# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Lentz, Dieter' ; Institut f\"ur Chemie und Biochemie-Anorganische Chemie Fachbereich Biologie-Chemie-Pharmazie der Freien Universit\"at Fabeckstr. 34-36 D-14195 Berlin Germany ; 'Weber, Manuela' ; Institut f\"ur Chemie und Biochemie-Anorganische Chemie Fachbereich Biologie-Chemie-Pharmazie der Freien Universit\"at Fabeckstr. 36a D-14195 Berlin Germany ; 'Mebs, Stefan' ; Institut f\"ur Chemie und Biochemie-Anorganische Chemie Fachbereich Biologie-Chemie-Pharmazie der Freien Universit\"at Fabeckstr. 36a D-14195 Berlin Germany ; 'Luger, Peter' ; Institut f\"ur Chemie und Biochemie-Anorganische Chemie Fachbereich Biologie-Chemie-Pharmazie der Freien Universit\"at Fabeckstr. 36a D-14195 Berlin Germany ; 'Schmidt, Bernd M.' ; Institut f\"ur Chemie und Biochemie-Anorganische Chemie Fachbereich Biologie-Chemie-Pharmazie der Freien Universit\"at Fabeckstr. 34-36 D-14195 Berlin Germany ; 'Sakurai, H.' ; Research Center for Molecular Scale Nanoscience Institute for Molecular Science Myodaiji Okaza Japan ; 'Higashibayashi, Shuhei' ; Research Center for Molecular Scale Nanoscience Institute for Molecular Science Myodaiji Okaza Japan ; 'Onogi, S.' ; Research Center for Molecular Scale Nanoscience Institute for Molecular Science Myodaiji Okaza Japan ; _publ_contact_author ; Prof. Dr. Peter Luger Freie Universit\"at Berlin Institut fuer Chemie und Biochemie Anorganische Chemie Fabeckstr. 36a 14195 Berlin Germany ; _publ_contact_author_email luger@chemie.fu-berlin.de _publ_contact_author_fax 0049-30-838-53464 _publ_contact_author_phone 0049-30-838-53411 _publ_section_title ; Experimental electron density of sumanene, a bowl shaped fullerene fragment; comparison with the related corannulene hydrocarbon. ; data_SUMA _database_code_depnum_ccdc_archive 'CCDC 831828' #TrackingRef 'suma-end.cif' _audit_update_record ; 2011-06-28 # Formatted by publCIF ; _chemical_name_systematic ; sumanene ; _chemical_name_common sumanene _chemical_melting_point ? _chemical_formula_moiety 'C21 H12' _chemical_formula_sum 'C21 H12' _chemical_formula_weight 264.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting rhombohedral _symmetry_space_group_name_H-M 'R 3c' _symmetry_space_group_name_hall 'R3 -2"c' #=============================================================================== _cell_length_a 16.5754(5) _cell_length_b 16.5754(5) _cell_length_c 7.5796(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 1803.45(14) _cell_formula_units_Z 6 _cell_measurement_temperature 100 _cell_measurement_reflns_used 1005 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 67.0 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.30 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 828 _exptl_absorpt_coefficient_mu 0.083 _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 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Bruker 1K CCD detector' _diffrn_measurement_method \w _diffrn_standards_decay_% 0 _diffrn_reflns_number 81481 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 67.37 _reflns_number_total 6996 _reflns_number_gt 6996 _reflns_threshold_expression >3sigma(I) _exptl_crystal_density_meas_temp 100 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -Y,+X-Y,+Z 3 -X+Y,-X,+Z 4 -Y,-X,1/2+Z 5 -X+Y,+Y,1/2+Z 6 +X,+X-Y,1/2+Z 7 1/3+X,2/3+Y,2/3+Z 8 1/3-Y,2/3+X-Y,2/3+Z 9 1/3-X+Y,2/3-X,2/3+Z 10 1/3-Y,2/3-X,1/6+Z 11 1/3-X+Y,2/3+Y,1/6+Z 12 1/3+X,2/3+X-Y,1/6+Z 13 2/3+X,1/3+Y,1/3+Z 14 2/3-Y,1/3+X-Y,1/3+Z 15 2/3-X+Y,1/3-X,1/3+Z 16 2/3-Y,1/3-X,5/6+Z 17 2/3-X+Y,1/3+Y,5/6+Z 18 2/3+X,1/3+X-Y,5/6+Z _computing_data_collection 'SMART (Bruker-AXS, 2004-2009)' _computing_cell_refinement 'SAINT (Bruker-AXS, 2004-2009)' _computing_data_reduction 'SORTAV (R.H. Blessing, 1987)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' _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_number_restraints 0 _refine_ls_R_factor_gt 0.022 _refine_ls_R_factor_all 0.031 _refine_ls_R_Fsqd_factor 0.036 _refine_ls_wR_factor_ref 0.046 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 6459 _refine_ls_number_parameters 155 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = 1/[s^2^(Fo^2^)] ; _refine_ls_shift/su_max 0 _refine_ls_extinction_method none _publ_section_references ; Volkov, A., Macchi, P., Farrugia, L. J., Gatti, C., Mallinson, P. R., Richter, T. & Koritsanszky, T. (2006). XD2006 - a computer program for multipole refinement, topological analysis and evaluation of intermolecular energies from experimental and theoretical structure factors. ; _refine_diff_density_max 0.266 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.046 _diffrn_measured_fraction_theta_max 0.98 _diffrn_reflns_theta_full 67.37 _diffrn_measured_fraction_theta_full 0.98 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags C1 C Uani 0.04619(1) 0.94824(1) 0.21787 1.000 0.0097(1) . . C2 C Uani 0.09778(1) 1.04450(1) 0.21792(3) 1.000 0.0097(1) . . C3 C Uani 0.18455(1) 1.09340(1) 0.13581(4) 1.000 0.0110(1) . . C4 C Uani 0.22166(1) 1.03979(1) 0.07079(4) 1.000 0.0126(1) . . C5 C Uani 0.16837(1) 0.94019(1) 0.07105(4) 1.000 0.0125(1) . . C6 C Uani 0.07721(1) 0.89316(1) 0.13649(4) 1.000 0.0110(1) . . C7 C Uani -0.00982(1) 0.79730(1) 0.09838(4) 1.000 0.0127(1) . . H4 H Uani 0.29203 1.07436 0.01928 1.000 0.0294 . . H5 H Uani 0.19905 0.90061 0.01991 1.000 0.0291 . . H7A H Uani -0.01076 0.77624 -0.03846 1.000 0.0288 . . H7B H Uani -0.01263 0.74360 0.18584 1.000 0.0300 . . 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 0.0095(1) 0.0093(1) 0.0108(1) 0.0003(1) -0.0005(1) 0.0050(1) C2 0.0088(1) 0.0093(1) 0.0108(1) -0.0005(1) -0.0008(1) 0.0043(1) C3 0.0085(1) 0.0107(1) 0.0132(1) -0.0006(1) -0.0007(1) 0.0042(1) C4 0.0092(1) 0.0137(1) 0.0155(1) -0.0001(1) 0.0000(1) 0.0062(1) C5 0.0112(1) 0.0135(1) 0.0151(1) -0.0002(1) -0.0002(1) 0.0080(1) C6 0.0110(1) 0.0106(1) 0.0129(1) 0.0003(1) -0.0004(1) 0.0066(1) C7 0.0136(1) 0.0097(1) 0.0160(1) 0.0000(1) -0.0003(1) 0.0067(1) H4 0.0165 0.0293 0.0403 0.0017 0.0072 0.0098 H5 0.0278 0.0282 0.0392 -0.0023 0.0047 0.0201 H7A 0.0307 0.0310 0.0246 -0.0069 -0.0012 0.0153 H7B 0.0324 0.0234 0.0365 0.0093 0.0008 0.0158 #=============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3829(2) . . no C1 C6 1.3956(3) . . no C2 C3 1.3954(3) . . no C3 C4 1.3991(3) . . no C4 C5 1.4310(3) . . no C5 C6 1.3997(4) . . no C6 C7 1.5482(3) . . no C4 H4 1.0830 . . no C5 H5 1.0830 . . no C7 H7A 1.0920 . . no C7 H7B 1.0920 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 122.50(2) . . . no C1 C2 C3 122.23(2) . . . no C2 C3 C4 116.16(2) . . . no C3 C4 C5 121.23(2) . . . no C4 C5 C6 120.99(2) . . . no C1 C6 C5 116.14(2) . . . no C1 C6 C7 107.15(2) . . . no C5 C6 C7 134.26(2) . . . no C3 C4 H4 119.36 . . . no C5 C4 H4 119.41 . . . no C4 C5 H5 119.50 . . . no C6 C5 H5 119.51 . . . no C6 C7 H7A 111.25 . . . no C6 C7 H7B 111.19 . . . no H7A C7 H7B 109.15 . . . no 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 0.24(3) . . . . no C2 C1 C6 C5 6.83(3) . . . . no C2 C1 C6 C7 -157.97(2) . . . . no C1 C2 C3 C4 -7.17(4) . . . . no C2 C3 C4 C5 6.95(4) . . . . no C3 C4 C5 C6 0.02(5) . . . . no C4 C5 C6 C1 -6.85(4) . . . . no C4 C5 C6 C7 152.67(3) . . . . no loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 C(1) 3.98(3) 0 -0.015(9) 0.005(10) -0.0047 -0.133(9) -0.048(7) -0.045(9) 0.032(8) 0.010(8) 0.004 -0.006(9) -0.010(16) -0.084(12) 0.089(9) 0.292(9) -0.022(9) 0.008(13) -0.008(10) 0.048(11) -0.034(11) 0.089(11) 0.035(11) -0.006(12) -0.014(10) -0.006(12) 1.010731 0.976641 0.976641 0.976641 0.976641 0.976641 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 3.9779 0 -0.0149 0.0047 -0.0047 -0.1329 -0.0484 -0.0446 0.0316 0.0096 0.004 -0.0057 -0.0101 -0.084 0.0893 0.2924 -0.022 0.0084 -0.0082 0.0484 -0.0342 0.0894 0.0348 -0.0058 -0.014 -0.0063 1.010731 0.976641 0.976641 0.976641 0.976641 0.976641 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 4.03(3) 0 0.044(12) 0.042(11) 0.0056 -0.186(10) 0.029(10) 0.044(9) 0.004(11) -0.068(9) -0.0257 -0.069(16) 0.034(12) -0.029(13) -0.010(13) 0.243(12) 0.026(11) 0.088(15) -0.022(12) -0.052(14) -0.016(15) 0.005(15) 0.049(15) 0.008(14) 0.036(15) -0.014(15) 1.0053 0.955932 0.955932 0.955932 0.955932 0.955932 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 4.35(3) 0 0.030(10) 0.018(12) -0.0072 -0.156(9) -0.034(9) -0.047(9) -0.019(8) -0.024(9) -0.0232 -0.014(9) -0.018(15) -0.101(10) 0.063(9) 0.278(11) 0.034(9) 0.042(13) -0.007(12) 0.023(12) 0.026(12) 0.038(12) 0.079(11) -0.021(12) 0.011(12) 0.018(12) 1.003768 0.983161 0.983161 0.983161 0.983161 0.983161 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 4.3495 0 0.0304 0.0178 -0.0072 -0.1561 -0.0339 -0.0469 -0.0193 -0.0241 -0.0232 -0.0137 -0.0179 -0.1014 0.0631 0.2775 0.0339 0.0415 -0.0067 0.0227 0.0258 0.0376 0.0787 -0.0209 0.0109 0.0184 1.003768 0.983161 0.983161 0.983161 0.983161 0.983161 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 4.0328 0 0.0441 0.0417 0.0056 -0.1858 0.0287 0.0437 0.0043 -0.068 -0.0257 -0.0692 0.0339 -0.0286 -0.0097 0.2432 0.026 0.088 -0.0224 -0.0516 -0.016 0.0049 0.0486 0.008 0.0363 -0.0136 1.0053 0.955932 0.955932 0.955932 0.955932 0.955932 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 4.23(5) 0 0.04(2) 0.03(2) -0.0168 -0.079(17) 0 0 -0.021(17) 0.063(15) -0.0178 -0.23(2) -0.273(18) 0 0 0.266(19) -0.171(18) -0.03(3) 0 0 -0.07(2) 0.12(2) 0 0 0.13(2) -0.03(2) 1.005833 0.910213 0.910213 0.910213 0.910213 0.910213 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(4) 0.745(17) 0 0 0 0.159(13) -0.019(17) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.209875 1.161222 1.161222 1.161222 1.161222 1.161222 0 2 1 2 2 2 3 2 4 2 H(5) 0.7446 0 0 0 0.1586 -0.0192 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.209875 1.161222 1.161222 1.161222 1.161222 1.161222 0 2 1 2 2 2 3 2 4 2 H(7A) 0.74(3) 0 0 0 0.085(19) 0.03(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.192215 1.343305 1.343305 1.343305 1.343305 1.343305 0 2 1 2 2 2 3 2 4 2 H(7B) 0.82(3) 0 0 0 0.20(2) 0.19(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.211807 1.109227 1.109227 1.109227 1.109227 1.109227 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 C(1) C(2) X C(1) C(6) Y C(2) C(1) -X C(2) C(3) Y C(3) C(2) X C(3) C(4) Y C(4) C(5) X C(4) C(3) Y C(5) C(4) -X C(5) C(6) Y C(6) C(1) -X C(6) C(5) Y C(7) H(7A) X C(7) H(7B) Y H(4) C(4) Z H(4) C(5) Y H(5) C(5) -Z H(5) C(4) Y H(7A) C(7) Z H(7A) H(7B) Y H(7B) C(7) Z H(7B) H(7A) Y # End of Crystallographic Information File