# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email ljb@sun.ac.za _publ_contact_author_name 'L. J. Barbour' loop_ _publ_author_name 'Dinabandhu Das' 'Tia Jacobs' 'Adam Pietraszako' 'L. J. Barbour' data_LT_210K _database_code_depnum_ccdc_archive 'CCDC 811708' #TrackingRef 'web_deposit_cif_file_0_DinabandhuDas_1296738574.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (s,s)-3,5-Ocatadiyn-2,7-diol ; _chemical_name_common ? _chemical_melting_point 343K _chemical_formula_moiety 'C8 H10 O2' _chemical_formula_sum 'C8 H10 O2' _chemical_formula_weight 138.16 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 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.1224(10) _cell_length_b 11.955(3) _cell_length_c 16.433(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 809.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used 1104 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 22.36 _chemical_absolute_configuration syn _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9723 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 210(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 4613 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.42 _reflns_number_total 1759 _reflns_number_gt 1298 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX-II' _computing_cell_refinement 'Bruker SMART APEX-II' _computing_data_reduction 'Bruker SAINT ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED (Barbour 2001)' _computing_publication_material ? _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^)+(0.0504P)^2^+0.0512P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 1759 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1118 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.0771(4) 0.60277(10) 0.00458(8) 0.0489(4) Uani 1 1 d . . . O2 O -0.2711(4) 0.25692(11) -0.39110(7) 0.0450(4) Uani 1 1 d . . . C4 C -0.0251(5) 0.38497(16) -0.12351(12) 0.0401(5) Uani 1 1 d . . . C5 C -0.1696(6) 0.33721(16) -0.19084(12) 0.0422(5) Uani 1 1 d . . . C7 C -0.4693(5) 0.24824(17) -0.31913(11) 0.0408(5) Uani 1 1 d . . . H7 H -0.6750 0.2890 -0.3285 0.049 Uiso 1 1 calc R . . C6 C -0.3000(6) 0.29939(15) -0.24978(12) 0.0411(5) Uani 1 1 d . . . C3 C 0.0964(5) 0.43015(16) -0.06649(11) 0.0415(5) Uani 1 1 d . . . C2 C 0.2349(6) 0.49587(16) 0.00124(11) 0.0426(5) Uani 1 1 d . . . H2 H 0.4698 0.5070 -0.0084 0.051 Uiso 1 1 calc R . . C8 C -0.5458(7) 0.12637(18) -0.30281(12) 0.0509(6) Uani 1 1 d . . . H8A H -0.6621 0.0953 -0.3489 0.076 Uiso 1 1 calc R . . H8B H -0.6788 0.1205 -0.2543 0.076 Uiso 1 1 calc R . . H8C H -0.3453 0.0853 -0.2948 0.076 Uiso 1 1 calc R . . C1 C 0.1870(7) 0.4394(2) 0.08286(12) 0.0627(7) Uani 1 1 d . . . H1A H 0.2959 0.4823 0.1248 0.094 Uiso 1 1 calc R . . H1B H 0.2773 0.3645 0.0810 0.094 Uiso 1 1 calc R . . H1C H -0.0429 0.4351 0.0950 0.094 Uiso 1 1 calc R . . H10 H 0.1317 0.6467 -0.0410 0.063(7) Uiso 1 1 d R . . H20 H -0.3981 0.3038 -0.4273 0.100(10) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0674(10) 0.0381(7) 0.0413(8) -0.0057(6) 0.0104(8) 0.0016(7) O2 0.0487(9) 0.0497(8) 0.0365(7) 0.0029(6) -0.0007(7) 0.0049(7) C4 0.0463(12) 0.0340(10) 0.0401(10) -0.0032(8) 0.0019(10) 0.0010(9) C5 0.0505(14) 0.0344(10) 0.0416(10) -0.0009(8) 0.0062(10) 0.0017(10) C7 0.0387(12) 0.0450(11) 0.0386(10) -0.0012(9) -0.0005(9) 0.0045(10) C6 0.0469(13) 0.0358(10) 0.0406(10) -0.0012(9) 0.0061(10) 0.0022(10) C3 0.0451(13) 0.0362(11) 0.0432(11) -0.0002(9) 0.0049(10) 0.0037(9) C2 0.0443(12) 0.0440(10) 0.0396(10) -0.0055(8) 0.0002(11) 0.0007(9) C8 0.0551(15) 0.0494(12) 0.0483(12) -0.0048(9) -0.0010(11) -0.0100(11) C1 0.0765(19) 0.0655(15) 0.0459(11) 0.0055(11) -0.0094(13) 0.0010(15) _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 C2 1.435(2) . ? O1 H10 0.9422 . ? O2 C7 1.441(2) . ? O2 H20 0.9710 . ? C4 C3 1.192(3) . ? C4 C5 1.380(3) . ? C5 C6 1.196(3) . ? C7 C6 1.470(3) . ? C7 C8 1.515(3) . ? C7 H7 0.9900 . ? C3 C2 1.477(3) . ? C2 C1 1.515(3) . ? C2 H2 0.9900 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 H1C 0.9700 . ? 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 O1 H10 110.9 . . ? C7 O2 H20 103.8 . . ? C3 C4 C5 177.5(2) . . ? C6 C5 C4 177.7(2) . . ? O2 C7 C6 109.70(17) . . ? O2 C7 C8 109.43(16) . . ? C6 C7 C8 111.21(17) . . ? O2 C7 H7 108.8 . . ? C6 C7 H7 108.8 . . ? C8 C7 H7 108.8 . . ? C5 C6 C7 176.7(2) . . ? C4 C3 C2 174.7(2) . . ? O1 C2 C3 109.10(17) . . ? O1 C2 C1 107.70(16) . . ? C3 C2 C1 112.31(17) . . ? O1 C2 H2 109.2 . . ? C3 C2 H2 109.2 . . ? C1 C2 H2 109.2 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.137 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.035 # Attachment 'web_deposit_cif_file_1_DinabandhuDas_1296738574.cif' data_LT_225K _database_code_depnum_ccdc_archive 'CCDC 811709' #TrackingRef 'web_deposit_cif_file_1_DinabandhuDas_1296738574.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (s,s)-3,5-Ocatadiyn-2,7-diol ; _chemical_name_common ? _chemical_melting_point 343K _chemical_formula_moiety 'C8 H10 O2' _chemical_formula_sum 'C8 H10 O2' _chemical_formula_weight 138.16 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 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.1314(11) _cell_length_b 11.955(3) _cell_length_c 16.429(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 811.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 225(2) _cell_measurement_reflns_used 1047 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 20.25 _chemical_absolute_configuration syn _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.131 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scaN _exptl_absorpt_correction_T_min 0.9724 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 225(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 4635 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.39 _reflns_number_total 1763 _reflns_number_gt 1283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX-II' _computing_cell_refinement 'Bruker SMART APEX-II' _computing_data_reduction 'Bruker SAINT ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED (Barbour 2001)' _computing_publication_material ? _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^)+(0.0545P)^2^+0.0450P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_ls_number_reflns 1763 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.0777(4) 0.60285(11) 0.00441(8) 0.0519(4) Uani 1 1 d . . . O2 O -0.2720(4) 0.25705(12) -0.39092(8) 0.0481(4) Uani 1 1 d . . . C4 C -0.0265(6) 0.38540(16) -0.12372(12) 0.0429(5) Uani 1 1 d . . . C5 C -0.1696(6) 0.33781(16) -0.19113(12) 0.0444(5) Uani 1 1 d . . . C7 C -0.4689(6) 0.24840(18) -0.31911(11) 0.0434(5) Uani 1 1 d . . . H7 H -0.6741 0.2892 -0.3285 0.052 Uiso 1 1 calc R . . C6 C -0.3000(6) 0.29968(15) -0.24981(12) 0.0440(5) Uani 1 1 d . . . C3 C 0.0958(6) 0.43044(16) -0.06685(12) 0.0435(5) Uani 1 1 d . . . C2 C 0.2343(6) 0.49569(17) 0.00095(12) 0.0457(5) Uani 1 1 d . . . H2 H 0.4686 0.5067 -0.0088 0.055 Uiso 1 1 calc R . . C8 C -0.5455(7) 0.12693(19) -0.30294(13) 0.0549(6) Uani 1 1 d . . . H8A H -0.6608 0.0959 -0.3491 0.082 Uiso 1 1 calc R . . H8B H -0.6793 0.1210 -0.2546 0.082 Uiso 1 1 calc R . . H8C H -0.3458 0.0858 -0.2947 0.082 Uiso 1 1 calc R . . C1 C 0.1871(8) 0.4394(2) 0.08267(13) 0.0676(8) Uani 1 1 d . . . H1A H 0.2911 0.4835 0.1248 0.101 Uiso 1 1 calc R . . H1B H 0.2824 0.3653 0.0813 0.101 Uiso 1 1 calc R . . H1C H -0.0424 0.4334 0.0943 0.101 Uiso 1 1 calc R . . H10 H 0.1652 0.6451 -0.0434 0.068(7) Uiso 1 1 d R . . H20 H -0.3803 0.3010 -0.4304 0.093(10) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0706(11) 0.0426(8) 0.0426(8) -0.0072(6) 0.0104(8) 0.0003(7) O2 0.0538(9) 0.0526(8) 0.0378(7) 0.0027(6) -0.0008(7) 0.0051(8) C4 0.0506(13) 0.0356(11) 0.0424(11) -0.0031(9) 0.0038(10) -0.0003(10) C5 0.0517(14) 0.0370(10) 0.0445(11) -0.0022(9) 0.0057(10) 0.0016(10) C7 0.0419(12) 0.0477(11) 0.0407(10) -0.0013(9) -0.0007(9) 0.0067(11) C6 0.0496(13) 0.0378(10) 0.0448(11) -0.0009(9) 0.0053(11) 0.0035(10) C3 0.0448(13) 0.0382(11) 0.0474(12) 0.0001(9) 0.0042(10) 0.0036(10) C2 0.0464(11) 0.0478(11) 0.0430(11) -0.0075(9) 0.0000(11) 0.0008(10) C8 0.0621(16) 0.0529(13) 0.0496(12) -0.0027(10) -0.0027(11) -0.0102(12) C1 0.083(2) 0.0693(16) 0.0500(12) 0.0066(11) -0.0092(13) -0.0004(16) _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 C2 1.436(2) . ? O1 H10 1.0012 . ? O2 C7 1.437(2) . ? O2 H20 0.9477 . ? C4 C3 1.191(3) . ? C4 C5 1.378(3) . ? C5 C6 1.195(3) . ? C7 C6 1.469(3) . ? C7 C8 1.510(3) . ? C7 H7 0.9900 . ? C3 C2 1.475(3) . ? C2 C1 1.514(3) . ? C2 H2 0.9900 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 H1C 0.9700 . ? 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 O1 H10 104.8 . . ? C7 O2 H20 109.6 . . ? C3 C4 C5 177.5(2) . . ? C6 C5 C4 177.8(2) . . ? O2 C7 C6 109.71(18) . . ? O2 C7 C8 109.42(17) . . ? C6 C7 C8 111.38(17) . . ? O2 C7 H7 108.8 . . ? C6 C7 H7 108.8 . . ? C8 C7 H7 108.8 . . ? C5 C6 C7 176.9(2) . . ? C4 C3 C2 174.8(2) . . ? O1 C2 C3 109.08(17) . . ? O1 C2 C1 107.65(16) . . ? C3 C2 C1 112.61(18) . . ? O1 C2 H2 109.1 . . ? C3 C2 H2 109.1 . . ? C1 C2 H2 109.1 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.097 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.034 # Attachment 'web_deposit_cif_file_2_DinabandhuDas_1296738574.cif' data_LT_240k _database_code_depnum_ccdc_archive 'CCDC 811710' #TrackingRef 'web_deposit_cif_file_2_DinabandhuDas_1296738574.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (s,s)-3,5-Ocatadiyn-2,7-diol ; _chemical_name_common ? _chemical_melting_point 343K _chemical_formula_moiety 'C8 H10 O2' _chemical_formula_sum 'C8 H10 O2' _chemical_formula_weight 138.16 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 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.1427(11) _cell_length_b 11.962(3) _cell_length_c 16.432(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 814.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 240(2) _cell_measurement_reflns_used 991 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 20.24 _chemical_absolute_configuration syn _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.127 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9725 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 240(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 4649 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1764 _reflns_number_gt 1243 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX-II' _computing_cell_refinement 'Bruker SMART APEX-II' _computing_data_reduction 'Bruker SAINT ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED (Barbour 2001)' _computing_publication_material ? _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^)+(0.0597P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(2) _refine_ls_number_reflns 1764 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.0792(4) 0.60260(11) 0.00438(8) 0.0563(4) Uani 1 1 d . . . O2 O -0.2734(4) 0.25718(12) -0.39115(7) 0.0519(4) Uani 1 1 d . . . C4 C -0.0256(6) 0.38578(16) -0.12387(12) 0.0465(5) Uani 1 1 d . . . C5 C -0.1709(6) 0.33820(16) -0.19122(12) 0.0469(5) Uani 1 1 d . . . C7 C -0.4701(5) 0.24904(17) -0.31909(11) 0.0455(5) Uani 1 1 d . . . H7 H -0.6744 0.2901 -0.3284 0.055 Uiso 1 1 calc R . . C6 C -0.3003(6) 0.30004(15) -0.24998(12) 0.0458(5) Uani 1 1 d . . . C3 C 0.0953(6) 0.43066(16) -0.06692(12) 0.0470(5) Uani 1 1 d . . . C2 C 0.2334(6) 0.49559(16) 0.00090(11) 0.0498(5) Uani 1 1 d . . . H2 H 0.4669 0.5066 -0.0091 0.060 Uiso 1 1 calc R . . C8 C -0.5472(7) 0.12763(18) -0.30281(13) 0.0581(6) Uani 1 1 d . . . H8A H -0.6625 0.0966 -0.3490 0.087 Uiso 1 1 calc R . . H8B H -0.6804 0.1219 -0.2544 0.087 Uiso 1 1 calc R . . H8C H -0.3482 0.0864 -0.2946 0.087 Uiso 1 1 calc R . . C1 C 0.1891(8) 0.4390(2) 0.08249(12) 0.0723(8) Uani 1 1 d . . . H1A H 0.2912 0.4834 0.1246 0.108 Uiso 1 1 calc R . . H1B H 0.2871 0.3653 0.0810 0.108 Uiso 1 1 calc R . . H1C H -0.0395 0.4318 0.0942 0.108 Uiso 1 1 calc R . . H10 H 0.1579 0.6462 -0.0413 0.080(8) Uiso 1 1 d R . . H20 H -0.3751 0.3071 -0.4316 0.104(10) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0782(11) 0.0436(8) 0.0471(8) -0.0061(6) 0.0125(8) -0.0002(7) O2 0.0589(9) 0.0565(9) 0.0403(7) 0.0028(6) 0.0009(7) 0.0053(8) C4 0.0541(13) 0.0393(11) 0.0461(11) -0.0032(9) 0.0035(10) 0.0007(10) C5 0.0535(14) 0.0385(10) 0.0488(11) -0.0016(9) 0.0080(10) 0.0028(10) C7 0.0432(12) 0.0489(11) 0.0445(10) -0.0022(9) -0.0009(9) 0.0063(11) C6 0.0492(13) 0.0411(11) 0.0473(11) -0.0020(9) 0.0043(11) 0.0027(10) C3 0.0509(13) 0.0404(11) 0.0498(12) -0.0009(9) 0.0029(10) 0.0023(10) C2 0.0527(12) 0.0492(11) 0.0476(11) -0.0066(9) 0.0005(11) 0.0009(10) C8 0.0629(16) 0.0546(13) 0.0568(13) -0.0047(10) -0.0018(12) -0.0132(12) C1 0.090(2) 0.0736(17) 0.0532(12) 0.0092(11) -0.0098(14) 0.0002(16) _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 C2 1.432(2) . ? O1 H10 0.9701 . ? O2 C7 1.441(2) . ? O2 H20 0.9883 . ? C4 C3 1.189(3) . ? C4 C5 1.382(3) . ? C5 C6 1.195(3) . ? C7 C6 1.468(3) . ? C7 C8 1.511(3) . ? C7 H7 0.9900 . ? C3 C2 1.474(3) . ? C2 C1 1.513(3) . ? C2 H2 0.9900 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 H1C 0.9700 . ? 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 O1 H10 107.5 . . ? C7 O2 H20 110.7 . . ? C3 C4 C5 177.4(2) . . ? C6 C5 C4 178.1(2) . . ? O2 C7 C6 109.66(17) . . ? O2 C7 C8 109.27(16) . . ? C6 C7 C8 111.33(17) . . ? O2 C7 H7 108.8 . . ? C6 C7 H7 108.8 . . ? C8 C7 H7 108.8 . . ? C5 C6 C7 176.7(2) . . ? C4 C3 C2 175.0(2) . . ? O1 C2 C3 109.16(18) . . ? O1 C2 C1 108.10(16) . . ? C3 C2 C1 112.76(18) . . ? O1 C2 H2 108.9 . . ? C3 C2 H2 108.9 . . ? C1 C2 H2 108.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.112 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.033 # Attachment 'web_deposit_cif_file_3_DinabandhuDas_1296738574.cif' data_LT_255k _database_code_depnum_ccdc_archive 'CCDC 811711' #TrackingRef 'web_deposit_cif_file_3_DinabandhuDas_1296738574.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (s,s)-3,5-Ocatadiyn-2,7-diol ; _chemical_name_common ? _chemical_melting_point 343K _chemical_formula_moiety 'C8 H10 O2' _chemical_formula_sum 'C8 H10 O2' _chemical_formula_weight 138.16 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 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.1524(11) _cell_length_b 11.963(3) _cell_length_c 16.429(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 816.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 255(2) _cell_measurement_reflns_used 953 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 20.25 _chemical_absolute_configuration syn _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.124 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9725 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 255(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 4655 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.33 _reflns_number_total 1769 _reflns_number_gt 1192 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX-II' _computing_cell_refinement 'Bruker SMART APEX-II' _computing_data_reduction 'Bruker SAINT ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED (Barbour 2001)' _computing_publication_material ? _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^)+(0.0564P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3(2) _refine_ls_number_reflns 1769 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1197 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.0807(4) 0.60221(11) 0.00440(8) 0.0600(5) Uani 1 1 d . . . O2 O -0.2748(4) 0.25727(13) -0.39131(8) 0.0557(4) Uani 1 1 d . . . C4 C -0.0257(6) 0.38604(17) -0.12411(13) 0.0500(5) Uani 1 1 d . . . C5 C -0.1707(6) 0.33834(17) -0.19145(12) 0.0503(6) Uani 1 1 d . . . C7 C -0.4689(6) 0.24872(18) -0.31904(11) 0.0502(5) Uani 1 1 d . . . H7 H -0.6710 0.2892 -0.3281 0.060 Uiso 1 1 calc R . . C6 C -0.3003(6) 0.30017(16) -0.25017(12) 0.0485(5) Uani 1 1 d . . . C3 C 0.0955(6) 0.43085(17) -0.06731(12) 0.0500(6) Uani 1 1 d . . . C2 C 0.2341(6) 0.49545(17) 0.00059(12) 0.0534(5) Uani 1 1 d . . . H2 H 0.4649 0.5062 -0.0092 0.064 Uiso 1 1 calc R . . C8 C -0.5460(7) 0.12799(19) -0.30269(13) 0.0616(7) Uani 1 1 d . . . H8A H -0.6567 0.0969 -0.3487 0.092 Uiso 1 1 calc R . . H8B H -0.6806 0.1226 -0.2553 0.092 Uiso 1 1 calc R . . H8C H -0.3498 0.0874 -0.2936 0.092 Uiso 1 1 calc R . . C1 C 0.1888(8) 0.4385(2) 0.08226(13) 0.0773(8) Uani 1 1 d . . . H1A H 0.2784 0.4845 0.1245 0.116 Uiso 1 1 calc R . . H1B H 0.2960 0.3674 0.0818 0.116 Uiso 1 1 calc R . . H1C H -0.0369 0.4276 0.0922 0.116 Uiso 1 1 calc R . . H10 H -0.3889 0.3141 -0.4279 0.115(11) Uiso 1 1 d R . . H20 H 0.1550 0.6532 -0.0393 0.105(10) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0814(12) 0.0473(8) 0.0513(8) -0.0072(7) 0.0118(8) -0.0004(8) O2 0.0622(10) 0.0596(9) 0.0454(7) 0.0028(7) 0.0013(7) 0.0065(8) C4 0.0576(14) 0.0416(11) 0.0507(11) -0.0039(9) 0.0044(11) 0.0032(11) C5 0.0563(15) 0.0430(11) 0.0515(12) -0.0025(9) 0.0073(11) 0.0012(11) C7 0.0469(13) 0.0546(12) 0.0491(11) 0.0000(10) -0.0004(10) 0.0058(12) C6 0.0505(13) 0.0440(11) 0.0511(12) -0.0027(9) 0.0049(11) 0.0032(11) C3 0.0532(14) 0.0434(12) 0.0533(12) -0.0018(9) 0.0040(10) 0.0037(11) C2 0.0538(13) 0.0548(12) 0.0516(12) -0.0063(9) -0.0007(12) 0.0010(11) C8 0.0664(17) 0.0579(14) 0.0606(14) -0.0043(10) -0.0008(12) -0.0126(12) C1 0.094(2) 0.0802(18) 0.0580(13) 0.0093(12) -0.0094(14) 0.0000(18) _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 C2 1.429(3) . ? O1 H20 0.9908 . ? O2 C7 1.439(2) . ? O2 H10 1.0241 . ? C4 C3 1.188(3) . ? C4 C5 1.383(3) . ? C5 C6 1.195(3) . ? C7 C6 1.466(3) . ? C7 C8 1.504(3) . ? C7 H7 0.9800 . ? C3 C2 1.474(3) . ? C2 C1 1.516(3) . ? C2 H2 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? 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 O1 H20 112.3 . . ? C7 O2 H10 105.8 . . ? C3 C4 C5 177.5(2) . . ? C6 C5 C4 178.0(2) . . ? O2 C7 C6 109.84(18) . . ? O2 C7 C8 109.57(17) . . ? C6 C7 C8 111.54(18) . . ? O2 C7 H7 108.6 . . ? C6 C7 H7 108.6 . . ? C8 C7 H7 108.6 . . ? C5 C6 C7 176.6(2) . . ? C4 C3 C2 175.1(2) . . ? O1 C2 C3 109.12(18) . . ? O1 C2 C1 107.89(17) . . ? C3 C2 C1 112.68(19) . . ? O1 C2 H2 109.0 . . ? C3 C2 H2 109.0 . . ? C1 C2 H2 109.0 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.100 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.032 # Attachment 'web_deposit_cif_file_4_DinabandhuDas_1296738574.cif' data_LT_270k _database_code_depnum_ccdc_archive 'CCDC 811712' #TrackingRef 'web_deposit_cif_file_4_DinabandhuDas_1296738574.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (s,s)-3,5-Ocatadiyn-2,7-diol ; _chemical_name_common ? _chemical_melting_point 343K _chemical_formula_moiety 'C8 H10 O2' _chemical_formula_sum 'C8 H10 O2' _chemical_formula_weight 138.16 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 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.1632(12) _cell_length_b 11.966(3) _cell_length_c 16.426(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 818.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 270(2) _cell_measurement_reflns_used 914 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 20.25 _chemical_absolute_configuration syn _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9726 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 270(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 4693 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1782 _reflns_number_gt 1131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX-II' _computing_cell_refinement 'Bruker SMART APEX-II' _computing_data_reduction 'Bruker SAINT ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED (Barbour 2001)' _computing_publication_material ? _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^)+(0.0570P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(2) _refine_ls_number_reflns 1782 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1188 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 0.0820(4) 0.60215(11) 0.00433(8) 0.0644(5) Uani 1 1 d . . . O2 O -0.2761(4) 0.25739(13) -0.39126(8) 0.0590(4) Uani 1 1 d . . . C4 C -0.0263(6) 0.38662(17) -0.12447(13) 0.0526(5) Uani 1 1 d . . . C5 C -0.1702(6) 0.33913(17) -0.19168(13) 0.0547(6) Uani 1 1 d . . . C7 C -0.4691(6) 0.24931(18) -0.31901(12) 0.0531(5) Uani 1 1 d . . . H7 H -0.6706 0.2897 -0.3281 0.064 Uiso 1 1 calc R . . C6 C -0.3006(6) 0.30087(16) -0.25013(13) 0.0527(6) Uani 1 1 d . . . C3 C 0.0950(6) 0.43112(17) -0.06759(12) 0.0529(6) Uani 1 1 d . . . C2 C 0.2335(6) 0.49536(18) 0.00021(12) 0.0566(6) Uani 1 1 d . . . H2 H 0.4635 0.5060 -0.0098 0.068 Uiso 1 1 calc R . . C8 C -0.5457(7) 0.12849(19) -0.30246(13) 0.0669(7) Uani 1 1 d . . . H8A H -0.6595 0.0976 -0.3480 0.100 Uiso 1 1 calc R . . H8B H -0.6768 0.1231 -0.2545 0.100 Uiso 1 1 calc R . . H8C H -0.3498 0.0877 -0.2942 0.100 Uiso 1 1 calc R . . C1 C 0.1898(8) 0.4380(2) 0.08179(13) 0.0839(9) Uani 1 1 d . . . H1A H 0.2925 0.4813 0.1235 0.126 Uiso 1 1 calc R . . H1B H 0.2843 0.3649 0.0798 0.126 Uiso 1 1 calc R . . H1C H -0.0353 0.4315 0.0937 0.126 Uiso 1 1 calc R . . H10 H 0.1473 0.6507 -0.0417 0.097(9) Uiso 1 1 d R . . H20 H -0.3844 0.3096 -0.4315 0.121(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 O1 0.0871(12) 0.0516(8) 0.0546(9) -0.0081(7) 0.0128(9) 0.0004(8) O2 0.0658(10) 0.0645(9) 0.0467(8) 0.0029(7) 0.0005(8) 0.0062(8) C4 0.0597(14) 0.0468(12) 0.0513(12) -0.0054(9) 0.0037(11) 0.0023(11) C5 0.0615(16) 0.0463(12) 0.0563(12) -0.0029(10) 0.0094(12) 0.0012(11) C7 0.0504(13) 0.0577(12) 0.0513(11) -0.0011(10) -0.0001(10) 0.0080(12) C6 0.0560(15) 0.0483(12) 0.0538(12) -0.0015(10) 0.0045(12) 0.0036(11) C3 0.0561(15) 0.0474(12) 0.0553(12) -0.0025(10) 0.0062(11) 0.0044(11) C2 0.0550(13) 0.0598(13) 0.0550(12) -0.0062(9) 0.0007(12) 0.0001(11) C8 0.0697(18) 0.0654(15) 0.0657(15) -0.0054(11) 0.0008(13) -0.0138(13) C1 0.102(2) 0.0875(19) 0.0617(13) 0.0108(13) -0.0130(15) -0.0025(19) _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 C2 1.427(3) . ? O1 H10 0.9910 . ? O2 C7 1.436(2) . ? O2 H20 1.0147 . ? C4 C3 1.188(3) . ? C4 C5 1.379(3) . ? C5 C6 1.194(3) . ? C7 C6 1.467(3) . ? C7 C8 1.505(3) . ? C7 H7 0.9800 . ? C3 C2 1.471(3) . ? C2 C1 1.517(3) . ? C2 H2 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? 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 O1 H10 111.6 . . ? C7 O2 H20 109.3 . . ? C3 C4 C5 177.7(2) . . ? C6 C5 C4 178.0(2) . . ? O2 C7 C6 109.97(19) . . ? O2 C7 C8 109.42(17) . . ? C6 C7 C8 111.47(18) . . ? O2 C7 H7 108.6 . . ? C6 C7 H7 108.6 . . ? C8 C7 H7 108.6 . . ? C5 C6 C7 176.9(2) . . ? C4 C3 C2 175.0(2) . . ? O1 C2 C3 109.32(18) . . ? O1 C2 C1 108.09(17) . . ? C3 C2 C1 112.66(19) . . ? O1 C2 H2 108.9 . . ? C3 C2 H2 108.9 . . ? C1 C2 H2 108.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.096 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.031 # Attachment 'web_deposit_cif_file_5_DinabandhuDas_1296738574.cif' data_LT_285k _database_code_depnum_ccdc_archive 'CCDC 811713' #TrackingRef 'web_deposit_cif_file_5_DinabandhuDas_1296738574.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (s,s)-3,5-Ocatadiyn-2,7-diol ; _chemical_name_common ? _chemical_melting_point 343K _chemical_formula_moiety 'C8 H10 O2' _chemical_formula_sum 'C8 H10 O2' _chemical_formula_weight 138.16 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 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.1770(12) _cell_length_b 11.975(3) _cell_length_c 16.430(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 821.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 285(2) _cell_measurement_reflns_used 866 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 20.25 _chemical_absolute_configuration syn _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.117 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9727 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 285(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 4717 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1790 _reflns_number_gt 1123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX-II' _computing_cell_refinement 'Bruker SMART APEX-II' _computing_data_reduction 'Bruker SAINT ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED (Barbour 2001)' _computing_publication_material ? _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^)+(0.0583P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 1790 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 0.0836(5) 0.60183(12) 0.00444(9) 0.0685(5) Uani 1 1 d . . . O2 O -0.2776(4) 0.25771(13) -0.39128(8) 0.0626(5) Uani 1 1 d . . . C4 C -0.0258(6) 0.38683(18) -0.12482(14) 0.0560(6) Uani 1 1 d . . . C5 C -0.1706(7) 0.33963(18) -0.19203(13) 0.0569(6) Uani 1 1 d . . . C7 C -0.4705(6) 0.25003(19) -0.31911(12) 0.0557(6) Uani 1 1 d . . . H7 H -0.6713 0.2906 -0.3281 0.067 Uiso 1 1 calc R . . C6 C -0.3000(6) 0.30099(17) -0.25022(14) 0.0558(6) Uani 1 1 d . . . C3 C 0.0937(6) 0.43134(18) -0.06815(13) 0.0557(6) Uani 1 1 d . . . C2 C 0.2344(7) 0.49490(19) 0.00000(13) 0.0606(6) Uani 1 1 d . . . H2 H 0.4636 0.5053 -0.0102 0.073 Uiso 1 1 calc R . . C8 C -0.5459(8) 0.1291(2) -0.30226(14) 0.0711(8) Uani 1 1 d . . . H8A H -0.6565 0.0977 -0.3481 0.107 Uiso 1 1 calc R . . H8B H -0.6788 0.1238 -0.2547 0.107 Uiso 1 1 calc R . . H8C H -0.3504 0.0888 -0.2932 0.107 Uiso 1 1 calc R . . C1 C 0.1911(9) 0.4375(2) 0.08145(14) 0.0894(10) Uani 1 1 d . . . H1A H 0.3022 0.4788 0.1228 0.134 Uiso 1 1 calc R . . H1B H 0.2765 0.3632 0.0786 0.134 Uiso 1 1 calc R . . H1C H -0.0326 0.4341 0.0946 0.134 Uiso 1 1 calc R . . H20 H -0.3776 0.3134 -0.4321 0.110(10) Uiso 1 1 d R . . H10 H 0.1329 0.6501 -0.0404 0.097(9) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0932(13) 0.0547(9) 0.0575(9) -0.0083(7) 0.0139(9) 0.0001(9) O2 0.0701(11) 0.0676(10) 0.0500(8) 0.0037(7) 0.0014(8) 0.0083(9) C4 0.0635(16) 0.0499(13) 0.0545(12) -0.0066(10) 0.0038(12) 0.0032(12) C5 0.0655(17) 0.0468(12) 0.0585(13) -0.0044(10) 0.0088(12) 0.0038(12) C7 0.0526(14) 0.0615(13) 0.0531(12) 0.0010(10) 0.0003(11) 0.0077(13) C6 0.0591(15) 0.0515(12) 0.0568(13) -0.0017(11) 0.0053(13) 0.0032(12) C3 0.0592(16) 0.0500(13) 0.0580(13) -0.0021(10) 0.0056(11) 0.0042(12) C2 0.0601(14) 0.0651(14) 0.0565(13) -0.0086(10) 0.0003(13) -0.0004(12) C8 0.0766(19) 0.0709(16) 0.0657(15) -0.0040(11) -0.0014(13) -0.0164(14) C1 0.111(3) 0.094(2) 0.0631(14) 0.0100(14) -0.0133(17) 0.000(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 O1 C2 1.429(3) . ? O1 H10 0.9589 . ? O2 C7 1.437(3) . ? O2 H20 1.0332 . ? C4 C3 1.183(3) . ? C4 C5 1.380(3) . ? C5 C6 1.192(3) . ? C7 C6 1.470(3) . ? C7 C8 1.508(3) . ? C7 H7 0.9800 . ? C3 C2 1.476(3) . ? C2 C1 1.515(3) . ? C2 H2 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? 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 O1 H10 114.0 . . ? C7 O2 H20 110.5 . . ? C3 C4 C5 177.4(2) . . ? C6 C5 C4 178.5(2) . . ? O2 C7 C6 109.71(19) . . ? O2 C7 C8 109.28(19) . . ? C6 C7 C8 111.01(19) . . ? O2 C7 H7 108.9 . . ? C6 C7 H7 108.9 . . ? C8 C7 H7 108.9 . . ? C5 C6 C7 177.0(2) . . ? C4 C3 C2 175.7(2) . . ? O1 C2 C3 109.0(2) . . ? O1 C2 C1 108.00(18) . . ? C3 C2 C1 112.9(2) . . ? O1 C2 H2 109.0 . . ? C3 C2 H2 109.0 . . ? C1 C2 H2 109.0 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.097 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.030 # Attachment 'web_deposit_cif_file_6_DinabandhuDas_1296738574.cif' data_LT_300k _database_code_depnum_ccdc_archive 'CCDC 811714' #TrackingRef 'web_deposit_cif_file_6_DinabandhuDas_1296738574.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (s,s)-3,5-Ocatadiyn-2,7-diol ; _chemical_name_common ? _chemical_melting_point 343K _chemical_formula_moiety 'C8 H10 O2' _chemical_formula_sum 'C8 H10 O2' _chemical_formula_weight 138.16 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 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.179(4) _cell_length_b 11.999(11) _cell_length_c 16.431(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 823.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 818 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 20.25 _chemical_absolute_configuration syn _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.114 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 4693 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.39 _reflns_number_total 1788 _reflns_number_gt 1032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX-II' _computing_cell_refinement 'Bruker SMART APEX-II' _computing_data_reduction 'Bruker SAINT ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED (Barbour 2001)' _computing_publication_material ? _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^)+(0.0611P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_ls_number_reflns 1788 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 0.0856(5) 0.60163(13) 0.00437(9) 0.0739(6) Uani 1 1 d . . . O2 O -0.2789(5) 0.25777(15) -0.39132(9) 0.0687(5) Uani 1 1 d . . . C4 C -0.0254(7) 0.38710(19) -0.12505(15) 0.0610(7) Uani 1 1 d . . . C5 C -0.1720(7) 0.33968(19) -0.19220(15) 0.0614(7) Uani 1 1 d . . . C7 C -0.4699(7) 0.2503(2) -0.31923(14) 0.0603(6) Uani 1 1 d . . . H7 H -0.6702 0.2909 -0.3283 0.072 Uiso 1 1 calc R . . C6 C -0.3007(7) 0.30151(18) -0.25061(15) 0.0607(7) Uani 1 1 d . . . C3 C 0.0950(7) 0.43147(19) -0.06840(15) 0.0601(7) Uani 1 1 d . . . C2 C 0.2362(8) 0.4945(2) -0.00024(14) 0.0650(7) Uani 1 1 d . . . H2 H 0.4655 0.5046 -0.0103 0.078 Uiso 1 1 calc R . . C8 C -0.5484(8) 0.1297(2) -0.30189(15) 0.0759(9) Uani 1 1 d . . . H8A H -0.6608 0.0984 -0.3475 0.114 Uiso 1 1 calc R . . H8B H -0.6804 0.1251 -0.2542 0.114 Uiso 1 1 calc R . . H8C H -0.3539 0.0889 -0.2930 0.114 Uiso 1 1 calc R . . C1 C 0.1909(10) 0.4372(3) 0.08093(15) 0.0965(11) Uani 1 1 d . . . H1A H 0.2980 0.4790 0.1226 0.145 Uiso 1 1 calc R . . H1B H 0.2793 0.3634 0.0784 0.145 Uiso 1 1 calc R . . H1C H -0.0333 0.4327 0.0932 0.145 Uiso 1 1 calc R . . H20 H -0.3913 0.3045 -0.4346 0.132(12) Uiso 1 1 d R . . H10 H 0.1654 0.6548 -0.0412 0.095(9) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0990(15) 0.0606(10) 0.0621(10) -0.0099(8) 0.0158(10) 0.0009(10) O2 0.0781(12) 0.0749(11) 0.0532(9) 0.0032(8) 0.0012(9) 0.0076(10) C4 0.0715(17) 0.0508(14) 0.0608(14) -0.0076(12) 0.0043(14) 0.0048(13) C5 0.0679(18) 0.0515(14) 0.0647(15) -0.0044(11) 0.0087(14) 0.0023(13) C7 0.0569(16) 0.0663(15) 0.0575(14) -0.0022(11) -0.0026(12) 0.0079(14) C6 0.0657(18) 0.0534(14) 0.0630(15) -0.0025(12) 0.0055(15) 0.0041(13) C3 0.0634(18) 0.0546(14) 0.0624(15) -0.0043(12) 0.0055(13) 0.0031(13) C2 0.0659(16) 0.0668(15) 0.0624(15) -0.0061(11) 0.0049(15) 0.0026(13) C8 0.083(2) 0.0706(17) 0.0744(18) -0.0028(12) -0.0029(15) -0.0161(16) C1 0.118(3) 0.101(2) 0.0703(16) 0.0139(15) -0.0122(19) 0.003(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 O1 C2 1.433(3) . ? O1 H10 1.0391 . ? O2 C7 1.431(3) . ? O2 H20 1.0203 . ? C4 C3 1.184(3) . ? C4 C5 1.384(4) . ? C5 C6 1.192(3) . ? C7 C6 1.466(4) . ? C7 C8 1.511(4) . ? C7 H7 0.9800 . ? C3 C2 1.475(4) . ? C2 C1 1.512(4) . ? C2 H2 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? 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 O1 H10 111.8 . . ? C7 O2 H20 110.8 . . ? C3 C4 C5 177.5(3) . . ? C6 C5 C4 178.3(3) . . ? O2 C7 C6 109.9(2) . . ? O2 C7 C8 109.7(2) . . ? C6 C7 C8 111.2(2) . . ? O2 C7 H7 108.6 . . ? C6 C7 H7 108.6 . . ? C8 C7 H7 108.6 . . ? C5 C6 C7 176.6(3) . . ? C4 C3 C2 175.8(3) . . ? O1 C2 C3 108.9(2) . . ? O1 C2 C1 107.8(2) . . ? C3 C2 C1 112.7(2) . . ? O1 C2 H2 109.1 . . ? C3 C2 H2 109.1 . . ? C1 C2 H2 109.1 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.093 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.031 # Attachment 'web_deposit_cif_file_7_DinabandhuDas_1296738574.cif' data_LT_315k _database_code_depnum_ccdc_archive 'CCDC 811715' #TrackingRef 'web_deposit_cif_file_7_DinabandhuDas_1296738574.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (s,s)-3,5-Ocatadiyn-2,7-diol ; _chemical_name_common ? _chemical_melting_point 343K _chemical_formula_moiety 'C8 H10 O2' _chemical_formula_sum 'C8 H10 O2' _chemical_formula_weight 138.16 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 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.209(6) _cell_length_b 11.980(16) _cell_length_c 16.40(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 827.0(19) _cell_formula_units_Z 4 _cell_measurement_temperature 315(2) _cell_measurement_reflns_used 590 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 20.29 _chemical_absolute_configuration syn _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.110 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9729 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 315(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 4763 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.61 _reflns_number_total 1807 _reflns_number_gt 867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX-II' _computing_cell_refinement 'Bruker SMART APEX-II' _computing_data_reduction 'Bruker SAINT ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSEED (Barbour 2001)' _computing_publication_material ? _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^)+(0.0620P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(3) _refine_ls_number_reflns 1807 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1380 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _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 0.0880(6) 0.60176(17) 0.00420(11) 0.0823(7) Uani 1 1 d . . . O2 O -0.2804(5) 0.25804(18) -0.39134(11) 0.0760(7) Uani 1 1 d . . . C4 C -0.0262(8) 0.3875(3) -0.1253(2) 0.0681(9) Uani 1 1 d . . . C5 C -0.1728(9) 0.3400(3) -0.19232(19) 0.0671(9) Uani 1 1 d . . . C7 C -0.4710(8) 0.2505(3) -0.31931(17) 0.0666(8) Uani 1 1 d . . . H7 H -0.6697 0.2913 -0.3284 0.080 Uiso 1 1 calc R . . C6 C -0.3010(8) 0.3023(2) -0.2507(2) 0.0670(9) Uani 1 1 d . . . C3 C 0.0943(8) 0.4316(3) -0.06906(18) 0.0654(9) Uani 1 1 d . . . C2 C 0.2376(9) 0.4946(3) -0.00070(18) 0.0734(9) Uani 1 1 d . . . H2 H 0.4651 0.5047 -0.0111 0.088 Uiso 1 1 calc R . . C8 C -0.5485(10) 0.1300(3) -0.30154(18) 0.0841(11) Uani 1 1 d . . . H8A H -0.6674 0.0992 -0.3462 0.126 Uiso 1 1 calc R . . H8B H -0.6725 0.1255 -0.2525 0.126 Uiso 1 1 calc R . . H8C H -0.3551 0.0886 -0.2946 0.126 Uiso 1 1 calc R . . C1 C 0.1933(11) 0.4366(3) 0.08061(18) 0.1070(14) Uani 1 1 d . . . H1A H 0.2944 0.4794 0.1227 0.160 Uiso 1 1 calc R . . H1B H 0.2869 0.3636 0.0783 0.160 Uiso 1 1 calc R . . H1C H -0.0294 0.4300 0.0923 0.160 Uiso 1 1 calc R . . H20 H -0.4120 0.3092 -0.4357 0.123(13) Uiso 1 1 d R . . H10 H 0.1433 0.6572 -0.0447 0.143(15) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1126(18) 0.0650(14) 0.0692(14) -0.0124(11) 0.0150(13) 0.0019(13) O2 0.0855(14) 0.0824(15) 0.0601(11) 0.0041(10) 0.0033(11) 0.0089(13) C4 0.080(2) 0.057(2) 0.0669(19) -0.0086(16) 0.0040(18) 0.0072(18) C5 0.077(2) 0.0546(19) 0.0699(19) -0.0031(15) 0.0100(18) 0.0065(17) C7 0.0632(19) 0.072(2) 0.0648(18) -0.0014(16) -0.0016(15) 0.0090(18) C6 0.070(2) 0.062(2) 0.0683(19) -0.0012(16) 0.0058(19) 0.0037(17) C3 0.069(2) 0.0566(19) 0.070(2) -0.0027(15) 0.0048(16) 0.0053(18) C2 0.073(2) 0.080(2) 0.0676(19) -0.0094(15) 0.0002(19) -0.0003(19) C8 0.090(3) 0.079(2) 0.084(2) -0.0061(17) -0.004(2) -0.015(2) C1 0.132(4) 0.112(3) 0.077(2) 0.013(2) -0.016(2) 0.001(3) _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 C2 1.432(4) . ? O1 H10 1.0670 . ? O2 C7 1.431(4) . ? O2 H20 1.1001 . ? C4 C3 1.178(4) . ? C4 C5 1.382(4) . ? C5 C6 1.189(4) . ? C7 C6 1.470(5) . ? C7 C8 1.508(5) . ? C7 H7 0.9800 . ? C3 C2 1.480(5) . ? C2 C1 1.515(5) . ? C2 H2 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? 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 O1 H10 114.8 . . ? C7 O2 H20 107.3 . . ? C3 C4 C5 177.6(3) . . ? C6 C5 C4 178.1(3) . . ? O2 C7 C6 109.4(3) . . ? O2 C7 C8 109.9(3) . . ? C6 C7 C8 111.2(3) . . ? O2 C7 H7 108.8 . . ? C6 C7 H7 108.8 . . ? C8 C7 H7 108.8 . . ? C5 C6 C7 176.2(3) . . ? C4 C3 C2 175.9(3) . . ? O1 C2 C3 108.7(3) . . ? O1 C2 C1 107.9(2) . . ? C3 C2 C1 112.5(3) . . ? O1 C2 H2 109.2 . . ? C3 C2 H2 109.2 . . ? C1 C2 H2 109.2 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.122 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.032