# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Lemmerer, Andreas' _publ_contact_author_name 'Lemmerer, Andreas' _publ_contact_author_email andreas.lemmerer@gmail.com _publ_section_title ; Steric effects in hydrogen bonded columns of salts of benzoic acid and 1-adamantanecarboxylic acid with the cyclic amines CnH2n+1NH2, n = 5, 6, 7, 8 and 12. ; _publ_requested_category FO # Attachment '- Lemmerer.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-10-13 at 11:14:19 # 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 : 7ag181_a apex5 data_1 _database_code_depnum_ccdc_archive 'CCDC 797973' #TrackingRef '- Lemmerer.cif' _audit_creation_date 2010-10-13T11:14:19-00:00 _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 ; (cyclopentylammonium).(benzoate) ; _chemical_formula_moiety 'C5 H12 N, C7 H5 O2' _chemical_formula_sum 'C12 H17 N O2' _chemical_formula_weight 207.27 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # 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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.0786(4) _cell_length_b 10.5312(8) _cell_length_c 17.6034(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1126.88(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1993 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.22 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 1 0.04 0 -1 -1 0.04 1 0 0 0.34 -1 0 0 0.32 0 -1 3 0.15 0 1 -3 0.15 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.9646 _exptl_absorpt_correction_T_max 0.9932 #----------------------------------------------------------------------------# # 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 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0764 _diffrn_reflns_av_unetI/netI 0.0537 _diffrn_reflns_number 5911 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1589 _reflns_number_gt 1246 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0577P)^2^+0.1646P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1589 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 1124 Friedel Pairs' _refine_ls_abs_structure_Flack -10(10) _refine_diff_density_max 0.215 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.048 #----------------------------------------------------------------------------# # 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 0.6803(4) 0.4640(2) 0.65798(14) 0.0237(5) Uani 1 1 d . . . C2 C 0.4712(4) 0.4133(2) 0.65162(15) 0.0278(6) Uani 1 1 d . . . H2 H 0.3668 0.4518 0.6187 0.033 Uiso 1 1 calc R . . C3 C 0.4132(5) 0.3060(2) 0.69326(17) 0.0347(6) Uani 1 1 d . . . H3 H 0.2703 0.2705 0.6882 0.042 Uiso 1 1 calc R . . C4 C 0.5636(5) 0.2516(3) 0.74189(17) 0.0400(8) Uani 1 1 d . . . H4 H 0.5243 0.1782 0.7702 0.048 Uiso 1 1 calc R . . C5 C 0.7707(6) 0.3031(3) 0.74964(16) 0.0404(7) Uani 1 1 d . . . H5 H 0.8735 0.2656 0.7835 0.048 Uiso 1 1 calc R . . C6 C 0.8288(5) 0.4093(3) 0.70813(15) 0.0325(6) Uani 1 1 d . . . H6 H 0.9713 0.445 0.714 0.039 Uiso 1 1 calc R . . C7 C 0.7516(4) 0.5756(2) 0.61040(14) 0.0241(5) Uani 1 1 d . . . O1 O 0.6200(3) 0.61671(16) 0.56053(11) 0.0335(5) Uani 1 1 d . . . O2 O 0.9388(3) 0.62020(16) 0.62136(11) 0.0314(4) Uani 1 1 d . . . C8 C 0.1080(5) 0.5548(2) 0.43666(16) 0.0312(6) Uani 1 1 d . . . H8 H -0.0422 0.5831 0.4207 0.037 Uiso 1 1 calc R . . C9 C 0.2610(6) 0.5491(3) 0.36843(16) 0.0406(7) Uani 1 1 d . . . H9A H 0.1828 0.5167 0.3231 0.049 Uiso 1 1 calc R . . H9B H 0.3221 0.6341 0.3568 0.049 Uiso 1 1 calc R . . C10 C 0.4410(6) 0.4586(3) 0.3927(2) 0.0524(9) Uani 1 1 d . . . H10A H 0.5592 0.5043 0.4199 0.063 Uiso 1 1 calc R . . H10B H 0.5054 0.4149 0.3481 0.063 Uiso 1 1 calc R . . C11 C 0.3273(7) 0.3638(3) 0.44502(19) 0.0556(10) Uani 1 1 d . . . H11A H 0.4154 0.3509 0.4917 0.067 Uiso 1 1 calc R . . H11B H 0.31 0.281 0.4191 0.067 Uiso 1 1 calc R . . C12 C 0.1012(6) 0.4192(2) 0.46505(18) 0.0434(8) Uani 1 1 d . . . H12A H -0.0176 0.371 0.4396 0.052 Uiso 1 1 calc R . . H12B H 0.0763 0.4169 0.5206 0.052 Uiso 1 1 calc R . . N1 N 0.1985(3) 0.64230(18) 0.49582(12) 0.0267(5) Uani 1 1 d . . . H1A H 0.3388 0.619 0.5073 0.04 Uiso 1 1 calc R . . H1B H 0.1138 0.6379 0.5384 0.04 Uiso 1 1 calc R . . H1C H 0.1981 0.7233 0.4778 0.04 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0305(13) 0.0248(10) 0.0159(11) -0.0021(10) 0.0018(10) 0.0026(10) C2 0.0309(13) 0.0275(11) 0.0248(13) 0.0005(11) 0.0003(11) -0.0003(11) C3 0.0366(15) 0.0330(13) 0.0345(15) -0.0005(12) 0.0087(13) -0.0075(13) C4 0.060(2) 0.0298(12) 0.0302(15) 0.0077(12) 0.0149(15) 0.0016(14) C5 0.0529(18) 0.0396(14) 0.0286(15) 0.0083(13) -0.0006(14) 0.0077(15) C6 0.0349(15) 0.0364(13) 0.0262(14) 0.0027(12) -0.0019(12) 0.0021(13) C7 0.0291(13) 0.0237(10) 0.0195(12) -0.0018(9) 0.0025(11) 0.0017(11) O1 0.0368(11) 0.0335(9) 0.0303(10) 0.0113(9) -0.0088(9) -0.0025(9) O2 0.0305(10) 0.0372(9) 0.0266(10) 0.0027(9) 0.0006(8) -0.0075(9) C8 0.0318(14) 0.0336(13) 0.0283(14) 0.0014(12) -0.0069(12) -0.0024(12) C9 0.0577(19) 0.0370(13) 0.0269(14) -0.0003(12) 0.0019(14) -0.0056(16) C10 0.052(2) 0.0515(17) 0.053(2) -0.0149(17) 0.0032(18) 0.0111(18) C11 0.098(3) 0.0360(14) 0.0325(17) -0.0042(13) -0.0180(19) 0.0216(19) C12 0.066(2) 0.0321(13) 0.0322(16) 0.0011(13) -0.0017(15) -0.0142(15) N1 0.0274(11) 0.0270(10) 0.0258(11) 0.0055(9) 0.0018(9) -0.0004(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 1.383(4) . ? C1 C6 1.388(4) . ? C1 C7 1.507(3) . ? C2 C3 1.392(4) . ? C2 H2 0.95 . ? C3 C4 1.378(4) . ? C3 H3 0.95 . ? C4 C5 1.377(4) . ? C4 H4 0.95 . ? C5 C6 1.382(4) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.246(3) . ? C7 O1 1.264(3) . ? C8 N1 1.495(3) . ? C8 C12 1.513(4) . ? C8 C9 1.520(4) . ? C8 H8 1 . ? C9 C10 1.513(4) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.524(5) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.534(5) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? N1 H1A 0.91 . ? N1 H1B 0.91 . ? N1 H1C 0.91 . ? 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 C6 119.3(2) . . ? C2 C1 C7 121.3(2) . . ? C6 C1 C7 119.4(2) . . ? C1 C2 C3 120.2(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.8(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120 . . ? C6 C5 H5 120 . . ? C5 C6 C1 120.4(3) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? O2 C7 O1 123.8(2) . . ? O2 C7 C1 118.0(2) . . ? O1 C7 C1 118.1(2) . . ? N1 C8 C12 111.2(2) . . ? N1 C8 C9 110.5(2) . . ? C12 C8 C9 103.9(2) . . ? N1 C8 H8 110.4 . . ? C12 C8 H8 110.4 . . ? C9 C8 H8 110.4 . . ? C10 C9 C8 104.2(2) . . ? C10 C9 H9A 110.9 . . ? C8 C9 H9A 110.9 . . ? C10 C9 H9B 110.9 . . ? C8 C9 H9B 110.9 . . ? H9A C9 H9B 108.9 . . ? C9 C10 C11 104.8(3) . . ? C9 C10 H10A 110.8 . . ? C11 C10 H10A 110.8 . . ? C9 C10 H10B 110.8 . . ? C11 C10 H10B 110.8 . . ? H10A C10 H10B 108.9 . . ? C10 C11 C12 107.2(2) . . ? C10 C11 H11A 110.3 . . ? C12 C11 H11A 110.3 . . ? C10 C11 H11B 110.3 . . ? C12 C11 H11B 110.3 . . ? H11A C11 H11B 108.5 . . ? C8 C12 C11 105.0(3) . . ? C8 C12 H12A 110.7 . . ? C11 C12 H12A 110.7 . . ? C8 C12 H12B 110.7 . . ? C11 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C8 N1 H1A 109.5 . . ? C8 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C8 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.1(4) . . . . ? C7 C1 C2 C3 176.6(2) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C1 -0.6(4) . . . . ? C2 C1 C6 C5 1.9(4) . . . . ? C7 C1 C6 C5 -176.9(2) . . . . ? C2 C1 C7 O2 176.8(2) . . . . ? C6 C1 C7 O2 -4.4(3) . . . . ? C2 C1 C7 O1 -4.8(3) . . . . ? C6 C1 C7 O1 173.9(2) . . . . ? N1 C8 C9 C10 79.9(3) . . . . ? C12 C8 C9 C10 -39.4(3) . . . . ? C8 C9 C10 C11 32.4(3) . . . . ? C9 C10 C11 C12 -13.4(3) . . . . ? N1 C8 C12 C11 -88.2(3) . . . . ? C9 C8 C12 C11 30.6(3) . . . . ? C10 C11 C12 C8 -10.8(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 0.91 1.95 2.817(3) 159 . N1 H1B O2 0.91 1.82 2.726(3) 177 1_455 N1 H1C O1 0.91 1.88 2.766(3) 165 4_466 ###END data_2 _database_code_depnum_ccdc_archive 'CCDC 797974' #TrackingRef '- Lemmerer.cif' _audit_creation_date 2010-10-13T11:27:16-00:00 _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 ; (cyclohexylammonium).(benzoate) ; _chemical_formula_moiety 'C6 H14 N, C7 H5 O2' _chemical_formula_sum 'C13 H19 N O2' _chemical_formula_weight 221.29 _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 22.1824(12) _cell_length_b 35.8905(19) _cell_length_c 6.3763(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5076.4(5) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1398 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 21.78 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 2 0.24 0 -1 -2 0.24 0 1 0 0.02 0 -1 0 0.02 1 0 0 0.05 -1 0 0 0.05 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.9647 _exptl_absorpt_correction_T_max 0.9966 #----------------------------------------------------------------------------# # 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 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.1217 _diffrn_reflns_av_unetI/netI 0.0842 _diffrn_reflns_number 6701 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.98 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1670 _reflns_number_gt 1090 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1406P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1670 _refine_ls_number_parameters 165 _refine_ls_number_restraints 223 _refine_ls_R_factor_all 0.1048 _refine_ls_R_factor_gt 0.0702 _refine_ls_wR_factor_ref 0.2219 _refine_ls_wR_factor_gt 0.1936 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 1242 Friedel pairs' _refine_ls_abs_structure_Flack 10(10) _refine_diff_density_max 0.363 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # 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 0.13322(17) 0.41591(10) 0.7122(7) 0.0325(9) Uani 1 1 d U . . C2 C 0.13444(18) 0.40473(11) 0.5063(7) 0.0352(9) Uani 1 1 d U . . H2 H 0.1658 0.4132 0.4168 0.042 Uiso 1 1 calc R . . C3 C 0.09033(19) 0.38111(12) 0.4274(8) 0.0418(10) Uani 1 1 d U . . H3 H 0.092 0.3732 0.2852 0.05 Uiso 1 1 calc R . . C4 C 0.0444(2) 0.36915(14) 0.5544(10) 0.0494(12) Uani 1 1 d U . . H4 H 0.0144 0.3529 0.501 0.059 Uiso 1 1 calc R . . C5 C 0.0421(2) 0.38074(15) 0.7582(9) 0.0567(14) Uani 1 1 d U . . H5 H 0.0101 0.3727 0.8461 0.068 Uiso 1 1 calc R . . C6 C 0.0863(2) 0.40419(13) 0.8377(9) 0.0471(11) Uani 1 1 d U . . H6 H 0.0842 0.4122 0.9795 0.057 Uiso 1 1 calc R . . C7 C 0.1825(2) 0.44004(12) 0.8041(8) 0.0399(10) Uani 1 1 d U . . O1 O 0.21293(14) 0.45952(8) 0.6802(5) 0.0451(9) Uani 1 1 d U . . O2 O 0.1908(2) 0.43838(10) 0.9956(6) 0.0626(12) Uani 1 1 d U . . C8 C 0.3644(2) 0.48991(17) 0.7726(9) 0.0604(14) Uani 1 1 d DU . . H8A H 0.3958 0.5099 0.7759 0.072 Uiso 0.789(9) 1 calc PR A 1 H8B H 0.3815 0.513 0.708 0.072 Uiso 0.211(9) 1 d PR A 2 C9A C 0.3745(3) 0.4646(2) 0.9494(13) 0.069(2) Uani 0.789(9) 1 d PDU A 1 H9A1 H 0.3449 0.4439 0.9462 0.083 Uiso 0.789(9) 1 calc PR A 1 H9A2 H 0.37 0.4781 1.0839 0.083 Uiso 0.789(9) 1 calc PR A 1 C9B C 0.4140(11) 0.4892(5) 0.933(4) 0.066(4) Uani 0.211(9) 1 d PDU A 2 H9B1 H 0.3978 0.4948 1.0738 0.08 Uiso 0.211(9) 1 calc PR A 2 H9B2 H 0.4452 0.5079 0.8977 0.08 Uiso 0.211(9) 1 calc PR A 2 C10 C 0.4415(4) 0.4487(3) 0.9268(13) 0.106(3) Uani 1 1 d DU . . H10A H 0.471 0.4693 0.9191 0.128 Uiso 0.789(9) 1 calc PR A 1 H10B H 0.4518 0.4325 1.0474 0.128 Uiso 0.789(9) 1 calc PR A 1 H10C H 0.4678 0.4436 1.0489 0.128 Uiso 0.211(9) 1 d PR A 2 H10D H 0.4089 0.4298 0.9209 0.128 Uiso 0.211(9) 1 d PR A 2 C11A C 0.4413(4) 0.4259(2) 0.7200(14) 0.076(2) Uani 0.789(9) 1 d PDU A 1 H11A H 0.4806 0.4132 0.7023 0.091 Uiso 0.789(9) 1 calc PR A 1 H11B H 0.4094 0.4067 0.726 0.091 Uiso 0.789(9) 1 calc PR A 1 C11B C 0.4771(9) 0.4488(11) 0.719(2) 0.091(5) Uani 0.211(9) 1 d PDU A 2 H11C H 0.5045 0.4705 0.713 0.11 Uiso 0.211(9) 1 calc PR A 2 H11D H 0.5015 0.4258 0.7059 0.11 Uiso 0.211(9) 1 calc PR A 2 C12 C 0.4303(4) 0.4509(3) 0.5409(13) 0.099(2) Uani 1 1 d DU . . H12A H 0.4312 0.4365 0.4086 0.119 Uiso 0.789(9) 1 calc PR A 1 H12B H 0.4622 0.4701 0.5342 0.119 Uiso 0.789(9) 1 calc PR A 1 H12C H 0.4501 0.463 0.4196 0.119 Uiso 0.211(9) 1 d PR A 2 H12D H 0.4227 0.4247 0.5001 0.119 Uiso 0.211(9) 1 d PR A 2 C13 C 0.3693(3) 0.4692(2) 0.5676(10) 0.0742(18) Uani 1 1 d DU A . H13A H 0.3625 0.4868 0.4504 0.089 Uiso 1 1 calc R . . H13B H 0.3375 0.4499 0.5612 0.089 Uiso 1 1 calc R . . N1 N 0.30430(15) 0.50750(11) 0.7921(6) 0.0421(9) Uani 1 1 d U A . H1A H 0.2752 0.4904 0.7618 0.063 Uiso 1 1 calc R . . H1B H 0.3016 0.5269 0.701 0.063 Uiso 1 1 calc R . . H1C H 0.2992 0.5159 0.9255 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0342(18) 0.0267(18) 0.037(2) 0.0036(16) -0.0026(17) -0.0014(15) C2 0.0328(19) 0.034(2) 0.038(2) 0.0017(16) 0.0022(18) 0.0007(15) C3 0.045(2) 0.038(2) 0.042(2) -0.008(2) 0.000(2) -0.0007(18) C4 0.039(2) 0.049(3) 0.061(3) 0.000(2) -0.005(2) -0.0087(19) C5 0.046(3) 0.064(3) 0.060(3) 0.000(3) 0.014(3) -0.018(2) C6 0.055(3) 0.047(3) 0.039(2) 0.0021(19) 0.011(2) -0.007(2) C7 0.050(2) 0.032(2) 0.038(2) 0.0040(17) -0.007(2) -0.0033(17) O1 0.0437(15) 0.0423(17) 0.0493(19) 0.0076(16) -0.0107(16) -0.0132(13) O2 0.096(3) 0.053(2) 0.0395(17) 0.0029(16) -0.017(2) -0.0219(19) C8 0.047(2) 0.076(4) 0.058(3) -0.018(2) -0.004(2) 0.009(2) C9A 0.071(4) 0.076(5) 0.060(4) -0.007(3) 0.009(4) 0.023(4) C9B 0.053(7) 0.088(8) 0.058(8) -0.017(9) -0.007(6) 0.013(8) C10 0.112(5) 0.138(6) 0.069(3) -0.012(4) -0.005(4) 0.082(5) C11A 0.071(4) 0.065(4) 0.091(5) -0.016(4) 0.011(4) 0.024(3) C11B 0.085(9) 0.104(12) 0.084(8) -0.005(10) 0.004(5) 0.049(9) C12 0.090(4) 0.140(6) 0.068(3) -0.012(4) 0.013(4) 0.042(4) C13 0.078(4) 0.091(4) 0.054(3) -0.027(3) -0.001(3) 0.028(3) N1 0.0395(18) 0.048(2) 0.039(2) -0.0085(18) 0.0046(18) -0.0078(15) #----------------------------------------------------------------------------# # 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 1.373(6) . ? C1 C6 1.379(6) . ? C1 C7 1.513(6) . ? C2 C3 1.389(6) . ? C2 H2 0.95 . ? C3 C4 1.370(7) . ? C3 H3 0.95 . ? C4 C5 1.365(9) . ? C4 H4 0.95 . ? C5 C6 1.387(7) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.236(6) . ? C7 O1 1.252(6) . ? C8 C9A 1.466(9) . ? C8 N1 1.479(6) . ? C8 C9B 1.501(15) . ? C8 C13 1.508(7) . ? C8 H8A 1 . ? C8 H8B 1 . ? C9A C10 1.598(9) . ? C9A H9A1 0.99 . ? C9A H9A2 0.99 . ? C9B C10 1.577(15) . ? C9B H9B1 0.99 . ? C9B H9B2 0.99 . ? C10 C11B 1.544(16) . ? C10 C11A 1.550(10) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C10 H10C 0.99 . ? C10 H10D 0.99 . ? C11A C12 1.471(10) . ? C11A H11A 0.99 . ? C11A H11B 0.99 . ? C11B C12 1.539(16) . ? C11B H11C 0.99 . ? C11B H11D 0.99 . ? C12 C13 1.514(8) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C12 H12C 0.99 . ? C12 H12D 0.99 . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? N1 H1A 0.91 . ? N1 H1B 0.91 . ? N1 H1C 0.91 . ? 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 C6 118.7(4) . . ? C2 C1 C7 121.5(4) . . ? C6 C1 C7 119.7(4) . . ? C1 C2 C3 120.7(4) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120 . . ? C2 C3 H3 120 . . ? C5 C4 C3 119.7(5) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.4(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 120.4(5) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? O2 C7 O1 124.8(4) . . ? O2 C7 C1 117.5(4) . . ? O1 C7 C1 117.7(4) . . ? C9A C8 N1 109.8(5) . . ? N1 C8 C9B 127.6(10) . . ? C9A C8 C13 110.5(5) . . ? N1 C8 C13 110.4(4) . . ? C9B C8 C13 121.8(10) . . ? C9A C8 H8A 108.7 . . ? N1 C8 H8A 108.7 . . ? C13 C8 H8A 108.7 . . ? C9A C8 H8B 140.6 . . ? N1 C8 H8B 91.3 . . ? C9B C8 H8B 90.9 . . ? C13 C8 H8B 91.3 . . ? C8 C9A C10 107.1(6) . . ? C8 C9A H9A1 110.3 . . ? C10 C9A H9A1 110.3 . . ? C8 C9A H9A2 110.3 . . ? C10 C9A H9A2 110.3 . . ? H9A1 C9A H9A2 108.5 . . ? C8 C9A H10D 120.6 . . ? C8 C9B C10 106.5(11) . . ? C8 C9B H9B1 110.4 . . ? C10 C9B H9B1 110.4 . . ? C8 C9B H9B2 110.4 . . ? C10 C9B H9B2 110.4 . . ? H9B1 C9B H9B2 108.6 . . ? C11B C10 C9B 102.5(19) . . ? C11A C10 C9B 120.3(10) . . ? C11B C10 C9A 123.6(10) . . ? C11A C10 C9A 105.2(7) . . ? C11A C10 H10A 110.7 . . ? C9A C10 H10A 110.7 . . ? C11B C10 H10B 123.4 . . ? C11A C10 H10B 110.7 . . ? C9B C10 H10B 127.6 . . ? C9A C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? C11B C10 H10C 112 . . ? C11A C10 H10C 125.1 . . ? C9B C10 H10C 112.2 . . ? C9A C10 H10C 122.8 . . ? C11B C10 H10D 110.1 . . ? C9B C10 H10D 110.4 . . ? H10C C10 H10D 109.6 . . ? C12 C11A C10 109.9(6) . . ? C12 C11A H10D 122.4 . . ? C12 C11A H11A 109.7 . . ? C10 C11A H11A 109.7 . . ? H10D C11A H11A 124.8 . . ? C12 C11A H11B 109.7 . . ? C10 C11A H11B 109.7 . . ? H11A C11A H11B 108.2 . . ? C12 C11B C10 106.7(12) . . ? C12 C11B H11C 110.4 . . ? C10 C11B H11C 110.4 . . ? C12 C11B H11D 110.4 . . ? C10 C11B H11D 110.4 . . ? H11C C11B H11D 108.6 . . ? C11A C12 C13 108.9(7) . . ? C13 C12 C11B 122.8(10) . . ? C11A C12 H12A 109.9 . . ? C13 C12 H12A 109.9 . . ? C11A C12 H12B 109.9 . . ? C13 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? C13 C12 H12C 107.1 . . ? C11B C12 H12C 107.3 . . ? C13 C12 H12D 106.9 . . ? C11B C12 H12D 105.2 . . ? H12C C12 H12D 106.6 . . ? C8 C13 C12 112.1(6) . . ? C8 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? C8 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C8 N1 H1A 109.5 . . ? C8 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C8 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.0(6) . . . . ? C7 C1 C2 C3 176.9(4) . . . . ? C1 C2 C3 C4 1.0(7) . . . . ? C2 C3 C4 C5 0.4(8) . . . . ? C3 C4 C5 C6 -0.7(9) . . . . ? C2 C1 C6 C5 1.7(7) . . . . ? C7 C1 C6 C5 -177.2(5) . . . . ? C4 C5 C6 C1 -0.4(9) . . . . ? C2 C1 C7 O2 -155.2(5) . . . . ? C6 C1 C7 O2 23.7(7) . . . . ? C2 C1 C7 O1 23.2(6) . . . . ? C6 C1 C7 O1 -157.9(4) . . . . ? N1 C8 C9A C10 -176.4(6) . . . . ? C9B C8 C9A C10 -53.3(12) . . . . ? C13 C8 C9A C10 61.6(8) . . . . ? C9A C8 C9B C10 54.0(12) . . . . ? N1 C8 C9B C10 138.7(11) . . . . ? C13 C8 C9B C10 -37(3) . . . . ? C8 C9B C10 C11B 73(2) . . . . ? C8 C9B C10 C11A 30(3) . . . . ? C8 C9B C10 C9A -51.6(11) . . . . ? C8 C9A C10 C11B -20(2) . . . . ? C8 C9A C10 C11A -63.9(9) . . . . ? C8 C9A C10 C9B 53.6(13) . . . . ? C11B C10 C11A C12 -58.6(14) . . . . ? C9B C10 C11A C12 16.7(16) . . . . ? C9A C10 C11A C12 64.6(9) . . . . ? C11A C10 C11B C12 53.2(14) . . . . ? C9B C10 C11B C12 -68(2) . . . . ? C9A C10 C11B C12 -23(3) . . . . ? C10 C11A C12 C13 -60.9(9) . . . . ? C10 C11A C12 C11B 56.9(13) . . . . ? C10 C11B C12 C11A -55.7(14) . . . . ? C10 C11B C12 C13 28(3) . . . . ? C9A C8 C13 C12 -58.6(9) . . . . ? N1 C8 C13 C12 179.8(7) . . . . ? C9B C8 C13 C12 -4.0(17) . . . . ? C11A C12 C13 C8 56.5(10) . . . . ? C11B C12 C13 C8 9(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 0.91 1.85 2.754(4) 174 . N1 H1B O2 0.91 1.81 2.713(6) 169 10_564 N1 H1C O1 0.91 1.87 2.769(5) 171 10_565 ###END data_3 _database_code_depnum_ccdc_archive 'CCDC 797975' #TrackingRef '- Lemmerer.cif' _audit_creation_date 2006-04-29T09:53:29-00:00 _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 ; (cycloheptylammonium).(benzoate) ; _chemical_formula_moiety 'C7 H16 N, C7 H5 O2' _chemical_formula_sum 'C14 H21 N O2' _chemical_formula_weight 235.32 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)/a _symmetry_space_group_name_Hall '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 29.9753(5) _cell_length_b 29.9753(5) _cell_length_c 6.0374(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5424.7(2) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3867 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 25.93 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 0 0.07 0 1 0 0.02 0 0 1 0.03 0 0 -1 0.02 1 0 0 0.25 -1 0 0 0.25 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_correction_T_min 0.9776 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Bruker SMART APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_unetI/netI 0.0335 _diffrn_reflns_number 29101 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3276 _reflns_number_gt 2299 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0445P)^2^+2.9342P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3276 _refine_ls_number_parameters 174 _refine_ls_number_restraints 192 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.208 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.035 #----------------------------------------------------------------------------# # 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 0.62338(4) 0.55635(4) 0.6950(2) 0.0237(3) Uani 1 1 d U . . C2 C 0.62602(5) 0.57602(5) 0.4878(2) 0.0312(3) Uani 1 1 d U . . H2 H 0.6006 0.5762 0.3936 0.037 Uiso 1 1 calc R . . C3 C 0.66564(5) 0.59544(5) 0.4173(3) 0.0413(4) Uani 1 1 d U . . H3 H 0.6672 0.609 0.2753 0.05 Uiso 1 1 calc R . . C4 C 0.70262(5) 0.59513(6) 0.5522(3) 0.0428(4) Uani 1 1 d U . . H4 H 0.7295 0.6089 0.5045 0.051 Uiso 1 1 calc R . . C5 C 0.70063(5) 0.57480(5) 0.7563(3) 0.0419(4) Uani 1 1 d U . . H5 H 0.7263 0.574 0.8482 0.05 Uiso 1 1 calc R . . C6 C 0.66114(5) 0.55556(5) 0.8281(3) 0.0316(3) Uani 1 1 d U . . H6 H 0.6599 0.5417 0.9695 0.038 Uiso 1 1 calc R . . C7 C 0.58053(4) 0.53654(4) 0.7797(2) 0.0243(3) Uani 1 1 d U . . O1 O 0.54588(3) 0.53908(3) 0.66040(17) 0.0312(2) Uani 1 1 d U . . O2 O 0.58087(3) 0.51875(3) 0.96692(16) 0.0336(3) Uani 1 1 d U . . C8 C 0.48241(5) 0.57295(5) 0.1690(2) 0.0308(3) Uani 1 1 d DU A . H8 H 0.4678 0.5651 0.0253 0.037 Uiso 1 1 calc R . . C9 C 0.44579(5) 0.57968(5) 0.3398(3) 0.0412(4) Uani 1 1 d U . . H9A H 0.4589 0.5766 0.4895 0.049 Uiso 0.864(2) 1 calc PR A 1 H9B H 0.4234 0.5557 0.322 0.049 Uiso 0.864(2) 1 calc PR A 1 H9C H 0.4371 0.5502 0.3995 0.049 Uiso 0.136(2) 1 d PR A 2 H9D H 0.4193 0.5925 0.265 0.049 Uiso 0.136(2) 1 d PR A 2 C10A C 0.42205(6) 0.62477(6) 0.3250(4) 0.0449(5) Uani 0.864(2) 1 d PU A 1 H10A H 0.3908 0.6212 0.3746 0.054 Uiso 0.864(2) 1 calc PR A 1 H10B H 0.4216 0.6347 0.1686 0.054 Uiso 0.864(2) 1 calc PR A 1 C10B C 0.4598(5) 0.6098(4) 0.548(2) 0.047(2) Uani 0.136(2) 1 d PU A 2 H10C H 0.4922 0.608 0.5759 0.057 Uiso 0.136(2) 1 calc PR A 2 H10D H 0.4435 0.6006 0.683 0.057 Uiso 0.136(2) 1 calc PR A 2 C11 C 0.44486(6) 0.66078(6) 0.4670(3) 0.0527(5) Uani 1 1 d U . . H11A H 0.424 0.6861 0.4858 0.063 Uiso 0.864(2) 1 calc PR A 1 H11B H 0.4509 0.6483 0.6158 0.063 Uiso 0.864(2) 1 calc PR A 1 H11C H 0.4208 0.6603 0.3546 0.063 Uiso 0.136(2) 1 d PR A 2 H11D H 0.4351 0.6788 0.5955 0.063 Uiso 0.136(2) 1 d PR A 2 C12 C 0.48824(6) 0.67816(6) 0.3704(4) 0.0533(5) Uani 1 1 d DU A . H12A H 0.5007 0.701 0.4717 0.064 Uiso 0.864(2) 1 calc PR A 1 H12B H 0.4818 0.693 0.2273 0.064 Uiso 0.864(2) 1 calc PR A 1 H12C H 0.5145 0.6666 0.4512 0.064 Uiso 0.136(2) 1 d PR A 2 H12D H 0.4892 0.7112 0.367 0.064 Uiso 0.136(2) 1 d PR A 2 C13A C 0.52360(6) 0.64185(6) 0.3324(4) 0.0410(5) Uani 0.864(2) 1 d PDU A 1 H13A H 0.5253 0.6225 0.4649 0.049 Uiso 0.864(2) 1 calc PR A 1 H13B H 0.5531 0.6561 0.3118 0.049 Uiso 0.864(2) 1 calc PR A 1 C13B C 0.4838(5) 0.6563(4) 0.1143(18) 0.051(3) Uani 0.136(2) 1 d PDU A 2 H13C H 0.4523 0.6492 0.0785 0.061 Uiso 0.136(2) 1 calc PR A 2 H13D H 0.4956 0.6771 0.0013 0.061 Uiso 0.136(2) 1 calc PR A 2 C14 C 0.51262(5) 0.61311(5) 0.1279(3) 0.0387(4) Uani 1 1 d DU . . H14A H 0.4982 0.6324 0.0158 0.046 Uiso 0.864(2) 1 calc PR A 1 H14B H 0.541 0.6022 0.0637 0.046 Uiso 0.864(2) 1 calc PR A 1 H14C H 0.5287 0.6093 -0.0141 0.046 Uiso 0.136(2) 1 d PR A 2 H14D H 0.535 0.6154 0.248 0.046 Uiso 0.136(2) 1 d PR A 2 N1 N 0.50995(4) 0.53383(4) 0.23895(19) 0.0266(3) Uani 1 1 d DU . . H1A H 0.523 0.5398 0.3718 0.04 Uiso 1 1 calc RD A . H1B H 0.5314 0.5286 0.1357 0.04 Uiso 1 1 calc RD . . H1C H 0.4922 0.5094 0.252 0.04 Uiso 1 1 calc RDU . . 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 0.0230(6) 0.0224(6) 0.0258(7) -0.0046(5) 0.0015(5) -0.0013(5) C2 0.0290(7) 0.0356(8) 0.0290(7) 0.0003(6) -0.0006(6) -0.0046(6) C3 0.0421(9) 0.0460(9) 0.0358(9) 0.0028(7) 0.0088(7) -0.0114(7) C4 0.0295(8) 0.0461(9) 0.0529(10) -0.0068(8) 0.0117(7) -0.0126(7) C5 0.0263(7) 0.0476(9) 0.0519(10) -0.0053(8) -0.0058(7) -0.0063(7) C6 0.0294(7) 0.0335(7) 0.0318(8) -0.0009(6) -0.0037(6) -0.0032(6) C7 0.0238(6) 0.0245(6) 0.0247(7) -0.0032(5) 0.0006(5) -0.0009(5) O1 0.0239(5) 0.0393(6) 0.0304(5) 0.0032(4) -0.0039(4) -0.0075(4) O2 0.0297(5) 0.0445(6) 0.0265(5) 0.0072(5) 0.0022(4) -0.0017(4) C8 0.0307(7) 0.0323(7) 0.0293(7) 0.0000(6) -0.0039(6) -0.0009(6) C9 0.0304(8) 0.0367(8) 0.0566(11) -0.0005(8) 0.0091(7) -0.0028(6) C10A 0.0286(9) 0.0408(10) 0.0654(14) -0.0028(10) 0.0023(9) 0.0036(7) C10B 0.052(7) 0.048(4) 0.042(5) -0.003(4) 0.012(5) 0.015(4) C11 0.0553(11) 0.0431(9) 0.0596(12) -0.0116(9) 0.0040(9) 0.0119(8) C12 0.0493(10) 0.0332(9) 0.0774(14) -0.0133(9) -0.0058(9) 0.0029(7) C13A 0.0312(9) 0.0327(9) 0.0590(13) -0.0032(9) -0.0039(9) -0.0047(7) C13B 0.063(7) 0.039(4) 0.050(4) 0.017(5) -0.001(5) 0.009(4) C14 0.0413(9) 0.0337(8) 0.0411(9) 0.0069(7) 0.0080(7) -0.0005(7) N1 0.0252(6) 0.0311(6) 0.0235(6) 0.0006(5) 0.0007(5) -0.0055(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 1.385(2) . ? C1 C6 1.3883(19) . ? C1 C7 1.5049(18) . ? C2 C3 1.389(2) . ? C2 H2 0.95 . ? C3 C4 1.375(2) . ? C3 H3 0.95 . ? C4 C5 1.376(2) . ? C4 H4 0.95 . ? C5 C6 1.386(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.2498(16) . ? C7 O1 1.2661(16) . ? C8 N1 1.4950(18) . ? C8 C9 1.520(2) . ? C8 C14 1.527(2) . ? C8 H8 1 . ? C9 C10A 1.530(2) . ? C9 C10B 1.601(14) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C9 H9C 0.99 . ? C9 H9D 0.99 . ? C10A C11 1.539(3) . ? C10A H9D 1.0369 . ? C10A H10A 0.99 . ? C10A H10B 0.99 . ? C10A H11C 1.0796 . ? C10B C11 1.666(13) . ? C10B H10C 0.99 . ? C10B H10D 0.99 . ? C11 C12 1.517(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C11 H11C 0.99 . ? C11 H11D 0.99 . ? C12 C13A 1.537(2) . ? C12 C13B 1.684(11) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C12 H12C 0.99 . ? C12 H12D 0.99 . ? C13A C14 1.541(2) . ? C13A H12C 1.0671 . ? C13A H13A 0.99 . ? C13A H13B 0.99 . ? C13A H14D 1.0039 . ? C13B C14 1.560(10) . ? C13B H13C 0.99 . ? C13B H13D 0.99 . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C14 H14C 0.99 . ? C14 H14D 0.99 . ? N1 H1A 0.91 . ? N1 H1B 0.91 . ? N1 H1C 0.91 . ? 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 C6 118.92(12) . . ? C2 C1 C7 121.57(12) . . ? C6 C1 C7 119.50(13) . . ? C1 C2 C3 120.25(14) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.31(15) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.88(14) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 120.07(15) . . ? C4 C5 H5 120 . . ? C6 C5 H5 120 . . ? C5 C6 C1 120.54(15) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O2 C7 O1 123.15(12) . . ? O2 C7 C1 117.96(12) . . ? O1 C7 C1 118.89(12) . . ? N1 C8 C9 108.13(12) . . ? N1 C8 C14 109.68(11) . . ? C9 C8 C14 115.72(13) . . ? N1 C8 H8 107.7 . . ? C9 C8 H8 107.7 . . ? C14 C8 H8 107.7 . . ? C8 C9 C10A 114.42(14) . . ? C8 C9 C10B 114.7(5) . . ? C10A C9 C10B 70.7(5) . . ? C8 C9 H9A 108.7 . . ? C10A C9 H9A 108.7 . . ? C8 C9 H9B 108.7 . . ? C10A C9 H9B 108.7 . . ? C10B C9 H9B 132.2 . . ? H9A C9 H9B 107.6 . . ? C8 C9 H9C 108.5 . . ? C10A C9 H9C 133.5 . . ? C10B C9 H9C 106.7 . . ? H9A C9 H9C 72 . . ? C8 C9 H9D 108.7 . . ? C10B C9 H9D 110.4 . . ? H9A C9 H9D 140.4 . . ? H9B C9 H9D 71.8 . . ? H9C C9 H9D 107.6 . . ? C9 C10A C11 112.35(15) . . ? C11 C10A H9D 152.2 . . ? C9 C10A H10A 109.1 . . ? C11 C10A H10A 109.1 . . ? H9D C10A H10A 86 . . ? C9 C10A H10B 109.1 . . ? C11 C10A H10B 109.1 . . ? H9D C10A H10B 86.9 . . ? H10A C10A H10B 107.9 . . ? C9 C10A H11C 151.2 . . ? H9D C10A H11C 167.3 . . ? H10A C10A H11C 91.4 . . ? H10B C10A H11C 82 . . ? C9 C10B C11 102.6(8) . . ? C9 C10B H10C 111.3 . . ? C11 C10B H10C 111.3 . . ? C9 C10B H10D 111.3 . . ? C11 C10B H10D 111.3 . . ? H10C C10B H10D 109.2 . . ? C12 C11 C10A 114.04(16) . . ? C12 C11 C10B 101.4(5) . . ? C10A C11 C10B 68.8(5) . . ? C12 C11 H11A 108.7 . . ? C10A C11 H11A 108.7 . . ? C10B C11 H11A 147.1 . . ? C12 C11 H11B 108.7 . . ? C10A C11 H11B 108.7 . . ? C10B C11 H11B 48.5 . . ? H11A C11 H11B 107.6 . . ? C12 C11 H11C 111.4 . . ? C10B C11 H11C 112.4 . . ? H11A C11 H11C 68.3 . . ? H11B C11 H11C 138.6 . . ? C12 C11 H11D 111.5 . . ? C10A C11 H11D 133.5 . . ? C10B C11 H11D 110.6 . . ? H11A C11 H11D 46 . . ? H11B C11 H11D 63.3 . . ? H11C C11 H11D 109.3 . . ? C11 C12 C13A 113.90(15) . . ? C11 C12 C13B 98.7(5) . . ? C13A C12 C13B 69.1(4) . . ? C11 C12 H12A 108.8 . . ? C13A C12 H12A 108.8 . . ? C13B C12 H12A 149.9 . . ? C11 C12 H12B 108.8 . . ? C13A C12 H12B 108.8 . . ? C13B C12 H12B 50 . . ? H12A C12 H12B 107.7 . . ? C11 C12 H12C 111.9 . . ? C13B C12 H12C 112.3 . . ? H12A C12 H12C 68.7 . . ? H12B C12 H12C 137.9 . . ? C11 C12 H12D 112.1 . . ? C13A C12 H12D 133.2 . . ? C13B C12 H12D 111.8 . . ? H12A C12 H12D 46.5 . . ? H12B C12 H12D 62.6 . . ? H12C C12 H12D 109.7 . . ? C12 C13A C14 111.60(15) . . ? C14 C13A H12C 150.8 . . ? C12 C13A H13A 109.3 . . ? C14 C13A H13A 109.3 . . ? H12C C13A H13A 83 . . ? C12 C13A H13B 109.3 . . ? C14 C13A H13B 109.3 . . ? H12C C13A H13B 90.7 . . ? H13A C13A H13B 108 . . ? C12 C13A H14D 150.6 . . ? H12C C13A H14D 168 . . ? H13A C13A H14D 85.9 . . ? H13B C13A H14D 88.4 . . ? C14 C13B C12 103.3(6) . . ? C14 C13B H13C 111.1 . . ? C12 C13B H13C 111.1 . . ? C14 C13B H13D 111.1 . . ? C12 C13B H13D 111.1 . . ? H13C C13B H13D 109.1 . . ? C8 C14 C13A 115.94(13) . . ? C8 C14 C13B 109.6(5) . . ? C13A C14 C13B 72.3(4) . . ? C8 C14 H14A 108.3 . . ? C13A C14 H14A 108.3 . . ? C8 C14 H14B 108.3 . . ? C13A C14 H14B 108.3 . . ? C13B C14 H14B 136.8 . . ? H14A C14 H14B 107.4 . . ? C8 C14 H14C 109.8 . . ? C13A C14 H14C 130.9 . . ? C13B C14 H14C 108.6 . . ? H14A C14 H14C 71.7 . . ? C8 C14 H14D 109.7 . . ? C13B C14 H14D 111 . . ? H14A C14 H14D 139.1 . . ? H14B C14 H14D 74.1 . . ? H14C C14 H14D 108.2 . . ? C8 N1 H1A 109.5 . . ? C8 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C8 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.4(2) . . . . ? C7 C1 C2 C3 177.71(13) . . . . ? C1 C2 C3 C4 0.3(2) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? C3 C4 C5 C6 -1.5(2) . . . . ? C4 C5 C6 C1 0.3(2) . . . . ? C2 C1 C6 C5 1.1(2) . . . . ? C7 C1 C6 C5 -178.04(13) . . . . ? C2 C1 C7 O2 178.93(12) . . . . ? C6 C1 C7 O2 -1.97(19) . . . . ? C2 C1 C7 O1 -1.93(19) . . . . ? C6 C1 C7 O1 177.17(12) . . . . ? N1 C8 C9 C10A 165.45(13) . . . . ? C14 C8 C9 C10A 42.0(2) . . . . ? N1 C8 C9 C10B 86.4(5) . . . . ? C14 C8 C9 C10B -37.0(5) . . . . ? C8 C9 C10A C11 -89.5(2) . . . . ? C10B C9 C10A C11 19.6(5) . . . . ? C8 C9 C10B C11 91.7(6) . . . . ? C10A C9 C10B C11 -17.1(4) . . . . ? C9 C10A C11 C12 74.4(2) . . . . ? C9 C10A C11 C10B -19.0(5) . . . . ? C9 C10B C11 C12 -94.4(6) . . . . ? C9 C10B C11 C10A 17.2(4) . . . . ? C10A C11 C12 C13A -58.3(2) . . . . ? C10B C11 C12 C13A 13.4(5) . . . . ? C10A C11 C12 C13B 12.6(4) . . . . ? C10B C11 C12 C13B 84.3(6) . . . . ? C11 C12 C13A C14 75.3(2) . . . . ? C13B C12 C13A C14 -15.2(5) . . . . ? C11 C12 C13B C14 -98.0(7) . . . . ? C13A C12 C13B C14 14.3(5) . . . . ? N1 C8 C14 C13A -86.40(16) . . . . ? C9 C8 C14 C13A 36.23(19) . . . . ? N1 C8 C14 C13B -165.7(4) . . . . ? C9 C8 C14 C13B -43.1(5) . . . . ? C12 C13A C14 C8 -87.54(18) . . . . ? C12 C13A C14 C13B 16.1(6) . . . . ? C12 C13B C14 C8 98.0(7) . . . . ? C12 C13B C14 C13A -14.0(5) . . . . ? 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 0.91 1.87 2.768(2) 167 . N1 H1B O2 0.91 1.82 2.724(2) 171 1_554 N1 H1C O1 0.91 1.92 2.819(2) 169 9_666 ###END data_4 _database_code_depnum_ccdc_archive 'CCDC 797976' #TrackingRef '- Lemmerer.cif' _audit_creation_date 2010-10-13T13:11:06-00:00 _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 ; (cyclooctylammonium).(benzoate) ; _chemical_formula_moiety 'C8 H18 N, C7 H5 O2' _chemical_formula_sum 'C15 H23 N O2' _chemical_formula_weight 249.34 #----------------------------------------------------------------------------# # 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 6.44820(10) _cell_length_b 9.0987(2) _cell_length_c 12.4471(2) _cell_angle_alpha 86.6030(10) _cell_angle_beta 87.8990(10) _cell_angle_gamma 77.9760(10) _cell_volume 712.78(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5925 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.27 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.1 0 0 -1 0.1 0 -1 0 0.1 0 1 0 0.1 1 0 0 0.23 -1 0 0 0.22 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.9704 _exptl_absorpt_correction_T_max 0.9865 #----------------------------------------------------------------------------# # 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 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_unetI/netI 0.0309 _diffrn_reflns_number 13370 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3443 _reflns_number_gt 2863 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0603P)^2^+0.1075P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3443 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.111 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.285 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # 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 0.35544(16) 0.32660(11) 0.20884(8) 0.0270(2) Uani 1 1 d . . . C2 C 0.5413(2) 0.3604(2) 0.16625(10) 0.0534(4) Uani 1 1 d . . . H2 H 0.6175 0.4165 0.2062 0.064 Uiso 1 1 calc R . . C3 C 0.6182(3) 0.3132(2) 0.06566(11) 0.0689(5) Uani 1 1 d . . . H3 H 0.7464 0.3374 0.0371 0.083 Uiso 1 1 calc R . . C4 C 0.5104(3) 0.23240(19) 0.00778(10) 0.0550(4) Uani 1 1 d . . . H4 H 0.5636 0.1998 -0.0609 0.066 Uiso 1 1 calc R . . C5 C 0.3254(3) 0.19821(17) 0.04872(10) 0.0513(4) Uani 1 1 d . . . H5 H 0.2504 0.1418 0.0083 0.062 Uiso 1 1 calc R . . C6 C 0.2466(2) 0.24555(14) 0.14910(9) 0.0377(3) Uani 1 1 d . . . H6 H 0.1173 0.2221 0.1767 0.045 Uiso 1 1 calc R . . C7 C 0.27350(16) 0.37333(11) 0.31939(8) 0.0252(2) Uani 1 1 d . . . O1 O 0.37137(13) 0.45483(9) 0.36839(6) 0.0335(2) Uani 1 1 d . . . O2 O 0.11355(12) 0.32889(9) 0.35675(6) 0.03313(19) Uani 1 1 d . . . C8 C 0.79221(15) 0.67797(11) 0.36948(8) 0.0246(2) Uani 1 1 d . . . H8 H 0.9176 0.7 0.4055 0.029 Uiso 1 1 calc R . . C9 C 0.84403(18) 0.66936(12) 0.24849(8) 0.0301(2) Uani 1 1 d . . . H9A H 0.8779 0.5622 0.2308 0.036 Uiso 1 1 calc R . . H9B H 0.7158 0.7186 0.2086 0.036 Uiso 1 1 calc R . . C10 C 1.0282(2) 0.74207(13) 0.20857(9) 0.0376(3) Uani 1 1 d . . . H10A H 1.0574 0.7192 0.132 0.045 Uiso 1 1 calc R . . H10B H 1.1552 0.6915 0.2489 0.045 Uiso 1 1 calc R . . C11 C 1.0057(2) 0.91213(14) 0.21652(10) 0.0400(3) Uani 1 1 d . . . H11A H 1.1299 0.9424 0.1794 0.048 Uiso 1 1 calc R . . H11B H 0.8779 0.964 0.1773 0.048 Uiso 1 1 calc R . . C12 C 0.98829(18) 0.96746(13) 0.33104(10) 0.0351(3) Uani 1 1 d . . . H12A H 1.0747 1.0452 0.334 0.042 Uiso 1 1 calc R . . H12B H 1.0512 0.8821 0.3807 0.042 Uiso 1 1 calc R . . C13 C 0.76334(18) 1.03349(13) 0.37257(10) 0.0362(3) Uani 1 1 d . . . H13A H 0.7671 1.0356 0.4519 0.043 Uiso 1 1 calc R . . H13B H 0.7242 1.1391 0.3439 0.043 Uiso 1 1 calc R . . C14 C 0.58805(17) 0.95407(13) 0.34571(9) 0.0336(3) Uani 1 1 d . . . H14A H 0.5896 0.9462 0.2667 0.04 Uiso 1 1 calc R . . H14B H 0.4504 1.0183 0.3663 0.04 Uiso 1 1 calc R . . C15 C 0.59802(17) 0.79769(13) 0.39845(9) 0.0331(2) Uani 1 1 d . . . H15A H 0.4697 0.7625 0.3789 0.04 Uiso 1 1 calc R . . H15B H 0.5924 0.8058 0.4775 0.04 Uiso 1 1 calc R . . N1 N 0.75394(14) 0.52946(10) 0.41523(7) 0.0263(2) Uani 1 1 d . . . H1A H 0.6398 0.5077 0.3835 0.039 Uiso 1 1 calc R . . H1B H 0.7284 0.5343 0.4875 0.039 Uiso 1 1 calc R . . H1C H 0.8704 0.4562 0.4025 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0292(5) 0.0277(5) 0.0232(5) -0.0029(4) 0.0009(4) -0.0034(4) C2 0.0455(7) 0.0926(11) 0.0317(6) -0.0227(7) 0.0119(5) -0.0331(8) C3 0.0505(8) 0.1287(16) 0.0345(7) -0.0254(9) 0.0177(6) -0.0321(10) C4 0.0614(9) 0.0742(10) 0.0249(6) -0.0154(6) 0.0048(6) -0.0008(7) C5 0.0734(10) 0.0519(8) 0.0324(6) -0.0135(6) -0.0057(6) -0.0174(7) C6 0.0468(7) 0.0385(6) 0.0309(5) -0.0058(5) -0.0014(5) -0.0149(5) C7 0.0253(5) 0.0242(5) 0.0254(5) -0.0032(4) 0.0030(4) -0.0041(4) O1 0.0373(4) 0.0414(4) 0.0265(4) -0.0107(3) 0.0072(3) -0.0180(3) O2 0.0292(4) 0.0334(4) 0.0382(4) -0.0071(3) 0.0104(3) -0.0103(3) C8 0.0241(5) 0.0280(5) 0.0227(4) -0.0038(4) 0.0040(4) -0.0080(4) C9 0.0365(6) 0.0326(5) 0.0224(5) -0.0046(4) 0.0037(4) -0.0098(4) C10 0.0445(6) 0.0361(6) 0.0325(6) -0.0052(4) 0.0167(5) -0.0113(5) C11 0.0449(7) 0.0350(6) 0.0410(6) -0.0007(5) 0.0148(5) -0.0135(5) C12 0.0311(5) 0.0322(6) 0.0442(6) -0.0046(5) 0.0020(5) -0.0112(4) C13 0.0358(6) 0.0314(6) 0.0407(6) -0.0082(5) 0.0014(5) -0.0042(5) C14 0.0259(5) 0.0329(6) 0.0395(6) -0.0025(4) -0.0001(4) -0.0002(4) C15 0.0270(5) 0.0339(6) 0.0370(6) -0.0040(4) 0.0075(4) -0.0038(4) N1 0.0264(4) 0.0304(4) 0.0233(4) -0.0049(3) 0.0055(3) -0.0088(3) #----------------------------------------------------------------------------# # 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 1.3778(16) . ? C1 C6 1.3816(15) . ? C1 C7 1.5086(13) . ? C2 C3 1.3882(17) . ? C2 H2 0.95 . ? C3 C4 1.362(2) . ? C3 H3 0.95 . ? C4 C5 1.368(2) . ? C4 H4 0.95 . ? C5 C6 1.3896(17) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.2489(12) . ? C7 O1 1.2636(12) . ? C8 N1 1.4995(13) . ? C8 C15 1.5263(14) . ? C8 C9 1.5336(13) . ? C8 H8 1 . ? C9 C10 1.5296(15) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.5325(17) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.5322(17) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 C13 1.5333(16) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 C14 1.5193(16) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.5211(15) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? N1 H1A 0.91 . ? N1 H1B 0.91 . ? N1 H1C 0.91 . ? 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 C6 118.62(10) . . ? C2 C1 C7 121.22(10) . . ? C6 C1 C7 120.15(10) . . ? C1 C2 C3 120.74(13) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 120.15(14) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 119.89(12) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 120.36(13) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 120.23(12) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? O2 C7 O1 124.16(9) . . ? O2 C7 C1 117.97(9) . . ? O1 C7 C1 117.87(9) . . ? N1 C8 C15 107.35(8) . . ? N1 C8 C9 109.98(8) . . ? C15 C8 C9 114.64(9) . . ? N1 C8 H8 108.2 . . ? C15 C8 H8 108.2 . . ? C9 C8 H8 108.2 . . ? C10 C9 C8 115.00(9) . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C9 C10 C11 118.83(10) . . ? C9 C10 H10A 107.6 . . ? C11 C10 H10A 107.6 . . ? C9 C10 H10B 107.6 . . ? C11 C10 H10B 107.6 . . ? H10A C10 H10B 107 . . ? C12 C11 C10 115.49(10) . . ? C12 C11 H11A 108.4 . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? C10 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C11 C12 C13 115.85(10) . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12B 108.3 . . ? C13 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C14 C13 C12 117.39(9) . . ? C14 C13 H13A 108 . . ? C12 C13 H13A 108 . . ? C14 C13 H13B 108 . . ? C12 C13 H13B 108 . . ? H13A C13 H13B 107.2 . . ? C13 C14 C15 116.57(9) . . ? C13 C14 H14A 108.2 . . ? C15 C14 H14A 108.2 . . ? C13 C14 H14B 108.2 . . ? C15 C14 H14B 108.2 . . ? H14A C14 H14B 107.3 . . ? C14 C15 C8 116.21(9) . . ? C14 C15 H15A 108.2 . . ? C8 C15 H15A 108.2 . . ? C14 C15 H15B 108.2 . . ? C8 C15 H15B 108.2 . . ? H15A C15 H15B 107.4 . . ? C8 N1 H1A 109.5 . . ? C8 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C8 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(2) . . . . ? C7 C1 C2 C3 178.22(15) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C2 C1 C6 C5 0.68(19) . . . . ? C7 C1 C6 C5 -177.91(11) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? C2 C1 C7 O2 -174.36(12) . . . . ? C6 C1 C7 O2 4.19(15) . . . . ? C2 C1 C7 O1 5.53(16) . . . . ? C6 C1 C7 O1 -175.91(10) . . . . ? N1 C8 C9 C10 -136.44(10) . . . . ? C15 C8 C9 C10 102.51(11) . . . . ? C8 C9 C10 C11 -64.03(14) . . . . ? C9 C10 C11 C12 65.09(15) . . . . ? C10 C11 C12 C13 -99.27(13) . . . . ? C11 C12 C13 C14 40.67(15) . . . . ? C12 C13 C14 C15 67.64(14) . . . . ? C13 C14 C15 C8 -62.44(13) . . . . ? N1 C8 C15 C14 -171.15(9) . . . . ? C9 C8 C15 C14 -48.66(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 0.91 1.91 2.782(1) 160 . N1 H1B O1 0.91 1.89 2.787(1) 171 2_666 N1 H1C O2 0.91 1.84 2.740(1) 170 1_655 ###END data_5 _database_code_depnum_ccdc_archive 'CCDC 797977' #TrackingRef '- Lemmerer.cif' _audit_creation_date 2010-10-13T13:27:05-00:00 _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 ; (cyclododecylammonium).(benzoate) ; _chemical_formula_moiety 'C12 H26 N, C7 H5 O2' _chemical_formula_sum 'C19 H31 N O2' _chemical_formula_weight 305.45 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # 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 6.2730(5) _cell_length_b 27.265(2) _cell_length_c 10.4419(8) _cell_angle_alpha 90 _cell_angle_beta 90.432(2) _cell_angle_gamma 90 _cell_volume 1785.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5780 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.51 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.28 1 0 0 0.29 0 0 1 0.05 0 0 -1 0.05 0 1 0 0.05 0 -1 0 0.05 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.9935 #----------------------------------------------------------------------------# # 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 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.1059 _diffrn_reflns_av_unetI/netI 0.062 _diffrn_reflns_number 18921 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _reflns_number_total 4330 _reflns_number_gt 3637 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0909P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4330 _refine_ls_number_parameters 399 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; Friedel Pairs 2084' _refine_ls_abs_structure_Flack 10(10) _refine_diff_density_max 0.51 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.072 #----------------------------------------------------------------------------# # 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 0.6229(4) 0.23153(10) 0.5491(2) 0.0226(5) Uani 1 1 d . . . C2 C 0.4226(4) 0.23407(11) 0.6053(3) 0.0285(6) Uani 1 1 d . . . H2 H 0.3588 0.265 0.6213 0.034 Uiso 1 1 calc R . . C3 C 0.3167(5) 0.19141(13) 0.6375(3) 0.0379(7) Uani 1 1 d . . . H3 H 0.1804 0.1932 0.6763 0.045 Uiso 1 1 calc R . . C4 C 0.4081(6) 0.14614(13) 0.6138(3) 0.0413(8) Uani 1 1 d . . . H4 H 0.3346 0.117 0.6365 0.05 Uiso 1 1 calc R . . C5 C 0.6039(6) 0.14334(12) 0.5578(3) 0.0381(7) Uani 1 1 d . . . H5 H 0.6651 0.1122 0.54 0.046 Uiso 1 1 calc R . . C6 C 0.7133(5) 0.18577(11) 0.5270(3) 0.0289(6) Uani 1 1 d . . . H6 H 0.8512 0.1836 0.4905 0.035 Uiso 1 1 calc R . . C7 C 0.7410(4) 0.27724(10) 0.5113(3) 0.0256(5) Uani 1 1 d . . . O1 O 0.6287(3) 0.31446(8) 0.4861(2) 0.0357(5) Uani 1 1 d . . . O2 O 0.9369(3) 0.27513(9) 0.5068(3) 0.0449(6) Uani 1 1 d . . . C8 C 0.1036(4) 0.48919(10) 0.2216(2) 0.0226(5) Uani 1 1 d . . . C9 C -0.0948(4) 0.48437(11) 0.1642(3) 0.0291(6) Uani 1 1 d . . . H9 H -0.1542 0.4527 0.1509 0.035 Uiso 1 1 calc R . . C10 C -0.2071(5) 0.52597(15) 0.1260(3) 0.0400(8) Uani 1 1 d . . . H10 H -0.342 0.5228 0.0849 0.048 Uiso 1 1 calc R . . C11 C -0.1218(6) 0.57176(13) 0.1480(3) 0.0446(8) Uani 1 1 d . . . H11 H -0.1995 0.6001 0.123 0.054 Uiso 1 1 calc R . . C12 C 0.0741(6) 0.57680(11) 0.2056(3) 0.0404(7) Uani 1 1 d . . . H12 H 0.1311 0.6086 0.2209 0.049 Uiso 1 1 calc R . . C13 C 0.1885(5) 0.53570(11) 0.2413(3) 0.0295(6) Uani 1 1 d . . . H13 H 0.3257 0.5392 0.2794 0.035 Uiso 1 1 calc R . . C14 C 0.2283(4) 0.44499(10) 0.2659(3) 0.0248(5) Uani 1 1 d . . . O3 O 0.1194(3) 0.40733(8) 0.2947(2) 0.0358(5) Uani 1 1 d . . . O4 O 0.4230(3) 0.44766(9) 0.2717(3) 0.0440(6) Uani 1 1 d . . . C15 C 0.2205(4) 0.28349(10) 0.2365(3) 0.0246(5) Uani 1 1 d . . . H15 H 0.0649 0.2794 0.2181 0.029 Uiso 1 1 calc R . . C16 C 0.3184(4) 0.30942(11) 0.1216(3) 0.0288(6) Uani 1 1 d . . . H16A H 0.2372 0.34 0.1057 0.035 Uiso 1 1 calc R . . H16B H 0.2991 0.2882 0.0455 0.035 Uiso 1 1 calc R . . C17 C 0.5549(4) 0.32265(11) 0.1327(3) 0.0306(6) Uani 1 1 d . . . H17A H 0.634 0.2941 0.1673 0.037 Uiso 1 1 calc R . . H17B H 0.5717 0.35 0.1942 0.037 Uiso 1 1 calc R . . C18 C 0.6525(5) 0.33758(11) 0.0044(3) 0.0331(6) Uani 1 1 d . . . H18A H 0.5648 0.3641 -0.0336 0.04 Uiso 1 1 calc R . . H18B H 0.7968 0.351 0.0206 0.04 Uiso 1 1 calc R . . C19 C 0.6695(5) 0.29588(11) -0.0923(3) 0.0323(6) Uani 1 1 d . . . H19A H 0.7032 0.3099 -0.1772 0.039 Uiso 1 1 calc R . . H19B H 0.5294 0.2793 -0.0994 0.039 Uiso 1 1 calc R . . C20 C 0.8386(5) 0.25781(12) -0.0573(3) 0.0316(6) Uani 1 1 d . . . H20A H 0.8511 0.2564 0.0372 0.038 Uiso 1 1 calc R . . H20B H 0.9774 0.2692 -0.0906 0.038 Uiso 1 1 calc R . . C21 C 0.7983(5) 0.20581(12) -0.1072(3) 0.0324(6) Uani 1 1 d . . . H21A H 0.7799 0.2072 -0.2014 0.039 Uiso 1 1 calc R . . H21B H 0.9258 0.1855 -0.0888 0.039 Uiso 1 1 calc R . . C22 C 0.6044(5) 0.18079(12) -0.0499(3) 0.0339(6) Uani 1 1 d . . . H22A H 0.5776 0.1499 -0.097 0.041 Uiso 1 1 calc R . . H22B H 0.4787 0.2022 -0.0629 0.041 Uiso 1 1 calc R . . C23 C 0.6251(4) 0.16912(11) 0.0923(3) 0.0304(6) Uani 1 1 d . . . H23A H 0.6794 0.1986 0.1372 0.036 Uiso 1 1 calc R . . H23B H 0.7322 0.1428 0.1034 0.036 Uiso 1 1 calc R . . C24 C 0.4179(5) 0.15299(10) 0.1557(3) 0.0317(6) Uani 1 1 d . . . H24A H 0.4509 0.1408 0.2429 0.038 Uiso 1 1 calc R . . H24B H 0.3563 0.1254 0.1061 0.038 Uiso 1 1 calc R . . C25 C 0.2517(4) 0.19375(11) 0.1651(3) 0.0294(6) Uani 1 1 d . . . H25A H 0.1125 0.1791 0.1878 0.035 Uiso 1 1 calc R . . H25B H 0.2356 0.2097 0.0804 0.035 Uiso 1 1 calc R . . C26 C 0.3110(4) 0.23270(10) 0.2649(3) 0.0270(6) Uani 1 1 d . . . H26A H 0.2591 0.2219 0.3496 0.032 Uiso 1 1 calc R . . H26B H 0.4683 0.2351 0.2703 0.032 Uiso 1 1 calc R . . N1 N 0.2411(3) 0.31450(8) 0.3539(2) 0.0239(4) Uani 1 1 d . . . H1A H 0.3748 0.3113 0.3872 0.036 Uiso 1 1 calc R . . H1B H 0.1438 0.3046 0.4128 0.036 Uiso 1 1 calc R . . H1C H 0.2171 0.3465 0.3331 0.036 Uiso 1 1 calc R . . C27 C 0.7175(4) 0.44128(10) 0.5401(3) 0.0255(5) Uani 1 1 d . . . H27 H 0.5625 0.4457 0.5585 0.031 Uiso 1 1 calc R . . C28 C 0.8187(4) 0.41659(11) 0.6570(3) 0.0300(6) Uani 1 1 d . . . H28A H 0.8055 0.4391 0.7309 0.036 Uiso 1 1 calc R . . H28B H 0.7354 0.3867 0.6769 0.036 Uiso 1 1 calc R . . C29 C 1.0528(5) 0.40202(12) 0.6448(3) 0.0334(6) Uani 1 1 d . . . H29A H 1.1333 0.4299 0.6084 0.04 Uiso 1 1 calc R . . H29B H 1.064 0.3742 0.5844 0.04 Uiso 1 1 calc R . . C30 C 1.1551(5) 0.38731(12) 0.7733(3) 0.0361(7) Uani 1 1 d . . . H30A H 1.0699 0.3605 0.8112 0.043 Uiso 1 1 calc R . . H30B H 1.2996 0.3742 0.7568 0.043 Uiso 1 1 calc R . . C31 C 1.1735(5) 0.42878(11) 0.8708(3) 0.0319(6) Uani 1 1 d . . . H31A H 1.213 0.4147 0.9551 0.038 Uiso 1 1 calc R . . H31B H 1.0323 0.4446 0.8798 0.038 Uiso 1 1 calc R . . C32 C 1.3371(5) 0.46789(12) 0.8354(3) 0.0350(7) Uani 1 1 d . . . H32A H 1.3492 0.4689 0.741 0.042 Uiso 1 1 calc R . . H32B H 1.4777 0.4579 0.8705 0.042 Uiso 1 1 calc R . . C33 C 1.2868(5) 0.51978(12) 0.8834(3) 0.0359(7) Uani 1 1 d . . . H33A H 1.2659 0.5185 0.9772 0.043 Uiso 1 1 calc R . . H33B H 1.4114 0.5411 0.867 0.043 Uiso 1 1 calc R . . C34 C 1.0921(5) 0.54268(11) 0.8221(3) 0.0325(6) Uani 1 1 d . . . H34A H 1.0543 0.5726 0.8706 0.039 Uiso 1 1 calc R . . H34B H 0.9715 0.5195 0.8293 0.039 Uiso 1 1 calc R . . C35 C 1.1193(5) 0.55637(12) 0.6812(3) 0.0321(6) Uani 1 1 d . . . H35A H 1.2245 0.5833 0.6756 0.039 Uiso 1 1 calc R . . H35B H 1.179 0.5278 0.6354 0.039 Uiso 1 1 calc R . . C36 C 0.9155(5) 0.57231(11) 0.6129(3) 0.0340(7) Uani 1 1 d . . . H36A H 0.9519 0.5837 0.5258 0.041 Uiso 1 1 calc R . . H36B H 0.8536 0.6005 0.6596 0.041 Uiso 1 1 calc R . . C37 C 0.7469(4) 0.53191(11) 0.6019(3) 0.0310(6) Uani 1 1 d . . . H37A H 0.7255 0.517 0.6872 0.037 Uiso 1 1 calc R . . H37B H 0.61 0.5467 0.5743 0.037 Uiso 1 1 calc R . . C38 C 0.8083(4) 0.49170(10) 0.5070(3) 0.0280(6) Uani 1 1 d . . . H38A H 0.7573 0.5012 0.4205 0.034 Uiso 1 1 calc R . . H38B H 0.9657 0.4894 0.504 0.034 Uiso 1 1 calc R . . N2 N 0.7337(3) 0.40897(9) 0.4245(2) 0.0250(5) Uani 1 1 d . . . H2A H 0.866 0.4119 0.3902 0.037 Uiso 1 1 calc R . . H2B H 0.634 0.4182 0.3655 0.037 Uiso 1 1 calc R . . H2C H 0.7108 0.3772 0.4476 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0245(12) 0.0233(13) 0.0199(12) 0.0019(10) 0.0019(9) -0.0030(10) C2 0.0269(13) 0.0324(15) 0.0262(13) 0.0027(11) 0.0065(10) -0.0016(11) C3 0.0320(14) 0.051(2) 0.0308(14) 0.0076(14) 0.0066(11) -0.0132(14) C4 0.061(2) 0.0322(17) 0.0311(16) 0.0057(13) 0.0028(14) -0.0205(15) C5 0.062(2) 0.0224(15) 0.0305(15) -0.0005(12) 0.0053(14) -0.0043(14) C6 0.0363(14) 0.0246(14) 0.0259(13) 0.0009(11) 0.0058(11) 0.0007(11) C7 0.0315(13) 0.0218(13) 0.0237(13) 0.0031(10) 0.0027(10) -0.0049(11) O1 0.0394(11) 0.0201(10) 0.0475(13) 0.0082(9) -0.0036(9) -0.0045(9) O2 0.0302(10) 0.0375(13) 0.0673(16) 0.0138(12) 0.0162(10) -0.0051(9) C8 0.0289(12) 0.0194(12) 0.0198(11) 0.0026(10) 0.0117(10) 0.0043(10) C9 0.0316(13) 0.0322(15) 0.0237(13) 0.0022(11) 0.0095(11) 0.0039(11) C10 0.0352(15) 0.056(2) 0.0286(15) 0.0080(14) 0.0074(12) 0.0172(15) C11 0.066(2) 0.0351(18) 0.0328(16) 0.0098(14) 0.0166(15) 0.0275(16) C12 0.066(2) 0.0190(15) 0.0362(16) 0.0035(12) 0.0147(15) 0.0049(14) C13 0.0379(14) 0.0237(14) 0.0270(13) 0.0030(11) 0.0110(11) 0.0003(11) C14 0.0312(13) 0.0194(13) 0.0239(13) 0.0014(10) 0.0075(10) 0.0034(10) O3 0.0386(10) 0.0181(10) 0.0509(13) 0.0082(9) 0.0199(9) 0.0049(8) O4 0.0298(11) 0.0347(13) 0.0673(16) 0.0140(11) -0.0026(10) 0.0046(9) C15 0.0256(12) 0.0224(13) 0.0257(13) -0.0002(10) 0.0042(10) 0.0010(10) C16 0.0348(14) 0.0251(14) 0.0267(13) 0.0044(11) 0.0044(11) 0.0042(11) C17 0.0371(15) 0.0263(15) 0.0285(14) -0.0022(11) 0.0082(11) -0.0048(11) C18 0.0405(16) 0.0230(14) 0.0358(15) 0.0044(12) 0.0123(13) -0.0028(12) C19 0.0407(15) 0.0302(15) 0.0262(13) 0.0049(11) 0.0071(12) 0.0006(12) C20 0.0343(14) 0.0293(15) 0.0314(14) -0.0017(12) 0.0038(11) -0.0021(12) C21 0.0367(14) 0.0338(16) 0.0266(14) -0.0068(12) 0.0071(11) 0.0011(12) C22 0.0398(15) 0.0312(16) 0.0307(15) -0.0075(12) 0.0035(12) -0.0055(12) C23 0.0335(14) 0.0237(14) 0.0340(15) 0.0002(12) 0.0016(12) 0.0042(11) C24 0.0432(16) 0.0167(13) 0.0351(15) 0.0001(11) 0.0055(12) 0.0003(11) C25 0.0311(13) 0.0233(14) 0.0337(15) -0.0053(12) -0.0005(11) 0.0007(11) C26 0.0335(13) 0.0198(13) 0.0276(13) 0.0000(11) 0.0022(11) 0.0006(11) N1 0.0254(10) 0.0163(10) 0.0302(11) 0.0001(9) 0.0075(8) -0.0002(8) C27 0.0262(12) 0.0197(13) 0.0308(14) -0.0008(11) 0.0079(10) 0.0012(10) C28 0.0318(13) 0.0276(15) 0.0309(14) 0.0039(12) 0.0094(11) -0.0017(11) C29 0.0392(15) 0.0324(17) 0.0287(14) -0.0033(12) 0.0060(12) 0.0051(12) C30 0.0428(16) 0.0276(16) 0.0379(16) 0.0026(13) 0.0020(13) 0.0055(13) C31 0.0408(15) 0.0315(16) 0.0235(13) 0.0066(11) 0.0062(12) 0.0019(12) C32 0.0369(15) 0.0373(17) 0.0310(15) 0.0012(13) 0.0103(12) 0.0007(13) C33 0.0440(17) 0.0385(18) 0.0254(14) -0.0028(12) 0.0087(12) -0.0117(13) C34 0.0434(16) 0.0266(15) 0.0279(14) -0.0056(11) 0.0179(12) -0.0061(12) C35 0.0396(15) 0.0272(15) 0.0296(14) -0.0011(12) 0.0120(12) -0.0094(12) C36 0.0457(16) 0.0188(14) 0.0379(16) -0.0045(12) 0.0129(13) 0.0010(12) C37 0.0325(13) 0.0243(14) 0.0363(15) -0.0060(12) 0.0128(11) 0.0020(11) C38 0.0345(14) 0.0190(13) 0.0306(14) -0.0012(11) 0.0081(11) 0.0003(11) N2 0.0257(10) 0.0194(11) 0.0299(11) -0.0013(9) 0.0054(9) 0.0007(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 C6 1.390(4) . ? C1 C2 1.393(4) . ? C1 C7 1.504(4) . ? C2 C3 1.382(4) . ? C2 H2 0.95 . ? C3 C4 1.384(5) . ? C3 H3 0.95 . ? C4 C5 1.367(5) . ? C4 H4 0.95 . ? C5 C6 1.384(4) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.232(3) . ? C7 O1 1.262(4) . ? C8 C9 1.384(4) . ? C8 C13 1.390(4) . ? C8 C14 1.508(4) . ? C9 C10 1.392(4) . ? C9 H9 0.95 . ? C10 C11 1.377(5) . ? C10 H10 0.95 . ? C11 C12 1.371(5) . ? C11 H11 0.95 . ? C12 C13 1.381(4) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 O4 1.224(3) . ? C14 O3 1.271(3) . ? C15 N1 1.494(3) . ? C15 C26 1.525(4) . ? C15 C16 1.526(4) . ? C15 H15 1 . ? C16 C17 1.530(4) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.532(4) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 C19 1.525(4) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 C20 1.527(4) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 C21 1.531(4) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 C22 1.522(4) . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 C23 1.523(4) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C23 C24 1.527(4) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 C25 1.528(4) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C25 C26 1.532(4) . ? C25 H25A 0.99 . ? C25 H25B 0.99 . ? C26 H26A 0.99 . ? C26 H26B 0.99 . ? N1 H1A 0.91 . ? N1 H1B 0.91 . ? N1 H1C 0.91 . ? C27 N2 1.498(4) . ? C27 C28 1.528(4) . ? C27 C38 1.529(4) . ? C27 H27 1 . ? C28 C29 1.527(4) . ? C28 H28A 0.99 . ? C28 H28B 0.99 . ? C29 C30 1.536(4) . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C30 C31 1.526(4) . ? C30 H30A 0.99 . ? C30 H30B 0.99 . ? C31 C32 1.527(4) . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C32 C33 1.534(5) . ? C32 H32A 0.99 . ? C32 H32B 0.99 . ? C33 C34 1.510(5) . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C34 C35 1.529(4) . ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? C35 C36 1.523(4) . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? C36 C37 1.531(4) . ? C36 H36A 0.99 . ? C36 H36B 0.99 . ? C37 C38 1.529(4) . ? C37 H37A 0.99 . ? C37 H37B 0.99 . ? C38 H38A 0.99 . ? C38 H38B 0.99 . ? N2 H2A 0.91 . ? N2 H2B 0.91 . ? N2 H2C 0.91 . ? 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 C6 C1 C2 119.0(2) . . ? C6 C1 C7 119.9(2) . . ? C2 C1 C7 121.1(3) . . ? C3 C2 C1 119.8(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 120 . . ? C3 C4 H4 120 . . ? C4 C5 C6 120.1(3) . . ? C4 C5 H5 120 . . ? C6 C5 H5 120 . . ? C5 C6 C1 120.5(3) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O2 C7 O1 125.8(3) . . ? O2 C7 C1 117.7(3) . . ? O1 C7 C1 116.5(2) . . ? C9 C8 C13 119.6(3) . . ? C9 C8 C14 121.3(3) . . ? C13 C8 C14 119.1(2) . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 119.7(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 120.7(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 120.0(3) . . ? C11 C12 H12 120 . . ? C13 C12 H12 120 . . ? C12 C13 C8 120.2(3) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? O4 C14 O3 125.1(3) . . ? O4 C14 C8 118.8(2) . . ? O3 C14 C8 116.1(2) . . ? N1 C15 C26 108.9(2) . . ? N1 C15 C16 110.5(2) . . ? C26 C15 C16 115.0(2) . . ? N1 C15 H15 107.4 . . ? C26 C15 H15 107.4 . . ? C16 C15 H15 107.4 . . ? C15 C16 C17 116.5(2) . . ? C15 C16 H16A 108.2 . . ? C17 C16 H16A 108.2 . . ? C15 C16 H16B 108.2 . . ? C17 C16 H16B 108.2 . . ? H16A C16 H16B 107.3 . . ? C16 C17 C18 113.0(2) . . ? C16 C17 H17A 109 . . ? C18 C17 H17A 109 . . ? C16 C17 H17B 109 . . ? C18 C17 H17B 109 . . ? H17A C17 H17B 107.8 . . ? C19 C18 C17 114.3(2) . . ? C19 C18 H18A 108.7 . . ? C17 C18 H18A 108.7 . . ? C19 C18 H18B 108.7 . . ? C17 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C18 C19 C20 113.6(2) . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19B 108.8 . . ? C20 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 C21 115.8(2) . . ? C19 C20 H20A 108.3 . . ? C21 C20 H20A 108.3 . . ? C19 C20 H20B 108.3 . . ? C21 C20 H20B 108.3 . . ? H20A C20 H20B 107.4 . . ? C22 C21 C20 114.3(2) . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21B 108.7 . . ? C20 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C21 C22 C23 114.5(2) . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C22 C23 C24 114.6(2) . . ? C22 C23 H23A 108.6 . . ? C24 C23 H23A 108.6 . . ? C22 C23 H23B 108.6 . . ? C24 C23 H23B 108.6 . . ? H23A C23 H23B 107.6 . . ? C23 C24 C25 113.7(2) . . ? C23 C24 H24A 108.8 . . ? C25 C24 H24A 108.8 . . ? C23 C24 H24B 108.8 . . ? C25 C24 H24B 108.8 . . ? H24A C24 H24B 107.7 . . ? C24 C25 C26 112.7(2) . . ? C24 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? C24 C25 H25B 109.1 . . ? C26 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? C15 C26 C25 114.1(2) . . ? C15 C26 H26A 108.7 . . ? C25 C26 H26A 108.7 . . ? C15 C26 H26B 108.7 . . ? C25 C26 H26B 108.7 . . ? H26A C26 H26B 107.6 . . ? C15 N1 H1A 109.5 . . ? C15 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C15 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? N2 C27 C28 110.8(2) . . ? N2 C27 C38 108.6(2) . . ? C28 C27 C38 115.1(2) . . ? N2 C27 H27 107.4 . . ? C28 C27 H27 107.4 . . ? C38 C27 H27 107.4 . . ? C29 C28 C27 116.2(2) . . ? C29 C28 H28A 108.2 . . ? C27 C28 H28A 108.2 . . ? C29 C28 H28B 108.2 . . ? C27 C28 H28B 108.2 . . ? H28A C28 H28B 107.4 . . ? C28 C29 C30 113.0(3) . . ? C28 C29 H29A 109 . . ? C30 C29 H29A 109 . . ? C28 C29 H29B 109 . . ? C30 C29 H29B 109 . . ? H29A C29 H29B 107.8 . . ? C31 C30 C29 114.7(3) . . ? C31 C30 H30A 108.6 . . ? C29 C30 H30A 108.6 . . ? C31 C30 H30B 108.6 . . ? C29 C30 H30B 108.6 . . ? H30A C30 H30B 107.6 . . ? C30 C31 C32 113.8(3) . . ? C30 C31 H31A 108.8 . . ? C32 C31 H31A 108.8 . . ? C30 C31 H31B 108.8 . . ? C32 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C31 C32 C33 115.1(3) . . ? C31 C32 H32A 108.5 . . ? C33 C32 H32A 108.5 . . ? C31 C32 H32B 108.5 . . ? C33 C32 H32B 108.5 . . ? H32A C32 H32B 107.5 . . ? C34 C33 C32 114.2(2) . . ? C34 C33 H33A 108.7 . . ? C32 C33 H33A 108.7 . . ? C34 C33 H33B 108.7 . . ? C32 C33 H33B 108.7 . . ? H33A C33 H33B 107.6 . . ? C33 C34 C35 114.4(2) . . ? C33 C34 H34A 108.7 . . ? C35 C34 H34A 108.7 . . ? C33 C34 H34B 108.7 . . ? C35 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? C36 C35 C34 114.9(2) . . ? C36 C35 H35A 108.5 . . ? C34 C35 H35A 108.5 . . ? C36 C35 H35B 108.5 . . ? C34 C35 H35B 108.5 . . ? H35A C35 H35B 107.5 . . ? C35 C36 C37 114.0(2) . . ? C35 C36 H36A 108.8 . . ? C37 C36 H36A 108.8 . . ? C35 C36 H36B 108.8 . . ? C37 C36 H36B 108.8 . . ? H36A C36 H36B 107.6 . . ? C38 C37 C36 112.8(2) . . ? C38 C37 H37A 109 . . ? C36 C37 H37A 109 . . ? C38 C37 H37B 109 . . ? C36 C37 H37B 109 . . ? H37A C37 H37B 107.8 . . ? C27 C38 C37 113.7(2) . . ? C27 C38 H38A 108.8 . . ? C37 C38 H38A 108.8 . . ? C27 C38 H38B 108.8 . . ? C37 C38 H38B 108.8 . . ? H38A C38 H38B 107.7 . . ? C27 N2 H2A 109.5 . . ? C27 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C27 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.3(4) . . . . ? C7 C1 C2 C3 179.2(2) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C3 C4 C5 C6 1.3(5) . . . . ? C4 C5 C6 C1 -1.9(4) . . . . ? C2 C1 C6 C5 1.4(4) . . . . ? C7 C1 C6 C5 -178.1(3) . . . . ? C6 C1 C7 O2 -26.4(4) . . . . ? C2 C1 C7 O2 154.2(3) . . . . ? C6 C1 C7 O1 153.2(3) . . . . ? C2 C1 C7 O1 -26.3(4) . . . . ? C13 C8 C9 C10 0.4(4) . . . . ? C14 C8 C9 C10 179.1(3) . . . . ? C8 C9 C10 C11 -1.3(4) . . . . ? C9 C10 C11 C12 0.9(5) . . . . ? C10 C11 C12 C13 0.5(5) . . . . ? C11 C12 C13 C8 -1.4(5) . . . . ? C9 C8 C13 C12 1.0(4) . . . . ? C14 C8 C13 C12 -177.8(3) . . . . ? C9 C8 C14 O4 153.5(3) . . . . ? C13 C8 C14 O4 -27.7(4) . . . . ? C9 C8 C14 O3 -26.5(4) . . . . ? C13 C8 C14 O3 152.2(3) . . . . ? N1 C15 C16 C17 59.2(3) . . . . ? C26 C15 C16 C17 -64.6(3) . . . . ? C15 C16 C17 C18 166.9(2) . . . . ? C16 C17 C18 C19 -68.1(3) . . . . ? C17 C18 C19 C20 -70.9(3) . . . . ? C18 C19 C20 C21 152.2(3) . . . . ? C19 C20 C21 C22 -65.8(3) . . . . ? C20 C21 C22 C23 -67.2(4) . . . . ? C21 C22 C23 C24 169.1(2) . . . . ? C22 C23 C24 C25 -68.2(3) . . . . ? C23 C24 C25 C26 -71.9(3) . . . . ? N1 C15 C26 C25 165.8(2) . . . . ? C16 C15 C26 C25 -69.5(3) . . . . ? C24 C25 C26 C15 152.0(2) . . . . ? N2 C27 C28 C29 57.7(3) . . . . ? C38 C27 C28 C29 -65.9(3) . . . . ? C27 C28 C29 C30 168.3(3) . . . . ? C28 C29 C30 C31 -65.7(4) . . . . ? C29 C30 C31 C32 -69.9(3) . . . . ? C30 C31 C32 C33 149.7(3) . . . . ? C31 C32 C33 C34 -66.7(3) . . . . ? C32 C33 C34 C35 -70.0(3) . . . . ? C33 C34 C35 C36 171.3(3) . . . . ? C34 C35 C36 C37 -64.5(3) . . . . ? C35 C36 C37 C38 -71.1(3) . . . . ? N2 C27 C38 C37 164.0(2) . . . . ? C28 C27 C38 C37 -71.2(3) . . . . ? C36 C37 C38 C27 150.2(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 0.91 1.89 2.787(3) 167 . N1 H1B O2 0.91 1.82 2.718(3) 168 1_455 N1 H1C O3 0.91 1.81 2.714(3) 170 . N2 H2A O3 0.91 1.89 2.782(3) 168 1_655 N2 H2B O4 0.91 1.83 2.722(3) 167 . N2 H2C O1 0.91 1.83 2.738(3) 172 . ###END data_6 _database_code_depnum_ccdc_archive 'CCDC 797978' #TrackingRef '- Lemmerer.cif' _audit_creation_date 2010-10-13T10:45:45-00:00 _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 ; (cyclopentylammonium).(adamantane carboxylate) ; _chemical_formula_moiety 'C11 H15 O2, C5 H12 N' _chemical_formula_sum 'C16 H27 N O2' _chemical_formula_weight 265.39 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # 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 6.4663(2) _cell_length_b 11.0134(4) _cell_length_c 21.0375(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1498.20(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2082 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 27.43 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.177 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 1 0.05 0 -1 -1 0.05 0 2 -1 0.114 -2 -2 -1 0.069 2 1 2 0.124 0 -2 3 0.152 1 1 -2 0.123 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.994 #----------------------------------------------------------------------------# # 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 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.066 _diffrn_reflns_av_unetI/netI 0.0505 _diffrn_reflns_number 7939 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2099 _reflns_number_gt 1685 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0787P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2099 _refine_ls_number_parameters 183 _refine_ls_number_restraints 69 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.07 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 1521 friedel pairs' _refine_ls_abs_structure_Flack 10(10) _refine_diff_density_max 0.32 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.048 #----------------------------------------------------------------------------# # 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 0.3081(4) 0.24035(19) 0.69079(9) 0.0175(5) Uani 1 1 d . . . C2 C 0.1059(4) 0.1702(2) 0.69906(10) 0.0219(5) Uani 1 1 d . . . H2A H 0.1223 0.0869 0.6821 0.026 Uiso 1 1 calc R . . H2B H -0.0056 0.2108 0.6748 0.026 Uiso 1 1 calc R . . C3 C 0.2759(4) 0.37070(18) 0.71678(10) 0.0208(5) Uani 1 1 d . . . H3A H 0.405 0.418 0.7117 0.025 Uiso 1 1 calc R . . H3B H 0.1655 0.4118 0.6923 0.025 Uiso 1 1 calc R . . C4 C 0.4798(4) 0.1794(2) 0.72989(10) 0.0225(5) Uani 1 1 d . . . H4A H 0.5037 0.0961 0.7138 0.027 Uiso 1 1 calc R . . H4B H 0.61 0.2258 0.7251 0.027 Uiso 1 1 calc R . . C5 C 0.0463(4) 0.1641(2) 0.76980(10) 0.0223(5) Uani 1 1 d . . . H5 H -0.0852 0.1172 0.7747 0.027 Uiso 1 1 calc R . . C6 C 0.0153(4) 0.2937(2) 0.79470(11) 0.0249(5) Uani 1 1 d . . . H6A H -0.0971 0.3339 0.7706 0.03 Uiso 1 1 calc R . . H6B H -0.0251 0.2912 0.8401 0.03 Uiso 1 1 calc R . . C7 C 0.2155(4) 0.3659(2) 0.78724(11) 0.0239(5) Uani 1 1 d . . . H7 H 0.1948 0.4503 0.8036 0.029 Uiso 1 1 calc R . . C8 C 0.3884(4) 0.3040(2) 0.82485(11) 0.0270(5) Uani 1 1 d . . . H8A H 0.3519 0.302 0.8705 0.032 Uiso 1 1 calc R . . H8B H 0.5185 0.3505 0.8201 0.032 Uiso 1 1 calc R . . C9 C 0.4193(4) 0.1741(2) 0.80026(10) 0.0248(5) Uani 1 1 d . . . H9 H 0.5318 0.1336 0.825 0.03 Uiso 1 1 calc R . . C10 C 0.2180(5) 0.1025(2) 0.80784(11) 0.0286(6) Uani 1 1 d . . . H10A H 0.2378 0.0184 0.7924 0.034 Uiso 1 1 calc R . . H10B H 0.179 0.0989 0.8533 0.034 Uiso 1 1 calc R . . C11 C 0.3772(4) 0.2523(2) 0.62139(10) 0.0226(5) Uani 1 1 d . . . O1 O 0.2493(3) 0.23255(19) 0.57769(8) 0.0382(5) Uani 1 1 d . . . O2 O 0.5576(3) 0.28779(18) 0.61126(8) 0.0362(5) Uani 1 1 d . . . C12 C 0.3135(5) 0.4582(2) 0.45369(14) 0.0372(7) Uani 1 1 d U A . H12 H 0.298 0.4801 0.4078 0.045 Uiso 1 1 calc R . . C13 C 0.1199(6) 0.4975(3) 0.48945(18) 0.0522(8) Uani 1 1 d U A . H13A H 0.0241 0.5422 0.4612 0.063 Uiso 1 1 calc R . . H13B H 0.0469 0.4265 0.5076 0.063 Uiso 1 1 calc R . . C14 C 0.2022(11) 0.5789(5) 0.5412(2) 0.1035(18) Uani 1 1 d DU . . H14A H 0.0999 0.6427 0.5517 0.124 Uiso 0.716(11) 1 calc PR A 1 H14B H 0.2313 0.5312 0.5801 0.124 Uiso 0.716(11) 1 calc PR A 1 H14C H 0.1663 0.6647 0.5324 0.124 Uiso 0.284(11) 1 d PR A 2 H14D H 0.1402 0.5559 0.5825 0.124 Uiso 0.284(11) 1 d PR A 2 C15A C 0.3905(10) 0.6331(5) 0.5172(3) 0.078(2) Uani 0.716(11) 1 d PDU A 1 H15A H 0.4797 0.6618 0.5524 0.093 Uiso 0.716(11) 1 calc PR A 1 H15B H 0.3599 0.7021 0.4885 0.093 Uiso 0.716(11) 1 calc PR A 1 C15B C 0.4265(15) 0.5649(13) 0.5437(5) 0.083(3) Uani 0.284(11) 1 d PDU A 2 H15C H 0.4929 0.6422 0.5564 0.099 Uiso 0.284(11) 1 calc PR A 2 H15D H 0.4652 0.5014 0.5748 0.099 Uiso 0.284(11) 1 calc PR A 2 C16 C 0.4898(7) 0.5310(3) 0.4819(3) 0.0749(12) Uani 1 1 d DU . . H16A H 0.5729 0.4801 0.5111 0.09 Uiso 0.716(11) 1 calc PR A 1 H16B H 0.5813 0.5625 0.448 0.09 Uiso 0.716(11) 1 calc PR A 1 H16C H 0.6176 0.4815 0.4832 0.09 Uiso 0.284(11) 1 d PR A 2 H16D H 0.5164 0.6045 0.4561 0.09 Uiso 0.284(11) 1 d PR A 2 N1 N 0.3505(4) 0.32512(19) 0.45912(9) 0.0269(5) Uani 1 1 d . . . H1A H 0.3422 0.3025 0.5007 0.04 Uiso 1 1 calc R A . H1B H 0.4785 0.3071 0.4438 0.04 Uiso 1 1 calc R . . H1C H 0.2533 0.2844 0.4362 0.04 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0183(11) 0.0174(10) 0.0168(10) -0.0011(8) 0.0011(9) 0.0007(9) C2 0.0233(13) 0.0241(11) 0.0183(10) -0.0015(8) -0.0008(9) -0.0035(10) C3 0.0241(13) 0.0167(10) 0.0216(11) 0.0005(8) 0.0027(10) 0.0008(9) C4 0.0209(12) 0.0236(11) 0.0230(11) -0.0020(8) -0.0017(9) 0.0044(10) C5 0.0228(13) 0.0242(11) 0.0200(11) 0.0018(8) 0.0039(9) -0.0049(10) C6 0.0242(13) 0.0304(12) 0.0202(11) -0.0013(9) 0.0058(10) 0.0038(11) C7 0.0289(14) 0.0208(11) 0.0219(11) -0.0047(8) 0.0030(10) 0.0013(10) C8 0.0286(14) 0.0335(13) 0.0191(11) -0.0050(9) -0.0025(10) -0.0008(12) C9 0.0241(13) 0.0298(12) 0.0204(11) 0.0019(9) -0.0031(10) 0.0087(11) C10 0.0361(16) 0.0246(11) 0.0251(12) 0.0064(9) 0.0018(11) 0.0014(11) C11 0.0253(13) 0.0225(11) 0.0199(11) -0.0009(8) 0.0051(9) 0.0003(10) O1 0.0309(11) 0.0663(13) 0.0175(8) 0.0051(8) -0.0014(8) -0.0078(11) O2 0.0273(10) 0.0553(12) 0.0261(9) -0.0068(8) 0.0094(8) -0.0090(9) C12 0.0413(17) 0.0349(14) 0.0354(14) 0.0055(10) 0.0029(13) 0.0023(13) C13 0.0447(19) 0.0420(17) 0.070(2) 0.0074(15) 0.0147(17) 0.0124(15) C14 0.140(4) 0.094(3) 0.077(3) -0.031(2) 0.043(3) -0.009(3) C15A 0.122(5) 0.060(3) 0.051(3) -0.007(2) -0.013(3) -0.024(3) C15B 0.138(6) 0.043(7) 0.066(5) 0.021(5) -0.040(5) -0.041(7) C16 0.053(2) 0.0459(19) 0.126(4) 0.001(2) -0.007(2) -0.0137(18) N1 0.0252(12) 0.0382(11) 0.0173(9) 0.0009(8) 0.0003(8) 0.0020(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 1.529(3) . ? C1 C11 1.533(3) . ? C1 C4 1.536(3) . ? C1 C3 1.550(3) . ? C2 C5 1.539(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C7 1.534(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C9 1.532(3) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C10 1.528(4) . ? C5 C6 1.534(3) . ? C5 H5 1 . ? C6 C7 1.528(4) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.530(4) . ? C7 H7 1 . ? C8 C9 1.534(3) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.530(4) . ? C9 H9 1 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 O2 1.248(3) . ? C11 O1 1.256(3) . ? C12 N1 1.490(3) . ? C12 C16 1.515(5) . ? C12 C13 1.523(4) . ? C12 H12 1 . ? C13 C14 1.508(6) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15A 1.447(7) . ? C14 C15B 1.459(9) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C14 H14C 0.99 . ? C14 H14D 0.99 . ? C15A C16 1.493(6) . ? C15A H15A 0.99 . ? C15A H15B 0.99 . ? C15B C16 1.412(8) . ? C15B H15C 0.99 . ? C15B H15D 0.99 . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C16 H16C 0.99 . ? C16 H16D 0.99 . ? N1 H1A 0.91 . ? N1 H1B 0.91 . ? N1 H1C 0.91 . ? 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 C11 113.66(18) . . ? C2 C1 C4 109.64(18) . . ? C11 C1 C4 109.69(19) . . ? C2 C1 C3 108.24(18) . . ? C11 C1 C3 107.20(17) . . ? C4 C1 C3 108.24(18) . . ? C1 C2 C5 110.25(17) . . ? C1 C2 H2A 109.6 . . ? C5 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C5 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C7 C3 C1 110.09(17) . . ? C7 C3 H3A 109.6 . . ? C1 C3 H3A 109.6 . . ? C7 C3 H3B 109.6 . . ? C1 C3 H3B 109.6 . . ? H3A C3 H3B 108.2 . . ? C9 C4 C1 110.47(19) . . ? C9 C4 H4A 109.6 . . ? C1 C4 H4A 109.6 . . ? C9 C4 H4B 109.6 . . ? C1 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C10 C5 C6 109.2(2) . . ? C10 C5 C2 110.1(2) . . ? C6 C5 C2 108.83(18) . . ? C10 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? C2 C5 H5 109.5 . . ? C7 C6 C5 109.8(2) . . ? C7 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? C7 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C6 C7 C8 109.52(19) . . ? C6 C7 C3 109.44(19) . . ? C8 C7 C3 109.2(2) . . ? C6 C7 H7 109.5 . . ? C8 C7 H7 109.5 . . ? C3 C7 H7 109.5 . . ? C7 C8 C9 109.65(19) . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C10 C9 C4 109.72(19) . . ? C10 C9 C8 109.6(2) . . ? C4 C9 C8 108.86(19) . . ? C10 C9 H9 109.6 . . ? C4 C9 H9 109.6 . . ? C8 C9 H9 109.6 . . ? C5 C10 C9 109.56(19) . . ? C5 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? C5 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? O2 C11 O1 123.0(2) . . ? O2 C11 C1 117.5(2) . . ? O1 C11 C1 119.4(2) . . ? N1 C12 C16 111.7(3) . . ? N1 C12 C13 111.9(2) . . ? C16 C12 C13 105.9(3) . . ? N1 C12 H12 109.1 . . ? C16 C12 H12 109.1 . . ? C13 C12 H12 109.1 . . ? C14 C13 C12 103.6(3) . . ? C14 C13 H13A 111 . . ? C12 C13 H13A 111 . . ? C14 C13 H13B 111 . . ? C12 C13 H13B 111 . . ? H13A C13 H13B 109 . . ? C15A C14 C13 106.9(4) . . ? C15B C14 C13 108.2(6) . . ? C15A C14 H14A 110.4 . . ? C13 C14 H14A 110.4 . . ? C15A C14 H14B 110.4 . . ? C13 C14 H14B 110.4 . . ? H14A C14 H14B 108.6 . . ? C15B C14 H14C 110 . . ? C13 C14 H14C 110.4 . . ? C15B C14 H14D 110.2 . . ? C13 C14 H14D 109.8 . . ? H14C C14 H14D 108.3 . . ? C14 C15A C16 103.0(4) . . ? C14 C15A H15A 111.2 . . ? C16 C15A H15A 111.2 . . ? H14C C15A H15A 109 . . ? C14 C15A H15B 111.2 . . ? C16 C15A H15B 111.2 . . ? H15A C15A H15B 109.1 . . ? H15A C15A H16D 112.2 . . ? C16 C15B C14 106.5(7) . . ? C16 C15B H15C 110.4 . . ? C14 C15B H15C 110.4 . . ? C16 C15B H15D 110.4 . . ? C14 C15B H15D 110.4 . . ? H15C C15B H15D 108.6 . . ? C15B C16 C12 106.4(6) . . ? C15A C16 C12 105.6(4) . . ? C15A C16 H16A 110.6 . . ? C12 C16 H16A 110.6 . . ? C15A C16 H16B 110.6 . . ? C12 C16 H16B 110.6 . . ? H16A C16 H16B 108.7 . . ? C15B C16 H16C 111.3 . . ? C15A C16 H16C 139.5 . . ? C12 C16 H16C 110.3 . . ? C15B C16 H16D 109.9 . . ? C12 C16 H16D 110.3 . . ? H16C C16 H16D 108.6 . . ? C12 N1 H1A 109.5 . . ? C12 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C12 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 C5 -179.15(19) . . . . ? C4 C1 C2 C5 57.7(2) . . . . ? C3 C1 C2 C5 -60.2(2) . . . . ? C2 C1 C3 C7 59.5(2) . . . . ? C11 C1 C3 C7 -177.5(2) . . . . ? C4 C1 C3 C7 -59.2(3) . . . . ? C2 C1 C4 C9 -58.2(2) . . . . ? C11 C1 C4 C9 176.33(18) . . . . ? C3 C1 C4 C9 59.7(2) . . . . ? C1 C2 C5 C10 -58.8(2) . . . . ? C1 C2 C5 C6 60.9(2) . . . . ? C10 C5 C6 C7 60.1(2) . . . . ? C2 C5 C6 C7 -60.1(3) . . . . ? C5 C6 C7 C8 -59.7(2) . . . . ? C5 C6 C7 C3 60.0(2) . . . . ? C1 C3 C7 C6 -59.8(3) . . . . ? C1 C3 C7 C8 60.1(3) . . . . ? C6 C7 C8 C9 59.3(3) . . . . ? C3 C7 C8 C9 -60.5(3) . . . . ? C1 C4 C9 C10 59.2(2) . . . . ? C1 C4 C9 C8 -60.7(3) . . . . ? C7 C8 C9 C10 -59.5(2) . . . . ? C7 C8 C9 C4 60.5(3) . . . . ? C6 C5 C10 C9 -60.1(3) . . . . ? C2 C5 C10 C9 59.3(2) . . . . ? C4 C9 C10 C5 -59.5(2) . . . . ? C8 C9 C10 C5 60.0(2) . . . . ? C2 C1 C11 O2 -166.9(2) . . . . ? C4 C1 C11 O2 -43.8(3) . . . . ? C3 C1 C11 O2 73.5(3) . . . . ? C2 C1 C11 O1 16.7(3) . . . . ? C4 C1 C11 O1 139.8(2) . . . . ? C3 C1 C11 O1 -102.9(3) . . . . ? N1 C12 C13 C14 115.3(3) . . . . ? C16 C12 C13 C14 -6.6(4) . . . . ? C12 C13 C14 C15A 28.8(5) . . . . ? C12 C13 C14 C15B -11.9(7) . . . . ? C15B C14 C15A C16 59.0(6) . . . . ? C13 C14 C15A C16 -39.4(6) . . . . ? C15A C14 C15B C16 -66.9(7) . . . . ? C13 C14 C15B C16 27.5(10) . . . . ? C14 C15B C16 C15A 63.3(7) . . . . ? C14 C15B C16 C12 -31.4(10) . . . . ? C14 C15A C16 C15B -62.6(7) . . . . ? C14 C15A C16 C12 34.3(6) . . . . ? N1 C12 C16 C15B -98.5(6) . . . . ? C13 C12 C16 C15B 23.6(7) . . . . ? N1 C12 C16 C15A -138.7(4) . . . . ? C13 C12 C16 C15A -16.6(5) . . . . ? 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 0.91 1.89 2.773(2) 162 . N1 H1B O1 0.91 1.86 2.767(3) 173 3_556 N1 H1C O2 0.91 1.8 2.706(3) 177 3_456 ###END data_7 _database_code_depnum_ccdc_archive 'CCDC 797979' #TrackingRef '- Lemmerer.cif' _audit_creation_date 2010-10-13T10:40:56-00:00 _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 ; (cyclohexylammonium).(adamantane carboxylate) ; _chemical_formula_moiety 'C11 H15 O2, C6 H14 N' _chemical_formula_sum 'C17 H29 N O2' _chemical_formula_weight 279.41 #----------------------------------------------------------------------------# # 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 6.5544(3) _cell_length_b 12.7452(4) _cell_length_c 19.7109(9) _cell_angle_alpha 76.690(3) _cell_angle_beta 89.615(3) _cell_angle_gamma 89.590(2) _cell_volume 1602.30(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2469 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 26.2 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.239 1 0 0 0.2534 0 0 1 0.055 0 0 -1 0.094 0 -1 0 0.027 0 1 0 0.048 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_T_max 0.9932 #----------------------------------------------------------------------------# # 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 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.1169 _diffrn_reflns_av_unetI/netI 0.1067 _diffrn_reflns_number 8569 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.06 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _reflns_number_total 5824 _reflns_number_gt 4056 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1206P)^2^+1.5543P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5824 _refine_ls_number_parameters 527 _refine_ls_number_restraints 681 _refine_ls_R_factor_all 0.1166 _refine_ls_R_factor_gt 0.0915 _refine_ls_wR_factor_ref 0.2709 _refine_ls_wR_factor_gt 0.2571 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.319 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.077 #----------------------------------------------------------------------------# # 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 C1A C 0.3004(5) 0.6060(3) 0.85440(16) 0.0229(7) Uani 1 1 d . . . C2A C 0.4601(6) 0.6162(3) 0.9096(2) 0.0308(9) Uani 0.848(4) 1 d PDU A 1 H2A1 H 0.479 0.5454 0.9425 0.037 Uiso 0.848(4) 1 calc PR A 1 H2A2 H 0.5927 0.6379 0.8864 0.037 Uiso 0.848(4) 1 calc PR A 1 C3A C 0.0970(6) 0.5733(3) 0.8921(2) 0.0302(9) Uani 0.848(4) 1 d PDU A 1 H3A1 H 0.1122 0.5019 0.9246 0.036 Uiso 0.848(4) 1 calc PR A 1 H3A2 H -0.0088 0.5675 0.8576 0.036 Uiso 0.848(4) 1 calc PR A 1 C4A C 0.2751(7) 0.7171(3) 0.8048(2) 0.0328(10) Uani 0.848(4) 1 d PDU A 1 H4A1 H 0.1726 0.713 0.7689 0.039 Uiso 0.848(4) 1 calc PR A 1 H4A2 H 0.4064 0.7397 0.781 0.039 Uiso 0.848(4) 1 calc PR A 1 C5A C 0.3921(9) 0.6997(5) 0.9498(3) 0.0351(11) Uani 0.848(4) 1 d PDU A 1 H5A H 0.4978 0.7055 0.985 0.042 Uiso 0.848(4) 1 calc PR A 1 C6A C 0.1897(7) 0.6652(4) 0.9867(2) 0.0341(10) Uani 0.848(4) 1 d PDU A 1 H6A1 H 0.2065 0.5945 1.0199 0.041 Uiso 0.848(4) 1 calc PR A 1 H6A2 H 0.1458 0.7187 1.0132 0.041 Uiso 0.848(4) 1 calc PR A 1 C7A C 0.0296(8) 0.6569(5) 0.9329(2) 0.0328(11) Uani 0.848(4) 1 d PDU A 1 H7A H -0.1035 0.6346 0.9569 0.039 Uiso 0.848(4) 1 calc PR A 1 C8A C 0.0043(8) 0.7661(4) 0.8818(3) 0.0394(11) Uani 0.848(4) 1 d PDU A 1 H8A1 H -0.1004 0.7608 0.8468 0.047 Uiso 0.848(4) 1 calc PR A 1 H8A2 H -0.042 0.8206 0.9072 0.047 Uiso 0.848(4) 1 calc PR A 1 C9A C 0.2063(8) 0.8006(4) 0.8454(3) 0.0383(10) Uani 0.848(4) 1 d PDU A 1 H9A H 0.1892 0.8725 0.8124 0.046 Uiso 0.848(4) 1 calc PR A 1 C10A C 0.3639(8) 0.8088(4) 0.8994(3) 0.0421(11) Uani 0.848(4) 1 d PDU A 1 H10A H 0.3195 0.8629 0.9253 0.05 Uiso 0.848(4) 1 calc PR A 1 H10B H 0.4954 0.8326 0.8761 0.05 Uiso 0.848(4) 1 calc PR A 1 C2B C 0.287(3) 0.5366(15) 0.9276(10) 0.031(4) Uani 0.152(4) 1 d PDU A 2 H2B1 H 0.4195 0.5009 0.9415 0.037 Uiso 0.152(4) 1 calc PR A 2 H2B2 H 0.1819 0.4803 0.93 0.037 Uiso 0.152(4) 1 calc PR A 2 C3B C 0.100(3) 0.6552(16) 0.8311(10) 0.033(4) Uani 0.152(4) 1 d PDU A 2 H3B1 H -0.0023 0.5982 0.8323 0.04 Uiso 0.152(4) 1 calc PR A 2 H3B2 H 0.111 0.6988 0.7827 0.04 Uiso 0.152(4) 1 calc PR A 2 C4B C 0.461(3) 0.6925(17) 0.8485(11) 0.036(4) Uani 0.152(4) 1 d PDU A 2 H4B1 H 0.4671 0.7363 0.8001 0.043 Uiso 0.152(4) 1 calc PR A 2 H4B2 H 0.5961 0.659 0.8608 0.043 Uiso 0.152(4) 1 calc PR A 2 C5B C 0.229(3) 0.6100(17) 0.9763(11) 0.036(3) Uani 0.152(4) 1 d PDU A 2 H5B H 0.2216 0.5661 1.0253 0.043 Uiso 0.152(4) 1 calc PR A 2 C6B C 0.024(4) 0.662(2) 0.9557(12) 0.036(4) Uani 0.152(4) 1 d PDU A 2 H6B1 H -0.0139 0.7088 0.9872 0.043 Uiso 0.152(4) 1 calc PR A 2 H6B2 H -0.0811 0.605 0.9599 0.043 Uiso 0.152(4) 1 calc PR A 2 C7B C 0.034(4) 0.7278(17) 0.8806(12) 0.037(3) Uani 0.152(4) 1 d PDU A 2 H7B H -0.102 0.7618 0.8662 0.044 Uiso 0.152(4) 1 calc PR A 2 C8B C 0.194(3) 0.8146(16) 0.8791(14) 0.041(3) Uani 0.152(4) 1 d PDU A 2 H8B1 H 0.2004 0.8622 0.8317 0.049 Uiso 0.152(4) 1 calc PR A 2 H8B2 H 0.1536 0.8592 0.912 0.049 Uiso 0.152(4) 1 calc PR A 2 C9B C 0.404(4) 0.7652(19) 0.8988(12) 0.041(3) Uani 0.152(4) 1 d PDU A 2 H9B H 0.5079 0.8229 0.8963 0.049 Uiso 0.152(4) 1 calc PR A 2 C10B C 0.388(4) 0.697(2) 0.9716(12) 0.040(4) Uani 0.152(4) 1 d PDU A 2 H10C H 0.352 0.7428 1.0041 0.048 Uiso 0.152(4) 1 calc PR A 2 H10D H 0.5226 0.6628 0.9858 0.048 Uiso 0.152(4) 1 calc PR A 2 C11A C 0.3714(5) 0.5254(3) 0.81168(16) 0.0253(7) Uani 1 1 d U A . O1 O 0.5510(4) 0.4953(2) 0.81654(13) 0.0401(7) Uani 1 1 d U . . O2 O 0.2415(4) 0.4930(2) 0.77464(13) 0.0353(6) Uani 1 1 d U . . C1C C 0.8108(5) 0.1261(3) 0.65552(16) 0.0225(7) Uani 1 1 d U . . C2C C 0.9694(6) 0.0812(3) 0.6124(2) 0.0280(8) Uani 0.899(4) 1 d PDU B 1 H2C1 H 1.1019 0.0723 0.637 0.034 Uiso 0.899(4) 1 calc PR B 1 H2C2 H 0.9886 0.1325 0.5668 0.034 Uiso 0.899(4) 1 calc PR B 1 C3C C 0.6059(6) 0.1393(3) 0.61651(19) 0.0262(8) Uani 0.899(4) 1 d PDU B 1 H3C1 H 0.5015 0.168 0.644 0.031 Uiso 0.899(4) 1 calc PR B 1 H3C2 H 0.6215 0.1912 0.571 0.031 Uiso 0.899(4) 1 calc PR B 1 C4C C 0.7827(6) 0.0463(3) 0.72581(18) 0.0279(9) Uani 0.899(4) 1 d PDU B 1 H4C1 H 0.6804 0.075 0.7541 0.033 Uiso 0.899(4) 1 calc PR B 1 H4C2 H 0.9134 0.0369 0.7514 0.033 Uiso 0.899(4) 1 calc PR B 1 C5C C 0.8998(7) -0.0277(4) 0.6009(2) 0.0355(10) Uani 0.899(4) 1 d PDU B 1 H5C H 1.0049 -0.0566 0.5728 0.043 Uiso 0.899(4) 1 calc PR B 1 C6C C 0.6981(7) -0.0142(4) 0.5625(2) 0.0368(10) Uani 0.899(4) 1 d PDU B 1 H6C1 H 0.6535 -0.0846 0.5549 0.044 Uiso 0.899(4) 1 calc PR B 1 H6C2 H 0.7149 0.0361 0.5164 0.044 Uiso 0.899(4) 1 calc PR B 1 C7C C 0.5372(6) 0.0298(4) 0.6051(2) 0.0309(9) Uani 0.899(4) 1 d PDU B 1 H7C H 0.4047 0.0389 0.5795 0.037 Uiso 0.899(4) 1 calc PR B 1 C8C C 0.5092(7) -0.0483(4) 0.6756(2) 0.0376(10) Uani 0.899(4) 1 d PDU B 1 H8C1 H 0.4616 -0.1187 0.6688 0.045 Uiso 0.899(4) 1 calc PR B 1 H8C2 H 0.4049 -0.0198 0.7032 0.045 Uiso 0.899(4) 1 calc PR B 1 C9C C 0.7113(7) -0.0632(4) 0.7146(2) 0.0366(10) Uani 0.899(4) 1 d PDU B 1 H9C H 0.693 -0.1149 0.7607 0.044 Uiso 0.899(4) 1 calc PR B 1 C10C C 0.8721(8) -0.1070(4) 0.6719(3) 0.0433(11) Uani 0.899(4) 1 d PDU B 1 H10E H 0.8288 -0.178 0.6649 0.052 Uiso 0.899(4) 1 calc PR B 1 H10F H 1.0033 -0.1168 0.6972 0.052 Uiso 0.899(4) 1 calc PR B 1 C2D C 0.983(4) 0.039(2) 0.6857(15) 0.029(3) Uani 0.101(4) 1 d PDU B 2 H2D1 H 1.1153 0.0641 0.6637 0.035 Uiso 0.101(4) 1 calc PR B 2 H2D2 H 0.9956 0.0328 0.7364 0.035 Uiso 0.101(4) 1 calc PR B 2 C3D C 0.784(4) 0.127(2) 0.5792(13) 0.027(3) Uani 0.101(4) 1 d PDU B 2 H3D1 H 0.9108 0.1521 0.5535 0.032 Uiso 0.101(4) 1 calc PR B 2 H3D2 H 0.6727 0.1775 0.5597 0.032 Uiso 0.101(4) 1 calc PR B 2 C4D C 0.611(4) 0.079(2) 0.6972(13) 0.023(3) Uani 0.101(4) 1 d PDU B 2 H4D1 H 0.6302 0.0745 0.7476 0.028 Uiso 0.101(4) 1 calc PR B 2 H4D2 H 0.4939 0.1278 0.6811 0.028 Uiso 0.101(4) 1 calc PR B 2 C5D C 0.937(4) -0.072(2) 0.6729(15) 0.036(3) Uani 0.101(4) 1 d PDU B 2 H5D H 1.0521 -0.1234 0.6905 0.044 Uiso 0.101(4) 1 calc PR B 2 C6D C 0.907(5) -0.064(3) 0.5957(15) 0.038(4) Uani 0.101(4) 1 d PDU B 2 H6D1 H 0.8756 -0.1359 0.5876 0.046 Uiso 0.101(4) 1 calc PR B 2 H6D2 H 1.0337 -0.0378 0.57 0.046 Uiso 0.101(4) 1 calc PR B 2 C7D C 0.732(5) 0.014(2) 0.5688(16) 0.034(3) Uani 0.101(4) 1 d PDU B 2 H7D H 0.713 0.0181 0.5179 0.041 Uiso 0.101(4) 1 calc PR B 2 C8D C 0.534(4) -0.025(3) 0.6074(14) 0.033(4) Uani 0.101(4) 1 d PDU B 2 H8D1 H 0.4956 -0.0955 0.5992 0.04 Uiso 0.101(4) 1 calc PR B 2 H8D2 H 0.4227 0.0275 0.5903 0.04 Uiso 0.101(4) 1 calc PR B 2 C9D C 0.567(5) -0.034(2) 0.6852(15) 0.029(3) Uani 0.101(4) 1 d PDU B 2 H9D H 0.4383 -0.0611 0.7106 0.035 Uiso 0.101(4) 1 calc PR B 2 C10D C 0.737(5) -0.114(2) 0.7113(16) 0.037(4) Uani 0.101(4) 1 d PDU B 2 H10G H 0.7029 -0.1852 0.7025 0.044 Uiso 0.101(4) 1 calc PR B 2 H10H H 0.7548 -0.1227 0.7621 0.044 Uiso 0.101(4) 1 calc PR B 2 C11C C 0.8780(5) 0.2333(3) 0.66873(16) 0.0233(7) Uani 1 1 d . B . O3 O 1.0565(4) 0.2642(2) 0.65524(12) 0.0321(6) Uani 1 1 d . . . O4 O 0.7480(4) 0.28621(19) 0.69608(13) 0.0326(6) Uani 1 1 d . . . C12A C 0.3157(5) 0.2102(3) 0.80699(17) 0.0260(7) Uani 1 1 d . . . H12A H 0.3211 0.1405 0.7919 0.031 Uiso 1 1 calc R . . C13A C 0.4846(6) 0.2084(3) 0.85962(18) 0.0313(8) Uani 1 1 d . . . H13A H 0.4852 0.2776 0.8743 0.038 Uiso 1 1 calc R . . H13B H 0.6183 0.1999 0.8378 0.038 Uiso 1 1 calc R . . C14A C 0.4532(6) 0.1161(3) 0.9229(2) 0.0374(9) Uani 1 1 d . . . H14A H 0.4697 0.0468 0.9089 0.045 Uiso 1 1 calc R . . H14B H 0.5588 0.1193 0.958 0.045 Uiso 1 1 calc R . . C15A C 0.2434(6) 0.1205(3) 0.95529(19) 0.0385(9) Uani 1 1 d . . . H15A H 0.2339 0.1847 0.9755 0.046 Uiso 1 1 calc R . . H15B H 0.224 0.0557 0.9935 0.046 Uiso 1 1 calc R . . C16A C 0.0753(6) 0.1258(3) 0.90146(19) 0.0370(9) Uani 1 1 d . . . H16A H 0.0735 0.0575 0.8857 0.044 Uiso 1 1 calc R . . H16B H -0.0585 0.1343 0.9232 0.044 Uiso 1 1 calc R . . C17A C 0.1080(5) 0.2196(3) 0.83892(18) 0.0300(8) Uani 1 1 d . . . H17A H 0.0009 0.2192 0.8038 0.036 Uiso 1 1 calc R . . H17B H 0.0979 0.2885 0.8538 0.036 Uiso 1 1 calc R . . N1 N 0.3480(4) 0.2996(2) 0.74397(14) 0.0258(6) Uani 1 1 d . . . H1A H 0.3397 0.3641 0.7563 0.039 Uiso 1 1 calc R . . H1B H 0.2505 0.2967 0.7118 0.039 Uiso 1 1 calc R . . H1C H 0.4735 0.2925 0.7255 0.039 Uiso 1 1 calc R . . C12B C 0.8159(5) 0.5670(3) 0.65731(18) 0.0303(8) Uani 1 1 d . . . H12B H 0.8216 0.6389 0.6693 0.036 Uiso 1 1 calc R . . C13B C 0.9849(6) 0.5612(3) 0.6055(2) 0.0406(10) Uani 1 1 d . . . H13C H 0.9876 0.4887 0.5954 0.049 Uiso 1 1 calc R . . H13D H 1.1181 0.5733 0.6258 0.049 Uiso 1 1 calc R . . C14B C 0.9506(7) 0.6466(4) 0.5380(2) 0.0561(13) Uani 1 1 d . . . H14C H 0.9624 0.7193 0.5475 0.067 Uiso 1 1 calc R . . H14D H 1.0574 0.6393 0.5036 0.067 Uiso 1 1 calc R . . C15B C 0.7440(7) 0.6352(4) 0.5080(2) 0.0501(11) Uani 1 1 d . . . H15C H 0.7376 0.5656 0.4939 0.06 Uiso 1 1 calc R . . H15D H 0.7236 0.6937 0.4658 0.06 Uiso 1 1 calc R . . C16B C 0.5760(7) 0.6398(4) 0.5596(2) 0.0483(11) Uani 1 1 d . . . H16C H 0.4432 0.6269 0.5393 0.058 Uiso 1 1 calc R . . H16D H 0.5715 0.7125 0.5695 0.058 Uiso 1 1 calc R . . C17B C 0.6100(6) 0.5547(3) 0.62798(19) 0.0375(9) Uani 1 1 d . . . H17C H 0.5035 0.5627 0.6623 0.045 Uiso 1 1 calc R . . H17D H 0.5981 0.4817 0.6191 0.045 Uiso 1 1 calc R . . N2 N 0.8484(4) 0.4814(2) 0.72263(14) 0.0263(6) Uani 1 1 d . . . H2A H 0.836 0.4152 0.713 0.039 Uiso 1 1 calc R . . H2B H 0.7535 0.489 0.7551 0.039 Uiso 1 1 calc R . . H2C H 0.9755 0.488 0.7394 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0280(18) 0.0243(16) 0.0162(15) -0.0042(13) 0.0080(13) -0.0056(13) C2A 0.033(2) 0.039(2) 0.020(2) -0.0074(17) 0.0055(16) -0.0035(18) C3A 0.033(2) 0.032(2) 0.027(2) -0.0083(17) 0.0089(17) -0.0065(17) C4A 0.046(3) 0.031(2) 0.019(2) -0.0003(16) 0.0086(17) -0.0014(19) C5A 0.037(2) 0.047(2) 0.026(2) -0.018(2) 0.0010(19) -0.007(2) C6A 0.043(2) 0.039(2) 0.021(2) -0.0103(17) 0.0115(16) -0.003(2) C7A 0.032(2) 0.044(2) 0.023(2) -0.010(2) 0.0135(18) -0.0046(18) C8A 0.049(2) 0.040(3) 0.032(2) -0.014(2) 0.0051(18) 0.010(2) C9A 0.061(3) 0.023(2) 0.027(2) 0.0004(17) 0.0113(19) 0.0002(19) C10A 0.056(3) 0.036(2) 0.038(2) -0.015(2) 0.018(2) -0.013(2) C2B 0.037(8) 0.038(8) 0.020(8) -0.012(6) 0.010(7) 0.003(7) C3B 0.048(9) 0.027(8) 0.025(7) -0.007(6) 0.014(7) 0.004(7) C4B 0.051(9) 0.032(8) 0.023(7) -0.002(7) 0.003(7) 0.002(7) C5B 0.046(7) 0.041(7) 0.024(6) -0.014(5) 0.010(6) 0.001(5) C6B 0.045(6) 0.036(8) 0.030(6) -0.015(6) 0.017(7) 0.003(6) C7B 0.052(6) 0.030(7) 0.032(6) -0.015(5) 0.006(6) 0.002(6) C8B 0.055(7) 0.031(6) 0.036(8) -0.008(6) 0.005(6) -0.001(5) C9B 0.052(6) 0.036(7) 0.036(7) -0.010(5) 0.008(7) -0.002(6) C10B 0.052(7) 0.042(7) 0.028(6) -0.015(6) 0.000(7) -0.001(6) C11A 0.0297(17) 0.0294(17) 0.0160(15) -0.0036(13) 0.0066(12) -0.0015(14) O1 0.0340(14) 0.0617(18) 0.0297(14) -0.0212(13) 0.0068(11) 0.0071(13) O2 0.0375(14) 0.0390(14) 0.0341(14) -0.0179(12) 0.0017(11) -0.0021(11) C1C 0.0268(16) 0.0254(15) 0.0156(15) -0.0055(12) 0.0084(12) -0.0047(13) C2C 0.0295(19) 0.0334(19) 0.0228(18) -0.0102(15) 0.0091(14) -0.0004(15) C3C 0.0275(18) 0.0325(18) 0.0185(17) -0.0060(14) 0.0045(14) -0.0010(15) C4C 0.038(2) 0.0307(19) 0.0130(16) -0.0006(14) 0.0034(14) -0.0064(16) C5C 0.040(2) 0.036(2) 0.035(2) -0.0167(18) 0.0112(17) 0.0007(19) C6C 0.048(2) 0.043(3) 0.0236(19) -0.0169(18) 0.0072(16) -0.0074(19) C7C 0.0310(19) 0.042(2) 0.0226(18) -0.0121(17) 0.0026(15) -0.0087(17) C8C 0.047(2) 0.039(2) 0.029(2) -0.0108(18) 0.0144(18) -0.0218(19) C9C 0.057(3) 0.027(2) 0.0227(19) 0.0004(17) 0.0063(16) -0.0078(19) C10C 0.060(3) 0.028(2) 0.042(2) -0.0077(18) -0.002(2) 0.002(2) C2D 0.036(6) 0.031(7) 0.021(8) -0.006(6) 0.003(7) 0.000(5) C3D 0.030(8) 0.036(6) 0.016(4) -0.010(6) 0.007(5) -0.006(6) C4D 0.032(6) 0.023(6) 0.016(7) -0.009(6) 0.009(6) -0.012(6) C5D 0.049(7) 0.031(5) 0.031(7) -0.012(7) 0.008(6) 0.001(6) C6D 0.051(7) 0.035(7) 0.032(6) -0.015(7) 0.011(7) -0.005(7) C7D 0.046(7) 0.038(7) 0.024(6) -0.015(5) 0.008(5) -0.008(6) C8D 0.047(6) 0.033(8) 0.025(6) -0.018(6) 0.007(6) -0.012(6) C9D 0.045(6) 0.024(6) 0.023(6) -0.014(7) 0.008(6) -0.010(5) C10D 0.055(8) 0.025(7) 0.031(7) -0.007(9) 0.009(6) -0.004(6) C11C 0.0296(18) 0.0261(16) 0.0135(15) -0.0030(13) 0.0034(12) -0.0043(14) O3 0.0333(14) 0.0434(14) 0.0220(12) -0.0122(11) 0.0087(10) -0.0129(11) O4 0.0377(14) 0.0281(13) 0.0358(14) -0.0155(11) 0.0110(11) -0.0002(11) C12A 0.0327(19) 0.0254(17) 0.0203(16) -0.0064(14) 0.0076(13) -0.0021(14) C13A 0.034(2) 0.0369(19) 0.0225(17) -0.0058(15) 0.0063(14) -0.0018(16) C14A 0.041(2) 0.041(2) 0.0262(19) 0.0014(16) 0.0013(16) 0.0037(17) C15A 0.045(2) 0.044(2) 0.0225(18) 0.0002(16) 0.0056(16) -0.0048(18) C16A 0.039(2) 0.043(2) 0.0257(19) -0.0019(16) 0.0106(15) -0.0069(17) C17A 0.0290(19) 0.038(2) 0.0208(17) -0.0026(15) 0.0043(13) -0.0060(15) N1 0.0316(16) 0.0302(15) 0.0170(14) -0.0083(12) 0.0055(11) -0.0056(12) C12B 0.038(2) 0.0226(16) 0.0273(18) 0.0000(14) 0.0091(15) -0.0026(15) C13B 0.033(2) 0.048(2) 0.033(2) 0.0051(18) 0.0110(16) -0.0047(18) C14B 0.050(3) 0.069(3) 0.036(2) 0.015(2) 0.0161(19) -0.007(2) C15B 0.051(3) 0.063(3) 0.026(2) 0.0099(19) 0.0077(18) 0.004(2) C16B 0.045(2) 0.057(3) 0.034(2) 0.008(2) 0.0012(18) 0.008(2) C17B 0.036(2) 0.046(2) 0.0262(19) 0.0003(17) 0.0098(15) -0.0031(17) N2 0.0320(16) 0.0267(14) 0.0207(14) -0.0066(12) 0.0051(11) -0.0028(12) #----------------------------------------------------------------------------# # 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 C1A C3B 1.48(2) . ? C1A C2B 1.51(2) . ? C1A C4B 1.51(2) . ? C1A C4A 1.532(5) . ? C1A C3A 1.535(5) . ? C1A C11A 1.539(4) . ? C1A C2A 1.542(5) . ? C2A C5A 1.528(7) . ? C2A H2A1 0.99 . ? C2A H2A2 0.99 . ? C3A C7A 1.536(6) . ? C3A H3A1 0.99 . ? C3A H3A2 0.99 . ? C4A C9A 1.534(6) . ? C4A H4A1 0.99 . ? C4A H4A2 0.99 . ? C5A C10A 1.522(8) . ? C5A C6A 1.526(7) . ? C5A H5A 1 . ? C6A C7A 1.518(7) . ? C6A H6A1 0.99 . ? C6A H6A2 0.99 . ? C7A C8A 1.528(7) . ? C7A H7A 1 . ? C8A C9A 1.520(7) . ? C8A H8A1 0.99 . ? C8A H8A2 0.99 . ? C9A C10A 1.509(7) . ? C9A H9A 1 . ? C10A H10A 0.99 . ? C10A H10B 0.99 . ? C2B C5B 1.529(17) . ? C2B H2B1 0.99 . ? C2B H2B2 0.99 . ? C3B C7B 1.549(18) . ? C3B H3B1 0.99 . ? C3B H3B2 0.99 . ? C4B C9B 1.546(18) . ? C4B H4B1 0.99 . ? C4B H4B2 0.99 . ? C5B C6B 1.508(18) . ? C5B C10B 1.513(19) . ? C5B H5B 1 . ? C6B C7B 1.528(18) . ? C6B H6B1 0.99 . ? C6B H6B2 0.99 . ? C7B C8B 1.525(19) . ? C7B H7B 1 . ? C8B C9B 1.523(19) . ? C8B H8B1 0.99 . ? C8B H8B2 0.99 . ? C9B C10B 1.501(18) . ? C9B H9B 1 . ? C10B H10C 0.99 . ? C10B H10D 0.99 . ? C11A O1 1.232(4) . ? C11A O2 1.257(4) . ? C1C C3D 1.51(2) . ? C1C C11C 1.517(5) . ? C1C C2C 1.528(5) . ? C1C C4C 1.529(4) . ? C1C C3C 1.540(5) . ? C1C C4D 1.59(3) . ? C1C C2D 1.60(3) . ? C2C C5C 1.531(6) . ? C2C H2C1 0.99 . ? C2C H2C2 0.99 . ? C3C C7C 1.535(6) . ? C3C H3C1 0.99 . ? C3C H3C2 0.99 . ? C4C C9C 1.540(6) . ? C4C H4C1 0.99 . ? C4C H4C2 0.99 . ? C5C C6C 1.516(6) . ? C5C C10C 1.536(6) . ? C5C H5C 1 . ? C6C C7C 1.526(6) . ? C6C H6C1 0.99 . ? C6C H6C2 0.99 . ? C7C C8C 1.522(6) . ? C7C H7C 1 . ? C8C C9C 1.524(7) . ? C8C H8C1 0.99 . ? C8C H8C2 0.99 . ? C9C C10C 1.525(7) . ? C9C H9C 1 . ? C10C H10E 0.99 . ? C10C H10F 0.99 . ? C2D C5D 1.529(19) . ? C2D H2D1 0.99 . ? C2D H2D2 0.99 . ? C3D C7D 1.538(19) . ? C3D H3D1 0.99 . ? C3D H3D2 0.99 . ? C4D C9D 1.541(19) . ? C4D H4D1 0.99 . ? C4D H4D2 0.99 . ? C5D C6D 1.516(19) . ? C5D C10D 1.543(19) . ? C5D H5D 1 . ? C6D C7D 1.525(19) . ? C6D H6D1 0.99 . ? C6D H6D2 0.99 . ? C7D C8D 1.525(19) . ? C7D H7D 1 . ? C8D C9D 1.526(19) . ? C8D H8D1 0.99 . ? C8D H8D2 0.99 . ? C9D C10D 1.521(19) . ? C9D H9D 1 . ? C10D H10G 0.99 . ? C10D H10H 0.99 . ? C11C O3 1.244(4) . ? C11C O4 1.275(4) . ? C12A N1 1.495(4) . ? C12A C17A 1.511(5) . ? C12A C13A 1.519(5) . ? C12A H12A 1 . ? C13A C14A 1.519(5) . ? C13A H13A 0.99 . ? C13A H13B 0.99 . ? C14A C15A 1.519(5) . ? C14A H14A 0.99 . ? C14A H14B 0.99 . ? C15A C16A 1.525(5) . ? C15A H15A 0.99 . ? C15A H15B 0.99 . ? C16A C17A 1.521(5) . ? C16A H16A 0.99 . ? C16A H16B 0.99 . ? C17A H17A 0.99 . ? C17A H17B 0.99 . ? N1 H1A 0.91 . ? N1 H1B 0.91 . ? N1 H1C 0.91 . ? C12B C17B 1.495(5) . ? C12B N2 1.499(4) . ? C12B C13B 1.514(5) . ? C12B H12B 1 . ? C13B C14B 1.530(5) . ? C13B H13C 0.99 . ? C13B H13D 0.99 . ? C14B C15B 1.503(6) . ? C14B H14C 0.99 . ? C14B H14D 0.99 . ? C15B C16B 1.504(6) . ? C15B H15C 0.99 . ? C15B H15D 0.99 . ? C16B C17B 1.540(5) . ? C16B H16C 0.99 . ? C16B H16D 0.99 . ? C17B H17C 0.99 . ? C17B H17D 0.99 . ? N2 H2A 0.91 . ? N2 H2B 0.91 . ? N2 H2C 0.91 . ? 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 C3B C1A C2B 111.0(11) . . ? C3B C1A C4B 110.2(11) . . ? C2B C1A C4B 111.7(12) . . ? C3B C1A C4A 56.3(9) . . ? C2B C1A C4A 148.7(7) . . ? C4B C1A C4A 58.3(9) . . ? C3B C1A C3A 55.3(8) . . ? C2B C1A C3A 56.9(9) . . ? C4B C1A C3A 139.0(8) . . ? C4A C1A C3A 108.9(3) . . ? C3B C1A C11A 112.3(7) . . ? C2B C1A C11A 102.8(7) . . ? C4B C1A C11A 108.6(8) . . ? C4A C1A C11A 108.5(3) . . ? C3A C1A C11A 112.3(3) . . ? C3B C1A C2A 136.6(7) . . ? C2B C1A C2A 59.4(9) . . ? C4B C1A C2A 53.0(8) . . ? C4A C1A C2A 107.9(3) . . ? C3A C1A C2A 108.0(3) . . ? C11A C1A C2A 111.1(3) . . ? C5A C2A C1A 110.7(3) . . ? C5A C2A H2A1 109.5 . . ? C1A C2A H2A1 109.5 . . ? C5A C2A H2A2 109.5 . . ? C1A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 108.1 . . ? C1A C3A C7A 110.6(3) . . ? C1A C3A H3A1 109.5 . . ? C7A C3A H3A1 109.5 . . ? C1A C3A H3A2 109.5 . . ? C7A C3A H3A2 109.5 . . ? H3A1 C3A H3A2 108.1 . . ? C1A C4A C9A 110.4(3) . . ? C1A C4A H4A1 109.6 . . ? C9A C4A H4A1 109.6 . . ? C1A C4A H4A2 109.6 . . ? C9A C4A H4A2 109.6 . . ? H4A1 C4A H4A2 108.1 . . ? C10A C5A C6A 109.1(5) . . ? C10A C5A C2A 109.6(4) . . ? C6A C5A C2A 109.5(4) . . ? C10A C5A H5A 109.5 . . ? C6A C5A H5A 109.5 . . ? C2A C5A H5A 109.5 . . ? C7A C6A C5A 109.3(4) . . ? C7A C6A H6A1 109.8 . . ? C5A C6A H6A1 109.8 . . ? C7A C6A H6A2 109.8 . . ? C5A C6A H6A2 109.8 . . ? H6A1 C6A H6A2 108.3 . . ? C6A C7A C8A 109.6(5) . . ? C6A C7A C3A 109.8(4) . . ? C8A C7A C3A 108.7(4) . . ? C6A C7A H7A 109.6 . . ? C8A C7A H7A 109.6 . . ? C3A C7A H7A 109.6 . . ? C9A C8A C7A 109.8(4) . . ? C9A C8A H8A1 109.7 . . ? C7A C8A H8A1 109.7 . . ? C9A C8A H8A2 109.7 . . ? C7A C8A H8A2 109.7 . . ? H8A1 C8A H8A2 108.2 . . ? C10A C9A C8A 109.1(4) . . ? C10A C9A C4A 109.8(4) . . ? C8A C9A C4A 109.5(4) . . ? C10A C9A H9A 109.5 . . ? C8A C9A H9A 109.5 . . ? C4A C9A H9A 109.5 . . ? C9A C10A C5A 110.0(4) . . ? C9A C10A H10A 109.7 . . ? C5A C10A H10A 109.7 . . ? C9A C10A H10B 109.7 . . ? C5A C10A H10B 109.7 . . ? H10A C10A H10B 108.2 . . ? C1A C2B C5B 107.7(14) . . ? C1A C2B H2B1 110.2 . . ? C5B C2B H2B1 110.2 . . ? C1A C2B H2B2 110.2 . . ? C5B C2B H2B2 110.2 . . ? H2B1 C2B H2B2 108.5 . . ? C1A C3B C7B 108.6(15) . . ? C1A C3B H3B1 110 . . ? C7B C3B H3B1 110 . . ? C1A C3B H3B2 110 . . ? C7B C3B H3B2 110 . . ? H3B1 C3B H3B2 108.4 . . ? C1A C4B C9B 108.8(15) . . ? C1A C4B H4B1 109.9 . . ? C9B C4B H4B1 109.9 . . ? C1A C4B H4B2 109.9 . . ? C9B C4B H4B2 109.9 . . ? H4B1 C4B H4B2 108.3 . . ? C6B C5B C10B 109.6(19) . . ? C6B C5B C2B 109.5(16) . . ? C10B C5B C2B 109.9(17) . . ? C6B C5B H5B 109.3 . . ? C10B C5B H5B 109.3 . . ? C2B C5B H5B 109.3 . . ? C5B C6B C7B 109.6(16) . . ? C5B C6B H6B1 109.7 . . ? C7B C6B H6B1 109.7 . . ? C5B C6B H6B2 109.7 . . ? C7B C6B H6B2 109.7 . . ? H6B1 C6B H6B2 108.2 . . ? C8B C7B C6B 106.4(19) . . ? C8B C7B C3B 109.5(18) . . ? C6B C7B C3B 110.1(17) . . ? C8B C7B H7B 110.3 . . ? C6B C7B H7B 110.3 . . ? C3B C7B H7B 110.3 . . ? C9B C8B C7B 111.4(16) . . ? C9B C8B H8B1 109.3 . . ? C7B C8B H8B1 109.3 . . ? C9B C8B H8B2 109.3 . . ? C7B C8B H8B2 109.3 . . ? H8B1 C8B H8B2 108 . . ? C10B C9B C8B 107.5(18) . . ? C10B C9B C4B 109.0(17) . . ? C8B C9B C4B 108.6(17) . . ? C10B C9B H9B 110.5 . . ? C8B C9B H9B 110.5 . . ? C4B C9B H9B 110.5 . . ? C9B C10B C5B 111.0(17) . . ? C9B C10B H10C 109.4 . . ? C5B C10B H10C 109.4 . . ? C9B C10B H10D 109.4 . . ? C5B C10B H10D 109.4 . . ? H10C C10B H10D 108 . . ? O1 C11A O2 124.0(3) . . ? O1 C11A C1A 118.2(3) . . ? O2 C11A C1A 117.8(3) . . ? C3D C1C C11C 114.2(9) . . ? C3D C1C C2C 56.5(11) . . ? C11C C1C C2C 111.2(3) . . ? C3D C1C C4C 137.3(9) . . ? C11C C1C C4C 108.5(3) . . ? C2C C1C C4C 109.2(3) . . ? C3D C1C C3C 54.6(11) . . ? C11C C1C C3C 110.3(3) . . ? C2C C1C C3C 108.9(3) . . ? C4C C1C C3C 108.8(3) . . ? C3D C1C C4D 109.1(14) . . ? C11C C1C C4D 113.8(8) . . ? C2C C1C C4D 134.4(9) . . ? C4C C1C C4D 48.7(10) . . ? C3C C1C C4D 61.5(10) . . ? C3D C1C C2D 107.5(14) . . ? C11C C1C C2D 107.7(9) . . ? C2C C1C C2D 54.2(10) . . ? C4C C1C C2D 59.0(10) . . ? C3C C1C C2D 142.0(9) . . ? C4D C1C C2D 103.9(13) . . ? C1C C2C C5C 110.2(3) . . ? C1C C2C H2C1 109.6 . . ? C5C C2C H2C1 109.6 . . ? C1C C2C H2C2 109.6 . . ? C5C C2C H2C2 109.6 . . ? H2C1 C2C H2C2 108.1 . . ? C7C C3C C1C 109.7(3) . . ? C7C C3C H3C1 109.7 . . ? C1C C3C H3C1 109.7 . . ? C7C C3C H3C2 109.7 . . ? C1C C3C H3C2 109.7 . . ? H3C1 C3C H3C2 108.2 . . ? C1C C4C C9C 110.0(3) . . ? C1C C4C H4C1 109.7 . . ? C9C C4C H4C1 109.7 . . ? C1C C4C H4C2 109.7 . . ? C9C C4C H4C2 109.7 . . ? H4C1 C4C H4C2 108.2 . . ? C6C C5C C2C 109.8(4) . . ? C6C C5C C10C 109.1(4) . . ? C2C C5C C10C 109.2(4) . . ? C6C C5C H5C 109.6 . . ? C2C C5C H5C 109.6 . . ? C10C C5C H5C 109.6 . . ? C5C C6C C7C 109.8(3) . . ? C5C C6C H6C1 109.7 . . ? C7C C6C H6C1 109.7 . . ? C5C C6C H6C2 109.7 . . ? C7C C6C H6C2 109.7 . . ? H6C1 C6C H6C2 108.2 . . ? C8C C7C C6C 109.7(4) . . ? C8C C7C C3C 109.2(3) . . ? C6C C7C C3C 109.6(4) . . ? C8C C7C H7C 109.4 . . ? C6C C7C H7C 109.4 . . ? C3C C7C H7C 109.4 . . ? C7C C8C C9C 109.6(3) . . ? C7C C8C H8C1 109.7 . . ? C9C C8C H8C1 109.7 . . ? C7C C8C H8C2 109.7 . . ? C9C C8C H8C2 109.7 . . ? H8C1 C8C H8C2 108.2 . . ? C8C C9C C10C 109.7(4) . . ? C8C C9C C4C 109.4(4) . . ? C10C C9C C4C 109.0(4) . . ? C8C C9C H9C 109.6 . . ? C10C C9C H9C 109.6 . . ? C4C C9C H9C 109.6 . . ? C9C C10C C5C 109.6(4) . . ? C9C C10C H10E 109.8 . . ? C5C C10C H10E 109.8 . . ? C9C C10C H10F 109.8 . . ? C5C C10C H10F 109.8 . . ? H10E C10C H10F 108.2 . . ? C5D C2D C1C 112.9(18) . . ? C5D C2D H2D1 109 . . ? C1C C2D H2D1 109 . . ? C5D C2D H2D2 109 . . ? C1C C2D H2D2 109 . . ? H2D1 C2D H2D2 107.8 . . ? C1C C3D C7D 111.8(18) . . ? C1C C3D H3D1 109.3 . . ? C7D C3D H3D1 109.3 . . ? C1C C3D H3D2 109.3 . . ? C7D C3D H3D2 109.3 . . ? H3D1 C3D H3D2 107.9 . . ? C9D C4D C1C 109.6(17) . . ? C9D C4D H4D1 109.7 . . ? C1C C4D H4D1 109.7 . . ? C9D C4D H4D2 109.7 . . ? C1C C4D H4D2 109.7 . . ? H4D1 C4D H4D2 108.2 . . ? C6D C5D C2D 110(2) . . ? C6D C5D C10D 108(2) . . ? C2D C5D C10D 109(2) . . ? C6D C5D H5D 110.1 . . ? C2D C5D H5D 110.1 . . ? C10D C5D H5D 110.1 . . ? C5D C6D C7D 110.1(19) . . ? C5D C6D H6D1 109.6 . . ? C7D C6D H6D1 109.6 . . ? C5D C6D H6D2 109.6 . . ? C7D C6D H6D2 109.6 . . ? H6D1 C6D H6D2 108.2 . . ? C8D C7D C6D 111(2) . . ? C8D C7D C3D 109(2) . . ? C6D C7D C3D 110(2) . . ? C8D C7D H7D 109.1 . . ? C6D C7D H7D 109.1 . . ? C3D C7D H7D 109.1 . . ? C7D C8D C9D 108.6(18) . . ? C7D C8D H8D1 110 . . ? C9D C8D H8D1 110 . . ? C7D C8D H8D2 110 . . ? C9D C8D H8D2 110 . . ? H8D1 C8D H8D2 108.3 . . ? C10D C9D C8D 110(2) . . ? C10D C9D C4D 113(2) . . ? C8D C9D C4D 109(2) . . ? C10D C9D H9D 108.5 . . ? C8D C9D H9D 108.5 . . ? C4D C9D H9D 108.5 . . ? C9D C10D C5D 109.1(18) . . ? C9D C10D H10G 109.9 . . ? C5D C10D H10G 109.9 . . ? C9D C10D H10H 109.9 . . ? C5D C10D H10H 109.9 . . ? H10G C10D H10H 108.3 . . ? O3 C11C O4 122.7(3) . . ? O3 C11C C1C 119.8(3) . . ? O4 C11C C1C 117.4(3) . . ? N1 C12A C17A 110.8(3) . . ? N1 C12A C13A 110.6(3) . . ? C17A C12A C13A 111.3(3) . . ? N1 C12A H12A 108 . . ? C17A C12A H12A 108 . . ? C13A C12A H12A 108 . . ? C12A C13A C14A 110.4(3) . . ? C12A C13A H13A 109.6 . . ? C14A C13A H13A 109.6 . . ? C12A C13A H13B 109.6 . . ? C14A C13A H13B 109.6 . . ? H13A C13A H13B 108.1 . . ? C15A C14A C13A 111.8(3) . . ? C15A C14A H14A 109.3 . . ? C13A C14A H14A 109.3 . . ? C15A C14A H14B 109.3 . . ? C13A C14A H14B 109.3 . . ? H14A C14A H14B 107.9 . . ? C14A C15A C16A 111.3(3) . . ? C14A C15A H15A 109.4 . . ? C16A C15A H15A 109.4 . . ? C14A C15A H15B 109.4 . . ? C16A C15A H15B 109.4 . . ? H15A C15A H15B 108 . . ? C17A C16A C15A 111.2(3) . . ? C17A C16A H16A 109.4 . . ? C15A C16A H16A 109.4 . . ? C17A C16A H16B 109.4 . . ? C15A C16A H16B 109.4 . . ? H16A C16A H16B 108 . . ? C12A C17A C16A 110.0(3) . . ? C12A C17A H17A 109.7 . . ? C16A C17A H17A 109.7 . . ? C12A C17A H17B 109.7 . . ? C16A C17A H17B 109.7 . . ? H17A C17A H17B 108.2 . . ? C12A N1 H1A 109.5 . . ? C12A N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C12A N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C17B C12B N2 110.0(3) . . ? C17B C12B C13B 111.8(3) . . ? N2 C12B C13B 109.7(3) . . ? C17B C12B H12B 108.4 . . ? N2 C12B H12B 108.4 . . ? C13B C12B H12B 108.4 . . ? C12B C13B C14B 110.1(3) . . ? C12B C13B H13C 109.6 . . ? C14B C13B H13C 109.6 . . ? C12B C13B H13D 109.6 . . ? C14B C13B H13D 109.6 . . ? H13C C13B H13D 108.1 . . ? C15B C14B C13B 111.2(4) . . ? C15B C14B H14C 109.4 . . ? C13B C14B H14C 109.4 . . ? C15B C14B H14D 109.4 . . ? C13B C14B H14D 109.4 . . ? H14C C14B H14D 108 . . ? C14B C15B C16B 111.6(4) . . ? C14B C15B H15C 109.3 . . ? C16B C15B H15C 109.3 . . ? C14B C15B H15D 109.3 . . ? C16B C15B H15D 109.3 . . ? H15C C15B H15D 108 . . ? C15B C16B C17B 110.9(3) . . ? C15B C16B H16C 109.5 . . ? C17B C16B H16C 109.5 . . ? C15B C16B H16D 109.5 . . ? C17B C16B H16D 109.5 . . ? H16C C16B H16D 108 . . ? C12B C17B C16B 110.8(3) . . ? C12B C17B H17C 109.5 . . ? C16B C17B H17C 109.5 . . ? C12B C17B H17D 109.5 . . ? C16B C17B H17D 109.5 . . ? H17C C17B H17D 108.1 . . ? C12B N2 H2A 109.5 . . ? C12B N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C12B N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3B C1A C2A C5A -0.6(13) . . . . ? C2B C1A C2A C5A -89.5(9) . . . . ? C4B C1A C2A C5A 79.8(10) . . . . ? C4A C1A C2A C5A 58.9(4) . . . . ? C3A C1A C2A C5A -58.7(4) . . . . ? C11A C1A C2A C5A 177.8(3) . . . . ? C3B C1A C3A C7A -76.5(9) . . . . ? C2B C1A C3A C7A 90.0(9) . . . . ? C4B C1A C3A C7A 4.5(14) . . . . ? C4A C1A C3A C7A -58.7(4) . . . . ? C11A C1A C3A C7A -178.9(3) . . . . ? C2A C1A C3A C7A 58.2(4) . . . . ? C3B C1A C4A C9A 75.6(9) . . . . ? C2B C1A C4A C9A 1.1(18) . . . . ? C4B C1A C4A C9A -78.5(9) . . . . ? C3A C1A C4A C9A 58.0(4) . . . . ? C11A C1A C4A C9A -179.4(3) . . . . ? C2A C1A C4A C9A -59.0(4) . . . . ? C1A C2A C5A C10A -59.4(5) . . . . ? C1A C2A C5A C6A 60.3(5) . . . . ? C10A C5A C6A C7A 59.9(5) . . . . ? C2A C5A C6A C7A -60.1(5) . . . . ? C5A C6A C7A C8A -59.5(5) . . . . ? C5A C6A C7A C3A 59.9(5) . . . . ? C1A C3A C7A C6A -60.0(5) . . . . ? C1A C3A C7A C8A 59.9(5) . . . . ? C6A C7A C8A C9A 59.5(5) . . . . ? C3A C7A C8A C9A -60.5(6) . . . . ? C7A C8A C9A C10A -59.6(6) . . . . ? C7A C8A C9A C4A 60.6(5) . . . . ? C1A C4A C9A C10A 60.3(5) . . . . ? C1A C4A C9A C8A -59.4(5) . . . . ? C8A C9A C10A C5A 60.5(6) . . . . ? C4A C9A C10A C5A -59.6(5) . . . . ? C6A C5A C10A C9A -60.8(5) . . . . ? C2A C5A C10A C9A 59.2(6) . . . . ? C3B C1A C2B C5B -63.1(17) . . . . ? C4B C1A C2B C5B 60.3(17) . . . . ? C4A C1A C2B C5B -4(3) . . . . ? C3A C1A C2B C5B -75.0(13) . . . . ? C11A C1A C2B C5B 176.6(12) . . . . ? C2A C1A C2B C5B 69.5(13) . . . . ? C2B C1A C3B C7B 61.1(17) . . . . ? C4B C1A C3B C7B -63.1(17) . . . . ? C4A C1A C3B C7B -86.4(15) . . . . ? C3A C1A C3B C7B 73.2(13) . . . . ? C11A C1A C3B C7B 175.6(12) . . . . ? C2A C1A C3B C7B -6(2) . . . . ? C3B C1A C4B C9B 63.8(17) . . . . ? C2B C1A C4B C9B -60.1(17) . . . . ? C4A C1A C4B C9B 86.5(15) . . . . ? C3A C1A C4B C9B 4(2) . . . . ? C11A C1A C4B C9B -172.7(12) . . . . ? C2A C1A C4B C9B -69.9(13) . . . . ? C1A C2B C5B C6B 61(2) . . . . ? C1A C2B C5B C10B -59(2) . . . . ? C10B C5B C6B C7B 61(2) . . . . ? C2B C5B C6B C7B -60(2) . . . . ? C5B C6B C7B C8B -61(2) . . . . ? C5B C6B C7B C3B 58(2) . . . . ? C1A C3B C7B C8B 59(2) . . . . ? C1A C3B C7B C6B -58(2) . . . . ? C6B C7B C8B C9B 62(2) . . . . ? C3B C7B C8B C9B -57(2) . . . . ? C7B C8B C9B C10B -61(2) . . . . ? C7B C8B C9B C4B 57(2) . . . . ? C1A C4B C9B C10B 58(2) . . . . ? C1A C4B C9B C8B -59(2) . . . . ? C8B C9B C10B C5B 58(2) . . . . ? C4B C9B C10B C5B -59(3) . . . . ? C6B C5B C10B C9B -60(2) . . . . ? C2B C5B C10B C9B 60(3) . . . . ? C3B C1A C11A O1 166.0(9) . . . . ? C2B C1A C11A O1 -74.7(9) . . . . ? C4B C1A C11A O1 43.8(10) . . . . ? C4A C1A C11A O1 105.6(4) . . . . ? C3A C1A C11A O1 -133.9(3) . . . . ? C2A C1A C11A O1 -12.8(4) . . . . ? C3B C1A C11A O2 -15.0(10) . . . . ? C2B C1A C11A O2 104.4(9) . . . . ? C4B C1A C11A O2 -137.2(9) . . . . ? C4A C1A C11A O2 -75.3(4) . . . . ? C3A C1A C11A O2 45.2(4) . . . . ? C2A C1A C11A O2 166.2(3) . . . . ? C3D C1C C2C C5C -75.3(11) . . . . ? C11C C1C C2C C5C 179.0(3) . . . . ? C4C C1C C2C C5C 59.4(4) . . . . ? C3C C1C C2C C5C -59.2(4) . . . . ? C4D C1C C2C C5C 9.0(15) . . . . ? C2D C1C C2C C5C 82.0(11) . . . . ? C3D C1C C3C C7C 75.6(11) . . . . ? C11C C1C C3C C7C -178.6(3) . . . . ? C2C C1C C3C C7C 59.1(4) . . . . ? C4C C1C C3C C7C -59.7(4) . . . . ? C4D C1C C3C C7C -71.8(10) . . . . ? C2D C1C C3C C7C 3.6(18) . . . . ? C3D C1C C4C C9C 1.5(17) . . . . ? C11C C1C C4C C9C 179.2(3) . . . . ? C2C C1C C4C C9C -59.5(4) . . . . ? C3C C1C C4C C9C 59.2(4) . . . . ? C4D C1C C4C C9C 73.3(11) . . . . ? C2D C1C C4C C9C -80.9(11) . . . . ? C1C C2C C5C C6C 59.9(4) . . . . ? C1C C2C C5C C10C -59.7(4) . . . . ? C2C C5C C6C C7C -59.6(5) . . . . ? C10C C5C C6C C7C 60.0(5) . . . . ? C5C C6C C7C C8C -60.2(5) . . . . ? C5C C6C C7C C3C 59.7(5) . . . . ? C1C C3C C7C C8C 60.7(4) . . . . ? C1C C3C C7C C6C -59.5(4) . . . . ? C6C C7C C8C C9C 59.4(5) . . . . ? C3C C7C C8C C9C -60.8(5) . . . . ? C7C C8C C9C C10C -59.3(5) . . . . ? C7C C8C C9C C4C 60.2(5) . . . . ? C1C C4C C9C C8C -59.7(4) . . . . ? C1C C4C C9C C10C 60.2(4) . . . . ? C8C C9C C10C C5C 59.5(5) . . . . ? C4C C9C C10C C5C -60.2(5) . . . . ? C6C C5C C10C C9C -59.8(5) . . . . ? C2C C5C C10C C9C 60.2(5) . . . . ? C3D C1C C2D C5D -54(2) . . . . ? C11C C1C C2D C5D -177.7(16) . . . . ? C2C C1C C2D C5D -73.9(18) . . . . ? C4C C1C C2D C5D 81.0(18) . . . . ? C3C C1C C2D C5D 0(3) . . . . ? C4D C1C C2D C5D 61(2) . . . . ? C11C C1C C3D C7D 175.5(15) . . . . ? C2C C1C C3D C7D 75.3(18) . . . . ? C4C C1C C3D C7D -7(3) . . . . ? C3C C1C C3D C7D -86.0(19) . . . . ? C4D C1C C3D C7D -56(2) . . . . ? C2D C1C C3D C7D 56(2) . . . . ? C3D C1C C4D C9D 56(2) . . . . ? C11C C1C C4D C9D -175.1(14) . . . . ? C2C C1C C4D C9D -5(3) . . . . ? C4C C1C C4D C9D -80.9(18) . . . . ? C3C C1C C4D C9D 83.8(17) . . . . ? C2D C1C C4D C9D -58(2) . . . . ? C1C C2D C5D C6D 56(3) . . . . ? C1C C2D C5D C10D -62(2) . . . . ? C2D C5D C6D C7D -59(3) . . . . ? C10D C5D C6D C7D 60(3) . . . . ? C5D C6D C7D C8D -59(3) . . . . ? C5D C6D C7D C3D 61(3) . . . . ? C1C C3D C7D C8D 60(2) . . . . ? C1C C3D C7D C6D -62(2) . . . . ? C6D C7D C8D C9D 58(3) . . . . ? C3D C7D C8D C9D -62(3) . . . . ? C7D C8D C9D C10D -60(3) . . . . ? C7D C8D C9D C4D 64(3) . . . . ? C1C C4D C9D C10D 62(2) . . . . ? C1C C4D C9D C8D -60(2) . . . . ? C8D C9D C10D C5D 62(3) . . . . ? C4D C9D C10D C5D -59(3) . . . . ? C6D C5D C10D C9D -61(3) . . . . ? C2D C5D C10D C9D 58(3) . . . . ? C3D C1C C11C O3 -73.3(12) . . . . ? C2C C1C C11C O3 -11.7(4) . . . . ? C4C C1C C11C O3 108.4(3) . . . . ? C3C C1C C11C O3 -132.6(3) . . . . ? C4D C1C C11C O3 160.6(11) . . . . ? C2D C1C C11C O3 46.0(11) . . . . ? C3D C1C C11C O4 109.3(12) . . . . ? C2C C1C C11C O4 170.9(3) . . . . ? C4C C1C C11C O4 -69.0(4) . . . . ? C3C C1C C11C O4 50.0(4) . . . . ? C4D C1C C11C O4 -16.8(12) . . . . ? C2D C1C C11C O4 -131.4(11) . . . . ? N1 C12A C13A C14A -178.9(3) . . . . ? C17A C12A C13A C14A 57.4(4) . . . . ? C12A C13A C14A C15A -54.9(4) . . . . ? C13A C14A C15A C16A 53.9(4) . . . . ? C14A C15A C16A C17A -54.7(4) . . . . ? N1 C12A C17A C16A 178.1(3) . . . . ? C13A C12A C17A C16A -58.3(4) . . . . ? C15A C16A C17A C12A 56.7(4) . . . . ? C17B C12B C13B C14B 56.5(5) . . . . ? N2 C12B C13B C14B 178.7(3) . . . . ? C12B C13B C14B C15B -55.8(5) . . . . ? C13B C14B C15B C16B 56.1(6) . . . . ? C14B C15B C16B C17B -55.2(5) . . . . ? N2 C12B C17B C16B -178.3(3) . . . . ? C13B C12B C17B C16B -56.2(4) . . . . ? C15B C16B C17B C12B 55.1(5) . . . . ? 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 0.91 1.87 2.754(4) 163 . N1 H1B O3 0.91 1.81 2.708(4) 169 1_455 N1 H1C O4 0.91 1.89 2.797(4) 173 . N2 H2A O4 0.91 1.85 2.743(4) 167 . N2 H2B O1 0.91 1.8 2.712(4) 175 . N2 H2C O2 0.91 1.89 2.797(4) 177 1_655 ###END data_8 _database_code_depnum_ccdc_archive 'CCDC 797980' #TrackingRef '- Lemmerer.cif' _audit_creation_date 2010-10-13T10:35:34-00:00 _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 ; (cycloheptylammonium).(adamantane carboxylate) ; _chemical_formula_moiety 'C11 H15 O2, C7 H16 N' _chemical_formula_sum 'C18 H31 N O2' _chemical_formula_weight 293.44 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.4749(10) _cell_length_b 6.4309(2) _cell_length_c 21.8759(10) _cell_angle_alpha 90 _cell_angle_beta 96.802(2) _cell_angle_gamma 90 _cell_volume 3279.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2652 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 28.2 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.033 -1 0 0 0.05 1 2 1 0.235 0 0 -1 0.069 0 0 1 0.079 -1 -1 -1 0.246 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9937 #----------------------------------------------------------------------------# # 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 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_unetI/netI 0.0587 _diffrn_reflns_number 9841 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3969 _reflns_number_gt 2792 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0652P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3969 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.05 _refine_ls_wR_factor_ref 0.1218 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.336 _refine_diff_density_min -0.23 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # 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 0.66437(5) 0.04540(19) 0.64919(6) 0.0153(3) Uani 1 1 d . . . C2 C 0.67008(6) -0.1259(2) 0.69824(6) 0.0186(3) Uani 1 1 d . . . H2A H 0.6528 -0.256 0.6804 0.022 Uiso 1 1 calc R . . H2B H 0.7112 -0.1526 0.7117 0.022 Uiso 1 1 calc R . . C3 C 0.60002(6) 0.0861(2) 0.62920(6) 0.0203(3) Uani 1 1 d . . . H3A H 0.5957 0.198 0.5979 0.024 Uiso 1 1 calc R . . H3B H 0.5818 -0.0413 0.6105 0.024 Uiso 1 1 calc R . . C4 C 0.69160(6) 0.2465(2) 0.67784(6) 0.0188(3) Uani 1 1 d . . . H4A H 0.733 0.2237 0.6906 0.023 Uiso 1 1 calc R . . H4B H 0.6876 0.3595 0.6469 0.023 Uiso 1 1 calc R . . C5 C 0.64016(6) -0.0621(2) 0.75384(6) 0.0213(3) Uani 1 1 d . . . H5 H 0.6442 -0.176 0.7852 0.026 Uiso 1 1 calc R . . C6 C 0.57644(6) -0.0226(2) 0.73311(6) 0.0247(3) Uani 1 1 d . . . H6A H 0.5583 -0.1514 0.7154 0.03 Uiso 1 1 calc R . . H6B H 0.5569 0.018 0.769 0.03 Uiso 1 1 calc R . . C7 C 0.57027(6) 0.1503(2) 0.68506(6) 0.0224(3) Uani 1 1 d . . . H7 H 0.5287 0.1765 0.6717 0.027 Uiso 1 1 calc R . . C8 C 0.59826(6) 0.3494(2) 0.71313(7) 0.0246(3) Uani 1 1 d . . . H8A H 0.5789 0.3929 0.7489 0.03 Uiso 1 1 calc R . . H8B H 0.594 0.4626 0.6823 0.03 Uiso 1 1 calc R . . C9 C 0.66214(6) 0.3099(2) 0.73375(6) 0.0213(3) Uani 1 1 d . . . H9 H 0.6802 0.44 0.7521 0.026 Uiso 1 1 calc R . . C10 C 0.66802(6) 0.1367(2) 0.78204(6) 0.0234(3) Uani 1 1 d . . . H10A H 0.649 0.1789 0.8182 0.028 Uiso 1 1 calc R . . H10B H 0.7091 0.1111 0.796 0.028 Uiso 1 1 calc R . . C11 C 0.69345(6) -0.0211(2) 0.59333(6) 0.0177(3) Uani 1 1 d . . . O1 O 0.69374(4) 0.10639(15) 0.54902(4) 0.0246(2) Uani 1 1 d . . . O2 O 0.71600(4) -0.19731(15) 0.59335(4) 0.0257(3) Uani 1 1 d . . . C12 C 0.66195(6) 0.5621(2) 0.45239(6) 0.0212(3) Uani 1 1 d . . . H12 H 0.6761 0.6878 0.4319 0.025 Uiso 1 1 calc R . . C13 C 0.65582(6) 0.3871(2) 0.40489(6) 0.0254(3) Uani 1 1 d . . . H13A H 0.6455 0.4501 0.3638 0.03 Uiso 1 1 calc R . . H13B H 0.6938 0.3206 0.4047 0.03 Uiso 1 1 calc R . . C14 C 0.61216(6) 0.2171(2) 0.41356(7) 0.0268(3) Uani 1 1 d . . . H14A H 0.6123 0.1901 0.4581 0.032 Uiso 1 1 calc R . . H14B H 0.624 0.0873 0.3942 0.032 Uiso 1 1 calc R . . C15 C 0.55124(7) 0.2725(3) 0.38589(7) 0.0318(4) Uani 1 1 d . . . H15A H 0.5525 0.3204 0.3431 0.038 Uiso 1 1 calc R . . H15B H 0.5276 0.1447 0.3841 0.038 Uiso 1 1 calc R . . C16 C 0.52177(7) 0.4381(3) 0.42018(7) 0.0333(4) Uani 1 1 d . . . H16A H 0.5145 0.3804 0.4605 0.04 Uiso 1 1 calc R . . H16B H 0.484 0.4686 0.3966 0.04 Uiso 1 1 calc R . . C17 C 0.55435(7) 0.6427(2) 0.43157(7) 0.0302(4) Uani 1 1 d . . . H17A H 0.5282 0.7482 0.4457 0.036 Uiso 1 1 calc R . . H17B H 0.5664 0.6921 0.3922 0.036 Uiso 1 1 calc R . . C18 C 0.60750(6) 0.6244(2) 0.47940(7) 0.0265(3) Uani 1 1 d . . . H18A H 0.6141 0.7597 0.5006 0.032 Uiso 1 1 calc R . . H18B H 0.5997 0.5201 0.5106 0.032 Uiso 1 1 calc R . . N1 N 0.70662(5) 0.50449(18) 0.50461(5) 0.0201(3) Uani 1 1 d . . . H1A H 0.6957 0.3864 0.523 0.03 Uiso 1 1 calc R . . H1B H 0.7104 0.6096 0.5326 0.03 Uiso 1 1 calc R . . H1C H 0.7408 0.4826 0.4898 0.03 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0160(6) 0.0148(6) 0.0153(6) 0.0009(5) 0.0018(5) -0.0010(5) C2 0.0209(7) 0.0172(6) 0.0179(6) 0.0017(5) 0.0026(5) 0.0007(6) C3 0.0186(7) 0.0211(7) 0.0202(7) 0.0011(5) -0.0023(5) -0.0011(6) C4 0.0197(7) 0.0177(6) 0.0187(6) -0.0003(5) 0.0014(5) -0.0038(6) C5 0.0267(8) 0.0201(7) 0.0175(7) 0.0048(5) 0.0048(6) 0.0009(6) C6 0.0232(8) 0.0247(7) 0.0274(7) 0.0009(6) 0.0085(6) -0.0031(6) C7 0.0167(7) 0.0250(7) 0.0254(7) 0.0013(6) 0.0019(6) 0.0016(6) C8 0.0270(8) 0.0203(7) 0.0276(8) -0.0001(6) 0.0072(6) 0.0051(6) C9 0.0257(7) 0.0176(7) 0.0205(7) -0.0043(5) 0.0028(6) -0.0030(6) C10 0.0277(8) 0.0271(7) 0.0156(6) -0.0014(6) 0.0033(6) -0.0007(6) C11 0.0171(6) 0.0196(7) 0.0155(6) -0.0021(5) -0.0021(5) -0.0031(6) O1 0.0314(6) 0.0258(5) 0.0175(5) 0.0043(4) 0.0070(4) 0.0012(5) O2 0.0360(6) 0.0208(5) 0.0207(5) -0.0026(4) 0.0051(4) 0.0053(5) C12 0.0236(7) 0.0219(7) 0.0176(7) 0.0011(5) 0.0007(6) -0.0009(6) C13 0.0264(8) 0.0321(8) 0.0181(7) -0.0052(6) 0.0043(6) -0.0022(7) C14 0.0318(8) 0.0251(8) 0.0233(7) -0.0046(6) 0.0027(6) -0.0022(7) C15 0.0296(8) 0.0368(9) 0.0279(8) -0.0044(7) -0.0014(7) -0.0066(7) C16 0.0236(8) 0.0433(10) 0.0322(9) -0.0012(7) -0.0009(7) -0.0003(7) C17 0.0254(8) 0.0315(8) 0.0330(8) 0.0012(7) 0.0002(7) 0.0062(7) C18 0.0268(8) 0.0282(8) 0.0240(7) -0.0053(6) 0.0016(6) 0.0031(7) N1 0.0243(6) 0.0188(6) 0.0174(6) -0.0015(5) 0.0036(5) 0.0003(5) #----------------------------------------------------------------------------# # 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 C11 1.5297(19) . ? C1 C2 1.5324(17) . ? C1 C4 1.5426(17) . ? C1 C3 1.5444(18) . ? C2 C5 1.5307(19) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C7 1.534(2) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C9 1.5299(19) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.5318(19) . ? C5 C10 1.5322(19) . ? C5 H5 1 . ? C6 C7 1.5253(19) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.534(2) . ? C7 H7 1 . ? C8 C9 1.535(2) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.5299(19) . ? C9 H9 1 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 O2 1.2507(16) . ? C11 O1 1.2703(16) . ? C12 N1 1.5027(16) . ? C12 C18 1.524(2) . ? C12 C13 1.5269(19) . ? C12 H12 1 . ? C13 C14 1.526(2) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.528(2) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 C16 1.516(2) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.527(2) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.5351(19) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? N1 H1A 0.91 . ? N1 H1B 0.91 . ? N1 H1C 0.91 . ? 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 C11 C1 C2 110.38(11) . . ? C11 C1 C4 110.87(11) . . ? C2 C1 C4 108.69(10) . . ? C11 C1 C3 109.60(10) . . ? C2 C1 C3 108.76(11) . . ? C4 C1 C3 108.49(10) . . ? C5 C2 C1 110.71(11) . . ? C5 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? C5 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C7 C3 C1 110.02(10) . . ? C7 C3 H3A 109.7 . . ? C1 C3 H3A 109.7 . . ? C7 C3 H3B 109.7 . . ? C1 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C9 C4 C1 110.08(11) . . ? C9 C4 H4A 109.6 . . ? C1 C4 H4A 109.6 . . ? C9 C4 H4B 109.6 . . ? C1 C4 H4B 109.6 . . ? H4A C4 H4B 108.2 . . ? C2 C5 C6 109.45(11) . . ? C2 C5 C10 109.22(11) . . ? C6 C5 C10 109.65(12) . . ? C2 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? C10 C5 H5 109.5 . . ? C7 C6 C5 109.55(12) . . ? C7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? C7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? C6 C7 C8 109.35(11) . . ? C6 C7 C3 109.75(12) . . ? C8 C7 C3 109.24(11) . . ? C6 C7 H7 109.5 . . ? C8 C7 H7 109.5 . . ? C3 C7 H7 109.5 . . ? C7 C8 C9 109.69(11) . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C4 C9 C10 110.22(11) . . ? C4 C9 C8 109.11(11) . . ? C10 C9 C8 109.17(12) . . ? C4 C9 H9 109.4 . . ? C10 C9 H9 109.4 . . ? C8 C9 H9 109.4 . . ? C9 C10 C5 109.28(10) . . ? C9 C10 H10A 109.8 . . ? C5 C10 H10A 109.8 . . ? C9 C10 H10B 109.8 . . ? C5 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? O2 C11 O1 122.99(13) . . ? O2 C11 C1 118.81(12) . . ? O1 C11 C1 118.19(12) . . ? N1 C12 C18 108.18(11) . . ? N1 C12 C13 109.66(11) . . ? C18 C12 C13 116.22(12) . . ? N1 C12 H12 107.5 . . ? C18 C12 H12 107.5 . . ? C13 C12 H12 107.5 . . ? C14 C13 C12 117.01(13) . . ? C14 C13 H13A 108 . . ? C12 C13 H13A 108 . . ? C14 C13 H13B 108 . . ? C12 C13 H13B 108 . . ? H13A C13 H13B 107.3 . . ? C13 C14 C15 113.24(13) . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 115.37(12) . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15A 108.4 . . ? C16 C15 H15B 108.4 . . ? C14 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? C15 C16 C17 115.91(14) . . ? C15 C16 H16A 108.3 . . ? C17 C16 H16A 108.3 . . ? C15 C16 H16B 108.3 . . ? C17 C16 H16B 108.3 . . ? H16A C16 H16B 107.4 . . ? C16 C17 C18 113.32(13) . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C12 C18 C17 114.04(12) . . ? C12 C18 H18A 108.7 . . ? C17 C18 H18A 108.7 . . ? C12 C18 H18B 108.7 . . ? C17 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C12 N1 H1A 109.5 . . ? C12 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C12 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 C5 -179.00(10) . . . . ? C4 C1 C2 C5 59.21(14) . . . . ? C3 C1 C2 C5 -58.74(13) . . . . ? C11 C1 C3 C7 179.29(11) . . . . ? C2 C1 C3 C7 58.54(14) . . . . ? C4 C1 C3 C7 -59.53(14) . . . . ? C11 C1 C4 C9 -179.75(10) . . . . ? C2 C1 C4 C9 -58.26(14) . . . . ? C3 C1 C4 C9 59.85(13) . . . . ? C1 C2 C5 C6 59.66(14) . . . . ? C1 C2 C5 C10 -60.39(14) . . . . ? C2 C5 C6 C7 -59.67(14) . . . . ? C10 C5 C6 C7 60.11(14) . . . . ? C5 C6 C7 C8 -59.74(15) . . . . ? C5 C6 C7 C3 60.07(14) . . . . ? C1 C3 C7 C6 -59.83(14) . . . . ? C1 C3 C7 C8 60.05(14) . . . . ? C6 C7 C8 C9 59.97(15) . . . . ? C3 C7 C8 C9 -60.15(14) . . . . ? C1 C4 C9 C10 59.34(14) . . . . ? C1 C4 C9 C8 -60.53(14) . . . . ? C7 C8 C9 C4 60.36(15) . . . . ? C7 C8 C9 C10 -60.15(14) . . . . ? C4 C9 C10 C5 -59.73(15) . . . . ? C8 C9 C10 C5 60.10(15) . . . . ? C2 C5 C10 C9 59.68(15) . . . . ? C6 C5 C10 C9 -60.25(15) . . . . ? C2 C1 C11 O2 1.44(16) . . . . ? C4 C1 C11 O2 121.93(13) . . . . ? C3 C1 C11 O2 -118.33(13) . . . . ? C2 C1 C11 O1 -178.30(11) . . . . ? C4 C1 C11 O1 -57.81(15) . . . . ? C3 C1 C11 O1 61.93(15) . . . . ? N1 C12 C13 C14 89.62(15) . . . . ? C18 C12 C13 C14 -33.42(17) . . . . ? C12 C13 C14 C15 84.87(16) . . . . ? C13 C14 C15 C16 -71.86(18) . . . . ? C14 C15 C16 C17 53.98(19) . . . . ? C15 C16 C17 C18 -70.82(18) . . . . ? N1 C12 C18 C17 -167.68(12) . . . . ? C13 C12 C18 C17 -43.87(18) . . . . ? C16 C17 C18 C12 88.35(17) . . . . ? 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 0.91 1.89 2.768(2) 161 . N1 H1B O2 0.91 1.81 2.719(1) 175 1_565 N1 H1C O1 0.91 1.93 2.830(2) 170 7_656 ###END data_9 _database_code_depnum_ccdc_archive 'CCDC 797981' #TrackingRef '- Lemmerer.cif' _audit_creation_date 2010-10-13T10:30:37-00:00 _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 ; (cyclooctylammonium).(adamantane carboxylate) ; _chemical_formula_moiety 'C11 H15 O2, C8 H18 N' _chemical_formula_sum 'C19 H33 N O2' _chemical_formula_weight 307.46 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.4758(3) _cell_length_b 11.2016(6) _cell_length_c 24.5573(14) _cell_angle_alpha 90 _cell_angle_beta 93.217(4) _cell_angle_gamma 90 _cell_volume 1778.56(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1380 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 28.14 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.027 0 0 -1 0.01 0 1 0 0.075 0 -1 0 0.042 1 0 0 0.212 -1 0 0 0.292 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_T_max 0.9967 #----------------------------------------------------------------------------# # 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 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.1404 _diffrn_reflns_av_unetI/netI 0.147 _diffrn_reflns_number 12847 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 4267 _reflns_number_gt 1985 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0523P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4267 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1684 _refine_ls_R_factor_gt 0.065 _refine_ls_wR_factor_ref 0.147 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.312 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # 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 0.6737(4) 0.3119(2) 0.36126(9) 0.0183(5) Uani 1 1 d . . . C2 C 0.4664(4) 0.3579(2) 0.33630(10) 0.0219(6) Uani 1 1 d . . . H2A H 0.3607 0.3541 0.3639 0.026 Uiso 1 1 calc R . . H2B H 0.4811 0.4422 0.3251 0.026 Uiso 1 1 calc R . . C3 C 0.8345(4) 0.3162(2) 0.31806(10) 0.0228(6) Uani 1 1 d . . . H3A H 0.9689 0.2865 0.3339 0.027 Uiso 1 1 calc R . . H3B H 0.8537 0.3998 0.3062 0.027 Uiso 1 1 calc R . . C4 C 0.6454(4) 0.1808(2) 0.37850(10) 0.0242(6) Uani 1 1 d . . . H4A H 0.7778 0.1494 0.3947 0.029 Uiso 1 1 calc R . . H4B H 0.5412 0.1763 0.4064 0.029 Uiso 1 1 calc R . . C5 C 0.3966(4) 0.2824(2) 0.28678(10) 0.0252(6) Uani 1 1 d . . . H5 H 0.2622 0.3139 0.2706 0.03 Uiso 1 1 calc R . . C6 C 0.5591(4) 0.2871(2) 0.24399(10) 0.0290(7) Uani 1 1 d . . . H6A H 0.5133 0.2382 0.212 0.035 Uiso 1 1 calc R . . H6B H 0.5767 0.3705 0.2316 0.035 Uiso 1 1 calc R . . C7 C 0.7645(4) 0.2395(2) 0.26878(10) 0.0273(6) Uani 1 1 d . . . H7 H 0.8711 0.2431 0.2409 0.033 Uiso 1 1 calc R . . C8 C 0.7376(4) 0.1106(2) 0.28691(11) 0.0310(7) Uani 1 1 d . . . H8A H 0.6941 0.0605 0.2551 0.037 Uiso 1 1 calc R . . H8B H 0.8707 0.0793 0.3028 0.037 Uiso 1 1 calc R . . C9 C 0.5747(4) 0.1051(2) 0.32920(11) 0.0268(6) Uani 1 1 d . . . H9 H 0.5568 0.0205 0.341 0.032 Uiso 1 1 calc R . . C10 C 0.3683(4) 0.1525(2) 0.30447(11) 0.0290(6) Uani 1 1 d . . . H10A H 0.2617 0.148 0.3318 0.035 Uiso 1 1 calc R . . H10B H 0.3219 0.1034 0.2726 0.035 Uiso 1 1 calc R . . C11 C 0.7534(4) 0.3821(2) 0.41158(10) 0.0211(6) Uani 1 1 d . . . O1 O 0.6391(3) 0.46158(14) 0.43104(7) 0.0270(4) Uani 1 1 d . . . O2 O 0.9306(2) 0.35724(15) 0.43145(7) 0.0287(4) Uani 1 1 d . . . C12 C 0.1746(4) 0.6357(2) 0.43704(10) 0.0220(6) Uani 1 1 d . . . H12 H 0.0502 0.6614 0.4564 0.026 Uiso 1 1 calc R . . C13 C 0.3498(4) 0.7235(2) 0.45145(11) 0.0292(6) Uani 1 1 d . . . H13A H 0.3582 0.735 0.4915 0.035 Uiso 1 1 calc R . . H13B H 0.4814 0.6865 0.4415 0.035 Uiso 1 1 calc R . . C14 C 0.3326(4) 0.8455(2) 0.42461(12) 0.0359(7) Uani 1 1 d . . . H14A H 0.3261 0.8339 0.3846 0.043 Uiso 1 1 calc R . . H14B H 0.4611 0.8903 0.4344 0.043 Uiso 1 1 calc R . . C15 C 0.1502(5) 0.9228(2) 0.43863(13) 0.0441(8) Uani 1 1 d . . . H15A H 0.1688 1.0025 0.4223 0.053 Uiso 1 1 calc R . . H15B H 0.1558 0.9334 0.4787 0.053 Uiso 1 1 calc R . . C16 C -0.0653(4) 0.8784(2) 0.42075(12) 0.0395(8) Uani 1 1 d . . . H16A H -0.1633 0.9457 0.4234 0.047 Uiso 1 1 calc R . . H16B H -0.1056 0.8164 0.4469 0.047 Uiso 1 1 calc R . . C17 C -0.0908(4) 0.8263(2) 0.36309(11) 0.0382(7) Uani 1 1 d . . . H17A H -0.2237 0.8553 0.3461 0.046 Uiso 1 1 calc R . . H17B H 0.0209 0.8587 0.3415 0.046 Uiso 1 1 calc R . . C18 C -0.0873(4) 0.6911(2) 0.35864(11) 0.0308(7) Uani 1 1 d . . . H18A H -0.1237 0.6698 0.3202 0.037 Uiso 1 1 calc R . . H18B H -0.1983 0.6593 0.3807 0.037 Uiso 1 1 calc R . . C19 C 0.1130(4) 0.6256(2) 0.37610(10) 0.0252(6) Uani 1 1 d . . . H19A H 0.2266 0.658 0.3551 0.03 Uiso 1 1 calc R . . H19B H 0.097 0.5401 0.3666 0.03 Uiso 1 1 calc R . . N1 N 0.2411(3) 0.51550(16) 0.45866(8) 0.0217(5) Uani 1 1 d . . . H1A H 0.3603 0.4933 0.4435 0.033 Uiso 1 1 calc R . . H1B H 0.1405 0.4609 0.45 0.033 Uiso 1 1 calc R . . H1C H 0.2627 0.5194 0.4956 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0181(13) 0.0160(12) 0.0206(13) -0.0030(10) -0.0020(10) 0.0006(9) C2 0.0210(13) 0.0198(13) 0.0246(14) -0.0030(11) -0.0009(11) 0.0033(10) C3 0.0194(13) 0.0233(13) 0.0258(14) -0.0021(12) 0.0010(11) -0.0010(10) C4 0.0270(15) 0.0203(13) 0.0250(15) 0.0009(12) -0.0019(11) -0.0013(11) C5 0.0190(14) 0.0277(14) 0.0282(15) -0.0039(12) -0.0055(11) 0.0036(10) C6 0.0350(17) 0.0293(15) 0.0220(15) -0.0032(12) -0.0047(12) -0.0003(12) C7 0.0234(14) 0.0341(15) 0.0251(15) -0.0079(13) 0.0063(11) -0.0038(11) C8 0.0266(15) 0.0245(14) 0.0409(17) -0.0142(13) -0.0062(13) 0.0058(11) C9 0.0279(15) 0.0149(13) 0.0368(16) -0.0009(12) -0.0052(12) -0.0017(10) C10 0.0228(14) 0.0278(15) 0.0359(16) -0.0069(13) -0.0018(12) -0.0054(11) C11 0.0214(14) 0.0193(13) 0.0232(14) 0.0021(11) 0.0056(11) -0.0042(10) O1 0.0276(10) 0.0261(10) 0.0271(10) -0.0072(8) -0.0012(8) 0.0037(8) O2 0.0213(10) 0.0309(10) 0.0330(11) -0.0051(9) -0.0057(8) 0.0004(8) C12 0.0209(13) 0.0196(13) 0.0255(14) 0.0002(11) 0.0012(11) 0.0040(10) C13 0.0253(15) 0.0248(14) 0.0372(17) -0.0009(13) 0.0000(12) -0.0005(11) C14 0.0351(17) 0.0267(15) 0.0460(18) 0.0014(14) 0.0019(14) -0.0081(13) C15 0.053(2) 0.0228(15) 0.057(2) -0.0031(15) 0.0009(16) 0.0029(14) C16 0.0399(18) 0.0272(15) 0.051(2) -0.0014(14) 0.0003(15) 0.0131(13) C17 0.0373(18) 0.0331(16) 0.0436(19) 0.0075(14) -0.0053(14) 0.0080(13) C18 0.0296(16) 0.0312(15) 0.0311(16) 0.0035(13) -0.0022(12) 0.0020(12) C19 0.0281(14) 0.0240(13) 0.0235(14) 0.0013(12) 0.0016(11) 0.0007(11) N1 0.0236(12) 0.0193(11) 0.0217(12) -0.0017(9) -0.0016(9) 0.0020(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 C3 1.528(3) . ? C1 C11 1.530(3) . ? C1 C2 1.534(3) . ? C1 C4 1.542(3) . ? C2 C5 1.528(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C7 1.532(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C9 1.527(3) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.530(4) . ? C5 C10 1.532(3) . ? C5 H5 1 . ? C6 C7 1.527(3) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.525(4) . ? C7 H7 1 . ? C8 C9 1.522(4) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.532(3) . ? C9 H9 1 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 O2 1.253(3) . ? C11 O1 1.268(3) . ? C12 N1 1.502(3) . ? C12 C13 1.527(3) . ? C12 C19 1.531(3) . ? C12 H12 1 . ? C13 C14 1.519(3) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.519(4) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 C16 1.523(4) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.532(4) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.519(3) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 C19 1.531(3) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? N1 H1A 0.91 . ? N1 H1B 0.91 . ? N1 H1C 0.91 . ? 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 C3 C1 C11 109.40(19) . . ? C3 C1 C2 109.1(2) . . ? C11 C1 C2 113.45(19) . . ? C3 C1 C4 108.51(19) . . ? C11 C1 C4 107.93(19) . . ? C2 C1 C4 108.33(19) . . ? C5 C2 C1 110.19(19) . . ? C5 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? C5 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C1 C3 C7 110.31(19) . . ? C1 C3 H3A 109.6 . . ? C7 C3 H3A 109.6 . . ? C1 C3 H3B 109.6 . . ? C7 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C9 C4 C1 110.2(2) . . ? C9 C4 H4A 109.6 . . ? C1 C4 H4A 109.6 . . ? C9 C4 H4B 109.6 . . ? C1 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C2 C5 C6 110.1(2) . . ? C2 C5 C10 109.5(2) . . ? C6 C5 C10 109.0(2) . . ? C2 C5 H5 109.4 . . ? C6 C5 H5 109.4 . . ? C10 C5 H5 109.4 . . ? C7 C6 C5 109.3(2) . . ? C7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? C7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? C8 C7 C6 109.6(2) . . ? C8 C7 C3 109.5(2) . . ? C6 C7 C3 109.4(2) . . ? C8 C7 H7 109.4 . . ? C6 C7 H7 109.4 . . ? C3 C7 H7 109.4 . . ? C9 C8 C7 109.4(2) . . ? C9 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? C9 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C8 C9 C4 109.3(2) . . ? C8 C9 C10 109.8(2) . . ? C4 C9 C10 109.7(2) . . ? C8 C9 H9 109.3 . . ? C4 C9 H9 109.3 . . ? C10 C9 H9 109.3 . . ? C9 C10 C5 109.03(19) . . ? C9 C10 H10A 109.9 . . ? C5 C10 H10A 109.9 . . ? C9 C10 H10B 109.9 . . ? C5 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? O2 C11 O1 123.4(2) . . ? O2 C11 C1 117.4(2) . . ? O1 C11 C1 119.2(2) . . ? N1 C12 C13 107.51(18) . . ? N1 C12 C19 109.43(18) . . ? C13 C12 C19 115.1(2) . . ? N1 C12 H12 108.2 . . ? C13 C12 H12 108.2 . . ? C19 C12 H12 108.2 . . ? C14 C13 C12 116.3(2) . . ? C14 C13 H13A 108.2 . . ? C12 C13 H13A 108.2 . . ? C14 C13 H13B 108.2 . . ? C12 C13 H13B 108.2 . . ? H13A C13 H13B 107.4 . . ? C13 C14 C15 117.0(2) . . ? C13 C14 H14A 108.1 . . ? C15 C14 H14A 108.1 . . ? C13 C14 H14B 108.1 . . ? C15 C14 H14B 108.1 . . ? H14A C14 H14B 107.3 . . ? C14 C15 C16 117.4(2) . . ? C14 C15 H15A 108 . . ? C16 C15 H15A 108 . . ? C14 C15 H15B 108 . . ? C16 C15 H15B 108 . . ? H15A C15 H15B 107.2 . . ? C15 C16 C17 116.1(3) . . ? C15 C16 H16A 108.3 . . ? C17 C16 H16A 108.3 . . ? C15 C16 H16B 108.3 . . ? C17 C16 H16B 108.3 . . ? H16A C16 H16B 107.4 . . ? C18 C17 C16 116.4(2) . . ? C18 C17 H17A 108.2 . . ? C16 C17 H17A 108.2 . . ? C18 C17 H17B 108.2 . . ? C16 C17 H17B 108.2 . . ? H17A C17 H17B 107.3 . . ? C17 C18 C19 118.3(2) . . ? C17 C18 H18A 107.7 . . ? C19 C18 H18A 107.7 . . ? C17 C18 H18B 107.7 . . ? C19 C18 H18B 107.7 . . ? H18A C18 H18B 107.1 . . ? C18 C19 C12 114.1(2) . . ? C18 C19 H19A 108.7 . . ? C12 C19 H19A 108.7 . . ? C18 C19 H19B 108.7 . . ? C12 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C12 N1 H1A 109.5 . . ? C12 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C12 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C1 C2 C5 58.4(3) . . . . ? C11 C1 C2 C5 -179.4(2) . . . . ? C4 C1 C2 C5 -59.6(3) . . . . ? C11 C1 C3 C7 176.22(19) . . . . ? C2 C1 C3 C7 -59.1(3) . . . . ? C4 C1 C3 C7 58.7(2) . . . . ? C3 C1 C4 C9 -59.1(2) . . . . ? C11 C1 C4 C9 -177.6(2) . . . . ? C2 C1 C4 C9 59.2(3) . . . . ? C1 C2 C5 C6 -59.1(3) . . . . ? C1 C2 C5 C10 60.8(3) . . . . ? C2 C5 C6 C7 59.5(3) . . . . ? C10 C5 C6 C7 -60.6(2) . . . . ? C5 C6 C7 C8 60.4(3) . . . . ? C5 C6 C7 C3 -59.8(3) . . . . ? C1 C3 C7 C8 -59.9(3) . . . . ? C1 C3 C7 C6 60.2(3) . . . . ? C6 C7 C8 C9 -59.8(3) . . . . ? C3 C7 C8 C9 60.2(3) . . . . ? C7 C8 C9 C4 -60.5(3) . . . . ? C7 C8 C9 C10 59.9(3) . . . . ? C1 C4 C9 C8 60.4(3) . . . . ? C1 C4 C9 C10 -60.0(3) . . . . ? C8 C9 C10 C5 -60.3(3) . . . . ? C4 C9 C10 C5 59.8(3) . . . . ? C2 C5 C10 C9 -60.0(3) . . . . ? C6 C5 C10 C9 60.5(3) . . . . ? C3 C1 C11 O2 -51.6(3) . . . . ? C2 C1 C11 O2 -173.7(2) . . . . ? C4 C1 C11 O2 66.3(3) . . . . ? C3 C1 C11 O1 128.4(2) . . . . ? C2 C1 C11 O1 6.4(3) . . . . ? C4 C1 C11 O1 -113.7(2) . . . . ? N1 C12 C13 C14 169.2(2) . . . . ? C19 C12 C13 C14 47.0(3) . . . . ? C12 C13 C14 C15 63.3(3) . . . . ? C13 C14 C15 C16 -65.1(4) . . . . ? C14 C15 C16 C17 -42.9(4) . . . . ? C15 C16 C17 C18 99.6(3) . . . . ? C16 C17 C18 C19 -65.0(3) . . . . ? C17 C18 C19 C12 65.5(3) . . . . ? N1 C12 C19 C18 135.5(2) . . . . ? C13 C12 C19 C18 -103.3(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 O1 0.91 1.88 2.769(3) 164 . N1 H1B O2 0.91 1.83 2.735(2) 177 1_455 N1 H1C O1 0.91 1.89 2.787(2) 169 3_666 ###END data_10 _database_code_depnum_ccdc_archive 'CCDC 797982' #TrackingRef '- Lemmerer.cif' _audit_creation_date 2010-10-13T10:19:18-00:00 _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 ; (cyclododecylammonium).(adamantanecarboxylate) ; _chemical_formula_moiety 'C11 H15 O2, C12 H26 N' _chemical_formula_sum 'C23 H41 N O2' _chemical_formula_weight 363.57 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.9710(6) _cell_length_b 6.5850(1) _cell_length_c 23.0547(5) _cell_angle_alpha 90 _cell_angle_beta 102.386(1) _cell_angle_gamma 90 _cell_volume 4295.87(15) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5411 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 28.26 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.124 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 0 0.261 0 1 0 0.275 -1 0 0 0.113 1 0 0 0.152 0 0 1 0.313 1 0 -2 0.286 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.07 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.9603 _exptl_absorpt_correction_T_max 0.9816 #----------------------------------------------------------------------------# # 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 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0681 _diffrn_reflns_av_unetI/netI 0.0464 _diffrn_reflns_number 13575 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 5186 _reflns_number_gt 3835 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1553P)^2^+5.2249P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5186 _refine_ls_number_parameters 318 _refine_ls_number_restraints 318 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1569 _refine_ls_wR_factor_gt 0.1231 _refine_ls_goodness_of_fit_ref 0.644 _refine_ls_restrained_S_all 0.628 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.301 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.048 #----------------------------------------------------------------------------# # 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 0.62914(4) 0.21537(17) 0.63390(5) 0.0197(2) Uani 1 1 d . . . C2A C 0.61686(5) 0.0633(2) 0.58253(6) 0.0284(3) Uani 0.928(2) 1 d PDU A 1 H2A1 H 0.6094 -0.0703 0.598 0.034 Uiso 0.928(2) 1 calc PR A 1 H2A2 H 0.6444 0.046 0.5639 0.034 Uiso 0.928(2) 1 calc PR A 1 C3A C 0.64016(5) 0.4223(2) 0.60885(6) 0.0244(3) Uani 0.928(2) 1 d PDU A 1 H3A1 H 0.6478 0.5226 0.6415 0.029 Uiso 0.928(2) 1 calc PR A 1 H3A2 H 0.668 0.4092 0.5906 0.029 Uiso 0.928(2) 1 calc PR A 1 C4A C 0.58581(5) 0.2406(2) 0.66214(6) 0.0263(3) Uani 0.928(2) 1 d PDU A 1 H4A1 H 0.5782 0.1089 0.6786 0.032 Uiso 0.928(2) 1 calc PR A 1 H4A2 H 0.5931 0.3397 0.6951 0.032 Uiso 0.928(2) 1 calc PR A 1 C5A C 0.57432(6) 0.1384(3) 0.53588(7) 0.0317(4) Uani 0.928(2) 1 d PDU A 1 H5A H 0.5668 0.0375 0.5028 0.038 Uiso 0.928(2) 1 calc PR A 1 C6A C 0.58605(6) 0.3425(3) 0.51141(7) 0.0327(4) Uani 0.928(2) 1 d PDU A 1 H6A1 H 0.5588 0.3907 0.4809 0.039 Uiso 0.928(2) 1 calc PR A 1 H6A2 H 0.6135 0.3275 0.4925 0.039 Uiso 0.928(2) 1 calc PR A 1 C7A C 0.59750(6) 0.4968(2) 0.56202(7) 0.0275(3) Uani 0.928(2) 1 d PDU A 1 H7A H 0.6051 0.631 0.546 0.033 Uiso 0.928(2) 1 calc PR A 1 C8A C 0.55507(6) 0.5200(3) 0.59101(8) 0.0319(4) Uani 0.928(2) 1 d PDU A 1 H8A1 H 0.5275 0.5705 0.5614 0.038 Uiso 0.928(2) 1 calc PR A 1 H8A2 H 0.5625 0.6202 0.6237 0.038 Uiso 0.928(2) 1 calc PR A 1 C9A C 0.54304(6) 0.3152(3) 0.61544(7) 0.0311(4) Uani 0.928(2) 1 d PDU A 1 H9A H 0.5151 0.3307 0.634 0.037 Uiso 0.928(2) 1 calc PR A 1 C10A C 0.53175(6) 0.1622(3) 0.56446(8) 0.0346(4) Uani 0.928(2) 1 d PDU A 1 H10A H 0.5237 0.0293 0.5798 0.041 Uiso 0.928(2) 1 calc PR A 1 H10B H 0.5041 0.2098 0.5344 0.041 Uiso 0.928(2) 1 calc PR A 1 C2B C 0.5871(5) 0.058(2) 0.6276(8) 0.032(3) Uani 0.072(2) 1 d PDU A 2 H2B1 H 0.5973 -0.0767 0.6163 0.038 Uiso 0.072(2) 1 calc PR A 2 H2B2 H 0.577 0.0452 0.6659 0.038 Uiso 0.072(2) 1 calc PR A 2 C3B C 0.6430(5) 0.232(3) 0.5742(7) 0.029(3) Uani 0.072(2) 1 d PDU A 2 H3B1 H 0.6546 0.0989 0.5636 0.035 Uiso 0.072(2) 1 calc PR A 2 H3B2 H 0.6692 0.3312 0.5774 0.035 Uiso 0.072(2) 1 calc PR A 2 C4B C 0.6117(5) 0.425(2) 0.6511(7) 0.024(3) Uani 0.072(2) 1 d PDU A 2 H4B1 H 0.6001 0.4131 0.6883 0.029 Uiso 0.072(2) 1 calc PR A 2 H4B2 H 0.6381 0.5237 0.6577 0.029 Uiso 0.072(2) 1 calc PR A 2 C5B C 0.5459(7) 0.137(3) 0.5794(9) 0.043(3) Uani 0.072(2) 1 d PDU A 2 H5B H 0.5186 0.0422 0.5753 0.052 Uiso 0.072(2) 1 calc PR A 2 C6B C 0.5624(8) 0.145(4) 0.5216(9) 0.046(3) Uani 0.072(2) 1 d PDU A 2 H6B1 H 0.5355 0.1799 0.4889 0.056 Uiso 0.072(2) 1 calc PR A 2 H6B2 H 0.5742 0.0093 0.5132 0.056 Uiso 0.072(2) 1 calc PR A 2 C7B C 0.6014(7) 0.301(3) 0.5244(9) 0.040(3) Uani 0.072(2) 1 d PDU A 2 H7B H 0.6114 0.3079 0.4856 0.048 Uiso 0.072(2) 1 calc PR A 2 C8B C 0.5871(9) 0.508(3) 0.5423(9) 0.041(3) Uani 0.072(2) 1 d PDU A 2 H8B1 H 0.6141 0.6023 0.5458 0.049 Uiso 0.072(2) 1 calc PR A 2 H8B2 H 0.5608 0.5603 0.5111 0.049 Uiso 0.072(2) 1 calc PR A 2 C9B C 0.5717(7) 0.499(3) 0.6005(8) 0.035(3) Uani 0.072(2) 1 d PDU A 2 H9B H 0.5609 0.6361 0.6103 0.042 Uiso 0.072(2) 1 calc PR A 2 C10B C 0.5313(6) 0.346(3) 0.5965(11) 0.041(3) Uani 0.072(2) 1 d PDU A 2 H10C H 0.522 0.3378 0.6353 0.049 Uiso 0.072(2) 1 calc PR A 2 H10D H 0.5035 0.3928 0.5666 0.049 Uiso 0.072(2) 1 calc PR A 2 C11 C 0.67102(4) 0.13883(18) 0.68123(5) 0.0215(2) Uani 1 1 d . A . O1 O 0.68704(3) -0.03421(14) 0.67574(4) 0.0314(2) Uani 1 1 d . . . O2 O 0.68786(3) 0.25602(13) 0.72441(4) 0.0270(2) Uani 1 1 d . . . C12 C 0.70224(4) -0.33621(18) 0.81451(5) 0.0224(2) Uani 1 1 d . . . H12 H 0.7191 -0.4494 0.8393 0.027 Uiso 1 1 calc R . . C13 C 0.72046(4) -0.13629(19) 0.84439(5) 0.0243(3) Uani 1 1 d . . . H13A H 0.7002 -0.024 0.8249 0.029 Uiso 1 1 calc R . . H13B H 0.7529 -0.112 0.8386 0.029 Uiso 1 1 calc R . . C14 C 0.72107(5) -0.1336(2) 0.91088(6) 0.0300(3) Uani 1 1 d . . . H14A H 0.6911 -0.1922 0.9173 0.036 Uiso 1 1 calc R . . H14B H 0.7472 -0.221 0.9318 0.036 Uiso 1 1 calc R . . C15 C 0.72719(5) 0.0789(2) 0.93805(6) 0.0334(3) Uani 1 1 d . . . H15A H 0.7557 0.142 0.9286 0.04 Uiso 1 1 calc R . . H15B H 0.7325 0.0668 0.9818 0.04 Uiso 1 1 calc R . . C16 C 0.68484(5) 0.2188(2) 0.91615(6) 0.0325(3) Uani 1 1 d . . . H16A H 0.6774 0.219 0.8722 0.039 Uiso 1 1 calc R . . H16B H 0.6937 0.359 0.9296 0.039 Uiso 1 1 calc R . . C17 C 0.64048(6) 0.1573(3) 0.93802(7) 0.0387(3) Uani 1 1 d . . . H17A H 0.6392 0.0072 0.9397 0.046 Uiso 1 1 calc R . . H17B H 0.6434 0.2088 0.979 0.046 Uiso 1 1 calc R . . C18 C 0.59409(6) 0.2345(2) 0.89992(7) 0.0399(4) Uani 1 1 d . . . H18A H 0.5966 0.383 0.8947 0.048 Uiso 1 1 calc R . . H18B H 0.5685 0.2103 0.9214 0.048 Uiso 1 1 calc R . . C19 C 0.58041(5) 0.1354(2) 0.83863(7) 0.0380(3) Uani 1 1 d . . . H19A H 0.553 0.2094 0.8149 0.046 Uiso 1 1 calc R . . H19B H 0.6071 0.1506 0.8184 0.046 Uiso 1 1 calc R . . C20 C 0.56772(5) -0.0898(2) 0.83961(8) 0.0398(4) Uani 1 1 d . . . H20A H 0.5905 -0.1571 0.872 0.048 Uiso 1 1 calc R . . H20B H 0.536 -0.1023 0.8487 0.048 Uiso 1 1 calc R . . C21 C 0.56775(5) -0.2012(2) 0.78150(7) 0.0370(3) Uani 1 1 d . . . H21A H 0.5467 -0.1281 0.7486 0.044 Uiso 1 1 calc R . . H21B H 0.5545 -0.339 0.7837 0.044 Uiso 1 1 calc R . . C22 C 0.61693(4) -0.2204(2) 0.76713(6) 0.0289(3) Uani 1 1 d . . . H22A H 0.6134 -0.266 0.7255 0.035 Uiso 1 1 calc R . . H22B H 0.6321 -0.085 0.7707 0.035 Uiso 1 1 calc R . . C23 C 0.64915(4) -0.3698(2) 0.80805(6) 0.0268(3) Uani 1 1 d . . . H23A H 0.6418 -0.362 0.848 0.032 Uiso 1 1 calc R . . H23B H 0.6414 -0.509 0.7929 0.032 Uiso 1 1 calc R . . N1 N 0.71452(3) -0.34748(15) 0.75467(4) 0.0217(2) Uani 1 1 d . . . H1A H 0.7009 -0.2417 0.7319 0.033 Uiso 1 1 calc R . . H1B H 0.7037 -0.4666 0.7368 0.033 Uiso 1 1 calc R . . H1C H 0.7465 -0.341 0.759 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0179(5) 0.0185(5) 0.0218(5) 0.0002(4) 0.0025(4) -0.0013(4) C2A 0.0282(7) 0.0246(6) 0.0300(7) -0.0067(5) 0.0007(5) -0.0003(5) C3A 0.0219(6) 0.0229(6) 0.0264(7) 0.0029(5) 0.0007(5) -0.0043(5) C4A 0.0199(6) 0.0341(7) 0.0250(6) 0.0030(5) 0.0049(5) -0.0001(5) C5A 0.0291(9) 0.0341(7) 0.0281(8) -0.0085(7) -0.0026(6) -0.0038(7) C6A 0.0297(8) 0.0426(9) 0.0236(7) 0.0012(6) 0.0008(6) 0.0001(7) C7A 0.0283(8) 0.0250(6) 0.0268(7) 0.0046(6) 0.0008(6) -0.0025(6) C8A 0.0270(8) 0.0324(7) 0.0330(8) -0.0004(6) -0.0010(6) 0.0088(7) C9A 0.0186(7) 0.0439(8) 0.0300(8) 0.0015(7) 0.0039(6) 0.0012(6) C10A 0.0231(8) 0.0390(8) 0.0373(9) 0.0013(7) -0.0029(6) -0.0075(6) C2B 0.019(6) 0.026(6) 0.043(6) 0.001(6) -0.010(6) -0.010(5) C3B 0.026(6) 0.039(7) 0.022(6) -0.004(6) 0.003(5) 0.008(5) C4B 0.020(6) 0.016(6) 0.035(6) 0.005(5) 0.002(5) 0.005(5) C5B 0.028(7) 0.040(5) 0.051(7) 0.008(6) -0.017(5) -0.006(5) C6B 0.037(7) 0.047(6) 0.043(6) -0.003(6) -0.019(6) 0.007(6) C7B 0.038(7) 0.048(6) 0.028(6) 0.006(5) -0.007(5) 0.009(5) C8B 0.034(7) 0.043(5) 0.040(6) 0.013(6) -0.006(6) 0.004(5) C9B 0.026(7) 0.031(6) 0.042(6) 0.004(5) -0.007(5) 0.008(5) C10B 0.024(6) 0.050(6) 0.044(8) 0.009(6) -0.005(5) 0.003(5) C11 0.0174(5) 0.0228(5) 0.0248(6) 0.0036(4) 0.0058(4) -0.0019(4) O1 0.0341(5) 0.0261(5) 0.0325(5) 0.0030(4) 0.0037(4) 0.0092(4) O2 0.0234(4) 0.0264(4) 0.0276(5) -0.0001(4) -0.0027(3) -0.0023(3) C12 0.0211(6) 0.0234(5) 0.0224(6) 0.0006(4) 0.0039(4) 0.0007(4) C13 0.0232(6) 0.0253(6) 0.0238(6) -0.0019(5) 0.0036(5) -0.0013(4) C14 0.0348(7) 0.0311(6) 0.0230(6) -0.0010(5) 0.0033(5) 0.0043(5) C15 0.0349(7) 0.0370(7) 0.0272(7) -0.0084(6) 0.0044(5) -0.0008(6) C16 0.0384(7) 0.0285(6) 0.0328(7) -0.0030(5) 0.0128(6) 0.0010(5) C17 0.0424(8) 0.0470(8) 0.0317(7) 0.0034(6) 0.0188(6) 0.0066(7) C18 0.0411(8) 0.0425(8) 0.0421(8) 0.0032(7) 0.0225(7) 0.0092(6) C19 0.0356(8) 0.0396(8) 0.0417(8) 0.0065(6) 0.0148(6) 0.0080(6) C20 0.0316(7) 0.0441(8) 0.0501(9) 0.0046(7) 0.0229(7) 0.0009(6) C21 0.0186(6) 0.0451(8) 0.0474(9) 0.0017(7) 0.0073(6) -0.0026(5) C22 0.0210(6) 0.0372(7) 0.0286(6) 0.0010(5) 0.0055(5) 0.0007(5) C23 0.0228(6) 0.0276(6) 0.0304(6) 0.0010(5) 0.0066(5) -0.0034(5) N1 0.0192(5) 0.0212(5) 0.0235(5) -0.0017(4) 0.0020(4) 0.0012(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 C3B 1.519(16) . ? C1 C11 1.5327(16) . ? C1 C2A 1.5332(17) . ? C1 C3A 1.5396(17) . ? C1 C4A 1.5422(17) . ? C1 C4B 1.550(15) . ? C1 C2B 1.580(15) . ? C2A C5A 1.533(2) . ? C2A H2A1 0.99 . ? C2A H2A2 0.99 . ? C3A C7A 1.5370(19) . ? C3A H3A1 0.99 . ? C3A H3A2 0.99 . ? C4A C9A 1.537(2) . ? C4A H4A1 0.99 . ? C4A H4A2 0.99 . ? C5A C6A 1.524(2) . ? C5A C10A 1.526(2) . ? C5A H5A 1 . ? C6A C7A 1.529(2) . ? C6A H6A1 0.99 . ? C6A H6A2 0.99 . ? C7A C8A 1.528(2) . ? C7A H7A 1 . ? C8A C9A 1.530(2) . ? C8A H8A1 0.99 . ? C8A H8A2 0.99 . ? C9A C10A 1.529(2) . ? C9A H9A 1 . ? C10A H10A 0.99 . ? C10A H10B 0.99 . ? C2B C5B 1.536(16) . ? C2B H2B1 0.99 . ? C2B H2B2 0.99 . ? C3B C7B 1.542(16) . ? C3B H3B1 0.99 . ? C3B H3B2 0.99 . ? C4B C9B 1.537(16) . ? C4B H4B1 0.99 . ? C4B H4B2 0.99 . ? C5B C6B 1.508(18) . ? C5B C10B 1.513(17) . ? C5B H5B 1 . ? C6B C7B 1.517(18) . ? C6B H6B1 0.99 . ? C6B H6B2 0.99 . ? C7B C8B 1.508(17) . ? C7B H7B 1 . ? C8B C9B 1.503(17) . ? C8B H8B1 0.99 . ? C8B H8B2 0.99 . ? C9B C10B 1.532(17) . ? C9B H9B 1 . ? C10B H10C 0.99 . ? C10B H10D 0.99 . ? C11 O1 1.2470(15) . ? C11 O2 1.2711(15) . ? C12 N1 1.4985(15) . ? C12 C13 1.5266(17) . ? C12 C23 1.5294(17) . ? C12 H12 1 . ? C13 C14 1.5293(18) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.5279(19) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 C16 1.531(2) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.532(2) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.526(2) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 C19 1.530(2) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 C20 1.529(2) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 C21 1.528(2) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 C22 1.5358(18) . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 C23 1.5335(18) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? N1 H1A 0.91 . ? N1 H1B 0.91 . ? N1 H1C 0.91 . ? 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 C3B C1 C11 110.3(5) . . ? C3B C1 C2A 53.9(7) . . ? C11 C1 C2A 110.63(10) . . ? C3B C1 C3A 58.6(7) . . ? C11 C1 C3A 111.21(9) . . ? C2A C1 C3A 108.70(10) . . ? C3B C1 C4A 140.6(5) . . ? C11 C1 C4A 109.07(10) . . ? C2A C1 C4A 108.74(10) . . ? C3A C1 C4A 108.42(10) . . ? C3B C1 C4B 109.3(9) . . ? C11 C1 C4B 111.2(5) . . ? C2A C1 C4B 138.1(5) . . ? C3A C1 C4B 54.0(6) . . ? C4A C1 C4B 57.1(6) . . ? C3B C1 C2B 108.3(9) . . ? C11 C1 C2B 109.1(6) . . ? C2A C1 C2B 57.0(7) . . ? C3A C1 C2B 139.6(6) . . ? C4A C1 C2B 55.1(7) . . ? C4B C1 C2B 108.6(9) . . ? C1 C2A C5A 110.47(12) . . ? C1 C2A H2A1 109.6 . . ? C5A C2A H2A1 109.6 . . ? C1 C2A H2A2 109.6 . . ? C5A C2A H2A2 109.6 . . ? H2A1 C2A H2A2 108.1 . . ? C7A C3A C1 110.24(11) . . ? C7A C3A H3A1 109.6 . . ? C1 C3A H3A1 109.6 . . ? C7A C3A H3A2 109.6 . . ? C1 C3A H3A2 109.6 . . ? H3A1 C3A H3A2 108.1 . . ? C9A C4A C1 110.22(11) . . ? C9A C4A H4A1 109.6 . . ? C1 C4A H4A1 109.6 . . ? C9A C4A H4A2 109.6 . . ? C1 C4A H4A2 109.6 . . ? H4A1 C4A H4A2 108.1 . . ? C6A C5A C10A 109.53(16) . . ? C6A C5A C2A 109.54(13) . . ? C10A C5A C2A 109.43(14) . . ? C6A C5A H5A 109.4 . . ? C10A C5A H5A 109.4 . . ? C2A C5A H5A 109.4 . . ? C5A C6A C7A 109.44(14) . . ? C5A C6A H6A1 109.8 . . ? C7A C6A H6A1 109.8 . . ? C5A C6A H6A2 109.8 . . ? C7A C6A H6A2 109.8 . . ? H6A1 C6A H6A2 108.2 . . ? C8A C7A C6A 109.69(14) . . ? C8A C7A C3A 109.02(13) . . ? C6A C7A C3A 109.50(13) . . ? C8A C7A H7A 109.5 . . ? C6A C7A H7A 109.5 . . ? C3A C7A H7A 109.5 . . ? C7A C8A C9A 109.96(13) . . ? C7A C8A H8A1 109.7 . . ? C9A C8A H8A1 109.7 . . ? C7A C8A H8A2 109.7 . . ? C9A C8A H8A2 109.7 . . ? H8A1 C8A H8A2 108.2 . . ? C10A C9A C8A 109.02(14) . . ? C10A C9A C4A 109.58(14) . . ? C8A C9A C4A 109.05(13) . . ? C10A C9A H9A 109.7 . . ? C8A C9A H9A 109.7 . . ? C4A C9A H9A 109.7 . . ? C5A C10A C9A 109.88(13) . . ? C5A C10A H10A 109.7 . . ? C9A C10A H10A 109.7 . . ? C5A C10A H10B 109.7 . . ? C9A C10A H10B 109.7 . . ? H10A C10A H10B 108.2 . . ? C5B C2B C1 108.0(12) . . ? C5B C2B H2B1 110.1 . . ? C1 C2B H2B1 110.1 . . ? C5B C2B H2B2 110.1 . . ? C1 C2B H2B2 110.1 . . ? H2B1 C2B H2B2 108.4 . . ? C1 C3B C7B 112.3(12) . . ? C1 C3B H3B1 109.1 . . ? C7B C3B H3B1 109.1 . . ? C1 C3B H3B2 109.1 . . ? C7B C3B H3B2 109.2 . . ? H3B1 C3B H3B2 107.9 . . ? C9B C4B C1 108.7(12) . . ? C9B C4B H4B1 109.9 . . ? C1 C4B H4B1 109.9 . . ? C9B C4B H4B2 109.9 . . ? C1 C4B H4B2 110 . . ? H4B1 C4B H4B2 108.3 . . ? C6B C5B C10B 111.1(17) . . ? C6B C5B C2B 107.8(16) . . ? C10B C5B C2B 109.6(15) . . ? C6B C5B H5B 109.4 . . ? C10B C5B H5B 109.4 . . ? C2B C5B H5B 109.4 . . ? C5B C6B C7B 111.0(16) . . ? C5B C6B H6B1 109.4 . . ? C7B C6B H6B1 109.4 . . ? C5B C6B H6B2 109.4 . . ? C7B C6B H6B2 109.4 . . ? H6B1 C6B H6B2 108 . . ? C8B C7B C6B 112.2(17) . . ? C8B C7B C3B 106.1(15) . . ? C6B C7B C3B 106.9(15) . . ? C8B C7B H7B 110.5 . . ? C6B C7B H7B 110.5 . . ? C3B C7B H7B 110.5 . . ? C9B C8B C7B 111.1(16) . . ? C9B C8B H8B1 109.4 . . ? C7B C8B H8B1 109.4 . . ? C9B C8B H8B2 109.4 . . ? C7B C8B H8B2 109.4 . . ? H8B1 C8B H8B2 108 . . ? C8B C9B C10B 110.0(16) . . ? C8B C9B C4B 111.8(15) . . ? C10B C9B C4B 106.3(14) . . ? C8B C9B H9B 109.6 . . ? C10B C9B H9B 109.6 . . ? C4B C9B H9B 109.6 . . ? C5B C10B C9B 111.0(15) . . ? C5B C10B H10C 109.4 . . ? C9B C10B H10C 109.4 . . ? C5B C10B H10D 109.4 . . ? C9B C10B H10D 109.4 . . ? H10C C10B H10D 108 . . ? O1 C11 O2 123.07(11) . . ? O1 C11 C1 118.89(11) . . ? O2 C11 C1 118.03(10) . . ? N1 C12 C13 109.31(10) . . ? N1 C12 C23 109.61(10) . . ? C13 C12 C23 114.32(10) . . ? N1 C12 H12 107.8 . . ? C13 C12 H12 107.8 . . ? C23 C12 H12 107.8 . . ? C12 C13 C14 113.00(11) . . ? C12 C13 H13A 109 . . ? C14 C13 H13A 109 . . ? C12 C13 H13B 109 . . ? C14 C13 H13B 109 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 113.38(11) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 C16 113.67(11) . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C15 C16 C17 113.70(12) . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16A 108.8 . . ? C15 C16 H16B 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C16 114.81(12) . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C16 C17 H17B 108.6 . . ? H17A C17 H17B 107.5 . . ? C17 C18 C19 114.28(12) . . ? C17 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? C17 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C18 114.56(13) . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19B 108.6 . . ? C18 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? C21 C20 C19 114.04(13) . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C20 C21 C22 113.81(12) . . ? C20 C21 H21A 108.8 . . ? C22 C21 H21A 108.8 . . ? C20 C21 H21B 108.8 . . ? C22 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C23 C22 C21 112.98(11) . . ? C23 C22 H22A 109 . . ? C21 C22 H22A 109 . . ? C23 C22 H22B 109 . . ? C21 C22 H22B 109 . . ? H22A C22 H22B 107.8 . . ? C12 C23 C22 115.72(11) . . ? C12 C23 H23A 108.4 . . ? C22 C23 H23A 108.4 . . ? C12 C23 H23B 108.4 . . ? C22 C23 H23B 108.4 . . ? H23A C23 H23B 107.4 . . ? C12 N1 H1A 109.5 . . ? C12 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C12 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3B C1 C2A C5A -80.5(7) . . . . ? C11 C1 C2A C5A 178.86(11) . . . . ? C3A C1 C2A C5A -58.76(15) . . . . ? C4A C1 C2A C5A 59.09(15) . . . . ? C4B C1 C2A C5A -2.2(9) . . . . ? C2B C1 C2A C5A 78.9(7) . . . . ? C3B C1 C3A C7A 79.2(7) . . . . ? C11 C1 C3A C7A -179.39(11) . . . . ? C2A C1 C3A C7A 58.58(14) . . . . ? C4A C1 C3A C7A -59.48(14) . . . . ? C4B C1 C3A C7A -78.0(7) . . . . ? C2B C1 C3A C7A -2.1(12) . . . . ? C3B C1 C4A C9A -3.2(11) . . . . ? C11 C1 C4A C9A -179.40(11) . . . . ? C2A C1 C4A C9A -58.67(14) . . . . ? C3A C1 C4A C9A 59.35(14) . . . . ? C4B C1 C4A C9A 77.2(6) . . . . ? C2B C1 C4A C9A -79.0(7) . . . . ? C1 C2A C5A C6A 60.10(17) . . . . ? C1 C2A C5A C10A -59.99(17) . . . . ? C10A C5A C6A C7A 59.89(18) . . . . ? C2A C5A C6A C7A -60.14(18) . . . . ? C5A C6A C7A C8A -59.52(18) . . . . ? C5A C6A C7A C3A 60.09(17) . . . . ? C1 C3A C7A C8A 60.29(15) . . . . ? C1 C3A C7A C6A -59.73(16) . . . . ? C6A C7A C8A C9A 59.50(18) . . . . ? C3A C7A C8A C9A -60.39(17) . . . . ? C7A C8A C9A C10A -59.30(18) . . . . ? C7A C8A C9A C4A 60.30(17) . . . . ? C1 C4A C9A C10A 59.26(16) . . . . ? C1 C4A C9A C8A -60.00(16) . . . . ? C6A C5A C10A C9A -60.37(19) . . . . ? C2A C5A C10A C9A 59.73(18) . . . . ? C8A C9A C10A C5A 59.72(19) . . . . ? C4A C9A C10A C5A -59.55(18) . . . . ? C3B C1 C2B C5B -59.2(15) . . . . ? C11 C1 C2B C5B -179.2(11) . . . . ? C2A C1 C2B C5B -76.5(13) . . . . ? C3A C1 C2B C5B 3(2) . . . . ? C4A C1 C2B C5B 80.4(13) . . . . ? C4B C1 C2B C5B 59.4(15) . . . . ? C11 C1 C3B C7B 177.7(11) . . . . ? C2A C1 C3B C7B 76.4(12) . . . . ? C3A C1 C3B C7B -79.3(12) . . . . ? C4A C1 C3B C7B 2(2) . . . . ? C4B C1 C3B C7B -59.8(15) . . . . ? C2B C1 C3B C7B 58.4(15) . . . . ? C3B C1 C4B C9B 54.9(14) . . . . ? C11 C1 C4B C9B 176.9(10) . . . . ? C2A C1 C4B C9B -2.1(17) . . . . ? C3A C1 C4B C9B 75.5(11) . . . . ? C4A C1 C4B C9B -83.5(11) . . . . ? C2B C1 C4B C9B -63.0(14) . . . . ? C1 C2B C5B C6B 62.5(18) . . . . ? C1 C2B C5B C10B -58.6(19) . . . . ? C10B C5B C6B C7B 55(2) . . . . ? C2B C5B C6B C7B -66(2) . . . . ? C5B C6B C7B C8B -54(2) . . . . ? C5B C6B C7B C3B 62(2) . . . . ? C1 C3B C7B C8B 61.2(18) . . . . ? C1 C3B C7B C6B -58.6(18) . . . . ? C6B C7B C8B C9B 56(2) . . . . ? C3B C7B C8B C9B -61(2) . . . . ? C7B C8B C9B C10B -57(2) . . . . ? C7B C8B C9B C4B 61(2) . . . . ? C1 C4B C9B C8B -56.4(18) . . . . ? C1 C4B C9B C10B 63.6(17) . . . . ? C6B C5B C10B C9B -57(2) . . . . ? C2B C5B C10B C9B 63(2) . . . . ? C8B C9B C10B C5B 57(2) . . . . ? C4B C9B C10B C5B -64(2) . . . . ? C3B C1 C11 O1 -63.3(7) . . . . ? C2A C1 C11 O1 -5.47(16) . . . . ? C3A C1 C11 O1 -126.37(12) . . . . ? C4A C1 C11 O1 114.10(12) . . . . ? C4B C1 C11 O1 175.3(7) . . . . ? C2B C1 C11 O1 55.5(8) . . . . ? C3B C1 C11 O2 116.6(7) . . . . ? C2A C1 C11 O2 174.43(11) . . . . ? C3A C1 C11 O2 53.53(14) . . . . ? C4A C1 C11 O2 -66.00(13) . . . . ? C4B C1 C11 O2 -4.8(7) . . . . ? C2B C1 C11 O2 -124.6(8) . . . . ? N1 C12 C13 C14 -165.26(10) . . . . ? C23 C12 C13 C14 71.47(14) . . . . ? C12 C13 C14 C15 -165.58(11) . . . . ? C13 C14 C15 C16 67.69(16) . . . . ? C14 C15 C16 C17 69.02(16) . . . . ? C15 C16 C17 C18 -157.19(13) . . . . ? C16 C17 C18 C19 69.17(18) . . . . ? C17 C18 C19 C20 67.46(17) . . . . ? C18 C19 C20 C21 -163.65(12) . . . . ? C19 C20 C21 C22 67.10(17) . . . . ? C20 C21 C22 C23 70.99(16) . . . . ? N1 C12 C23 C22 -58.22(14) . . . . ? C13 C12 C23 C22 64.89(15) . . . . ? C21 C22 C23 C12 -156.05(12) . . . . ? 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 0.91 1.87 2.753(1) 164 . N1 H1B O2 0.91 1.89 2.769(1) 162 1_545 N1 H1C O2 0.91 1.97 2.848(1) 163 4_646