# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global #TrackingRef 'anti-tetrabenzo-dihydroheptafulvalene.cif' _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _publ_contact_author 'Qian Miao' _publ_contact_author_email miaoqian@cuhk.edu.hk _publ_contact_author_name 'Qian Miao' loop_ _publ_author_name 'J. Luo' 'K. Song' 'F. Gu' 'Q. Miao' data_anti-tetrabenzo-dihydroheptafulvalene _database_code_depnum_ccdc_archive 'CCDC 817215' _audit_creation_method SHELXL-97 _chemical_formula_moiety '2(C15 H11)' _chemical_formula_sum 'C30 H22' _chemical_formula_weight 382.48 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ; anti-4,5-tetrahydro-2,3;6,7,2,3;6,7-tetrabenzoheptafulvalene ; 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' _space_group_IT_number 14 _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 93.189(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.5511(3) _cell_length_b 7.0723(3) _cell_length_c 16.9235(6) _cell_measurement_reflns_used 2658 _cell_measurement_temperature 233(2) _cell_measurement_theta_max 28.0157 _cell_measurement_theta_min 3.6101 _cell_volume 1021.88(7) _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.94095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 404 _exptl_crystal_colour ? _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.61 _exptl_crystal_size_min 0.41 _exptl_special_details ? _diffrn_ambient_temperature 233.0 _diffrn_detector_area_resol_mean 16.127 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -86.00 10.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -16.6379 -77.0000 60.0000 96 #__ type_ start__ end____ width___ exp.time_ 2 omega -41.00 55.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -16.6379 37.0000 -30.0000 96 #__ type_ start__ end____ width___ exp.time_ 3 omega -84.00 -57.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -16.6379 -37.0000 150.0000 27 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0677489 _diffrn_orient_matrix_UB_12 -0.0273325 _diffrn_orient_matrix_UB_13 0.01949 _diffrn_orient_matrix_UB_21 0.0430615 _diffrn_orient_matrix_UB_22 -0.073742 _diffrn_orient_matrix_UB_23 0.0195031 _diffrn_orient_matrix_UB_31 0.0213248 _diffrn_orient_matrix_UB_32 0.0623106 _diffrn_orient_matrix_UB_33 0.031639 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0120 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 3592 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.76 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1444 _reflns_number_total 1800 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.164 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.026 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0345 _refine_ls_extinction_coef 0.068(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 1800 _refine_ls_number_restraints 62 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0884 _refine_ls_wR_factor_ref 0.0925 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+0.1726P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.2927(7) 0.3903(12) 0.4758(5) 0.0453(13) Uani 0.50 1 d PU A 1 H1A H 0.2504 0.5138 0.4899 0.054 Uiso 0.50 1 calc PR A 1 H1B H 0.4060 0.3926 0.4883 0.054 Uiso 0.50 1 calc PR A 1 C2 C 0.2640(18) 0.3596(19) 0.3924(8) 0.0446(19) Uani 0.50 1 d PU A 1 H2B H 0.3168 0.4605 0.3645 0.054 Uiso 0.50 1 calc PR A 1 H2A H 0.1513 0.3743 0.3801 0.054 Uiso 0.50 1 calc PR A 1 C1A C 0.2379(7) 0.3641(14) 0.4734(6) 0.0521(16) Uani 0.50 1 d PU A 2 H1AA H 0.2157 0.4892 0.4879 0.063 Uiso 0.50 1 calc PR A 2 C2A C 0.2916(17) 0.338(2) 0.3970(9) 0.054(3) Uani 0.50 1 d PU A 2 H2AA H 0.3145 0.4489 0.3692 0.064 Uiso 0.50 1 calc PR A 2 C3 C 0.31501(14) 0.16756(17) 0.35729(7) 0.0349(3) Uani 1 1 d . . . C4 C 0.27729(16) 0.1488(2) 0.27638(7) 0.0457(4) Uani 1 1 d . A . H4 H 0.2320 0.2519 0.2485 0.055 Uiso 1 1 calc R . . C5 C 0.30416(16) -0.0151(2) 0.23634(7) 0.0465(4) Uani 1 1 d . . . H5 H 0.2759 -0.0241 0.1820 0.056 Uiso 1 1 calc R A . C6 C 0.37271(15) -0.1668(2) 0.27577(7) 0.0415(3) Uani 1 1 d . A . H6 H 0.3909 -0.2802 0.2488 0.050 Uiso 1 1 calc R . . C7 C 0.41427(14) -0.15028(18) 0.35526(7) 0.0349(3) Uani 1 1 d . . . H7 H 0.4625 -0.2534 0.3819 0.042 Uiso 1 1 calc R A . C8 C 0.38711(12) 0.01438(17) 0.39740(7) 0.0297(3) Uani 1 1 d . A . C9 C 0.42780(13) 0.01951(16) 0.48419(7) 0.0280(3) Uani 1 1 d . . . C10 C 0.29183(13) 0.05546(18) 0.53349(6) 0.0331(3) Uani 1 1 d . A . C11 C 0.23838(15) -0.0844(2) 0.58284(7) 0.0421(4) Uani 1 1 d . . . H11 H 0.2905 -0.2013 0.5863 0.051 Uiso 1 1 calc R A . C12 C 0.11003(17) -0.0541(3) 0.62685(9) 0.0597(5) Uani 1 1 d . A . H12 H 0.0746 -0.1502 0.6598 0.072 Uiso 1 1 calc R . . C13 C 0.03406(17) 0.1166(3) 0.62251(10) 0.0683(6) Uani 1 1 d . . . H13 H -0.0537 0.1374 0.6524 0.082 Uiso 1 1 calc R A . C14 C 0.08617(17) 0.2573(3) 0.57448(9) 0.0610(5) Uani 1 1 d . A . H14 H 0.0344 0.3745 0.5727 0.073 Uiso 1 1 calc R . . C15 C 0.21478(16) 0.2293(2) 0.52828(7) 0.0444(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 C1 0.052(3) 0.029(2) 0.054(2) -0.0050(17) -0.003(3) 0.009(3) C2 0.053(4) 0.023(3) 0.057(3) -0.008(3) -0.006(3) 0.009(3) C1A 0.049(4) 0.037(3) 0.070(3) -0.008(2) -0.005(3) 0.010(3) C2A 0.060(5) 0.038(4) 0.062(3) 0.018(3) -0.003(3) 0.007(3) C3 0.0337(7) 0.0328(7) 0.0379(7) 0.0046(5) 0.0001(5) -0.0031(5) C4 0.0482(8) 0.0520(9) 0.0363(7) 0.0142(6) -0.0034(6) 0.0033(7) C5 0.0462(8) 0.0646(10) 0.0283(7) -0.0006(6) -0.0015(5) -0.0002(7) C6 0.0383(7) 0.0514(8) 0.0348(7) -0.0093(6) 0.0015(5) 0.0023(6) C7 0.0295(6) 0.0391(7) 0.0359(7) -0.0013(5) 0.0000(5) 0.0046(5) C8 0.0212(5) 0.0356(7) 0.0321(6) 0.0000(5) 0.0003(4) -0.0031(5) C9 0.0272(6) 0.0259(6) 0.0306(6) -0.0007(5) -0.0010(4) 0.0004(5) C10 0.0245(6) 0.0449(8) 0.0293(6) -0.0069(5) -0.0048(5) 0.0023(5) C11 0.0334(7) 0.0565(9) 0.0363(7) -0.0056(6) 0.0012(5) -0.0074(6) C12 0.0369(8) 0.0950(13) 0.0478(8) -0.0126(8) 0.0083(6) -0.0176(9) C13 0.0274(7) 0.1275(17) 0.0501(9) -0.0298(10) 0.0038(6) -0.0016(10) C14 0.0381(8) 0.0917(13) 0.0515(9) -0.0300(9) -0.0138(7) 0.0291(8) C15 0.0375(7) 0.0570(9) 0.0375(7) -0.0115(7) -0.0078(6) 0.0167(7) _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 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 C2 1.436(17) . ? C1 C15 1.611(8) . ? C2 H2B 0.9800 . ? C2 H2A 0.9800 . ? C2 C3 1.555(12) . ? C1A H1AA 0.9400 . ? C1A C2A 1.41(2) . ? C1A C15 1.354(10) . ? C2A H2AA 0.9400 . ? C2A C3 1.401(14) . ? C3 C4 1.3955(18) . ? C3 C8 1.4028(16) . ? C4 H4 0.9400 . ? C4 C5 1.3685(19) . ? C5 H5 0.9400 . ? C5 C6 1.3773(19) . ? C6 H6 0.9400 . ? C6 C7 1.3772(17) . ? C7 H7 0.9400 . ? C7 C8 1.3917(17) . ? C8 C9 1.4909(16) . ? C9 C9 1.347(2) 3_656 ? C9 C10 1.4902(16) . ? C10 C11 1.3882(18) . ? C10 C15 1.3951(18) . ? C11 H11 0.9400 . ? C11 C12 1.3770(19) . ? C12 H12 0.9400 . ? C12 C13 1.371(3) . ? C13 H13 0.9400 . ? C13 C14 1.375(3) . ? C14 H14 0.9400 . ? C14 C15 1.398(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 H2B 107.8 . . ? C1 C2 H2A 107.8 . . ? C1 C2 C3 118.1(11) . . ? H1A C1 H1B 107.9 . . ? C2 C1 H1A 109.1 . . ? C2 C1 H1B 109.1 . . ? C2 C1 C15 112.4(7) . . ? H2B C2 H2A 107.1 . . ? C1A C2A H2AA 116.0 . . ? C1A C15 C1 16.8(4) . . ? C1A C15 C10 125.3(4) . . ? C1A C15 C14 115.7(4) . . ? C2A C1A H1AA 116.4 . . ? C2A C3 C2 9.4(11) . . ? C2A C3 C8 120.3(6) . . ? C3 C2 H2B 107.8 . . ? C3 C2 H2A 107.8 . . ? C3 C2A C1A 128.0(12) . . ? C3 C2A H2AA 116.0 . . ? C3 C4 H4 119.0 . . ? C3 C8 C9 122.01(10) . . ? C4 C3 C2 113.8(6) . . ? C4 C3 C2A 121.4(6) . . ? C4 C3 C8 118.21(12) . . ? C4 C5 H5 120.0 . . ? C4 C5 C6 119.92(12) . . ? C5 C4 C3 122.03(12) . . ? C5 C4 H4 119.0 . . ? C5 C6 H6 120.4 . . ? C6 C5 H5 120.0 . . ? C6 C7 H7 119.0 . . ? C6 C7 C8 122.03(11) . . ? C7 C6 C5 119.13(12) . . ? C7 C6 H6 120.4 . . ? C7 C8 C3 118.66(10) . . ? C7 C8 C9 119.25(10) . . ? C8 C3 C2 127.9(6) . . ? C8 C7 H7 119.0 . . ? C9 C9 C8 123.03(13) 3_656 . ? C9 C9 C10 122.62(13) 3_656 . ? C10 C9 C8 114.15(9) . . ? C10 C11 H11 119.5 . . ? C10 C15 C1 116.7(3) . . ? C10 C15 C14 118.22(15) . . ? C11 C10 C9 120.57(11) . . ? C11 C10 C15 119.71(12) . . ? C11 C12 H12 120.1 . . ? C12 C11 C10 120.91(15) . . ? C12 C11 H11 119.5 . . ? C12 C13 H13 120.0 . . ? C12 C13 C14 120.06(14) . . ? C13 C12 C11 119.84(16) . . ? C13 C12 H12 120.1 . . ? C13 C14 H14 119.4 . . ? C13 C14 C15 121.26(15) . . ? C14 C13 H13 120.0 . . ? C14 C15 C1 124.8(3) . . ? C15 C1 H1A 109.1 . . ? C15 C1 H1B 109.1 . . ? C15 C1A H1AA 116.4 . . ? C15 C1A C2A 127.3(10) . . ? C15 C10 C9 119.70(11) . . ? C15 C14 H14 119.4 . . ? # Attachment 'syn-hexabenzo-heptafulvalene.cif' data_syn-hexabenzo-heptafulvalene _database_code_depnum_ccdc_archive 'CCDC 817216' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C38 H24' _chemical_formula_sum 'C38 H24' _chemical_formula_weight 480.57 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ; syn-2,3;4,5;6,7;2,3;4,5;6,7-hexabenzoheptafulvalene ; 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' _space_group_IT_number 14 _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 105.143(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.0613(8) _cell_length_b 15.6693(8) _cell_length_c 17.3989(12) _cell_measurement_reflns_used 4721 _cell_measurement_temperature 293 _cell_measurement_theta_max 29.1449 _cell_measurement_theta_min 3.3348 _cell_volume 2647.8(3) _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.85567 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 1008 _exptl_crystal_colour ? _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.7 _exptl_crystal_size_min 0.4 _exptl_special_details ? _diffrn_ambient_temperature 293 _diffrn_detector_area_resol_mean 16.127 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -86.00 47.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - -18.8337 0.0000 -150.0000 133 #__ type_ start__ end____ width___ exp.time_ 2 omega -33.00 20.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 19.2243 -37.0000 -180.0000 53 #__ type_ start__ end____ width___ exp.time_ 3 omega -2.00 56.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 19.2243 77.0000 150.0000 58 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.034449 _diffrn_orient_matrix_UB_12 0.036609 _diffrn_orient_matrix_UB_13 -0.0195057 _diffrn_orient_matrix_UB_21 -0.064141 _diffrn_orient_matrix_UB_22 -0.0181632 _diffrn_orient_matrix_UB_23 0.000869 _diffrn_orient_matrix_UB_31 0.004946 _diffrn_orient_matrix_UB_32 0.0195175 _diffrn_orient_matrix_UB_33 0.0374276 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 10126 _diffrn_reflns_theta_full 25.10 _diffrn_reflns_theta_max 25.10 _diffrn_reflns_theta_min 3.34 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3355 _reflns_number_total 4691 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.155 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.040 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0532 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 343 _refine_ls_number_reflns 4691 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1163 _refine_ls_wR_factor_ref 0.1377 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.6019P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.21214(17) 0.86381(11) 0.24263(10) 0.0323(4) Uani 1 1 d . . . C2 C 0.21811(19) 0.78366(11) 0.28931(10) 0.0362(4) Uani 1 1 d . . . C3 C 0.1027(2) 0.73417(13) 0.28446(12) 0.0509(5) Uani 1 1 d . . . H3 H 0.0198 0.7492 0.2488 0.061 Uiso 1 1 calc R . . C4 C 0.1083(3) 0.66288(15) 0.33159(14) 0.0672(7) Uani 1 1 d . . . H4 H 0.0298 0.6299 0.3275 0.081 Uiso 1 1 calc R . . C5 C 0.2298(3) 0.64075(14) 0.38446(14) 0.0688(7) Uani 1 1 d . . . H5 H 0.2339 0.5927 0.4164 0.083 Uiso 1 1 calc R . . C6 C 0.3454(3) 0.68932(14) 0.39044(12) 0.0585(6) Uani 1 1 d . . . H6 H 0.4274 0.6733 0.4264 0.070 Uiso 1 1 calc R . . C7 C 0.3430(2) 0.76268(12) 0.34357(10) 0.0418(5) Uani 1 1 d . . . C8 C 0.4695(2) 0.81408(14) 0.35216(10) 0.0450(5) Uani 1 1 d . . . C9 C 0.5942(2) 0.77129(17) 0.35938(13) 0.0627(7) Uani 1 1 d . . . H9 H 0.5939 0.7120 0.3565 0.075 Uiso 1 1 calc R . . C10 C 0.7167(3) 0.8139(2) 0.37051(15) 0.0786(8) Uani 1 1 d . . . H10 H 0.7979 0.7837 0.3750 0.094 Uiso 1 1 calc R . . C11 C 0.7190(3) 0.9016(2) 0.37507(15) 0.0759(8) Uani 1 1 d . . . H11 H 0.8020 0.9308 0.3830 0.091 Uiso 1 1 calc R . . C12 C 0.5987(2) 0.94610(17) 0.36795(12) 0.0596(6) Uani 1 1 d . . . H12 H 0.6014 1.0054 0.3709 0.072 Uiso 1 1 calc R . . C13 C 0.4721(2) 0.90419(14) 0.35638(10) 0.0440(5) Uani 1 1 d . . . C14 C 0.3473(2) 0.95645(12) 0.35165(10) 0.0390(5) Uani 1 1 d . . . C15 C 0.3514(2) 1.02533(13) 0.40348(11) 0.0519(6) Uani 1 1 d . . . H15 H 0.4337 1.0383 0.4406 0.062 Uiso 1 1 calc R . . C16 C 0.2371(3) 1.07411(14) 0.40090(13) 0.0588(6) Uani 1 1 d . . . H16 H 0.2423 1.1191 0.4364 0.071 Uiso 1 1 calc R . . C17 C 0.1152(3) 1.05667(15) 0.34602(13) 0.0599(6) Uani 1 1 d . . . H17 H 0.0375 1.0896 0.3441 0.072 Uiso 1 1 calc R . . C18 C 0.1089(2) 0.98969(13) 0.29363(11) 0.0476(5) Uani 1 1 d . . . H18 H 0.0260 0.9776 0.2566 0.057 Uiso 1 1 calc R . . C19 C 0.22340(19) 0.94013(11) 0.29507(10) 0.0352(4) Uani 1 1 d . . . C20 C 0.20576(17) 0.86634(11) 0.16516(10) 0.0317(4) Uani 1 1 d . . . C21 C 0.21956(19) 0.94594(12) 0.12140(10) 0.0360(4) Uani 1 1 d . . . C22 C 0.1138(2) 1.00489(13) 0.09911(11) 0.0472(5) Uani 1 1 d . . . H22 H 0.0323 0.9961 0.1137 0.057 Uiso 1 1 calc R . . C23 C 0.1274(3) 1.07671(14) 0.05540(12) 0.0602(6) Uani 1 1 d . . . H23 H 0.0562 1.1162 0.0415 0.072 Uiso 1 1 calc R . . C24 C 0.2464(3) 1.08921(14) 0.03273(12) 0.0628(7) Uani 1 1 d . . . H24 H 0.2558 1.1371 0.0031 0.075 Uiso 1 1 calc R . . C25 C 0.3520(3) 1.03104(14) 0.05375(12) 0.0544(6) Uani 1 1 d . . . H25 H 0.4323 1.0403 0.0380 0.065 Uiso 1 1 calc R . . C26 C 0.3413(2) 0.95827(12) 0.09833(10) 0.0410(5) Uani 1 1 d . . . C27 C 0.4598(2) 0.89803(14) 0.12215(11) 0.0447(5) Uani 1 1 d . . . C28 C 0.5919(2) 0.93263(18) 0.14815(13) 0.0633(7) Uani 1 1 d . . . H28 H 0.6021 0.9916 0.1520 0.076 Uiso 1 1 calc R . . C29 C 0.7071(3) 0.8817(2) 0.16814(16) 0.0799(9) Uani 1 1 d . . . H29 H 0.7939 0.9064 0.1849 0.096 Uiso 1 1 calc R . . C30 C 0.6941(3) 0.7947(2) 0.16333(16) 0.0805(8) Uani 1 1 d . . . H30 H 0.7721 0.7602 0.1765 0.097 Uiso 1 1 calc R . . C31 C 0.5664(2) 0.75880(17) 0.13910(14) 0.0632(7) Uani 1 1 d . . . H31 H 0.5585 0.6997 0.1366 0.076 Uiso 1 1 calc R . . C32 C 0.4468(2) 0.80866(14) 0.11790(11) 0.0441(5) Uani 1 1 d . . . C33 C 0.3132(2) 0.76391(12) 0.08979(10) 0.0391(5) Uani 1 1 d . . . C34 C 0.3014(2) 0.69328(14) 0.03862(12) 0.0517(5) Uani 1 1 d . . . H34 H 0.3784 0.6746 0.0234 0.062 Uiso 1 1 calc R . . C35 C 0.1784(3) 0.65136(14) 0.01072(13) 0.0592(6) Uani 1 1 d . . . H35 H 0.1725 0.6048 -0.0232 0.071 Uiso 1 1 calc R . . C36 C 0.0643(2) 0.67823(14) 0.03289(12) 0.0561(6) Uani 1 1 d . . . H36 H -0.0193 0.6503 0.0135 0.067 Uiso 1 1 calc R . . C37 C 0.0730(2) 0.74687(13) 0.08400(11) 0.0445(5) Uani 1 1 d . . . H37 H -0.0050 0.7647 0.0987 0.053 Uiso 1 1 calc R . . C38 C 0.19691(18) 0.78944(11) 0.11353(10) 0.0345(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 C1 0.0339(9) 0.0305(10) 0.0316(9) 0.0009(8) 0.0070(7) 0.0011(8) C2 0.0510(11) 0.0280(10) 0.0306(9) -0.0009(8) 0.0127(8) 0.0010(9) C3 0.0651(14) 0.0439(12) 0.0440(11) 0.0005(10) 0.0148(10) -0.0115(11) C4 0.101(2) 0.0469(14) 0.0572(14) 0.0027(11) 0.0272(14) -0.0245(14) C5 0.121(2) 0.0338(12) 0.0555(14) 0.0111(11) 0.0307(15) -0.0024(14) C6 0.0925(18) 0.0393(12) 0.0427(11) 0.0084(10) 0.0155(12) 0.0193(13) C7 0.0608(13) 0.0320(11) 0.0332(9) 0.0020(8) 0.0131(9) 0.0088(9) C8 0.0534(13) 0.0467(13) 0.0317(10) 0.0019(9) 0.0052(9) 0.0110(10) C9 0.0600(15) 0.0679(17) 0.0542(13) 0.0036(12) 0.0042(11) 0.0202(13) C10 0.0515(16) 0.108(3) 0.0700(16) -0.0003(17) 0.0046(12) 0.0227(17) C11 0.0484(15) 0.108(2) 0.0644(16) 0.0005(16) 0.0018(12) -0.0058(16) C12 0.0549(14) 0.0670(16) 0.0509(12) 0.0004(12) 0.0030(11) -0.0067(12) C13 0.0485(12) 0.0492(13) 0.0313(9) 0.0020(9) 0.0053(8) -0.0003(10) C14 0.0529(12) 0.0316(10) 0.0318(9) 0.0011(8) 0.0097(8) -0.0016(9) C15 0.0729(15) 0.0401(12) 0.0380(10) -0.0039(9) 0.0063(10) -0.0065(11) C16 0.0926(18) 0.0383(12) 0.0474(12) -0.0095(10) 0.0216(12) 0.0073(13) C17 0.0769(17) 0.0496(14) 0.0540(13) -0.0038(11) 0.0186(12) 0.0209(12) C18 0.0565(13) 0.0428(12) 0.0418(10) -0.0021(9) 0.0099(9) 0.0092(10) C19 0.0482(11) 0.0296(10) 0.0286(9) 0.0034(8) 0.0114(8) 0.0019(8) C20 0.0321(9) 0.0309(10) 0.0317(9) -0.0007(8) 0.0075(7) -0.0013(8) C21 0.0489(11) 0.0308(10) 0.0266(8) -0.0015(8) 0.0072(8) -0.0041(9) C22 0.0608(13) 0.0392(12) 0.0391(10) 0.0020(9) 0.0089(9) 0.0058(10) C23 0.0938(18) 0.0372(12) 0.0443(12) 0.0048(10) 0.0086(12) 0.0094(13) C24 0.114(2) 0.0326(12) 0.0406(12) 0.0054(10) 0.0188(13) -0.0099(14) C25 0.0811(16) 0.0406(13) 0.0456(11) -0.0021(10) 0.0242(11) -0.0201(12) C26 0.0561(12) 0.0348(11) 0.0317(9) -0.0044(8) 0.0107(9) -0.0105(9) C27 0.0476(12) 0.0530(13) 0.0363(10) -0.0043(9) 0.0158(9) -0.0107(10) C28 0.0555(15) 0.0781(18) 0.0586(13) -0.0070(13) 0.0191(11) -0.0230(13) C29 0.0419(15) 0.122(3) 0.0752(17) -0.0083(18) 0.0139(12) -0.0197(16) C30 0.0456(15) 0.112(3) 0.0828(18) 0.0025(18) 0.0152(13) 0.0109(16) C31 0.0515(14) 0.0726(17) 0.0670(15) 0.0005(13) 0.0183(11) 0.0136(12) C32 0.0473(12) 0.0493(13) 0.0390(10) -0.0020(9) 0.0173(9) 0.0025(10) C33 0.0494(12) 0.0342(10) 0.0357(9) 0.0005(8) 0.0146(8) 0.0020(9) C34 0.0726(15) 0.0392(12) 0.0493(12) -0.0039(10) 0.0268(11) 0.0052(11) C35 0.0918(19) 0.0395(13) 0.0490(12) -0.0144(10) 0.0231(12) -0.0119(13) C36 0.0722(16) 0.0494(14) 0.0449(11) -0.0088(10) 0.0121(11) -0.0203(12) C37 0.0516(12) 0.0447(12) 0.0373(10) -0.0015(9) 0.0121(9) -0.0081(10) C38 0.0437(11) 0.0303(10) 0.0289(9) 0.0014(7) 0.0085(8) -0.0010(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 C1 C2 1.488(2) . ? C1 C19 1.490(2) . ? C1 C20 1.333(2) . ? C2 C3 1.380(3) . ? C2 C7 1.399(3) . ? C3 H3 0.9300 . ? C3 C4 1.378(3) . ? C4 H4 0.9300 . ? C4 C5 1.369(4) . ? C5 H5 0.9300 . ? C5 C6 1.371(3) . ? C6 H6 0.9300 . ? C6 C7 1.406(3) . ? C7 C8 1.481(3) . ? C8 C9 1.399(3) . ? C8 C13 1.414(3) . ? C9 H9 0.9300 . ? C9 C10 1.370(3) . ? C10 H10 0.9300 . ? C10 C11 1.377(4) . ? C11 H11 0.9300 . ? C11 C12 1.374(3) . ? C12 H12 0.9300 . ? C12 C13 1.400(3) . ? C13 C14 1.483(3) . ? C14 C15 1.400(3) . ? C14 C19 1.396(3) . ? C15 H15 0.9300 . ? C15 C16 1.372(3) . ? C16 H16 0.9300 . ? C16 C17 1.371(3) . ? C17 H17 0.9300 . ? C17 C18 1.381(3) . ? C18 H18 0.9300 . ? C18 C19 1.384(3) . ? C20 C21 1.487(2) . ? C20 C38 1.492(2) . ? C21 C22 1.386(3) . ? C21 C26 1.399(3) . ? C22 H22 0.9300 . ? C22 C23 1.385(3) . ? C23 H23 0.9300 . ? C23 C24 1.368(3) . ? C24 H24 0.9300 . ? C24 C25 1.375(3) . ? C25 H25 0.9300 . ? C25 C26 1.399(3) . ? C26 C27 1.492(3) . ? C27 C28 1.396(3) . ? C27 C32 1.407(3) . ? C28 H28 0.9300 . ? C28 C29 1.375(4) . ? C29 H29 0.9300 . ? C29 C30 1.371(4) . ? C30 H30 0.9300 . ? C30 C31 1.365(3) . ? C31 H31 0.9300 . ? C31 C32 1.401(3) . ? C32 C33 1.481(3) . ? C33 C34 1.406(3) . ? C33 C38 1.397(2) . ? C34 H34 0.9300 . ? C34 C35 1.373(3) . ? C35 H35 0.9300 . ? C35 C36 1.369(3) . ? C36 H36 0.9300 . ? C36 C37 1.384(3) . ? C37 H37 0.9300 . ? C37 C38 1.389(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C20 C21 123.81(16) . . ? C1 C20 C38 124.36(16) . . ? C2 C1 C19 110.93(14) . . ? C2 C3 H3 119.5 . . ? C2 C7 C6 117.4(2) . . ? C2 C7 C8 122.48(17) . . ? C3 C2 C1 121.83(17) . . ? C3 C2 C7 120.12(18) . . ? C3 C4 H4 120.1 . . ? C4 C3 C2 121.1(2) . . ? C4 C3 H3 119.5 . . ? C4 C5 H5 119.9 . . ? C4 C5 C6 120.1(2) . . ? C5 C4 C3 119.7(2) . . ? C5 C4 H4 120.1 . . ? C5 C6 H6 119.2 . . ? C5 C6 C7 121.6(2) . . ? C6 C5 H5 119.9 . . ? C6 C7 C8 120.13(19) . . ? C7 C2 C1 117.88(16) . . ? C7 C6 H6 119.2 . . ? C8 C9 H9 118.9 . . ? C8 C13 C14 123.01(18) . . ? C9 C8 C7 118.4(2) . . ? C9 C8 C13 118.1(2) . . ? C9 C10 H10 120.2 . . ? C9 C10 C11 119.7(2) . . ? C10 C9 C8 122.1(2) . . ? C10 C9 H9 118.9 . . ? C10 C11 H11 120.0 . . ? C11 C10 H10 120.2 . . ? C11 C12 H12 119.3 . . ? C11 C12 C13 121.5(2) . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 120.0 . . ? C12 C13 C8 118.7(2) . . ? C12 C13 C14 118.3(2) . . ? C13 C8 C7 123.50(18) . . ? C13 C12 H12 119.3 . . ? C14 C15 H15 119.2 . . ? C14 C19 C1 119.33(16) . . ? C15 C14 C13 120.51(18) . . ? C15 C16 H16 119.9 . . ? C16 C15 C14 121.7(2) . . ? C16 C15 H15 119.2 . . ? C16 C17 H17 120.3 . . ? C16 C17 C18 119.3(2) . . ? C17 C16 C15 120.1(2) . . ? C17 C16 H16 119.9 . . ? C17 C18 H18 119.3 . . ? C17 C18 C19 121.3(2) . . ? C18 C17 H17 120.3 . . ? C18 C19 C1 120.61(17) . . ? C18 C19 C14 119.73(17) . . ? C19 C14 C13 121.69(16) . . ? C19 C14 C15 117.79(18) . . ? C19 C18 H18 119.3 . . ? C20 C1 C2 124.14(16) . . ? C20 C1 C19 124.82(16) . . ? C21 C20 C38 111.61(14) . . ? C21 C22 H22 119.5 . . ? C21 C26 C25 118.1(2) . . ? C21 C26 C27 121.95(17) . . ? C22 C21 C20 122.33(17) . . ? C22 C21 C26 119.60(18) . . ? C22 C23 H23 120.2 . . ? C23 C22 C21 121.1(2) . . ? C23 C22 H22 119.5 . . ? C23 C24 H24 120.0 . . ? C23 C24 C25 120.1(2) . . ? C24 C23 C22 119.6(2) . . ? C24 C23 H23 120.2 . . ? C24 C25 H25 119.3 . . ? C24 C25 C26 121.5(2) . . ? C25 C24 H24 120.0 . . ? C25 C26 C27 119.90(18) . . ? C26 C21 C20 117.96(17) . . ? C26 C25 H25 119.3 . . ? C27 C28 H28 119.2 . . ? C27 C32 C33 123.56(18) . . ? C28 C27 C26 117.9(2) . . ? C28 C27 C32 118.1(2) . . ? C28 C29 H29 120.0 . . ? C29 C28 C27 121.7(3) . . ? C29 C28 H28 119.2 . . ? C29 C30 H30 120.2 . . ? C30 C29 C28 120.1(2) . . ? C30 C29 H29 120.0 . . ? C30 C31 H31 119.1 . . ? C30 C31 C32 121.8(3) . . ? C31 C30 C29 119.7(3) . . ? C31 C30 H30 120.2 . . ? C31 C32 C27 118.6(2) . . ? C31 C32 C33 117.8(2) . . ? C32 C27 C26 123.95(17) . . ? C32 C31 H31 119.1 . . ? C33 C34 H34 119.3 . . ? C33 C38 C20 119.11(16) . . ? C34 C33 C32 120.08(17) . . ? C34 C35 H35 120.1 . . ? C35 C34 C33 121.3(2) . . ? C35 C34 H34 119.3 . . ? C35 C36 H36 119.9 . . ? C35 C36 C37 120.2(2) . . ? C36 C35 C34 119.8(2) . . ? C36 C35 H35 120.1 . . ? C36 C37 H37 119.6 . . ? C36 C37 C38 120.74(19) . . ? C37 C36 H36 119.9 . . ? C37 C38 C20 121.16(16) . . ? C37 C38 C33 119.55(17) . . ? C38 C33 C32 121.64(16) . . ? C38 C33 C34 118.28(18) . . ? C38 C37 H37 119.6 . . ?