# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sa2398a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N2 O2' _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_weight 292.33 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' 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 21.092(13) _cell_length_b 6.521(3) _cell_length_c 12.149(7) _cell_angle_alpha 90.00 _cell_angle_beta 119.587(8) _cell_angle_gamma 90.00 _cell_volume 1453.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2651 _cell_measurement_theta_min 1.92 _cell_measurement_theta_max 27.48 _exptl_crystal_description 1.86 _exptl_crystal_colour 26.49 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2185 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6159 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2101 _reflns_number_gt 2033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'Olex2 ver 1.1' _computing_molecular_graphics 'Olex2 ver 1.1' _computing_publication_material 'SHELX97 (Sheldrick, 2008)' _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^)+(0.0648P)^2^+1.0151P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_ls_number_reflns 2101 _refine_ls_number_parameters 201 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1341 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.41373(14) 0.2497(4) 0.5318(2) 0.0455(6) Uani 1 1 d . . . O2 O 0.49516(15) 0.4875(4) 0.6540(2) 0.0464(6) Uani 1 1 d . . . N1 N 0.63182(17) 1.3631(4) 0.5773(3) 0.0401(7) Uani 1 1 d . . . N2 N 0.36675(17) 0.2078(4) 0.3987(3) 0.0441(7) Uani 1 1 d . . . C1 C 0.33750(18) 0.3596(5) 0.1973(3) 0.0344(7) Uani 1 1 d . . . C2 C 0.2948(2) 0.5290(5) 0.1341(3) 0.0424(8) Uani 1 1 d . . . H2 H 0.2910 0.6402 0.1810 0.051 Uiso 1 1 calc R . . C3 C 0.2580(2) 0.5360(6) 0.0031(3) 0.0468(9) Uani 1 1 d . . . H3 H 0.2273 0.6491 -0.0399 0.056 Uiso 1 1 calc R . . C4 C 0.2659(2) 0.3776(6) -0.0651(3) 0.0456(9) Uani 1 1 d . . . H4 H 0.2420 0.3848 -0.1548 0.055 Uiso 1 1 calc R . . C5 C 0.3082(2) 0.2102(6) -0.0037(4) 0.0477(9) Uani 1 1 d . . . H5 H 0.3132 0.1014 -0.0509 0.057 Uiso 1 1 calc R . . C6 C 0.3438(2) 0.2006(5) 0.1277(4) 0.0439(8) Uani 1 1 d . . . H6 H 0.3726 0.0841 0.1701 0.053 Uiso 1 1 calc R . . C7 C 0.37829(18) 0.3549(5) 0.3378(3) 0.0358(7) Uani 1 1 d . . . C8 C 0.43067(18) 0.5042(5) 0.4202(3) 0.0342(7) Uani 1 1 d . . . C9 C 0.45258(19) 0.4300(5) 0.5481(3) 0.0385(7) Uani 1 1 d . . . C10 C 0.45520(19) 0.6636(5) 0.3776(3) 0.0352(7) Uani 1 1 d . . . H10 H 0.4353 0.6617 0.2883 0.042 Uiso 1 1 calc R . . C11 C 0.50370(19) 0.8316(5) 0.4365(3) 0.0345(7) Uani 1 1 d . . . C12 C 0.53878(19) 0.8819(5) 0.5668(3) 0.0366(7) Uani 1 1 d . . . H12 H 0.5318 0.7962 0.6231 0.044 Uiso 1 1 calc R . . C13 C 0.5825(2) 1.0510(5) 0.6134(3) 0.0395(8) Uani 1 1 d . . . H13 H 0.6064 1.0775 0.7017 0.047 Uiso 1 1 calc R . . C14 C 0.59307(18) 1.1877(5) 0.5331(3) 0.0333(7) Uani 1 1 d . . . C15 C 0.56036(19) 1.1336(5) 0.4037(3) 0.0357(7) Uani 1 1 d . . . H15 H 0.5683 1.2175 0.3477 0.043 Uiso 1 1 calc R . . C16 C 0.51743(19) 0.9624(5) 0.3576(3) 0.0350(7) Uani 1 1 d . . . H16 H 0.4963 0.9307 0.2702 0.042 Uiso 1 1 calc R . . C17 C 0.6702(2) 1.4131(6) 0.7111(3) 0.0507(10) Uani 1 1 d . . . H17A H 0.7094 1.3134 0.7568 0.076 Uiso 1 1 calc R . . H17B H 0.6361 1.4088 0.7439 0.076 Uiso 1 1 calc R . . H17C H 0.6911 1.5510 0.7230 0.076 Uiso 1 1 calc R . . C18 C 0.6445(2) 1.4983(6) 0.4947(4) 0.0463(9) Uani 1 1 d . . . H18A H 0.5980 1.5291 0.4188 0.069 Uiso 1 1 calc R . . H18B H 0.6772 1.4306 0.4701 0.069 Uiso 1 1 calc R . . H18C H 0.6670 1.6260 0.5396 0.069 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 O1 0.0481(15) 0.0454(13) 0.0443(13) 0.0122(11) 0.0238(12) 0.0017(11) O2 0.0579(16) 0.0499(14) 0.0351(12) 0.0068(11) 0.0257(12) 0.0033(13) N1 0.0483(17) 0.0411(15) 0.0320(14) -0.0051(12) 0.0207(13) -0.0057(13) N2 0.0480(18) 0.0424(16) 0.0402(16) 0.0075(13) 0.0204(14) -0.0010(14) C1 0.0345(16) 0.0369(16) 0.0350(16) -0.0020(14) 0.0197(14) -0.0027(14) C2 0.057(2) 0.0397(17) 0.0372(17) 0.0026(14) 0.0283(17) 0.0091(16) C3 0.062(2) 0.0432(18) 0.0402(19) 0.0058(16) 0.0289(19) 0.0116(18) C4 0.051(2) 0.050(2) 0.0381(19) -0.0077(15) 0.0232(18) -0.0049(17) C5 0.049(2) 0.045(2) 0.047(2) -0.0161(17) 0.0222(18) -0.0016(17) C6 0.0387(18) 0.0369(16) 0.0470(19) -0.0077(15) 0.0140(16) 0.0021(15) C7 0.0356(17) 0.0342(16) 0.0412(18) 0.0042(14) 0.0217(15) 0.0046(13) C8 0.0349(16) 0.0360(15) 0.0353(15) 0.0049(13) 0.0202(13) 0.0040(13) C9 0.0433(19) 0.0383(17) 0.0380(17) 0.0067(15) 0.0231(15) 0.0052(15) C10 0.0422(18) 0.0385(16) 0.0315(16) 0.0018(13) 0.0232(15) 0.0020(13) C11 0.0456(19) 0.0322(15) 0.0345(17) -0.0002(13) 0.0266(15) 0.0037(14) C12 0.048(2) 0.0380(16) 0.0301(16) 0.0035(13) 0.0247(15) 0.0021(15) C13 0.049(2) 0.0436(17) 0.0304(16) -0.0001(14) 0.0227(16) 0.0009(16) C14 0.0353(16) 0.0352(15) 0.0302(15) 0.0000(12) 0.0168(13) 0.0026(13) C15 0.0457(19) 0.0356(16) 0.0316(16) 0.0019(13) 0.0235(15) -0.0012(14) C16 0.0457(19) 0.0372(16) 0.0293(15) -0.0009(12) 0.0241(15) 0.0008(14) C17 0.056(2) 0.053(2) 0.0343(18) -0.0072(17) 0.0154(17) -0.0100(18) C18 0.060(2) 0.0415(18) 0.049(2) -0.0029(16) 0.0361(19) -0.0070(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.390(4) . ? O1 N2 1.445(4) . ? O2 C9 1.209(4) . ? N1 C14 1.353(4) . ? N1 C17 1.451(4) . ? N1 C18 1.456(5) . ? N2 C7 1.306(4) . ? C1 C6 1.385(5) . ? C1 C2 1.392(5) . ? C1 C7 1.484(5) . ? C2 C3 1.384(5) . ? C2 H2 0.9500 . ? C3 C4 1.385(5) . ? C3 H3 0.9500 . ? C4 C5 1.373(5) . ? C4 H4 0.9500 . ? C5 C6 1.390(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.441(5) . ? C8 C10 1.371(5) . ? C8 C9 1.468(5) . ? C10 C11 1.427(5) . ? C10 H10 0.9500 . ? C11 C12 1.416(4) . ? C11 C16 1.416(4) . ? C12 C13 1.368(5) . ? C12 H12 0.9500 . ? C13 C14 1.418(5) . ? C13 H13 0.9500 . ? C14 C15 1.415(4) . ? C15 C16 1.371(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 C9 O1 N2 110.5(2) . . ? C14 N1 C17 121.9(3) . . ? C14 N1 C18 121.3(3) . . ? C17 N1 C18 116.4(3) . . ? C7 N2 O1 106.2(3) . . ? C6 C1 C2 119.2(3) . . ? C6 C1 C7 120.7(3) . . ? C2 C1 C7 120.0(3) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 120.5(3) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? N2 C7 C8 113.3(3) . . ? N2 C7 C1 120.1(3) . . ? C8 C7 C1 126.5(3) . . ? C10 C8 C7 123.5(3) . . ? C10 C8 C9 132.0(3) . . ? C7 C8 C9 104.2(3) . . ? O2 C9 O1 119.4(3) . . ? O2 C9 C8 134.8(3) . . ? O1 C9 C8 105.8(3) . . ? C8 C10 C11 134.7(3) . . ? C8 C10 H10 112.6 . . ? C11 C10 H10 112.6 . . ? C12 C11 C16 116.6(3) . . ? C12 C11 C10 126.0(3) . . ? C16 C11 C10 117.3(3) . . ? C13 C12 C11 121.5(3) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 121.7(3) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? N1 C14 C15 121.3(3) . . ? N1 C14 C13 121.9(3) . . ? C15 C14 C13 116.9(3) . . ? C16 C15 C14 121.2(3) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 122.0(3) . . ? C15 C16 H16 119.0 . . ? C11 C16 H16 119.0 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C9 O1 N2 C7 1.3(4) . . . . ? C6 C1 C2 C3 1.3(6) . . . . ? C7 C1 C2 C3 178.6(3) . . . . ? C1 C2 C3 C4 -2.6(6) . . . . ? C2 C3 C4 C5 2.2(6) . . . . ? C3 C4 C5 C6 -0.6(6) . . . . ? C2 C1 C6 C5 0.3(6) . . . . ? C7 C1 C6 C5 -176.9(3) . . . . ? C4 C5 C6 C1 -0.7(6) . . . . ? O1 N2 C7 C8 -0.9(4) . . . . ? O1 N2 C7 C1 -179.3(3) . . . . ? C6 C1 C7 N2 -61.1(4) . . . . ? C2 C1 C7 N2 121.7(4) . . . . ? C6 C1 C7 C8 120.8(4) . . . . ? C2 C1 C7 C8 -56.4(5) . . . . ? N2 C7 C8 C10 175.1(3) . . . . ? C1 C7 C8 C10 -6.6(5) . . . . ? N2 C7 C8 C9 0.2(4) . . . . ? C1 C7 C8 C9 178.4(3) . . . . ? N2 O1 C9 O2 -179.4(3) . . . . ? N2 O1 C9 C8 -1.2(3) . . . . ? C10 C8 C9 O2 4.1(7) . . . . ? C7 C8 C9 O2 178.4(4) . . . . ? C10 C8 C9 O1 -173.7(3) . . . . ? C7 C8 C9 O1 0.6(3) . . . . ? C7 C8 C10 C11 177.7(3) . . . . ? C9 C8 C10 C11 -8.9(7) . . . . ? C8 C10 C11 C12 -3.5(6) . . . . ? C8 C10 C11 C16 177.5(4) . . . . ? C16 C11 C12 C13 1.3(5) . . . . ? C10 C11 C12 C13 -177.7(3) . . . . ? C11 C12 C13 C14 2.0(5) . . . . ? C17 N1 C14 C15 -175.3(3) . . . . ? C18 N1 C14 C15 -3.1(5) . . . . ? C17 N1 C14 C13 5.5(5) . . . . ? C18 N1 C14 C13 177.7(3) . . . . ? C12 C13 C14 N1 175.0(3) . . . . ? C12 C13 C14 C15 -4.2(5) . . . . ? N1 C14 C15 C16 -176.0(3) . . . . ? C13 C14 C15 C16 3.3(5) . . . . ? C14 C15 C16 C11 -0.1(5) . . . . ? C12 C11 C16 C15 -2.3(5) . . . . ? C10 C11 C16 C15 176.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.190 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 947161' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sa2373 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H22 N2 O2' _chemical_formula_sum 'C26 H22 N2 O2' _chemical_formula_weight 394.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.844(4) _cell_length_b 7.720(5) _cell_length_c 44.76(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2019(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4139 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 26.28 _exptl_crystal_description platelet _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9741 _exptl_absorpt_correction_T_max 0.9967 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15388 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -55 _diffrn_reflns_limit_l_max 55 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4053 _reflns_number_gt 3653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Olex2 ver 1.1' _computing_publication_material 'SHELX97 (Sheldrick, 2008)' _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^)+(0.0388P)^2^+1.5898P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(3) _refine_ls_number_reflns 4053 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0942 _refine_ls_R_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.1635 _refine_ls_wR_factor_gt 0.1588 _refine_ls_goodness_of_fit_ref 1.206 _refine_ls_restrained_S_all 1.206 _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 C14 C 1.0090(6) 0.4500(5) 0.19358(8) 0.0333(8) Uani 1 1 d . . . N2 N 0.3587(5) 0.4507(4) 0.35208(7) 0.0379(7) Uani 1 1 d . . . C22 C 0.4417(6) 0.4455(5) 0.32321(8) 0.0327(8) Uani 1 1 d . . . C17 C 0.9215(6) 0.4624(5) 0.22412(8) 0.0364(9) Uani 1 1 d . . . H17 H 1.0153 0.5211 0.2382 0.044 Uiso 1 1 calc R . . C24 C 0.4180(6) 0.3488(5) 0.27165(8) 0.0353(8) Uani 1 1 d . . . H24 H 0.3342 0.2904 0.2565 0.042 Uiso 1 1 calc R . . C11 C 1.1914(6) 0.4466(5) 0.13474(8) 0.0317(8) Uani 1 1 d . . . C15 C 0.8984(6) 0.3619(5) 0.17035(8) 0.0372(9) Uani 1 1 d . . . H15 H 0.7596 0.3024 0.1744 0.045 Uiso 1 1 calc R . . O1 O 1.1927(5) 0.1543(4) 0.04524(6) 0.0539(8) Uani 1 1 d . . . C19 C 0.6296(6) 0.4214(4) 0.26444(8) 0.0323(8) Uani 1 1 d . . . C16 C 0.9856(6) 0.3593(5) 0.14161(8) 0.0347(8) Uani 1 1 d . . . H16 H 0.9064 0.2982 0.1264 0.042 Uiso 1 1 calc R . . C21 C 0.6508(6) 0.5265(5) 0.31557(8) 0.0357(8) Uani 1 1 d . . . H21 H 0.7309 0.5909 0.3303 0.043 Uiso 1 1 calc R . . C12 C 1.2999(6) 0.5365(5) 0.15809(8) 0.0373(9) Uani 1 1 d . . . H12 H 1.4369 0.5983 0.1540 0.045 Uiso 1 1 calc R . . C18 C 0.7213(6) 0.3989(5) 0.23431(8) 0.0355(8) Uani 1 1 d . . . H18 H 0.6316 0.3335 0.2207 0.043 Uiso 1 1 calc R . . C23 C 0.3254(6) 0.3589(5) 0.30024(8) 0.0342(8) Uani 1 1 d . . . H23 H 0.1815 0.3065 0.3042 0.041 Uiso 1 1 calc R . . C13 C 1.2131(6) 0.5373(5) 0.18669(8) 0.0355(8) Uani 1 1 d . . . H13 H 1.2926 0.5978 0.2020 0.043 Uiso 1 1 calc R . . C20 C 0.7410(6) 0.5140(5) 0.28718(8) 0.0346(8) Uani 1 1 d . . . H20 H 0.8822 0.5696 0.2829 0.042 Uiso 1 1 calc R . . C3 C 1.4108(6) 0.3843(5) 0.05282(8) 0.0366(8) Uani 1 1 d . . . O2 O 0.9703(5) 0.1448(4) 0.08548(7) 0.0576(8) Uani 1 1 d . . . C2 C 1.2695(6) 0.3661(5) 0.07933(8) 0.0357(8) Uani 1 1 d . . . C10 C 1.3020(6) 0.4543(5) 0.10544(8) 0.0375(9) Uani 1 1 d . . . H10 H 1.4209 0.5379 0.1044 0.045 Uiso 1 1 calc R . . C25 C 0.4992(7) 0.5160(6) 0.37614(9) 0.0500(11) Uani 1 1 d . . . H25A H 0.6314 0.4396 0.3789 0.075 Uiso 1 1 calc R . . H25B H 0.4092 0.5197 0.3946 0.075 Uiso 1 1 calc R . . H25C H 0.5524 0.6329 0.3712 0.075 Uiso 1 1 calc R . . N1 N 1.3711(6) 0.2650(4) 0.03309(7) 0.0476(9) Uani 1 1 d . . . C1 C 1.1234(7) 0.2171(5) 0.07237(9) 0.0426(9) Uani 1 1 d . . . C26 C 0.1581(7) 0.3497(5) 0.36033(9) 0.0436(10) Uani 1 1 d . . . H26A H 0.0293 0.3821 0.3475 0.065 Uiso 1 1 calc R . . H26B H 0.1188 0.3729 0.3812 0.065 Uiso 1 1 calc R . . H26C H 0.1913 0.2261 0.3578 0.065 Uiso 1 1 calc R . . C4 C 1.5868(6) 0.5169(5) 0.04608(8) 0.0365(8) Uani 1 1 d . . . C6 C 1.9443(7) 0.5901(6) 0.02227(9) 0.0507(11) Uani 1 1 d . . . H6 H 2.0748 0.5567 0.0110 0.061 Uiso 1 1 calc R . . C5 C 1.7801(7) 0.4664(6) 0.02996(9) 0.0440(9) Uani 1 1 d . . . H5 H 1.7998 0.3488 0.0243 0.053 Uiso 1 1 calc R . . C9 C 1.5580(7) 0.6897(5) 0.05418(8) 0.0403(9) Uani 1 1 d . . . H9 H 1.4249 0.7248 0.0648 0.048 Uiso 1 1 calc R . . C8 C 1.7255(8) 0.8110(6) 0.04670(9) 0.0508(11) Uani 1 1 d . . . H8 H 1.7069 0.9286 0.0525 0.061 Uiso 1 1 calc R . . C7 C 1.9179(7) 0.7614(6) 0.03100(9) 0.0499(11) Uani 1 1 d . . . H7 H 2.0321 0.8445 0.0262 0.060 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 C14 0.0299(18) 0.0384(19) 0.0317(19) 0.0005(16) 0.0008(16) 0.0038(15) N2 0.0311(16) 0.0474(18) 0.0352(17) -0.0027(15) 0.0035(14) -0.0068(14) C22 0.0274(18) 0.0356(19) 0.0351(19) 0.0016(16) 0.0006(15) 0.0046(16) C17 0.0338(19) 0.0364(19) 0.039(2) -0.0004(16) -0.0013(17) 0.0021(17) C24 0.0318(19) 0.0375(19) 0.037(2) 0.0018(16) -0.0031(17) 0.0023(16) C11 0.0302(18) 0.0348(18) 0.0300(19) -0.0005(15) 0.0018(15) -0.0003(15) C15 0.0312(19) 0.040(2) 0.040(2) -0.0023(17) 0.0029(17) 0.0009(18) O1 0.0661(19) 0.0500(16) 0.0455(17) -0.0132(14) 0.0115(15) -0.0212(15) C19 0.0306(19) 0.0334(18) 0.0328(19) 0.0052(15) 0.0025(16) 0.0021(15) C16 0.0307(18) 0.0361(19) 0.037(2) 0.0015(16) 0.0003(16) -0.0028(16) C21 0.0348(19) 0.0366(19) 0.036(2) -0.0024(16) -0.0028(17) -0.0005(17) C12 0.0305(19) 0.0378(19) 0.043(2) -0.0050(17) 0.0013(17) -0.0044(16) C18 0.036(2) 0.0353(18) 0.036(2) -0.0003(16) -0.0046(17) 0.0024(16) C23 0.0256(17) 0.0382(19) 0.039(2) 0.0004(16) 0.0026(16) -0.0003(16) C13 0.0308(19) 0.0420(19) 0.034(2) -0.0032(17) 0.0025(16) -0.0023(17) C20 0.0247(17) 0.0392(19) 0.040(2) 0.0033(16) 0.0027(16) -0.0038(16) C3 0.038(2) 0.0410(19) 0.0303(19) -0.0013(16) -0.0024(17) -0.0022(17) O2 0.067(2) 0.0563(18) 0.0499(18) -0.0035(15) 0.0103(16) -0.0280(16) C2 0.038(2) 0.0371(18) 0.032(2) -0.0002(16) 0.0003(17) 0.0000(16) C10 0.036(2) 0.0382(19) 0.039(2) 0.0013(17) -0.0021(17) 0.0001(17) C25 0.045(2) 0.064(3) 0.041(2) -0.009(2) 0.0085(19) -0.015(2) N1 0.054(2) 0.0478(19) 0.0413(19) -0.0086(16) 0.0073(17) -0.0113(17) C1 0.046(2) 0.040(2) 0.042(2) -0.0012(18) 0.0036(19) -0.0075(19) C26 0.038(2) 0.052(2) 0.041(2) -0.0002(19) 0.0060(19) -0.0039(19) C4 0.038(2) 0.044(2) 0.0282(19) -0.0019(16) -0.0004(16) 0.0004(17) C6 0.037(2) 0.076(3) 0.039(2) 0.007(2) 0.0046(19) 0.000(2) C5 0.046(2) 0.050(2) 0.036(2) 0.0012(18) 0.0014(19) 0.002(2) C9 0.044(2) 0.046(2) 0.0303(19) -0.0037(17) 0.0022(18) -0.0082(18) C8 0.060(3) 0.052(2) 0.040(2) 0.0014(19) -0.001(2) -0.015(2) C7 0.043(2) 0.063(3) 0.044(2) 0.008(2) 0.000(2) -0.021(2) _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 C14 C15 1.400(5) . ? C14 C13 1.405(5) . ? C14 C17 1.463(5) . ? N2 C22 1.381(5) . ? N2 C25 1.445(5) . ? N2 C26 1.455(5) . ? C22 C23 1.403(5) . ? C22 C21 1.414(5) . ? C17 C18 1.348(5) . ? C17 H17 0.9500 . ? C24 C23 1.392(5) . ? C24 C19 1.396(5) . ? C24 H24 0.9500 . ? C11 C12 1.405(5) . ? C11 C16 1.413(5) . ? C11 C10 1.463(5) . ? C15 C16 1.384(5) . ? C15 H15 0.9500 . ? O1 C1 1.369(5) . ? O1 N1 1.453(4) . ? C19 C20 1.404(5) . ? C19 C18 1.461(5) . ? C16 H16 0.9500 . ? C21 C20 1.379(5) . ? C21 H21 0.9500 . ? C12 C13 1.377(5) . ? C12 H12 0.9500 . ? C18 H18 0.9500 . ? C23 H23 0.9500 . ? C13 H13 0.9500 . ? C20 H20 0.9500 . ? C3 N1 1.297(5) . ? C3 C2 1.452(5) . ? C3 C4 1.482(5) . ? O2 C1 1.207(5) . ? C2 C10 1.366(5) . ? C2 C1 1.466(5) . ? C10 H10 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C4 C9 1.392(5) . ? C4 C5 1.396(5) . ? C6 C7 1.388(6) . ? C6 C5 1.396(6) . ? C6 H6 0.9500 . ? C5 H5 0.9500 . ? C9 C8 1.395(6) . ? C9 H9 0.9500 . ? C8 C7 1.380(6) . ? C8 H8 0.9500 . ? C7 H7 0.9500 . ? 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 C15 C14 C13 117.5(3) . . ? C15 C14 C17 124.4(3) . . ? C13 C14 C17 118.1(3) . . ? C22 N2 C25 120.5(3) . . ? C22 N2 C26 120.3(3) . . ? C25 N2 C26 117.1(3) . . ? N2 C22 C23 122.0(3) . . ? N2 C22 C21 121.1(3) . . ? C23 C22 C21 116.9(3) . . ? C18 C17 C14 126.6(4) . . ? C18 C17 H17 116.7 . . ? C14 C17 H17 116.7 . . ? C23 C24 C19 122.3(3) . . ? C23 C24 H24 118.8 . . ? C19 C24 H24 118.8 . . ? C12 C11 C16 117.2(3) . . ? C12 C11 C10 116.6(3) . . ? C16 C11 C10 126.2(3) . . ? C16 C15 C14 121.8(3) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C1 O1 N1 109.6(3) . . ? C24 C19 C20 116.6(3) . . ? C24 C19 C18 119.3(3) . . ? C20 C19 C18 124.1(3) . . ? C15 C16 C11 120.6(3) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C20 C21 C22 121.5(3) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C13 C12 C11 121.9(3) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C17 C18 C19 125.9(3) . . ? C17 C18 H18 117.0 . . ? C19 C18 H18 117.0 . . ? C24 C23 C22 120.8(3) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C12 C13 C14 121.0(3) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C21 C20 C19 121.8(3) . . ? C21 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? N1 C3 C2 112.7(3) . . ? N1 C3 C4 118.4(3) . . ? C2 C3 C4 128.9(3) . . ? C10 C2 C3 124.9(3) . . ? C10 C2 C1 130.9(3) . . ? C3 C2 C1 103.5(3) . . ? C2 C10 C11 133.3(3) . . ? C2 C10 H10 113.4 . . ? C11 C10 H10 113.4 . . ? N2 C25 H25A 109.5 . . ? N2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C3 N1 O1 106.9(3) . . ? O2 C1 O1 119.1(4) . . ? O2 C1 C2 133.7(4) . . ? O1 C1 C2 107.1(3) . . ? N2 C26 H26A 109.5 . . ? N2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C9 C4 C5 120.0(4) . . ? C9 C4 C3 121.7(3) . . ? C5 C4 C3 118.3(3) . . ? C7 C6 C5 120.4(4) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C4 C5 C6 119.5(4) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C4 C9 C8 119.7(4) . . ? C4 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C7 C8 C9 120.5(4) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C7 C6 119.9(4) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? 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 C25 N2 C22 C23 169.9(4) . . . . ? C26 N2 C22 C23 6.7(5) . . . . ? C25 N2 C22 C21 -9.5(5) . . . . ? C26 N2 C22 C21 -172.7(3) . . . . ? C15 C14 C17 C18 -2.8(6) . . . . ? C13 C14 C17 C18 174.7(4) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? C17 C14 C15 C16 177.9(3) . . . . ? C23 C24 C19 C20 -3.2(5) . . . . ? C23 C24 C19 C18 177.1(3) . . . . ? C14 C15 C16 C11 -0.1(6) . . . . ? C12 C11 C16 C15 -0.7(5) . . . . ? C10 C11 C16 C15 -180.0(4) . . . . ? N2 C22 C21 C20 176.5(3) . . . . ? C23 C22 C21 C20 -2.9(5) . . . . ? C16 C11 C12 C13 1.3(5) . . . . ? C10 C11 C12 C13 -179.4(4) . . . . ? C14 C17 C18 C19 -176.0(4) . . . . ? C24 C19 C18 C17 179.5(3) . . . . ? C20 C19 C18 C17 -0.1(6) . . . . ? C19 C24 C23 C22 0.7(6) . . . . ? N2 C22 C23 C24 -177.0(3) . . . . ? C21 C22 C23 C24 2.3(5) . . . . ? C11 C12 C13 C14 -1.1(6) . . . . ? C15 C14 C13 C12 0.3(5) . . . . ? C17 C14 C13 C12 -177.4(3) . . . . ? C22 C21 C20 C19 0.3(5) . . . . ? C24 C19 C20 C21 2.7(5) . . . . ? C18 C19 C20 C21 -177.7(3) . . . . ? N1 C3 C2 C10 168.2(4) . . . . ? C4 C3 C2 C10 -11.7(6) . . . . ? N1 C3 C2 C1 -2.6(4) . . . . ? C4 C3 C2 C1 177.5(4) . . . . ? C3 C2 C10 C11 -175.2(4) . . . . ? C1 C2 C10 C11 -7.1(7) . . . . ? C12 C11 C10 C2 168.6(4) . . . . ? C16 C11 C10 C2 -12.1(7) . . . . ? C2 C3 N1 O1 0.4(4) . . . . ? C4 C3 N1 O1 -179.8(3) . . . . ? C1 O1 N1 C3 2.2(4) . . . . ? N1 O1 C1 O2 177.7(4) . . . . ? N1 O1 C1 C2 -3.8(4) . . . . ? C10 C2 C1 O2 12.0(8) . . . . ? C3 C2 C1 O2 -178.0(5) . . . . ? C10 C2 C1 O1 -166.2(4) . . . . ? C3 C2 C1 O1 3.8(4) . . . . ? N1 C3 C4 C9 141.5(4) . . . . ? C2 C3 C4 C9 -38.6(6) . . . . ? N1 C3 C4 C5 -35.4(5) . . . . ? C2 C3 C4 C5 144.4(4) . . . . ? C9 C4 C5 C6 0.5(6) . . . . ? C3 C4 C5 C6 177.5(3) . . . . ? C7 C6 C5 C4 1.1(6) . . . . ? C5 C4 C9 C8 -1.4(6) . . . . ? C3 C4 C9 C8 -178.3(4) . . . . ? C4 C9 C8 C7 0.8(6) . . . . ? C9 C8 C7 C6 0.7(6) . . . . ? C5 C6 C7 C8 -1.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.197 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 947162' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_jd _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H24 N2 O2' _chemical_formula_weight 516.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.6077(15) _cell_length_b 8.2169(8) _cell_length_c 20.052(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.011(11) _cell_angle_gamma 90.00 _cell_volume 2587.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rodlike _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.650 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8809 _exptl_absorpt_correction_T_max 0.9808 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 10.3415 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9652 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.20 _diffrn_reflns_theta_max 65.07 _reflns_number_total 4420 _reflns_number_gt 3221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Agilent Technologies.' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies.' _computing_data_reduction 'CrysAlisPro, Agilent Technologies.' _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^)+(0.0844P)^2^+0.6392P] 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 4420 _refine_ls_number_parameters 457 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1649 _refine_ls_wR_factor_gt 0.1428 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.15573(14) 0.6979(3) 0.15163(13) 0.0617(6) Uani 1 1 d . . . C2 C 0.42022(15) 0.7584(3) 0.28891(13) 0.0656(6) Uani 1 1 d . . . C3 C 0.05432(15) 0.7006(3) 0.13479(14) 0.0666(6) Uani 1 1 d . . . C4 C -0.00197(14) 0.7617(3) 0.16708(13) 0.0632(6) Uani 1 1 d . . . C5 C 0.74155(15) 0.8093(3) 0.45949(13) 0.0629(6) Uani 1 1 d . . . N6 N -0.09132(11) 0.7635(3) 0.12908(11) 0.0654(5) Uani 1 1 d . . . C7 C 0.14099(15) 0.7049(3) 0.16985(14) 0.0673(6) Uani 1 1 d . . . C8 C -0.23453(14) 0.7203(3) 0.09739(13) 0.0612(6) Uani 1 1 d . . . C10 C 0.56521(16) 0.7334(3) 0.28902(14) 0.0693(7) Uani 1 1 d . . . C11 C 0.11660(15) 0.8244(3) 0.26984(15) 0.0696(7) Uani 1 1 d . . . O12 O 0.80203(12) 0.9317(3) 0.56642(10) 0.0865(6) Uani 1 1 d . . . C13 C 0.83405(15) 0.7990(3) 0.48357(13) 0.0655(6) Uani 1 1 d . . . C14 C 0.17408(15) 0.7695(3) 0.23803(13) 0.0646(6) Uani 1 1 d . . . C15 C 0.95641(15) 0.8207(3) 0.43867(14) 0.0693(7) Uani 1 1 d . . . C16 C -0.12821(14) 0.8295(3) 0.06199(13) 0.0630(6) Uani 1 1 d . . . C17 C -0.21720(14) 0.8058(3) 0.04066(12) 0.0599(6) Uani 1 1 d . . . C18 C 0.59726(14) 0.7628(3) 0.36166(13) 0.0639(6) Uani 1 1 d . . . C19 C 0.26604(15) 0.7806(3) 0.27631(15) 0.0675(6) Uani 1 1 d . . . C20 C -0.30870(15) 0.6601(3) 0.10679(14) 0.0661(6) Uani 1 1 d . . . C21 C 0.88202(16) 0.5665(3) 0.42436(14) 0.0695(7) Uani 1 1 d . . . C22 C 0.53900(16) 0.7906(4) 0.39729(15) 0.0713(7) Uani 1 1 d . . . C23 C 0.32855(16) 0.7508(3) 0.24998(15) 0.0684(6) Uani 1 1 d . . . C24 C 0.68931(15) 0.7601(3) 0.39527(13) 0.0637(6) Uani 1 1 d . . . C25 C 0.02905(15) 0.8216(3) 0.23427(14) 0.0683(6) Uani 1 1 d . . . C26 C -0.30360(16) 0.5811(3) 0.16827(15) 0.0707(7) Uani 1 1 d . . . C27 C 0.72352(17) 0.8986(3) 0.51584(14) 0.0728(7) Uani 1 1 d . . . C28 C 0.93930(16) 0.5006(4) 0.39461(15) 0.0742(7) Uani 1 1 d . . . C29 C -0.15035(16) 0.6183(3) 0.21290(15) 0.0701(7) Uani 1 1 d . . . C30 C 0.47845(16) 0.7328(3) 0.25304(15) 0.0708(7) Uani 1 1 d . . . C31 C -0.22528(17) 0.5599(4) 0.22119(16) 0.0739(7) Uani 1 1 d . . . N32 N 0.86909(14) 0.8672(3) 0.54392(12) 0.0797(6) Uani 1 1 d . . . C33 C 1.00439(16) 0.5944(4) 0.38651(15) 0.0751(7) Uani 1 1 d . . . C34 C 0.89057(14) 0.7272(3) 0.44752(13) 0.0637(6) Uani 1 1 d . . . C35 C -0.26774(16) 0.8650(3) -0.02500(14) 0.0696(7) Uani 1 1 d . . . C36 C -0.23095(17) 0.9460(4) -0.06710(15) 0.0735(7) Uani 1 1 d . . . C37 C 0.45215(16) 0.7887(4) 0.36114(14) 0.0715(7) Uani 1 1 d . . . C38 C -0.09129(16) 0.9116(4) 0.01954(15) 0.0741(7) Uani 1 1 d . . . C39 C -0.14319(17) 0.9699(4) -0.04461(15) 0.0765(7) Uani 1 1 d . . . C40 C 1.01181(16) 0.7557(4) 0.40767(15) 0.0758(7) Uani 1 1 d . . . O1 O 0.65959(12) 0.9483(3) 0.52578(10) 0.0869(6) Uani 1 1 d . . . H11 H 0.1349(16) 0.868(3) 0.3139(14) 0.074(8) Uiso 1 1 d . . . H19 H 0.2762(14) 0.818(3) 0.3219(12) 0.058(6) Uiso 1 1 d . . . H30 H 0.4603(17) 0.721(3) 0.2014(14) 0.075(7) Uiso 1 1 d . . . H22 H 0.5549(15) 0.818(3) 0.4437(13) 0.064(7) Uiso 1 1 d . . . H10 H 0.6043(17) 0.717(3) 0.2610(13) 0.076(7) Uiso 1 1 d . . . H25 H -0.0058(15) 0.864(3) 0.2581(12) 0.061(6) Uiso 1 1 d . . . H20 H -0.3641(16) 0.672(3) 0.0692(13) 0.066(7) Uiso 1 1 d . . . H37 H 0.4140(17) 0.814(3) 0.3885(13) 0.077(8) Uiso 1 1 d . . . H31 H -0.2260(15) 0.504(3) 0.2602(14) 0.069(7) Uiso 1 1 d . . . H23 H 0.3170(17) 0.720(3) 0.1993(15) 0.079(8) Uiso 1 1 d . . . H7 H 0.1779(16) 0.655(3) 0.1433(13) 0.073(7) Uiso 1 1 d . . . H26 H -0.3530(16) 0.534(3) 0.1805(12) 0.067(7) Uiso 1 1 d . . . H15 H 0.9597(18) 0.939(4) 0.4574(15) 0.097(9) Uiso 1 1 d . . . H40 H 1.0590(19) 0.829(3) 0.4020(14) 0.092(9) Uiso 1 1 d . . . H3 H 0.0319(16) 0.656(3) 0.0883(14) 0.076(8) Uiso 1 1 d . . . H21 H 0.8333(17) 0.501(3) 0.4323(13) 0.079(8) Uiso 1 1 d . . . H35 H -0.3254(17) 0.846(3) -0.0390(13) 0.071(7) Uiso 1 1 d . . . H36 H -0.2652(16) 0.991(3) -0.1113(14) 0.071(7) Uiso 1 1 d . . . H29 H -0.0983(17) 0.601(3) 0.2511(13) 0.075(7) Uiso 1 1 d . . . H24 H 0.7200(14) 0.718(3) 0.3626(11) 0.053(6) Uiso 1 1 d . . . H38 H -0.0343(18) 0.925(4) 0.0338(15) 0.094(9) Uiso 1 1 d . . . H39 H -0.1183(16) 1.024(3) -0.0761(14) 0.079(8) Uiso 1 1 d . . . H33 H 1.0439(17) 0.540(3) 0.3595(15) 0.091(9) Uiso 1 1 d . . . H28 H 0.9359(18) 0.377(4) 0.3776(15) 0.097(9) Uiso 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 C1 0.0446(12) 0.0647(14) 0.0722(15) -0.0022(12) 0.0140(10) 0.0008(10) C2 0.0479(13) 0.0692(15) 0.0747(16) 0.0088(12) 0.0131(11) 0.0008(11) C3 0.0496(13) 0.0765(16) 0.0696(15) 0.0043(13) 0.0136(11) 0.0023(11) C4 0.0429(12) 0.0663(14) 0.0744(15) 0.0088(12) 0.0110(11) -0.0021(10) C5 0.0545(13) 0.0625(14) 0.0706(15) 0.0090(11) 0.0188(11) -0.0043(11) N6 0.0407(10) 0.0740(13) 0.0776(13) 0.0080(10) 0.0140(9) -0.0018(9) C7 0.0488(13) 0.0788(16) 0.0722(15) 0.0083(13) 0.0170(12) 0.0059(12) C8 0.0442(12) 0.0600(13) 0.0765(15) -0.0101(11) 0.0158(11) -0.0004(10) C10 0.0491(13) 0.0799(17) 0.0775(16) -0.0026(13) 0.0187(12) -0.0014(12) C11 0.0504(13) 0.0816(17) 0.0726(16) -0.0046(14) 0.0143(12) -0.0063(12) O12 0.0796(13) 0.0987(14) 0.0775(12) -0.0128(10) 0.0204(10) -0.0073(11) C13 0.0564(13) 0.0658(14) 0.0665(14) 0.0071(12) 0.0092(11) -0.0076(11) C14 0.0465(12) 0.0690(15) 0.0758(16) 0.0095(12) 0.0163(11) 0.0005(11) C15 0.0457(12) 0.0701(16) 0.0819(17) 0.0073(13) 0.0069(12) -0.0031(11) C16 0.0446(12) 0.0641(14) 0.0759(15) 0.0005(12) 0.0135(11) 0.0035(10) C17 0.0467(12) 0.0605(13) 0.0697(14) -0.0064(11) 0.0151(10) 0.0021(10) C18 0.0479(13) 0.0687(15) 0.0726(15) 0.0082(11) 0.0163(11) -0.0015(10) C19 0.0496(13) 0.0755(16) 0.0742(17) 0.0038(13) 0.0156(12) -0.0030(11) C20 0.0470(13) 0.0698(15) 0.0790(16) -0.0106(13) 0.0173(12) -0.0028(11) C21 0.0528(13) 0.0733(16) 0.0759(16) 0.0050(13) 0.0119(12) -0.0075(12) C22 0.0522(14) 0.0902(19) 0.0683(16) 0.0077(14) 0.0152(12) -0.0005(12) C23 0.0496(13) 0.0768(17) 0.0749(16) 0.0087(13) 0.0149(12) 0.0018(11) C24 0.0507(13) 0.0671(15) 0.0712(15) 0.0068(12) 0.0167(12) -0.0016(11) C25 0.0489(13) 0.0763(16) 0.0815(17) 0.0013(13) 0.0237(12) 0.0001(12) C26 0.0561(14) 0.0749(16) 0.0855(18) -0.0111(14) 0.0291(13) -0.0104(12) C27 0.0646(15) 0.0771(17) 0.0745(16) 0.0027(13) 0.0196(13) -0.0063(13) C28 0.0572(15) 0.0763(18) 0.0855(18) -0.0014(14) 0.0183(13) -0.0026(13) C29 0.0544(14) 0.0752(16) 0.0750(16) 0.0002(13) 0.0132(12) -0.0039(12) C30 0.0505(13) 0.0850(18) 0.0739(17) -0.0016(13) 0.0162(12) -0.0021(12) C31 0.0627(16) 0.0813(18) 0.0786(17) -0.0003(14) 0.0241(13) -0.0056(13) N32 0.0664(13) 0.0867(16) 0.0795(15) -0.0042(12) 0.0147(11) -0.0016(12) C33 0.0492(14) 0.0861(19) 0.0834(18) 0.0026(14) 0.0126(12) 0.0019(13) C34 0.0414(12) 0.0726(15) 0.0683(14) 0.0094(12) 0.0059(10) -0.0002(10) C35 0.0499(14) 0.0739(16) 0.0766(16) -0.0092(13) 0.0094(12) 0.0001(12) C36 0.0635(15) 0.0812(18) 0.0701(16) 0.0049(13) 0.0142(13) 0.0062(13) C37 0.0510(14) 0.0873(18) 0.0770(17) 0.0101(14) 0.0220(12) 0.0058(12) C38 0.0476(13) 0.0825(18) 0.0877(18) 0.0117(14) 0.0157(13) -0.0005(13) C39 0.0619(15) 0.0885(19) 0.0774(17) 0.0110(14) 0.0203(13) 0.0018(14) C40 0.0425(13) 0.0870(19) 0.0904(18) 0.0105(15) 0.0111(12) -0.0059(12) O1 0.0776(13) 0.0955(14) 0.0950(14) -0.0075(11) 0.0380(11) -0.0049(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 C1 C29 1.369(4) . ? C1 N6 1.398(3) . ? C1 C8 1.415(3) . ? C2 C37 1.393(4) . ? C2 C30 1.396(4) . ? C2 C23 1.469(3) . ? C3 C7 1.381(3) . ? C3 C4 1.393(3) . ? C4 C25 1.367(4) . ? C4 N6 1.430(3) . ? C5 C24 1.359(3) . ? C5 C13 1.455(3) . ? C5 C27 1.458(4) . ? N6 C16 1.394(3) . ? C7 C14 1.401(4) . ? C8 C20 1.396(3) . ? C8 C17 1.443(3) . ? C10 C30 1.385(3) . ? C10 C18 1.399(4) . ? C11 C14 1.385(3) . ? C11 C25 1.396(3) . ? O12 C27 1.393(3) . ? O12 N32 1.432(3) . ? C13 N32 1.288(3) . ? C13 C34 1.481(3) . ? C14 C19 1.472(3) . ? C15 C40 1.375(4) . ? C15 C34 1.394(3) . ? C16 C38 1.377(4) . ? C16 C17 1.412(3) . ? C17 C35 1.398(3) . ? C18 C22 1.396(3) . ? C18 C24 1.456(3) . ? C19 C23 1.332(4) . ? C20 C26 1.371(4) . ? C21 C28 1.387(4) . ? C21 C34 1.392(4) . ? C22 C37 1.387(3) . ? C26 C31 1.396(4) . ? C27 O1 1.213(3) . ? C28 C33 1.380(4) . ? C29 C31 1.393(4) . ? C33 C40 1.386(4) . ? C35 C36 1.366(4) . ? C36 C39 1.392(4) . ? C38 C39 1.380(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C29 C1 N6 129.9(2) . . ? C29 C1 C8 121.7(2) . . ? N6 C1 C8 108.4(2) . . ? C37 C2 C30 118.0(2) . . ? C37 C2 C23 122.5(2) . . ? C30 C2 C23 119.4(2) . . ? C7 C3 C4 120.0(3) . . ? C25 C4 C3 119.6(2) . . ? C25 C4 N6 120.9(2) . . ? C3 C4 N6 119.5(2) . . ? C24 C5 C13 125.2(2) . . ? C24 C5 C27 130.9(2) . . ? C13 C5 C27 103.5(2) . . ? C16 N6 C1 108.67(18) . . ? C16 N6 C4 124.87(19) . . ? C1 N6 C4 126.4(2) . . ? C3 C7 C14 121.2(2) . . ? C20 C8 C1 119.1(2) . . ? C20 C8 C17 133.6(2) . . ? C1 C8 C17 107.3(2) . . ? C30 C10 C18 121.4(2) . . ? C14 C11 C25 121.3(3) . . ? C27 O12 N32 109.74(19) . . ? N32 C13 C5 113.1(2) . . ? N32 C13 C34 117.9(2) . . ? C5 C13 C34 129.0(2) . . ? C11 C14 C7 117.6(2) . . ? C11 C14 C19 119.6(2) . . ? C7 C14 C19 122.9(2) . . ? C40 C15 C34 120.8(3) . . ? C38 C16 N6 130.0(2) . . ? C38 C16 C17 120.9(2) . . ? N6 C16 C17 109.0(2) . . ? C35 C17 C16 119.0(2) . . ? C35 C17 C8 134.3(2) . . ? C16 C17 C8 106.6(2) . . ? C22 C18 C10 118.0(2) . . ? C22 C18 C24 124.3(2) . . ? C10 C18 C24 117.7(2) . . ? C23 C19 C14 126.3(3) . . ? C26 C20 C8 119.4(2) . . ? C28 C21 C34 120.3(2) . . ? C37 C22 C18 120.4(3) . . ? C19 C23 C2 126.0(3) . . ? C5 C24 C18 133.2(2) . . ? C4 C25 C11 120.3(2) . . ? C20 C26 C31 120.8(2) . . ? O1 C27 O12 118.4(3) . . ? O1 C27 C5 135.1(3) . . ? O12 C27 C5 106.4(2) . . ? C33 C28 C21 120.4(3) . . ? C1 C29 C31 118.2(3) . . ? C10 C30 C2 120.6(3) . . ? C29 C31 C26 120.9(3) . . ? C13 N32 O12 107.3(2) . . ? C28 C33 C40 119.6(3) . . ? C21 C34 C15 118.6(2) . . ? C21 C34 C13 121.9(2) . . ? C15 C34 C13 119.4(2) . . ? C36 C35 C17 120.0(2) . . ? C35 C36 C39 120.0(3) . . ? C22 C37 C2 121.6(2) . . ? C16 C38 C39 118.5(2) . . ? C38 C39 C36 121.5(3) . . ? C15 C40 C33 120.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 65.07 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.202 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 947163'