# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Christopher Bielawski' _publ_contact_author_address ; Chemistry and Biochemistry University of Texas at Austin 1 University Station, A5300 Austin Texas 78712 UNITED STATES OF AMERICA ; _publ_contact_author_email BIELAWSKI@MAIL.CM.UTEXAS.EDU _publ_section_title ; Triazene formation via reaction of imidazol-2-ylidenes with azides. ; loop_ _publ_author_name 'Christopher Bielawski' 'Dimitri Khramov' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # If this CIF has been generated directly or indirectly from an entry in the # Cambridge Structural Database, then it will include bibliographic, chemical, # crystal, experimental, refinement or atomic coordinate data resulting from # the CCDC's data processing and validation procedures. Files generated from # CSD entries are Copyright 2005 Cambridge Crystallographic Data Centre. They # may be used in bona fide research applications only, and may not be copied or # further disseminated in any form, whether machine-readable or not, except for # the purposes of generating routine backup copies on your local computer # system. # # Files arising from any other source may also contain material that is the # copyright of third parties, including the originator, and you should check # with the originator concerning the permitted uses of the information # contained in this CIF. # # For further information on the CCDC and the free tools enCIFer and Mercury # for validating and visualising CIF files, please visit www.ccdc.cam.ac.uk # ####################################################################### data_bismes2 _database_code_depnum_ccdc_archive 'CCDC 275071' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 14.6396(3) _cell_length_b 12.1965(2) _cell_length_c 28.0462(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.6340(10) _cell_angle_gamma 90.00 _cell_volume 5007.4 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z N1 N 0.00915(15) 0.0787(2) 0.18477(8) C2 C 0.0229(2) 0.1724(3) 0.21269(10) H2 H 0.0497 0.2398 0.2020 C3 C -0.0080(2) 0.1512(3) 0.25621(11) H3 H -0.0074 0.2001 0.2831 N4 N -0.04103(16) 0.0441(2) 0.25629(8) C5 C -0.03065(18) -0.0017(3) 0.21218(10) N6 N -0.05192(15) -0.1057(2) 0.20269(8) N7 N -0.05171(15) -0.1213(2) 0.15426(8) N8 N -0.05132(16) -0.2220(2) 0.14352(8) C9 C -0.0528(2) -0.2345(3) 0.09145(10) H9A H -0.0530 -0.1625 0.0776 H9B H -0.1078 -0.2713 0.0815 C10 C 0.0296(2) -0.2952(3) 0.07306(10) C11 C 0.0261(3) -0.3446(3) 0.02822(11) H11 H -0.0305 -0.3435 0.0106 C12 C 0.1031(3) -0.3948(3) 0.00945(12) H12 H 0.0997 -0.4263 -0.0219 C13 C 0.1830(3) -0.3978(3) 0.03487(14) H13 H 0.2359 -0.4322 0.0215 C14 C 0.1868(2) -0.3523(3) 0.07965(13) H14 H 0.2422 -0.3565 0.0981 C15 C 0.1108(2) -0.3007(3) 0.09841(11) H15 H 0.1138 -0.2682 0.1296 C16 C 0.0493(2) 0.0627(2) 0.13851(10) C17 C 0.0056(2) 0.1050(2) 0.09823(10) C18 C 0.0457(2) 0.0880(3) 0.05452(10) H18 H 0.0171 0.1181 0.0265 C19 C 0.1268(2) 0.0289(3) 0.05052(10) C20 C 0.1677(2) -0.0132(2) 0.09137(10) H20A H 0.2225 -0.0559 0.0889 C21 C 0.1306(2) 0.0051(2) 0.13616(10) C22 C -0.0857(2) 0.1615(3) 0.10249(10) H22C H -0.0839 0.2156 0.1273 H22A H -0.1318 0.1076 0.1089 H22B H -0.1004 0.1950 0.0724 C23 C 0.1703(2) 0.0112(3) 0.00258(10) H23A H 0.1337 0.0452 -0.0218 H23B H 0.2302 0.0432 0.0029 H23C H 0.1750 -0.0660 -0.0037 C24 C 0.17563(19) -0.0415(3) 0.18074(10) H24A H 0.1418 -0.0210 0.2085 H24B H 0.1766 -0.1200 0.1780 H24C H 0.2371 -0.0146 0.1836 C25 C -0.0813(2) -0.0102(2) 0.29643(9) C26 C -0.1755(2) -0.0238(3) 0.29754(10) C27 C -0.2116(2) -0.0776(3) 0.33663(11) H27 H -0.2762 -0.0911 0.3376 C28 C -0.1574(2) -0.1147(3) 0.37383(10) C29 C -0.0644(2) -0.0965(3) 0.37192(10) H29 H -0.0266 -0.1220 0.3978 C30 C -0.0241(2) -0.0446(2) 0.33335(10) C31 C -0.23617(19) 0.0192(3) 0.25837(10) H31C H -0.2204 -0.0153 0.2288 H31A H -0.2287 0.0971 0.2555 H31B H -0.2990 0.0042 0.2654 C32 C -0.2000(2) -0.1736(3) 0.41551(10) H32A H -0.1534 -0.1921 0.4385 H32B H -0.2445 -0.1270 0.4302 H32C H -0.2291 -0.2393 0.4043 C33 C 0.0773(2) -0.0278(3) 0.33177(10) H33A H 0.1055 -0.0563 0.3602 H33B H 0.1008 -0.0657 0.3045 H33C H 0.0906 0.0490 0.3291 #END data_bismes _database_code_depnum_ccdc_archive 'CCDC 275072' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 9.1191(1) _cell_length_b 15.4148(2) _cell_length_c 18.4677(3) _cell_angle_alpha 104.680(1) _cell_angle_beta 92.260(1) _cell_angle_gamma 90.110(1) _cell_volume 2509.1 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z N1 N 0.77213(17) 0.39923(11) 0.21585(9) C2 C 0.6645(2) 0.34574(15) 0.17009(12) H2 H 0.6160 0.2950 0.1803 C3 C 0.6423(2) 0.37857(15) 0.11053(12) H3 H 0.5731 0.3562 0.0695 N4 N 0.73564(16) 0.45222(11) 0.11800(9) C5 C 0.8169(2) 0.46472(14) 0.18347(11) N6 N 0.9195(4) 0.5232(2) 0.2192(3) N7 N 0.9425(2) 0.59218(16) 0.18886(11) N8 N 1.0402(2) 0.64971(14) 0.22210(12) C9 C 1.1164(5) 0.6316(3) 0.2858(3) H9A H 1.1733 0.5781 0.2705 H9B H 1.0462 0.6225 0.3206 C10 C 1.2162(3) 0.70970(17) 0.32470(12) C11 C 1.3614(3) 0.69379(17) 0.33549(13) H11 H 1.3964 0.6341 0.3158 C12 C 1.4573(3) 0.7608(2) 0.37343(15) H12 H 1.5590 0.7477 0.3803 C13 C 1.4066(3) 0.84668(18) 0.40047(13) H13 H 1.4726 0.8937 0.4269 C14 C 1.2610(3) 0.86387(16) 0.38995(12) H14A H 1.2247 0.9235 0.4084 C15 C 1.1659(3) 0.79587(16) 0.35283(12) H15 H 1.0637 0.8079 0.3460 C16 C 0.8191(2) 0.39150(14) 0.28966(11) C17 C 0.9023(2) 0.31823(14) 0.29551(11) C18 C 0.9381(2) 0.30988(15) 0.36756(12) H18 H 0.9932 0.2588 0.3731 C19 C 0.8957(2) 0.37165(17) 0.43103(13) C20 C 0.8161(3) 0.44439(17) 0.42196(13) H20A H 0.7861 0.4878 0.4658 C21 C 0.7738(2) 0.45533(16) 0.35171(13) C22 C 0.9519(2) 0.24944(15) 0.22842(12) H22C H 1.0035 0.2789 0.1969 H22A H 0.8686 0.2173 0.2009 H22B H 1.0154 0.2072 0.2438 C23 C 0.9316(3) 0.3585(2) 0.50864(13) H23A H 0.9892 0.3057 0.5053 H23B H 0.9854 0.4099 0.5378 H23C H 0.8414 0.3525 0.5322 C24 C 0.6796(3) 0.53336(18) 0.34409(14) H24C H 0.6508 0.5661 0.3928 H24A H 0.5938 0.5119 0.3128 H24B H 0.7337 0.5722 0.3213 C25 C 0.7370(2) 0.50401(14) 0.06272(11) C26 C 0.8043(2) 0.46784(13) -0.00432(11) C27 C 0.8008(2) 0.51819(14) -0.05721(11) H27 H 0.8464 0.4942 -0.1039 C28 C 0.7332(2) 0.60057(15) -0.04433(12) C29 C 0.6638(2) 0.63244(14) 0.02211(12) H29 H 0.6136 0.6886 0.0309 C30 C 0.6628(2) 0.58442(14) 0.07663(11) C31 C 0.8767(2) 0.37765(14) -0.02088(12) H31C H 0.9292 0.3690 0.0228 H31A H 0.9418 0.3740 -0.0611 H31B H 0.8022 0.3322 -0.0380 C32 C 0.7395(3) 0.65476(16) -0.10218(13) H32C H 0.6778 0.7062 -0.0885 H32A H 0.7072 0.6173 -0.1501 H32B H 0.8388 0.6733 -0.1060 C33 C 0.5831(3) 0.61935(16) 0.14806(12) H33C H 0.5255 0.6704 0.1450 H33A H 0.6533 0.6353 0.1895 H33B H 0.5213 0.5724 0.1559 #END data_triazaco _database_code_depnum_ccdc_archive 'CCDC 275073' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H29 N5 O' _chemical_formula_weight 451.56 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 Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 14.0109(3) _cell_length_b 14.0230(3) _cell_length_c 12.6469(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2484.80(8) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour orange _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9725 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5434 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5434 _reflns_number_gt 3543 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.0440P)^2^+0.0100P] 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 0.0120(15) _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' _refine_ls_abs_structure_Flack 1.5(17) _refine_ls_number_reflns 5434 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1135 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_restrained_S_all 1.191 _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 N1 N 0.22192(13) 0.35717(12) 0.09931(13) 0.0326(5) Uani 1 1 d . . . C2 C 0.25360(17) 0.40386(16) 0.00837(16) 0.0371(6) Uani 1 1 d . . . H2 H 0.2671 0.3741 -0.0583 0.044 Uiso 1 1 d R . . C3 C 0.26259(17) 0.49579(17) 0.03107(17) 0.0375(6) Uani 1 1 d . . . H3 H 0.2834 0.5452 -0.0162 0.045 Uiso 1 1 d R . . N4 N 0.23610(14) 0.50809(12) 0.13681(13) 0.0318(5) Uani 1 1 d . . . C5 C 0.21233(16) 0.42218(15) 0.17820(16) 0.0299(5) Uani 1 1 d . . . N6 N 0.18224(13) 0.41365(12) 0.27957(13) 0.0303(4) Uani 1 1 d . . . N7 N 0.18387(13) 0.32289(12) 0.30950(13) 0.0292(4) Uani 1 1 d . . . N8 N 0.14564(13) 0.31030(12) 0.40169(13) 0.0299(4) Uani 1 1 d . . . C9 C 0.15892(16) 0.21518(15) 0.43577(16) 0.0297(5) Uani 1 1 d . . . O10 O 0.22921(12) 0.16780(11) 0.41577(12) 0.0452(4) Uani 1 1 d . . . C11 C 0.08023(15) 0.17794(15) 0.50283(15) 0.0264(5) Uani 1 1 d . . . C12 C 0.09385(17) 0.09287(16) 0.55642(18) 0.0372(6) Uani 1 1 d . . . H12 H 0.1548 0.0618 0.5533 0.045 Uiso 1 1 d R . . C13 C 0.02065(17) 0.05429(17) 0.6155(2) 0.0431(6) Uani 1 1 d . . . H13 H 0.0307 -0.0044 0.6530 0.052 Uiso 1 1 d R . . C14 C -0.06678(18) 0.09944(17) 0.62021(19) 0.0430(6) Uani 1 1 d . . . H14 H -0.1171 0.0716 0.6615 0.052 Uiso 1 1 d R . . C15 C -0.08173(17) 0.18364(17) 0.56696(17) 0.0379(6) Uani 1 1 d . . . H15 H -0.1428 0.2145 0.5699 0.045 Uiso 1 1 d R . . C16 C -0.00773(16) 0.22364(16) 0.50873(17) 0.0306(6) Uani 1 1 d . . . H16 H -0.0168 0.2827 0.4717 0.037 Uiso 1 1 d R . . C17 C 0.18815(17) 0.25937(15) 0.09714(16) 0.0332(6) Uani 1 1 d . . . C18 C 0.09799(18) 0.24331(17) 0.05494(17) 0.0399(6) Uani 1 1 d . . . C19 C 0.06602(19) 0.14924(18) 0.04756(19) 0.0465(7) Uani 1 1 d . . . H19 H 0.0038 0.1365 0.0190 0.056 Uiso 1 1 d R . . C20 C 0.1233(2) 0.07361(17) 0.08021(19) 0.0475(7) Uani 1 1 d . . . C21 C 0.21126(19) 0.09391(17) 0.12350(17) 0.0421(6) Uani 1 1 d . . . H21 H 0.2498 0.0421 0.1488 0.051 Uiso 1 1 d R . . C22 C 0.24647(17) 0.18602(16) 0.13246(16) 0.0345(6) Uani 1 1 d . . . C23 C 0.0348(2) 0.32477(19) 0.0215(2) 0.0581(8) Uani 1 1 d . . . H23C H 0.0280 0.3688 0.0791 0.087 Uiso 1 1 d R . . H23A H -0.0270 0.3016 0.0009 0.087 Uiso 1 1 d R . . H23B H 0.0628 0.3568 -0.0380 0.087 Uiso 1 1 d R . . C24 C 0.0891(2) -0.02888(18) 0.0677(2) 0.0639(9) Uani 1 1 d . . . H24A H 0.1374 -0.0714 0.0938 0.096 Uiso 1 1 d R . . H24B H 0.0317 -0.0371 0.1080 0.096 Uiso 1 1 d R . . H24C H 0.0766 -0.0428 -0.0054 0.096 Uiso 1 1 d R . . C25 C 0.34197(17) 0.20486(18) 0.18176(19) 0.0456(7) Uani 1 1 d . . . H25A H 0.3539 0.2723 0.1808 0.068 Uiso 1 1 d R . . H25B H 0.3429 0.1824 0.2534 0.068 Uiso 1 1 d R . . H25C H 0.3904 0.1726 0.1418 0.068 Uiso 1 1 d R . . C26 C 0.23401(18) 0.59850(15) 0.19144(15) 0.0339(6) Uani 1 1 d . . . C27 C 0.3198(2) 0.64587(17) 0.20712(17) 0.0423(7) Uani 1 1 d . . . C28 C 0.3155(2) 0.73657(19) 0.25469(18) 0.0512(8) Uani 1 1 d . . . H28 H 0.3737 0.7708 0.2678 0.061 Uiso 1 1 d R . . C29 C 0.2302(3) 0.77786(18) 0.28313(18) 0.0548(8) Uani 1 1 d . . . C30 C 0.1463(2) 0.72739(18) 0.26542(17) 0.0465(7) Uani 1 1 d . . . H30 H 0.0864 0.7552 0.2858 0.056 Uiso 1 1 d R . . C31 C 0.14603(19) 0.63717(16) 0.21950(17) 0.0377(6) Uani 1 1 d . . . C32 C 0.41320(18) 0.60373(19) 0.1743(2) 0.0512(7) Uani 1 1 d . . . H32C H 0.4144 0.5964 0.0989 0.077 Uiso 1 1 d R . . H32A H 0.4222 0.5427 0.2073 0.077 Uiso 1 1 d R . . H32B H 0.4644 0.6449 0.1958 0.077 Uiso 1 1 d R . . C33 C 0.2287(3) 0.87619(18) 0.3329(2) 0.0789(11) Uani 1 1 d . . . H33A H 0.1637 0.8935 0.3476 0.118 Uiso 1 1 d R . . H33B H 0.2645 0.8756 0.3976 0.118 Uiso 1 1 d R . . H33C H 0.2561 0.9217 0.2851 0.118 Uiso 1 1 d R . . C34 C 0.05425(18) 0.58485(18) 0.20322(17) 0.0428(6) Uani 1 1 d . . . H34C H 0.0026 0.6279 0.2176 0.064 Uiso 1 1 d R . . H34A H 0.0488 0.5314 0.2503 0.064 Uiso 1 1 d R . . H34B H 0.0483 0.5630 0.1316 0.064 Uiso 1 1 d 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 N1 0.0422(11) 0.0280(10) 0.0275(10) 0.0000(8) 0.0001(8) -0.0039(9) C2 0.0505(16) 0.0358(14) 0.0249(11) 0.0056(11) 0.0054(10) -0.0038(12) C3 0.0444(15) 0.0370(14) 0.0310(13) 0.0059(10) 0.0017(11) -0.0070(12) N4 0.0425(12) 0.0272(10) 0.0258(10) 0.0048(8) 0.0001(8) -0.0061(9) C5 0.0353(13) 0.0283(12) 0.0262(12) 0.0045(11) -0.0016(10) -0.0025(11) N6 0.0363(11) 0.0294(11) 0.0250(9) 0.0041(8) 0.0002(8) -0.0039(9) N7 0.0335(11) 0.0257(10) 0.0284(10) 0.0051(8) -0.0012(8) -0.0038(8) N8 0.0376(11) 0.0256(10) 0.0265(9) 0.0039(8) 0.0034(8) -0.0047(8) C9 0.0318(14) 0.0279(13) 0.0294(12) -0.0010(10) -0.0027(10) -0.0004(11) O10 0.0392(10) 0.0393(10) 0.0569(10) 0.0148(8) 0.0108(8) 0.0078(8) C11 0.0304(13) 0.0221(12) 0.0268(11) 0.0014(10) -0.0007(9) -0.0027(10) C12 0.0346(14) 0.0361(14) 0.0408(13) 0.0107(12) 0.0009(11) 0.0063(11) C13 0.0458(16) 0.0318(14) 0.0517(16) 0.0161(12) 0.0069(13) 0.0036(12) C14 0.0450(16) 0.0372(15) 0.0469(14) 0.0070(12) 0.0121(12) -0.0034(13) C15 0.0328(14) 0.0389(15) 0.0418(13) -0.0026(12) 0.0055(11) 0.0030(11) C16 0.0359(14) 0.0256(13) 0.0304(12) 0.0000(10) -0.0034(10) -0.0001(11) C17 0.0449(15) 0.0276(13) 0.0271(12) -0.0019(10) 0.0039(10) -0.0049(11) C18 0.0502(16) 0.0361(15) 0.0335(13) 0.0003(11) -0.0043(12) -0.0049(12) C19 0.0550(17) 0.0451(17) 0.0394(14) -0.0029(12) -0.0050(12) -0.0139(14) C20 0.067(2) 0.0347(15) 0.0404(15) -0.0061(12) 0.0073(14) -0.0104(14) C21 0.0590(17) 0.0308(14) 0.0366(13) -0.0016(11) 0.0143(13) 0.0025(13) C22 0.0409(15) 0.0337(14) 0.0290(12) -0.0033(10) 0.0063(10) 0.0024(12) C23 0.0586(18) 0.0503(18) 0.0653(17) 0.0109(15) -0.0248(15) -0.0018(15) C24 0.086(2) 0.0379(16) 0.0676(19) -0.0072(15) 0.0066(17) -0.0187(15) C25 0.0403(16) 0.0496(17) 0.0468(14) -0.0043(13) 0.0059(12) 0.0082(12) C26 0.0527(16) 0.0235(12) 0.0256(12) 0.0048(10) -0.0037(11) -0.0055(12) C27 0.0614(19) 0.0368(15) 0.0286(13) 0.0134(11) -0.0113(12) -0.0169(14) C28 0.080(2) 0.0385(17) 0.0351(15) 0.0125(12) -0.0180(14) -0.0253(17) C29 0.101(3) 0.0340(15) 0.0296(13) 0.0045(12) -0.0091(15) -0.0148(18) C30 0.080(2) 0.0304(14) 0.0289(13) 0.0040(11) -0.0003(12) 0.0047(15) C31 0.0599(18) 0.0269(13) 0.0262(12) 0.0062(10) -0.0066(12) -0.0007(12) C32 0.0493(18) 0.0523(18) 0.0520(15) 0.0199(14) -0.0134(13) -0.0182(14) C33 0.157(3) 0.0367(16) 0.0427(15) -0.0050(13) -0.013(2) -0.0115(19) C34 0.0495(16) 0.0448(15) 0.0341(14) 0.0076(12) -0.0026(11) 0.0049(13) _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 N1 C5 1.358(3) . ? N1 C2 1.396(3) . ? N1 C17 1.451(3) . ? C2 C3 1.327(3) . ? C2 H2 0.9599 . ? C3 N4 1.398(3) . ? C3 H3 0.9600 . ? N4 C5 1.355(3) . ? N4 C26 1.444(3) . ? C5 N6 1.355(3) . ? N6 N7 1.328(2) . ? N7 N8 1.295(2) . ? N8 C9 1.414(3) . ? C9 O10 1.215(2) . ? C9 C11 1.486(3) . ? C11 C12 1.385(3) . ? C11 C16 1.391(3) . ? C12 C13 1.380(3) . ? C12 H12 0.9600 . ? C13 C14 1.380(3) . ? C13 H13 0.9601 . ? C14 C15 1.375(3) . ? C14 H14 0.9600 . ? C15 C16 1.390(3) . ? C15 H15 0.9600 . ? C16 H16 0.9600 . ? C17 C22 1.388(3) . ? C17 C18 1.390(3) . ? C18 C19 1.396(3) . ? C18 C23 1.506(4) . ? C19 C20 1.393(4) . ? C19 H19 0.9600 . ? C20 C21 1.378(4) . ? C20 C24 1.523(3) . ? C21 C22 1.387(3) . ? C21 H21 0.9600 . ? C22 C25 1.500(3) . ? C23 H23C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9601 . ? C24 H24A 0.9600 . ? C24 H24B 0.9599 . ? C24 H24C 0.9600 . ? C25 H25A 0.9601 . ? C25 H25B 0.9600 . ? C25 H25C 0.9599 . ? C26 C27 1.387(3) . ? C26 C31 1.393(3) . ? C27 C28 1.408(3) . ? C27 C32 1.495(4) . ? C28 C29 1.376(4) . ? C28 H28 0.9600 . ? C29 C30 1.391(4) . ? C29 C33 1.516(3) . ? C30 C31 1.392(3) . ? C30 H30 0.9601 . ? C31 C34 1.495(3) . ? C32 H32C 0.9600 . ? C32 H32A 0.9599 . ? C32 H32B 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9601 . ? C33 H33C 0.9600 . ? C34 H34C 0.9600 . ? C34 H34A 0.9600 . ? C34 H34B 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 C5 N1 C2 108.77(17) . . ? C5 N1 C17 128.03(18) . . ? C2 N1 C17 122.10(18) . . ? C3 C2 N1 107.92(19) . . ? C3 C2 H2 126.4 . . ? N1 C2 H2 125.6 . . ? C2 C3 N4 107.6(2) . . ? C2 C3 H3 126.5 . . ? N4 C3 H3 125.9 . . ? C5 N4 C3 108.96(18) . . ? C5 N4 C26 126.20(16) . . ? C3 N4 C26 124.83(18) . . ? N6 C5 N4 121.37(19) . . ? N6 C5 N1 131.8(2) . . ? N4 C5 N1 106.78(17) . . ? N7 N6 C5 110.43(17) . . ? N8 N7 N6 112.34(16) . . ? N7 N8 C9 110.40(17) . . ? O10 C9 N8 124.0(2) . . ? O10 C9 C11 121.90(19) . . ? N8 C9 C11 114.07(19) . . ? C12 C11 C16 119.5(2) . . ? C12 C11 C9 118.7(2) . . ? C16 C11 C9 121.75(19) . . ? C13 C12 C11 120.0(2) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 120.2(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.5(2) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 119.5(2) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.2 . . ? C15 C16 C11 120.2(2) . . ? C15 C16 H16 120.5 . . ? C11 C16 H16 119.3 . . ? C22 C17 C18 122.6(2) . . ? C22 C17 N1 120.2(2) . . ? C18 C17 N1 117.2(2) . . ? C17 C18 C19 118.1(2) . . ? C17 C18 C23 121.3(2) . . ? C19 C18 C23 120.6(2) . . ? C20 C19 C18 121.0(2) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C21 C20 C19 118.4(2) . . ? C21 C20 C24 121.1(2) . . ? C19 C20 C24 120.4(2) . . ? C20 C21 C22 122.9(2) . . ? C20 C21 H21 118.7 . . ? C22 C21 H21 118.5 . . ? C21 C22 C17 117.0(2) . . ? C21 C22 C25 121.0(2) . . ? C17 C22 C25 121.9(2) . . ? C18 C23 H23C 109.5 . . ? C18 C23 H23A 110.5 . . ? H23C C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23C C23 H23B 109.5 . . ? H23A C23 H23B 108.4 . . ? C20 C24 H24A 109.2 . . ? C20 C24 H24B 108.8 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 110.4 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 108.9 . . ? C22 C25 H25B 110.3 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.2 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C31 122.9(2) . . ? C27 C26 N4 118.1(2) . . ? C31 C26 N4 118.8(2) . . ? C26 C27 C28 117.2(2) . . ? C26 C27 C32 122.0(2) . . ? C28 C27 C32 120.8(2) . . ? C29 C28 C27 121.9(3) . . ? C29 C28 H28 118.8 . . ? C27 C28 H28 119.4 . . ? C28 C29 C30 118.6(2) . . ? C28 C29 C33 120.3(3) . . ? C30 C29 C33 121.2(3) . . ? C29 C30 C31 122.1(3) . . ? C29 C30 H30 119.3 . . ? C31 C30 H30 118.6 . . ? C30 C31 C26 117.3(2) . . ? C30 C31 C34 120.4(2) . . ? C26 C31 C34 122.4(2) . . ? C27 C32 H32C 109.4 . . ? C27 C32 H32A 110.3 . . ? H32C C32 H32A 109.5 . . ? C27 C32 H32B 109.8 . . ? H32C C32 H32B 109.5 . . ? H32A C32 H32B 108.4 . . ? C29 C33 H33A 108.9 . . ? C29 C33 H33B 109.8 . . ? H33A C33 H33B 109.5 . . ? C29 C33 H33C 109.7 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C31 C34 H34C 108.3 . . ? C31 C34 H34A 111.5 . . ? H34C C34 H34A 108.3 . . ? C31 C34 H34B 111.2 . . ? H34C C34 H34B 108.3 . . ? H34A C34 H34B 109.2 . . ? 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 C5 N1 C2 C3 -0.4(3) . . . . ? C17 N1 C2 C3 168.5(2) . . . . ? N1 C2 C3 N4 -0.3(3) . . . . ? C2 C3 N4 C5 0.9(3) . . . . ? C2 C3 N4 C26 -178.6(2) . . . . ? C3 N4 C5 N6 -178.9(2) . . . . ? C26 N4 C5 N6 0.6(3) . . . . ? C3 N4 C5 N1 -1.1(2) . . . . ? C26 N4 C5 N1 178.3(2) . . . . ? C2 N1 C5 N6 178.4(2) . . . . ? C17 N1 C5 N6 10.3(4) . . . . ? C2 N1 C5 N4 0.9(2) . . . . ? C17 N1 C5 N4 -167.1(2) . . . . ? N4 C5 N6 N7 -165.96(19) . . . . ? N1 C5 N6 N7 16.9(3) . . . . ? C5 N6 N7 N8 -172.77(17) . . . . ? N6 N7 N8 C9 -173.10(17) . . . . ? N7 N8 C9 O10 34.1(3) . . . . ? N7 N8 C9 C11 -148.09(17) . . . . ? O10 C9 C11 C12 9.7(3) . . . . ? N8 C9 C11 C12 -168.11(18) . . . . ? O10 C9 C11 C16 -167.0(2) . . . . ? N8 C9 C11 C16 15.2(3) . . . . ? C16 C11 C12 C13 -0.3(3) . . . . ? C9 C11 C12 C13 -177.1(2) . . . . ? C11 C12 C13 C14 1.0(4) . . . . ? C12 C13 C14 C15 -0.6(4) . . . . ? C13 C14 C15 C16 -0.5(3) . . . . ? C14 C15 C16 C11 1.2(3) . . . . ? C12 C11 C16 C15 -0.8(3) . . . . ? C9 C11 C16 C15 175.93(19) . . . . ? C5 N1 C17 C22 -90.8(3) . . . . ? C2 N1 C17 C22 102.5(3) . . . . ? C5 N1 C17 C18 91.6(3) . . . . ? C2 N1 C17 C18 -75.1(3) . . . . ? C22 C17 C18 C19 -0.5(3) . . . . ? N1 C17 C18 C19 177.0(2) . . . . ? C22 C17 C18 C23 177.4(2) . . . . ? N1 C17 C18 C23 -5.0(3) . . . . ? C17 C18 C19 C20 -0.8(4) . . . . ? C23 C18 C19 C20 -178.8(2) . . . . ? C18 C19 C20 C21 2.2(4) . . . . ? C18 C19 C20 C24 -177.6(2) . . . . ? C19 C20 C21 C22 -2.3(3) . . . . ? C24 C20 C21 C22 177.4(2) . . . . ? C20 C21 C22 C17 1.1(3) . . . . ? C20 C21 C22 C25 179.0(2) . . . . ? C18 C17 C22 C21 0.4(3) . . . . ? N1 C17 C22 C21 -177.06(19) . . . . ? C18 C17 C22 C25 -177.5(2) . . . . ? N1 C17 C22 C25 5.0(3) . . . . ? C5 N4 C26 C27 115.4(2) . . . . ? C3 N4 C26 C27 -65.2(3) . . . . ? C5 N4 C26 C31 -68.9(3) . . . . ? C3 N4 C26 C31 110.5(2) . . . . ? C31 C26 C27 C28 0.7(3) . . . . ? N4 C26 C27 C28 176.18(17) . . . . ? C31 C26 C27 C32 -178.7(2) . . . . ? N4 C26 C27 C32 -3.2(3) . . . . ? C26 C27 C28 C29 -1.1(3) . . . . ? C32 C27 C28 C29 178.4(2) . . . . ? C27 C28 C29 C30 0.9(3) . . . . ? C27 C28 C29 C33 -179.2(2) . . . . ? C28 C29 C30 C31 -0.4(3) . . . . ? C33 C29 C30 C31 179.8(2) . . . . ? C29 C30 C31 C26 0.0(3) . . . . ? C29 C30 C31 C34 179.2(2) . . . . ? C27 C26 C31 C30 -0.2(3) . . . . ? N4 C26 C31 C30 -175.64(17) . . . . ? C27 C26 C31 C34 -179.3(2) . . . . ? N4 C26 C31 C34 5.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.222 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.044