# 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_3a_dax41 #TrackingRef '17840_web_deposit_cif_file_0_DmitryYufit_1361176984.3a.cif' _audit_creation_date 2011-12-23 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; (3aRS,6aRS)-6a-Hydroxy-2-(4-methylphenyl)-3a-[4-(4-methylphenyl)- 2H-1,2,3-triazol-2-yl]-3,5,6,6a-tetrahydropyrrolo[3,4-b]pyrrole-4(3H)-one ; _chemical_formula_moiety 'C22 H21 N5 O2, C4 H8 O2' _chemical_formula_sum 'C26 H29 N5 O4' _chemical_formula_weight 475.54 _chemical_melting_point '194-200 C' 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 10.9436(5) _cell_length_b 11.0673(6) _cell_length_c 11.6719(5) _cell_angle_alpha 94.869(4) _cell_angle_beta 113.495(4) _cell_angle_gamma 104.707(4) _cell_volume 1226.08(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5233 _cell_measurement_temperature 120 _cell_measurement_theta_max 32.7898 _cell_measurement_theta_min 3.0213 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.91339 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 1.288 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.28 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_unetI/netI 0.0365 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 15824 _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 29.00 _diffrn_reflns_theta_min 3.03 _diffrn_ambient_temperature 120 _diffrn_detector CCD _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -103.00 -77.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -27.3632 -179.0000 90.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -92.00 -8.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -27.3632 -38.0000 30.0000 84 #__ type_ start__ end____ width___ exp.time_ 3 omega -71.00 -34.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -27.3632 -179.0000 -120.0000 37 #__ type_ start__ end____ width___ exp.time_ 4 omega -43.00 45.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -27.3632 38.0000 -150.0000 88 #__ type_ start__ end____ width___ exp.time_ 5 omega -40.00 -6.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -27.3632 -57.0000 60.0000 34 #__ type_ start__ end____ width___ exp.time_ 6 omega -63.00 -32.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -27.3632 179.0000 -180.0000 31 #__ type_ start__ end____ width___ exp.time_ 7 omega -104.00 -78.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -27.3632 179.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 5.00 69.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 27.9882 -100.0000 30.0000 64 #__ type_ start__ end____ width___ exp.time_ 9 omega 56.00 82.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 27.9882 179.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 10 omega 70.00 96.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 27.9882 77.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega -1.00 25.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 27.9882 77.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 44.00 70.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 27.9882 -100.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 13 omega -96.00 -71.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -27.3632 -57.0000 150.0000 25 #__ type_ start__ end____ width___ exp.time_ 14 omega -96.00 -6.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -27.3632 -57.0000 -120.0000 90 ; _diffrn_measurement_device '3-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method \w-scan _diffrn_orient_matrix_UB_11 0.0025908000 _diffrn_orient_matrix_UB_12 0.0610126000 _diffrn_orient_matrix_UB_13 0.0269996000 _diffrn_orient_matrix_UB_21 0.0691064000 _diffrn_orient_matrix_UB_22 0.0095575000 _diffrn_orient_matrix_UB_23 0.0470521000 _diffrn_orient_matrix_UB_31 0.0276031000 _diffrn_orient_matrix_UB_32 0.0279050000 _diffrn_orient_matrix_UB_33 -0.0406211000 _diffrn_radiation_collimation monochromator _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_xray_symbol Mo _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_type 'sealed tube' _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5298 _reflns_number_total 6486 _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.93 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.377 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.054 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 432 _refine_ls_number_reflns 6486 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0458 _refine_ls_restrained_S_all 1.010 _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^)+(0.0600P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1136 _refine_ls_wR_factor_ref 0.1232 _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 O1 O 0.47985(9) 0.38710(9) 0.10555(8) 0.01747(19) Uani 1 1 d . . . O2 O -0.00910(9) 0.32201(8) -0.03204(8) 0.01534(18) Uani 1 1 d . . . O3 O 0.57899(11) 0.82708(9) 0.29106(9) 0.0254(2) Uani 1 1 d . . . O4 O 0.6211(2) 0.64888(14) 0.34738(15) 0.0662(5) Uani 1 1 d . . . N1 N 0.31637(11) 0.46008(10) -0.04104(9) 0.0159(2) Uani 1 1 d . . . N2 N 0.15864(10) 0.51008(10) 0.11414(9) 0.0137(2) Uani 1 1 d . . . N3 N 0.19633(10) 0.19672(9) 0.03944(9) 0.0134(2) Uani 1 1 d . . . N4 N 0.19273(11) 0.11288(10) 0.11484(10) 0.0169(2) Uani 1 1 d . . . N5 N 0.17065(11) 0.14801(10) -0.07957(9) 0.0163(2) Uani 1 1 d . . . C1 C 0.36134(12) 0.39637(11) 0.05152(11) 0.0139(2) Uani 1 1 d . . . C2 C 0.23926(12) 0.33392(11) 0.08378(10) 0.0123(2) Uani 1 1 d . . . C3 C 0.27707(13) 0.37420(12) 0.22485(11) 0.0143(2) Uani 1 1 d . . . C4 C 0.23526(12) 0.49427(11) 0.22554(11) 0.0134(2) Uani 1 1 d . . . C5 C 0.12917(12) 0.40078(11) 0.01407(10) 0.0127(2) Uani 1 1 d . . . C6 C 0.16853(13) 0.44975(12) -0.08993(11) 0.0158(2) Uani 1 1 d . . . C7 C 0.27877(12) 0.58494(12) 0.34468(11) 0.0148(2) Uani 1 1 d . . . C8 C 0.28419(14) 0.71264(13) 0.34519(12) 0.0202(3) Uani 1 1 d . . . C9 C 0.32898(15) 0.79701(13) 0.45944(13) 0.0240(3) Uani 1 1 d . . . C10 C 0.36601(14) 0.75627(13) 0.57554(12) 0.0218(3) Uani 1 1 d . . . C11 C 0.35727(13) 0.62858(13) 0.57391(12) 0.0196(3) Uani 1 1 d . . . C12 C 0.31666(13) 0.54410(12) 0.46054(11) 0.0170(2) Uani 1 1 d . . . C13 C 0.41692(18) 0.84879(17) 0.69988(14) 0.0316(3) Uani 1 1 d . . . C14 C 0.15961(13) 0.00163(12) 0.03800(12) 0.0178(2) Uani 1 1 d . . . C15 C 0.14585(12) 0.02219(11) -0.08327(11) 0.0144(2) Uani 1 1 d . . . C16 C 0.10935(12) -0.06904(12) -0.19970(11) 0.0153(2) Uani 1 1 d . . . C17 C 0.10980(14) -0.02677(13) -0.30932(12) 0.0195(3) Uani 1 1 d . . . C18 C 0.07062(14) -0.11406(13) -0.42031(12) 0.0216(3) Uani 1 1 d . . . C19 C 0.02965(13) -0.24512(13) -0.42690(12) 0.0203(3) Uani 1 1 d . . . C20 C 0.03209(14) -0.28698(13) -0.31641(13) 0.0211(3) Uani 1 1 d . . . C21 C 0.07145(13) -0.20073(12) -0.20469(12) 0.0184(2) Uani 1 1 d . . . C22 C -0.01783(18) -0.33818(16) -0.54956(14) 0.0295(3) Uani 1 1 d . . . C23 C 0.6883(2) 0.83005(19) 0.51135(16) 0.0365(4) Uani 1 1 d . . . C24 C 0.62755(17) 0.75754(15) 0.37697(16) 0.0317(3) Uani 1 1 d . . . C25 C 0.5205(2) 0.76306(16) 0.15814(15) 0.0330(3) Uani 1 1 d . . . C26 C 0.4714(3) 0.8538(2) 0.07631(17) 0.0472(5) Uani 1 1 d . . . H1 H 0.3742(18) 0.5016(17) -0.0688(16) 0.029(4) Uiso 1 1 d . . . H2 H -0.062(2) 0.369(2) -0.0647(19) 0.046(6) Uiso 1 1 d . . . H3A H 0.3767(16) 0.3894(15) 0.2798(15) 0.019(4) Uiso 1 1 d . . . H3B H 0.2219(17) 0.3094(16) 0.2522(15) 0.022(4) Uiso 1 1 d . . . H6A H 0.1541(15) 0.5311(15) -0.0995(14) 0.016(4) Uiso 1 1 d . . . H6B H 0.1149(17) 0.3885(16) -0.1729(16) 0.024(4) Uiso 1 1 d . . . H8 H 0.2602(17) 0.7449(16) 0.2641(16) 0.025(4) Uiso 1 1 d . . . H9 H 0.3375(19) 0.8848(19) 0.4576(17) 0.034(5) Uiso 1 1 d . . . H11 H 0.3816(17) 0.6000(15) 0.6536(16) 0.024(4) Uiso 1 1 d . . . H12 H 0.3139(17) 0.4590(17) 0.4630(15) 0.026(4) Uiso 1 1 d . . . H13A H 0.503(3) 0.846(3) 0.762(3) 0.080(8) Uiso 1 1 d . . . H13B H 0.340(3) 0.835(3) 0.736(3) 0.099(10) Uiso 1 1 d . . . H13C H 0.425(3) 0.926(3) 0.688(3) 0.098(10) Uiso 1 1 d . . . H14 H 0.1479(17) -0.0760(17) 0.0692(16) 0.026(4) Uiso 1 1 d . . . H17 H 0.1380(16) 0.0629(16) -0.3086(14) 0.020(4) Uiso 1 1 d . . . H18 H 0.0710(19) -0.0797(18) -0.4952(18) 0.037(5) Uiso 1 1 d . . . H20 H 0.0008(18) -0.3795(18) -0.3193(16) 0.031(4) Uiso 1 1 d . . . H21 H 0.0719(17) -0.2321(16) -0.1269(16) 0.028(4) Uiso 1 1 d . . . H22A H -0.106(3) -0.398(3) -0.574(2) 0.082(8) Uiso 1 1 d . . . H22B H -0.033(3) -0.295(3) -0.619(3) 0.103(10) Uiso 1 1 d . . . H22C H 0.053(3) -0.381(3) -0.542(3) 0.084(8) Uiso 1 1 d . . . H23A H 0.625(3) 0.797(3) 0.551(3) 0.090(9) Uiso 1 1 d . . . H23B H 0.783(3) 0.822(2) 0.564(2) 0.074(8) Uiso 1 1 d . . . H23C H 0.699(3) 0.918(3) 0.518(3) 0.097(10) Uiso 1 1 d . . . H25A H 0.446(2) 0.684(2) 0.145(2) 0.061(7) Uiso 1 1 d . . . H25B H 0.598(2) 0.742(2) 0.146(2) 0.057(6) Uiso 1 1 d . . . H26A H 0.400(3) 0.872(2) 0.090(2) 0.062(7) Uiso 1 1 d . . . H26B H 0.428(3) 0.808(2) -0.012(2) 0.066(7) Uiso 1 1 d . . . H26C H 0.561(4) 0.938(3) 0.095(3) 0.110(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0155(4) 0.0196(5) 0.0184(4) 0.0054(3) 0.0072(3) 0.0070(3) O2 0.0130(4) 0.0137(4) 0.0162(4) 0.0027(3) 0.0036(3) 0.0040(3) O3 0.0336(5) 0.0202(5) 0.0268(5) 0.0070(4) 0.0154(4) 0.0109(4) O4 0.1182(14) 0.0335(7) 0.0578(9) 0.0194(7) 0.0354(9) 0.0433(9) N1 0.0168(5) 0.0180(5) 0.0152(5) 0.0059(4) 0.0085(4) 0.0061(4) N2 0.0144(4) 0.0133(5) 0.0123(4) 0.0011(4) 0.0048(4) 0.0048(4) N3 0.0165(5) 0.0130(5) 0.0107(4) 0.0018(4) 0.0057(4) 0.0055(4) N4 0.0209(5) 0.0143(5) 0.0159(5) 0.0053(4) 0.0076(4) 0.0063(4) N5 0.0208(5) 0.0154(5) 0.0130(5) 0.0011(4) 0.0077(4) 0.0063(4) C1 0.0161(5) 0.0125(5) 0.0126(5) 0.0002(4) 0.0065(4) 0.0040(4) C2 0.0141(5) 0.0122(5) 0.0114(5) 0.0026(4) 0.0055(4) 0.0058(4) C3 0.0172(5) 0.0157(6) 0.0107(5) 0.0024(4) 0.0054(4) 0.0076(4) C4 0.0129(5) 0.0138(5) 0.0137(5) 0.0023(4) 0.0061(4) 0.0044(4) C5 0.0135(5) 0.0127(5) 0.0112(5) 0.0020(4) 0.0044(4) 0.0052(4) C6 0.0183(6) 0.0184(6) 0.0117(5) 0.0050(4) 0.0062(4) 0.0074(5) C7 0.0140(5) 0.0157(6) 0.0132(5) 0.0002(4) 0.0046(4) 0.0056(4) C8 0.0242(6) 0.0185(6) 0.0160(6) 0.0021(5) 0.0060(5) 0.0089(5) C9 0.0293(7) 0.0167(6) 0.0211(6) -0.0011(5) 0.0058(5) 0.0096(5) C10 0.0195(6) 0.0254(7) 0.0158(6) -0.0036(5) 0.0032(5) 0.0092(5) C11 0.0184(6) 0.0259(7) 0.0131(5) 0.0017(5) 0.0046(5) 0.0092(5) C12 0.0181(6) 0.0173(6) 0.0142(5) 0.0022(5) 0.0049(4) 0.0071(5) C13 0.0358(8) 0.0314(8) 0.0176(6) -0.0081(6) 0.0014(6) 0.0156(7) C14 0.0224(6) 0.0154(6) 0.0170(6) 0.0043(5) 0.0089(5) 0.0072(5) C15 0.0139(5) 0.0128(5) 0.0163(5) 0.0023(4) 0.0066(4) 0.0043(4) C16 0.0149(5) 0.0152(6) 0.0146(5) 0.0003(4) 0.0059(4) 0.0046(4) C17 0.0242(6) 0.0157(6) 0.0187(6) 0.0031(5) 0.0095(5) 0.0064(5) C18 0.0277(7) 0.0225(7) 0.0162(6) 0.0042(5) 0.0105(5) 0.0089(5) C19 0.0204(6) 0.0218(6) 0.0171(6) -0.0014(5) 0.0072(5) 0.0072(5) C20 0.0257(6) 0.0144(6) 0.0223(6) 0.0007(5) 0.0110(5) 0.0049(5) C21 0.0230(6) 0.0152(6) 0.0182(6) 0.0028(5) 0.0106(5) 0.0055(5) C22 0.0373(8) 0.0266(8) 0.0204(7) -0.0053(6) 0.0114(6) 0.0082(6) C23 0.0433(9) 0.0401(10) 0.0326(8) 0.0166(7) 0.0164(7) 0.0210(8) C24 0.0389(8) 0.0260(8) 0.0408(8) 0.0163(7) 0.0225(7) 0.0157(6) C25 0.0458(9) 0.0232(8) 0.0297(8) -0.0001(6) 0.0178(7) 0.0100(7) C26 0.0661(13) 0.0508(12) 0.0247(8) 0.0015(8) 0.0116(8) 0.0339(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2315(14) . ? O2 C5 1.3931(14) . ? O2 H2 0.87(2) . ? O3 C24 1.3394(17) . ? O3 C25 1.4526(18) . ? O4 C24 1.199(2) . ? N1 C1 1.3372(15) . ? N1 C6 1.4544(16) . ? N1 H1 0.871(18) . ? N2 C4 1.2916(14) . ? N2 C5 1.4810(15) . ? N3 N4 1.3358(14) . ? N3 N5 1.3357(13) . ? N3 C2 1.4508(15) . ? N4 C14 1.3336(16) . ? N5 C15 1.3428(15) . ? C1 C2 1.5429(16) . ? C2 C3 1.5230(15) . ? C2 C5 1.5602(15) . ? C3 C4 1.5116(16) . ? C3 H3A 0.980(15) . ? C3 H3B 0.977(16) . ? C4 C7 1.4696(16) . ? C5 C6 1.5371(16) . ? C6 H6A 0.961(15) . ? C6 H6B 0.987(17) . ? C7 C8 1.3989(17) . ? C7 C12 1.3988(16) . ? C8 C9 1.3876(18) . ? C8 H8 1.000(16) . ? C9 C10 1.4009(19) . ? C9 H9 0.955(19) . ? C10 C11 1.3900(19) . ? C10 C13 1.5095(18) . ? C11 C12 1.3902(17) . ? C11 H11 0.965(16) . ? C12 H12 0.938(17) . ? C13 H13A 0.94(3) . ? C13 H13B 1.06(3) . ? C13 H13C 0.87(3) . ? C14 C15 1.4072(16) . ? C14 H14 0.960(17) . ? C15 C16 1.4681(16) . ? C16 C17 1.4004(17) . ? C16 C21 1.3996(17) . ? C17 C18 1.3892(18) . ? C17 H17 0.960(16) . ? C18 C19 1.3908(19) . ? C18 H18 0.984(19) . ? C19 C20 1.3996(18) . ? C19 C22 1.5050(18) . ? C20 C21 1.3890(18) . ? C20 H20 0.987(18) . ? C21 H21 0.998(17) . ? C22 H22A 0.94(3) . ? C22 H22B 0.96(3) . ? C22 H22C 0.99(3) . ? C23 C24 1.493(2) . ? C23 H23A 0.99(3) . ? C23 H23B 1.00(3) . ? C23 H23C 0.94(3) . ? C25 C26 1.496(2) . ? C25 H25A 0.99(2) . ? C25 H25B 0.99(2) . ? C26 H26A 0.92(3) . ? C26 H26B 0.97(3) . ? C26 H26C 1.10(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O2 H2 106.5(14) . . ? C24 O3 C25 115.46(12) . . ? C1 N1 C6 115.01(10) . . ? C1 N1 H1 119.7(11) . . ? C6 N1 H1 125.2(11) . . ? C4 N2 C5 110.20(9) . . ? N4 N3 C2 123.71(9) . . ? N5 N3 N4 115.75(10) . . ? N5 N3 C2 120.24(9) . . ? C14 N4 N3 103.12(10) . . ? N3 N5 C15 103.84(9) . . ? O1 C1 N1 127.46(11) . . ? O1 C1 C2 123.55(10) . . ? N1 C1 C2 108.99(10) . . ? N3 C2 C1 108.17(9) . . ? N3 C2 C3 113.61(9) . . ? N3 C2 C5 115.82(9) . . ? C1 C2 C5 102.17(9) . . ? C3 C2 C1 112.00(9) . . ? C3 C2 C5 104.56(9) . . ? C2 C3 H3A 112.5(9) . . ? C2 C3 H3B 110.9(9) . . ? C4 C3 C2 101.06(9) . . ? C4 C3 H3A 112.9(9) . . ? C4 C3 H3B 111.0(10) . . ? H3A C3 H3B 108.3(12) . . ? N2 C4 C3 114.86(10) . . ? N2 C4 C7 123.13(11) . . ? C7 C4 C3 122.00(10) . . ? O2 C5 N2 110.41(9) . . ? O2 C5 C2 113.25(9) . . ? O2 C5 C6 114.04(9) . . ? N2 C5 C2 103.55(8) . . ? N2 C5 C6 109.87(9) . . ? C6 C5 C2 105.11(9) . . ? N1 C6 C5 102.96(9) . . ? N1 C6 H6A 111.6(9) . . ? N1 C6 H6B 109.7(10) . . ? C5 C6 H6A 110.6(9) . . ? C5 C6 H6B 111.9(9) . . ? H6A C6 H6B 109.9(13) . . ? C8 C7 C4 121.28(11) . . ? C8 C7 C12 118.81(11) . . ? C12 C7 C4 119.90(11) . . ? C7 C8 H8 120.5(10) . . ? C9 C8 C7 120.11(12) . . ? C9 C8 H8 119.4(10) . . ? C8 C9 C10 121.23(12) . . ? C8 C9 H9 118.2(11) . . ? C10 C9 H9 120.5(11) . . ? C9 C10 C13 121.07(13) . . ? C11 C10 C9 118.32(12) . . ? C11 C10 C13 120.60(12) . . ? C10 C11 C12 120.92(12) . . ? C10 C11 H11 118.5(10) . . ? C12 C11 H11 120.6(10) . . ? C7 C12 H12 120.7(10) . . ? C11 C12 C7 120.56(12) . . ? C11 C12 H12 118.8(10) . . ? C10 C13 H13A 112.5(16) . . ? C10 C13 H13B 111.8(17) . . ? C10 C13 H13C 111(2) . . ? H13A C13 H13B 111(2) . . ? H13A C13 H13C 110(3) . . ? H13B C13 H13C 101(2) . . ? N4 C14 C15 109.57(11) . . ? N4 C14 H14 119.9(10) . . ? C15 C14 H14 130.5(10) . . ? N5 C15 C14 107.71(10) . . ? N5 C15 C16 121.98(10) . . ? C14 C15 C16 130.31(11) . . ? C17 C16 C15 120.92(11) . . ? C21 C16 C15 120.90(11) . . ? C21 C16 C17 118.18(11) . . ? C16 C17 H17 120.5(9) . . ? C18 C17 C16 120.45(12) . . ? C18 C17 H17 119.1(9) . . ? C17 C18 C19 121.69(12) . . ? C17 C18 H18 117.4(11) . . ? C19 C18 H18 120.9(11) . . ? C18 C19 C20 117.70(12) . . ? C18 C19 C22 120.86(12) . . ? C20 C19 C22 121.43(13) . . ? C19 C20 H20 119.2(10) . . ? C21 C20 C19 121.18(12) . . ? C21 C20 H20 119.5(10) . . ? C16 C21 H21 119.0(10) . . ? C20 C21 C16 120.76(11) . . ? C20 C21 H21 120.2(10) . . ? C19 C22 H22A 112.4(16) . . ? C19 C22 H22B 110.3(19) . . ? C19 C22 H22C 110.2(16) . . ? H22A C22 H22B 103(2) . . ? H22A C22 H22C 111(2) . . ? H22B C22 H22C 110(2) . . ? C24 C23 H23A 109.7(17) . . ? C24 C23 H23B 111.4(15) . . ? C24 C23 H23C 113.8(18) . . ? H23A C23 H23B 109(2) . . ? H23A C23 H23C 106(2) . . ? H23B C23 H23C 107(2) . . ? O3 C24 C23 112.52(13) . . ? O4 C24 O3 122.86(16) . . ? O4 C24 C23 124.62(15) . . ? O3 C25 C26 108.22(13) . . ? O3 C25 H25A 106.9(13) . . ? O3 C25 H25B 106.5(13) . . ? C26 C25 H25A 114.5(13) . . ? C26 C25 H25B 110.4(13) . . ? H25A C25 H25B 110.0(19) . . ? C25 C26 H26A 108.5(14) . . ? C25 C26 H26B 107.3(14) . . ? C25 C26 H26C 109.5(17) . . ? H26A C26 H26B 105(2) . . ? H26A C26 H26C 115(2) . . ? H26B C26 H26C 111(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.871(18) 1.972(18) 2.8356(14) 171.2(16) 2_665 O2 H2 N2 0.87(2) 1.90(2) 2.7651(13) 171(2) 2_565 _database_code_depnum_ccdc_archive 'CCDC 924896' ####################################################################### # # 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_3b_dax49 #TrackingRef '17841_web_deposit_cif_file_1_DmitryYufit_1361176984.3b.cif' _audit_creation_date 2012-02-24 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.01.17 svn.r2163, GUI svn.r4036) ; _chemical_name_common ? _chemical_name_systematic ; (3aRS,6aRS)-5-Acetyl-6a-hydroxy-2-(4-methylphenyl)-3a-[4- -(4-methylphenyl)-2H-1,2,3-triazol-2-yl]-3,5,6,6a-tetrahydropyrrolo[3,4-b] pyrrol-4(3H)-one ethyl acetate solvate (1:1) ; _chemical_formula_moiety 'C24 H23 N5 O3, C2 H4 O' _chemical_formula_sum 'C26 H27 N5 O4' _chemical_formula_weight 473.53 _chemical_melting_point '188-193 C' 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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.883(2) _cell_length_b 17.0326(17) _cell_length_c 14.7571(15) _cell_angle_alpha 90.00 _cell_angle_beta 124.209(2) _cell_angle_gamma 90.00 _cell_volume 4756.6(8) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4365 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.33 _cell_measurement_theta_min 2.39 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _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 1.322 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 2000 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (5 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_unetI/netI 0.0524 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 22209 _diffrn_reflns_theta_full 28.50 _diffrn_reflns_theta_max 28.50 _diffrn_reflns_theta_min 1.61 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3598 _reflns_number_total 6031 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.639 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.054 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 373 _refine_ls_number_reflns 6031 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0564 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1507 _refine_ls_wR_factor_ref 0.1688 _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. The solvent ethyl acetate molecule is disordered over two positions (except terminal Me atoms) and was refined with fixed SOF = 0.5 ; _atom_sites_solution_hydrogens difmap _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 O1 O 0.23677(7) 0.57672(8) 0.33821(11) 0.0368(3) Uani 1 1 d . . . O2 O 0.48007(7) 0.54470(8) 0.61845(11) 0.0326(3) Uani 1 1 d . . . O3 O 0.28327(8) 0.64204(9) 0.64423(12) 0.0469(4) Uani 1 1 d . . . N1 N 0.30716(8) 0.59266(9) 0.52759(12) 0.0303(4) Uani 1 1 d . . . N2 N 0.40022(8) 0.44119(9) 0.58529(12) 0.0294(3) Uani 1 1 d . . . N3 N 0.38700(8) 0.59302(9) 0.40115(13) 0.0322(4) Uani 1 1 d . . . N4 N 0.43334(10) 0.57395(10) 0.37703(14) 0.0399(4) Uani 1 1 d . . . N5 N 0.37548(8) 0.66985(9) 0.40092(12) 0.0315(4) Uani 1 1 d . . . C1 C 0.36010(10) 0.53740(11) 0.44312(15) 0.0304(4) Uani 1 1 d . . . C2 C 0.29268(10) 0.57193(10) 0.42579(15) 0.0292(4) Uani 1 1 d . . . C3 C 0.38011(10) 0.57620(13) 0.61925(16) 0.0341(4) Uani 1 1 d . . . C4 C 0.40969(10) 0.52410(11) 0.57039(14) 0.0290(4) Uani 1 1 d . . . C5 C 0.36513(10) 0.40584(11) 0.49214(15) 0.0296(4) Uani 1 1 d . . . C6 C 0.34643(13) 0.45543(12) 0.39399(17) 0.0353(5) Uani 1 1 d . . . C7 C 0.26210(11) 0.63034(12) 0.54934(17) 0.0377(5) Uani 1 1 d . . . C8 C 0.19139(13) 0.65654(19) 0.4549(2) 0.0642(8) Uani 1 1 d . . . H8A H 0.1611 0.6117 0.4213 0.096 Uiso 1 1 calc R . . H8B H 0.1966 0.6827 0.4022 0.096 Uiso 1 1 calc R . . H8C H 0.1710 0.6920 0.4803 0.096 Uiso 1 1 calc R . . C9 C 0.45161(12) 0.64277(13) 0.35799(17) 0.0406(5) Uani 1 1 d . . . C10 C 0.41605(10) 0.70303(12) 0.37206(15) 0.0337(4) Uani 1 1 d . . . C11 C 0.41983(10) 0.78779(12) 0.36088(15) 0.0351(5) Uani 1 1 d . . . C12 C 0.47774(12) 0.82005(14) 0.36687(19) 0.0458(5) Uani 1 1 d . . . C13 C 0.48306(13) 0.89982(16) 0.3587(2) 0.0542(6) Uani 1 1 d . . . C14 C 0.43116(12) 0.95085(14) 0.34489(19) 0.0500(6) Uani 1 1 d . . . C15 C 0.37358(13) 0.91813(13) 0.33872(18) 0.0444(5) Uani 1 1 d . . . C16 C 0.36740(11) 0.83785(12) 0.34672(16) 0.0365(5) Uani 1 1 d . . . C17 C 0.43898(15) 1.03785(15) 0.3388(2) 0.0686(8) Uani 1 1 d . . . H17A H 0.4438 1.0493 0.2796 0.103 Uiso 1 1 calc R . . H17B H 0.4802 1.0558 0.4065 0.103 Uiso 1 1 calc R . . H17C H 0.3980 1.0640 0.3265 0.103 Uiso 1 1 calc R . . C18 C 0.34517(10) 0.32270(11) 0.48199(15) 0.0303(4) Uani 1 1 d . . . C19 C 0.31426(11) 0.28342(12) 0.38207(16) 0.0363(5) Uani 1 1 d . . . C20 C 0.29533(12) 0.20509(13) 0.37317(18) 0.0409(5) Uani 1 1 d . . . C21 C 0.30549(11) 0.16421(12) 0.46208(18) 0.0386(5) Uani 1 1 d . . . C22 C 0.33600(11) 0.20363(13) 0.56155(17) 0.0372(5) Uani 1 1 d . . . C23 C 0.35551(10) 0.28163(12) 0.57207(16) 0.0336(4) Uani 1 1 d . . . C24 C 0.28330(14) 0.07983(13) 0.4508(2) 0.0541(6) Uani 1 1 d . . . H24A H 0.3056 0.0567 0.5223 0.081 Uiso 1 1 calc R . . H24B H 0.2973 0.0518 0.4095 0.081 Uiso 1 1 calc R . . H24C H 0.2329 0.0770 0.4136 0.081 Uiso 1 1 calc R . . H2 H 0.5009(13) 0.5109(14) 0.609(2) 0.049(7) Uiso 1 1 d . . . H3A H 0.4053(11) 0.6245(12) 0.6419(17) 0.031(5) Uiso 1 1 d . . . H3B H 0.3827(12) 0.5474(12) 0.6830(19) 0.042(6) Uiso 1 1 d . . . H6A H 0.2968(13) 0.4483(13) 0.332(2) 0.044(6) Uiso 1 1 d . . . H6B H 0.3752(13) 0.4419(13) 0.365(2) 0.052(7) Uiso 1 1 d . . . H9 H 0.4874(13) 0.6455(12) 0.3406(19) 0.048(6) Uiso 1 1 d . . . H12 H 0.5114(13) 0.7860(14) 0.3706(19) 0.050(7) Uiso 1 1 d . . . H13 H 0.5276(12) 0.9222(12) 0.3639(17) 0.038(6) Uiso 1 1 d . . . H15 H 0.3348(14) 0.9512(14) 0.327(2) 0.057(7) Uiso 1 1 d . . . H16 H 0.3262(12) 0.8156(12) 0.3451(17) 0.041(6) Uiso 1 1 d . . . H19 H 0.3077(10) 0.3135(11) 0.3226(17) 0.031(5) Uiso 1 1 d . . . H20 H 0.2715(12) 0.1791(13) 0.3002(19) 0.048(6) Uiso 1 1 d . . . H22 H 0.3442(12) 0.1751(14) 0.624(2) 0.052(7) Uiso 1 1 d . . . H23 H 0.3778(10) 0.3100(11) 0.6456(17) 0.031(5) Uiso 1 1 d . . . O1S O 0.4664(3) 0.8075(3) 0.6484(4) 0.0823(15) Uiso 0.50 1 d P A -1 O2S O 0.54598(15) 0.74972(15) 0.8010(2) 0.0379(6) Uiso 0.50 1 d P A -1 C1S C 0.54927(13) 0.73401(15) 0.6551(2) 0.0542(6) Uani 1 1 d . A -1 H1SA H 0.5968 0.7538 0.6954 0.081 Uiso 1 1 d R A -1 H1SB H 0.5501 0.6781 0.6638 0.081 Uiso 1 1 d R A -1 H1SC H 0.5262 0.7466 0.5789 0.081 Uiso 1 1 d R A -1 C2S C 0.5145(2) 0.7661(2) 0.6930(4) 0.0356(9) Uiso 0.50 1 d P A -1 C3S C 0.5248(3) 0.7811(4) 0.8645(5) 0.0515(14) Uiso 0.50 1 d P A -1 H3SA H 0.5468 0.7683 0.9325 0.062 Uiso 0.50 1 d PR A -1 H3SB H 0.4897 0.8132 0.8365 0.062 Uiso 0.50 1 d PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0303(8) 0.0459(8) 0.0255(7) 0.0027(6) 0.0104(7) 0.0016(6) O2 0.0270(7) 0.0347(7) 0.0345(8) -0.0045(6) 0.0164(7) 0.0023(6) O3 0.0367(9) 0.0722(11) 0.0326(8) -0.0049(7) 0.0199(8) 0.0123(7) N1 0.0249(8) 0.0390(9) 0.0236(8) -0.0002(6) 0.0115(7) 0.0061(7) N2 0.0241(8) 0.0378(9) 0.0234(8) -0.0004(6) 0.0117(7) 0.0029(6) N3 0.0346(9) 0.0372(9) 0.0285(9) 0.0020(7) 0.0201(8) 0.0091(7) N4 0.0444(10) 0.0504(11) 0.0362(10) 0.0100(8) 0.0294(9) 0.0167(8) N5 0.0295(9) 0.0375(9) 0.0278(8) 0.0039(7) 0.0163(8) 0.0080(7) C1 0.0317(10) 0.0342(10) 0.0247(10) 0.0009(7) 0.0155(9) 0.0055(8) C2 0.0293(10) 0.0311(9) 0.0241(10) 0.0030(7) 0.0131(9) 0.0025(7) C3 0.0266(10) 0.0455(12) 0.0253(10) -0.0041(9) 0.0116(9) 0.0062(9) C4 0.0245(10) 0.0365(10) 0.0222(9) -0.0004(7) 0.0108(8) 0.0034(7) C5 0.0245(9) 0.0393(10) 0.0248(10) 0.0020(7) 0.0138(8) 0.0067(8) C6 0.0443(13) 0.0348(10) 0.0254(10) -0.0013(8) 0.0187(10) 0.0050(9) C7 0.0303(11) 0.0492(12) 0.0347(11) -0.0002(9) 0.0190(10) 0.0061(9) C8 0.0420(14) 0.105(2) 0.0431(14) 0.0068(13) 0.0223(12) 0.0306(14) C9 0.0403(12) 0.0548(13) 0.0360(12) 0.0141(9) 0.0271(11) 0.0172(10) C10 0.0287(10) 0.0470(12) 0.0257(10) 0.0098(8) 0.0155(9) 0.0094(8) C11 0.0296(11) 0.0479(12) 0.0266(10) 0.0096(8) 0.0151(9) 0.0069(8) C12 0.0338(12) 0.0573(14) 0.0465(14) 0.0164(11) 0.0227(11) 0.0093(10) C13 0.0379(13) 0.0656(16) 0.0514(15) 0.0182(12) 0.0203(12) 0.0008(12) C14 0.0396(13) 0.0519(13) 0.0366(13) 0.0115(10) 0.0080(11) 0.0011(10) C15 0.0388(13) 0.0482(13) 0.0342(12) 0.0050(9) 0.0133(11) 0.0105(10) C16 0.0313(11) 0.0461(12) 0.0307(11) 0.0052(9) 0.0166(9) 0.0058(9) C17 0.0558(17) 0.0562(16) 0.0631(18) 0.0136(13) 0.0146(15) -0.0033(12) C18 0.0235(9) 0.0390(10) 0.0256(9) -0.0006(8) 0.0121(8) 0.0035(8) C19 0.0393(12) 0.0413(11) 0.0285(11) -0.0009(8) 0.0192(10) 0.0027(9) C20 0.0412(12) 0.0440(12) 0.0382(12) -0.0112(9) 0.0226(11) -0.0054(9) C21 0.0322(11) 0.0414(11) 0.0475(13) -0.0039(9) 0.0257(11) -0.0003(8) C22 0.0344(11) 0.0433(12) 0.0353(11) 0.0038(9) 0.0203(10) 0.0020(9) C23 0.0301(11) 0.0415(11) 0.0284(10) -0.0011(8) 0.0160(9) 0.0010(8) C24 0.0583(16) 0.0445(13) 0.0680(17) -0.0092(11) 0.0407(15) -0.0080(11) C1S 0.0496(15) 0.0550(14) 0.0410(14) 0.0065(11) 0.0150(12) -0.0080(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.206(2) . ? O2 C4 1.391(2) . ? O2 H2 0.81(3) . ? O3 C7 1.214(2) . ? N1 C2 1.390(2) . ? N1 C3 1.468(2) . ? N1 C7 1.397(2) . ? N2 C4 1.464(2) . ? N2 C5 1.287(2) . ? N3 N4 1.335(2) . ? N3 N5 1.335(2) . ? N3 C1 1.445(2) . ? N4 C9 1.327(3) . ? N5 C10 1.344(2) . ? C1 C2 1.532(3) . ? C1 C4 1.572(3) . ? C1 C6 1.522(3) . ? C3 C4 1.521(3) . ? C3 H3A 0.95(2) . ? C3 H3B 1.03(2) . ? C5 C6 1.516(3) . ? C5 C18 1.470(3) . ? C6 H6A 0.98(2) . ? C6 H6B 1.00(3) . ? C7 C8 1.491(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.396(3) . ? C9 H9 0.99(2) . ? C10 C11 1.461(3) . ? C11 C12 1.391(3) . ? C11 C16 1.389(3) . ? C12 C13 1.375(3) . ? C12 H12 0.94(2) . ? C13 C14 1.391(4) . ? C13 H13 1.05(2) . ? C14 C15 1.386(3) . ? C14 C17 1.501(3) . ? C15 C16 1.386(3) . ? C15 H15 0.98(3) . ? C16 H16 1.00(2) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.396(3) . ? C18 C23 1.399(3) . ? C19 C20 1.386(3) . ? C19 H19 0.95(2) . ? C20 C21 1.385(3) . ? C20 H20 1.00(2) . ? C21 C22 1.393(3) . ? C21 C24 1.502(3) . ? C22 C23 1.382(3) . ? C22 H22 0.96(2) . ? C23 H23 1.02(2) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? O1S C2S 1.152(7) . ? O2S C2S 1.358(5) . ? O2S C3S 1.383(6) . ? C1S H1SA 0.9602 . ? C1S H1SB 0.9598 . ? C1S H1SC 0.9601 . ? C1S C2S 1.321(5) . ? C3S H3SA 0.8601 . ? C3S H3SB 0.8599 . ? 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 C4 O2 H2 111.0(18) . . ? C2 N1 C3 113.83(15) . . ? C2 N1 C7 127.37(16) . . ? C7 N1 C3 118.68(15) . . ? C5 N2 C4 110.31(15) . . ? N4 N3 C1 123.26(15) . . ? N5 N3 N4 115.06(16) . . ? N5 N3 C1 120.85(14) . . ? C9 N4 N3 103.52(16) . . ? N3 N5 C10 104.02(15) . . ? N3 C1 C2 107.96(14) . . ? N3 C1 C4 114.29(16) . . ? N3 C1 C6 114.84(15) . . ? C2 C1 C4 103.74(14) . . ? C6 C1 C2 110.76(17) . . ? C6 C1 C4 104.70(15) . . ? O1 C2 N1 127.29(18) . . ? O1 C2 C1 124.53(17) . . ? N1 C2 C1 108.13(15) . . ? N1 C3 C4 104.66(15) . . ? N1 C3 H3A 108.1(12) . . ? N1 C3 H3B 112.6(13) . . ? C4 C3 H3A 109.1(12) . . ? C4 C3 H3B 109.9(12) . . ? H3A C3 H3B 112.2(18) . . ? O2 C4 N2 113.17(15) . . ? O2 C4 C1 115.08(15) . . ? O2 C4 C3 107.90(15) . . ? N2 C4 C1 104.49(14) . . ? N2 C4 C3 110.41(16) . . ? C3 C4 C1 105.52(14) . . ? N2 C5 C6 115.56(17) . . ? N2 C5 C18 122.09(16) . . ? C18 C5 C6 122.34(16) . . ? C1 C6 H6A 111.9(13) . . ? C1 C6 H6B 114.2(13) . . ? C5 C6 C1 100.60(15) . . ? C5 C6 H6A 111.9(13) . . ? C5 C6 H6B 112.7(13) . . ? H6A C6 H6B 105.8(19) . . ? O3 C7 N1 118.25(18) . . ? O3 C7 C8 123.29(19) . . ? N1 C7 C8 118.42(18) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C9 C10 109.79(18) . . ? N4 C9 H9 120.2(13) . . ? C10 C9 H9 129.9(13) . . ? N5 C10 C9 107.60(18) . . ? N5 C10 C11 123.11(17) . . ? C9 C10 C11 129.29(18) . . ? C12 C11 C10 119.86(18) . . ? C16 C11 C10 121.52(18) . . ? C16 C11 C12 118.6(2) . . ? C11 C12 H12 118.7(14) . . ? C13 C12 C11 120.8(2) . . ? C13 C12 H12 120.3(14) . . ? C12 C13 C14 121.3(2) . . ? C12 C13 H13 118.8(11) . . ? C14 C13 H13 119.9(11) . . ? C13 C14 C17 120.3(2) . . ? C15 C14 C13 117.4(2) . . ? C15 C14 C17 122.3(2) . . ? C14 C15 C16 122.0(2) . . ? C14 C15 H15 121.0(14) . . ? C16 C15 H15 117.0(14) . . ? C11 C16 H16 119.5(12) . . ? C15 C16 C11 119.8(2) . . ? C15 C16 H16 120.6(12) . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C5 120.88(17) . . ? C19 C18 C23 118.58(18) . . ? C23 C18 C5 120.53(17) . . ? C18 C19 H19 116.0(12) . . ? C20 C19 C18 120.47(19) . . ? C20 C19 H19 123.5(12) . . ? C19 C20 H20 118.8(13) . . ? C21 C20 C19 121.14(19) . . ? C21 C20 H20 120.0(13) . . ? C20 C21 C22 118.3(2) . . ? C20 C21 C24 120.68(19) . . ? C22 C21 C24 121.0(2) . . ? C21 C22 H22 118.5(14) . . ? C23 C22 C21 121.36(19) . . ? C23 C22 H22 120.1(14) . . ? C18 C23 H23 119.2(11) . . ? C22 C23 C18 120.15(18) . . ? C22 C23 H23 120.7(11) . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C2S O2S C3S 124.0(4) . . ? H1SA C1S H1SB 109.6 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? C2S C1S H1SA 109.5 . . ? C2S C1S H1SB 108.9 . . ? C2S C1S H1SC 109.8 . . ? O1S C2S O2S 120.1(4) . . ? O1S C2S C1S 128.3(5) . . ? C1S C2S O2S 111.3(4) . . ? O2S C3S H3SA 119.5 . . ? O2S C3S H3SB 120.5 . . ? H3SA C3S H3SB 120.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 N4 0.81(3) 2.01(3) 2.805(2) 167(2) 5_666 # start Validation Reply Form _vrf_PLAT412_I ; PROBLEM: Short Intra XH3 .. XHn H1SC .. H3SA .. 1.62 Ang. RESPONSE: This short contact exists between hydrogen atoms of different components of disordered solvent molecule (refined with fixed SOF=0.5) and is not real. ; _database_code_depnum_ccdc_archive 'CCDC 924897' ####################################################################### # # 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_6a_DAX13_SAD _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C22 H20 N4 O3' _chemical_formula_sum 'C22 H20 N4 O3' _chemical_formula_weight 388.42 _chemical_melting_point '203-204 c' _chemical_name_common ? _chemical_name_systematic ; (3aRS,6aSR)-6a-Hydroxy-2-(4-methylphenyl)-3a-[4-(4-methylphenyl)- 1,2,3-triazol-2-yl]-6,6a-dihydro-3H-furo[3,4-b]pyrrol-4(3aH)-one ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, z' 'x-1/2, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 100.571(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.2557(3) _cell_length_b 7.9016(2) _cell_length_c 21.4436(6) _cell_measurement_reflns_used 5039 _cell_measurement_temperature 120 _cell_measurement_theta_max 31.911 _cell_measurement_theta_min 3.136 _cell_volume 1874.78(9) _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.3833 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0365 before and 0.0252 after correction. The Ratio of minimum to maximum transmission is 0.3833. The \l/2 correction factor is 0.0015 ; _exptl_crystal_F_000 816 _exptl_crystal_colour less _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_special_details ? _diffrn_ambient_temperature 120.0 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 20470 _diffrn_reflns_theta_full 29.50 _diffrn_reflns_theta_max 29.50 _diffrn_reflns_theta_min 1.92 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3865 _reflns_number_total 5197 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 0.434 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.057 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0462 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 342 _refine_ls_number_reflns 5197 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1201 _refine_ls_wR_factor_ref 0.1358 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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 difmap _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 O1 O 0.79209(9) 0.52141(12) 0.48828(4) 0.0235(2) Uani 1 1 d . . . O2 O 0.64965(9) 0.12186(12) 0.47199(5) 0.0267(2) Uani 1 1 d . . . O3 O 0.79173(10) -0.07947(13) 0.48312(5) 0.0299(2) Uani 1 1 d . . . N1 N 0.76287(10) 0.37120(14) 0.39029(5) 0.0210(2) Uani 1 1 d . . . N2 N 0.91482(10) 0.23721(14) 0.54754(5) 0.0204(2) Uani 1 1 d . . . N3 N 1.01856(10) 0.32027(14) 0.56488(5) 0.0218(2) Uani 1 1 d . . . N4 N 0.85581(10) 0.20079(14) 0.59455(5) 0.0218(2) Uani 1 1 d . . . C1 C 0.76523(12) 0.36565(16) 0.45886(6) 0.0203(3) Uani 1 1 d . . . C2 C 0.64502(13) 0.30481(18) 0.47368(7) 0.0247(3) Uani 1 1 d . . . C3 C 0.76512(12) 0.06680(17) 0.48076(6) 0.0229(3) Uani 1 1 d . . . C4 C 0.85269(12) 0.21730(16) 0.48265(6) 0.0198(2) Uani 1 1 d . . . C5 C 0.93067(12) 0.19706(17) 0.43244(6) 0.0214(3) Uani 1 1 d . . . C6 C 0.84916(12) 0.27977(15) 0.37647(6) 0.0188(2) Uani 1 1 d . . . C7 C 0.86933(12) 0.26259(15) 0.31091(6) 0.0189(2) Uani 1 1 d . . . C8 C 0.79319(12) 0.34385(17) 0.26057(6) 0.0216(3) Uani 1 1 d . . . C9 C 0.81581(12) 0.33080(17) 0.19913(6) 0.0227(3) Uani 1 1 d . . . C10 C 0.91376(12) 0.23674(16) 0.18579(6) 0.0209(3) Uani 1 1 d . . . C11 C 0.98719(12) 0.15409(17) 0.23586(6) 0.0224(3) Uani 1 1 d . . . C12 C 0.96632(12) 0.16697(17) 0.29761(6) 0.0215(3) Uani 1 1 d . . . C13 C 0.94097(15) 0.22709(19) 0.11980(6) 0.0265(3) Uani 1 1 d . . . C14 C 1.02945(12) 0.33304(17) 0.62777(6) 0.0218(3) Uani 1 1 d . . . C15 C 0.92782(12) 0.26023(16) 0.64672(6) 0.0197(3) Uani 1 1 d . . . C16 C 0.89678(12) 0.24728(15) 0.70990(6) 0.0197(3) Uani 1 1 d . . . C17 C 0.97243(13) 0.31807(18) 0.76218(6) 0.0241(3) Uani 1 1 d . . . C18 C 0.94102(14) 0.31176(18) 0.82182(6) 0.0271(3) Uani 1 1 d . . . C19 C 0.83519(14) 0.23326(18) 0.83117(7) 0.0274(3) Uani 1 1 d . . . C20 C 0.76121(13) 0.15964(18) 0.77879(7) 0.0259(3) Uani 1 1 d . . . C21 C 0.79053(12) 0.16728(17) 0.71876(6) 0.0226(3) Uani 1 1 d . . . C22 C 0.7996(2) 0.2312(3) 0.89545(8) 0.0445(4) Uani 1 1 d . . . H1 H 0.850(2) 0.571(3) 0.4720(10) 0.054(6) Uiso 1 1 d . . . H2B H 0.6351(15) 0.339(2) 0.5158(8) 0.023(4) Uiso 1 1 d . . . H2A H 0.5734(16) 0.343(2) 0.4428(8) 0.027(4) Uiso 1 1 d . . . H5B H 1.0054(16) 0.2581(19) 0.4431(8) 0.021(4) Uiso 1 1 d . . . H5A H 0.9465(15) 0.078(2) 0.4256(8) 0.025(4) Uiso 1 1 d . . . H8 H 0.7235(15) 0.415(2) 0.2686(8) 0.028(4) Uiso 1 1 d . . . H9 H 0.7644(15) 0.391(2) 0.1640(8) 0.027(4) Uiso 1 1 d . . . H11 H 1.0556(15) 0.088(2) 0.2274(8) 0.026(4) Uiso 1 1 d . . . H12 H 1.0207(15) 0.106(2) 0.3313(8) 0.027(4) Uiso 1 1 d . . . H13C H 0.978(2) 0.332(3) 0.1061(12) 0.075(8) Uiso 1 1 d . . . H13B H 0.998(2) 0.131(3) 0.1151(11) 0.065(7) Uiso 1 1 d . . . H13A H 0.870(2) 0.212(3) 0.0887(12) 0.065(7) Uiso 1 1 d . . . H14 H 1.0996(15) 0.382(2) 0.6523(8) 0.026(4) Uiso 1 1 d . . . H17 H 1.0475(17) 0.373(2) 0.7589(8) 0.033(5) Uiso 1 1 d . . . H18 H 0.9939(16) 0.363(2) 0.8576(9) 0.035(5) Uiso 1 1 d . . . H20 H 0.6875(16) 0.100(2) 0.7840(8) 0.031(4) Uiso 1 1 d . . . H21 H 0.7386(15) 0.115(2) 0.6825(8) 0.027(4) Uiso 1 1 d . . . H22C H 0.862(3) 0.247(4) 0.9290(19) 0.117(13) Uiso 1 1 d . . . H22B H 0.740(3) 0.323(4) 0.8985(15) 0.104(11) Uiso 1 1 d . . . H22A H 0.755(3) 0.135(4) 0.9017(15) 0.103(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0296(5) 0.0207(4) 0.0215(4) -0.0032(3) 0.0086(4) -0.0021(4) O2 0.0258(5) 0.0255(5) 0.0285(5) -0.0001(4) 0.0040(4) -0.0055(4) O3 0.0401(6) 0.0225(5) 0.0253(5) -0.0005(4) 0.0014(4) -0.0020(4) N1 0.0235(5) 0.0218(5) 0.0177(5) -0.0006(4) 0.0034(4) 0.0004(4) N2 0.0209(5) 0.0237(5) 0.0162(5) -0.0002(4) 0.0027(4) -0.0023(4) N3 0.0212(5) 0.0244(5) 0.0193(5) -0.0003(4) 0.0025(4) -0.0013(4) N4 0.0243(6) 0.0247(5) 0.0166(5) 0.0008(4) 0.0040(4) -0.0015(4) C1 0.0229(6) 0.0202(6) 0.0176(6) -0.0006(4) 0.0034(5) 0.0007(5) C2 0.0237(7) 0.0254(7) 0.0259(7) -0.0010(5) 0.0070(5) -0.0008(5) C3 0.0280(7) 0.0243(6) 0.0154(5) -0.0002(4) 0.0013(5) -0.0033(5) C4 0.0219(6) 0.0215(6) 0.0151(5) -0.0013(4) 0.0011(4) -0.0014(5) C5 0.0221(6) 0.0253(6) 0.0160(5) 0.0011(5) 0.0017(5) 0.0034(5) C6 0.0209(6) 0.0185(6) 0.0167(5) 0.0000(4) 0.0023(4) -0.0018(5) C7 0.0211(6) 0.0187(6) 0.0166(5) -0.0013(4) 0.0022(5) -0.0016(5) C8 0.0213(6) 0.0232(6) 0.0200(6) -0.0004(5) 0.0028(5) 0.0007(5) C9 0.0248(6) 0.0242(6) 0.0179(6) 0.0005(5) 0.0005(5) -0.0010(5) C10 0.0249(6) 0.0198(6) 0.0179(6) -0.0023(4) 0.0038(5) -0.0034(5) C11 0.0234(6) 0.0237(6) 0.0205(6) -0.0012(5) 0.0052(5) 0.0020(5) C12 0.0223(6) 0.0235(6) 0.0181(6) 0.0005(5) 0.0018(5) 0.0020(5) C13 0.0328(8) 0.0304(7) 0.0167(6) -0.0004(5) 0.0061(5) -0.0006(6) C14 0.0229(6) 0.0236(6) 0.0183(6) -0.0005(5) 0.0026(5) -0.0025(5) C15 0.0222(6) 0.0190(6) 0.0173(6) 0.0006(4) 0.0022(5) 0.0008(5) C16 0.0236(6) 0.0198(6) 0.0156(6) 0.0012(4) 0.0035(5) 0.0011(5) C17 0.0278(7) 0.0263(6) 0.0178(6) 0.0008(5) 0.0032(5) -0.0033(5) C18 0.0333(8) 0.0298(7) 0.0168(6) -0.0007(5) 0.0013(5) 0.0012(6) C19 0.0327(7) 0.0312(7) 0.0202(6) 0.0063(5) 0.0098(5) 0.0098(6) C20 0.0242(7) 0.0272(7) 0.0278(7) 0.0059(5) 0.0089(5) 0.0028(5) C21 0.0235(6) 0.0223(6) 0.0218(6) 0.0006(5) 0.0040(5) 0.0003(5) C22 0.0439(10) 0.0692(13) 0.0238(8) 0.0075(8) 0.0153(7) 0.0076(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3908(15) . ? O1 H1 0.88(2) . ? O2 C2 1.4472(17) . ? O2 C3 1.3506(17) . ? O3 C3 1.1926(17) . ? N1 C1 1.4664(16) . ? N1 C6 1.2880(17) . ? N2 N3 1.3315(16) . ? N2 N4 1.3364(15) . ? N2 C4 1.4467(16) . ? N3 C14 1.3353(17) . ? N4 C15 1.3402(17) . ? C1 C2 1.5234(19) . ? C1 C4 1.5554(18) . ? C2 H2B 0.967(17) . ? C2 H2A 0.991(17) . ? C3 C4 1.5403(18) . ? C4 C5 1.5174(18) . ? C5 C6 1.5183(17) . ? C5 H5B 0.960(17) . ? C5 H5A 0.971(17) . ? C6 C7 1.4709(17) . ? C7 C8 1.4044(18) . ? C7 C12 1.3993(18) . ? C8 C9 1.3909(18) . ? C8 H8 1.007(17) . ? C9 C10 1.4020(19) . ? C9 H9 0.986(17) . ? C10 C11 1.3918(18) . ? C10 C13 1.5037(18) . ? C11 C12 1.3902(18) . ? C11 H11 0.976(17) . ? C12 H12 0.983(17) . ? C13 H13C 0.99(3) . ? C13 H13B 1.01(2) . ? C13 H13A 0.95(3) . ? C14 C15 1.4053(18) . ? C14 H14 0.946(17) . ? C15 C16 1.4636(17) . ? C16 C17 1.3944(18) . ? C16 C21 1.3962(19) . ? C17 C18 1.3887(19) . ? C17 H17 0.965(19) . ? C18 C19 1.390(2) . ? C18 H18 0.971(19) . ? C19 C20 1.397(2) . ? C19 C22 1.505(2) . ? C20 C21 1.3874(19) . ? C20 H20 0.980(18) . ? C21 H21 0.973(17) . ? C22 H22C 0.92(4) . ? C22 H22B 1.00(3) . ? C22 H22A 0.94(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 113.01(10) . . ? O1 C1 C2 108.18(11) . . ? O1 C1 C4 116.51(10) . . ? O2 C2 C1 105.81(11) . . ? O2 C2 H2B 108.0(10) . . ? O2 C2 H2A 108.4(10) . . ? O2 C3 C4 110.47(11) . . ? O3 C3 O2 123.08(13) . . ? O3 C3 C4 126.34(13) . . ? N1 C1 C2 111.42(11) . . ? N1 C1 C4 104.21(10) . . ? N1 C6 C5 115.56(11) . . ? N1 C6 C7 121.80(11) . . ? N2 N3 C14 103.45(11) . . ? N2 N4 C15 104.23(11) . . ? N2 C4 C1 113.50(10) . . ? N2 C4 C3 107.66(10) . . ? N2 C4 C5 116.97(11) . . ? N3 N2 N4 115.29(10) . . ? N3 N2 C4 124.51(11) . . ? N3 C14 C15 109.41(12) . . ? N3 C14 H14 120.3(10) . . ? N4 N2 C4 118.86(11) . . ? N4 C15 C14 107.57(11) . . ? N4 C15 C16 122.52(12) . . ? C1 O1 H1 109.0(14) . . ? C1 C2 H2B 111.5(10) . . ? C1 C2 H2A 114.2(10) . . ? C2 C1 C4 103.10(10) . . ? C3 O2 C2 110.89(10) . . ? C3 C4 C1 102.11(10) . . ? C4 C5 C6 99.86(10) . . ? C4 C5 H5B 111.9(10) . . ? C4 C5 H5A 110.8(10) . . ? C5 C4 C1 105.09(10) . . ? C5 C4 C3 110.53(10) . . ? C6 N1 C1 109.77(10) . . ? C6 C5 H5B 110.4(10) . . ? C6 C5 H5A 113.4(10) . . ? C7 C6 C5 122.61(11) . . ? C7 C8 H8 120.6(10) . . ? C7 C12 H12 121.3(10) . . ? C8 C7 C6 120.86(11) . . ? C8 C9 C10 121.33(12) . . ? C8 C9 H9 120.3(10) . . ? C9 C8 C7 120.15(12) . . ? C9 C8 H8 119.2(10) . . ? C9 C10 C13 121.50(12) . . ? C10 C9 H9 118.4(10) . . ? C10 C11 H11 119.1(10) . . ? C10 C13 H13C 113.7(15) . . ? C10 C13 H13B 112.0(13) . . ? C10 C13 H13A 112.3(16) . . ? C11 C10 C9 117.98(12) . . ? C11 C10 C13 120.51(12) . . ? C11 C12 C7 120.53(12) . . ? C11 C12 H12 118.1(10) . . ? C12 C7 C6 120.50(11) . . ? C12 C7 C8 118.63(12) . . ? C12 C11 C10 121.35(12) . . ? C12 C11 H11 119.6(10) . . ? C14 C15 C16 129.90(12) . . ? C15 C14 H14 130.3(10) . . ? C16 C17 H17 122.4(11) . . ? C16 C21 H21 119.1(10) . . ? C17 C16 C15 120.13(12) . . ? C17 C16 C21 118.96(12) . . ? C17 C18 C19 121.23(13) . . ? C17 C18 H18 119.4(11) . . ? C18 C17 C16 120.32(13) . . ? C18 C17 H17 117.3(11) . . ? C18 C19 C20 118.06(12) . . ? C18 C19 C22 121.10(15) . . ? C19 C18 H18 119.4(11) . . ? C19 C20 H20 120.2(10) . . ? C19 C22 H22C 115(2) . . ? C19 C22 H22B 110.3(18) . . ? C19 C22 H22A 112.5(19) . . ? C20 C19 C22 120.83(15) . . ? C20 C21 C16 120.09(13) . . ? C20 C21 H21 120.8(10) . . ? C21 C16 C15 120.90(12) . . ? C21 C20 C19 121.32(13) . . ? C21 C20 H20 118.5(10) . . ? H2B C2 H2A 108.7(14) . . ? H5B C5 H5A 110.1(13) . . ? H13C C13 H13B 107(2) . . ? H13C C13 H13A 104(2) . . ? H13B C13 H13A 108(2) . . ? H22C C22 H22B 106(3) . . ? H22C C22 H22A 111(3) . . ? H22B C22 H22A 101(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N3 0.88(2) 2.00(2) 2.8808(15) 179(2) 2_766 _database_code_depnum_ccdc_archive 'CCDC 924898' ####################################################################### # # 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_7a_DAX14_SAD _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C22 H20 N4 O3' _chemical_formula_sum 'C22 H20 N4 O3' _chemical_formula_weight 388.42 _chemical_melting_point 138-140 _chemical_name_common ? _chemical_name_systematic ; (5RS,9SR)-3-(4-methylphenyl)-9-[4-(4-methylphenyl)-1,2,3-triazol-2-yl]- 1,7-dioxa-4-azaspiro[4.4]non-3-en-8-one ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, z' 'x, -y, z-1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, -z' '-x, y, -z+1/2' 'x+1/2, -y+1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 102.53(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 26.8700(9) _cell_length_b 14.9778(5) _cell_length_c 10.1263(4) _cell_measurement_reflns_used 3948 _cell_measurement_temperature 120 _cell_measurement_theta_max 30.954 _cell_measurement_theta_min 2.45 _cell_volume 3978.3(2) _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.139 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0968 before and 0.0378 after correction. The Ratio of minimum to maximum transmission is 0.139. The \l/2 correction factor is 0.0015 ; _exptl_crystal_F_000 1632 _exptl_crystal_colour less _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_special_details ? _diffrn_ambient_temperature 120.0 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 21597 _diffrn_reflns_theta_full 28.50 _diffrn_reflns_theta_max 28.50 _diffrn_reflns_theta_min 1.57 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 40.0 _diffrn_source_power 2.0 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3353 _reflns_number_total 5041 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 0.288 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.068 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0553 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 342 _refine_ls_number_reflns 5041 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1355 _refine_ls_wR_factor_ref 0.1551 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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 difmap _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 O1 O 0.74016(5) 0.59263(8) 0.21044(11) 0.0277(3) Uani 1 1 d . . . O2 O 0.77189(5) 0.77814(8) 0.15270(12) 0.0311(3) Uani 1 1 d . . . O3 O 0.85276(5) 0.76443(8) 0.26388(12) 0.0311(3) Uani 1 1 d . . . N1 N 0.69289(5) 0.66216(9) 0.34829(13) 0.0246(3) Uani 1 1 d . . . N2 N 0.81179(5) 0.63955(9) 0.44339(13) 0.0248(3) Uani 1 1 d . . . N3 N 0.79892(6) 0.61384(10) 0.55862(14) 0.0290(3) Uani 1 1 d . . . N4 N 0.84564(6) 0.58829(10) 0.40125(13) 0.0262(3) Uani 1 1 d . . . C1 C 0.73198(7) 0.67504(11) 0.27264(16) 0.0256(4) Uani 1 1 d . . . C2 C 0.72159(7) 0.74958(12) 0.16763(18) 0.0298(4) Uani 1 1 d . . . C3 C 0.80863(7) 0.75113(11) 0.25844(16) 0.0266(4) Uani 1 1 d . . . C4 C 0.78267(6) 0.70810(11) 0.36181(16) 0.0241(3) Uani 1 1 d . . . C5 C 0.71612(7) 0.52481(12) 0.27320(16) 0.0254(4) Uani 1 1 d . . . C6 C 0.68443(6) 0.57809(11) 0.35098(15) 0.0226(3) Uani 1 1 d . . . C7 C 0.64906(6) 0.53817(11) 0.42602(15) 0.0237(3) Uani 1 1 d . . . C8 C 0.64277(7) 0.44607(12) 0.42789(17) 0.0284(4) Uani 1 1 d . . . C9 C 0.61003(7) 0.40840(13) 0.50151(19) 0.0327(4) Uani 1 1 d . . . C10 C 0.58317(7) 0.46164(13) 0.57435(17) 0.0326(4) Uani 1 1 d . . . C11 C 0.58975(7) 0.55390(13) 0.57162(17) 0.0305(4) Uani 1 1 d . . . C12 C 0.62177(6) 0.59216(12) 0.49752(16) 0.0256(4) Uani 1 1 d . . . C13 C 0.54760(8) 0.42109(19) 0.6536(2) 0.0453(6) Uani 1 1 d . . . C14 C 0.82756(7) 0.54205(12) 0.59371(17) 0.0299(4) Uani 1 1 d . . . C15 C 0.85726(7) 0.52592(11) 0.49807(17) 0.0280(4) Uani 1 1 d . . . C16 C 0.89697(7) 0.45902(12) 0.49743(17) 0.0317(4) Uani 1 1 d . . . C17 C 0.93004(9) 0.46698(16) 0.4095(2) 0.0453(5) Uani 1 1 d . . . C18 C 0.96946(10) 0.40664(19) 0.4155(2) 0.0570(7) Uani 1 1 d . . . C19 C 0.97725(10) 0.33705(16) 0.5090(2) 0.0548(7) Uani 1 1 d . . . C20 C 0.94352(10) 0.32846(15) 0.5933(2) 0.0510(6) Uani 1 1 d . . . C21 C 0.90377(9) 0.38803(13) 0.5888(2) 0.0396(5) Uani 1 1 d . . . C22 C 1.02231(14) 0.2757(2) 0.5195(4) 0.0771(10) Uani 1 1 d . . . H2B H 0.7051(7) 0.8016(13) 0.205(2) 0.035(5) Uiso 1 1 d . . . H12 H 0.6262(6) 0.6582(12) 0.4969(18) 0.020(4) Uiso 1 1 d . . . H5A H 0.6953(7) 0.4866(11) 0.206(2) 0.022(4) Uiso 1 1 d . . . H4 H 0.7746(7) 0.7573(12) 0.420(2) 0.029(5) Uiso 1 1 d . . . H5B H 0.7424(7) 0.4871(12) 0.333(2) 0.026(5) Uiso 1 1 d . . . H8 H 0.6636(9) 0.4044(14) 0.378(2) 0.044(6) Uiso 1 1 d . . . H9 H 0.6059(7) 0.3461(14) 0.506(2) 0.033(5) Uiso 1 1 d . . . H11 H 0.5700(8) 0.5937(13) 0.623(2) 0.038(5) Uiso 1 1 d . . . H2A H 0.7023(8) 0.7248(13) 0.079(2) 0.034(5) Uiso 1 1 d . . . H14 H 0.8271(8) 0.5080(13) 0.680(2) 0.039(6) Uiso 1 1 d . . . H17 H 0.9254(9) 0.5189(16) 0.345(3) 0.063(7) Uiso 1 1 d . . . H13A H 0.5116(9) 0.4193(15) 0.607(2) 0.050(6) Uiso 1 1 d . . . H21 H 0.8779(10) 0.3809(17) 0.652(3) 0.071(8) Uiso 1 1 d . . . H20 H 0.9469(10) 0.2779(19) 0.658(3) 0.073(9) Uiso 1 1 d . . . H13C H 0.5480(10) 0.4565(19) 0.740(3) 0.078(9) Uiso 1 1 d . . . H18 H 0.9944(10) 0.4179(16) 0.364(3) 0.056(7) Uiso 1 1 d . . . H13B H 0.5545(11) 0.3595(19) 0.675(3) 0.073(9) Uiso 1 1 d . . . H22C H 1.0547(11) 0.2971(19) 0.566(3) 0.073(9) Uiso 1 1 d . . . H22B H 1.0300(12) 0.260(2) 0.434(4) 0.093(11) Uiso 1 1 d . . . H22A H 1.0151(14) 0.210(3) 0.552(4) 0.115(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0363(7) 0.0325(6) 0.0172(5) -0.0059(5) 0.0122(5) -0.0034(5) O2 0.0395(7) 0.0388(7) 0.0163(6) 0.0043(5) 0.0092(5) -0.0025(5) O3 0.0371(7) 0.0362(7) 0.0233(6) -0.0015(5) 0.0139(5) -0.0053(5) N1 0.0310(7) 0.0302(7) 0.0137(6) -0.0009(5) 0.0072(5) 0.0002(6) N2 0.0328(8) 0.0314(7) 0.0122(6) 0.0006(5) 0.0095(5) -0.0011(6) N3 0.0391(8) 0.0380(8) 0.0121(6) 0.0008(6) 0.0106(6) -0.0038(6) N4 0.0332(8) 0.0310(7) 0.0154(6) -0.0011(6) 0.0076(6) 0.0002(6) C1 0.0333(9) 0.0312(8) 0.0144(7) -0.0025(6) 0.0096(6) -0.0006(7) C2 0.0361(10) 0.0371(10) 0.0170(8) 0.0033(7) 0.0072(7) -0.0020(8) C3 0.0402(10) 0.0268(8) 0.0153(7) -0.0024(6) 0.0115(7) -0.0020(7) C4 0.0328(9) 0.0281(8) 0.0131(7) -0.0012(6) 0.0088(6) -0.0015(7) C5 0.0297(9) 0.0309(8) 0.0166(7) -0.0051(7) 0.0073(7) -0.0023(7) C6 0.0263(8) 0.0309(8) 0.0100(6) -0.0016(6) 0.0023(6) 0.0020(6) C7 0.0258(8) 0.0322(8) 0.0121(7) -0.0009(6) 0.0020(6) -0.0001(6) C8 0.0328(9) 0.0336(9) 0.0187(8) -0.0011(7) 0.0051(7) -0.0011(7) C9 0.0336(10) 0.0359(10) 0.0268(9) 0.0036(8) 0.0025(8) -0.0060(8) C10 0.0253(9) 0.0522(11) 0.0184(8) 0.0066(8) 0.0006(7) -0.0040(8) C11 0.0267(9) 0.0484(11) 0.0167(8) 0.0011(7) 0.0052(7) 0.0035(8) C12 0.0275(8) 0.0346(9) 0.0145(7) -0.0007(7) 0.0039(6) 0.0026(7) C13 0.0306(11) 0.0746(17) 0.0309(11) 0.0141(11) 0.0071(9) -0.0103(10) C14 0.0402(10) 0.0355(9) 0.0150(7) 0.0018(7) 0.0082(7) -0.0006(8) C15 0.0357(9) 0.0318(9) 0.0164(7) 0.0000(7) 0.0055(7) -0.0023(7) C16 0.0413(10) 0.0352(9) 0.0172(8) -0.0021(7) 0.0031(7) 0.0025(8) C17 0.0522(13) 0.0601(14) 0.0254(9) 0.0053(9) 0.0124(9) 0.0190(11) C18 0.0572(15) 0.0816(18) 0.0324(11) -0.0045(12) 0.0104(11) 0.0289(13) C19 0.0620(15) 0.0548(14) 0.0371(12) -0.0166(10) -0.0122(11) 0.0247(11) C20 0.0662(15) 0.0384(11) 0.0391(12) -0.0017(10) -0.0095(11) 0.0104(10) C21 0.0509(12) 0.0349(10) 0.0287(10) 0.0009(8) -0.0008(9) 0.0005(9) C22 0.076(2) 0.077(2) 0.0645(19) -0.0220(17) -0.0140(17) 0.0426(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.424(2) . ? O1 C5 1.425(2) . ? O2 C2 1.456(2) . ? O2 C3 1.351(2) . ? O3 C3 1.192(2) . ? N1 C1 1.441(2) . ? N1 C6 1.281(2) . ? N2 N3 1.3433(18) . ? N2 N4 1.329(2) . ? N2 C4 1.438(2) . ? N3 C14 1.325(2) . ? N4 C15 1.341(2) . ? C1 C2 1.525(2) . ? C1 C4 1.543(2) . ? C2 H2B 1.01(2) . ? C2 H2A 1.00(2) . ? C3 C4 1.521(2) . ? C4 H4 0.994(19) . ? C5 C6 1.508(2) . ? C5 H5A 0.970(18) . ? C5 H5B 1.001(19) . ? C6 C7 1.467(2) . ? C7 C8 1.390(2) . ? C7 C12 1.395(2) . ? C8 C9 1.390(3) . ? C8 H8 1.04(2) . ? C9 C10 1.390(3) . ? C9 H9 0.94(2) . ? C10 C11 1.394(3) . ? C10 C13 1.503(3) . ? C11 C12 1.383(2) . ? C11 H11 1.02(2) . ? C12 H12 0.997(17) . ? C13 H13A 0.98(2) . ? C13 H13C 1.02(3) . ? C13 H13B 0.96(3) . ? C14 C15 1.403(2) . ? C14 H14 1.01(2) . ? C15 C16 1.465(3) . ? C16 C17 1.393(3) . ? C16 C21 1.395(3) . ? C17 C18 1.384(3) . ? C17 H17 1.00(3) . ? C18 C19 1.393(4) . ? C18 H18 0.95(3) . ? C19 C20 1.379(4) . ? C19 C22 1.506(3) . ? C20 C21 1.385(3) . ? C20 H20 0.99(3) . ? C21 H21 1.04(3) . ? C22 H22C 0.95(3) . ? C22 H22B 0.96(4) . ? C22 H22A 1.07(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 108.62(13) . . ? O1 C1 C2 110.39(13) . . ? O1 C1 C4 109.60(13) . . ? O1 C5 C6 102.57(13) . . ? O1 C5 H5A 110.8(11) . . ? O1 C5 H5B 110.1(11) . . ? O2 C2 C1 104.70(14) . . ? O2 C2 H2B 107.8(11) . . ? O2 C2 H2A 109.2(12) . . ? O2 C3 C4 107.86(14) . . ? O3 C3 O2 122.36(15) . . ? O3 C3 C4 129.72(16) . . ? N1 C1 C2 115.11(14) . . ? N1 C1 C4 112.61(13) . . ? N1 C6 C5 112.73(14) . . ? N1 C6 C7 123.33(14) . . ? N2 N4 C15 103.58(13) . . ? N2 C4 C1 114.08(14) . . ? N2 C4 C3 115.10(14) . . ? N2 C4 H4 110.6(11) . . ? N3 N2 C4 119.56(14) . . ? N3 C14 C15 109.81(15) . . ? N3 C14 H14 121.6(12) . . ? N4 N2 N3 115.86(14) . . ? N4 N2 C4 123.56(13) . . ? N4 C15 C14 107.91(15) . . ? N4 C15 C16 121.85(16) . . ? C1 O1 C5 106.98(12) . . ? C1 C2 H2B 109.4(12) . . ? C1 C2 H2A 109.4(11) . . ? C1 C4 H4 107.7(11) . . ? C2 C1 C4 100.25(13) . . ? C3 O2 C2 111.39(13) . . ? C3 C4 C1 102.21(13) . . ? C3 C4 H4 106.4(11) . . ? C6 N1 C1 107.22(13) . . ? C6 C5 H5A 111.9(11) . . ? C6 C5 H5B 112.7(11) . . ? C7 C6 C5 123.90(14) . . ? C7 C8 H8 120.7(12) . . ? C7 C12 H12 119.7(11) . . ? C8 C7 C6 120.38(15) . . ? C8 C7 C12 119.28(16) . . ? C8 C9 H9 121.7(13) . . ? C9 C8 C7 120.19(17) . . ? C9 C8 H8 119.1(12) . . ? C9 C10 C11 118.38(17) . . ? C9 C10 C13 121.0(2) . . ? C10 C9 C8 120.91(18) . . ? C10 C9 H9 117.4(13) . . ? C10 C11 H11 119.2(12) . . ? C10 C13 H13A 115.6(14) . . ? C10 C13 H13C 110.9(16) . . ? C10 C13 H13B 113.2(18) . . ? C11 C10 C13 120.60(19) . . ? C11 C12 C7 120.02(17) . . ? C11 C12 H12 120.2(11) . . ? C12 C7 C6 120.34(15) . . ? C12 C11 C10 121.21(17) . . ? C12 C11 H11 119.6(12) . . ? C14 N3 N2 102.81(14) . . ? C14 C15 C16 130.15(16) . . ? C15 C14 H14 128.6(12) . . ? C16 C17 H17 118.3(14) . . ? C16 C21 H21 118.2(15) . . ? C17 C16 C15 120.70(17) . . ? C17 C16 C21 118.62(18) . . ? C17 C18 C19 121.3(2) . . ? C17 C18 H18 119.0(15) . . ? C18 C17 C16 120.3(2) . . ? C18 C17 H17 121.4(14) . . ? C18 C19 C22 120.3(3) . . ? C19 C18 H18 119.1(15) . . ? C19 C20 C21 121.7(2) . . ? C19 C20 H20 120.1(16) . . ? C19 C22 H22C 117.6(17) . . ? C19 C22 H22B 114(2) . . ? C19 C22 H22A 113(2) . . ? C20 C19 C18 117.9(2) . . ? C20 C19 C22 121.7(3) . . ? C20 C21 C16 120.1(2) . . ? C20 C21 H21 121.7(15) . . ? C21 C16 C15 120.62(18) . . ? C21 C20 H20 118.2(16) . . ? H2B C2 H2A 115.8(16) . . ? H5A C5 H5B 108.6(15) . . ? H13A C13 H13C 104(2) . . ? H13A C13 H13B 102(2) . . ? H13C C13 H13B 110(2) . . ? H22C C22 H22B 100(3) . . ? H22C C22 H22A 111(3) . . ? H22B C22 H22A 98(3) . . ? _database_code_depnum_ccdc_archive 'CCDC 924899'