Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _audit_creation_date '28 October 2004' _audit_creation_method 'SHELXL-97 plus manual editing' _publ_contact_author_name 'Andrew D. Bond' _publ_contact_author_address ; University of Southern Denmark Department of Chemistry Campusvej 55 5230 Odense Denmark ; _publ_contact_author_email adb@chem.sdu.dk _publ_contact_author_fax '+45 6615 8780' _publ_contact_author_phone '+45 6650 2545' _publ_section_title ; Inversion of the melting point alternation in n-alkyl carboxylic acids by co-crystallization with pyrazine ; _publ_author_name 'Andrew Bond' ## CCDC 246214 data_C11 _database_code_depnum_ccdc_archive 'CCDC 246214' _chemical_name_systematic ? _chemical_name_common '1:2 pyrazine/undecanoic acid' _chemical_melting_point ? _chemical_formula_moiety '(C11 H22 O2)2, C4 H4 N2' _chemical_formula_sum 'C26 H48 N2 O4' _chemical_formula_weight 452.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4567(3) _cell_length_b 6.8657(5) _cell_length_c 18.9798(12) _cell_angle_alpha 84.785(3) _cell_angle_beta 90.874(2) _cell_angle_gamma 75.585(3) _cell_volume 685.30(8) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 12926 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_rad 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.097 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 250 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in 0.30 mm glass capillary at ca. 295 K. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 4963 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0593 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.35 _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 27.35 _diffrn_measured_fraction_theta_full 0.923 _reflns_number_total 2853 _reflns_number_gt 2096 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-8 (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a (Bruker, 2003)' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL v.6.10 (Sheldrick, 2000)' _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^)+(0.0542P)^2^+0.3244P] 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 2853 _refine_ls_number_parameters 149 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1667 _refine_ls_wR_factor_gt 0.1475 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.174 _refine_diff_density_min -0.189 _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 -0.3785(3) 0.6410(2) 0.11313(9) 0.0485(4) Uani 1 1 d D . . H1 H -0.510(4) 0.714(4) 0.0891(13) 0.073 Uiso 1 1 d D . . O2 O -0.5710(3) 0.3952(2) 0.10039(9) 0.0481(4) Uani 1 1 d . . . C1 C -0.3964(3) 0.4513(3) 0.12355(10) 0.0327(4) Uani 1 1 d . . . C2 C -0.1752(3) 0.3201(3) 0.16804(10) 0.0339(4) Uani 1 1 d . . . H2A H -0.1717 0.3754 0.2143 0.041 Uiso 1 1 calc R . . H2B H -0.0171 0.3285 0.1445 0.041 Uiso 1 1 calc R . . C3 C -0.1772(3) 0.0987(3) 0.18131(10) 0.0330(4) Uani 1 1 d . . . H3A H -0.1797 0.0409 0.1355 0.040 Uiso 1 1 calc R . . H3B H -0.3324 0.0875 0.2060 0.040 Uiso 1 1 calc R . . C4 C 0.0552(4) -0.0209(3) 0.22614(11) 0.0367(4) Uani 1 1 d . . . H4A H 0.2090 -0.0079 0.2011 0.044 Uiso 1 1 calc R . . H4B H 0.0573 0.0398 0.2714 0.044 Uiso 1 1 calc R . . C5 C 0.0671(4) -0.2446(3) 0.24230(11) 0.0369(4) Uani 1 1 d . . . H5A H 0.0792 -0.3086 0.1974 0.044 Uiso 1 1 calc R . . H5B H -0.0915 -0.2587 0.2644 0.044 Uiso 1 1 calc R . . C6 C 0.2918(4) -0.3553(3) 0.29159(11) 0.0375(5) Uani 1 1 d . . . H6A H 0.4498 -0.3409 0.2692 0.045 Uiso 1 1 calc R . . H6B H 0.2800 -0.2895 0.3362 0.045 Uiso 1 1 calc R . . C7 C 0.3088(4) -0.5793(3) 0.30944(11) 0.0377(5) Uani 1 1 d . . . H7A H 0.3259 -0.6463 0.2651 0.045 Uiso 1 1 calc R . . H7B H 0.1491 -0.5942 0.3307 0.045 Uiso 1 1 calc R . . C8 C 0.5301(4) -0.6863(3) 0.36035(11) 0.0390(5) Uani 1 1 d . . . H8A H 0.5118 -0.6199 0.4048 0.047 Uiso 1 1 calc R . . H8B H 0.6894 -0.6698 0.3392 0.047 Uiso 1 1 calc R . . C9 C 0.5509(4) -0.9111(3) 0.37802(11) 0.0386(5) Uani 1 1 d . . . H9A H 0.3925 -0.9281 0.3996 0.046 Uiso 1 1 calc R . . H9B H 0.5686 -0.9778 0.3336 0.046 Uiso 1 1 calc R . . C10 C 0.7737(4) -1.0152(3) 0.42848(12) 0.0475(5) Uani 1 1 d . . . H10A H 0.7543 -0.9495 0.4731 0.057 Uiso 1 1 calc R . . H10B H 0.9315 -0.9958 0.4072 0.057 Uiso 1 1 calc R . . C11 C 0.7994(5) -1.2403(3) 0.44570(13) 0.0591(7) Uani 1 1 d . . . H11A H 0.9450 -1.2973 0.4786 0.089 Uiso 1 1 calc R . . H11B H 0.8248 -1.3076 0.4020 0.089 Uiso 1 1 calc R . . H11C H 0.6451 -1.2610 0.4675 0.089 Uiso 1 1 calc R . . N1A N -0.7840(3) 0.8854(2) 0.03725(8) 0.0359(4) Uani 1 1 d . . . C1A C -0.9602(4) 0.8015(3) 0.01408(10) 0.0365(4) Uani 1 1 d . . . H1AA H -0.9378 0.6598 0.0235 0.044 Uiso 1 1 calc R . . C2A C -0.8233(4) 1.0847(3) 0.02354(11) 0.0367(4) Uani 1 1 d . . . H2AA H -0.7017 1.1500 0.0397 0.044 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 0.0388(8) 0.0322(7) 0.0718(11) 0.0122(7) -0.0203(7) -0.0112(6) O2 0.0393(8) 0.0337(8) 0.0701(10) 0.0010(7) -0.0177(7) -0.0104(6) C1 0.0283(9) 0.0296(9) 0.0391(10) -0.0006(7) -0.0007(7) -0.0060(7) C2 0.0300(9) 0.0288(9) 0.0414(10) 0.0003(7) -0.0053(8) -0.0062(7) C3 0.0292(9) 0.0300(9) 0.0388(10) -0.0002(7) -0.0018(7) -0.0068(7) C4 0.0317(9) 0.0290(9) 0.0473(11) 0.0012(8) -0.0050(8) -0.0059(7) C5 0.0327(10) 0.0285(9) 0.0474(11) 0.0002(8) -0.0045(8) -0.0058(7) C6 0.0328(10) 0.0301(9) 0.0473(11) 0.0010(8) -0.0051(8) -0.0056(8) C7 0.0335(10) 0.0311(10) 0.0467(11) 0.0003(8) -0.0050(8) -0.0068(8) C8 0.0362(10) 0.0346(10) 0.0441(11) 0.0023(8) -0.0063(8) -0.0077(8) C9 0.0388(10) 0.0327(10) 0.0419(11) 0.0019(8) -0.0040(8) -0.0067(8) C10 0.0461(12) 0.0407(11) 0.0490(13) 0.0067(9) -0.0098(10) -0.0030(9) C11 0.0676(16) 0.0407(12) 0.0587(15) 0.0070(10) -0.0068(12) 0.0009(11) N1A 0.0313(8) 0.0337(9) 0.0406(9) -0.0006(7) -0.0019(6) -0.0054(7) C1A 0.0333(10) 0.0302(9) 0.0446(11) -0.0009(8) -0.0004(8) -0.0066(8) C2A 0.0324(9) 0.0343(10) 0.0441(11) -0.0044(8) -0.0019(8) -0.0096(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 1.328(2) . ? O1 H1 0.861(10) . ? O2 C1 1.204(2) . ? C1 C2 1.507(2) . ? C2 C3 1.521(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.526(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.523(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.526(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.524(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.525(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.525(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.521(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.521(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? N1A C1A 1.326(2) . ? N1A C2A 1.332(2) . ? C1A C2A 1.389(3) 2_375 ? C1A H1AA 0.9500 . ? C2A C1A 1.389(3) 2_375 ? C2A H2AA 0.9500 . ? 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 109.8(19) . . ? O2 C1 O1 123.12(16) . . ? O2 C1 C2 125.35(17) . . ? O1 C1 C2 111.53(15) . . ? C1 C2 C3 115.12(15) . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 110.95(15) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 114.33(15) . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? C3 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 112.62(15) . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 114.13(16) . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C6 C7 C8 113.43(16) . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 113.94(16) . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C10 C9 C8 113.10(17) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 C11 113.73(19) . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? 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 . . ? C1A N1A C2A 117.29(16) . . ? N1A C1A C2A 121.81(18) . 2_375 ? N1A C1A H1AA 119.1 . . ? C2A C1A H1AA 119.1 2_375 . ? N1A C2A C1A 120.90(17) . 2_375 ? N1A C2A H2AA 119.6 . . ? C1A C2A H2AA 119.6 2_375 . ? 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 2.0(3) . . . . ? O1 C1 C2 C3 -178.69(16) . . . . ? C1 C2 C3 C4 179.48(16) . . . . ? C2 C3 C4 C5 179.65(17) . . . . ? C3 C4 C5 C6 -175.81(17) . . . . ? C4 C5 C6 C7 179.55(17) . . . . ? C5 C6 C7 C8 -178.41(17) . . . . ? C6 C7 C8 C9 -179.39(17) . . . . ? C7 C8 C9 C10 179.63(18) . . . . ? C8 C9 C10 C11 -179.08(19) . . . . ? C2A N1A C1A C2A 0.6(3) . . . 2_375 ? C1A N1A C2A C1A -0.6(3) . . . 2_375 ? #===END ## CCDC 246215 data_C12 _database_code_depnum_ccdc_archive 'CCDC 246215' _chemical_name_systematic ? _chemical_name_common '1:2 pyrazine/dodecanoic acid' _chemical_melting_point ? _chemical_formula_moiety '2(C12 H24 O2), C4 H4 N2' _chemical_formula_sum 'C28 H52 N2 O4' _chemical_formula_weight 480.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4447(2) _cell_length_b 6.9028(3) _cell_length_c 20.307(8) _cell_angle_alpha 89.796(1) _cell_angle_beta 88.441(1) _cell_angle_gamma 75.432(1) _cell_volume 738.4(3) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 1915 _cell_measurement_theta_min 3.66 _cell_measurement_theta_max 25.55 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_rad 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.081 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 266 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.5 mm capillary at 312 K. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 3380 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 25.03 _diffrn_measured_fraction_theta_max 0.875 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.875 _reflns_number_total 2282 _reflns_number_gt 1899 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-8 (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a (Bruker, 2003)' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL v.6.10 (Sheldrick, 2000)' _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^)+(0.0941P)^2^+0.2341P] 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 SHELXL _refine_ls_extinction_coef 0.045(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2282 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1724 _refine_ls_wR_factor_gt 0.1640 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.273 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.053 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0953(3) 0.3288(2) 0.39487(8) 0.0438(4) Uani 1 1 d . . . H1 H 0.058(6) 0.246(4) 0.4224(14) 0.078(9) Uiso 1 1 d . . . O2 O 0.0960(3) 0.5753(2) 0.40657(7) 0.0439(4) Uani 1 1 d . . . C1 C -0.0751(3) 0.5146(3) 0.38469(9) 0.0289(4) Uani 1 1 d . . . C2 C -0.2838(3) 0.6331(3) 0.34311(9) 0.0292(5) Uani 1 1 d . . . H2A H -0.4486 0.6315 0.3646 0.035 Uiso 1 1 calc R . . H2B H -0.2748 0.5649 0.3000 0.035 Uiso 1 1 calc R . . C3 C -0.2795(3) 0.8502(3) 0.33087(9) 0.0288(5) Uani 1 1 d . . . H3A H -0.2891 0.9206 0.3736 0.035 Uiso 1 1 calc R . . H3B H -0.1174 0.8542 0.3083 0.035 Uiso 1 1 calc R . . C4 C -0.4999(4) 0.9570(3) 0.28895(9) 0.0317(5) Uani 1 1 d . . . H4A H -0.6607 0.9513 0.3119 0.038 Uiso 1 1 calc R . . H4B H -0.4899 0.8838 0.2467 0.038 Uiso 1 1 calc R . . C5 C -0.5085(3) 1.1754(3) 0.27408(9) 0.0316(5) Uani 1 1 d . . . H5A H -0.5331 1.2519 0.3159 0.038 Uiso 1 1 calc R . . H5B H -0.3435 1.1832 0.2540 0.038 Uiso 1 1 calc R . . C6 C -0.7198(4) 1.2718(3) 0.22780(9) 0.0323(5) Uani 1 1 d . . . H6A H -0.8845 1.2655 0.2484 0.039 Uiso 1 1 calc R . . H6B H -0.6967 1.1930 0.1865 0.039 Uiso 1 1 calc R . . C7 C -0.7305(4) 1.4901(3) 0.21087(9) 0.0320(5) Uani 1 1 d . . . H7A H -0.7564 1.5693 0.2522 0.038 Uiso 1 1 calc R . . H7B H -0.5648 1.4967 0.1910 0.038 Uiso 1 1 calc R . . C8 C -0.9387(4) 1.5857(3) 0.16378(9) 0.0333(5) Uani 1 1 d . . . H8A H -1.1047 1.5788 0.1834 0.040 Uiso 1 1 calc R . . H8B H -0.9123 1.5076 0.1222 0.040 Uiso 1 1 calc R . . C9 C -0.9472(4) 1.8039(3) 0.14795(9) 0.0332(5) Uani 1 1 d . . . H9A H -0.9696 1.8806 0.1897 0.040 Uiso 1 1 calc R . . H9B H -0.7816 1.8097 0.1278 0.040 Uiso 1 1 calc R . . C10 C -1.1565(4) 1.9051(3) 0.10188(10) 0.0357(5) Uani 1 1 d . . . H10A H -1.3225 1.8984 0.1216 0.043 Uiso 1 1 calc R . . H10B H -1.1328 1.8307 0.0596 0.043 Uiso 1 1 calc R . . C11 C -1.1613(4) 2.1239(3) 0.08818(11) 0.0427(6) Uani 1 1 d . . . H11A H -1.1826 2.1972 0.1306 0.051 Uiso 1 1 calc R . . H11B H -0.9953 2.1298 0.0683 0.051 Uiso 1 1 calc R . . C12 C -1.3694(5) 2.2296(4) 0.04291(12) 0.0569(7) Uani 1 1 d . . . H12A H -1.3588 2.3679 0.0362 0.085 Uiso 1 1 calc R . . H12B H -1.5353 2.2295 0.0629 0.085 Uiso 1 1 calc R . . H12C H -1.3488 2.1597 0.0004 0.085 Uiso 1 1 calc R . . N1 N 0.2923(3) 0.1050(2) 0.46509(7) 0.0318(4) Uani 1 1 d . . . C13 C 0.4643(4) 0.1944(3) 0.48730(9) 0.0321(5) Uani 1 1 d . . . H13A H 0.4446 0.3330 0.4791 0.039 Uiso 1 1 calc R . . C14 C 0.3294(3) -0.0903(3) 0.47796(9) 0.0324(5) Uani 1 1 d . . . H14A H 0.2109 -0.1592 0.4628 0.039 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 0.0408(8) 0.0332(8) 0.0632(10) 0.0187(7) -0.0207(8) -0.0184(6) O2 0.0403(8) 0.0336(8) 0.0622(10) 0.0066(7) -0.0191(7) -0.0158(6) C1 0.0293(9) 0.0275(10) 0.0316(9) 0.0026(7) -0.0014(8) -0.0104(8) C2 0.0302(9) 0.0270(10) 0.0326(9) 0.0029(7) -0.0066(8) -0.0107(8) C3 0.0291(9) 0.0256(10) 0.0328(9) 0.0023(7) -0.0031(8) -0.0087(8) C4 0.0330(10) 0.0254(10) 0.0380(10) 0.0039(8) -0.0063(9) -0.0096(8) C5 0.0318(10) 0.0256(10) 0.0381(10) 0.0044(8) -0.0056(9) -0.0082(8) C6 0.0334(10) 0.0257(10) 0.0389(10) 0.0046(8) -0.0084(9) -0.0088(8) C7 0.0321(10) 0.0266(10) 0.0387(10) 0.0054(8) -0.0086(9) -0.0093(8) C8 0.0341(10) 0.0283(10) 0.0387(10) 0.0045(8) -0.0071(9) -0.0096(8) C9 0.0354(10) 0.0290(10) 0.0368(10) 0.0069(8) -0.0074(9) -0.0103(8) C10 0.0363(10) 0.0333(11) 0.0380(11) 0.0064(8) -0.0058(9) -0.0092(9) C11 0.0475(12) 0.0350(12) 0.0449(12) 0.0111(9) -0.0068(10) -0.0085(10) C12 0.0580(15) 0.0475(14) 0.0578(14) 0.0187(11) -0.0096(12) 0.0011(12) N1 0.0301(8) 0.0309(9) 0.0357(9) 0.0038(6) -0.0036(7) -0.0097(7) C13 0.0338(10) 0.0243(9) 0.0401(10) 0.0031(7) -0.0006(8) -0.0110(8) C14 0.0311(9) 0.0310(10) 0.0383(10) 0.0008(8) -0.0044(8) -0.0135(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 1.330(2) . ? O1 H1 1.06(3) . ? O2 C1 1.209(2) . ? C1 C2 1.501(3) . ? C2 C3 1.524(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.522(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.526(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.523(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.531(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.521(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.529(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.522(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.529(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.516(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N1 C13 1.333(2) . ? N1 C14 1.338(2) . ? C13 C14 1.382(3) 2_656 ? C13 H13A 0.9500 . ? C14 C13 1.382(3) 2_656 ? C14 H14A 0.9500 . ? 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 110.8(15) . . ? O2 C1 O1 122.25(18) . . ? O2 C1 C2 125.53(16) . . ? O1 C1 C2 112.21(15) . . ? C1 C2 C3 115.57(14) . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 111.31(14) . . ? 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 . . ? C3 C4 C5 114.61(15) . . ? 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 . . ? C6 C5 C4 112.83(15) . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C5 C6 C7 114.14(15) . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 114.23(15) . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C9 113.35(15) . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C10 C9 C8 114.67(16) . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C9 C10 C11 113.07(17) . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 114.37(19) . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 . . ? 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 . . ? C13 N1 C14 116.80(16) . . ? N1 C13 C14 121.53(17) . 2_656 ? N1 C13 H13A 119.2 . . ? C14 C13 H13A 119.2 2_656 . ? N1 C14 C13 121.67(16) . 2_656 ? N1 C14 H14A 119.2 . . ? C13 C14 H14A 119.2 2_656 . ? 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 -2.7(3) . . . . ? O1 C1 C2 C3 178.13(14) . . . . ? C1 C2 C3 C4 -179.39(14) . . . . ? C2 C3 C4 C5 -179.68(14) . . . . ? C3 C4 C5 C6 175.63(14) . . . . ? C4 C5 C6 C7 -178.93(14) . . . . ? C5 C6 C7 C8 179.07(15) . . . . ? C6 C7 C8 C9 179.59(14) . . . . ? C7 C8 C9 C10 -178.97(15) . . . . ? C8 C9 C10 C11 179.06(15) . . . . ? C9 C10 C11 C12 -179.46(17) . . . . ? C14 N1 C13 C14 -0.1(3) . . . 2_656 ? C13 N1 C14 C13 0.1(3) . . . 2_656 ? #===END ## CCDC 246216 data_C13 _database_code_depnum_ccdc_archive 'CCDC 246216' _chemical_name_systematic ? _chemical_name_common '2:1 pyrazine/tridecanoic acid' _chemical_melting_point ? _chemical_formula_moiety '2(C13 H26 O2), C4 H4 N2' _chemical_formula_sum 'C30 H56 N2 O4' _chemical_formula_weight 508.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4407(9) _cell_length_b 6.8439(11) _cell_length_c 21.498(4) _cell_angle_alpha 84.694(3) _cell_angle_beta 92.957(3) _cell_angle_gamma 75.574(3) _cell_volume 769.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 578 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 24.60 _exptl_crystal_description cyinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_rad 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 282 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.993 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.5 mm capillary at ??? K. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 3495 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.1476 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 23.26 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.967 _reflns_number_total 2134 _reflns_number_gt 1004 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-8 (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a (Bruker, 2003)' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL v.6.10 (Sheldrick, 2000)' _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^)+(0.1026P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2134 _refine_ls_number_parameters 167 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1760 _refine_ls_R_factor_gt 0.0809 _refine_ls_wR_factor_ref 0.2334 _refine_ls_wR_factor_gt 0.1857 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.275 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.075 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 0.4251(6) -0.7069(5) 0.09975(16) 0.0473(11) Uani 1 1 d D . . H1 H 0.548(7) -0.765(7) 0.079(2) 0.071 Uiso 1 1 d D . . O2 O 0.6140(6) -0.4545(5) 0.08865(15) 0.0464(11) Uani 1 1 d . . . C1 C 0.4473(9) -0.5242(8) 0.1091(2) 0.0326(13) Uani 1 1 d . . . C2 C 0.2466(9) -0.4193(7) 0.1482(2) 0.0325(13) Uani 1 1 d . . . H2A H 0.2629 -0.5022 0.1892 0.039 Uiso 1 1 calc R . . H2B H 0.0779 -0.4138 0.1275 0.039 Uiso 1 1 calc R . . C3 C 0.2537(9) -0.2073(7) 0.1599(2) 0.0341(13) Uani 1 1 d . . . H3A H 0.2364 -0.1223 0.1193 0.041 Uiso 1 1 calc R . . H3B H 0.4201 -0.2108 0.1815 0.041 Uiso 1 1 calc R . . C4 C 0.0406(8) -0.1129(7) 0.1998(2) 0.0327(13) Uani 1 1 d . . . H4A H -0.1246 -0.1120 0.1780 0.039 Uiso 1 1 calc R . . H4B H 0.0589 -0.1999 0.2400 0.039 Uiso 1 1 calc R . . C5 C 0.0344(8) 0.1000(7) 0.2134(2) 0.0336(13) Uani 1 1 d . . . H5A H 0.0028 0.1899 0.1735 0.040 Uiso 1 1 calc R . . H5B H 0.2030 0.1018 0.2327 0.040 Uiso 1 1 calc R . . C6 C -0.1684(9) 0.1834(7) 0.2570(2) 0.0366(13) Uani 1 1 d . . . H6A H -0.3367 0.1829 0.2372 0.044 Uiso 1 1 calc R . . H6B H -0.1383 0.0911 0.2964 0.044 Uiso 1 1 calc R . . C7 C -0.1775(9) 0.3951(7) 0.2727(2) 0.0334(13) Uani 1 1 d . . . H7A H -0.2133 0.4886 0.2335 0.040 Uiso 1 1 calc R . . H7B H -0.0080 0.3970 0.2914 0.040 Uiso 1 1 calc R . . C8 C -0.3762(9) 0.4731(7) 0.3177(2) 0.0356(13) Uani 1 1 d . . . H8A H -0.5457 0.4714 0.2990 0.043 Uiso 1 1 calc R . . H8B H -0.3405 0.3795 0.3569 0.043 Uiso 1 1 calc R . . C9 C -0.3853(9) 0.6861(7) 0.3337(2) 0.0347(13) Uani 1 1 d . . . H9A H -0.4174 0.7791 0.2944 0.042 Uiso 1 1 calc R . . H9B H -0.2168 0.6870 0.3532 0.042 Uiso 1 1 calc R . . C10 C -0.5877(9) 0.7667(7) 0.3778(2) 0.0369(13) Uani 1 1 d . . . H10A H -0.7555 0.7616 0.3588 0.044 Uiso 1 1 calc R . . H10B H -0.5526 0.6758 0.4176 0.044 Uiso 1 1 calc R . . C11 C -0.6030(9) 0.9807(7) 0.3924(2) 0.0355(13) Uani 1 1 d . . . H11A H -0.6398 1.0722 0.3527 0.043 Uiso 1 1 calc R . . H11B H -0.4353 0.9863 0.4112 0.043 Uiso 1 1 calc R . . C12 C -0.8046(10) 1.0577(7) 0.4367(2) 0.0429(14) Uani 1 1 d . . . H12A H -0.7668 0.9665 0.4764 0.051 Uiso 1 1 calc R . . H12B H -0.9718 1.0504 0.4180 0.051 Uiso 1 1 calc R . . C13 C -0.8238(10) 1.2733(8) 0.4514(2) 0.0572(17) Uani 1 1 d . . . H13A H -0.9575 1.3122 0.4800 0.086 Uiso 1 1 calc R . . H13B H -0.8656 1.3656 0.4125 0.086 Uiso 1 1 calc R . . H13C H -0.6607 1.2815 0.4711 0.086 Uiso 1 1 calc R . . N1A N 0.7974(7) -0.9064(6) 0.03277(17) 0.0322(11) Uani 1 1 d . . . C1A C 0.9677(9) -0.8092(8) 0.0125(2) 0.0349(13) Uani 1 1 d . . . H1AA H 0.9525 -0.6734 0.0213 0.042 Uiso 1 1 calc R . . C2A C 0.8356(8) -1.0973(7) 0.0207(2) 0.0314(13) Uani 1 1 d . . . H2AA H 0.7222 -1.1731 0.0357 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.038(2) 0.042(3) 0.076(3) -0.032(2) 0.0327(19) -0.0213(19) O2 0.041(2) 0.040(2) 0.070(2) -0.0169(18) 0.0301(19) -0.0227(18) C1 0.029(3) 0.032(4) 0.039(3) -0.015(2) 0.005(2) -0.009(3) C2 0.028(3) 0.032(3) 0.040(3) -0.006(2) 0.009(2) -0.011(2) C3 0.028(3) 0.032(3) 0.045(3) -0.008(2) 0.004(2) -0.010(2) C4 0.028(3) 0.029(3) 0.045(3) -0.009(2) 0.013(2) -0.010(2) C5 0.025(3) 0.029(3) 0.049(3) -0.009(2) 0.011(2) -0.008(2) C6 0.034(3) 0.032(3) 0.050(3) -0.013(3) 0.015(3) -0.014(2) C7 0.025(3) 0.031(3) 0.046(3) -0.013(2) 0.010(2) -0.005(2) C8 0.028(3) 0.031(3) 0.051(3) -0.011(3) 0.009(2) -0.010(2) C9 0.030(3) 0.032(3) 0.045(3) -0.009(2) 0.012(2) -0.011(2) C10 0.033(3) 0.030(3) 0.052(3) -0.014(3) 0.010(2) -0.012(2) C11 0.032(3) 0.032(3) 0.046(3) -0.011(3) 0.009(2) -0.010(2) C12 0.046(3) 0.036(4) 0.049(3) -0.015(3) 0.012(3) -0.008(3) C13 0.059(4) 0.048(4) 0.064(4) -0.023(3) 0.014(3) -0.005(3) N1A 0.028(2) 0.027(3) 0.045(3) -0.010(2) 0.0086(19) -0.011(2) C1A 0.032(3) 0.030(3) 0.048(3) -0.016(3) 0.013(3) -0.012(3) C2A 0.027(3) 0.025(3) 0.046(3) -0.004(2) 0.009(2) -0.011(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 1.318(6) . ? O1 H1 0.854(10) . ? O2 C1 1.208(5) . ? C1 C2 1.494(6) . ? C2 C3 1.504(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.526(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.506(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.520(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.508(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.519(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.517(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.522(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.509(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.516(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.517(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1A C2A 1.323(5) . ? N1A C1A 1.336(5) . ? C1A C2A 1.374(6) 2_735 ? C1A H1AA 0.9500 . ? C2A C1A 1.374(6) 2_735 ? C2A H2AA 0.9500 . ? 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 109(4) . . ? O2 C1 O1 122.9(4) . . ? O2 C1 C2 125.2(4) . . ? O1 C1 C2 111.8(4) . . ? C1 C2 C3 115.4(4) . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 111.4(4) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 114.7(3) . . ? C5 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 113.1(3) . . ? 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 114.7(4) . . ? 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 . . ? C6 C7 C8 113.8(4) . . ? 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 113.9(4) . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C7 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C8 C9 C10 114.1(4) . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C9 114.4(4) . . ? 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 113.6(4) . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 114.2(4) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? 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 . . ? C2A N1A C1A 116.1(4) . . ? N1A C1A C2A 121.0(4) . 2_735 ? N1A C1A H1AA 119.5 . . ? C2A C1A H1AA 119.5 2_735 . ? N1A C2A C1A 122.8(4) . 2_735 ? N1A C2A H2AA 118.6 . . ? C1A C2A H2AA 118.6 2_735 . ? 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 2.5(7) . . . . ? O1 C1 C2 C3 -178.5(4) . . . . ? C1 C2 C3 C4 179.6(4) . . . . ? C2 C3 C4 C5 -179.9(4) . . . . ? C3 C4 C5 C6 -176.0(4) . . . . ? C4 C5 C6 C7 179.0(4) . . . . ? C5 C6 C7 C8 -178.3(4) . . . . ? C6 C7 C8 C9 179.9(4) . . . . ? C7 C8 C9 C10 178.8(4) . . . . ? C8 C9 C10 C11 -178.3(4) . . . . ? C9 C10 C11 C12 -179.6(4) . . . . ? C10 C11 C12 C13 -179.5(4) . . . . ? C2A N1A C1A C2A 2.3(7) . . . 2_735 ? C1A N1A C2A C1A -2.3(7) . . . 2_735 ? #===END