Supplementary Material (ESI) for Photochemical & Photobiological Sciences This journal is © The Royal Society of Chemistry and Owner Societies 2005 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_Cambridge 0171 _publ_contact_author_name 'Paul Margaretha' _publ_contact_author_address ; Inst. F. Organische Chemie Universitaet Hamburg M.L. King Platz 6 Hamburg D-20146 GERMANY ; _publ_contact_author_email PAUL.MARGARETHA@CHEMIE.UNI-HAMBURG.DE _publ_section_title ; Photocycloaddition of Cyclohex-2-enones to Alkylidenemalononitriles (1,1-Dicyanoethylenes) ; loop_ _publ_author_name 'Paul Margaretha' 'Britta Lohmeyer' data_b20-p5 _database_code_depnum_ccdc_archive 'CCDC 266744' _audit_creation_method SHELXL-97 _chemical_name_systematic ; exo-3,5,5-trimethyl-1-(2,2-trimethylpropanoyl)-7-oxo-3,3a,4,5,6,7- hexahydro-2H-indene-2,2-dicarbonitrile ; _chemical_name_common ; exo-3,5,5-trimethyl-1-(2,2-trimethylpropanoyl)-7-oxo- 3,3a,4,5,6,7-hexahydro-2H-indene-2,2-dicarbonitrile ; _chemical_melting_point '159 - 160' _chemical_formula_moiety 'C19 H24 N2 O2' _chemical_formula_sum 'C19 H24 N2 O2' _chemical_formula_weight 312.40 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 'P 21/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 17.287(7) _cell_length_b 12.249(7) _cell_length_c 17.804(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.09(4) _cell_angle_gamma 90.00 _cell_volume 3672(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.61 _cell_measurement_theta_max 17.48 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.074 _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 'Hilger & Watts (Y290)' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6223 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 22.50 _reflns_number_total 4804 _reflns_number_gt 2899 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Program system Y290 (Kopf, 2000)' _computing_cell_refinement 'Program system Y290 (Kopf, 2000)' _computing_data_reduction 'Program system Y290 (Kopf, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0423P)^2^+2.5997P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4804 _refine_ls_number_parameters 427 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1542 _refine_ls_wR_factor_gt 0.1329 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 O5 O 0.13147(18) 0.1670(2) 0.49921(15) 0.0701(9) Uani 1 1 d . . . O71 O 0.22734(18) -0.0439(3) 0.41280(18) 0.0747(9) Uani 1 1 d . . . N81 N 0.3420(3) 0.1258(4) 0.3051(3) 0.1083(17) Uani 1 1 d . . . N82 N 0.1453(3) -0.0392(4) 0.1708(2) 0.1122(17) Uani 1 1 d . . . C1 C 0.1481(2) 0.2898(3) 0.3156(2) 0.0481(10) Uani 1 1 d . . . H1 H 0.1999 0.3250 0.3339 0.058 Uiso 1 1 calc R . . C2 C 0.0832(2) 0.3753(3) 0.3102(2) 0.0558(11) Uani 1 1 d . . . H2A H 0.0326 0.3435 0.2850 0.067 Uiso 1 1 calc R . . H2B H 0.0938 0.4355 0.2786 0.067 Uiso 1 1 calc R . . C3 C 0.0772(2) 0.4194(3) 0.3894(2) 0.0582(11) Uani 1 1 d . . . C4 C 0.0606(3) 0.3236(3) 0.4392(2) 0.0622(12) Uani 1 1 d . . . H4A H 0.0649 0.3502 0.4913 0.075 Uiso 1 1 calc R . . H4B H 0.0061 0.3003 0.4198 0.075 Uiso 1 1 calc R . . C5 C 0.1129(2) 0.2260(3) 0.4431(2) 0.0495(10) Uani 1 1 d . . . C6 C 0.1397(2) 0.2002(3) 0.37051(19) 0.0443(10) Uani 1 1 d . . . C7 C 0.1564(2) 0.1013(3) 0.3478(2) 0.0458(10) Uani 1 1 d . . . C8 C 0.1870(2) 0.1143(3) 0.2733(2) 0.0532(11) Uani 1 1 d . . . C9 C 0.1490(2) 0.2262(3) 0.2413(2) 0.0549(11) Uani 1 1 d . . . H9 H 0.0937 0.2118 0.2153 0.066 Uiso 1 1 calc R . . C31 C 0.0080(3) 0.5006(4) 0.3786(3) 0.0824(15) Uani 1 1 d . . . H31A H -0.0402 0.4650 0.3529 0.124 Uiso 1 1 calc R . . H31B H 0.0183 0.5612 0.3481 0.124 Uiso 1 1 calc R . . H31C H 0.0027 0.5264 0.4281 0.124 Uiso 1 1 calc R . . C32 C 0.1536(3) 0.4778(4) 0.4291(3) 0.0859(16) Uani 1 1 d . . . H32A H 0.1477 0.5069 0.4776 0.129 Uiso 1 1 calc R . . H32B H 0.1641 0.5362 0.3969 0.129 Uiso 1 1 calc R . . H32C H 0.1970 0.4269 0.4379 0.129 Uiso 1 1 calc R . . C71 C 0.1614(3) -0.0078(3) 0.3878(2) 0.0510(10) Uani 1 1 d . . . C72 C 0.0872(3) -0.0726(4) 0.3907(2) 0.0624(12) Uani 1 1 d . . . C73 C 0.0118(3) -0.0064(5) 0.3712(4) 0.136(3) Uani 1 1 d . . . H73A H 0.0172 0.0566 0.4041 0.203 Uiso 1 1 calc R . . H73B H -0.0318 -0.0501 0.3789 0.203 Uiso 1 1 calc R . . H73C H 0.0021 0.0165 0.3184 0.203 Uiso 1 1 calc R . . C74 C 0.0944(4) -0.1168(6) 0.4719(4) 0.144(3) Uani 1 1 d . . . H74A H 0.1365 -0.1695 0.4833 0.216 Uiso 1 1 calc R . . H74B H 0.0453 -0.1509 0.4755 0.216 Uiso 1 1 calc R . . H74C H 0.1058 -0.0578 0.5083 0.216 Uiso 1 1 calc R . . C75 C 0.0824(5) -0.1663(6) 0.3360(5) 0.196(5) Uani 1 1 d . . . H75A H 0.0666 -0.1401 0.2840 0.294 Uiso 1 1 calc R . . H75B H 0.0441 -0.2183 0.3454 0.294 Uiso 1 1 calc R . . H75C H 0.1335 -0.2008 0.3435 0.294 Uiso 1 1 calc R . . C81 C 0.2749(3) 0.1194(4) 0.2921(3) 0.0704(13) Uani 1 1 d . . . C82 C 0.1636(3) 0.0258(4) 0.2166(3) 0.0734(14) Uani 1 1 d . . . C91 C 0.1880(3) 0.2826(4) 0.1837(2) 0.0808(15) Uani 1 1 d . . . H91A H 0.1599 0.3488 0.1663 0.121 Uiso 1 1 calc R . . H91B H 0.1867 0.2353 0.1405 0.121 Uiso 1 1 calc R . . H91C H 0.2421 0.2996 0.2078 0.121 Uiso 1 1 calc R . . O55 O 0.49822(18) 0.0970(3) 0.60482(17) 0.0713(9) Uani 1 1 d . . . O571 O 0.44286(19) 0.3424(3) 0.69418(17) 0.0808(10) Uani 1 1 d . . . N581 N 0.3545(2) 0.2288(4) 0.8419(2) 0.0936(14) Uani 1 1 d . . . N582 N 0.1895(2) 0.3579(3) 0.6464(2) 0.0812(13) Uani 1 1 d . . . C51 C 0.3212(2) 0.0149(3) 0.6723(2) 0.0450(10) Uani 1 1 d . . . H51 H 0.3477 -0.0087 0.7243 0.054 Uiso 1 1 calc R . . C52 C 0.3010(2) -0.0856(3) 0.6216(2) 0.0532(11) Uani 1 1 d . . . H52A H 0.2653 -0.0645 0.5735 0.064 Uiso 1 1 calc R . . H52B H 0.2731 -0.1374 0.6471 0.064 Uiso 1 1 calc R . . C53 C 0.3734(2) -0.1417(3) 0.6036(2) 0.0550(11) Uani 1 1 d . . . C54 C 0.4179(3) -0.0609(3) 0.5624(2) 0.0653(12) Uani 1 1 d . . . H54A H 0.4668 -0.0947 0.5564 0.078 Uiso 1 1 calc R . . H54B H 0.3856 -0.0466 0.5112 0.078 Uiso 1 1 calc R . . C55 C 0.4374(3) 0.0460(3) 0.6038(2) 0.0544(11) Uani 1 1 d . . . C56 C 0.3759(2) 0.0895(3) 0.6423(2) 0.0433(9) Uani 1 1 d . . . C57 C 0.3608(2) 0.1947(3) 0.6517(2) 0.0460(10) Uani 1 1 d . . . C58 C 0.2933(2) 0.2033(3) 0.6940(2) 0.0450(10) Uani 1 1 d . . . C59 C 0.2520(2) 0.0893(3) 0.6779(2) 0.0473(10) Uani 1 1 d . . . H59 H 0.2164 0.0926 0.6266 0.057 Uiso 1 1 calc R . . C531 C 0.3441(3) -0.2386(4) 0.5489(3) 0.0857(16) Uani 1 1 d . . . H53A H 0.3146 -0.2883 0.5734 0.129 Uiso 1 1 calc R . . H53B H 0.3889 -0.2758 0.5374 0.129 Uiso 1 1 calc R . . H53C H 0.3105 -0.2119 0.5020 0.129 Uiso 1 1 calc R . . C532 C 0.4299(3) -0.1837(4) 0.6766(3) 0.0809(15) Uani 1 1 d . . . H53D H 0.4515 -0.1230 0.7088 0.121 Uiso 1 1 calc R . . H53E H 0.4723 -0.2239 0.6628 0.121 Uiso 1 1 calc R . . H53F H 0.4015 -0.2306 0.7042 0.121 Uiso 1 1 calc R . . C571 C 0.4055(2) 0.2950(3) 0.6373(2) 0.0517(10) Uani 1 1 d . . . C572 C 0.4004(2) 0.3402(3) 0.5562(2) 0.0557(11) Uani 1 1 d . . . C573 C 0.3485(3) 0.2702(4) 0.4943(2) 0.0826(15) Uani 1 1 d . . . H57A H 0.3733 0.2004 0.4925 0.124 Uiso 1 1 calc R . . H57B H 0.3421 0.3056 0.4452 0.124 Uiso 1 1 calc R . . H57C H 0.2975 0.2602 0.5061 0.124 Uiso 1 1 calc R . . C574 C 0.4835(3) 0.3511(4) 0.5417(3) 0.0890(16) Uani 1 1 d . . . H57D H 0.5143 0.3999 0.5790 0.134 Uiso 1 1 calc R . . H57E H 0.4801 0.3796 0.4908 0.134 Uiso 1 1 calc R . . H57F H 0.5086 0.2808 0.5461 0.134 Uiso 1 1 calc R . . C575 C 0.3638(3) 0.4553(4) 0.5556(3) 0.0873(16) Uani 1 1 d . . . H57G H 0.3128 0.4501 0.5683 0.131 Uiso 1 1 calc R . . H57H H 0.3576 0.4869 0.5052 0.131 Uiso 1 1 calc R . . H57I H 0.3982 0.5005 0.5929 0.131 Uiso 1 1 calc R . . C581 C 0.3278(2) 0.2196(4) 0.7781(2) 0.0604(12) Uani 1 1 d . . . C582 C 0.2357(3) 0.2925(3) 0.6674(2) 0.0534(11) Uani 1 1 d . . . C591 C 0.2021(3) 0.0561(4) 0.7345(3) 0.0723(13) Uani 1 1 d . . . H59A H 0.1769 -0.0127 0.7191 0.108 Uiso 1 1 calc R . . H59B H 0.1622 0.1106 0.7348 0.108 Uiso 1 1 calc R . . H59C H 0.2356 0.0496 0.7853 0.108 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 O5 0.102(2) 0.070(2) 0.0379(16) 0.0064(16) 0.0148(15) 0.0150(18) O71 0.061(2) 0.074(2) 0.091(2) 0.0222(18) 0.0208(17) 0.0182(18) N81 0.068(3) 0.132(4) 0.132(4) 0.012(3) 0.038(3) 0.010(3) N82 0.168(5) 0.100(4) 0.064(3) -0.025(3) 0.016(3) 0.017(3) C1 0.051(2) 0.048(2) 0.045(2) 0.0032(19) 0.0106(18) -0.002(2) C2 0.065(3) 0.052(3) 0.047(2) 0.006(2) 0.006(2) 0.001(2) C3 0.065(3) 0.052(3) 0.054(3) -0.008(2) 0.005(2) 0.011(2) C4 0.072(3) 0.068(3) 0.047(2) -0.007(2) 0.014(2) 0.019(2) C5 0.056(3) 0.050(2) 0.040(2) -0.007(2) 0.0067(19) 0.004(2) C6 0.046(2) 0.051(3) 0.033(2) -0.0019(19) 0.0047(17) 0.000(2) C7 0.046(2) 0.051(3) 0.039(2) 0.0001(19) 0.0076(18) -0.001(2) C8 0.061(3) 0.060(3) 0.041(2) -0.004(2) 0.018(2) 0.006(2) C9 0.062(3) 0.063(3) 0.042(2) 0.006(2) 0.017(2) -0.001(2) C31 0.094(4) 0.071(3) 0.079(3) -0.005(3) 0.012(3) 0.027(3) C32 0.088(4) 0.073(3) 0.085(4) -0.023(3) -0.003(3) -0.002(3) C71 0.058(3) 0.055(3) 0.042(2) -0.003(2) 0.015(2) 0.004(2) C72 0.060(3) 0.064(3) 0.062(3) 0.000(2) 0.012(2) -0.010(2) C73 0.061(4) 0.115(5) 0.220(8) 0.038(5) 0.011(4) -0.020(4) C74 0.104(5) 0.202(8) 0.123(5) 0.082(5) 0.018(4) -0.045(5) C75 0.218(9) 0.178(8) 0.234(9) -0.141(7) 0.138(7) -0.134(7) C81 0.069(3) 0.079(4) 0.071(3) 0.007(3) 0.032(3) 0.010(3) C82 0.102(4) 0.074(3) 0.048(3) -0.008(3) 0.024(3) 0.012(3) C91 0.100(4) 0.087(4) 0.064(3) 0.016(3) 0.037(3) 0.008(3) O55 0.064(2) 0.070(2) 0.087(2) 0.0017(17) 0.0335(17) -0.0018(18) O571 0.097(2) 0.069(2) 0.068(2) -0.0127(18) 0.0013(18) -0.027(2) N581 0.090(3) 0.126(4) 0.057(2) -0.023(3) -0.001(2) 0.029(3) N582 0.082(3) 0.066(3) 0.086(3) -0.008(2) -0.001(2) 0.028(2) C51 0.051(2) 0.047(2) 0.039(2) 0.0000(18) 0.0117(18) -0.001(2) C52 0.064(3) 0.045(2) 0.052(2) 0.002(2) 0.017(2) -0.004(2) C53 0.066(3) 0.047(2) 0.056(2) -0.001(2) 0.021(2) 0.004(2) C54 0.085(3) 0.055(3) 0.067(3) -0.007(2) 0.041(3) 0.001(3) C55 0.060(3) 0.051(3) 0.055(3) 0.013(2) 0.019(2) 0.004(2) C56 0.045(2) 0.045(2) 0.040(2) -0.0001(18) 0.0096(18) 0.001(2) C57 0.049(2) 0.049(3) 0.039(2) -0.0029(18) 0.0083(18) -0.002(2) C58 0.050(2) 0.042(2) 0.042(2) -0.0040(18) 0.0083(18) 0.007(2) C59 0.045(2) 0.051(2) 0.048(2) -0.0041(19) 0.0134(18) 0.005(2) C531 0.113(4) 0.054(3) 0.095(4) -0.021(3) 0.035(3) 0.000(3) C532 0.084(3) 0.076(3) 0.084(3) 0.016(3) 0.021(3) 0.022(3) C571 0.049(2) 0.043(2) 0.059(3) -0.007(2) 0.004(2) -0.002(2) C572 0.059(3) 0.046(2) 0.062(3) 0.005(2) 0.012(2) 0.001(2) C573 0.116(4) 0.070(3) 0.053(3) 0.013(3) 0.002(3) -0.010(3) C574 0.078(4) 0.093(4) 0.104(4) 0.029(3) 0.038(3) -0.003(3) C575 0.094(4) 0.052(3) 0.109(4) 0.013(3) 0.008(3) 0.007(3) C581 0.059(3) 0.070(3) 0.050(3) -0.010(2) 0.009(2) 0.017(2) C582 0.057(3) 0.046(3) 0.054(2) -0.010(2) 0.007(2) 0.003(2) C591 0.064(3) 0.074(3) 0.090(3) 0.011(3) 0.039(3) 0.014(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 O5 C5 1.216(4) . ? O71 C71 1.210(4) . ? N81 C81 1.134(5) . ? N82 C82 1.132(6) . ? C1 C6 1.498(5) . ? C1 C2 1.523(5) . ? C1 C9 1.538(5) . ? C1 H1 0.9800 . ? C2 C3 1.535(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C32 1.527(6) . ? C3 C31 1.534(6) . ? C3 C4 1.538(6) . ? C4 C5 1.490(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.502(5) . ? C6 C7 1.330(5) . ? C7 C71 1.508(5) . ? C7 C8 1.542(5) . ? C8 C82 1.475(6) . ? C8 C81 1.480(6) . ? C8 C9 1.570(5) . ? C9 C91 1.515(5) . ? C9 H9 0.9800 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C71 C72 1.519(6) . ? C72 C75 1.495(7) . ? C72 C73 1.507(7) . ? C72 C74 1.523(7) . ? C73 H73A 0.9600 . ? C73 H73B 0.9600 . ? C73 H73C 0.9600 . ? C74 H74A 0.9600 . ? C74 H74B 0.9600 . ? C74 H74C 0.9600 . ? C75 H75A 0.9600 . ? C75 H75B 0.9600 . ? C75 H75C 0.9600 . ? C91 H91A 0.9600 . ? C91 H91B 0.9600 . ? C91 H91C 0.9600 . ? O55 C55 1.220(5) . ? O571 C571 1.218(4) . ? N581 C581 1.131(5) . ? N582 C582 1.134(5) . ? C51 C56 1.498(5) . ? C51 C52 1.519(5) . ? C51 C59 1.525(5) . ? C51 H51 0.9800 . ? C52 C53 1.524(5) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 C532 1.528(6) . ? C53 C54 1.538(6) . ? C53 C531 1.547(6) . ? C54 C55 1.503(6) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C55 C56 1.488(5) . ? C56 C57 1.332(5) . ? C57 C571 1.503(5) . ? C57 C58 1.530(5) . ? C58 C582 1.482(6) . ? C58 C581 1.494(5) . ? C58 C59 1.565(5) . ? C59 C591 1.522(5) . ? C59 H59 0.9800 . ? C531 H53A 0.9600 . ? C531 H53B 0.9600 . ? C531 H53C 0.9600 . ? C532 H53D 0.9600 . ? C532 H53E 0.9600 . ? C532 H53F 0.9600 . ? C571 C572 1.530(6) . ? C572 C573 1.520(6) . ? C572 C574 1.523(6) . ? C572 C575 1.544(6) . ? C573 H57A 0.9600 . ? C573 H57B 0.9600 . ? C573 H57C 0.9600 . ? C574 H57D 0.9600 . ? C574 H57E 0.9600 . ? C574 H57F 0.9600 . ? C575 H57G 0.9600 . ? C575 H57H 0.9600 . ? C575 H57I 0.9600 . ? C591 H59A 0.9600 . ? C591 H59B 0.9600 . ? C591 H59C 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 C6 C1 C2 111.5(3) . . ? C6 C1 C9 102.3(3) . . ? C2 C1 C9 116.4(3) . . ? C6 C1 H1 108.8 . . ? C2 C1 H1 108.8 . . ? C9 C1 H1 108.8 . . ? C1 C2 C3 112.7(3) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C32 C3 C31 108.8(4) . . ? C32 C3 C2 111.0(4) . . ? C31 C3 C2 109.0(3) . . ? C32 C3 C4 110.2(4) . . ? C31 C3 C4 109.0(4) . . ? C2 C3 C4 108.8(3) . . ? C5 C4 C3 116.6(3) . . ? C5 C4 H4A 108.1 . . ? C3 C4 H4A 108.1 . . ? C5 C4 H4B 108.1 . . ? C3 C4 H4B 108.1 . . ? H4A C4 H4B 107.3 . . ? O5 C5 C4 124.0(4) . . ? O5 C5 C6 120.4(4) . . ? C4 C5 C6 115.6(3) . . ? C7 C6 C1 114.1(3) . . ? C7 C6 C5 125.8(4) . . ? C1 C6 C5 120.1(3) . . ? C6 C7 C71 131.0(3) . . ? C6 C7 C8 108.0(3) . . ? C71 C7 C8 120.3(3) . . ? C82 C8 C81 107.1(4) . . ? C82 C8 C7 114.7(4) . . ? C81 C8 C7 110.2(3) . . ? C82 C8 C9 111.4(3) . . ? C81 C8 C9 111.6(4) . . ? C7 C8 C9 101.9(3) . . ? C91 C9 C1 116.3(4) . . ? C91 C9 C8 115.5(3) . . ? C1 C9 C8 102.4(3) . . ? C91 C9 H9 107.3 . . ? C1 C9 H9 107.3 . . ? C8 C9 H9 107.3 . . ? C3 C31 H31A 109.5 . . ? C3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C3 C32 H32A 109.5 . . ? C3 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C3 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O71 C71 C7 116.4(4) . . ? O71 C71 C72 121.9(4) . . ? C7 C71 C72 121.4(4) . . ? C75 C72 C73 110.2(5) . . ? C75 C72 C71 107.6(4) . . ? C73 C72 C71 113.8(4) . . ? C75 C72 C74 109.1(5) . . ? C73 C72 C74 106.9(5) . . ? C71 C72 C74 109.3(4) . . ? C72 C73 H73A 109.5 . . ? C72 C73 H73B 109.5 . . ? H73A C73 H73B 109.5 . . ? C72 C73 H73C 109.5 . . ? H73A C73 H73C 109.5 . . ? H73B C73 H73C 109.5 . . ? C72 C74 H74A 109.5 . . ? C72 C74 H74B 109.5 . . ? H74A C74 H74B 109.5 . . ? C72 C74 H74C 109.5 . . ? H74A C74 H74C 109.5 . . ? H74B C74 H74C 109.5 . . ? C72 C75 H75A 109.5 . . ? C72 C75 H75B 109.5 . . ? H75A C75 H75B 109.5 . . ? C72 C75 H75C 109.5 . . ? H75A C75 H75C 109.5 . . ? H75B C75 H75C 109.5 . . ? N81 C81 C8 178.0(6) . . ? N82 C82 C8 177.3(5) . . ? C9 C91 H91A 109.5 . . ? C9 C91 H91B 109.5 . . ? H91A C91 H91B 109.5 . . ? C9 C91 H91C 109.5 . . ? H91A C91 H91C 109.5 . . ? H91B C91 H91C 109.5 . . ? C56 C51 C52 111.2(3) . . ? C56 C51 C59 103.1(3) . . ? C52 C51 C59 116.4(3) . . ? C56 C51 H51 108.6 . . ? C52 C51 H51 108.6 . . ? C59 C51 H51 108.6 . . ? C51 C52 C53 113.6(3) . . ? C51 C52 H52A 108.8 . . ? C53 C52 H52A 108.8 . . ? C51 C52 H52B 108.8 . . ? C53 C52 H52B 108.8 . . ? H52A C52 H52B 107.7 . . ? C52 C53 C532 111.8(3) . . ? C52 C53 C54 109.5(3) . . ? C532 C53 C54 109.3(4) . . ? C52 C53 C531 108.1(4) . . ? C532 C53 C531 109.4(4) . . ? C54 C53 C531 108.7(3) . . ? C55 C54 C53 114.0(3) . . ? C55 C54 H54A 108.7 . . ? C53 C54 H54A 108.7 . . ? C55 C54 H54B 108.7 . . ? C53 C54 H54B 108.7 . . ? H54A C54 H54B 107.6 . . ? O55 C55 C56 120.8(4) . . ? O55 C55 C54 123.4(4) . . ? C56 C55 C54 115.7(4) . . ? C57 C56 C55 125.8(4) . . ? C57 C56 C51 112.8(3) . . ? C55 C56 C51 121.3(3) . . ? C56 C57 C571 130.3(4) . . ? C56 C57 C58 108.7(3) . . ? C571 C57 C58 120.4(3) . . ? C582 C58 C581 107.9(3) . . ? C582 C58 C57 115.1(3) . . ? C581 C58 C57 109.2(3) . . ? C582 C58 C59 110.7(3) . . ? C581 C58 C59 111.4(3) . . ? C57 C58 C59 102.5(3) . . ? C591 C59 C51 117.1(3) . . ? C591 C59 C58 114.9(3) . . ? C51 C59 C58 102.3(3) . . ? C591 C59 H59 107.4 . . ? C51 C59 H59 107.4 . . ? C58 C59 H59 107.4 . . ? C53 C531 H53A 109.5 . . ? C53 C531 H53B 109.5 . . ? H53A C531 H53B 109.5 . . ? C53 C531 H53C 109.5 . . ? H53A C531 H53C 109.5 . . ? H53B C531 H53C 109.5 . . ? C53 C532 H53D 109.5 . . ? C53 C532 H53E 109.5 . . ? H53D C532 H53E 109.5 . . ? C53 C532 H53F 109.5 . . ? H53D C532 H53F 109.5 . . ? H53E C532 H53F 109.5 . . ? O571 C571 C57 116.4(4) . . ? O571 C571 C572 121.2(4) . . ? C57 C571 C572 122.3(3) . . ? C573 C572 C574 110.5(4) . . ? C573 C572 C571 112.3(3) . . ? C574 C572 C571 109.7(3) . . ? C573 C572 C575 109.7(4) . . ? C574 C572 C575 108.6(4) . . ? C571 C572 C575 105.9(4) . . ? C572 C573 H57A 109.5 . . ? C572 C573 H57B 109.5 . . ? H57A C573 H57B 109.5 . . ? C572 C573 H57C 109.5 . . ? H57A C573 H57C 109.5 . . ? H57B C573 H57C 109.5 . . ? C572 C574 H57D 109.5 . . ? C572 C574 H57E 109.5 . . ? H57D C574 H57E 109.5 . . ? C572 C574 H57F 109.5 . . ? H57D C574 H57F 109.5 . . ? H57E C574 H57F 109.5 . . ? C572 C575 H57G 109.5 . . ? C572 C575 H57H 109.5 . . ? H57G C575 H57H 109.5 . . ? C572 C575 H57I 109.5 . . ? H57G C575 H57I 109.5 . . ? H57H C575 H57I 109.5 . . ? N581 C581 C58 178.0(5) . . ? N582 C582 C58 177.4(4) . . ? C59 C591 H59A 109.5 . . ? C59 C591 H59B 109.5 . . ? H59A C591 H59B 109.5 . . ? C59 C591 H59C 109.5 . . ? H59A C591 H59C 109.5 . . ? H59B C591 H59C 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 C6 C1 C2 C3 52.7(4) . . . . ? C9 C1 C2 C3 169.5(3) . . . . ? C1 C2 C3 C32 62.8(5) . . . . ? C1 C2 C3 C31 -177.3(4) . . . . ? C1 C2 C3 C4 -58.6(4) . . . . ? C32 C3 C4 C5 -72.5(5) . . . . ? C31 C3 C4 C5 168.2(4) . . . . ? C2 C3 C4 C5 49.5(5) . . . . ? C3 C4 C5 O5 148.0(4) . . . . ? C3 C4 C5 C6 -34.6(5) . . . . ? C2 C1 C6 C7 141.7(3) . . . . ? C9 C1 C6 C7 16.6(4) . . . . ? C2 C1 C6 C5 -37.2(5) . . . . ? C9 C1 C6 C5 -162.3(3) . . . . ? O5 C5 C6 C7 27.2(6) . . . . ? C4 C5 C6 C7 -150.3(4) . . . . ? O5 C5 C6 C1 -154.0(4) . . . . ? C4 C5 C6 C1 28.5(5) . . . . ? C1 C6 C7 C71 174.9(4) . . . . ? C5 C6 C7 C71 -6.3(7) . . . . ? C1 C6 C7 C8 5.1(4) . . . . ? C5 C6 C7 C8 -176.1(3) . . . . ? C6 C7 C8 C82 -144.6(4) . . . . ? C71 C7 C8 C82 44.3(5) . . . . ? C6 C7 C8 C81 94.5(4) . . . . ? C71 C7 C8 C81 -76.6(5) . . . . ? C6 C7 C8 C9 -24.1(4) . . . . ? C71 C7 C8 C9 164.8(3) . . . . ? C6 C1 C9 C91 -156.9(4) . . . . ? C2 C1 C9 C91 81.4(5) . . . . ? C6 C1 C9 C8 -29.9(4) . . . . ? C2 C1 C9 C8 -151.7(3) . . . . ? C82 C8 C9 C91 -76.9(5) . . . . ? C81 C8 C9 C91 42.8(5) . . . . ? C7 C8 C9 C91 160.3(4) . . . . ? C82 C8 C9 C1 155.6(3) . . . . ? C81 C8 C9 C1 -84.7(4) . . . . ? C7 C8 C9 C1 32.8(4) . . . . ? C6 C7 C71 O71 -105.5(5) . . . . ? C8 C7 C71 O71 63.2(5) . . . . ? C6 C7 C71 C72 79.2(6) . . . . ? C8 C7 C71 C72 -112.1(4) . . . . ? O71 C71 C72 C75 -68.8(6) . . . . ? C7 C71 C72 C75 106.1(6) . . . . ? O71 C71 C72 C73 168.7(5) . . . . ? C7 C71 C72 C73 -16.3(6) . . . . ? O71 C71 C72 C74 49.4(6) . . . . ? C7 C71 C72 C74 -135.6(5) . . . . ? C82 C8 C81 N81 102(17) . . . . ? C7 C8 C81 N81 -132(17) . . . . ? C9 C8 C81 N81 -20(17) . . . . ? C81 C8 C82 N82 -95(12) . . . . ? C7 C8 C82 N82 142(12) . . . . ? C9 C8 C82 N82 27(12) . . . . ? C56 C51 C52 C53 49.1(4) . . . . ? C59 C51 C52 C53 166.8(3) . . . . ? C51 C52 C53 C532 62.1(5) . . . . ? C51 C52 C53 C54 -59.1(4) . . . . ? C51 C52 C53 C531 -177.4(3) . . . . ? C52 C53 C54 C55 52.3(5) . . . . ? C532 C53 C54 C55 -70.5(5) . . . . ? C531 C53 C54 C55 170.1(4) . . . . ? C53 C54 C55 O55 144.6(4) . . . . ? C53 C54 C55 C56 -37.6(5) . . . . ? O55 C55 C56 C57 29.7(6) . . . . ? C54 C55 C56 C57 -148.2(4) . . . . ? O55 C55 C56 C51 -152.9(4) . . . . ? C54 C55 C56 C51 29.1(5) . . . . ? C52 C51 C56 C57 143.6(3) . . . . ? C59 C51 C56 C57 18.1(4) . . . . ? C52 C51 C56 C55 -34.0(5) . . . . ? C59 C51 C56 C55 -159.5(3) . . . . ? C55 C56 C57 C571 -9.2(7) . . . . ? C51 C56 C57 C571 173.3(4) . . . . ? C55 C56 C57 C58 -179.9(3) . . . . ? C51 C56 C57 C58 2.5(4) . . . . ? C56 C57 C58 C582 -141.8(3) . . . . ? C571 C57 C58 C582 46.4(5) . . . . ? C56 C57 C58 C581 96.7(4) . . . . ? C571 C57 C58 C581 -75.2(4) . . . . ? C56 C57 C58 C59 -21.5(4) . . . . ? C571 C57 C58 C59 166.6(3) . . . . ? C56 C51 C59 C591 -156.2(3) . . . . ? C52 C51 C59 C591 81.8(4) . . . . ? C56 C51 C59 C58 -29.7(3) . . . . ? C52 C51 C59 C58 -151.8(3) . . . . ? C582 C58 C59 C591 -77.7(4) . . . . ? C581 C58 C59 C591 42.4(4) . . . . ? C57 C58 C59 C591 159.0(3) . . . . ? C582 C58 C59 C51 154.4(3) . . . . ? C581 C58 C59 C51 -85.5(4) . . . . ? C57 C58 C59 C51 31.1(3) . . . . ? C56 C57 C571 O571 -106.5(5) . . . . ? C58 C57 C571 O571 63.3(5) . . . . ? C56 C57 C571 C572 77.3(6) . . . . ? C58 C57 C571 C572 -112.8(4) . . . . ? O571 C571 C572 C573 -178.1(4) . . . . ? C57 C571 C572 C573 -2.1(5) . . . . ? O571 C571 C572 C574 58.6(5) . . . . ? C57 C571 C572 C574 -125.4(4) . . . . ? O571 C571 C572 C575 -58.4(5) . . . . ? C57 C571 C572 C575 117.6(4) . . . . ? C582 C58 C581 N581 161(14) . . . . ? C57 C58 C581 N581 -74(14) . . . . ? C59 C58 C581 N581 39(14) . . . . ? C581 C58 C582 N582 -118(10) . . . . ? C57 C58 C582 N582 120(10) . . . . ? C59 C58 C582 N582 4(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.302 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.038 data_b10f _database_code_depnum_ccdc_archive 'CCDC 266745' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1\a,6\a-4,4,8,8-tetramethyl-2-oxobicyclo[4.2.0]octane-7,7-dicarbonitrile ; _chemical_name_common ;1alpha,6alpha-4,4,8,8-tetramethyl-2-oxobicyclo(4.2.0)octane- 7,7-dicarbonitrile ; _chemical_melting_point '127 - 128' _chemical_formula_moiety 'C14 H18 N2 O' _chemical_formula_sum 'C14 H18 N2 O' _chemical_formula_weight 230.30 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.7448(14) _cell_length_b 6.7681(5) _cell_length_c 22.9068(17) _cell_angle_alpha 90.00 _cell_angle_beta 111.4830(10) _cell_angle_gamma 90.00 _cell_volume 2704.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.131 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'SADABS (Bruker, 2000)' _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 'CCD Apex area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% 0 _diffrn_reflns_number 26375 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4752 _reflns_number_gt 3355 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0749P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4752 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 O12 O 0.53175(8) -0.2773(2) 0.20307(7) 0.0916(5) Uani 1 1 d . . . N171 N 0.39997(10) 0.3113(3) -0.02503(8) 0.0880(6) Uani 1 1 d . . . N172 N 0.30299(10) 0.4093(2) 0.11524(9) 0.0775(5) Uani 1 1 d . . . C11 C 0.47517(8) 0.0286(2) 0.16384(7) 0.0446(4) Uani 1 1 d . . . H11 H 0.4570 0.0435 0.1986 0.048(4) Uiso 1 1 calc R . . C12 C 0.53975(10) -0.1169(3) 0.18209(8) 0.0587(5) Uani 1 1 d . . . C13 C 0.61210(11) -0.0626(3) 0.17256(9) 0.0736(6) Uani 1 1 d . . . H13A H 0.6111 -0.1230 0.1339 0.092(7) Uiso 1 1 calc R . . H13B H 0.6550 -0.1194 0.2065 0.094(7) Uiso 1 1 calc R . . C14 C 0.62690(10) 0.1592(3) 0.16951(8) 0.0640(5) Uani 1 1 d . . . C15 C 0.55559(9) 0.2519(3) 0.12078(8) 0.0590(5) Uani 1 1 d . . . H15A H 0.5654 0.3902 0.1155 0.077(6) Uiso 1 1 calc R . . H15B H 0.5443 0.1862 0.0808 0.062(5) Uiso 1 1 calc R . . C16 C 0.48709(8) 0.2348(2) 0.14053(7) 0.0445(4) Uani 1 1 d . . . H16 H 0.4876 0.3379 0.1707 0.047(4) Uiso 1 1 calc R . . C17 C 0.40571(8) 0.2168(2) 0.08650(7) 0.0438(4) Uani 1 1 d . . . C18 C 0.40499(9) -0.0124(2) 0.10206(7) 0.0458(4) Uani 1 1 d . . . C141 C 0.69524(12) 0.1895(6) 0.14945(12) 0.1071(10) Uani 1 1 d . . . H14A H 0.7399 0.1287 0.1795 0.097(7) Uiso 1 1 calc R . . H14B H 0.7043 0.3283 0.1472 0.149(14) Uiso 1 1 calc R . . H14C H 0.6846 0.1304 0.1090 0.118(9) Uiso 1 1 calc R . . C142 C 0.64443(11) 0.2524(4) 0.23385(9) 0.0801(6) Uani 1 1 d . . . H14D H 0.6031 0.2259 0.2480 0.075(6) Uiso 1 1 calc R . . H14E H 0.6503 0.3926 0.2310 0.118(9) Uiso 1 1 calc R . . H14F H 0.6910 0.1974 0.2631 0.087(6) Uiso 1 1 calc R . . C171 C 0.40119(10) 0.2707(3) 0.02333(8) 0.0570(5) Uani 1 1 d . . . C172 C 0.34736(10) 0.3272(2) 0.10124(8) 0.0519(4) Uani 1 1 d . . . C181 C 0.42251(12) -0.1415(3) 0.05465(8) 0.0678(6) Uani 1 1 d . . . H18A H 0.4331 -0.2739 0.0706 0.124(9) Uiso 1 1 calc R . . H18B H 0.4664 -0.0899 0.0476 0.067(6) Uiso 1 1 calc R . . H18C H 0.3791 -0.1423 0.0158 0.080(6) Uiso 1 1 calc R . . C182 C 0.33396(10) -0.0850(3) 0.11190(9) 0.0626(5) Uani 1 1 d . . . H18D H 0.2908 -0.0770 0.0731 0.086(6) Uiso 1 1 calc R . . H18E H 0.3247 -0.0043 0.1429 0.076(6) Uiso 1 1 calc R . . H18F H 0.3413 -0.2196 0.1260 0.091(7) Uiso 1 1 calc R . . O22 O -0.00813(9) 1.1371(2) 0.43626(7) 0.0837(4) Uani 1 1 d . . . N271 N 0.21821(9) 0.4329(3) 0.46134(8) 0.0756(5) Uani 1 1 d . . . N272 N 0.09252(10) 0.5858(4) 0.27160(9) 0.1107(8) Uani 1 1 d . . . C21 C 0.04465(9) 0.8247(2) 0.43219(7) 0.0474(4) Uani 1 1 d . . . H21 H 0.0659 0.8071 0.4778 0.058(5) Uiso 1 1 calc R . . C22 C -0.02077(10) 0.9703(3) 0.41521(8) 0.0554(5) Uani 1 1 d . . . C23 C -0.09842(10) 0.9085(3) 0.37209(9) 0.0638(5) Uani 1 1 d . . . H23A H -0.1092 0.9749 0.3322 0.087(6) Uiso 1 1 calc R . . H23B H -0.1355 0.9558 0.3893 0.087(6) Uiso 1 1 calc R . . C24 C -0.11179(9) 0.6876(3) 0.35927(8) 0.0563(5) Uani 1 1 d . . . C25 C -0.04399(9) 0.6050(3) 0.34455(8) 0.0552(5) Uani 1 1 d . . . H25A H -0.0536 0.4674 0.3324 0.072(6) Uiso 1 1 calc R . . H25B H -0.0393 0.6771 0.3095 0.061(5) Uiso 1 1 calc R . . C26 C 0.03005(8) 0.6214(2) 0.40043(7) 0.0449(4) Uani 1 1 d . . . H26 H 0.0347 0.5156 0.4308 0.057(5) Uiso 1 1 calc R . . C27 C 0.10606(8) 0.6452(2) 0.38668(7) 0.0451(4) Uani 1 1 d . . . C28 C 0.11130(9) 0.8698(2) 0.40862(7) 0.0477(4) Uani 1 1 d . . . C241 C -0.18527(11) 0.6559(4) 0.30258(10) 0.0881(7) Uani 1 1 d . . . H24A H -0.2273 0.7181 0.3099 0.082(6) Uiso 1 1 calc R . . H24B H -0.1951 0.5169 0.2961 0.120(10) Uiso 1 1 calc R . . H24C H -0.1797 0.7128 0.2661 0.093(7) Uiso 1 1 calc R . . C242 C -0.11833(12) 0.5850(3) 0.41665(10) 0.0759(6) Uani 1 1 d . . . H24D H -0.1630 0.6325 0.4233 0.084(6) Uiso 1 1 calc R . . H24E H -0.0735 0.6131 0.4529 0.102(8) Uiso 1 1 calc R . . H24F H -0.1226 0.4449 0.4097 0.119(9) Uiso 1 1 calc R . . C271 C 0.16930(10) 0.5243(3) 0.42808(8) 0.0531(4) Uani 1 1 d . . . C272 C 0.09913(9) 0.6101(3) 0.32181(9) 0.0653(5) Uani 1 1 d . . . C281 C 0.09086(12) 1.0127(3) 0.35394(9) 0.0721(6) Uani 1 1 d . . . H28A H 0.0842 1.1427 0.3679 0.107(8) Uiso 1 1 calc R . . H28B H 0.0441 0.9710 0.3216 0.076(6) Uiso 1 1 calc R . . H28C H 0.1313 1.0148 0.3377 0.074(6) Uiso 1 1 calc R . . C282 C 0.18596(11) 0.9293(3) 0.45975(10) 0.0741(6) Uani 1 1 d . . . H28D H 0.2263 0.9289 0.4433 0.115(9) Uiso 1 1 calc R . . H28E H 0.1981 0.8373 0.4939 0.089(7) Uiso 1 1 calc R . . H28F H 0.1809 1.0594 0.4745 0.084(6) 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 O12 0.1034(12) 0.0702(10) 0.0953(11) 0.0297(8) 0.0295(9) 0.0244(9) N171 0.0898(13) 0.1145(16) 0.0602(10) 0.0218(10) 0.0279(9) -0.0044(11) N172 0.0695(11) 0.0610(11) 0.1142(14) -0.0038(9) 0.0481(10) 0.0054(9) C11 0.0497(9) 0.0465(10) 0.0391(8) -0.0014(7) 0.0180(7) 0.0015(7) C12 0.0656(12) 0.0585(12) 0.0462(10) 0.0014(9) 0.0135(9) 0.0115(9) C13 0.0595(12) 0.0921(17) 0.0633(13) -0.0033(11) 0.0155(10) 0.0260(11) C14 0.0440(10) 0.0927(16) 0.0568(11) -0.0049(10) 0.0202(8) -0.0010(10) C15 0.0505(11) 0.0760(14) 0.0523(11) 0.0036(9) 0.0210(9) -0.0059(9) C16 0.0454(9) 0.0479(10) 0.0421(8) -0.0030(7) 0.0181(7) -0.0026(7) C17 0.0429(9) 0.0452(9) 0.0452(9) 0.0036(7) 0.0184(7) 0.0011(7) C18 0.0506(10) 0.0415(9) 0.0439(9) -0.0007(7) 0.0156(7) 0.0001(7) C141 0.0506(14) 0.184(4) 0.092(2) 0.0021(19) 0.0328(13) 0.0007(15) C142 0.0574(13) 0.109(2) 0.0640(13) -0.0143(12) 0.0100(11) -0.0097(12) C171 0.0536(11) 0.0642(12) 0.0522(11) 0.0109(9) 0.0181(9) -0.0015(9) C172 0.0501(10) 0.0435(10) 0.0634(11) 0.0037(8) 0.0225(9) -0.0007(8) C181 0.0783(14) 0.0624(14) 0.0548(11) -0.0140(9) 0.0152(10) 0.0070(11) C182 0.0640(12) 0.0534(12) 0.0666(12) 0.0056(10) 0.0195(10) -0.0122(9) O22 0.1062(11) 0.0532(9) 0.0992(10) -0.0110(7) 0.0464(9) 0.0124(8) N271 0.0586(10) 0.0596(11) 0.0987(13) -0.0006(9) 0.0170(9) 0.0046(8) N272 0.0687(12) 0.202(2) 0.0662(11) -0.0482(13) 0.0305(10) -0.0093(13) C21 0.0598(10) 0.0441(10) 0.0395(9) -0.0002(7) 0.0197(8) 0.0040(8) C22 0.0736(13) 0.0487(11) 0.0546(10) 0.0017(8) 0.0360(9) 0.0082(9) C23 0.0637(12) 0.0685(13) 0.0680(12) 0.0145(10) 0.0347(10) 0.0198(10) C24 0.0437(10) 0.0694(13) 0.0610(11) 0.0036(9) 0.0254(8) 0.0025(8) C25 0.0448(10) 0.0645(12) 0.0602(11) -0.0135(9) 0.0237(8) -0.0070(8) C26 0.0452(9) 0.0461(10) 0.0479(9) -0.0024(7) 0.0225(7) -0.0027(7) C27 0.0400(9) 0.0515(10) 0.0441(9) -0.0095(7) 0.0159(7) -0.0039(7) C28 0.0475(9) 0.0448(10) 0.0473(9) -0.0014(7) 0.0133(7) -0.0047(7) C241 0.0480(12) 0.126(2) 0.0900(17) -0.0009(14) 0.0249(11) 0.0028(12) C242 0.0613(14) 0.0865(17) 0.0963(16) 0.0221(12) 0.0481(13) 0.0059(11) C271 0.0475(10) 0.0462(11) 0.0658(11) -0.0116(9) 0.0212(9) -0.0042(9) C272 0.0414(10) 0.1006(16) 0.0566(11) -0.0264(10) 0.0213(9) -0.0095(10) C281 0.0685(14) 0.0746(16) 0.0747(13) 0.0211(11) 0.0282(12) -0.0011(11) C282 0.0686(14) 0.0534(13) 0.0799(14) -0.0125(11) 0.0029(12) -0.0086(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O12 C12 1.219(2) . ? N171 C171 1.133(2) . ? N172 C172 1.140(2) . ? C11 C12 1.496(2) . ? C11 C16 1.540(2) . ? C11 C18 1.564(2) . ? C11 H11 0.9800 . ? C12 C13 1.496(3) . ? C13 C14 1.533(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C142 1.524(3) . ? C14 C141 1.525(3) . ? C14 C15 1.528(2) . ? C15 C16 1.514(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.578(2) . ? C16 H16 0.9800 . ? C17 C172 1.462(2) . ? C17 C171 1.465(2) . ? C17 C18 1.593(2) . ? C18 C182 1.512(2) . ? C18 C181 1.521(2) . ? C141 H14A 0.9600 . ? C141 H14B 0.9600 . ? C141 H14C 0.9600 . ? C142 H14D 0.9600 . ? C142 H14E 0.9600 . ? C142 H14F 0.9600 . ? C181 H18A 0.9600 . ? C181 H18B 0.9600 . ? C181 H18C 0.9600 . ? C182 H18D 0.9600 . ? C182 H18E 0.9600 . ? C182 H18F 0.9600 . ? O22 C22 1.216(2) . ? N271 C271 1.137(2) . ? N272 C272 1.123(2) . ? C21 C22 1.509(2) . ? C21 C26 1.534(2) . ? C21 C28 1.562(2) . ? C21 H21 0.9800 . ? C22 C23 1.489(2) . ? C23 C24 1.527(2) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C241 1.523(2) . ? C24 C242 1.531(2) . ? C24 C25 1.535(2) . ? C25 C26 1.509(2) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.576(2) . ? C26 H26 0.9800 . ? C27 C272 1.463(2) . ? C27 C271 1.466(2) . ? C27 C28 1.593(2) . ? C28 C282 1.514(2) . ? C28 C281 1.516(2) . ? C241 H24A 0.9600 . ? C241 H24B 0.9600 . ? C241 H24C 0.9600 . ? C242 H24D 0.9600 . ? C242 H24E 0.9600 . ? C242 H24F 0.9600 . ? C281 H28A 0.9600 . ? C281 H28B 0.9600 . ? C281 H28C 0.9600 . ? C282 H28D 0.9600 . ? C282 H28E 0.9600 . ? C282 H28F 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 C12 C11 C16 119.21(14) . . ? C12 C11 C18 117.55(13) . . ? C16 C11 C18 91.59(11) . . ? C12 C11 H11 109.1 . . ? C16 C11 H11 109.1 . . ? C18 C11 H11 109.1 . . ? O12 C12 C13 121.68(17) . . ? O12 C12 C11 119.52(17) . . ? C13 C12 C11 118.78(17) . . ? C12 C13 C14 115.84(15) . . ? C12 C13 H13A 108.3 . . ? C14 C13 H13A 108.3 . . ? C12 C13 H13B 108.3 . . ? C14 C13 H13B 108.3 . . ? H13A C13 H13B 107.4 . . ? C142 C14 C141 109.17(18) . . ? C142 C14 C15 110.97(16) . . ? C141 C14 C15 109.37(17) . . ? C142 C14 C13 109.85(17) . . ? C141 C14 C13 109.3(2) . . ? C15 C14 C13 108.12(15) . . ? C16 C15 C14 111.17(14) . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C11 114.81(13) . . ? C15 C16 C17 116.96(12) . . ? C11 C16 C17 88.89(11) . . ? C15 C16 H16 111.5 . . ? C11 C16 H16 111.5 . . ? C17 C16 H16 111.5 . . ? C172 C17 C171 108.86(13) . . ? C172 C17 C16 111.68(13) . . ? C171 C17 C16 116.44(13) . . ? C172 C17 C18 112.17(13) . . ? C171 C17 C18 117.48(13) . . ? C16 C17 C18 89.13(11) . . ? C182 C18 C181 110.62(15) . . ? C182 C18 C11 114.68(13) . . ? C181 C18 C11 114.71(13) . . ? C182 C18 C17 115.47(13) . . ? C181 C18 C17 112.23(13) . . ? C11 C18 C17 87.50(11) . . ? C14 C141 H14A 109.5 . . ? C14 C141 H14B 109.5 . . ? H14A C141 H14B 109.5 . . ? C14 C141 H14C 109.5 . . ? H14A C141 H14C 109.5 . . ? H14B C141 H14C 109.5 . . ? C14 C142 H14D 109.5 . . ? C14 C142 H14E 109.5 . . ? H14D C142 H14E 109.5 . . ? C14 C142 H14F 109.5 . . ? H14D C142 H14F 109.5 . . ? H14E C142 H14F 109.5 . . ? N171 C171 C17 177.94(19) . . ? N172 C172 C17 177.00(18) . . ? C18 C181 H18A 109.5 . . ? C18 C181 H18B 109.5 . . ? H18A C181 H18B 109.5 . . ? C18 C181 H18C 109.5 . . ? H18A C181 H18C 109.5 . . ? H18B C181 H18C 109.5 . . ? C18 C182 H18D 109.5 . . ? C18 C182 H18E 109.5 . . ? H18D C182 H18E 109.5 . . ? C18 C182 H18F 109.5 . . ? H18D C182 H18F 109.5 . . ? H18E C182 H18F 109.5 . . ? C22 C21 C26 118.48(14) . . ? C22 C21 C28 117.45(13) . . ? C26 C21 C28 92.15(11) . . ? C22 C21 H21 109.2 . . ? C26 C21 H21 109.2 . . ? C28 C21 H21 109.2 . . ? O22 C22 C23 121.68(17) . . ? O22 C22 C21 118.81(17) . . ? C23 C22 C21 119.49(15) . . ? C22 C23 C24 117.04(15) . . ? C22 C23 H23A 108.0 . . ? C24 C23 H23A 108.0 . . ? C22 C23 H23B 108.0 . . ? C24 C23 H23B 108.0 . . ? H23A C23 H23B 107.3 . . ? C241 C24 C23 109.61(17) . . ? C241 C24 C242 109.66(17) . . ? C23 C24 C242 109.78(16) . . ? C241 C24 C25 108.92(15) . . ? C23 C24 C25 107.96(14) . . ? C242 C24 C25 110.88(15) . . ? C26 C25 C24 111.43(13) . . ? C26 C25 H25A 109.3 . . ? C24 C25 H25A 109.3 . . ? C26 C25 H25B 109.3 . . ? C24 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? C25 C26 C21 114.66(14) . . ? C25 C26 C27 117.14(13) . . ? C21 C26 C27 89.19(11) . . ? C25 C26 H26 111.4 . . ? C21 C26 H26 111.4 . . ? C27 C26 H26 111.4 . . ? C272 C27 C271 108.45(14) . . ? C272 C27 C26 115.84(12) . . ? C271 C27 C26 112.94(13) . . ? C272 C27 C28 116.59(14) . . ? C271 C27 C28 112.75(12) . . ? C26 C27 C28 89.43(11) . . ? C282 C28 C281 110.58(16) . . ? C282 C28 C21 114.49(14) . . ? C281 C28 C21 114.70(14) . . ? C282 C28 C27 115.51(14) . . ? C281 C28 C27 112.36(14) . . ? C21 C28 C27 87.61(11) . . ? C24 C241 H24A 109.5 . . ? C24 C241 H24B 109.5 . . ? H24A C241 H24B 109.5 . . ? C24 C241 H24C 109.5 . . ? H24A C241 H24C 109.5 . . ? H24B C241 H24C 109.5 . . ? C24 C242 H24D 109.5 . . ? C24 C242 H24E 109.5 . . ? H24D C242 H24E 109.5 . . ? C24 C242 H24F 109.5 . . ? H24D C242 H24F 109.5 . . ? H24E C242 H24F 109.5 . . ? N271 C271 C27 178.40(19) . . ? N272 C272 C27 178.6(2) . . ? C28 C281 H28A 109.5 . . ? C28 C281 H28B 109.5 . . ? H28A C281 H28B 109.5 . . ? C28 C281 H28C 109.5 . . ? H28A C281 H28C 109.5 . . ? H28B C281 H28C 109.5 . . ? C28 C282 H28D 109.5 . . ? C28 C282 H28E 109.5 . . ? H28D C282 H28E 109.5 . . ? C28 C282 H28F 109.5 . . ? H28D C282 H28F 109.5 . . ? H28E C282 H28F 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 C16 C11 C12 O12 176.93(15) . . . . ? C18 C11 C12 O12 -73.9(2) . . . . ? C16 C11 C12 C13 -4.5(2) . . . . ? C18 C11 C12 C13 104.59(18) . . . . ? O12 C12 C13 C14 -158.42(18) . . . . ? C11 C12 C13 C14 23.1(2) . . . . ? C12 C13 C14 C142 69.1(2) . . . . ? C12 C13 C14 C141 -171.08(16) . . . . ? C12 C13 C14 C15 -52.1(2) . . . . ? C142 C14 C15 C16 -56.5(2) . . . . ? C141 C14 C15 C16 -177.00(19) . . . . ? C13 C14 C15 C16 64.02(19) . . . . ? C14 C15 C16 C11 -46.94(19) . . . . ? C14 C15 C16 C17 -149.13(15) . . . . ? C12 C11 C16 C15 16.69(19) . . . . ? C18 C11 C16 C15 -106.37(14) . . . . ? C12 C11 C16 C17 136.08(14) . . . . ? C18 C11 C16 C17 13.01(11) . . . . ? C15 C16 C17 C172 -141.73(15) . . . . ? C11 C16 C17 C172 100.82(14) . . . . ? C15 C16 C17 C171 -15.8(2) . . . . ? C11 C16 C17 C171 -133.30(14) . . . . ? C15 C16 C17 C18 104.68(15) . . . . ? C11 C16 C17 C18 -12.77(11) . . . . ? C12 C11 C18 C182 105.71(17) . . . . ? C16 C11 C18 C182 -129.88(14) . . . . ? C12 C11 C18 C181 -23.9(2) . . . . ? C16 C11 C18 C181 100.48(15) . . . . ? C12 C11 C18 C17 -137.31(15) . . . . ? C16 C11 C18 C17 -12.90(11) . . . . ? C172 C17 C18 C182 15.69(19) . . . . ? C171 C17 C18 C182 -111.58(16) . . . . ? C16 C17 C18 C182 128.81(13) . . . . ? C172 C17 C18 C181 143.72(14) . . . . ? C171 C17 C18 C181 16.45(19) . . . . ? C16 C17 C18 C181 -103.16(14) . . . . ? C172 C17 C18 C11 -100.55(13) . . . . ? C171 C17 C18 C11 132.19(14) . . . . ? C16 C17 C18 C11 12.58(10) . . . . ? C172 C17 C171 N171 150(6) . . . . ? C16 C17 C171 N171 23(6) . . . . ? C18 C17 C171 N171 -81(6) . . . . ? C171 C17 C172 N172 -179(100) . . . . ? C16 C17 C172 N172 -49(4) . . . . ? C18 C17 C172 N172 49(4) . . . . ? C26 C21 C22 O22 -174.10(15) . . . . ? C28 C21 C22 O22 -64.8(2) . . . . ? C26 C21 C22 C23 4.4(2) . . . . ? C28 C21 C22 C23 113.67(16) . . . . ? O22 C22 C23 C24 -167.81(16) . . . . ? C21 C22 C23 C24 13.7(2) . . . . ? C22 C23 C24 C241 -165.40(15) . . . . ? C22 C23 C24 C242 74.09(19) . . . . ? C22 C23 C24 C25 -46.9(2) . . . . ? C241 C24 C25 C26 -176.68(17) . . . . ? C23 C24 C25 C26 64.37(19) . . . . ? C242 C24 C25 C26 -55.9(2) . . . . ? C24 C25 C26 C21 -48.06(19) . . . . ? C24 C25 C26 C27 -150.65(14) . . . . ? C22 C21 C26 C25 13.1(2) . . . . ? C28 C21 C26 C25 -109.91(14) . . . . ? C22 C21 C26 C27 132.82(14) . . . . ? C28 C21 C26 C27 9.79(11) . . . . ? C25 C26 C27 C272 -11.6(2) . . . . ? C21 C26 C27 C272 -129.10(15) . . . . ? C25 C26 C27 C271 -137.53(15) . . . . ? C21 C26 C27 C271 104.97(14) . . . . ? C25 C26 C27 C28 107.91(15) . . . . ? C21 C26 C27 C28 -9.59(11) . . . . ? C22 C21 C28 C282 109.40(17) . . . . ? C26 C21 C28 C282 -126.73(15) . . . . ? C22 C21 C28 C281 -20.0(2) . . . . ? C26 C21 C28 C281 103.88(16) . . . . ? C22 C21 C28 C27 -133.56(14) . . . . ? C26 C21 C28 C27 -9.69(11) . . . . ? C272 C27 C28 C282 -115.64(17) . . . . ? C271 C27 C28 C282 10.8(2) . . . . ? C26 C27 C28 C282 125.51(16) . . . . ? C272 C27 C28 C281 12.49(19) . . . . ? C271 C27 C28 C281 138.90(15) . . . . ? C26 C27 C28 C281 -106.36(14) . . . . ? C272 C27 C28 C21 128.27(14) . . . . ? C271 C27 C28 C21 -105.31(14) . . . . ? C26 C27 C28 C21 9.42(11) . . . . ? C272 C27 C271 N271 170(7) . . . . ? C26 C27 C271 N271 -61(7) . . . . ? C28 C27 C271 N271 39(7) . . . . ? C271 C27 C272 N272 178(100) . . . . ? C26 C27 C272 N272 50(10) . . . . ? C28 C27 C272 N272 -53(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.143 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.035