# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/264 # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_global _audit_creation_method 'maXus' _publ_contact_author_name 'Marcel Pierrot ' _publ_contact_author_address ; LBS-UMR 6517 Facult\'e des Sciences et Techniques de Saint J\'er\^ome Avenue Escadrille Normandie Niemen 13397 Marseille Cedex 20 France ; _publ_contact_author_email 'marcel.pierrot@lbs.u-3mrs.fr' _publ_contact_author_fax '(33) 4 91 98 32 08' _publ_contact_author_phone '(33) 4 91 28 84 24' _publ_requested_journal 'J. Chem.Soc., Dalton Trans. ' _publ_section_title ; 3(5)-(1-Adamanttyl)pyrazoles:chemistry and molecular structure ; loop_ _publ_author_name _publ_author_address 'Claramunt, R.M.' #<--'Last name, first name' ; Dep. Quimica Organica, Facultad de Ciencias, UNED Senda del Rey 9,E-28040 Madrid, Spain ; 'Lopez, C.' #<--'Last name, first name' ; Dep. Quimica Organica, Facultad de Ciencias, UNED Senda del Rey 9,E-28040 Madrid, Spain ; 'Garcia, M.A.' #<--'Last name, first name' ; Dep. Quimica Organica, Facultad de Ciencias, UNED Senda del Rey 9,E-28040 Madrid, Spain ; 'Pierrot, M.' #<--'Last name, first name' ; LBS-UMR 6517, Centre Scientifique Saint-J\'er\^ome, 13397 Marseille, Cedex 20 , France ; 'Giorgi, M.' #<--'Last name, first name' ; LBS-UMR 6517, Centre Scientifique Saint-J\'er\^ome, 13397 Marseille, Cedex 20 , France ; 'Elguero, J.' #<--'Last name, first name' ;Centro de Quimica Organica, CSIC Juan de la Cierva 3, E-28006 Madrid, Spain ; _publ_section_abstract ; We present the crystal and molecular structure of ; _publ_section_comment ; The study of the titled structure was undertaken to establish its threedimensional structure. Geometries are tabulated below. All Diagrams andcalculations were performed using maXus (Nonius, Delft & MacScience, Japan). ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Prism' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment 'noref' # Submission details _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_measurement_method 'phi-scan' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 33 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _cell_formula_units_Z 16 _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 282.226 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _cell_measurement_reflns_used '31742' _diffrn_reflns_av_R_equivalents 0.069 _cell_measurement_theta_min '1' _cell_measurement_theta_max '25.02' _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting 'Monoclinic' _chemical_formula_moiety 'C13 H18 Br N2 ' _chemical_formula_sum 'C13 H18 Br N2 ' _chemical_name_systematic ; ? ; _cell_length_a 20.8303(9) _cell_length_b 18.8385(9) _cell_length_c 28.3817(9) _cell_angle_alpha 90.00(1) _cell_angle_beta 152.539(1) _cell_angle_gamma 90.00(1) _cell_volume 5135.9(4) _diffrn_reflns_number 8607 _diffrn_reflns_theta_max 25.02 _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap # Absorption correction _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.781 _exptl_absorpt_correction_T_max 1.380 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_absorpt_coefficient_mu 3.18 _exptl_crystal_F_000 2351 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 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0061 0.0033 'Waasmaier & Kirfel, 1995' 'Br' 'Br' -0.2901 2.4595 'Waasmaier & Kirfel, 1995' _reflns_number_total 8450 _reflns_number_gt 4615 _reflns_threshold_expression 'I> 2.00 sigma(I)' _reflns_d_resolution_low 1.85 _reflns_d_resolution_high 0.65 _reflns_limit_h_max 24 _reflns_limit_h_min 0 _reflns_limit_k_max 21 _reflns_limit_k_min 0 _reflns_limit_l_max 24 _reflns_limit_l_min -27 _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0906 _refine_ls_wR_factor_all 0.066 _refine_ls_R_factor_gt 0.059 _refine_ls_wR_factor_gt 0.056 _refine_ls_wR_factor_ref 0.056 _refine_ls_goodness_of_fit_gt 1.654 _refine_ls_goodness_of_fit_ref 1.654 _refine_ls_goodness_of_fit_all 1.507 _refine_ls_number_parameters 517 _refine_ls_number_reflns 4615 _refine_ls_shift/su_max 0.044 _refine_ls_shift/su_mean 0.009 _refine_ls_structure_factor_coef F^2^ _refine_special_details ; Refinement on F^2^. ; _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1 / ( s^2^(Fo^2^) + 0.03000 * Fo^2^) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _computing_structure_refinement 'maxus(Mackay et al., 1999)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maxus(Mackay et al., 1999)' _atom_sites_solution_hydrogens 'geom, diff' _refine_diff_density_max 1.16 _refine_diff_density_min -0.60 _refine_diff_density_rms 0.09 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Br3 0.953641(10) -0.882357(5) 0.042881(7) 0.15279(7) 1.00 Uij Br4 0.744667(10) -0.583623(6) 0.048678(7) 0.15069(7) 1.00 Uij Br2 0.328312(13) -0.905086(5) -0.368693(9) 0.26707(9) 1.00 Uij Br1 0.786278(13) -0.664900(6) -0.201130(8) 0.19405(8) 1.00 Uij N42 1.12124(7) -0.83148(3) 0.27679(5) 0.0943(4) 1.00 Uij N2 0.46134(6) -0.74282(3) -0.48372(4) 0.0762(4) 1.00 Uij N62 1.14674(6) -0.64103(3) 0.31270(4) 0.0986(4) 1.00 Uij N41 1.23191(7) -0.82018(3) 0.32189(5) 0.1143(4) 1.00 Uij N22 0.23539(7) -0.76163(3) -0.52762(5) 0.1274(4) 1.00 Uij C69 1.01454(7) -0.53401(4) 0.13391(5) 0.0909(5) 1.00 Uij C63 1.03664(7) -0.61967(4) 0.21533(5) 0.03429(18) 1.00 Uiso C23 0.28076(7) -0.77378(4) -0.45423(5) 0.03546(18) 1.00 Uiso N21 0.20015(7) -0.82075(4) -0.57512(5) 0.1579(5) 1.00 Uij N61 1.11958(7) -0.64746(3) 0.34146(5) 0.1245(5) 1.00 Uij C26 0.32253(8) -0.71627(4) -0.39371(5) 0.0941(5) 1.00 Uij N1 0.43021(6) -0.67383(4) -0.50718(5) 0.0992(4) 1.00 Uij C66 1.04259(7) -0.61103(4) 0.16702(5) 0.0866(5) 1.00 Uij C68 1.18621(8) -0.63206(4) 0.24098(5) 0.0955(5) 1.00 Uij C3 0.57919(7) -0.75598(4) -0.38304(5) 0.03761(19) 1.00 Uiso C6 0.63414(7) -0.82945(4) -0.33799(5) 0.0758(5) 1.00 Uij C44 1.05226(7) -0.85608(4) 0.16188(5) 0.03905(19) 1.00 Uiso C74 1.02023(8) -0.52606(4) 0.08453(6) 0.1111(5) 1.00 Uij C43 1.00727(8) -0.85409(4) 0.17775(5) 0.03837(19) 1.00 Uiso C15 0.63398(8) -0.84425(4) -0.28472(6) 0.1065(5) 1.00 Uij C46 0.87315(8) -0.87080(4) 0.11489(5) 0.0982(5) 1.00 Uij C24 0.27716(8) -0.84772(4) -0.45297(6) 0.0493(2) 1.00 Uiso C75 1.16235(9) -0.54799(4) 0.15867(6) 0.1348(6) 1.00 Uij C45 1.19270(8) -0.83538(4) 0.25261(6) 0.0472(2) 1.00 Uiso C13 0.83704(10) -0.92451(5) -0.16114(7) 0.1536(7) 1.00 Uij C67 0.93312(8) -0.66013(4) 0.07186(6) 0.1111(5) 1.00 Uij C70 0.93832(9) -0.65158(4) 0.02183(6) 0.1144(5) 1.00 Uij C73 0.90889(8) -0.57415(4) -0.01007(5) 0.1038(5) 1.00 Uij C7 0.78153(9) -0.83707(4) -0.26106(6) 0.1399(6) 1.00 Uij C25 0.22663(9) -0.87189(5) -0.52797(6) 0.0588(2) 1.00 Uiso C72 1.19169(8) -0.62466(5) 0.19134(6) 0.1081(6) 1.00 Uij C11 0.53825(8) -0.88534(4) -0.42337(6) 0.1209(5) 1.00 Uij C4 0.63063(8) -0.68900(4) -0.33688(6) 0.0490(2) 1.00 Uiso C32 0.22194(9) -0.71281(5) -0.41851(7) 0.1733(7) 1.00 Uij C49 0.83929(9) -0.94934(5) 0.08743(6) 0.1323(6) 1.00 Uij C64 0.93042(7) -0.61070(4) 0.17895(5) 0.0450(2) 1.00 Uiso C65 0.98994(9) -0.62961(5) 0.26034(7) 0.0610(2) 1.00 Uiso C10 0.59869(11) -0.96027(5) -0.37380(7) 0.1874(7) 1.00 Uij C9 0.74505(13) -0.96658(5) -0.29770(9) 0.2457(9) 1.00 Uij C5 0.53199(9) -0.64022(4) -0.41835(7) 0.0577(2) 1.00 Uiso C8 0.83880(9) -0.91279(5) -0.21288(7) 0.1346(6) 1.00 Uij C12 0.59773(11) -0.97293(5) -0.32192(8) 0.2000(7) 1.00 Uij C47 0.75113(10) -0.82974(5) 0.01284(7) 0.1649(7) 1.00 Uij C54 0.69686(11) -0.96756(5) 0.01864(8) 0.1668(7) 1.00 Uij C28 0.46976(10) -0.72869(5) -0.27887(7) 0.1414(7) 1.00 Uij C53 0.58545(10) -0.92546(6) -0.07538(7) 0.1574(7) 1.00 Uij C14 0.69107(10) -0.91768(5) -0.23749(7) 0.1647(7) 1.00 Uij C30 0.35923(17) -0.58480(5) -0.35867(11) 0.2903(10) 1.00 Uij C71 1.08183(10) -0.67331(4) 0.09736(7) 0.1576(7) 1.00 Uij C34 0.26239(11) -0.65527(6) -0.35672(9) 0.2085(9) 1.00 Uij C52 0.61301(10) -0.84828(6) -0.05351(8) 0.1540(7) 1.00 Uij C55 0.71014(11) -0.95127(8) 0.07647(8) 0.1753(9) 1.00 Uij C27 0.32102(13) -0.64405(5) -0.41864(8) 0.3099(9) 1.00 Uij C35 0.40466(17) -0.66910(6) -0.24720(10) 0.2875(10) 1.00 Uij C33 0.25879(12) -0.58463(6) -0.38324(7) 0.1979(8) 1.00 Uij C29 0.50398(16) -0.60016(8) -0.24600(13) 0.3187(13) 1.00 Uij C50 0.73748(14) -0.87256(10) 0.10244(10) 0.2526(13) 1.00 Uij C31 0.50910(12) -0.66940(8) -0.21862(7) 0.1446(8) 1.00 Uij C48 0.87337(11) -0.85277(6) 0.16701(8) 0.1912(8) 1.00 Uij C51 0.62058(14) -0.82881(6) 0.00230(13) 0.2817(10) 1.00 Uij H69A 1.082974 -0.503407 0.192444 0.050000 1.00 Uiso H69B 0.923586 -0.520699 0.085553 0.050000 1.00 Uiso H68A 1.205631 -0.680394 0.262116 0.050000 1.00 Uiso H68B 1.255037 -0.601474 0.299566 0.050000 1.00 Uiso H74 1.002829 -0.477651 0.064410 0.050000 1.00 Uiso H15A 0.540680 -0.840879 -0.333551 0.050000 1.00 Uiso H15B 0.691444 -0.809379 -0.232122 0.050000 1.00 Uiso H75A 1.231755 -0.518228 0.218084 0.050000 1.00 Uiso H75B 1.165719 -0.542671 0.127240 0.050000 1.00 Uiso H45A 1.247187 -0.873878 0.275787 0.050000 1.00 Uiso H45B 1.202553 -0.794693 0.238927 0.050000 1.00 Uiso H13A 0.895219 -0.889575 -0.108459 0.050000 1.00 Uiso H13B 0.872926 -0.971061 -0.131293 0.050000 1.00 Uiso H67A 0.842711 -0.645470 0.023623 0.050000 1.00 Uiso H67B 0.948100 -0.708922 0.089950 0.050000 1.00 Uiso H70 0.870390 -0.681741 -0.037072 0.050000 1.00 Uiso H73A 0.908778 -0.568562 -0.043761 0.050000 1.00 Uiso H73B 0.819200 -0.561431 -0.056168 0.050000 1.00 Uiso H7A 0.840403 -0.802672 -0.207684 0.050000 1.00 Uiso H7B 0.780992 -0.828875 -0.294794 0.050000 1.00 Uiso H25A 0.294332 -0.903297 -0.497472 0.050000 1.00 Uiso H25B 0.141939 -0.897502 -0.577321 0.050000 1.00 Uiso H72 1.282001 -0.638035 0.238699 0.050000 1.00 Uiso H11A 0.533712 -0.877838 -0.459749 0.050000 1.00 Uiso H11B 0.446369 -0.882256 -0.470062 0.050000 1.00 Uiso H32A 0.223124 -0.757421 -0.401388 0.050000 1.00 Uiso H32B 0.129797 -0.703704 -0.490138 0.050000 1.00 Uiso H49A 0.912365 -0.977475 0.148579 0.050000 1.00 Uiso H49B 0.830360 -0.960539 0.048756 0.050000 1.00 Uiso H65A 0.981267 -0.589627 0.275463 0.050000 1.00 Uiso H65B 0.938152 -0.668919 0.239105 0.050000 1.00 Uiso H10 0.542624 -0.995711 -0.425505 0.050000 1.00 Uiso H9A 0.742752 -0.957026 -0.332409 0.050000 1.00 Uiso H9B 0.781423 -1.013383 -0.268748 0.050000 1.00 Uiso H5A 0.493664 -0.614169 -0.417292 0.050000 1.00 Uiso H5B 0.578861 -0.608099 -0.408748 0.050000 1.00 Uiso H8 0.931923 -0.917249 -0.164160 0.050000 1.00 Uiso H12A 0.628610 -1.020202 -0.294720 0.050000 1.00 Uiso H12B 0.504662 -0.966480 -0.370974 0.050000 1.00 Uiso H47A 0.745887 -0.842619 -0.023256 0.050000 1.00 Uiso H47B 0.768410 -0.779702 0.026755 0.050000 1.00 Uiso H54 0.676279 -1.017269 0.002535 0.050000 1.00 Uiso H28A 0.534618 -0.727811 -0.262358 0.050000 1.00 Uiso H28B 0.474760 -0.773848 -0.260025 0.050000 1.00 Uiso H53A 0.497650 -0.936825 -0.118262 0.050000 1.00 Uiso H53B 0.582421 -0.937177 -0.110256 0.050000 1.00 Uiso H14 0.693107 -0.925641 -0.202763 0.050000 1.00 Uiso H30 0.356188 -0.539735 -0.376418 0.050000 1.00 Uiso H71A 1.086121 -0.669046 0.066476 0.050000 1.00 Uiso H71B 1.100204 -0.721582 0.118223 0.050000 1.00 Uiso H34 0.199488 -0.654196 -0.371407 0.050000 1.00 Uiso H52 0.539048 -0.821486 -0.115871 0.050000 1.00 Uiso H55A 0.786057 -0.977314 0.139518 0.050000 1.00 Uiso H55B 0.625172 -0.963707 0.036909 0.050000 1.00 Uiso H27A 0.229135 -0.635688 -0.490571 0.050000 1.00 Uiso H27B 0.386512 -0.644352 -0.401538 0.050000 1.00 Uiso H35A 0.404181 -0.714631 -0.232318 0.050000 1.00 Uiso H35B 0.429327 -0.633134 -0.208669 0.050000 1.00 Uiso H33A 0.166670 -0.576651 -0.455244 0.050000 1.00 Uiso H33B 0.282662 -0.547430 -0.346031 0.050000 1.00 Uiso H29A 0.532246 -0.562753 -0.206707 0.050000 1.00 Uiso H29B 0.565709 -0.601754 -0.232379 0.050000 1.00 Uiso H50 0.741662 -0.860773 0.138039 0.050000 1.00 Uiso H31 0.600610 -0.677448 -0.146519 0.050000 1.00 Uiso H48A 0.892594 -0.803139 0.183600 0.050000 1.00 Uiso H48B 0.945458 -0.880221 0.228690 0.050000 1.00 Uiso H51A 0.534758 -0.842083 -0.038655 0.050000 1.00 Uiso H51B 0.635947 -0.778842 0.016455 0.050000 1.00 Uiso H42 1.113215 -0.833222 0.309077 0.050000 1.00 Uiso H2 0.392286 -0.782548 -0.542388 0.050000 1.00 Uiso H22 0.200625 -0.715653 -0.563645 0.050000 1.00 Uiso H62 1.235831 -0.664333 0.361603 0.050000 1.00 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br3 0.07195(7) 0.09289(8) 0.05845(6) -.00908(6) 0.05936(6) -.01530(5) Br4 0.05213(6) 0.11562(9) 0.06467(6) 0.02565(6) 0.05100(6) 0.02696(6) Br2 0.15495(11) 0.04740(6) 0.11671(9) -.00805(7) 0.12551(10) 0.00238(6) Br1 0.11337(10) 0.06070(7) 0.05200(7) -.01745(7) 0.06140(8) -.01895(5) N42 0.0420(4) 0.0554(5) 0.0376(4) -.0107(4) 0.0352(4) -.0110(3) N2 0.0329(4) 0.0406(4) 0.0290(4) 0.0000(3) 0.0247(4) 0.0029(3) N62 0.0458(4) 0.0451(4) 0.0425(4) 0.0144(3) 0.0394(4) 0.0176(3) N41 0.0531(5) 0.0488(5) 0.0480(4) -.0073(4) 0.0434(4) -.0042(3) N22 0.0710(5) 0.0341(4) 0.0520(4) -.0023(4) 0.0552(5) -.0015(3) C69 0.0440(5) 0.0355(5) 0.0384(5) 0.0028(4) 0.0359(5) 0.0019(4) N21 0.0890(6) 0.0501(5) 0.0603(5) -.0188(4) 0.0668(5) -.0185(4) N61 0.0601(5) 0.0689(5) 0.0504(4) 0.0077(4) 0.0516(5) 0.0104(3) C26 0.0467(5) 0.0339(5) 0.0419(5) -.0075(4) 0.0403(5) -.0052(4) N1 0.0411(4) 0.0502(5) 0.0400(4) 0.0051(4) 0.0321(4) 0.0099(3) C66 0.0410(5) 0.0282(5) 0.0410(5) 0.0065(4) 0.0369(5) 0.0076(4) C68 0.0455(5) 0.0391(5) 0.0412(5) 0.0073(4) 0.0384(5) 0.0125(4) C6 0.0311(5) 0.0407(5) 0.0335(5) 0.0016(4) 0.0280(4) 0.0026(4) C74 0.0545(6) 0.0298(5) 0.0527(5) 0.0026(4) 0.0480(5) 0.0081(4) C15 0.0485(5) 0.0536(6) 0.0453(5) -.0054(4) 0.0419(5) -.0037(4) C46 0.0482(5) 0.0353(5) 0.0435(5) -.0025(4) 0.0412(5) -.0041(4) C75 0.0619(6) 0.0500(6) 0.0639(6) -.0055(5) 0.0568(6) 0.0024(4) C13 0.0771(7) 0.0525(6) 0.0626(7) 0.0210(5) 0.0596(7) 0.0247(5) C67 0.0535(6) 0.0393(5) 0.0506(5) -.0052(4) 0.0467(5) -.0013(4) C70 0.0577(6) 0.0437(5) 0.0492(5) -.0020(5) 0.0487(6) -.0023(4) C73 0.0482(5) 0.0571(6) 0.0409(5) 0.0011(5) 0.0395(5) 0.0052(4) C7 0.0678(6) 0.0531(6) 0.0641(6) 0.0069(5) 0.0608(6) 0.0105(5) C72 0.0393(5) 0.0623(6) 0.0525(5) 0.0206(5) 0.0407(5) 0.0235(5) C11 0.0633(6) 0.0442(6) 0.0488(5) -.0066(5) 0.0500(5) -.0041(4) C32 0.0768(7) 0.0612(7) 0.0870(7) -.0094(5) 0.0747(7) -.0141(5) C49 0.0550(6) 0.0494(6) 0.0602(6) -.0067(5) 0.0466(6) -.0017(5) C10 0.1082(9) 0.0377(6) 0.0776(7) -.0141(6) 0.0837(8) -.0106(5) C9 0.1350(11) 0.0483(7) 0.1147(9) 0.0421(7) 0.1163(10) 0.0413(6) C8 0.0551(6) 0.0640(7) 0.0605(6) 0.0234(5) 0.0489(6) 0.0218(5) C12 0.1018(9) 0.0485(6) 0.0906(8) -.0109(6) 0.0846(8) 0.0041(5) C47 0.0677(7) 0.0660(7) 0.0829(7) 0.0136(5) 0.0671(7) 0.0181(6) C54 0.0761(8) 0.0493(6) 0.0757(8) -.0077(6) 0.0629(8) -.0001(6) C28 0.0582(7) 0.0825(8) 0.0493(7) 0.0060(6) 0.0392(6) -.0154(5) C53 0.0602(7) 0.0833(8) 0.0735(7) -.0205(6) 0.0575(7) -.0228(6) C14 0.0858(8) 0.0633(7) 0.0688(7) 0.0028(6) 0.0710(7) 0.0117(6) C30 0.1777(13) 0.0385(6) 0.1225(10) -.0324(8) 0.1387(12) -.0215(7) C71 0.0818(7) 0.0551(6) 0.0695(7) 0.0089(5) 0.0705(7) 0.0054(5) C34 0.0951(9) 0.0927(9) 0.0994(9) 0.0050(7) 0.0915(9) -.0099(7) C52 0.0462(6) 0.1003(10) 0.0740(8) 0.0215(6) 0.0487(7) 0.0359(7) C55 0.0698(8) 0.1360(12) 0.0576(8) -.0219(8) 0.0501(8) 0.0061(7) C27 0.1943(12) 0.0507(7) 0.1285(9) -.0309(7) 0.1531(10) -.0240(6) C35 0.1825(14) 0.0673(8) 0.1016(10) 0.0336(9) 0.1296(11) 0.0187(7) C33 0.1102(10) 0.0636(8) 0.0672(7) 0.0323(7) 0.0728(8) 0.0080(6) C29 0.1263(12) 0.1074(11) 0.1737(14) -.0826(10) 0.1346(13) -.1108(11) C50 0.0964(10) 0.1984(16) 0.1092(11) -.0509(11) 0.0977(10) -.0648(11) C31 0.0572(8) 0.1130(11) 0.0347(6) 0.0221(8) 0.0267(7) -.0124(6) C48 0.0765(8) 0.1467(10) 0.0745(7) -.0417(7) 0.0678(7) -.0495(7) C51 0.0975(10) 0.0630(8) 0.1799(14) -.0196(7) 0.1251(11) -.0317(9) _geom_special_details ; All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N42 N41 1.3271(9) . . ? N42 C43 1.3696(8) . . ? N2 N1 1.3365(7) . . ? N2 C3 1.3432(8) . . ? N62 C63 1.3457(8) . . ? N62 N61 1.3494(7) . . ? N41 C45 1.3288(8) . . ? N22 C23 1.3380(8) . . ? N22 N21 1.3565(7) . . ? C69 C66 1.5346(9) . . ? C69 C74 1.5147(9) . . ? C63 C66 1.4910(9) . . ? C63 C64 1.3914(9) . . ? C23 C26 1.4929(9) . . ? C23 C24 1.3970(9) . . ? N21 C25 1.3088(9) . . ? N61 C65 1.2933(9) . . ? C26 C32 1.5077(10) . . ? C26 C28 1.5311(11) . . ? C26 C27 1.5206(10) . . ? N1 C5 1.3289(9) . . ? C66 C68 1.5389(9) . . ? C66 C67 1.5557(10) . . ? C68 C72 1.5177(10) . . ? C3 C6 1.5044(9) . . ? C3 C4 1.4018(9) . . ? C6 C15 1.5402(9) . . ? C6 C7 1.5224(10) . . ? C6 C11 1.5429(9) . . ? C44 C43 1.3535(8) . . ? C44 C45 1.4044(10) . . ? C74 C75 1.5192(10) . . ? C74 C73 1.5355(10) . . ? C43 C46 1.4971(9) . . ? C15 C14 1.5150(10) . . ? C46 C49 1.5225(11) . . ? C46 C47 1.5437(10) . . ? C46 C48 1.5138(11) . . ? C24 C25 1.3677(9) . . ? C75 C72 1.5208(10) . . ? C13 C8 1.5173(11) . . ? C13 C14 1.5048(12) . . ? C67 C70 1.5254(9) . . ? C70 C73 1.5290(10) . . ? C70 C71 1.5254(10) . . ? C7 C8 1.5598(11) . . ? C72 C71 1.5359(11) . . ? C11 C10 1.5534(12) . . ? C4 C5 1.4075(10) . . ? C32 C34 1.5289(12) . . ? C49 C54 1.5660(12) . . ? C64 C65 1.3847(9) . . ? C10 C9 1.5126(13) . . ? C10 C12 1.5090(12) . . ? C9 C8 1.5141(13) . . ? C12 C14 1.5287(12) . . ? C47 C52 1.5267(12) . . ? C54 C53 1.4647(12) . . ? C54 C55 1.4346(14) . . ? C28 C31 1.5349(13) . . ? C53 C52 1.4820(13) . . ? C30 C27 1.5401(12) . . ? C30 C33 1.5081(15) . . ? C30 C29 1.513(2) . . ? C34 C35 1.4712(14) . . ? C34 C33 1.4976(14) . . ? C52 C51 1.4919(15) . . ? C55 C50 1.523(2) . . ? C35 C31 1.503(2) . . ? C29 C31 1.473(2) . . ? C50 C48 1.5179(14) . . ? C50 C51 1.551(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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N41 N42 C43 113.18(6) . . . ? N1 N2 C3 113.73(6) . . . ? C63 N62 N61 113.82(5) . . . ? N42 N41 C45 106.11(7) . . . ? C23 N22 N21 114.74(6) . . . ? C66 C69 C74 111.12(6) . . . ? N62 C63 C66 122.70(6) . . . ? N62 C63 C64 104.50(6) . . . ? C66 C63 C64 132.79(6) . . . ? N22 C23 C26 123.53(6) . . . ? N22 C23 C24 103.33(6) . . . ? C26 C23 C24 133.13(6) . . . ? N22 N21 C25 102.88(6) . . . ? N62 N61 C65 103.51(6) . . . ? C23 C26 C32 110.15(6) . . . ? C23 C26 C28 111.10(6) . . . ? C23 C26 C27 111.32(6) . . . ? C32 C26 C28 109.22(7) . . . ? C32 C26 C27 107.32(7) . . . ? C28 C26 C27 107.62(7) . . . ? N2 N1 C5 105.42(6) . . . ? C69 C66 C63 111.67(6) . . . ? C69 C66 C68 107.56(6) . . . ? C69 C66 C67 108.89(6) . . . ? C63 C66 C68 111.38(6) . . . ? C63 C66 C67 109.98(6) . . . ? C68 C66 C67 107.20(6) . . . ? C66 C68 C72 111.50(6) . . . ? N2 C3 C6 123.64(6) . . . ? N2 C3 C4 105.09(6) . . . ? C6 C3 C4 131.27(7) . . . ? C3 C6 C15 109.76(6) . . . ? C3 C6 C7 110.54(6) . . . ? C3 C6 C11 110.15(6) . . . ? C15 C6 C7 109.47(6) . . . ? C15 C6 C11 106.91(6) . . . ? C7 C6 C11 109.93(6) . . . ? C43 C44 C45 108.25(6) . . . ? C69 C74 C75 110.35(6) . . . ? C69 C74 C73 108.82(6) . . . ? C75 C74 C73 108.96(6) . . . ? N42 C43 C44 103.91(6) . . . ? N42 C43 C46 120.97(6) . . . ? C44 C43 C46 135.11(7) . . . ? C6 C15 C14 110.48(6) . . . ? C43 C46 C49 109.96(7) . . . ? C43 C46 C47 110.82(6) . . . ? C43 C46 C48 113.82(7) . . . ? C49 C46 C47 106.43(6) . . . ? C49 C46 C48 108.45(7) . . . ? C47 C46 C48 107.05(7) . . . ? C23 C24 C25 106.06(7) . . . ? C74 C75 C72 109.74(6) . . . ? N41 C45 C44 108.55(7) . . . ? C8 C13 C14 110.31(7) . . . ? C66 C67 C70 110.36(6) . . . ? C67 C70 C73 109.23(6) . . . ? C67 C70 C71 109.44(6) . . . ? C73 C70 C71 110.14(7) . . . ? C74 C73 C70 109.73(6) . . . ? C6 C7 C8 110.11(7) . . . ? N21 C25 C24 112.97(8) . . . ? C68 C72 C75 109.44(6) . . . ? C68 C72 C71 109.50(7) . . . ? C75 C72 C71 109.54(6) . . . ? C6 C11 C10 108.55(6) . . . ? C3 C4 C5 105.15(7) . . . ? C26 C32 C34 111.84(7) . . . ? C46 C49 C54 110.85(7) . . . ? C63 C64 C65 104.51(7) . . . ? N61 C65 C64 113.65(7) . . . ? C11 C10 C9 110.58(7) . . . ? C11 C10 C12 108.99(8) . . . ? C9 C10 C12 110.44(8) . . . ? C10 C9 C8 109.85(8) . . . ? N1 C5 C4 110.58(7) . . . ? C13 C8 C7 108.96(7) . . . ? C13 C8 C9 109.67(8) . . . ? C7 C8 C9 108.30(7) . . . ? C10 C12 C14 108.80(7) . . . ? C46 C47 C52 111.29(7) . . . ? C49 C54 C53 109.81(8) . . . ? C49 C54 C55 107.33(9) . . . ? C53 C54 C55 110.72(9) . . . ? C26 C28 C31 109.95(7) . . . ? C54 C53 C52 111.68(8) . . . ? C15 C14 C13 110.42(7) . . . ? C15 C14 C12 109.06(7) . . . ? C13 C14 C12 109.48(8) . . . ? C27 C30 C33 110.24(10) . . . ? C27 C30 C29 107.67(11) . . . ? C33 C30 C29 108.84(9) . . . ? C70 C71 C72 108.81(6) . . . ? C32 C34 C35 108.94(9) . . . ? C32 C34 C33 108.82(8) . . . ? C35 C34 C33 109.14(9) . . . ? C47 C52 C53 110.29(9) . . . ? C47 C52 C51 109.03(9) . . . ? C53 C52 C51 108.81(9) . . . ? C54 C55 C50 111.81(9) . . . ? C26 C27 C30 110.92(7) . . . ? C34 C35 C31 112.23(8) . . . ? C30 C33 C34 109.60(8) . . . ? C30 C29 C31 111.10(9) . . . ? C55 C50 C48 108.61(11) . . . ? C55 C50 C51 109.00(9) . . . ? C48 C50 C51 107.20(11) . . . ? C28 C31 C35 108.37(11) . . . ? C28 C31 C29 109.85(11) . . . ? C35 C31 C29 108.62(10) . . . ? C46 C48 C50 112.32(8) . . . ? C52 C51 C50 109.26(8) . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag N42 N21 2.8546(8) 1_555 1_656 ? N2 N41 2.9343(8) 1_555 1_454 ? N2 H62 2.6319(5) 1_555 1_454 ? N62 N1 2.7951(8) 1_555 1_656 ? N41 H2 1.9141(6) 1_555 1_656 ? N22 N61 2.8885(8) 1_555 1_454 ? N21 C48 3.4427(12) 1_555 1_454 ? N21 H42 1.8907(6) 1_555 1_454 ? N61 H22 1.9195(6) 1_555 1_656 ? N1 H62 1.8803(6) 1_555 1_454 ? C44 C9 3.8681(11) 1_555 2_735 ? C44 H9B 2.9327(6) 1_555 2_735 ? C74 C73 3.9683(10) 1_555 2_745 ? C74 H73A 3.1208(7) 1_555 2_745 ? C75 C73 3.7651(10) 1_555 2_745 ? C75 H73A 3.0127(8) 1_555 2_745 ? C45 C9 3.7802(11) 1_555 2_735 ? C45 H9B 2.8597(8) 1_555 2_735 ? C45 H2 3.0332(7) 1_555 1_656 ? C13 H33A 3.1762(10) 1_555 4_646 ? C73 H75B 3.0241(7) 1_555 2_745 ? C7 C65 3.8640(12) 1_555 4_545 ? C25 H42 2.8479(8) 1_555 1_454 ? C72 C53 3.9533(13) 1_555 4_646 ? C72 H53A 3.1688(9) 1_555 4_646 ? C4 H50 3.1075(7) 1_555 4_545 ? C32 C71 3.9565(12) 1_555 4_445 ? C49 C65 3.9467(12) 1_555 3_745 ? C65 C8 3.9208(13) 1_555 4_546 ? C65 H7B 3.1492(9) 1_555 4_546 ? C65 H49A 3.1145(9) 1_555 3_755 ? C65 H22 2.8171(8) 1_555 1_656 ? C9 H45A 3.0440(9) 1_555 2_735 ? C5 C50 3.7744(13) 1_555 4_545 ? C5 H50 3.0385(8) 1_555 4_545 ? C5 H62 2.9823(8) 1_555 1_454 ? C12 H33B 3.1342(9) 1_555 3_644 ? C53 H72 3.1681(10) 1_555 4_445 ? C14 H33B 3.0968(8) 1_555 3_644 ? C71 H32A 3.1906(8) 1_555 4_646 ? C52 H72 3.1976(9) 1_555 4_445 ? C50 H5B 3.0477(10) 1_555 4_546 ? H45A H9B 2.1665 1_555 2_735 ? H49A H65A 2.3544 1_555 3_745 ? H5B H50 2.3697 1_555 4_545 ? N42 N21 2.8546(8) 1_555 1_656 ? N2 N41 2.9343(8) 1_555 1_454 ? N2 H62 2.6319(5) 1_555 1_454 ? N62 N1 2.7951(8) 1_555 1_656 ? N41 H2 1.9141(6) 1_555 1_656 ? N22 N61 2.8885(8) 1_555 1_454 ? N21 C48 3.4427(12) 1_555 1_454 ? N21 H42 1.8907(6) 1_555 1_454 ? N61 H22 1.9195(6) 1_555 1_656 ? N1 H62 1.8803(6) 1_555 1_454 ? C44 C9 3.8681(11) 1_555 2_735 ? C44 H9B 2.9327(6) 1_555 2_735 ? C74 C73 3.9683(10) 1_555 2_745 ? C74 H73A 3.1208(7) 1_555 2_745 ? C75 C73 3.7651(10) 1_555 2_745 ? C75 H73A 3.0127(8) 1_555 2_745 ? C45 C9 3.7802(11) 1_555 2_735 ? C45 H9B 2.8597(8) 1_555 2_735 ? C45 H2 3.0332(7) 1_555 1_656 ? C13 H33A 3.1762(10) 1_555 4_646 ? C73 H75B 3.0241(7) 1_555 2_745 ? C7 C65 3.8640(12) 1_555 4_545 ? C25 H42 2.8479(8) 1_555 1_454 ? C72 C53 3.9533(13) 1_555 4_646 ? C72 H53A 3.1688(9) 1_555 4_646 ? C4 H50 3.1075(7) 1_555 4_545 ? C32 C71 3.9565(12) 1_555 4_445 ? C49 C65 3.9467(12) 1_555 3_745 ? C65 C8 3.9208(13) 1_555 4_546 ? C65 H7B 3.1492(9) 1_555 4_546 ? C65 H49A 3.1145(9) 1_555 3_755 ? C65 H22 2.8171(8) 1_555 1_656 ? C9 H45A 3.0440(9) 1_555 2_735 ? C5 C50 3.7744(13) 1_555 4_545 ? C5 H50 3.0385(8) 1_555 4_545 ? C5 H62 2.9823(8) 1_555 1_454 ? C12 H33B 3.1342(9) 1_555 3_644 ? C53 H72 3.1681(10) 1_555 4_445 ? C14 H33B 3.0968(8) 1_555 3_644 ? C71 H32A 3.1906(8) 1_555 4_646 ? C52 H72 3.1976(9) 1_555 4_445 ? C50 H5B 3.0477(10) 1_555 4_546 ? H45A H9B 2.1665 1_555 2_735 ? H49A H65A 2.3544 1_555 3_745 ? H5B H50 2.3697 1_555 4_545 ? #=================================================== _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Waasmaier, D. & Kirfel, A. (1995). Acta Cryst. A51, 416-431. ;