H482 . 109.5 no C45 . C48 . H483 . 109.2 no H481 . C48 . H483 . 109.5 no H482 . C48 . H483 . 109.5 no _iucr_refine_instruction_details_constraints ; # # Punched on 15/10/11 at 19:33:54 # #LIST 12 BLOCK SCALE X'S, U'S CONT H(2,X'S,U[ISO]) UNTIL H(2) RIDE N ( 3,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) H ( 83,X'S) RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S) H ( 93,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,X'S) H ( 193,X'S) RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) H ( 203,X'S) RIDE C ( 21,X'S) H ( 211,X'S) H ( 212,X'S) H ( 213,X'S) RIDE C ( 24,X'S) H ( 241,X'S) H ( 242,X'S) RIDE C ( 25,X'S) H ( 251,X'S) H ( 252,X'S) RIDE C ( 26,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 271,X'S) H ( 272,X'S) RIDE C ( 31,X'S) H ( 311,X'S) RIDE C ( 34,X'S) H ( 341,X'S) RIDE C ( 35,X'S) H ( 351,X'S) H ( 352,X'S) H ( 353,X'S) RIDE C ( 36,X'S) H ( 361,X'S) H ( 362,X'S) H ( 363,X'S) RIDE C ( 37,X'S) H ( 371,X'S) RIDE C ( 39,X'S) H ( 391,X'S) RIDE C ( 41,X'S) H ( 411,X'S) H ( 412,X'S) RIDE C ( 46,X'S) H ( 461,X'S) H ( 462,X'S) H ( 463,X'S) RIDE C ( 47,X'S) H ( 471,X'S) H ( 472,X'S) H ( 473,X'S) RIDE C ( 48,X'S) H ( 481,X'S) H ( 482,X'S) H ( 483,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 15/10/11 at 19:33:54 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ;