# Supplementary Material (ESI) for PCCP # This journal is (c) The Owner Societies 2008 data_global _journal_coden_Cambridge 1326 loop_ _publ_author_name 'Abil Aliev' _publ_contact_author_name 'Abil Aliev' _publ_contact_author_email A.E.ALIEV@UCL.AC.UK _publ_section_title ; Probing weak non-covalent interactions in solution and solid states with designed molecules ; # Attachment 'SSE0583.CIF' data_sse0583 _database_code_depnum_ccdc_archive 'CCDC 701931' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 O' _chemical_formula_sum 'C18 H16 O' _chemical_formula_weight 248.31 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 0.0000 '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' O O 0.0106 0.0000 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 16.312(8) _cell_length_b 7.247(3) _cell_length_c 16.383(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.243(7) _cell_angle_gamma 90.00 _cell_volume 1936.7(16) _cell_formula_units_Z 6 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2391 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 21.88 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.077 _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 120(2) _diffrn_radiation_wavelength 0.6751 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX2 CCD diffractometer' _diffrn_measurement_method 'thin-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10797 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 20.81 _reflns_number_total 2577 _reflns_number_gt 2262 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.1225P)^2^+1.4485P] 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 0.128(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details none _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 2577 _refine_ls_number_parameters 516 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.1837 _refine_ls_wR_factor_gt 0.1699 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2663(6) 0.9843(11) -0.1115(5) 0.049(2) Uani 1 1 d . . . C101 C 0.2824(8) 0.7097(18) 0.0902(7) 0.048(3) Uani 1 1 d . . . H101 H 0.2855 0.7603 0.1469 0.057 Uiso 1 1 calc R . . C102 C 0.2962(9) 0.8689(16) 0.0273(7) 0.050(3) Uani 1 1 d . . . H10A H 0.2710 0.9834 0.0485 0.060 Uiso 1 1 calc R . . H10B H 0.3558 0.8913 0.0217 0.060 Uiso 1 1 calc R . . C103 C 0.2601(8) 0.8270(15) -0.0566(7) 0.038(3) Uani 1 1 d . . . C104 C 0.2789(8) 0.6450(16) -0.0957(7) 0.044(3) Uani 1 1 d . . . H10C H 0.3367 0.6464 -0.1138 0.053 Uiso 1 1 calc R . . H10D H 0.2441 0.6319 -0.1451 0.053 Uiso 1 1 calc R . . C105 C 0.2658(7) 0.4739(16) -0.0412(7) 0.039(3) Uani 1 1 d . . . H105 H 0.2577 0.3632 -0.0767 0.047 Uiso 1 1 calc R . . C106 C 0.1871(8) 0.9277(19) -0.0818(7) 0.052(3) Uani 1 1 d . . . H10E H 0.1493 0.8668 -0.1208 0.062 Uiso 1 1 calc R . . H10F H 0.1601 1.0072 -0.0408 0.062 Uiso 1 1 calc R . . C107 C 0.3501(7) 0.5659(16) 0.0783(7) 0.037(3) Uani 1 1 d . . . C108 C 0.4177(8) 0.5545(16) 0.1283(6) 0.041(3) Uani 1 1 d . . . H108 H 0.4232 0.6360 0.1734 0.049 Uiso 1 1 calc R . . C109 C 0.4786(8) 0.4231(19) 0.1130(7) 0.048(3) Uani 1 1 d . . . H109 H 0.5263 0.4180 0.1464 0.058 Uiso 1 1 calc R . . C110 C 0.4690(8) 0.3007(18) 0.0490(7) 0.049(3) Uani 1 1 d . . . H110 H 0.5095 0.2091 0.0395 0.059 Uiso 1 1 calc R . . C111 C 0.4019(8) 0.3104(17) -0.0005(7) 0.043(3) Uani 1 1 d . . . H111 H 0.3972 0.2270 -0.0451 0.052 Uiso 1 1 calc R . . C112 C 0.3387(7) 0.4424(16) 0.0128(7) 0.039(3) Uani 1 1 d . . . C113 C 0.1979(8) 0.6242(17) 0.0756(7) 0.042(3) Uani 1 1 d . . . C114 C 0.1308(8) 0.6622(19) 0.1232(7) 0.048(4) Uani 1 1 d . . . H114 H 0.1366 0.7429 0.1686 0.057 Uiso 1 1 calc R . . C115 C 0.0551(9) 0.5853(17) 0.1065(8) 0.054(4) Uani 1 1 d . . . H115 H 0.0091 0.6153 0.1393 0.065 Uiso 1 1 calc R . . C116 C 0.0469(9) 0.466(2) 0.0425(8) 0.053(4) Uani 1 1 d . . . H116 H -0.0047 0.4104 0.0310 0.063 Uiso 1 1 calc R . . C117 C 0.1138(7) 0.4263(16) -0.0050(7) 0.042(3) Uani 1 1 d . . . H117 H 0.1077 0.3442 -0.0498 0.050 Uiso 1 1 calc R . . C118 C 0.1891(8) 0.5023(16) 0.0107(7) 0.046(3) Uani 1 1 d . . . O2 O 0.2015(5) 0.9311(11) 0.6209(5) 0.044(2) Uani 1 1 d . . . C201 C 0.4142(8) 0.7102(15) 0.5802(7) 0.040(3) Uani 1 1 d . . . H201 H 0.4691 0.7690 0.5885 0.048 Uiso 1 1 calc R . . C202 C 0.3452(7) 0.8655(14) 0.5844(7) 0.035(3) Uani 1 1 d . . . H20A H 0.3615 0.9593 0.6253 0.042 Uiso 1 1 calc R . . H20B H 0.3412 0.9275 0.5307 0.042 Uiso 1 1 calc R . . C203 C 0.2624(7) 0.7889(15) 0.6068(7) 0.039(3) Uani 1 1 d . . . C204 C 0.2265(8) 0.6229(16) 0.5592(7) 0.041(3) Uani 1 1 d . . . H20C H 0.2113 0.6625 0.5034 0.049 Uiso 1 1 calc R . . H20D H 0.1762 0.5791 0.5868 0.049 Uiso 1 1 calc R . . C205 C 0.2902(7) 0.4606(15) 0.5543(7) 0.037(3) Uani 1 1 d . . . H205 H 0.2594 0.3435 0.5440 0.045 Uiso 1 1 calc R . . C206 C 0.2306(7) 0.8205(19) 0.6899(7) 0.044(3) Uani 1 1 d . . . H20E H 0.1928 0.7273 0.7129 0.053 Uiso 1 1 calc R . . H20F H 0.2673 0.8804 0.7302 0.053 Uiso 1 1 calc R . . C207 C 0.4118(7) 0.6206(16) 0.4965(7) 0.037(3) Uani 1 1 d . . . C208 C 0.4638(7) 0.6679(17) 0.4364(7) 0.041(3) Uani 1 1 d . . . H208 H 0.5054 0.7570 0.4459 0.049 Uiso 1 1 calc R . . C209 C 0.4558(7) 0.5841(16) 0.3591(7) 0.041(3) Uani 1 1 d . . . H209 H 0.4924 0.6135 0.3161 0.049 Uiso 1 1 calc R . . C210 C 0.3930(7) 0.4576(17) 0.3475(7) 0.040(3) Uani 1 1 d . . . H210 H 0.3870 0.4023 0.2953 0.048 Uiso 1 1 calc R . . C211 C 0.3399(7) 0.4092(17) 0.4071(7) 0.039(3) Uani 1 1 d . . . H211 H 0.2984 0.3198 0.3971 0.047 Uiso 1 1 calc R . . C212 C 0.3469(8) 0.4927(15) 0.4836(7) 0.043(3) Uani 1 1 d . . . C213 C 0.4004(7) 0.5707(17) 0.6462(7) 0.038(3) Uani 1 1 d . . . C214 C 0.4451(7) 0.5692(18) 0.7174(7) 0.039(3) Uani 1 1 d . . . H214 H 0.4866 0.6587 0.7269 0.046 Uiso 1 1 calc R . . C215 C 0.4284(7) 0.4336(18) 0.7754(7) 0.043(3) Uani 1 1 d . . . H215 H 0.4602 0.4278 0.8241 0.051 Uiso 1 1 calc R . . C216 C 0.3656(7) 0.3069(18) 0.7627(7) 0.044(3) Uani 1 1 d . . . H216 H 0.3534 0.2180 0.8035 0.052 Uiso 1 1 calc R . . C217 C 0.3205(7) 0.3101(16) 0.6905(7) 0.037(3) Uani 1 1 d . . . H217 H 0.2780 0.2225 0.6817 0.045 Uiso 1 1 calc R . . C218 C 0.3373(7) 0.4393(16) 0.6319(7) 0.042(3) Uani 1 1 d . . . O3 O 0.0551(5) 0.4208(12) 0.4558(5) 0.046(2) Uani 1 1 d . . . C301 C 0.1272(7) -0.0497(16) 0.3717(7) 0.042(3) Uani 1 1 d . . . H301 H 0.1373 -0.1656 0.4033 0.051 Uiso 1 1 calc R . . C302 C 0.1207(8) 0.1159(15) 0.4318(8) 0.042(3) Uani 1 1 d . . . H30A H 0.0938 0.0736 0.4825 0.050 Uiso 1 1 calc R . . H30B H 0.1766 0.1583 0.4462 0.050 Uiso 1 1 calc R . . C303 C 0.0731(7) 0.2756(15) 0.3973(7) 0.037(3) Uani 1 1 d . . . C304 C 0.0961(9) 0.3500(18) 0.3144(7) 0.048(3) Uani 1 1 d . . . H30C H 0.1492 0.4153 0.3189 0.057 Uiso 1 1 calc R . . H30D H 0.0543 0.4411 0.2970 0.057 Uiso 1 1 calc R . . C305 C 0.1032(8) 0.1977(17) 0.2476(8) 0.046(3) Uani 1 1 d . . . H305 H 0.0964 0.2559 0.1926 0.056 Uiso 1 1 calc R . . C306 C -0.0109(8) 0.3032(19) 0.4265(9) 0.053(3) Uani 1 1 d . . . H30E H -0.0512 0.3576 0.3881 0.064 Uiso 1 1 calc R . . H30F H -0.0336 0.2107 0.4647 0.064 Uiso 1 1 calc R . . C307 C 0.1989(7) -0.0145(15) 0.3152(6) 0.036(3) Uani 1 1 d . . . C308 C 0.2767(8) -0.0909(16) 0.3271(7) 0.040(3) Uani 1 1 d . . . H308 H 0.2850 -0.1771 0.3700 0.048 Uiso 1 1 calc R . . C309 C 0.3423(7) -0.0433(18) 0.2772(7) 0.043(3) Uani 1 1 d . . . H309 H 0.3948 -0.0966 0.2861 0.051 Uiso 1 1 calc R . . C310 C 0.3305(8) 0.0818(19) 0.2147(7) 0.047(3) Uani 1 1 d . . . H310 H 0.3745 0.1147 0.1798 0.056 Uiso 1 1 calc R . . C311 C 0.2517(8) 0.1604(17) 0.2034(7) 0.043(3) Uani 1 1 d . . . H311 H 0.2431 0.2473 0.1608 0.052 Uiso 1 1 calc R . . C312 C 0.1879(8) 0.1125(16) 0.2532(7) 0.039(3) Uani 1 1 d . . . C313 C 0.0483(7) -0.0682(16) 0.3239(7) 0.041(3) Uani 1 1 d . . . C314 C -0.0108(7) -0.2032(16) 0.3410(7) 0.042(3) Uani 1 1 d . . . H314 H -0.0017 -0.2882 0.3842 0.050 Uiso 1 1 calc R . . C315 C -0.0831(8) -0.2138(19) 0.2949(7) 0.047(3) Uani 1 1 d . . . H315 H -0.1232 -0.3052 0.3063 0.056 Uiso 1 1 calc R . . C316 C -0.0950(8) -0.0867(18) 0.2318(8) 0.052(3) Uani 1 1 d . . . H316 H -0.1441 -0.0892 0.2005 0.062 Uiso 1 1 calc R . . C317 C -0.0350(8) 0.0427(16) 0.2151(8) 0.046(3) Uani 1 1 d . . . H317 H -0.0437 0.1272 0.1716 0.056 Uiso 1 1 calc R . . C318 C 0.0367(7) 0.0536(18) 0.2590(7) 0.044(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.079(6) 0.019(4) 0.049(5) 0.001(4) 0.008(4) -0.007(4) C101 0.075(9) 0.030(7) 0.037(7) 0.000(6) 0.002(6) -0.003(7) C102 0.079(10) 0.016(6) 0.054(8) -0.005(6) -0.002(7) -0.010(6) C103 0.063(8) 0.012(6) 0.039(6) 0.012(6) -0.010(5) -0.001(6) C104 0.061(8) 0.029(6) 0.041(7) -0.009(6) -0.007(6) 0.000(6) C105 0.062(8) 0.020(6) 0.035(6) -0.003(5) 0.006(6) -0.004(6) C106 0.066(9) 0.042(8) 0.047(7) 0.006(7) 0.003(6) -0.007(8) C107 0.050(7) 0.020(6) 0.042(7) -0.003(6) -0.010(6) -0.008(6) C108 0.072(8) 0.020(7) 0.030(6) -0.004(5) 0.000(6) -0.015(7) C109 0.060(8) 0.043(8) 0.041(7) 0.004(7) -0.012(6) -0.013(8) C110 0.062(8) 0.030(7) 0.055(8) 0.012(7) -0.013(6) -0.012(7) C111 0.065(8) 0.025(6) 0.040(7) 0.001(6) 0.002(6) 0.003(7) C112 0.062(8) 0.015(6) 0.041(6) 0.000(6) 0.006(5) -0.013(6) C113 0.053(8) 0.024(7) 0.049(7) 0.010(6) 0.000(6) -0.004(6) C114 0.076(10) 0.023(7) 0.044(7) 0.003(6) -0.021(7) 0.013(7) C115 0.085(11) 0.025(8) 0.054(8) 0.016(7) 0.007(7) 0.015(8) C116 0.068(9) 0.030(8) 0.060(8) -0.001(7) -0.003(7) -0.008(7) C117 0.062(8) 0.024(7) 0.040(6) -0.013(6) -0.006(6) -0.005(7) C118 0.079(9) 0.020(6) 0.040(7) -0.009(6) -0.023(6) 0.006(7) O2 0.058(5) 0.022(4) 0.052(5) -0.008(4) -0.011(4) 0.008(4) C201 0.051(7) 0.020(6) 0.050(7) 0.003(6) -0.019(6) -0.004(6) C202 0.049(7) 0.009(5) 0.047(7) 0.002(5) -0.007(6) 0.000(5) C203 0.055(7) 0.017(6) 0.046(7) 0.000(6) 0.001(6) 0.001(6) C204 0.059(8) 0.024(7) 0.039(7) -0.006(6) -0.006(5) 0.002(6) C205 0.047(7) 0.011(5) 0.053(7) -0.007(6) -0.015(5) 0.000(5) C206 0.054(7) 0.037(7) 0.041(7) -0.002(6) -0.009(6) 0.006(7) C207 0.050(7) 0.022(6) 0.040(7) -0.005(5) -0.005(6) 0.001(6) C208 0.049(7) 0.024(6) 0.049(7) 0.007(6) -0.014(6) 0.001(6) C209 0.059(8) 0.026(7) 0.036(6) -0.002(6) -0.012(5) 0.009(6) C210 0.060(7) 0.023(7) 0.038(6) -0.014(6) -0.020(6) 0.008(6) C211 0.051(7) 0.029(7) 0.038(6) -0.009(6) -0.001(6) 0.003(7) C212 0.061(8) 0.014(6) 0.053(7) -0.003(6) -0.007(6) 0.008(6) C213 0.046(7) 0.028(6) 0.042(7) 0.001(6) 0.004(6) 0.001(6) C214 0.040(7) 0.034(7) 0.042(7) -0.007(6) -0.016(5) 0.007(6) C215 0.051(7) 0.030(7) 0.047(7) -0.001(6) -0.015(5) 0.007(7) C216 0.051(7) 0.031(7) 0.049(7) 0.005(6) -0.003(6) 0.008(7) C217 0.050(7) 0.020(6) 0.043(6) -0.007(6) -0.008(5) 0.000(6) C218 0.056(7) 0.020(6) 0.050(7) -0.008(6) -0.006(6) -0.001(6) O3 0.063(5) 0.032(5) 0.044(4) -0.006(4) -0.009(4) -0.003(5) C301 0.067(8) 0.022(6) 0.038(6) 0.000(6) -0.010(6) -0.006(7) C302 0.050(7) 0.019(7) 0.057(7) 0.000(6) -0.007(6) -0.004(6) C303 0.059(8) 0.014(6) 0.037(6) -0.004(5) 0.005(5) -0.001(6) C304 0.067(8) 0.023(6) 0.053(8) 0.007(6) -0.002(6) -0.001(6) C305 0.073(9) 0.023(7) 0.043(7) 0.003(6) -0.002(6) 0.000(6) C306 0.068(9) 0.027(7) 0.064(8) -0.010(7) -0.007(7) 0.006(7) C307 0.054(7) 0.014(5) 0.039(6) 0.003(5) -0.020(5) 0.009(6) C308 0.073(9) 0.013(6) 0.033(6) -0.006(5) -0.021(6) 0.007(7) C309 0.050(7) 0.031(7) 0.048(7) 0.001(6) -0.010(6) 0.000(6) C310 0.063(8) 0.031(7) 0.047(7) -0.006(7) -0.011(6) 0.003(7) C311 0.070(9) 0.021(6) 0.038(7) 0.000(6) -0.007(6) -0.007(7) C312 0.064(8) 0.019(7) 0.035(6) -0.011(6) -0.013(6) 0.004(6) C313 0.072(8) 0.016(6) 0.035(6) 0.005(6) 0.006(5) 0.007(7) C314 0.061(8) 0.021(7) 0.044(7) -0.009(6) -0.007(6) 0.006(7) C315 0.067(8) 0.029(7) 0.045(7) 0.000(6) -0.010(6) 0.006(7) C316 0.056(8) 0.044(8) 0.055(8) -0.010(7) -0.018(6) 0.012(8) C317 0.059(8) 0.028(7) 0.051(7) 0.007(6) -0.013(6) 0.007(7) C318 0.054(8) 0.034(7) 0.045(7) -0.010(6) -0.005(6) 0.004(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C103 1.456(13) . ? O1 C106 1.442(15) . ? C101 H101 1.000 . ? C101 C102 1.565(17) . ? C101 C107 1.531(17) . ? C101 C113 1.529(18) . ? C102 H10A 0.990 . ? C102 H10B 0.990 . ? C102 C103 1.524(16) . ? C103 C104 1.498(17) . ? C103 C106 1.455(17) . ? C104 H10C 0.990 . ? C104 H10D 0.990 . ? C104 C105 1.544(17) . ? C105 H105 1.000 . ? C105 C112 1.496(16) . ? C105 C118 1.530(18) . ? C106 H10E 0.990 . ? C106 H10F 0.990 . ? C107 C108 1.374(16) . ? C107 C112 1.408(16) . ? C108 H108 0.950 . ? C108 C109 1.399(18) . ? C109 H109 0.950 . ? C109 C110 1.381(18) . ? C110 H110 0.950 . ? C110 C111 1.361(16) . ? C111 H111 0.950 . ? C111 C112 1.425(17) . ? C113 C114 1.376(18) . ? C113 C118 1.389(16) . ? C114 H114 0.950 . ? C114 C115 1.381(18) . ? C115 H115 0.950 . ? C115 C116 1.366(18) . ? C116 H116 0.950 . ? C116 C117 1.373(17) . ? C117 H117 0.950 . ? C117 C118 1.369(16) . ? O2 C203 1.451(13) . ? O2 C206 1.463(14) . ? C201 H201 1.000 . ? C201 C202 1.593(16) . ? C201 C207 1.517(16) . ? C201 C213 1.499(16) . ? C202 H20A 0.990 . ? C202 H20B 0.990 . ? C202 C203 1.507(16) . ? C203 C204 1.547(16) . ? C203 C206 1.478(16) . ? C204 H20C 0.990 . ? C204 H20D 0.990 . ? C204 C205 1.571(16) . ? C205 H205 1.000 . ? C205 C212 1.504(17) . ? C205 C218 1.491(16) . ? C206 H20E 0.990 . ? C206 H20F 0.990 . ? C207 C208 1.346(17) . ? C207 C212 1.422(17) . ? C208 H208 0.950 . ? C208 C209 1.409(16) . ? C209 H209 0.950 . ? C209 C210 1.386(17) . ? C210 H210 0.950 . ? C210 C211 1.355(17) . ? C211 H211 0.950 . ? C211 C212 1.395(16) . ? C213 C214 1.373(16) . ? C213 C218 1.421(16) . ? C214 H214 0.950 . ? C214 C215 1.395(17) . ? C215 H215 0.950 . ? C215 C216 1.391(17) . ? C216 H216 0.950 . ? C216 C217 1.391(15) . ? C217 H217 0.950 . ? C217 C218 1.369(16) . ? O3 C303 1.455(14) . ? O3 C306 1.453(15) . ? C301 H301 1.000 . ? C301 C302 1.556(16) . ? C301 C307 1.517(17) . ? C301 C313 1.509(17) . ? C302 H30A 0.990 . ? C302 H30B 0.990 . ? C302 C303 1.503(16) . ? C303 C304 1.510(16) . ? C303 C306 1.466(18) . ? C304 H30C 0.990 . ? C304 H30D 0.990 . ? C304 C305 1.559(18) . ? C305 H305 1.000 . ? C305 C312 1.515(18) . ? C305 C318 1.517(18) . ? C306 H30E 0.990 . ? C306 H30F 0.990 . ? C307 C308 1.397(16) . ? C307 C312 1.381(16) . ? C308 H308 0.950 . ? C308 C309 1.392(17) . ? C309 H309 0.950 . ? C309 C310 1.381(17) . ? C310 H310 0.950 . ? C310 C311 1.417(17) . ? C311 H311 0.950 . ? C311 C312 1.371(18) . ? C313 C314 1.402(17) . ? C313 C318 1.395(17) . ? C314 H314 0.950 . ? C314 C315 1.399(16) . ? C315 H315 0.950 . ? C315 C316 1.398(17) . ? C316 H316 0.950 . ? C316 C317 1.384(17) . ? C317 H317 0.950 . ? C317 C318 1.372(18) . ? 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 C103 O1 C106 60.3(8) . . ? H101 C101 C102 109.6 . . ? H101 C101 C107 109.6 . . ? H101 C101 C113 109.6 . . ? C102 C101 C107 108.2(10) . . ? C102 C101 C113 109.1(10) . . ? C107 C101 C113 110.8(10) . . ? C101 C102 H10A 109.0 . . ? C101 C102 H10B 109.0 . . ? C101 C102 C103 113.0(10) . . ? H10A C102 H10B 107.8 . . ? H10A C102 C103 109.0 . . ? H10B C102 C103 109.0 . . ? O1 C103 C102 111.9(9) . . ? O1 C103 C104 114.2(9) . . ? O1 C103 C106 59.4(7) . . ? C102 C103 C104 118.8(10) . . ? C102 C103 C106 117.9(11) . . ? C104 C103 C106 119.3(10) . . ? C103 C104 H10C 108.4 . . ? C103 C104 H10D 108.4 . . ? C103 C104 C105 115.5(9) . . ? H10C C104 H10D 107.5 . . ? H10C C104 C105 108.4 . . ? H10D C104 C105 108.4 . . ? C104 C105 H105 109.0 . . ? C104 C105 C112 110.7(10) . . ? C104 C105 C118 109.2(10) . . ? H105 C105 C112 109.0 . . ? H105 C105 C118 109.0 . . ? C112 C105 C118 110.0(9) . . ? O1 C106 C103 60.3(8) . . ? O1 C106 H10E 117.7 . . ? O1 C106 H10F 117.7 . . ? C103 C106 H10E 117.7 . . ? C103 C106 H10F 117.7 . . ? H10E C106 H10F 114.9 . . ? C101 C107 C108 122.9(10) . . ? C101 C107 C112 115.9(10) . . ? C108 C107 C112 121.3(11) . . ? C107 C108 H108 119.9 . . ? C107 C108 C109 120.2(10) . . ? H108 C108 C109 119.9 . . ? C108 C109 H109 120.2 . . ? C108 C109 C110 119.7(11) . . ? H109 C109 C110 120.2 . . ? C109 C110 H110 119.8 . . ? C109 C110 C111 120.5(13) . . ? H110 C110 C111 119.8 . . ? C110 C111 H111 119.2 . . ? C110 C111 C112 121.6(12) . . ? H111 C111 C112 119.2 . . ? C105 C112 C107 117.1(11) . . ? C105 C112 C111 125.9(10) . . ? C107 C112 C111 116.7(10) . . ? C101 C113 C114 123.3(11) . . ? C101 C113 C118 117.9(11) . . ? C114 C113 C118 118.7(12) . . ? C113 C114 H114 119.3 . . ? C113 C114 C115 121.3(12) . . ? H114 C114 C115 119.3 . . ? C114 C115 H115 120.2 . . ? C114 C115 C116 119.5(13) . . ? H115 C115 C116 120.2 . . ? C115 C116 H116 120.3 . . ? C115 C116 C117 119.4(13) . . ? H116 C116 C117 120.3 . . ? C116 C117 H117 119.2 . . ? C116 C117 C118 121.6(11) . . ? H117 C117 C118 119.2 . . ? C105 C118 C113 115.3(11) . . ? C105 C118 C117 125.3(10) . . ? C113 C118 C117 119.3(12) . . ? C203 O2 C206 61.0(7) . . ? H201 C201 C202 109.0 . . ? H201 C201 C207 109.0 . . ? H201 C201 C213 109.0 . . ? C202 C201 C207 109.0(9) . . ? C202 C201 C213 109.7(10) . . ? C207 C201 C213 111.1(9) . . ? C201 C202 H20A 109.1 . . ? C201 C202 H20B 109.1 . . ? C201 C202 C203 112.6(9) . . ? H20A C202 H20B 107.8 . . ? H20A C202 C203 109.1 . . ? H20B C202 C203 109.1 . . ? O2 C203 C202 113.1(9) . . ? O2 C203 C204 112.0(9) . . ? O2 C203 C206 59.9(7) . . ? C202 C203 C204 120.1(10) . . ? C202 C203 C206 119.1(10) . . ? C204 C203 C206 116.8(11) . . ? C203 C204 H20C 109.4 . . ? C203 C204 H20D 109.4 . . ? C203 C204 C205 111.1(9) . . ? H20C C204 H20D 108.0 . . ? H20C C204 C205 109.4 . . ? H20D C204 C205 109.4 . . ? C204 C205 H205 108.2 . . ? C204 C205 C212 109.4(9) . . ? C204 C205 C218 111.8(9) . . ? H205 C205 C212 108.2 . . ? H205 C205 C218 108.2 . . ? C212 C205 C218 110.9(10) . . ? O2 C206 C203 59.1(7) . . ? O2 C206 H20E 117.9 . . ? O2 C206 H20F 117.9 . . ? C203 C206 H20E 117.9 . . ? C203 C206 H20F 117.9 . . ? H20E C206 H20F 115.0 . . ? C201 C207 C208 122.5(11) . . ? C201 C207 C212 115.5(11) . . ? C208 C207 C212 121.8(11) . . ? C207 C208 H208 120.3 . . ? C207 C208 C209 119.4(12) . . ? H208 C208 C209 120.3 . . ? C208 C209 H209 120.9 . . ? C208 C209 C210 118.3(11) . . ? H209 C209 C210 120.9 . . ? C209 C210 H210 118.4 . . ? C209 C210 C211 123.1(10) . . ? H210 C210 C211 118.4 . . ? C210 C211 H211 120.5 . . ? C210 C211 C212 118.9(11) . . ? H211 C211 C212 120.5 . . ? C205 C212 C207 116.5(10) . . ? C205 C212 C211 125.1(11) . . ? C207 C212 C211 118.4(11) . . ? C201 C213 C214 122.5(11) . . ? C201 C213 C218 116.4(10) . . ? C214 C213 C218 121.1(11) . . ? C213 C214 H214 120.7 . . ? C213 C214 C215 118.7(11) . . ? H214 C214 C215 120.7 . . ? C214 C215 H215 119.7 . . ? C214 C215 C216 120.6(10) . . ? H215 C215 C216 119.7 . . ? C215 C216 H216 119.9 . . ? C215 C216 C217 120.2(12) . . ? H216 C216 C217 119.9 . . ? C216 C217 H217 120.0 . . ? C216 C217 C218 120.0(11) . . ? H217 C217 C218 120.0 . . ? C205 C218 C213 116.2(10) . . ? C205 C218 C217 124.3(10) . . ? C213 C218 C217 119.3(10) . . ? C303 O3 C306 60.6(8) . . ? H301 C301 C302 109.4 . . ? H301 C301 C307 109.4 . . ? H301 C301 C313 109.4 . . ? C302 C301 C307 108.2(9) . . ? C302 C301 C313 109.6(10) . . ? C307 C301 C313 110.9(9) . . ? C301 C302 H30A 109.0 . . ? C301 C302 H30B 109.0 . . ? C301 C302 C303 113.1(9) . . ? H30A C302 H30B 107.8 . . ? H30A C302 C303 109.0 . . ? H30B C302 C303 109.0 . . ? O3 C303 C302 114.5(9) . . ? O3 C303 C304 112.7(9) . . ? O3 C303 C306 59.7(7) . . ? C302 C303 C304 118.9(11) . . ? C302 C303 C306 117.6(11) . . ? C304 C303 C306 118.8(11) . . ? C303 C304 H30C 108.9 . . ? C303 C304 H30D 108.9 . . ? C303 C304 C305 113.4(10) . . ? H30C C304 H30D 107.7 . . ? H30C C304 C305 108.9 . . ? H30D C304 C305 108.9 . . ? C304 C305 H305 108.9 . . ? C304 C305 C312 108.4(10) . . ? C304 C305 C318 110.2(10) . . ? H305 C305 C312 108.9 . . ? H305 C305 C318 108.9 . . ? C312 C305 C318 111.3(10) . . ? O3 C306 C303 59.8(8) . . ? O3 C306 H30E 117.8 . . ? O3 C306 H30F 117.8 . . ? C303 C306 H30E 117.8 . . ? C303 C306 H30F 117.8 . . ? H30E C306 H30F 114.9 . . ? C301 C307 C308 123.4(10) . . ? C301 C307 C312 117.5(11) . . ? C308 C307 C312 118.8(11) . . ? C307 C308 H308 119.4 . . ? C307 C308 C309 121.3(10) . . ? H308 C308 C309 119.4 . . ? C308 C309 H309 120.2 . . ? C308 C309 C310 119.6(11) . . ? H309 C309 C310 120.2 . . ? C309 C310 H310 120.5 . . ? C309 C310 C311 118.9(12) . . ? H310 C310 C311 120.5 . . ? C310 C311 H311 119.6 . . ? C310 C311 C312 120.8(11) . . ? H311 C311 C312 119.6 . . ? C305 C312 C307 115.6(12) . . ? C305 C312 C311 123.7(11) . . ? C307 C312 C311 120.6(12) . . ? C301 C313 C314 123.0(10) . . ? C301 C313 C318 116.8(11) . . ? C314 C313 C318 120.2(11) . . ? C313 C314 H314 119.7 . . ? C313 C314 C315 120.6(12) . . ? H314 C314 C315 119.7 . . ? C314 C315 H315 120.8 . . ? C314 C315 C316 118.5(13) . . ? H315 C315 C316 120.8 . . ? C315 C316 H316 120.1 . . ? C315 C316 C317 119.8(11) . . ? H316 C316 C317 120.1 . . ? C316 C317 H317 118.7 . . ? C316 C317 C318 122.5(11) . . ? H317 C317 C318 118.7 . . ? C305 C318 C313 115.8(10) . . ? C305 C318 C317 125.7(11) . . ? C313 C318 C317 118.4(12) . . ? 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 C107 C101 C102 C103 83.6(13) . . . . ? C113 C101 C102 C103 -37.0(14) . . . . ? C106 O1 C103 C102 -110.4(12) . . . . ? C106 O1 C103 C104 110.9(11) . . . . ? C101 C102 C103 O1 174.1(11) . . . . ? C101 C102 C103 C104 -49.3(16) . . . . ? C101 C102 C103 C106 108.2(13) . . . . ? O1 C103 C104 C105 -175.1(11) . . . . ? C102 C103 C104 C105 49.3(15) . . . . ? C106 C103 C104 C105 -107.9(13) . . . . ? C103 C104 C105 C112 -82.7(13) . . . . ? C103 C104 C105 C118 38.5(14) . . . . ? C102 C103 C106 O1 100.2(11) . . . . ? C104 C103 C106 O1 -102.4(11) . . . . ? C102 C101 C107 C108 100.9(13) . . . . ? C102 C101 C107 C112 -79.9(13) . . . . ? C113 C101 C107 C108 -139.5(11) . . . . ? C113 C101 C107 C112 39.7(14) . . . . ? C101 C107 C108 C109 -178.3(11) . . . . ? C112 C107 C108 C109 2.5(18) . . . . ? C107 C108 C109 C110 -2.2(17) . . . . ? C108 C109 C110 C111 1.8(18) . . . . ? C109 C110 C111 C112 -1.6(18) . . . . ? C101 C107 C112 C105 4.5(15) . . . . ? C101 C107 C112 C111 178.5(10) . . . . ? C108 C107 C112 C105 -176.3(10) . . . . ? C108 C107 C112 C111 -2.2(17) . . . . ? C110 C111 C112 C105 175.2(11) . . . . ? C110 C111 C112 C107 1.8(17) . . . . ? C104 C105 C112 C107 72.7(13) . . . . ? C104 C105 C112 C111 -100.8(13) . . . . ? C118 C105 C112 C107 -48.1(13) . . . . ? C118 C105 C112 C111 138.4(11) . . . . ? C102 C101 C113 C114 -102.0(14) . . . . ? C102 C101 C113 C118 78.0(13) . . . . ? C107 C101 C113 C114 139.0(12) . . . . ? C107 C101 C113 C118 -41.0(14) . . . . ? C101 C113 C114 C115 178.4(11) . . . . ? C118 C113 C114 C115 -1.6(18) . . . . ? C113 C114 C115 C116 1.5(18) . . . . ? C114 C115 C116 C117 -1.0(18) . . . . ? C115 C116 C117 C118 0.7(19) . . . . ? C116 C117 C118 C105 -176.8(12) . . . . ? C116 C117 C118 C113 -0.8(18) . . . . ? C101 C113 C118 C105 -2.3(15) . . . . ? C101 C113 C118 C117 -178.7(11) . . . . ? C114 C113 C118 C105 177.6(11) . . . . ? C114 C113 C118 C117 1.2(17) . . . . ? C104 C105 C118 C113 -74.9(12) . . . . ? C104 C105 C118 C117 101.3(13) . . . . ? C112 C105 C118 C113 46.8(13) . . . . ? C112 C105 C118 C117 -137.0(12) . . . . ? C207 C201 C202 C203 84.5(12) . . . . ? C213 C201 C202 C203 -37.3(12) . . . . ? C206 O2 C203 C202 -111.3(11) . . . . ? C206 O2 C203 C204 109.1(11) . . . . ? C201 C202 C203 O2 172.6(9) . . . . ? C201 C202 C203 C204 -51.4(13) . . . . ? C201 C202 C203 C206 105.3(12) . . . . ? O2 C203 C204 C205 -172.8(8) . . . . ? C202 C203 C204 C205 50.8(13) . . . . ? C206 C203 C204 C205 -106.5(12) . . . . ? C203 C204 C205 C212 -84.4(12) . . . . ? C203 C204 C205 C218 38.8(13) . . . . ? C202 C203 C206 O2 101.4(10) . . . . ? C204 C203 C206 O2 -101.1(11) . . . . ? C202 C201 C207 C208 98.9(13) . . . . ? C202 C201 C207 C212 -76.5(12) . . . . ? C213 C201 C207 C208 -140.1(12) . . . . ? C213 C201 C207 C212 44.5(14) . . . . ? C201 C207 C208 C209 -177.4(10) . . . . ? C212 C207 C208 C209 -2.3(18) . . . . ? C207 C208 C209 C210 1.3(16) . . . . ? C208 C209 C210 C211 -0.9(16) . . . . ? C209 C210 C211 C212 1.4(18) . . . . ? C210 C211 C212 C205 176.8(11) . . . . ? C210 C211 C212 C207 -2.3(16) . . . . ? C201 C207 C212 C205 -0.9(14) . . . . ? C201 C207 C212 C211 178.3(10) . . . . ? C208 C207 C212 C205 -176.4(12) . . . . ? C208 C207 C212 C211 2.8(17) . . . . ? C204 C205 C212 C207 79.6(12) . . . . ? C204 C205 C212 C211 -99.5(12) . . . . ? C218 C205 C212 C207 -44.2(13) . . . . ? C218 C205 C212 C211 136.7(11) . . . . ? C202 C201 C213 C214 -101.7(13) . . . . ? C202 C201 C213 C218 77.6(12) . . . . ? C207 C201 C213 C214 137.8(12) . . . . ? C207 C201 C213 C218 -43.0(15) . . . . ? C201 C213 C214 C215 -179.7(11) . . . . ? C218 C213 C214 C215 1.0(17) . . . . ? C213 C214 C215 C216 -2.4(17) . . . . ? C214 C215 C216 C217 2.3(18) . . . . ? C215 C216 C217 C218 -0.7(18) . . . . ? C216 C217 C218 C205 -176.9(11) . . . . ? C216 C217 C218 C213 -0.7(16) . . . . ? C201 C213 C218 C205 -2.3(15) . . . . ? C201 C213 C218 C217 -178.8(10) . . . . ? C214 C213 C218 C205 177.0(11) . . . . ? C214 C213 C218 C217 0.5(17) . . . . ? C204 C205 C218 C213 -76.4(12) . . . . ? C204 C205 C218 C217 99.9(13) . . . . ? C212 C205 C218 C213 46.0(13) . . . . ? C212 C205 C218 C217 -137.7(11) . . . . ? C307 C301 C302 C303 84.5(12) . . . . ? C313 C301 C302 C303 -36.5(13) . . . . ? C306 O3 C303 C302 -108.9(12) . . . . ? C306 O3 C303 C304 111.1(13) . . . . ? C301 C302 C303 O3 171.1(9) . . . . ? C301 C302 C303 C304 -51.5(14) . . . . ? C301 C302 C303 C306 104.0(13) . . . . ? O3 C303 C304 C305 -171.7(10) . . . . ? C302 C303 C304 C305 50.2(16) . . . . ? C306 C303 C304 C305 -104.9(13) . . . . ? C303 C304 C305 C312 -83.7(14) . . . . ? C303 C304 C305 C318 38.4(15) . . . . ? C302 C303 C306 O3 103.6(11) . . . . ? C304 C303 C306 O3 -100.9(11) . . . . ? C302 C301 C307 C308 98.0(12) . . . . ? C302 C301 C307 C312 -76.1(12) . . . . ? C313 C301 C307 C308 -141.8(11) . . . . ? C313 C301 C307 C312 44.1(13) . . . . ? C301 C307 C308 C309 -174.9(11) . . . . ? C312 C307 C308 C309 -0.9(16) . . . . ? C307 C308 C309 C310 0.0(17) . . . . ? C308 C309 C310 C311 0.7(17) . . . . ? C309 C310 C311 C312 -0.5(18) . . . . ? C310 C311 C312 C305 176.8(11) . . . . ? C310 C311 C312 C307 -0.4(17) . . . . ? C301 C307 C312 C305 -2.0(15) . . . . ? C301 C307 C312 C311 175.5(11) . . . . ? C308 C307 C312 C305 -176.4(10) . . . . ? C308 C307 C312 C311 1.1(16) . . . . ? C304 C305 C312 C307 78.5(12) . . . . ? C304 C305 C312 C311 -98.9(13) . . . . ? C318 C305 C312 C307 -42.9(14) . . . . ? C318 C305 C312 C311 139.7(11) . . . . ? C302 C301 C313 C314 -103.2(12) . . . . ? C302 C301 C313 C318 78.6(13) . . . . ? C307 C301 C313 C314 137.4(11) . . . . ? C307 C301 C313 C318 -40.7(14) . . . . ? C301 C313 C314 C315 179.8(11) . . . . ? C318 C313 C314 C315 -2.1(17) . . . . ? C313 C314 C315 C316 -0.1(17) . . . . ? C314 C315 C316 C317 1.5(18) . . . . ? C315 C316 C317 C318 -0.7(19) . . . . ? C316 C317 C318 C305 -176.4(11) . . . . ? C316 C317 C318 C313 -1.5(18) . . . . ? C301 C313 C318 C305 -3.5(16) . . . . ? C301 C313 C318 C317 -178.9(11) . . . . ? C314 C313 C318 C305 178.2(10) . . . . ? C314 C313 C318 C317 2.8(17) . . . . ? C304 C305 C318 C313 -74.4(13) . . . . ? C304 C305 C318 C317 100.6(14) . . . . ? C312 C305 C318 C313 46.0(15) . . . . ? C312 C305 C318 C317 -139.0(12) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.256 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.061 # Attachment 'str0215.cif' data_str0215 _database_code_depnum_ccdc_archive 'CCDC 701932' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 N2' _chemical_formula_weight 260.33 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 13.8169(18) _cell_length_b 11.8799(15) _cell_length_c 8.5789(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.271(2) _cell_angle_gamma 90.00 _cell_volume 1385.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9753 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12052 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3318 _reflns_number_gt 2412 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0685P)^2^+0.2468P] 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 3318 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1536 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.31821(17) 0.3225(2) 0.5809(3) 0.0728(6) Uani 1 1 d . . . H1N H 0.326(2) 0.253(3) 0.542(4) 0.114(12) Uiso 1 1 d . . . H2N H 0.375(2) 0.344(2) 0.649(3) 0.087(9) Uiso 1 1 d . . . N2 N 0.45773(12) 0.37057(15) 0.3058(2) 0.0629(5) Uani 1 1 d . . . C1 C 0.30283(12) 0.59834(14) 0.2434(2) 0.0411(4) Uani 1 1 d . . . C2 C 0.38276(14) 0.65311(16) 0.2014(2) 0.0494(5) Uani 1 1 d . . . H2A H 0.4159 0.7080 0.2676 0.059 Uiso 1 1 calc R . . C3 C 0.41334(16) 0.62624(18) 0.0611(2) 0.0585(5) Uani 1 1 d . . . H3A H 0.4681 0.6616 0.0343 0.070 Uiso 1 1 calc R . . C4 C 0.36305(16) 0.5477(2) -0.0382(2) 0.0621(6) Uani 1 1 d . . . H4A H 0.3835 0.5305 -0.1330 0.075 Uiso 1 1 calc R . . C5 C 0.28187(15) 0.49364(18) 0.0011(2) 0.0552(5) Uani 1 1 d . . . H5A H 0.2475 0.4412 -0.0681 0.066 Uiso 1 1 calc R . . C6 C 0.25163(12) 0.51748(15) 0.14342(19) 0.0425(4) Uani 1 1 d . . . C7 C 0.26875(12) 0.61729(15) 0.3991(2) 0.0440(4) Uani 1 1 d . . . H7A H 0.2957 0.6888 0.4445 0.053 Uiso 1 1 calc R . . C8 C 0.15785(13) 0.62316(15) 0.3723(2) 0.0455(4) Uani 1 1 d . . . C9 C 0.10652(16) 0.70077(17) 0.4470(3) 0.0608(5) Uani 1 1 d . . . H9A H 0.1403 0.7557 0.5125 0.073 Uiso 1 1 calc R . . C10 C 0.00491(17) 0.6961(2) 0.4237(3) 0.0709(6) Uani 1 1 d . . . H10A H -0.0295 0.7479 0.4742 0.085 Uiso 1 1 calc R . . C11 C -0.04540(16) 0.6161(2) 0.3269(3) 0.0702(7) Uani 1 1 d . . . H11A H -0.1137 0.6135 0.3121 0.084 Uiso 1 1 calc R . . C12 C 0.00530(14) 0.53908(19) 0.2513(3) 0.0610(5) Uani 1 1 d . . . H12A H -0.0290 0.4850 0.1850 0.073 Uiso 1 1 calc R . . C13 C 0.10726(13) 0.54221(15) 0.2738(2) 0.0459(4) Uani 1 1 d . . . C14 C 0.16940(12) 0.45725(15) 0.2042(2) 0.0458(4) Uani 1 1 d . . . H14A H 0.1280 0.4187 0.1155 0.055 Uiso 1 1 calc R . . C15 C 0.21067(13) 0.36917(15) 0.3318(2) 0.0481(4) Uani 1 1 d . . . H15A H 0.1601 0.3528 0.3938 0.058 Uiso 1 1 calc R . . H15B H 0.2235 0.3002 0.2785 0.058 Uiso 1 1 calc R . . C16 C 0.30533(13) 0.40244(16) 0.4467(2) 0.0466(4) Uani 1 1 d . . . C17 C 0.30562(13) 0.52145(16) 0.5161(2) 0.0475(4) Uani 1 1 d . . . H17A H 0.3723 0.5391 0.5672 0.057 Uiso 1 1 calc R . . H17B H 0.2653 0.5208 0.5979 0.057 Uiso 1 1 calc R . . C18 C 0.39068(13) 0.38916(15) 0.3624(2) 0.0476(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0706(14) 0.0799(16) 0.0704(13) 0.0321(12) 0.0194(11) 0.0077(12) N2 0.0478(10) 0.0673(12) 0.0760(12) 0.0017(9) 0.0172(9) 0.0092(8) C1 0.0429(9) 0.0387(9) 0.0419(9) 0.0015(7) 0.0081(7) 0.0016(7) C2 0.0502(10) 0.0449(10) 0.0553(11) 0.0042(8) 0.0153(9) -0.0039(8) C3 0.0581(12) 0.0641(13) 0.0571(12) 0.0170(10) 0.0206(10) 0.0032(10) C4 0.0670(13) 0.0839(15) 0.0393(10) 0.0103(10) 0.0198(9) 0.0154(12) C5 0.0600(12) 0.0662(13) 0.0372(9) -0.0051(9) 0.0022(8) 0.0073(10) C6 0.0420(9) 0.0467(10) 0.0374(9) -0.0011(7) 0.0031(7) 0.0048(8) C7 0.0448(10) 0.0429(9) 0.0458(10) -0.0128(7) 0.0123(8) -0.0104(7) C8 0.0476(10) 0.0424(10) 0.0490(10) -0.0011(8) 0.0153(8) 0.0005(8) C9 0.0686(13) 0.0477(11) 0.0720(14) -0.0059(10) 0.0280(11) 0.0049(10) C10 0.0679(14) 0.0637(14) 0.0897(16) 0.0081(13) 0.0371(13) 0.0227(12) C11 0.0449(11) 0.0818(16) 0.0856(17) 0.0163(13) 0.0165(11) 0.0174(11) C12 0.0407(10) 0.0719(14) 0.0682(13) 0.0025(11) 0.0038(9) 0.0029(9) C13 0.0400(9) 0.0476(10) 0.0493(10) 0.0007(8) 0.0061(8) 0.0023(8) C14 0.0388(9) 0.0494(10) 0.0464(10) -0.0130(8) 0.0002(7) -0.0054(8) C15 0.0430(10) 0.0409(9) 0.0625(11) -0.0043(8) 0.0151(8) -0.0071(8) C16 0.0415(9) 0.0539(11) 0.0458(10) 0.0103(8) 0.0117(8) 0.0011(8) C17 0.0418(9) 0.0665(12) 0.0340(8) -0.0059(8) 0.0066(7) -0.0066(8) C18 0.0406(10) 0.0475(10) 0.0540(11) 0.0064(8) 0.0068(8) 0.0020(8) _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 C16 1.478(2) . ? N2 C18 1.141(2) . ? C1 C2 1.384(2) . ? C1 C6 1.394(2) . ? C1 C7 1.510(2) . ? C2 C3 1.382(3) . ? C3 C4 1.366(3) . ? C4 C5 1.385(3) . ? C5 C6 1.388(2) . ? C6 C14 1.512(3) . ? C7 C8 1.510(2) . ? C7 C17 1.543(3) . ? C8 C13 1.384(3) . ? C8 C9 1.388(3) . ? C9 C10 1.383(3) . ? C10 C11 1.367(3) . ? C11 C12 1.383(3) . ? C12 C13 1.388(3) . ? C13 C14 1.515(2) . ? C14 C15 1.548(3) . ? C15 C16 1.542(3) . ? C16 C18 1.498(3) . ? C16 C17 1.534(3) . ? 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 C2 C1 C6 120.31(16) . . ? C2 C1 C7 123.33(16) . . ? C6 C1 C7 116.31(15) . . ? C3 C2 C1 120.02(19) . . ? C4 C3 C2 120.00(19) . . ? C3 C4 C5 120.59(18) . . ? C4 C5 C6 120.19(19) . . ? C5 C6 C1 118.86(17) . . ? C5 C6 C14 124.70(17) . . ? C1 C6 C14 116.36(14) . . ? C8 C7 C1 109.87(14) . . ? C8 C7 C17 109.98(14) . . ? C1 C7 C17 110.28(14) . . ? C13 C8 C9 119.96(18) . . ? C13 C8 C7 116.69(15) . . ? C9 C8 C7 123.26(17) . . ? C10 C9 C8 119.7(2) . . ? C11 C10 C9 120.6(2) . . ? C10 C11 C12 120.0(2) . . ? C11 C12 C13 120.2(2) . . ? C8 C13 C12 119.56(18) . . ? C8 C13 C14 116.32(15) . . ? C12 C13 C14 124.03(17) . . ? C6 C14 C13 109.52(15) . . ? C6 C14 C15 111.05(14) . . ? C13 C14 C15 109.54(15) . . ? C16 C15 C14 116.25(14) . . ? N1 C16 C18 108.22(15) . . ? N1 C16 C17 107.36(17) . . ? C18 C16 C17 109.69(15) . . ? N1 C16 C15 107.68(16) . . ? C18 C16 C15 108.36(15) . . ? C17 C16 C15 115.31(15) . . ? C16 C17 C7 116.74(14) . . ? N2 C18 C16 173.91(19) . . ? 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 -1.2(3) . . . . ? C7 C1 C2 C3 175.95(17) . . . . ? C1 C2 C3 C4 1.7(3) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C4 C5 C6 C1 1.5(3) . . . . ? C4 C5 C6 C14 -174.95(18) . . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? C7 C1 C6 C5 -177.77(16) . . . . ? C2 C1 C6 C14 176.35(16) . . . . ? C7 C1 C6 C14 -1.0(2) . . . . ? C2 C1 C7 C8 138.35(17) . . . . ? C6 C1 C7 C8 -44.4(2) . . . . ? C2 C1 C7 C17 -100.27(19) . . . . ? C6 C1 C7 C17 76.99(18) . . . . ? C1 C7 C8 C13 45.1(2) . . . . ? C17 C7 C8 C13 -76.43(19) . . . . ? C1 C7 C8 C9 -138.26(18) . . . . ? C17 C7 C8 C9 100.2(2) . . . . ? C13 C8 C9 C10 0.5(3) . . . . ? C7 C8 C9 C10 -175.95(19) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 C13 0.4(3) . . . . ? C9 C8 C13 C12 -0.3(3) . . . . ? C7 C8 C13 C12 176.44(17) . . . . ? C9 C8 C13 C14 -176.87(17) . . . . ? C7 C8 C13 C14 -0.2(2) . . . . ? C11 C12 C13 C8 -0.2(3) . . . . ? C11 C12 C13 C14 176.12(19) . . . . ? C5 C6 C14 C13 -137.68(18) . . . . ? C1 C6 C14 C13 45.8(2) . . . . ? C5 C6 C14 C15 101.2(2) . . . . ? C1 C6 C14 C15 -75.35(19) . . . . ? C8 C13 C14 C6 -45.2(2) . . . . ? C12 C13 C14 C6 138.39(19) . . . . ? C8 C13 C14 C15 76.83(19) . . . . ? C12 C13 C14 C15 -99.6(2) . . . . ? C6 C14 C15 C16 37.6(2) . . . . ? C13 C14 C15 C16 -83.53(18) . . . . ? C14 C15 C16 N1 165.88(16) . . . . ? C14 C15 C16 C18 -77.28(19) . . . . ? C14 C15 C16 C17 46.1(2) . . . . ? N1 C16 C17 C7 -165.77(15) . . . . ? C18 C16 C17 C7 76.85(19) . . . . ? C15 C16 C17 C7 -45.8(2) . . . . ? C8 C7 C17 C16 82.97(18) . . . . ? C1 C7 C17 C16 -38.3(2) . . . . ? N1 C16 C18 N2 12(2) . . . . ? C17 C16 C18 N2 128.5(19) . . . . ? C15 C16 C18 N2 -104.9(19) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.229 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.033