# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- 5j.txt' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2011-11-21 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #============================================================================== # # SUBMISSION DETAILS _publ_contact_author_name 'Jose L. Vicario' # Name of author for correspondence _publ_contact_author_address ; Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia, Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644, 48080 Bilbao, Spain ; # Address of author for correspondence _publ_contact_author_email joseluis.vicario@ehu.es _publ_contact_author_fax (+34)946012748 _publ_contact_author_phone (+34)946015454 _publ_contact_letter ; Submission dated :????? Please consider this CIF for submission to the Cambridge Crystallographic Data Centre. I certify that all authors have seen and approved of this submission, that all have made significant scientific contributions to the work reported, and that all share responsibility and accountability for the results. This CIF is submitted as part of a journal submission ; #============================================================================== # # TITLE AND AUTHOR LIST _publ_section_title ; Organocatalytic Enantioselective Synthesis of 2,3-Dyhidropyridazines ; _publ_section_title_footnote ; ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Fernandez, Maitane' ; Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia, Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644, 48080 Bilbao, Spain ; 'Vicario, Jose L.' ; Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia, Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644, 48080 Bilbao, Spain ; 'Reyes, Efraim' ; Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia, Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644, 48080 Bilbao, Spain ; 'Carrillo, Luisa' ; Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia, Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644, 48080 Bilbao, Spain ; 'Badia, Dolores' ; Departamento de Quimica Organica II, Facultad de Ciencia y Tecnologia, Universidad del Pais Vasco/Euskal Herriko Unibertsitatea. P.O. Box 644, 48080 Bilbao, Spain ; #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_mf464 _database_code_depnum_ccdc_archive 'CCDC 855796' #TrackingRef '- 5j.txt' _audit_creation_date 2011-11-21T15:06:00-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H19 N3 O5 S1' _chemical_formula_sum 'C19 H19 N3 O5 S' _chemical_formula_weight 401.43 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.0573(2) _cell_length_b 10.8477(2) _cell_length_c 11.3405(2) _cell_angle_alpha 90 _cell_angle_beta 107.716(2) _cell_angle_gamma 90 _cell_volume 944.19(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6172 _cell_measurement_theta_min 4.0719 _cell_measurement_theta_max 75.9792 _cell_measurement_wavelength 1.54184 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.849 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.85289 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Nova (Cu) X-ray micro-source' _diffrn_radiation_monochromator 'Multilayer optics' _diffrn_source_voltage 50 _diffrn_source_current 0.8 _diffrn_source_power 0.04 _diffrn_detector_area_resol_mean 10.4023 _diffrn_orient_matrix_ub_11 -0.184322 _diffrn_orient_matrix_ub_12 0.0042798 _diffrn_orient_matrix_ub_13 -0.0934746 _diffrn_orient_matrix_ub_21 -0.0767561 _diffrn_orient_matrix_ub_22 0.0272192 _diffrn_orient_matrix_ub_23 0.1061639 _diffrn_orient_matrix_ub_31 0.0206275 _diffrn_orient_matrix_ub_32 0.1393605 _diffrn_orient_matrix_ub_33 -0.0178338 _diffrn_measurement_device_type 'Agilent SuperNova' _diffrn_measurement_method '\w scans' _diffrn_detector 'CCD plate' _diffrn_detector_type Atlas _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_av_unetI/netI 0.0207 _diffrn_reflns_number 8056 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 72.47 _diffrn_reflns_theta_full 72.47 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3637 _reflns_number_gt 3585 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -58.00 35.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -40.6693 38.0000 -180.0000 93 #__ type_ start__ end____ width___ exp.time_ 2 omega -97.00 -13.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -40.6693 125.0000 -180.0000 84 #__ type_ start__ end____ width___ exp.time_ 3 omega 71.00 116.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 40.6693 77.0000 90.0000 45 #__ type_ start__ end____ width___ exp.time_ 4 omega 27.00 57.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 40.6693 77.0000 120.0000 30 #__ type_ start__ end____ width___ exp.time_ 5 omega 16.00 117.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 40.6693 38.0000 60.0000 101 #__ type_ start__ end____ width___ exp.time_ 6 omega 9.00 45.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 40.6693 77.0000 90.0000 36 #__ type_ start__ end____ width___ exp.time_ 7 omega -75.00 -49.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega -80.00 -53.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -65.0000 113.0000 27 #__ type_ start__ end____ width___ exp.time_ 9 omega -75.00 -49.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 10 omega -74.00 -49.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 11 omega -74.00 -49.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 12 omega -79.00 -52.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -70.0000 32.0000 27 #__ type_ start__ end____ width___ exp.time_ 13 omega -74.00 -49.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 150.0000 25 #__ type_ start__ end____ width___ exp.time_ 14 omega -78.00 -52.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -70.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 15 omega -77.00 -51.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -83.0000 -71.0000 91.0000 26 #__ type_ start__ end____ width___ exp.time_ 16 omega 132.00 158.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 17 omega 79.00 111.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 150.0000 32 #__ type_ start__ end____ width___ exp.time_ 18 omega 43.00 74.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 60.0000 31 #__ type_ start__ end____ width___ exp.time_ 19 omega 110.00 158.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 45.0000 -180.0000 48 #__ type_ start__ end____ width___ exp.time_ 20 omega 39.00 71.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 120.0000 32 #__ type_ start__ end____ width___ exp.time_ 21 omega 128.00 157.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 45.0000 -120.0000 29 #__ type_ start__ end____ width___ exp.time_ 22 omega 38.00 76.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 30.0000 38 #__ type_ start__ end____ width___ exp.time_ 23 omega 90.00 133.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 0.0000 43 #__ type_ start__ end____ width___ exp.time_ 24 omega 79.00 143.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 60.0000 64 #__ type_ start__ end____ width___ exp.time_ 25 omega 41.00 73.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -180.0000 32 #__ type_ start__ end____ width___ exp.time_ 26 omega 107.00 154.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 90.0000 47 #__ type_ start__ end____ width___ exp.time_ 27 omega 46.00 73.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 150.0000 27 #__ type_ start__ end____ width___ exp.time_ 28 omega 60.00 115.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -112.0000 34.0000 55 #__ type_ start__ end____ width___ exp.time_ 29 omega 79.00 106.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 90.0000 27 #__ type_ start__ end____ width___ exp.time_ 30 omega 80.00 145.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 30.0000 65 #__ type_ start__ end____ width___ exp.time_ 31 omega 40.00 66.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 32 omega 44.00 77.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -90.0000 33 #__ type_ start__ end____ width___ exp.time_ 33 omega 79.00 154.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 77.0000 120.0000 75 #__ type_ start__ end____ width___ exp.time_ 34 omega 55.00 132.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -77.0000 30.0000 77 #__ type_ start__ end____ width___ exp.time_ 35 omega 40.00 65.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 0.0000 25 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlis Pro (Oxford Diffraction Ltd., 2011)' _computing_cell_refinement 'CrysAlis Pro (Oxford Diffraction Ltd., 2011)' _computing_data_reduction 'CrysAlis Pro (Oxford Diffraction Ltd., 2011)' _computing_structure_solution 'SIR92 (Altomare et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2f (Crystal Impact GbR, 2008)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993) J. Appl. Cryst. 26, 343--350. Branderburg, K. (2010), Diamond, Crystal Impact GbR, Bonn, Germany Oxford Diffraction (2010). CrysAlisPro. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837--838. Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; The nitro oxygen atoms showed signs of disorder so that they were refined in two alternate positions, whose occupancy factors refined to 0.921(5):0.079(5). In order to improve the refinement, the N--O, O...O distances and O ADPs were restrained to be the same. 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.1568P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0014(4) _refine_ls_number_reflns 3637 _refine_ls_number_parameters 276 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.025 _refine_ls_wR_factor_ref 0.066 _refine_ls_wR_factor_gt 0.0656 _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_Flack -0.008(11) _refine_diff_density_max 0.271 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.033 _refine_ls_abs_structure_details ; The Friedel pair coverage of the experiment is almost complete (94%). Analysis of the absolute structure using likelihood methods (Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011). The results indicated that the absolute structure had been correctly assigned. The method calculated that the probability that the structure is inverted is smaller than 10-99. The absolute structure parameter y (Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek, 2010). The resulting value was y=-0.028(5), which together with Flack parameter value, indicate that the absolute structure has surely been determined correctly. Flack, H. D. (1983), Acta Cryst. A39, 876-881 Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148. R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103 A. L. Spek (2010) PLATON, Utrecht, The Netherlands; A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13 A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717 ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C3 C 0.92135(18) 0.56568(13) -0.11122(12) 0.0221(3) Uani 1 1 d . . . H3 H 0.8545 0.6435 -0.1393 0.027 Uiso 1 1 calc R . . C4 C 1.11175(18) 0.59162(14) -0.09578(13) 0.0233(3) Uani 1 1 d . . . C5 C 1.23323(17) 0.54769(15) 0.00273(14) 0.0261(3) Uani 1 1 d . . . H5 H 1.3522 0.5653 0.0126 0.031 Uiso 1 1 calc R . . C6 C 1.18907(18) 0.47312(15) 0.09621(14) 0.0251(3) Uani 1 1 d . . . C7 C 0.73481(18) 0.62697(14) 0.16130(13) 0.0226(3) Uani 1 1 d . . . C8 C 0.66611(19) 0.74528(15) 0.14096(14) 0.0262(3) Uani 1 1 d . . . H8 H 0.606 0.7721 0.0594 0.031 Uiso 1 1 calc R . . C9 C 0.6860(2) 0.82370(15) 0.24061(16) 0.0311(3) Uani 1 1 d . . . H9 H 0.6362 0.9038 0.2273 0.037 Uiso 1 1 calc R . . C10 C 0.7785(2) 0.78651(17) 0.36057(15) 0.0345(4) Uani 1 1 d . . . C11 C 0.8437(2) 0.66647(18) 0.37797(15) 0.0361(4) Uani 1 1 d . . . H11 H 0.9052 0.6398 0.4593 0.043 Uiso 1 1 calc R . . C12 C 0.8215(2) 0.58516(16) 0.28044(14) 0.0305(3) Uani 1 1 d . . . H12 H 0.8642 0.5031 0.2942 0.037 Uiso 1 1 calc R . . C13 C 0.8067(3) 0.8742(2) 0.46750(18) 0.0510(5) Uani 1 1 d . . . H13A H 0.8736 0.8329 0.5441 0.076 Uiso 0.5 1 calc PR . . H13B H 0.6937 0.9003 0.4746 0.076 Uiso 0.5 1 calc PR . . H13C H 0.8712 0.9464 0.4535 0.076 Uiso 0.5 1 calc PR . . H13D H 0.7521 0.9535 0.4374 0.076 Uiso 0.5 1 calc PR . . H13E H 0.9319 0.8861 0.5069 0.076 Uiso 0.5 1 calc PR . . H13F H 0.7545 0.84 0.528 0.076 Uiso 0.5 1 calc PR . . C14 C 0.84815(17) 0.46759(14) -0.20877(13) 0.0221(3) Uani 1 1 d . . . C15 C 0.7703(2) 0.50417(15) -0.33069(15) 0.0367(4) Uani 1 1 d . . . H15 H 0.7635 0.5893 -0.3513 0.044 Uiso 1 1 calc R . . C16 C 0.7026(3) 0.41720(18) -0.42250(17) 0.0438(4) Uani 1 1 d . . . H16 H 0.6518 0.4415 -0.5063 0.053 Uiso 1 1 calc R . . C17 C 0.7109(2) 0.29524(16) -0.38917(16) 0.0346(4) Uani 1 1 d . A . C18 C 0.7880(2) 0.25551(16) -0.26931(17) 0.0365(4) Uani 1 1 d . . . H18 H 0.7922 0.1704 -0.249 0.044 Uiso 1 1 calc R . . C19 C 0.8590(2) 0.34326(15) -0.17973(16) 0.0324(3) Uani 1 1 d . . . H19 H 0.916 0.3179 -0.0971 0.039 Uiso 1 1 calc R . . C20 C 1.15148(19) 0.65868(14) -0.20013(15) 0.0277(3) Uani 1 1 d . . . H20A H 1.2706 0.6934 -0.1697 0.033 Uiso 1 1 calc R . . H20B H 1.1492 0.5991 -0.2668 0.033 Uiso 1 1 calc R . . C21 C 1.32847(19) 0.40502(18) 0.19208(15) 0.0322(3) Uani 1 1 d . . . H21A H 1.3788 0.3415 0.1518 0.048 Uiso 1 1 calc R . . H21B H 1.278 0.3661 0.2512 0.048 Uiso 1 1 calc R . . H21C H 1.4198 0.4629 0.2359 0.048 Uiso 1 1 calc R . . N1 N 1.03163(16) 0.46530(13) 0.10087(11) 0.0248(3) Uani 1 1 d . . . N2 N 0.90772(14) 0.53435(14) 0.01219(10) 0.0251(2) Uani 1 1 d . . . N3 N 0.6303(2) 0.20298(16) -0.48380(17) 0.0524(5) Uani 1 1 d D . . O1 O 0.59814(12) 0.58583(11) -0.07505(9) 0.0281(2) Uani 1 1 d . . . O2 O 0.67998(14) 0.40703(11) 0.06794(11) 0.0309(2) Uani 1 1 d . . . O3 O 0.5922(4) 0.2333(2) -0.59377(18) 0.0773(9) Uani 0.921(5) 1 d PDU A 1 O4 O 0.6056(3) 0.09913(16) -0.44800(18) 0.0627(7) Uani 0.921(5) 1 d PDU A 1 O3B O 0.515(4) 0.245(2) -0.569(2) 0.071(3) Uani 0.079(5) 1 d PDU A 2 O4B O 0.697(3) 0.1016(16) -0.478(3) 0.066(3) Uani 0.079(5) 1 d PDU A 2 O5 O 1.03178(14) 0.75543(10) -0.24991(11) 0.0311(2) Uani 1 1 d . . . H5A H 1.0499 0.8142 -0.1993 0.047 Uiso 1 1 calc R . . S1 S 0.71373(4) 0.52956(3) 0.03362(3) 0.02305(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C3 0.0197(6) 0.0242(7) 0.0240(7) -0.0016(5) 0.0090(5) -0.0005(5) C4 0.0217(7) 0.0214(7) 0.0304(7) -0.0037(6) 0.0134(6) -0.0017(5) C5 0.0171(6) 0.0324(9) 0.0305(7) -0.0028(6) 0.0096(5) -0.0033(6) C6 0.0195(7) 0.0318(8) 0.0250(7) -0.0030(6) 0.0083(5) -0.0010(6) C7 0.0195(6) 0.0259(7) 0.0254(7) -0.0004(5) 0.0115(5) -0.0004(5) C8 0.0235(7) 0.0282(7) 0.0274(7) 0.0036(6) 0.0085(6) 0.0008(6) C9 0.0342(8) 0.0269(8) 0.0342(8) 0.0017(6) 0.0135(7) 0.0013(6) C10 0.0373(9) 0.0392(9) 0.0292(8) -0.0010(7) 0.0136(7) 0.0018(7) C11 0.0403(9) 0.0459(10) 0.0230(8) 0.0060(7) 0.0112(7) 0.0087(8) C12 0.0322(8) 0.0337(8) 0.0289(8) 0.0067(6) 0.0141(6) 0.0100(7) C13 0.0673(14) 0.0514(12) 0.0353(10) -0.0084(8) 0.0172(9) 0.0065(10) C14 0.0162(6) 0.0237(7) 0.0276(7) -0.0010(6) 0.0083(5) -0.0005(5) C15 0.0483(10) 0.0246(9) 0.0306(8) 0.0011(6) 0.0023(7) 0.0016(7) C16 0.0552(11) 0.0351(10) 0.0296(8) -0.0022(7) -0.0040(8) 0.0037(8) C17 0.0307(8) 0.0299(9) 0.0375(9) -0.0113(7) 0.0017(7) 0.0041(7) C18 0.0431(9) 0.0219(8) 0.0406(9) -0.0021(7) 0.0071(7) 0.0016(7) C19 0.0382(9) 0.0261(8) 0.0300(8) 0.0020(6) 0.0062(7) 0.0019(6) C20 0.0234(7) 0.0296(8) 0.0333(8) 0.0023(6) 0.0135(6) -0.0001(6) C21 0.0197(7) 0.0460(10) 0.0305(8) 0.0037(7) 0.0071(6) 0.0027(7) N1 0.0206(6) 0.0314(6) 0.0226(6) -0.0005(5) 0.0067(4) 0.0013(5) N2 0.0150(5) 0.0371(7) 0.0242(5) 0.0011(6) 0.0073(4) 0.0012(5) N3 0.0494(10) 0.0402(10) 0.0539(11) -0.0195(8) -0.0050(8) 0.0084(8) O1 0.0165(4) 0.0404(6) 0.0274(5) -0.0017(5) 0.0068(4) 0.0016(4) O2 0.0225(5) 0.0301(6) 0.0436(6) -0.0037(5) 0.0153(5) -0.0039(4) O3 0.110(2) 0.0595(12) 0.0402(11) -0.0229(9) -0.0095(11) 0.0032(13) O4 0.0783(16) 0.0332(9) 0.0690(12) -0.0222(8) 0.0108(10) -0.0104(9) O3B 0.102(6) 0.058(5) 0.033(5) -0.023(5) -0.006(5) 0.006(5) O4B 0.078(5) 0.039(5) 0.074(5) -0.018(5) 0.011(5) -0.011(5) O5 0.0297(6) 0.0270(6) 0.0374(6) 0.0026(4) 0.0111(5) 0.0002(4) S1 0.01556(14) 0.02805(18) 0.02750(16) -0.00214(13) 0.00947(11) -0.00068(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 N2 1.4763(17) . ? C3 C4 1.5166(18) . ? C3 C14 1.5188(19) . ? C3 H3 1 . ? C4 C5 1.329(2) . ? C4 C20 1.504(2) . ? C5 C6 1.461(2) . ? C5 H5 0.95 . ? C6 N1 1.288(2) . ? C6 C21 1.499(2) . ? C7 C8 1.389(2) . ? C7 C12 1.395(2) . ? C7 S1 1.7585(15) . ? C8 C9 1.384(2) . ? C8 H8 0.95 . ? C9 C10 1.397(2) . ? C9 H9 0.95 . ? C10 C11 1.396(3) . ? C10 C13 1.503(3) . ? C11 C12 1.383(2) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C13 H13D 0.98 . ? C13 H13E 0.98 . ? C13 H13F 0.98 . ? C14 C19 1.385(2) . ? C14 C15 1.391(2) . ? C15 C16 1.388(2) . ? C15 H15 0.95 . ? C16 C17 1.372(3) . ? C16 H16 0.95 . ? C17 C18 1.380(3) . ? C17 N3 1.467(2) . ? C18 C19 1.383(2) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 O5 1.4209(19) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? N1 N2 1.3993(17) . ? N2 S1 1.6541(10) . ? N3 O3B 1.211(14) . ? N3 O4B 1.217(14) . ? N3 O4 1.234(3) . ? N3 O3 1.235(3) . ? O1 S1 1.4354(11) . ? O2 S1 1.4341(12) . ? O5 H5A 0.84 . ? 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 N2 C3 C4 107.32(11) . . ? N2 C3 C14 113.88(12) . . ? C4 C3 C14 111.66(11) . . ? N2 C3 H3 107.9 . . ? C4 C3 H3 107.9 . . ? C14 C3 H3 107.9 . . ? C5 C4 C20 123.77(13) . . ? C5 C4 C3 119.39(13) . . ? C20 C4 C3 116.67(12) . . ? C4 C5 C6 121.91(12) . . ? C4 C5 H5 119 . . ? C6 C5 H5 119 . . ? N1 C6 C5 121.76(14) . . ? N1 C6 C21 117.89(14) . . ? C5 C6 C21 120.34(12) . . ? C8 C7 C12 121.22(14) . . ? C8 C7 S1 118.99(11) . . ? C12 C7 S1 119.79(12) . . ? C9 C8 C7 119.40(14) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 120.84(15) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 118.25(16) . . ? C11 C10 C13 121.21(17) . . ? C9 C10 C13 120.54(17) . . ? C12 C11 C10 122.04(15) . . ? C12 C11 H11 119 . . ? C10 C11 H11 119 . . ? C11 C12 C7 118.17(15) . . ? C11 C12 H12 120.9 . . ? C7 C12 H12 120.9 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C13 H13D 109.5 . . ? H13A C13 H13D 141.1 . . ? H13B C13 H13D 56.3 . . ? H13C C13 H13D 56.3 . . ? C10 C13 H13E 109.5 . . ? H13A C13 H13E 56.3 . . ? H13B C13 H13E 141.1 . . ? H13C C13 H13E 56.3 . . ? H13D C13 H13E 109.5 . . ? C10 C13 H13F 109.5 . . ? H13A C13 H13F 56.3 . . ? H13B C13 H13F 56.3 . . ? H13C C13 H13F 141.1 . . ? H13D C13 H13F 109.5 . . ? H13E C13 H13F 109.5 . . ? C19 C14 C15 119.41(15) . . ? C19 C14 C3 121.78(14) . . ? C15 C14 C3 118.81(14) . . ? C16 C15 C14 120.48(16) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 118.27(16) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C16 C17 C18 122.82(16) . . ? C16 C17 N3 118.87(16) . . ? C18 C17 N3 118.29(16) . . ? C17 C18 C19 118.04(16) . . ? C17 C18 H18 121 . . ? C19 C18 H18 121 . . ? C18 C19 C14 120.91(16) . . ? C18 C19 H19 119.5 . . ? C14 C19 H19 119.5 . . ? O5 C20 C4 112.87(12) . . ? O5 C20 H20A 109 . . ? C4 C20 H20A 109 . . ? O5 C20 H20B 109 . . ? C4 C20 H20B 109 . . ? H20A C20 H20B 107.8 . . ? C6 C21 H21A 109.5 . . ? C6 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C6 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C6 N1 N2 115.56(12) . . ? N1 N2 C3 124.18(11) . . ? N1 N2 S1 112.15(9) . . ? C3 N2 S1 119.52(9) . . ? O3B N3 O4B 127.4(13) . . ? O3B N3 O4 116.6(16) . . ? O4B N3 O4 43.1(16) . . ? O3B N3 O3 36.7(16) . . ? O4B N3 O3 105.5(14) . . ? O4 N3 O3 124.06(18) . . ? O3B N3 C17 112.7(12) . . ? O4B N3 C17 119.1(10) . . ? O4 N3 C17 117.52(18) . . ? O3 N3 C17 118.42(19) . . ? C20 O5 H5A 109.5 . . ? O2 S1 O1 120.01(7) . . ? O2 S1 N2 109.55(7) . . ? O1 S1 N2 104.82(6) . . ? O2 S1 C7 108.19(7) . . ? O1 S1 C7 109.04(7) . . ? N2 S1 C7 104.08(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C3 C4 C5 20.92(18) . . . . ? C14 C3 C4 C5 -104.54(16) . . . . ? N2 C3 C4 C20 -163.62(13) . . . . ? C14 C3 C4 C20 70.92(16) . . . . ? C20 C4 C5 C6 -174.13(14) . . . . ? C3 C4 C5 C6 1.0(2) . . . . ? C4 C5 C6 N1 -13.3(2) . . . . ? C4 C5 C6 C21 168.08(15) . . . . ? C12 C7 C8 C9 0.9(2) . . . . ? S1 C7 C8 C9 -178.33(12) . . . . ? C7 C8 C9 C10 1.8(2) . . . . ? C8 C9 C10 C11 -2.7(3) . . . . ? C8 C9 C10 C13 177.14(17) . . . . ? C9 C10 C11 C12 1.0(3) . . . . ? C13 C10 C11 C12 -178.90(18) . . . . ? C10 C11 C12 C7 1.6(3) . . . . ? C8 C7 C12 C11 -2.6(2) . . . . ? S1 C7 C12 C11 176.62(13) . . . . ? N2 C3 C14 C19 -33.89(19) . . . . ? C4 C3 C14 C19 87.85(17) . . . . ? N2 C3 C14 C15 146.97(14) . . . . ? C4 C3 C14 C15 -91.29(17) . . . . ? C19 C14 C15 C16 0.6(3) . . . . ? C3 C14 C15 C16 179.73(16) . . . . ? C14 C15 C16 C17 1.5(3) . . . . ? C15 C16 C17 C18 -2.0(3) . . . . ? C15 C16 C17 N3 176.28(18) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? N3 C17 C18 C19 -178.02(17) . . . . ? C17 C18 C19 C14 2.0(3) . . . . ? C15 C14 C19 C18 -2.4(3) . . . . ? C3 C14 C19 C18 178.50(15) . . . . ? C5 C4 C20 O5 -144.01(15) . . . . ? C3 C4 C20 O5 40.75(18) . . . . ? C5 C6 N1 N2 -1.0(2) . . . . ? C21 C6 N1 N2 177.66(14) . . . . ? C6 N1 N2 C3 28.7(2) . . . . ? C6 N1 N2 S1 -174.43(11) . . . . ? C4 C3 N2 N1 -37.52(19) . . . . ? C14 C3 N2 N1 86.59(16) . . . . ? C4 C3 N2 S1 167.21(10) . . . . ? C14 C3 N2 S1 -68.68(15) . . . . ? C16 C17 N3 O3B -25(2) . . . . ? C18 C17 N3 O3B 154(2) . . . . ? C16 C17 N3 O4B 146(2) . . . . ? C18 C17 N3 O4B -36(2) . . . . ? C16 C17 N3 O4 -164.6(2) . . . . ? C18 C17 N3 O4 13.7(3) . . . . ? C16 C17 N3 O3 15.8(3) . . . . ? C18 C17 N3 O3 -165.9(2) . . . . ? N1 N2 S1 O2 -40.40(12) . . . . ? C3 N2 S1 O2 117.66(12) . . . . ? N1 N2 S1 O1 -170.41(10) . . . . ? C3 N2 S1 O1 -12.35(14) . . . . ? N1 N2 S1 C7 75.11(12) . . . . ? C3 N2 S1 C7 -126.83(12) . . . . ? C8 C7 S1 O2 -141.61(11) . . . . ? C12 C7 S1 O2 39.19(14) . . . . ? C8 C7 S1 O1 -9.52(13) . . . . ? C12 C7 S1 O1 171.28(11) . . . . ? C8 C7 S1 N2 101.92(12) . . . . ? C12 C7 S1 N2 -77.28(13) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF