Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_HAGI-159 _database_code_CSD 169360 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Hagimoto, Yuri' 'Hasegawa, Hiroaki' 'Nishide, Kiyoharu' 'Node, Manabu' 'Shiro, Motoo' _publ_contact_author_name 'Prof Manabu Node' _publ_contact_author_address ; Dept of Pharmaceutical Manufacturing Chemistry Kyoto Pharmaceutical University Misasagi Yamashina Kyoto 607-8414 JAPAN ; _publ_contact_author_email 'NODE@MB.KYOTO-PHU.AC.JP' _publ_contact_author_fax ' +81-75-595-4775 ' _publ_contact_author_phone ' +81-75-595-4639 ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_section_title ; A Novel Intramolecular Through-Space Interaction between F and CN: A Strategy for the Conformational Control of an Acyclic System ; # TEXT _publ_section_abstract ; X-Ray crystallographic analyses of fluorocyanides anti-1 and 2 revealed a no vel intramolecular through-space interaction between F and CN in an acyclic system, which was applied to a stereoselective protonation of an acyclic flu orocyanides 2 having flexible conformation. ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; We are grateful for a Grant-in-Aid (No. 11672126 to KN) from the Ministry of Education, Science, Sports and Culture of Japan, in partial financial support of this research. We are also grateful to Prof. Tamejiro Hiyama, Kyoto University, for helpful discussions at Sagami Chemical Research Center. We also thank the Japan Energy Corporation, Toda, Saitama, Japan, for its kind gift of (R)-epoxyoctane. ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. ; _publ_section_figure_captions ; none ; _publ_section_exptl_prep ; See supporting Information ; _publ_section_exptl_refinement ; See supporting Information ; #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C17 H24 F N O ' _chemical_formula_moiety 'C17 H24 F N O ' _chemical_formula_weight 277.38 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z _cell_length_a 7.696(4) _cell_length_b 5.627(3) _cell_length_c 18.628(2) _cell_angle_alpha 90 _cell_angle_beta 95.02(2) _cell_angle_gamma 90 _cell_volume 803.6(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 27.9 _cell_measurement_theta_max 29.9 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.146 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.628 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.919 _exptl_absorpt_correction_T_max 0.998 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 1449 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_theta_max 60.15 _diffrn_measured_fraction_theta_max 0.6018 _diffrn_reflns_theta_full 60.15 _diffrn_measured_fraction_theta_full 0.6018 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.00 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1431 _reflns_number_gt 994 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1923 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1431 _refine_ls_number_parameters 181 _refine_ls_goodness_of_fit_ref 1.597 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.08000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.18 _refine_diff_density_min 0.00 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack -3.2(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'F' 'F' 0.073 0.053 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F(1) F 0.3657(4) -0.5174 -0.1767(2) 0.0956(10) Uani 1.00 d . . . O(1) O -0.2743(4) -0.1691(9) -0.4381(2) 0.0800(10) Uani 1.00 d . . . N(1) N 0.5426(5) -0.660(1) -0.3251(2) 0.079(1) Uani 1.00 d . . . C(1) C -0.3280(6) 0.030(1) -0.4811(2) 0.087(2) Uani 1.00 d . . . C(2) C -0.1026(6) -0.177(1) -0.4089(2) 0.063(1) Uani 1.00 d . . . C(3) C 0.0172(6) -0.001(1) -0.4188(2) 0.068(1) Uani 1.00 d . . . C(4) C 0.1873(6) -0.025(1) -0.3859(2) 0.066(1) Uani 1.00 d . . . C(5) C 0.2337(5) -0.216(1) -0.3430(2) 0.060(1) Uani 1.00 d . . . C(6) C 0.1126(6) -0.392(1) -0.3356(2) 0.066(1) Uani 1.00 d . . . C(7) C -0.0586(6) -0.372(1) -0.3671(2) 0.068(1) Uani 1.00 d . . . C(8) C 0.4217(6) -0.238(1) -0.3079(2) 0.066(1) Uani 1.00 d . . . C(9) C 0.4906(6) -0.477(1) -0.3170(2) 0.068(1) Uani 1.00 d . . . C(10) C 0.4393(6) -0.156(1) -0.2288(2) 0.071(1) Uani 1.00 d . . . C(11) C 0.3291(7) -0.278(1) -0.1780(2) 0.071(1) Uani 1.00 d . . . C(12) C 0.3572(7) -0.181(1) -0.1019(2) 0.080(1) Uani 1.00 d . . . C(13) C 0.2421(7) -0.302(1) -0.0500(2) 0.085(2) Uani 1.00 d . . . C(14) C 0.2657(7) -0.198(1) 0.0257(2) 0.083(1) Uani 1.00 d . . . C(15) C 0.1540(7) -0.317(1) 0.0784(2) 0.085(2) Uani 1.00 d . . . C(16) C 0.1780(7) -0.222(1) 0.1540(2) 0.088(2) Uani 1.00 d . . . C(17) C 0.0735(8) -0.349(2) 0.2057(3) 0.105(2) Uani 1.00 d . . . H(1) H -0.2601 0.0344 -0.5224 0.1102 Uiso 1.00 calc . . . H(2) H -0.3109 0.1688 -0.4546 0.1102 Uiso 1.00 calc . . . H(3) H -0.4476 0.0119 -0.4986 0.1102 Uiso 1.00 calc . . . H(4) H -0.0167 0.1338 -0.4477 0.0826 Uiso 1.00 calc . . . H(5) H 0.2757 0.0875 -0.3948 0.0820 Uiso 1.00 calc . . . H(6) H 0.1442 -0.5355 -0.3074 0.0784 Uiso 1.00 calc . . . H(7) H -0.1436 -0.4986 -0.3589 0.0823 Uiso 1.00 calc . . . H(8) H 0.4921 -0.1379 -0.3352 0.0792 Uiso 1.00 calc . . . H(9) H 0.4212 0.0033 -0.2259 0.0877 Uiso 1.00 calc . . . H(10) H 0.5606 -0.1930 -0.2095 0.0877 Uiso 1.00 calc . . . H(11) H 0.2091 -0.2601 -0.1969 0.0838 Uiso 1.00 calc . . . H(12) H 0.3323 -0.0194 -0.1021 0.0998 Uiso 1.00 calc . . . H(13) H 0.4763 -0.2087 -0.0846 0.0998 Uiso 1.00 calc . . . H(14) H 0.1229 -0.2912 -0.0690 0.1028 Uiso 1.00 calc . . . H(15) H 0.2702 -0.4735 -0.0486 0.1028 Uiso 1.00 calc . . . H(16) H 0.2406 -0.0357 0.0239 0.1004 Uiso 1.00 calc . . . H(17) H 0.3866 -0.2197 0.0445 0.1004 Uiso 1.00 calc . . . H(18) H 0.0314 -0.2997 0.0594 0.1084 Uiso 1.00 calc . . . H(19) H 0.1743 -0.4904 0.0773 0.1084 Uiso 1.00 calc . . . H(20) H 0.1531 -0.0593 0.1549 0.1080 Uiso 1.00 calc . . . H(21) H 0.3015 -0.2428 0.1717 0.1080 Uiso 1.00 calc . . . H(22) H 0.0885 -0.2930 0.2528 0.1227 Uiso 1.00 calc . . . H(23) H 0.0983 -0.5201 0.2061 0.1227 Uiso 1.00 calc . . . H(24) H -0.0506 -0.3377 0.1888 0.1227 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.125(2) 0.073(2) 0.089(2) -0.004(2) 0.010(2) 0.004(2) O(1) 0.071(2) 0.089(2) 0.077(2) -0.001(2) -0.011(1) 0.017(2) N(1) 0.077(3) 0.070(2) 0.089(2) -0.007(2) -0.001(2) -0.002(2) C(1) 0.094(4) 0.089(4) 0.073(3) 0.010(3) -0.014(3) 0.013(2) C(2) 0.069(2) 0.067(2) 0.051(2) -0.003(2) -0.004(2) -0.003(2) C(3) 0.080(2) 0.063(3) 0.058(2) -0.005(2) -0.008(2) 0.007(2) C(4) 0.077(2) 0.060(2) 0.060(2) -0.002(2) -0.002(2) -0.001(2) C(5) 0.064(2) 0.059(2) 0.056(2) -0.002(2) -0.003(2) -0.005(2) C(6) 0.069(2) 0.060(3) 0.067(2) -0.006(2) -0.004(2) 0.002(2) C(7) 0.071(2) 0.067(3) 0.064(2) -0.004(3) -0.004(2) 0.007(2) C(8) 0.065(2) 0.066(2) 0.065(2) -0.009(2) -0.008(2) 0.003(2) C(9) 0.071(3) 0.066(2) 0.065(3) -0.011(2) -0.007(2) 0.006(2) C(10) 0.080(3) 0.066(3) 0.064(2) -0.004(2) -0.006(2) -0.003(2) C(11) 0.075(3) 0.074(2) 0.061(2) 0.001(2) -0.007(2) 0.000(2) C(12) 0.087(3) 0.089(4) 0.060(2) 0.009(3) -0.010(2) -0.009(2) C(13) 0.095(3) 0.095(4) 0.061(2) -0.007(3) -0.007(2) -0.010(2) C(14) 0.095(3) 0.090(4) 0.062(2) -0.005(3) -0.008(2) -0.009(2) C(15) 0.082(3) 0.102(4) 0.069(2) -0.005(3) -0.003(2) -0.013(2) C(16) 0.097(4) 0.098(4) 0.068(2) 0.003(3) -0.006(2) -0.009(2) C(17) 0.098(4) 0.142(6) 0.078(3) -0.010(4) 0.020(3) -0.014(3) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SHELXS86 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(9) 2.872(6) . . yes F(1) C(11) 1.375(10) . . yes O(1) C(1) 1.417(9) . . yes O(1) C(2) 1.385(6) . . yes N(1) C(9) 1.118(8) . . yes C(2) C(3) 1.376(8) . . yes C(2) C(7) 1.372(8) . . yes C(3) C(4) 1.403(7) . . yes C(4) C(5) 1.367(8) . . yes C(5) C(6) 1.376(8) . . yes C(5) C(8) 1.540(8) . . yes C(6) C(7) 1.399(7) . . yes C(8) C(9) 1.463(9) . . yes C(8) C(10) 1.538(7) . . yes C(10) C(11) 1.493(8) . . yes C(11) C(12) 1.516(8) . . yes C(12) C(13) 1.527(9) . . yes C(13) C(14) 1.522(8) . . yes C(14) C(15) 1.516(9) . . yes C(15) C(16) 1.503(8) . . yes C(16) C(17) 1.49(1) . . yes #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) O(1) C(2) 117.8(5) . . . yes O(1) C(2) C(3) 123.5(5) . . . yes O(1) C(2) C(7) 115.3(5) . . . yes C(3) C(2) C(7) 121.2(5) . . . yes C(2) C(3) C(4) 118.8(5) . . . yes C(3) C(4) C(5) 121.1(5) . . . yes C(4) C(5) C(6) 118.7(5) . . . yes C(4) C(5) C(8) 120.0(5) . . . yes C(6) C(5) C(8) 121.2(5) . . . yes C(5) C(6) C(7) 121.5(5) . . . yes C(2) C(7) C(6) 118.6(5) . . . yes C(5) C(8) C(9) 111.3(5) . . . yes C(5) C(8) C(10) 112.5(5) . . . yes C(9) C(8) C(10) 112.6(5) . . . yes C(9) F(1) C(11) 89.4(4) . . . yes N(1) C(9) C(8) 178.9(7) . . . yes C(8) C(10) C(11) 117.5(5) . . . yes F(1) C(9) N(1) 101.6(5) . . . yes F(1) C(9) C(8) 79.2(4) . . . yes F(1) C(11) C(10) 109.6(5) . . . yes F(1) C(11) C(12) 108.9(5) . . . yes C(10) C(11) C(12) 112.6(5) . . . yes C(11) C(12) C(13) 112.9(6) . . . yes C(12) C(13) C(14) 112.9(5) . . . yes C(13) C(14) C(15) 113.7(6) . . . yes C(14) C(15) C(16) 114.7(6) . . . yes C(15) C(16) C(17) 113.9(7) . . . yes #------------------------------------------------------------------------------ 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 F(1) C(11) C(8) C(9) -6.7(5) . . . . yes F(1) C(11) C(10) C(8) 59.0(7) . . . . yes F(1) C(11) C(12) C(13) -59.4(7) . . . . yes O(1) C(2) C(3) C(4) 179.2(5) . . . . yes O(1) C(2) C(7) C(6) -179.9(5) . . . . yes N(1) C(9) C(8) C(5) 53(34) . . . . yes N(1) C(9) C(8) C(10) -179(33) . . . . yes C(1) O(1) C(2) C(3) 0.5(8) . . . . yes C(1) O(1) C(2) C(7) 179.2(5) . . . . yes C(2) C(3) C(4) C(5) -1.7(8) . . . . yes C(2) C(7) C(6) C(5) 3.0(8) . . . . yes C(3) C(2) C(7) C(6) -1.3(8) . . . . yes C(3) C(4) C(5) C(6) 3.4(8) . . . . yes C(3) C(4) C(5) C(8) 179.7(5) . . . . yes C(4) C(3) C(2) C(7) 0.6(8) . . . . yes C(4) C(5) C(6) C(7) -4.1(8) . . . . yes C(4) C(5) C(8) C(9) -133.2(6) . . . . yes C(4) C(5) C(8) C(10) 99.3(6) . . . . yes C(5) C(8) C(10) C(11) 58.0(7) . . . . yes C(6) C(5) C(8) C(9) 42.9(7) . . . . yes C(6) C(5) C(8) C(10) -84.6(7) . . . . yes C(7) C(6) C(5) C(8) 179.7(5) . . . . yes C(8) C(10) C(11) C(12) -179.6(5) . . . . yes C(9) C(8) C(10) C(11) -68.8(7) . . . . yes C(10) C(11) C(12) C(13) 178.8(5) . . . . yes C(11) C(12) C(13) C(14) -178.0(5) . . . . yes C(12) C(13) C(14) C(15) -179.4(6) . . . . yes C(13) C(14) C(15) C(16) 178.6(6) . . . . yes C(14) C(15) C(16) C(17) -177.2(6) . . . . yes C(14) C(15) C(16) C(17) -177.2(6) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F(1) C(9) 2.872(6) . . ? O(1) C(9) 3.477(7) . 1_455 ? O(1) C(8) 3.537(7) . 1_455 ? N(1) C(8) 3.405(9) . 1_545 ? N(1) C(10) 3.447(8) . 1_545 ? N(1) C(4) 3.525(8) . 1_545 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_hagi-57-1 _database_code_CSD 169361 _audit_creation_date 'Wed Oct 10 18:42:15 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # TEXT _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Hagimoto, Yuri' 'Hasegawa, Hiroaki' 'Nishide, Kiyoharu' 'Node, Manabu' 'Shiro, Motoo' _publ_contact_author_name 'Prof Manabu Node' _publ_contact_author_address ; Dept of Pharmaceutical Manufacturing Chemistry Kyoto Pharmaceutical University Misasagi Yamashina Kyoto 607-8414 JAPAN ; _publ_contact_author_email 'NODE@MB.KYOTO-PHU.AC.JP' _publ_contact_author_fax ' +81-75-595-4775 ' _publ_contact_author_phone ' +81-75-595-4639 ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_section_title ; A Novel Intramolecular Through-Space Interaction between F and CN: A Strategy for the Conformational Control of an Acyclic System ; _publ_section_abstract ; X-Ray crystallographic analyses of fluorocyanides anti-1 and 2 revealed a novel intramolecular through-space interaction between F and CN in an acyc lic system, which was applied to a stereoselective protonation of an acyclic fluorocyanides 2 having flexible conformation. ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; We are grateful for a Grant-in-Aid (No. 11672126 to KN) from the Ministr y of Education, Science, Sports and Culture of Japan, in partial financial s upport of this research. We are also grateful to Prof. Tamejiro Hiyama, Kyo to University, for helpful discussions at Sagami Chemical Research Center. We also thank the Japan Energy Corporation, Toda, Saitama, Japan, for its ki nd gift of (R)-epoxyoctane. ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; _publ_section_figure_captions ; Figure 1 ; _publ_section_exptl_prep ; See supporting Information ; _publ_section_exptl_refinement ; See supporting Information ; #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C16 H22 F N O ' _chemical_formula_moiety 'C16 H22 F N O ' _chemical_formula_weight 263.35 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z _cell_length_a 7.855(2) _cell_length_b 5.462(2) _cell_length_c 17.607(1) _cell_angle_alpha 90 _cell_angle_beta 100.90(1) _cell_angle_gamma 90 _cell_volume 741.7(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25.5 _cell_measurement_theta_max 29.8 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.655 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 1337 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_theta_max 60.06 _diffrn_measured_fraction_theta_max 0.9992 _diffrn_reflns_theta_full 60.06 _diffrn_measured_fraction_theta_full 0.9992 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.38 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1233 _reflns_number_gt 843 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0839 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1233 _refine_ls_number_parameters 174 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.03000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0011 _refine_diff_density_max 0.26 _refine_diff_density_min -0.25 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.11(2) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack 0.5(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'F' 'F' 0.073 0.053 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F(1) F 0.9876(3) 0.665(2) 0.6921(1) 0.0678(7) Uani 1.00 d . . . O(1) O 0.5171(3) 0.303(2) 0.9647(1) 0.0561(8) Uani 1.00 d . . . N(1) N 1.2709(4) 0.801(2) 0.8539(2) 0.0576(10) Uani 1.00 d . . . C(1) C 1.2034(4) 0.616(2) 0.8437(2) 0.0436(10) Uani 1.00 d . . . C(2) C 1.1238(4) 0.371(2) 0.8335(2) 0.0431(9) Uani 1.00 d . . . C(3) C 1.0921(4) 0.288(2) 0.7490(2) 0.049(1) Uani 1.00 d . . . C(4) C 0.9505(5) 0.413(2) 0.6931(2) 0.0489(9) Uani 1.00 d . . . C(5) C 0.9267(5) 0.318(2) 0.6120(2) 0.059(1) Uani 1.00 d . . . C(6) C 0.7820(5) 0.439(2) 0.5554(2) 0.064(1) Uani 1.00 d . . . C(7) C 0.7513(5) 0.330(2) 0.4749(2) 0.064(1) Uani 1.00 d . . . C(8) C 0.6086(5) 0.457(2) 0.4185(2) 0.066(1) Uani 1.00 d . . . C(9) C 0.5785(5) 0.356(2) 0.3374(2) 0.072(1) Uani 1.00 d . . . C(10) C 0.4416(6) 0.493(2) 0.2825(3) 0.090(2) Uani 1.00 d . . . C(11) C 0.9627(4) 0.358(2) 0.8707(2) 0.0400(9) Uani 1.00 d . . . C(12) C 0.9401(4) 0.158(2) 0.9163(2) 0.0425(10) Uani 1.00 d . . . C(13) C 0.7925(4) 0.136(2) 0.9483(2) 0.0445(10) Uani 1.00 d . . . C(14) C 0.6677(4) 0.316(2) 0.9346(2) 0.0412(9) Uani 1.00 d . . . C(15) C 0.6884(4) 0.515(2) 0.8904(2) 0.0452(10) Uani 1.00 d . . . C(16) C 0.8363(4) 0.536(2) 0.8588(2) 0.0443(10) Uani 1.00 d . . . H(1) H 1.2054 0.2658 0.8613 0.0509 Uiso 1.00 calc . . . H(2) H 1.0655 0.1226 0.7478 0.0583 Uiso 1.00 calc . . . H(3) H 1.1971 0.3164 0.7302 0.0583 Uiso 1.00 calc . . . H(4) H 0.8449 0.3968 0.7112 0.0578 Uiso 1.00 calc . . . H(5) H 0.9012 0.1523 0.6131 0.0700 Uiso 1.00 calc . . . H(6) H 1.0312 0.3458 0.5939 0.0700 Uiso 1.00 calc . . . H(7) H 0.6786 0.4285 0.5755 0.0768 Uiso 1.00 calc . . . H(8) H 0.8111 0.6107 0.5520 0.0768 Uiso 1.00 calc . . . H(9) H 0.7195 0.1669 0.4782 0.0762 Uiso 1.00 calc . . . H(10) H 0.8558 0.3442 0.4554 0.0762 Uiso 1.00 calc . . . H(11) H 0.5047 0.4485 0.4377 0.0786 Uiso 1.00 calc . . . H(12) H 0.6403 0.6297 0.4164 0.0786 Uiso 1.00 calc . . . H(13) H 0.5422 0.1952 0.3386 0.0847 Uiso 1.00 calc . . . H(14) H 0.6834 0.3687 0.3183 0.0847 Uiso 1.00 calc . . . H(15) H 0.3332 0.4782 0.2977 0.1074 Uiso 1.00 calc . . . H(16) H 0.4714 0.6668 0.2834 0.1074 Uiso 1.00 calc . . . H(17) H 0.4354 0.4358 0.2316 0.1074 Uiso 1.00 calc . . . H(18) H 1.0269 0.0394 0.9255 0.0511 Uiso 1.00 calc . . . H(19) H 0.7787 0.0033 0.9797 0.0526 Uiso 1.00 calc . . . H(20) H 0.5148 0.1705 0.9915 0.1138 Uiso 1.00 calc . . . H(21) H 0.6017 0.6423 0.8806 0.0537 Uiso 1.00 calc . . . H(22) H 0.8514 0.6811 0.8291 0.0521 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.082(2) 0.046(1) 0.071(2) -0.001(1) 0.005(1) 0.003(1) O(1) 0.044(1) 0.070(2) 0.059(2) 0.006(2) 0.024(1) 0.011(2) N(1) 0.048(2) 0.048(2) 0.077(2) 0.000(2) 0.011(2) 0.004(2) C(1) 0.036(2) 0.044(2) 0.052(2) 0.007(2) 0.014(2) 0.003(2) C(2) 0.041(2) 0.038(2) 0.052(2) 0.011(2) 0.013(1) 0.005(2) C(3) 0.051(2) 0.045(2) 0.056(2) 0.000(2) 0.019(1) -0.002(2) C(4) 0.049(2) 0.046(2) 0.055(2) -0.002(2) 0.017(2) -0.004(2) C(5) 0.068(2) 0.060(3) 0.052(2) -0.001(2) 0.017(2) -0.003(2) C(6) 0.063(2) 0.077(3) 0.055(2) 0.004(2) 0.016(2) -0.007(2) C(7) 0.072(2) 0.071(3) 0.053(2) -0.002(2) 0.019(2) -0.002(2) C(8) 0.062(2) 0.078(4) 0.060(2) 0.001(2) 0.016(2) -0.007(2) C(9) 0.070(3) 0.089(4) 0.061(2) -0.007(3) 0.020(2) -0.013(2) C(10) 0.072(3) 0.121(5) 0.070(3) 0.011(3) -0.004(2) -0.026(3) C(11) 0.038(2) 0.040(2) 0.041(2) 0.000(1) 0.004(1) -0.002(2) C(12) 0.043(2) 0.037(2) 0.048(2) 0.008(2) 0.008(1) 0.002(2) C(13) 0.048(2) 0.041(2) 0.045(2) -0.001(2) 0.012(2) 0.007(2) C(14) 0.040(2) 0.048(2) 0.035(2) 0.000(2) 0.009(1) -0.006(2) C(15) 0.039(2) 0.045(2) 0.051(2) 0.009(2) 0.008(2) 0.003(2) C(16) 0.044(2) 0.039(2) 0.051(2) 0.004(2) 0.013(2) 0.005(2) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(1) 2.890(4) . . yes F(1) C(4) 1.411(7) . . yes O(1) C(14) 1.389(4) . . yes N(1) C(1) 1.140(5) . . yes C(1) C(2) 1.473(6) . . yes C(2) C(3) 1.534(6) . . yes C(2) C(11) 1.530(5) . . yes C(3) C(4) 1.497(6) . . yes C(4) C(5) 1.500(6) . . yes C(5) C(6) 1.502(7) . . yes C(6) C(7) 1.520(7) . . yes C(7) C(8) 1.513(7) . . yes C(8) C(9) 1.511(7) . . yes C(9) C(10) 1.494(9) . . yes C(11) C(12) 1.386(5) . . yes C(11) C(16) 1.378(5) . . yes C(12) C(13) 1.387(5) . . yes C(13) C(14) 1.378(5) . . yes C(14) C(15) 1.368(6) . . yes C(15) C(16) 1.380(5) . . yes #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N(1) C(1) C(2) 177.0(4) . . . yes C(1) C(2) C(3) 112.1(3) . . . yes C(1) C(2) C(11) 111.1(3) . . . yes C(1) F(1) C(4) 89.1(3) . . . yes C(3) C(2) C(11) 114.2(3) . . . yes C(2) C(3) C(4) 117.4(4) . . . yes F(1) C(1) N(1) 103.9(3) . . . yes F(1) C(1) C(2) 78.9(3) . . . yes F(1) C(4) C(3) 108.9(4) . . . yes F(1) C(4) C(5) 108.4(4) . . . yes C(3) C(4) C(5) 114.3(4) . . . yes C(4) C(5) C(6) 114.9(4) . . . yes C(5) C(6) C(7) 114.5(4) . . . yes C(6) C(7) C(8) 113.9(4) . . . yes C(7) C(8) C(9) 114.9(4) . . . yes C(8) C(9) C(10) 113.4(5) . . . yes C(2) C(11) C(12) 119.6(3) . . . yes C(2) C(11) C(16) 122.0(3) . . . yes C(12) C(11) C(16) 118.4(3) . . . yes C(11) C(12) C(13) 120.8(4) . . . yes C(12) C(13) C(14) 119.3(4) . . . yes O(1) C(14) C(13) 121.9(4) . . . yes O(1) C(14) C(15) 117.5(4) . . . yes C(13) C(14) C(15) 120.6(3) . . . yes C(14) C(15) C(16) 119.7(4) . . . yes C(11) C(16) C(15) 121.2(4) . . . yes #------------------------------------------------------------------------------ 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 F(1) C(4) C(2) C(1) -8.6(3) . . . . yes F(1) C(4) C(3) C(2) 59.6(5) . . . . yes F(1) C(4) C(5) C(6) -59.3(5) . . . . yes O(1) C(14) C(13) C(12) 179.7(4) . . . . yes O(1) C(14) C(15) C(16) 179.7(4) . . . . yes N(1) C(1) C(2) C(3) -124(7) . . . . yes N(1) C(1) C(2) C(11) 106(7) . . . . yes C(1) C(2) C(3) C(4) -71.7(4) . . . . yes C(1) C(2) C(11) C(12) -134.1(4) . . . . yes C(1) C(2) C(11) C(16) 47.6(5) . . . . yes C(2) C(3) C(4) C(5) -179.1(4) . . . . yes C(2) C(11) C(12) C(13) -177.4(3) . . . . yes C(2) C(11) C(16) C(15) 176.7(4) . . . . yes C(3) C(2) C(11) C(12) 97.9(4) . . . . yes C(3) C(2) C(11) C(16) -80.4(5) . . . . yes C(3) C(4) C(5) C(6) 179.0(4) . . . . yes C(4) C(3) C(2) C(11) 55.8(5) . . . . yes C(4) C(5) C(6) C(7) -176.1(5) . . . . yes C(5) C(6) C(7) C(8) -178.5(5) . . . . yes C(6) C(7) C(8) C(9) 178.6(5) . . . . yes C(7) C(8) C(9) C(10) -177.8(5) . . . . yes C(11) C(12) C(13) C(14) 0.0(6) . . . . yes C(11) C(16) C(15) C(14) 1.3(6) . . . . yes C(12) C(11) C(16) C(15) -1.6(5) . . . . yes C(12) C(13) C(14) C(15) -0.4(6) . . . . yes C(13) C(12) C(11) C(16) 0.9(5) . . . . yes C(13) C(14) C(15) C(16) -0.3(6) . . . . yes C(13) C(14) C(15) C(16) -0.3(6) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F(1) C(1) 2.890(4) . . ? F(1) C(3) 3.594(7) . 1_565 ? O(1) O(1) 3.031(2) . 2_657 ? O(1) O(1) 3.031(2) . 2_647 ? O(1) N(1) 3.309(4) . 2_747 ? O(1) C(1) 3.399(5) . 1_455 ? O(1) C(2) 3.515(4) . 1_455 ? N(1) C(2) 3.321(6) . 1_565 ? N(1) C(3) 3.388(6) . 1_565 ? N(1) C(15) 3.579(5) . 1_655 ? N(1) C(12) 3.583(5) . 1_565 ? C(12) C(16) 3.591(6) . 1_545 ? C(13) C(15) 3.593(6) . 1_545 ? #------------------------------------------------------------------------------ #Intermolecular Distances #atom atom distance ADC(*) #O(1) H(20) 2.14(6) 65702 #Contacts out to 3.60 angstroms. Estimated standard deviations #in the least significant figure are given in parentheses. #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_(2S, 4S)-4-Fluoro-2-(4-hydroxyphenyl)decanenitrile (syn-1) _database_code_CSD 169362 _audit_creation_date 'Wed Oct 10 15:25:39 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Hagimoto, Yuri' 'Hasegawa, Hiroaki' 'Nishide, Kiyoharu' 'Node, Manabu' 'Shiro, Motoo' _publ_contact_author_name 'Prof Manabu Node' _publ_contact_author_address ; Dept of Pharmaceutical Manufacturing Chemistry Kyoto Pharmaceutical University Misasagi Yamashina Kyoto 607-8414 JAPAN ; _publ_contact_author_email 'NODE@MB.KYOTO-PHU.AC.JP' _publ_contact_author_fax ' +81-75-595-4775 ' _publ_contact_author_phone ' +81-75-595-4639 ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_section_title ; A Novel Intramolecular Through-Space Interaction between F and CN: A Strategy for the Conformational Control of an Acyclic System ; # TEXT _publ_section_abstract ; X-Ray crystallographic analyses of fluorocyanides anti-1 and 2 revealed a novel intramolecular through-space interaction between F and CN in an acyc lic system, which was applied to a stereoselective protonation of an acyclic fluorocyanides 2 having flexible conformation. ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; We are grateful for a Grant-in-Aid (No. 11672126 to KN) from the Ministr y of Education, Science, Sports and Culture of Japan, in partial financial s upport of this research. We are also grateful to Prof. Tamejiro Hiyama, Kyo to University, for helpful discussions at Sagami Chemical Research Center. We also thank the Japan Energy Corporation, Toda, Saitama, Japan, for its ki nd gift of (R)-epoxyoctane. ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; _publ_section_figure_captions ; none ; _publ_section_exptl_prep ; See supporting Information ; _publ_section_exptl_refinement ; See supporting Information ; #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C16 H22 F N O ' _chemical_formula_moiety 'C16 H22 F N O ' _chemical_formula_weight 263.35 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 7.509(1) _cell_length_b 35.774(4) _cell_length_c 5.596(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1503.3(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 772 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 20.0 _cell_measurement_temperature 143.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 1400 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 25.15 _diffrn_measured_fraction_theta_max 0.8701 _diffrn_reflns_theta_full 25.15 _diffrn_measured_fraction_theta_full 0.8701 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 0 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1400 _reflns_number_gt 1262 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.0565 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1262 _refine_ls_number_parameters 173 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00156|Fo|^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.18 _refine_diff_density_min -0.14 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.056(9) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'F' 'F' 0.017 0.010 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F(1) F 0.3965(2) 0.12711(5) 0.7137(3) 0.0385(5) Uani 1.00 d . . . O(1) O 0.4202(3) -0.05599(5) 0.2395(4) 0.0397(6) Uani 1.00 d . . . N(1) N 0.9043(4) 0.10263(7) 0.0888(6) 0.0475(8) Uani 1.00 d . . . C(1) C 0.6228(4) 0.09568(7) 0.3630(6) 0.0317(7) Uani 1.00 d . . . C(2) C 0.4842(4) 0.12617(7) 0.3068(5) 0.0338(8) Uani 1.00 d . . . C(3) C 0.3277(4) 0.12516(8) 0.4772(5) 0.0311(8) Uani 1.00 d . . . C(4) C 0.1995(4) 0.15747(8) 0.4426(6) 0.0342(8) Uani 1.00 d . . . C(5) C 0.0468(4) 0.15764(8) 0.6203(6) 0.0336(8) Uani 1.00 d . . . C(6) C -0.0863(4) 0.18894(8) 0.5790(6) 0.0368(8) Uani 1.00 d . . . C(7) C -0.2347(4) 0.19057(8) 0.7621(6) 0.0360(8) Uani 1.00 d . . . C(8) C -0.3704(4) 0.22149(8) 0.7173(6) 0.0410(8) Uani 1.00 d . . . C(9) C -0.5165(5) 0.22351(9) 0.9017(7) 0.051(1) Uani 1.00 d . . . C(10) C 0.7813(4) 0.10062(7) 0.2120(6) 0.0358(8) Uani 1.00 d . . . C(11) C 0.5578(3) 0.05558(7) 0.3351(5) 0.0277(7) Uani 1.00 d . . . C(12) C 0.5999(4) 0.02948(7) 0.5099(5) 0.0284(7) Uani 1.00 d . . . C(13) C 0.5548(4) -0.00786(7) 0.4841(5) 0.0314(8) Uani 1.00 d . . . C(14) C 0.4676(4) -0.01963(7) 0.2806(5) 0.0296(7) Uani 1.00 d . . . C(15) C 0.4232(4) 0.00620(8) 0.1039(6) 0.0316(8) Uani 1.00 d . . . C(16) C 0.4682(4) 0.04348(7) 0.1336(5) 0.0305(8) Uani 1.00 d . . . H(1) H 0.6588 0.0989 0.5245 0.0380 Uiso 1.00 calc . . . H(1O) H 0.4732 -0.0691 0.3261 0.0429 Uiso 1.00 calc . . . H(2a) H 0.5400 0.1499 0.3182 0.0406 Uiso 1.00 calc . . . H(2b) H 0.4415 0.1226 0.1487 0.0406 Uiso 1.00 calc . . . H(3) H 0.2654 0.1023 0.4574 0.0373 Uiso 1.00 calc . . . H(4a) H 0.2639 0.1802 0.4592 0.0410 Uiso 1.00 calc . . . H(4b) H 0.1513 0.1560 0.2859 0.0410 Uiso 1.00 calc . . . H(5a) H -0.0143 0.1344 0.6087 0.0404 Uiso 1.00 calc . . . H(5b) H 0.0948 0.1603 0.7765 0.0404 Uiso 1.00 calc . . . H(6a) H -0.0239 0.2120 0.5827 0.0442 Uiso 1.00 calc . . . H(6b) H -0.1382 0.1856 0.4257 0.0442 Uiso 1.00 calc . . . H(7a) H -0.2955 0.1673 0.7607 0.0432 Uiso 1.00 calc . . . H(7b) H -0.1829 0.1945 0.9149 0.0432 Uiso 1.00 calc . . . H(8a) H -0.3093 0.2447 0.7161 0.0492 Uiso 1.00 calc . . . H(8b) H -0.4235 0.2173 0.5655 0.0492 Uiso 1.00 calc . . . H(9a) H -0.4673 0.2306 1.0514 0.0615 Uiso 1.00 calc . . . H(9b) H -0.6025 0.2415 0.8537 0.0615 Uiso 1.00 calc . . . H(9c) H -0.5718 0.1997 0.9162 0.0615 Uiso 1.00 calc . . . H(12) H 0.6609 0.0374 0.6498 0.0340 Uiso 1.00 calc . . . H(13) H 0.5838 -0.0253 0.6061 0.0377 Uiso 1.00 calc . . . H(15) H 0.3625 -0.0017 -0.0362 0.0379 Uiso 1.00 calc . . . H(16) H 0.4368 0.0610 0.0133 0.0366 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.0374(9) 0.0473(10) 0.0307(9) 0.0077(8) -0.0011(8) 0.0011(7) O(1) 0.045(1) 0.0286(10) 0.045(1) -0.0028(9) -0.009(1) -0.0018(9) N(1) 0.048(2) 0.037(1) 0.058(2) -0.005(1) 0.016(2) 0.000(1) C(1) 0.035(1) 0.028(1) 0.032(2) -0.002(1) 0.004(1) 0.001(1) C(2) 0.039(2) 0.027(1) 0.035(2) 0.002(1) 0.004(1) 0.001(1) C(3) 0.035(2) 0.032(1) 0.026(2) 0.001(1) -0.001(1) 0.000(1) C(4) 0.036(2) 0.032(1) 0.034(2) 0.001(1) 0.002(1) 0.002(1) C(5) 0.034(2) 0.034(1) 0.033(2) 0.001(1) 0.001(1) 0.002(1) C(6) 0.036(2) 0.033(1) 0.042(2) 0.001(1) 0.001(1) 0.002(1) C(7) 0.033(1) 0.034(1) 0.042(2) 0.001(1) 0.001(1) -0.001(1) C(8) 0.039(2) 0.034(1) 0.050(2) 0.006(1) 0.001(2) -0.001(1) C(9) 0.047(2) 0.048(2) 0.058(2) 0.013(2) 0.010(2) -0.003(2) C(10) 0.037(2) 0.027(1) 0.043(2) -0.003(1) 0.005(2) -0.001(1) C(11) 0.023(1) 0.028(1) 0.032(2) 0.003(1) 0.004(1) 0.000(1) C(12) 0.027(1) 0.030(1) 0.028(2) 0.002(1) -0.001(1) -0.001(1) C(13) 0.031(1) 0.029(1) 0.034(2) 0.005(1) -0.003(1) 0.001(1) C(14) 0.027(1) 0.029(1) 0.032(2) -0.001(1) 0.005(1) -0.004(1) C(15) 0.028(2) 0.039(1) 0.028(2) 0.002(1) -0.002(1) -0.002(1) C(16) 0.031(2) 0.035(1) 0.026(2) 0.004(1) 0.001(1) 0.003(1) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS' _computing_cell_refinement 'PROCESS' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(3) 1.423(3) . . yes O(1) C(14) 1.368(3) . . yes N(1) C(10) 1.155(4) . . yes C(1) C(2) 1.540(4) . . yes C(1) C(10) 1.470(4) . . yes C(1) C(11) 1.523(4) . . yes C(2) C(3) 1.514(4) . . yes C(3) C(4) 1.516(4) . . yes C(4) C(5) 1.518(4) . . yes C(5) C(6) 1.518(4) . . yes C(6) C(7) 1.515(4) . . yes C(7) C(8) 1.524(4) . . yes C(8) C(9) 1.508(5) . . yes C(11) C(12) 1.389(4) . . yes C(11) C(16) 1.383(4) . . yes C(12) C(13) 1.386(4) . . yes C(13) C(14) 1.379(4) . . yes C(14) C(15) 1.394(4) . . yes C(15) C(16) 1.385(4) . . yes #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(2) C(1) C(10) 110.2(2) . . . yes C(2) C(1) C(11) 115.4(2) . . . yes C(10) C(1) C(11) 108.3(2) . . . yes C(1) C(2) C(3) 112.3(2) . . . yes F(1) C(3) C(2) 107.6(2) . . . yes F(1) C(3) C(4) 108.2(2) . . . yes C(2) C(3) C(4) 113.2(2) . . . yes C(3) C(4) C(5) 113.5(2) . . . yes C(4) C(5) C(6) 113.6(2) . . . yes C(5) C(6) C(7) 114.2(2) . . . yes C(6) C(7) C(8) 114.1(2) . . . yes C(7) C(8) C(9) 114.1(3) . . . yes N(1) C(10) C(1) 176.4(3) . . . yes C(1) C(11) C(12) 119.2(2) . . . yes C(1) C(11) C(16) 122.3(2) . . . yes C(12) C(11) C(16) 118.3(2) . . . yes C(11) C(12) C(13) 121.3(3) . . . yes C(12) C(13) C(14) 119.8(2) . . . yes O(1) C(14) C(13) 123.5(2) . . . yes O(1) C(14) C(15) 116.7(3) . . . yes C(13) C(14) C(15) 119.8(2) . . . yes C(14) C(15) C(16) 119.6(3) . . . yes C(11) C(16) C(15) 121.2(2) . . . yes #------------------------------------------------------------------------------ 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 F(1) C(3) C(1) C(10) -118.6(4) . . . . yes F(1) C(3) C(2) C(1) 54.2(3) . . . . yes F(1) C(3) C(4) C(5) -58.1(3) . . . . yes O(1) C(14) C(13) C(12) 179.1(3) . . . . yes O(1) C(14) C(15) C(16) -179.7(3) . . . . yes N(1) C(10) C(1) C(2) -121(5) . . . . yes N(1) C(10) C(1) C(11) 5(5) . . . . yes C(1) C(2) C(3) C(4) 173.7(2) . . . . yes C(1) C(11) C(12) C(13) -175.3(2) . . . . yes C(1) C(11) C(16) C(15) 174.7(3) . . . . yes C(2) C(1) C(11) C(12) -135.7(3) . . . . yes C(2) C(1) C(11) C(16) 48.8(4) . . . . yes C(2) C(3) C(4) C(5) -177.3(2) . . . . yes C(3) C(2) C(1) C(10) -173.2(2) . . . . yes C(3) C(2) C(1) C(11) 63.8(3) . . . . yes C(3) C(4) C(5) C(6) -177.4(2) . . . . yes C(4) C(5) C(6) C(7) -177.2(2) . . . . yes C(5) C(6) C(7) C(8) -178.8(2) . . . . yes C(6) C(7) C(8) C(9) -179.1(2) . . . . yes C(10) C(1) C(11) C(12) 100.3(3) . . . . yes C(10) C(1) C(11) C(16) -75.2(3) . . . . yes C(11) C(12) C(13) C(14) 0.5(4) . . . . yes C(11) C(16) C(15) C(14) 0.5(4) . . . . yes C(12) C(11) C(16) C(15) -0.9(4) . . . . yes C(12) C(13) C(14) C(15) -0.9(4) . . . . yes C(13) C(12) C(11) C(16) 0.3(4) . . . . yes C(13) C(14) C(15) C(16) 0.4(4) . . . . yes C(13) C(14) C(15) C(16) 0.4(4) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F(1) C(2) 3.384(4) . 1_556 ? F(1) O(1) 3.486(3) . 2_555 ? F(1) C(7) 3.591(3) . 1_655 ? O(1) N(1) 2.888(3) . 2_655 ? O(1) C(3) 3.427(4) . 2_554 ? N(1) C(5) 3.448(4) . 1_654 ? N(1) C(13) 3.454(4) . 2_654 ? N(1) C(4) 3.561(4) . 1_655 ? N(1) C(14) 3.566(4) . 2_654 ? C(14) C(15) 3.481(4) . 2_555 ? #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_site_distance_DH _geom_hbond_site_distance_HA _geom_hbond_site_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(1O) N(1) . . 2_655 0.782 2.110 2.888(3) 173.732 no #------------------------------------------------------------------------------