# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _publ_contact_author_email adb@chem.sdu.dk _publ_contact_author_name 'Andrew D. Bond' _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _audit_creation_method 'SHELXL-97 plus manual editing' _publ_contact_author_address ; University of Southern Denmark Department of Chemistry Campusvej 55 5230 Odense M Denmark ; _publ_contact_author_fax '+45 6550 2509' _publ_contact_author_phone '+45 6615 8780' _publ_section_title ; On the crystal structures and melting point alternation of the n-alkyl carboxylic acids ; _publ_author_name 'Andrew Bond' ################### ## hexanoic acid ## ################### data_C6 _database_code_CSD 197245 _chemical_name_common 'hexanoic acid' _chemical_name_systematic 'hexanoic acid' _chemical_melting_point 271 _chemical_formula_moiety 'C6 H12 O2' _chemical_formula_sum 'C6 H12 O2' _chemical_formula_weight 116.16 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 monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.0180(15) _cell_length_b 5.0236(5) _cell_length_c 9.9426(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.549(5) _cell_angle_gamma 90.00 _cell_volume 719.04(11) _cell_formula_units_Z 4 _cell_measurement_temperature 240(2) _cell_measurement_reflns_used 4861 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.073 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.776 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystal grown in situ in 0.3 mm glass capillary. ; _diffrn_ambient_temperature 240(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 4974 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 24.95 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.987 _reflns_number_total 1233 _reflns_number_gt 886 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0639P)^2^+0.1124P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1233 _refine_ls_number_parameters 77 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1253 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.129 _refine_diff_density_min -0.106 _refine_diff_density_rms 0.027 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 0.48997(10) 0.7518(3) 0.61916(14) 0.0779(5) Uani 1 1 d D . . H1 H 0.5264(13) 0.697(4) 0.570(2) 0.093 Uiso 1 1 d D . . O2 O 0.40079(9) 0.4038(3) 0.53266(13) 0.0753(5) Uani 1 1 d . . . C1 C 0.41891(12) 0.6006(4) 0.61010(17) 0.0613(5) Uani 1 1 d . . . C2 C 0.36028(12) 0.6831(4) 0.70074(19) 0.0698(5) Uani 1 1 d . . . H2A H 0.3377 0.8641 0.6742 0.084 Uiso 1 1 calc R . . H2B H 0.3995 0.6897 0.7981 0.084 Uiso 1 1 calc R . . C3 C 0.27810(13) 0.5085(4) 0.6950(2) 0.0720(6) Uani 1 1 d . . . H3A H 0.2997 0.3247 0.7150 0.086 Uiso 1 1 calc R . . H3B H 0.2358 0.5129 0.5996 0.086 Uiso 1 1 calc R . . C4 C 0.22504(14) 0.5887(4) 0.7966(2) 0.0784(6) Uani 1 1 d . . . H4A H 0.2674 0.5803 0.8919 0.094 Uiso 1 1 calc R . . H4B H 0.2056 0.7746 0.7781 0.094 Uiso 1 1 calc R . . C5 C 0.14229(17) 0.4274(6) 0.7922(3) 0.1066(9) Uani 1 1 d . . . H5A H 0.1615 0.2410 0.8087 0.128 Uiso 1 1 calc R . . H5B H 0.0993 0.4392 0.6975 0.128 Uiso 1 1 calc R . . C6 C 0.09060(18) 0.5051(6) 0.8964(3) 0.1149(10) Uani 1 1 d . . . H6A H 0.0380 0.3869 0.8863 0.172 Uiso 1 1 calc R . . H6B H 0.0687 0.6870 0.8788 0.172 Uiso 1 1 calc R . . H6C H 0.1319 0.4911 0.9909 0.172 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0836(10) 0.0729(9) 0.0874(10) -0.0202(7) 0.0408(7) -0.0105(7) O2 0.0766(9) 0.0754(9) 0.0792(8) -0.0231(7) 0.0305(6) -0.0062(7) C1 0.0652(11) 0.0590(10) 0.0598(10) -0.0007(8) 0.0180(8) 0.0072(9) C2 0.0768(12) 0.0660(11) 0.0715(11) -0.0088(9) 0.0289(9) 0.0079(10) C3 0.0727(12) 0.0696(12) 0.0785(12) -0.0084(9) 0.0290(9) 0.0076(9) C4 0.0783(13) 0.0799(14) 0.0838(12) -0.0058(10) 0.0338(10) 0.0063(11) C5 0.0966(17) 0.116(2) 0.1236(19) -0.0234(16) 0.0580(15) -0.0128(15) C6 0.1009(18) 0.146(3) 0.1182(19) -0.0049(18) 0.0641(16) -0.0014(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 C1 1.292(2) . ? O1 H1 0.88(2) . ? O2 C1 1.235(2) . ? C1 C2 1.487(2) . ? C2 C3 1.502(3) . ? C2 H2A 0.980 . ? C2 H2B 0.980 . ? C3 C4 1.509(3) . ? C3 H3A 0.980 . ? C3 H3B 0.980 . ? C4 C5 1.474(3) . ? C4 H4A 0.980 . ? C4 H4B 0.980 . ? C5 C6 1.512(3) . ? C5 H5A 0.980 . ? C5 H5B 0.980 . ? C6 H6A 0.970 . ? C6 H6B 0.970 . ? C6 H6C 0.970 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 114.4(15) . . ? O2 C1 O1 123.03(16) . . ? O2 C1 C2 122.51(17) . . ? O1 C1 C2 114.46(16) . . ? C1 C2 C3 115.86(16) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C2 C3 C4 113.79(16) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C5 C4 C3 115.76(19) . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4B 108.3 . . ? C3 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? C4 C5 C6 115.5(2) . . ? C4 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? C4 C5 H5B 108.4 . . ? C6 C5 H5B 108.4 . . ? H5A C5 H5B 107.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 1.2(3) . . . . ? O1 C1 C2 C3 -178.81(15) . . . . ? C1 C2 C3 C4 175.69(16) . . . . ? C2 C3 C4 C5 178.44(19) . . . . ? C3 C4 C5 C6 178.7(2) . . . . ? #===END #################### ## heptanoic acid ## #################### data_C7 _database_code_CSD 197246 _chemical_name_common 'heptanoic acid' _chemical_name_systematic 'heptanoic acid' _chemical_melting_point 262 _chemical_formula_moiety 'C7 H14 O2' _chemical_formula_sum 'C7 H14 O2' _chemical_formula_weight 130.18 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.0089(15) _cell_length_b 5.0764(4) _cell_length_c 10.1589(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.864(3) _cell_angle_gamma 90.00 _cell_volume 824.56(12) _cell_formula_units_Z 4 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used 4280 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.049 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.899 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystal grown in situ in 0.3 mm glass capillary. ; _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 2970 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.02 _diffrn_reflns_theta_max 25.42 _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 25.42 _diffrn_measured_fraction_theta_full 0.880 _reflns_number_total 1340 _reflns_number_gt 845 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0747P)^2^+0.2284P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1340 _refine_ls_number_parameters 86 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1010 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1855 _refine_ls_wR_factor_gt 0.1569 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.130 _refine_diff_density_min -0.098 _refine_diff_density_rms 0.026 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 0.00855(13) 0.7572(4) 0.61959(18) 0.0921(7) Uani 1 1 d D . . H1 H -0.0231(16) 0.706(6) 0.549(2) 0.111 Uiso 1 1 d D . . O2 O 0.08719(11) 0.4069(3) 0.58479(17) 0.0908(7) Uani 1 1 d . . . C1 C 0.07195(17) 0.6048(5) 0.6496(2) 0.0751(7) Uani 1 1 d . . . C2 C 0.12348(17) 0.6903(5) 0.7664(3) 0.0849(8) Uani 1 1 d . . . H2A H 0.0869 0.7097 0.8404 0.102 Uiso 1 1 calc R . . H2B H 0.1465 0.8646 0.7482 0.102 Uiso 1 1 calc R . . C3 C 0.19476(17) 0.5104(5) 0.8089(3) 0.0869(9) Uani 1 1 d . . . H3A H 0.1723 0.3333 0.8221 0.104 Uiso 1 1 calc R . . H3B H 0.2334 0.4998 0.7373 0.104 Uiso 1 1 calc R . . C4 C 0.24303(19) 0.5921(6) 0.9321(3) 0.0975(9) Uani 1 1 d . . . H4A H 0.2039 0.6086 1.0028 0.117 Uiso 1 1 calc R . . H4B H 0.2668 0.7670 0.9177 0.117 Uiso 1 1 calc R . . C5 C 0.31257(19) 0.4111(6) 0.9783(3) 0.1002(10) Uani 1 1 d . . . H5A H 0.2885 0.2363 0.9922 0.120 Uiso 1 1 calc R . . H5B H 0.3513 0.3946 0.9071 0.120 Uiso 1 1 calc R . . C6 C 0.3620(2) 0.4862(7) 1.1007(3) 0.1224(12) Uani 1 1 d . . . H6A H 0.3236 0.5020 1.1725 0.147 Uiso 1 1 calc R . . H6B H 0.3865 0.6605 1.0873 0.147 Uiso 1 1 calc R . . C7 C 0.4307(2) 0.3012(8) 1.1435(4) 0.1376(14) Uani 1 1 d . . . H7A H 0.4585 0.3659 1.2242 0.206 Uiso 1 1 calc R . . H7B H 0.4707 0.2895 1.0752 0.206 Uiso 1 1 calc R . . H7C H 0.4074 0.1282 1.1590 0.206 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1124(15) 0.0717(12) 0.0921(13) -0.0196(10) 0.0041(10) 0.0093(11) O2 0.1036(14) 0.0748(12) 0.0947(13) -0.0266(10) 0.0138(10) 0.0047(10) C1 0.0877(18) 0.0616(15) 0.0777(16) -0.0054(14) 0.0216(13) -0.0099(14) C2 0.106(2) 0.0635(15) 0.0859(17) -0.0163(14) 0.0149(15) -0.0078(15) C3 0.0923(19) 0.0761(17) 0.0934(19) -0.0172(15) 0.0155(15) -0.0104(14) C4 0.117(2) 0.0819(19) 0.0938(19) -0.0152(16) 0.0068(16) -0.0058(18) C5 0.099(2) 0.099(2) 0.104(2) -0.0146(18) 0.0102(16) -0.0112(19) C6 0.133(3) 0.107(3) 0.125(3) -0.006(2) -0.011(2) -0.011(2) C7 0.122(3) 0.140(3) 0.149(3) 0.014(3) -0.014(2) -0.013(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 C1 1.300(3) . ? O1 H1 0.89(2) . ? O2 C1 1.232(3) . ? C1 C2 1.476(3) . ? C2 C3 1.508(4) . ? C2 H2A 0.980 . ? C2 H2B 0.980 . ? C3 C4 1.496(4) . ? C3 H3A 0.980 . ? C3 H3B 0.980 . ? C4 C5 1.501(4) . ? C4 H4A 0.980 . ? C4 H4B 0.980 . ? C5 C6 1.490(4) . ? C5 H5A 0.980 . ? C5 H5B 0.980 . ? C6 C7 1.494(4) . ? C6 H6A 0.980 . ? C6 H6B 0.980 . ? C7 H7A 0.970 . ? C7 H7B 0.970 . ? C7 H7C 0.970 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 115(2) . . ? O2 C1 O1 122.2(2) . . ? O2 C1 C2 123.5(3) . . ? O1 C1 C2 114.3(2) . . ? C1 C2 C3 115.9(2) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 115.1(2) . . ? C4 C3 H3A 108.5 . . ? C2 C3 H3A 108.5 . . ? C4 C3 H3B 108.5 . . ? C2 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? C3 C4 C5 115.9(2) . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4B 108.3 . . ? C5 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? C6 C5 C4 117.4(3) . . ? C6 C5 H5A 108.0 . . ? C4 C5 H5A 108.0 . . ? C6 C5 H5B 108.0 . . ? C4 C5 H5B 108.0 . . ? H5A C5 H5B 107.2 . . ? C5 C6 C7 115.8(3) . . ? C5 C6 H6A 108.3 . . ? C7 C6 H6A 108.3 . . ? C5 C6 H6B 108.3 . . ? C7 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -3.6(4) . . . . ? O1 C1 C2 C3 176.7(2) . . . . ? C1 C2 C3 C4 -176.5(2) . . . . ? C2 C3 C4 C5 178.2(2) . . . . ? C3 C4 C5 C6 180.0(3) . . . . ? C4 C5 C6 C7 -180.0(3) . . . . ? #===END ################### ## octanoic acid ## ################### data_C8 _database_code_CSD 197247 _chemical_name_common 'octanoic acid' _chemical_name_systematic 'octanoic acid' _chemical_melting_point 289 _chemical_formula_moiety 'C8 H16 O2' _chemical_formula_sum 'C8 H16 O2' _chemical_formula_weight 144.21 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.6641(11) _cell_length_b 4.9756(3) _cell_length_c 9.5741(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.774(2) _cell_angle_gamma 90.00 _cell_volume 884.59(9) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 19391 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.083 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.678 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystal grown in situ in 0.3 mm glass capillary. ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 6645 _diffrn_reflns_av_R_equivalents 0.1199 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.24 _diffrn_reflns_theta_max 27.44 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.951 _reflns_number_total 1923 _reflns_number_gt 1585 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0775P)^2^+0.3235P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1923 _refine_ls_number_parameters 95 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.1963 _refine_ls_wR_factor_gt 0.1860 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.222 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.044 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 0.49215(7) 0.2559(3) 0.37098(14) 0.0455(4) Uani 1 1 d D . . H1 H 0.5178(12) 0.305(5) 0.445(2) 0.055 Uiso 1 1 d D . . O2 O 0.42161(7) 0.6054(3) 0.40635(14) 0.0432(4) Uani 1 1 d . . . C1 C 0.43726(9) 0.4074(4) 0.33691(18) 0.0352(4) Uani 1 1 d . . . C2 C 0.39213(9) 0.3237(4) 0.20576(19) 0.0380(5) Uani 1 1 d . . . H2A H 0.3763 0.1359 0.2178 0.046 Uiso 1 1 calc R . . H2B H 0.4228 0.3256 0.1272 0.046 Uiso 1 1 calc R . . C3 C 0.32591(10) 0.4944(4) 0.1643(2) 0.0392(5) Uani 1 1 d . . . H3A H 0.2929 0.4841 0.2389 0.047 Uiso 1 1 calc R . . H3B H 0.3406 0.6843 0.1554 0.047 Uiso 1 1 calc R . . C4 C 0.28666(10) 0.4012(4) 0.0266(2) 0.0426(5) Uani 1 1 d . . . H4A H 0.2767 0.2065 0.0335 0.051 Uiso 1 1 calc R . . H4B H 0.3188 0.4260 -0.0485 0.051 Uiso 1 1 calc R . . C5 C 0.21627(11) 0.5456(5) -0.0158(2) 0.0452(5) Uani 1 1 d . . . H5A H 0.2259 0.7406 -0.0227 0.054 Uiso 1 1 calc R . . H5B H 0.1837 0.5196 0.0584 0.054 Uiso 1 1 calc R . . C6 C 0.17872(11) 0.4485(5) -0.1547(2) 0.0470(5) Uani 1 1 d . . . H6A H 0.2107 0.4826 -0.2293 0.056 Uiso 1 1 calc R . . H6B H 0.1717 0.2518 -0.1490 0.056 Uiso 1 1 calc R . . C7 C 0.10636(12) 0.5793(6) -0.1969(3) 0.0587(6) Uani 1 1 d . . . H7A H 0.0741 0.5445 -0.1229 0.070 Uiso 1 1 calc R . . H7B H 0.1132 0.7762 -0.2028 0.070 Uiso 1 1 calc R . . C8 C 0.07045(14) 0.4792(7) -0.3358(3) 0.0674(8) Uani 1 1 d . . . H8A H 0.0248 0.5746 -0.3584 0.101 Uiso 1 1 calc R . . H8B H 0.0611 0.2860 -0.3293 0.101 Uiso 1 1 calc R . . H8C H 0.1021 0.5122 -0.4096 0.101 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0456(8) 0.0444(9) 0.0436(8) -0.0083(6) -0.0090(6) 0.0071(6) O2 0.0426(8) 0.0449(9) 0.0409(7) -0.0133(6) -0.0023(5) 0.0031(6) C1 0.0345(9) 0.0354(10) 0.0352(9) -0.0019(7) 0.0012(7) -0.0026(7) C2 0.0369(9) 0.0379(10) 0.0380(9) -0.0067(7) -0.0026(7) -0.0032(8) C3 0.0388(10) 0.0374(10) 0.0400(9) -0.0055(8) -0.0024(7) -0.0017(8) C4 0.0395(10) 0.0438(11) 0.0425(10) -0.0072(8) -0.0062(8) 0.0003(8) C5 0.0402(10) 0.0457(12) 0.0474(11) -0.0037(9) -0.0064(8) 0.0004(8) C6 0.0417(10) 0.0508(13) 0.0461(11) -0.0041(9) -0.0067(8) -0.0014(9) C7 0.0471(12) 0.0672(16) 0.0581(13) -0.0029(11) -0.0124(10) 0.0051(11) C8 0.0522(14) 0.090(2) 0.0554(14) 0.0023(13) -0.0165(10) -0.0046(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.287(2) . ? O1 H1 0.85(2) . ? O2 C1 1.240(2) . ? C1 C2 1.499(2) . ? C2 C3 1.519(3) . ? C2 H2A 0.990 . ? C2 H2B 0.990 . ? C3 C4 1.515(2) . ? C3 H3A 0.990 . ? C3 H3B 0.990 . ? C4 C5 1.516(3) . ? C4 H4A 0.990 . ? C4 H4B 0.990 . ? C5 C6 1.518(3) . ? C5 H5A 0.990 . ? C5 H5B 0.990 . ? C6 C7 1.517(3) . ? C6 H6A 0.990 . ? C6 H6B 0.990 . ? C7 C8 1.512(3) . ? C7 H7A 0.990 . ? C7 H7B 0.990 . ? C8 H8A 0.980 . ? C8 H8B 0.980 . ? C8 H8C 0.980 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 114.0(18) . . ? O2 C1 O1 123.63(16) . . ? O2 C1 C2 121.82(16) . . ? O1 C1 C2 114.55(16) . . ? C1 C2 C3 115.93(16) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 111.46(16) . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 114.72(17) . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4A 108.6 . . ? C3 C4 H4B 108.6 . . ? C5 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 113.27(18) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 114.64(19) . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6B 108.6 . . ? C5 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 113.4(2) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? 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 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -0.6(3) . . . . ? O1 C1 C2 C3 178.65(16) . . . . ? C1 C2 C3 C4 176.93(17) . . . . ? C2 C3 C4 C5 174.86(17) . . . . ? C3 C4 C5 C6 179.60(18) . . . . ? C4 C5 C6 C7 177.18(19) . . . . ? C5 C6 C7 C8 179.8(2) . . . . ? #===END ################### ## nonanoic acid ## ################### data_C9 _database_code_CSD 197248 _chemical_name_common 'nonanoic acid' _chemical_name_systematic 'nonanoic acid' _chemical_melting_point 285 _chemical_formula_moiety 'C9 H18 O2' _chemical_formula_sum 'C9 H18 O2' _chemical_formula_weight 158.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.1130(3) _cell_length_b 4.9188(6) _cell_length_c 10.1177(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.778(7) _cell_angle_gamma 90.00 _cell_volume 1048.45(15) _cell_formula_units_Z 4 _cell_measurement_temperature 270(2) _cell_measurement_reflns_used 4888 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.002 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.729 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystal grown in situ in 0.3 mm glass capillary. ; _diffrn_ambient_temperature 270(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 4082 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 23.37 _diffrn_measured_fraction_theta_max 0.868 _diffrn_reflns_theta_full 23.37 _diffrn_measured_fraction_theta_full 0.868 _reflns_number_total 1334 _reflns_number_gt 842 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.1100P)^2^+0.1230P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1334 _refine_ls_number_parameters 105 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1142 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.2205 _refine_ls_wR_factor_gt 0.1874 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.109 _refine_diff_density_min -0.081 _refine_diff_density_rms 0.020 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 0.00691(13) 0.7614(5) 0.8822(2) 0.1167(10) Uani 1 1 d D . . H1 H -0.0192(14) 0.710(7) 0.940(3) 0.140 Uiso 1 1 d D . . O2 O 0.06846(10) 0.4067(5) 0.9352(2) 0.1152(9) Uani 1 1 d . . . C1 C 0.05612(16) 0.6130(7) 0.8678(3) 0.0981(10) Uani 1 1 d . . . C2 C 0.09727(17) 0.7051(7) 0.7638(3) 0.1153(11) Uani 1 1 d D . . H2A H 0.1140 0.8827 0.7892 0.138 Uiso 1 1 calc R . . H2B H 0.0708 0.7288 0.6826 0.138 Uiso 1 1 calc R . . C3 C 0.15169(16) 0.5289(7) 0.7339(3) 0.1143(11) Uani 1 1 d D . . H3A H 0.1782 0.5032 0.8149 0.137 Uiso 1 1 calc R . . H3B H 0.1352 0.3520 0.7066 0.137 Uiso 1 1 calc R . . C4 C 0.19201(18) 0.6303(8) 0.6307(4) 0.1300(13) Uani 1 1 d D . . H4A H 0.1651 0.6553 0.5502 0.156 Uiso 1 1 calc R . . H4B H 0.2075 0.8085 0.6581 0.156 Uiso 1 1 calc R . . C5 C 0.24678(18) 0.4676(8) 0.5973(4) 0.1369(13) Uani 1 1 d D . . H5A H 0.2311 0.2903 0.5689 0.164 Uiso 1 1 calc R . . H5B H 0.2732 0.4403 0.6782 0.164 Uiso 1 1 calc R . . C6 C 0.2879(2) 0.5672(10) 0.4962(4) 0.1569(16) Uani 1 1 d D . . H6A H 0.2614 0.5900 0.4150 0.188 Uiso 1 1 calc R . . H6B H 0.3023 0.7471 0.5236 0.188 Uiso 1 1 calc R . . C7 C 0.3432(2) 0.4156(12) 0.4633(5) 0.1742(19) Uani 1 1 d D . . H7A H 0.3288 0.2369 0.4341 0.209 Uiso 1 1 calc R . . H7B H 0.3694 0.3897 0.5448 0.209 Uiso 1 1 calc R . . C8 C 0.3844(3) 0.5186(14) 0.3646(7) 0.225(3) Uani 1 1 d D . . H8A H 0.3585 0.5452 0.2828 0.270 Uiso 1 1 calc R . . H8B H 0.3995 0.6963 0.3938 0.270 Uiso 1 1 calc R . . C9 C 0.4384(3) 0.3603(16) 0.3345(8) 0.283(4) Uani 1 1 d D . . H9A H 0.4624 0.4569 0.2724 0.424 Uiso 1 1 calc R . . H9B H 0.4245 0.1897 0.2968 0.424 Uiso 1 1 calc R . . H9C H 0.4645 0.3279 0.4143 0.424 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.139(2) 0.0984(18) 0.1146(18) 0.0171(12) 0.0214(13) 0.0083(15) O2 0.1335(18) 0.0966(16) 0.1160(16) 0.0239(13) 0.0101(12) 0.0052(13) C1 0.111(2) 0.086(2) 0.096(2) -0.0030(17) 0.0027(17) -0.007(2) C2 0.132(3) 0.099(2) 0.116(2) 0.0173(18) 0.017(2) -0.002(2) C3 0.123(2) 0.106(2) 0.114(2) 0.0075(19) 0.0093(19) -0.013(2) C4 0.136(3) 0.130(3) 0.127(3) 0.021(2) 0.027(2) 0.005(3) C5 0.135(3) 0.132(3) 0.145(3) 0.010(2) 0.022(2) -0.006(3) C6 0.145(3) 0.172(4) 0.159(3) 0.020(3) 0.046(3) 0.004(3) C7 0.149(4) 0.190(5) 0.188(4) 0.004(4) 0.049(3) -0.002(4) C8 0.181(5) 0.244(7) 0.262(6) 0.011(6) 0.098(5) 0.018(5) C9 0.198(6) 0.318(10) 0.344(10) -0.056(9) 0.109(6) -0.018(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.286(4) . ? O1 H1 0.87(2) . ? O2 C1 1.241(4) . ? C1 C2 1.479(4) . ? C2 C3 1.486(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.476(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.464(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.468(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.443(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.457(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.430(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 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 C1 O1 H1 118(2) . . ? O2 C1 O1 123.0(3) . . ? O2 C1 C2 122.0(3) . . ? O1 C1 C2 115.0(3) . . ? C1 C2 C3 117.7(3) . . ? C1 C2 H2A 107.9 . . ? C3 C2 H2A 107.9 . . ? C1 C2 H2B 107.9 . . ? C3 C2 H2B 107.9 . . ? H2A C2 H2B 107.2 . . ? C4 C3 C2 115.9(3) . . ? C4 C3 H3A 108.3 . . ? C2 C3 H3A 108.3 . . ? C4 C3 H3B 108.3 . . ? C2 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? C5 C4 C3 118.7(3) . . ? C5 C4 H4A 107.6 . . ? C3 C4 H4A 107.6 . . ? C5 C4 H4B 107.6 . . ? C3 C4 H4B 107.6 . . ? H4A C4 H4B 107.1 . . ? C4 C5 C6 119.4(4) . . ? C4 C5 H5A 107.5 . . ? C6 C5 H5A 107.5 . . ? C4 C5 H5B 107.5 . . ? C6 C5 H5B 107.5 . . ? H5A C5 H5B 107.0 . . ? C7 C6 C5 120.9(4) . . ? C7 C6 H6A 107.1 . . ? C5 C6 H6A 107.1 . . ? C7 C6 H6B 107.1 . . ? C5 C6 H6B 107.1 . . ? H6A C6 H6B 106.8 . . ? C6 C7 C8 120.5(5) . . ? C6 C7 H7A 107.2 . . ? C8 C7 H7A 107.2 . . ? C6 C7 H7B 107.2 . . ? C8 C7 H7B 107.2 . . ? H7A C7 H7B 106.8 . . ? C9 C8 C7 118.5(6) . . ? C9 C8 H8A 107.7 . . ? C7 C8 H8A 107.7 . . ? C9 C8 H8B 107.7 . . ? C7 C8 H8B 107.7 . . ? H8A C8 H8B 107.1 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 5.1(5) . . . . ? O1 C1 C2 C3 -174.6(3) . . . . ? C1 C2 C3 C4 -179.2(3) . . . . ? C2 C3 C4 C5 179.5(3) . . . . ? C3 C4 C5 C6 -179.2(3) . . . . ? C4 C5 C6 C7 178.4(4) . . . . ? C5 C6 C7 C8 -178.9(5) . . . . ? C6 C7 C8 C9 -179.5(5) . . . . ? #===END ################### ## decanoic acid ## ################### data_C10 _database_code_CSD 197249 _chemical_name_common 'decanoic acid' _chemical_name_systematic 'decanoic acid' _chemical_melting_point 305 _chemical_formula_moiety 'C10 H20 O2' _chemical_formula_sum 'C10 H20 O2' _chemical_formula_weight 172.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.8440(16) _cell_length_b 4.9612(3) _cell_length_c 9.3977(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.559(4) _cell_angle_gamma 90.00 _cell_volume 1063.02(12) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 30834 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.076 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.753 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystal grown in situ in 0.3 mm glass capillary. More than one crystal component present - relatively high merging R and resultant R-factors. ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 8141 _diffrn_reflns_av_R_equivalents 0.1061 _diffrn_reflns_av_sigmaI/netI 0.0769 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.20 _diffrn_reflns_theta_max 27.53 _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.914 _reflns_number_total 2242 _reflns_number_gt 1549 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.1063P)^2^+0.6578P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2242 _refine_ls_number_parameters 113 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1261 _refine_ls_R_factor_gt 0.0925 _refine_ls_wR_factor_ref 0.2350 _refine_ls_wR_factor_gt 0.2108 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.685 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.069 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 0.50744(8) 0.7376(4) 0.37148(19) 0.0430(5) Uani 1 1 d D . . H1 H 0.4875(12) 0.679(6) 0.438(3) 0.052 Uiso 1 1 d D . . O2 O 0.56454(8) 0.3878(4) 0.43117(18) 0.0413(5) Uani 1 1 d . . . C1 C 0.55189(11) 0.5867(5) 0.3551(3) 0.0333(6) Uani 1 1 d . . . C2 C 0.58850(11) 0.6667(5) 0.2349(2) 0.0345(6) Uani 1 1 d . . . H2A H 0.6005 0.8570 0.2490 0.041 Uiso 1 1 calc R . . H2B H 0.5636 0.6574 0.1449 0.041 Uiso 1 1 calc R . . C3 C 0.64314(11) 0.4993(5) 0.2171(2) 0.0330(6) Uani 1 1 d . . . H3A H 0.6696 0.5142 0.3043 0.040 Uiso 1 1 calc R . . H3B H 0.6320 0.3075 0.2046 0.040 Uiso 1 1 calc R . . C4 C 0.67523(11) 0.5924(5) 0.0895(3) 0.0389(6) Uani 1 1 d . . . H4A H 0.6493 0.5636 0.0025 0.047 Uiso 1 1 calc R . . H4B H 0.6823 0.7887 0.0986 0.047 Uiso 1 1 calc R . . C5 C 0.73296(12) 0.4560(6) 0.0691(3) 0.0412(7) Uani 1 1 d . . . H5A H 0.7262 0.2597 0.0586 0.049 Uiso 1 1 calc R . . H5B H 0.7592 0.4843 0.1556 0.049 Uiso 1 1 calc R . . C6 C 0.76333(12) 0.5573(6) -0.0593(3) 0.0415(7) Uani 1 1 d . . . H6A H 0.7377 0.5202 -0.1458 0.050 Uiso 1 1 calc R . . H6B H 0.7677 0.7553 -0.0510 0.050 Uiso 1 1 calc R . . C7 C 0.82299(12) 0.4367(6) -0.0796(3) 0.0455(7) Uani 1 1 d . . . H7A H 0.8486 0.4702 0.0075 0.055 Uiso 1 1 calc R . . H7B H 0.8187 0.2391 -0.0906 0.055 Uiso 1 1 calc R . . C8 C 0.85287(12) 0.5456(6) -0.2063(3) 0.0443(7) Uani 1 1 d . . . H8A H 0.8276 0.5080 -0.2935 0.053 Uiso 1 1 calc R . . H8B H 0.8561 0.7438 -0.1965 0.053 Uiso 1 1 calc R . . C9 C 0.91282(13) 0.4336(7) -0.2264(3) 0.0559(8) Uani 1 1 d . . . H9A H 0.9099 0.2350 -0.2341 0.067 Uiso 1 1 calc R . . H9B H 0.9385 0.4753 -0.1405 0.067 Uiso 1 1 calc R . . C10 C 0.94147(15) 0.5395(8) -0.3555(3) 0.0638(10) Uani 1 1 d . . . H10A H 0.9799 0.4536 -0.3620 0.096 Uiso 1 1 calc R . . H10B H 0.9466 0.7350 -0.3468 0.096 Uiso 1 1 calc R . . H10C H 0.9166 0.4985 -0.4415 0.096 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0455(11) 0.0422(11) 0.0429(10) 0.0079(8) 0.0150(8) 0.0062(9) O2 0.0444(11) 0.0412(11) 0.0391(10) 0.0119(8) 0.0088(8) 0.0024(8) C1 0.0348(13) 0.0296(12) 0.0357(12) 0.0024(10) 0.0050(10) -0.0020(10) C2 0.0377(14) 0.0328(12) 0.0335(12) 0.0045(10) 0.0062(10) -0.0045(10) C3 0.0344(13) 0.0294(12) 0.0356(13) 0.0012(10) 0.0056(10) -0.0042(10) C4 0.0389(15) 0.0392(14) 0.0394(13) 0.0035(11) 0.0094(11) -0.0011(11) C5 0.0423(15) 0.0418(15) 0.0403(14) 0.0021(11) 0.0088(11) -0.0021(12) C6 0.0389(15) 0.0439(15) 0.0424(14) 0.0049(12) 0.0092(11) 0.0013(12) C7 0.0414(16) 0.0493(16) 0.0467(15) 0.0025(13) 0.0102(12) 0.0033(13) C8 0.0413(15) 0.0480(16) 0.0448(15) -0.0011(13) 0.0108(12) -0.0025(13) C9 0.0442(17) 0.069(2) 0.0565(18) 0.0016(16) 0.0156(14) 0.0070(15) C10 0.0504(19) 0.088(3) 0.0557(19) -0.0027(18) 0.0209(15) -0.0102(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 C1 1.278(3) . ? O1 H1 0.846(18) . ? O2 C1 1.242(3) . ? C1 C2 1.500(3) . ? C2 C3 1.517(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.516(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.505(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.514(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.511(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.509(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.501(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.508(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 111(2) . . ? O2 C1 O1 123.7(2) . . ? O2 C1 C2 121.5(2) . . ? O1 C1 C2 114.8(2) . . ? C1 C2 C3 116.0(2) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 111.2(2) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 115.7(2) . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4B 108.3 . . ? C3 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? C4 C5 C6 113.6(2) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 115.5(2) . . ? C7 C6 H6A 108.4 . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6B 108.4 . . ? C5 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C8 C7 C6 114.5(2) . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C7 115.3(2) . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8B 108.4 . . ? C7 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C8 C9 C10 114.7(3) . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -3.0(3) . . . . ? O1 C1 C2 C3 177.2(2) . . . . ? C1 C2 C3 C4 178.0(2) . . . . ? C2 C3 C4 C5 174.9(2) . . . . ? C3 C4 C5 C6 -179.7(2) . . . . ? C4 C5 C6 C7 176.9(2) . . . . ? C5 C6 C7 C8 -178.7(2) . . . . ? C6 C7 C8 C9 178.5(2) . . . . ? C7 C8 C9 C10 178.6(3) . . . . ? #===END ##################### ## undecanoic acid ## ##################### data_C11 _database_code_CSD 197250 _chemical_name_common 'undecanoic acid' _chemical_name_systematic 'undecanoic acid' _chemical_melting_point 302 _chemical_formula_moiety 'C11 H22 O2' _chemical_formula_sum 'C11 H22 O2' _chemical_formula_weight 186.29 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 25.839(3) _cell_length_b 4.9123(4) _cell_length_c 10.0285(11) _cell_angle_alpha 90.00 _cell_angle_beta 99.010(3) _cell_angle_gamma 90.00 _cell_volume 1257.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 10992 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 18.00 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.984 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.770 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystal grown in situ in 0.3 mm capillary. Crystal degraded significantly on cooling and destroyed completely at 280K. Diffraction observed only to 2\q = 18\% (equivalent to ca. 1.1 \%A resolution). ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 2909 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.99 _diffrn_reflns_theta_max 18.04 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 18.04 _diffrn_measured_fraction_theta_full 0.978 _reflns_number_total 859 _reflns_number_gt 609 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.1025P)^2^+0.4038P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 859 _refine_ls_number_parameters 123 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1022 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.2063 _refine_ls_wR_factor_gt 0.1830 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.092 _refine_diff_density_min -0.083 _refine_diff_density_rms 0.023 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 0.5064(2) 0.7563(9) 0.8821(4) 0.1237(16) Uani 1 1 d D . . H1 H 0.486(2) 0.688(13) 0.929(5) 0.18(3) Uiso 1 1 d D . . O2 O 0.55713(14) 0.4023(9) 0.9495(4) 0.1222(16) Uani 1 1 d . . . C1 C 0.5477(3) 0.6039(16) 0.8785(6) 0.1043(18) Uani 1 1 d . . . C2 C 0.5806(3) 0.6988(12) 0.7795(5) 0.125(2) Uani 1 1 d . . . H2A H 0.5934 0.8796 0.8058 0.150 Uiso 1 1 calc R . . H2B H 0.5586 0.7147 0.6921 0.150 Uiso 1 1 calc R . . C3 C 0.6267(2) 0.5222(11) 0.7637(5) 0.1183(19) Uani 1 1 d . . . H3A H 0.6487 0.5037 0.8509 0.142 Uiso 1 1 calc R . . H3B H 0.6141 0.3422 0.7351 0.142 Uiso 1 1 calc R . . C4 C 0.6592(3) 0.6293(13) 0.6644(6) 0.141(2) Uani 1 1 d . . . H4A H 0.6369 0.6460 0.5776 0.169 Uiso 1 1 calc R . . H4B H 0.6709 0.8111 0.6926 0.169 Uiso 1 1 calc R . . C5 C 0.7055(2) 0.4691(13) 0.6454(6) 0.138(2) Uani 1 1 d . . . H5A H 0.6937 0.2886 0.6152 0.166 Uiso 1 1 calc R . . H5B H 0.7273 0.4484 0.7328 0.166 Uiso 1 1 calc R . . C6 C 0.7389(3) 0.5759(15) 0.5496(7) 0.161(2) Uani 1 1 d . . . H6A H 0.7171 0.5875 0.4618 0.193 Uiso 1 1 calc R . . H6B H 0.7484 0.7610 0.5771 0.193 Uiso 1 1 calc R . . C7 C 0.7867(3) 0.4391(15) 0.5301(7) 0.163(3) Uani 1 1 d . . . H7A H 0.7772 0.2554 0.5001 0.196 Uiso 1 1 calc R . . H7B H 0.8083 0.4235 0.6180 0.196 Uiso 1 1 calc R . . C8 C 0.8198(3) 0.5511(18) 0.4374(8) 0.190(3) Uani 1 1 d . . . H8A H 0.7985 0.5598 0.3488 0.228 Uiso 1 1 calc R . . H8B H 0.8279 0.7374 0.4652 0.228 Uiso 1 1 calc R . . C9 C 0.8682(4) 0.424(2) 0.4206(9) 0.214(4) Uani 1 1 d . . . H9A H 0.8599 0.2393 0.3900 0.257 Uiso 1 1 calc R . . H9B H 0.8891 0.4102 0.5095 0.257 Uiso 1 1 calc R . . C10 C 0.9010(5) 0.538(2) 0.3328(11) 0.281(6) Uani 1 1 d . . . H10A H 0.8800 0.5563 0.2442 0.337 Uiso 1 1 calc R . . H10B H 0.9102 0.7210 0.3647 0.337 Uiso 1 1 calc R . . C11 C 0.9471(5) 0.408(3) 0.3156(13) 0.343(8) Uani 1 1 d . . . H11A H 0.9630 0.5037 0.2489 0.515 Uiso 1 1 calc R . . H11B H 0.9395 0.2248 0.2862 0.515 Uiso 1 1 calc R . . H11C H 0.9706 0.4069 0.3997 0.515 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.143(4) 0.111(3) 0.122(3) 0.020(2) 0.038(3) 0.003(3) O2 0.140(3) 0.104(3) 0.124(3) 0.030(2) 0.025(2) 0.009(2) C1 0.108(5) 0.093(5) 0.112(5) -0.004(4) 0.018(4) -0.002(4) C2 0.145(5) 0.118(5) 0.116(4) 0.018(3) 0.037(4) -0.013(4) C3 0.116(4) 0.111(5) 0.129(5) 0.000(3) 0.025(4) -0.009(4) C4 0.142(5) 0.147(5) 0.142(5) 0.021(4) 0.052(4) 0.003(5) C5 0.139(5) 0.133(5) 0.148(5) 0.003(4) 0.042(4) -0.005(4) C6 0.152(6) 0.178(6) 0.165(6) 0.017(5) 0.062(5) 0.004(5) C7 0.147(6) 0.165(6) 0.186(6) -0.005(5) 0.053(5) 0.010(5) C8 0.162(7) 0.218(8) 0.209(7) 0.002(6) 0.088(6) -0.001(7) C9 0.170(7) 0.239(10) 0.253(9) -0.010(7) 0.094(7) 0.003(7) C10 0.211(9) 0.311(14) 0.362(14) 0.017(11) 0.173(11) 0.027(10) C11 0.226(10) 0.385(19) 0.45(2) -0.061(16) 0.157(13) -0.014(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.308(7) . ? O1 H1 0.82(1) . ? O2 C1 1.222(7) . ? C1 C2 1.480(7) . ? C2 C3 1.503(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.495(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.469(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.484(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.444(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.467(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.430(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.431(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.384(12) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 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 C1 O1 H1 112(5) . . ? O2 C1 O1 122.5(5) . . ? O2 C1 C2 124.2(6) . . ? O1 C1 C2 113.3(7) . . ? C1 C2 C3 116.0(5) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 113.9(5) . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C5 C4 C3 116.9(5) . . ? C5 C4 H4A 108.1 . . ? C3 C4 H4A 108.1 . . ? C5 C4 H4B 108.1 . . ? C3 C4 H4B 108.1 . . ? H4A C4 H4B 107.3 . . ? C4 C5 C6 117.5(6) . . ? C4 C5 H5A 107.9 . . ? C6 C5 H5A 107.9 . . ? C4 C5 H5B 107.9 . . ? C6 C5 H5B 107.9 . . ? H5A C5 H5B 107.2 . . ? C7 C6 C5 121.2(6) . . ? C7 C6 H6A 107.0 . . ? C5 C6 H6A 107.0 . . ? C7 C6 H6B 107.0 . . ? C5 C6 H6B 107.0 . . ? H6A C6 H6B 106.8 . . ? C6 C7 C8 120.5(7) . . ? C6 C7 H7A 107.2 . . ? C8 C7 H7A 107.2 . . ? C6 C7 H7B 107.2 . . ? C8 C7 H7B 107.2 . . ? H7A C7 H7B 106.8 . . ? C9 C8 C7 121.2(8) . . ? C9 C8 H8A 107.0 . . ? C7 C8 H8A 107.0 . . ? C9 C8 H8B 107.0 . . ? C7 C8 H8B 107.0 . . ? H8A C8 H8B 106.8 . . ? C8 C9 C10 121.0(9) . . ? C8 C9 H9A 107.1 . . ? C10 C9 H9A 107.1 . . ? C8 C9 H9B 107.1 . . ? C10 C9 H9B 107.1 . . ? H9A C9 H9B 106.8 . . ? C11 C10 C9 120.0(11) . . ? C11 C10 H10A 107.3 . . ? C9 C10 H10A 107.3 . . ? C11 C10 H10B 107.3 . . ? C9 C10 H10B 107.3 . . ? H10A C10 H10B 106.9 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 3.1(8) . . . . ? O1 C1 C2 C3 -176.1(4) . . . . ? C1 C2 C3 C4 -179.0(5) . . . . ? C2 C3 C4 C5 179.1(5) . . . . ? C3 C4 C5 C6 -178.6(5) . . . . ? C4 C5 C6 C7 176.7(5) . . . . ? C5 C6 C7 C8 -178.6(6) . . . . ? C6 C7 C8 C9 177.7(7) . . . . ? C7 C8 C9 C10 -178.3(8) . . . . ? C8 C9 C10 C11 -178.5(10) . . . . ? #===END ##################### ## dodecanoic acid ## ##################### data_C12 _database_code_CSD 197251 _chemical_name_common 'dodecanoic acid' _chemical_name_systematic 'dodecanoic acid' _chemical_melting_point 317 _chemical_formula_moiety 'C12 H24 O2' _chemical_formula_sum 'C12 H24 O2' _chemical_formula_weight 200.31 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 27.563(2) _cell_length_b 4.9627(3) _cell_length_c 9.5266(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.006(2) _cell_angle_gamma 90.00 _cell_volume 1290.41(15) _cell_formula_units_Z 4 _cell_measurement_temperature 270(2) _cell_measurement_reflns_used 58223 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 22.46 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.585 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Grown in situ in 0.3 mm glass capillary. ; _diffrn_ambient_temperature 270(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 5775 _diffrn_reflns_av_R_equivalents 0.0994 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 22.45 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 22.45 _diffrn_measured_fraction_theta_full 0.956 _reflns_number_total 1614 _reflns_number_gt 1258 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0704P)^2^+0.4277P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1614 _refine_ls_number_parameters 132 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.1813 _refine_ls_wR_factor_gt 0.1621 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.186 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.193 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.037 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 0.05420(8) 0.6093(4) 0.9444(2) 0.0641(7) Uani 1 1 d D . . H1 H 0.0329(15) 0.638(12) 0.996(5) 0.19(3) Uiso 1 1 d D . . O2 O 0.00620(7) 0.2607(4) 0.8759(2) 0.0654(7) Uani 1 1 d . . . C1 C 0.04368(10) 0.4083(6) 0.8667(3) 0.0508(8) Uani 1 1 d . . . C2 C 0.07515(11) 0.3313(5) 0.7584(3) 0.0552(8) Uani 1 1 d . . . H2A H 0.0551 0.3367 0.6662 0.066 Uiso 1 1 calc R . . H2B H 0.0853 0.1458 0.7759 0.066 Uiso 1 1 calc R . . C3 C 0.12048(11) 0.4982(5) 0.7501(3) 0.0572(8) Uani 1 1 d . . . H3A H 0.1418 0.4873 0.8399 0.069 Uiso 1 1 calc R . . H3B H 0.1111 0.6853 0.7342 0.069 Uiso 1 1 calc R . . C4 C 0.14840(10) 0.4051(6) 0.6320(3) 0.0600(8) Uani 1 1 d . . . H4A H 0.1547 0.2135 0.6438 0.072 Uiso 1 1 calc R . . H4B H 0.1274 0.4294 0.5423 0.072 Uiso 1 1 calc R . . C5 C 0.19623(11) 0.5442(6) 0.6232(3) 0.0630(9) Uani 1 1 d . . . H5A H 0.2174 0.5211 0.7126 0.076 Uiso 1 1 calc R . . H5B H 0.1902 0.7356 0.6096 0.076 Uiso 1 1 calc R . . C6 C 0.22263(11) 0.4412(6) 0.5045(3) 0.0661(9) Uani 1 1 d . . . H6A H 0.2265 0.2477 0.5151 0.079 Uiso 1 1 calc R . . H6B H 0.2019 0.4737 0.4152 0.079 Uiso 1 1 calc R . . C7 C 0.27226(12) 0.5626(6) 0.4961(3) 0.0698(9) Uani 1 1 d . . . H7A H 0.2928 0.5342 0.5861 0.084 Uiso 1 1 calc R . . H7B H 0.2684 0.7555 0.4825 0.084 Uiso 1 1 calc R . . C8 C 0.29836(11) 0.4502(6) 0.3788(3) 0.0684(9) Uani 1 1 d . . . H8A H 0.3014 0.2567 0.3913 0.082 Uiso 1 1 calc R . . H8B H 0.2780 0.4821 0.2888 0.082 Uiso 1 1 calc R . . C9 C 0.34844(12) 0.5648(7) 0.3707(4) 0.0749(10) Uani 1 1 d . . . H9A H 0.3689 0.5332 0.4607 0.090 Uiso 1 1 calc R . . H9B H 0.3454 0.7583 0.3578 0.090 Uiso 1 1 calc R . . C10 C 0.37407(12) 0.4509(7) 0.2537(4) 0.0758(10) Uani 1 1 d . . . H10A H 0.3766 0.2571 0.2657 0.091 Uiso 1 1 calc R . . H10B H 0.3539 0.4852 0.1637 0.091 Uiso 1 1 calc R . . C11 C 0.42436(14) 0.5624(8) 0.2474(4) 0.0936(12) Uani 1 1 d . . . H11A H 0.4447 0.5255 0.3369 0.112 Uiso 1 1 calc R . . H11B H 0.4219 0.7565 0.2368 0.112 Uiso 1 1 calc R . . C12 C 0.44958(15) 0.4505(9) 0.1285(5) 0.1113(14) Uani 1 1 d . . . H12A H 0.4812 0.5333 0.1310 0.167 Uiso 1 1 calc R . . H12B H 0.4301 0.4881 0.0391 0.167 Uiso 1 1 calc R . . H12C H 0.4535 0.2592 0.1399 0.167 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0697(15) 0.0637(13) 0.0625(13) -0.0174(11) 0.0222(11) -0.0043(11) O2 0.0710(14) 0.0594(13) 0.0700(14) -0.0123(10) 0.0248(10) -0.0139(11) C1 0.0563(19) 0.0476(16) 0.0492(16) -0.0055(14) 0.0093(13) 0.0065(14) C2 0.0630(19) 0.0492(15) 0.0558(17) -0.0058(13) 0.0165(14) 0.0038(14) C3 0.066(2) 0.0501(16) 0.0579(18) -0.0031(13) 0.0170(15) 0.0054(14) C4 0.0614(19) 0.0587(17) 0.0639(18) -0.0084(14) 0.0225(15) -0.0006(15) C5 0.065(2) 0.0583(18) 0.070(2) -0.0018(15) 0.0221(16) 0.0042(15) C6 0.066(2) 0.0653(19) 0.071(2) -0.0031(15) 0.0251(16) -0.0021(16) C7 0.071(2) 0.067(2) 0.075(2) -0.0027(16) 0.0240(17) -0.0018(16) C8 0.069(2) 0.0663(19) 0.075(2) 0.0001(16) 0.0271(17) 0.0021(16) C9 0.071(2) 0.075(2) 0.085(2) -0.0013(18) 0.0306(18) -0.0040(18) C10 0.070(2) 0.079(2) 0.084(2) 0.0032(18) 0.0290(18) 0.0053(18) C11 0.077(2) 0.107(3) 0.105(3) -0.005(2) 0.042(2) -0.007(2) C12 0.090(3) 0.140(4) 0.114(3) 0.006(3) 0.050(2) 0.009(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 C1 1.252(3) . ? O1 H1 0.83(1) . ? O2 C1 1.279(3) . ? C1 C2 1.487(4) . ? C2 C3 1.510(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.521(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.501(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.516(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.507(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.517(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.505(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.510(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.502(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.515(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C1 O1 H1 111(4) . . ? O1 C1 O2 122.6(2) . . ? O1 C1 C2 120.4(3) . . ? O2 C1 C2 117.1(2) . . ? C1 C2 C3 117.5(2) . . ? C1 C2 H2A 107.9 . . ? C3 C2 H2A 107.9 . . ? C1 C2 H2B 107.9 . . ? C3 C2 H2B 107.9 . . ? H2A C2 H2B 107.2 . . ? C2 C3 C4 112.3(2) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 116.1(2) . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4B 108.3 . . ? C3 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? C4 C5 C6 113.8(3) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 116.0(3) . . ? C7 C6 H6A 108.3 . . ? C5 C6 H6A 108.3 . . ? C7 C6 H6B 108.3 . . ? C5 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C6 C7 C8 114.8(3) . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C7 115.5(3) . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8B 108.4 . . ? C7 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C8 C9 C10 115.0(3) . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C11 C10 C9 114.9(3) . . ? C11 C10 H10A 108.5 . . ? C9 C10 H10A 108.5 . . ? C11 C10 H10B 108.5 . . ? C9 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C10 C11 C12 114.7(3) . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? #===END ###################### ## tridecanoic acid ## ###################### data_C13 _database_code_CSD 197252 _chemical_name_common 'tridecanoic acid' _chemical_name_systematic 'tridecanoic acid' _chemical_melting_point 314 _chemical_formula_moiety 'C13 H26 O2' _chemical_formula_sum 'C13 H26 O2' _chemical_formula_weight 214.34 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 59.880(2) _cell_length_b 4.9425(2) _cell_length_c 9.8118(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.800(2) _cell_angle_gamma 90.00 _cell_volume 2897.5(2) _cell_formula_units_Z 8 _cell_measurement_temperature 310(2) _cell_measurement_reflns_used 11049 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 20.82 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.983 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.635 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystal grown in situ in 0.3 mm glass capillary. Diffraction only observed to low resolution (2\q = 18.7\%, equivalent to 1.1 \%A resolution. ; _diffrn_ambient_temperature 310(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 4645 _diffrn_reflns_av_R_equivalents 0.0810 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -52 _diffrn_reflns_limit_h_max 52 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 18.70 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 18.70 _diffrn_measured_fraction_theta_full 0.981 _reflns_number_total 1094 _reflns_number_gt 748 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0850P)^2^+1.6098P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1094 _refine_ls_number_parameters 140 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1770 _refine_ls_wR_factor_gt 0.1496 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.100 _refine_diff_density_min -0.087 _refine_diff_density_rms 0.025 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 0.24700(6) 0.0024(6) 0.6223(3) 0.1089(12) Uani 1 1 d D . . H1 H 0.2558(6) 0.043(9) 0.560(3) 0.131 Uiso 1 1 d D . . O2 O 0.22562(5) 0.3553(6) 0.5639(3) 0.1077(12) Uani 1 1 d . . . C1 C 0.22982(8) 0.1553(11) 0.6362(5) 0.0892(14) Uani 1 1 d . . . C2 C 0.21572(8) 0.0669(8) 0.7480(4) 0.1004(14) Uani 1 1 d . . . H2A H 0.2251 0.0616 0.8325 0.120 Uiso 1 1 calc R . . H2B H 0.2106 -0.1163 0.7285 0.120 Uiso 1 1 calc R . . C3 C 0.19572(7) 0.2379(8) 0.7702(4) 0.0990(14) Uani 1 1 d . . . H3A H 0.2006 0.4216 0.7900 0.119 Uiso 1 1 calc R . . H3B H 0.1861 0.2420 0.6865 0.119 Uiso 1 1 calc R . . C4 C 0.18245(8) 0.1395(9) 0.8838(4) 0.1149(16) Uani 1 1 d . . . H4A H 0.1786 -0.0484 0.8660 0.138 Uiso 1 1 calc R . . H4B H 0.1920 0.1445 0.9675 0.138 Uiso 1 1 calc R . . C5 C 0.16149(8) 0.2892(9) 0.9077(5) 0.1128(15) Uani 1 1 d . . . H5A H 0.1519 0.2849 0.8242 0.135 Uiso 1 1 calc R . . H5B H 0.1653 0.4770 0.9264 0.135 Uiso 1 1 calc R . . C6 C 0.14846(8) 0.1848(10) 1.0220(5) 0.1270(17) Uani 1 1 d . . . H6A H 0.1457 -0.0064 1.0061 0.152 Uiso 1 1 calc R . . H6B H 0.1579 0.2001 1.1059 0.152 Uiso 1 1 calc R . . C7 C 0.12671(8) 0.3139(10) 1.0453(5) 0.1305(18) Uani 1 1 d . . . H7A H 0.1173 0.3042 0.9610 0.157 Uiso 1 1 calc R . . H7B H 0.1294 0.5038 1.0653 0.157 Uiso 1 1 calc R . . C8 C 0.11402(9) 0.1961(11) 1.1573(6) 0.1431(19) Uani 1 1 d . . . H8A H 0.1118 0.0049 1.1387 0.172 Uiso 1 1 calc R . . H8B H 0.1233 0.2107 1.2419 0.172 Uiso 1 1 calc R . . C9 C 0.09212(9) 0.3152(11) 1.1798(6) 0.154(2) Uani 1 1 d . . . H9A H 0.0830 0.3061 1.0944 0.184 Uiso 1 1 calc R . . H9B H 0.0944 0.5052 1.2014 0.184 Uiso 1 1 calc R . . C10 C 0.07928(10) 0.1948(12) 1.2868(6) 0.170(2) Uani 1 1 d . . . H10A H 0.0883 0.2081 1.3726 0.204 Uiso 1 1 calc R . . H10B H 0.0774 0.0038 1.2664 0.204 Uiso 1 1 calc R . . C11 C 0.05703(12) 0.3085(14) 1.3080(7) 0.205(3) Uani 1 1 d . . . H11A H 0.0589 0.4987 1.3303 0.246 Uiso 1 1 calc R . . H11B H 0.0481 0.2984 1.2219 0.246 Uiso 1 1 calc R . . C12 C 0.04413(14) 0.1829(16) 1.4138(9) 0.256(4) Uani 1 1 d D . . H12A H 0.0418 -0.0060 1.3900 0.307 Uiso 1 1 calc R . . H12B H 0.0532 0.1880 1.4994 0.307 Uiso 1 1 calc R . . C13 C 0.02291(15) 0.300(2) 1.4360(10) 0.347(6) Uani 1 1 d D . . H13A H 0.0161 0.2018 1.5068 0.520 Uiso 1 1 calc R . . H13B H 0.0135 0.2905 1.3531 0.520 Uiso 1 1 calc R . . H13C H 0.0249 0.4853 1.4629 0.520 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.124(3) 0.101(2) 0.105(3) 0.0219(19) 0.0322(19) 0.007(2) O2 0.120(2) 0.096(2) 0.109(2) 0.0296(19) 0.0187(17) 0.0055(18) C1 0.089(3) 0.085(3) 0.094(4) -0.008(3) 0.014(3) -0.004(3) C2 0.106(3) 0.100(3) 0.098(3) 0.014(3) 0.023(3) -0.006(3) C3 0.098(3) 0.098(3) 0.103(3) 0.001(3) 0.022(3) -0.011(3) C4 0.112(4) 0.119(4) 0.117(4) 0.011(3) 0.033(3) 0.001(3) C5 0.114(4) 0.111(4) 0.115(4) 0.003(3) 0.027(3) -0.009(3) C6 0.125(4) 0.126(4) 0.133(4) 0.011(3) 0.036(3) 0.006(3) C7 0.111(4) 0.130(4) 0.154(5) -0.001(4) 0.037(3) 0.005(3) C8 0.129(4) 0.147(5) 0.159(5) 0.005(4) 0.054(4) 0.000(4) C9 0.126(4) 0.166(5) 0.175(5) -0.002(4) 0.056(4) 0.002(4) C10 0.141(5) 0.182(6) 0.197(6) -0.008(5) 0.078(5) -0.007(4) C11 0.159(6) 0.237(7) 0.231(7) -0.004(6) 0.092(6) -0.005(6) C12 0.189(7) 0.261(9) 0.335(11) 0.007(8) 0.145(8) 0.020(7) C13 0.199(8) 0.391(15) 0.467(17) -0.024(11) 0.151(10) -0.001(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.291(5) . ? O1 H1 0.86(1) . ? O2 C1 1.233(5) . ? C1 C2 1.493(5) . ? C2 C3 1.493(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.493(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.489(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.500(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.481(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.495(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.468(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.468(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.474(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.472(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.426(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 C1 O1 H1 118(3) . . ? O2 C1 O1 122.8(4) . . ? O2 C1 C2 123.6(4) . . ? O1 C1 C2 113.6(5) . . ? C1 C2 C3 116.1(4) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 113.4(4) . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C5 C4 C3 116.8(4) . . ? C5 C4 H4A 108.1 . . ? C3 C4 H4A 108.1 . . ? C5 C4 H4B 108.1 . . ? C3 C4 H4B 108.1 . . ? H4A C4 H4B 107.3 . . ? C4 C5 C6 115.6(4) . . ? C4 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? C4 C5 H5B 108.4 . . ? C6 C5 H5B 108.4 . . ? H5A C5 H5B 107.4 . . ? C7 C6 C5 118.2(4) . . ? C7 C6 H6A 107.7 . . ? C5 C6 H6A 107.7 . . ? C7 C6 H6B 107.7 . . ? C5 C6 H6B 107.7 . . ? H6A C6 H6B 107.1 . . ? C6 C7 C8 116.1(5) . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C9 C8 C7 117.2(5) . . ? C9 C8 H8A 108.0 . . ? C7 C8 H8A 108.0 . . ? C9 C8 H8B 108.0 . . ? C7 C8 H8B 108.0 . . ? H8A C8 H8B 107.2 . . ? C8 C9 C10 117.4(5) . . ? C8 C9 H9A 107.9 . . ? C10 C9 H9A 107.9 . . ? C8 C9 H9B 107.9 . . ? C10 C9 H9B 107.9 . . ? H9A C9 H9B 107.2 . . ? C9 C10 C11 117.9(6) . . ? C9 C10 H10A 107.8 . . ? C11 C10 H10A 107.8 . . ? C9 C10 H10B 107.8 . . ? C11 C10 H10B 107.8 . . ? H10A C10 H10B 107.2 . . ? C12 C11 C10 117.4(6) . . ? C12 C11 H11A 108.0 . . ? C10 C11 H11A 108.0 . . ? C12 C11 H11B 108.0 . . ? C10 C11 H11B 108.0 . . ? H11A C11 H11B 107.2 . . ? C13 C12 C11 116.8(8) . . ? C13 C12 H12A 108.1 . . ? C11 C12 H12A 108.1 . . ? C13 C12 H12B 108.1 . . ? C11 C12 H12B 108.1 . . ? H12A C12 H12B 107.3 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -0.5(6) . . . . ? O1 C1 C2 C3 179.3(3) . . . . ? C1 C2 C3 C4 -179.6(3) . . . . ? C2 C3 C4 C5 -176.6(3) . . . . ? C3 C4 C5 C6 179.7(4) . . . . ? C4 C5 C6 C7 -176.1(4) . . . . ? C5 C6 C7 C8 177.9(4) . . . . ? C6 C7 C8 C9 -178.3(4) . . . . ? C7 C8 C9 C10 178.1(4) . . . . ? C8 C9 C10 C11 -178.5(5) . . . . ? C9 C10 C11 C12 178.9(6) . . . . ? C10 C11 C12 C13 178.2(7) . . . . ? #===END ######################## ## tetradecanoic acid ## ######################## data_C14 _database_code_CSD 197253 _chemical_name_common 'tetradecanoic acid' _chemical_name_systematic 'tetradecanoic acid' _chemical_melting_point 328 _chemical_formula_moiety 'C14 H28 O2' _chemical_formula_sum 'C14 H28 O2' _chemical_formula_weight 228.36 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 31.559(3) _cell_length_b 4.9652(5) _cell_length_c 9.4260(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.432(4) _cell_angle_gamma 90.00 _cell_volume 1472.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 270(2) _cell_measurement_reflns_used 58505 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 22.46 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.030 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.735 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Crystal grown in situ in 0.3 mm glass capillary. ; _diffrn_ambient_temperature 270(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 3920 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 22.51 _diffrn_measured_fraction_theta_max 0.781 _diffrn_reflns_theta_full 22.51 _diffrn_measured_fraction_theta_full 0.781 _reflns_number_total 1509 _reflns_number_gt 1206 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0640P)^2^+0.4988P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1509 _refine_ls_number_parameters 150 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1526 _refine_ls_wR_factor_gt 0.1420 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.121 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.173 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.027 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 0.00608(6) 0.2378(4) -0.3700(2) 0.0660(6) Uani 1 1 d D . . H1 H -0.0112(10) 0.194(9) -0.442(3) 0.164(19) Uiso 1 1 d D . . O2 O 0.04713(5) -0.1134(4) -0.41174(18) 0.0627(6) Uani 1 1 d . . . C1 C 0.03862(8) 0.0861(6) -0.3388(3) 0.0515(8) Uani 1 1 d . . . C2 C 0.06548(7) 0.1651(5) -0.2083(3) 0.0555(8) Uani 1 1 d . . . H2A H 0.0481 0.1565 -0.1280 0.067 Uiso 1 1 calc R . . H2B H 0.0740 0.3515 -0.2187 0.067 Uiso 1 1 calc R . . C3 C 0.10512(8) -0.0009(5) -0.1729(3) 0.0570(8) Uani 1 1 d . . . H3A H 0.1235 0.0126 -0.2503 0.068 Uiso 1 1 calc R . . H3B H 0.0972 -0.1885 -0.1635 0.068 Uiso 1 1 calc R . . C4 C 0.12922(7) 0.0920(6) -0.0359(3) 0.0592(8) Uani 1 1 d . . . H4A H 0.1345 0.2838 -0.0432 0.071 Uiso 1 1 calc R . . H4B H 0.1111 0.0657 0.0416 0.071 Uiso 1 1 calc R . . C5 C 0.17111(8) -0.0467(6) 0.0023(3) 0.0616(8) Uani 1 1 d . . . H5A H 0.1894 -0.0229 -0.0750 0.074 Uiso 1 1 calc R . . H5B H 0.1661 -0.2382 0.0126 0.074 Uiso 1 1 calc R . . C6 C 0.19394(8) 0.0594(6) 0.1393(3) 0.0616(8) Uani 1 1 d . . . H6A H 0.1974 0.2527 0.1303 0.074 Uiso 1 1 calc R . . H6B H 0.1760 0.0281 0.2167 0.074 Uiso 1 1 calc R . . C7 C 0.23713(8) -0.0639(6) 0.1787(3) 0.0651(9) Uani 1 1 d . . . H7A H 0.2550 -0.0360 0.1009 0.078 Uiso 1 1 calc R . . H7B H 0.2338 -0.2566 0.1906 0.078 Uiso 1 1 calc R . . C8 C 0.25936(8) 0.0514(6) 0.3140(3) 0.0634(8) Uani 1 1 d . . . H8A H 0.2621 0.2445 0.3024 0.076 Uiso 1 1 calc R . . H8B H 0.2415 0.0210 0.3917 0.076 Uiso 1 1 calc R . . C9 C 0.30292(8) -0.0648(6) 0.3549(3) 0.0663(9) Uani 1 1 d . . . H9A H 0.3207 -0.0363 0.2769 0.080 Uiso 1 1 calc R . . H9B H 0.3001 -0.2577 0.3677 0.080 Uiso 1 1 calc R . . C10 C 0.32512(8) 0.0537(6) 0.4894(3) 0.0667(8) Uani 1 1 d . . . H10A H 0.3277 0.2468 0.4769 0.080 Uiso 1 1 calc R . . H10B H 0.3074 0.0237 0.5675 0.080 Uiso 1 1 calc R . . C11 C 0.36874(8) -0.0602(6) 0.5296(3) 0.0712(9) Uani 1 1 d . . . H11A H 0.3865 -0.0290 0.4516 0.085 Uiso 1 1 calc R . . H11B H 0.3662 -0.2535 0.5412 0.085 Uiso 1 1 calc R . . C12 C 0.39091(8) 0.0551(6) 0.6639(3) 0.0715(9) Uani 1 1 d . . . H12A H 0.3932 0.2487 0.6529 0.086 Uiso 1 1 calc R . . H12B H 0.3734 0.0215 0.7423 0.086 Uiso 1 1 calc R . . C13 C 0.43475(9) -0.0579(7) 0.7019(3) 0.0894(11) Uani 1 1 d . . . H13A H 0.4525 -0.0203 0.6246 0.107 Uiso 1 1 calc R . . H13B H 0.4326 -0.2520 0.7107 0.107 Uiso 1 1 calc R . . C14 C 0.45627(10) 0.0539(8) 0.8385(4) 0.1052(13) Uani 1 1 d . . . H14A H 0.4838 -0.0275 0.8562 0.158 Uiso 1 1 calc R . . H14B H 0.4393 0.0147 0.9161 0.158 Uiso 1 1 calc R . . H14C H 0.4594 0.2453 0.8299 0.158 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0711(13) 0.0665(14) 0.0575(13) -0.0097(12) -0.0126(10) 0.0106(11) O2 0.0709(12) 0.0620(13) 0.0539(12) -0.0172(11) -0.0045(8) 0.0057(10) C1 0.0535(16) 0.0533(19) 0.0468(18) 0.0035(16) -0.0026(13) -0.0034(14) C2 0.0604(16) 0.0554(18) 0.0492(16) -0.0069(14) -0.0055(13) -0.0027(13) C3 0.0586(16) 0.0556(17) 0.0550(17) -0.0009(15) -0.0068(13) -0.0046(13) C4 0.0578(16) 0.0638(19) 0.0539(18) -0.0058(15) -0.0083(13) -0.0018(14) C5 0.0641(17) 0.0596(19) 0.0594(18) -0.0005(16) -0.0052(13) -0.0020(14) C6 0.0614(17) 0.065(2) 0.0555(18) -0.0031(16) -0.0108(13) 0.0016(14) C7 0.0643(17) 0.066(2) 0.0627(19) -0.0015(16) -0.0104(14) 0.0006(15) C8 0.0627(17) 0.066(2) 0.0597(19) -0.0011(16) -0.0093(14) -0.0024(14) C9 0.0600(17) 0.071(2) 0.065(2) 0.0007(17) -0.0131(14) 0.0028(15) C10 0.0677(18) 0.067(2) 0.0632(19) -0.0005(17) -0.0109(14) -0.0022(15) C11 0.0634(18) 0.075(2) 0.071(2) -0.0023(18) -0.0161(15) 0.0038(15) C12 0.0665(18) 0.077(2) 0.068(2) 0.0026(18) -0.0140(15) -0.0046(16) C13 0.074(2) 0.106(3) 0.084(2) -0.004(2) -0.0222(17) 0.0071(19) C14 0.085(2) 0.137(4) 0.087(3) 0.000(2) -0.0309(19) -0.009(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 C1 1.289(3) . ? O1 H1 0.86(1) . ? O2 C1 1.247(3) . ? C1 C2 1.491(3) . ? C2 C3 1.514(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.519(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.509(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.523(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.514(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.519(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.513(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.518(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.509(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.511(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.510(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.514(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 C1 O1 H1 119(3) . . ? O2 C1 O1 122.7(2) . . ? O2 C1 C2 122.1(2) . . ? O1 C1 C2 115.2(3) . . ? C1 C2 C3 116.5(2) . . ? C1 C2 H2A 108.2 . . ? C3 C2 H2A 108.2 . . ? C1 C2 H2B 108.2 . . ? C3 C2 H2B 108.2 . . ? H2A C2 H2B 107.3 . . ? C2 C3 C4 111.9(2) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 115.8(2) . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4B 108.3 . . ? C3 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? C4 C5 C6 113.1(2) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 115.2(2) . . ? C7 C6 H6A 108.5 . . ? C5 C6 H6A 108.5 . . ? C7 C6 H6B 108.5 . . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C6 C7 C8 113.7(2) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C9 C8 C7 115.0(3) . . ? C9 C8 H8A 108.5 . . ? C7 C8 H8A 108.5 . . ? C9 C8 H8B 108.5 . . ? C7 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? C8 C9 C10 114.6(3) . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C9 114.7(3) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 115.0(3) . . ? C10 C11 H11A 108.5 . . ? C12 C11 H11A 108.5 . . ? C10 C11 H11B 108.5 . . ? C12 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C13 C12 C11 114.5(3) . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12B 108.6 . . ? C11 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C12 C13 C14 114.1(3) . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 3.2(4) . . . . ? O1 C1 C2 C3 -177.1(2) . . . . ? C1 C2 C3 C4 -178.3(2) . . . . ? C2 C3 C4 C5 -175.3(2) . . . . ? C3 C4 C5 C6 179.0(2) . . . . ? C4 C5 C6 C7 -177.2(2) . . . . ? C5 C6 C7 C8 178.7(2) . . . . ? C6 C7 C8 C9 -179.1(2) . . . . ? C7 C8 C9 C10 179.4(2) . . . . ? C8 C9 C10 C11 -179.5(2) . . . . ? C9 C10 C11 C12 -179.5(2) . . . . ? C10 C11 C12 C13 -179.2(2) . . . . ? C11 C12 C13 C14 -178.6(3) . . . . ? #===END ######################## ## pentadecanoic acid ## ######################## data_C15 _database_code_CSD 198903 _chemical_name_common 'pentadecanoic acid' _chemical_name_systematic 'pentadecanoic acid' _chemical_melting_point 325 _chemical_formula_moiety 'C15 H30 O2' _chemical_formula_sum 'C15 H30 O2' _chemical_formula_weight 242.39 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x, y, -z-1/2' '-x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z-1/2' _cell_length_a 69.258(3) _cell_length_b 4.9556(2) _cell_length_c 9.7197(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.024(2) _cell_angle_gamma 90.00 _cell_volume 3303.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 330(2) _cell_measurement_reflns_used 15078 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 22.46 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.975 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm glass capilary at ca. 331 K with external heater at ca. 373 K. Crystal destroyed on any further cooling. ; _diffrn_ambient_temperature 330(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 6196 _diffrn_reflns_av_R_equivalents 0.1036 _diffrn_reflns_av_sigmaI/netI 0.0638 _diffrn_reflns_limit_h_min -60 _diffrn_reflns_limit_h_max 58 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 18.00 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 18.00 _diffrn_measured_fraction_theta_full 0.991 _reflns_number_total 1141 _reflns_number_gt 671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0761P)^2^+1.7337P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1141 _refine_ls_number_parameters 157 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1315 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.1889 _refine_ls_wR_factor_gt 0.1564 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.115 _refine_diff_density_min -0.096 _refine_diff_density_rms 0.026 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 0.25281(7) 0.0041(8) 0.3786(4) 0.1056(16) Uani 1 1 d D . . H1 H 0.2429(6) 0.069(11) 0.415(5) 0.127 Uiso 1 1 d D . . O2 O 0.27136(6) 0.3576(8) 0.4471(4) 0.1059(16) Uani 1 1 d . . . C1 C 0.26750(10) 0.1579(15) 0.3719(6) 0.0837(19) Uani 1 1 d . . . C2 C 0.27983(10) 0.0741(11) 0.2666(6) 0.0973(19) Uani 1 1 d . . . H2A H 0.2718 0.0734 0.1766 0.117 Uiso 1 1 calc R . . H2B H 0.2840 -0.1103 0.2867 0.117 Uiso 1 1 calc R . . C3 C 0.29772(9) 0.2418(11) 0.2547(6) 0.0946(19) Uani 1 1 d . . . H3A H 0.2937 0.4272 0.2355 0.114 Uiso 1 1 calc R . . H3B H 0.3061 0.2393 0.3435 0.114 Uiso 1 1 calc R . . C4 C 0.30931(9) 0.1482(11) 0.1439(6) 0.108(2) Uani 1 1 d . . . H4A H 0.3123 -0.0415 0.1597 0.130 Uiso 1 1 calc R . . H4B H 0.3010 0.1623 0.0550 0.130 Uiso 1 1 calc R . . C5 C 0.32783(9) 0.2908(11) 0.1323(6) 0.105(2) Uani 1 1 d . . . H5A H 0.3362 0.2776 0.2207 0.126 Uiso 1 1 calc R . . H5B H 0.3250 0.4804 0.1150 0.126 Uiso 1 1 calc R . . C6 C 0.33881(10) 0.1872(12) 0.0204(6) 0.116(2) Uani 1 1 d . . . H6A H 0.3408 -0.0051 0.0347 0.139 Uiso 1 1 calc R . . H6B H 0.3306 0.2102 -0.0682 0.139 Uiso 1 1 calc R . . C7 C 0.35795(10) 0.3125(12) 0.0101(7) 0.117(2) Uani 1 1 d . . . H7A H 0.3661 0.2943 0.0993 0.140 Uiso 1 1 calc R . . H7B H 0.3559 0.5038 -0.0074 0.140 Uiso 1 1 calc R . . C8 C 0.36888(11) 0.1998(12) -0.0996(7) 0.123(2) Uani 1 1 d . . . H8A H 0.3704 0.0072 -0.0836 0.148 Uiso 1 1 calc R . . H8B H 0.3608 0.2229 -0.1888 0.148 Uiso 1 1 calc R . . C9 C 0.38834(11) 0.3131(13) -0.1108(7) 0.134(2) Uani 1 1 d . . . H9A H 0.3964 0.2917 -0.0214 0.161 Uiso 1 1 calc R . . H9B H 0.3868 0.5053 -0.1279 0.161 Uiso 1 1 calc R . . C10 C 0.39924(11) 0.1984(13) -0.2190(7) 0.137(2) Uani 1 1 d . . . H10A H 0.4006 0.0057 -0.2027 0.164 Uiso 1 1 calc R . . H10B H 0.3913 0.2223 -0.3085 0.164 Uiso 1 1 calc R . . C11 C 0.41875(11) 0.3075(14) -0.2293(8) 0.152(3) Uani 1 1 d . . . H11A H 0.4174 0.4993 -0.2482 0.182 Uiso 1 1 calc R . . H11B H 0.4266 0.2884 -0.1390 0.182 Uiso 1 1 calc R . . C12 C 0.42975(13) 0.1901(15) -0.3333(9) 0.169(3) Uani 1 1 d . . . H12A H 0.4221 0.2142 -0.4241 0.203 Uiso 1 1 calc R . . H12B H 0.4309 -0.0025 -0.3162 0.203 Uiso 1 1 calc R . . C13 C 0.44962(15) 0.2980(17) -0.3392(10) 0.207(4) Uani 1 1 d . . . H13A H 0.4485 0.4910 -0.3550 0.248 Uiso 1 1 calc R . . H13B H 0.4573 0.2717 -0.2487 0.248 Uiso 1 1 calc R . . C14 C 0.46042(17) 0.184(2) -0.4432(13) 0.263(6) Uani 1 1 d D . . H14A H 0.4616 -0.0086 -0.4269 0.315 Uiso 1 1 calc R . . H14B H 0.4527 0.2088 -0.5336 0.315 Uiso 1 1 calc R . . C15 C 0.47939(17) 0.289(2) -0.4501(16) 0.344(8) Uani 1 1 d D . . H15A H 0.4848 0.2021 -0.5242 0.517 Uiso 1 1 calc R . . H15B H 0.4876 0.2554 -0.3636 0.517 Uiso 1 1 calc R . . H15C H 0.4786 0.4796 -0.4669 0.517 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.109(4) 0.104(3) 0.110(3) -0.018(2) 0.037(3) -0.009(3) O2 0.126(4) 0.100(3) 0.094(3) -0.027(2) 0.023(2) -0.008(3) C1 0.080(5) 0.088(6) 0.086(5) 0.004(4) 0.023(4) 0.011(5) C2 0.103(5) 0.096(5) 0.095(4) -0.014(3) 0.023(4) 0.005(4) C3 0.100(5) 0.089(4) 0.098(5) -0.003(3) 0.023(4) 0.017(4) C4 0.110(6) 0.104(5) 0.116(5) -0.014(4) 0.033(4) 0.004(4) C5 0.108(5) 0.103(5) 0.107(5) -0.005(4) 0.032(4) -0.001(4) C6 0.112(6) 0.120(5) 0.122(6) -0.010(4) 0.044(5) -0.007(5) C7 0.106(6) 0.116(5) 0.137(6) -0.003(4) 0.044(5) 0.001(5) C8 0.112(6) 0.124(5) 0.142(6) 0.000(4) 0.044(5) 0.003(5) C9 0.117(7) 0.143(6) 0.152(7) -0.001(5) 0.051(5) -0.002(5) C10 0.112(6) 0.154(6) 0.154(7) 0.007(5) 0.053(5) -0.005(5) C11 0.111(6) 0.170(7) 0.187(8) -0.003(6) 0.064(6) -0.006(5) C12 0.142(8) 0.185(8) 0.198(8) 0.008(6) 0.086(7) 0.013(6) C13 0.165(9) 0.236(10) 0.243(10) 0.002(8) 0.113(8) 0.006(8) C14 0.190(11) 0.276(12) 0.355(16) -0.006(10) 0.153(11) -0.024(10) C15 0.194(12) 0.381(18) 0.49(2) 0.006(13) 0.159(13) -0.015(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.280(6) . ? O1 H1 0.88(2) . ? O2 C1 1.237(7) . ? C1 C2 1.481(7) . ? C2 C3 1.510(6) . ? C2 H2A 0.970 . ? C2 H2B 0.970 . ? C3 C4 1.504(7) . ? C3 H3A 0.970 . ? C3 H3B 0.970 . ? C4 C5 1.483(7) . ? C4 H4A 0.970 . ? C4 H4B 0.970 . ? C5 C6 1.501(7) . ? C5 H5A 0.970 . ? C5 H5B 0.970 . ? C6 C7 1.480(7) . ? C6 H6A 0.970 . ? C6 H6B 0.970 . ? C7 C8 1.499(7) . ? C7 H7A 0.970 . ? C7 H7B 0.970 . ? C8 C9 1.478(7) . ? C8 H8A 0.970 . ? C8 H8B 0.970 . ? C9 C10 1.490(8) . ? C9 H9A 0.970 . ? C9 H9B 0.970 . ? C10 C11 1.472(8) . ? C10 H10A 0.970 . ? C10 H10B 0.970 . ? C11 C12 1.468(8) . ? C11 H11A 0.970 . ? C11 H11B 0.970 . ? C12 C13 1.485(9) . ? C12 H12A 0.970 . ? C12 H12B 0.970 . ? C13 C14 1.453(10) . ? C13 H13A 0.970 . ? C13 H13B 0.970 . ? C14 C15 1.423(8) . ? C14 H14A 0.970 . ? C14 H14B 0.970 . ? C15 H15A 0.960 . ? C15 H15B 0.960 . ? C15 H15C 0.960 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 119(4) . . ? O2 C1 O1 123.6(6) . . ? O2 C1 C2 122.4(6) . . ? O1 C1 C2 114.0(6) . . ? C1 C2 C3 117.2(5) . . ? C1 C2 H2A 108.0 . . ? C3 C2 H2A 108.0 . . ? C1 C2 H2B 108.0 . . ? C3 C2 H2B 108.0 . . ? H2A C2 H2B 107.2 . . ? C4 C3 C2 114.2(5) . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3B 108.7 . . ? C2 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C5 C4 C3 117.5(5) . . ? C5 C4 H4A 107.9 . . ? C3 C4 H4A 107.9 . . ? C5 C4 H4B 107.9 . . ? C3 C4 H4B 107.9 . . ? H4A C4 H4B 107.2 . . ? C4 C5 C6 115.0(5) . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C7 C6 C5 117.0(5) . . ? C7 C6 H6A 108.0 . . ? C5 C6 H6A 108.0 . . ? C7 C6 H6B 108.0 . . ? C5 C6 H6B 108.0 . . ? H6A C6 H6B 107.3 . . ? C6 C7 C8 116.0(5) . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C9 C8 C7 117.8(6) . . ? C9 C8 H8A 107.8 . . ? C7 C8 H8A 107.8 . . ? C9 C8 H8B 107.8 . . ? C7 C8 H8B 107.8 . . ? H8A C8 H8B 107.2 . . ? C8 C9 C10 117.6(6) . . ? C8 C9 H9A 107.9 . . ? C10 C9 H9A 107.9 . . ? C8 C9 H9B 107.9 . . ? C10 C9 H9B 107.9 . . ? H9A C9 H9B 107.2 . . ? C11 C10 C9 117.9(7) . . ? C11 C10 H10A 107.8 . . ? C9 C10 H10A 107.8 . . ? C11 C10 H10B 107.8 . . ? C9 C10 H10B 107.8 . . ? H10A C10 H10B 107.2 . . ? C12 C11 C10 118.1(7) . . ? C12 C11 H11A 107.8 . . ? C10 C11 H11A 107.8 . . ? C12 C11 H11B 107.8 . . ? C10 C11 H11B 107.8 . . ? H11A C11 H11B 107.1 . . ? C11 C12 C13 117.2(7) . . ? C11 C12 H12A 108.0 . . ? C13 C12 H12A 108.0 . . ? C11 C12 H12B 108.0 . . ? C13 C12 H12B 108.0 . . ? H12A C12 H12B 107.2 . . ? C14 C13 C12 117.2(9) . . ? C14 C13 H13A 108.0 . . ? C12 C13 H13A 108.0 . . ? C14 C13 H13B 108.0 . . ? C12 C13 H13B 108.0 . . ? H13A C13 H13B 107.2 . . ? C15 C14 C13 117.3(11) . . ? C15 C14 H14A 108.0 . . ? C13 C14 H14A 108.0 . . ? C15 C14 H14B 108.0 . . ? C13 C14 H14B 108.0 . . ? H14A C14 H14B 107.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 0.7(8) . . . . ? O1 C1 C2 C3 -178.6(5) . . . . ? C1 C2 C3 C4 -178.9(5) . . . . ? C2 C3 C4 C5 -175.9(4) . . . . ? C3 C4 C5 C6 179.6(5) . . . . ? C4 C5 C6 C7 -176.5(5) . . . . ? C5 C6 C7 C8 178.2(5) . . . . ? C6 C7 C8 C9 -178.1(5) . . . . ? C7 C8 C9 C10 179.4(5) . . . . ? C8 C9 C10 C11 -179.1(5) . . . . ? C9 C10 C11 C12 178.4(6) . . . . ? C10 C11 C12 C13 -178.3(6) . . . . ? C11 C12 C13 C14 -179.2(8) . . . . ? C12 C13 C14 C15 179.4(9) . . . . ? #===END