# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Andreas Lemmerer' _publ_contact_author_email ANDREAS.LEMMERER@GMAIL.COM _publ_section_title ; Structural and melting point characterisation of six chiral ammonium carboxylate salts ; _publ_requested_category FO loop_ _publ_author_name 'Andreas Lemmerer' 'Susan Bourne' 'Manuel A Fernandes' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-11-16 at 19:59:14 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : 7ag418_a nonius data_1 _database_code_depnum_ccdc_archive 'CCDC 691820' _audit_creation_date 2008-07-28T18:18:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ((R)-1-phenylethylammonium) 2-naphthalenecarboxylate ; _chemical_formula_moiety 'C8 H12 N, C11 H7 O2' _chemical_formula_sum 'C19 H19 N O2' _chemical_formula_weight 293.35 _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.3682(13) _cell_length_b 14.511(3) _cell_length_c 17.457(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1613.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 15605 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.1 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.26 1 0 0 0.25 0 1 1 0.091 0 -1 -1 0.049 0 1 -1 0.081 0 -1 1 0.084 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.992 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '2.0\% \w and \p scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_av_R_equivalents 0.0854 _diffrn_reflns_av_unetI/netI 0.0376 _diffrn_reflns_number 14277 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 1745 _reflns_number_gt 1517 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _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 ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0973P)^2^+0.0176P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.035(8) _refine_ls_number_reflns 1745 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1334 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details . _refine_ls_abs_structure_Flack . _refine_diff_density_max 0.252 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.057 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0292(4) 0.55450(16) 0.35805(12) 0.0342(6) Uani 1 1 d . . . H1 H 0.1682 0.5598 0.3773 0.041 Uiso 1 1 calc R . . C2 C -0.0749(4) 0.47242(16) 0.36554(12) 0.0307(5) Uani 1 1 d . . . C3 C -0.2796(4) 0.46395(18) 0.33574(13) 0.0399(6) Uani 1 1 d . . . H3 H -0.3531 0.4074 0.3411 0.048 Uiso 1 1 calc R . . C4 C -0.3736(4) 0.5364(2) 0.29909(14) 0.0428(6) Uani 1 1 d . . . H4 H -0.5102 0.5288 0.2781 0.051 Uiso 1 1 calc R . . C4A C -0.2704(4) 0.62246(19) 0.29202(13) 0.0395(6) Uani 1 1 d . . . C5 C -0.3649(6) 0.7006(2) 0.25694(15) 0.0538(8) Uani 1 1 d . . . H5 H -0.502 0.6957 0.2359 0.065 Uiso 1 1 calc R . . C6 C -0.2602(6) 0.7827(2) 0.25319(17) 0.0622(9) Uani 1 1 d . . . H6 H -0.3249 0.8341 0.2292 0.075 Uiso 1 1 calc R . . C7 C -0.0597(6) 0.7918(2) 0.28415(18) 0.0603(9) Uani 1 1 d . . . H7 H 0.0103 0.8495 0.2818 0.072 Uiso 1 1 calc R . . C8 C 0.0368(5) 0.71811(19) 0.31782(16) 0.0504(7) Uani 1 1 d . . . H8 H 0.1739 0.725 0.3385 0.06 Uiso 1 1 calc R . . C8A C -0.0653(4) 0.63153(16) 0.32226(13) 0.0358(6) Uani 1 1 d . . . C9 C 0.0278(4) 0.39402(16) 0.40897(13) 0.0343(6) Uani 1 1 d . . . O1 O -0.0945(3) 0.33073(12) 0.43257(12) 0.0478(5) Uani 1 1 d . . . O2 O 0.2188(3) 0.39584(13) 0.41834(11) 0.0463(5) Uani 1 1 d . . . C10 C 0.6395(4) 0.49089(19) 0.56202(14) 0.0416(6) Uani 1 1 d . . . C11 C 0.5311(5) 0.54355(18) 0.50858(15) 0.0468(7) Uani 1 1 d . . . H11 H 0.4027 0.5214 0.488 0.056 Uiso 1 1 calc R . . C12 C 0.6088(7) 0.62803(19) 0.48514(18) 0.0597(9) Uani 1 1 d . . . H12 H 0.5345 0.6631 0.448 0.072 Uiso 1 1 calc R . . C13 C 0.7901(7) 0.6608(3) 0.5149(2) 0.0733(11) Uani 1 1 d . . . H13 H 0.8433 0.7185 0.4981 0.088 Uiso 1 1 calc R . . C14 C 0.8967(6) 0.6119(3) 0.5688(2) 0.0766(11) Uani 1 1 d . . . H14 H 1.0217 0.6364 0.5905 0.092 Uiso 1 1 calc R . . C15 C 0.8225(5) 0.5249(3) 0.59261(18) 0.0615(9) Uani 1 1 d . . . H15 H 0.8984 0.4901 0.6295 0.074 Uiso 1 1 calc R . . C16 C 0.5572(5) 0.39655(19) 0.58507(14) 0.0446(7) Uani 1 1 d . . . H16 H 0.6628 0.3674 0.6199 0.053 Uiso 1 1 calc R . . C17 C 0.3500(6) 0.3999(3) 0.62660(19) 0.0695(10) Uani 1 1 d . . . H17A H 0.2433 0.4271 0.5931 0.104 Uiso 1 1 calc R . . H17B H 0.3644 0.4375 0.6729 0.104 Uiso 1 1 calc R . . H17C H 0.3076 0.3373 0.6408 0.104 Uiso 1 1 calc R . . N1 N 0.5348(4) 0.33657(15) 0.51545(13) 0.0388(5) Uani 1 1 d . . . H1A H 0.406(6) 0.358(2) 0.4828(19) 0.058 Uiso 1 1 d . . . H1C H 0.502(5) 0.273(3) 0.5325(17) 0.058 Uiso 1 1 d . . . H1B H 0.674(6) 0.337(2) 0.493(2) 0.058 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0358(12) 0.0353(12) 0.0314(10) 0.0032(10) -0.0006(10) 0.0008(11) C2 0.0349(13) 0.0288(12) 0.0284(10) -0.0010(9) 0.0016(9) 0.0036(10) C3 0.0442(15) 0.0370(13) 0.0384(12) -0.0030(11) -0.0009(11) -0.0033(12) C4 0.0362(13) 0.0560(16) 0.0363(12) -0.0025(12) -0.0092(11) 0.0011(14) C4A 0.0458(14) 0.0463(15) 0.0263(11) 0.0001(11) 0.0017(10) 0.0114(13) C5 0.0660(19) 0.0615(19) 0.0340(13) 0.0090(12) -0.0011(13) 0.0201(17) C6 0.088(3) 0.0511(18) 0.0478(17) 0.0172(14) 0.0098(17) 0.026(2) C7 0.085(2) 0.0367(15) 0.0586(17) 0.0157(13) 0.0171(18) 0.0049(16) C8 0.0623(18) 0.0405(14) 0.0483(14) 0.0078(12) 0.0055(14) -0.0026(14) C8A 0.0462(15) 0.0330(12) 0.0281(11) 0.0041(9) 0.0056(10) 0.0027(11) C9 0.0412(14) 0.0289(12) 0.0327(11) -0.0009(10) 0.0024(10) 0.0028(12) O1 0.0479(11) 0.0316(9) 0.0640(11) 0.0137(8) 0.0105(10) 0.0024(9) O2 0.0429(11) 0.0409(10) 0.0551(11) 0.0070(9) -0.0085(9) 0.0036(9) C10 0.0468(15) 0.0419(14) 0.0360(12) -0.0045(10) 0.0013(11) 0.0048(13) C11 0.0637(18) 0.0327(13) 0.0439(13) -0.0029(11) -0.0026(13) 0.0069(13) C12 0.100(3) 0.0318(14) 0.0475(15) -0.0078(12) 0.0088(18) 0.0015(17) C13 0.113(3) 0.0493(18) 0.0579(19) -0.0154(17) 0.018(2) -0.016(2) C14 0.067(2) 0.084(3) 0.079(2) -0.036(2) 0.008(2) -0.029(2) C15 0.0554(19) 0.080(2) 0.0489(15) -0.0155(17) -0.0034(13) 0.0043(17) C16 0.0510(15) 0.0431(14) 0.0395(13) 0.0083(12) -0.0060(12) 0.0069(13) C17 0.085(3) 0.066(2) 0.0572(17) 0.0137(16) 0.0260(17) 0.009(2) N1 0.0382(13) 0.0300(11) 0.0483(12) 0.0081(9) -0.0001(10) 0.0026(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.369(3) . ? C1 C8A 1.415(3) . ? C1 H1 0.95 . ? C2 C3 1.409(4) . ? C2 C9 1.515(3) . ? C3 C4 1.369(4) . ? C3 H3 0.95 . ? C4 C4A 1.417(4) . ? C4 H4 0.95 . ? C4A C8A 1.415(4) . ? C4A C5 1.422(4) . ? C5 C6 1.367(5) . ? C5 H5 0.95 . ? C6 C7 1.393(5) . ? C6 H6 0.95 . ? C7 C8 1.366(4) . ? C7 H7 0.95 . ? C8 C8A 1.417(4) . ? C8 H8 0.95 . ? C9 O2 1.228(3) . ? C9 O1 1.272(3) . ? C10 C15 1.373(4) . ? C10 C11 1.390(4) . ? C10 C16 1.520(4) . ? C11 C12 1.384(4) . ? C11 H11 0.95 . ? C12 C13 1.353(6) . ? C12 H12 0.95 . ? C13 C14 1.360(6) . ? C13 H13 0.95 . ? C14 C15 1.411(6) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? C16 N1 1.502(4) . ? C16 C17 1.506(4) . ? C16 H16 1 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? N1 H1A 1.04(3) . ? N1 H1C 0.99(4) . ? N1 H1B 0.97(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C8A 121.6(2) . . ? C2 C1 H1 119.2 . . ? C8A C1 H1 119.2 . . ? C1 C2 C3 119.2(2) . . ? C1 C2 C9 119.5(2) . . ? C3 C2 C9 121.2(2) . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C4A 121.0(2) . . ? C3 C4 H4 119.5 . . ? C4A C4 H4 119.5 . . ? C8A C4A C4 118.5(2) . . ? C8A C4A C5 118.5(3) . . ? C4 C4A C5 123.0(3) . . ? C6 C5 C4A 120.6(3) . . ? C6 C5 H5 119.7 . . ? C4A C5 H5 119.7 . . ? C5 C6 C7 120.8(3) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.3(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C8A 120.7(3) . . ? C7 C8 H8 119.6 . . ? C8A C8 H8 119.6 . . ? C4A C8A C1 118.9(2) . . ? C4A C8A C8 119.1(2) . . ? C1 C8A C8 122.0(2) . . ? O2 C9 O1 125.3(2) . . ? O2 C9 C2 118.5(2) . . ? O1 C9 C2 116.1(2) . . ? C15 C10 C11 119.0(3) . . ? C15 C10 C16 120.9(3) . . ? C11 C10 C16 120.1(3) . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.6(3) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 119.4(3) . . ? C10 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? N1 C16 C17 109.0(3) . . ? N1 C16 C10 109.9(2) . . ? C17 C16 C10 113.6(3) . . ? N1 C16 H16 108.1 . . ? C17 C16 H16 108.1 . . ? C10 C16 H16 108.1 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 N1 H1A 110.0(18) . . ? C16 N1 H1C 108.3(18) . . ? H1A N1 H1C 106(2) . . ? C16 N1 H1B 104(2) . . ? H1A N1 H1B 119(3) . . ? H1C N1 H1B 109(3) . . ? 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 C8A C1 C2 C3 1.1(3) . . . . ? C8A C1 C2 C9 -175.95(19) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C9 C2 C3 C4 177.6(2) . . . . ? C2 C3 C4 C4A -1.8(4) . . . . ? C3 C4 C4A C8A 1.4(4) . . . . ? C3 C4 C4A C5 -177.6(2) . . . . ? C8A C4A C5 C6 -0.5(4) . . . . ? C4 C4A C5 C6 178.5(3) . . . . ? C4A C5 C6 C7 -0.5(4) . . . . ? C5 C6 C7 C8 1.0(4) . . . . ? C6 C7 C8 C8A -0.4(4) . . . . ? C4 C4A C8A C1 0.3(3) . . . . ? C5 C4A C8A C1 179.3(2) . . . . ? C4 C4A C8A C8 -177.9(2) . . . . ? C5 C4A C8A C8 1.1(3) . . . . ? C2 C1 C8A C4A -1.5(3) . . . . ? C2 C1 C8A C8 176.6(2) . . . . ? C7 C8 C8A C4A -0.7(4) . . . . ? C7 C8 C8A C1 -178.8(2) . . . . ? C1 C2 C9 O2 -19.5(3) . . . . ? C3 C2 C9 O2 163.5(2) . . . . ? C1 C2 C9 O1 160.8(2) . . . . ? C3 C2 C9 O1 -16.2(3) . . . . ? C15 C10 C11 C12 1.5(4) . . . . ? C16 C10 C11 C12 -177.6(3) . . . . ? C10 C11 C12 C13 -0.9(4) . . . . ? C11 C12 C13 C14 -0.8(5) . . . . ? C12 C13 C14 C15 1.9(5) . . . . ? C11 C10 C15 C14 -0.4(4) . . . . ? C16 C10 C15 C14 178.7(3) . . . . ? C13 C14 C15 C10 -1.3(5) . . . . ? C15 C10 C16 N1 -122.1(3) . . . . ? C11 C10 C16 N1 57.0(3) . . . . ? C15 C10 C16 C17 115.5(3) . . . . ? C11 C10 C16 C17 -65.4(3) . . . . ? 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 N1 H1A O2 1.04(3) 1.73(4) 2.768(3) 172(3) . N1 H1C O1 0.99(4) 1.74(4) 2.719(3) 171(3) 3_556 N1 H1B O1 0.97(4) 1.82(4) 2.771(3) 168(3) 1_655 _chemical_name_common '((R)-1-phenylethylammonium) 2-naphthalenecarboxylate' ###END data_2 _database_code_depnum_ccdc_archive 'CCDC 691821' _audit_creation_date 2008-07-28T18:27:54-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ((S)-1-phenylethylammonium) 2-naphthalenecarboxylate ; _chemical_formula_moiety 'C8 H12 N, C11 H7 O2' _chemical_formula_sum 'C19 H19 N O2' _chemical_formula_weight 293.35 _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.3709(13) _cell_length_b 14.513(3) _cell_length_c 17.445(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1612.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16602 _cell_measurement_theta_min 0.21 _cell_measurement_theta_max 27.1 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.244 _exptl_crystal_size_min 0.135 _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.25 -1 0 0 0.25 0 0 1 0.105 0 0 -1 0.139 0 1 0 0.067 0 -1 0 0.068 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.9614 _exptl_absorpt_correction_T_max 0.987 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '2.0\% \w and \p scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_unetI/netI 0.0333 _diffrn_reflns_number 15206 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 1749 _reflns_number_gt 1496 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _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 ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0657P)^2^+0.0592P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.031(4) _refine_ls_number_reflns 1749 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.037 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details . _refine_ls_abs_structure_Flack . _refine_diff_density_max 0.138 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9711(3) 0.44549(13) 0.64174(11) 0.0347(4) Uani 1 1 d . . . H1 H 0.8321 0.4403 0.6225 0.042 Uiso 1 1 calc R . . C2 C 1.0750(3) 0.52741(12) 0.63420(10) 0.0317(4) Uani 1 1 d . . . C3 C 1.2796(3) 0.53577(14) 0.66411(11) 0.0405(5) Uani 1 1 d . . . H3 H 1.3533 0.5923 0.6587 0.049 Uiso 1 1 calc R . . C4 C 1.3725(4) 0.46375(16) 0.70069(11) 0.0443(5) Uani 1 1 d . . . H4 H 1.5087 0.4714 0.722 0.053 Uiso 1 1 calc R . . C4A C 1.2702(4) 0.37769(14) 0.70764(11) 0.0403(5) Uani 1 1 d . . . C5 C 1.3653(4) 0.29943(17) 0.74265(13) 0.0548(6) Uani 1 1 d . . . H5 H 1.5027 0.3044 0.7634 0.066 Uiso 1 1 calc R . . C6 C 1.2608(5) 0.21739(17) 0.74666(14) 0.0619(7) Uani 1 1 d . . . H6 H 1.3255 0.166 0.7708 0.074 Uiso 1 1 calc R . . C7 C 1.0602(5) 0.20840(16) 0.71566(15) 0.0609(7) Uani 1 1 d . . . H7 H 0.9903 0.1507 0.718 0.073 Uiso 1 1 calc R . . C8 C 0.9638(4) 0.28166(15) 0.68205(13) 0.0503(6) Uani 1 1 d . . . H8 H 0.8267 0.2747 0.6614 0.06 Uiso 1 1 calc R . . C8A C 1.0655(3) 0.36806(12) 0.67751(11) 0.0362(5) Uani 1 1 d . . . C9 C 0.9731(3) 0.60601(12) 0.59120(11) 0.0349(5) Uani 1 1 d . . . O1 O 1.0941(2) 0.66918(9) 0.56749(9) 0.0485(4) Uani 1 1 d . . . O2 O 0.7809(2) 0.60392(10) 0.58144(9) 0.0458(4) Uani 1 1 d . . . C10 C 0.3607(4) 0.50962(14) 0.43803(12) 0.0419(5) Uani 1 1 d . . . C11 C 0.4676(4) 0.45642(14) 0.49144(13) 0.0475(6) Uani 1 1 d . . . H11 H 0.5962 0.4782 0.5122 0.057 Uiso 1 1 calc R . . C12 C 0.3892(5) 0.37224(15) 0.51464(14) 0.0599(7) Uani 1 1 d . . . H12 H 0.4627 0.3374 0.5521 0.072 Uiso 1 1 calc R . . C13 C 0.2111(6) 0.3391(2) 0.48497(18) 0.0730(9) Uani 1 1 d . . . H13 H 0.1595 0.281 0.5014 0.088 Uiso 1 1 calc R . . C14 C 0.1026(5) 0.3884(2) 0.43106(18) 0.0783(9) Uani 1 1 d . . . H14 H -0.0229 0.364 0.4097 0.094 Uiso 1 1 calc R . . C15 C 0.1771(4) 0.4750(2) 0.40727(15) 0.0609(7) Uani 1 1 d . . . H15 H 0.1015 0.5096 0.3702 0.073 Uiso 1 1 calc R . . C16 C 0.4431(4) 0.60359(15) 0.41511(12) 0.0456(5) Uani 1 1 d . . . H16 H 0.3377 0.6328 0.3802 0.055 Uiso 1 1 calc R . . C17 C 0.6502(5) 0.60012(19) 0.37363(16) 0.0684(8) Uani 1 1 d . . . H17A H 0.7569 0.5731 0.4073 0.103 Uiso 1 1 calc R . . H17B H 0.6926 0.6627 0.3592 0.103 Uiso 1 1 calc R . . H17C H 0.636 0.5623 0.3274 0.103 Uiso 1 1 calc R . . N1 N 0.4656(3) 0.66353(12) 0.48447(11) 0.0391(4) Uani 1 1 d . . . H1A H 0.588(4) 0.6424(16) 0.5191(15) 0.059 Uiso 1 1 d . . . H1B H 0.332(5) 0.6650(17) 0.5104(16) 0.059 Uiso 1 1 d . . . H1C H 0.498(4) 0.7257(19) 0.4665(14) 0.059 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0328(10) 0.0397(10) 0.0316(9) 0.0029(8) -0.0008(9) 0.0002(9) C2 0.0330(11) 0.0348(10) 0.0272(9) -0.0008(8) 0.0023(8) 0.0014(8) C3 0.0396(12) 0.0432(11) 0.0386(11) -0.0039(9) -0.0002(10) -0.0034(9) C4 0.0348(11) 0.0608(13) 0.0373(11) -0.0035(10) -0.0075(10) 0.0030(11) C4A 0.0445(12) 0.0501(12) 0.0263(10) -0.0006(9) 0.0027(9) 0.0105(10) C5 0.0614(15) 0.0674(16) 0.0357(12) 0.0089(10) -0.0014(12) 0.0216(13) C6 0.086(2) 0.0557(14) 0.0442(14) 0.0183(11) 0.0096(14) 0.0270(15) C7 0.0843(19) 0.0419(12) 0.0564(14) 0.0150(11) 0.0170(15) 0.0044(13) C8 0.0584(14) 0.0439(11) 0.0486(12) 0.0075(10) 0.0029(12) -0.0025(11) C8A 0.0413(12) 0.0387(10) 0.0286(10) 0.0031(8) 0.0050(9) 0.0030(8) C9 0.0402(12) 0.0317(10) 0.0328(10) -0.0007(8) 0.0026(9) 0.0030(9) O1 0.0448(9) 0.0365(7) 0.0642(10) 0.0136(7) 0.0108(8) 0.0021(7) O2 0.0385(9) 0.0477(8) 0.0512(9) 0.0072(7) -0.0084(7) 0.0030(7) C10 0.0437(12) 0.0462(11) 0.0357(11) -0.0050(9) -0.0002(10) 0.0053(10) C11 0.0596(14) 0.0374(11) 0.0455(12) -0.0034(9) -0.0031(11) 0.0044(10) C12 0.098(2) 0.0338(11) 0.0476(13) -0.0103(10) 0.0067(15) 0.0032(13) C13 0.107(3) 0.0542(15) 0.0573(17) -0.0175(14) 0.0185(18) -0.0174(16) C14 0.0648(17) 0.091(2) 0.079(2) -0.0373(18) 0.0093(17) -0.0299(17) C15 0.0515(15) 0.0835(18) 0.0477(14) -0.0148(13) -0.0029(11) 0.0039(13) C16 0.0497(13) 0.0494(12) 0.0376(11) 0.0087(10) -0.0066(10) 0.0084(10) C17 0.0763(19) 0.0727(16) 0.0562(15) 0.0156(13) 0.0240(14) 0.0083(15) N1 0.0356(10) 0.0344(9) 0.0474(11) 0.0088(8) -0.0006(9) 0.0033(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.367(3) . ? C1 C8A 1.419(3) . ? C1 H1 0.95 . ? C2 C3 1.409(3) . ? C2 C9 1.512(3) . ? C3 C4 1.360(3) . ? C3 H3 0.95 . ? C4 C4A 1.414(3) . ? C4 H4 0.95 . ? C4A C8A 1.413(3) . ? C4A C5 1.425(3) . ? C5 C6 1.366(4) . ? C5 H5 0.95 . ? C6 C7 1.394(4) . ? C6 H6 0.95 . ? C7 C8 1.361(3) . ? C7 H7 0.95 . ? C8 C8A 1.414(3) . ? C8 H8 0.95 . ? C9 O2 1.236(2) . ? C9 O1 1.267(2) . ? C10 C15 1.381(3) . ? C10 C11 1.389(3) . ? C10 C16 1.515(3) . ? C11 C12 1.380(3) . ? C11 H11 0.95 . ? C12 C13 1.336(4) . ? C12 H12 0.95 . ? C13 C14 1.369(4) . ? C13 H13 0.95 . ? C14 C15 1.407(4) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? C16 N1 1.497(3) . ? C16 C17 1.506(3) . ? C16 H16 1 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? N1 H1A 1.03(3) . ? N1 H1B 0.96(3) . ? N1 H1C 0.98(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C8A 121.72(17) . . ? C2 C1 H1 119.1 . . ? C8A C1 H1 119.1 . . ? C1 C2 C3 119.16(17) . . ? C1 C2 C9 119.73(17) . . ? C3 C2 C9 121.06(17) . . ? C4 C3 C2 120.67(19) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C4A 121.2(2) . . ? C3 C4 H4 119.4 . . ? C4A C4 H4 119.4 . . ? C8A C4A C4 118.75(18) . . ? C8A C4A C5 118.2(2) . . ? C4 C4A C5 123.0(2) . . ? C6 C5 C4A 120.6(2) . . ? C6 C5 H5 119.7 . . ? C4A C5 H5 119.7 . . ? C5 C6 C7 120.6(2) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.5(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C8A 120.7(2) . . ? C7 C8 H8 119.7 . . ? C8A C8 H8 119.7 . . ? C4A C8A C8 119.34(19) . . ? C4A C8A C1 118.45(18) . . ? C8 C8A C1 122.19(18) . . ? O2 C9 O1 125.11(19) . . ? O2 C9 C2 118.37(17) . . ? O1 C9 C2 116.52(17) . . ? C15 C10 C11 118.3(2) . . ? C15 C10 C16 121.2(2) . . ? C11 C10 C16 120.5(2) . . ? C12 C11 C10 120.7(2) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 120.5(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120 . . ? C15 C14 H14 120 . . ? C10 C15 C14 119.7(3) . . ? C10 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? N1 C16 C17 108.9(2) . . ? N1 C16 C10 110.06(17) . . ? C17 C16 C10 113.6(2) . . ? N1 C16 H16 108 . . ? C17 C16 H16 108 . . ? C10 C16 H16 108 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 N1 H1A 111.9(14) . . ? C16 N1 H1B 107.9(16) . . ? H1A N1 H1B 113(2) . . ? C16 N1 H1C 107.3(14) . . ? H1A N1 H1C 107.6(19) . . ? H1B N1 H1C 108(2) . . ? 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 C8A C1 C2 C3 -1.3(3) . . . . ? C8A C1 C2 C9 176.11(16) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C9 C2 C3 C4 -177.98(18) . . . . ? C2 C3 C4 C4A 2.1(3) . . . . ? C3 C4 C4A C8A -1.6(3) . . . . ? C3 C4 C4A C5 177.3(2) . . . . ? C8A C4A C5 C6 0.2(3) . . . . ? C4 C4A C5 C6 -178.8(2) . . . . ? C4A C5 C6 C7 0.8(4) . . . . ? C5 C6 C7 C8 -1.1(4) . . . . ? C6 C7 C8 C8A 0.4(3) . . . . ? C4 C4A C8A C8 178.15(19) . . . . ? C5 C4A C8A C8 -0.9(3) . . . . ? C4 C4A C8A C1 -0.2(3) . . . . ? C5 C4A C8A C1 -179.23(19) . . . . ? C7 C8 C8A C4A 0.6(3) . . . . ? C7 C8 C8A C1 178.9(2) . . . . ? C2 C1 C8A C4A 1.7(3) . . . . ? C2 C1 C8A C8 -176.62(18) . . . . ? C1 C2 C9 O2 18.8(3) . . . . ? C3 C2 C9 O2 -163.78(19) . . . . ? C1 C2 C9 O1 -160.78(17) . . . . ? C3 C2 C9 O1 16.6(3) . . . . ? C15 C10 C11 C12 -1.7(3) . . . . ? C16 C10 C11 C12 177.6(2) . . . . ? C10 C11 C12 C13 1.5(4) . . . . ? C11 C12 C13 C14 -0.2(4) . . . . ? C12 C13 C14 C15 -0.8(4) . . . . ? C11 C10 C15 C14 0.7(3) . . . . ? C16 C10 C15 C14 -178.6(2) . . . . ? C13 C14 C15 C10 0.6(4) . . . . ? C15 C10 C16 N1 122.3(2) . . . . ? C11 C10 C16 N1 -57.0(3) . . . . ? C15 C10 C16 C17 -115.4(2) . . . . ? C11 C10 C16 C17 65.3(3) . . . . ? 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 N1 H1A O2 1.03(3) 1.74(3) 2.765(2) 176(2) . N1 H1B O1 0.96(3) 1.82(3) 2.776(3) 175(2) 1_455 N1 H1C O1 0.98(3) 1.75(3) 2.718(2) 171(2) 3_466 _chemical_name_common '((S)-1-phenylethylammonium) 2-naphthalenecarboxylate' ###END data_3 _database_code_depnum_ccdc_archive 'CCDC 691822' _audit_creation_date 2008-07-28T18:32:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; bis((RS)-1-phenylethylammonium) 26-naphthalenedicarboxylate ; _chemical_formula_moiety 'C8 H12 N, C11 H7 O2' _chemical_formula_sum 'C19 H19 N O2' _chemical_formula_weight 293.35 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 6.1388(5) _cell_length_b 10.6194(5) _cell_length_c 12.8861(9) _cell_angle_alpha 105.398(4) _cell_angle_beta 101.879(3) _cell_angle_gamma 98.163(5) _cell_volume 775.14(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 17035 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 28.28 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.264 0 0 -1 0.16 1 0 0 0.25 -1 -8 12 0.099 2 1 -13 0.25 -1 2 4 0.269 -1 8 0 0.25 0 1 -1 0.239 -1 1 0 0.226 -6 -7 2 0.34 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.9803 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '2.0\% \w and \p scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_unetI/netI 0.0276 _diffrn_reflns_number 14817 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 2849 _reflns_number_gt 2588 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _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 ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0510P)^2^+0.1709P] 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_number_reflns 2849 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.094 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.209 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.031 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.07642(17) 0.03190(10) 0.22281(8) 0.0214(2) Uani 1 1 d . . . H1 H -0.2016 0.0364 0.2554 0.026 Uiso 1 1 calc R . . C2 C 0.09932(17) 0.14092(10) 0.25549(8) 0.0201(2) Uani 1 1 d . . . C3 C 0.28499(18) 0.13471(10) 0.20618(9) 0.0240(2) Uani 1 1 d . . . H3 H 0.4076 0.2098 0.229 0.029 Uiso 1 1 calc R . . C4 C 0.28961(18) 0.02162(11) 0.12587(9) 0.0251(2) Uani 1 1 d . . . H4A H 0.4143 0.0198 0.0928 0.03 Uiso 1 1 calc R . . C4A C 0.11120(18) -0.09268(10) 0.09144(8) 0.0233(2) Uani 1 1 d . . . C5 C 0.1130(2) -0.21278(11) 0.01077(9) 0.0297(3) Uani 1 1 d . . . H5 H 0.2357 -0.2175 -0.0236 0.036 Uiso 1 1 calc R . . C6 C -0.0602(2) -0.32181(11) -0.01791(9) 0.0337(3) Uani 1 1 d . . . H6 H -0.0563 -0.4019 -0.0716 0.04 Uiso 1 1 calc R . . C7 C -0.2441(2) -0.31636(11) 0.03148(10) 0.0327(3) Uani 1 1 d . . . H7 H -0.3636 -0.3927 0.0106 0.039 Uiso 1 1 calc R . . C8 C -0.25242(19) -0.20208(11) 0.10939(9) 0.0274(2) Uani 1 1 d . . . H8 H -0.3775 -0.1995 0.1422 0.033 Uiso 1 1 calc R . . C8A C -0.07491(17) -0.08755(10) 0.14123(8) 0.0220(2) Uani 1 1 d . . . C9 C 0.08888(17) 0.26544(10) 0.34257(8) 0.0206(2) Uani 1 1 d . . . O1 O 0.24762(12) 0.36737(7) 0.36788(6) 0.0266(2) Uani 1 1 d . . . O2 O -0.07805(12) 0.26288(7) 0.38428(6) 0.0269(2) Uani 1 1 d . . . C10 C 0.64831(18) 0.66773(10) 0.34922(9) 0.0240(2) Uani 1 1 d . . . C11 C 0.41672(19) 0.64061(11) 0.29692(10) 0.0302(3) Uani 1 1 d . . . H11 H 0.3372 0.5507 0.2613 0.036 Uiso 1 1 calc R . . C12 C 0.3016(2) 0.74391(12) 0.29647(10) 0.0343(3) Uani 1 1 d . . . H12 H 0.1442 0.7245 0.26 0.041 Uiso 1 1 calc R . . C13 C 0.4151(2) 0.87483(12) 0.34891(10) 0.0348(3) Uani 1 1 d . . . H13 H 0.336 0.9455 0.3486 0.042 Uiso 1 1 calc R . . C14 C 0.6440(2) 0.90272(12) 0.40182(10) 0.0351(3) Uani 1 1 d . . . H14 H 0.7221 0.9927 0.4384 0.042 Uiso 1 1 calc R . . C15 C 0.7606(2) 0.79961(11) 0.40182(9) 0.0291(3) Uani 1 1 d . . . H15 H 0.9182 0.8196 0.4381 0.035 Uiso 1 1 calc R . . C16 C 0.77979(17) 0.55673(10) 0.34559(9) 0.0241(2) Uani 1 1 d . . . H16 H 0.945 0.5987 0.3778 0.029 Uiso 1 1 calc R . . C17 C 0.7507(2) 0.46667(12) 0.22812(9) 0.0334(3) Uani 1 1 d . . . H17A H 0.5906 0.4215 0.196 0.05 Uiso 1 1 calc R . . H17B H 0.8452 0.3999 0.2303 0.05 Uiso 1 1 calc R . . H17C H 0.7975 0.5205 0.1823 0.05 Uiso 1 1 calc R . . N1 N 0.70974(15) 0.47275(9) 0.41505(7) 0.0215(2) Uani 1 1 d . . . H1A H 0.550(2) 0.4312(13) 0.3907(11) 0.032 Uiso 1 1 d . . . H1B H 0.732(2) 0.5269(13) 0.4902(12) 0.032 Uiso 1 1 d . . . H1C H 0.791(2) 0.4038(13) 0.4114(11) 0.032 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0209(5) 0.0231(5) 0.0222(5) 0.0086(4) 0.0059(4) 0.0068(4) C2 0.0220(5) 0.0195(5) 0.0198(5) 0.0076(4) 0.0035(4) 0.0069(4) C3 0.0230(5) 0.0215(5) 0.0264(5) 0.0070(4) 0.0059(4) 0.0025(4) C4 0.0244(5) 0.0279(6) 0.0248(5) 0.0075(4) 0.0098(4) 0.0070(4) C4A 0.0266(5) 0.0239(5) 0.0194(5) 0.0072(4) 0.0030(4) 0.0081(4) C5 0.0349(6) 0.0298(6) 0.0229(5) 0.0040(4) 0.0069(5) 0.0109(5) C6 0.0453(7) 0.0247(6) 0.0235(6) -0.0006(4) 0.0030(5) 0.0075(5) C7 0.0385(6) 0.0238(6) 0.0272(6) 0.0051(4) -0.0008(5) -0.0023(5) C8 0.0271(6) 0.0268(5) 0.0256(5) 0.0083(4) 0.0031(4) 0.0016(4) C8A 0.0240(5) 0.0217(5) 0.0195(5) 0.0077(4) 0.0017(4) 0.0051(4) C9 0.0223(5) 0.0201(5) 0.0204(5) 0.0077(4) 0.0034(4) 0.0080(4) O1 0.0269(4) 0.0205(4) 0.0277(4) 0.0019(3) 0.0063(3) 0.0018(3) O2 0.0281(4) 0.0238(4) 0.0315(4) 0.0066(3) 0.0130(3) 0.0092(3) C10 0.0269(5) 0.0255(5) 0.0229(5) 0.0098(4) 0.0091(4) 0.0075(4) C11 0.0284(6) 0.0269(6) 0.0365(6) 0.0130(5) 0.0069(5) 0.0049(4) C12 0.0292(6) 0.0423(7) 0.0408(7) 0.0229(6) 0.0115(5) 0.0141(5) C13 0.0498(7) 0.0348(6) 0.0340(6) 0.0185(5) 0.0207(5) 0.0236(6) C14 0.0536(8) 0.0240(6) 0.0278(6) 0.0058(4) 0.0127(5) 0.0085(5) C15 0.0325(6) 0.0284(6) 0.0239(5) 0.0066(4) 0.0052(4) 0.0038(5) C16 0.0228(5) 0.0260(5) 0.0253(5) 0.0091(4) 0.0076(4) 0.0061(4) C17 0.0453(7) 0.0358(6) 0.0256(6) 0.0116(5) 0.0134(5) 0.0180(5) N1 0.0227(5) 0.0208(4) 0.0211(5) 0.0048(4) 0.0061(3) 0.0067(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3715(15) . ? C1 C8A 1.4189(15) . ? C1 H1 0.95 . ? C2 C3 1.4158(15) . ? C2 C9 1.5091(14) . ? C3 C4 1.3696(15) . ? C3 H3 0.95 . ? C4 C4A 1.4164(15) . ? C4 H4A 0.95 . ? C4A C5 1.4185(15) . ? C4A C8A 1.4215(15) . ? C5 C6 1.3672(17) . ? C5 H5 0.95 . ? C6 C7 1.4061(18) . ? C6 H6 0.95 . ? C7 C8 1.3694(16) . ? C7 H7 0.95 . ? C8 C8A 1.4176(15) . ? C8 H8 0.95 . ? C9 O2 1.2515(12) . ? C9 O1 1.2688(12) . ? C10 C15 1.3877(16) . ? C10 C11 1.3945(16) . ? C10 C16 1.5163(14) . ? C11 C12 1.3871(16) . ? C11 H11 0.95 . ? C12 C13 1.3810(18) . ? C12 H12 0.95 . ? C13 C14 1.3810(19) . ? C13 H13 0.95 . ? C14 C15 1.3905(17) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? C16 N1 1.5016(13) . ? C16 C17 1.5197(15) . ? C16 H16 1 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? N1 H1A 0.967(14) . ? N1 H1B 0.956(14) . ? N1 H1C 0.940(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C8A 121.30(10) . . ? C2 C1 H1 119.4 . . ? C8A C1 H1 119.4 . . ? C1 C2 C3 119.41(9) . . ? C1 C2 C9 119.08(9) . . ? C3 C2 C9 121.51(9) . . ? C4 C3 C2 120.68(9) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C4A 120.97(10) . . ? C3 C4 H4A 119.5 . . ? C4A C4 H4A 119.5 . . ? C4 C4A C5 122.58(10) . . ? C4 C4A C8A 118.66(9) . . ? C5 C4A C8A 118.75(10) . . ? C6 C5 C4A 120.59(10) . . ? C6 C5 H5 119.7 . . ? C4A C5 H5 119.7 . . ? C5 C6 C7 120.50(10) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.65(10) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C8A 120.18(10) . . ? C7 C8 H8 119.9 . . ? C8A C8 H8 119.9 . . ? C8 C8A C1 121.69(10) . . ? C8 C8A C4A 119.33(10) . . ? C1 C8A C4A 118.98(9) . . ? O2 C9 O1 123.77(9) . . ? O2 C9 C2 118.05(9) . . ? O1 C9 C2 118.17(9) . . ? C15 C10 C11 118.83(10) . . ? C15 C10 C16 119.86(10) . . ? C11 C10 C16 121.27(10) . . ? C12 C11 C10 120.47(11) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.23(11) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 119.76(10) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.25(11) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 120.45(11) . . ? C10 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? N1 C16 C10 110.80(8) . . ? N1 C16 C17 108.88(9) . . ? C10 C16 C17 112.93(9) . . ? N1 C16 H16 108 . . ? C10 C16 H16 108 . . ? C17 C16 H16 108 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 N1 H1A 113.0(8) . . ? C16 N1 H1B 110.4(8) . . ? H1A N1 H1B 104.9(11) . . ? C16 N1 H1C 109.9(8) . . ? H1A N1 H1C 107.1(11) . . ? H1B N1 H1C 111.3(11) . . ? 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 C8A C1 C2 C3 0.59(15) . . . . ? C8A C1 C2 C9 179.97(8) . . . . ? C1 C2 C3 C4 0.51(15) . . . . ? C9 C2 C3 C4 -178.85(9) . . . . ? C2 C3 C4 C4A -1.11(16) . . . . ? C3 C4 C4A C5 -178.23(10) . . . . ? C3 C4 C4A C8A 0.59(15) . . . . ? C4 C4A C5 C6 178.34(10) . . . . ? C8A C4A C5 C6 -0.48(16) . . . . ? C4A C5 C6 C7 0.51(17) . . . . ? C5 C6 C7 C8 -0.26(18) . . . . ? C6 C7 C8 C8A -0.02(17) . . . . ? C7 C8 C8A C1 -179.09(10) . . . . ? C7 C8 C8A C4A 0.04(15) . . . . ? C2 C1 C8A C8 178.05(9) . . . . ? C2 C1 C8A C4A -1.09(15) . . . . ? C4 C4A C8A C8 -178.66(9) . . . . ? C5 C4A C8A C8 0.20(15) . . . . ? C4 C4A C8A C1 0.49(14) . . . . ? C5 C4A C8A C1 179.36(9) . . . . ? C1 C2 C9 O2 2.11(14) . . . . ? C3 C2 C9 O2 -178.53(9) . . . . ? C1 C2 C9 O1 -176.68(8) . . . . ? C3 C2 C9 O1 2.68(14) . . . . ? C15 C10 C11 C12 0.75(16) . . . . ? C16 C10 C11 C12 -176.84(10) . . . . ? C10 C11 C12 C13 -0.65(17) . . . . ? C11 C12 C13 C14 0.07(17) . . . . ? C12 C13 C14 C15 0.41(17) . . . . ? C11 C10 C15 C14 -0.27(16) . . . . ? C16 C10 C15 C14 177.36(9) . . . . ? C13 C14 C15 C10 -0.31(17) . . . . ? C15 C10 C16 N1 112.15(11) . . . . ? C11 C10 C16 N1 -70.28(12) . . . . ? C15 C10 C16 C17 -125.40(11) . . . . ? C11 C10 C16 C17 52.17(13) . . . . ? 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 N1 H1A O1 0.97(1) 1.82(1) 2.774(1) 170.6(1) . N1 H1B O1 0.96(1) 1.84(2) 2.797(1) 175.6(1) 2_666 N1 H1C O2 0.94(1) 1.79(1) 2.718(1) 171.8(1) 1_655 _chemical_name_common 'bis((RS)-1-phenylethylammonium) 26-naphthalenedicarboxylate' ###END data_4 _database_code_depnum_ccdc_archive 'CCDC 691823' _audit_creation_date 2008-07-28T18:39:16-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; bis((R)-1-phenylethylammonium) naphthalene-2,6-dicarboxylate ; _chemical_formula_moiety 'C12 H6 O4, 2(C8 H12 N)' _chemical_formula_sum 'C28 H30 N2 O4' _chemical_formula_weight 458.54 _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.6633(4) _cell_length_b 6.3731(3) _cell_length_c 19.7210(7) _cell_angle_alpha 90 _cell_angle_beta 96.041(2) _cell_angle_gamma 90 _cell_volume 1207.78(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 37785 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 28.28 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 1 0.089 1 0 1 0.17 4 1 7 0.152 1 -10 -8 0.291 -1 2 1 0.303 1 0 -7 0.027 -1 0 7 0.092 5 0 -1 0.132 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.9526 _exptl_absorpt_correction_T_max 0.9919 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '1.8\% \w and \p scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.067 _diffrn_reflns_av_unetI/netI 0.0233 _diffrn_reflns_number 32802 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 2456 _reflns_number_gt 2156 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _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 ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0564P)^2^+0.1265P] 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_number_reflns 2456 _refine_ls_number_parameters 327 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details . _refine_ls_abs_structure_Flack . _refine_diff_density_max 0.186 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.07025(18) 0.5860(4) 0.81689(9) 0.0219(4) Uani 1 1 d . . . H1 H 0.0533 0.7252 0.8312 0.026 Uiso 1 1 calc R . . C2 C 0.18024(18) 0.4755(4) 0.84910(9) 0.0219(5) Uani 1 1 d . . . C3 C 0.2038(2) 0.2664(4) 0.82889(10) 0.0256(5) Uani 1 1 d . . . H3 H 0.2776 0.1878 0.8522 0.031 Uiso 1 1 calc R . . C4 C 0.12149(19) 0.1767(4) 0.77618(10) 0.0265(5) Uani 1 1 d . . . H4 H 0.1397 0.037 0.7628 0.032 Uiso 1 1 calc R . . C4A C 0.00922(18) 0.2891(4) 0.74108(9) 0.0221(5) Uani 1 1 d . . . C5 C -0.0776(2) 0.2003(4) 0.68622(9) 0.0244(5) Uani 1 1 d . . . H5 H -0.0601 0.0614 0.6719 0.029 Uiso 1 1 calc R . . C6 C -0.1868(2) 0.3112(4) 0.65335(9) 0.0244(5) Uani 1 1 d . . . C7 C -0.2136(2) 0.5173(4) 0.67506(10) 0.0273(5) Uani 1 1 d . . . H7 H -0.2887 0.5946 0.6523 0.033 Uiso 1 1 calc R . . C8 C -0.1330(2) 0.6069(4) 0.72831(9) 0.0266(5) Uani 1 1 d . . . H8 H -0.1537 0.7447 0.7426 0.032 Uiso 1 1 calc R . . C8A C -0.01844(18) 0.4964(4) 0.76280(9) 0.0211(5) Uani 1 1 d . . . C9 C 0.2797(2) 0.5809(4) 0.90297(10) 0.0232(5) Uani 1 1 d . . . C9A C -0.2782(2) 0.2078(4) 0.59589(10) 0.0274(5) Uani 1 1 d . . . O1 O 0.37032(14) 0.4675(3) 0.93629(7) 0.0296(4) Uani 1 1 d . . . O2 O 0.26950(16) 0.7749(3) 0.90950(8) 0.0373(4) Uani 1 1 d . . . O3 O -0.36561(14) 0.3210(3) 0.56059(7) 0.0316(4) Uani 1 1 d . . . O4 O -0.2627(2) 0.0171(3) 0.58685(9) 0.0541(5) Uani 1 1 d . . . C10 C 0.28751(19) 0.2799(4) 1.09714(9) 0.0255(5) Uani 1 1 d . . . C11 C 0.1824(2) 0.4279(4) 1.09566(11) 0.0348(5) Uani 1 1 d . . . H11 H 0.1004 0.4096 1.0652 0.042 Uiso 1 1 calc R . . C12 C 0.1943(3) 0.6017(4) 1.13763(12) 0.0392(6) Uani 1 1 d . . . H12 H 0.1205 0.7006 1.1359 0.047 Uiso 1 1 calc R . . C13 C 0.3119(2) 0.6331(5) 1.18192(12) 0.0421(6) Uani 1 1 d . . . H13 H 0.3195 0.7517 1.2113 0.05 Uiso 1 1 calc R . . C14 C 0.4183(3) 0.4896(5) 1.18301(13) 0.0491(7) Uani 1 1 d . . . H14 H 0.5012 0.5118 1.2125 0.059 Uiso 1 1 calc R . . C15 C 0.4066(2) 0.3134(5) 1.14176(11) 0.0392(6) Uani 1 1 d . . . H15 H 0.4805 0.2146 1.144 0.047 Uiso 1 1 calc R . . C16 C 0.27370(19) 0.0820(4) 1.05426(10) 0.0277(5) Uani 1 1 d . . . H16 H 0.2988 -0.0396 1.0852 0.033 Uiso 1 1 calc R . . C17 C 0.1284(2) 0.0426(5) 1.01909(12) 0.0435(6) Uani 1 1 d . . . H17A H 0.1045 0.1526 0.9851 0.065 Uiso 1 1 calc R . . H17B H 0.0612 0.0443 1.053 0.065 Uiso 1 1 calc R . . H17C H 0.1258 -0.0944 0.9965 0.065 Uiso 1 1 calc R . . N1 N 0.37292(17) 0.0837(3) 1.00054(8) 0.0241(4) Uani 1 1 d . . . H1A H 0.366(2) 0.218(5) 0.9749(12) 0.036 Uiso 1 1 d . . . H1C H 0.351(2) -0.028(5) 0.9680(12) 0.036 Uiso 1 1 d . . . H1B H 0.461(2) 0.062(4) 1.0206(10) 0.036 Uiso 1 1 d . . . C18 C -0.2903(2) -0.1505(4) 0.39709(10) 0.0317(5) Uani 1 1 d . . . C19 C -0.2039(3) 0.0233(4) 0.40423(12) 0.0419(6) Uani 1 1 d . . . H19 H -0.1361 0.0335 0.4426 0.05 Uiso 1 1 calc R . . C20 C -0.2150(3) 0.1825(5) 0.35608(13) 0.0486(7) Uani 1 1 d . . . H20 H -0.1548 0.3004 0.3616 0.058 Uiso 1 1 calc R . . C21 C -0.3126(3) 0.1707(5) 0.30049(14) 0.0507(7) Uani 1 1 d . . . H21 H -0.3203 0.2796 0.2674 0.061 Uiso 1 1 calc R . . C22 C -0.3995(3) -0.0012(6) 0.29320(13) 0.0575(8) Uani 1 1 d . . . H22 H -0.468 -0.0099 0.255 0.069 Uiso 1 1 calc R . . C23 C -0.3881(2) -0.1604(5) 0.34062(11) 0.0448(6) Uani 1 1 d . . . H23 H -0.4481 -0.2786 0.3345 0.054 Uiso 1 1 calc R . . C24 C -0.2807(2) -0.3279(4) 0.44804(11) 0.0322(5) Uani 1 1 d . . . H24 H -0.3142 -0.4583 0.4233 0.039 Uiso 1 1 calc R . . C25 C -0.1347(2) -0.3716(5) 0.48284(13) 0.0453(7) Uani 1 1 d . . . H25A H -0.1053 -0.2551 0.5135 0.068 Uiso 1 1 calc R . . H25B H -0.0696 -0.3857 0.4482 0.068 Uiso 1 1 calc R . . H25C H -0.1356 -0.5019 0.5092 0.068 Uiso 1 1 calc R . . N2 N -0.37508(18) -0.2862(4) 0.50209(9) 0.0263(4) Uani 1 1 d . . . H2A H -0.352(3) -0.170(5) 0.5291(13) 0.039 Uiso 1 1 d . . . H2C H -0.376(3) -0.406(5) 0.5308(13) 0.039 Uiso 1 1 d . . . H2B H -0.468(2) -0.273(4) 0.4805(11) 0.039 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0228(9) 0.0203(11) 0.0219(9) -0.0008(9) -0.0006(8) 0.0001(9) C2 0.0205(10) 0.0242(12) 0.0211(9) 0.0009(10) 0.0019(8) -0.0033(9) C3 0.0239(10) 0.0253(13) 0.0259(10) -0.0018(10) -0.0051(8) 0.0054(10) C4 0.0292(11) 0.0222(13) 0.0269(10) -0.0042(10) -0.0031(9) 0.0062(10) C4A 0.0233(10) 0.0224(12) 0.0199(9) 0.0000(9) -0.0016(8) -0.0002(9) C5 0.0308(11) 0.0203(11) 0.0212(10) -0.0027(9) -0.0017(8) 0.0002(10) C6 0.0259(10) 0.0264(12) 0.0194(9) -0.0012(10) -0.0048(8) -0.0027(10) C7 0.0284(10) 0.0257(13) 0.0258(10) 0.0003(10) -0.0068(8) 0.0019(10) C8 0.0300(11) 0.0217(12) 0.0264(10) -0.0022(9) -0.0048(9) 0.0035(9) C8A 0.0225(10) 0.0196(11) 0.0207(9) 0.0007(9) 0.0001(8) 0.0004(9) C9 0.0201(10) 0.0255(13) 0.0235(10) 0.0003(10) -0.0004(8) -0.0002(10) C9A 0.0284(11) 0.0295(15) 0.0220(11) -0.0008(10) -0.0078(9) -0.0029(11) O1 0.0253(7) 0.0283(9) 0.0323(8) 0.0046(8) -0.0106(6) -0.0051(7) O2 0.0366(9) 0.0290(10) 0.0419(9) -0.0097(8) -0.0161(7) 0.0008(8) O3 0.0291(7) 0.0317(10) 0.0306(8) 0.0005(8) -0.0125(6) -0.0014(8) O4 0.0759(13) 0.0268(11) 0.0505(10) -0.0119(9) -0.0358(9) 0.0056(10) C10 0.0258(10) 0.0265(11) 0.0243(9) 0.0020(9) 0.0026(8) -0.0036(9) C11 0.0334(12) 0.0350(13) 0.0347(11) 0.0018(10) -0.0022(9) 0.0046(11) C12 0.0433(13) 0.0326(15) 0.0430(13) 0.0014(12) 0.0108(10) 0.0082(12) C13 0.0508(14) 0.0371(16) 0.0406(13) -0.0100(12) 0.0157(11) -0.0069(12) C14 0.0375(13) 0.0613(19) 0.0470(14) -0.0208(14) -0.0028(11) -0.0041(13) C15 0.0269(10) 0.0487(15) 0.0404(12) -0.0094(12) -0.0031(9) 0.0050(11) C16 0.0256(10) 0.0257(12) 0.0312(10) -0.0005(10) 0.0002(8) -0.0055(9) C17 0.0248(11) 0.0520(17) 0.0534(14) -0.0163(13) 0.0024(10) -0.0101(12) N1 0.0201(8) 0.0236(10) 0.0266(9) -0.0033(9) -0.0062(7) -0.0007(8) C18 0.0303(11) 0.0360(13) 0.0289(10) -0.0032(10) 0.0039(9) 0.0028(10) C19 0.0476(13) 0.0374(15) 0.0397(13) -0.0038(11) -0.0007(11) -0.0059(12) C20 0.0557(16) 0.0373(16) 0.0552(15) -0.0025(14) 0.0170(13) -0.0065(14) C21 0.0496(15) 0.056(2) 0.0487(15) 0.0138(14) 0.0159(13) 0.0065(15) C22 0.0480(15) 0.084(2) 0.0392(13) 0.0160(16) -0.0027(11) -0.0074(17) C23 0.0386(12) 0.0592(17) 0.0356(12) 0.0043(13) -0.0008(10) -0.0110(13) C24 0.0305(11) 0.0299(13) 0.0352(11) -0.0042(10) -0.0016(9) 0.0032(10) C25 0.0298(12) 0.0484(17) 0.0573(15) 0.0075(14) 0.0020(11) 0.0085(12) N2 0.0257(9) 0.0258(11) 0.0256(9) -0.0005(9) -0.0061(7) -0.0001(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.374(3) . ? C1 C8A 1.416(2) . ? C1 H1 0.95 . ? C2 C3 1.416(3) . ? C2 C9 1.513(3) . ? C3 C4 1.366(3) . ? C3 H3 0.95 . ? C4 C4A 1.418(3) . ? C4 H4 0.95 . ? C4A C5 1.416(3) . ? C4A C8A 1.423(3) . ? C5 C6 1.375(3) . ? C5 H5 0.95 . ? C6 C7 1.414(4) . ? C6 C9A 1.513(3) . ? C7 C8 1.365(3) . ? C7 H7 0.95 . ? C8 C8A 1.423(3) . ? C8 H8 0.95 . ? C9 O2 1.248(3) . ? C9 O1 1.265(3) . ? C9A O4 1.240(3) . ? C9A O3 1.263(3) . ? C10 C11 1.385(3) . ? C10 C15 1.390(3) . ? C10 C16 1.516(3) . ? C11 C12 1.380(4) . ? C11 H11 0.95 . ? C12 C13 1.373(3) . ? C12 H12 0.95 . ? C13 C14 1.374(4) . ? C13 H13 0.95 . ? C14 C15 1.385(4) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? C16 N1 1.502(3) . ? C16 C17 1.520(3) . ? C16 H16 1 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? N1 H1A 0.99(3) . ? N1 H1C 0.97(3) . ? N1 H1B 0.91(2) . ? C18 C23 1.384(3) . ? C18 C19 1.385(3) . ? C18 C24 1.509(3) . ? C19 C20 1.386(4) . ? C19 H19 0.95 . ? C20 C21 1.371(4) . ? C20 H20 0.95 . ? C21 C22 1.379(4) . ? C21 H21 0.95 . ? C22 C23 1.376(4) . ? C22 H22 0.95 . ? C23 H23 0.95 . ? C24 N2 1.498(3) . ? C24 C25 1.528(3) . ? C24 H24 1 . ? C25 H25A 0.98 . ? C25 H25B 0.98 . ? C25 H25C 0.98 . ? N2 H2A 0.92(3) . ? N2 H2C 0.95(3) . ? N2 H2B 0.95(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C8A 121.3(2) . . ? C2 C1 H1 119.4 . . ? C8A C1 H1 119.4 . . ? C1 C2 C3 119.45(19) . . ? C1 C2 C9 120.0(2) . . ? C3 C2 C9 120.42(19) . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C4A 120.9(2) . . ? C3 C4 H4 119.5 . . ? C4A C4 H4 119.5 . . ? C5 C4A C4 122.2(2) . . ? C5 C4A C8A 119.10(17) . . ? C4 C4A C8A 118.73(17) . . ? C6 C5 C4A 121.2(2) . . ? C6 C5 H5 119.4 . . ? C4A C5 H5 119.4 . . ? C5 C6 C7 119.40(19) . . ? C5 C6 C9A 119.2(2) . . ? C7 C6 C9A 121.4(2) . . ? C8 C7 C6 120.9(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C8A 120.9(2) . . ? C7 C8 H8 119.6 . . ? C8A C8 H8 119.6 . . ? C1 C8A C4A 118.89(16) . . ? C1 C8A C8 122.6(2) . . ? C4A C8A C8 118.48(17) . . ? O2 C9 O1 124.7(2) . . ? O2 C9 C2 117.45(19) . . ? O1 C9 C2 117.7(2) . . ? O4 C9A O3 124.4(2) . . ? O4 C9A C6 117.7(2) . . ? O3 C9A C6 117.9(2) . . ? C11 C10 C15 117.7(2) . . ? C11 C10 C16 122.25(18) . . ? C15 C10 C16 120.0(2) . . ? C12 C11 C10 121.3(2) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 120.7(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 118.7(2) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C13 C14 C15 121.1(2) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C10 120.5(2) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? N1 C16 C10 111.26(18) . . ? N1 C16 C17 107.87(16) . . ? C10 C16 C17 114.51(19) . . ? N1 C16 H16 107.6 . . ? C10 C16 H16 107.6 . . ? C17 C16 H16 107.6 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 N1 H1A 110.5(14) . . ? C16 N1 H1C 110.5(14) . . ? H1A N1 H1C 107.2(19) . . ? C16 N1 H1B 109.3(12) . . ? H1A N1 H1B 111(2) . . ? H1C N1 H1B 108(2) . . ? C23 C18 C19 118.1(2) . . ? C23 C18 C24 119.4(2) . . ? C19 C18 C24 122.51(19) . . ? C18 C19 C20 120.9(2) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C21 C20 C19 120.3(3) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 119.2(3) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C23 C22 C21 120.7(2) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 C18 120.8(3) . . ? C22 C23 H23 119.6 . . ? C18 C23 H23 119.6 . . ? N2 C24 C18 109.97(19) . . ? N2 C24 C25 108.38(17) . . ? C18 C24 C25 115.1(2) . . ? N2 C24 H24 107.7 . . ? C18 C24 H24 107.7 . . ? C25 C24 H24 107.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 N2 H2A 114.9(16) . . ? C24 N2 H2C 108.9(16) . . ? H2A N2 H2C 108(2) . . ? C24 N2 H2B 108.1(12) . . ? H2A N2 H2B 111(2) . . ? H2C N2 H2B 106(2) . . ? 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 C8A C1 C2 C3 -1.4(3) . . . . ? C8A C1 C2 C9 175.28(17) . . . . ? C1 C2 C3 C4 2.4(3) . . . . ? C9 C2 C3 C4 -174.23(18) . . . . ? C2 C3 C4 C4A -1.0(3) . . . . ? C3 C4 C4A C5 179.90(18) . . . . ? C3 C4 C4A C8A -1.4(3) . . . . ? C4 C4A C5 C6 179.31(19) . . . . ? C8A C4A C5 C6 0.7(3) . . . . ? C4A C5 C6 C7 -0.5(3) . . . . ? C4A C5 C6 C9A -178.85(18) . . . . ? C5 C6 C7 C8 -0.3(3) . . . . ? C9A C6 C7 C8 177.98(19) . . . . ? C6 C7 C8 C8A 1.0(3) . . . . ? C2 C1 C8A C4A -1.0(3) . . . . ? C2 C1 C8A C8 -179.87(18) . . . . ? C5 C4A C8A C1 -178.87(19) . . . . ? C4 C4A C8A C1 2.4(3) . . . . ? C5 C4A C8A C8 0.0(3) . . . . ? C4 C4A C8A C8 -178.7(2) . . . . ? C7 C8 C8A C1 178.01(18) . . . . ? C7 C8 C8A C4A -0.8(3) . . . . ? C1 C2 C9 O2 -10.0(3) . . . . ? C3 C2 C9 O2 166.6(2) . . . . ? C1 C2 C9 O1 172.64(17) . . . . ? C3 C2 C9 O1 -10.7(3) . . . . ? C5 C6 C9A O4 9.7(3) . . . . ? C7 C6 C9A O4 -168.6(2) . . . . ? C5 C6 C9A O3 -170.65(19) . . . . ? C7 C6 C9A O3 11.0(3) . . . . ? C15 C10 C11 C12 -0.8(3) . . . . ? C16 C10 C11 C12 176.7(2) . . . . ? C10 C11 C12 C13 0.4(4) . . . . ? C11 C12 C13 C14 0.9(4) . . . . ? C12 C13 C14 C15 -1.7(4) . . . . ? C13 C14 C15 C10 1.3(4) . . . . ? C11 C10 C15 C14 0.0(3) . . . . ? C16 C10 C15 C14 -177.6(2) . . . . ? C11 C10 C16 N1 113.0(2) . . . . ? C15 C10 C16 N1 -69.5(2) . . . . ? C11 C10 C16 C17 -9.6(3) . . . . ? C15 C10 C16 C17 167.9(2) . . . . ? C23 C18 C19 C20 -0.1(4) . . . . ? C24 C18 C19 C20 179.5(2) . . . . ? C18 C19 C20 C21 0.3(4) . . . . ? C19 C20 C21 C22 0.1(4) . . . . ? C20 C21 C22 C23 -0.6(4) . . . . ? C21 C22 C23 C18 0.7(4) . . . . ? C19 C18 C23 C22 -0.4(4) . . . . ? C24 C18 C23 C22 180.0(2) . . . . ? C23 C18 C24 N2 -89.8(2) . . . . ? C19 C18 C24 N2 90.6(3) . . . . ? C23 C18 C24 C25 147.4(2) . . . . ? C19 C18 C24 C25 -32.2(3) . . . . ? 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 N1 H1A O1 0.99(3) 1.77(3) 2.754(3) 173(2) . N1 H1C O2 0.97(3) 1.83(3) 2.778(2) 167(2) 1_545 N1 H1B O1 0.91(2) 1.86(2) 2.758(2) 169(3) 2_647 N2 H2A O4 0.92(3) 1.80(3) 2.707(3) 165(2) . N2 H2C O3 0.95(3) 1.84(3) 2.754(3) 161(2) 1_545 N2 H2B O3 0.95(2) 1.83(2) 2.761(2) 166(3) 2_446 _chemical_name_common 'bis((R)-1-phenylethylammonium) naphthalene-2,6-dicarboxylate' ###END data_5 _database_code_depnum_ccdc_archive 'CCDC 691824' _audit_creation_date 2008-07-28T18:48:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; bis((S)1-phenylethylammonium) 2,6-naphthalenedicarboxylate ; _chemical_formula_moiety 'C12 H6 O4, 2(C8 H12 N)' _chemical_formula_sum 'C28 H30 N2 O4' _chemical_formula_weight 458.54 _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.6656(12) _cell_length_b 6.3707(9) _cell_length_c 19.708(2) _cell_angle_alpha 90 _cell_angle_beta 96.025(7) _cell_angle_gamma 90 _cell_volume 1206.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 15524 _cell_measurement_theta_min 0.81 _cell_measurement_theta_max 27.1 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.061 0 0 1 0.017 0 -1 0 0.156 0 1 0 0.116 1 0 0 0.02 -1 0 0 0.02 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 0.996 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '1.5\% \w and \p scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.1662 _diffrn_reflns_av_unetI/netI 0.1065 _diffrn_reflns_number 21242 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 2441 _reflns_number_gt 1497 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _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 ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0000P)^2^+0.4221P] 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_number_reflns 2441 _refine_ls_number_parameters 327 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1241 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details . _refine_ls_abs_structure_Flack . _refine_diff_density_max 0.214 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9300(5) 0.4137(8) 0.1832(2) 0.0280(13) Uani 1 1 d . . . H1 H 0.9468 0.2744 0.1689 0.034 Uiso 1 1 calc R . . C2 C 0.8202(5) 0.5243(9) 0.1512(2) 0.0271(13) Uani 1 1 d . . . C3 C 0.7966(5) 0.7345(9) 0.1716(2) 0.0320(13) Uani 1 1 d . . . H3 H 0.7225 0.8134 0.1486 0.038 Uiso 1 1 calc R . . C4 C 0.8792(5) 0.8228(9) 0.2237(2) 0.0326(14) Uani 1 1 d . . . H4 H 0.8616 0.963 0.2368 0.039 Uiso 1 1 calc R . . C4A C 0.9910(4) 0.7111(8) 0.2590(2) 0.0272(12) Uani 1 1 d . . . C5 C 1.0782(5) 0.7995(8) 0.3138(2) 0.0308(14) Uani 1 1 d . . . H5 H 1.0619 0.9391 0.3278 0.037 Uiso 1 1 calc R . . C6 C 1.1867(5) 0.6866(9) 0.3473(2) 0.0308(13) Uani 1 1 d . . . C7 C 1.2140(5) 0.4842(10) 0.3250(3) 0.0345(14) Uani 1 1 d . . . H7 H 1.2904 0.408 0.3471 0.041 Uiso 1 1 calc R . . C8 C 1.1326(5) 0.3933(8) 0.2718(2) 0.0331(14) Uani 1 1 d . . . H8 H 1.1527 0.2547 0.2579 0.04 Uiso 1 1 calc R . . C8A C 1.0186(5) 0.5039(9) 0.2372(2) 0.0265(13) Uani 1 1 d . . . C9 C 0.7199(5) 0.4191(9) 0.0970(3) 0.0288(14) Uani 1 1 d . . . C9A C 1.2772(6) 0.7924(10) 0.4038(3) 0.0361(16) Uani 1 1 d . . . O1 O 0.6298(3) 0.5318(6) 0.06383(16) 0.0366(10) Uani 1 1 d . . . O2 O 0.7305(3) 0.2242(6) 0.09068(18) 0.0438(10) Uani 1 1 d . . . O3 O 1.3660(3) 0.6798(6) 0.43947(16) 0.0386(10) Uani 1 1 d . . . O4 O 1.2628(4) 0.9840(7) 0.4133(2) 0.0602(13) Uani 1 1 d . . . C10 C 0.7132(4) 0.7201(8) -0.0974(2) 0.0312(11) Uani 1 1 d . . . C11 C 0.8180(5) 0.5740(8) -0.0959(2) 0.0401(13) Uani 1 1 d . . . H11 H 0.9 0.5935 -0.0655 0.048 Uiso 1 1 calc R . . C12 C 0.8063(6) 0.3976(9) -0.1381(3) 0.0416(15) Uani 1 1 d . . . H12 H 0.8803 0.299 -0.1365 0.05 Uiso 1 1 calc R . . C13 C 0.6888(6) 0.3671(11) -0.1814(3) 0.0540(18) Uani 1 1 d . . . H13 H 0.681 0.2481 -0.2107 0.065 Uiso 1 1 calc R . . C14 C 0.5819(5) 0.5087(10) -0.1827(3) 0.0558(16) Uani 1 1 d . . . H14 H 0.4988 0.4855 -0.212 0.067 Uiso 1 1 calc R . . C15 C 0.5945(5) 0.6890(9) -0.1409(2) 0.0455(13) Uani 1 1 d . . . H15 H 0.5211 0.7886 -0.1428 0.055 Uiso 1 1 calc R . . C16 C 0.7263(5) 0.9187(8) -0.0543(2) 0.0320(13) Uani 1 1 d . . . H16 H 0.702 1.0406 -0.0853 0.038 Uiso 1 1 calc R . . C17 C 0.8710(5) 0.9560(10) -0.0190(3) 0.0485(16) Uani 1 1 d . . . H17A H 0.8758 1.0964 0.0014 0.073 Uiso 1 1 calc R . . H17B H 0.9391 0.9452 -0.0524 0.073 Uiso 1 1 calc R . . H17C H 0.8918 0.8504 0.0168 0.073 Uiso 1 1 calc R . . N1 N 0.6264(5) 0.9174(7) -0.0008(2) 0.0289(11) Uani 1 1 d . . . H1A H 0.638(5) 0.783(8) 0.025(2) 0.043 Uiso 1 1 d . . . H1B H 0.520(5) 0.927(8) -0.024(2) 0.043 Uiso 1 1 d . . . H1C H 0.649(5) 1.019(9) 0.031(2) 0.043 Uiso 1 1 d . . . C18 C 1.2906(5) 1.1507(8) 0.6033(2) 0.0396(13) Uani 1 1 d . . . C19 C 1.2041(5) 0.9761(9) 0.5956(3) 0.0489(14) Uani 1 1 d . . . H19 H 1.1372 0.965 0.5569 0.059 Uiso 1 1 calc R . . C20 C 1.2151(6) 0.8176(11) 0.6444(3) 0.0577(19) Uani 1 1 d . . . H20 H 1.154 0.7006 0.6395 0.069 Uiso 1 1 calc R . . C21 C 1.3127(6) 0.8292(11) 0.6991(3) 0.0500(17) Uani 1 1 d . . . H21 H 1.3204 0.7195 0.7319 0.06 Uiso 1 1 calc R . . C22 C 1.4002(6) 0.9987(12) 0.7070(3) 0.0628(18) Uani 1 1 d . . . H22 H 1.4689 1.0059 0.7451 0.075 Uiso 1 1 calc R . . C23 C 1.3883(5) 1.1598(10) 0.6594(2) 0.0502(15) Uani 1 1 d . . . H23 H 1.4484 1.2778 0.6655 0.06 Uiso 1 1 calc R . . C24 C 1.2802(5) 1.3288(9) 0.5520(3) 0.0360(14) Uani 1 1 d . . . H24 H 1.3138 1.4595 0.5766 0.043 Uiso 1 1 calc R . . C25 C 1.1348(5) 1.3722(9) 0.5174(3) 0.0511(16) Uani 1 1 d . . . H25A H 1.135 1.5044 0.492 0.077 Uiso 1 1 calc R . . H25B H 1.0694 1.3826 0.552 0.077 Uiso 1 1 calc R . . H25C H 1.1063 1.2574 0.4859 0.077 Uiso 1 1 calc R . . N2 N 1.3750(5) 1.2858(8) 0.4981(2) 0.0301(12) Uani 1 1 d . . . H2A H 1.356(5) 1.144(9) 0.465(2) 0.045 Uiso 1 1 d . . . H2B H 1.482(5) 1.251(8) 0.523(2) 0.045 Uiso 1 1 d . . . H2C H 1.372(5) 1.392(8) 0.469(3) 0.045 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.027(3) 0.024(3) 0.034(3) -0.001(3) 0.002(2) 0.001(2) C2 0.025(3) 0.028(4) 0.029(3) -0.001(3) 0.005(2) -0.007(3) C3 0.033(3) 0.023(4) 0.038(3) -0.003(3) -0.006(2) 0.004(3) C4 0.039(3) 0.023(4) 0.035(3) -0.007(3) -0.001(3) 0.003(3) C4A 0.032(3) 0.018(3) 0.031(3) 0.001(3) 0.000(2) -0.003(3) C5 0.042(3) 0.019(3) 0.030(3) -0.006(2) -0.001(3) -0.002(3) C6 0.036(3) 0.025(4) 0.030(3) 0.001(3) -0.001(2) 0.004(3) C7 0.032(3) 0.032(4) 0.037(3) 0.001(3) -0.005(2) 0.002(3) C8 0.039(3) 0.020(3) 0.038(3) -0.001(3) -0.006(3) 0.007(2) C8A 0.030(3) 0.022(4) 0.028(3) 0.001(3) 0.004(2) -0.001(3) C9 0.023(3) 0.028(4) 0.035(3) -0.003(3) 0.003(2) 0.000(3) C9A 0.044(3) 0.034(4) 0.028(3) 0.000(3) -0.006(3) -0.006(3) O1 0.035(2) 0.032(3) 0.040(2) 0.004(2) -0.0116(17) -0.0030(19) O2 0.049(2) 0.028(3) 0.050(2) -0.012(2) -0.0128(18) 0.000(2) O3 0.037(2) 0.035(3) 0.041(2) 0.001(2) -0.0097(18) 0.000(2) O4 0.082(3) 0.027(3) 0.063(3) -0.011(2) -0.033(2) 0.008(2) C10 0.026(2) 0.031(3) 0.037(3) 0.003(2) 0.001(2) -0.003(2) C11 0.033(3) 0.041(4) 0.044(3) 0.002(3) -0.003(2) 0.003(3) C12 0.054(4) 0.023(4) 0.049(3) -0.003(3) 0.010(3) 0.009(3) C13 0.060(4) 0.055(5) 0.050(4) -0.004(3) 0.018(3) -0.002(4) C14 0.040(3) 0.069(5) 0.056(4) -0.022(3) -0.008(3) -0.005(3) C15 0.038(3) 0.044(4) 0.053(3) -0.012(3) 0.000(2) 0.006(3) C16 0.032(3) 0.023(3) 0.041(3) -0.009(3) 0.005(2) -0.009(2) C17 0.033(3) 0.048(4) 0.065(4) -0.019(3) 0.010(3) -0.009(3) N1 0.032(2) 0.022(3) 0.032(2) -0.004(2) -0.002(2) -0.002(2) C18 0.043(3) 0.034(4) 0.042(3) -0.002(3) 0.008(3) 0.004(3) C19 0.059(3) 0.039(4) 0.048(3) -0.007(3) 0.001(3) -0.003(3) C20 0.061(4) 0.044(5) 0.070(5) 0.004(4) 0.017(4) -0.004(3) C21 0.056(4) 0.045(4) 0.052(4) 0.013(3) 0.020(3) 0.001(3) C22 0.059(4) 0.084(5) 0.044(3) 0.017(4) -0.002(3) -0.010(4) C23 0.047(3) 0.060(4) 0.043(3) 0.004(3) 0.004(3) -0.006(3) C24 0.038(3) 0.030(3) 0.039(3) 0.003(3) 0.001(3) 0.003(3) C25 0.042(3) 0.043(4) 0.068(4) 0.005(3) 0.007(3) 0.010(3) N2 0.037(3) 0.023(3) 0.029(2) 0.000(2) -0.002(2) 0.004(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.371(6) . ? C1 C8A 1.416(6) . ? C1 H1 0.95 . ? C2 C3 1.424(8) . ? C2 C9 1.520(6) . ? C3 C4 1.354(7) . ? C3 H3 0.95 . ? C4 C4A 1.415(6) . ? C4 H4 0.95 . ? C4A C5 1.415(6) . ? C4A C8A 1.422(5) . ? C5 C6 1.381(6) . ? C5 H5 0.95 . ? C6 C7 1.396(8) . ? C6 C9A 1.501(7) . ? C7 C8 1.371(7) . ? C7 H7 0.95 . ? C8 C8A 1.421(6) . ? C8 H8 0.95 . ? C9 O2 1.254(7) . ? C9 O1 1.258(6) . ? C9A O4 1.245(7) . ? C9A O3 1.273(6) . ? C10 C15 1.372(6) . ? C10 C11 1.373(6) . ? C10 C16 1.522(7) . ? C11 C12 1.395(7) . ? C11 H11 0.95 . ? C12 C13 1.362(8) . ? C12 H12 0.95 . ? C13 C14 1.370(8) . ? C13 H13 0.95 . ? C14 C15 1.412(8) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? C16 N1 1.503(6) . ? C16 C17 1.514(6) . ? C16 H16 1 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? N1 H1A 1.00(5) . ? N1 H1B 1.08(5) . ? N1 H1C 0.91(5) . ? C18 C23 1.377(6) . ? C18 C19 1.391(7) . ? C18 C24 1.516(7) . ? C19 C20 1.391(8) . ? C19 H19 0.95 . ? C20 C21 1.357(8) . ? C20 H20 0.95 . ? C21 C22 1.370(8) . ? C21 H21 0.95 . ? C22 C23 1.387(8) . ? C22 H22 0.95 . ? C23 H23 0.95 . ? C24 N2 1.499(6) . ? C24 C25 1.522(7) . ? C24 H24 1 . ? C25 H25A 0.98 . ? C25 H25B 0.98 . ? C25 H25C 0.98 . ? N2 H2A 1.12(5) . ? N2 H2B 1.12(5) . ? N2 H2C 0.89(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C8A 121.0(5) . . ? C2 C1 H1 119.5 . . ? C8A C1 H1 119.5 . . ? C1 C2 C3 119.5(5) . . ? C1 C2 C9 120.2(5) . . ? C3 C2 C9 120.3(5) . . ? C4 C3 C2 120.4(5) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C4A 121.6(5) . . ? C3 C4 H4 119.2 . . ? C4A C4 H4 119.2 . . ? C4 C4A C5 122.6(5) . . ? C4 C4A C8A 118.4(4) . . ? C5 C4A C8A 119.0(4) . . ? C6 C5 C4A 121.3(5) . . ? C6 C5 H5 119.4 . . ? C4A C5 H5 119.4 . . ? C5 C6 C7 119.3(5) . . ? C5 C6 C9A 118.3(5) . . ? C7 C6 C9A 122.3(5) . . ? C8 C7 C6 121.2(5) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C8A 120.8(5) . . ? C7 C8 H8 119.6 . . ? C8A C8 H8 119.6 . . ? C1 C8A C8 122.5(5) . . ? C1 C8A C4A 119.1(4) . . ? C8 C8A C4A 118.4(4) . . ? O2 C9 O1 125.0(5) . . ? O2 C9 C2 117.0(5) . . ? O1 C9 C2 118.0(5) . . ? O4 C9A O3 123.3(5) . . ? O4 C9A C6 119.1(5) . . ? O3 C9A C6 117.6(5) . . ? C15 C10 C11 118.9(5) . . ? C15 C10 C16 118.9(4) . . ? C11 C10 C16 122.2(4) . . ? C10 C11 C12 121.3(5) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C13 C12 C11 119.9(5) . . ? C13 C12 H12 120 . . ? C11 C12 H12 120 . . ? C12 C13 C14 119.7(6) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 120.4(5) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C10 C15 C14 119.8(5) . . ? C10 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? N1 C16 C17 108.0(4) . . ? N1 C16 C10 111.4(4) . . ? C17 C16 C10 113.9(4) . . ? N1 C16 H16 107.8 . . ? C17 C16 H16 107.8 . . ? C10 C16 H16 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 N1 H1A 109(3) . . ? C16 N1 H1B 110(2) . . ? H1A N1 H1B 109(4) . . ? C16 N1 H1C 111(3) . . ? H1A N1 H1C 104(4) . . ? H1B N1 H1C 114(4) . . ? C23 C18 C19 118.4(5) . . ? C23 C18 C24 119.7(5) . . ? C19 C18 C24 121.9(5) . . ? C18 C19 C20 120.2(5) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 120.4(6) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.1(6) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C23 120.0(5) . . ? C21 C22 H22 120 . . ? C23 C22 H22 120 . . ? C18 C23 C22 120.8(5) . . ? C18 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? N2 C24 C18 109.4(4) . . ? N2 C24 C25 108.7(4) . . ? C18 C24 C25 115.4(5) . . ? N2 C24 H24 107.7 . . ? C18 C24 H24 107.7 . . ? C25 C24 H24 107.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 N2 H2A 119(2) . . ? C24 N2 H2B 109(2) . . ? H2A N2 H2B 101(3) . . ? C24 N2 H2C 110(3) . . ? H2A N2 H2C 103(4) . . ? H2B N2 H2C 113(4) . . ? 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 C8A C1 C2 C3 1.3(7) . . . . ? C8A C1 C2 C9 -175.4(4) . . . . ? C1 C2 C3 C4 -2.1(7) . . . . ? C9 C2 C3 C4 174.6(4) . . . . ? C2 C3 C4 C4A 0.3(8) . . . . ? C3 C4 C4A C5 -179.7(5) . . . . ? C3 C4 C4A C8A 2.1(7) . . . . ? C4 C4A C5 C6 -179.9(5) . . . . ? C8A C4A C5 C6 -1.7(7) . . . . ? C4A C5 C6 C7 2.4(7) . . . . ? C4A C5 C6 C9A 178.5(4) . . . . ? C5 C6 C7 C8 -1.9(8) . . . . ? C9A C6 C7 C8 -177.8(5) . . . . ? C6 C7 C8 C8A 0.7(8) . . . . ? C2 C1 C8A C8 179.5(5) . . . . ? C2 C1 C8A C4A 1.2(6) . . . . ? C7 C8 C8A C1 -178.3(4) . . . . ? C7 C8 C8A C4A 0.0(7) . . . . ? C4 C4A C8A C1 -2.9(5) . . . . ? C5 C4A C8A C1 178.9(5) . . . . ? C4 C4A C8A C8 178.8(5) . . . . ? C5 C4A C8A C8 0.5(6) . . . . ? C1 C2 C9 O2 10.0(7) . . . . ? C3 C2 C9 O2 -166.6(5) . . . . ? C1 C2 C9 O1 -172.5(4) . . . . ? C3 C2 C9 O1 10.9(7) . . . . ? C5 C6 C9A O4 -8.5(8) . . . . ? C7 C6 C9A O4 167.4(5) . . . . ? C5 C6 C9A O3 171.8(5) . . . . ? C7 C6 C9A O3 -12.3(8) . . . . ? C15 C10 C11 C12 0.8(7) . . . . ? C16 C10 C11 C12 -177.1(5) . . . . ? C10 C11 C12 C13 -0.5(8) . . . . ? C11 C12 C13 C14 -0.8(9) . . . . ? C12 C13 C14 C15 1.9(9) . . . . ? C11 C10 C15 C14 0.3(7) . . . . ? C16 C10 C15 C14 178.2(5) . . . . ? C13 C14 C15 C10 -1.6(8) . . . . ? C15 C10 C16 N1 68.7(6) . . . . ? C11 C10 C16 N1 -113.4(5) . . . . ? C15 C10 C16 C17 -168.8(5) . . . . ? C11 C10 C16 C17 9.1(7) . . . . ? C23 C18 C19 C20 1.3(8) . . . . ? C24 C18 C19 C20 -178.8(5) . . . . ? C18 C19 C20 C21 -1.7(9) . . . . ? C19 C20 C21 C22 0.8(9) . . . . ? C20 C21 C22 C23 0.5(9) . . . . ? C19 C18 C23 C22 0.0(8) . . . . ? C24 C18 C23 C22 -179.9(5) . . . . ? C21 C22 C23 C18 -0.9(9) . . . . ? C23 C18 C24 N2 89.5(5) . . . . ? C19 C18 C24 N2 -90.4(6) . . . . ? C23 C18 C24 C25 -147.6(5) . . . . ? C19 C18 C24 C25 32.4(7) . . . . ? 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 N1 H1A O1 1.00(5) 1.77(5) 2.766(6) 170(4) . N1 H1B O1 1.08(5) 1.71(5) 2.749(5) 160(4) 2_655 N1 H1C O2 0.91(5) 1.87(5) 2.776(6) 169(4) 1_565 N2 H2A O4 1.12(5) 1.64(5) 2.699(6) 156(4) . N2 H2B O3 1.12(5) 1.64(5) 2.756(6) 175(4) 2_856 N2 H2C O3 0.89(5) 1.92(5) 2.760(6) 156(5) 1_565 _chemical_name_common 'bis((S)1-phenylethylammonium) 2,6-naphthalenedicarboxylate' ###END data_6 _database_code_depnum_ccdc_archive 'CCDC 691825' _audit_creation_date 2008-07-28T18:56:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; bis((RS)-1-phenylethylammonium) naphthalenedicarboxylate ; _chemical_formula_moiety 'C12 H6 O4, 2(C8 H12 N)' _chemical_formula_sum 'C28 H30 N2 O4' _chemical_formula_weight 458.54 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 6.1211(5) _cell_length_b 9.6478(8) _cell_length_c 10.5813(11) _cell_angle_alpha 94.483(4) _cell_angle_beta 98.503(4) _cell_angle_gamma 103.126(5) _cell_volume 597.80(9) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8221 _cell_measurement_theta_min 0.21 _cell_measurement_theta_max 27.1 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.301 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.083 _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.079 0 -1 0 0.171 1 0 0 0.121 -1 0 0 0.18 0 -2 3 0.075 0 2 -3 0.008 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.9731 _exptl_absorpt_correction_T_max 0.9929 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '1.5\% \w and \p scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0788 _diffrn_reflns_av_unetI/netI 0.0668 _diffrn_reflns_number 7594 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 2192 _reflns_number_gt 1521 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _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 ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0427P)^2^+0.1827P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.097(14) _refine_ls_number_reflns 2192 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.241 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0876(3) 0.3579(2) 0.90326(18) 0.0268(5) Uani 1 1 d . . . H1 H 1.2117 0.3137 0.9059 0.032 Uiso 1 1 calc R . . C2 C 0.9075(3) 0.3149(2) 0.80377(18) 0.0249(5) Uani 1 1 d . . . C3 C 0.7230(3) 0.3814(2) 0.80014(19) 0.0292(5) Uani 1 1 d . . . H3 H 0.5966 0.3512 0.732 0.035 Uiso 1 1 calc R . . C4 C 1.2757(3) 0.5118(2) 1.10678(19) 0.0295(5) Uani 1 1 d . . . H4 H 1.3996 0.4672 1.1122 0.035 Uiso 1 1 calc R . . C4A C 1.0926(3) 0.4667(2) 1.00239(18) 0.0258(5) Uani 1 1 d . . . C9 C 0.9104(3) 0.1999(2) 0.69971(18) 0.0266(5) Uani 1 1 d . . . O1 O 0.7483(2) 0.16698(15) 0.60556(13) 0.0336(4) Uani 1 1 d . . . O2 O 1.0766(2) 0.14258(15) 0.71030(13) 0.0332(4) Uani 1 1 d . . . C10 C 0.3498(4) 0.2016(2) 0.2972(2) 0.0341(5) Uani 1 1 d . . . C11 C 0.5761(4) 0.2738(3) 0.3150(2) 0.0393(6) Uani 1 1 d . . . H11 H 0.6495 0.3229 0.3969 0.047 Uiso 1 1 calc R . . C12 C 0.6977(4) 0.2751(3) 0.2135(2) 0.0449(6) Uani 1 1 d . . . H12 H 0.8531 0.3258 0.2264 0.054 Uiso 1 1 calc R . . C13 C 0.5937(5) 0.2033(3) 0.0948(2) 0.0474(6) Uani 1 1 d . . . H13 H 0.6769 0.204 0.0257 0.057 Uiso 1 1 calc R . . C14 C 0.3683(5) 0.1305(3) 0.0764(2) 0.0466(6) Uani 1 1 d . . . H14 H 0.2957 0.0806 -0.0054 0.056 Uiso 1 1 calc R . . C15 C 0.2470(4) 0.1299(2) 0.1774(2) 0.0404(6) Uani 1 1 d . . . H15 H 0.0914 0.0795 0.164 0.048 Uiso 1 1 calc R . . C16 C 0.2114(4) 0.2017(2) 0.4045(2) 0.0339(5) Uani 1 1 d . . . H16 H 0.0484 0.1569 0.367 0.041 Uiso 1 1 calc R . . C17 C 0.2256(4) 0.3506(2) 0.4691(2) 0.0416(6) Uani 1 1 d . . . H17A H 0.1157 0.3444 0.5283 0.062 Uiso 1 1 calc R . . H17B H 0.1906 0.4123 0.4034 0.062 Uiso 1 1 calc R . . H17C H 0.3797 0.3912 0.5171 0.062 Uiso 1 1 calc R . . N1 N 0.2864(3) 0.1125(2) 0.50478(17) 0.0288(4) Uani 1 1 d . . . H1A H 0.443(5) 0.146(3) 0.542(2) 0.043 Uiso 1 1 d . . . H1B H 0.262(4) 0.012(3) 0.468(2) 0.043 Uiso 1 1 d . . . H1C H 0.206(4) 0.119(3) 0.573(2) 0.043 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0237(10) 0.0292(11) 0.0286(11) 0.0014(9) 0.0064(8) 0.0081(8) C2 0.0263(10) 0.0256(11) 0.0228(10) 0.0011(8) 0.0065(8) 0.0055(8) C3 0.0246(10) 0.0348(12) 0.0270(11) -0.0004(9) 0.0016(8) 0.0079(9) C4 0.0238(10) 0.0332(12) 0.0313(11) -0.0009(9) 0.0019(8) 0.0099(9) C4A 0.0245(9) 0.0285(11) 0.0250(10) 0.0025(8) 0.0064(8) 0.0068(8) C9 0.0263(10) 0.0271(11) 0.0257(11) 0.0022(8) 0.0086(8) 0.0025(9) O1 0.0310(8) 0.0364(9) 0.0294(8) -0.0074(6) 0.0000(6) 0.0074(6) O2 0.0312(8) 0.0389(9) 0.0317(8) -0.0036(6) 0.0071(6) 0.0142(7) C10 0.0377(12) 0.0336(12) 0.0351(12) 0.0074(10) 0.0100(9) 0.0134(10) C11 0.0368(13) 0.0470(14) 0.0343(13) 0.0053(10) 0.0051(10) 0.0112(11) C12 0.0402(13) 0.0556(16) 0.0455(15) 0.0169(12) 0.0148(11) 0.0168(12) C13 0.0630(17) 0.0481(15) 0.0446(15) 0.0150(12) 0.0265(12) 0.0268(13) C14 0.0704(18) 0.0372(13) 0.0352(13) 0.0016(10) 0.0125(12) 0.0173(13) C15 0.0425(13) 0.0355(13) 0.0426(14) 0.0039(10) 0.0054(10) 0.0096(10) C16 0.0282(11) 0.0381(13) 0.0362(12) 0.0042(10) 0.0055(9) 0.0098(9) C17 0.0452(13) 0.0360(13) 0.0488(14) 0.0062(11) 0.0188(11) 0.0130(10) N1 0.0270(9) 0.0303(10) 0.0297(10) 0.0005(8) 0.0073(7) 0.0073(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.370(3) . ? C1 C4A 1.417(3) . ? C1 H1 0.95 . ? C2 C3 1.417(3) . ? C2 C9 1.506(3) . ? C3 C4 1.367(3) 2_767 ? C3 H3 0.95 . ? C4 C3 1.367(3) 2_767 ? C4 C4A 1.415(3) . ? C4 H4 0.95 . ? C4A C4A 1.421(4) 2_767 ? C9 O2 1.259(2) . ? C9 O1 1.262(2) . ? C10 C11 1.380(3) . ? C10 C15 1.383(3) . ? C10 C16 1.513(3) . ? C11 C12 1.393(3) . ? C11 H11 0.95 . ? C12 C13 1.375(4) . ? C12 H12 0.95 . ? C13 C14 1.376(4) . ? C13 H13 0.95 . ? C14 C15 1.388(3) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? C16 N1 1.502(3) . ? C16 C17 1.521(3) . ? C16 H16 1 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? N1 H1A 0.95(3) . ? N1 H1B 0.98(3) . ? N1 H1C 0.94(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C4A 121.42(17) . . ? C2 C1 H1 119.3 . . ? C4A C1 H1 119.3 . . ? C1 C2 C3 119.08(18) . . ? C1 C2 C9 119.63(17) . . ? C3 C2 C9 121.29(17) . . ? C4 C3 C2 120.94(18) 2_767 . ? C4 C3 H3 119.5 2_767 . ? C2 C3 H3 119.5 . . ? C3 C4 C4A 120.94(18) 2_767 . ? C3 C4 H4 119.5 2_767 . ? C4A C4 H4 119.5 . . ? C4 C4A C1 122.39(17) . . ? C4 C4A C4A 118.5(2) . 2_767 ? C1 C4A C4A 119.1(2) . 2_767 ? O2 C9 O1 123.24(18) . . ? O2 C9 C2 118.15(17) . . ? O1 C9 C2 118.60(17) . . ? C11 C10 C15 118.8(2) . . ? C11 C10 C16 121.69(19) . . ? C15 C10 C16 119.5(2) . . ? C10 C11 C12 120.5(2) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 120.2(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 119.7(2) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 120.1(2) . . ? C13 C14 H14 120 . . ? C15 C14 H14 120 . . ? C10 C15 C14 120.8(2) . . ? C10 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? N1 C16 C10 110.11(16) . . ? N1 C16 C17 108.84(18) . . ? C10 C16 C17 113.65(18) . . ? N1 C16 H16 108 . . ? C10 C16 H16 108 . . ? C17 C16 H16 108 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 N1 H1A 113.0(15) . . ? C16 N1 H1B 110.6(14) . . ? H1A N1 H1B 108(2) . . ? C16 N1 H1C 108.9(14) . . ? H1A N1 H1C 106(2) . . ? H1B N1 H1C 111(2) . . ? 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 C4A C1 C2 C3 0.2(3) . . . . ? C4A C1 C2 C9 179.36(18) . . . . ? C1 C2 C3 C4 0.8(3) . . . 2_767 ? C9 C2 C3 C4 -178.33(18) . . . 2_767 ? C3 C4 C4A C1 179.0(2) 2_767 . . . ? C3 C4 C4A C4A -1.1(3) 2_767 . . 2_767 ? C2 C1 C4A C4 179.35(19) . . . . ? C2 C1 C4A C4A -0.5(3) . . . 2_767 ? C1 C2 C9 O2 2.6(3) . . . . ? C3 C2 C9 O2 -178.22(18) . . . . ? C1 C2 C9 O1 -176.46(18) . . . . ? C3 C2 C9 O1 2.7(3) . . . . ? C15 C10 C11 C12 0.5(3) . . . . ? C16 C10 C11 C12 -178.2(2) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? C11 C10 C15 C14 -0.2(3) . . . . ? C16 C10 C15 C14 178.6(2) . . . . ? C13 C14 C15 C10 -0.1(3) . . . . ? C11 C10 C16 N1 -71.2(2) . . . . ? C15 C10 C16 N1 110.0(2) . . . . ? C11 C10 C16 C17 51.2(3) . . . . ? C15 C10 C16 C17 -127.6(2) . . . . ? 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 N1 H1A O1 0.95(3) 1.85(3) 2.784(2) 167(2) . N1 H1B O1 0.98(3) 1.82(3) 2.802(2) 173(2) 2_656 N1 H1C O2 0.94(3) 1.78(3) 2.713(2) 174(2) 1_455 _chemical_name_common 'bis((RS)-1-phenylethylammonium) naphthalenedicarboxylate'