# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_4hacr _database_code_depnum_ccdc_archive 'CCDC 883137' #TrackingRef '4hacr.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2,3,4-tetrahydroacridine' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N' _chemical_formula_sum 'C13 H13 N' _chemical_formula_weight 183.24 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.5830(3) _cell_length_b 6.4220(3) _cell_length_c 9.2358(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.460(3) _cell_angle_gamma 90.00 _cell_volume 497.09(4) _cell_formula_units_Z 2 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 6109 _cell_measurement_theta_min 5.28 _cell_measurement_theta_max 67.19 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.543 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.26727 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Agilent Technologies' _exptl_special_details ? _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Saphire 3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6109 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.28 _diffrn_reflns_theta_max 67.19 _reflns_number_total 1711 _reflns_number_gt 1667 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (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^)+(0.0787P)^2^+0.0083P] 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 1711 _refine_ls_number_parameters 159 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 N10 N 0.23148(12) 0.6313(2) 0.54629(12) 0.0478(3) Uani 1 1 d . . . C1 C 0.07151(19) 0.2711(3) 0.22382(16) 0.0552(4) Uani 1 1 d . . . H1A H 0.1395(17) 0.172(3) 0.1762(17) 0.068(5) Uiso 1 1 d . . . H1B H -0.014(2) 0.174(4) 0.251(2) 0.081(6) Uiso 1 1 d . . . C2 C -0.0095(2) 0.4405(3) 0.12063(16) 0.0594(4) Uani 1 1 d . . . H2A H -0.0918(19) 0.371(4) 0.0339(19) 0.073(5) Uiso 1 1 d . . . H2B H 0.075(2) 0.521(3) 0.0689(18) 0.074(5) Uiso 1 1 d . . . C3 C -0.08559(19) 0.5974(3) 0.20482(19) 0.0613(4) Uani 1 1 d . . . H3A H -0.141(2) 0.713(4) 0.134(2) 0.090(6) Uiso 1 1 d . . . H3B H -0.1580(19) 0.515(4) 0.2555(18) 0.077(5) Uiso 1 1 d . . . C4 C 0.03968(17) 0.7047(2) 0.32106(16) 0.0514(4) Uani 1 1 d . . . H4A H -0.0063(18) 0.801(3) 0.3823(17) 0.066(5) Uiso 1 1 d . . . H4B H 0.1093(17) 0.807(3) 0.2651(16) 0.063(5) Uiso 1 1 d . . . C4A C 0.15288(14) 0.5576(2) 0.41787(13) 0.0415(3) Uani 1 1 d . . . C5 C 0.42286(17) 0.5808(3) 0.77436(15) 0.0590(5) Uani 1 1 d . . . H5 H 0.4018 0.7145 0.8038 0.071 Uiso 1 1 calc R . . C6 C 0.53283(17) 0.4601(4) 0.86573(15) 0.0680(5) Uani 1 1 d . . . H6 H 0.5862 0.5120 0.9570 0.082 Uiso 1 1 calc R . . C7 C 0.56589(17) 0.2578(4) 0.82264(16) 0.0647(5) Uani 1 1 d . . . H7 H 0.6414 0.1770 0.8856 0.078 Uiso 1 1 calc R . . C8 C 0.48821(16) 0.1786(3) 0.68914(16) 0.0553(4) Uani 1 1 d . . . H8 H 0.5108 0.0446 0.6615 0.066 Uiso 1 1 calc R . . C8A C 0.37284(14) 0.3016(2) 0.59270(14) 0.0446(4) Uani 1 1 d . . . C9 C 0.28452(14) 0.2271(2) 0.45518(14) 0.0446(3) Uani 1 1 d . . . H9 H 0.3018 0.0928 0.4245 0.054 Uiso 1 1 calc R . . C9A C 0.17383(14) 0.3518(2) 0.36716(14) 0.0419(3) Uani 1 1 d . . . C10A C 0.34072(14) 0.5043(2) 0.63543(13) 0.0455(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 N10 0.0545(6) 0.0432(8) 0.0453(6) -0.0045(5) 0.0102(4) 0.0033(5) C1 0.0667(8) 0.0456(10) 0.0483(8) -0.0064(7) 0.0012(6) 0.0005(8) C2 0.0680(8) 0.0544(11) 0.0492(7) -0.0016(7) -0.0022(6) 0.0018(8) C3 0.0568(8) 0.0596(12) 0.0617(8) 0.0027(8) 0.0004(6) 0.0103(7) C4 0.0598(8) 0.0422(10) 0.0510(8) -0.0001(6) 0.0094(6) 0.0113(7) C4A 0.0463(6) 0.0380(8) 0.0412(6) 0.0010(5) 0.0121(5) 0.0002(6) C5 0.0639(8) 0.0637(12) 0.0478(7) -0.0080(8) 0.0087(6) -0.0030(8) C6 0.0591(8) 0.0948(15) 0.0457(7) -0.0025(9) 0.0019(6) -0.0012(10) C7 0.0500(7) 0.0901(14) 0.0521(8) 0.0149(8) 0.0065(5) 0.0105(8) C8 0.0493(6) 0.0618(12) 0.0556(7) 0.0104(7) 0.0128(5) 0.0103(7) C8A 0.0434(6) 0.0478(10) 0.0443(6) 0.0043(6) 0.0134(5) 0.0017(6) C9 0.0519(6) 0.0356(8) 0.0470(7) -0.0004(6) 0.0122(5) 0.0021(6) C9A 0.0467(6) 0.0369(8) 0.0429(6) 0.0007(6) 0.0114(5) -0.0003(6) C10A 0.0473(6) 0.0490(10) 0.0410(6) 0.0008(6) 0.0112(5) -0.0022(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 N10 C4A 1.3191(16) . ? N10 C10A 1.3743(17) . ? C1 C2 1.513(2) . ? C1 C9A 1.5136(19) . ? C1 H1A 1.026(19) . ? C1 H1B 1.03(2) . ? C2 C3 1.505(2) . ? C2 H2A 1.047(18) . ? C2 H2B 1.084(19) . ? C3 C4 1.512(2) . ? C3 H3A 1.03(2) . ? C3 H3B 1.01(2) . ? C4 C4A 1.5036(18) . ? C4 H4A 0.977(18) . ? C4 H4B 1.090(18) . ? C4A C9A 1.427(2) . ? C5 C6 1.364(2) . ? C5 C10A 1.4123(18) . ? C5 H5 0.9300 . ? C6 C7 1.406(3) . ? C6 H6 0.9300 . ? C7 C8 1.367(2) . ? C7 H7 0.9300 . ? C8 C8A 1.4202(19) . ? C8 H8 0.9300 . ? C8A C10A 1.405(2) . ? C8A C9 1.4145(18) . ? C9 C9A 1.3679(17) . ? C9 H9 0.9300 . ? 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 C4A N10 C10A 118.45(12) . . ? C2 C1 C9A 113.92(14) . . ? C2 C1 H1A 113.8(10) . . ? C9A C1 H1A 108.2(8) . . ? C2 C1 H1B 109.5(11) . . ? C9A C1 H1B 107.6(10) . . ? H1A C1 H1B 103.1(16) . . ? C3 C2 C1 110.35(14) . . ? C3 C2 H2A 112.6(10) . . ? C1 C2 H2A 108.5(13) . . ? C3 C2 H2B 108.4(11) . . ? C1 C2 H2B 111.1(10) . . ? H2A C2 H2B 105.8(12) . . ? C2 C3 C4 110.53(13) . . ? C2 C3 H3A 110.3(12) . . ? C4 C3 H3A 106.1(12) . . ? C2 C3 H3B 105.5(13) . . ? C4 C3 H3B 109.1(10) . . ? H3A C3 H3B 115.3(15) . . ? C4A C4 C3 113.91(13) . . ? C4A C4 H4A 110.1(9) . . ? C3 C4 H4A 112.7(9) . . ? C4A C4 H4B 108.1(8) . . ? C3 C4 H4B 108.4(8) . . ? H4A C4 H4B 102.9(15) . . ? N10 C4A C9A 123.44(12) . . ? N10 C4A C4 116.68(12) . . ? C9A C4A C4 119.86(11) . . ? C6 C5 C10A 120.50(16) . . ? C6 C5 H5 119.7 . . ? C10A C5 H5 119.7 . . ? C5 C6 C7 120.34(15) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.69(15) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C8A 119.81(16) . . ? C7 C8 H8 120.1 . . ? C8A C8 H8 120.1 . . ? C10A C8A C9 117.76(12) . . ? C10A C8A C8 119.45(14) . . ? C9 C8A C8 122.77(14) . . ? C9A C9 C8A 120.32(13) . . ? C9A C9 H9 119.8 . . ? C8A C9 H9 119.8 . . ? C9 C9A C4A 117.89(12) . . ? C9 C9A C1 121.12(14) . . ? C4A C9A C1 120.94(12) . . ? N10 C10A C8A 122.11(12) . . ? N10 C10A C5 118.69(13) . . ? C8A C10A C5 119.21(13) . . ? 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 C9A C1 C2 C3 -46.7(2) . . . . ? C1 C2 C3 C4 62.8(2) . . . . ? C2 C3 C4 C4A -49.84(19) . . . . ? C10A N10 C4A C9A 0.77(19) . . . . ? C10A N10 C4A C4 -177.49(10) . . . . ? C3 C4 C4A N10 -159.95(12) . . . . ? C3 C4 C4A C9A 21.72(18) . . . . ? C10A C5 C6 C7 0.0(2) . . . . ? C5 C6 C7 C8 -0.2(2) . . . . ? C6 C7 C8 C8A 0.0(2) . . . . ? C7 C8 C8A C10A 0.4(2) . . . . ? C7 C8 C8A C9 -177.97(12) . . . . ? C10A C8A C9 C9A 1.00(18) . . . . ? C8 C8A C9 C9A 179.45(11) . . . . ? C8A C9 C9A C4A 0.82(18) . . . . ? C8A C9 C9A C1 -176.48(11) . . . . ? N10 C4A C9A C9 -1.80(19) . . . . ? C4 C4A C9A C9 176.41(11) . . . . ? N10 C4A C9A C1 175.51(13) . . . . ? C4 C4A C9A C1 -6.28(18) . . . . ? C2 C1 C9A C9 -163.78(13) . . . . ? C2 C1 C9A C4A 19.0(2) . . . . ? C4A N10 C10A C8A 1.23(18) . . . . ? C4A N10 C10A C5 -178.72(11) . . . . ? C9 C8A C10A N10 -2.10(17) . . . . ? C8 C8A C10A N10 179.40(12) . . . . ? C9 C8A C10A C5 177.85(12) . . . . ? C8 C8A C10A C5 -0.65(18) . . . . ? C6 C5 C10A N10 -179.64(12) . . . . ? C6 C5 C10A C8A 0.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 67.19 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.104 _refine_diff_density_min -0.108 _refine_diff_density_rms 0.026 # Attachment '4hanthr.cif' _audit_update_record ; 2012-05-21 # Formatted by publCIF ; data_4hanthr _database_code_depnum_ccdc_archive 'CCDC 883138' #TrackingRef '4hanthr.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2,3,4-tetrahydroanthracene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14' _chemical_formula_sum 'C14 H14' _chemical_formula_weight 182.25 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.2543(4) _cell_length_b 7.8898(5) _cell_length_c 10.5305(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.611(7) _cell_angle_gamma 90.00 _cell_volume 512.33(6) _cell_formula_units_Z 2 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 6498 _cell_measurement_theta_min 4.26 _cell_measurement_theta_max 67.10 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.765 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'CrysAlisPro, Agilent Technologies' _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, saphire 3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6498 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.26 _diffrn_reflns_theta_max 67.10 _reflns_number_total 1788 _reflns_number_gt 1655 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (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^)+(0.0873P)^2^+0.0074P] 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 SHELXL _refine_ls_extinction_coef 0.028(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1788 _refine_ls_number_parameters 179 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1342 _refine_ls_wR_factor_gt 0.1311 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.105 _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 C1 C 0.2153(3) 0.2562(3) -0.32792(15) 0.0673(5) Uani 1 1 d . . . H1A H 0.351(3) 0.250(3) -0.345(2) 0.103(7) Uiso 1 1 d . . . H1B H 0.176(5) 0.386(5) -0.341(3) 0.153(11) Uiso 1 1 d . . . C2 C 0.0675(14) 0.1506(11) -0.4237(6) 0.0716(14) Uani 0.697(18) 1 d P A 1 H2A H 0.065(4) 0.217(5) -0.517(3) 0.087(9) Uiso 0.697(18) 1 d P A 1 H2B H 0.149(5) 0.034(5) -0.425(3) 0.100(11) Uiso 0.697(18) 1 d P A 1 C3 C -0.1602(8) 0.1460(11) -0.3852(4) 0.0691(14) Uani 0.697(18) 1 d P A 1 H3A H -0.282(5) 0.089(4) -0.447(3) 0.083(8) Uiso 0.697(18) 1 d P A 1 H3B H -0.234(5) 0.265(5) -0.384(3) 0.092(11) Uiso 0.697(18) 1 d P A 1 C2A C 0.015(3) 0.205(3) -0.4138(15) 0.078(3) Uani 0.303(18) 1 d P A 2 H2C H -0.0817 0.3024 -0.4239 0.094 Uiso 0.303(18) 1 calc PR A 2 H2D H 0.0520 0.1814 -0.4977 0.094 Uiso 0.303(18) 1 calc PR A 2 C3A C -0.108(3) 0.061(3) -0.3781(10) 0.082(3) Uani 0.303(18) 1 d P A 2 H3C H -0.2435 0.0532 -0.4380 0.098 Uiso 0.303(18) 1 calc PR A 2 H3D H -0.0264 -0.0418 -0.3863 0.098 Uiso 0.303(18) 1 calc PR A 2 C4 C -0.1537(3) 0.0710(3) -0.25240(17) 0.0688(5) Uani 1 1 d D . . H4A H -0.289(2) 0.087(3) -0.2285(19) 0.088(6) Uiso 1 1 d D . . H4B H -0.145(5) -0.042(5) -0.261(4) 0.166(15) Uiso 1 1 d . . . C4A C 0.0325(2) 0.12743(19) -0.15162(14) 0.0474(4) Uani 1 1 d . A . C5 C 0.2134(2) 0.0942(2) 0.20386(14) 0.0573(5) Uani 1 1 d . . . H5 H 0.0956 0.0393 0.2288 0.069 Uiso 1 1 calc R . . C6 C 0.3887(3) 0.1342(3) 0.29445(15) 0.0659(5) Uani 1 1 d . . . H6 H 0.3900 0.1056 0.3802 0.079 Uiso 1 1 calc R . . C7 C 0.5667(3) 0.2182(2) 0.25865(16) 0.0659(5) Uani 1 1 d . . . H7 H 0.6857 0.2443 0.3210 0.079 Uiso 1 1 calc R . . C8 C 0.5678(2) 0.2622(2) 0.13357(15) 0.0592(5) Uani 1 1 d . . . H8 H 0.6861 0.3198 0.1116 0.071 Uiso 1 1 calc R . . C8A C 0.3884(2) 0.2203(2) 0.03634(14) 0.0466(4) Uani 1 1 d . A . C9 C 0.3835(2) 0.2604(2) -0.09437(14) 0.0502(4) Uani 1 1 d . . . H9 H 0.4991 0.3196 -0.1182 0.060 Uiso 1 1 calc R A . C9A C 0.2124(2) 0.21442(19) -0.18798(13) 0.0478(4) Uani 1 1 d . A . C10 C 0.0332(2) 0.09212(19) -0.02438(15) 0.0490(4) Uani 1 1 d . . . H10 H -0.0865 0.0378 -0.0011 0.059 Uiso 1 1 calc R A . C10A C 0.2083(2) 0.1348(2) 0.07288(13) 0.0464(4) Uani 1 1 d . A . 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 0.0642(9) 0.0889(15) 0.0511(8) 0.0051(9) 0.0159(7) -0.0066(10) C2 0.074(3) 0.091(4) 0.0515(15) -0.008(2) 0.0157(16) 0.004(2) C3 0.0582(19) 0.087(4) 0.0573(15) -0.0056(18) -0.0044(12) -0.002(2) C2A 0.075(7) 0.112(11) 0.043(4) -0.004(5) -0.001(4) 0.014(6) C3A 0.079(6) 0.104(9) 0.058(4) -0.022(5) 0.000(4) -0.014(6) C4 0.0561(9) 0.0814(15) 0.0646(10) 0.0003(9) -0.0019(7) -0.0156(10) C4A 0.0442(7) 0.0450(8) 0.0526(7) -0.0018(7) 0.0064(6) -0.0010(6) C5 0.0571(8) 0.0600(11) 0.0568(8) 0.0072(8) 0.0150(6) 0.0033(8) C6 0.0743(10) 0.0726(12) 0.0501(8) 0.0064(9) 0.0079(7) 0.0112(9) C7 0.0625(9) 0.0707(11) 0.0588(9) -0.0042(9) -0.0060(7) 0.0045(9) C8 0.0499(8) 0.0633(12) 0.0629(9) -0.0027(8) 0.0048(6) -0.0051(8) C8A 0.0434(7) 0.0429(8) 0.0537(8) -0.0014(6) 0.0086(5) 0.0011(6) C9 0.0463(8) 0.0520(11) 0.0543(8) 0.0009(7) 0.0141(6) -0.0076(7) C9A 0.0466(7) 0.0480(9) 0.0502(8) 0.0014(7) 0.0117(6) 0.0021(6) C10 0.0411(7) 0.0495(10) 0.0577(8) 0.0021(7) 0.0119(6) -0.0049(6) C10A 0.0463(7) 0.0435(9) 0.0509(7) -0.0012(6) 0.0121(6) 0.0024(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2A 1.475(15) . ? C1 C2 1.501(7) . ? C1 C9A 1.5132(19) . ? C1 H1A 0.90(2) . ? C1 H1B 1.06(4) . ? C2 C3 1.545(11) . ? C2 H2A 1.11(3) . ? C2 H2B 1.05(4) . ? C3 C4 1.513(5) . ? C3 H3A 1.02(3) . ? C3 H3B 1.05(4) . ? C2A C3A 1.46(3) . ? C2A H2C 0.9700 . ? C2A H2D 0.9700 . ? C3A C4 1.402(10) . ? C3A H3A 1.22(4) . ? C3A H3C 0.9700 . ? C3A H3D 0.9700 . ? C4 C4A 1.506(2) . ? C4 H4A 0.928(10) . ? C4 H4B 0.90(4) . ? C4A C10 1.368(2) . ? C4A C9A 1.4242(19) . ? C5 C6 1.365(2) . ? C5 C10A 1.411(2) . ? C5 H5 0.9300 . ? C6 C7 1.400(2) . ? C6 H6 0.9300 . ? C7 C8 1.363(2) . ? C7 H7 0.9300 . ? C8 C8A 1.426(2) . ? C8 H8 0.9300 . ? C8A C9 1.408(2) . ? C8A C10A 1.4200(18) . ? C9 C9A 1.3769(19) . ? C9 H9 0.9300 . ? C10 C10A 1.410(2) . ? C10 H10 0.9300 . ? 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 C2A C1 C9A 113.0(7) . . ? C2 C1 C9A 115.3(3) . . ? C2A C1 H1A 127.0(18) . . ? C2 C1 H1A 109.7(16) . . ? C9A C1 H1A 110.3(15) . . ? C2A C1 H1B 92(2) . . ? C2 C1 H1B 110.4(18) . . ? C9A C1 H1B 107.2(19) . . ? H1A C1 H1B 103(2) . . ? C1 C2 C3 109.2(6) . . ? C1 C2 H2A 104.3(17) . . ? C3 C2 H2A 111.5(16) . . ? C1 C2 H2B 104.5(19) . . ? C3 C2 H2B 116.9(19) . . ? H2A C2 H2B 109(3) . . ? C4 C3 C2 111.6(6) . . ? C4 C3 H3A 108.7(16) . . ? C2 C3 H3A 117.6(15) . . ? C4 C3 H3B 106.6(17) . . ? C2 C3 H3B 114.1(18) . . ? H3A C3 H3B 97(3) . . ? C3A C2A C1 119.1(14) . . ? C3A C2A H2A 122(3) . . ? C1 C2A H2A 102(2) . . ? C3A C2A H2C 107.5 . . ? C1 C2A H2C 107.5 . . ? H2A C2A H2C 95.3 . . ? C3A C2A H2D 107.5 . . ? C1 C2A H2D 107.5 . . ? H2C C2A H2D 107.0 . . ? C4 C3A C2A 113.5(16) . . ? C4 C3A H3A 104.5(17) . . ? C2A C3A H3A 99(3) . . ? C4 C3A H3C 108.9 . . ? C2A C3A H3C 108.9 . . ? C4 C3A H3D 108.9 . . ? C2A C3A H3D 108.9 . . ? H3A C3A H3D 121.8 . . ? H3C C3A H3D 107.7 . . ? C2A C3A H4B 141.5(17) . . ? H3A C3A H4B 109.7(19) . . ? H3C C3A H4B 104.9 . . ? H3D C3A H4B 77.2 . . ? C3A C4 C4A 115.2(5) . . ? C4A C4 C3 115.7(2) . . ? C3A C4 H4A 127.0(15) . . ? C4A C4 H4A 113.6(13) . . ? C3 C4 H4A 108.3(13) . . ? C3A C4 H4B 80(3) . . ? C4A C4 H4B 108(2) . . ? C3 C4 H4B 107(3) . . ? H4A C4 H4B 103(2) . . ? C10 C4A C9A 119.21(12) . . ? C10 C4A C4 120.38(14) . . ? C9A C4A C4 120.39(13) . . ? C6 C5 C10A 121.00(14) . . ? C6 C5 H5 119.5 . . ? C10A C5 H5 119.5 . . ? C5 C6 C7 120.22(14) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.88(14) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C8A 120.30(15) . . ? C7 C8 H8 119.9 . . ? C8A C8 H8 119.9 . . ? C9 C8A C10A 118.88(12) . . ? C9 C8A C8 122.43(14) . . ? C10A C8A C8 118.70(13) . . ? C9A C9 C8A 121.89(13) . . ? C9A C9 H9 119.1 . . ? C8A C9 H9 119.1 . . ? C9 C9A C4A 119.28(12) . . ? C9 C9A C1 120.37(13) . . ? C4A C9A C1 120.35(12) . . ? C4A C10 C10A 122.55(13) . . ? C4A C10 H10 118.7 . . ? C10A C10 H10 118.7 . . ? C10 C10A C5 122.95(13) . . ? C10 C10A C8A 118.16(12) . . ? C5 C10A C8A 118.89(13) . . ? 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 C2A C1 C2 C3 -40(2) . . . . ? C9A C1 C2 C3 48.8(9) . . . . ? C1 C2 C3 C4 -59.7(10) . . . . ? C2 C1 C2A C3A 72(3) . . . . ? C9A C1 C2A C3A -29(3) . . . . ? C1 C2A C3A C4 51(4) . . . . ? C2A C3A C4 C4A -44(3) . . . . ? C2A C3A C4 C3 54(2) . . . . ? C2 C3 C4 C3A -53.9(11) . . . . ? C2 C3 C4 C4A 42.3(8) . . . . ? C3A C4 C4A C10 -159.3(13) . . . . ? C3 C4 C4A C10 168.2(4) . . . . ? C3A C4 C4A C9A 19.1(13) . . . . ? C3 C4 C4A C9A -13.4(4) . . . . ? C10A C5 C6 C7 0.6(3) . . . . ? C5 C6 C7 C8 0.4(3) . . . . ? C6 C7 C8 C8A -1.2(3) . . . . ? C7 C8 C8A C9 -178.90(14) . . . . ? C7 C8 C8A C10A 1.0(3) . . . . ? C10A C8A C9 C9A -2.1(2) . . . . ? C8 C8A C9 C9A 177.86(14) . . . . ? C8A C9 C9A C4A 1.6(3) . . . . ? C8A C9 C9A C1 -178.56(13) . . . . ? C10 C4A C9A C9 0.3(2) . . . . ? C4 C4A C9A C9 -178.14(17) . . . . ? C10 C4A C9A C1 -179.59(17) . . . . ? C4 C4A C9A C1 2.0(2) . . . . ? C2A C1 C9A C9 -177.1(11) . . . . ? C2 C1 C9A C9 159.1(4) . . . . ? C2A C1 C9A C4A 2.8(11) . . . . ? C2 C1 C9A C4A -21.0(5) . . . . ? C9A C4A C10 C10A -1.6(2) . . . . ? C4 C4A C10 C10A 176.82(14) . . . . ? C4A C10 C10A C5 -177.95(12) . . . . ? C4A C10 C10A C8A 1.1(2) . . . . ? C6 C5 C10A C10 178.34(14) . . . . ? C6 C5 C10A C8A -0.7(2) . . . . ? C9 C8A C10A C10 0.8(2) . . . . ? C8 C8A C10A C10 -179.18(17) . . . . ? C9 C8A C10A C5 179.83(18) . . . . ? C8 C8A C10A C5 -0.12(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 67.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.153 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.038 data_andl0710 _database_code_depnum_ccdc_archive 'CCDC 883448' #TrackingRef 'publiandl0710.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H16' _chemical_formula_sum 'C15 H16' _chemical_formula_weight 196.28 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.9319(11) _cell_length_b 11.2138(16) _cell_length_c 13.945(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1084.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2700 _cell_measurement_theta_min 3.2711 _cell_measurement_theta_max 31.9923 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.9140 _exptl_absorpt_correction_T_max 0.9790 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford-Diffraction XCALIBUR' _diffrn_measurement_method \w-\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_unetI/netI 0.0235 _diffrn_reflns_number 11492 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 32.07 _diffrn_reflns_theta_full 32.07 _diffrn_measured_fraction_theta_full 0.965 _diffrn_measured_fraction_theta_max 0.965 _reflns_number_total 2103 _reflns_number_gt 1730 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0863P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2103 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.3 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.2090(2) -0.08160(13) 0.14820(11) 0.0301(3) Uani 1 1 d . . . H1A H 0.0939 -0.0797 0.1062 0.036 Uiso 1 1 calc R . . H1B H 0.1629 -0.0843 0.2154 0.036 Uiso 1 1 calc R . . C2 C 0.3203(2) -0.19494(13) 0.12777(12) 0.0317(3) Uani 1 1 d . . . H2A H 0.4061 -0.2127 0.1827 0.038 Uiso 1 1 calc R . . H2B H 0.2287 -0.2621 0.1208 0.038 Uiso 1 1 calc R . . C3 C 0.4396(2) -0.18456(13) 0.03784(12) 0.0353(4) Uani 1 1 d . . . H3A H 0.3548 -0.1668 -0.0175 0.042 Uiso 1 1 calc R . . H3B H 0.5063 -0.261 0.0252 0.042 Uiso 1 1 calc R . . C4 C 0.5871(2) -0.08566(13) 0.04976(11) 0.0321(3) Uani 1 1 d . . . H4A H 0.6868 -0.112 0.0959 0.038 Uiso 1 1 calc R . . H4B H 0.6514 -0.0716 -0.0126 0.038 Uiso 1 1 calc R . . C4A C 0.5008(2) 0.03005(12) 0.08458(9) 0.0247(3) Uani 1 1 d . . . C5 C 0.6324(3) 0.35237(13) 0.08777(11) 0.0337(3) Uani 1 1 d . . . H5 H 0.752 0.3506 0.0545 0.04 Uiso 1 1 calc R . . C6 C 0.5624(3) 0.45826(14) 0.12101(11) 0.0390(4) Uani 1 1 d . . . H6 H 0.6332 0.5296 0.1105 0.047 Uiso 1 1 calc R . . C7 C 0.3865(3) 0.46240(13) 0.17054(11) 0.0378(4) Uani 1 1 d . . . H7 H 0.3401 0.5363 0.1945 0.045 Uiso 1 1 calc R . . C8 C 0.2817(2) 0.36098(14) 0.18456(11) 0.0323(3) Uani 1 1 d . . . H8 H 0.1614 0.3657 0.217 0.039 Uiso 1 1 calc R . . C8A C 0.3486(2) 0.24826(12) 0.15166(9) 0.0249(3) Uani 1 1 d . . . C9 C 0.24511(19) 0.13973(13) 0.16610(10) 0.0252(3) Uani 1 1 d . . . C9A C 0.32052(19) 0.03212(12) 0.13385(9) 0.0232(3) Uani 1 1 d . . . C10 C 0.5991(2) 0.13458(13) 0.06914(10) 0.0264(3) Uani 1 1 d . . . H10 H 0.7178 0.1324 0.0351 0.032 Uiso 1 1 calc R . . C10A C 0.5287(2) 0.24485(12) 0.10231(9) 0.0254(3) Uani 1 1 d . . . C11 C 0.0521(2) 0.14299(16) 0.21668(13) 0.0419(4) Uani 1 1 d . . . H11A H -0.0252 0.0741 0.1969 0.063 Uiso 1 1 calc R . . H11B H -0.0159 0.2166 0.1997 0.063 Uiso 1 1 calc R . . H11C H 0.0724 0.1404 0.2862 0.063 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 C1 0.0291(7) 0.0286(7) 0.0326(7) -0.0021(6) 0.0056(6) -0.0043(6) C2 0.0351(8) 0.0244(7) 0.0355(7) 0.0001(6) 0.0005(7) -0.0042(6) C3 0.0398(9) 0.0268(7) 0.0393(8) -0.0054(6) 0.0040(7) 0.0004(7) C4 0.0306(7) 0.0267(6) 0.0390(8) -0.0032(6) 0.0071(6) 0.0015(6) C4A 0.0255(6) 0.0260(6) 0.0226(6) -0.0005(5) 0.0025(5) 0.0011(5) C5 0.0414(8) 0.0301(7) 0.0296(7) 0.0027(6) 0.0029(7) -0.0083(7) C6 0.0544(11) 0.0267(7) 0.0359(8) 0.0028(6) -0.0025(8) -0.0095(7) C7 0.0533(10) 0.0254(7) 0.0348(8) -0.0017(6) -0.0053(7) 0.0051(7) C8 0.0366(8) 0.0300(7) 0.0304(7) -0.0021(6) -0.0006(6) 0.0064(7) C8A 0.0270(6) 0.0256(6) 0.0220(6) -0.0002(5) -0.0007(5) 0.0027(5) C9 0.0224(6) 0.0280(6) 0.0252(6) -0.0003(5) 0.0026(5) 0.0011(6) C9A 0.0213(6) 0.0251(6) 0.0232(6) 0.0007(5) 0.0008(5) -0.0007(5) C10 0.0239(6) 0.0299(6) 0.0253(6) 0.0003(5) 0.0041(5) 0.0000(6) C10A 0.0290(7) 0.0256(6) 0.0216(6) 0.0011(5) 0.0006(5) -0.0021(6) C11 0.0288(7) 0.0450(9) 0.0519(10) -0.0042(8) 0.0132(7) 0.0028(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C9A 1.5047(19) . ? C1 C2 1.514(2) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.507(2) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.517(2) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C4A 1.5090(19) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C4A C10 1.3727(18) . ? C4A C9A 1.4264(18) . ? C5 C6 1.364(2) . ? C5 C10A 1.418(2) . ? C5 H5 0.95 . ? C6 C7 1.402(3) . ? C6 H6 0.95 . ? C7 C8 1.364(2) . ? C7 H7 0.95 . ? C8 C8A 1.4223(19) . ? C8 H8 0.95 . ? C8A C10A 1.4259(19) . ? C8A C9 1.4270(19) . ? C9 C9A 1.3898(19) . ? C9 C11 1.513(2) . ? C10 C10A 1.408(2) . ? C10 H10 0.95 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? 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 C9A C1 C2 115.11(12) . . ? C9A C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? C9A C1 H1B 108.5 . . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C3 C2 C1 111.81(12) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 109.57(13) . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? C4A C4 C3 113.38(12) . . ? C4A C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C4A C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C10 C4A C9A 119.76(12) . . ? C10 C4A C4 119.15(12) . . ? C9A C4A C4 121.08(11) . . ? C6 C5 C10A 120.74(15) . . ? C6 C5 H5 119.6 . . ? C10A C5 H5 119.6 . . ? C5 C6 C7 120.37(14) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.42(14) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C8A 121.41(14) . . ? C7 C8 H8 119.3 . . ? C8A C8 H8 119.3 . . ? C8 C8A C10A 117.70(13) . . ? C8 C8A C9 123.27(13) . . ? C10A C8A C9 119.03(12) . . ? C9A C9 C8A 120.38(12) . . ? C9A C9 C11 120.30(13) . . ? C8A C9 C11 119.32(13) . . ? C9 C9A C4A 119.97(12) . . ? C9 C9A C1 119.97(12) . . ? C4A C9A C1 120.03(12) . . ? C4A C10 C10A 121.78(12) . . ? C4A C10 H10 119.1 . . ? C10A C10 H10 119.1 . . ? C10 C10A C5 121.60(13) . . ? C10 C10A C8A 119.06(12) . . ? C5 C10A C8A 119.34(13) . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF