#============================================================================== data_global #============================================================================== _publ_contact_author 'Darren J Dixon' _publ_contact_author_email darren.dixon@chem.ox.ac.uk loop_ _publ_author_name _publ_author_address 'Aillaud, Isabelle' ; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; 'Barber, David M.' ; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; 'Thompson, Amber L.' ; Chemical Crystallography, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; 'Dixon, Darren J.' ; Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; _journal_name_full 'Organic Letters' _journal_volume '.' _journal_page_first '.' _journal_page_last '.' _journal_year '2013' _ccdc_journal_depnumber '.' _publ_section_title ; Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas ; _publ_section_abstract ; A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on the distal nitrogen atom of the urea moiety, affording polyheterocyclic products in good yields and good to excellent enantioselectivities. ; #============================================================================== data_9r #============================================================================== _audit_creation_date "12-01-19" _audit_creation_method CRYSTALS_ver_14.40 _oxford_structure_analysis_title '6402' _chemical_name_systematic . _chemical_melting_point 'not measured' _refine_special_details ; The Flack x parameter [Flack, 1983; Flack & Bernardinelli (2000)] refined to 0.05(12), reducing to -0.001(8) on the application of Bijvoet difference restraints [Thompson & Watkin, 2010]. Analysis of the Bijvoet differences [Hooft et al., 2008] gave a Hooft y parameter of -0.03(3), G of 1.06(6), and a probability that the structure was the correct hand of >99.99% given that the structure is enantiopure or a racemic twin using the Bayesian method. ; _cell_length_a 7.1383(1) _cell_length_b 10.6018(1) _cell_length_c 12.0383(1) _cell_angle_alpha 90 _cell_angle_beta 102.3752(6) _cell_angle_gamma 90 _cell_volume 889.876(17) _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,y+1/2,-z' 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 0.0181 0.0091 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' F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 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' O 0.0492 0.0322 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' _cell_formula_units_Z 2 # Given Formula = C21 H20 F1 N3 O1 # Dc = 1.30 Fooo = 368.00 Mu = 7.24 M = 349.41 # Found Formula = C21 H20 F1 N3 O1 # Dc = 1.30 FOOO = 368.00 Mu = 7.24 M = 349.41 _chemical_formula_sum 'C21 H20 F1 N3 O1' _chemical_formula_moiety 'C21 H20 F1 N3 O1' _chemical_compound_source . _chemical_formula_weight 349.41 _cell_measurement_reflns_used 59434 _cell_measurement_theta_min 4 _cell_measurement_theta_max 77 _cell_measurement_temperature 150 _exptl_crystal_description 'block' _exptl_crystal_colour 'clear_pale_colourless' _exptl_crystal_size_min 0.080 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.724 # Sheldrick geometric approximatio 0.90 0.94 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.94 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device 'Area' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _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 76919 _reflns_number_total 3711 _diffrn_reflns_av_R_equivalents 0.020 # Number of reflections without Friedels Law is 3711 # Number of reflections with Friedels Law is 1968 # Theoretical number of reflections is about 1880 _diffrn_reflns_theta_min 3.759 _diffrn_reflns_theta_max 76.912 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 76.912 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -9 _reflns_limit_h_max 8 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 1.77 _oxford_diffrn_Wilson_scale 0.01 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.14 _refine_diff_density_max 0.14 # 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 3711 _refine_ls_number_restraints 1 _refine_ls_number_parameters 236 _oxford_refine_ls_R_factor_ref 0.0259 _refine_ls_wR_factor_ref 0.0665 _refine_ls_goodness_of_fit_ref 0.9678 _refine_ls_shift/su_max 0.0004298 _refine_ls_shift/su_mean 0.0000373 # The values computed with all filters except I/sigma _oxford_reflns_number_all 3711 _refine_ls_R_factor_all 0.0259 _refine_ls_wR_factor_all 0.0665 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3698 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_gt 0.0664 _refine_ls_abs_structure_Flack 0.06(11) _refine_ls_abs_structure_details 'Flack (1983), 1743 Friedel-pairs' # 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 'ad' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.17P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst., 33, 1143-1148. Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst., 41, 96-103. Oxford Diffraction, (2010). CrysAlisPro. Oxford Diffraction, (2010). Supernova User Manual. Thompson, A. L. & Watkin, D. J. (2011). J. Appl. Cryst., 44, 1017-1022. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 F1 F -0.00358(14) 0.99563(10) 0.98412(8) 0.0521 1.0000 Uani . . . . . . C2 C 0.08003(19) 0.91592(13) 0.92023(10) 0.0338 1.0000 Uani . . . . . . C3 C 0.03623(17) 0.78974(13) 0.92022(10) 0.0307 1.0000 Uani . . . . . . C4 C 0.12329(16) 0.70895(12) 0.85599(9) 0.0265 1.0000 Uani . . . . . . C5 C 0.24939(15) 0.75645(12) 0.79293(9) 0.0234 1.0000 Uani . . . . . . N6 N 0.34433(12) 0.67285(11) 0.72988(8) 0.0266 1.0000 Uani . . . . . . C7 C 0.24483(14) 0.61977(12) 0.63222(9) 0.0245 1.0000 Uani . . . . . . O8 O 0.06797(10) 0.63142(11) 0.60392(7) 0.0354 1.0000 Uani . . . . . . N9 N 0.34627(13) 0.55022(10) 0.56999(8) 0.0253 1.0000 Uani . . . . . . C10 C 0.55571(14) 0.56518(11) 0.57476(9) 0.0218 1.0000 Uani . . . . . . C11 C 0.63833(15) 0.66469(13) 0.66405(9) 0.0263 1.0000 Uani . . . . . . C12 C 0.55036(14) 0.65099(13) 0.76740(9) 0.0295 1.0000 Uani . . . . . . H122 H 0.5690 0.5654 0.8010 0.0358 1.0000 Uiso R . . . . . H121 H 0.6061 0.7131 0.8290 0.0358 1.0000 Uiso R . . . . . H111 H 0.6023 0.7505 0.6305 0.0308 1.0000 Uiso R . . . . . H112 H 0.7748 0.6552 0.6829 0.0315 1.0000 Uiso R . . . . . C13 C 0.66062(18) 0.43964(12) 0.60394(11) 0.0347 1.0000 Uani . . . . . . H131 H 0.7933 0.4519 0.6016 0.0510 1.0000 Uiso R . . . . . H132 H 0.6064 0.3733 0.5510 0.0514 1.0000 Uiso R . . . . . H133 H 0.6515 0.4144 0.6805 0.0517 1.0000 Uiso R . . . . . C14 C 0.57102(14) 0.61045(11) 0.45813(8) 0.0212 1.0000 Uani . . . . . . N15 N 0.73261(13) 0.66928(10) 0.43752(7) 0.0239 1.0000 Uani . . . . . . C16 C 0.69180(16) 0.71246(11) 0.32716(9) 0.0254 1.0000 Uani . . . . . . C17 C 0.50181(16) 0.67627(12) 0.27700(9) 0.0273 1.0000 Uani . . . . . . C18 C 0.42830(14) 0.61120(12) 0.36264(9) 0.0251 1.0000 Uani . . . . . . C19 C 0.23178(16) 0.55907(15) 0.36077(10) 0.0356 1.0000 Uani . . . . . . C20 C 0.23698(17) 0.48506(13) 0.46907(10) 0.0329 1.0000 Uani . . . . . . H201 H 0.1072 0.4720 0.4813 0.0390 1.0000 Uiso R . . . . . H202 H 0.3000 0.4056 0.4636 0.0387 1.0000 Uiso R . . . . . H192 H 0.1893 0.5047 0.2969 0.0433 1.0000 Uiso R . . . . . H191 H 0.1373 0.6304 0.3556 0.0438 1.0000 Uiso R . . . . . C21 C 0.4220(2) 0.71176(14) 0.16416(10) 0.0375 1.0000 Uani . . . . . . C22 C 0.5310(2) 0.78393(14) 0.10684(11) 0.0435 1.0000 Uani . . . . . . C23 C 0.7175(2) 0.82134(13) 0.15866(12) 0.0414 1.0000 Uani . . . . . . C24 C 0.8014(2) 0.78619(12) 0.26938(11) 0.0329 1.0000 Uani . . . . . . H241 H 0.9257 0.8092 0.3035 0.0375 1.0000 Uiso R . . . . . H231 H 0.7898 0.8695 0.1190 0.0488 1.0000 Uiso R . . . . . H221 H 0.4770 0.8096 0.0284 0.0521 1.0000 Uiso R . . . . . H211 H 0.2899 0.6869 0.1277 0.0455 1.0000 Uiso R . . . . . H151 H 0.8427 0.6708 0.4829 0.0304 1.0000 Uiso R . . . . . C25 C 0.28774(18) 0.88460(13) 0.79390(10) 0.0307 1.0000 Uani . . . . . . C26 C 0.20334(19) 0.96629(13) 0.85882(10) 0.0349 1.0000 Uani . . . . . . H261 H 0.2290 1.0539 0.8611 0.0430 1.0000 Uiso R . . . . . H251 H 0.3739 0.9162 0.7481 0.0371 1.0000 Uiso R . . . . . H41 H 0.0949 0.6206 0.8546 0.0315 1.0000 Uiso R . . . . . H31 H -0.0490 0.7586 0.9615 0.0371 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0684(6) 0.0416(4) 0.0565(5) -0.0078(4) 0.0357(4) 0.0120(4) C2 0.0395(6) 0.0338(6) 0.0304(6) -0.0018(5) 0.0125(5) 0.0095(5) C3 0.0290(6) 0.0386(6) 0.0272(5) -0.0001(4) 0.0124(4) 0.0000(5) C4 0.0272(5) 0.0276(5) 0.0255(5) 0.0002(4) 0.0075(4) -0.0021(4) C5 0.0211(5) 0.0291(5) 0.0200(5) -0.0007(4) 0.0045(4) 0.0014(4) N6 0.0186(4) 0.0368(5) 0.0248(4) -0.0041(4) 0.0058(3) 0.0014(4) C7 0.0211(4) 0.0288(5) 0.0250(5) -0.0016(4) 0.0081(4) -0.0027(4) O8 0.0184(4) 0.0559(5) 0.0319(4) -0.0121(4) 0.0052(3) -0.0008(4) N9 0.0203(4) 0.0284(5) 0.0290(4) -0.0052(4) 0.0094(3) -0.0048(3) C10 0.0184(5) 0.0237(5) 0.0244(5) 0.0015(4) 0.0074(4) 0.0001(4) C11 0.0185(4) 0.0362(5) 0.0244(5) -0.0017(4) 0.0055(4) -0.0024(4) C12 0.0199(5) 0.0443(7) 0.0240(5) 0.0009(5) 0.0042(4) 0.0030(4) C13 0.0356(6) 0.0293(6) 0.0421(6) 0.0101(5) 0.0149(5) 0.0087(5) C14 0.0206(4) 0.0194(4) 0.0247(5) -0.0008(4) 0.0076(4) 0.0021(4) N15 0.0221(4) 0.0277(4) 0.0224(4) -0.0007(4) 0.0060(3) -0.0021(3) C16 0.0343(6) 0.0212(5) 0.0224(5) -0.0023(4) 0.0098(4) 0.0027(4) C17 0.0307(5) 0.0285(5) 0.0229(5) -0.0025(4) 0.0060(4) 0.0085(4) C18 0.0225(5) 0.0290(5) 0.0240(5) -0.0047(4) 0.0052(4) 0.0028(4) C19 0.0234(5) 0.0512(7) 0.0316(6) -0.0137(6) 0.0042(4) -0.0045(5) C20 0.0268(5) 0.0365(6) 0.0384(6) -0.0156(5) 0.0135(5) -0.0107(5) C21 0.0429(7) 0.0448(7) 0.0233(5) -0.0002(5) 0.0038(5) 0.0136(6) C22 0.0631(9) 0.0436(8) 0.0250(6) 0.0064(5) 0.0121(6) 0.0160(6) C23 0.0690(9) 0.0284(6) 0.0342(6) 0.0050(5) 0.0277(6) 0.0037(6) C24 0.0444(7) 0.0264(5) 0.0322(6) -0.0027(4) 0.0175(5) -0.0043(5) C25 0.0339(6) 0.0319(6) 0.0288(6) 0.0045(5) 0.0126(4) -0.0026(5) C26 0.0441(7) 0.0263(6) 0.0360(6) 0.0028(5) 0.0124(5) 0.0033(5) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 12.4(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 F1 . C2 . 1.3634(13) yes C2 . C3 . 1.3738(18) yes C2 . C26 . 1.3730(18) yes C3 . C4 . 1.3869(16) yes C3 . H31 . 0.925 no C4 . C5 . 1.3903(15) yes C4 . H41 . 0.958 no C5 . N6 . 1.4288(14) yes C5 . C25 . 1.3855(17) yes N6 . C7 . 1.3585(14) yes N6 . C12 . 1.4615(13) yes C7 . O8 . 1.2413(13) yes C7 . N9 . 1.3644(14) yes N9 . C10 . 1.4923(12) yes N9 . C20 . 1.4682(14) yes C10 . C11 . 1.5311(15) yes C10 . C13 . 1.5307(15) yes C10 . C14 . 1.5098(14) yes C11 . C12 . 1.5160(14) yes C11 . H111 . 1.006 no C11 . H112 . 0.957 no C12 . H122 . 0.990 no C12 . H121 . 1.008 no C13 . H131 . 0.962 no C13 . H132 . 0.972 no C13 . H133 . 0.975 no C14 . N15 . 1.3798(13) yes C14 . C18 . 1.3628(14) yes N15 . C16 . 1.3761(14) yes N15 . H151 . 0.856 no C16 . C17 . 1.4143(16) yes C16 . C24 . 1.3931(16) yes C17 . C18 . 1.4304(15) yes C17 . C21 . 1.4070(16) yes C18 . C19 . 1.5035(15) yes C19 . C20 . 1.5152(19) yes C19 . H192 . 0.956 no C19 . H191 . 1.006 no C20 . H201 . 0.978 no C20 . H202 . 0.964 no C21 . C22 . 1.377(2) yes C21 . H211 . 0.987 no C22 . C23 . 1.401(2) yes C22 . H221 . 0.980 no C23 . C24 . 1.3900(19) yes C23 . H231 . 0.928 no C24 . H241 . 0.927 no C25 . C26 . 1.3877(17) yes C25 . H251 . 0.969 no C26 . H261 . 0.946 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 F1 . C2 . C3 . 118.46(11) yes F1 . C2 . C26 . 118.12(12) yes C3 . C2 . C26 . 123.42(11) yes C2 . C3 . C4 . 118.18(11) yes C2 . C3 . H31 . 121.6 no C4 . C3 . H31 . 120.3 no C3 . C4 . C5 . 120.04(10) yes C3 . C4 . H41 . 119.7 no C5 . C4 . H41 . 120.3 no C4 . C5 . N6 . 120.11(10) yes C4 . C5 . C25 . 120.03(10) yes N6 . C5 . C25 . 119.83(10) yes C5 . N6 . C7 . 119.81(9) yes C5 . N6 . C12 . 119.65(9) yes C7 . N6 . C12 . 120.44(9) yes N6 . C7 . O8 . 120.57(10) yes N6 . C7 . N9 . 117.29(9) yes O8 . C7 . N9 . 122.10(10) yes C7 . N9 . C10 . 124.52(9) yes C7 . N9 . C20 . 117.27(9) yes C10 . N9 . C20 . 115.60(8) yes N9 . C10 . C11 . 109.41(8) yes N9 . C10 . C13 . 110.69(9) yes C11 . C10 . C13 . 110.01(9) yes N9 . C10 . C14 . 105.64(8) yes C11 . C10 . C14 . 109.88(9) yes C13 . C10 . C14 . 111.12(9) yes C10 . C11 . C12 . 110.19(9) yes C10 . C11 . H111 . 108.3 no C12 . C11 . H111 . 107.5 no C10 . C11 . H112 . 108.3 no C12 . C11 . H112 . 112.0 no H111 . C11 . H112 . 110.5 no C11 . C12 . N6 . 107.31(8) yes C11 . C12 . H122 . 112.4 no N6 . C12 . H122 . 108.0 no C11 . C12 . H121 . 112.0 no N6 . C12 . H121 . 109.7 no H122 . C12 . H121 . 107.4 no C10 . C13 . H131 . 108.2 no C10 . C13 . H132 . 111.9 no H131 . C13 . H132 . 109.5 no C10 . C13 . H133 . 109.1 no H131 . C13 . H133 . 109.3 no H132 . C13 . H133 . 108.9 no C10 . C14 . N15 . 122.74(9) yes C10 . C14 . C18 . 126.60(9) yes N15 . C14 . C18 . 110.38(9) yes C14 . N15 . C16 . 108.17(9) yes C14 . N15 . H151 . 125.6 no C16 . N15 . H151 . 125.8 no N15 . C16 . C17 . 107.89(9) yes N15 . C16 . C24 . 130.05(11) yes C17 . C16 . C24 . 121.94(11) yes C16 . C17 . C18 . 106.83(9) yes C16 . C17 . C21 . 119.49(11) yes C18 . C17 . C21 . 133.61(11) yes C17 . C18 . C14 . 106.70(9) yes C17 . C18 . C19 . 130.67(10) yes C14 . C18 . C19 . 122.47(10) yes C18 . C19 . C20 . 109.07(10) yes C18 . C19 . H192 . 111.5 no C20 . C19 . H192 . 109.0 no C18 . C19 . H191 . 109.6 no C20 . C19 . H191 . 109.6 no H192 . C19 . H191 . 108.1 no C19 . C20 . N9 . 112.27(10) yes C19 . C20 . H201 . 110.7 no N9 . C20 . H201 . 107.1 no C19 . C20 . H202 . 108.6 no N9 . C20 . H202 . 107.1 no H201 . C20 . H202 . 111.0 no C17 . C21 . C22 . 118.50(13) yes C17 . C21 . H211 . 120.5 no C22 . C21 . H211 . 120.9 no C21 . C22 . C23 . 121.26(12) yes C21 . C22 . H221 . 119.4 no C23 . C22 . H221 . 119.4 no C22 . C23 . C24 . 121.64(12) yes C22 . C23 . H231 . 120.5 no C24 . C23 . H231 . 117.9 no C16 . C24 . C23 . 117.14(13) yes C16 . C24 . H241 . 120.8 no C23 . C24 . H241 . 122.0 no C5 . C25 . C26 . 120.52(11) yes C5 . C25 . H251 . 118.8 no C26 . C25 . H251 . 120.6 no C25 . C26 . C2 . 117.79(12) yes C25 . C26 . H261 . 121.6 no C2 . C26 . H261 . 120.6 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C11 . H112 . O8 1_655 144.67 0.957 2.490 3.3175(18) yes N15 . H151 . O8 1_655 163.90 0.856 1.970 2.8017(18) yes _iucr_refine_instruction_details_constraints ; # # Punched on 19/01/12 at 17:30:57 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 11,X'S) H ( 111,X'S) H ( 112,X'S) RIDE C ( 12,X'S) H ( 122,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) H ( 133,X'S) RIDE N ( 15,X'S) H ( 151,X'S) RIDE C ( 19,X'S) H ( 192,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 19/01/12 at 17:30:57 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ;