# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_publication_text _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Paul M. Lahti' _publ_contact_author_address ;Dept of Chemistry Univ of Massachusetts Amherst, MA 01003 USA ; _publ_contact_author_email lahti@chem.umass.edu loop_ _publ_author_name _publ_author_address 'Handan Akpinar' ;Dept of Chemistry Univ of Massachusetts Amherst, MA 01003 USA ; 'Joel T. Mague' ;Dept of Chemistry Tulane University New Orleans, LA 70118 USA ; 'Miguel A. Novak' ;Institutor de F\'isica Universidade Federal do Rio de Janeiro Rio de Janeiro-RJ, 21945-970, Brazil ; 'Jonathan A. Friedman' ;Department of Physics Amherst College Amherst, MA 01002 USA ; 'Paul M. Lahti' ;Department of Chemistry University of Massachusetts Amherst, MA 01003 USA ; data_phl004_0m _database_code_depnum_ccdc_archive 'CCDC 840778' #TrackingRef 'PyrIN-b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 N2 O' _chemical_formula_sum 'C23 H21 N2 O' _chemical_formula_weight 341.42 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6366(7) _cell_length_b 15.5557(14) _cell_length_c 15.0141(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.3950(10) _cell_angle_gamma 90.00 _cell_volume 1783.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9954 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.44 _exptl_crystal_description Block _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9333 _exptl_absorpt_correction_T_max 0.9875 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008a)' _exptl_special_details ; The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5 deg. in omega, colllected at phi = 0.00, 90.00 and 180.00 deg. and 2 sets of 800 frames, each of width 0.45 deg in phi, collected at omega = -30.00 and 210.00 deg. The scan time was 20 sec/frame. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29677 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.54 _reflns_number_total 8133 _reflns_number_gt 6382 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (Bruker-AXS, 2009)' _computing_cell_refinement 'Bruker SAINT (Bruker-AXS 2009a)' _computing_data_reduction 'Bruker SAINT (Bruker-AXS 2009a)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL(Bruker-AXS 2008)' _computing_publication_material 'Bruker SHELXTL(Bruker-AXS 2008)' _publ_section_references ; Bruker-AXS (2009). APEX2, Version 2009.11-0, Madison, WI. Bruker-AXS (2009a). SAINT, Version 7.68A, Madison, WI Bruker-AXS (2008). SHELXTL, Version 2008/4, Madison, WI Sheldrick, G. M. (2008). SHELXS and SHELXL. Acta Cryst. A64, 112-122. Sheldrick, G, M. (2008a). SADABS, Version 2008/2. University of G\"ottingen, Germany. ; _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. H-atoms were placed in calculated positions (C---H = 0.95 - 0.98 \%A) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. Both independent molecules are disordered over two approximately equally populated sites. The disorder involves a "flipping over" of the pyrenyl portion and a twisting of the 5-membered ring. Because of the significant overlap between the two sites, the refinement was carried out with the pyrenyl and the 5-membered ring portions of the molecules treated as rigid groups with geometries taken from an ordered structure of the same molecule. ; _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^)+(0.1367P)^2^+1.7451P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Flack H D (1983), Acta Cryst. A39, 876-881. The absolute configuration could not be determined with certainty. ; _refine_ls_abs_structure_Flack 1(4) _refine_ls_number_reflns 8133 _refine_ls_number_parameters 322 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1182 _refine_ls_R_factor_gt 0.0989 _refine_ls_wR_factor_ref 0.2891 _refine_ls_wR_factor_gt 0.2711 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 C1 C 0.99496(14) 0.600(11) 0.05133(7) 0.0402(12) Uani 0.6345(19) 1 d PG A 1 O1 O 1.21604(17) 0.519(11) -0.02515(8) 0.082(2) Uani 0.6345(19) 1 d PG A 1 N1 N 1.10730(16) 0.581(11) -0.01987(7) 0.0488(13) Uani 0.6345(19) 1 d PG A 1 N2 N 0.89789(15) 0.667(11) 0.03622(6) 0.0579(18) Uani 0.6345(19) 1 d PG A 1 C2 C 1.10844(18) 0.657(11) -0.08156(8) 0.0590(17) Uani 0.6345(19) 1 d PG A 1 C3 C 0.92637(18) 0.695(11) -0.05771(7) 0.0494(12) Uani 0.6345(19) 1 d PG A 1 C4 C 1.26173(18) 0.714(11) -0.05101(9) 0.090(3) Uani 0.6345(19) 1 d PG A 1 H4A H 1.2435 0.7317 0.0108 0.135 Uiso 0.6345(19) 1 calc PR A 1 H4B H 1.2684 0.7648 -0.0892 0.135 Uiso 0.6345(19) 1 calc PR A 1 H4C H 1.3713 0.6813 -0.0551 0.135 Uiso 0.6345(19) 1 calc PR A 1 C5 C 1.1328(2) 0.628(11) -0.17685(8) 0.097(3) Uani 0.6345(19) 1 d PGU A 1 H5A H 1.0337 0.5922 -0.1951 0.146 Uiso 0.6345(19) 1 calc PR A 1 H5B H 1.2417 0.5954 -0.1816 0.146 Uiso 0.6345(19) 1 calc PR A 1 H5C H 1.1388 0.6789 -0.2157 0.146 Uiso 0.6345(19) 1 calc PR A 1 C6 C 0.77818(19) 0.656(11) -0.11356(6) 0.080(3) Uani 0.6345(19) 1 d PG A 1 H6A H 0.7848 0.5931 -0.1102 0.120 Uiso 0.6345(19) 1 calc PR A 1 H6B H 0.7899 0.6742 -0.1757 0.120 Uiso 0.6345(19) 1 calc PR A 1 H6C H 0.6651 0.6753 -0.0905 0.120 Uiso 0.6345(19) 1 calc PR A 1 C7 C 0.9173(2) 0.793(11) -0.06252(8) 0.0509(17) Uani 0.6345(19) 1 d PG A 1 H7A H 1.0124 0.8176 -0.0267 0.076 Uiso 0.6345(19) 1 calc PR A 1 H7B H 0.8045 0.8124 -0.0394 0.076 Uiso 0.6345(19) 1 calc PR A 1 H7C H 0.9293 0.8113 -0.1246 0.076 Uiso 0.6345(19) 1 calc PR A 1 C8 C 1.00452(12) 0.552(11) 0.13545(7) 0.0408(11) Uani 0.6345(19) 1 d PG A 1 C9 C 1.16460(12) 0.549(11) 0.18094(8) 0.0427(11) Uani 0.6345(19) 1 d PG A 1 H9 H 1.2567 0.5863 0.1638 0.051 Uiso 0.6345(19) 1 calc PR A 1 C10 C 1.19054(12) 0.492(11) 0.25057(8) 0.0414(11) Uani 0.6345(19) 1 d PG A 1 H10 H 1.3000 0.4914 0.2810 0.050 Uiso 0.6345(19) 1 calc PR A 1 C11 C 1.05856(13) 0.436(11) 0.27701(7) 0.0367(11) Uani 0.6345(19) 1 d PG A 1 C12 C 1.08017(15) 0.378(11) 0.35085(8) 0.0460(13) Uani 0.6345(19) 1 d PG A 1 H12 H 1.1899 0.3752 0.3810 0.055 Uiso 0.6345(19) 1 calc PR A 1 C13 C 0.94783(17) 0.327(11) 0.37841(8) 0.0504(13) Uani 0.6345(19) 1 d PG A 1 H13 H 0.9654 0.2905 0.4286 0.060 Uiso 0.6345(19) 1 calc PR A 1 C14 C 0.78171(17) 0.326(11) 0.33363(8) 0.0404(10) Uani 0.6345(19) 1 d PG A 1 C15 C 0.64310(19) 0.273(11) 0.36018(8) 0.0510(13) Uani 0.6345(19) 1 d PG A 1 H15 H 0.6578 0.2370 0.4104 0.061 Uiso 0.6345(19) 1 calc PR A 1 C16 C 0.48523(19) 0.274(11) 0.31467(9) 0.0486(13) Uani 0.6345(19) 1 d PG A 1 H16 H 0.3930 0.2371 0.3338 0.058 Uiso 0.6345(19) 1 calc PR A 1 C17 C 0.46017(17) 0.326(11) 0.24117(8) 0.0458(13) Uani 0.6345(19) 1 d PG A 1 H17 H 0.3515 0.3255 0.2100 0.055 Uiso 0.6345(19) 1 calc PR A 1 C18 C 0.59400(15) 0.381(11) 0.21274(7) 0.0395(11) Uani 0.6345(19) 1 d PG A 1 C19 C 0.57254(14) 0.439(11) 0.13851(6) 0.0432(12) Uani 0.6345(19) 1 d PG A 1 H19 H 0.4652 0.4381 0.1061 0.052 Uiso 0.6345(19) 1 calc PR A 1 C20 C 0.70079(13) 0.493(11) 0.11334(6) 0.0386(10) Uani 0.6345(19) 1 d PG A 1 H20 H 0.6805 0.5309 0.0645 0.046 Uiso 0.6345(19) 1 calc PR A 1 C21 C 0.86733(13) 0.496(11) 0.15894(6) 0.0332(7) Uani 0.6345(19) 1 d PG A 1 C22 C 0.89459(13) 0.437(11) 0.23099(7) 0.0332(9) Uani 0.6345(19) 1 d PG A 1 C23 C 0.75739(15) 0.381(11) 0.25855(7) 0.0381(12) Uani 0.6345(19) 1 d PG A 1 C1A C 0.89817(15) 0.589(11) 0.02664(6) 0.0402(12) Uani 0.3655(19) 1 d PG A 2 O1A O 1.13584(17) 0.494(11) -0.00783(8) 0.082(2) Uani 0.3655(19) 1 d PG A 2 N1A N 1.05411(16) 0.565(11) -0.01582(7) 0.0488(13) Uani 0.3655(19) 1 d PG A 2 N2A N 0.84599(16) 0.665(11) 0.00377(6) 0.0579(18) Uani 0.3655(19) 1 d PG A 2 C2A C 1.13233(17) 0.643(11) -0.05764(8) 0.0590(17) Uani 0.3655(19) 1 d PG A 2 C3A C 0.96208(18) 0.698(11) -0.06881(7) 0.0494(12) Uani 0.3655(19) 1 d PG A 2 C4A C 1.25915(16) 0.681(11) 0.01196(9) 0.090(3) Uani 0.3655(19) 1 d PG A 2 H4A1 H 1.1946 0.6954 0.0661 0.135 Uiso 0.3655(19) 1 calc PR A 2 H4A2 H 1.3141 0.7328 -0.0120 0.135 Uiso 0.3655(19) 1 calc PR A 2 H4A3 H 1.3497 0.6383 0.0262 0.135 Uiso 0.3655(19) 1 calc PR A 2 C5A C 1.2282(2) 0.620(11) -0.14206(9) 0.097(3) Uani 0.3655(19) 1 d PGU A 2 H5A1 H 1.1450 0.5966 -0.1856 0.146 Uiso 0.3655(19) 1 calc PR A 2 H5A2 H 1.3186 0.5775 -0.1286 0.146 Uiso 0.3655(19) 1 calc PR A 2 H5A3 H 1.2830 0.6720 -0.1667 0.146 Uiso 0.3655(19) 1 calc PR A 2 C6A C 0.8672(2) 0.679(11) -0.15687(6) 0.080(3) Uani 0.3655(19) 1 d PG A 2 H6A1 H 0.8507 0.6164 -0.1631 0.120 Uiso 0.3655(19) 1 calc PR A 2 H6A2 H 0.9375 0.6999 -0.2066 0.120 Uiso 0.3655(19) 1 calc PR A 2 H6A3 H 0.7529 0.7072 -0.1573 0.120 Uiso 0.3655(19) 1 calc PR A 2 C7A C 0.9884(2) 0.794(11) -0.05848(8) 0.0509(17) Uani 0.3655(19) 1 d PG A 2 H7A1 H 1.0491 0.8056 -0.0021 0.076 Uiso 0.3655(19) 1 calc PR A 2 H7A2 H 0.8743 0.8227 -0.0587 0.076 Uiso 0.3655(19) 1 calc PR A 2 H7A3 H 1.0589 0.8154 -0.1080 0.076 Uiso 0.3655(19) 1 calc PR A 2 C8A C 0.79621(14) 0.534(11) 0.08565(6) 0.0408(11) Uani 0.3655(19) 1 d PG A 2 C9A C 0.62370(14) 0.516(11) 0.06029(6) 0.0427(11) Uani 0.3655(19) 1 d PG A 2 H9A H 0.5727 0.5460 0.0113 0.051 Uiso 0.3655(19) 1 calc PR A 2 C10A C 0.52629(14) 0.456(11) 0.10559(6) 0.0414(11) Uani 0.3655(19) 1 d PG A 2 H10A H 0.4096 0.4440 0.0869 0.050 Uiso 0.3655(19) 1 calc PR A 2 C11A C 0.59644(14) 0.411(11) 0.17842(6) 0.0367(11) Uani 0.3655(19) 1 d PG A 2 C12A C 0.50002(16) 0.346(11) 0.22492(8) 0.0460(13) Uani 0.3655(19) 1 d PG A 2 H12A H 0.3821 0.3348 0.2080 0.055 Uiso 0.3655(19) 1 calc PR A 2 C13A C 0.57337(18) 0.301(11) 0.29214(8) 0.0504(13) Uani 0.3655(19) 1 d PG A 2 H13A H 0.5071 0.2568 0.3203 0.060 Uiso 0.3655(19) 1 calc PR A 2 C14A C 0.74874(17) 0.317(11) 0.32187(8) 0.0404(10) Uani 0.3655(19) 1 d PG A 2 C15A C 0.82719(19) 0.271(11) 0.39197(8) 0.0510(13) Uani 0.3655(19) 1 d PG A 2 H15A H 0.7633 0.2272 0.4208 0.061 Uiso 0.3655(19) 1 calc PR A 2 C16A C 0.99584(19) 0.290(11) 0.41996(9) 0.0486(13) Uani 0.3655(19) 1 d PG A 2 H16A H 1.0463 0.2581 0.4678 0.058 Uiso 0.3655(19) 1 calc PR A 2 C17A C 1.09217(16) 0.354(11) 0.37877(8) 0.0458(13) Uani 0.3655(19) 1 d PG A 2 H17A H 1.2075 0.3665 0.3990 0.055 Uiso 0.3655(19) 1 calc PR A 2 C18A C 1.02032(14) 0.401(11) 0.30764(8) 0.0395(11) Uani 0.3655(19) 1 d PG A 2 C19A C 1.11651(12) 0.466(11) 0.26165(8) 0.0432(12) Uani 0.3655(19) 1 d PG A 2 H19A H 1.2316 0.4799 0.2814 0.052 Uiso 0.3655(19) 1 calc PR A 2 C20A C 1.04790(12) 0.509(11) 0.19107(7) 0.0386(10) Uani 0.3655(19) 1 d PG A 2 H20A H 1.1167 0.5510 0.1618 0.046 Uiso 0.3655(19) 1 calc PR A 2 C21A C 0.87290(13) 0.492(11) 0.15927(6) 0.0332(7) Uani 0.3655(19) 1 d PG A 2 C22A C 0.77185(14) 0.429(11) 0.20589(6) 0.0332(9) Uani 0.3655(19) 1 d PG A 2 C23A C 0.84648(15) 0.383(11) 0.27881(7) 0.0381(12) Uani 0.3655(19) 1 d PG A 2 C24 C 0.39357(14) 0.578(11) 0.47515(6) 0.0385(11) Uani 0.5395(17) 1 d PG B 1 O2 O 0.63983(16) 0.670(11) 0.50640(6) 0.0586(13) Uani 0.5395(17) 1 d PG B 1 N3 N 0.55317(16) 0.600(11) 0.51635(6) 0.0405(12) Uani 0.5395(17) 1 d PG B 1 N4 N 0.33677(15) 0.504(11) 0.49992(7) 0.0506(16) Uani 0.5395(17) 1 d PG B 1 C25 C 0.62739(17) 0.521(11) 0.55951(6) 0.0575(17) Uani 0.5395(17) 1 d PG B 1 C26 C 0.45370(18) 0.470(11) 0.57265(6) 0.0468(11) Uani 0.5395(17) 1 d PG B 1 C27 C 0.74804(15) 0.480(11) 0.49017(6) 0.076(2) Uani 0.5395(17) 1 d PG B 1 H27A H 0.6799 0.4658 0.4367 0.113 Uiso 0.5395(17) 1 calc PR B 1 H27B H 0.8002 0.4277 0.5150 0.113 Uiso 0.5395(17) 1 calc PR B 1 H27C H 0.8411 0.5207 0.4746 0.113 Uiso 0.5395(17) 1 calc PR B 1 C28 C 0.7288(2) 0.544(11) 0.64295(6) 0.083(3) Uani 0.5395(17) 1 d PG B 1 H28A H 0.6495 0.5703 0.6863 0.124 Uiso 0.5395(17) 1 calc PR B 1 H28B H 0.8218 0.5851 0.6281 0.124 Uiso 0.5395(17) 1 calc PR B 1 H28C H 0.7808 0.4921 0.6685 0.124 Uiso 0.5395(17) 1 calc PR B 1 C29 C 0.3645(2) 0.493(11) 0.66070(7) 0.080(3) Uani 0.5395(17) 1 d PG B 1 H29A H 0.3529 0.5555 0.6656 0.119 Uiso 0.5395(17) 1 calc PR B 1 H29B H 0.4353 0.4713 0.7105 0.119 Uiso 0.5395(17) 1 calc PR B 1 H29C H 0.2481 0.4665 0.6623 0.119 Uiso 0.5395(17) 1 calc PR B 1 C30 C 0.47232(19) 0.374(11) 0.56432(7) 0.0508(17) Uani 0.5395(17) 1 d PG B 1 H30A H 0.5295 0.3597 0.5079 0.076 Uiso 0.5395(17) 1 calc PR B 1 H30B H 0.3561 0.3469 0.5657 0.076 Uiso 0.5395(17) 1 calc PR B 1 H30C H 0.5434 0.3518 0.6140 0.076 Uiso 0.5395(17) 1 calc PR B 1 C31 C 0.29242(13) 0.634(11) 0.41676(7) 0.0408(11) Uani 0.5395(17) 1 d PG B 1 C32 C 0.12021(14) 0.653(11) 0.44084(8) 0.0426(12) Uani 0.5395(17) 1 d PG B 1 H32 H 0.0690 0.6237 0.4898 0.051 Uiso 0.5395(17) 1 calc PR B 1 C33 C 0.02339(14) 0.713(11) 0.39425(9) 0.0432(12) Uani 0.5395(17) 1 d PG B 1 H33 H -0.0931 0.7254 0.4121 0.052 Uiso 0.5395(17) 1 calc PR B 1 C34 C 0.09384(14) 0.757(11) 0.32135(9) 0.0377(13) Uani 0.5395(17) 1 d PG B 1 C35 C -0.00194(16) 0.822(11) 0.27352(10) 0.0457(14) Uani 0.5395(17) 1 d PG B 1 H35 H -0.1196 0.8335 0.2895 0.055 Uiso 0.5395(17) 1 calc PR B 1 C36 C 0.07174(18) 0.866(11) 0.20625(10) 0.0521(14) Uani 0.5395(17) 1 d PG B 1 H36 H 0.0059 0.9099 0.1772 0.062 Uiso 0.5395(17) 1 calc PR B 1 C37 C 0.24682(17) 0.849(11) 0.17780(9) 0.0401(10) Uani 0.5395(17) 1 d PG B 1 C38 C 0.32559(19) 0.894(11) 0.10768(9) 0.0508(14) Uani 0.5395(17) 1 d PG B 1 H38 H 0.2622 0.9377 0.0779 0.061 Uiso 0.5395(17) 1 calc PR B 1 C39 C 0.49393(19) 0.874(11) 0.08095(8) 0.0571(16) Uani 0.5395(17) 1 d PG B 1 H39 H 0.5447 0.9054 0.0331 0.069 Uiso 0.5395(17) 1 calc PR B 1 C40 C 0.58961(16) 0.810(11) 0.12346(7) 0.0538(17) Uani 0.5395(17) 1 d PG B 1 H40 H 0.7048 0.7973 0.1041 0.065 Uiso 0.5395(17) 1 calc PR B 1 C41 C 0.51743(14) 0.765(11) 0.19467(7) 0.0412(12) Uani 0.5395(17) 1 d PG B 1 C42 C 0.61298(12) 0.699(11) 0.24198(6) 0.0427(13) Uani 0.5395(17) 1 d PG B 1 H42 H 0.7279 0.6852 0.2232 0.051 Uiso 0.5395(17) 1 calc PR B 1 C43 C 0.54408(12) 0.658(11) 0.31262(6) 0.0352(10) Uani 0.5395(17) 1 d PG B 1 H43 H 0.6125 0.6156 0.3428 0.042 Uiso 0.5395(17) 1 calc PR B 1 C44 C 0.36939(13) 0.676(11) 0.34313(7) 0.0323(7) Uani 0.5395(17) 1 d PG B 1 C45 C 0.26895(14) 0.738(11) 0.29519(7) 0.0347(10) Uani 0.5395(17) 1 d PG B 1 C46 C 0.34390(15) 0.783(11) 0.22221(8) 0.0388(13) Uani 0.5395(17) 1 d PG B 1 C24A C 0.49312(14) 0.568(11) 0.45123(6) 0.0385(11) Uani 0.4605(17) 1 d PG B 2 O2A O 0.72073(17) 0.645(11) 0.52849(6) 0.0586(13) Uani 0.4605(17) 1 d PG B 2 N3A N 0.60861(16) 0.584(11) 0.52253(5) 0.0405(12) Uani 0.4605(17) 1 d PG B 2 N4A N 0.39306(14) 0.502(11) 0.46560(6) 0.0506(16) Uani 0.4605(17) 1 d PG B 2 C25A C 0.60771(18) 0.508(11) 0.58324(6) 0.0575(17) Uani 0.4605(17) 1 d PG B 2 C26A C 0.42295(17) 0.472(11) 0.55911(7) 0.0468(11) Uani 0.4605(17) 1 d PG B 2 C27A C 0.75702(18) 0.450(11) 0.55176(6) 0.076(2) Uani 0.4605(17) 1 d PG B 2 H27D H 0.7359 0.4327 0.4897 0.113 Uiso 0.4605(17) 1 calc PR B 2 H27E H 0.7622 0.3981 0.5893 0.113 Uiso 0.4605(17) 1 calc PR B 2 H27F H 0.8683 0.4807 0.5562 0.113 Uiso 0.4605(17) 1 calc PR B 2 C28A C 0.6365(2) 0.535(11) 0.67886(5) 0.083(3) Uani 0.4605(17) 1 d PG B 2 H28D H 0.5400 0.5722 0.6977 0.124 Uiso 0.4605(17) 1 calc PR B 2 H28E H 0.7473 0.5666 0.6839 0.124 Uiso 0.4605(17) 1 calc PR B 2 H28F H 0.6411 0.4840 0.7170 0.124 Uiso 0.4605(17) 1 calc PR B 2 C29A C 0.27862(19) 0.513(11) 0.61565(7) 0.080(3) Uani 0.4605(17) 1 d PG B 2 H29D H 0.2884 0.5755 0.6131 0.119 Uiso 0.4605(17) 1 calc PR B 2 H29E H 0.2913 0.4936 0.6775 0.119 Uiso 0.4605(17) 1 calc PR B 2 H29F H 0.1638 0.4951 0.5925 0.119 Uiso 0.4605(17) 1 calc PR B 2 C30A C 0.40896(19) 0.375(11) 0.56266(8) 0.0508(17) Uani 0.4605(17) 1 d PG B 2 H30D H 0.5016 0.3493 0.5264 0.076 Uiso 0.4605(17) 1 calc PR B 2 H30E H 0.2944 0.3569 0.5394 0.076 Uiso 0.4605(17) 1 calc PR B 2 H30F H 0.4219 0.3554 0.6245 0.076 Uiso 0.4605(17) 1 calc PR B 2 C31A C 0.50338(12) 0.616(11) 0.36698(6) 0.0408(11) Uani 0.4605(17) 1 d PG B 2 C32A C 0.66301(11) 0.618(11) 0.32214(5) 0.0426(12) Uani 0.4605(17) 1 d PG B 2 H32A H 0.7550 0.5804 0.3401 0.051 Uiso 0.4605(17) 1 calc PR B 2 C33A C 0.68869(12) 0.674(11) 0.25197(6) 0.0432(12) Uani 0.4605(17) 1 d PG B 2 H33A H 0.7979 0.6740 0.2220 0.052 Uiso 0.4605(17) 1 calc PR B 2 C34A C 0.55692(13) 0.730(11) 0.22431(6) 0.0377(13) Uani 0.4605(17) 1 d PG B 2 C35A C 0.57824(15) 0.787(11) 0.14989(7) 0.0457(14) Uani 0.4605(17) 1 d PG B 2 H35A H 0.6876 0.7893 0.1202 0.055 Uiso 0.4605(17) 1 calc PR B 2 C36A C 0.44605(17) 0.838(11) 0.12117(8) 0.0521(14) Uani 0.4605(17) 1 d PG B 2 H36A H 0.4634 0.8739 0.0706 0.062 Uiso 0.4605(17) 1 calc PR B 2 C37A C 0.28041(17) 0.840(11) 0.16524(8) 0.0401(10) Uani 0.4605(17) 1 d PG B 2 C38A C 0.14197(19) 0.892(11) 0.13749(10) 0.0508(14) Uani 0.4605(17) 1 d PG B 2 H38A H 0.1565 0.9283 0.0869 0.061 Uiso 0.4605(17) 1 calc PR B 2 C39A C -0.01541(19) 0.893(11) 0.18232(11) 0.0571(16) Uani 0.4605(17) 1 d PG B 2 H39A H -0.1075 0.9296 0.1624 0.069 Uiso 0.4605(17) 1 calc PR B 2 C40A C -0.04014(17) 0.841(11) 0.25633(11) 0.0538(17) Uani 0.4605(17) 1 d PG B 2 H40A H -0.1485 0.8426 0.2870 0.065 Uiso 0.4605(17) 1 calc PR B 2 C41A C 0.09352(15) 0.786(11) 0.28596(9) 0.0412(12) Uani 0.4605(17) 1 d PG B 2 C42A C 0.07236(14) 0.730(11) 0.36077(9) 0.0427(13) Uani 0.4605(17) 1 d PG B 2 H42A H -0.0346 0.7309 0.3927 0.051 Uiso 0.4605(17) 1 calc PR B 2 C43A C 0.20040(13) 0.675(11) 0.38711(8) 0.0352(10) Uani 0.4605(17) 1 d PG B 2 H43A H 0.1804 0.6381 0.4363 0.042 Uiso 0.4605(17) 1 calc PR B 2 C44A C 0.36643(12) 0.672(11) 0.34226(7) 0.0323(7) Uani 0.4605(17) 1 d PG B 2 C45A C 0.39342(13) 0.730(11) 0.26965(7) 0.0347(10) Uani 0.4605(17) 1 d PG B 2 C46A C 0.25642(15) 0.786(11) 0.24085(8) 0.0388(13) Uani 0.4605(17) 1 d PG B 2 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 C1 0.051(3) 0.029(2) 0.041(3) 0.001(2) 0.006(2) -0.007(2) O1 0.105(5) 0.063(4) 0.078(3) -0.001(3) 0.004(3) 0.042(4) N1 0.062(3) 0.039(2) 0.045(2) -0.0003(17) 0.008(2) 0.013(2) N2 0.068(4) 0.034(2) 0.071(4) 0.010(3) 0.021(3) 0.011(2) C2 0.080(4) 0.043(3) 0.055(4) 0.005(3) 0.024(3) 0.006(3) C3 0.064(3) 0.032(2) 0.052(3) 0.0091(18) 0.005(2) -0.001(2) C4 0.065(4) 0.088(6) 0.117(8) 0.027(5) 0.015(5) -0.029(4) C5 0.126(6) 0.094(5) 0.072(5) -0.001(4) 0.026(4) 0.014(5) C6 0.106(7) 0.045(4) 0.089(6) 0.019(4) -0.036(5) -0.010(4) C7 0.067(5) 0.033(2) 0.054(3) 0.0027(19) 0.006(3) -0.012(3) C8 0.047(3) 0.030(2) 0.045(3) 0.006(2) 0.007(2) -0.002(2) C9 0.039(3) 0.029(2) 0.059(3) 0.005(2) 0.005(2) -0.001(2) C10 0.047(3) 0.024(2) 0.053(3) 0.005(2) -0.009(2) -0.003(2) C11 0.037(3) 0.032(3) 0.041(3) -0.004(2) -0.001(2) -0.010(2) C12 0.048(3) 0.052(3) 0.038(3) 0.014(3) -0.001(2) -0.003(3) C13 0.064(4) 0.044(3) 0.043(3) 0.005(2) 0.003(2) -0.005(3) C14 0.053(3) 0.0259(19) 0.042(2) -0.0041(16) 0.0015(19) -0.0043(18) C15 0.062(3) 0.033(3) 0.057(3) 0.009(2) 0.012(3) -0.004(2) C16 0.053(3) 0.042(3) 0.052(3) 0.004(2) 0.007(2) -0.009(2) C17 0.043(3) 0.048(3) 0.046(3) 0.005(3) 0.008(2) -0.004(2) C18 0.039(3) 0.033(3) 0.046(3) 0.003(2) 0.009(2) 0.000(2) C19 0.047(3) 0.039(3) 0.044(3) 0.002(2) -0.006(2) -0.008(2) C20 0.040(3) 0.035(2) 0.041(2) 0.002(2) -0.004(2) -0.001(2) C21 0.0350(17) 0.0276(16) 0.0371(16) -0.0044(13) 0.0009(13) 0.0008(13) C22 0.039(2) 0.025(2) 0.036(2) -0.0035(18) 0.0032(18) 0.0011(19) C23 0.047(4) 0.029(2) 0.038(3) -0.0091(19) 0.002(2) -0.006(3) C1A 0.051(3) 0.029(2) 0.041(3) 0.001(2) 0.006(2) -0.007(2) O1A 0.105(5) 0.063(4) 0.078(3) -0.001(3) 0.004(3) 0.042(4) N1A 0.062(3) 0.039(2) 0.045(2) -0.0003(17) 0.008(2) 0.013(2) N2A 0.068(4) 0.034(2) 0.071(4) 0.010(3) 0.021(3) 0.011(2) C2A 0.080(4) 0.043(3) 0.055(4) 0.005(3) 0.024(3) 0.006(3) C3A 0.064(3) 0.032(2) 0.052(3) 0.0091(18) 0.005(2) -0.001(2) C4A 0.065(4) 0.088(6) 0.117(8) 0.027(5) 0.015(5) -0.029(4) C5A 0.126(6) 0.094(5) 0.072(5) -0.001(4) 0.026(4) 0.014(5) C6A 0.106(7) 0.045(4) 0.089(6) 0.019(4) -0.036(5) -0.010(4) C7A 0.067(5) 0.033(2) 0.054(3) 0.0027(19) 0.006(3) -0.012(3) C8A 0.047(3) 0.030(2) 0.045(3) 0.006(2) 0.007(2) -0.002(2) C9A 0.039(3) 0.029(2) 0.059(3) 0.005(2) 0.005(2) -0.001(2) C10A 0.047(3) 0.024(2) 0.053(3) 0.005(2) -0.009(2) -0.003(2) C11A 0.037(3) 0.032(3) 0.041(3) -0.004(2) -0.001(2) -0.010(2) C12A 0.048(3) 0.052(3) 0.038(3) 0.014(3) -0.001(2) -0.003(3) C13A 0.064(4) 0.044(3) 0.043(3) 0.005(2) 0.003(2) -0.005(3) C14A 0.053(3) 0.0259(19) 0.042(2) -0.0041(16) 0.0015(19) -0.0043(18) C15A 0.062(3) 0.033(3) 0.057(3) 0.009(2) 0.012(3) -0.004(2) C16A 0.053(3) 0.042(3) 0.052(3) 0.004(2) 0.007(2) -0.009(2) C17A 0.043(3) 0.048(3) 0.046(3) 0.005(3) 0.008(2) -0.004(2) C18A 0.039(3) 0.033(3) 0.046(3) 0.003(2) 0.009(2) 0.000(2) C19A 0.047(3) 0.039(3) 0.044(3) 0.002(2) -0.006(2) -0.008(2) C20A 0.040(3) 0.035(2) 0.041(2) 0.002(2) -0.004(2) -0.001(2) C21A 0.0350(17) 0.0276(16) 0.0371(16) -0.0044(13) 0.0009(13) 0.0008(13) C22A 0.039(2) 0.025(2) 0.036(2) -0.0035(18) 0.0032(18) 0.0011(19) C23A 0.047(4) 0.029(2) 0.038(3) -0.0091(19) 0.002(2) -0.006(3) C24 0.049(3) 0.027(2) 0.039(3) -0.004(2) -0.001(2) 0.004(2) O2 0.058(3) 0.053(3) 0.064(3) -0.002(2) -0.010(2) -0.019(3) N3 0.045(3) 0.032(2) 0.044(2) -0.0010(17) -0.003(2) 0.005(2) N4 0.070(4) 0.0294(18) 0.053(4) 0.009(2) -0.007(3) -0.006(2) C25 0.074(4) 0.045(3) 0.054(4) -0.002(3) -0.014(3) 0.006(3) C26 0.067(3) 0.0276(18) 0.046(2) 0.0069(17) -0.006(2) 0.0011(19) C27 0.079(5) 0.075(5) 0.072(5) 0.006(4) -0.004(4) 0.027(4) C28 0.120(9) 0.072(5) 0.056(5) 0.015(4) -0.028(5) -0.019(6) C29 0.111(8) 0.061(5) 0.067(5) 0.019(4) 0.026(5) 0.006(5) C30 0.068(5) 0.030(2) 0.054(3) 0.0037(19) -0.017(3) 0.011(3) C31 0.044(3) 0.032(2) 0.047(3) 0.004(2) -0.003(2) -0.002(2) C32 0.051(3) 0.032(3) 0.044(3) 0.003(2) 0.004(2) 0.002(2) C33 0.039(3) 0.033(3) 0.057(3) 0.004(2) 0.013(2) 0.003(2) C34 0.034(3) 0.043(3) 0.036(3) -0.007(2) 0.002(2) 0.006(2) C35 0.044(3) 0.045(3) 0.048(3) 0.003(3) 0.004(2) -0.003(3) C36 0.075(4) 0.041(3) 0.041(3) -0.002(2) -0.001(3) 0.003(3) C37 0.049(3) 0.0251(19) 0.047(2) -0.0042(17) -0.001(2) 0.0016(18) C38 0.066(4) 0.032(3) 0.055(3) 0.011(2) -0.010(3) -0.002(3) C39 0.058(4) 0.055(4) 0.058(4) 0.017(3) -0.008(3) -0.004(3) C40 0.051(3) 0.068(5) 0.042(3) 0.006(3) -0.009(2) 0.003(3) C41 0.039(3) 0.041(3) 0.044(3) 0.003(2) -0.005(2) 0.000(2) C42 0.041(3) 0.043(3) 0.045(3) -0.001(3) 0.014(2) 0.000(2) C43 0.033(2) 0.030(2) 0.043(2) -0.001(2) 0.0055(19) -0.0013(19) C44 0.0356(16) 0.0269(16) 0.0343(16) -0.0034(12) -0.0002(12) -0.0005(13) C45 0.041(3) 0.026(2) 0.037(2) -0.0037(19) -0.0049(19) -0.001(2) C46 0.053(4) 0.030(2) 0.034(3) -0.004(2) 0.003(3) -0.003(3) C24A 0.049(3) 0.027(2) 0.039(3) -0.004(2) -0.001(2) 0.004(2) O2A 0.058(3) 0.053(3) 0.064(3) -0.002(2) -0.010(2) -0.019(3) N3A 0.045(3) 0.032(2) 0.044(2) -0.0010(17) -0.003(2) 0.005(2) N4A 0.070(4) 0.0294(18) 0.053(4) 0.009(2) -0.007(3) -0.006(2) C25A 0.074(4) 0.045(3) 0.054(4) -0.002(3) -0.014(3) 0.006(3) C26A 0.067(3) 0.0276(18) 0.046(2) 0.0069(17) -0.006(2) 0.0011(19) C27A 0.079(5) 0.075(5) 0.072(5) 0.006(4) -0.004(4) 0.027(4) C28A 0.120(9) 0.072(5) 0.056(5) 0.015(4) -0.028(5) -0.019(6) C29A 0.111(8) 0.061(5) 0.067(5) 0.019(4) 0.026(5) 0.006(5) C30A 0.068(5) 0.030(2) 0.054(3) 0.0037(19) -0.017(3) 0.011(3) C31A 0.044(3) 0.032(2) 0.047(3) 0.004(2) -0.003(2) -0.002(2) C32A 0.051(3) 0.032(3) 0.044(3) 0.003(2) 0.004(2) 0.002(2) C33A 0.039(3) 0.033(3) 0.057(3) 0.004(2) 0.013(2) 0.003(2) C34A 0.034(3) 0.043(3) 0.036(3) -0.007(2) 0.002(2) 0.006(2) C35A 0.044(3) 0.045(3) 0.048(3) 0.003(3) 0.004(2) -0.003(3) C36A 0.075(4) 0.041(3) 0.041(3) -0.002(2) -0.001(3) 0.003(3) C37A 0.049(3) 0.0251(19) 0.047(2) -0.0042(17) -0.001(2) 0.0016(18) C38A 0.066(4) 0.032(3) 0.055(3) 0.011(2) -0.010(3) -0.002(3) C39A 0.058(4) 0.055(4) 0.058(4) 0.017(3) -0.008(3) -0.004(3) C40A 0.051(3) 0.068(5) 0.042(3) 0.006(3) -0.009(2) 0.003(3) C41A 0.039(3) 0.041(3) 0.044(3) 0.003(2) -0.005(2) 0.000(2) C42A 0.041(3) 0.043(3) 0.045(3) -0.001(3) 0.014(2) 0.000(2) C43A 0.033(2) 0.030(2) 0.043(2) -0.001(2) 0.0055(19) -0.0013(19) C44A 0.0356(16) 0.0269(16) 0.0343(16) -0.0034(12) -0.0002(12) -0.0005(13) C45A 0.041(3) 0.026(2) 0.037(2) -0.0037(19) -0.0049(19) -0.001(2) C46A 0.053(4) 0.030(2) 0.034(3) -0.004(2) 0.003(3) -0.003(3) _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 C1 N2 1.2944 . ? C1 N1 1.4050 . ? C1 C8 1.4683 . ? O1 N1 1.2767 . ? N1 C2 1.4960 . ? N2 C3 1.4970 . ? C2 C5 1.5111 . ? C2 C4 1.5344 . ? C2 C3 1.5575 . ? C3 C7 1.5183 . ? C3 C6 1.5321 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.3970 . ? C8 C21 1.4117 . ? C9 C10 1.3826 . ? C9 H9 0.9500 . ? C10 C11 1.3973 . ? C10 H10 0.9500 . ? C11 C22 1.4262 . ? C11 C12 1.4364 . ? C12 C13 1.3510 . ? C12 H12 0.9500 . ? C13 C14 1.4317 . ? C13 H13 0.9500 . ? C14 C15 1.3996 . ? C14 C23 1.4252 . ? C15 C16 1.3817 . ? C15 H15 0.9500 . ? C16 C17 1.3890 . ? C16 H16 0.9500 . ? C17 C18 1.3992 . ? C17 H17 0.9500 . ? C18 C23 1.4206 . ? C18 C19 1.4358 . ? C19 C20 1.3532 . ? C19 H19 0.9500 . ? C20 C21 1.4407 . ? C20 H20 0.9500 . ? C21 C22 1.4291 . ? C22 C23 1.4256 . ? C1A N2A 1.2944 . ? C1A N1A 1.4049 . ? C1A C8A 1.4595 . ? O1A N1A 1.2767 . ? N1A C2A 1.4960 . ? N2A C3A 1.4970 . ? C2A C5A 1.5111 . ? C2A C4A 1.5345 . ? C2A C3A 1.5575 . ? C3A C7A 1.5183 . ? C3A C6A 1.5321 . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 0.9800 . ? C5A H5A1 0.9800 . ? C5A H5A2 0.9800 . ? C5A H5A3 0.9800 . ? C6A H6A1 0.9800 . ? C6A H6A2 0.9800 . ? C6A H6A3 0.9800 . ? C7A H7A1 0.9800 . ? C7A H7A2 0.9800 . ? C7A H7A3 0.9800 . ? C8A C9A 1.3970 . ? C8A C21A 1.4118 . ? C9A C10A 1.3826 . ? C9A H9A 0.9500 . ? C10A C11A 1.3973 . ? C10A H10A 0.9500 . ? C11A C22A 1.4262 . ? C11A C12A 1.4364 . ? C12A C13A 1.3510 . ? C12A H12A 0.9500 . ? C13A C14A 1.4317 . ? C13A H13A 0.9500 . ? C14A C15A 1.3996 . ? C14A C23A 1.4252 . ? C15A C16A 1.3816 . ? C15A H15A 0.9500 . ? C16A C17A 1.3891 . ? C16A H16A 0.9500 . ? C17A C18A 1.3992 . ? C17A H17A 0.9500 . ? C18A C23A 1.4205 . ? C18A C19A 1.4358 . ? C19A C20A 1.3532 . ? C19A H19A 0.9500 . ? C20A C21A 1.4407 . ? C20A H20A 0.9500 . ? C21A C22A 1.4291 . ? C22A C23A 1.4256 . ? C24 N4 1.2944 . ? C24 N3 1.4050 . ? C24 C31 1.4543 . ? O2 N3 1.2768 . ? N3 C25 1.4959 . ? N4 C26 1.4969 . ? C25 C28 1.5111 . ? C25 C27 1.5344 . ? C25 C26 1.5575 . ? C26 C30 1.5183 . ? C26 C29 1.5321 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.3970 . ? C31 C44 1.4118 . ? C32 C33 1.3826 . ? C32 H32 0.9500 . ? C33 C34 1.3973 . ? C33 H33 0.9500 . ? C34 C45 1.4262 . ? C34 C35 1.4364 . ? C35 C36 1.3510 . ? C35 H35 0.9500 . ? C36 C37 1.4316 . ? C36 H36 0.9500 . ? C37 C38 1.3996 . ? C37 C46 1.4252 . ? C38 C39 1.3817 . ? C38 H38 0.9500 . ? C39 C40 1.3891 . ? C39 H39 0.9500 . ? C40 C41 1.3991 . ? C40 H40 0.9500 . ? C41 C46 1.4205 . ? C41 C42 1.4358 . ? C42 C43 1.3532 . ? C42 H42 0.9500 . ? C43 C44 1.4407 . ? C43 H43 0.9500 . ? C44 C45 1.4291 . ? C45 C46 1.4257 . ? C24A N4A 1.2944 . ? C24A N3A 1.4050 . ? C24A C31A 1.4678 . ? O2A N3A 1.2767 . ? N3A C25A 1.4959 . ? N4A C26A 1.4969 . ? C25A C28A 1.5112 . ? C25A C27A 1.5344 . ? C25A C26A 1.5575 . ? C26A C30A 1.5182 . ? C26A C29A 1.5321 . ? C27A H27D 0.9800 . ? C27A H27E 0.9800 . ? C27A H27F 0.9800 . ? C28A H28D 0.9800 . ? C28A H28E 0.9800 . ? C28A H28F 0.9800 . ? C29A H29D 0.9800 . ? C29A H29E 0.9800 . ? C29A H29F 0.9800 . ? C30A H30D 0.9800 . ? C30A H30E 0.9800 . ? C30A H30F 0.9800 . ? C31A C32A 1.3970 . ? C31A C44A 1.4118 . ? C32A C33A 1.3826 . ? C32A H32A 0.9500 . ? C33A C34A 1.3973 . ? C33A H33A 0.9500 . ? C34A C45A 1.4262 . ? C34A C35A 1.4364 . ? C35A C36A 1.3510 . ? C35A H35A 0.9500 . ? C36A C37A 1.4316 . ? C36A H36A 0.9500 . ? C37A C38A 1.3996 . ? C37A C46A 1.4253 . ? C38A C39A 1.3816 . ? C38A H38A 0.9500 . ? C39A C40A 1.3891 . ? C39A H39A 0.9500 . ? C40A C41A 1.3992 . ? C40A H40A 0.9500 . ? C41A C46A 1.4205 . ? C41A C42A 1.4358 . ? C42A C43A 1.3532 . ? C42A H42A 0.9500 . ? C43A C44A 1.4407 . ? C43A H43A 0.9500 . ? C44A C45A 1.4291 . ? C45A C46A 1.4256 . ? 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 C1 N1 112.5 . . ? N2 C1 C8 125.7 . . ? N1 C1 C8 121.6 . . ? O1 N1 C1 127.1 . . ? O1 N1 C2 123.3 . . ? C1 N1 C2 108.5 . . ? C1 N2 C3 108.6 . . ? N1 C2 C5 110.9 . . ? N1 C2 C4 106.0 . . ? C5 C2 C4 110.7 . . ? N1 C2 C3 98.6 . . ? C5 C2 C3 116.5 . . ? C4 C2 C3 113.0 . . ? N2 C3 C7 109.7 . . ? N2 C3 C6 106.5 . . ? C7 C3 C6 109.9 . . ? N2 C3 C2 103.7 . . ? C7 C3 C2 114.4 . . ? C6 C3 C2 112.2 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C21 120.3 . . ? C9 C8 C1 118.4 . . ? C21 C8 C1 119.8 . . ? C10 C9 C8 120.8 . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 121.2 . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C22 119.0 . . ? C10 C11 C12 122.3 . . ? C22 C11 C12 118.7 . . ? C13 C12 C11 121.4 . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 121.5 . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C23 118.8 . . ? C15 C14 C13 122.6 . . ? C23 C14 C13 118.6 . . ? C16 C15 C14 121.2 . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 120.5 . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 120.4 . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C23 119.5 . . ? C17 C18 C19 122.3 . . ? C23 C18 C19 118.1 . . ? C20 C19 C18 121.9 . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C21 121.5 . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C8 C21 C22 118.7 . . ? C8 C21 C20 123.5 . . ? C22 C21 C20 117.8 . . ? C23 C22 C11 119.6 . . ? C23 C22 C21 120.4 . . ? C11 C22 C21 120.0 . . ? C18 C23 C14 119.5 . . ? C18 C23 C22 120.2 . . ? C14 C23 C22 120.2 . . ? N2A C1A N1A 112.5 . . ? N2A C1A C8A 122.1 . . ? N1A C1A C8A 125.3 . . ? O1A N1A C1A 127.1 . . ? O1A N1A C2A 123.3 . . ? C1A N1A C2A 108.5 . . ? C1A N2A C3A 108.6 . . ? N1A C2A C5A 110.9 . . ? N1A C2A C4A 106.0 . . ? C5A C2A C4A 110.7 . . ? N1A C2A C3A 98.6 . . ? C5A C2A C3A 116.5 . . ? C4A C2A C3A 113.0 . . ? N2A C3A C7A 109.7 . . ? N2A C3A C6A 106.5 . . ? C7A C3A C6A 109.9 . . ? N2A C3A C2A 103.7 . . ? C7A C3A C2A 114.4 . . ? C6A C3A C2A 112.2 . . ? C2A C4A H4A1 109.5 . . ? C2A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? C2A C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 109.5 . . ? C2A C5A H5A1 109.5 . . ? C2A C5A H5A2 109.5 . . ? H5A1 C5A H5A2 109.5 . . ? C2A C5A H5A3 109.5 . . ? H5A1 C5A H5A3 109.5 . . ? H5A2 C5A H5A3 109.5 . . ? C3A C6A H6A1 109.5 . . ? C3A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 109.5 . . ? C3A C6A H6A3 109.5 . . ? H6A1 C6A H6A3 109.5 . . ? H6A2 C6A H6A3 109.5 . . ? C3A C7A H7A1 109.5 . . ? C3A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C3A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C9A C8A C21A 120.3 . . ? C9A C8A C1A 117.2 . . ? C21A C8A C1A 121.9 . . ? C10A C9A C8A 120.8 . . ? C10A C9A H9A 119.6 . . ? C8A C9A H9A 119.6 . . ? C9A C10A C11A 121.2 . . ? C9A C10A H10A 119.4 . . ? C11A C10A H10A 119.4 . . ? C10A C11A C22A 119.0 . . ? C10A C11A C12A 122.3 . . ? C22A C11A C12A 118.7 . . ? C13A C12A C11A 121.4 . . ? C13A C12A H12A 119.3 . . ? C11A C12A H12A 119.3 . . ? C12A C13A C14A 121.5 . . ? C12A C13A H13A 119.3 . . ? C14A C13A H13A 119.3 . . ? C15A C14A C23A 118.8 . . ? C15A C14A C13A 122.6 . . ? C23A C14A C13A 118.6 . . ? C16A C15A C14A 121.2 . . ? C16A C15A H15A 119.4 . . ? C14A C15A H15A 119.4 . . ? C15A C16A C17A 120.5 . . ? C15A C16A H16A 119.7 . . ? C17A C16A H16A 119.7 . . ? C16A C17A C18A 120.4 . . ? C16A C17A H17A 119.8 . . ? C18A C17A H17A 119.8 . . ? C17A C18A C23A 119.5 . . ? C17A C18A C19A 122.3 . . ? C23A C18A C19A 118.1 . . ? C20A C19A C18A 121.9 . . ? C20A C19A H19A 119.1 . . ? C18A C19A H19A 119.1 . . ? C19A C20A C21A 121.5 . . ? C19A C20A H20A 119.3 . . ? C21A C20A H20A 119.3 . . ? C8A C21A C22A 118.7 . . ? C8A C21A C20A 123.5 . . ? C22A C21A C20A 117.8 . . ? C23A C22A C11A 119.6 . . ? C23A C22A C21A 120.4 . . ? C11A C22A C21A 120.0 . . ? C18A C23A C14A 119.5 . . ? C18A C23A C22A 120.2 . . ? C14A C23A C22A 120.2 . . ? N4 C24 N3 112.5 . . ? N4 C24 C31 122.2 . . ? N3 C24 C31 125.1 . . ? O2 N3 C24 127.1 . . ? O2 N3 C25 123.3 . . ? C24 N3 C25 108.5 . . ? C24 N4 C26 108.6 . . ? N3 C25 C28 110.9 . . ? N3 C25 C27 106.0 . . ? C28 C25 C27 110.7 . . ? N3 C25 C26 98.6 . . ? C28 C25 C26 116.5 . . ? C27 C25 C26 112.99(5) . . ? N4 C26 C30 109.7 . . ? N4 C26 C29 106.5 . . ? C30 C26 C29 109.9 . . ? N4 C26 C25 103.7 . . ? C30 C26 C25 114.4 . . ? C29 C26 C25 112.2 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 C30 H30A 109.5 . . ? C26 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C26 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C32 C31 C44 120.3 . . ? C32 C31 C24 117.8 . . ? C44 C31 C24 121.6 . . ? C33 C32 C31 120.8 . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C32 C33 C34 121.2 . . ? C32 C33 H33 119.4 . . ? C34 C33 H33 119.4 . . ? C33 C34 C45 119.0 . . ? C33 C34 C35 122.3 . . ? C45 C34 C35 118.7 . . ? C36 C35 C34 121.4 . . ? C36 C35 H35 119.3 . . ? C34 C35 H35 119.3 . . ? C35 C36 C37 121.5 . . ? C35 C36 H36 119.3 . . ? C37 C36 H36 119.3 . . ? C38 C37 C46 118.8 . . ? C38 C37 C36 122.6 . . ? C46 C37 C36 118.6 . . ? C39 C38 C37 121.2 . . ? C39 C38 H38 119.4 . . ? C37 C38 H38 119.4 . . ? C38 C39 C40 120.5 . . ? C38 C39 H39 119.7 . . ? C40 C39 H39 119.7 . . ? C39 C40 C41 120.4 . . ? C39 C40 H40 119.8 . . ? C41 C40 H40 119.8 . . ? C40 C41 C46 119.5 . . ? C40 C41 C42 122.3 . . ? C46 C41 C42 118.1 . . ? C43 C42 C41 121.9 . . ? C43 C42 H42 119.1 . . ? C41 C42 H42 119.1 . . ? C42 C43 C44 121.5 . . ? C42 C43 H43 119.3 . . ? C44 C43 H43 119.3 . . ? C31 C44 C45 118.7 . . ? C31 C44 C43 123.5 . . ? C45 C44 C43 117.8 . . ? C46 C45 C34 119.6 . . ? C46 C45 C44 120.4 . . ? C34 C45 C44 120.0 . . ? C41 C46 C37 119.5 . . ? C41 C46 C45 120.2 . . ? C37 C46 C45 120.2 . . ? N4A C24A N3A 112.5 . . ? N4A C24A C31A 125.2 . . ? N3A C24A C31A 122.0 . . ? O2A N3A C24A 127.1 . . ? O2A N3A C25A 123.3 . . ? C24A N3A C25A 108.47(6) . . ? C24A N4A C26A 108.6 . . ? N3A C25A C28A 110.9 . . ? N3A C25A C27A 106.0 . . ? C28A C25A C27A 110.7 . . ? N3A C25A C26A 98.6 . . ? C28A C25A C26A 116.5 . . ? C27A C25A C26A 112.99(5) . . ? N4A C26A C30A 109.7 . . ? N4A C26A C29A 106.5 . . ? C30A C26A C29A 109.9 . . ? N4A C26A C25A 103.7 . . ? C30A C26A C25A 114.4 . . ? C29A C26A C25A 112.2 . . ? C25A C27A H27D 109.5 . . ? C25A C27A H27E 109.5 . . ? H27D C27A H27E 109.5 . . ? C25A C27A H27F 109.5 . . ? H27D C27A H27F 109.5 . . ? H27E C27A H27F 109.5 . . ? C25A C28A H28D 109.5 . . ? C25A C28A H28E 109.5 . . ? H28D C28A H28E 109.5 . . ? C25A C28A H28F 109.5 . . ? H28D C28A H28F 109.5 . . ? H28E C28A H28F 109.5 . . ? C26A C29A H29D 109.5 . . ? C26A C29A H29E 109.5 . . ? H29D C29A H29E 109.5 . . ? C26A C29A H29F 109.5 . . ? H29D C29A H29F 109.5 . . ? H29E C29A H29F 109.5 . . ? C26A C30A H30D 109.5 . . ? C26A C30A H30E 109.5 . . ? H30D C30A H30E 109.5 . . ? C26A C30A H30F 109.5 . . ? H30D C30A H30F 109.5 . . ? H30E C30A H30F 109.5 . . ? C32A C31A C44A 120.3 . . ? C32A C31A C24A 118.7 . . ? C44A C31A C24A 119.7 . . ? C33A C32A C31A 120.8 . . ? C33A C32A H32A 119.6 . . ? C31A C32A H32A 119.6 . . ? C32A C33A C34A 121.2 . . ? C32A C33A H33A 119.4 . . ? C34A C33A H33A 119.4 . . ? C33A C34A C45A 119.0 . . ? C33A C34A C35A 122.3 . . ? C45A C34A C35A 118.7 . . ? C36A C35A C34A 121.4 . . ? C36A C35A H35A 119.3 . . ? C34A C35A H35A 119.3 . . ? C35A C36A C37A 121.5 . . ? C35A C36A H36A 119.3 . . ? C37A C36A H36A 119.3 . . ? C38A C37A C46A 118.8 . . ? C38A C37A C36A 122.6 . . ? C46A C37A C36A 118.6 . . ? C39A C38A C37A 121.2 . . ? C39A C38A H38A 119.4 . . ? C37A C38A H38A 119.4 . . ? C38A C39A C40A 120.5 . . ? C38A C39A H39A 119.7 . . ? C40A C39A H39A 119.7 . . ? C39A C40A C41A 120.4 . . ? C39A C40A H40A 119.8 . . ? C41A C40A H40A 119.8 . . ? C40A C41A C46A 119.5 . . ? C40A C41A C42A 122.3 . . ? C46A C41A C42A 118.1 . . ? C43A C42A C41A 121.9 . . ? C43A C42A H42A 119.1 . . ? C41A C42A H42A 119.1 . . ? C42A C43A C44A 121.5 . . ? C42A C43A H43A 119.3 . . ? C44A C43A H43A 119.3 . . ? C31A C44A C45A 118.7 . . ? C31A C44A C43A 123.5 . . ? C45A C44A C43A 117.8 . . ? C46A C45A C34A 119.6 . . ? C46A C45A C44A 120.4 . . ? C34A C45A C44A 120.0 . . ? C41A C46A C37A 119.5 . . ? C41A C46A C45A 120.2 . . ? C37A C46A C45A 120.2 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.537 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.061 # Attachment 'PyrNN-a.cif' data_phl006_0m _database_code_depnum_ccdc_archive 'CCDC 840779' #TrackingRef 'PyrNN-a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 N2 O2' _chemical_formula_sum 'C23 H21 N2 O2' _chemical_formula_weight 357.42 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.428(2) _cell_length_b 7.4072(12) _cell_length_c 33.289(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.483(2) _cell_angle_gamma 90.00 _cell_volume 3556.4(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1065 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 26.36 _exptl_crystal_description Plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8069 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2008a)' _exptl_special_details ; The diffraction data were collected in three sets of 606 frames (0.3 deg. width in omega) at phi = 0, 120 and 240 deg. A scan time of 150 sec/frame was used. Analysis of 1342 reflections chosen form the full data set and having I/\s(I) > 10.0 with CELL_NOW (Sheldrick, 2008b) indicated the crystal to consist of two major components with one dominant. The raw intensity data were processed using the multi-component version of SAINT under control of the two-component instruction file generated by CELL_NOW. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7335 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1333 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 26.47 _reflns_number_total 7335 _reflns_number_gt 3478 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (Bruker-AXS, 2009)' _computing_cell_refinement 'Bruker SAINT (Bruker-AXS 2009a)' _computing_data_reduction 'Bruker SAINT (Bruker-AXS 2009a)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL(Bruker-AXS 2008)' _computing_publication_material 'Bruker SHELXTL(Bruker-AXS 2008)' _publ_section_references ; Bruker-AXS (2009). APEX2, Version 2009.9-0, Madison, WI. Bruker-AXS (2009a). SAINT, Version 7.68A, Madison, WI Bruker-AXS (2008). SHELXTL, Version 2008/4, Madison, WI Sheldrick, G. M. (2008). SHELXS and SHELXL. Acta Cryst. A64, 112-122. Sheldrick, G, M. (2008a). TWINABS, Version 2008/4. University of G\"ottingen, Germany. Sheldrick, G, M. (2008b). CELL_NOW, Version 2008/2 University of G\"ottingen, Germany. ; _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. H-atoms were placed in calculated positions (C---H = 0.95 - 0.98 \%A) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. For the solution and refinement of the structure, the one-component (major) reflection file generated by CELL_NOW proved to be satisfactory. ; _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^)+(0.0489P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7335 _refine_ls_number_parameters 495 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1664 _refine_ls_R_factor_gt 0.0723 _refine_ls_wR_factor_ref 0.1407 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.20310(15) 0.4329(3) 0.10340(6) 0.0339(6) Uani 1 1 d . . . O2 O -0.02934(16) 0.2864(3) 0.01008(7) 0.0349(6) Uani 1 1 d . . . N1 N 0.12299(19) 0.4146(4) 0.08588(8) 0.0279(7) Uani 1 1 d . . . N2 N 0.01315(19) 0.3389(4) 0.04237(8) 0.0262(7) Uani 1 1 d . . . C1 C 0.1062(2) 0.3560(4) 0.04800(9) 0.0256(8) Uani 1 1 d . . . C2 C 0.0348(2) 0.4770(4) 0.10484(9) 0.0246(8) Uani 1 1 d . . . C3 C -0.0356(2) 0.3598(5) 0.08138(9) 0.0262(8) Uani 1 1 d . . . C4 C 0.0381(2) 0.4479(5) 0.14990(9) 0.0301(9) Uani 1 1 d . . . H4A H 0.0508 0.3204 0.1557 0.045 Uiso 1 1 calc R . . H4B H -0.0217 0.4816 0.1610 0.045 Uiso 1 1 calc R . . H4C H 0.0872 0.5228 0.1621 0.045 Uiso 1 1 calc R . . C5 C 0.0264(2) 0.6782(4) 0.09499(10) 0.0322(9) Uani 1 1 d . . . H5A H 0.0828 0.7409 0.1043 0.048 Uiso 1 1 calc R . . H5B H -0.0272 0.7288 0.1085 0.048 Uiso 1 1 calc R . . H5C H 0.0183 0.6938 0.0659 0.048 Uiso 1 1 calc R . . C6 C -0.1306(2) 0.4419(5) 0.07506(10) 0.0334(9) Uani 1 1 d . . . H6A H -0.1250 0.5578 0.0612 0.050 Uiso 1 1 calc R . . H6B H -0.1589 0.4610 0.1012 0.050 Uiso 1 1 calc R . . H6C H -0.1695 0.3601 0.0588 0.050 Uiso 1 1 calc R . . C7 C -0.0431(2) 0.1686(5) 0.09849(10) 0.0365(9) Uani 1 1 d . . . H7A H -0.0758 0.0909 0.0790 0.055 Uiso 1 1 calc R . . H7B H -0.0774 0.1720 0.1235 0.055 Uiso 1 1 calc R . . H7C H 0.0192 0.1203 0.1039 0.055 Uiso 1 1 calc R . . C8 C 0.1747(2) 0.3045(5) 0.01866(9) 0.0268(8) Uani 1 1 d . . . C9 C 0.1651(3) 0.1354(5) 0.00031(10) 0.0330(9) Uani 1 1 d . . . H9 H 0.1153 0.0587 0.0072 0.040 Uiso 1 1 calc R . . C10 C 0.2272(2) 0.0799(5) -0.02764(10) 0.0316(9) Uani 1 1 d . . . H10 H 0.2199 -0.0359 -0.0396 0.038 Uiso 1 1 calc R . . C11 C 0.3008(2) 0.1888(5) -0.03894(9) 0.0284(8) Uani 1 1 d . . . C12 C 0.3661(3) 0.1356(5) -0.06812(10) 0.0349(9) Uani 1 1 d . . . H12 H 0.3607 0.0191 -0.0799 0.042 Uiso 1 1 calc R . . C13 C 0.4348(3) 0.2444(5) -0.07954(10) 0.0328(9) Uani 1 1 d . . . H13 H 0.4764 0.2041 -0.0993 0.039 Uiso 1 1 calc R . . C14 C 0.4464(2) 0.4213(5) -0.06235(10) 0.0308(9) Uani 1 1 d . . . C15 C 0.5192(3) 0.5354(5) -0.07317(10) 0.0326(9) Uani 1 1 d . . . H15 H 0.5619 0.4969 -0.0926 0.039 Uiso 1 1 calc R . . C16 C 0.5289(2) 0.7028(5) -0.05574(10) 0.0346(9) Uani 1 1 d . . . H16 H 0.5789 0.7785 -0.0630 0.042 Uiso 1 1 calc R . . C17 C 0.4663(2) 0.7624(5) -0.02766(10) 0.0327(9) Uani 1 1 d . . . H17 H 0.4734 0.8793 -0.0163 0.039 Uiso 1 1 calc R . . C18 C 0.3929(2) 0.6521(4) -0.01590(9) 0.0246(8) Uani 1 1 d . . . C19 C 0.3274(2) 0.7081(5) 0.01306(9) 0.0277(8) Uani 1 1 d . . . H19 H 0.3332 0.8250 0.0246 0.033 Uiso 1 1 calc R . . C20 C 0.2578(2) 0.6003(4) 0.02451(9) 0.0262(8) Uani 1 1 d . . . H20 H 0.2151 0.6433 0.0435 0.031 Uiso 1 1 calc R . . C21 C 0.2468(2) 0.4207(5) 0.00840(9) 0.0253(8) Uani 1 1 d . . . C22 C 0.3102(2) 0.3635(5) -0.02102(9) 0.0248(8) Uani 1 1 d . . . C23 C 0.3835(2) 0.4787(4) -0.03313(9) 0.0243(8) Uani 1 1 d . . . O3 O 0.41459(16) 0.6497(3) 0.15964(6) 0.0330(6) Uani 1 1 d . . . O4 O 0.39078(15) 1.1046(3) 0.25399(6) 0.0304(6) Uani 1 1 d . . . N3 N 0.38949(18) 0.7947(3) 0.17731(7) 0.0239(7) Uani 1 1 d . . . N4 N 0.38207(19) 1.0135(4) 0.22131(8) 0.0245(7) Uani 1 1 d . . . C24 C 0.4210(2) 0.8521(4) 0.21383(9) 0.0230(8) Uani 1 1 d . . . C25 C 0.3109(2) 0.9108(4) 0.16177(9) 0.0234(8) Uani 1 1 d . . . C26 C 0.3335(2) 1.0894(4) 0.18426(9) 0.0226(8) Uani 1 1 d . . . C27 C 0.2226(2) 0.8174(5) 0.17529(10) 0.0328(9) Uani 1 1 d . . . H27A H 0.2208 0.6936 0.1649 0.049 Uiso 1 1 calc R . . H27B H 0.1683 0.8839 0.1649 0.049 Uiso 1 1 calc R . . H27C H 0.2219 0.8147 0.2047 0.049 Uiso 1 1 calc R . . C28 C 0.3117(2) 0.9204(5) 0.11626(9) 0.0326(9) Uani 1 1 d . . . H28A H 0.3731 0.9594 0.1077 0.049 Uiso 1 1 calc R . . H28B H 0.2649 1.0071 0.1067 0.049 Uiso 1 1 calc R . . H28C H 0.2978 0.8010 0.1050 0.049 Uiso 1 1 calc R . . C29 C 0.2505(2) 1.2001(5) 0.19550(10) 0.0324(9) Uani 1 1 d . . . H29A H 0.2090 1.1263 0.2116 0.049 Uiso 1 1 calc R . . H29B H 0.2175 1.2406 0.1710 0.049 Uiso 1 1 calc R . . H29C H 0.2711 1.3053 0.2112 0.049 Uiso 1 1 calc R . . C30 C 0.4043(2) 1.2047(4) 0.16321(10) 0.0313(9) Uani 1 1 d . . . H30A H 0.4271 1.2992 0.1816 0.047 Uiso 1 1 calc R . . H30B H 0.3752 1.2606 0.1394 0.047 Uiso 1 1 calc R . . H30C H 0.4562 1.1289 0.1551 0.047 Uiso 1 1 calc R . . C31 C 0.4824(2) 0.7478(4) 0.24082(9) 0.0228(8) Uani 1 1 d . . . C32 C 0.4591(2) 0.5693(4) 0.24929(9) 0.0252(8) Uani 1 1 d . . . H32 H 0.4056 0.5175 0.2367 0.030 Uiso 1 1 calc R . . C33 C 0.5123(2) 0.4669(4) 0.27557(9) 0.0243(8) Uani 1 1 d . . . H33 H 0.4946 0.3458 0.2809 0.029 Uiso 1 1 calc R . . C34 C 0.5918(2) 0.5381(4) 0.29450(9) 0.0238(8) Uani 1 1 d . . . C35 C 0.6492(2) 0.4372(5) 0.32189(9) 0.0276(8) Uani 1 1 d . . . H35 H 0.6318 0.3170 0.3283 0.033 Uiso 1 1 calc R . . C36 C 0.7275(2) 0.5064(4) 0.33912(10) 0.0275(8) Uani 1 1 d . . . H36 H 0.7642 0.4342 0.3569 0.033 Uiso 1 1 calc R . . C37 C 0.7552(2) 0.6877(4) 0.33062(9) 0.0249(8) Uani 1 1 d . . . C38 C 0.8365(2) 0.7649(5) 0.34713(10) 0.0312(9) Uani 1 1 d . . . H38 H 0.8738 0.6964 0.3655 0.037 Uiso 1 1 calc R . . C39 C 0.8636(2) 0.9378(5) 0.33733(10) 0.0315(9) Uani 1 1 d . . . H39 H 0.9192 0.9865 0.3488 0.038 Uiso 1 1 calc R . . C40 C 0.8101(2) 1.0400(5) 0.31102(9) 0.0269(8) Uani 1 1 d . . . H40 H 0.8296 1.1588 0.3045 0.032 Uiso 1 1 calc R . . C41 C 0.7275(2) 0.9721(4) 0.29372(9) 0.0233(8) Uani 1 1 d . . . C42 C 0.6721(2) 1.0719(5) 0.26550(9) 0.0263(8) Uani 1 1 d . . . H42 H 0.6910 1.1902 0.2583 0.032 Uiso 1 1 calc R . . C43 C 0.5935(2) 1.0037(4) 0.24860(9) 0.0256(8) Uani 1 1 d . . . H43 H 0.5580 1.0752 0.2302 0.031 Uiso 1 1 calc R . . C44 C 0.5628(2) 0.8236(4) 0.25814(9) 0.0198(7) Uani 1 1 d . . . C45 C 0.6175(2) 0.7196(4) 0.28573(9) 0.0225(8) Uani 1 1 d . . . C46 C 0.6993(2) 0.7939(4) 0.30399(9) 0.0221(8) 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 O1 0.0237(14) 0.0482(16) 0.0291(13) 0.0009(12) -0.0132(11) -0.0062(12) O2 0.0405(15) 0.0355(15) 0.0279(14) -0.0012(11) -0.0152(12) -0.0061(12) N1 0.0300(17) 0.0292(18) 0.0239(15) 0.0043(13) -0.0096(13) -0.0050(14) N2 0.0300(17) 0.0259(17) 0.0223(15) -0.0001(13) -0.0098(13) -0.0035(14) C1 0.026(2) 0.023(2) 0.0269(19) 0.0036(15) -0.0092(16) -0.0016(16) C2 0.022(2) 0.031(2) 0.0207(18) 0.0012(15) -0.0024(15) -0.0014(16) C3 0.0228(19) 0.032(2) 0.0234(18) 0.0044(15) -0.0068(15) -0.0047(16) C4 0.025(2) 0.040(2) 0.0247(19) 0.0032(16) -0.0041(16) -0.0047(17) C5 0.030(2) 0.034(2) 0.032(2) 0.0010(17) -0.0072(17) -0.0014(18) C6 0.028(2) 0.040(2) 0.032(2) 0.0004(17) -0.0070(17) -0.0009(18) C7 0.037(2) 0.034(2) 0.038(2) 0.0120(18) -0.0083(18) -0.0116(18) C8 0.032(2) 0.024(2) 0.0234(18) 0.0027(15) -0.0071(16) -0.0009(17) C9 0.039(2) 0.029(2) 0.030(2) 0.0003(17) -0.0131(18) -0.0047(18) C10 0.040(2) 0.023(2) 0.031(2) -0.0048(17) -0.0161(18) 0.0029(18) C11 0.032(2) 0.030(2) 0.0229(18) -0.0030(16) -0.0137(16) 0.0095(17) C12 0.044(2) 0.031(2) 0.028(2) -0.0089(17) -0.0098(18) 0.014(2) C13 0.038(2) 0.040(2) 0.0203(19) -0.0025(17) -0.0034(17) 0.017(2) C14 0.034(2) 0.037(2) 0.0206(18) 0.0017(17) -0.0082(17) 0.0063(19) C15 0.037(2) 0.044(3) 0.0169(18) 0.0069(17) -0.0048(16) 0.0065(19) C16 0.030(2) 0.047(3) 0.026(2) 0.0127(18) -0.0068(17) -0.0003(19) C17 0.039(2) 0.031(2) 0.028(2) 0.0056(16) -0.0109(18) -0.0034(18) C18 0.027(2) 0.028(2) 0.0184(17) 0.0062(15) -0.0123(15) 0.0023(17) C19 0.031(2) 0.027(2) 0.0256(19) -0.0030(16) -0.0055(16) 0.0002(17) C20 0.027(2) 0.029(2) 0.0218(18) -0.0014(16) -0.0070(15) 0.0051(17) C21 0.027(2) 0.027(2) 0.0212(18) 0.0008(15) -0.0104(15) 0.0067(17) C22 0.025(2) 0.031(2) 0.0182(17) -0.0014(15) -0.0127(15) 0.0071(16) C23 0.024(2) 0.028(2) 0.0198(18) 0.0017(15) -0.0088(15) 0.0037(16) O3 0.0430(16) 0.0265(14) 0.0292(13) -0.0100(11) -0.0045(11) 0.0060(12) O4 0.0355(15) 0.0318(15) 0.0233(12) -0.0104(11) -0.0060(11) 0.0008(12) N3 0.0273(16) 0.0201(16) 0.0240(15) -0.0024(13) -0.0053(13) 0.0016(13) N4 0.0297(17) 0.0234(16) 0.0200(15) -0.0025(12) -0.0050(12) 0.0002(13) C24 0.0214(19) 0.025(2) 0.0223(18) -0.0026(15) -0.0030(15) -0.0018(16) C25 0.0229(19) 0.028(2) 0.0189(17) 0.0009(15) -0.0088(14) 0.0008(16) C26 0.0237(19) 0.0233(19) 0.0204(17) -0.0008(15) -0.0059(14) 0.0028(15) C27 0.028(2) 0.037(2) 0.033(2) 0.0053(17) -0.0062(16) -0.0091(18) C28 0.040(2) 0.036(2) 0.0217(18) -0.0023(16) -0.0114(16) -0.0002(18) C29 0.035(2) 0.033(2) 0.029(2) 0.0013(17) -0.0038(17) 0.0072(18) C30 0.039(2) 0.027(2) 0.028(2) 0.0003(16) -0.0028(17) -0.0040(18) C31 0.0225(19) 0.028(2) 0.0176(17) -0.0017(15) -0.0008(15) 0.0024(16) C32 0.030(2) 0.021(2) 0.0237(18) -0.0065(15) -0.0033(16) -0.0026(16) C33 0.032(2) 0.0171(19) 0.0241(18) -0.0012(14) -0.0010(16) 0.0022(16) C34 0.025(2) 0.021(2) 0.0250(18) -0.0038(15) 0.0005(15) -0.0014(15) C35 0.037(2) 0.0214(19) 0.0247(19) 0.0008(15) -0.0010(17) 0.0031(17) C36 0.027(2) 0.030(2) 0.0247(18) 0.0028(16) -0.0039(16) 0.0041(17) C37 0.026(2) 0.028(2) 0.0210(18) 0.0009(15) -0.0014(15) 0.0024(16) C38 0.024(2) 0.041(2) 0.027(2) 0.0029(17) -0.0076(16) 0.0051(18) C39 0.031(2) 0.036(2) 0.0272(19) -0.0037(17) -0.0006(17) -0.0043(18) C40 0.025(2) 0.027(2) 0.0284(19) 0.0020(16) -0.0009(16) -0.0002(16) C41 0.021(2) 0.031(2) 0.0185(17) -0.0024(15) 0.0019(15) 0.0017(16) C42 0.028(2) 0.026(2) 0.0254(18) -0.0031(16) -0.0010(16) -0.0027(16) C43 0.025(2) 0.026(2) 0.0256(18) 0.0008(15) -0.0022(15) 0.0015(16) C44 0.0232(19) 0.0181(19) 0.0178(16) -0.0015(14) -0.0038(14) -0.0041(15) C45 0.0252(19) 0.025(2) 0.0168(17) -0.0047(15) -0.0006(15) 0.0004(16) C46 0.027(2) 0.0230(19) 0.0168(17) -0.0024(14) 0.0002(15) 0.0002(16) _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 N1 1.288(3) . ? O2 N2 1.284(3) . ? N1 C1 1.350(4) . ? N1 C2 1.507(4) . ? N2 C1 1.357(4) . ? N2 C3 1.501(4) . ? C1 C8 1.459(4) . ? C2 C4 1.515(4) . ? C2 C5 1.530(4) . ? C2 C3 1.535(4) . ? C3 C6 1.508(4) . ? C3 C7 1.532(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.399(4) . ? C8 C21 1.399(5) . ? C9 C10 1.372(5) . ? C9 H9 0.9500 . ? C10 C11 1.393(5) . ? C10 H10 0.9500 . ? C11 C12 1.426(4) . ? C11 C22 1.430(4) . ? C12 C13 1.340(5) . ? C12 H12 0.9500 . ? C13 C14 1.438(5) . ? C13 H13 0.9500 . ? C14 C15 1.402(5) . ? C14 C23 1.413(4) . ? C15 C16 1.375(5) . ? C15 H15 0.9500 . ? C16 C17 1.388(5) . ? C16 H16 0.9500 . ? C17 C18 1.401(4) . ? C17 H17 0.9500 . ? C18 C23 1.412(4) . ? C18 C19 1.429(4) . ? C19 C20 1.347(4) . ? C19 H19 0.9500 . ? C20 C21 1.442(4) . ? C20 H20 0.9500 . ? C21 C22 1.422(4) . ? C22 C23 1.424(4) . ? O3 N3 1.281(3) . ? O4 N4 1.283(3) . ? N3 C24 1.355(4) . ? N3 C25 1.504(4) . ? N4 C24 1.346(4) . ? N4 C26 1.511(4) . ? C24 C31 1.466(4) . ? C25 C28 1.517(4) . ? C25 C27 1.528(4) . ? C25 C26 1.551(4) . ? C26 C29 1.506(4) . ? C26 C30 1.517(4) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.394(4) . ? C31 C44 1.399(4) . ? C32 C33 1.376(4) . ? C32 H32 0.9500 . ? C33 C34 1.399(4) . ? C33 H33 0.9500 . ? C34 C45 1.427(4) . ? C34 C35 1.427(4) . ? C35 C36 1.354(4) . ? C35 H35 0.9500 . ? C36 C37 1.432(4) . ? C36 H36 0.9500 . ? C37 C38 1.404(4) . ? C37 C46 1.421(4) . ? C38 C39 1.381(5) . ? C38 H38 0.9500 . ? C39 C40 1.378(4) . ? C39 H39 0.9500 . ? C40 C41 1.403(4) . ? C40 H40 0.9500 . ? C41 C42 1.425(4) . ? C41 C46 1.426(4) . ? C42 C43 1.350(4) . ? C42 H42 0.9500 . ? C43 C44 1.444(4) . ? C43 H43 0.9500 . ? C44 C45 1.422(4) . ? C45 C46 1.423(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 N1 C1 126.4(3) . . ? O1 N1 C2 122.4(2) . . ? C1 N1 C2 110.9(3) . . ? O2 N2 C1 126.4(3) . . ? O2 N2 C3 122.1(3) . . ? C1 N2 C3 110.8(2) . . ? N1 C1 N2 108.2(3) . . ? N1 C1 C8 127.0(3) . . ? N2 C1 C8 124.7(3) . . ? N1 C2 C4 111.5(3) . . ? N1 C2 C5 105.8(3) . . ? C4 C2 C5 110.6(3) . . ? N1 C2 C3 99.7(2) . . ? C4 C2 C3 115.2(3) . . ? C5 C2 C3 113.2(3) . . ? N2 C3 C6 111.4(2) . . ? N2 C3 C7 105.4(3) . . ? C6 C3 C7 110.6(3) . . ? N2 C3 C2 100.3(2) . . ? C6 C3 C2 115.5(3) . . ? C7 C3 C2 112.7(3) . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C21 120.7(3) . . ? C9 C8 C1 117.7(3) . . ? C21 C8 C1 121.6(3) . . ? C10 C9 C8 120.4(3) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 121.7(3) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C10 C11 C12 123.0(3) . . ? C10 C11 C22 118.5(3) . . ? C12 C11 C22 118.5(3) . . ? C13 C12 C11 122.2(3) . . ? C13 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? C12 C13 C14 121.0(3) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C23 119.6(3) . . ? C15 C14 C13 121.9(3) . . ? C23 C14 C13 118.5(3) . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.7(4) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C17 C18 C23 118.8(3) . . ? C17 C18 C19 122.5(3) . . ? C23 C18 C19 118.6(3) . . ? C20 C19 C18 122.0(3) . . ? C20 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C19 C20 C21 121.2(3) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C8 C21 C22 118.7(3) . . ? C8 C21 C20 123.5(3) . . ? C22 C21 C20 117.7(3) . . ? C21 C22 C23 120.8(3) . . ? C21 C22 C11 120.1(3) . . ? C23 C22 C11 119.1(3) . . ? C18 C23 C14 119.7(3) . . ? C18 C23 C22 119.6(3) . . ? C14 C23 C22 120.6(3) . . ? O3 N3 C24 125.7(3) . . ? O3 N3 C25 122.7(2) . . ? C24 N3 C25 111.2(3) . . ? O4 N4 C24 126.2(3) . . ? O4 N4 C26 122.0(3) . . ? C24 N4 C26 111.5(3) . . ? N4 C24 N3 108.3(3) . . ? N4 C24 C31 127.1(3) . . ? N3 C24 C31 124.6(3) . . ? N3 C25 C28 110.2(3) . . ? N3 C25 C27 105.5(3) . . ? C28 C25 C27 110.1(3) . . ? N3 C25 C26 100.1(2) . . ? C28 C25 C26 115.8(3) . . ? C27 C25 C26 114.2(3) . . ? C29 C26 N4 110.8(3) . . ? C29 C26 C30 110.9(3) . . ? N4 C26 C30 106.4(3) . . ? C29 C26 C25 115.2(3) . . ? N4 C26 C25 99.4(2) . . ? C30 C26 C25 113.1(3) . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 C30 H30A 109.5 . . ? C26 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C26 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C32 C31 C44 119.9(3) . . ? C32 C31 C24 118.6(3) . . ? C44 C31 C24 121.5(3) . . ? C33 C32 C31 121.2(3) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C32 C33 C34 121.0(3) . . ? C32 C33 H33 119.5 . . ? C34 C33 H33 119.5 . . ? C33 C34 C45 118.6(3) . . ? C33 C34 C35 123.1(3) . . ? C45 C34 C35 118.4(3) . . ? C36 C35 C34 122.4(3) . . ? C36 C35 H35 118.8 . . ? C34 C35 H35 118.8 . . ? C35 C36 C37 120.4(3) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C38 C37 C46 118.3(3) . . ? C38 C37 C36 122.7(3) . . ? C46 C37 C36 119.0(3) . . ? C39 C38 C37 121.6(3) . . ? C39 C38 H38 119.2 . . ? C37 C38 H38 119.2 . . ? C40 C39 C38 120.2(3) . . ? C40 C39 H39 119.9 . . ? C38 C39 H39 119.9 . . ? C39 C40 C41 121.3(3) . . ? C39 C40 H40 119.4 . . ? C41 C40 H40 119.4 . . ? C40 C41 C42 122.7(3) . . ? C40 C41 C46 118.6(3) . . ? C42 C41 C46 118.6(3) . . ? C43 C42 C41 122.1(3) . . ? C43 C42 H42 119.0 . . ? C41 C42 H42 119.0 . . ? C42 C43 C44 120.9(3) . . ? C42 C43 H43 119.6 . . ? C44 C43 H43 119.6 . . ? C31 C44 C45 119.3(3) . . ? C31 C44 C43 122.4(3) . . ? C45 C44 C43 118.3(3) . . ? C44 C45 C46 120.4(3) . . ? C44 C45 C34 120.0(3) . . ? C46 C45 C34 119.6(3) . . ? C37 C46 C45 120.2(3) . . ? C37 C46 C41 120.0(3) . . ? C45 C46 C41 119.6(3) . . ? 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 O1 N1 C1 N2 174.0(3) . . . . ? C2 N1 C1 N2 -12.1(4) . . . . ? O1 N1 C1 C8 -1.3(5) . . . . ? C2 N1 C1 C8 172.6(3) . . . . ? O2 N2 C1 N1 180.0(3) . . . . ? C3 N2 C1 N1 -9.6(4) . . . . ? O2 N2 C1 C8 -4.6(5) . . . . ? C3 N2 C1 C8 165.8(3) . . . . ? O1 N1 C2 C4 -36.3(4) . . . . ? C1 N1 C2 C4 149.5(3) . . . . ? O1 N1 C2 C5 83.9(3) . . . . ? C1 N1 C2 C5 -90.3(3) . . . . ? O1 N1 C2 C3 -158.4(3) . . . . ? C1 N1 C2 C3 27.3(3) . . . . ? O2 N2 C3 C6 -40.3(4) . . . . ? C1 N2 C3 C6 148.7(3) . . . . ? O2 N2 C3 C7 79.7(3) . . . . ? C1 N2 C3 C7 -91.3(3) . . . . ? O2 N2 C3 C2 -163.1(3) . . . . ? C1 N2 C3 C2 25.9(3) . . . . ? N1 C2 C3 N2 -29.5(3) . . . . ? C4 C2 C3 N2 -148.9(3) . . . . ? C5 C2 C3 N2 82.4(3) . . . . ? N1 C2 C3 C6 -149.4(3) . . . . ? C4 C2 C3 C6 91.2(4) . . . . ? C5 C2 C3 C6 -37.5(4) . . . . ? N1 C2 C3 C7 82.1(3) . . . . ? C4 C2 C3 C7 -37.3(4) . . . . ? C5 C2 C3 C7 -166.0(3) . . . . ? N1 C1 C8 C9 127.4(4) . . . . ? N2 C1 C8 C9 -47.1(5) . . . . ? N1 C1 C8 C21 -53.9(5) . . . . ? N2 C1 C8 C21 131.6(3) . . . . ? C21 C8 C9 C10 1.0(5) . . . . ? C1 C8 C9 C10 179.7(3) . . . . ? C8 C9 C10 C11 -0.6(5) . . . . ? C9 C10 C11 C12 -179.5(3) . . . . ? C9 C10 C11 C22 -0.7(5) . . . . ? C10 C11 C12 C13 177.9(3) . . . . ? C22 C11 C12 C13 -0.8(5) . . . . ? C11 C12 C13 C14 0.6(5) . . . . ? C12 C13 C14 C15 178.4(3) . . . . ? C12 C13 C14 C23 -0.2(5) . . . . ? C23 C14 C15 C16 -0.6(5) . . . . ? C13 C14 C15 C16 -179.2(3) . . . . ? C14 C15 C16 C17 -0.9(5) . . . . ? C15 C16 C17 C18 1.1(5) . . . . ? C16 C17 C18 C23 0.0(5) . . . . ? C16 C17 C18 C19 179.6(3) . . . . ? C17 C18 C19 C20 -179.2(3) . . . . ? C23 C18 C19 C20 0.4(5) . . . . ? C18 C19 C20 C21 1.0(5) . . . . ? C9 C8 C21 C22 -0.1(5) . . . . ? C1 C8 C21 C22 -178.8(3) . . . . ? C9 C8 C21 C20 176.5(3) . . . . ? C1 C8 C21 C20 -2.2(5) . . . . ? C19 C20 C21 C8 -178.7(3) . . . . ? C19 C20 C21 C22 -2.1(4) . . . . ? C8 C21 C22 C23 178.5(3) . . . . ? C20 C21 C22 C23 1.8(4) . . . . ? C8 C21 C22 C11 -1.2(4) . . . . ? C20 C21 C22 C11 -178.0(3) . . . . ? C10 C11 C22 C21 1.6(4) . . . . ? C12 C11 C22 C21 -179.6(3) . . . . ? C10 C11 C22 C23 -178.1(3) . . . . ? C12 C11 C22 C23 0.6(4) . . . . ? C17 C18 C23 C14 -1.4(4) . . . . ? C19 C18 C23 C14 178.9(3) . . . . ? C17 C18 C23 C22 178.9(3) . . . . ? C19 C18 C23 C22 -0.7(4) . . . . ? C15 C14 C23 C18 1.7(5) . . . . ? C13 C14 C23 C18 -179.6(3) . . . . ? C15 C14 C23 C22 -178.6(3) . . . . ? C13 C14 C23 C22 0.0(4) . . . . ? C21 C22 C23 C18 -0.4(4) . . . . ? C11 C22 C23 C18 179.4(3) . . . . ? C21 C22 C23 C14 180.0(3) . . . . ? C11 C22 C23 C14 -0.3(4) . . . . ? O4 N4 C24 N3 175.4(3) . . . . ? C26 N4 C24 N3 -11.0(4) . . . . ? O4 N4 C24 C31 -1.2(5) . . . . ? C26 N4 C24 C31 172.4(3) . . . . ? O3 N3 C24 N4 177.0(3) . . . . ? C25 N3 C24 N4 -10.4(4) . . . . ? O3 N3 C24 C31 -6.3(5) . . . . ? C25 N3 C24 C31 166.2(3) . . . . ? O3 N3 C25 C28 -38.8(4) . . . . ? C24 N3 C25 C28 148.4(3) . . . . ? O3 N3 C25 C27 80.0(3) . . . . ? C24 N3 C25 C27 -92.8(3) . . . . ? O3 N3 C25 C26 -161.2(3) . . . . ? C24 N3 C25 C26 26.0(3) . . . . ? O4 N4 C26 C29 -38.2(4) . . . . ? C24 N4 C26 C29 147.9(3) . . . . ? O4 N4 C26 C30 82.5(3) . . . . ? C24 N4 C26 C30 -91.4(3) . . . . ? O4 N4 C26 C25 -159.9(3) . . . . ? C24 N4 C26 C25 26.3(3) . . . . ? N3 C25 C26 C29 -147.1(3) . . . . ? C28 C25 C26 C29 94.5(3) . . . . ? C27 C25 C26 C29 -35.0(4) . . . . ? N3 C25 C26 N4 -28.7(3) . . . . ? C28 C25 C26 N4 -147.1(3) . . . . ? C27 C25 C26 N4 83.4(3) . . . . ? N3 C25 C26 C30 83.8(3) . . . . ? C28 C25 C26 C30 -34.6(4) . . . . ? C27 C25 C26 C30 -164.1(3) . . . . ? N4 C24 C31 C32 126.0(4) . . . . ? N3 C24 C31 C32 -50.0(4) . . . . ? N4 C24 C31 C44 -53.7(5) . . . . ? N3 C24 C31 C44 130.3(3) . . . . ? C44 C31 C32 C33 2.2(5) . . . . ? C24 C31 C32 C33 -177.6(3) . . . . ? C31 C32 C33 C34 -0.4(5) . . . . ? C32 C33 C34 C45 -0.6(5) . . . . ? C32 C33 C34 C35 -179.9(3) . . . . ? C33 C34 C35 C36 178.1(3) . . . . ? C45 C34 C35 C36 -1.2(5) . . . . ? C34 C35 C36 C37 0.8(5) . . . . ? C35 C36 C37 C38 -178.9(3) . . . . ? C35 C36 C37 C46 0.2(5) . . . . ? C46 C37 C38 C39 -1.5(5) . . . . ? C36 C37 C38 C39 177.6(3) . . . . ? C37 C38 C39 C40 0.5(5) . . . . ? C38 C39 C40 C41 0.1(5) . . . . ? C39 C40 C41 C42 -178.0(3) . . . . ? C39 C40 C41 C46 0.2(5) . . . . ? C40 C41 C42 C43 178.9(3) . . . . ? C46 C41 C42 C43 0.7(5) . . . . ? C41 C42 C43 C44 -0.9(5) . . . . ? C32 C31 C44 C45 -2.9(4) . . . . ? C24 C31 C44 C45 176.8(3) . . . . ? C32 C31 C44 C43 176.1(3) . . . . ? C24 C31 C44 C43 -4.2(5) . . . . ? C42 C43 C44 C31 -179.2(3) . . . . ? C42 C43 C44 C45 -0.1(5) . . . . ? C31 C44 C45 C46 -179.6(3) . . . . ? C43 C44 C45 C46 1.4(4) . . . . ? C31 C44 C45 C34 2.0(4) . . . . ? C43 C44 C45 C34 -177.1(3) . . . . ? C33 C34 C45 C44 -0.2(4) . . . . ? C35 C34 C45 C44 179.1(3) . . . . ? C33 C34 C45 C46 -178.7(3) . . . . ? C35 C34 C45 C46 0.6(4) . . . . ? C38 C37 C46 C45 178.4(3) . . . . ? C36 C37 C46 C45 -0.8(4) . . . . ? C38 C37 C46 C41 1.8(4) . . . . ? C36 C37 C46 C41 -177.3(3) . . . . ? C44 C45 C46 C37 -178.1(3) . . . . ? C34 C45 C46 C37 0.3(4) . . . . ? C44 C45 C46 C41 -1.6(4) . . . . ? C34 C45 C46 C41 176.9(3) . . . . ? C40 C41 C46 C37 -1.2(4) . . . . ? C42 C41 C46 C37 177.1(3) . . . . ? C40 C41 C46 C45 -177.8(3) . . . . ? C42 C41 C46 C45 0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.229 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.055 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 840780' #TrackingRef 'PyrNN-b_293K_new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H21 N2 O2' _chemical_formula_weight 357.42 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9817(2) _cell_length_b 7.36870(10) _cell_length_c 25.0583(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.737(1) _cell_angle_gamma 90.00 _cell_volume 1836.80(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 2 _exptl_crystal_size_mid 0.8 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5953 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3197 _reflns_number_gt 2754 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0595P)^2^+0.2825P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3197 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 O2 O 0.44896(9) 0.71769(14) 0.49580(3) 0.0580(3) Uani 1 1 d . . . O1 O 0.37525(10) 0.58890(14) 0.67154(3) 0.0581(3) Uani 1 1 d . . . N2 N 0.39542(10) 0.66118(15) 0.53739(4) 0.0455(3) Uani 1 1 d . . . N1 N 0.36272(10) 0.59292(14) 0.62037(4) 0.0450(3) Uani 1 1 d . . . C21 C 0.67441(12) 0.66316(16) 0.64181(5) 0.0405(3) Uani 1 1 d . . . C20 C 0.65883(12) 0.48048(17) 0.66030(5) 0.0459(3) Uani 1 1 d . . . H20 H 0.5839 0.4138 0.6475 0.055 Uiso 1 1 calc R . . C19 C 0.75049(13) 0.40363(18) 0.69587(5) 0.0477(3) Uani 1 1 d . . . H19 H 0.7369 0.2851 0.7070 0.057 Uiso 1 1 calc R . . C18 C 0.86832(12) 0.49913(18) 0.71703(5) 0.0452(3) Uani 1 1 d . . . C17 C 0.96256(14) 0.4230(2) 0.75487(5) 0.0557(4) Uani 1 1 d . . . H17 H 0.9500 0.3055 0.7671 0.067 Uiso 1 1 calc R . . C16 C 1.07430(15) 0.5207(2) 0.77434(6) 0.0638(4) Uani 1 1 d . . . H16 H 1.1360 0.4682 0.7996 0.077 Uiso 1 1 calc R . . C15 C 1.09532(14) 0.6944(2) 0.75681(6) 0.0609(4) Uani 1 1 d . . . H6 H 1.1710 0.7581 0.7704 0.073 Uiso 1 1 calc R . . C14 C 1.00450(12) 0.77678(19) 0.71875(5) 0.0498(3) Uani 1 1 d . . . C13 C 1.02364(14) 0.9557(2) 0.69900(6) 0.0596(4) Uani 1 1 d . . . H13 H 1.0987 1.0218 0.7121 0.072 Uiso 1 1 calc R . . C12 C 0.93592(14) 1.0307(2) 0.66206(6) 0.0588(4) Uani 1 1 d . . . H12 H 0.9529 1.1464 0.6494 0.071 Uiso 1 1 calc R . . C11 C 0.81605(13) 0.93719(17) 0.64135(5) 0.0474(3) Uani 1 1 d . . . C22 C 0.79325(12) 0.75916(16) 0.66036(5) 0.0410(3) Uani 1 1 d . . . C23 C 0.88881(12) 0.67810(17) 0.69855(5) 0.0425(3) Uani 1 1 d . . . C10 C 0.72049(14) 1.01572(18) 0.60466(6) 0.0541(3) Uani 1 1 d . . . H10 H 0.7353 1.1318 0.5918 0.065 Uiso 1 1 calc R . . C9 C 0.60462(14) 0.92462(18) 0.58706(5) 0.0514(3) Uani 1 1 d . . . H9 H 0.5427 0.9794 0.5624 0.062 Uiso 1 1 calc R . . C8 C 0.57946(12) 0.75082(17) 0.60600(5) 0.0437(3) Uani 1 1 d . . . C1 C 0.45099(12) 0.66563(17) 0.58832(5) 0.0433(3) Uani 1 1 d . . . C3 C 0.25110(12) 0.60316(18) 0.53478(5) 0.0477(3) Uani 1 1 d . . . C2 C 0.24952(12) 0.49845(18) 0.58842(5) 0.0467(3) Uani 1 1 d . . . C6 C 0.21720(16) 0.4909(2) 0.48502(5) 0.0630(4) Uani 1 1 d . . . H6A H 0.2794 0.3918 0.4842 0.094 Uiso 1 1 calc R . . H6B H 0.2232 0.5654 0.4539 0.094 Uiso 1 1 calc R . . H6C H 0.1275 0.4443 0.4854 0.094 Uiso 1 1 calc R . . C7 C 0.16978(16) 0.7797(2) 0.53330(7) 0.0674(4) Uani 1 1 d . . . H7A H 0.1901 0.8454 0.5660 0.101 Uiso 1 1 calc R . . H7B H 0.0755 0.7518 0.5293 0.101 Uiso 1 1 calc R . . H7C H 0.1927 0.8524 0.5036 0.101 Uiso 1 1 calc R . . C4 C 0.12143(14) 0.5160(2) 0.61659(6) 0.0656(4) Uani 1 1 d . . . H4A H 0.1028 0.6420 0.6223 0.098 Uiso 1 1 calc R . . H4B H 0.1323 0.4546 0.6504 0.098 Uiso 1 1 calc R . . H4C H 0.0481 0.4626 0.5948 0.098 Uiso 1 1 calc R . . C5 C 0.29125(17) 0.3000(2) 0.58476(6) 0.0630(4) Uani 1 1 d . . . H5A H 0.3720 0.2917 0.5666 0.095 Uiso 1 1 calc R . . H5B H 0.2209 0.2327 0.5652 0.095 Uiso 1 1 calc R . . H5C H 0.3072 0.2505 0.6202 0.095 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0602(6) 0.0718(7) 0.0431(5) 0.0124(4) 0.0105(4) -0.0047(5) O1 0.0610(6) 0.0778(7) 0.0359(5) -0.0013(4) 0.0056(4) -0.0094(5) N2 0.0459(6) 0.0504(6) 0.0407(6) 0.0034(4) 0.0059(4) 0.0005(4) N1 0.0453(6) 0.0528(6) 0.0372(6) -0.0016(4) 0.0049(4) -0.0032(4) C21 0.0416(6) 0.0423(7) 0.0384(6) -0.0013(5) 0.0086(5) -0.0019(5) C20 0.0449(7) 0.0441(7) 0.0492(7) 0.0013(5) 0.0071(5) -0.0061(5) C19 0.0508(7) 0.0448(7) 0.0489(7) 0.0075(5) 0.0123(6) -0.0006(5) C18 0.0462(7) 0.0526(8) 0.0382(6) -0.0002(5) 0.0111(5) 0.0029(5) C17 0.0558(8) 0.0660(9) 0.0459(7) 0.0069(6) 0.0080(6) 0.0077(7) C16 0.0565(8) 0.0842(11) 0.0494(8) 0.0000(7) -0.0031(6) 0.0090(8) C15 0.0470(7) 0.0793(11) 0.0556(8) -0.0149(7) -0.0014(6) 0.0010(7) C14 0.0433(7) 0.0575(8) 0.0492(7) -0.0137(6) 0.0081(5) -0.0008(6) C13 0.0460(7) 0.0587(9) 0.0745(10) -0.0167(7) 0.0063(7) -0.0104(6) C12 0.0550(8) 0.0464(8) 0.0759(10) -0.0051(7) 0.0121(7) -0.0120(6) C11 0.0484(7) 0.0427(7) 0.0521(7) -0.0037(6) 0.0106(6) -0.0048(5) C22 0.0427(6) 0.0418(7) 0.0398(6) -0.0052(5) 0.0110(5) -0.0014(5) C23 0.0411(6) 0.0491(7) 0.0386(6) -0.0068(5) 0.0111(5) 0.0013(5) C10 0.0621(8) 0.0410(7) 0.0599(8) 0.0058(6) 0.0088(6) -0.0067(6) C9 0.0553(8) 0.0465(7) 0.0519(8) 0.0055(6) 0.0023(6) 0.0012(6) C8 0.0459(7) 0.0434(7) 0.0421(7) -0.0007(5) 0.0064(5) -0.0018(5) C1 0.0441(6) 0.0445(7) 0.0415(7) 0.0016(5) 0.0043(5) 0.0006(5) C3 0.0422(7) 0.0567(8) 0.0439(7) -0.0013(6) 0.0026(5) -0.0010(5) C2 0.0450(7) 0.0551(8) 0.0405(7) -0.0041(5) 0.0054(5) -0.0059(5) C6 0.0642(9) 0.0786(10) 0.0454(8) -0.0062(7) 0.0003(6) -0.0106(7) C7 0.0575(8) 0.0699(10) 0.0746(10) 0.0059(8) 0.0034(7) 0.0115(7) C4 0.0488(8) 0.0947(12) 0.0548(8) -0.0054(8) 0.0127(6) -0.0107(7) C5 0.0774(10) 0.0523(8) 0.0599(9) 0.0009(7) 0.0089(7) -0.0079(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 N2 1.2795(13) . ? O1 N1 1.2784(13) . ? N2 C1 1.3493(15) . ? N2 C3 1.4989(16) . ? N1 C1 1.3510(16) . ? N1 C2 1.5009(16) . ? C21 C8 1.4073(17) . ? C21 C22 1.4257(17) . ? C21 C20 1.4362(17) . ? C20 C19 1.3482(18) . ? C20 H20 0.9300 . ? C19 C18 1.4341(18) . ? C19 H19 0.9300 . ? C18 C17 1.3967(18) . ? C18 C23 1.4182(18) . ? C17 C16 1.382(2) . ? C17 H17 0.9300 . ? C16 C15 1.375(2) . ? C16 H16 0.9300 . ? C15 C14 1.399(2) . ? C15 H6 0.9300 . ? C14 C23 1.4220(17) . ? C14 C13 1.427(2) . ? C13 C12 1.340(2) . ? C13 H13 0.9300 . ? C12 C11 1.4397(19) . ? C12 H12 0.9300 . ? C11 C10 1.3947(19) . ? C11 C22 1.4204(18) . ? C22 C23 1.4253(18) . ? C10 C9 1.3779(19) . ? C10 H10 0.9300 . ? C9 C8 1.3957(18) . ? C9 H9 0.9300 . ? C8 C1 1.4632(17) . ? C3 C6 1.5114(19) . ? C3 C7 1.532(2) . ? C3 C2 1.5511(18) . ? C2 C4 1.5161(18) . ? C2 C5 1.526(2) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 O2 N2 C1 126.57(11) . . ? O2 N2 C3 121.46(10) . . ? C1 N2 C3 111.51(10) . . ? O1 N1 C1 126.22(10) . . ? O1 N1 C2 122.09(10) . . ? C1 N1 C2 111.47(10) . . ? C8 C21 C22 118.59(11) . . ? C8 C21 C20 123.42(11) . . ? C22 C21 C20 117.98(11) . . ? C19 C20 C21 121.42(12) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C20 C19 C18 121.97(12) . . ? C20 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C17 C18 C23 119.20(12) . . ? C17 C18 C19 122.67(12) . . ? C23 C18 C19 118.13(11) . . ? C16 C17 C18 120.61(14) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C15 C16 C17 120.79(14) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C15 C14 120.95(14) . . ? C16 C15 H6 119.5 . . ? C14 C15 H6 119.5 . . ? C15 C14 C23 118.84(13) . . ? C15 C14 C13 122.66(13) . . ? C23 C14 C13 118.50(12) . . ? C12 C13 C14 121.47(13) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C13 C12 C11 121.88(13) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C10 C11 C22 118.98(11) . . ? C10 C11 C12 122.82(12) . . ? C22 C11 C12 118.19(12) . . ? C11 C22 C23 119.69(11) . . ? C11 C22 C21 120.06(11) . . ? C23 C22 C21 120.24(11) . . ? C18 C23 C14 119.61(12) . . ? C18 C23 C22 120.16(11) . . ? C14 C23 C22 120.23(12) . . ? C9 C10 C11 121.28(12) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C9 C8 120.54(12) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C8 C21 120.49(12) . . ? C9 C8 C1 117.94(11) . . ? C21 C8 C1 121.56(11) . . ? N2 C1 N1 108.38(11) . . ? N2 C1 C8 125.33(11) . . ? N1 C1 C8 126.05(11) . . ? N2 C3 C6 109.94(11) . . ? N2 C3 C7 105.32(11) . . ? C6 C3 C7 111.26(12) . . ? N2 C3 C2 100.52(9) . . ? C6 C3 C2 115.16(12) . . ? C7 C3 C2 113.58(11) . . ? N1 C2 C4 109.80(10) . . ? N1 C2 C5 106.23(11) . . ? C4 C2 C5 110.79(12) . . ? N1 C2 C3 99.81(9) . . ? C4 C2 C3 115.48(11) . . ? C5 C2 C3 113.72(11) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? 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 C8 C21 C20 C19 -178.01(12) . . . . ? C22 C21 C20 C19 2.77(18) . . . . ? C21 C20 C19 C18 -0.20(19) . . . . ? C20 C19 C18 C17 178.42(12) . . . . ? C20 C19 C18 C23 -1.50(18) . . . . ? C23 C18 C17 C16 0.3(2) . . . . ? C19 C18 C17 C16 -179.65(12) . . . . ? C18 C17 C16 C15 -0.2(2) . . . . ? C17 C16 C15 C14 -0.2(2) . . . . ? C16 C15 C14 C23 0.4(2) . . . . ? C16 C15 C14 C13 -179.11(13) . . . . ? C15 C14 C13 C12 179.19(14) . . . . ? C23 C14 C13 C12 -0.3(2) . . . . ? C14 C13 C12 C11 1.7(2) . . . . ? C13 C12 C11 C10 177.11(13) . . . . ? C13 C12 C11 C22 -1.2(2) . . . . ? C10 C11 C22 C23 -178.95(12) . . . . ? C12 C11 C22 C23 -0.54(17) . . . . ? C10 C11 C22 C21 0.22(18) . . . . ? C12 C11 C22 C21 178.63(11) . . . . ? C8 C21 C22 C11 -2.07(17) . . . . ? C20 C21 C22 C11 177.19(11) . . . . ? C8 C21 C22 C23 177.10(10) . . . . ? C20 C21 C22 C23 -3.64(17) . . . . ? C17 C18 C23 C14 0.00(17) . . . . ? C19 C18 C23 C14 179.92(11) . . . . ? C17 C18 C23 C22 -179.36(11) . . . . ? C19 C18 C23 C22 0.56(17) . . . . ? C15 C14 C23 C18 -0.33(18) . . . . ? C13 C14 C23 C18 179.21(11) . . . . ? C15 C14 C23 C22 179.03(11) . . . . ? C13 C14 C23 C22 -1.43(17) . . . . ? C11 C22 C23 C18 -178.80(10) . . . . ? C21 C22 C23 C18 2.03(17) . . . . ? C11 C22 C23 C14 1.84(17) . . . . ? C21 C22 C23 C14 -177.33(10) . . . . ? C22 C11 C10 C9 0.6(2) . . . . ? C12 C11 C10 C9 -177.74(13) . . . . ? C11 C10 C9 C8 0.5(2) . . . . ? C10 C9 C8 C21 -2.4(2) . . . . ? C10 C9 C8 C1 176.34(12) . . . . ? C22 C21 C8 C9 3.16(18) . . . . ? C20 C21 C8 C9 -176.05(11) . . . . ? C22 C21 C8 C1 -175.55(10) . . . . ? C20 C21 C8 C1 5.23(19) . . . . ? O2 N2 C1 N1 -179.83(11) . . . . ? C3 N2 C1 N1 7.93(14) . . . . ? O2 N2 C1 C8 5.5(2) . . . . ? C3 N2 C1 C8 -166.70(12) . . . . ? O1 N1 C1 N2 -173.30(11) . . . . ? C2 N1 C1 N2 12.03(14) . . . . ? O1 N1 C1 C8 1.3(2) . . . . ? C2 N1 C1 C8 -173.39(11) . . . . ? C9 C8 C1 N2 46.21(18) . . . . ? C21 C8 C1 N2 -135.05(13) . . . . ? C9 C8 C1 N1 -127.49(14) . . . . ? C21 C8 C1 N1 51.26(19) . . . . ? O2 N2 C3 C6 42.44(16) . . . . ? C1 N2 C3 C6 -144.86(12) . . . . ? O2 N2 C3 C7 -77.52(14) . . . . ? C1 N2 C3 C7 95.18(12) . . . . ? O2 N2 C3 C2 164.27(11) . . . . ? C1 N2 C3 C2 -23.04(13) . . . . ? O1 N1 C2 C4 37.96(16) . . . . ? C1 N1 C2 C4 -147.12(12) . . . . ? O1 N1 C2 C5 -81.89(14) . . . . ? C1 N1 C2 C5 93.03(12) . . . . ? O1 N1 C2 C3 159.72(11) . . . . ? C1 N1 C2 C3 -25.36(13) . . . . ? N2 C3 C2 N1 26.75(11) . . . . ? C6 C3 C2 N1 144.81(11) . . . . ? C7 C3 C2 N1 -85.24(12) . . . . ? N2 C3 C2 C4 144.35(11) . . . . ? C6 C3 C2 C4 -97.59(15) . . . . ? C7 C3 C2 C4 32.36(16) . . . . ? N2 C3 C2 C5 -85.95(12) . . . . ? C6 C3 C2 C5 32.11(16) . . . . ? C7 C3 C2 C5 162.07(12) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.165 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.027 data_ha7 _database_code_depnum_ccdc_archive 'CCDC 840781' #TrackingRef 'PyrNN-C6F6-293K_new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H42 F6 N4 O4' _chemical_formula_weight 900.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.3540(3) _cell_length_b 7.5164(2) _cell_length_c 18.7218(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.9670(13) _cell_angle_gamma 90.00 _cell_volume 2139.77(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour green-blue _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6935 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.21 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3715 _reflns_number_gt 2970 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0579P)^2^+0.8164P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3715 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1290 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 C22 C 0.39647(11) 0.0969(3) 0.31781(9) 0.0476(4) Uani 1 1 d . . . C23 C 0.32133(11) 0.0218(3) 0.34298(9) 0.0495(4) Uani 1 1 d . . . C21 C 0.44358(11) -0.0029(2) 0.27066(9) 0.0453(4) Uani 1 1 d . . . C8 C 0.51432(12) 0.0802(3) 0.24342(10) 0.0527(5) Uani 1 1 d . . . C9 C 0.53677(13) 0.2551(3) 0.26206(11) 0.0600(5) Uani 1 1 d . . . H9 H 0.5825 0.3094 0.2425 0.072 Uiso 1 1 calc R . . C10 C 0.49268(13) 0.3490(3) 0.30874(11) 0.0595(5) Uani 1 1 d . . . H10 H 0.5102 0.4644 0.3216 0.071 Uiso 1 1 calc R . . C11 C 0.42208(12) 0.2739(3) 0.33712(10) 0.0523(5) Uani 1 1 d . . . C12 C 0.37219(15) 0.3704(3) 0.38384(11) 0.0637(5) Uani 1 1 d . . . H12 H 0.3892 0.4854 0.3978 0.076 Uiso 1 1 calc R . . C13 C 0.30205(15) 0.2994(3) 0.40775(12) 0.0678(6) Uani 1 1 d . . . H13 H 0.2715 0.3659 0.4380 0.081 Uiso 1 1 calc R . . C14 C 0.27250(13) 0.1223(3) 0.38783(10) 0.0577(5) Uani 1 1 d . . . C15 C 0.19623(15) 0.0495(4) 0.40872(12) 0.0718(6) Uani 1 1 d . . . H15 H 0.1645 0.1142 0.4387 0.086 Uiso 1 1 calc R . . C16 C 0.16760(15) -0.1162(4) 0.38561(13) 0.0757(7) Uani 1 1 d . . . H16 H 0.1154 -0.1608 0.3984 0.091 Uiso 1 1 calc R . . C17 C 0.21601(14) -0.2179(3) 0.34320(11) 0.0663(6) Uani 1 1 d . . . H17 H 0.1968 -0.3317 0.3294 0.080 Uiso 1 1 calc R . . C18 C 0.29280(12) -0.1522(3) 0.32107(10) 0.0542(5) Uani 1 1 d . . . C19 C 0.34181(13) -0.2488(3) 0.27503(10) 0.0580(5) Uani 1 1 d . . . H19 H 0.3243 -0.3637 0.2612 0.070 Uiso 1 1 calc R . . C20 C 0.41347(13) -0.1784(3) 0.25060(10) 0.0552(5) Uani 1 1 d . . . H20 H 0.4436 -0.2454 0.2202 0.066 Uiso 1 1 calc R . . C1 C 0.56456(12) -0.0116(3) 0.19326(10) 0.0541(5) Uani 1 1 d . . . N1 N 0.60336(11) -0.1726(3) 0.20215(9) 0.0625(5) Uani 1 1 d . . . O1 O 0.60541(11) -0.2730(2) 0.25738(9) 0.0848(5) Uani 1 1 d . . . C2 C 0.63767(15) -0.2321(3) 0.13440(12) 0.0694(6) Uani 1 1 d . . . C3 C 0.64980(13) -0.0490(3) 0.09915(12) 0.0637(6) Uani 1 1 d . . . N2 N 0.58239(11) 0.0587(2) 0.13063(9) 0.0573(4) Uani 1 1 d . . . O2 O 0.55416(11) 0.2072(2) 0.10312(9) 0.0770(5) Uani 1 1 d . . . C4 C 0.5645(2) -0.3439(4) 0.09314(16) 0.0935(8) Uani 1 1 d . . . H4A H 0.5129 -0.2718 0.0811 0.140 Uiso 1 1 calc R . . H4B H 0.5511 -0.4420 0.1226 0.140 Uiso 1 1 calc R . . H4C H 0.5833 -0.3884 0.0497 0.140 Uiso 1 1 calc R . . C5 C 0.7203(2) -0.3424(5) 0.15388(19) 0.1206(12) Uani 1 1 d . . . H5A H 0.7657 -0.2695 0.1793 0.181 Uiso 1 1 calc R . . H5B H 0.7394 -0.3874 0.1107 0.181 Uiso 1 1 calc R . . H5C H 0.7080 -0.4400 0.1840 0.181 Uiso 1 1 calc R . . C7 C 0.63049(18) -0.0464(4) 0.01744(13) 0.0815(7) Uani 1 1 d . . . H7A H 0.5752 -0.1039 0.0023 0.122 Uiso 1 1 calc R . . H7B H 0.6763 -0.1081 -0.0024 0.122 Uiso 1 1 calc R . . H7C H 0.6277 0.0745 0.0008 0.122 Uiso 1 1 calc R . . C6 C 0.73815(16) 0.0385(5) 0.12457(18) 0.1041(10) Uani 1 1 d . . . H6A H 0.7495 0.0353 0.1763 0.156 Uiso 1 1 calc R . . H6B H 0.7369 0.1598 0.1085 0.156 Uiso 1 1 calc R . . H6C H 0.7838 -0.0246 0.1050 0.156 Uiso 1 1 calc R . . C25 C 0.57096(15) -0.0280(4) 0.46490(12) 0.0722(6) Uani 1 1 d . . . C24 C 0.55848(15) 0.1347(3) 0.49428(13) 0.0722(6) Uani 1 1 d . . . C26 C 0.48747(16) 0.1630(3) 0.52939(13) 0.0718(6) Uani 1 1 d . . . F2 F 0.64077(10) -0.0565(3) 0.43118(9) 0.1088(6) Uani 1 1 d . . . F1 F 0.61593(11) 0.2663(2) 0.48913(10) 0.1091(6) Uani 1 1 d . . . F3 F 0.47400(12) 0.3219(2) 0.55732(10) 0.1074(5) 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 C22 0.0479(9) 0.0496(11) 0.0449(9) -0.0001(8) 0.0054(7) 0.0049(8) C23 0.0483(9) 0.0552(11) 0.0448(9) 0.0048(8) 0.0064(7) 0.0047(8) C21 0.0457(9) 0.0437(10) 0.0464(9) -0.0019(7) 0.0061(7) 0.0036(8) C8 0.0501(10) 0.0526(11) 0.0566(11) -0.0029(9) 0.0114(8) 0.0029(9) C9 0.0550(11) 0.0561(12) 0.0708(12) -0.0039(10) 0.0152(9) -0.0075(9) C10 0.0636(12) 0.0484(11) 0.0679(12) -0.0105(9) 0.0143(10) -0.0045(9) C11 0.0580(11) 0.0449(11) 0.0534(10) -0.0058(8) 0.0056(8) 0.0030(9) C12 0.0767(13) 0.0516(12) 0.0647(12) -0.0092(10) 0.0171(10) 0.0034(10) C13 0.0761(14) 0.0663(14) 0.0651(12) -0.0059(11) 0.0243(11) 0.0153(12) C14 0.0566(11) 0.0667(13) 0.0518(10) 0.0055(10) 0.0142(8) 0.0097(10) C15 0.0660(13) 0.0849(17) 0.0694(13) 0.0102(12) 0.0270(10) 0.0085(13) C16 0.0595(12) 0.0956(19) 0.0752(14) 0.0222(14) 0.0205(11) -0.0034(13) C17 0.0652(12) 0.0705(14) 0.0628(12) 0.0102(11) 0.0074(10) -0.0129(11) C18 0.0549(10) 0.0573(12) 0.0494(10) 0.0052(9) 0.0036(8) -0.0038(9) C19 0.0628(12) 0.0520(11) 0.0579(11) -0.0019(9) 0.0036(9) -0.0081(10) C20 0.0606(11) 0.0492(11) 0.0566(11) -0.0082(9) 0.0106(9) 0.0016(9) C1 0.0508(10) 0.0531(12) 0.0601(11) -0.0018(9) 0.0140(8) 0.0029(9) N1 0.0611(10) 0.0656(11) 0.0639(10) 0.0046(9) 0.0191(8) 0.0132(9) O1 0.0878(11) 0.0884(12) 0.0819(11) 0.0225(10) 0.0252(8) 0.0295(9) C2 0.0680(13) 0.0689(14) 0.0761(14) -0.0044(12) 0.0277(11) 0.0144(11) C3 0.0575(11) 0.0663(14) 0.0723(13) -0.0134(11) 0.0269(10) -0.0052(10) N2 0.0614(9) 0.0512(10) 0.0626(10) -0.0043(8) 0.0203(8) -0.0006(8) O2 0.1007(12) 0.0553(9) 0.0800(10) 0.0069(8) 0.0298(9) 0.0053(8) C4 0.124(2) 0.0622(16) 0.1008(19) -0.0152(14) 0.0395(17) -0.0200(15) C5 0.109(2) 0.131(3) 0.133(3) 0.015(2) 0.0558(19) 0.063(2) C7 0.0983(17) 0.0798(17) 0.0746(15) -0.0106(13) 0.0407(13) -0.0081(14) C6 0.0667(15) 0.123(3) 0.130(2) -0.040(2) 0.0370(15) -0.0258(16) C25 0.0622(13) 0.0844(18) 0.0698(14) 0.0021(12) 0.0082(10) -0.0092(12) C24 0.0707(14) 0.0695(15) 0.0740(14) 0.0067(12) 0.0016(11) -0.0237(12) C26 0.0776(15) 0.0629(14) 0.0717(14) -0.0045(11) -0.0010(11) -0.0067(12) F2 0.0886(10) 0.1307(15) 0.1138(12) -0.0118(11) 0.0382(9) -0.0137(10) F1 0.1090(12) 0.0933(11) 0.1269(13) -0.0034(10) 0.0236(10) -0.0483(10) F3 0.1209(13) 0.0802(11) 0.1202(13) -0.0264(9) 0.0138(10) -0.0075(9) _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 C22 C11 1.420(3) . ? C22 C23 1.422(2) . ? C22 C21 1.429(2) . ? C23 C14 1.419(3) . ? C23 C18 1.421(3) . ? C21 C8 1.408(3) . ? C21 C20 1.430(3) . ? C8 C9 1.391(3) . ? C8 C1 1.467(3) . ? C9 C10 1.373(3) . ? C9 H9 0.9300 . ? C10 C11 1.391(3) . ? C10 H10 0.9300 . ? C11 C12 1.436(3) . ? C12 C13 1.334(3) . ? C12 H12 0.9300 . ? C13 C14 1.439(3) . ? C13 H13 0.9300 . ? C14 C15 1.397(3) . ? C15 C16 1.370(4) . ? C15 H15 0.9300 . ? C16 C17 1.389(3) . ? C16 H16 0.9300 . ? C17 C18 1.393(3) . ? C17 H17 0.9300 . ? C18 C19 1.420(3) . ? C19 C20 1.356(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C1 N2 1.348(2) . ? C1 N1 1.349(3) . ? N1 O1 1.277(2) . ? N1 C2 1.507(3) . ? C2 C5 1.517(3) . ? C2 C4 1.525(4) . ? C2 C3 1.548(3) . ? C3 N2 1.498(2) . ? C3 C7 1.517(3) . ? C3 C6 1.523(3) . ? N2 O2 1.280(2) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C25 F2 1.334(3) . ? C25 C24 1.365(3) . ? C25 C26 1.369(3) 3_656 ? C24 F1 1.338(3) . ? C24 C26 1.366(3) . ? C26 F3 1.331(3) . ? C26 C25 1.369(3) 3_656 ? 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 C11 C22 C23 119.78(17) . . ? C11 C22 C21 120.21(16) . . ? C23 C22 C21 119.95(17) . . ? C14 C23 C18 119.59(17) . . ? C14 C23 C22 120.27(18) . . ? C18 C23 C22 120.10(17) . . ? C8 C21 C22 118.21(17) . . ? C8 C21 C20 123.44(17) . . ? C22 C21 C20 118.26(16) . . ? C9 C8 C21 120.32(17) . . ? C9 C8 C1 118.06(17) . . ? C21 C8 C1 121.58(18) . . ? C10 C9 C8 121.25(18) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.89(18) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C22 119.08(17) . . ? C10 C11 C12 122.50(18) . . ? C22 C11 C12 118.40(18) . . ? C13 C12 C11 121.7(2) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 121.56(19) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C15 C14 C23 119.3(2) . . ? C15 C14 C13 122.4(2) . . ? C23 C14 C13 118.21(18) . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 120.4(2) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C18 121.1(2) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C19 122.7(2) . . ? C17 C18 C23 118.68(19) . . ? C19 C18 C23 118.55(17) . . ? C20 C19 C18 121.84(19) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C21 121.29(18) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? N2 C1 N1 108.63(16) . . ? N2 C1 C8 124.10(18) . . ? N1 C1 C8 127.22(18) . . ? O1 N1 C1 126.24(17) . . ? O1 N1 C2 122.26(18) . . ? C1 N1 C2 111.23(17) . . ? N1 C2 C5 109.7(2) . . ? N1 C2 C4 105.70(18) . . ? C5 C2 C4 110.7(2) . . ? N1 C2 C3 99.89(17) . . ? C5 C2 C3 116.3(2) . . ? C4 C2 C3 113.4(2) . . ? N2 C3 C7 109.91(18) . . ? N2 C3 C6 106.14(18) . . ? C7 C3 C6 110.5(2) . . ? N2 C3 C2 100.50(15) . . ? C7 C3 C2 115.01(19) . . ? C6 C3 C2 113.9(2) . . ? O2 N2 C1 126.41(16) . . ? O2 N2 C3 121.81(16) . . ? C1 N2 C3 111.42(17) . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? F2 C25 C24 120.1(2) . . ? F2 C25 C26 119.7(2) . 3_656 ? C24 C25 C26 120.2(2) . 3_656 ? F1 C24 C25 120.2(2) . . ? F1 C24 C26 119.9(2) . . ? C25 C24 C26 120.0(2) . . ? F3 C26 C24 120.4(2) . . ? F3 C26 C25 119.7(2) . 3_656 ? C24 C26 C25 119.9(2) . 3_656 ? 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 C11 C22 C23 C14 -0.6(3) . . . . ? C21 C22 C23 C14 -177.87(16) . . . . ? C11 C22 C23 C18 176.96(16) . . . . ? C21 C22 C23 C18 -0.3(3) . . . . ? C11 C22 C21 C8 -1.1(3) . . . . ? C23 C22 C21 C8 176.17(16) . . . . ? C11 C22 C21 C20 -177.76(16) . . . . ? C23 C22 C21 C20 -0.5(2) . . . . ? C22 C21 C8 C9 -0.3(3) . . . . ? C20 C21 C8 C9 176.22(18) . . . . ? C22 C21 C8 C1 -178.40(16) . . . . ? C20 C21 C8 C1 -1.9(3) . . . . ? C21 C8 C9 C10 1.9(3) . . . . ? C1 C8 C9 C10 -179.94(19) . . . . ? C8 C9 C10 C11 -2.1(3) . . . . ? C9 C10 C11 C22 0.7(3) . . . . ? C9 C10 C11 C12 -177.50(19) . . . . ? C23 C22 C11 C10 -176.36(17) . . . . ? C21 C22 C11 C10 0.9(3) . . . . ? C23 C22 C11 C12 1.9(3) . . . . ? C21 C22 C11 C12 179.14(17) . . . . ? C10 C11 C12 C13 176.7(2) . . . . ? C22 C11 C12 C13 -1.6(3) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C18 C23 C14 C15 -1.1(3) . . . . ? C22 C23 C14 C15 176.55(17) . . . . ? C18 C23 C14 C13 -178.65(17) . . . . ? C22 C23 C14 C13 -1.0(3) . . . . ? C12 C13 C14 C15 -176.1(2) . . . . ? C12 C13 C14 C23 1.5(3) . . . . ? C23 C14 C15 C16 -0.9(3) . . . . ? C13 C14 C15 C16 176.6(2) . . . . ? C14 C15 C16 C17 2.6(3) . . . . ? C15 C16 C17 C18 -2.3(3) . . . . ? C16 C17 C18 C19 -177.0(2) . . . . ? C16 C17 C18 C23 0.3(3) . . . . ? C14 C23 C18 C17 1.4(3) . . . . ? C22 C23 C18 C17 -176.24(17) . . . . ? C14 C23 C18 C19 178.79(17) . . . . ? C22 C23 C18 C19 1.2(3) . . . . ? C17 C18 C19 C20 176.00(19) . . . . ? C23 C18 C19 C20 -1.3(3) . . . . ? C18 C19 C20 C21 0.5(3) . . . . ? C8 C21 C20 C19 -176.09(18) . . . . ? C22 C21 C20 C19 0.4(3) . . . . ? C9 C8 C1 N2 -48.0(3) . . . . ? C21 C8 C1 N2 130.1(2) . . . . ? C9 C8 C1 N1 129.0(2) . . . . ? C21 C8 C1 N1 -52.8(3) . . . . ? N2 C1 N1 O1 175.26(19) . . . . ? C8 C1 N1 O1 -2.1(3) . . . . ? N2 C1 N1 C2 -10.6(2) . . . . ? C8 C1 N1 C2 171.99(19) . . . . ? O1 N1 C2 C5 -38.4(3) . . . . ? C1 N1 C2 C5 147.3(2) . . . . ? O1 N1 C2 C4 81.1(3) . . . . ? C1 N1 C2 C4 -93.3(2) . . . . ? O1 N1 C2 C3 -161.01(19) . . . . ? C1 N1 C2 C3 24.6(2) . . . . ? N1 C2 C3 N2 -26.88(19) . . . . ? C5 C2 C3 N2 -144.8(2) . . . . ? C4 C2 C3 N2 85.2(2) . . . . ? N1 C2 C3 C7 -144.83(18) . . . . ? C5 C2 C3 C7 97.2(3) . . . . ? C4 C2 C3 C7 -32.8(3) . . . . ? N1 C2 C3 C6 86.2(2) . . . . ? C5 C2 C3 C6 -31.8(3) . . . . ? C4 C2 C3 C6 -161.8(2) . . . . ? N1 C1 N2 O2 177.47(18) . . . . ? C8 C1 N2 O2 -5.0(3) . . . . ? N1 C1 N2 C3 -9.4(2) . . . . ? C8 C1 N2 C3 168.12(18) . . . . ? C7 C3 N2 O2 -40.8(3) . . . . ? C6 C3 N2 O2 78.7(3) . . . . ? C2 C3 N2 O2 -162.46(18) . . . . ? C7 C3 N2 C1 145.64(19) . . . . ? C6 C3 N2 C1 -94.8(2) . . . . ? C2 C3 N2 C1 24.0(2) . . . . ? F2 C25 C24 F1 0.3(4) . . . . ? C26 C25 C24 F1 179.5(2) 3_656 . . . ? F2 C25 C24 C26 -179.3(2) . . . . ? C26 C25 C24 C26 -0.1(4) 3_656 . . . ? F1 C24 C26 F3 1.3(3) . . . . ? C25 C24 C26 F3 -179.0(2) . . . . ? F1 C24 C26 C25 -179.5(2) . . . 3_656 ? C25 C24 C26 C25 0.1(4) . . . 3_656 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.161 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.029 # Attachment 'Pyrin-a.cif' data_phl004a_0m _database_code_depnum_ccdc_archive 'CCDC 840782' #TrackingRef 'Pyrin-a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 N2 O' _chemical_formula_sum 'C23 H21 N2 O' _chemical_formula_weight 341.42 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.322(5) _cell_length_b 7.181(3) _cell_length_c 24.037(11) _cell_angle_alpha 90.00 _cell_angle_beta 98.018(6) _cell_angle_gamma 90.00 _cell_volume 1764.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6885 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour red _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8906 _exptl_absorpt_correction_T_max 0.9976 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008a)' _exptl_special_details ; The diffraction data were collected in three sets of 606 frames (0.3 deg. width in omega) at phi = 0, 120 and 240 deg. A scan time of 50 sec/frame was used. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14608 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4021 _reflns_number_gt 3050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (Bruker-AXS, 2009)' _computing_cell_refinement 'Bruker SAINT (Bruker-AXS 2009a)' _computing_data_reduction 'Bruker SAINT (Bruker-AXS 2009a)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL(Bruker-AXS 2008)' _computing_publication_material 'Bruker SHELXTL(Bruker-AXS 2008)' _publ_section_references ; Bruker-AXS (2009). APEX2, Version 2009.9-0, Madison, WI. Bruker-AXS (2009a). SAINT, Version 7.68A, Madison, WI Bruker-AXS (2008). SHELXTL, Version 2008/4, Madison, WI Sheldrick, G. M. (2008). SHELXS and SHELXL. Acta Cryst. A64, 112-122. Sheldrick, G, M. (2008a). SADABS, Version 2008/2. University of G\"ottingen, Germany. ; _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. H-atoms were placed in calculated positions (C---H = 0.95 - 0.98 \%A) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. In the final stages of refinement, a peak corresponding to ca. 0.1 of an oxygen atom appeared near N2. After several trials, it was concluded that this resulted from co-crystallization of the corresponding nitronylnitroxide compound which is also formed in the reaction used to prepare the present compound. The refinement was concluded by restraining the N-O distance to this oxygen to be that found in an authentic sample of the latter compound while letting the site occupancy and displacement parameters refine. ; _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^)+(0.0482P)^2^+0.5800P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4021 _refine_ls_number_parameters 249 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 -0.06211(11) 0.20041(15) -0.00926(4) 0.0322(3) Uani 1 1 d . . . O1A O -0.1157(12) 0.0556(16) 0.17504(12) 0.037(4) Uani 0.097(4) 1 d PD . . N1 N -0.10803(12) 0.13264(17) 0.03304(5) 0.0265(3) Uani 1 1 d . . . N2 N -0.11671(13) 0.04466(18) 0.12207(5) 0.0286(3) Uani 1 1 d D . . C1 C -0.24943(14) 0.0859(2) 0.03253(6) 0.0257(3) Uani 1 1 d . . . C2 C -0.31975(16) 0.2723(2) 0.03731(7) 0.0335(4) Uani 1 1 d . . . H2A H -0.3053 0.3529 0.0059 0.050 Uiso 1 1 calc R . . H2B H -0.2851 0.3328 0.0728 0.050 Uiso 1 1 calc R . . H2C H -0.4137 0.2501 0.0363 0.050 Uiso 1 1 calc R . . C3 C -0.30338(15) -0.0135(2) -0.02114(6) 0.0293(3) Uani 1 1 d . . . H3A H -0.3935 -0.0528 -0.0191 0.044 Uiso 1 1 calc R . . H3B H -0.2495 -0.1231 -0.0260 0.044 Uiso 1 1 calc R . . H3C H -0.3021 0.0708 -0.0531 0.044 Uiso 1 1 calc R . . C4 C -0.23709(14) -0.0312(2) 0.08757(6) 0.0263(3) Uani 1 1 d . . . C5 C -0.20987(16) -0.2371(2) 0.07719(7) 0.0322(4) Uani 1 1 d . . . H5A H -0.1390 -0.2474 0.0542 0.048 Uiso 1 1 calc R . . H5B H -0.2890 -0.2957 0.0575 0.048 Uiso 1 1 calc R . . H5C H -0.1842 -0.2999 0.1132 0.048 Uiso 1 1 calc R . . C6 C -0.35272(15) -0.0132(2) 0.11993(6) 0.0335(4) Uani 1 1 d . . . H6A H -0.3363 -0.0870 0.1545 0.050 Uiso 1 1 calc R . . H6B H -0.4320 -0.0590 0.0967 0.050 Uiso 1 1 calc R . . H6C H -0.3645 0.1178 0.1294 0.050 Uiso 1 1 calc R . . C7 C -0.04547(14) 0.1247(2) 0.08878(6) 0.0257(3) Uani 1 1 d . . . C8 C 0.08318(14) 0.2123(2) 0.10562(6) 0.0259(3) Uani 1 1 d . . . C9 C 0.10395(15) 0.3903(2) 0.08510(6) 0.0289(3) Uani 1 1 d . . . H9 H 0.0380 0.4470 0.0590 0.035 Uiso 1 1 calc R . . C10 C 0.21927(15) 0.4849(2) 0.10230(6) 0.0299(3) Uani 1 1 d . . . H10 H 0.2310 0.6062 0.0881 0.036 Uiso 1 1 calc R . . C11 C 0.31883(15) 0.4051(2) 0.14018(6) 0.0271(3) Uani 1 1 d . . . C12 C 0.43785(16) 0.5025(2) 0.16006(7) 0.0333(4) Uani 1 1 d . . . H12 H 0.4521 0.6226 0.1455 0.040 Uiso 1 1 calc R . . C13 C 0.52994(16) 0.4269(2) 0.19898(7) 0.0343(4) Uani 1 1 d . . . H13 H 0.6064 0.4966 0.2121 0.041 Uiso 1 1 calc R . . C14 C 0.51491(15) 0.2440(2) 0.22094(6) 0.0289(3) Uani 1 1 d . . . C15 C 0.60942(16) 0.1616(2) 0.26081(7) 0.0347(4) Uani 1 1 d . . . H15 H 0.6863 0.2293 0.2746 0.042 Uiso 1 1 calc R . . C16 C 0.59283(16) -0.0163(2) 0.28052(6) 0.0355(4) Uani 1 1 d . . . H16 H 0.6584 -0.0695 0.3075 0.043 Uiso 1 1 calc R . . C17 C 0.48111(16) -0.1180(2) 0.26119(6) 0.0314(3) Uani 1 1 d . . . H17 H 0.4712 -0.2407 0.2747 0.038 Uiso 1 1 calc R . . C18 C 0.38304(15) -0.0408(2) 0.22189(6) 0.0265(3) Uani 1 1 d . . . C19 C 0.26454(14) -0.1389(2) 0.20177(6) 0.0271(3) Uani 1 1 d . . . H19 H 0.2533 -0.2623 0.2145 0.032 Uiso 1 1 calc R . . C20 C 0.16841(15) -0.0607(2) 0.16515(6) 0.0272(3) Uani 1 1 d . . . H20 H 0.0908 -0.1296 0.1534 0.033 Uiso 1 1 calc R . . C21 C 0.18106(14) 0.1246(2) 0.14359(6) 0.0238(3) Uani 1 1 d . . . C22 C 0.30008(14) 0.2229(2) 0.16130(6) 0.0246(3) Uani 1 1 d . . . C23 C 0.39958(14) 0.1414(2) 0.20096(6) 0.0253(3) 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 O1 0.0389(6) 0.0314(6) 0.0272(5) 0.0044(4) 0.0080(5) -0.0039(5) O1A 0.039(8) 0.038(7) 0.032(7) 0.005(5) -0.004(5) -0.014(5) N1 0.0294(7) 0.0264(6) 0.0241(6) 0.0000(5) 0.0048(5) -0.0039(5) N2 0.0301(7) 0.0292(7) 0.0262(6) -0.0023(5) 0.0030(5) -0.0045(5) C1 0.0262(8) 0.0255(7) 0.0256(7) -0.0001(6) 0.0039(6) -0.0018(6) C2 0.0371(9) 0.0260(8) 0.0374(8) 0.0002(7) 0.0048(7) 0.0025(7) C3 0.0315(8) 0.0301(8) 0.0259(7) -0.0008(6) 0.0024(6) -0.0020(6) C4 0.0277(8) 0.0266(7) 0.0245(7) 0.0000(6) 0.0035(6) -0.0029(6) C5 0.0373(9) 0.0255(8) 0.0333(8) 0.0030(6) 0.0034(7) -0.0020(6) C6 0.0315(9) 0.0410(9) 0.0287(8) 0.0024(7) 0.0067(7) -0.0023(7) C7 0.0289(8) 0.0229(7) 0.0248(7) -0.0017(6) 0.0024(6) -0.0009(6) C8 0.0287(8) 0.0253(7) 0.0243(7) -0.0044(6) 0.0057(6) -0.0034(6) C9 0.0327(8) 0.0250(7) 0.0289(7) -0.0013(6) 0.0044(6) -0.0005(6) C10 0.0372(9) 0.0208(7) 0.0327(8) -0.0020(6) 0.0085(7) -0.0044(6) C11 0.0308(8) 0.0224(7) 0.0292(7) -0.0054(6) 0.0076(6) -0.0028(6) C12 0.0341(9) 0.0233(8) 0.0438(9) -0.0048(7) 0.0093(7) -0.0055(6) C13 0.0300(8) 0.0307(8) 0.0424(9) -0.0119(7) 0.0061(7) -0.0072(7) C14 0.0281(8) 0.0311(8) 0.0281(7) -0.0107(6) 0.0058(6) -0.0031(6) C15 0.0306(8) 0.0411(9) 0.0313(8) -0.0114(7) 0.0006(7) -0.0046(7) C16 0.0341(9) 0.0457(10) 0.0255(7) -0.0033(7) 0.0002(7) 0.0020(7) C17 0.0348(9) 0.0357(8) 0.0240(7) -0.0002(6) 0.0055(6) 0.0004(7) C18 0.0294(8) 0.0293(8) 0.0221(7) -0.0035(6) 0.0083(6) -0.0003(6) C19 0.0309(8) 0.0256(7) 0.0260(7) 0.0008(6) 0.0084(6) -0.0019(6) C20 0.0283(8) 0.0258(7) 0.0286(7) -0.0021(6) 0.0076(6) -0.0053(6) C21 0.0278(7) 0.0234(7) 0.0213(6) -0.0041(6) 0.0070(6) -0.0021(6) C22 0.0273(8) 0.0241(7) 0.0237(7) -0.0059(6) 0.0078(6) -0.0018(6) C23 0.0267(7) 0.0279(8) 0.0226(7) -0.0070(6) 0.0080(6) -0.0017(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.2767(16) . ? O1A N2 1.274(2) . ? N1 C7 1.4049(19) . ? N1 C1 1.496(2) . ? N2 C7 1.2944(19) . ? N2 C4 1.4969(19) . ? C1 C3 1.511(2) . ? C1 C2 1.534(2) . ? C1 C4 1.558(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C6 1.518(2) . ? C4 C5 1.532(2) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.474(2) . ? C8 C9 1.397(2) . ? C8 C21 1.412(2) . ? C9 C10 1.383(2) . ? C9 H9 0.9500 . ? C10 C11 1.397(2) . ? C10 H10 0.9500 . ? C11 C22 1.426(2) . ? C11 C12 1.436(2) . ? C12 C13 1.351(2) . ? C12 H12 0.9500 . ? C13 C14 1.432(2) . ? C13 H13 0.9500 . ? C14 C15 1.400(2) . ? C14 C23 1.425(2) . ? C15 C16 1.382(2) . ? C15 H15 0.9500 . ? C16 C17 1.389(2) . ? C16 H16 0.9500 . ? C17 C18 1.399(2) . ? C17 H17 0.9500 . ? C18 C23 1.421(2) . ? C18 C19 1.436(2) . ? C19 C20 1.353(2) . ? C19 H19 0.9500 . ? C20 C21 1.441(2) . ? C20 H20 0.9500 . ? C21 C22 1.429(2) . ? C22 C23 1.426(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 N1 C7 127.06(13) . . ? O1 N1 C1 123.31(12) . . ? C7 N1 C1 108.47(11) . . ? O1A N2 C7 131.6(5) . . ? O1A N2 C4 117.8(5) . . ? C7 N2 C4 108.55(12) . . ? N1 C1 C3 110.86(12) . . ? N1 C1 C2 105.95(12) . . ? C3 C1 C2 110.75(13) . . ? N1 C1 C4 98.63(11) . . ? C3 C1 C4 116.54(13) . . ? C2 C1 C4 112.99(12) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 C6 109.66(12) . . ? N2 C4 C5 106.52(12) . . ? C6 C4 C5 109.91(13) . . ? N2 C4 C1 103.74(11) . . ? C6 C4 C1 114.36(13) . . ? C5 C4 C1 112.19(12) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 N1 112.48(13) . . ? N2 C7 C8 125.97(13) . . ? N1 C7 C8 121.40(13) . . ? C9 C8 C21 120.34(14) . . ? C9 C8 C7 118.05(14) . . ? C21 C8 C7 121.53(13) . . ? C10 C9 C8 120.79(15) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 121.17(14) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C22 118.96(14) . . ? C10 C11 C12 122.29(14) . . ? C22 C11 C12 118.72(14) . . ? C13 C12 C11 121.42(15) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 121.45(15) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C23 118.81(15) . . ? C15 C14 C13 122.62(14) . . ? C23 C14 C13 118.57(14) . . ? C16 C15 C14 121.18(15) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 120.55(15) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 120.41(16) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C23 119.52(14) . . ? C17 C18 C19 122.34(14) . . ? C23 C18 C19 118.14(13) . . ? C20 C19 C18 121.89(14) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C21 121.49(14) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C8 C21 C22 118.70(13) . . ? C8 C21 C20 123.51(13) . . ? C22 C21 C20 117.79(13) . . ? C23 C22 C11 119.57(13) . . ? C23 C22 C21 120.39(13) . . ? C11 C22 C21 120.04(13) . . ? C18 C23 C14 119.52(14) . . ? C18 C23 C22 120.24(13) . . ? C14 C23 C22 120.21(14) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.249 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.042