# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 188/154 data_global #============================================================================== # Paper 8/08320G Perkin 2 #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_autor ; Martin Nieger Institut f\"ur Anorganische Chemie Universit\"at Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Bundesrepublik Deutschland ; _publ_contact_author_phone '049 228 73-5823' _publ_contact_author_fax '049 228 73-5327' _publ_contact_author_email 'NIEGER@OC3062.CHEMIE.UNI-BONN.DE' _publ_requested_journal 'J. Chem. Soc., Perkin 2 Trans.' _publ_requested_coeditor_name ? _publ_contact_letter ; Please find enclosed necessary x-ray data for our publication in J. Chem. Soc., Perkin 2 Trans. ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Experimental and Theoretical Studies of a Chiral Azulenophane: Synthesis, Strcture and Circular Dichroism Spectra of 14,17-dimethyl-[2](1,3)azuleno- [2]paracyclophane ; loop_ _publ_author_name _publ_author_address 'Grimme, Stefan' ; Institut f\"ur Physikalische und Theoretische Chemie Universit\"at Bonn Wegelerstr. 12 D-53115 Bonn Bundesrepublik Deutschland ; 'Mennike, Wolfram' ; Kekule-Institut f\"ur Organische Chemie und Biochemie Universit\"at Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Bundesrepublik Deutschland ; 'V\"ogtle, Fritz' ; Kekule-Institut f\"ur Organische Chemie und Biochemie Universit\"at Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Bundesrepublik Deutschland ; 'Nieger, Martin' ; Institut f\"ur Anorganische Chemie Universit\"at Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Bundesrepublik Deutschland ; #============================================================================== Paper 8/08320G Perkin 2 #============================================================================== data_voe346_compound_2c _audit_creation_method SHELXL-97 _chemical_name_systematic ; 14,17-Dimethyl-[2](1,3)azuleno[2]paracyclophane ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22' _chemical_formula_weight 286.40 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1) (no.4)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.9870(2) _cell_length_b 12.6805(4) _cell_length_c 8.1337(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.788(2) _cell_angle_gamma 90.00 _cell_volume 792.70(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 10319 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min '0.9801 (theor.)' _exptl_absorpt_correction_T_max '0.9946 (theor.)' _exptl_special_details ; dx = 29.902(4), 2 x 90 sec, 1 deg., 404 frames (phi + omega), mos.= 0.480(2) ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg,' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11472 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3718 _reflns_number_gt 3258 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.0000P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.088(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack '-2(7) cannot be determined reliabl.' _refine_ls_number_reflns 3718 _refine_ls_number_parameters 202 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.21365(19) 0.30967(12) 0.56792(18) 0.0273(3) Uani 1 d . . . H1A H 0.1312 0.2768 0.6241 0.033 Uiso 1 calc R . . H1B H 0.3327 0.3025 0.6449 0.033 Uiso 1 calc R . . C2 C 0.20186(17) 0.25224(12) 0.39214(17) 0.0237(3) Uani 1 d . . . H2A H 0.3191 0.2502 0.3732 0.028 Uiso 1 calc R . . H2B H 0.1635 0.1785 0.3991 0.028 Uiso 1 calc R . . C3 C 0.07733(16) 0.30593(10) 0.24108(17) 0.0201(3) Uani 1 d . . . C3A C -0.10511(17) 0.29714(11) 0.18493(17) 0.0203(3) Uani 1 d . . . C4 C -0.20495(18) 0.21922(12) 0.23307(18) 0.0235(3) Uani 1 d . . . H4 H -0.1420 0.1681 0.3112 0.028 Uiso 1 calc R . . C5 C -0.38496(18) 0.20608(13) 0.18194(19) 0.0287(3) Uani 1 d . . . H5 H -0.4278 0.1457 0.2265 0.034 Uiso 1 calc R . . C6 C -0.51038(18) 0.26941(14) 0.0746(2) 0.0313(4) Uani 1 d . . . H6 H -0.6267 0.2454 0.0559 0.038 Uiso 1 calc R . . C7 C -0.49212(18) 0.36245(14) -0.00989(19) 0.0318(4) Uani 1 d . . . H7 H -0.5975 0.3946 -0.0728 0.038 Uiso 1 calc R . . C8 C -0.34036(17) 0.41464(13) -0.01449(17) 0.0263(3) Uani 1 d . . . H8 H -0.3563 0.4772 -0.0811 0.032 Uiso 1 calc R . . C8A C -0.16867(17) 0.38801(11) 0.06479(17) 0.0225(3) Uani 1 d . . . C9 C -0.02020(17) 0.44457(11) 0.05509(18) 0.0226(3) Uani 1 d . . . C10 C 0.12485(17) 0.39076(11) 0.15369(17) 0.0215(3) Uani 1 d . . . H10 H 0.2417 0.4095 0.1606 0.026 Uiso 1 calc R . . C11 C -0.0104(2) 0.55583(12) -0.00701(19) 0.0278(3) Uani 1 d . . . H11A H -0.1091 0.5682 -0.1092 0.033 Uiso 1 calc R . . H11B H 0.0987 0.5645 -0.0412 0.033 Uiso 1 calc R . . C12 C -0.0158(2) 0.64047(12) 0.13375(19) 0.0291(3) Uani 1 d . . . H12A H 0.0527 0.7032 0.1198 0.035 Uiso 1 calc R . . H12B H -0.1375 0.6630 0.1207 0.035 Uiso 1 calc R . . C13 C 0.05886(18) 0.59327(11) 0.30968(18) 0.0239(3) Uani 1 d . . . C14 C 0.23739(18) 0.57607(12) 0.37772(19) 0.0254(3) Uani 1 d . . . C15 C 0.28842(18) 0.49120(12) 0.48966(18) 0.0255(3) Uani 1 d . . . H15 H 0.4092 0.4786 0.5373 0.031 Uiso 1 calc R . . C16 C 0.16988(18) 0.42439(12) 0.53435(17) 0.0230(3) Uani 1 d . . . C17 C -0.00494(17) 0.45816(12) 0.49907(18) 0.0222(3) Uani 1 d . . . C18 C -0.05530(18) 0.54130(11) 0.38506(17) 0.0225(3) Uani 1 d . . . H18 H -0.1731 0.5638 0.3571 0.027 Uiso 1 calc R . . C19 C -0.13807(19) 0.40202(13) 0.56721(19) 0.0301(3) Uani 1 d . . . H19A H -0.2485 0.4406 0.5335 0.045 Uiso 1 calc R . . H19B H -0.0971 0.3985 0.6921 0.045 Uiso 1 calc R . . H19C H -0.1553 0.3304 0.5203 0.045 Uiso 1 calc R . . C20 C 0.3709(2) 0.63599(15) 0.3147(2) 0.0391(4) Uani 1 d . . . H20A H 0.4878 0.6183 0.3855 0.059 Uiso 1 calc R . . H20B H 0.3511 0.7119 0.3220 0.059 Uiso 1 calc R . . H20C H 0.3607 0.6167 0.1957 0.059 Uiso 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 0.0310(7) 0.0251(8) 0.0227(8) 0.0028(6) 0.0022(6) 0.0038(6) C2 0.0243(7) 0.0217(7) 0.0240(7) 0.0010(6) 0.0048(5) 0.0030(6) C3 0.0239(7) 0.0162(7) 0.0204(7) -0.0033(5) 0.0066(5) 0.0003(5) C3A 0.0254(7) 0.0189(7) 0.0175(7) -0.0036(5) 0.0073(5) 0.0011(5) C4 0.0279(7) 0.0221(7) 0.0212(7) -0.0028(6) 0.0076(5) -0.0002(6) C5 0.0300(8) 0.0287(8) 0.0297(8) -0.0053(7) 0.0121(6) -0.0067(6) C6 0.0226(7) 0.0389(10) 0.0322(8) -0.0104(7) 0.0072(6) -0.0033(6) C7 0.0236(7) 0.0431(10) 0.0258(8) -0.0074(7) 0.0017(6) 0.0061(6) C8 0.0307(7) 0.0279(8) 0.0186(7) -0.0012(6) 0.0041(5) 0.0081(6) C8A 0.0276(7) 0.0214(7) 0.0181(7) -0.0043(5) 0.0057(5) 0.0017(6) C9 0.0294(7) 0.0219(8) 0.0170(7) -0.0020(5) 0.0072(5) -0.0001(6) C10 0.0255(7) 0.0216(8) 0.0194(7) -0.0047(5) 0.0092(5) -0.0012(6) C11 0.0390(8) 0.0238(8) 0.0209(7) 0.0027(6) 0.0088(6) -0.0004(6) C12 0.0403(8) 0.0210(8) 0.0251(8) 0.0017(6) 0.0073(6) 0.0016(6) C13 0.0331(8) 0.0162(7) 0.0227(7) -0.0037(6) 0.0082(6) -0.0009(6) C14 0.0306(8) 0.0208(7) 0.0252(8) -0.0057(6) 0.0083(6) -0.0052(6) C15 0.0234(7) 0.0279(8) 0.0223(7) -0.0066(6) 0.0016(5) -0.0004(6) C16 0.0280(7) 0.0239(7) 0.0143(6) -0.0044(6) 0.0009(5) 0.0001(6) C17 0.0279(7) 0.0221(7) 0.0165(6) -0.0052(5) 0.0058(5) -0.0024(5) C18 0.0256(7) 0.0214(8) 0.0200(7) -0.0039(6) 0.0055(5) 0.0031(6) C19 0.0359(8) 0.0311(9) 0.0259(8) -0.0059(7) 0.0127(6) -0.0044(7) C20 0.0370(9) 0.0372(10) 0.0450(11) -0.0005(8) 0.0146(8) -0.0116(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 C16 1.504(2) . ? C1 C2 1.584(2) . ? C2 C3 1.5158(18) . ? C3 C10 1.3976(19) . ? C3 C3A 1.4079(18) . ? C3A C4 1.3912(19) . ? C3A C8A 1.507(2) . ? C4 C5 1.394(2) . ? C5 C6 1.391(2) . ? C6 C7 1.393(2) . ? C7 C8 1.390(2) . ? C8 C8A 1.3889(19) . ? C8A C9 1.4064(19) . ? C9 C10 1.395(2) . ? C9 C11 1.508(2) . ? C11 C12 1.579(2) . ? C12 C13 1.516(2) . ? C13 C18 1.3949(19) . ? C13 C14 1.3992(19) . ? C14 C15 1.397(2) . ? C14 C20 1.508(2) . ? C15 C16 1.391(2) . ? C16 C17 1.4133(19) . ? C17 C18 1.389(2) . ? C17 C19 1.505(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 C16 C1 C2 109.09(11) . . ? C3 C2 C1 112.94(12) . . ? C10 C3 C3A 107.23(12) . . ? C10 C3 C2 123.29(12) . . ? C3A C3 C2 128.34(12) . . ? C4 C3A C3 125.93(13) . . ? C4 C3A C8A 127.44(12) . . ? C3 C3A C8A 106.63(11) . . ? C3A C4 C5 128.66(14) . . ? C6 C5 C4 128.79(15) . . ? C5 C6 C7 130.14(14) . . ? C8 C7 C6 128.72(14) . . ? C8A C8 C7 129.02(15) . . ? C8 C8A C9 126.23(14) . . ? C8 C8A C3A 127.08(13) . . ? C9 C8A C3A 106.61(11) . . ? C10 C9 C8A 107.42(12) . . ? C10 C9 C11 122.66(13) . . ? C8A C9 C11 128.13(13) . . ? C9 C10 C3 111.78(12) . . ? C9 C11 C12 112.27(12) . . ? C13 C12 C11 109.56(12) . . ? C18 C13 C14 118.05(13) . . ? C18 C13 C12 117.71(12) . . ? C14 C13 C12 122.14(13) . . ? C15 C14 C13 117.59(13) . . ? C15 C14 C20 120.11(13) . . ? C13 C14 C20 121.73(14) . . ? C16 C15 C14 122.76(13) . . ? C15 C16 C17 117.88(14) . . ? C15 C16 C1 119.72(12) . . ? C17 C16 C1 119.87(13) . . ? C18 C17 C16 117.13(13) . . ? C18 C17 C19 119.97(12) . . ? C16 C17 C19 122.68(14) . . ? C17 C18 C13 123.15(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C1 C2 C3 -26.61(16) . . . . ? C1 C2 C3 C10 85.04(15) . . . . ? C1 C2 C3 C3A -81.20(17) . . . . ? C10 C3 C3A C4 176.29(13) . . . . ? C2 C3 C3A C4 -15.7(2) . . . . ? C10 C3 C3A C8A -3.92(14) . . . . ? C2 C3 C3A C8A 164.07(13) . . . . ? C3 C3A C4 C5 -179.81(14) . . . . ? C8A C3A C4 C5 0.4(2) . . . . ? C3A C4 C5 C6 -2.4(3) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C5 C6 C7 C8 3.1(3) . . . . ? C6 C7 C8 C8A -0.6(3) . . . . ? C7 C8 C8A C9 -179.92(15) . . . . ? C7 C8 C8A C3A -3.6(2) . . . . ? C4 C3A C8A C8 3.6(2) . . . . ? C3 C3A C8A C8 -176.21(13) . . . . ? C4 C3A C8A C9 -179.50(13) . . . . ? C3 C3A C8A C9 0.71(14) . . . . ? C8 C8A C9 C10 179.75(13) . . . . ? C3A C8A C9 C10 2.79(14) . . . . ? C8 C8A C9 C11 14.9(2) . . . . ? C3A C8A C9 C11 -162.09(13) . . . . ? C8A C9 C10 C3 -5.51(16) . . . . ? C11 C9 C10 C3 160.39(13) . . . . ? C3A C3 C10 C9 5.97(15) . . . . ? C2 C3 C10 C9 -162.77(12) . . . . ? C10 C9 C11 C12 -82.14(17) . . . . ? C8A C9 C11 C12 80.67(18) . . . . ? C9 C11 C12 C13 28.03(17) . . . . ? C11 C12 C13 C18 -89.46(16) . . . . ? C11 C12 C13 C14 73.73(17) . . . . ? C18 C13 C14 C15 14.13(19) . . . . ? C12 C13 C14 C15 -149.01(14) . . . . ? C18 C13 C14 C20 -174.55(14) . . . . ? C12 C13 C14 C20 22.3(2) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C20 C14 C15 C16 -171.26(14) . . . . ? C14 C15 C16 C17 -15.6(2) . . . . ? C14 C15 C16 C1 146.30(14) . . . . ? C2 C1 C16 C15 -72.97(15) . . . . ? C2 C1 C16 C17 88.62(15) . . . . ? C15 C16 C17 C18 16.03(19) . . . . ? C1 C16 C17 C18 -145.89(13) . . . . ? C15 C16 C17 C19 -169.45(13) . . . . ? C1 C16 C17 C19 28.6(2) . . . . ? C16 C17 C18 C13 -1.8(2) . . . . ? C19 C17 C18 C13 -176.47(13) . . . . ? C14 C13 C18 C17 -13.6(2) . . . . ? C12 C13 C18 C17 150.27(14) . . . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.286 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.051 #==============================================================================