# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Nikoletta Bathori' _publ_contact_author_email nikoletta.bathori@uct.ac.za _publ_section_title ; Investigation of sublimation with and without dissociation in the chloride and nitrate salts of 4-(1-hydroxy-1,2-diphenylethyl)pyridine ; loop_ _publ_author_name N.B.Bathori 'Petra Bombicz' S.A.Bourne G.A.Venter # Attachment '- structure1.txt' data_1 _database_code_depnum_ccdc_archive 'CCDC 666826' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(1-hydroxy-1,2-diphenylethyl)pyridine ; _chemical_name_common 4-(1-hydroxy-1,2-diphenylethyl)pyridine _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 N O' _chemical_formula_sum 'C19 H17 N O' _chemical_formula_weight 275.34 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' 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 Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 9.3446(19) _cell_length_b 10.612(2) _cell_length_c 15.267(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.70(3) _cell_angle_gamma 90.00 _cell_volume 1442.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 30355 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 26.03 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30355 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.03 _reflns_number_total 2835 _reflns_number_gt 2129 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0485P)^2^+0.1690P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0127(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2835 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0932 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.41716(12) 0.28226(10) 0.07606(7) 0.0257(3) Uani 1 1 d . . . C2 C 0.53275(14) 0.33874(13) 0.13733(9) 0.0257(3) Uani 1 1 d . . . H2 H 0.6040 0.3818 0.1153 0.031 Uiso 1 1 calc R . . C3 C 0.55435(13) 0.33791(12) 0.23096(9) 0.0230(3) Uani 1 1 d . . . H3 H 0.6377 0.3808 0.2714 0.028 Uiso 1 1 calc R . . C4 C 0.45363(13) 0.27399(11) 0.26575(8) 0.0188(3) Uani 1 1 d . . . C5 C 0.33489(14) 0.21305(12) 0.20290(9) 0.0238(3) Uani 1 1 d . . . H5 H 0.2637 0.1670 0.2232 0.029 Uiso 1 1 calc R . . C6 C 0.32128(14) 0.22005(12) 0.11040(9) 0.0261(3) Uani 1 1 d . . . H6 H 0.2388 0.1781 0.0684 0.031 Uiso 1 1 calc R . . C7 C 0.46825(13) 0.27833(11) 0.36775(8) 0.0185(3) Uani 1 1 d . . . O8 O 0.37336(9) 0.18173(8) 0.38465(6) 0.0212(2) Uani 1 1 d . . . C9 C 0.41213(13) 0.40903(11) 0.38954(9) 0.0205(3) Uani 1 1 d . . . H9B H 0.4214 0.4122 0.4559 0.025 Uiso 1 1 calc R . . H9A H 0.4787 0.4749 0.3775 0.025 Uiso 1 1 calc R . . C10 C 0.25194(13) 0.43990(11) 0.33521(8) 0.0212(3) Uani 1 1 d . . . C11 C 0.22223(15) 0.53026(12) 0.26623(9) 0.0281(3) Uani 1 1 d . . . H11 H 0.3034 0.5715 0.2529 0.034 Uiso 1 1 calc R . . C12 C 0.07553(16) 0.56137(14) 0.21641(10) 0.0346(4) Uani 1 1 d . . . H12 H 0.0574 0.6235 0.1695 0.042 Uiso 1 1 calc R . . C13 C -0.04380(15) 0.50245(14) 0.23480(10) 0.0344(4) Uani 1 1 d . . . H13 H -0.1440 0.5236 0.2006 0.041 Uiso 1 1 calc R . . C14 C -0.01642(14) 0.41260(14) 0.30320(10) 0.0328(4) Uani 1 1 d . . . H14 H -0.0981 0.3718 0.3163 0.039 Uiso 1 1 calc R . . C15 C 0.13010(13) 0.38154(13) 0.35305(9) 0.0267(3) Uani 1 1 d . . . H15 H 0.1476 0.3196 0.4000 0.032 Uiso 1 1 calc R . . C16 C 0.63064(13) 0.25196(11) 0.42695(8) 0.0195(3) Uani 1 1 d . . . C17 C 0.73016(14) 0.34427(13) 0.47395(9) 0.0252(3) Uani 1 1 d . . . H17 H 0.7005 0.4302 0.4674 0.030 Uiso 1 1 calc R . . C18 C 0.87292(14) 0.31219(13) 0.53063(10) 0.0304(3) Uani 1 1 d . . . H18 H 0.9394 0.3764 0.5625 0.036 Uiso 1 1 calc R . . C19 C 0.91850(15) 0.18829(13) 0.54090(9) 0.0295(3) Uani 1 1 d . . . H19 H 1.0154 0.1666 0.5802 0.035 Uiso 1 1 calc R . . C20 C 0.82145(14) 0.09557(13) 0.49332(9) 0.0300(3) Uani 1 1 d . . . H20 H 0.8524 0.0099 0.4993 0.036 Uiso 1 1 calc R . . C21 C 0.67950(14) 0.12724(12) 0.43704(9) 0.0256(3) Uani 1 1 d . . . H21 H 0.6142 0.0627 0.4047 0.031 Uiso 1 1 calc R . . H8 H 0.3885 0.1887 0.4500 0.059(5) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0274(6) 0.0310(6) 0.0197(6) 0.0004(5) 0.0087(5) 0.0050(5) C2 0.0244(7) 0.0312(7) 0.0238(7) 0.0036(6) 0.0106(6) 0.0004(6) C3 0.0200(6) 0.0272(7) 0.0214(7) 0.0006(5) 0.0054(5) -0.0008(5) C4 0.0183(6) 0.0197(6) 0.0186(7) 0.0005(5) 0.0058(5) 0.0043(5) C5 0.0245(7) 0.0270(7) 0.0204(7) -0.0029(5) 0.0077(5) -0.0039(5) C6 0.0259(7) 0.0307(7) 0.0201(7) -0.0039(5) 0.0044(5) -0.0012(6) C7 0.0180(6) 0.0212(6) 0.0166(6) -0.0012(5) 0.0058(5) -0.0023(5) O8 0.0218(5) 0.0240(5) 0.0183(5) -0.0005(4) 0.0069(4) -0.0048(3) C9 0.0204(6) 0.0224(7) 0.0188(6) -0.0030(5) 0.0059(5) -0.0018(5) C10 0.0224(6) 0.0219(6) 0.0186(7) -0.0055(5) 0.0050(5) 0.0017(5) C11 0.0315(7) 0.0252(7) 0.0276(7) 0.0000(6) 0.0091(6) 0.0031(6) C12 0.0406(8) 0.0328(8) 0.0265(8) 0.0030(6) 0.0044(6) 0.0130(6) C13 0.0264(7) 0.0405(9) 0.0296(8) -0.0108(7) -0.0016(6) 0.0121(6) C14 0.0214(7) 0.0402(9) 0.0360(9) -0.0071(7) 0.0074(6) 0.0007(6) C15 0.0232(7) 0.0303(8) 0.0265(8) -0.0007(6) 0.0075(6) 0.0021(5) C16 0.0207(6) 0.0251(7) 0.0138(6) -0.0008(5) 0.0069(5) 0.0005(5) C17 0.0240(7) 0.0245(7) 0.0254(7) -0.0026(6) 0.0047(5) 0.0019(5) C18 0.0233(7) 0.0350(8) 0.0289(8) -0.0073(6) 0.0020(6) -0.0021(6) C19 0.0219(7) 0.0387(8) 0.0253(8) 0.0024(6) 0.0033(6) 0.0058(6) C20 0.0282(7) 0.0283(7) 0.0335(8) 0.0031(6) 0.0092(6) 0.0065(6) C21 0.0250(7) 0.0244(7) 0.0265(7) -0.0024(6) 0.0067(5) 0.0003(5) _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O8 C7 1.4293(15) . . yes O8 H8 0.9700 . . no N1 C6 1.3413(18) . . yes N1 C2 1.3366(17) . . yes C2 C3 1.3816(19) . . no C3 C4 1.3900(18) . . no C4 C7 1.5220(17) . . no C4 C5 1.3866(18) . . no C5 C6 1.3809(19) . . no C7 C16 1.5375(18) . . no C7 C9 1.5542(17) . . no C9 C10 1.5103(18) . . no C10 C11 1.3885(18) . . no C10 C15 1.3938(18) . . no C11 C12 1.390(2) . . no C12 C13 1.380(2) . . no C13 C14 1.379(2) . . no C14 C15 1.3888(19) . . no C16 C21 1.3933(18) . . no C16 C17 1.3905(18) . . no C17 C18 1.394(2) . . no C18 C19 1.376(2) . . no C19 C20 1.385(2) . . no C20 C21 1.3848(19) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C9 H9A 0.9900 . . no C9 H9B 0.9900 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no C13 H13 0.9500 . . no C14 H14 0.9500 . . no C15 H15 0.9500 . . no C17 H17 0.9500 . . no C18 H18 0.9500 . . no C19 H19 0.9500 . . no C20 H20 0.9500 . . no C21 H21 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O8 H8 103.00 . . . no C2 N1 C6 116.16(11) . . . yes N1 C2 C3 123.64(13) . . . yes C2 C3 C4 119.71(12) . . . no C3 C4 C7 121.04(11) . . . no C5 C4 C7 121.75(12) . . . no C3 C4 C5 117.10(12) . . . no C4 C5 C6 119.22(13) . . . no N1 C6 C5 124.16(13) . . . yes O8 C7 C4 107.18(10) . . . yes O8 C7 C16 108.60(10) . . . yes C4 C7 C9 108.35(10) . . . no C4 C7 C16 111.19(11) . . . no C9 C7 C16 111.94(10) . . . no O8 C7 C9 109.46(10) . . . yes C7 C9 C10 114.75(11) . . . no C9 C10 C11 120.17(12) . . . no C11 C10 C15 117.92(12) . . . no C9 C10 C15 121.90(11) . . . no C10 C11 C12 121.03(13) . . . no C11 C12 C13 120.30(14) . . . no C12 C13 C14 119.47(14) . . . no C13 C14 C15 120.26(13) . . . no C10 C15 C14 121.01(13) . . . no C7 C16 C17 124.11(11) . . . no C17 C16 C21 117.83(12) . . . no C7 C16 C21 118.01(11) . . . no C16 C17 C18 120.80(13) . . . no C17 C18 C19 120.58(13) . . . no C18 C19 C20 119.24(13) . . . no C19 C20 C21 120.27(13) . . . no C16 C21 C20 121.27(12) . . . no N1 C2 H2 118.00 . . . no C3 C2 H2 118.00 . . . no C2 C3 H3 120.00 . . . no C4 C3 H3 120.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no N1 C6 H6 118.00 . . . no C5 C6 H6 118.00 . . . no C7 C9 H9A 109.00 . . . no C7 C9 H9B 109.00 . . . no C10 C9 H9A 109.00 . . . no C10 C9 H9B 109.00 . . . no H9A C9 H9B 108.00 . . . no C10 C11 H11 119.00 . . . no C12 C11 H11 119.00 . . . no C11 C12 H12 120.00 . . . no C13 C12 H12 120.00 . . . no C12 C13 H13 120.00 . . . no C14 C13 H13 120.00 . . . no C13 C14 H14 120.00 . . . no C15 C14 H14 120.00 . . . no C10 C15 H15 119.00 . . . no C14 C15 H15 120.00 . . . no C16 C17 H17 120.00 . . . no C18 C17 H17 120.00 . . . no C17 C18 H18 120.00 . . . no C19 C18 H18 120.00 . . . no C18 C19 H19 120.00 . . . no C20 C19 H19 120.00 . . . no C19 C20 H20 120.00 . . . no C21 C20 H20 120.00 . . . no C16 C21 H21 119.00 . . . no C20 C21 H21 119.00 . . . no 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 C6 N1 C2 C3 -1.5(2) . . . . no C2 N1 C6 C5 0.8(2) . . . . no N1 C2 C3 C4 1.1(2) . . . . no C2 C3 C4 C5 0.21(19) . . . . no C2 C3 C4 C7 -175.95(12) . . . . no C3 C4 C5 C6 -0.90(19) . . . . no C7 C4 C5 C6 175.24(12) . . . . no C3 C4 C7 O8 -166.52(11) . . . . no C3 C4 C7 C9 75.45(15) . . . . no C3 C4 C7 C16 -47.97(15) . . . . no C5 C4 C7 O8 17.50(16) . . . . no C5 C4 C7 C9 -100.54(14) . . . . no C5 C4 C7 C16 136.05(12) . . . . no C4 C5 C6 N1 0.4(2) . . . . no O8 C7 C9 C10 -58.26(13) . . . . no C4 C7 C9 C10 58.31(14) . . . . no C16 C7 C9 C10 -178.72(10) . . . . no O8 C7 C16 C17 -138.48(12) . . . . no O8 C7 C16 C21 38.96(15) . . . . no C4 C7 C16 C17 103.83(14) . . . . no C4 C7 C16 C21 -78.73(14) . . . . no C9 C7 C16 C17 -17.52(17) . . . . no C9 C7 C16 C21 159.93(12) . . . . no C7 C9 C10 C11 -108.28(13) . . . . no C7 C9 C10 C15 72.87(16) . . . . no C9 C10 C11 C12 -179.01(12) . . . . no C15 C10 C11 C12 -0.11(19) . . . . no C9 C10 C15 C14 179.04(13) . . . . no C11 C10 C15 C14 0.2(2) . . . . no C10 C11 C12 C13 0.0(2) . . . . no C11 C12 C13 C14 0.2(2) . . . . no C12 C13 C14 C15 -0.1(2) . . . . no C13 C14 C15 C10 -0.1(2) . . . . no C7 C16 C17 C18 176.21(12) . . . . no C21 C16 C17 C18 -1.24(19) . . . . no C7 C16 C21 C20 -176.43(12) . . . . no C17 C16 C21 C20 1.18(19) . . . . no C16 C17 C18 C19 0.3(2) . . . . no C17 C18 C19 C20 0.8(2) . . . . no C18 C19 C20 C21 -0.8(2) . . . . no C19 C20 C21 C16 -0.2(2) . . . . no _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.168 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.045 _exptl_crystal_recrystallization_method methanol # Attachment '- structure1HCl.txt' data_1.HCl _database_code_depnum_ccdc_archive 'CCDC 666827' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(1-hydroxy-1,2-diphenylethyl)pyridium chloride ; _chemical_name_common '4-(1-hydroxy-1,2-diphenylethyl)pyridium chloride' _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 N O, Cl' _chemical_formula_sum 'C19 H18 Cl N O' _chemical_formula_weight 311.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3219(13) _cell_length_b 8.4477(17) _cell_length_c 15.349(3) _cell_angle_alpha 102.22(3) _cell_angle_beta 92.54(3) _cell_angle_gamma 106.21(3) _cell_volume 764.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12756 _cell_measurement_theta_min 3.29 _cell_measurement_theta_max 26.34 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.879 _exptl_absorpt_correction_T_max 0.882 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12756 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 26.34 _reflns_number_total 3103 _reflns_number_gt 2637 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0443P)^2^+0.3508P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.003(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3103 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.68004(6) 0.88693(4) 0.04004(2) 0.01796(13) Uani 1 1 d . . . N1 N -0.1669(2) 0.28393(17) 0.07394(9) 0.0212(3) Uani 1 1 d . . . H1 H -0.254(3) 0.185(3) 0.0504(14) 0.038(6) Uiso 1 1 d . . . C2 C 0.0337(3) 0.2981(2) 0.11194(10) 0.0225(3) Uani 1 1 d . . . H2 H 0.0807 0.1998 0.1091 0.027 Uiso 1 1 calc R . . C3 C 0.1724(3) 0.45503(19) 0.15523(10) 0.0203(3) Uani 1 1 d . . . H3 H 0.3152 0.4651 0.1822 0.024 Uiso 1 1 calc R . . C4 C 0.1033(2) 0.59981(18) 0.15950(9) 0.0159(3) Uani 1 1 d . . . C5 C -0.1055(2) 0.57852(19) 0.11668(11) 0.0214(3) Uani 1 1 d . . . H5 H -0.1558 0.6744 0.1165 0.026 Uiso 1 1 calc R . . C6 C -0.2385(3) 0.4187(2) 0.07477(11) 0.0239(3) Uani 1 1 d . . . H6 H -0.3815 0.4042 0.0464 0.029 Uiso 1 1 calc R . . C7 C 0.2550(2) 0.77155(18) 0.21420(10) 0.0161(3) Uani 1 1 d . . . O8 O 0.47954(16) 0.77556(13) 0.20577(7) 0.0195(2) Uani 1 1 d . . . H8 H 0.518(4) 0.806(3) 0.1575(16) 0.049(6) Uiso 1 1 d . . . C9 C 0.2053(2) 0.92277(18) 0.18447(10) 0.0174(3) Uani 1 1 d . . . H9A H 0.2505 0.9238 0.1236 0.021 Uiso 1 1 calc R . . H9B H 0.0434 0.9056 0.1808 0.021 Uiso 1 1 calc R . . C10 C 0.3217(2) 1.09351(18) 0.24653(10) 0.0170(3) Uani 1 1 d . . . C11 C 0.2011(3) 1.17763(19) 0.30335(10) 0.0204(3) Uani 1 1 d . . . H11 H 0.0466 1.1268 0.3029 0.024 Uiso 1 1 calc R . . C12 C 0.3038(3) 1.3349(2) 0.36069(11) 0.0234(3) Uani 1 1 d . . . H12 H 0.2197 1.3908 0.3990 0.028 Uiso 1 1 calc R . . C13 C 0.5290(3) 1.4096(2) 0.36181(11) 0.0246(4) Uani 1 1 d . . . H13 H 0.5999 1.5165 0.4014 0.030 Uiso 1 1 calc R . . C14 C 0.6509(3) 1.3288(2) 0.30536(11) 0.0249(4) Uani 1 1 d . . . H14 H 0.8051 1.3807 0.3059 0.030 Uiso 1 1 calc R . . C15 C 0.5481(3) 1.17135(19) 0.24776(10) 0.0210(3) Uani 1 1 d . . . H15 H 0.6326 1.1166 0.2091 0.025 Uiso 1 1 calc R . . C16 C 0.2183(2) 0.77920(17) 0.31292(10) 0.0159(3) Uani 1 1 d . . . C17 C 0.0134(2) 0.78082(19) 0.34277(10) 0.0200(3) Uani 1 1 d . . . H17 H -0.1072 0.7724 0.3011 0.024 Uiso 1 1 calc R . . C18 C -0.0154(2) 0.7946(2) 0.43279(11) 0.0224(3) Uani 1 1 d . . . H18 H -0.1543 0.7988 0.4527 0.027 Uiso 1 1 calc R . . C19 C 0.1578(3) 0.8024(2) 0.49389(11) 0.0233(3) Uani 1 1 d . . . H19 H 0.1373 0.8102 0.5554 0.028 Uiso 1 1 calc R . . C20 C 0.3600(3) 0.7986(2) 0.46460(11) 0.0263(4) Uani 1 1 d . . . H20 H 0.4786 0.8029 0.5061 0.032 Uiso 1 1 calc R . . C21 C 0.3910(3) 0.7885(2) 0.37467(11) 0.0220(3) Uani 1 1 d . . . H21 H 0.5316 0.7880 0.3554 0.026 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 Cl1 0.0193(2) 0.01504(19) 0.0196(2) 0.00434(14) 0.00222(13) 0.00508(14) N1 0.0294(7) 0.0133(7) 0.0165(7) 0.0009(5) 0.0039(5) 0.0007(6) C2 0.0331(9) 0.0169(8) 0.0211(8) 0.0061(6) 0.0096(7) 0.0108(7) C3 0.0238(8) 0.0199(8) 0.0188(8) 0.0051(6) 0.0038(6) 0.0085(6) C4 0.0207(7) 0.0153(7) 0.0123(7) 0.0046(6) 0.0051(6) 0.0050(6) C5 0.0226(8) 0.0163(7) 0.0243(8) 0.0028(6) -0.0002(6) 0.0063(6) C6 0.0246(8) 0.0201(8) 0.0240(9) 0.0036(7) -0.0007(7) 0.0034(6) C7 0.0149(7) 0.0154(7) 0.0190(8) 0.0050(6) 0.0025(6) 0.0054(6) O8 0.0160(5) 0.0234(6) 0.0220(6) 0.0091(5) 0.0054(4) 0.0069(4) C9 0.0187(7) 0.0152(7) 0.0183(8) 0.0049(6) 0.0009(6) 0.0042(6) C10 0.0217(7) 0.0130(7) 0.0169(7) 0.0060(6) 0.0008(6) 0.0043(6) C11 0.0213(7) 0.0174(7) 0.0229(8) 0.0064(6) 0.0032(6) 0.0051(6) C12 0.0292(8) 0.0186(8) 0.0227(8) 0.0038(7) 0.0055(7) 0.0079(7) C13 0.0303(9) 0.0150(8) 0.0238(9) 0.0019(6) -0.0017(7) 0.0017(6) C14 0.0219(8) 0.0201(8) 0.0306(9) 0.0087(7) 0.0019(7) 0.0009(6) C15 0.0225(8) 0.0184(8) 0.0224(8) 0.0064(6) 0.0047(6) 0.0048(6) C16 0.0182(7) 0.0096(6) 0.0184(8) 0.0028(6) 0.0015(6) 0.0020(5) C17 0.0167(7) 0.0197(8) 0.0212(8) 0.0033(6) -0.0005(6) 0.0028(6) C18 0.0173(7) 0.0219(8) 0.0258(9) 0.0037(7) 0.0065(6) 0.0029(6) C19 0.0287(8) 0.0234(8) 0.0169(8) 0.0049(6) 0.0047(6) 0.0059(7) C20 0.0247(8) 0.0343(9) 0.0219(8) 0.0073(7) -0.0009(6) 0.0120(7) C21 0.0188(7) 0.0272(8) 0.0225(8) 0.0063(7) 0.0036(6) 0.0102(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.335(2) . ? N1 C6 1.335(2) . ? C2 C3 1.376(2) . ? C3 C4 1.399(2) . ? C4 C5 1.395(2) . ? C4 C7 1.538(2) . ? C5 C6 1.376(2) . ? C7 O8 1.4227(17) . ? C7 C16 1.534(2) . ? C7 C9 1.548(2) . ? C9 C10 1.514(2) . ? C10 C11 1.394(2) . ? C10 C15 1.396(2) . ? C11 C12 1.390(2) . ? C12 C13 1.385(2) . ? C13 C14 1.383(2) . ? C14 C15 1.393(2) . ? C16 C21 1.387(2) . ? C16 C17 1.396(2) . ? C17 C18 1.386(2) . ? C18 C19 1.387(2) . ? C19 C20 1.380(2) . ? C20 C21 1.391(2) . ? C2 H2 0.9500 . . C3 H3 0.9500 . . C5 H5 0.9500 . . C6 H6 0.9500 . . C9 H9A 0.9900 . . C9 H9B 0.9900 . . C11 H11 0.9500 . . C12 H12 0.9500 . . C13 H13 0.9500 . . C14 H14 0.9500 . . C15 H15 0.9500 . . C17 H17 0.9500 . . C18 H18 0.9500 . . C19 H19 0.9500 . . C20 H20 0.9500 . . C21 H21 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 C2 N1 C6 122.13(14) . . ? N1 C2 C3 120.02(14) . . ? C2 C3 C4 120.02(15) . . ? C5 C4 C3 117.66(14) . . ? C5 C4 C7 123.53(13) . . ? C3 C4 C7 118.75(13) . . ? C6 C5 C4 120.05(14) . . ? N1 C6 C5 120.09(15) . . ? O8 C7 C16 107.39(12) . . ? O8 C7 C4 108.79(12) . . ? C16 C7 C4 106.94(11) . . ? O8 C7 C9 110.78(11) . . ? C16 C7 C9 110.59(12) . . ? C4 C7 C9 112.16(12) . . ? C10 C9 C7 113.93(12) . . ? C11 C10 C15 118.54(14) . . ? C11 C10 C9 119.83(13) . . ? C15 C10 C9 121.63(14) . . ? C12 C11 C10 120.97(14) . . ? C13 C12 C11 119.81(15) . . ? C14 C13 C12 120.04(15) . . ? C13 C14 C15 120.19(15) . . ? C14 C15 C10 120.46(15) . . ? C21 C16 C17 118.80(14) . . ? C21 C16 C7 120.24(13) . . ? C17 C16 C7 120.94(13) . . ? C18 C17 C16 120.45(14) . . ? C17 C18 C19 120.30(14) . . ? C20 C19 C18 119.51(14) . . ? C19 C20 C21 120.39(15) . . ? C16 C21 C20 120.53(14) . . ? N1 C2 H2 120.00 . . . C3 C2 H2 120.00 . . . C2 C3 H3 120.00 . . . C4 C3 H3 120.00 . . . C4 C5 H5 120.00 . . . C6 C5 H5 120.00 . . . N1 C6 H6 120.00 . . . C5 C6 H6 120.00 . . . C7 C9 H9A 109.00 . . . C7 C9 H9B 109.00 . . . C10 C9 H9A 109.00 . . . C10 C9 H9B 109.00 . . . H9A C9 H9B 108.00 . . . C10 C11 H11 120.00 . . . C12 C11 H11 119.00 . . . C11 C12 H12 120.00 . . . C13 C12 H12 120.00 . . . C12 C13 H13 120.00 . . . C14 C13 H13 120.00 . . . C13 C14 H14 120.00 . . . C15 C14 H14 120.00 . . . C10 C15 H15 120.00 . . . C14 C15 H15 120.00 . . . C16 C17 H17 120.00 . . . C18 C17 H17 120.00 . . . C17 C18 H18 120.00 . . . C19 C18 H18 120.00 . . . C18 C19 H19 120.00 . . . C20 C19 H19 120.00 . . . C19 C20 H20 120.00 . . . C21 C20 H20 120.00 . . . C16 C21 H21 120.00 . . . C20 C21 H21 120.00 . . . 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 C6 N1 C2 C3 1.3(2) . . . . no C2 N1 C6 C5 -0.8(2) . . . . no N1 C2 C3 C4 0.0(2) . . . . no C2 C3 C4 C5 -1.7(2) . . . . no C2 C3 C4 C7 175.57(14) . . . . no C3 C4 C5 C6 2.1(2) . . . . no C7 C4 C5 C6 -175.00(15) . . . . no C3 C4 C7 O8 35.22(18) . . . . no C3 C4 C7 C9 158.12(13) . . . . no C3 C4 C7 C16 -80.49(16) . . . . no C5 C4 C7 O8 -147.70(14) . . . . no C5 C4 C7 C9 -24.80(19) . . . . no C5 C4 C7 C16 96.60(16) . . . . no C4 C5 C6 N1 -0.9(2) . . . . no O8 C7 C9 C10 -68.37(15) . . . . no C4 C7 C9 C10 169.87(12) . . . . no C16 C7 C9 C10 50.59(15) . . . . no O8 C7 C16 C17 178.70(13) . . . . no O8 C7 C16 C21 0.15(19) . . . . no C4 C7 C16 C17 -64.68(17) . . . . no C4 C7 C16 C21 116.77(15) . . . . no C9 C7 C16 C17 57.71(18) . . . . no C9 C7 C16 C21 -120.84(15) . . . . no C7 C9 C10 C11 -106.20(16) . . . . no C7 C9 C10 C15 74.72(18) . . . . no C9 C10 C11 C12 -179.70(15) . . . . no C15 C10 C11 C12 -0.6(2) . . . . no C9 C10 C15 C14 179.80(15) . . . . no C11 C10 C15 C14 0.7(2) . . . . no C10 C11 C12 C13 -0.1(2) . . . . no C11 C12 C13 C14 0.7(3) . . . . no C12 C13 C14 C15 -0.6(3) . . . . no C13 C14 C15 C10 -0.1(2) . . . . no C7 C16 C17 C18 -177.41(15) . . . . no C21 C16 C17 C18 1.2(2) . . . . no C7 C16 C21 C20 178.82(15) . . . . no C17 C16 C21 C20 0.2(2) . . . . no C16 C17 C18 C19 -1.7(2) . . . . no C17 C18 C19 C20 0.9(3) . . . . no C18 C19 C20 C21 0.6(3) . . . . no C19 C20 C21 C16 -1.1(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl1 O8 3.0977(13) . . no Cl1 N1 3.1400(16) . 1_665 no Cl1 C2 3.4791(19) . 1_665 no Cl1 Cl1 3.6764(9) . 2_675 no Cl1 N1 3.3884(16) . 2_565 no Cl1 C2 3.4015(19) . 2_665 no Cl1 C6 3.3433(19) . 2_565 no Cl1 C5 3.6247(17) . 1_655 no Cl1 H9B 3.0300 . 1_655 no Cl1 H15 2.9700 . . no Cl1 H9A 3.1200 . . no Cl1 H1 2.40(2) . 1_665 no Cl1 H2 3.0600 . 1_665 no Cl1 H5 2.7400 . 1_655 no Cl1 H8 2.25(2) . . no Cl1 H1 2.82(2) . 2_565 no Cl1 H2 2.8800 . 2_665 no Cl1 H6 2.6800 . 2_565 no O8 Cl1 3.0977(13) . . no O8 C15 3.168(2) . . no O8 H15 2.7600 . . no O8 H3 2.4800 . . no O8 H21 2.2800 . . no N1 Cl1 3.1400(16) . 1_445 no N1 C15 3.437(2) . 1_445 no N1 Cl1 3.3884(16) . 2_565 no N1 H15 2.9000 . 1_445 no C2 C11 3.518(2) . 1_545 no C2 Cl1 3.4015(19) . 2_665 no C2 Cl1 3.4791(19) . 1_445 no C5 C17 3.474(2) . . no C5 Cl1 3.6247(17) . 1_455 no C6 Cl1 3.3433(19) . 2_565 no C10 C17 3.463(2) . . no C11 C16 3.431(2) . . no C11 C2 3.518(2) . 1_565 no C11 C17 3.422(2) . . no C13 C21 3.515(3) . 1_565 no C15 O8 3.168(2) . . no C15 N1 3.437(2) . 1_665 no C16 C11 3.431(2) . . no C17 C11 3.422(2) . . no C17 C5 3.474(2) . . no C17 C10 3.463(2) . . no C18 C18 3.591(2) . 2_576 no C20 C20 3.285(2) . 2_676 no C21 C13 3.515(3) . 1_545 no C4 H17 2.9400 . . no C5 H17 2.9600 . . no C5 H9B 2.6100 . . no C9 H5 2.6200 . . no C9 H2 3.0900 . 1_565 no C9 H17 2.9300 . . no C10 H2 2.9800 . 1_565 no C12 H20 3.0100 . 2_676 no C13 H20 2.9700 . 2_676 no C14 H19 3.0700 . 2_676 no C15 H8 3.05(2) . . no C17 H11 3.0600 . . no C17 H21 3.0800 . 1_455 no C17 H9B 2.8900 . . no C18 H13 2.8100 . 1_445 no C18 H21 3.0300 . 1_455 no C20 H18 3.0800 . 1_655 no C21 H18 3.0400 . 1_655 no C21 H13 3.0400 . 1_545 no H1 Cl1 2.40(2) . 1_445 no H1 Cl1 2.82(2) . 2_565 no H2 C9 3.0900 . 1_545 no H2 C10 2.9800 . 1_545 no H2 Cl1 3.0600 . 1_445 no H2 Cl1 2.8800 . 2_665 no H3 O8 2.4800 . . no H5 Cl1 2.7400 . 1_455 no H5 H9B 2.0200 . . no H5 C9 2.6200 . . no H6 Cl1 2.6800 . 2_565 no H8 Cl1 2.25(2) . . no H8 C15 3.05(2) . . no H8 H9A 2.2800 . . no H8 H15 2.4600 . . no H9A Cl1 3.1200 . . no H9A H8 2.2800 . . no H9B C5 2.6100 . . no H9B H11 2.3400 . . no H9B C17 2.8900 . . no H9B H5 2.0200 . . no H9B Cl1 3.0300 . 1_455 no H9B H17 2.4500 . . no H11 H19 2.5400 . 2_576 no H11 H9B 2.3400 . . no H11 C17 3.0600 . . no H13 C18 2.8100 . 1_665 no H13 C21 3.0400 . 1_565 no H13 H18 2.4000 . 1_665 no H15 Cl1 2.9700 . . no H15 H8 2.4600 . . no H15 O8 2.7600 . . no H15 N1 2.9000 . 1_665 no H17 C4 2.9400 . . no H17 H9B 2.4500 . . no H17 C5 2.9600 . . no H17 C9 2.9300 . . no H17 H21 2.4900 . 1_455 no H18 H20 2.5000 . 1_455 no H18 H21 2.4000 . 1_455 no H18 H13 2.4000 . 1_445 no H18 C20 3.0800 . 1_455 no H18 C21 3.0400 . 1_455 no H19 C14 3.0700 . 2_676 no H19 H11 2.5400 . 2_576 no H20 H18 2.5000 . 1_655 no H20 C12 3.0100 . 2_676 no H20 C13 2.9700 . 2_676 no H21 C17 3.0800 . 1_655 no H21 H18 2.4000 . 1_655 no H21 C18 3.0300 . 1_655 no H21 H17 2.4900 . 1_655 no H21 O8 2.2800 . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1 Cl1 0.85(2) 2.40(2) 3.1400(16) 144.7(18) 1_445 yes N1 H1 Cl1 0.85(2) 2.82(2) 3.3884(16) 125.6(18) 2_565 yes O8 H8 Cl1 0.86(2) 2.25(2) 3.0977(13) 170(2) . yes C5 H5 Cl1 0.9500 2.7400 3.6247(17) 156.00 1_455 yes C6 H6 Cl1 0.9500 2.6800 3.3433(19) 128.00 2_565 yes C21 H21 O8 0.9500 2.2800 2.663(2) 103.00 . yes _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.34 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.269 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.049 _exptl_crystal_recrystallization_method methanol # Attachment '- structure1HNO3.txt' data_1.HNO3 _database_code_depnum_ccdc_archive 'CCDC 743052' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(1-hydroxy-1,2-diphenylethyl)pyridium nitrate ; _chemical_name_common '4-(1-hydroxy-1,2-diphenylethyl)pyridium nitrate' _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 N O, N O3' _chemical_formula_sum 'C19 H18 N2 O4' _chemical_formula_weight 338.35 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_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3168(13) _cell_length_b 8.1971(16) _cell_length_c 16.497(3) _cell_angle_alpha 100.78(3) _cell_angle_beta 91.20(3) _cell_angle_gamma 100.44(3) _cell_volume 823.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3025 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 25.63 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3025 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0789 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 25.63 _reflns_number_total 3025 _reflns_number_gt 1900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0419P)^2^+0.2058P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.009(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3025 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.0998 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4844(3) 0.7674(2) 0.44791(11) 0.0356(5) Uani 1 1 d . . . N1 N 1.1319(3) 1.1867(2) 0.40682(13) 0.0296(5) Uani 1 1 d . . . O2 O 0.2222(3) 0.5517(2) 0.43076(12) 0.0405(5) Uani 1 1 d . . . N2 N 0.3706(3) 0.6492(3) 0.47541(12) 0.0258(5) Uani 1 1 d . . . C2 C 0.9445(4) 1.1930(3) 0.36926(16) 0.0280(6) Uani 1 1 d . . . H2 H 0.8999 1.2985 0.3724 0.034 Uiso 1 1 calc R . . O3 O 0.4109(3) 0.6354(2) 0.54817(11) 0.0373(5) Uani 1 1 d . . . C3 C 0.8164(4) 1.0478(3) 0.32621(15) 0.0261(6) Uani 1 1 d . . . H3 H 0.6842 1.0536 0.2994 0.031 Uiso 1 1 calc R . . C4 C 0.8791(3) 0.8918(3) 0.32166(14) 0.0198(5) Uani 1 1 d . . . C5 C 1.0737(4) 0.8919(3) 0.36282(15) 0.0285(6) Uani 1 1 d . . . H5 H 1.1214 0.7881 0.3618 0.034 Uiso 1 1 calc R . . C6 C 1.1978(4) 1.0398(3) 0.40482(16) 0.0345(7) Uani 1 1 d . . . H6 H 1.3305 1.0380 0.4325 0.041 Uiso 1 1 calc R . . C7 C 0.7396(3) 0.7324(3) 0.26980(14) 0.0198(5) Uani 1 1 d . . . O8 O 0.5183(2) 0.7422(2) 0.28041(10) 0.0239(4) Uani 1 1 d . . . C9 C 0.7887(4) 0.5692(3) 0.29487(14) 0.0225(6) Uani 1 1 d . . . H9A H 0.9457 0.5714 0.2931 0.027 Uiso 1 1 calc R . . H9B H 0.7493 0.5690 0.3526 0.027 Uiso 1 1 calc R . . C10 C 0.6715(3) 0.4084(3) 0.24073(15) 0.0214(6) Uani 1 1 d . . . C11 C 0.7805(4) 0.3178(3) 0.18068(16) 0.0290(6) Uani 1 1 d . . . H11 H 0.9281 0.3599 0.1740 0.035 Uiso 1 1 calc R . . C12 C 0.6785(4) 0.1682(3) 0.13052(16) 0.0348(7) Uani 1 1 d . . . H12 H 0.7564 0.1079 0.0904 0.042 Uiso 1 1 calc R . . C13 C 0.4636(4) 0.1067(3) 0.13890(17) 0.0350(7) Uani 1 1 d . . . H13 H 0.3920 0.0054 0.1039 0.042 Uiso 1 1 calc R . . C14 C 0.3530(4) 0.1935(3) 0.19855(18) 0.0347(7) Uani 1 1 d . . . H14 H 0.2056 0.1504 0.2050 0.042 Uiso 1 1 calc R . . C15 C 0.4556(4) 0.3431(3) 0.24908(16) 0.0297(6) Uani 1 1 d . . . H15 H 0.3777 0.4015 0.2898 0.036 Uiso 1 1 calc R . . C16 C 0.7804(3) 0.7289(3) 0.17834(14) 0.0185(5) Uani 1 1 d . . . C17 C 0.9874(4) 0.7401(3) 0.15099(15) 0.0270(6) Uani 1 1 d . . . H17 H 1.1066 0.7560 0.1896 0.032 Uiso 1 1 calc R . . C18 C 1.0214(4) 0.7282(3) 0.06761(16) 0.0336(7) Uani 1 1 d . . . H18 H 1.1637 0.7338 0.0493 0.040 Uiso 1 1 calc R . . C19 C 0.8504(4) 0.7083(3) 0.01081(16) 0.0322(6) Uani 1 1 d . . . H19 H 0.8747 0.7025 -0.0462 0.039 Uiso 1 1 calc R . . C20 C 0.6449(4) 0.6970(3) 0.03773(15) 0.0314(6) Uani 1 1 d . . . H20 H 0.5265 0.6832 -0.0010 0.038 Uiso 1 1 calc R . . C21 C 0.6086(4) 0.7057(3) 0.12072(15) 0.0275(6) Uani 1 1 d . . . H21 H 0.4655 0.6957 0.1384 0.033 Uiso 1 1 calc R . . H1 H 1.2333 1.3012 0.4391 0.084(11) Uiso 1 1 d R . . H8 H 0.4974 0.7422 0.3408 0.062(9) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0407(11) 0.0319(10) 0.0309(11) 0.0100(9) -0.0012(8) -0.0049(8) N1 0.0357(12) 0.0219(12) 0.0290(13) 0.0032(10) -0.0036(10) 0.0021(10) O2 0.0308(10) 0.0300(11) 0.0563(13) 0.0046(10) -0.0160(9) 0.0001(8) N2 0.0267(11) 0.0311(13) 0.0231(13) 0.0058(11) 0.0007(10) 0.0141(10) C2 0.0322(14) 0.0207(14) 0.0331(15) 0.0076(12) 0.0064(12) 0.0078(11) O3 0.0453(11) 0.0430(12) 0.0278(11) 0.0109(9) 0.0039(9) 0.0153(9) C3 0.0251(13) 0.0263(15) 0.0282(15) 0.0063(12) -0.0009(11) 0.0075(11) C4 0.0222(12) 0.0202(13) 0.0177(13) 0.0046(11) 0.0016(10) 0.0048(10) C5 0.0299(14) 0.0216(14) 0.0333(16) 0.0031(12) -0.0102(12) 0.0073(11) C6 0.0350(15) 0.0276(16) 0.0388(17) 0.0051(13) -0.0129(13) 0.0039(12) C7 0.0154(11) 0.0231(13) 0.0225(14) 0.0069(11) -0.0006(10) 0.0054(10) O8 0.0186(8) 0.0307(10) 0.0240(10) 0.0076(8) 0.0023(7) 0.0062(7) C9 0.0257(13) 0.0211(13) 0.0211(13) 0.0078(11) -0.0018(10) 0.0023(10) C10 0.0241(12) 0.0185(13) 0.0241(14) 0.0094(11) -0.0003(11) 0.0057(10) C11 0.0286(13) 0.0241(14) 0.0353(16) 0.0098(13) 0.0040(12) 0.0029(11) C12 0.0465(17) 0.0263(15) 0.0308(16) 0.0030(13) 0.0039(13) 0.0075(13) C13 0.0437(17) 0.0212(14) 0.0357(17) 0.0041(13) -0.0084(14) -0.0024(12) C14 0.0274(14) 0.0268(15) 0.0481(18) 0.0096(14) -0.0027(13) -0.0012(12) C15 0.0278(14) 0.0275(15) 0.0362(16) 0.0106(13) 0.0037(12) 0.0064(12) C16 0.0217(12) 0.0134(12) 0.0199(13) 0.0016(10) -0.0014(10) 0.0036(9) C17 0.0204(13) 0.0379(15) 0.0211(14) 0.0054(12) -0.0017(10) 0.0018(11) C18 0.0229(13) 0.0447(17) 0.0300(16) 0.0049(14) 0.0043(12) 0.0005(12) C19 0.0376(15) 0.0380(16) 0.0196(15) 0.0043(13) 0.0042(12) 0.0043(12) C20 0.0316(14) 0.0398(16) 0.0224(15) 0.0045(13) -0.0061(12) 0.0084(12) C21 0.0216(13) 0.0336(15) 0.0283(15) 0.0071(12) -0.0009(11) 0.0070(11) _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O8 C7 1.427(2) . . yes O8 H8 1.0100 . . no O1 N2 1.260(3) . . yes O2 N2 1.241(3) . . yes O3 N2 1.252(3) . . yes N1 C6 1.339(3) . . yes N1 C2 1.338(3) . . yes N1 H1 1.0800 . . no C2 C3 1.374(4) . . no C3 C4 1.395(3) . . no C4 C7 1.533(3) . . no C4 C5 1.392(3) . . no C5 C6 1.372(4) . . no C7 C9 1.552(3) . . no C7 C16 1.532(3) . . no C9 C10 1.504(3) . . no C10 C11 1.395(3) . . no C10 C15 1.392(3) . . no C11 C12 1.384(4) . . no C12 C13 1.379(4) . . no C13 C14 1.382(4) . . no C14 C15 1.388(4) . . no C16 C21 1.390(3) . . no C16 C17 1.385(3) . . no C17 C18 1.385(4) . . no C18 C19 1.381(4) . . no C19 C20 1.374(4) . . no C20 C21 1.384(3) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C9 H9B 0.9900 . . no C9 H9A 0.9900 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no C13 H13 0.9500 . . no C14 H14 0.9500 . . no C15 H15 0.9500 . . no C17 H17 0.9500 . . no C18 H18 0.9500 . . no C19 H19 0.9500 . . no C20 H20 0.9500 . . no C21 H21 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O8 H8 105.00 . . . no C2 N1 C6 121.3(2) . . . yes C6 N1 H1 119.00 . . . no C2 N1 H1 120.00 . . . no O1 N2 O2 119.8(2) . . . yes O1 N2 O3 118.2(2) . . . yes O2 N2 O3 122.0(2) . . . yes N1 C2 C3 120.4(2) . . . yes C2 C3 C4 120.4(2) . . . no C3 C4 C5 116.9(2) . . . no C5 C4 C7 123.4(2) . . . no C3 C4 C7 119.67(19) . . . no C4 C5 C6 120.9(2) . . . no N1 C6 C5 120.0(2) . . . yes C9 C7 C16 109.90(19) . . . no C4 C7 C16 108.92(19) . . . no O8 C7 C9 110.16(19) . . . yes O8 C7 C16 107.55(17) . . . yes C4 C7 C9 111.74(18) . . . no O8 C7 C4 108.47(18) . . . yes C7 C9 C10 114.0(2) . . . no C9 C10 C11 120.0(2) . . . no C11 C10 C15 117.8(2) . . . no C9 C10 C15 122.2(2) . . . no C10 C11 C12 121.5(2) . . . no C11 C12 C13 119.9(2) . . . no C12 C13 C14 119.6(2) . . . no C13 C14 C15 120.5(2) . . . no C10 C15 C14 120.7(2) . . . no C7 C16 C21 120.33(19) . . . no C17 C16 C21 118.8(2) . . . no C7 C16 C17 120.75(19) . . . no C16 C17 C18 120.3(2) . . . no C17 C18 C19 120.6(2) . . . no C18 C19 C20 119.2(2) . . . no C19 C20 C21 120.7(2) . . . no C16 C21 C20 120.4(2) . . . no N1 C2 H2 120.00 . . . no C3 C2 H2 120.00 . . . no C4 C3 H3 120.00 . . . no C2 C3 H3 120.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no C5 C6 H6 120.00 . . . no N1 C6 H6 120.00 . . . no C7 C9 H9A 109.00 . . . no C7 C9 H9B 109.00 . . . no C10 C9 H9A 109.00 . . . no C10 C9 H9B 109.00 . . . no H9A C9 H9B 108.00 . . . no C12 C11 H11 119.00 . . . no C10 C11 H11 119.00 . . . no C11 C12 H12 120.00 . . . no C13 C12 H12 120.00 . . . no C12 C13 H13 120.00 . . . no C14 C13 H13 120.00 . . . no C15 C14 H14 120.00 . . . no C13 C14 H14 120.00 . . . no C14 C15 H15 120.00 . . . no C10 C15 H15 120.00 . . . no C16 C17 H17 120.00 . . . no C18 C17 H17 120.00 . . . no C17 C18 H18 120.00 . . . no C19 C18 H18 120.00 . . . no C20 C19 H19 120.00 . . . no C18 C19 H19 120.00 . . . no C19 C20 H20 120.00 . . . no C21 C20 H20 120.00 . . . no C16 C21 H21 120.00 . . . no C20 C21 H21 120.00 . . . no 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 C6 N1 C2 C3 -1.2(4) . . . . no C2 N1 C6 C5 0.8(4) . . . . no N1 C2 C3 C4 0.5(4) . . . . no C2 C3 C4 C5 0.4(4) . . . . no C2 C3 C4 C7 -177.0(2) . . . . no C3 C4 C5 C6 -0.8(4) . . . . no C7 C4 C5 C6 176.5(2) . . . . no C3 C4 C7 O8 -39.2(3) . . . . no C3 C4 C7 C9 -160.8(2) . . . . no C3 C4 C7 C16 77.6(2) . . . . no C5 C4 C7 O8 143.6(2) . . . . no C5 C4 C7 C9 22.0(3) . . . . no C5 C4 C7 C16 -99.6(3) . . . . no C4 C5 C6 N1 0.2(4) . . . . no O8 C7 C9 C10 64.8(2) . . . . no C4 C7 C9 C10 -174.57(18) . . . . no C16 C7 C9 C10 -53.5(2) . . . . no O8 C7 C16 C17 172.2(2) . . . . no O8 C7 C16 C21 -11.1(3) . . . . no C4 C7 C16 C17 54.8(3) . . . . no C4 C7 C16 C21 -128.5(2) . . . . no C9 C7 C16 C17 -67.9(3) . . . . no C9 C7 C16 C21 108.8(2) . . . . no C7 C9 C10 C11 102.7(3) . . . . no C7 C9 C10 C15 -78.5(3) . . . . no C9 C10 C11 C12 179.1(2) . . . . no C15 C10 C11 C12 0.3(4) . . . . no C9 C10 C15 C14 -179.4(2) . . . . no C11 C10 C15 C14 -0.6(4) . . . . no C10 C11 C12 C13 0.7(4) . . . . no C11 C12 C13 C14 -1.3(4) . . . . no C12 C13 C14 C15 1.0(4) . . . . no C13 C14 C15 C10 -0.1(4) . . . . no C7 C16 C17 C18 176.7(2) . . . . no C21 C16 C17 C18 0.0(4) . . . . no C7 C16 C21 C20 -177.9(2) . . . . no C17 C16 C21 C20 -1.1(4) . . . . no C16 C17 C18 C19 1.3(4) . . . . no C17 C18 C19 C20 -1.3(4) . . . . no C18 C19 C20 C21 0.1(4) . . . . no C19 C20 C21 C16 1.1(4) . . . . no _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.63 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.395 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.051 _exptl_crystal_recrystallization_method methanol