data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Andrew Whiting' 'Jonathan H. Barnard' 'A Batsanov' 'Caroline E. Bridgens' 'Emily B. Cartmell' 'Victoria B. Christie' 'Jonathan C Collings' 'Daniel J. Maltman' 'Todd Marder' 'Stefan A. Przyborski' 'Christopher P. F. Redfern' _publ_contact_author_name 'Andrew Whiting' _publ_contact_author_email ANDY.WHITING@DURHAM.AC. _publ_section_title ; Synthesis and Evaluation of Synthetic Retinoid Derivatives as Inducers of Stem Cell Differentiation ; #Attachment 'retinoid.cif' data_(1) _database_code_depnum_ccdc_archive 'CCDC 688676' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene ; _chemical_name_common ? _chemical_melting_point 317 _chemical_formula_moiety 'C14 H19 Br' _chemical_formula_sum 'C14 H19 Br' _chemical_formula_weight 267.20 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.760(1) _cell_length_b 10.508(1) _cell_length_c 15.461(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1260.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5961 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 30.0 _exptl_crystal_description block _exptl_crystal_colour off-white _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 3.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3756 _exptl_absorpt_correction_T_max 0.4546 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker,2003), R(int)=0.054 before correction' _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of 600 scans (0.3\% \w, 5s exposure) each; every set at different \f angle. Crystal to detector distance 4.84 cm. 2101 unique reflections and 1565 Friedel equivalents. ; _diffrn_ambient_temperature 120(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 'Bruker SMART 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 5.6 _diffrn_standards_number 0 _diffrn_reflns_number 23007 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 29.97 _reflns_number_total 3666 _reflns_number_gt 3423 _reflns_threshold_expression I>2\s(I) _reflns_Friedel_coverage 0.74 _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT version 6.02A (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL version 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL version 6.12 (Bruker, 2001)' _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. Methyl groups: rotating bodies with refined C---H distance and refined U(iso) common to all three H atoms. Other H atoms: refall. ; _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^)+(0.0210P)^2^+0.1690P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.013(6) _refine_ls_number_reflns 3666 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0201 _refine_ls_R_factor_gt 0.0170 _refine_ls_wR_factor_ref 0.0413 _refine_ls_wR_factor_gt 0.0402 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br Br 0.399828(14) 0.498965(13) 0.393150(7) 0.02444(4) Uani 1 1 d . . . C1 C 0.39496(19) -0.09321(11) 0.39672(8) 0.0168(2) Uani 1 1 d . . . C2 C 0.25713(17) -0.14997(14) 0.33706(10) 0.0206(3) Uani 1 1 d . . . H21 H 0.293(2) -0.1442(15) 0.2789(10) 0.022(4) Uiso 1 1 d . . . H22 H 0.2410(19) -0.2327(19) 0.3497(10) 0.022(5) Uiso 1 1 d . . . C3 C 0.0856(2) -0.08112(12) 0.34380(9) 0.0209(3) Uani 1 1 d . . . H31 H 0.0441(19) -0.0837(13) 0.4021(10) 0.013(3) Uiso 1 1 d . . . H32 H -0.003(2) -0.1227(15) 0.3105(11) 0.025(4) Uiso 1 1 d . . . C4 C 0.09764(19) 0.05747(11) 0.31341(8) 0.0161(2) Uani 1 1 d . . . C5 C 0.26156(15) 0.25502(13) 0.35596(8) 0.0163(2) Uani 1 1 d . . . H5 H 0.173(2) 0.3029(16) 0.3294(11) 0.033(5) Uiso 1 1 d . . . C6 C 0.39709(15) 0.31778(11) 0.39496(7) 0.01671(19) Uani 1 1 d . . . C7 C 0.52818(16) 0.25221(12) 0.43618(8) 0.0194(2) Uani 1 1 d . . . H7 H 0.624(2) 0.2983(15) 0.4646(10) 0.025(4) Uiso 1 1 d . . . C8 C 0.52108(16) 0.12035(12) 0.43596(8) 0.0185(2) Uani 1 1 d . . . H8 H 0.606(2) 0.0734(15) 0.4650(10) 0.025(4) Uiso 1 1 d . . . C9 C 0.38766(17) 0.05256(11) 0.39530(8) 0.0145(2) Uani 1 1 d . . . C10 C 0.25298(14) 0.12130(13) 0.35624(7) 0.0142(3) Uani 1 1 d . . . C11 C 0.36707(18) -0.13974(13) 0.48999(8) 0.0245(3) Uani 1 1 d . . . H111 H 0.2576(12) -0.1119(9) 0.5100(3) 0.034(3) Uiso 1 1 d R . . H112 H 0.4547(12) -0.1059(9) 0.5263(4) 0.034(3) Uiso 1 1 d R . . H113 H 0.3717(13) -0.2301(9) 0.49137(14) 0.034(3) Uiso 1 1 d R . . C12 C 0.57198(17) -0.13999(12) 0.36517(9) 0.0225(3) Uani 1 1 d . . . H121 H 0.6609(8) -0.1100(9) 0.4044(5) 0.027(2) Uiso 1 1 d R . . H122 H 0.5938(6) -0.1071(8) 0.3075(6) 0.027(2) Uiso 1 1 d R . . H123 H 0.5730(5) -0.2324(9) 0.3637(6) 0.027(2) Uiso 1 1 d R . . C13 C -0.07120(16) 0.12447(13) 0.33775(9) 0.0212(2) Uani 1 1 d . . . H131 H -0.0831(6) 0.1261(8) 0.4001(6) 0.027(2) Uiso 1 1 d R . . H132 H -0.1674(9) 0.0788(7) 0.3127(6) 0.027(2) Uiso 1 1 d R . . H133 H -0.0697(6) 0.2107(8) 0.3158(6) 0.027(2) Uiso 1 1 d R . . C14 C 0.11872(18) 0.06380(12) 0.21414(8) 0.0225(2) Uani 1 1 d . . . H141 H 0.0235(11) 0.0248(9) 0.1875(3) 0.026(2) Uiso 1 1 d R . . H142 H 0.2202(11) 0.0211(9) 0.19794(18) 0.026(2) Uiso 1 1 d R . . H143 H 0.1254(13) 0.1493(8) 0.19659(19) 0.026(2) Uiso 1 1 d 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 Br 0.02631(6) 0.01307(5) 0.03395(6) -0.00114(7) -0.00087(5) -0.00361(7) C1 0.0180(5) 0.0142(5) 0.0183(5) 0.0018(4) 0.0028(5) 0.0006(5) C2 0.0219(7) 0.0133(6) 0.0266(7) -0.0023(5) -0.0039(5) -0.0001(4) C3 0.0205(6) 0.0153(5) 0.0270(6) 0.0014(5) -0.0030(6) -0.0049(5) C4 0.0146(5) 0.0163(5) 0.0175(5) 0.0008(4) -0.0020(5) -0.0026(5) C5 0.0158(5) 0.0154(5) 0.0176(5) 0.0010(4) -0.0013(4) -0.0005(4) C6 0.0178(5) 0.0122(4) 0.0201(5) -0.0009(4) 0.0025(5) -0.0015(4) C7 0.0176(5) 0.0200(6) 0.0207(6) -0.0029(5) -0.0024(5) -0.0018(5) C8 0.0152(5) 0.0204(6) 0.0199(6) -0.0011(4) -0.0051(4) 0.0014(5) C9 0.0154(5) 0.0144(5) 0.0137(5) 0.0001(4) -0.0004(5) 0.0007(5) C10 0.0153(6) 0.0138(6) 0.0136(5) 0.0002(4) 0.0008(4) -0.0011(4) C11 0.0303(7) 0.0222(6) 0.0211(6) 0.0063(5) 0.0022(5) 0.0017(5) C12 0.0220(6) 0.0167(5) 0.0290(6) -0.0008(5) 0.0028(5) 0.0041(5) C13 0.0145(5) 0.0226(6) 0.0265(6) 0.0003(5) -0.0020(5) -0.0010(5) C14 0.0233(6) 0.0252(6) 0.0189(5) -0.0002(4) -0.0027(5) -0.0045(5) _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 Br C6 1.9042(12) . ? C1 C9 1.5329(18) . ? C1 C2 1.5331(19) . ? C1 C11 1.5381(17) . ? C1 C12 1.5383(19) . ? C2 C3 1.519(2) . ? C2 H21 0.945(15) . ? C2 H22 0.90(2) . ? C3 C4 1.5331(17) . ? C3 H31 0.957(15) . ? C3 H32 0.962(17) . ? C4 C10 1.5302(17) . ? C4 C13 1.5342(19) . ? C4 C14 1.5450(17) . ? C5 C6 1.3800(17) . ? C5 C10 1.4067(18) . ? C5 H5 0.946(19) . ? C6 C7 1.3841(17) . ? C7 C8 1.3867(17) . ? C7 H7 0.989(16) . ? C8 C9 1.4052(17) . ? C8 H8 0.935(16) . ? C9 C10 1.4067(17) . ? C11 H111 0.9503 . ? C11 H112 0.9503 . ? C11 H113 0.9504 . ? C12 H121 0.9708 . ? C12 H122 0.9708 . ? C12 H123 0.9709 . ? C13 H131 0.9680 . ? C13 H132 0.9678 . ? C13 H133 0.9680 . ? C14 H141 0.9404 . ? C14 H142 0.9403 . ? C14 H143 0.9403 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 C1 C2 110.75(12) . . ? C9 C1 C11 109.02(11) . . ? C2 C1 C11 110.01(11) . . ? C9 C1 C12 110.35(12) . . ? C2 C1 C12 107.93(11) . . ? C11 C1 C12 108.74(11) . . ? C3 C2 C1 112.64(12) . . ? C3 C2 H21 107.2(10) . . ? C1 C2 H21 109.9(10) . . ? C3 C2 H22 108.9(10) . . ? C1 C2 H22 110.0(10) . . ? H21 C2 H22 108.0(14) . . ? C2 C3 C4 112.21(13) . . ? C2 C3 H31 110.2(9) . . ? C4 C3 H31 109.6(9) . . ? C2 C3 H32 111.8(10) . . ? C4 C3 H32 108.1(10) . . ? H31 C3 H32 104.5(13) . . ? C10 C4 C3 109.38(12) . . ? C10 C4 C13 111.44(10) . . ? C3 C4 C13 107.98(12) . . ? C10 C4 C14 109.13(11) . . ? C3 C4 C14 110.60(9) . . ? C13 C4 C14 108.32(11) . . ? C6 C5 C10 120.80(11) . . ? C6 C5 H5 119.3(11) . . ? C10 C5 H5 119.9(10) . . ? C5 C6 C7 121.56(11) . . ? C5 C6 Br 118.68(9) . . ? C7 C6 Br 119.76(9) . . ? C6 C7 C8 117.85(11) . . ? C6 C7 H7 120.8(9) . . ? C8 C7 H7 121.4(9) . . ? C7 C8 C9 122.47(11) . . ? C7 C8 H8 119.9(10) . . ? C9 C8 H8 117.6(10) . . ? C8 C9 C10 118.63(11) . . ? C8 C9 C1 118.22(12) . . ? C10 C9 C1 123.14(12) . . ? C9 C10 C5 118.63(11) . . ? C9 C10 C4 123.09(12) . . ? C5 C10 C4 118.28(11) . . ? C1 C11 H111 109.5 . . ? C1 C11 H112 109.5 . . ? H111 C11 H112 109.5 . . ? C1 C11 H113 109.5 . . ? H111 C11 H113 109.5 . . ? H112 C11 H113 109.5 . . ? C1 C12 H121 109.4 . . ? C1 C12 H122 109.5 . . ? H121 C12 H122 109.5 . . ? C1 C12 H123 109.5 . . ? H121 C12 H123 109.5 . . ? H122 C12 H123 109.5 . . ? C4 C13 H131 109.5 . . ? C4 C13 H132 109.5 . . ? H131 C13 H132 109.5 . . ? C4 C13 H133 109.5 . . ? H131 C13 H133 109.5 . . ? H132 C13 H133 109.5 . . ? C4 C14 H141 109.5 . . ? C4 C14 H142 109.4 . . ? H141 C14 H142 109.5 . . ? C4 C14 H143 109.5 . . ? H141 C14 H143 109.5 . . ? H142 C14 H143 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 -41.76(16) . . . . ? C11 C1 C2 C3 78.83(14) . . . . ? C12 C1 C2 C3 -162.66(11) . . . . ? C1 C2 C3 C4 64.09(15) . . . . ? C2 C3 C4 C10 -48.61(14) . . . . ? C2 C3 C4 C13 -170.03(12) . . . . ? C2 C3 C4 C14 71.61(16) . . . . ? C10 C5 C6 C7 -0.53(18) . . . . ? C10 C5 C6 Br -179.44(9) . . . . ? C5 C6 C7 C8 1.08(18) . . . . ? Br C6 C7 C8 179.98(9) . . . . ? C6 C7 C8 C9 0.46(19) . . . . ? C7 C8 C9 C10 -2.49(19) . . . . ? C7 C8 C9 C1 178.29(13) . . . . ? C2 C1 C9 C8 -170.58(11) . . . . ? C11 C1 C9 C8 68.24(16) . . . . ? C12 C1 C9 C8 -51.13(16) . . . . ? C2 C1 C9 C10 10.23(19) . . . . ? C11 C1 C9 C10 -110.94(13) . . . . ? C12 C1 C9 C10 129.69(13) . . . . ? C8 C9 C10 C5 2.96(17) . . . . ? C1 C9 C10 C5 -177.86(12) . . . . ? C8 C9 C10 C4 -177.45(12) . . . . ? C1 C9 C10 C4 1.74(19) . . . . ? C6 C5 C10 C9 -1.53(18) . . . . ? C6 C5 C10 C4 178.85(10) . . . . ? C3 C4 C10 C9 17.15(16) . . . . ? C13 C4 C10 C9 136.47(12) . . . . ? C14 C4 C10 C9 -103.96(13) . . . . ? C3 C4 C10 C5 -163.25(11) . . . . ? C13 C4 C10 C5 -43.93(15) . . . . ? C14 C4 C10 C5 75.64(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.316 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.041 #===================================END data_(2a) _database_code_depnum_ccdc_archive 'CCDC 688677' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-trimethylsilylethynyl-1,1,4,4-tetramethyl-1,2,3,4- tetrahydronaphthalene ; _chemical_name_common ? _chemical_melting_point 325 _chemical_formula_moiety 'C19 H28 Si' _chemical_formula_sum 'C19 H28 Si' _chemical_formula_weight 284.50 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.0434(7) _cell_length_b 13.3512(15) _cell_length_c 22.597(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1823.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7139 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 29.02 _exptl_crystal_description lump _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.036 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 10s exposure), every run at a different \f angle. Crystal to detector distance 4.41 cm. 2786 unique reflections after merging Friedel equivalents. ; _diffrn_ambient_temperature 120(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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 21097 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 29.01 _reflns_number_total 4839 _reflns_number_gt 4331 _reflns_threshold_expression I>2\s(I) _reflns_Friedel_coverage 0.74 _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0324P)^2^+0.3815P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(9) _refine_ls_number_reflns 4839 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 Si Si -0.01406(6) 0.58080(3) 0.594869(16) 0.02653(9) Uani 1 1 d . . . C1 C 0.8528(2) 0.29916(11) 0.32915(6) 0.0265(3) Uani 1 1 d . . . C2 C 0.8898(3) 0.37274(12) 0.27819(7) 0.0355(3) Uani 1 1 d . . . H21 H 1.009(4) 0.3427(13) 0.2489(8) 0.044(5) Uiso 1 1 d . . . H22 H 0.742(4) 0.3834(16) 0.2550(9) 0.058(6) Uiso 1 1 d . . . C3 C 0.9716(3) 0.47326(12) 0.29970(7) 0.0375(3) Uani 1 1 d . . . H31 H 1.018(3) 0.5162(14) 0.2665(8) 0.044(5) Uiso 1 1 d . . . H32 H 1.107(3) 0.4615(13) 0.3224(8) 0.040(5) Uiso 1 1 d . . . C4 C 0.8030(2) 0.52697(10) 0.33947(6) 0.0271(3) Uani 1 1 d . . . C5 C 0.5491(2) 0.49159(10) 0.42503(6) 0.0252(3) Uani 1 1 d . . . H5 H 0.532(3) 0.5650(13) 0.4286(7) 0.036(4) Uiso 1 1 d . . . C6 C 0.4409(2) 0.43101(10) 0.46598(6) 0.0256(3) Uani 1 1 d . . . C7 C 0.4778(2) 0.32715(10) 0.46387(6) 0.0264(3) Uani 1 1 d . . . H7 H 0.408(3) 0.2841(13) 0.4918(8) 0.041(5) Uiso 1 1 d . . . C8 C 0.6114(2) 0.28830(10) 0.42013(6) 0.0245(3) Uani 1 1 d . . . H8 H 0.634(3) 0.2166(13) 0.4184(7) 0.028(4) Uiso 1 1 d . . . C9 C 0.7149(2) 0.34850(10) 0.37740(6) 0.0214(2) Uani 1 1 d . . . C10 C 0.6885(2) 0.45320(9) 0.38122(6) 0.0218(2) Uani 1 1 d . . . C11 C 1.0730(3) 0.26478(17) 0.35536(9) 0.0479(5) Uani 1 1 d . . . H111 H 1.037(3) 0.2099(15) 0.3830(9) 0.051(5) Uiso 1 1 d . . . H112 H 1.159(4) 0.325(2) 0.3732(11) 0.086(8) Uiso 1 1 d . . . H113 H 1.167(4) 0.2315(16) 0.3225(9) 0.060(6) Uiso 1 1 d . . . C12 C 0.7313(4) 0.20787(15) 0.30302(9) 0.0462(5) Uani 1 1 d . . . H121 H 0.577(4) 0.2288(17) 0.2892(10) 0.075(7) Uiso 1 1 d . . . H122 H 0.726(4) 0.1482(18) 0.3361(10) 0.077(7) Uiso 1 1 d . . . H123 H 0.811(5) 0.1902(19) 0.2675(12) 0.085(8) Uiso 1 1 d . . . C13 C 0.9282(3) 0.60707(12) 0.37513(8) 0.0378(4) Uani 1 1 d . . . H131 H 1.012(3) 0.6522(13) 0.3487(8) 0.044(5) Uiso 1 1 d . . . H132 H 1.037(3) 0.5741(14) 0.4030(8) 0.047(5) Uiso 1 1 d . . . H133 H 0.825(3) 0.6485(14) 0.4005(9) 0.048(5) Uiso 1 1 d . . . C14 C 0.6282(3) 0.57881(14) 0.30075(7) 0.0378(3) Uani 1 1 d . . . H141 H 0.552(3) 0.5300(14) 0.2767(8) 0.044(5) Uiso 1 1 d . . . H142 H 0.707(3) 0.6315(15) 0.2725(9) 0.053(6) Uiso 1 1 d . . . H143 H 0.522(3) 0.6154(12) 0.3262(7) 0.033(4) Uiso 1 1 d . . . C15 C 0.2928(2) 0.47490(11) 0.50880(6) 0.0286(3) Uani 1 1 d . . . C16 C 0.1688(2) 0.51423(11) 0.54317(6) 0.0307(3) Uani 1 1 d . . . C17 C -0.1396(4) 0.68843(16) 0.55489(9) 0.0489(5) Uani 1 1 d . . . H171 H -0.027(5) 0.7294(18) 0.5387(11) 0.082(8) Uiso 1 1 d . . . H172 H -0.248(5) 0.667(2) 0.5229(11) 0.084(8) Uiso 1 1 d . . . H173 H -0.231(5) 0.721(2) 0.5815(11) 0.087(8) Uiso 1 1 d . . . C18 C -0.2313(3) 0.49380(14) 0.62139(8) 0.0377(3) Uani 1 1 d . . . H181 H -0.314(3) 0.4689(15) 0.5872(9) 0.055(6) Uiso 1 1 d . . . H182 H -0.325(4) 0.5300(16) 0.6497(9) 0.059(6) Uiso 1 1 d . . . H183 H -0.160(4) 0.4382(17) 0.6402(9) 0.062(6) Uiso 1 1 d . . . C19 C 0.1591(3) 0.62400(14) 0.65805(8) 0.0380(4) Uani 1 1 d . . . H191 H 0.294(3) 0.6609(14) 0.6456(8) 0.044(5) Uiso 1 1 d . . . H192 H 0.227(3) 0.5657(14) 0.6806(8) 0.041(5) Uiso 1 1 d . . . H193 H 0.078(3) 0.6660(14) 0.6851(9) 0.048(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si 0.02773(18) 0.02680(17) 0.02506(17) -0.00168(15) 0.00325(15) 0.00332(15) C1 0.0274(7) 0.0258(7) 0.0262(7) -0.0043(5) 0.0030(5) 0.0012(5) C2 0.0395(9) 0.0369(8) 0.0300(7) -0.0020(6) 0.0085(6) -0.0009(7) C3 0.0383(9) 0.0329(8) 0.0413(8) 0.0018(6) 0.0159(7) -0.0038(7) C4 0.0298(7) 0.0237(7) 0.0279(7) 0.0021(5) 0.0005(5) -0.0003(5) C5 0.0276(6) 0.0228(6) 0.0252(6) -0.0003(5) -0.0016(5) 0.0033(5) C6 0.0243(6) 0.0307(7) 0.0218(6) -0.0019(5) 0.0004(5) 0.0030(5) C7 0.0290(6) 0.0282(6) 0.0222(6) 0.0043(5) 0.0014(6) -0.0011(6) C8 0.0296(6) 0.0207(6) 0.0232(6) 0.0014(5) -0.0021(5) 0.0020(5) C9 0.0198(6) 0.0239(6) 0.0203(6) -0.0012(5) -0.0033(5) 0.0013(5) C10 0.0209(6) 0.0229(6) 0.0216(6) 0.0010(5) -0.0030(5) 0.0011(5) C11 0.0361(9) 0.0604(12) 0.0474(10) -0.0044(9) 0.0007(8) 0.0225(9) C12 0.0536(11) 0.0426(9) 0.0424(10) -0.0194(8) 0.0141(9) -0.0130(8) C13 0.0429(9) 0.0293(8) 0.0412(9) 0.0006(6) 0.0009(7) -0.0092(6) C14 0.0412(8) 0.0375(8) 0.0345(8) 0.0110(8) -0.0025(7) 0.0023(7) C15 0.0294(7) 0.0308(7) 0.0256(6) 0.0010(5) -0.0011(6) 0.0019(6) C16 0.0324(7) 0.0328(7) 0.0270(7) -0.0005(6) 0.0013(6) 0.0015(6) C17 0.0589(12) 0.0432(11) 0.0444(10) 0.0079(8) 0.0055(9) 0.0210(9) C18 0.0320(8) 0.0432(9) 0.0380(8) -0.0022(7) 0.0019(7) -0.0056(7) C19 0.0381(8) 0.0392(9) 0.0367(8) -0.0080(7) 0.0003(7) -0.0047(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 Si C16 1.8374(15) . ? Si C18 1.8527(17) . ? Si C17 1.8592(19) . ? Si C19 1.8619(17) . ? C1 C9 1.5224(18) . ? C1 C11 1.527(2) . ? C1 C2 1.530(2) . ? C1 C12 1.540(2) . ? C2 C3 1.510(2) . ? C2 H21 1.06(2) . ? C2 H22 1.04(2) . ? C3 C4 1.536(2) . ? C3 H31 0.986(19) . ? C3 H32 0.981(19) . ? C4 C10 1.5294(19) . ? C4 C14 1.536(2) . ? C4 C13 1.538(2) . ? C5 C6 1.3919(19) . ? C5 C10 1.3975(18) . ? C5 H5 0.989(17) . ? C6 C7 1.4053(19) . ? C6 C15 1.4427(18) . ? C7 C8 1.3774(19) . ? C7 H7 0.953(18) . ? C8 C9 1.4035(19) . ? C8 H8 0.968(16) . ? C9 C10 1.4096(18) . ? C11 H111 0.99(2) . ? C11 H112 1.04(3) . ? C11 H113 1.04(2) . ? C12 H121 1.02(3) . ? C12 H122 1.09(2) . ? C12 H123 0.97(3) . ? C13 H131 0.988(19) . ? C13 H132 1.012(19) . ? C13 H133 1.01(2) . ? C14 H141 0.965(19) . ? C14 H142 1.06(2) . ? C14 H143 0.992(17) . ? C15 C16 1.2000(19) . ? C17 H171 0.95(3) . ? C17 H172 1.02(3) . ? C17 H173 0.93(3) . ? C18 H181 0.98(2) . ? C18 H182 0.98(2) . ? C18 H183 0.96(2) . ? C19 H191 0.99(2) . ? C19 H192 1.016(19) . ? C19 H193 0.96(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 Si C18 109.19(8) . . ? C16 Si C17 108.07(8) . . ? C18 Si C17 110.65(10) . . ? C16 Si C19 107.42(7) . . ? C18 Si C19 110.16(8) . . ? C17 Si C19 111.26(10) . . ? C9 C1 C11 109.23(12) . . ? C9 C1 C2 109.96(12) . . ? C11 C1 C2 110.94(14) . . ? C9 C1 C12 110.85(12) . . ? C11 C1 C12 109.03(15) . . ? C2 C1 C12 106.81(13) . . ? C3 C2 C1 112.08(13) . . ? C3 C2 H21 108.5(10) . . ? C1 C2 H21 109.1(10) . . ? C3 C2 H22 108.6(12) . . ? C1 C2 H22 110.0(12) . . ? H21 C2 H22 108.5(15) . . ? C2 C3 C4 112.72(13) . . ? C2 C3 H31 111.4(10) . . ? C4 C3 H31 111.3(11) . . ? C2 C3 H32 107.5(11) . . ? C4 C3 H32 108.8(11) . . ? H31 C3 H32 104.7(16) . . ? C10 C4 C3 111.12(11) . . ? C10 C4 C14 109.27(12) . . ? C3 C4 C14 109.47(12) . . ? C10 C4 C13 110.31(12) . . ? C3 C4 C13 107.76(13) . . ? C14 C4 C13 108.86(13) . . ? C6 C5 C10 122.75(12) . . ? C6 C5 H5 118.2(10) . . ? C10 C5 H5 119.0(10) . . ? C5 C6 C7 118.45(12) . . ? C5 C6 C15 120.08(13) . . ? C7 C6 C15 121.46(12) . . ? C8 C7 C6 119.27(12) . . ? C8 C7 H7 120.6(11) . . ? C6 C7 H7 120.1(11) . . ? C7 C8 C9 122.63(13) . . ? C7 C8 H8 118.9(9) . . ? C9 C8 H8 118.4(9) . . ? C8 C9 C10 118.38(12) . . ? C8 C9 C1 119.28(12) . . ? C10 C9 C1 122.34(12) . . ? C5 C10 C9 118.38(12) . . ? C5 C10 C4 118.28(11) . . ? C9 C10 C4 123.34(12) . . ? C1 C11 H111 106.0(12) . . ? C1 C11 H112 110.8(14) . . ? H111 C11 H112 116.0(18) . . ? C1 C11 H113 109.2(12) . . ? H111 C11 H113 104.9(16) . . ? H112 C11 H113 109.6(17) . . ? C1 C12 H121 109.6(13) . . ? C1 C12 H122 109.2(13) . . ? H121 C12 H122 112.4(19) . . ? C1 C12 H123 105.9(16) . . ? H121 C12 H123 105(2) . . ? H122 C12 H123 114(2) . . ? C4 C13 H131 111.1(10) . . ? C4 C13 H132 110.1(10) . . ? H131 C13 H132 107.7(15) . . ? C4 C13 H133 112.0(11) . . ? H131 C13 H133 109.0(15) . . ? H132 C13 H133 106.7(14) . . ? C4 C14 H141 110.1(11) . . ? C4 C14 H142 109.4(11) . . ? H141 C14 H142 108.8(15) . . ? C4 C14 H143 109.7(10) . . ? H141 C14 H143 110.6(15) . . ? H142 C14 H143 108.2(14) . . ? C16 C15 C6 177.74(16) . . ? C15 C16 Si 176.97(14) . . ? Si C17 H171 110.0(16) . . ? Si C17 H172 112.8(15) . . ? H171 C17 H172 110.7(19) . . ? Si C17 H173 107.1(16) . . ? H171 C17 H173 114(2) . . ? H172 C17 H173 102(2) . . ? Si C18 H181 108.7(12) . . ? Si C18 H182 108.1(12) . . ? H181 C18 H182 112.6(16) . . ? Si C18 H183 108.2(13) . . ? H181 C18 H183 108.4(17) . . ? H182 C18 H183 110.6(17) . . ? Si C19 H191 113.4(11) . . ? Si C19 H192 112.0(10) . . ? H191 C19 H192 101.0(15) . . ? Si C19 H193 112.3(12) . . ? H191 C19 H193 108.0(15) . . ? H192 C19 H193 109.5(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C10 C4 C3 -7.89(19) . . . . ? C10 C4 C3 C2 39.84(18) . . . . ? C4 C3 C2 C1 -63.40(18) . . . . ? C3 C2 C1 C9 49.62(17) . . . . ? C2 C1 C9 C10 -17.67(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.294 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.035 #=========================================END data_(3) _database_code_depnum_ccdc_archive 'CCDC 688678' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-Ethynyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene ; _chemical_name_common ? _chemical_melting_point 322 _chemical_formula_moiety 'C16 H20' _chemical_formula_sum 'C16 H20' _chemical_formula_weight 212.32 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 'P 21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.3245(7) _cell_length_b 14.6772(12) _cell_length_c 10.6166(9) _cell_angle_alpha 90.00 _cell_angle_beta 102.35(1) _cell_angle_gamma 90.00 _cell_volume 1267.12(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4162 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 29.99 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 3 runs of narrow-frame \w-scans (scan width 0.3\% \w, 20s exposure), every run at a different \f angle. Crystal to detector distance 5.05 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '60W microfocus Bede Microsource with glass polycapillary optics' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ProteumM APEX CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 14597 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 29.99 _reflns_number_total 3692 _reflns_number_gt 3035 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT version 6.28A (Bruker, 2002)' _computing_data_reduction 'SAINT version 6.28A (Bruker, 2002)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0710P)^2^+0.1063P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3692 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.30882(12) 0.67249(7) 0.37533(10) 0.0180(2) Uani 1 1 d . . . C2 C 0.37873(14) 0.75726(7) 0.45210(11) 0.0211(2) Uani 1 1 d . . . H21 H 0.4063(17) 0.8044(10) 0.3911(13) 0.029(4) Uiso 1 1 d . . . H22 H 0.2907(16) 0.7857(9) 0.4921(13) 0.025(3) Uiso 1 1 d . . . C3 C 0.52962(13) 0.73533(8) 0.55555(11) 0.0211(2) Uani 1 1 d . . . H31 H 0.4995(15) 0.6874(9) 0.6136(12) 0.022(3) Uiso 1 1 d . . . H32 H 0.5680(17) 0.7902(10) 0.6108(14) 0.034(4) Uiso 1 1 d . . . C4 C 0.67398(12) 0.70251(7) 0.49854(10) 0.0167(2) Uani 1 1 d . . . C5 C 0.73324(13) 0.59416(7) 0.33105(10) 0.0167(2) Uani 1 1 d . . . H5 H 0.8520(15) 0.6072(9) 0.3668(12) 0.019(3) Uiso 1 1 d . . . C6 C 0.69150(13) 0.53299(7) 0.22888(10) 0.0174(2) Uani 1 1 d . . . C7 C 0.52505(13) 0.51440(7) 0.17918(10) 0.0197(2) Uani 1 1 d . . . H7 H 0.4905(16) 0.4700(9) 0.1087(13) 0.024(3) Uiso 1 1 d . . . C8 C 0.40674(13) 0.55917(7) 0.22925(10) 0.0193(2) Uani 1 1 d . . . H8 H 0.2878(15) 0.5446(8) 0.1921(12) 0.019(3) Uiso 1 1 d . . . C9 C 0.44706(12) 0.62287(7) 0.32929(10) 0.0154(2) Uani 1 1 d . . . C10 C 0.61451(12) 0.63842(7) 0.38418(9) 0.0147(2) Uani 1 1 d . . . C11 C 0.23191(15) 0.60777(8) 0.45980(12) 0.0256(3) Uani 1 1 d . . . H111 H 0.1724(18) 0.5569(10) 0.4071(14) 0.032(4) Uiso 1 1 d . . . H112 H 0.3167(18) 0.5833(10) 0.5309(14) 0.032(4) Uiso 1 1 d . . . H113 H 0.1481(18) 0.6413(10) 0.4976(14) 0.036(4) Uiso 1 1 d . . . C12 C 0.17384(15) 0.70396(10) 0.26183(12) 0.0295(3) Uani 1 1 d . . . H121 H 0.089(2) 0.7416(11) 0.2957(16) 0.043(4) Uiso 1 1 d . . . H122 H 0.1160(19) 0.6530(11) 0.2113(15) 0.038(4) Uiso 1 1 d . . . H123 H 0.2208(18) 0.7444(11) 0.2025(15) 0.041(4) Uiso 1 1 d . . . C13 C 0.79588(14) 0.65350(9) 0.60595(10) 0.0239(2) Uani 1 1 d . . . H131 H 0.9001(19) 0.6330(10) 0.5778(14) 0.035(4) Uiso 1 1 d . . . H132 H 0.7437(17) 0.5978(10) 0.6367(13) 0.030(4) Uiso 1 1 d . . . H133 H 0.8304(18) 0.6956(10) 0.6813(15) 0.036(4) Uiso 1 1 d . . . C14 C 0.76087(15) 0.78501(8) 0.45371(12) 0.0247(2) Uani 1 1 d . . . H141 H 0.8601(18) 0.7669(10) 0.4193(14) 0.035(4) Uiso 1 1 d . . . H142 H 0.6862(16) 0.8197(9) 0.3823(13) 0.026(3) Uiso 1 1 d . . . H143 H 0.7996(18) 0.8268(10) 0.5270(15) 0.037(4) Uiso 1 1 d . . . C15 C 0.81831(14) 0.49052(7) 0.17516(10) 0.0212(2) Uani 1 1 d . . . C16 C 0.92166(16) 0.45651(8) 0.13042(13) 0.0292(3) Uani 1 1 d . . . H16 H 1.007(2) 0.4296(12) 0.0967(16) 0.049(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0153(5) 0.0216(5) 0.0180(5) 0.0016(4) 0.0056(4) 0.0022(4) C2 0.0218(5) 0.0192(5) 0.0242(5) -0.0007(4) 0.0090(4) 0.0031(4) C3 0.0217(5) 0.0234(5) 0.0197(5) -0.0063(4) 0.0081(4) -0.0008(4) C4 0.0174(5) 0.0180(5) 0.0156(5) -0.0033(4) 0.0053(4) -0.0025(4) C5 0.0170(5) 0.0177(5) 0.0159(5) 0.0006(4) 0.0042(4) 0.0010(4) C6 0.0227(5) 0.0147(5) 0.0161(5) 0.0017(4) 0.0069(4) 0.0015(4) C7 0.0251(5) 0.0174(5) 0.0169(5) -0.0032(4) 0.0050(4) -0.0033(4) C8 0.0187(5) 0.0204(5) 0.0184(5) -0.0007(4) 0.0033(4) -0.0034(4) C9 0.0166(5) 0.0159(4) 0.0144(4) 0.0026(3) 0.0048(4) -0.0004(3) C10 0.0175(5) 0.0145(4) 0.0129(4) 0.0011(3) 0.0048(4) -0.0001(3) C11 0.0244(6) 0.0273(6) 0.0292(6) 0.0006(5) 0.0144(5) -0.0036(4) C12 0.0230(6) 0.0385(7) 0.0258(6) 0.0010(5) 0.0022(5) 0.0095(5) C13 0.0219(5) 0.0329(6) 0.0160(5) -0.0033(4) 0.0021(4) 0.0010(4) C14 0.0293(6) 0.0210(5) 0.0267(6) -0.0057(5) 0.0123(5) -0.0079(4) C15 0.0275(6) 0.0171(5) 0.0199(5) -0.0010(4) 0.0068(4) -0.0003(4) C16 0.0332(7) 0.0254(6) 0.0319(6) -0.0032(5) 0.0132(5) 0.0036(5) _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 C9 1.5278(14) . ? C1 C2 1.5324(15) . ? C1 C12 1.5326(16) . ? C1 C11 1.5369(15) . ? C2 C3 1.5158(16) . ? C2 H21 1.007(14) . ? C2 H22 1.012(14) . ? C3 C4 1.5342(14) . ? C3 H31 1.002(13) . ? C3 H32 1.007(15) . ? C4 C10 1.5319(14) . ? C4 C13 1.5338(15) . ? C4 C14 1.5373(15) . ? C5 C6 1.3936(14) . ? C5 C10 1.3983(14) . ? C5 H5 0.999(12) . ? C6 C7 1.4000(15) . ? C6 C15 1.4442(14) . ? C7 C8 1.3814(15) . ? C7 H7 0.987(14) . ? C8 C9 1.4008(14) . ? C8 H8 1.008(12) . ? C9 C10 1.4097(14) . ? C11 H111 0.999(15) . ? C11 H112 0.984(15) . ? C11 H113 1.005(15) . ? C12 H121 1.020(16) . ? C12 H122 0.984(16) . ? C12 H123 1.004(16) . ? C13 H131 1.022(15) . ? C13 H132 1.013(15) . ? C13 H133 1.003(15) . ? C14 H141 1.008(15) . ? C14 H142 1.009(14) . ? C14 H143 0.989(15) . ? C15 C16 1.1789(16) . ? C16 H16 0.946(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 C1 C2 109.32(8) . . ? C9 C1 C12 111.59(9) . . ? C2 C1 C12 107.74(9) . . ? C9 C1 C11 109.17(9) . . ? C2 C1 C11 110.47(9) . . ? C12 C1 C11 108.55(10) . . ? C3 C2 C1 111.99(9) . . ? C3 C2 H21 110.1(8) . . ? C1 C2 H21 109.2(8) . . ? C3 C2 H22 110.2(7) . . ? C1 C2 H22 109.3(8) . . ? H21 C2 H22 105.8(11) . . ? C2 C3 C4 112.24(9) . . ? C2 C3 H31 108.5(7) . . ? C4 C3 H31 110.0(7) . . ? C2 C3 H32 111.3(8) . . ? C4 C3 H32 107.7(8) . . ? H31 C3 H32 107.0(11) . . ? C10 C4 C13 110.58(8) . . ? C10 C4 C3 110.97(8) . . ? C13 C4 C3 107.66(9) . . ? C10 C4 C14 109.39(8) . . ? C13 C4 C14 108.62(9) . . ? C3 C4 C14 109.57(9) . . ? C6 C5 C10 122.22(9) . . ? C6 C5 H5 118.8(7) . . ? C10 C5 H5 119.0(7) . . ? C5 C6 C7 118.74(9) . . ? C5 C6 C15 120.25(9) . . ? C7 C6 C15 121.01(9) . . ? C8 C7 C6 119.46(10) . . ? C8 C7 H7 119.3(8) . . ? C6 C7 H7 121.2(8) . . ? C7 C8 C9 122.29(10) . . ? C7 C8 H8 118.0(7) . . ? C9 C8 H8 119.7(7) . . ? C8 C9 C10 118.48(9) . . ? C8 C9 C1 119.07(9) . . ? C10 C9 C1 122.44(9) . . ? C5 C10 C9 118.67(9) . . ? C5 C10 C4 117.93(9) . . ? C9 C10 C4 123.39(9) . . ? C1 C11 H111 110.7(8) . . ? C1 C11 H112 110.7(8) . . ? H111 C11 H112 110.2(12) . . ? C1 C11 H113 110.0(8) . . ? H111 C11 H113 106.7(12) . . ? H112 C11 H113 108.5(12) . . ? C1 C12 H121 109.4(9) . . ? C1 C12 H122 113.0(9) . . ? H121 C12 H122 108.0(12) . . ? C1 C12 H123 110.7(9) . . ? H121 C12 H123 106.9(13) . . ? H122 C12 H123 108.6(12) . . ? C4 C13 H131 112.9(9) . . ? C4 C13 H132 110.9(8) . . ? H131 C13 H132 107.9(12) . . ? C4 C13 H133 109.6(9) . . ? H131 C13 H133 107.4(12) . . ? H132 C13 H133 108.1(11) . . ? C4 C14 H141 112.4(9) . . ? C4 C14 H142 112.0(8) . . ? H141 C14 H142 106.3(11) . . ? C4 C14 H143 109.9(9) . . ? H141 C14 H143 107.1(12) . . ? H142 C14 H143 108.9(11) . . ? C16 C15 C6 179.36(12) . . ? C15 C16 H16 178.3(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 -50.42(11) . . . . ? C12 C1 C2 C3 -171.85(9) . . . . ? C11 C1 C2 C3 69.73(11) . . . . ? C1 C2 C3 C4 64.75(12) . . . . ? C2 C3 C4 C10 -40.57(12) . . . . ? C2 C3 C4 C13 -161.72(9) . . . . ? C2 C3 C4 C14 80.32(11) . . . . ? C10 C5 C6 C7 -0.93(15) . . . . ? C10 C5 C6 C15 178.53(9) . . . . ? C5 C6 C7 C8 2.21(15) . . . . ? C15 C6 C7 C8 -177.25(10) . . . . ? C6 C7 C8 C9 -0.29(16) . . . . ? C7 C8 C9 C10 -2.92(15) . . . . ? C7 C8 C9 C1 177.37(9) . . . . ? C2 C1 C9 C8 -162.49(9) . . . . ? C12 C1 C9 C8 -43.42(13) . . . . ? C11 C1 C9 C8 76.56(12) . . . . ? C2 C1 C9 C10 17.80(13) . . . . ? C12 C1 C9 C10 136.87(11) . . . . ? C11 C1 C9 C10 -103.14(11) . . . . ? C6 C5 C10 C9 -2.27(15) . . . . ? C6 C5 C10 C4 178.48(9) . . . . ? C8 C9 C10 C5 4.10(14) . . . . ? C1 C9 C10 C5 -176.19(9) . . . . ? C8 C9 C10 C4 -176.69(9) . . . . ? C1 C9 C10 C4 3.01(14) . . . . ? C13 C4 C10 C5 -53.24(12) . . . . ? C3 C4 C10 C5 -172.65(9) . . . . ? C14 C4 C10 C5 66.35(12) . . . . ? C13 C4 C10 C9 127.55(10) . . . . ? C3 C4 C10 C9 8.14(13) . . . . ? C14 C4 C10 C9 -112.86(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.432 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.048 #==========================================END data_(6) _database_code_depnum_ccdc_archive 'CCDC 688679' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-iodo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene ; _chemical_name_common ? _chemical_melting_point 343 _chemical_formula_moiety 'C14 H19 I' _chemical_formula_sum 'C14 H19 I' _chemical_formula_weight 314.19 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' I I -0.4742 1.8119 '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/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.3105(10) _cell_length_b 10.6990(13) _cell_length_c 15.0376(19) _cell_angle_alpha 90.00 _cell_angle_beta 99.67(1) _cell_angle_gamma 90.00 _cell_volume 1318.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 28.94 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 2.398 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.5880 _exptl_absorpt_correction_T_max 0.7269 _exptl_absorpt_process_details 'XPREP 6.14 (Bruker, 2003), R(int)=0.039 before correction' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 -2.00 0.0900 0.00 1.00 2.00 0.0900 1.00 0.00 0.00 0.1200 0.00 1.00 -2.00 0.0900 0.00 -1.00 2.00 0.0900 -3.00 -1.00 3.00 0.1000 _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 5s exposure), every run at a different \f angle. Crystal to detector distance 4.44 cm. ; _diffrn_ambient_temperature 125(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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 15257 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.98 _reflns_number_total 3494 _reflns_number_gt 3127 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0244P)^2^+0.6893P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3494 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0511 _refine_ls_wR_factor_gt 0.0496 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.003 _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 I I 0.840562(15) 0.862105(12) 0.527347(9) 0.03068(5) Uani 1 1 d . . . C1 C 0.1658(2) 0.62571(16) 0.32753(12) 0.0215(3) Uani 1 1 d . . . C2 C 0.1933(2) 0.54552(19) 0.24691(13) 0.0278(4) Uani 1 1 d . . . H21 H 0.218(3) 0.602(2) 0.1984(18) 0.040(7) Uiso 1 1 d . . . H22 H 0.099(3) 0.504(2) 0.2251(17) 0.037(6) Uiso 1 1 d . . . C3 C 0.3262(2) 0.44878(18) 0.27313(14) 0.0264(4) Uani 1 1 d . . . H31 H 0.333(3) 0.391(2) 0.2246(16) 0.030(6) Uiso 1 1 d . . . H32 H 0.302(3) 0.397(2) 0.3219(16) 0.029(6) Uiso 1 1 d . . . C4 C 0.4939(2) 0.50878(15) 0.30518(11) 0.0190(3) Uani 1 1 d . . . C5 C 0.6239(2) 0.67706(16) 0.41035(11) 0.0189(3) Uani 1 1 d . . . H5 H 0.717(3) 0.6450(18) 0.4006(15) 0.020(5) Uiso 1 1 d . . . C6 C 0.6201(2) 0.77939(16) 0.46575(11) 0.0199(3) Uani 1 1 d . . . C7 C 0.4731(2) 0.82949(15) 0.48037(11) 0.0202(3) Uani 1 1 d . . . H7 H 0.471(3) 0.898(2) 0.5192(15) 0.022(5) Uiso 1 1 d . . . C8 C 0.3298(2) 0.77740(16) 0.43501(11) 0.0197(3) Uani 1 1 d . . . H8 H 0.231(3) 0.809(2) 0.4435(14) 0.023(5) Uiso 1 1 d . . . C9 C 0.3292(2) 0.67613(15) 0.37619(11) 0.0170(3) Uani 1 1 d . . . C10 C 0.4792(2) 0.62258(14) 0.36541(11) 0.0165(3) Uani 1 1 d . . . C11 C 0.0864(2) 0.5487(2) 0.39478(15) 0.0309(4) Uani 1 1 d . . . H111 H 0.153(3) 0.479(2) 0.4193(16) 0.032(6) Uiso 1 1 d . . . H112 H 0.061(3) 0.601(2) 0.4415(17) 0.034(6) Uiso 1 1 d . . . H113 H -0.014(3) 0.514(3) 0.3635(19) 0.047(7) Uiso 1 1 d . . . C12 C 0.0502(2) 0.7331(2) 0.29137(15) 0.0297(4) Uani 1 1 d . . . H121 H 0.015(3) 0.782(2) 0.3374(15) 0.029(6) Uiso 1 1 d . . . H122 H -0.042(3) 0.700(2) 0.2538(18) 0.040(7) Uiso 1 1 d . . . H123 H 0.103(3) 0.789(2) 0.2551(17) 0.040(7) Uiso 1 1 d . . . C13 C 0.6045(2) 0.40935(18) 0.35783(15) 0.0272(4) Uani 1 1 d . . . H131 H 0.556(3) 0.390(2) 0.4110(17) 0.030(6) Uiso 1 1 d . . . H132 H 0.603(3) 0.337(2) 0.3216(18) 0.037(7) Uiso 1 1 d . . . H133 H 0.713(3) 0.436(2) 0.3743(15) 0.030(6) Uiso 1 1 d . . . C14 C 0.5701(3) 0.55070(19) 0.22384(13) 0.0287(4) Uani 1 1 d . . . H141 H 0.685(3) 0.589(2) 0.2441(15) 0.029(6) Uiso 1 1 d . . . H142 H 0.583(3) 0.478(3) 0.1885(17) 0.042(7) Uiso 1 1 d . . . H143 H 0.499(3) 0.603(2) 0.1890(18) 0.037(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.02573(7) 0.03314(8) 0.03172(8) -0.01150(5) 0.00067(5) -0.00849(5) C1 0.0172(8) 0.0217(8) 0.0245(8) -0.0004(7) 0.0005(6) -0.0001(6) C2 0.0223(9) 0.0297(9) 0.0281(9) -0.0066(8) -0.0051(7) -0.0025(7) C3 0.0243(9) 0.0209(8) 0.0327(10) -0.0085(8) 0.0010(7) -0.0032(7) C4 0.0212(8) 0.0160(7) 0.0199(8) -0.0027(6) 0.0036(6) -0.0006(6) C5 0.0180(8) 0.0195(7) 0.0192(8) 0.0001(6) 0.0032(6) -0.0008(6) C6 0.0227(8) 0.0195(8) 0.0169(7) 0.0003(6) 0.0012(6) -0.0058(6) C7 0.0291(9) 0.0152(7) 0.0166(8) -0.0017(6) 0.0052(6) -0.0021(6) C8 0.0219(8) 0.0176(7) 0.0207(8) 0.0022(6) 0.0072(6) 0.0018(6) C9 0.0193(8) 0.0160(7) 0.0157(7) 0.0031(6) 0.0028(6) -0.0008(6) C10 0.0201(8) 0.0150(7) 0.0144(7) 0.0008(6) 0.0030(6) -0.0021(6) C11 0.0232(9) 0.0303(10) 0.0401(11) 0.0036(9) 0.0077(8) -0.0055(8) C12 0.0219(9) 0.0312(10) 0.0338(10) 0.0016(9) -0.0018(8) 0.0047(8) C13 0.0267(9) 0.0174(8) 0.0366(11) -0.0001(8) 0.0031(8) 0.0010(7) C14 0.0399(11) 0.0258(9) 0.0232(9) -0.0044(8) 0.0135(8) -0.0017(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 I C6 2.1039(17) . ? C1 C9 1.528(2) . ? C1 C2 1.533(3) . ? C1 C11 1.537(3) . ? C1 C12 1.538(3) . ? C2 C3 1.517(3) . ? C2 H21 0.99(3) . ? C2 H22 0.91(2) . ? C3 C4 1.537(2) . ? C3 H31 0.96(2) . ? C3 H32 0.97(2) . ? C4 C10 1.535(2) . ? C4 C14 1.536(3) . ? C4 C13 1.536(2) . ? C5 C6 1.379(2) . ? C5 C10 1.404(2) . ? C5 H5 0.88(2) . ? C6 C7 1.385(2) . ? C7 C8 1.386(2) . ? C7 H7 0.94(2) . ? C8 C9 1.398(2) . ? C8 H8 0.92(2) . ? C9 C10 1.406(2) . ? C11 H111 0.96(2) . ? C11 H112 0.95(3) . ? C11 H113 0.96(3) . ? C12 H121 0.95(2) . ? C12 H122 0.94(3) . ? C12 H123 0.96(3) . ? C13 H131 0.98(2) . ? C13 H132 0.94(3) . ? C13 H133 0.94(2) . ? C14 H141 1.03(2) . ? C14 H142 0.96(3) . ? C14 H143 0.92(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 C1 C2 109.75(15) . . ? C9 C1 C11 108.63(15) . . ? C2 C1 C11 110.95(16) . . ? C9 C1 C12 110.95(15) . . ? C2 C1 C12 107.80(15) . . ? C11 C1 C12 108.76(16) . . ? C3 C2 C1 112.02(15) . . ? C3 C2 H21 112.1(15) . . ? C1 C2 H21 108.4(15) . . ? C3 C2 H22 107.8(16) . . ? C1 C2 H22 108.9(16) . . ? H21 C2 H22 107(2) . . ? C2 C3 C4 112.28(15) . . ? C2 C3 H31 111.8(14) . . ? C4 C3 H31 110.0(14) . . ? C2 C3 H32 110.5(14) . . ? C4 C3 H32 107.4(14) . . ? H31 C3 H32 104.5(19) . . ? C10 C4 C14 108.83(14) . . ? C10 C4 C13 110.21(14) . . ? C14 C4 C13 108.77(16) . . ? C10 C4 C3 111.00(14) . . ? C14 C4 C3 110.22(16) . . ? C13 C4 C3 107.76(15) . . ? C6 C5 C10 121.06(16) . . ? C6 C5 H5 121.3(14) . . ? C10 C5 H5 117.6(14) . . ? C5 C6 C7 120.88(16) . . ? C5 C6 I 119.57(13) . . ? C7 C6 I 119.55(12) . . ? C6 C7 C8 118.30(16) . . ? C6 C7 H7 120.5(13) . . ? C8 C7 H7 121.1(13) . . ? C7 C8 C9 122.32(16) . . ? C7 C8 H8 120.1(14) . . ? C9 C8 H8 117.6(14) . . ? C8 C9 C10 118.66(15) . . ? C8 C9 C1 119.02(15) . . ? C10 C9 C1 122.31(15) . . ? C5 C10 C9 118.68(15) . . ? C5 C10 C4 117.82(15) . . ? C9 C10 C4 123.48(14) . . ? C1 C11 H111 112.5(14) . . ? C1 C11 H112 110.0(15) . . ? H111 C11 H112 111(2) . . ? C1 C11 H113 108.7(16) . . ? H111 C11 H113 106(2) . . ? H112 C11 H113 108(2) . . ? C1 C12 H121 113.7(14) . . ? C1 C12 H122 109.3(16) . . ? H121 C12 H122 109(2) . . ? C1 C12 H123 110.5(15) . . ? H121 C12 H123 107(2) . . ? H122 C12 H123 107(2) . . ? C4 C13 H131 106.0(14) . . ? C4 C13 H132 108.7(16) . . ? H131 C13 H132 109(2) . . ? C4 C13 H133 112.8(14) . . ? H131 C13 H133 111(2) . . ? H132 C13 H133 109(2) . . ? C4 C14 H141 111.3(13) . . ? C4 C14 H142 107.9(15) . . ? H141 C14 H142 107.3(19) . . ? C4 C14 H143 108.7(16) . . ? H141 C14 H143 114(2) . . ? H142 C14 H143 108(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 50.1(2) . . . . ? C11 C1 C2 C3 -70.0(2) . . . . ? C12 C1 C2 C3 171.03(16) . . . . ? C1 C2 C3 C4 -64.0(2) . . . . ? C2 C3 C4 C10 41.1(2) . . . . ? C2 C3 C4 C14 -79.5(2) . . . . ? C2 C3 C4 C13 161.90(17) . . . . ? C10 C5 C6 C7 1.6(3) . . . . ? C10 C5 C6 I -177.49(12) . . . . ? C5 C6 C7 C8 -2.6(3) . . . . ? I C6 C7 C8 176.49(12) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C7 C8 C9 C10 2.4(2) . . . . ? C7 C8 C9 C1 -178.92(16) . . . . ? C2 C1 C9 C8 162.45(16) . . . . ? C11 C1 C9 C8 -76.1(2) . . . . ? C12 C1 C9 C8 43.4(2) . . . . ? C2 C1 C9 C10 -18.9(2) . . . . ? C11 C1 C9 C10 102.53(19) . . . . ? C12 C1 C9 C10 -137.97(17) . . . . ? C14 C4 C10 C5 -67.3(2) . . . . ? C13 C4 C10 C5 51.9(2) . . . . ? C3 C4 C10 C5 171.21(15) . . . . ? C14 C4 C10 C9 111.31(18) . . . . ? C13 C4 C10 C9 -129.49(17) . . . . ? C3 C4 C10 C9 -10.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.767 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.067 #======================================END data_(7a) _database_code_depnum_ccdc_archive 'CCDC 688680' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2- ylethynyl)benzoic acid methyl ester ; _chemical_name_common ? _chemical_melting_point 402 _chemical_formula_moiety 'C24 H26 O2' _chemical_formula_sum 'C24 H26 O2' _chemical_formula_weight 346.45 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0253(4) _cell_length_b 8.1167(3) _cell_length_c 15.0326(7) _cell_angle_alpha 90.00(1) _cell_angle_beta 84.50(1) _cell_angle_gamma 79.19(1) _cell_volume 957.24(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3768 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 60.58 _exptl_crystal_description splinter _exptl_crystal_colour colourless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.581 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal habit: parallelogramm plate. The data collection nominally covered full sphere of reciprocal space, by a combination of 7 runs of narrow-frame \w-scans (scan width 0.3\% \w), every run at different \f and/or 2\q angle. Exposure 5s for low-2\q, 10s for high-2\q frames. Crystal to detector distance 4.83 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMARt 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 5.6 _diffrn_standards_number 0 _diffrn_reflns_number 4473 _diffrn_reflns_av_R_equivalents 0.0712 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 60.57 _reflns_number_total 2516 _reflns_number_gt 2393 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT version 6.02A (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. Methyl groups were refined as rigid bodies rotating around C---C or O---C bonds (with a common refined U for three H atoms). Other H atoms: "riding" model (constr). ; _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^)+(0.0781P)^2^+0.3561P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0158(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2516 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.78188(16) 1.30843(14) 0.69099(8) 0.0329(4) Uani 1 1 d . . . O2 O 0.96086(16) 1.12144(15) 0.76293(9) 0.0372(4) Uani 1 1 d . . . C1 C 0.5741(2) 0.05537(19) 0.17405(10) 0.0218(4) Uani 1 1 d . . . C2 C 0.6967(2) 0.0232(2) 0.08878(11) 0.0242(4) Uani 1 1 d . . . H2A H 0.8107 -0.0319 0.1045 0.029 Uiso 1 1 d R . . H2B H 0.6559 -0.0544 0.0488 0.029 Uiso 1 1 d R . . C3 C 0.7120(2) 0.1841(2) 0.03939(11) 0.0254(4) Uani 1 1 d . . . H3A H 0.5976 0.2402 0.0247 0.031 Uiso 1 1 d R . . H3B H 0.7848 0.1558 -0.0175 0.031 Uiso 1 1 d R . . C4 C 0.7882(2) 0.30568(19) 0.09437(10) 0.0216(4) Uani 1 1 d . . . C5 C 0.74364(19) 0.43989(19) 0.24801(10) 0.0201(4) Uani 1 1 d . . . H5 H 0.8111 0.5166 0.2238 0.024 Uiso 1 1 d R . . C6 C 0.6815(2) 0.45678(19) 0.33796(10) 0.0213(4) Uani 1 1 d . . . C7 C 0.5766(2) 0.3476(2) 0.37198(11) 0.0233(4) Uani 1 1 d . . . H7 H 0.5279 0.3593 0.4323 0.028 Uiso 1 1 d R . . C8 C 0.5441(2) 0.22314(19) 0.31773(10) 0.0215(4) Uani 1 1 d . . . H8 H 0.4724 0.1500 0.3418 0.026 Uiso 1 1 d R . . C9 C 0.61277(19) 0.20023(19) 0.22835(10) 0.0189(4) Uani 1 1 d . . . C10 C 0.71092(19) 0.31481(18) 0.19197(10) 0.0190(4) Uani 1 1 d . . . C11 C 0.5954(2) -0.1075(2) 0.22731(11) 0.0276(4) Uani 1 1 d . . . H11A H 0.5764 -0.1995 0.1897 0.033(3) Uiso 1 1 d R . . H11B H 0.5125 -0.0933 0.2803 0.033(3) Uiso 1 1 d R . . H11C H 0.7111 -0.1336 0.2459 0.033(3) Uiso 1 1 d R . . C12 C 0.3884(2) 0.1006(2) 0.15130(11) 0.0270(4) Uani 1 1 d . . . H12A H 0.3744 0.2011 0.1146 0.034(3) Uiso 1 1 d R . . H12B H 0.3121 0.1224 0.2067 0.034(3) Uiso 1 1 d R . . H12C H 0.3604 0.0071 0.1182 0.034(3) Uiso 1 1 d R . . C13 C 0.9815(2) 0.2453(2) 0.09227(11) 0.0281(4) Uani 1 1 d . . . H13A H 1.0307 0.3262 0.1248 0.033(3) Uiso 1 1 d R . . H13B H 1.0324 0.2354 0.0301 0.033(3) Uiso 1 1 d R . . H13C H 1.0050 0.1356 0.1205 0.033(3) Uiso 1 1 d R . . C14 C 0.7529(2) 0.4787(2) 0.05152(11) 0.0298(4) Uani 1 1 d . . . H14A H 0.6298 0.5219 0.0568 0.034(3) Uiso 1 1 d R . . H14B H 0.7966 0.4688 -0.0118 0.034(3) Uiso 1 1 d R . . H14C H 0.8097 0.5560 0.0821 0.034(3) Uiso 1 1 d R . . C15 C 0.7267(2) 0.5799(2) 0.39486(11) 0.0238(4) Uani 1 1 d . . . C16 C 0.7673(2) 0.6782(2) 0.44509(10) 0.0237(4) Uani 1 1 d . . . C17 C 0.8045(2) 0.7985(2) 0.50627(10) 0.0219(4) Uani 1 1 d . . . C18 C 0.7344(2) 0.9686(2) 0.49805(11) 0.0266(4) Uani 1 1 d . . . H18 H 0.6692 1.0040 0.4496 0.032 Uiso 1 1 d R . . C19 C 0.7591(2) 1.0849(2) 0.55964(11) 0.0266(4) Uani 1 1 d . . . H19 H 0.7099 1.1998 0.5538 0.032 Uiso 1 1 d R . . C20 C 0.85561(19) 1.0354(2) 0.63040(10) 0.0213(4) Uani 1 1 d . . . C21 C 0.9314(2) 0.8669(2) 0.63706(11) 0.0247(4) Uani 1 1 d . . . H21 H 1.0013 0.8328 0.6838 0.030 Uiso 1 1 d R . . C22 C 0.9053(2) 0.7499(2) 0.57600(11) 0.0256(4) Uani 1 1 d . . . H22 H 0.9562 0.6353 0.5814 0.031 Uiso 1 1 d R . . C23 C 0.8755(2) 1.1553(2) 0.70147(11) 0.0240(4) Uani 1 1 d . . . C24 C 0.7823(3) 1.4301(2) 0.76024(14) 0.0432(5) Uani 1 1 d . . . H24A H 0.7466 1.3859 0.8182 0.081(5) Uiso 1 1 d R . . H24B H 0.7031 1.5337 0.7488 0.081(5) Uiso 1 1 d R . . H24C H 0.8975 1.4539 0.7610 0.081(5) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0429(7) 0.0213(6) 0.0341(7) -0.0050(5) -0.0157(6) 0.0007(5) O2 0.0450(8) 0.0316(7) 0.0354(8) -0.0040(6) -0.0198(7) 0.0003(6) C1 0.0252(9) 0.0203(8) 0.0194(9) -0.0001(7) -0.0011(7) -0.0037(6) C2 0.0275(9) 0.0228(8) 0.0214(9) -0.0049(7) -0.0001(7) -0.0035(6) C3 0.0285(9) 0.0291(9) 0.0179(8) -0.0019(7) -0.0001(7) -0.0045(7) C4 0.0265(9) 0.0220(8) 0.0152(8) 0.0008(6) -0.0005(6) -0.0024(6) C5 0.0215(8) 0.0181(8) 0.0201(9) 0.0026(6) -0.0023(6) -0.0017(6) C6 0.0244(8) 0.0196(8) 0.0181(9) 0.0008(6) -0.0050(6) 0.0024(6) C7 0.0273(9) 0.0245(9) 0.0159(8) 0.0016(7) -0.0011(6) 0.0007(7) C8 0.0232(8) 0.0216(8) 0.0191(8) 0.0046(6) -0.0013(6) -0.0028(6) C9 0.0189(8) 0.0183(8) 0.0177(9) 0.0030(6) -0.0050(6) 0.0029(6) C10 0.0182(8) 0.0194(8) 0.0174(9) 0.0030(6) -0.0035(6) 0.0029(6) C11 0.0348(10) 0.0199(9) 0.0272(9) -0.0002(7) -0.0005(7) -0.0041(7) C12 0.0264(9) 0.0285(9) 0.0265(9) -0.0021(7) -0.0029(7) -0.0063(7) C13 0.0267(9) 0.0299(10) 0.0262(9) -0.0048(7) 0.0039(7) -0.0052(7) C14 0.0420(11) 0.0267(9) 0.0198(9) 0.0029(7) -0.0009(7) -0.0055(8) C15 0.0266(9) 0.0224(9) 0.0198(9) 0.0019(7) -0.0010(7) 0.0013(7) C16 0.0270(9) 0.0241(9) 0.0181(9) 0.0017(7) 0.0003(7) -0.0016(7) C17 0.0250(9) 0.0230(9) 0.0167(8) -0.0006(7) 0.0027(7) -0.0042(7) C18 0.0342(10) 0.0248(9) 0.0213(9) 0.0040(7) -0.0091(7) -0.0037(7) C19 0.0344(10) 0.0193(8) 0.0252(10) 0.0032(7) -0.0062(7) -0.0015(7) C20 0.0218(8) 0.0229(9) 0.0191(9) 0.0026(7) -0.0014(7) -0.0040(6) C21 0.0253(9) 0.0264(9) 0.0211(9) 0.0013(7) -0.0058(7) 0.0001(7) C22 0.0274(9) 0.0217(9) 0.0248(9) 0.0000(7) -0.0018(7) 0.0027(7) C23 0.0240(9) 0.0240(9) 0.0241(9) 0.0015(7) -0.0045(7) -0.0039(7) C24 0.0560(13) 0.0273(10) 0.0457(12) -0.0138(9) -0.0218(10) 0.0024(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C23 1.344(2) . ? O1 C24 1.436(2) . ? O2 C23 1.204(2) . ? C1 C9 1.527(2) . ? C1 C2 1.530(2) . ? C1 C11 1.536(2) . ? C1 C12 1.538(2) . ? C2 C3 1.522(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.535(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C10 1.533(2) . ? C4 C14 1.534(2) . ? C4 C13 1.534(2) . ? C5 C6 1.393(2) . ? C5 C10 1.397(2) . ? C5 H5 0.9500 . ? C6 C7 1.398(2) . ? C6 C15 1.434(2) . ? C7 C8 1.376(2) . ? C7 H7 0.9500 . ? C8 C9 1.401(2) . ? C8 H8 0.9500 . ? C9 C10 1.406(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.208(2) . ? C16 C17 1.432(2) . ? C17 C22 1.397(3) . ? C17 C18 1.400(2) . ? C18 C19 1.376(2) . ? C18 H18 0.9500 . ? C19 C20 1.391(2) . ? C19 H19 0.9500 . ? C20 C21 1.397(2) . ? C20 C23 1.485(2) . ? C21 C22 1.379(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9801 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C23 O1 C24 116.06(13) . . ? C9 C1 C2 110.23(12) . . ? C9 C1 C11 111.25(12) . . ? C2 C1 C11 107.58(13) . . ? C9 C1 C12 108.48(12) . . ? C2 C1 C12 110.71(13) . . ? C11 C1 C12 108.59(13) . . ? C3 C2 C1 112.24(13) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 112.39(13) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C10 C4 C14 110.77(13) . . ? C10 C4 C13 108.50(13) . . ? C14 C4 C13 109.05(14) . . ? C10 C4 C3 110.84(13) . . ? C14 C4 C3 108.04(13) . . ? C13 C4 C3 109.63(13) . . ? C6 C5 C10 122.76(14) . . ? C6 C5 H5 118.6 . . ? C10 C5 H5 118.6 . . ? C5 C6 C7 118.11(14) . . ? C5 C6 C15 121.21(14) . . ? C7 C6 C15 120.67(14) . . ? C8 C7 C6 119.74(14) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 122.47(14) . . ? C7 C8 H8 118.8 . . ? C9 C8 H8 118.8 . . ? C8 C9 C10 118.31(14) . . ? C8 C9 C1 118.80(13) . . ? C10 C9 C1 122.87(14) . . ? C5 C10 C9 118.46(14) . . ? C5 C10 C4 118.46(13) . . ? C9 C10 C4 123.05(14) . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C4 C13 H13A 109.5 . . ? C4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C6 177.27(16) . . ? C15 C16 C17 176.44(16) . . ? C22 C17 C18 118.89(15) . . ? C22 C17 C16 121.56(14) . . ? C18 C17 C16 119.52(15) . . ? C19 C18 C17 120.46(15) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 120.50(15) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.8 . . ? C19 C20 C21 119.34(15) . . ? C19 C20 C23 122.01(14) . . ? C21 C20 C23 118.61(15) . . ? C22 C21 C20 120.25(15) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C17 120.49(15) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.8 . . ? O2 C23 O1 122.97(15) . . ? O2 C23 C20 125.18(15) . . ? O1 C23 C20 111.83(14) . . ? O1 C24 H24A 109.5 . . ? O1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 C20 C23 O1 3.9(2) . . . . ? C21 C20 C23 O2 4.5(2) . . . . ? C1 C9 C10 C4 0.1(2) . . . . ? C9 C10 C4 C3 12.6(2) . . . . ? C10 C4 C3 C2 -43.02(17) . . . . ? C4 C3 C2 C1 63.41(18) . . . . ? C3 C2 C1 C9 -47.52(18) . . . . ? C2 C1 C9 C10 17.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 60.57 _diffrn_measured_fraction_theta_full 0.871 _refine_diff_density_max 0.206 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.047 #========================================END data_(7b) _database_code_depnum_ccdc_archive 'CCDC 688681' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2- ylethynyl)benzoic acid methyl ester ; _chemical_name_common ? _chemical_melting_point 374 _chemical_formula_moiety 'C24 H26 O2' _chemical_formula_sum 'C24 H26 O2' _chemical_formula_weight 346.45 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.2333(16) _cell_length_b 5.9012(6) _cell_length_c 23.004(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.534(3) _cell_angle_gamma 90.00 _cell_volume 1932.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5416 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 28.94 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 0.00 0.0500 1.00 0.00 0.00 0.0500 0.00 1.00 0.00 0.2300 0.00 -1.00 0.00 0.2300 0.00 0.00 1.00 0.1150 0.00 0.00 -1.00 0.1150 1.00 0.00 2.00 0.0950 1.00 0.00 -2.00 0.0950 _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 10s exposure), every run at a different \f angle. Crystal to detector distance 4.41 cm. ; _diffrn_ambient_temperature 120(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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 21562 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 29.06 _reflns_number_total 5116 _reflns_number_gt 3878 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0483P)^2^+0.4755P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5116 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.83083(6) 0.40976(15) 0.69892(4) 0.0272(2) Uani 1 1 d . . . O2 O 0.87249(7) 0.06077(17) 0.72771(5) 0.0362(2) Uani 1 1 d . . . C1 C 0.22068(8) 1.1465(2) 0.47779(5) 0.0226(2) Uani 1 1 d . . . C2 C 0.15610(10) 1.2867(2) 0.51700(6) 0.0276(3) Uani 1 1 d . . . H2A H 0.1978(10) 1.396(3) 0.5401(6) 0.030(4) Uiso 1 1 d . . . H2B H 0.1119(11) 1.375(3) 0.4921(6) 0.033(4) Uiso 1 1 d . . . C3 C 0.10194(9) 1.1398(2) 0.55895(5) 0.0254(3) Uani 1 1 d . . . H3A H 0.0613(10) 1.026(3) 0.5368(6) 0.029(4) Uiso 1 1 d . . . H3B H 0.0576(11) 1.232(3) 0.5828(6) 0.034(4) Uiso 1 1 d . . . C4 C 0.16532(8) 1.0060(2) 0.60096(5) 0.0206(2) Uani 1 1 d . . . C5 C 0.30897(8) 0.7583(2) 0.60014(5) 0.0208(2) Uani 1 1 d . . . H5 H 0.2908(10) 0.705(2) 0.6391(6) 0.027(4) Uiso 1 1 d . . . C6 C 0.39261(8) 0.6755(2) 0.57741(5) 0.0228(2) Uani 1 1 d . . . C7 C 0.42185(9) 0.7552(2) 0.52325(5) 0.0255(3) Uani 1 1 d . . . H7 H 0.4819(11) 0.703(3) 0.5067(6) 0.032(4) Uiso 1 1 d . . . C8 C 0.36602(9) 0.9075(2) 0.49314(5) 0.0239(3) Uani 1 1 d . . . H8 H 0.3862(11) 0.961(3) 0.4545(7) 0.036(4) Uiso 1 1 d . . . C9 C 0.28136(8) 0.9894(2) 0.51523(5) 0.0194(2) Uani 1 1 d . . . C10 C 0.25271(8) 0.9145(2) 0.57042(5) 0.0184(2) Uani 1 1 d . . . C11 C 0.27980(11) 1.3116(3) 0.44200(6) 0.0341(3) Uani 1 1 d . . . H111 H 0.3189(11) 1.238(3) 0.4111(7) 0.040(4) Uiso 1 1 d . . . H112 H 0.2369(13) 1.425(3) 0.4220(7) 0.050(5) Uiso 1 1 d . . . H113 H 0.3230(12) 1.402(3) 0.4666(7) 0.040(4) Uiso 1 1 d . . . C12 C 0.16309(10) 0.9977(3) 0.43573(6) 0.0309(3) Uani 1 1 d . . . H121 H 0.1200(11) 0.889(3) 0.4562(7) 0.039(4) Uiso 1 1 d . . . H122 H 0.2067(11) 0.914(3) 0.4102(7) 0.036(4) Uiso 1 1 d . . . H123 H 0.1212(12) 1.096(3) 0.4107(7) 0.046(5) Uiso 1 1 d . . . C13 C 0.19902(10) 1.1607(2) 0.65079(6) 0.0279(3) Uani 1 1 d . . . H131 H 0.2410(11) 1.075(3) 0.6787(7) 0.036(4) Uiso 1 1 d . . . H132 H 0.2377(11) 1.290(3) 0.6353(7) 0.036(4) Uiso 1 1 d . . . H133 H 0.1444(11) 1.221(3) 0.6718(6) 0.031(4) Uiso 1 1 d . . . C14 C 0.10574(10) 0.8139(2) 0.62654(6) 0.0283(3) Uani 1 1 d . . . H141 H 0.1400(10) 0.728(3) 0.6580(6) 0.031(4) Uiso 1 1 d . . . H142 H 0.0477(11) 0.878(3) 0.6444(6) 0.032(4) Uiso 1 1 d . . . H143 H 0.0869(11) 0.704(3) 0.5954(7) 0.039(4) Uiso 1 1 d . . . C15 C 0.44820(9) 0.5123(2) 0.60877(5) 0.0251(3) Uani 1 1 d . . . C16 C 0.49611(8) 0.3770(2) 0.63410(5) 0.0241(3) Uani 1 1 d . . . C17 C 0.55769(8) 0.2222(2) 0.66399(5) 0.0212(2) Uani 1 1 d . . . C18 C 0.52639(9) 0.0090(2) 0.68227(5) 0.0246(3) Uani 1 1 d . . . H18 H 0.4607(11) -0.033(3) 0.6754(6) 0.035(4) Uiso 1 1 d . . . C19 C 0.58766(9) -0.1384(2) 0.71016(5) 0.0264(3) Uani 1 1 d . . . H19 H 0.5659(10) -0.288(3) 0.7222(6) 0.032(4) Uiso 1 1 d . . . C20 C 0.68071(9) -0.0781(2) 0.71993(5) 0.0244(3) Uani 1 1 d . . . H20 H 0.7245(11) -0.178(3) 0.7378(6) 0.034(4) Uiso 1 1 d . . . C21 C 0.71237(8) 0.1347(2) 0.70227(5) 0.0197(2) Uani 1 1 d . . . C22 C 0.65101(8) 0.2840(2) 0.67460(5) 0.0200(2) Uani 1 1 d . . . H22 H 0.6725(10) 0.430(2) 0.6627(6) 0.022(3) Uiso 1 1 d . . . C23 C 0.81313(9) 0.1923(2) 0.71129(5) 0.0228(3) Uani 1 1 d . . . C24 C 0.92766(10) 0.4813(3) 0.70483(7) 0.0341(3) Uani 1 1 d . . . H241 H 0.9641(12) 0.405(3) 0.6749(8) 0.049(5) Uiso 1 1 d . . . H242 H 0.9259(12) 0.645(3) 0.6999(7) 0.051(5) Uiso 1 1 d . . . H243 H 0.9512(12) 0.447(3) 0.7439(8) 0.049(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0213(4) 0.0242(5) 0.0359(5) 0.0037(4) -0.0030(4) -0.0020(4) O2 0.0293(5) 0.0296(5) 0.0494(6) 0.0037(4) -0.0131(4) 0.0052(4) C1 0.0233(6) 0.0241(6) 0.0206(5) 0.0022(4) -0.0003(4) 0.0014(5) C2 0.0310(7) 0.0258(7) 0.0258(6) 0.0030(5) 0.0001(5) 0.0072(6) C3 0.0217(6) 0.0299(7) 0.0248(6) -0.0011(5) 0.0018(5) 0.0062(5) C4 0.0204(6) 0.0213(6) 0.0201(5) -0.0008(4) 0.0014(4) -0.0002(5) C5 0.0202(6) 0.0204(6) 0.0216(5) -0.0006(4) -0.0018(4) -0.0026(5) C6 0.0187(6) 0.0213(6) 0.0282(6) -0.0027(5) -0.0047(4) -0.0009(5) C7 0.0189(6) 0.0274(7) 0.0301(6) -0.0029(5) 0.0023(5) 0.0012(5) C8 0.0222(6) 0.0258(6) 0.0238(6) -0.0002(5) 0.0035(5) -0.0020(5) C9 0.0192(6) 0.0185(6) 0.0204(5) -0.0017(4) -0.0016(4) -0.0028(4) C10 0.0171(5) 0.0179(5) 0.0202(5) -0.0027(4) -0.0009(4) -0.0020(4) C11 0.0342(8) 0.0336(8) 0.0347(7) 0.0121(6) 0.0048(6) 0.0004(6) C12 0.0273(7) 0.0409(8) 0.0245(6) -0.0032(6) -0.0043(5) 0.0015(6) C13 0.0305(7) 0.0289(7) 0.0242(6) -0.0064(5) 0.0004(5) 0.0015(6) C14 0.0248(7) 0.0281(7) 0.0321(7) 0.0019(5) 0.0062(5) -0.0025(5) C15 0.0206(6) 0.0251(6) 0.0296(6) -0.0036(5) -0.0023(5) -0.0005(5) C16 0.0197(6) 0.0252(6) 0.0276(6) -0.0015(5) -0.0007(5) -0.0001(5) C17 0.0218(6) 0.0212(6) 0.0205(5) -0.0021(4) 0.0012(4) 0.0023(5) C18 0.0228(6) 0.0245(6) 0.0264(6) -0.0035(5) 0.0026(5) -0.0027(5) C19 0.0331(7) 0.0194(6) 0.0267(6) 0.0018(5) 0.0044(5) -0.0027(5) C20 0.0306(7) 0.0212(6) 0.0214(6) 0.0034(4) -0.0009(5) 0.0028(5) C21 0.0231(6) 0.0193(6) 0.0167(5) 0.0000(4) 0.0002(4) 0.0017(5) C22 0.0221(6) 0.0172(6) 0.0208(5) 0.0015(4) 0.0016(4) 0.0005(5) C23 0.0255(6) 0.0222(6) 0.0204(5) -0.0007(4) -0.0025(4) 0.0017(5) C24 0.0218(7) 0.0348(8) 0.0457(9) -0.0008(7) -0.0006(6) -0.0056(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 O1 C23 1.3387(15) . ? O1 C24 1.4466(16) . ? O2 C23 1.2055(15) . ? C1 C9 1.5276(16) . ? C1 C11 1.5321(18) . ? C1 C2 1.5357(17) . ? C1 C12 1.5379(18) . ? C2 C3 1.5134(19) . ? C2 H2A 1.024(15) . ? C2 H2B 0.994(15) . ? C3 C4 1.5345(17) . ? C3 H3A 1.020(15) . ? C3 H3B 1.000(16) . ? C4 C10 1.5326(16) . ? C4 C14 1.5363(17) . ? C4 C13 1.5384(17) . ? C5 C6 1.3933(17) . ? C5 C10 1.3956(16) . ? C5 H5 0.988(14) . ? C6 C7 1.3988(17) . ? C6 C15 1.4362(17) . ? C7 C8 1.3814(18) . ? C7 H7 0.989(15) . ? C8 C9 1.3984(17) . ? C8 H8 0.989(16) . ? C9 C10 1.4083(16) . ? C11 H111 1.006(17) . ? C11 H112 1.014(18) . ? C11 H113 0.988(17) . ? C12 H121 1.009(17) . ? C12 H122 0.989(17) . ? C12 H123 1.010(17) . ? C13 H131 1.009(16) . ? C13 H132 1.008(17) . ? C13 H133 0.986(15) . ? C14 H141 1.007(15) . ? C14 H142 1.002(16) . ? C14 H143 1.000(16) . ? C15 C16 1.1982(17) . ? C16 C17 1.4366(17) . ? C17 C22 1.3968(17) . ? C17 C18 1.4006(18) . ? C18 C19 1.3851(18) . ? C18 H18 0.977(16) . ? C19 C20 1.3876(19) . ? C19 H19 0.976(16) . ? C20 C21 1.3959(17) . ? C20 H20 0.948(15) . ? C21 C22 1.3909(16) . ? C21 C23 1.4866(17) . ? C22 H22 0.958(15) . ? C24 H241 0.975(19) . ? C24 H242 0.97(2) . ? C24 H243 0.977(18) . ? 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 C23 O1 C24 116.16(11) . . ? C9 C1 C11 112.23(10) . . ? C9 C1 C2 109.52(9) . . ? C11 C1 C2 107.94(11) . . ? C9 C1 C12 107.66(10) . . ? C11 C1 C12 108.49(11) . . ? C2 C1 C12 111.03(11) . . ? C3 C2 C1 112.16(11) . . ? C3 C2 H2A 109.1(8) . . ? C1 C2 H2A 107.4(8) . . ? C3 C2 H2B 110.0(9) . . ? C1 C2 H2B 108.9(9) . . ? H2A C2 H2B 109.2(12) . . ? C2 C3 C4 113.35(10) . . ? C2 C3 H3A 110.4(8) . . ? C4 C3 H3A 107.6(8) . . ? C2 C3 H3B 111.5(9) . . ? C4 C3 H3B 107.7(9) . . ? H3A C3 H3B 105.9(12) . . ? C10 C4 C3 111.56(9) . . ? C10 C4 C14 111.64(10) . . ? C3 C4 C14 107.32(10) . . ? C10 C4 C13 107.57(10) . . ? C3 C4 C13 109.97(10) . . ? C14 C4 C13 108.77(10) . . ? C6 C5 C10 122.43(11) . . ? C6 C5 H5 117.4(8) . . ? C10 C5 H5 120.2(8) . . ? C5 C6 C7 118.58(11) . . ? C5 C6 C15 121.03(11) . . ? C7 C6 C15 120.39(11) . . ? C8 C7 C6 119.41(11) . . ? C8 C7 H7 120.3(9) . . ? C6 C7 H7 120.3(9) . . ? C7 C8 C9 122.43(11) . . ? C7 C8 H8 119.3(9) . . ? C9 C8 H8 118.3(9) . . ? C8 C9 C10 118.47(11) . . ? C8 C9 C1 119.31(10) . . ? C10 C9 C1 122.14(10) . . ? C5 C10 C9 118.65(11) . . ? C5 C10 C4 118.20(10) . . ? C9 C10 C4 123.06(10) . . ? C1 C11 H111 114.4(10) . . ? C1 C11 H112 109.4(10) . . ? H111 C11 H112 107.6(13) . . ? C1 C11 H113 112.1(9) . . ? H111 C11 H113 107.0(13) . . ? H112 C11 H113 105.9(14) . . ? C1 C12 H121 113.1(9) . . ? C1 C12 H122 109.0(9) . . ? H121 C12 H122 110.3(13) . . ? C1 C12 H123 109.8(10) . . ? H121 C12 H123 106.0(13) . . ? H122 C12 H123 108.5(13) . . ? C4 C13 H131 110.9(9) . . ? C4 C13 H132 110.8(9) . . ? H131 C13 H132 106.4(13) . . ? C4 C13 H133 109.8(9) . . ? H131 C13 H133 109.4(12) . . ? H132 C13 H133 109.5(13) . . ? C4 C14 H141 112.5(9) . . ? C4 C14 H142 109.7(9) . . ? H141 C14 H142 107.1(12) . . ? C4 C14 H143 110.4(9) . . ? H141 C14 H143 108.1(12) . . ? H142 C14 H143 108.9(12) . . ? C16 C15 C6 178.60(14) . . ? C15 C16 C17 177.02(14) . . ? C22 C17 C18 119.13(11) . . ? C22 C17 C16 119.50(11) . . ? C18 C17 C16 121.36(11) . . ? C19 C18 C17 120.17(12) . . ? C19 C18 H18 121.0(9) . . ? C17 C18 H18 118.9(9) . . ? C18 C19 C20 120.66(12) . . ? C18 C19 H19 119.9(9) . . ? C20 C19 H19 119.4(9) . . ? C19 C20 C21 119.58(12) . . ? C19 C20 H20 122.3(9) . . ? C21 C20 H20 118.1(9) . . ? C22 C21 C20 120.02(11) . . ? C22 C21 C23 121.31(11) . . ? C20 C21 C23 118.61(11) . . ? C21 C22 C17 120.42(11) . . ? C21 C22 H22 120.1(8) . . ? C17 C22 H22 119.4(8) . . ? O2 C23 O1 123.44(12) . . ? O2 C23 C21 124.66(11) . . ? O1 C23 C21 111.90(10) . . ? O1 C24 H241 108.2(10) . . ? O1 C24 H242 104.8(10) . . ? H241 C24 H242 112.7(15) . . ? O1 C24 H243 110.2(10) . . ? H241 C24 H243 111.9(15) . . ? H242 C24 H243 108.9(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 -51.41(14) . . . . ? C11 C1 C2 C3 -173.87(11) . . . . ? C12 C1 C2 C3 67.35(14) . . . . ? C1 C2 C3 C4 61.30(14) . . . . ? C2 C3 C4 C10 -39.76(14) . . . . ? C2 C3 C4 C14 -162.34(11) . . . . ? C2 C3 C4 C13 79.51(13) . . . . ? C15 C6 C7 C8 178.25(11) . . . . ? C6 C7 C8 C9 1.23(19) . . . . ? C7 C8 C9 C1 -176.39(11) . . . . ? C11 C1 C9 C8 -37.53(15) . . . . ? C2 C1 C9 C8 -157.39(11) . . . . ? C12 C1 C9 C8 81.78(14) . . . . ? C11 C1 C9 C10 145.75(12) . . . . ? C2 C1 C9 C10 25.89(15) . . . . ? C12 C1 C9 C10 -94.94(13) . . . . ? C6 C5 C10 C9 0.51(17) . . . . ? C6 C5 C10 C4 -176.22(11) . . . . ? C8 C9 C10 C5 -1.30(16) . . . . ? C1 C9 C10 C5 175.45(11) . . . . ? C8 C9 C10 C4 175.26(11) . . . . ? C1 C9 C10 C4 -8.00(17) . . . . ? C3 C4 C10 C5 -169.48(10) . . . . ? C14 C4 C10 C5 -49.40(14) . . . . ? C13 C4 C10 C5 69.84(13) . . . . ? C3 C4 C10 C9 13.95(16) . . . . ? C14 C4 C10 C9 134.03(12) . . . . ? C13 C4 C10 C9 -106.73(12) . . . . ? C23 C21 C22 C17 176.83(10) . . . . ? C16 C17 C22 C21 -178.51(10) . . . . ? C24 O1 C23 O2 1.58(18) . . . . ? C24 O1 C23 C21 -178.39(11) . . . . ? C22 C21 C23 O2 -169.62(12) . . . . ? C20 C21 C23 O2 7.62(18) . . . . ? C22 C21 C23 O1 10.34(15) . . . . ? C20 C21 C23 O1 -172.41(10) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 29.06 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.293 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.040 #=========================================END