# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/157 data_global _publ_section_title ; Establishing structural repetitivity in systems with interaction interference: crystal engineering in the gem-alkynol family ; _publ_contact_author_name ; Professor Gautam R. Desiraju ; _publ_contact_author_address ; School of Chemistry University of Hyderabad Hyderabad 500 046 India ; _publ_contact_author_phone '91 40 3010567' _publ_contact_author_fax '91 40 3010567' _publ_contact_author_email grdch@uohyd.ernet.in _publ_requested_journal 'NJC' data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-1,4-Diethynyl-1,4-dihydroxy-2,5-cyclohexadiene ; _chemical_name_common ; trans-1,4-Diethynyl-1,4-dihydroxy-2,5-cyclohexadiene ; _chemical_melting_point '452-453 K (sublimes)' _chemical_formula_moiety 'C10 H8 O2' _chemical_formula_sum 'C10 H8 O2' _chemical_formula_weight 160.16 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 'orthorhombic' _symmetry_space_group_name_H-M 'P 21/b 21/c 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.8316(2) _cell_length_b 5.90030(10) _cell_length_c 15.6123(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 813.54(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 490 _cell_measurement_theta_min 5.30 _cell_measurement_theta_max 21.41 _exptl_crystal_description block _exptl_crystal_colour colourles _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.236 _exptl_absorpt_correction_T_max 0.266 _exptl_absorpt_process_details 'empirical using psi-scans' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _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 'Brucker SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 'not relevant' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 5130 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.45 _reflns_number_total 934 _reflns_number_gt 837 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Brucker SMART' _computing_cell_refinement 'Brucker SMART' _computing_data_reduction 'Brucker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.3064P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 934 _refine_ls_number_parameters 71 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0880 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.309 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.049 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.38988(15) 0.3628(2) 0.68883(8) 0.0262(3) Uani 1 1 d . . . H1 H 0.329(2) 0.445(3) 0.7261(12) 0.046(5) Uiso 1 1 d . . . C2 C 0.46345(12) 0.25097(19) 0.64093(7) 0.0199(3) Uani 1 1 d . . . C3 C 0.55305(12) 0.10419(18) 0.58250(7) 0.0172(3) Uani 1 1 d . . . O1 O 0.70092(9) 0.06232(15) 0.62009(5) 0.0225(2) Uani 1 1 d . . . HA H 0.747(2) 0.194(3) 0.6248(10) 0.044(5) Uiso 1 1 d . . . C4 C 0.47605(13) -0.12408(18) 0.57682(7) 0.0178(3) Uani 1 1 d . . . H4 H 0.4615(17) -0.199(2) 0.6319(9) 0.024(3) Uiso 1 1 d . . . C5 C 0.42888(13) -0.21613(18) 0.50397(7) 0.0181(3) Uani 1 1 d . . . H5 H 0.3761(17) -0.359(3) 0.5039(9) 0.023(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0318(7) 0.0216(6) 0.0253(6) -0.0020(4) 0.0050(5) 0.0010(5) C2 0.0219(5) 0.0176(5) 0.0203(5) 0.0009(4) 0.0000(4) -0.0022(4) C3 0.0171(5) 0.0164(5) 0.0180(5) 0.0001(4) -0.0005(4) -0.0002(4) O1 0.0175(4) 0.0247(5) 0.0254(4) 0.0013(3) -0.0032(3) -0.0007(3) C4 0.0194(5) 0.0153(5) 0.0188(5) 0.0029(4) 0.0022(4) 0.0005(4) C5 0.0190(5) 0.0142(5) 0.0210(5) 0.0016(4) 0.0019(4) -0.0016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.1905(17) . yes C1 H1 0.927(19) . yes C2 C3 1.4861(15) . yes C3 O1 1.4529(13) . yes C3 C5 1.5113(14) 5_656 yes C3 C4 1.5115(15) . yes O1 HA 0.88(2) . yes C4 C5 1.3274(15) . yes C4 H4 0.977(14) . yes C5 C3 1.5113(14) 5_656 yes C5 H5 0.965(15) . yes 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 C2 C1 H1 177.6(12) . . yes C1 C2 C3 178.03(12) . . yes O1 C3 C2 109.25(8) . . yes O1 C3 C5 109.89(9) . 5_656 yes C2 C3 C5 110.48(9) . 5_656 yes O1 C3 C4 106.05(8) . . yes C2 C3 C4 108.40(9) . . yes C5 C3 C4 112.62(9) 5_656 . yes C3 O1 HA 107.4(12) . . yes C5 C4 C3 123.78(9) . . yes C5 C4 H4 121.8(8) . . yes C3 C4 H4 114.4(8) . . yes C4 C5 C3 123.60(10) . 5_656 yes C4 C5 H5 120.7(8) . . yes C3 C5 H5 115.7(8) 5_656 . yes #===END data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-9,10-Diethynyl-9,10-dihydroxy-9,10-dihydroanthracene ; _chemical_name_common ; trans-9,10-Diethynyl-9,10-dihydroxy-9,10-dihydroanthracene ; _chemical_melting_point '479-480 K' _chemical_formula_moiety 'C18 H12 O2' _chemical_formula_sum 'C18 H12 O2' _chemical_formula_weight 260.28 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 8.7684(18) _cell_length_b 8.9558(18) _cell_length_c 10.315(2) _cell_angle_alpha 113.78(3) _cell_angle_beta 102.06(3) _cell_angle_gamma 102.59(3) _cell_volume 682.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 440 _cell_measurement_theta_min 5.78 _cell_measurement_theta_max 26.23 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3520 _exptl_absorpt_correction_T_max 0.4119 _exptl_absorpt_process_details 'empirical correction using psi-scans' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _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 'Brucker SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_number 'not relevant' _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 6577 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 30.38 _reflns_number_total 3623 _reflns_number_gt 2404 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Brucker SMART' _computing_cell_refinement 'Brucker SMART' _computing_data_reduction 'Brucker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXS-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.5022P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3623 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0973 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 30.38 _diffrn_measured_fraction_theta_full 0.880 _refine_diff_density_max 0.396 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.053 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2626(3) -0.2681(3) 0.0455(3) 0.0338(5) Uani 1 1 d . . . H1 H 0.290(3) -0.363(3) 0.046(3) 0.048(7) Uiso 1 1 d . . . C2 C 0.3852(3) -0.1105(3) 0.0951(2) 0.0304(5) Uani 1 1 d . . . H2 H 0.500(3) -0.100(3) 0.127(3) 0.035(6) Uiso 1 1 d . . . C3 C 0.3410(2) 0.0283(3) 0.0941(2) 0.0256(4) Uani 1 1 d . . . H3 H 0.427(3) 0.140(3) 0.130(3) 0.034(6) Uiso 1 1 d . . . C4 C 0.1736(2) 0.0129(2) 0.04628(19) 0.0186(4) Uani 1 1 d . . . C5 C 0.1330(2) 0.1706(2) 0.0485(2) 0.0190(4) Uani 1 1 d . . . O1 O 0.21482(17) 0.31803(17) 0.19720(15) 0.0275(3) Uani 1 1 d . . . HA H 0.194(4) 0.276(4) 0.269(4) 0.087(11) Uiso 1 1 d . . . C6 C 0.2069(2) 0.2237(2) -0.0505(2) 0.0249(4) Uani 1 1 d . . . C7 C 0.2679(3) 0.2669(3) -0.1283(3) 0.0334(5) Uani 1 1 d . . . H7 H 0.317(3) 0.304(3) -0.195(3) 0.053(8) Uiso 1 1 d . . . C8 C -0.0513(2) 0.1439(2) 0.0007(2) 0.0197(4) Uani 1 1 d . . . C9 C -0.0974(3) 0.2856(3) 0.0023(2) 0.0282(4) Uani 1 1 d . . . H9 H -0.006(3) 0.396(3) 0.043(3) 0.035(6) Uiso 1 1 d . . . C21 C 0.8055(3) 0.2958(3) 0.3612(3) 0.0363(5) Uani 1 1 d . . . H21 H 0.889(3) 0.274(3) 0.314(3) 0.048(7) Uiso 1 1 d . . . C22 C 0.7475(3) 0.4286(3) 0.3655(2) 0.0301(4) Uani 1 1 d . . . H22 H 0.791(3) 0.500(3) 0.320(3) 0.034(6) Uiso 1 1 d . . . C23 C 0.6262(2) 0.4628(2) 0.4319(2) 0.0206(4) Uani 1 1 d . . . C24 C 0.5697(2) 0.6133(2) 0.4337(2) 0.0205(4) Uani 1 1 d . . . O2 O 0.51293(18) 0.59111(18) 0.28344(15) 0.0262(3) Uani 1 1 d . . . HB H 0.418(4) 0.502(4) 0.234(3) 0.058(8) Uiso 1 1 d . . . C25 C 0.7171(2) 0.7758(2) 0.5189(2) 0.0246(4) Uani 1 1 d . . . C26 C 0.8354(3) 0.9037(3) 0.5925(2) 0.0332(5) Uani 1 1 d . . . H26 H 0.931(3) 1.003(3) 0.652(3) 0.044(7) Uiso 1 1 d . . . C27 C 0.4359(2) 0.6393(2) 0.5062(2) 0.0206(4) Uani 1 1 d . . . C28 C 0.3738(3) 0.7721(3) 0.5092(2) 0.0292(4) Uani 1 1 d . . . H28 H 0.416(3) 0.840(3) 0.462(3) 0.039(6) Uiso 1 1 d . . . C29 C 0.2540(3) 0.8040(3) 0.5739(3) 0.0357(5) Uani 1 1 d . . . H29 H 0.210(3) 0.896(3) 0.575(3) 0.043(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0370(12) 0.0332(11) 0.0436(13) 0.0243(10) 0.0150(10) 0.0206(10) C2 0.0229(10) 0.0411(12) 0.0342(11) 0.0197(10) 0.0107(9) 0.0183(9) C3 0.0178(9) 0.0294(10) 0.0269(10) 0.0117(8) 0.0082(8) 0.0056(8) C4 0.0201(9) 0.0208(9) 0.0179(8) 0.0104(7) 0.0090(7) 0.0069(7) C5 0.0187(8) 0.0169(8) 0.0191(8) 0.0082(7) 0.0061(7) 0.0023(7) O1 0.0285(7) 0.0220(7) 0.0230(7) 0.0066(6) 0.0049(6) 0.0032(6) C6 0.0234(10) 0.0235(9) 0.0282(10) 0.0133(8) 0.0082(8) 0.0066(8) C7 0.0369(12) 0.0368(12) 0.0427(13) 0.0271(10) 0.0226(10) 0.0164(10) C8 0.0198(9) 0.0213(9) 0.0227(9) 0.0133(7) 0.0098(7) 0.0072(7) C9 0.0294(11) 0.0238(10) 0.0374(12) 0.0185(9) 0.0126(9) 0.0104(8) C21 0.0322(12) 0.0404(12) 0.0397(13) 0.0165(10) 0.0184(10) 0.0168(10) C22 0.0263(10) 0.0353(11) 0.0316(11) 0.0173(9) 0.0149(9) 0.0077(9) C23 0.0195(9) 0.0204(9) 0.0192(9) 0.0087(7) 0.0058(7) 0.0036(7) C24 0.0209(9) 0.0234(9) 0.0193(9) 0.0133(7) 0.0073(7) 0.0043(7) O2 0.0263(7) 0.0299(7) 0.0208(7) 0.0160(6) 0.0051(6) 0.0012(6) C25 0.0255(10) 0.0277(10) 0.0234(9) 0.0158(8) 0.0084(8) 0.0062(8) C26 0.0310(11) 0.0320(11) 0.0307(11) 0.0166(9) 0.0058(9) 0.0005(9) C27 0.0205(9) 0.0211(9) 0.0187(9) 0.0095(7) 0.0060(7) 0.0043(7) C28 0.0317(11) 0.0272(10) 0.0315(11) 0.0167(9) 0.0103(9) 0.0099(9) C29 0.0339(12) 0.0326(11) 0.0418(13) 0.0159(10) 0.0118(10) 0.0174(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 C1 C9 1.381(3) 2 yes C1 C2 1.391(3) . yes C1 H1 0.94(3) . yes C2 C3 1.383(3) . yes C2 H2 0.96(2) . yes C3 C4 1.404(3) . yes C3 H3 0.98(2) . yes C4 C8 1.391(2) 2 yes C4 C5 1.523(2) . yes C5 O1 1.450(2) . yes C5 C6 1.491(3) . yes C5 C8 1.522(2) . yes O1 HA 0.99(3) . yes C6 C7 1.191(3) . yes C7 H7 1.01(3) . yes C8 C4 1.391(2) 2 yes C8 C9 1.408(3) . yes C9 C1 1.381(3) 2 yes C9 H9 0.99(2) . yes C21 C22 1.380(3) . yes C21 C29 1.394(3) 2_666 yes C21 H21 0.97(3) . yes C22 C23 1.404(3) . yes C22 H22 0.99(2) . yes C23 C27 1.393(2) 2_666 yes C23 C24 1.529(3) . yes C24 O2 1.440(2) . yes C24 C25 1.494(3) . yes C24 C27 1.529(3) . yes O2 HB 0.89(3) . yes C25 C26 1.190(3) . yes C26 H26 0.94(3) . yes C27 C23 1.393(2) 2_666 yes C27 C28 1.403(3) . yes C28 C29 1.379(3) . yes C28 H28 0.98(2) . yes C29 C21 1.394(3) 2_666 yes C29 H29 0.98(2) . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 C1 C2 120.27(19) 2 . yes C9 C1 H1 118.9(16) 2 . yes C2 C1 H1 120.8(16) . . yes C3 C2 C1 119.74(19) . . yes C3 C2 H2 120.5(14) . . yes C1 C2 H2 119.7(14) . . yes C2 C3 C4 120.72(19) . . yes C2 C3 H3 120.0(13) . . yes C4 C3 H3 119.3(13) . . yes C8 C4 C3 119.44(17) 2 . yes C8 C4 C5 122.36(15) 2 . yes C3 C4 C5 118.20(16) . . yes O1 C5 C6 104.47(14) . . yes O1 C5 C8 109.21(15) . . yes C6 C5 C8 108.97(15) . . yes O1 C5 C4 109.89(14) . . yes C6 C5 C4 109.36(15) . . yes C8 C5 C4 114.46(14) . . yes C5 O1 HA 107(2) . . yes C7 C6 C5 179.2(2) . . yes C6 C7 H7 178.8(15) . . yes C4 C8 C9 119.44(17) 2 . yes C4 C8 C5 123.15(15) 2 . yes C9 C8 C5 117.40(16) . . yes C1 C9 C8 120.37(19) 2 . yes C1 C9 H9 123.3(13) 2 . yes C8 C9 H9 116.3(13) . . yes C22 C21 C29 120.0(2) . 2_666 yes C22 C21 H21 119.6(15) . . yes C29 C21 H21 120.4(15) 2_666 . yes C21 C22 C23 120.87(19) . . yes C21 C22 H22 119.5(13) . . yes C23 C22 H22 119.7(13) . . yes C27 C23 C22 119.18(17) 2_666 . yes C27 C23 C24 123.08(16) 2_666 . yes C22 C23 C24 117.73(16) . . yes O2 C24 C25 105.98(14) . . yes O2 C24 C27 109.72(14) . . yes C25 C24 C27 108.40(15) . . yes O2 C24 C23 110.19(15) . . yes C25 C24 C23 108.16(15) . . yes C27 C24 C23 114.05(14) . . yes C24 O2 HB 107.2(18) . . yes C26 C25 C24 176.9(2) . . yes C25 C26 H26 178.0(16) . . yes C23 C27 C28 119.31(17) 2_666 . yes C23 C27 C24 122.85(16) 2_666 . yes C28 C27 C24 117.84(16) . . yes C29 C28 C27 121.03(19) . . yes C29 C28 H28 120.8(14) . . yes C27 C28 H28 118.2(14) . . yes C28 C29 C21 119.6(2) . 2_666 yes C28 C29 H29 121.0(14) . . yes C21 C29 H29 119.4(14) 2_666 . yes #===END data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-1,4-Diethynyl-1,4-dihydroxy-1,4-dihydronaphthalene ; _chemical_name_common ; trans-1,4-Diethynyl-1,4-dihydroxy-1,4-dihydronaphthalene ; _chemical_melting_point '407 K' _chemical_formula_moiety 'C14 H10 O2' _chemical_formula_sum 'C14 H10 O2' _chemical_formula_weight 210.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 10.8247(3) _cell_length_b 22.6384(8) _cell_length_c 10.4783(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.1850(10) _cell_angle_gamma 90.00 _cell_volume 2263.28(12) _cell_formula_units_Z 8 _cell_measurement_temperature 150 _cell_measurement_reflns_used 935 _cell_measurement_theta_min 5.18 _cell_measurement_theta_max 23.24 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3984 _exptl_absorpt_correction_T_max 0.6141 _exptl_absorpt_process_details 'empirical correction using psi-scans' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _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 'Brucker SMART CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 'not relevant' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 17967 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0654 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 30.33 _reflns_number_total 6159 _reflns_number_gt 3713 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXS-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0897P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6159 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1083 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1597 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 30.33 _diffrn_measured_fraction_theta_full 0.905 _refine_diff_density_max 0.342 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.063 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6057(2) 0.16584(9) 0.0655(2) 0.0358(5) Uani 1 1 d . . . H1 H 0.703(2) 0.1669(8) 0.105(2) 0.028(5) Uiso 1 1 d . . . C2 C 0.48196(19) 0.16350(8) 0.01449(19) 0.0278(4) Uani 1 1 d . . . C3 C 0.32622(18) 0.16012(8) -0.05833(17) 0.0237(4) Uani 1 1 d . . . O1 O 0.28541(14) 0.17313(6) 0.05084(13) 0.0305(3) Uani 1 1 d . . . H1A H 0.192(2) 0.1761(8) 0.008(2) 0.031(5) Uiso 1 1 d . . . C4 C 0.28267(17) 0.09749(8) -0.11667(17) 0.0229(4) Uani 1 1 d . . . C5 C 0.3303(2) 0.05028(8) -0.0182(2) 0.0317(4) Uani 1 1 d . . . H5 H 0.387(2) 0.0605(9) 0.086(2) 0.036(5) Uiso 1 1 d . . . C6 C 0.2980(2) -0.00698(9) -0.0650(2) 0.0390(5) Uani 1 1 d . . . H6 H 0.339(2) -0.0405(9) 0.004(3) 0.041(6) Uiso 1 1 d . . . C7 C 0.2183(2) -0.01898(9) -0.2132(2) 0.0397(5) Uani 1 1 d . . . H7 H 0.198(2) -0.0609(11) -0.241(3) 0.050(7) Uiso 1 1 d . . . C8 C 0.1701(2) 0.02680(9) -0.3109(2) 0.0330(4) Uani 1 1 d . . . H8 H 0.112(2) 0.0179(9) -0.413(3) 0.039(6) Uiso 1 1 d . . . C9 C 0.19988(17) 0.08572(7) -0.26428(17) 0.0229(4) Uani 1 1 d . . . C10 C 0.13988(18) 0.13488(8) -0.37732(17) 0.0249(4) Uani 1 1 d . . . C11 C -0.01601(19) 0.13251(8) -0.44756(18) 0.0288(4) Uani 1 1 d . . . C12 C -0.1393(2) 0.13167(9) -0.4965(2) 0.0365(5) Uani 1 1 d . . . H12 H -0.238(3) 0.1306(10) -0.533(3) 0.047(7) Uiso 1 1 d . . . O2 O 0.17743(15) 0.12550(6) -0.49066(13) 0.0327(3) Uani 1 1 d . . . H1B H 0.276(3) 0.1259(10) -0.448(3) 0.054(7) Uiso 1 1 d . . . C13 C 0.18568(19) 0.19571(8) -0.31458(19) 0.0281(4) Uani 1 1 d . . . H13 H 0.149(2) 0.2288(10) -0.382(3) 0.048(6) Uiso 1 1 d . . . C14 C 0.26793(19) 0.20682(8) -0.17528(19) 0.0275(4) Uani 1 1 d . . . H14 H 0.2925(19) 0.2480(9) -0.146(2) 0.027(5) Uiso 1 1 d . . . C21 C 0.0004(2) 0.15781(10) 0.1815(2) 0.0379(5) Uani 1 1 d . . . H21 H 0.044(3) 0.1561(11) 0.293(3) 0.068(8) Uiso 1 1 d . . . C22 C -0.05315(18) 0.16146(8) 0.05225(19) 0.0282(4) Uani 1 1 d . . . C23 C -0.11749(17) 0.16598(8) -0.10767(18) 0.0248(4) Uani 1 1 d . . . O21 O -0.00582(14) 0.18835(6) -0.13431(15) 0.0325(3) Uani 1 1 d . . . H2A H -0.036(3) 0.1888(14) -0.230(4) 0.090(10) Uiso 1 1 d . . . C24 C -0.16527(17) 0.10569(8) -0.17697(17) 0.0234(4) Uani 1 1 d . . . C25 C -0.0664(2) 0.06005(9) -0.1399(2) 0.0312(4) Uani 1 1 d . . . H25 H 0.032(2) 0.0682(9) -0.079(2) 0.036(6) Uiso 1 1 d . . . C26 C -0.1044(2) 0.00488(9) -0.2001(2) 0.0384(5) Uani 1 1 d . . . H26 H -0.039(3) -0.0254(10) -0.178(3) 0.045(6) Uiso 1 1 d . . . C27 C -0.2444(2) -0.00721(10) -0.2976(2) 0.0413(5) Uani 1 1 d . . . H27 H -0.267(2) -0.0479(10) -0.337(3) 0.045(6) Uiso 1 1 d . . . C28 C -0.3427(2) 0.03720(9) -0.3345(2) 0.0360(5) Uani 1 1 d . . . H28 H -0.442(3) 0.0287(10) -0.397(3) 0.052(7) Uiso 1 1 d . . . C29 C -0.30452(18) 0.09391(8) -0.27648(18) 0.0251(4) Uani 1 1 d . . . C30 C -0.41771(18) 0.14099(8) -0.32551(18) 0.0262(4) Uani 1 1 d . . . C31 C -0.48351(19) 0.14777(9) -0.48569(19) 0.0300(4) Uani 1 1 d . . . C32 C -0.5363(2) 0.15364(10) -0.6138(2) 0.0382(5) Uani 1 1 d . . . H32 H -0.582(3) 0.1582(13) -0.720(4) 0.084(9) Uiso 1 1 d . . . O22 O -0.53108(14) 0.12168(7) -0.29872(16) 0.0354(3) Uani 1 1 d . . . H2B H -0.500(3) 0.1227(12) -0.214(3) 0.065(9) Uiso 1 1 d . . . C33 C -0.3652(2) 0.20015(9) -0.25591(19) 0.0293(4) Uani 1 1 d . . . H33 H -0.436(2) 0.2292(10) -0.285(2) 0.042(6) Uiso 1 1 d . . . C34 C -0.2337(2) 0.21101(8) -0.15949(19) 0.0285(4) Uani 1 1 d . . . H34 H -0.208(2) 0.2508(10) -0.123(3) 0.046(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0271(10) 0.0463(12) 0.0301(10) -0.0069(8) 0.0103(8) -0.0026(8) C2 0.0315(10) 0.0308(10) 0.0195(8) -0.0043(7) 0.0109(7) 0.0003(7) C3 0.0254(9) 0.0316(9) 0.0151(8) -0.0025(6) 0.0105(7) 0.0008(7) O1 0.0276(7) 0.0480(8) 0.0154(6) -0.0054(5) 0.0097(5) 0.0047(6) C4 0.0213(8) 0.0301(9) 0.0165(8) 0.0001(6) 0.0083(7) 0.0009(7) C5 0.0328(10) 0.0371(11) 0.0227(9) 0.0050(8) 0.0110(8) 0.0037(8) C6 0.0400(12) 0.0349(11) 0.0399(12) 0.0115(9) 0.0170(10) 0.0056(9) C7 0.0411(12) 0.0287(11) 0.0457(12) -0.0040(9) 0.0177(10) -0.0025(8) C8 0.0328(10) 0.0360(11) 0.0273(10) -0.0085(8) 0.0117(8) -0.0035(8) C9 0.0209(8) 0.0306(9) 0.0170(7) -0.0008(6) 0.0087(7) -0.0004(7) C10 0.0251(9) 0.0366(10) 0.0119(7) 0.0015(7) 0.0079(7) 0.0017(7) C11 0.0288(10) 0.0401(11) 0.0167(8) 0.0029(7) 0.0102(7) 0.0013(8) C12 0.0298(11) 0.0525(13) 0.0253(10) 0.0041(8) 0.0114(9) 0.0023(9) O2 0.0266(7) 0.0588(9) 0.0137(6) -0.0003(5) 0.0103(5) 0.0012(6) C13 0.0298(10) 0.0306(10) 0.0241(9) 0.0076(7) 0.0129(8) 0.0024(7) C14 0.0297(10) 0.0255(9) 0.0247(9) 0.0002(7) 0.0108(8) -0.0001(7) C21 0.0372(11) 0.0505(13) 0.0206(9) 0.0001(8) 0.0093(8) -0.0048(9) C22 0.0247(9) 0.0362(10) 0.0201(8) 0.0000(7) 0.0077(7) -0.0035(7) C23 0.0218(8) 0.0352(10) 0.0168(8) 0.0016(7) 0.0085(7) -0.0028(7) O21 0.0285(7) 0.0470(8) 0.0231(7) 0.0039(6) 0.0131(6) -0.0070(6) C24 0.0239(9) 0.0311(9) 0.0151(7) 0.0049(6) 0.0091(7) 0.0015(7) C25 0.0275(10) 0.0411(11) 0.0250(9) 0.0078(8) 0.0124(8) 0.0040(8) C26 0.0474(13) 0.0352(11) 0.0367(11) 0.0095(9) 0.0233(10) 0.0119(9) C27 0.0569(14) 0.0325(11) 0.0358(11) -0.0042(9) 0.0228(10) 0.0001(10) C28 0.0383(11) 0.0388(11) 0.0260(10) -0.0047(8) 0.0110(9) -0.0028(9) C29 0.0263(9) 0.0328(9) 0.0161(8) 0.0008(7) 0.0099(7) 0.0007(7) C30 0.0205(8) 0.0402(10) 0.0158(8) 0.0008(7) 0.0069(7) 0.0005(7) C31 0.0244(9) 0.0423(11) 0.0201(8) 0.0000(7) 0.0079(7) 0.0036(7) C32 0.0371(11) 0.0539(13) 0.0205(9) 0.0026(9) 0.0110(8) 0.0087(9) O22 0.0246(7) 0.0601(10) 0.0213(7) -0.0005(6) 0.0108(6) -0.0028(6) C33 0.0306(10) 0.0349(10) 0.0202(8) 0.0026(7) 0.0103(7) 0.0071(8) C34 0.0350(10) 0.0288(10) 0.0212(8) 0.0004(7) 0.0129(8) 0.0004(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.185(3) . yes C2 C3 1.488(2) . yes C3 O1 1.438(2) . yes C3 C14 1.512(2) . yes C3 C4 1.528(2) . yes C4 C9 1.399(2) . yes C4 C5 1.404(2) . yes C5 C6 1.371(3) . yes C6 C7 1.401(3) . yes C7 C8 1.374(3) . yes C8 C9 1.405(3) . yes C9 C10 1.529(2) . yes C10 O2 1.441(2) . yes C10 C11 1.490(2) . yes C10 C13 1.505(3) . yes C11 C12 1.183(3) . yes C13 C14 1.326(2) . yes C21 C22 1.198(3) . yes C22 C23 1.484(2) . yes C23 O21 1.454(2) . yes C23 C34 1.507(3) . yes C23 C24 1.518(2) . yes C24 C29 1.395(2) . yes C24 C25 1.404(3) . yes C25 C26 1.372(3) . yes C26 C27 1.397(3) . yes C27 C28 1.380(3) . yes C28 C29 1.397(3) . yes C29 C30 1.519(2) . yes C30 O22 1.450(2) . yes C30 C31 1.490(2) . yes C30 C33 1.502(3) . yes C31 C32 1.192(3) . yes C33 C34 1.323(3) . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 176.53(19) . . yes O1 C3 C2 106.31(13) . . yes O1 C3 C14 109.52(14) . . yes C2 C3 C14 108.51(15) . . yes O1 C3 C4 110.83(14) . . yes C2 C3 C4 108.27(14) . . yes C14 C3 C4 113.13(14) . . yes C9 C4 C5 119.27(16) . . yes C9 C4 C3 122.32(15) . . yes C5 C4 C3 118.40(15) . . yes C6 C5 C4 120.91(18) . . yes C5 C6 C7 119.93(18) . . yes C8 C7 C6 119.83(19) . . yes C7 C8 C9 120.87(18) . . yes C4 C9 C8 119.15(16) . . yes C4 C9 C10 122.27(15) . . yes C8 C9 C10 118.58(16) . . yes O2 C10 C11 106.39(13) . . yes O2 C10 C13 109.37(14) . . yes C11 C10 C13 108.13(15) . . yes O2 C10 C9 110.45(14) . . yes C11 C10 C9 108.92(14) . . yes C13 C10 C9 113.32(14) . . yes C12 C11 C10 176.43(19) . . yes C14 C13 C10 124.44(16) . . yes C13 C14 C3 124.44(16) . . yes C21 C22 C23 179.2(2) . . yes O21 C23 C22 104.57(13) . . yes O21 C23 C34 108.87(14) . . yes C22 C23 C34 108.68(15) . . yes O21 C23 C24 110.35(14) . . yes C22 C23 C24 110.52(14) . . yes C34 C23 C24 113.46(14) . . yes C29 C24 C25 118.65(17) . . yes C29 C24 C23 122.24(15) . . yes C25 C24 C23 119.11(16) . . yes C26 C25 C24 121.25(19) . . yes C25 C26 C27 120.04(19) . . yes C28 C27 C26 119.2(2) . . yes C27 C28 C29 121.2(2) . . yes C24 C29 C28 119.62(17) . . yes C24 C29 C30 122.20(16) . . yes C28 C29 C30 118.17(16) . . yes O22 C30 C31 104.56(14) . . yes O22 C30 C33 109.59(15) . . yes C31 C30 C33 108.96(15) . . yes O22 C30 C29 110.15(15) . . yes C31 C30 C29 109.48(15) . . yes C33 C30 C29 113.69(14) . . yes C32 C31 C30 179.5(2) . . yes C34 C33 C30 124.07(17) . . yes C33 C34 C23 124.31(17) . . yes #===END OF FILE