# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Marilena Giarrusso' _publ_contact_author_email marilena.giarrusso@sci.monash.edu.au loop_ _publ_author_name 'Anthony E. Rosamilia' 'Marilena A. Giarrusso' 'Janet L. Scott' 'Christopher R. Strauss' data_1n _database_code_depnum_ccdc_archive 'CCDC 605464' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E,E)-2-(4-Ethoxy-3-methoxybenzylidene)-6-(4-methoxybenzylidene)cyclohexanone ; _chemical_name_common ;(E,E)-2-(4-Ethoxy-3-methoxybenzylidene)-6-(4- methoxybenzylidene)cyclohexanone ; _chemical_melting_point ? _chemical_formula_moiety 'C24 H26 04' _chemical_formula_sum 'C24 H26 O4' _chemical_formula_weight 378.45 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2190(3) _cell_length_b 12.8515(3) _cell_length_c 14.1651(4) _cell_angle_alpha 82.2720(10) _cell_angle_beta 88.4670(10) _cell_angle_gamma 75.7150(10) _cell_volume 1961.17(9) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _exptl_crystal_description prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9788 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 'Bruker Kappa Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 112188 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 30.06 _reflns_number_total 11417 _reflns_number_gt 8758 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _computing_data_reduction 'Bruker Apex2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material ciftab _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.7262P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11417 _refine_ls_number_parameters 511 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1177 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C1A C 0.92904(16) 1.16572(13) -0.80513(11) 0.0379(4) Uani 1 1 d . . . H1A1 H 0.9067 1.2091 -0.7526 0.057 Uiso 1 1 calc R . . H1A2 H 0.9253 1.2140 -0.8653 0.057 Uiso 1 1 calc R . . H1A3 H 1.0128 1.1200 -0.7949 0.057 Uiso 1 1 calc R . . O2A O 0.84509(10) 1.09882(8) -0.80887(7) 0.0296(2) Uani 1 1 d . . . C3A C 0.83531(12) 1.02862(10) -0.72916(9) 0.0213(2) Uani 1 1 d . . . C4A C 0.90771(12) 1.01263(10) -0.64804(9) 0.0224(3) Uani 1 1 d . . . H4A H 0.9696 1.0510 -0.6453 0.027 Uiso 1 1 calc R . . C5A C 0.74742(12) 0.96923(10) -0.73347(9) 0.0219(3) Uani 1 1 d . . . H5A H 0.7015 0.9769 -0.7904 0.026 Uiso 1 1 calc R . . C6A C 0.88842(11) 0.93981(10) -0.57096(9) 0.0196(2) Uani 1 1 d . . . H6A H 0.9402 0.9269 -0.5165 0.024 Uiso 1 1 calc R . . C7A C 0.72689(11) 0.89927(10) -0.65524(9) 0.0202(2) Uani 1 1 d . . . H7A H 0.6656 0.8604 -0.6586 0.024 Uiso 1 1 calc R . . C8A C 0.79526(11) 0.88474(9) -0.57083(9) 0.0172(2) Uani 1 1 d . . . C9A C 0.77517(11) 0.81871(9) -0.48222(8) 0.0168(2) Uani 1 1 d . . . H9A H 0.8463 0.7869 -0.4439 0.020 Uiso 1 1 calc R . . C10A C 0.66962(10) 0.79669(9) -0.44727(8) 0.0159(2) Uani 1 1 d . . . C11A C 0.54478(11) 0.83765(10) -0.49425(9) 0.0188(2) Uani 1 1 d . . . H11A H 0.5326 0.7863 -0.5371 0.023 Uiso 1 1 calc R . . H11B H 0.5400 0.9086 -0.5331 0.023 Uiso 1 1 calc R . . C12A C 0.44395(11) 0.84970(9) -0.41937(9) 0.0191(2) Uani 1 1 d . . . H12C H 0.4572 0.8996 -0.3754 0.023 Uiso 1 1 calc R . . H12D H 0.3629 0.8810 -0.4508 0.023 Uiso 1 1 calc R . . C13A C 0.44531(10) 0.73970(9) -0.36353(9) 0.0182(2) Uani 1 1 d . . . H13A H 0.3820 0.7488 -0.3132 0.022 Uiso 1 1 calc R . . H13B H 0.4244 0.6924 -0.4068 0.022 Uiso 1 1 calc R . . C14A C 0.56955(10) 0.68619(9) -0.31827(8) 0.0154(2) Uani 1 1 d . . . C15A C 0.67755(10) 0.73079(9) -0.35088(8) 0.0159(2) Uani 1 1 d . . . O16A O 0.76970(8) 0.71273(7) -0.30062(6) 0.02224(19) Uani 1 1 d . . . C17A C 0.59483(10) 0.59884(9) -0.25116(8) 0.0161(2) Uani 1 1 d . . . H17A H 0.6770 0.5796 -0.2278 0.019 Uiso 1 1 calc R . . C18A C 0.51845(10) 0.52845(9) -0.20796(8) 0.0157(2) Uani 1 1 d . . . C19A C 0.40565(11) 0.52308(10) -0.24352(9) 0.0185(2) Uani 1 1 d . . . H19A H 0.3703 0.5716 -0.2978 0.022 Uiso 1 1 calc R . . C20A C 0.56673(10) 0.45703(9) -0.12580(8) 0.0161(2) Uani 1 1 d . . . H20A H 0.6441 0.4587 -0.1012 0.019 Uiso 1 1 calc R . . C21A C 0.34425(11) 0.44751(10) -0.20053(9) 0.0195(2) Uani 1 1 d . . . H21A H 0.2688 0.4435 -0.2268 0.023 Uiso 1 1 calc R . . C22A C 0.50421(10) 0.38479(9) -0.08042(8) 0.0154(2) Uani 1 1 d . . . O23A O 0.54282(8) 0.31433(7) -0.00046(6) 0.02027(18) Uani 1 1 d . . . C24A C 0.65619(11) 0.31759(10) 0.04154(9) 0.0197(2) Uani 1 1 d . . . H24A H 0.7228 0.3018 -0.0045 0.030 Uiso 1 1 calc R . . H24B H 0.6741 0.2635 0.0983 0.030 Uiso 1 1 calc R . . H24C H 0.6494 0.3898 0.0596 0.030 Uiso 1 1 calc R . . C25A C 0.39245(11) 0.37817(9) -0.11969(9) 0.0171(2) Uani 1 1 d . . . O26A O 0.34202(8) 0.29975(7) -0.07280(6) 0.02010(18) Uani 1 1 d . . . C27A C 0.24551(12) 0.27112(11) -0.12047(10) 0.0249(3) Uani 1 1 d . . . H27C H 0.2741 0.2482 -0.1829 0.030 Uiso 1 1 calc R . . H27D H 0.1730 0.3336 -0.1310 0.030 Uiso 1 1 calc R . . C28A C 0.21325(14) 0.17915(12) -0.05597(11) 0.0338(3) Uani 1 1 d . . . H28D H 0.2871 0.1198 -0.0430 0.051 Uiso 1 1 calc R . . H28E H 0.1510 0.1534 -0.0870 0.051 Uiso 1 1 calc R . . H28F H 0.1807 0.2043 0.0041 0.051 Uiso 1 1 calc R . . C1B C 0.53421(15) 0.88386(12) -0.12106(11) 0.0352(3) Uani 1 1 d . . . H1B1 H 0.4957 0.8687 -0.1773 0.053 Uiso 1 1 calc R . . H1B2 H 0.4923 0.8602 -0.0635 0.053 Uiso 1 1 calc R . . H1B3 H 0.6211 0.8447 -0.1179 0.053 Uiso 1 1 calc R . . O2B O 0.52468(10) 0.99772(8) -0.12749(7) 0.0303(2) Uani 1 1 d . . . C3B C 0.58423(12) 1.04351(10) -0.20021(9) 0.0221(3) Uani 1 1 d . . . C4B C 0.57200(12) 1.15474(10) -0.20324(10) 0.0233(3) Uani 1 1 d . . . H4B H 0.5241 1.1924 -0.1564 0.028 Uiso 1 1 calc R . . C5B C 0.65563(13) 0.98820(10) -0.26755(9) 0.0244(3) Uani 1 1 d . . . H5B H 0.6660 0.9123 -0.2657 0.029 Uiso 1 1 calc R . . C6B C 0.62842(12) 1.21053(10) -0.27325(9) 0.0209(2) Uani 1 1 d . . . H6B H 0.6191 1.2861 -0.2739 0.025 Uiso 1 1 calc R . . C7B C 0.71178(12) 1.04530(10) -0.33778(9) 0.0218(3) Uani 1 1 d . . . H7B H 0.7606 1.0069 -0.3838 0.026 Uiso 1 1 calc R . . C8B C 0.69966(11) 1.15720(9) -0.34378(9) 0.0180(2) Uani 1 1 d . . . C9B C 0.76611(11) 1.20549(10) -0.42070(9) 0.0180(2) Uani 1 1 d . . . H9B H 0.8206 1.1538 -0.4537 0.022 Uiso 1 1 calc R . . C10B C 0.76552(10) 1.30893(9) -0.45423(8) 0.0168(2) Uani 1 1 d . . . C11B C 0.68642(11) 1.40879(10) -0.41895(9) 0.0200(2) Uani 1 1 d . . . H11C H 0.7268 1.4246 -0.3631 0.024 Uiso 1 1 calc R . . H11D H 0.6062 1.3948 -0.3981 0.024 Uiso 1 1 calc R . . C12B C 0.66464(11) 1.50699(10) -0.49541(9) 0.0191(2) Uani 1 1 d . . . H12A H 0.6181 1.4938 -0.5491 0.023 Uiso 1 1 calc R . . H12B H 0.6145 1.5710 -0.4688 0.023 Uiso 1 1 calc R . . C13B C 0.78554(11) 1.53002(10) -0.53181(9) 0.0198(2) Uani 1 1 d . . . H13C H 0.7685 1.5931 -0.5823 0.024 Uiso 1 1 calc R . . H13D H 0.8291 1.5487 -0.4791 0.024 Uiso 1 1 calc R . . C14B C 0.86684(11) 1.43368(9) -0.57116(9) 0.0173(2) Uani 1 1 d . . . C15B C 0.85262(11) 1.32245(10) -0.53454(9) 0.0177(2) Uani 1 1 d . . . O16B O 0.91204(9) 1.24321(7) -0.56982(7) 0.0261(2) Uani 1 1 d . . . C17B C 0.95130(11) 1.43768(10) -0.64014(9) 0.0185(2) Uani 1 1 d . . . H17B H 0.9947 1.3687 -0.6555 0.022 Uiso 1 1 calc R . . C18B C 0.98825(10) 1.52880(10) -0.69562(9) 0.0177(2) Uani 1 1 d . . . C19B C 0.97474(11) 1.63213(10) -0.66976(9) 0.0193(2) Uani 1 1 d . . . H19B H 0.9386 1.6481 -0.6103 0.023 Uiso 1 1 calc R . . C20B C 1.04374(10) 1.50787(10) -0.78389(9) 0.0183(2) Uani 1 1 d . . . H20B H 1.0564 1.4373 -0.8017 0.022 Uiso 1 1 calc R . . C21B C 1.01370(11) 1.71223(10) -0.73032(9) 0.0185(2) Uani 1 1 d . . . H21B H 1.0044 1.7820 -0.7114 0.022 Uiso 1 1 calc R . . C22B C 1.07992(10) 1.58674(10) -0.84475(9) 0.0178(2) Uani 1 1 d . . . O23B O 1.12901(8) 1.57263(7) -0.93280(7) 0.0241(2) Uani 1 1 d . . . C24B C 1.15493(13) 1.46577(11) -0.95911(10) 0.0276(3) Uani 1 1 d . . . H24D H 1.2141 1.4164 -0.9138 0.041 Uiso 1 1 calc R . . H24E H 1.1897 1.4664 -1.0233 0.041 Uiso 1 1 calc R . . H24F H 1.0787 1.4413 -0.9582 0.041 Uiso 1 1 calc R . . C25B C 1.06588(10) 1.69108(10) -0.81777(9) 0.0174(2) Uani 1 1 d . . . O26B O 1.10547(8) 1.76324(7) -0.88262(6) 0.02140(19) Uani 1 1 d . . . C27B C 1.09225(12) 1.87094(10) -0.86008(9) 0.0215(2) Uani 1 1 d . . . H27A H 1.1339 1.8690 -0.7989 0.026 Uiso 1 1 calc R . . H27B H 1.0042 1.9076 -0.8546 0.026 Uiso 1 1 calc R . . C28B C 1.15054(15) 1.92979(12) -0.94017(11) 0.0316(3) Uani 1 1 d . . . H28A H 1.2383 1.8943 -0.9431 0.047 Uiso 1 1 calc R . . H28B H 1.1406 2.0051 -0.9291 0.047 Uiso 1 1 calc R . . H28C H 1.1107 1.9283 -1.0005 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0511(9) 0.0342(8) 0.0304(8) 0.0054(6) 0.0058(7) -0.0195(7) O2A 0.0392(6) 0.0278(5) 0.0200(5) 0.0058(4) 0.0021(4) -0.0098(4) C3A 0.0258(6) 0.0174(6) 0.0181(6) -0.0003(5) 0.0046(5) -0.0018(5) C4A 0.0253(6) 0.0226(6) 0.0206(6) -0.0019(5) 0.0039(5) -0.0093(5) C5A 0.0232(6) 0.0241(6) 0.0164(6) -0.0032(5) -0.0008(5) -0.0014(5) C6A 0.0206(6) 0.0212(6) 0.0175(6) -0.0021(5) 0.0009(4) -0.0063(5) C7A 0.0203(6) 0.0210(6) 0.0196(6) -0.0048(5) 0.0019(5) -0.0049(5) C8A 0.0176(5) 0.0140(5) 0.0189(6) -0.0029(4) 0.0029(4) -0.0019(4) C9A 0.0188(5) 0.0133(5) 0.0177(6) -0.0020(4) 0.0005(4) -0.0030(4) C10A 0.0185(5) 0.0113(5) 0.0174(6) -0.0014(4) 0.0004(4) -0.0027(4) C11A 0.0188(5) 0.0168(5) 0.0190(6) 0.0017(4) -0.0011(4) -0.0029(4) C12A 0.0174(5) 0.0149(5) 0.0224(6) 0.0006(5) -0.0001(4) -0.0004(4) C13A 0.0160(5) 0.0173(6) 0.0203(6) 0.0001(5) -0.0002(4) -0.0033(4) C14A 0.0159(5) 0.0145(5) 0.0161(5) -0.0033(4) 0.0019(4) -0.0037(4) C15A 0.0167(5) 0.0113(5) 0.0189(6) -0.0012(4) 0.0010(4) -0.0024(4) O16A 0.0195(4) 0.0224(4) 0.0237(5) 0.0048(4) -0.0045(3) -0.0068(3) C17A 0.0164(5) 0.0161(5) 0.0161(6) -0.0026(4) 0.0005(4) -0.0041(4) C18A 0.0174(5) 0.0143(5) 0.0154(5) -0.0023(4) 0.0010(4) -0.0036(4) C19A 0.0198(5) 0.0191(6) 0.0166(6) 0.0000(4) -0.0026(4) -0.0060(4) C20A 0.0159(5) 0.0156(5) 0.0173(6) -0.0010(4) -0.0010(4) -0.0055(4) C21A 0.0177(5) 0.0211(6) 0.0209(6) -0.0014(5) -0.0032(4) -0.0071(5) C22A 0.0171(5) 0.0134(5) 0.0154(5) -0.0013(4) -0.0004(4) -0.0036(4) O23A 0.0204(4) 0.0200(4) 0.0206(4) 0.0059(3) -0.0047(3) -0.0095(3) C24A 0.0164(5) 0.0220(6) 0.0193(6) 0.0022(5) -0.0033(4) -0.0043(4) C25A 0.0178(5) 0.0155(5) 0.0194(6) -0.0022(4) 0.0015(4) -0.0069(4) O26A 0.0191(4) 0.0201(4) 0.0233(5) 0.0008(3) -0.0016(3) -0.0107(3) C27A 0.0222(6) 0.0245(6) 0.0306(7) -0.0012(5) -0.0047(5) -0.0119(5) C28A 0.0326(7) 0.0323(8) 0.0409(9) 0.0045(6) -0.0065(6) -0.0205(6) C1B 0.0459(9) 0.0244(7) 0.0369(8) 0.0093(6) -0.0055(7) -0.0181(6) O2B 0.0403(6) 0.0242(5) 0.0282(5) 0.0035(4) 0.0057(4) -0.0154(4) C3B 0.0249(6) 0.0208(6) 0.0216(6) 0.0018(5) -0.0025(5) -0.0093(5) C4B 0.0260(6) 0.0182(6) 0.0247(7) -0.0022(5) 0.0055(5) -0.0047(5) C5B 0.0333(7) 0.0153(6) 0.0256(7) -0.0012(5) -0.0032(5) -0.0083(5) C6B 0.0246(6) 0.0145(5) 0.0235(6) -0.0023(5) 0.0028(5) -0.0047(5) C7B 0.0259(6) 0.0179(6) 0.0217(6) -0.0048(5) 0.0003(5) -0.0046(5) C8B 0.0180(5) 0.0162(5) 0.0199(6) -0.0019(4) -0.0024(4) -0.0045(4) C9B 0.0170(5) 0.0184(6) 0.0191(6) -0.0049(5) 0.0005(4) -0.0042(4) C10B 0.0149(5) 0.0172(5) 0.0178(6) -0.0033(4) -0.0010(4) -0.0022(4) C11B 0.0198(6) 0.0174(6) 0.0202(6) -0.0025(5) 0.0030(5) -0.0001(4) C12B 0.0184(5) 0.0167(5) 0.0198(6) -0.0033(5) 0.0017(4) 0.0004(4) C13B 0.0216(6) 0.0157(5) 0.0215(6) -0.0034(5) 0.0021(5) -0.0031(4) C14B 0.0170(5) 0.0150(5) 0.0193(6) -0.0020(4) -0.0021(4) -0.0025(4) C15B 0.0171(5) 0.0167(5) 0.0187(6) -0.0025(4) 0.0000(4) -0.0032(4) O16B 0.0296(5) 0.0168(4) 0.0309(5) -0.0051(4) 0.0118(4) -0.0041(4) C17B 0.0183(5) 0.0147(5) 0.0214(6) -0.0024(4) -0.0007(4) -0.0018(4) C18B 0.0150(5) 0.0173(5) 0.0193(6) -0.0012(4) -0.0006(4) -0.0018(4) C19B 0.0189(5) 0.0207(6) 0.0181(6) -0.0036(5) 0.0007(4) -0.0042(5) C20B 0.0159(5) 0.0159(5) 0.0221(6) -0.0035(5) 0.0010(4) -0.0017(4) C21B 0.0189(5) 0.0162(5) 0.0207(6) -0.0036(5) -0.0004(4) -0.0045(4) C22B 0.0135(5) 0.0205(6) 0.0189(6) -0.0042(5) 0.0021(4) -0.0027(4) O23B 0.0257(5) 0.0237(5) 0.0245(5) -0.0077(4) 0.0088(4) -0.0077(4) C24B 0.0285(7) 0.0286(7) 0.0285(7) -0.0129(6) 0.0061(5) -0.0081(6) C25B 0.0143(5) 0.0179(6) 0.0194(6) -0.0005(4) 0.0003(4) -0.0041(4) O26B 0.0239(4) 0.0183(4) 0.0232(5) -0.0029(3) 0.0061(3) -0.0080(3) C27B 0.0246(6) 0.0190(6) 0.0229(6) -0.0031(5) -0.0001(5) -0.0091(5) C28B 0.0420(8) 0.0256(7) 0.0305(8) -0.0009(6) 0.0036(6) -0.0162(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 C1A O2A 1.4296(18) . ? O2A C3A 1.3672(15) . ? C3A C4A 1.3879(18) . ? C3A C5A 1.3949(18) . ? C4A C6A 1.3882(17) . ? C5A C7A 1.3819(18) . ? C6A C8A 1.3992(16) . ? C7A C8A 1.4040(17) . ? C8A C9A 1.4626(16) . ? C9A C10A 1.3505(16) . ? C10A C15A 1.4993(16) . ? C10A C11A 1.5078(16) . ? C11A C12A 1.5238(17) . ? C12A C13A 1.5211(16) . ? C13A C14A 1.5109(16) . ? C14A C17A 1.3470(16) . ? C14A C15A 1.5005(15) . ? C15A O16A 1.2272(14) . ? C17A C18A 1.4604(15) . ? C18A C19A 1.3952(16) . ? C18A C20A 1.4112(16) . ? C19A C21A 1.3918(16) . ? C20A C22A 1.3798(15) . ? C21A C25A 1.3852(17) . ? C22A O23A 1.3591(14) . ? C22A C25A 1.4111(15) . ? O23A C24A 1.4307(14) . ? C25A O26A 1.3633(13) . ? O26A C27A 1.4374(14) . ? C27A C28A 1.5051(18) . ? C1B O2B 1.4312(17) . ? O2B C3B 1.3594(15) . ? C3B C5B 1.3847(19) . ? C3B C4B 1.3968(17) . ? C4B C6B 1.3775(17) . ? C5B C7B 1.3868(18) . ? C6B C8B 1.4063(18) . ? C7B C8B 1.4018(17) . ? C8B C9B 1.4598(17) . ? C9B C10B 1.3486(16) . ? C10B C15B 1.5001(16) . ? C10B C11B 1.5070(17) . ? C11B C12B 1.5231(17) . ? C12B C13B 1.5208(17) . ? C13B C14B 1.5089(17) . ? C14B C17B 1.3477(17) . ? C14B C15B 1.4988(16) . ? C15B O16B 1.2310(15) . ? C17B C18B 1.4613(16) . ? C18B C19B 1.3960(17) . ? C18B C20B 1.4105(17) . ? C19B C21B 1.3968(17) . ? C20B C22B 1.3728(17) . ? C21B C25B 1.3872(17) . ? C22B O23B 1.3662(15) . ? C22B C25B 1.4140(17) . ? O23B C24B 1.4298(16) . ? C25B O26B 1.3615(14) . ? O26B C27B 1.4333(14) . ? C27B C28B 1.5034(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 C3A O2A C1A 117.41(11) . . ? O2A C3A C4A 124.29(12) . . ? O2A C3A C5A 115.80(11) . . ? C4A C3A C5A 119.90(11) . . ? C3A C4A C6A 119.10(11) . . ? C7A C5A C3A 120.29(12) . . ? C4A C6A C8A 122.19(12) . . ? C5A C7A C8A 121.02(11) . . ? C6A C8A C7A 117.28(11) . . ? C6A C8A C9A 117.40(11) . . ? C7A C8A C9A 125.31(11) . . ? C10A C9A C8A 129.08(11) . . ? C9A C10A C15A 116.43(10) . . ? C9A C10A C11A 125.65(11) . . ? C15A C10A C11A 117.83(10) . . ? C10A C11A C12A 110.40(10) . . ? C13A C12A C11A 109.91(10) . . ? C14A C13A C12A 111.61(9) . . ? C17A C14A C15A 115.31(10) . . ? C17A C14A C13A 126.07(10) . . ? C15A C14A C13A 118.61(10) . . ? O16A C15A C10A 121.27(10) . . ? O16A C15A C14A 120.96(10) . . ? C10A C15A C14A 117.76(10) . . ? C14A C17A C18A 131.48(11) . . ? C19A C18A C20A 118.06(10) . . ? C19A C18A C17A 125.46(11) . . ? C20A C18A C17A 116.41(10) . . ? C21A C19A C18A 120.85(11) . . ? C22A C20A C18A 121.52(10) . . ? C25A C21A C19A 120.46(10) . . ? O23A C22A C20A 125.50(10) . . ? O23A C22A C25A 115.14(10) . . ? C20A C22A C25A 119.32(10) . . ? C22A O23A C24A 117.13(9) . . ? O26A C25A C21A 125.63(10) . . ? O26A C25A C22A 114.68(10) . . ? C21A C25A C22A 119.68(10) . . ? C25A O26A C27A 117.52(9) . . ? O26A C27A C28A 106.12(11) . . ? C3B O2B C1B 117.57(11) . . ? O2B C3B C5B 125.11(11) . . ? O2B C3B C4B 115.28(12) . . ? C5B C3B C4B 119.59(11) . . ? C6B C4B C3B 120.89(12) . . ? C3B C5B C7B 118.97(11) . . ? C4B C6B C8B 120.96(11) . . ? C5B C7B C8B 122.85(12) . . ? C7B C8B C6B 116.72(11) . . ? C7B C8B C9B 116.47(11) . . ? C6B C8B C9B 126.78(11) . . ? C10B C9B C8B 132.79(11) . . ? C9B C10B C15B 115.11(11) . . ? C9B C10B C11B 126.19(11) . . ? C15B C10B C11B 118.70(10) . . ? C10B C11B C12B 112.05(10) . . ? C13B C12B C11B 111.23(10) . . ? C14B C13B C12B 111.50(10) . . ? C17B C14B C15B 115.17(11) . . ? C17B C14B C13B 125.75(11) . . ? C15B C14B C13B 119.04(10) . . ? O16B C15B C14B 120.32(11) . . ? O16B C15B C10B 120.48(11) . . ? C14B C15B C10B 119.20(10) . . ? C14B C17B C18B 131.69(11) . . ? C19B C18B C20B 117.88(11) . . ? C19B C18B C17B 126.76(11) . . ? C20B C18B C17B 115.36(11) . . ? C18B C19B C21B 120.74(11) . . ? C22B C20B C18B 121.77(11) . . ? C25B C21B C19B 120.72(11) . . ? O23B C22B C20B 124.39(11) . . ? O23B C22B C25B 115.80(10) . . ? C20B C22B C25B 119.81(11) . . ? C22B O23B C24B 117.39(10) . . ? O26B C25B C21B 125.62(11) . . ? O26B C25B C22B 115.34(10) . . ? C21B C25B C22B 119.04(11) . . ? C25B O26B C27B 118.07(9) . . ? O26B C27B C28B 106.57(10) . . ? 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 C1A O2A C3A C4A -4.96(19) . . . . ? C1A O2A C3A C5A 176.41(12) . . . . ? O2A C3A C4A C6A 179.35(12) . . . . ? C5A C3A C4A C6A -2.08(19) . . . . ? O2A C3A C5A C7A -177.39(11) . . . . ? C4A C3A C5A C7A 3.91(19) . . . . ? C3A C4A C6A C8A -2.40(19) . . . . ? C3A C5A C7A C8A -1.31(19) . . . . ? C4A C6A C8A C7A 4.88(18) . . . . ? C4A C6A C8A C9A -173.77(11) . . . . ? C5A C7A C8A C6A -2.98(18) . . . . ? C5A C7A C8A C9A 175.55(12) . . . . ? C6A C8A C9A C10A 148.41(13) . . . . ? C7A C8A C9A C10A -30.1(2) . . . . ? C8A C9A C10A C15A -176.62(11) . . . . ? C8A C9A C10A C11A -0.2(2) . . . . ? C9A C10A C11A C12A -150.03(12) . . . . ? C15A C10A C11A C12A 26.35(14) . . . . ? C10A C11A C12A C13A -62.89(13) . . . . ? C11A C12A C13A C14A 56.49(13) . . . . ? C12A C13A C14A C17A 167.27(11) . . . . ? C12A C13A C14A C15A -14.18(15) . . . . ? C9A C10A C15A O16A 11.07(17) . . . . ? C11A C10A C15A O16A -165.65(11) . . . . ? C9A C10A C15A C14A -168.10(10) . . . . ? C11A C10A C15A C14A 15.18(15) . . . . ? C17A C14A C15A O16A -22.27(16) . . . . ? C13A C14A C15A O16A 159.03(11) . . . . ? C17A C14A C15A C10A 156.91(10) . . . . ? C13A C14A C15A C10A -21.80(15) . . . . ? C15A C14A C17A C18A -174.31(11) . . . . ? C13A C14A C17A C18A 4.3(2) . . . . ? C14A C17A C18A C19A 15.4(2) . . . . ? C14A C17A C18A C20A -167.58(12) . . . . ? C20A C18A C19A C21A -1.64(18) . . . . ? C17A C18A C19A C21A 175.36(12) . . . . ? C19A C18A C20A C22A -1.00(18) . . . . ? C17A C18A C20A C22A -178.27(11) . . . . ? C18A C19A C21A C25A 1.94(19) . . . . ? C18A C20A C22A O23A -179.05(11) . . . . ? C18A C20A C22A C25A 3.28(18) . . . . ? C20A C22A O23A C24A 1.84(17) . . . . ? C25A C22A O23A C24A 179.60(10) . . . . ? C19A C21A C25A O26A -178.56(12) . . . . ? C19A C21A C25A C22A 0.39(18) . . . . ? O23A C22A C25A O26A -1.80(15) . . . . ? C20A C22A C25A O26A 176.10(11) . . . . ? O23A C22A C25A C21A 179.14(11) . . . . ? C20A C22A C25A C21A -2.96(18) . . . . ? C21A C25A O26A C27A 13.34(18) . . . . ? C22A C25A O26A C27A -165.66(11) . . . . ? C25A O26A C27A C28A 176.49(11) . . . . ? C1B O2B C3B C5B -1.42(19) . . . . ? C1B O2B C3B C4B 180.00(12) . . . . ? O2B C3B C4B C6B 179.71(12) . . . . ? C5B C3B C4B C6B 1.1(2) . . . . ? O2B C3B C5B C7B -179.66(12) . . . . ? C4B C3B C5B C7B -1.15(19) . . . . ? C3B C4B C6B C8B 0.2(2) . . . . ? C3B C5B C7B C8B 0.1(2) . . . . ? C5B C7B C8B C6B 1.09(18) . . . . ? C5B C7B C8B C9B 178.93(12) . . . . ? C4B C6B C8B C7B -1.19(18) . . . . ? C4B C6B C8B C9B -178.77(12) . . . . ? C7B C8B C9B C10B 171.53(13) . . . . ? C6B C8B C9B C10B -10.9(2) . . . . ? C8B C9B C10B C15B 178.38(12) . . . . ? C8B C9B C10B C11B -2.0(2) . . . . ? C9B C10B C11B C12B -154.36(12) . . . . ? C15B C10B C11B C12B 25.29(15) . . . . ? C10B C11B C12B C13B -57.39(13) . . . . ? C11B C12B C13B C14B 57.70(14) . . . . ? C12B C13B C14B C17B 151.55(12) . . . . ? C12B C13B C14B C15B -26.31(15) . . . . ? C17B C14B C15B O16B -2.87(17) . . . . ? C13B C14B C15B O16B 175.22(11) . . . . ? C17B C14B C15B C10B 176.91(10) . . . . ? C13B C14B C15B C10B -5.00(16) . . . . ? C9B C10B C15B O16B 5.02(17) . . . . ? C11B C10B C15B O16B -174.67(11) . . . . ? C9B C10B C15B C14B -174.76(10) . . . . ? C11B C10B C15B C14B 5.55(16) . . . . ? C15B C14B C17B C18B 177.33(12) . . . . ? C13B C14B C17B C18B -0.6(2) . . . . ? C14B C17B C18B C19B 23.5(2) . . . . ? C14B C17B C18B C20B -156.93(13) . . . . ? C20B C18B C19B C21B 0.81(17) . . . . ? C17B C18B C19B C21B -179.59(11) . . . . ? C19B C18B C20B C22B -2.23(17) . . . . ? C17B C18B C20B C22B 178.13(11) . . . . ? C18B C19B C21B C25B 0.46(18) . . . . ? C18B C20B C22B O23B -176.96(11) . . . . ? C18B C20B C22B C25B 2.33(18) . . . . ? C20B C22B O23B C24B -6.20(17) . . . . ? C25B C22B O23B C24B 174.49(11) . . . . ? C19B C21B C25B O26B 179.13(11) . . . . ? C19B C21B C25B C22B -0.39(17) . . . . ? O23B C22B C25B O26B -1.20(15) . . . . ? C20B C22B C25B O26B 179.45(10) . . . . ? O23B C22B C25B C21B 178.36(10) . . . . ? C20B C22B C25B C21B -0.99(17) . . . . ? C21B C25B O26B C27B -0.36(17) . . . . ? C22B C25B O26B C27B 179.17(10) . . . . ? C25B O26B C27B C28B 176.28(11) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.423 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.049 # Attachment 'O.CIF' data_1o _database_code_depnum_ccdc_archive 'CCDC 605465' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E,E)-2-(4-Methoxybenzylidene)-6-(4-nitrobenzylidene)cyclohexanone ; _chemical_name_common ;(E,E)-2-(4-Methoxybenzylidene)-6-(4- nitrobenzylidene)cyclohexanone ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H19 N 04' _chemical_formula_sum 'C21 H19 N O4' _chemical_formula_weight 349.37 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' N N 0.0061 0.0033 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8646(3) _cell_length_b 9.6830(3) _cell_length_c 11.3746(5) _cell_angle_alpha 95.5870(10) _cell_angle_beta 102.8010(10) _cell_angle_gamma 91.992(2) _cell_volume 839.25(6) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _exptl_crystal_description block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.096 _exptl_special_details ; ? ; _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_reflns_number 6955 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.66 _reflns_number_total 3102 _reflns_number_gt 2280 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.0562P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3102 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0904 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 1.09975(15) -0.10826(11) 0.91272(10) 0.0240(3) Uani 1 1 d . . . C22 C -0.0103(2) 0.65761(16) 0.10201(15) 0.0195(4) Uani 1 1 d . . . H22 H -0.0039 0.7371 0.0600 0.023 Uiso 1 1 calc R . . C18 C 0.1315(2) 0.47759(16) 0.21632(14) 0.0181(4) Uani 1 1 d . . . C21 C -0.1839(2) 0.48448(16) 0.17268(14) 0.0198(4) Uani 1 1 d . . . H21 H -0.2950 0.4474 0.1780 0.024 Uiso 1 1 calc R . . C19 C -0.0335(2) 0.42268(16) 0.22288(14) 0.0192(4) Uani 1 1 d . . . H19 H -0.0415 0.3416 0.2626 0.023 Uiso 1 1 calc R . . C5 C 0.8341(2) -0.04018(16) 0.80382(14) 0.0204(4) Uani 1 1 d . . . H5 H 0.7789 -0.0833 0.8582 0.024 Uiso 1 1 calc R . . C11 C 0.4402(2) 0.21769(16) 0.59702(15) 0.0200(4) Uani 1 1 d . . . H11A H 0.5102 0.2261 0.6815 0.024 Uiso 1 1 calc R . . H11B H 0.3715 0.1275 0.5815 0.024 Uiso 1 1 calc R . . C23 C -0.1694(2) 0.60182(16) 0.11426(14) 0.0186(4) Uani 1 1 d . . . C3 C 1.0145(2) -0.04321(15) 0.81798(14) 0.0200(4) Uani 1 1 d . . . C13 C 0.2121(2) 0.33023(16) 0.45321(15) 0.0209(4) Uani 1 1 d . . . H13A H 0.1430 0.2405 0.4296 0.025 Uiso 1 1 calc R . . H13B H 0.1297 0.4056 0.4470 0.025 Uiso 1 1 calc R . . C7 C 0.7348(2) 0.02474(16) 0.71176(15) 0.0205(4) Uani 1 1 d . . . H7 H 0.6119 0.0253 0.7036 0.025 Uiso 1 1 calc R . . C15 C 0.5084(2) 0.28763(16) 0.39731(15) 0.0197(4) Uani 1 1 d . . . C14 C 0.3315(2) 0.34692(16) 0.36755(15) 0.0191(4) Uani 1 1 d . . . C4 C 1.0942(2) 0.01675(16) 0.73609(15) 0.0223(4) Uani 1 1 d . . . H4 H 1.2167 0.0137 0.7435 0.027 Uiso 1 1 calc R . . C6 C 0.9923(2) 0.08120(16) 0.64337(15) 0.0214(4) Uani 1 1 d . . . H6 H 1.0476 0.1206 0.5872 0.026 Uiso 1 1 calc R . . C10 C 0.5621(2) 0.21899(16) 0.51126(14) 0.0188(4) Uani 1 1 d . . . C8 C 0.8122(2) 0.09054(16) 0.62922(14) 0.0187(4) Uani 1 1 d . . . C12 C 0.3156(2) 0.33470(16) 0.58345(15) 0.0216(4) Uani 1 1 d . . . H12A H 0.2342 0.3260 0.6377 0.026 Uiso 1 1 calc R . . H12B H 0.3828 0.4252 0.6078 0.026 Uiso 1 1 calc R . . C20 C 0.1386(2) 0.59378(16) 0.15292(14) 0.0200(4) Uani 1 1 d . . . H20 H 0.2489 0.6297 0.1447 0.024 Uiso 1 1 calc R . . O25 O -0.32143(16) 0.76067(13) -0.00272(12) 0.0342(3) Uani 1 1 d . . . O16 O 0.60686(15) 0.29419(12) 0.32714(11) 0.0291(3) Uani 1 1 d . . . N24 N -0.32882(18) 0.67007(14) 0.06475(12) 0.0229(3) Uani 1 1 d . . . C17 C 0.2941(2) 0.41461(16) 0.26801(15) 0.0192(4) Uani 1 1 d . . . H17 H 0.3849 0.4226 0.2258 0.023 Uiso 1 1 calc R . . O26 O -0.46432(16) 0.63478(14) 0.09346(13) 0.0420(4) Uani 1 1 d . . . C9 C 0.7205(2) 0.16457(15) 0.53094(15) 0.0190(4) Uani 1 1 d . . . H9 H 0.7831 0.1768 0.4699 0.023 Uiso 1 1 calc R . . C1 C 1.2849(2) -0.11740(18) 0.92877(16) 0.0269(4) Uani 1 1 d . . . H1A H 1.3103 -0.1671 0.8560 0.040 Uiso 1 1 calc R . . H1B H 1.3294 -0.1677 0.9989 0.040 Uiso 1 1 calc R . . H1C H 1.3415 -0.0236 0.9424 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0219(7) 0.0270(7) 0.0235(7) 0.0091(5) 0.0027(5) 0.0062(5) C22 0.0233(9) 0.0170(8) 0.0192(9) 0.0040(6) 0.0062(7) -0.0003(7) C18 0.0193(9) 0.0187(8) 0.0164(9) 0.0013(6) 0.0050(7) 0.0007(6) C21 0.0177(9) 0.0229(9) 0.0198(9) 0.0024(7) 0.0068(7) -0.0014(7) C19 0.0218(9) 0.0169(8) 0.0197(9) 0.0048(7) 0.0055(7) -0.0004(7) C5 0.0217(9) 0.0205(9) 0.0208(9) 0.0054(7) 0.0075(7) 0.0005(7) C11 0.0193(9) 0.0210(8) 0.0199(9) 0.0054(7) 0.0038(7) 0.0009(7) C23 0.0188(9) 0.0205(8) 0.0167(9) 0.0021(7) 0.0041(7) 0.0049(7) C3 0.0239(10) 0.0165(8) 0.0189(9) 0.0020(7) 0.0032(7) 0.0027(7) C13 0.0203(9) 0.0205(9) 0.0240(9) 0.0053(7) 0.0078(7) 0.0033(7) C7 0.0180(9) 0.0193(9) 0.0247(9) 0.0022(7) 0.0060(7) -0.0001(7) C15 0.0204(9) 0.0170(8) 0.0231(9) 0.0035(7) 0.0078(8) -0.0016(7) C14 0.0186(9) 0.0168(8) 0.0225(9) 0.0025(6) 0.0055(7) -0.0001(6) C4 0.0179(9) 0.0230(9) 0.0264(10) 0.0052(7) 0.0049(7) 0.0020(7) C6 0.0203(9) 0.0215(9) 0.0249(10) 0.0055(7) 0.0096(8) 0.0006(7) C10 0.0203(9) 0.0150(8) 0.0210(9) 0.0022(6) 0.0044(7) -0.0014(6) C8 0.0196(9) 0.0174(8) 0.0187(9) 0.0014(6) 0.0041(7) 0.0009(6) C12 0.0215(9) 0.0215(9) 0.0229(9) 0.0013(7) 0.0075(7) 0.0009(7) C20 0.0183(9) 0.0220(9) 0.0207(9) 0.0036(7) 0.0066(7) -0.0021(7) O25 0.0292(8) 0.0355(7) 0.0422(8) 0.0236(6) 0.0083(6) 0.0076(6) O16 0.0267(7) 0.0370(7) 0.0306(7) 0.0160(6) 0.0147(6) 0.0101(5) N24 0.0215(8) 0.0258(8) 0.0231(8) 0.0063(6) 0.0065(6) 0.0052(6) C17 0.0185(9) 0.0180(8) 0.0224(9) 0.0026(7) 0.0076(7) -0.0001(6) O26 0.0208(7) 0.0570(9) 0.0587(10) 0.0312(7) 0.0193(7) 0.0132(6) C9 0.0192(9) 0.0188(8) 0.0199(9) 0.0038(6) 0.0061(7) -0.0009(7) C1 0.0214(10) 0.0296(10) 0.0291(11) 0.0063(8) 0.0020(8) 0.0076(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 O2 C3 1.3597(19) . ? O2 C1 1.434(2) . ? C22 C20 1.382(2) . ? C22 C23 1.386(2) . ? C18 C20 1.400(2) . ? C18 C19 1.405(2) . ? C18 C17 1.464(2) . ? C21 C19 1.378(2) . ? C21 C23 1.385(2) . ? C5 C7 1.379(2) . ? C5 C3 1.394(2) . ? C11 C10 1.513(2) . ? C11 C12 1.521(2) . ? C23 N24 1.464(2) . ? C3 C4 1.391(2) . ? C13 C14 1.511(2) . ? C13 C12 1.520(2) . ? C7 C8 1.414(2) . ? C15 O16 1.2332(19) . ? C15 C10 1.498(2) . ? C15 C14 1.505(2) . ? C14 C17 1.345(2) . ? C4 C6 1.390(2) . ? C6 C8 1.397(2) . ? C10 C9 1.351(2) . ? C8 C9 1.455(2) . ? O25 N24 1.2285(16) . ? N24 O26 1.2286(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 C3 O2 C1 117.76(12) . . ? C20 C22 C23 117.78(15) . . ? C20 C18 C19 118.11(15) . . ? C20 C18 C17 119.09(14) . . ? C19 C18 C17 122.73(14) . . ? C19 C21 C23 118.51(15) . . ? C21 C19 C18 121.10(14) . . ? C7 C5 C3 120.74(14) . . ? C10 C11 C12 112.59(13) . . ? C21 C23 C22 122.67(16) . . ? C21 C23 N24 118.38(14) . . ? C22 C23 N24 118.95(14) . . ? O2 C3 C4 124.76(15) . . ? O2 C3 C5 115.80(14) . . ? C4 C3 C5 119.44(15) . . ? C14 C13 C12 111.17(14) . . ? C5 C7 C8 121.31(15) . . ? O16 C15 C10 120.59(15) . . ? O16 C15 C14 119.86(14) . . ? C10 C15 C14 119.55(14) . . ? C17 C14 C15 117.06(14) . . ? C17 C14 C13 124.98(15) . . ? C15 C14 C13 117.94(14) . . ? C6 C4 C3 119.15(16) . . ? C4 C6 C8 122.87(15) . . ? C9 C10 C15 116.57(14) . . ? C9 C10 C11 124.53(15) . . ? C15 C10 C11 118.88(14) . . ? C6 C8 C7 116.41(15) . . ? C6 C8 C9 117.78(14) . . ? C7 C8 C9 125.80(15) . . ? C13 C12 C11 110.82(14) . . ? C22 C20 C18 121.76(15) . . ? O25 N24 O26 122.81(14) . . ? O25 N24 C23 118.83(13) . . ? O26 N24 C23 118.35(13) . . ? C14 C17 C18 128.38(15) . . ? C10 C9 C8 131.35(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 C23 C21 C19 C18 0.6(2) . . . . ? C20 C18 C19 C21 -2.6(2) . . . . ? C17 C18 C19 C21 -179.71(15) . . . . ? C19 C21 C23 C22 1.4(2) . . . . ? C19 C21 C23 N24 -177.89(14) . . . . ? C20 C22 C23 C21 -1.4(2) . . . . ? C20 C22 C23 N24 177.97(14) . . . . ? C1 O2 C3 C4 -0.8(2) . . . . ? C1 O2 C3 C5 178.26(14) . . . . ? C7 C5 C3 O2 179.11(14) . . . . ? C7 C5 C3 C4 -1.8(2) . . . . ? C3 C5 C7 C8 -0.2(2) . . . . ? O16 C15 C14 C17 -4.8(2) . . . . ? C10 C15 C14 C17 176.14(14) . . . . ? O16 C15 C14 C13 177.08(15) . . . . ? C10 C15 C14 C13 -1.9(2) . . . . ? C12 C13 C14 C17 -144.57(16) . . . . ? C12 C13 C14 C15 33.34(19) . . . . ? O2 C3 C4 C6 -179.54(14) . . . . ? C5 C3 C4 C6 1.4(2) . . . . ? C3 C4 C6 C8 0.9(3) . . . . ? O16 C15 C10 C9 -0.8(2) . . . . ? C14 C15 C10 C9 178.23(14) . . . . ? O16 C15 C10 C11 177.85(15) . . . . ? C14 C15 C10 C11 -3.1(2) . . . . ? C12 C11 C10 C9 154.80(15) . . . . ? C12 C11 C10 C15 -23.7(2) . . . . ? C4 C6 C8 C7 -2.8(2) . . . . ? C4 C6 C8 C9 178.02(15) . . . . ? C5 C7 C8 C6 2.4(2) . . . . ? C5 C7 C8 C9 -178.48(15) . . . . ? C14 C13 C12 C11 -60.60(17) . . . . ? C10 C11 C12 C13 55.77(17) . . . . ? C23 C22 C20 C18 -0.8(2) . . . . ? C19 C18 C20 C22 2.7(2) . . . . ? C17 C18 C20 C22 179.92(15) . . . . ? C21 C23 N24 O25 -169.07(15) . . . . ? C22 C23 N24 O25 11.6(2) . . . . ? C21 C23 N24 O26 11.5(2) . . . . ? C22 C23 N24 O26 -167.85(16) . . . . ? C15 C14 C17 C18 177.73(15) . . . . ? C13 C14 C17 C18 -4.3(3) . . . . ? C20 C18 C17 C14 149.93(17) . . . . ? C19 C18 C17 C14 -33.0(3) . . . . ? C15 C10 C9 C8 -179.22(15) . . . . ? C11 C10 C9 C8 2.2(3) . . . . ? C6 C8 C9 C10 -162.11(17) . . . . ? C7 C8 C9 C10 18.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.186 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.053 # Attachment 'P.CIF' data_1p _database_code_depnum_ccdc_archive 'CCDC 605466' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E,E)-2-((6-Bromopyridin-2-yl)methylene)-6-(4-methoxybenzylidene)cyclohexanone ; _chemical_name_common ;(E,E)-2-((6-Bromopyridin-2-yl)methylene)-6-(4- methoxybenzylidene)cyclohexanone ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 Br N O2' _chemical_formula_sum 'C20 H18 Br N O2' _chemical_formula_weight 384.26 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' N N 0.0061 0.0033 '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' Br Br -0.2901 2.4595 '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~/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 18.57480(10) _cell_length_b 6.26410(10) _cell_length_c 15.93370(10) _cell_angle_alpha 90.00 _cell_angle_beta 115.1940(10) _cell_angle_gamma 90.00 _cell_volume 1677.59(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _exptl_crystal_description block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 2.462 _exptl_special_details ; ? ; _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_reflns_number 6923 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3878 _reflns_number_gt 2825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0305P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3878 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0697 _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 Br24 Br 0.478808(14) 0.10323(4) 0.145038(16) 0.02794(9) Uani 1 1 d . . . O2 O 0.94044(9) 0.0843(3) -0.44222(10) 0.0257(4) Uani 1 1 d . . . C4 C 0.87781(13) -0.0929(4) -0.36280(15) 0.0200(5) Uani 1 1 d . . . H4 H 0.8714 -0.2119 -0.4023 0.024 Uiso 1 1 calc R . . C7 C 0.89741(13) 0.2515(4) -0.24689(15) 0.0204(5) Uani 1 1 d . . . H7 H 0.9051 0.3695 -0.2065 0.024 Uiso 1 1 calc R . . C22 C 0.54691(13) 0.2920(4) 0.11702(14) 0.0194(5) Uani 1 1 d . . . O16 O 0.79354(10) -0.0254(3) -0.01764(11) 0.0264(4) Uani 1 1 d . . . N20 N 0.59584(11) 0.1989(3) 0.08785(11) 0.0198(4) Uani 1 1 d . . . C23 C 0.54103(14) 0.5089(4) 0.12826(14) 0.0216(5) Uani 1 1 d . . . H23 H 0.5037 0.5654 0.1486 0.026 Uiso 1 1 calc R . . C13 C 0.69940(13) 0.5086(4) -0.07890(14) 0.0197(5) Uani 1 1 d . . . H13A H 0.7390 0.6136 -0.0389 0.024 Uiso 1 1 calc R . . H13B H 0.6465 0.5532 -0.0842 0.024 Uiso 1 1 calc R . . C18 C 0.64341(13) 0.3299(4) 0.06517(14) 0.0181(5) Uani 1 1 d . . . C6 C 0.84956(13) -0.1022(4) -0.29599(15) 0.0187(5) Uani 1 1 d . . . H6 H 0.8247 -0.2294 -0.2891 0.022 Uiso 1 1 calc R . . C5 C 0.92709(13) 0.2623(4) -0.31354(14) 0.0201(5) Uani 1 1 d . . . H5 H 0.9547 0.3857 -0.3185 0.024 Uiso 1 1 calc R . . C9 C 0.82473(13) 0.0548(4) -0.16809(15) 0.0196(5) Uani 1 1 d . . . H9 H 0.8263 -0.0841 -0.1434 0.023 Uiso 1 1 calc R . . C3 C 0.91573(13) 0.0901(4) -0.37260(14) 0.0186(5) Uani 1 1 d . . . C14 C 0.71924(13) 0.2923(4) -0.03316(14) 0.0168(5) Uani 1 1 d . . . C8 C 0.85664(13) 0.0727(4) -0.23750(15) 0.0179(5) Uani 1 1 d . . . C15 C 0.77057(13) 0.1436(4) -0.05868(15) 0.0183(5) Uani 1 1 d . . . C11 C 0.77750(15) 0.4334(4) -0.17040(16) 0.0231(6) Uani 1 1 d . . . H11A H 0.7761 0.4393 -0.2332 0.028 Uiso 1 1 calc R . . H11B H 0.8209 0.5278 -0.1292 0.028 Uiso 1 1 calc R . . C17 C 0.69413(13) 0.2180(4) 0.02863(15) 0.0198(5) Uani 1 1 d . . . H17 H 0.7108 0.0779 0.0515 0.024 Uiso 1 1 calc R . . C1 C 0.98345(15) 0.2644(4) -0.45180(16) 0.0288(6) Uani 1 1 d . . . H1A H 0.9498 0.3918 -0.4654 0.043 Uiso 1 1 calc R . . H1B H 0.9988 0.2390 -0.5027 0.043 Uiso 1 1 calc R . . H1C H 1.0313 0.2860 -0.3940 0.043 Uiso 1 1 calc R . . C10 C 0.79357(12) 0.2080(4) -0.13449(14) 0.0173(5) Uani 1 1 d . . . C21 C 0.59144(14) 0.6399(4) 0.10869(14) 0.0240(6) Uani 1 1 d . . . H21 H 0.5906 0.7900 0.1168 0.029 Uiso 1 1 calc R . . C19 C 0.64342(13) 0.5497(4) 0.07695(14) 0.0211(6) Uani 1 1 d . . . H19 H 0.6788 0.6375 0.0634 0.025 Uiso 1 1 calc R . . C12 C 0.69848(14) 0.5120(4) -0.17452(15) 0.0248(6) Uani 1 1 d . . . H12A H 0.6884 0.6594 -0.1993 0.030 Uiso 1 1 calc R . . H12B H 0.6549 0.4199 -0.2169 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br24 0.02949(15) 0.02857(15) 0.03506(17) 0.00828(12) 0.02268(12) 0.00727(13) O2 0.0330(10) 0.0267(10) 0.0224(9) -0.0041(7) 0.0165(8) -0.0048(8) C4 0.0196(12) 0.0163(12) 0.0206(13) -0.0032(10) 0.0054(10) 0.0016(11) C7 0.0215(12) 0.0173(13) 0.0231(13) -0.0043(10) 0.0103(10) -0.0003(10) C22 0.0208(12) 0.0260(14) 0.0114(12) 0.0039(10) 0.0068(10) 0.0045(11) O16 0.0382(10) 0.0163(9) 0.0340(10) 0.0093(8) 0.0244(8) 0.0083(8) N20 0.0222(11) 0.0220(12) 0.0161(10) 0.0037(9) 0.0090(8) 0.0052(9) C23 0.0204(13) 0.0277(15) 0.0166(12) -0.0014(11) 0.0078(10) 0.0052(11) C13 0.0195(13) 0.0154(13) 0.0237(13) 0.0020(10) 0.0087(10) 0.0038(10) C18 0.0178(12) 0.0217(13) 0.0126(12) 0.0025(9) 0.0044(10) 0.0035(10) C6 0.0167(12) 0.0166(12) 0.0220(13) 0.0001(10) 0.0074(10) -0.0015(10) C5 0.0184(12) 0.0206(13) 0.0194(13) -0.0004(10) 0.0062(10) -0.0035(10) C9 0.0207(13) 0.0128(13) 0.0256(13) 0.0040(9) 0.0102(10) -0.0010(9) C3 0.0154(11) 0.0243(14) 0.0140(12) 0.0012(10) 0.0044(9) 0.0019(11) C14 0.0156(12) 0.0148(12) 0.0181(12) -0.0011(10) 0.0052(10) -0.0008(10) C8 0.0174(12) 0.0145(13) 0.0219(13) 0.0028(10) 0.0083(10) 0.0021(10) C15 0.0176(12) 0.0136(13) 0.0244(13) 0.0003(10) 0.0096(10) -0.0024(9) C11 0.0295(14) 0.0181(14) 0.0256(13) 0.0048(10) 0.0156(11) 0.0019(11) C17 0.0212(13) 0.0155(13) 0.0225(13) 0.0012(10) 0.0091(10) 0.0029(10) C1 0.0318(15) 0.0333(17) 0.0281(14) -0.0038(12) 0.0194(12) -0.0080(13) C10 0.0150(12) 0.0154(13) 0.0209(12) 0.0014(10) 0.0072(10) -0.0005(10) C21 0.0286(14) 0.0229(15) 0.0171(13) -0.0047(10) 0.0065(11) 0.0042(11) C19 0.0204(13) 0.0225(14) 0.0193(13) 0.0000(10) 0.0074(10) -0.0008(10) C12 0.0274(14) 0.0232(14) 0.0226(14) 0.0062(11) 0.0096(11) 0.0084(12) _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 Br24 C22 1.918(2) . ? O2 C3 1.370(3) . ? O2 C1 1.428(3) . ? C4 C6 1.374(3) . ? C4 C3 1.389(3) . ? C7 C5 1.391(3) . ? C7 C8 1.395(3) . ? C22 N20 1.320(3) . ? C22 C23 1.381(3) . ? O16 C15 1.221(3) . ? N20 C18 1.363(3) . ? C23 C21 1.377(3) . ? C13 C14 1.508(3) . ? C13 C12 1.516(3) . ? C18 C19 1.389(3) . ? C18 C17 1.478(3) . ? C6 C8 1.408(3) . ? C5 C3 1.387(3) . ? C9 C10 1.344(3) . ? C9 C8 1.465(3) . ? C14 C17 1.340(3) . ? C14 C15 1.508(3) . ? C15 C10 1.498(3) . ? C11 C10 1.505(3) . ? C11 C12 1.523(3) . ? C21 C19 1.387(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 C3 O2 C1 117.47(18) . . ? C6 C4 C3 120.1(2) . . ? C5 C7 C8 122.1(2) . . ? N20 C22 C23 125.8(2) . . ? N20 C22 Br24 115.50(18) . . ? C23 C22 Br24 118.70(17) . . ? C22 N20 C18 116.6(2) . . ? C21 C23 C22 117.3(2) . . ? C14 C13 C12 113.23(19) . . ? N20 C18 C19 121.6(2) . . ? N20 C18 C17 114.4(2) . . ? C19 C18 C17 124.0(2) . . ? C4 C6 C8 121.4(2) . . ? C3 C5 C7 119.0(2) . . ? C10 C9 C8 128.9(2) . . ? O2 C3 C5 124.3(2) . . ? O2 C3 C4 115.5(2) . . ? C5 C3 C4 120.2(2) . . ? C17 C14 C13 125.3(2) . . ? C17 C14 C15 116.2(2) . . ? C13 C14 C15 118.52(18) . . ? C7 C8 C6 117.1(2) . . ? C7 C8 C9 123.7(2) . . ? C6 C8 C9 119.1(2) . . ? O16 C15 C10 120.7(2) . . ? O16 C15 C14 120.53(19) . . ? C10 C15 C14 118.76(19) . . ? C10 C11 C12 110.58(19) . . ? C14 C17 C18 127.2(2) . . ? C9 C10 C15 116.6(2) . . ? C9 C10 C11 124.6(2) . . ? C15 C10 C11 118.7(2) . . ? C23 C21 C19 119.1(2) . . ? C21 C19 C18 119.5(2) . . ? C13 C12 C11 110.70(19) . . ? 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 C23 C22 N20 C18 -1.4(3) . . . . ? Br24 C22 N20 C18 178.35(14) . . . . ? N20 C22 C23 C21 -1.1(3) . . . . ? Br24 C22 C23 C21 179.19(16) . . . . ? C22 N20 C18 C19 3.4(3) . . . . ? C22 N20 C18 C17 -177.16(18) . . . . ? C3 C4 C6 C8 1.3(3) . . . . ? C8 C7 C5 C3 0.1(3) . . . . ? C1 O2 C3 C5 2.6(3) . . . . ? C1 O2 C3 C4 -176.8(2) . . . . ? C7 C5 C3 O2 178.33(19) . . . . ? C7 C5 C3 C4 -2.3(3) . . . . ? C6 C4 C3 O2 -178.95(19) . . . . ? C6 C4 C3 C5 1.6(3) . . . . ? C12 C13 C14 C17 -151.1(2) . . . . ? C12 C13 C14 C15 28.1(3) . . . . ? C5 C7 C8 C6 2.7(3) . . . . ? C5 C7 C8 C9 179.8(2) . . . . ? C4 C6 C8 C7 -3.4(3) . . . . ? C4 C6 C8 C9 179.4(2) . . . . ? C10 C9 C8 C7 34.6(4) . . . . ? C10 C9 C8 C6 -148.4(2) . . . . ? C17 C14 C15 O16 -6.9(3) . . . . ? C13 C14 C15 O16 173.8(2) . . . . ? C17 C14 C15 C10 173.75(19) . . . . ? C13 C14 C15 C10 -5.5(3) . . . . ? C13 C14 C17 C18 -0.6(4) . . . . ? C15 C14 C17 C18 -179.9(2) . . . . ? N20 C18 C17 C14 149.1(2) . . . . ? C19 C18 C17 C14 -31.4(3) . . . . ? C8 C9 C10 C15 -176.1(2) . . . . ? C8 C9 C10 C11 6.6(4) . . . . ? O16 C15 C10 C9 14.1(3) . . . . ? C14 C15 C10 C9 -166.6(2) . . . . ? O16 C15 C10 C11 -168.4(2) . . . . ? C14 C15 C10 C11 10.9(3) . . . . ? C12 C11 C10 C9 139.4(2) . . . . ? C12 C11 C10 C15 -37.9(3) . . . . ? C22 C23 C21 C19 1.6(3) . . . . ? C23 C21 C19 C18 0.3(3) . . . . ? N20 C18 C19 C21 -2.9(3) . . . . ? C17 C18 C19 C21 177.7(2) . . . . ? C14 C13 C12 C11 -55.8(3) . . . . ? C10 C11 C12 C13 60.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.428 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.077 data_8a _database_code_depnum_ccdc_archive 'CCDC 605784' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E)-N,N-dimethyl-9-(naphthalen-1-yl)-5-(naphthalen-2-ylmethylene) -2,3,4,4a,5,6,7,8,9,9a-decahydro-1H-xanthen-4a-amine hydrochloride salt ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C36 H37 N O) (H Cl)' _chemical_formula_sum 'C36 H38 Cl N O' _chemical_formula_weight 536.12 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.5683(4) _cell_length_b 12.3023(4) _cell_length_c 13.6088(5) _cell_angle_alpha 98.8250(10) _cell_angle_beta 110.125(2) _cell_angle_gamma 111.483(2) _cell_volume 1603.30(10) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9440 _exptl_absorpt_correction_T_max 0.9576 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 27554 _diffrn_reflns_av_R_equivalents 0.0872 _diffrn_reflns_av_sigmaI/netI 0.1195 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 28.20 _reflns_number_total 7612 _reflns_number_gt 3336 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material ciftab _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1033P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7612 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1809 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.2063 _refine_ls_wR_factor_gt 0.1623 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 Cl1 Cl -0.93164(7) 0.15751(7) 0.44028(6) 0.0552(3) Uani 1 1 d . . . O10 O -0.52418(17) 0.27958(16) 0.82871(13) 0.0432(5) Uani 1 1 d . . . N1 N -0.7203(2) 0.19333(19) 0.66656(16) 0.0369(5) Uani 1 1 d . . . C9A C -0.4981(2) 0.3447(2) 0.67395(19) 0.0354(6) Uani 1 1 d . . . H9A H -0.4916 0.2689 0.6436 0.042 Uiso 1 1 calc R . . C4A C -0.5868(2) 0.3128(2) 0.73568(19) 0.0351(6) Uani 1 1 d . . . C9' C -0.2162(3) 0.3440(3) 0.6926(2) 0.0399(7) Uani 1 1 d . . . C8A C -0.3045(2) 0.4423(2) 0.87105(19) 0.0366(6) Uani 1 1 d . . . C5 C -0.3475(3) 0.3501(3) 1.0127(2) 0.0421(7) Uani 1 1 d . . . C4 C -0.6184(3) 0.4177(3) 0.7699(2) 0.0431(7) Uani 1 1 d . . . H4A H -0.5313 0.4902 0.8238 0.052 Uiso 1 1 calc R . . H4B H -0.6793 0.3930 0.8071 0.052 Uiso 1 1 calc R . . C2 C -0.6006(3) 0.4869(3) 0.6100(2) 0.0501(8) Uani 1 1 d . . . H2A H -0.5144 0.5633 0.6576 0.060 Uiso 1 1 calc R . . H2B H -0.6510 0.5031 0.5433 0.060 Uiso 1 1 calc R . . C10A C -0.3876(3) 0.3640(3) 0.9028(2) 0.0398(7) Uani 1 1 d . . . C1' C -0.2471(3) 0.4454(2) 0.7078(2) 0.0384(7) Uani 1 1 d . . . C2' C -0.1849(3) 0.5425(3) 0.6761(2) 0.0457(7) Uani 1 1 d . . . H2' H -0.2038 0.6112 0.6874 0.055 Uiso 1 1 calc R . . C8 C -0.1616(3) 0.5370(3) 0.9533(2) 0.0492(8) Uani 1 1 d . . . H8A H -0.1413 0.6158 0.9371 0.059 Uiso 1 1 calc R . . H8B H -0.0938 0.5094 0.9458 0.059 Uiso 1 1 calc R . . C9 C -0.3499(2) 0.4460(2) 0.75364(19) 0.0355(6) Uani 1 1 d . . . H9 H -0.3525 0.5268 0.7565 0.043 Uiso 1 1 calc R . . C1 C -0.5650(3) 0.3845(3) 0.5760(2) 0.0434(7) Uani 1 1 d . . . H1A H -0.5007 0.4128 0.5422 0.052 Uiso 1 1 calc R . . H1B H -0.6501 0.3123 0.5194 0.052 Uiso 1 1 calc R . . C1" C -0.4164(3) 0.2387(3) 1.1399(2) 0.0500(8) Uani 1 1 d . . . C6 C -0.1987(3) 0.4355(3) 1.0926(2) 0.0554(8) Uani 1 1 d . . . H6A H -0.1407 0.3946 1.0867 0.067 Uiso 1 1 calc R . . H6B H -0.1902 0.4514 1.1690 0.067 Uiso 1 1 calc R . . C11" C -0.4390(3) 0.2671(3) 1.0358(2) 0.0485(8) Uani 1 1 d . . . H11" H -0.5296 0.2210 0.9777 0.058 Uiso 1 1 calc R . . C7 C -0.1458(3) 0.5577(3) 1.0705(2) 0.0542(8) Uani 1 1 d . . . H7A H -0.1981 0.6023 1.0830 0.065 Uiso 1 1 calc R . . H7B H -0.0473 0.6093 1.1227 0.065 Uiso 1 1 calc R . . C3 C -0.6884(3) 0.4540(3) 0.6717(2) 0.0472(7) Uani 1 1 d . . . H3A H -0.7798 0.3844 0.6211 0.057 Uiso 1 1 calc R . . H3B H -0.7025 0.5254 0.6984 0.057 Uiso 1 1 calc R . . C8' C -0.2666(3) 0.2402(3) 0.7274(2) 0.0486(8) Uani 1 1 d . . . H8' H -0.3236 0.2376 0.7642 0.058 Uiso 1 1 calc R . . C9" C -0.5194(3) 0.2162(3) 1.1799(2) 0.0514(8) Uani 1 1 d . . . C10' C -0.1272(3) 0.3450(3) 0.6404(2) 0.0455(7) Uani 1 1 d . . . C2" C -0.2993(3) 0.2302(3) 1.2004(3) 0.0639(9) Uani 1 1 d . . . H2" H -0.2316 0.2416 1.1734 0.077 Uiso 1 1 calc R . . C2N C -0.8128(3) 0.1589(3) 0.7223(2) 0.0557(8) Uani 1 1 d . . . H2N1 H -0.8943 0.0803 0.6753 0.083 Uiso 1 1 calc R . . H2N2 H -0.8419 0.2231 0.7352 0.083 Uiso 1 1 calc R . . H2N3 H -0.7632 0.1507 0.7932 0.083 Uiso 1 1 calc R . . C4' C -0.0685(3) 0.4478(4) 0.6093(2) 0.0621(10) Uani 1 1 d . . . H4' H -0.0095 0.4486 0.5747 0.075 Uiso 1 1 calc R . . C1N C -0.6978(3) 0.0851(3) 0.6296(3) 0.0595(9) Uani 1 1 d . . . H1N1 H -0.6316 0.0780 0.6932 0.089 Uiso 1 1 calc R . . H1N2 H -0.6615 0.0965 0.5746 0.089 Uiso 1 1 calc R . . H1N3 H -0.7857 0.0099 0.5967 0.089 Uiso 1 1 calc R . . C5' C -0.1022(3) 0.2407(4) 0.6207(2) 0.0617(9) Uani 1 1 d . . . H5' H -0.0473 0.2388 0.5828 0.074 Uiso 1 1 calc R . . C3' C -0.0950(3) 0.5461(3) 0.6280(2) 0.0577(9) Uani 1 1 d . . . H3' H -0.0529 0.6163 0.6086 0.069 Uiso 1 1 calc R . . C8" C -0.6466(3) 0.2189(3) 1.1238(3) 0.0600(9) Uani 1 1 d . . . H8" H -0.6664 0.2352 1.0555 0.072 Uiso 1 1 calc R . . C7' C -0.2357(3) 0.1449(3) 0.7095(3) 0.0629(9) Uani 1 1 d . . . H7' H -0.2699 0.0777 0.7350 0.076 Uiso 1 1 calc R . . C10" C -0.4941(4) 0.1923(3) 1.2832(2) 0.0583(9) Uani 1 1 d . . . C3" C -0.2760(4) 0.2053(3) 1.3013(3) 0.0757(11) Uani 1 1 d . . . H3" H -0.1933 0.2008 1.3410 0.091 Uiso 1 1 calc R . . C6' C -0.1547(4) 0.1445(4) 0.6545(3) 0.0700(10) Uani 1 1 d . . . H6' H -0.1361 0.0760 0.6406 0.084 Uiso 1 1 calc R . . C5" C -0.5946(5) 0.1741(3) 1.3240(3) 0.0752(11) Uani 1 1 d . . . H5" H -0.5764 0.1606 1.3935 0.090 Uiso 1 1 calc R . . C4" C -0.3701(4) 0.1877(3) 1.3415(3) 0.0709(11) Uani 1 1 d . . . H4" H -0.3528 0.1720 1.4100 0.085 Uiso 1 1 calc R . . C6" C -0.7161(5) 0.1753(3) 1.2674(3) 0.0762(11) Uani 1 1 d . . . H6" H -0.7828 0.1607 1.2958 0.091 Uiso 1 1 calc R . . C7" C -0.7413(4) 0.1985(3) 1.1663(3) 0.0738(10) Uani 1 1 d . . . H7" H -0.8258 0.2000 1.1264 0.089 Uiso 1 1 calc R . . H1N H -0.7644 0.2127 0.5921 0.091(11) 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 Cl1 0.0436(4) 0.0551(5) 0.0446(4) 0.0140(3) 0.0065(3) 0.0124(4) O10 0.0338(10) 0.0490(11) 0.0341(10) 0.0174(9) 0.0073(9) 0.0112(9) N1 0.0338(12) 0.0358(12) 0.0348(11) 0.0100(10) 0.0127(10) 0.0118(10) C9A 0.0329(14) 0.0392(15) 0.0319(13) 0.0087(12) 0.0143(12) 0.0149(12) C4A 0.0284(13) 0.0388(15) 0.0276(12) 0.0095(11) 0.0056(11) 0.0113(12) C9' 0.0335(14) 0.0455(17) 0.0303(14) 0.0067(12) 0.0068(12) 0.0161(13) C8A 0.0289(14) 0.0419(16) 0.0318(14) 0.0075(12) 0.0095(12) 0.0138(12) C5 0.0384(15) 0.0528(17) 0.0312(14) 0.0140(13) 0.0107(13) 0.0204(14) C4 0.0343(15) 0.0473(17) 0.0394(15) 0.0065(13) 0.0148(13) 0.0143(13) C2 0.0378(16) 0.0514(18) 0.0502(17) 0.0242(15) 0.0084(14) 0.0159(14) C10A 0.0304(14) 0.0473(16) 0.0291(13) 0.0063(12) 0.0053(12) 0.0141(13) C1' 0.0327(14) 0.0435(16) 0.0315(14) 0.0136(12) 0.0094(12) 0.0134(13) C2' 0.0378(15) 0.0505(18) 0.0448(16) 0.0187(14) 0.0138(14) 0.0185(14) C8 0.0322(15) 0.0622(19) 0.0360(15) 0.0100(14) 0.0088(13) 0.0119(14) C9 0.0307(14) 0.0389(15) 0.0319(13) 0.0086(12) 0.0110(12) 0.0142(12) C1 0.0333(15) 0.0553(18) 0.0313(14) 0.0132(13) 0.0109(12) 0.0128(14) C1" 0.0520(18) 0.0495(18) 0.0380(15) 0.0148(14) 0.0145(14) 0.0167(15) C6 0.0445(17) 0.077(2) 0.0323(15) 0.0147(15) 0.0098(14) 0.0219(16) C11" 0.0440(17) 0.0570(19) 0.0347(15) 0.0145(14) 0.0092(14) 0.0204(15) C7 0.0381(16) 0.061(2) 0.0362(15) 0.0036(14) 0.0078(13) 0.0077(15) C3 0.0394(15) 0.0413(16) 0.0521(17) 0.0090(14) 0.0124(14) 0.0186(13) C8' 0.0435(16) 0.0486(18) 0.0571(18) 0.0185(15) 0.0233(15) 0.0222(15) C9" 0.063(2) 0.0418(17) 0.0389(16) 0.0122(13) 0.0185(16) 0.0172(15) C10' 0.0329(15) 0.065(2) 0.0349(15) 0.0140(14) 0.0114(13) 0.0219(15) C2" 0.062(2) 0.074(2) 0.0516(19) 0.0300(17) 0.0157(17) 0.0303(18) C2N 0.0411(17) 0.0554(19) 0.0486(17) 0.0147(15) 0.0159(15) 0.0038(14) C4' 0.0417(18) 0.102(3) 0.0460(18) 0.0287(19) 0.0207(15) 0.0323(19) C1N 0.0572(19) 0.0405(17) 0.068(2) 0.0070(15) 0.0182(17) 0.0215(15) C5' 0.0506(19) 0.091(3) 0.0466(18) 0.0110(19) 0.0178(16) 0.042(2) C3' 0.0443(17) 0.077(2) 0.0586(19) 0.0384(18) 0.0256(16) 0.0249(17) C8" 0.062(2) 0.061(2) 0.0570(19) 0.0222(17) 0.0276(18) 0.0249(17) C7' 0.058(2) 0.051(2) 0.079(2) 0.0159(17) 0.0276(19) 0.0281(17) C10" 0.076(2) 0.0400(18) 0.0462(17) 0.0125(14) 0.0258(18) 0.0140(16) C3" 0.075(3) 0.072(3) 0.063(2) 0.032(2) 0.009(2) 0.032(2) C6' 0.068(2) 0.067(2) 0.068(2) 0.0041(19) 0.020(2) 0.040(2) C5" 0.115(3) 0.043(2) 0.061(2) 0.0195(17) 0.048(2) 0.021(2) C4" 0.086(3) 0.060(2) 0.0440(18) 0.0218(16) 0.013(2) 0.022(2) C6" 0.096(3) 0.054(2) 0.086(3) 0.021(2) 0.059(3) 0.025(2) C7" 0.075(2) 0.067(2) 0.085(3) 0.027(2) 0.043(2) 0.029(2) _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 O10 C10A 1.404(3) . ? O10 C4A 1.428(3) . ? N1 C2N 1.493(3) . ? N1 C1N 1.493(3) . ? N1 C4A 1.531(3) . ? C9A C4A 1.521(4) . ? C9A C1 1.544(3) . ? C9A C9 1.552(3) . ? C4A C4 1.514(4) . ? C9' C1' 1.423(4) . ? C9' C8' 1.423(4) . ? C9' C10' 1.436(4) . ? C8A C10A 1.332(4) . ? C8A C8 1.503(4) . ? C8A C9 1.515(3) . ? C5 C11" 1.340(4) . ? C5 C10A 1.463(4) . ? C5 C6 1.512(4) . ? C4 C3 1.531(4) . ? C2 C3 1.513(4) . ? C2 C1 1.518(4) . ? C1' C2' 1.369(4) . ? C1' C9 1.523(4) . ? C2' C3' 1.399(4) . ? C8 C7 1.511(4) . ? C1" C2" 1.373(4) . ? C1" C9" 1.430(4) . ? C1" C11" 1.471(4) . ? C6 C7 1.522(4) . ? C8' C7' 1.357(4) . ? C9" C8" 1.422(4) . ? C9" C10" 1.433(4) . ? C10' C4' 1.404(4) . ? C10' C5' 1.423(4) . ? C2" C3" 1.409(4) . ? C4' C3' 1.361(5) . ? C5' C6' 1.347(5) . ? C8" C7" 1.369(5) . ? C7' C6' 1.387(5) . ? C10" C4" 1.407(5) . ? C10" C5" 1.415(5) . ? C3" C4" 1.344(5) . ? C5" C6" 1.358(5) . ? C6" C7" 1.401(5) . ? 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 C10A O10 C4A 116.0(2) . . ? C2N N1 C1N 108.5(2) . . ? C2N N1 C4A 113.53(19) . . ? C1N N1 C4A 114.0(2) . . ? C4A C9A C1 110.8(2) . . ? C4A C9A C9 110.6(2) . . ? C1 C9A C9 111.2(2) . . ? O10 C4A C4 111.1(2) . . ? O10 C4A C9A 111.5(2) . . ? C4 C4A C9A 111.0(2) . . ? O10 C4A N1 100.97(19) . . ? C4 C4A N1 110.7(2) . . ? C9A C4A N1 111.23(19) . . ? C1' C9' C8' 124.2(3) . . ? C1' C9' C10' 119.1(3) . . ? C8' C9' C10' 116.7(3) . . ? C10A C8A C8 120.7(2) . . ? C10A C8A C9 122.6(2) . . ? C8 C8A C9 116.6(2) . . ? C11" C5 C10A 120.6(2) . . ? C11" C5 C6 125.3(2) . . ? C10A C5 C6 114.1(2) . . ? C4A C4 C3 112.4(2) . . ? C3 C2 C1 111.7(2) . . ? C8A C10A O10 121.7(2) . . ? C8A C10A C5 125.3(2) . . ? O10 C10A C5 112.9(2) . . ? C2' C1' C9' 117.9(3) . . ? C2' C1' C9 120.0(3) . . ? C9' C1' C9 122.0(2) . . ? C1' C2' C3' 123.5(3) . . ? C8A C8 C7 111.8(2) . . ? C8A C9 C1' 112.8(2) . . ? C8A C9 C9A 113.3(2) . . ? C1' C9 C9A 111.3(2) . . ? C2 C1 C9A 112.8(2) . . ? C2" C1" C9" 117.8(3) . . ? C2" C1" C11" 122.1(3) . . ? C9" C1" C11" 120.0(3) . . ? C5 C6 C7 112.2(2) . . ? C5 C11" C1" 128.0(3) . . ? C8 C7 C6 110.8(2) . . ? C2 C3 C4 110.4(2) . . ? C7' C8' C9' 121.9(3) . . ? C8" C9" C1" 123.5(3) . . ? C8" C9" C10" 117.1(3) . . ? C1" C9" C10" 119.4(3) . . ? C4' C10' C5' 121.8(3) . . ? C4' C10' C9' 119.5(3) . . ? C5' C10' C9' 118.7(3) . . ? C1" C2" C3" 122.3(3) . . ? C3' C4' C10' 120.8(3) . . ? C6' C5' C10' 121.4(3) . . ? C4' C3' C2' 119.2(3) . . ? C7" C8" C9" 121.4(3) . . ? C8' C7' C6' 120.7(4) . . ? C4" C10" C5" 121.7(3) . . ? C4" C10" C9" 119.3(3) . . ? C5" C10" C9" 119.0(3) . . ? C4" C3" C2" 120.4(3) . . ? C5' C6' C7' 120.3(3) . . ? C6" C5" C10" 122.3(4) . . ? C3" C4" C10" 120.7(3) . . ? C5" C6" C7" 118.8(4) . . ? C8" C7" C6" 121.4(4) . . ? 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 C10A O10 C4A C4 -71.7(3) . . . . ? C10A O10 C4A C9A 52.7(3) . . . . ? C10A O10 C4A N1 170.93(19) . . . . ? C1 C9A C4A O10 -178.1(2) . . . . ? C9 C9A C4A O10 -54.3(3) . . . . ? C1 C9A C4A C4 -53.7(3) . . . . ? C9 C9A C4A C4 70.1(3) . . . . ? C1 C9A C4A N1 70.0(3) . . . . ? C9 C9A C4A N1 -166.2(2) . . . . ? C2N N1 C4A O10 62.7(3) . . . . ? C1N N1 C4A O10 -62.2(3) . . . . ? C2N N1 C4A C4 -54.9(3) . . . . ? C1N N1 C4A C4 -179.9(2) . . . . ? C2N N1 C4A C9A -178.8(2) . . . . ? C1N N1 C4A C9A 56.2(3) . . . . ? O10 C4A C4 C3 -178.8(2) . . . . ? C9A C4A C4 C3 56.5(3) . . . . ? N1 C4A C4 C3 -67.5(3) . . . . ? C8 C8A C10A O10 176.3(2) . . . . ? C9 C8A C10A O10 -0.3(4) . . . . ? C8 C8A C10A C5 -7.7(4) . . . . ? C9 C8A C10A C5 175.7(2) . . . . ? C4A O10 C10A C8A -25.0(4) . . . . ? C4A O10 C10A C5 158.5(2) . . . . ? C11" C5 C10A C8A -179.1(3) . . . . ? C6 C5 C10A C8A 0.7(4) . . . . ? C11" C5 C10A O10 -2.8(4) . . . . ? C6 C5 C10A O10 177.0(2) . . . . ? C8' C9' C1' C2' 176.2(2) . . . . ? C10' C9' C1' C2' -2.9(3) . . . . ? C8' C9' C1' C9 -6.1(4) . . . . ? C10' C9' C1' C9 174.8(2) . . . . ? C9' C1' C2' C3' 1.2(4) . . . . ? C9 C1' C2' C3' -176.5(2) . . . . ? C10A C8A C8 C7 -18.4(4) . . . . ? C9 C8A C8 C7 158.4(2) . . . . ? C10A C8A C9 C1' -131.3(3) . . . . ? C8 C8A C9 C1' 52.0(3) . . . . ? C10A C8A C9 C9A -3.8(4) . . . . ? C8 C8A C9 C9A 179.5(2) . . . . ? C2' C1' C9 C8A -118.7(3) . . . . ? C9' C1' C9 C8A 63.6(3) . . . . ? C2' C1' C9 C9A 112.6(3) . . . . ? C9' C1' C9 C9A -65.0(3) . . . . ? C4A C9A C9 C8A 30.1(3) . . . . ? C1 C9A C9 C8A 153.7(2) . . . . ? C4A C9A C9 C1' 158.4(2) . . . . ? C1 C9A C9 C1' -78.0(3) . . . . ? C3 C2 C1 C9A -53.6(3) . . . . ? C4A C9A C1 C2 52.9(3) . . . . ? C9 C9A C1 C2 -70.5(3) . . . . ? C11" C5 C6 C7 -148.6(3) . . . . ? C10A C5 C6 C7 31.6(4) . . . . ? C10A C5 C11" C1" 178.5(3) . . . . ? C6 C5 C11" C1" -1.3(5) . . . . ? C2" C1" C11" C5 -41.7(5) . . . . ? C9" C1" C11" C5 139.7(3) . . . . ? C8A C8 C7 C6 49.6(3) . . . . ? C5 C6 C7 C8 -57.0(3) . . . . ? C1 C2 C3 C4 54.1(3) . . . . ? C4A C4 C3 C2 -56.3(3) . . . . ? C1' C9' C8' C7' 179.0(3) . . . . ? C10' C9' C8' C7' -1.8(4) . . . . ? C2" C1" C9" C8" -178.3(3) . . . . ? C11" C1" C9" C8" 0.4(4) . . . . ? C2" C1" C9" C10" 3.2(4) . . . . ? C11" C1" C9" C10" -178.1(3) . . . . ? C1' C9' C10' C4' 2.4(4) . . . . ? C8' C9' C10' C4' -176.8(2) . . . . ? C1' C9' C10' C5' -177.0(2) . . . . ? C8' C9' C10' C5' 3.8(3) . . . . ? C9" C1" C2" C3" -2.5(5) . . . . ? C11" C1" C2" C3" 178.8(3) . . . . ? C5' C10' C4' C3' 179.3(3) . . . . ? C9' C10' C4' C3' 0.0(4) . . . . ? C4' C10' C5' C6' 177.5(3) . . . . ? C9' C10' C5' C6' -3.2(4) . . . . ? C10' C4' C3' C2' -1.8(4) . . . . ? C1' C2' C3' C4' 1.2(4) . . . . ? C1" C9" C8" C7" -179.0(3) . . . . ? C10" C9" C8" C7" -0.5(5) . . . . ? C9' C8' C7' C6' -1.1(5) . . . . ? C8" C9" C10" C4" 179.5(3) . . . . ? C1" C9" C10" C4" -1.9(4) . . . . ? C8" C9" C10" C5" -0.6(4) . . . . ? C1" C9" C10" C5" 177.9(3) . . . . ? C1" C2" C3" C4" 0.6(5) . . . . ? C10' C5' C6' C7' 0.3(5) . . . . ? C8' C7' C6' C5' 1.9(5) . . . . ? C4" C10" C5" C6" -178.4(3) . . . . ? C9" C10" C5" C6" 1.8(5) . . . . ? C2" C3" C4" C10" 0.8(5) . . . . ? C5" C10" C4" C3" -180.0(3) . . . . ? C9" C10" C4" C3" -0.1(5) . . . . ? C10" C5" C6" C7" -1.6(5) . . . . ? C9" C8" C7" C6" 0.7(5) . . . . ? C5" C6" C7" C8" 0.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 28.20 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.656 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.063 # Attachment '8b.CIF' data_8b _database_code_depnum_ccdc_archive 'CCDC 605785' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E)-N,N-dimethyl-9-(pyridin-4-yl)-5-(pyridin-4-ylmethylene) -2,3,4,4a,5,6,7,8,9,9a-decahydro-1H-xanthen-4a-amine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H31 N3 O' _chemical_formula_sum 'C26 H31 N3 O' _chemical_formula_weight 401.54 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' N N 0.0061 0.0033 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.08960(10) _cell_length_b 13.2900(2) _cell_length_c 16.6649(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.9810(10) _cell_angle_gamma 90.00 _cell_volume 2168.41(6) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _exptl_crystal_description colourless _exptl_crystal_colour block _exptl_crystal_size_max .45 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.076 _exptl_special_details ; ? ; _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 'phi and omega scans' _diffrn_reflns_number 30375 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 28.19 _reflns_number_total 5297 _reflns_number_gt 3772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material ciftab _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.7951P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5297 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 O10 O 0.79851(10) 0.94087(7) 0.07655(6) 0.0200(2) Uani 1 1 d . . . N1 N 0.92494(11) 0.86695(9) 0.19829(7) 0.0201(3) Uani 1 1 d . . . C9A C 0.88833(13) 0.77121(10) 0.06742(8) 0.0161(3) Uani 1 1 d . . . H9A H 0.9759 0.8002 0.0598 0.019 Uiso 1 1 calc R . . C1 C 0.92004(14) 0.66968(10) 0.11179(8) 0.0205(3) Uani 1 1 d . . . H1A H 0.9557 0.6226 0.0760 0.025 Uiso 1 1 calc R . . H1B H 0.9920 0.6793 0.1634 0.025 Uiso 1 1 calc R . . C4A C 0.82840(13) 0.84453(10) 0.12047(8) 0.0170(3) Uani 1 1 d . . . C8A C 0.72015(13) 0.85448(10) -0.05231(8) 0.0179(3) Uani 1 1 d . . . C5 C 0.68567(13) 1.03762(11) -0.04013(8) 0.0187(3) Uani 1 1 d . . . C5A C 0.73294(13) 0.93821(10) -0.00598(8) 0.0175(3) Uani 1 1 d . . . C4 C 0.69751(14) 0.79950(11) 0.13612(9) 0.0207(3) Uani 1 1 d . . . H4A H 0.6296 0.7905 0.0827 0.025 Uiso 1 1 calc R . . H4B H 0.6585 0.8464 0.1704 0.025 Uiso 1 1 calc R . . C9 C 0.79018(14) 0.75778(10) -0.01914(8) 0.0173(3) Uani 1 1 d . . . H9 H 0.7184 0.7079 -0.0141 0.021 Uiso 1 1 calc R . . C7 C 0.53530(14) 0.94154(11) -0.15574(8) 0.0217(3) Uani 1 1 d . . . H7A H 0.4656 0.9346 -0.1233 0.026 Uiso 1 1 calc R . . H7B H 0.4879 0.9441 -0.2151 0.026 Uiso 1 1 calc R . . C12 C 0.70641(14) 1.12004(10) 0.00789(9) 0.0203(3) Uani 1 1 d . . . H12 H 0.7460 1.1094 0.0650 0.024 Uiso 1 1 calc R . . C6 C 0.61662(14) 1.03784(11) -0.13112(8) 0.0204(3) Uani 1 1 d . . . H6A H 0.6864 1.0442 -0.1636 0.024 Uiso 1 1 calc R . . H6B H 0.5547 1.0965 -0.1440 0.024 Uiso 1 1 calc R . . N1" N 0.61472(14) 1.42951(10) -0.06116(8) 0.0308(3) Uani 1 1 d . . . C4' C 0.86952(14) 0.71511(10) -0.07798(8) 0.0188(3) Uani 1 1 d . . . C3' C 0.85499(15) 0.61551(11) -0.10394(8) 0.0236(3) Uani 1 1 d . . . H3' H 0.7930 0.5722 -0.0860 0.028 Uiso 1 1 calc R . . C8 C 0.63159(14) 0.85235(11) -0.13953(8) 0.0218(3) Uani 1 1 d . . . H8A H 0.5779 0.7892 -0.1482 0.026 Uiso 1 1 calc R . . H8B H 0.6904 0.8534 -0.1792 0.026 Uiso 1 1 calc R . . N1' N 1.02138(14) 0.63541(11) -0.18509(8) 0.0320(3) Uani 1 1 d . . . C3 C 0.72573(15) 0.69768(11) 0.18029(9) 0.0240(3) Uani 1 1 d . . . H3A H 0.7856 0.7081 0.2362 0.029 Uiso 1 1 calc R . . H3B H 0.6385 0.6687 0.1868 0.029 Uiso 1 1 calc R . . C2' C 0.93228(17) 0.58016(12) -0.15652(9) 0.0298(4) Uani 1 1 d . . . H2' H 0.9210 0.5118 -0.1734 0.036 Uiso 1 1 calc R . . C2 C 0.79383(15) 0.62360(11) 0.13281(9) 0.0232(3) Uani 1 1 d . . . H2A H 0.7277 0.6036 0.0811 0.028 Uiso 1 1 calc R . . H2B H 0.8207 0.5623 0.1666 0.028 Uiso 1 1 calc R . . C3" C 0.68563(15) 1.26471(11) -0.09372(10) 0.0268(3) Uani 1 1 d . . . H3" H 0.7137 1.2229 -0.1328 0.032 Uiso 1 1 calc R . . C6' C 1.03388(16) 0.73129(13) -0.15967(9) 0.0303(4) Uani 1 1 d . . . H6' H 1.0964 0.7729 -0.1788 0.036 Uiso 1 1 calc R . . C4" C 0.67467(14) 1.22510(11) -0.01810(9) 0.0207(3) Uani 1 1 d . . . C5' C 0.96181(15) 0.77388(12) -0.10742(9) 0.0253(3) Uani 1 1 d . . . H5' H 0.9752 0.8426 -0.0918 0.030 Uiso 1 1 calc R . . C5" C 0.63421(15) 1.29258(11) 0.03540(9) 0.0249(3) Uani 1 1 d . . . H5" H 0.6267 1.2706 0.0884 0.030 Uiso 1 1 calc R . . C1N C 1.05603(15) 0.90623(13) 0.18997(10) 0.0302(4) Uani 1 1 d . . . H1N1 H 1.0981 0.8580 0.1591 0.045 Uiso 1 1 calc R . . H1N2 H 1.1163 0.9166 0.2450 0.045 Uiso 1 1 calc R . . H1N3 H 1.0417 0.9704 0.1602 0.045 Uiso 1 1 calc R . . C6" C 0.60484(16) 1.39165(12) 0.01162(10) 0.0285(3) Uani 1 1 d . . . H6" H 0.5760 1.4353 0.0492 0.034 Uiso 1 1 calc R . . C2N C 0.87104(16) 0.93231(12) 0.25392(9) 0.0295(4) Uani 1 1 d . . . H2N1 H 0.8409 0.9962 0.2261 0.044 Uiso 1 1 calc R . . H2N2 H 0.9427 0.9452 0.3041 0.044 Uiso 1 1 calc R . . H2N3 H 0.7935 0.8992 0.2687 0.044 Uiso 1 1 calc R . . C2" C 0.65564(17) 1.36500(12) -0.11169(11) 0.0316(4) Uani 1 1 d . . . H2" H 0.6648 1.3897 -0.1636 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O10 0.0267(5) 0.0154(5) 0.0155(5) 0.0002(4) 0.0007(4) 0.0039(4) N1 0.0211(6) 0.0216(6) 0.0162(6) -0.0026(5) 0.0016(4) 0.0007(5) C9A 0.0161(6) 0.0159(6) 0.0166(6) -0.0005(5) 0.0044(5) 0.0014(5) C1 0.0238(7) 0.0189(7) 0.0183(7) 0.0006(6) 0.0039(6) 0.0044(6) C4A 0.0190(7) 0.0156(7) 0.0156(6) 0.0007(5) 0.0027(5) 0.0028(5) C8A 0.0182(6) 0.0194(7) 0.0163(7) 0.0009(5) 0.0049(5) 0.0015(6) C5 0.0158(6) 0.0206(7) 0.0201(7) 0.0025(6) 0.0050(5) 0.0024(5) C5A 0.0170(6) 0.0195(7) 0.0155(6) 0.0005(5) 0.0032(5) 0.0019(5) C4 0.0189(7) 0.0245(7) 0.0189(7) -0.0025(6) 0.0051(5) 0.0029(6) C9 0.0210(7) 0.0155(7) 0.0161(6) -0.0018(5) 0.0059(5) -0.0003(5) C7 0.0191(7) 0.0274(8) 0.0174(7) 0.0025(6) 0.0018(5) 0.0009(6) C12 0.0199(7) 0.0185(7) 0.0216(7) 0.0027(6) 0.0035(5) 0.0024(6) C6 0.0204(7) 0.0214(7) 0.0195(7) 0.0048(6) 0.0050(5) 0.0049(6) N1" 0.0380(8) 0.0200(7) 0.0347(8) 0.0025(6) 0.0096(6) 0.0038(6) C4' 0.0206(7) 0.0205(7) 0.0143(6) -0.0006(5) 0.0023(5) 0.0034(6) C3' 0.0314(8) 0.0197(7) 0.0191(7) 0.0000(6) 0.0047(6) 0.0039(6) C8 0.0247(7) 0.0222(7) 0.0172(7) -0.0010(6) 0.0023(6) -0.0003(6) N1' 0.0309(7) 0.0441(9) 0.0206(7) -0.0052(6) 0.0056(5) 0.0107(6) C3 0.0235(7) 0.0284(8) 0.0213(7) 0.0019(6) 0.0079(6) -0.0040(6) C2' 0.0396(9) 0.0259(8) 0.0222(8) -0.0044(6) 0.0039(7) 0.0112(7) C2 0.0305(8) 0.0179(7) 0.0197(7) 0.0034(6) 0.0034(6) -0.0017(6) C3" 0.0298(8) 0.0212(8) 0.0330(8) 0.0022(6) 0.0144(7) 0.0035(6) C6' 0.0258(8) 0.0434(10) 0.0234(8) -0.0043(7) 0.0090(6) -0.0013(7) C4" 0.0173(7) 0.0180(7) 0.0259(7) 0.0004(6) 0.0037(5) 0.0006(5) C5' 0.0277(8) 0.0263(8) 0.0232(7) -0.0041(6) 0.0088(6) -0.0022(6) C5" 0.0291(8) 0.0210(8) 0.0234(7) 0.0010(6) 0.0039(6) 0.0007(6) C1N 0.0223(8) 0.0383(9) 0.0281(8) -0.0086(7) 0.0022(6) -0.0040(7) C6" 0.0338(8) 0.0206(8) 0.0301(8) -0.0035(6) 0.0055(7) 0.0039(6) C2N 0.0334(8) 0.0340(9) 0.0209(7) -0.0091(7) 0.0060(6) -0.0008(7) C2" 0.0391(9) 0.0248(8) 0.0339(9) 0.0064(7) 0.0147(7) 0.0024(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 O10 C5A 1.3750(15) . ? O10 C4A 1.4696(16) . ? N1 C4A 1.4522(17) . ? N1 C1N 1.4593(19) . ? N1 C2N 1.4675(18) . ? C9A C4A 1.5346(18) . ? C9A C1 1.5348(18) . ? C9A C9 1.5501(18) . ? C1 C2 1.528(2) . ? C4A C4 1.5287(19) . ? C8A C5A 1.3427(19) . ? C8A C9 1.5060(18) . ? C8A C8 1.5114(19) . ? C5 C12 1.343(2) . ? C5 C5A 1.4715(19) . ? C5 C6 1.5081(19) . ? C4 C3 1.534(2) . ? C9 C4' 1.5177(18) . ? C7 C8 1.515(2) . ? C7 C6 1.522(2) . ? C12 C4" 1.4740(19) . ? N1" C2" 1.335(2) . ? N1" C6" 1.339(2) . ? C4' C3' 1.389(2) . ? C4' C5' 1.392(2) . ? C3' C2' 1.388(2) . ? N1' C2' 1.335(2) . ? N1' C6' 1.339(2) . ? C3 C2 1.527(2) . ? C3" C2" 1.383(2) . ? C3" C4" 1.395(2) . ? C6' C5' 1.383(2) . ? C4" C5" 1.393(2) . ? C5" C6" 1.386(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 C5A O10 C4A 117.84(10) . . ? C4A N1 C1N 114.60(11) . . ? C4A N1 C2N 114.49(11) . . ? C1N N1 C2N 109.32(12) . . ? C4A C9A C1 110.24(11) . . ? C4A C9A C9 110.93(10) . . ? C1 C9A C9 111.04(11) . . ? C2 C1 C9A 111.99(11) . . ? N1 C4A O10 106.19(10) . . ? N1 C4A C4 110.41(11) . . ? O10 C4A C4 110.14(10) . . ? N1 C4A C9A 111.85(11) . . ? O10 C4A C9A 109.17(10) . . ? C4 C4A C9A 109.06(11) . . ? C5A C8A C9 121.66(12) . . ? C5A C8A C8 121.39(12) . . ? C9 C8A C8 116.94(11) . . ? C12 C5 C5A 120.84(12) . . ? C12 C5 C6 124.42(13) . . ? C5A C5 C6 114.74(12) . . ? C8A C5A O10 123.54(12) . . ? C8A C5A C5 122.99(12) . . ? O10 C5A C5 113.35(11) . . ? C4A C4 C3 111.06(11) . . ? C8A C9 C4' 110.83(11) . . ? C8A C9 C9A 112.39(11) . . ? C4' C9 C9A 109.04(11) . . ? C8 C7 C6 109.21(11) . . ? C5 C12 C4" 127.31(13) . . ? C5 C6 C7 110.94(11) . . ? C2" N1" C6" 115.60(13) . . ? C3' C4' C5' 117.00(13) . . ? C3' C4' C9 121.65(13) . . ? C5' C4' C9 121.34(12) . . ? C2' C3' C4' 119.07(14) . . ? C8A C8 C7 111.19(11) . . ? C2' N1' C6' 115.52(13) . . ? C2 C3 C4 112.01(11) . . ? N1' C2' C3' 124.65(15) . . ? C3 C2 C1 111.39(12) . . ? C2" C3" C4" 119.89(14) . . ? N1' C6' C5' 124.40(15) . . ? C5" C4" C3" 115.76(13) . . ? C5" C4" C12 119.88(13) . . ? C3" C4" C12 124.33(13) . . ? C6' C5' C4' 119.36(14) . . ? C6" C5" C4" 120.25(14) . . ? N1" C6" C5" 123.94(14) . . ? N1" C2" C3" 124.54(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 C4A C9A C1 C2 57.04(14) . . . . ? C9 C9A C1 C2 -66.31(14) . . . . ? C1N N1 C4A O10 -63.22(14) . . . . ? C2N N1 C4A O10 64.27(14) . . . . ? C1N N1 C4A C4 177.41(12) . . . . ? C2N N1 C4A C4 -55.11(15) . . . . ? C1N N1 C4A C9A 55.77(15) . . . . ? C2N N1 C4A C9A -176.75(12) . . . . ? C5A O10 C4A N1 166.31(10) . . . . ? C5A O10 C4A C4 -74.14(14) . . . . ? C5A O10 C4A C9A 45.58(14) . . . . ? C1 C9A C4A N1 63.00(14) . . . . ? C9 C9A C4A N1 -173.59(11) . . . . ? C1 C9A C4A O10 -179.79(10) . . . . ? C9 C9A C4A O10 -56.38(13) . . . . ? C1 C9A C4A C4 -59.41(14) . . . . ? C9 C9A C4A C4 64.00(14) . . . . ? C9 C8A C5A O10 -6.5(2) . . . . ? C8 C8A C5A O10 171.88(12) . . . . ? C9 C8A C5A C5 169.43(12) . . . . ? C8 C8A C5A C5 -12.2(2) . . . . ? C4A O10 C5A C8A -14.29(18) . . . . ? C4A O10 C5A C5 169.44(11) . . . . ? C12 C5 C5A C8A -176.87(13) . . . . ? C6 C5 C5A C8A 2.14(19) . . . . ? C12 C5 C5A O10 -0.58(18) . . . . ? C6 C5 C5A O10 178.43(11) . . . . ? N1 C4A C4 C3 -64.28(14) . . . . ? O10 C4A C4 C3 178.77(10) . . . . ? C9A C4A C4 C3 58.99(14) . . . . ? C5A C8A C9 C4' -129.14(14) . . . . ? C8 C8A C9 C4' 52.44(15) . . . . ? C5A C8A C9 C9A -6.84(18) . . . . ? C8 C8A C9 C9A 174.73(11) . . . . ? C4A C9A C9 C8A 37.88(15) . . . . ? C1 C9A C9 C8A 160.83(11) . . . . ? C4A C9A C9 C4' 161.17(11) . . . . ? C1 C9A C9 C4' -75.87(13) . . . . ? C5A C5 C12 C4" 175.12(13) . . . . ? C6 C5 C12 C4" -3.8(2) . . . . ? C12 C5 C6 C7 -146.27(14) . . . . ? C5A C5 C6 C7 34.76(16) . . . . ? C8 C7 C6 C5 -61.64(15) . . . . ? C8A C9 C4' C3' -129.62(13) . . . . ? C9A C9 C4' C3' 106.16(14) . . . . ? C8A C9 C4' C5' 51.35(17) . . . . ? C9A C9 C4' C5' -72.87(16) . . . . ? C5' C4' C3' C2' 0.4(2) . . . . ? C9 C4' C3' C2' -178.72(13) . . . . ? C5A C8A C8 C7 -15.82(19) . . . . ? C9 C8A C8 C7 162.61(12) . . . . ? C6 C7 C8 C8A 51.44(15) . . . . ? C4A C4 C3 C2 -55.80(15) . . . . ? C6' N1' C2' C3' 0.0(2) . . . . ? C4' C3' C2' N1' -0.2(2) . . . . ? C4 C3 C2 C1 51.96(16) . . . . ? C9A C1 C2 C3 -52.85(15) . . . . ? C2' N1' C6' C5' 0.0(2) . . . . ? C2" C3" C4" C5" -0.6(2) . . . . ? C2" C3" C4" C12 -178.86(14) . . . . ? C5 C12 C4" C5" 146.76(15) . . . . ? C5 C12 C4" C3" -35.1(2) . . . . ? N1' C6' C5' C4' 0.2(2) . . . . ? C3' C4' C5' C6' -0.3(2) . . . . ? C9 C4' C5' C6' 178.73(13) . . . . ? C3" C4" C5" C6" 1.4(2) . . . . ? C12 C4" C5" C6" 179.67(13) . . . . ? C2" N1" C6" C5" 0.0(2) . . . . ? C4" C5" C6" N1" -1.1(2) . . . . ? C6" N1" C2" C3" 0.7(2) . . . . ? C4" C3" C2" N1" -0.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.19 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.223 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.054 # Attachment '9.CIF' data_9 _database_code_depnum_ccdc_archive 'CCDC 605786' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7a-Dimethylamino-5,6,7,7a-tetrahydro-4H-benzofuran-2-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H15 N O2' _chemical_formula_sum 'C10 H15 N O2' _chemical_formula_weight 181.23 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' N N 0.0061 0.0033 '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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7630(2) _cell_length_b 10.9240(2) _cell_length_c 20.1019(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1924.29(7) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max .5 _exptl_crystal_size_mid .45 _exptl_crystal_size_min .4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.087 _exptl_special_details ; ? ; _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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 2322 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 28.26 _reflns_number_total 2322 _reflns_number_gt 1545 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material ciftab _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.9323P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2322 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0935 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.23504(14) 0.29942(10) 0.37949(6) 0.0221(3) Uani 1 1 d . . . O2 O 0.45453(15) 0.20677(13) 0.40684(7) 0.0339(4) Uani 1 1 d . . . C1 C 0.0731(2) 0.26240(15) 0.37049(8) 0.0185(4) Uani 1 1 d . . . C2 C 0.0761(2) 0.12726(15) 0.38636(8) 0.0208(4) Uani 1 1 d . . . N1 N 0.02179(18) 0.28578(14) 0.30422(7) 0.0251(4) Uani 1 1 d . . . C2' C 0.2166(2) 0.09362(16) 0.40256(9) 0.0256(4) Uani 1 1 d . . . H2' H 0.2464 0.0135 0.4156 0.031 Uiso 1 1 calc R . . C6 C -0.0230(2) 0.32452(16) 0.42422(9) 0.0231(4) Uani 1 1 d . . . H6A H 0.0269 0.3147 0.4681 0.028 Uiso 1 1 calc R . . H6B H -0.0314 0.4132 0.4146 0.028 Uiso 1 1 calc R . . C4 C -0.1750(2) 0.13011(17) 0.44009(9) 0.0284(4) Uani 1 1 d . . . H4A H -0.2794 0.0956 0.4383 0.034 Uiso 1 1 calc R . . H4B H -0.1344 0.1166 0.4855 0.034 Uiso 1 1 calc R . . C1' C 0.3188(2) 0.19954(16) 0.39722(9) 0.0236(4) Uani 1 1 d . . . C3 C -0.0731(2) 0.06274(17) 0.38937(9) 0.0283(5) Uani 1 1 d . . . H3A H -0.0579 -0.0233 0.4033 0.034 Uiso 1 1 calc R . . H3B H -0.1220 0.0629 0.3450 0.034 Uiso 1 1 calc R . . C5 C -0.1821(2) 0.26738(17) 0.42611(9) 0.0263(4) Uani 1 1 d . . . H5A H -0.2434 0.3079 0.4611 0.032 Uiso 1 1 calc R . . H5B H -0.2334 0.2813 0.3829 0.032 Uiso 1 1 calc R . . C8 C 0.0006(3) 0.41443(19) 0.28658(11) 0.0406(6) Uani 1 1 d . . . H8A H -0.0726 0.4520 0.3172 0.061 Uiso 1 1 calc R . . H8B H -0.0383 0.4202 0.2410 0.061 Uiso 1 1 calc R . . H8C H 0.0986 0.4573 0.2897 0.061 Uiso 1 1 calc R . . C7 C 0.1121(2) 0.2237(2) 0.25321(10) 0.0356(5) Uani 1 1 d . . . H7A H 0.2143 0.2600 0.2513 0.053 Uiso 1 1 calc R . . H7B H 0.0621 0.2329 0.2099 0.053 Uiso 1 1 calc R . . H7C H 0.1205 0.1365 0.2642 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0180(7) 0.0214(6) 0.0270(6) -0.0006(5) -0.0019(5) -0.0037(5) O2 0.0169(8) 0.0525(9) 0.0322(8) 0.0011(6) 0.0002(6) 0.0023(6) C1 0.0139(9) 0.0190(8) 0.0225(9) 0.0013(7) -0.0007(7) -0.0026(7) C2 0.0243(10) 0.0175(8) 0.0207(9) -0.0031(7) 0.0032(7) -0.0014(7) N1 0.0246(9) 0.0293(8) 0.0215(8) 0.0039(6) -0.0028(6) -0.0032(6) C2' 0.0267(11) 0.0206(8) 0.0293(9) 0.0025(8) 0.0049(8) 0.0057(7) C6 0.0214(10) 0.0211(9) 0.0267(9) -0.0021(7) -0.0002(7) 0.0028(7) C4 0.0219(11) 0.0341(10) 0.0293(10) 0.0008(8) 0.0029(7) -0.0063(8) C1' 0.0218(11) 0.0296(10) 0.0194(8) -0.0020(8) 0.0030(7) 0.0034(7) C3 0.0288(11) 0.0230(9) 0.0331(10) -0.0008(8) 0.0034(8) -0.0069(8) C5 0.0211(10) 0.0331(10) 0.0247(9) -0.0007(8) 0.0016(7) 0.0042(8) C8 0.0459(14) 0.0370(12) 0.0391(12) 0.0174(10) -0.0044(10) 0.0022(10) C7 0.0378(13) 0.0461(12) 0.0228(10) -0.0035(9) 0.0010(8) -0.0099(10) _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 C1' 1.362(2) . ? O1 C1 1.487(2) . ? O2 C1' 1.208(2) . ? C1 N1 1.429(2) . ? C1 C2 1.510(2) . ? C1 C6 1.529(2) . ? C2 C2' 1.325(3) . ? C2 C3 1.486(3) . ? N1 C8 1.461(2) . ? N1 C7 1.462(2) . ? C2' C1' 1.467(3) . ? C6 C5 1.527(3) . ? C4 C5 1.527(3) . ? C4 C3 1.542(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 C1' O1 C1 109.16(13) . . ? N1 C1 O1 111.43(13) . . ? N1 C1 C2 112.15(14) . . ? O1 C1 C2 102.92(13) . . ? N1 C1 C6 113.94(15) . . ? O1 C1 C6 108.62(13) . . ? C2 C1 C6 107.11(14) . . ? C2' C2 C3 132.47(17) . . ? C2' C2 C1 109.83(16) . . ? C3 C2 C1 117.18(16) . . ? C1 N1 C8 115.99(15) . . ? C1 N1 C7 113.61(15) . . ? C8 N1 C7 110.15(16) . . ? C2 C2' C1' 109.29(16) . . ? C5 C6 C1 109.82(14) . . ? C5 C4 C3 111.74(15) . . ? O2 C1' O1 121.34(17) . . ? O2 C1' C2' 129.89(17) . . ? O1 C1' C2' 108.76(15) . . ? C2 C3 C4 108.07(15) . . ? C4 C5 C6 111.65(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 C1' O1 C1 N1 -119.78(15) . . . . ? C1' O1 C1 C2 0.59(16) . . . . ? C1' O1 C1 C6 113.91(15) . . . . ? N1 C1 C2 C2' 120.57(17) . . . . ? O1 C1 C2 C2' 0.70(18) . . . . ? C6 C1 C2 C2' -113.71(16) . . . . ? N1 C1 C2 C3 -66.7(2) . . . . ? O1 C1 C2 C3 173.45(14) . . . . ? C6 C1 C2 C3 59.04(19) . . . . ? O1 C1 N1 C8 -71.1(2) . . . . ? C2 C1 N1 C8 174.13(16) . . . . ? C6 C1 N1 C8 52.2(2) . . . . ? O1 C1 N1 C7 58.05(19) . . . . ? C2 C1 N1 C7 -56.7(2) . . . . ? C6 C1 N1 C7 -178.62(15) . . . . ? C3 C2 C2' C1' -172.90(18) . . . . ? C1 C2 C2' C1' -1.6(2) . . . . ? N1 C1 C6 C5 67.54(19) . . . . ? O1 C1 C6 C5 -167.61(13) . . . . ? C2 C1 C6 C5 -57.09(18) . . . . ? C1 O1 C1' O2 179.41(15) . . . . ? C1 O1 C1' C2' -1.56(18) . . . . ? C2 C2' C1' O2 -179.02(18) . . . . ? C2 C2' C1' O1 2.1(2) . . . . ? C2' C2 C3 C4 115.2(2) . . . . ? C1 C2 C3 C4 -55.5(2) . . . . ? C5 C4 C3 C2 51.3(2) . . . . ? C3 C4 C5 C6 -55.7(2) . . . . ? C1 C6 C5 C4 58.77(19) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.288 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.062