# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_RE88 #TrackingRef 'web_deposit_cif_file_0_AkioICHIKAWA_1366000417.RE88CIF.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H20 F3 N O3' _chemical_formula_moiety 'C18 H20 F3 N O3' _chemical_formula_weight 355.36 _chemical_melting_point ? _chemical_absolute_configuration rm #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 11.364(5) _cell_length_b 6.636(3) _cell_length_c 12.345(5) _cell_angle_alpha 90.0000 _cell_angle_beta 106.424(4) _cell_angle_gamma 90.0000 _cell_volume 893.0(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2746 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 123 #------------------------------------------------------------------------------ _exptl_crystal_description unknown _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372.00 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 0.989 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.314 _diffrn_reflns_number 6941 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. 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 4008 _reflns_number_gt 3711 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0896 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 4008 _refine_ls_number_parameters 295 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.0138P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.150 _refine_diff_density_min -0.250 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.02578(10) 0.57688(18) 0.91992(9) 0.0391(3) Uani 1.0 2 d . . . F2 F 0.20390(10) 0.43777(18) 0.96097(9) 0.0407(3) Uani 1.0 2 d . . . F3 F 0.18324(11) 0.7342(2) 1.02386(9) 0.0488(4) Uani 1.0 2 d . . . O1 O 0.06139(10) 0.69870(16) 0.63068(9) 0.0236(3) Uani 1.0 2 d . . . O2 O 0.09046(10) 0.40924(16) 0.72770(10) 0.0265(3) Uani 1.0 2 d . . . O3 O 0.13357(11) 0.91837(18) 0.82212(10) 0.0283(3) Uani 1.0 2 d . . . N1 N 0.10015(11) 1.09446(19) 0.57715(11) 0.0217(3) Uani 1.0 2 d . . . C1 C 0.09934(13) 0.5946(3) 0.71950(13) 0.0207(3) Uani 1.0 2 d . . . C2 C 0.16813(14) 0.7135(3) 0.82819(13) 0.0236(3) Uani 1.0 2 d . . . C3 C 0.14540(17) 0.6130(3) 0.93264(15) 0.0319(4) Uani 1.0 2 d . . . C4 C 0.00816(17) 0.9651(3) 0.81633(17) 0.0331(4) Uani 1.0 2 d . . . C5 C 0.30660(15) 0.7127(3) 0.83984(13) 0.0268(4) Uani 1.0 2 d . . . C6 C 0.36442(15) 0.5393(3) 0.81632(15) 0.0313(4) Uani 1.0 2 d . . . C7 C 0.49001(17) 0.5415(4) 0.82697(16) 0.0401(5) Uani 1.0 2 d . . . C8 C 0.55772(17) 0.7147(4) 0.86242(17) 0.0454(5) Uani 1.0 2 d . . . C9 C 0.50126(19) 0.8840(4) 0.88756(17) 0.0426(5) Uani 1.0 2 d . . . C10 C 0.37553(17) 0.8858(4) 0.87610(15) 0.0353(4) Uani 1.0 2 d . . . C11 C 0.23071(15) 1.1243(3) 0.57684(14) 0.0243(4) Uani 1.0 2 d . . . C12 C 0.24536(19) 1.3324(3) 0.53206(18) 0.0329(4) Uani 1.0 2 d . . . C13 C 0.27338(14) 0.9625(3) 0.50947(13) 0.0247(4) Uani 1.0 2 d . . . C14 C 0.37467(15) 0.8453(3) 0.56185(15) 0.0269(4) Uani 1.0 2 d . . . C15 C 0.42567(16) 0.7139(3) 0.49929(16) 0.0306(4) Uani 1.0 2 d . . . C16 C 0.37300(16) 0.6963(3) 0.38421(17) 0.0345(4) Uani 1.0 2 d . . . C17 C 0.26996(18) 0.8087(3) 0.33146(17) 0.0363(5) Uani 1.0 2 d . . . C18 C 0.22037(16) 0.9422(3) 0.39335(15) 0.0305(4) Uani 1.0 2 d . . . H1 H -0.004(2) 1.121(4) 0.7989(19) 0.040(6) Uiso 1.0 2 d . . . H1A H 0.0805 1.1866 0.6238 0.0261 Uiso 1.0 2 calc R . . H1B H 0.0907 0.9680 0.6019 0.0261 Uiso 1.0 2 calc R . . H1C H 0.0499 1.1107 0.5059 0.0261 Uiso 1.0 2 calc R . . H2 H -0.016(2) 0.927(4) 0.887(2) 0.048(7) Uiso 1.0 2 d . . . H3 H -0.048(2) 0.875(4) 0.754(2) 0.046(7) Uiso 1.0 2 d . . . H4 H 0.3154(18) 0.407(4) 0.7911(17) 0.035(6) Uiso 1.0 2 d . . . H5 H 0.530(2) 0.419(4) 0.8091(18) 0.040(6) Uiso 1.0 2 d . . . H6 H 0.640(2) 0.718(4) 0.868(2) 0.054(7) Uiso 1.0 2 d . . . H7 H 0.5479(18) 1.009(4) 0.9103(18) 0.042(6) Uiso 1.0 2 d . . . H8 H 0.3337(18) 1.009(4) 0.8925(18) 0.041(6) Uiso 1.0 2 d . . . H9 H 0.2193(17) 1.445(4) 0.5777(17) 0.035(6) Uiso 1.0 2 d . . . H10 H 0.199(3) 1.349(4) 0.454(3) 0.060(8) Uiso 1.0 2 d . . . H11 H 0.336(2) 1.352(4) 0.5384(18) 0.040(6) Uiso 1.0 2 d . . . H12 H 0.2851(18) 1.120(3) 0.6584(17) 0.029(5) Uiso 1.0 2 d . . . H13 H 0.409(2) 0.857(4) 0.650(2) 0.044(6) Uiso 1.0 2 d . . . H14 H 0.497(2) 0.630(4) 0.5378(17) 0.039(6) Uiso 1.0 2 d . . . H15 H 0.408(3) 0.605(4) 0.340(2) 0.054(7) Uiso 1.0 2 d . . . H16 H 0.2309(19) 0.795(4) 0.2483(19) 0.039(6) Uiso 1.0 2 d . . . H17 H 0.149(2) 1.023(4) 0.3535(19) 0.050(7) Uiso 1.0 2 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.0391(6) 0.0478(7) 0.0348(6) -0.0002(5) 0.0177(5) 0.0090(5) F2 0.0460(6) 0.0424(7) 0.0324(6) 0.0071(5) 0.0090(5) 0.0152(5) F3 0.0660(8) 0.0597(8) 0.0214(5) -0.0042(7) 0.0134(5) -0.0066(6) O1 0.0277(6) 0.0210(6) 0.0201(6) -0.0001(5) 0.0033(5) 0.0021(5) O2 0.0319(6) 0.0192(6) 0.0281(6) -0.0001(5) 0.0081(5) 0.0011(5) O3 0.0337(6) 0.0227(6) 0.0284(6) 0.0004(5) 0.0088(5) -0.0040(5) N1 0.0237(7) 0.0187(7) 0.0226(7) -0.0009(6) 0.0062(5) -0.0005(6) C1 0.0216(7) 0.0191(8) 0.0225(8) 0.0003(6) 0.0082(6) -0.0008(6) C2 0.0278(8) 0.0227(8) 0.0200(7) 0.0008(7) 0.0060(6) 0.0001(7) C3 0.0382(10) 0.0359(10) 0.0209(8) 0.0014(8) 0.0070(7) 0.0009(8) C4 0.0369(10) 0.0306(10) 0.0369(10) 0.0062(8) 0.0188(8) -0.0027(8) C5 0.0282(8) 0.0316(9) 0.0179(7) -0.0022(7) 0.0021(6) -0.0004(7) C6 0.0272(9) 0.0372(10) 0.0257(8) 0.0014(8) 0.0014(7) 0.0008(8) C7 0.0300(9) 0.0553(14) 0.0320(10) 0.0092(9) 0.0040(8) 0.0028(10) C8 0.0267(9) 0.0697(15) 0.0348(10) -0.0054(11) 0.0009(8) 0.0011(11) C9 0.0348(10) 0.0563(14) 0.0311(10) -0.0137(10) 0.0003(8) -0.0045(10) C10 0.0362(10) 0.0410(11) 0.0253(9) -0.0070(9) 0.0029(7) -0.0067(8) C11 0.0218(8) 0.0242(8) 0.0261(8) -0.0001(7) 0.0055(7) -0.0019(7) C12 0.0385(11) 0.0233(9) 0.0430(11) -0.0052(8) 0.0213(9) -0.0013(8) C13 0.0231(7) 0.0235(8) 0.0286(9) -0.0026(7) 0.0091(7) -0.0020(7) C14 0.0265(8) 0.0217(8) 0.0342(10) -0.0022(7) 0.0112(7) 0.0032(7) C15 0.0283(8) 0.0246(8) 0.0417(10) 0.0010(8) 0.0146(8) 0.0045(8) C16 0.0343(9) 0.0296(9) 0.0464(11) -0.0012(8) 0.0226(9) -0.0050(9) C17 0.0357(10) 0.0402(11) 0.0350(10) -0.0017(8) 0.0130(8) -0.0095(9) C18 0.0260(8) 0.0350(10) 0.0290(9) 0.0027(8) 0.0055(7) -0.0049(8) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C3 1.345(3) yes . . F2 C3 1.336(3) yes . . F3 C3 1.352(3) yes . . O1 C1 1.2641(19) yes . . O2 C1 1.241(2) yes . . O3 C2 1.411(2) yes . . O3 C4 1.440(3) yes . . N1 C11 1.498(3) yes . . C1 C2 1.562(2) yes . . C2 C3 1.537(3) yes . . C2 C5 1.539(3) yes . . C5 C6 1.396(3) yes . . C5 C10 1.391(3) yes . . C6 C7 1.396(3) yes . . C7 C8 1.383(4) yes . . C8 C9 1.372(4) yes . . C9 C10 1.395(3) yes . . C11 C12 1.514(3) yes . . C11 C13 1.519(3) yes . . C13 C14 1.388(3) yes . . C13 C18 1.396(3) yes . . C14 C15 1.395(3) yes . . C15 C16 1.382(3) yes . . C16 C17 1.386(3) yes . . C17 C18 1.389(3) yes . . N1 H1A 0.910 no . . N1 H1B 0.910 no . . N1 H1C 0.910 no . . C4 H1 1.06(3) no . . C4 H2 1.02(3) no . . C4 H3 1.04(2) no . . C6 H4 1.04(2) no . . C7 H5 0.99(3) no . . C8 H6 0.92(3) no . . C9 H7 0.98(3) no . . C10 H8 1.00(3) no . . C11 H12 1.022(19) no . . C12 H9 1.03(3) no . . C12 H10 0.96(3) no . . C12 H11 1.02(3) no . . C14 H13 1.05(3) no . . C15 H14 0.99(2) no . . C16 H15 0.97(3) no . . C17 H16 1.00(2) no . . C18 H17 0.98(3) no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 O3 C4 117.82(14) yes . . . O1 C1 O2 126.64(14) yes . . . O1 C1 C2 115.74(14) yes . . . O2 C1 C2 117.58(14) yes . . . O3 C2 C1 112.13(12) yes . . . O3 C2 C3 110.63(15) yes . . . O3 C2 C5 105.65(14) yes . . . C1 C2 C3 109.85(14) yes . . . C1 C2 C5 109.19(14) yes . . . C3 C2 C5 109.27(13) yes . . . F1 C3 F2 106.69(16) yes . . . F1 C3 F3 106.04(17) yes . . . F1 C3 C2 112.54(13) yes . . . F2 C3 F3 106.41(14) yes . . . F2 C3 C2 114.08(17) yes . . . F3 C3 C2 110.57(16) yes . . . C2 C5 C6 120.80(16) yes . . . C2 C5 C10 119.69(17) yes . . . C6 C5 C10 119.51(17) yes . . . C5 C6 C7 120.01(18) yes . . . C6 C7 C8 120.1(2) yes . . . C7 C8 C9 119.9(2) yes . . . C8 C9 C10 121.0(2) yes . . . C5 C10 C9 119.5(2) yes . . . N1 C11 C12 109.43(14) yes . . . N1 C11 C13 112.18(13) yes . . . C12 C11 C13 111.10(17) yes . . . C11 C13 C14 119.47(14) yes . . . C11 C13 C18 121.22(15) yes . . . C14 C13 C18 119.01(17) yes . . . C13 C14 C15 120.78(16) yes . . . C14 C15 C16 119.69(16) yes . . . C15 C16 C17 120.0(2) yes . . . C16 C17 C18 120.34(18) yes . . . C13 C18 C17 120.13(16) yes . . . C11 N1 H1A 109.468 no . . . C11 N1 H1B 109.471 no . . . C11 N1 H1C 109.473 no . . . H1A N1 H1B 109.477 no . . . H1A N1 H1C 109.468 no . . . H1B N1 H1C 109.470 no . . . O3 C4 H1 106.7(13) no . . . O3 C4 H2 114.2(12) no . . . O3 C4 H3 107.9(14) no . . . H1 C4 H2 111(2) no . . . H1 C4 H3 113.4(16) no . . . H2 C4 H3 103.3(19) no . . . C5 C6 H4 121.0(12) no . . . C7 C6 H4 119.0(12) no . . . C6 C7 H5 119.4(13) no . . . C8 C7 H5 120.5(13) no . . . C7 C8 H6 120.5(17) no . . . C9 C8 H6 119.6(17) no . . . C8 C9 H7 120.4(14) no . . . C10 C9 H7 118.5(14) no . . . C5 C10 H8 119.2(13) no . . . C9 C10 H8 121.3(13) no . . . N1 C11 H12 108.5(13) no . . . C12 C11 H12 106.8(12) no . . . C13 C11 H12 108.7(12) no . . . C11 C12 H9 112.6(13) no . . . C11 C12 H10 112.5(16) no . . . C11 C12 H11 107.6(12) no . . . H9 C12 H10 108(2) no . . . H9 C12 H11 107.8(17) no . . . H10 C12 H11 108(2) no . . . C13 C14 H13 117.1(13) no . . . C15 C14 H13 122.1(13) no . . . C14 C15 H14 120.0(13) no . . . C16 C15 H14 120.3(13) no . . . C15 C16 H15 120.3(13) no . . . C17 C16 H15 119.7(13) no . . . C16 C17 H16 120.3(14) no . . . C18 C17 H16 119.3(14) no . . . C13 C18 H17 121.3(15) no . . . C17 C18 H17 118.6(15) no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C4 O3 C2 C1 64.13(19) no . . . . C4 O3 C2 C3 -58.87(16) no . . . . C4 O3 C2 C5 -177.02(13) no . . . . O1 C1 C2 O3 24.8(2) no . . . . O1 C1 C2 C3 148.23(13) no . . . . O1 C1 C2 C5 -91.96(16) no . . . . O2 C1 C2 O3 -157.26(14) no . . . . O2 C1 C2 C3 -33.82(19) no . . . . O2 C1 C2 C5 86.00(17) no . . . . O3 C2 C3 F1 74.81(17) no . . . . O3 C2 C3 F2 -163.45(12) no . . . . O3 C2 C3 F3 -43.57(17) no . . . . O3 C2 C5 C6 -161.73(13) no . . . . O3 C2 C5 C10 19.38(18) no . . . . C1 C2 C3 F1 -49.51(19) no . . . . C1 C2 C3 F2 72.24(17) no . . . . C1 C2 C3 F3 -167.88(13) no . . . . C1 C2 C5 C6 -40.96(19) no . . . . C1 C2 C5 C10 140.16(13) no . . . . C3 C2 C5 C6 79.21(18) no . . . . C3 C2 C5 C10 -99.67(17) no . . . . C5 C2 C3 F1 -169.28(14) no . . . . C5 C2 C3 F2 -47.53(18) no . . . . C5 C2 C3 F3 72.35(18) no . . . . C2 C5 C6 C7 179.78(13) no . . . . C2 C5 C10 C9 179.41(13) no . . . . C6 C5 C10 C9 0.5(3) no . . . . C10 C5 C6 C7 -1.3(3) no . . . . C5 C6 C7 C8 1.0(3) no . . . . C6 C7 C8 C9 0.3(3) no . . . . C7 C8 C9 C10 -1.1(3) no . . . . C8 C9 C10 C5 0.7(3) no . . . . N1 C11 C13 C14 -122.28(14) no . . . . N1 C11 C13 C18 64.09(19) no . . . . C12 C11 C13 C14 114.87(16) no . . . . C12 C11 C13 C18 -58.76(19) no . . . . C11 C13 C14 C15 -171.65(14) no . . . . C11 C13 C18 C17 172.68(15) no . . . . C14 C13 C18 C17 -1.0(3) no . . . . C18 C13 C14 C15 2.1(3) no . . . . C13 C14 C15 C16 -1.6(3) no . . . . C14 C15 C16 C17 -0.0(3) no . . . . C15 C16 C17 C18 1.2(3) no . . . . C16 C17 C18 C13 -0.7(3) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 O2 2.897(2) no . . F1 O3 2.988(2) no . . F1 C1 2.829(3) no . . F1 C4 2.858(3) no . . F2 O2 2.8092(19) no . . F2 C1 3.062(2) no . . F2 C5 2.813(3) no . . F2 C6 2.968(3) no . . F3 O3 2.6870(19) no . . F3 C4 3.160(3) no . . F3 C5 2.991(3) no . . F3 C10 3.372(3) no . . O1 O3 2.6995(18) no . . O1 C4 3.087(3) no . . O1 C5 3.221(2) no . . O2 O3 3.562(2) no . . O2 C3 2.780(3) no . . O2 C5 3.175(3) no . . O2 C6 3.116(3) no . . O3 C10 2.648(3) no . . N1 C14 3.583(3) no . . N1 C18 3.129(3) no . . C1 C4 3.041(3) no . . C1 C6 2.933(3) no . . C3 C4 2.948(3) no . . C3 C6 3.243(3) no . . C3 C10 3.411(3) no . . C5 C8 2.788(3) no . . C6 C9 2.766(3) no . . C7 C10 2.780(4) no . . C12 C14 3.527(3) no . . C12 C18 3.073(3) no . . C13 C16 2.790(3) no . . C14 C17 2.766(3) no . . C15 C18 2.779(3) no . . F1 F3 3.497(2) no . 2_547 F1 C4 3.466(3) no . 2_547 F2 C8 3.308(3) no . 2_647 F2 C9 3.363(3) no . 2_647 F3 F1 3.497(2) no . 2_557 O1 N1 2.774(2) no . . O1 N1 2.7871(18) no . 2_546 O1 C11 3.584(3) no . . O1 C18 3.564(3) no . 2_546 O2 O3 3.448(2) no . 1_545 O2 N1 2.819(2) no . 1_545 O2 C4 3.367(3) no . 1_545 O2 C11 3.356(3) no . 1_545 O2 C12 3.405(3) no . 1_545 O2 C18 3.431(3) no . 2_546 O3 O2 3.448(2) no . 1_565 O3 N1 3.163(3) no . . N1 O1 2.774(2) no . . N1 O1 2.7871(18) no . 2_556 N1 O2 2.819(2) no . 1_565 N1 O3 3.163(3) no . . N1 C4 3.506(3) no . . C4 F1 3.466(3) no . 2_557 C4 O2 3.367(3) no . 1_565 C4 N1 3.506(3) no . . C8 F2 3.308(3) no . 2_657 C9 F2 3.363(3) no . 2_657 C11 O1 3.584(3) no . . C11 O2 3.356(3) no . 1_565 C12 O2 3.405(3) no . 1_565 C12 C15 3.353(3) no . 1_565 C12 C16 3.572(4) no . 1_565 C14 C15 3.560(3) no . 2_656 C15 C12 3.353(3) no . 1_545 C15 C14 3.560(3) no . 2_646 C16 C12 3.572(4) no . 1_545 C18 O1 3.564(3) no . 2_556 C18 O2 3.431(3) no . 2_556 F1 H2 2.39(3) no . . F1 H3 2.80(3) no . . F2 H4 2.75(3) no . . F3 H2 2.73(2) no . . F3 H8 3.23(3) no . . O1 H3 2.51(3) no . . O1 H4 3.573(19) no . . O2 H3 3.53(3) no . . O2 H4 2.45(2) no . . O3 H8 2.27(2) no . . N1 H9 2.69(3) no . . N1 H10 2.72(3) no . . N1 H11 3.32(3) no . . N1 H17 3.00(3) no . . C1 H2 3.52(3) no . . C1 H3 2.62(3) no . . C1 H4 2.67(2) no . . C2 H1 3.29(3) no . . C2 H2 2.79(3) no . . C2 H3 2.60(3) no . . C2 H4 2.75(3) no . . C2 H8 2.68(3) no . . C3 H2 2.73(3) no . . C3 H3 3.16(2) no . . C3 H4 3.25(3) no . . C3 H8 3.51(3) no . . C4 H8 3.56(2) no . . C5 H5 3.30(3) no . . C5 H7 3.28(3) no . . C6 H6 3.24(3) no . . C6 H8 3.30(3) no . . C7 H7 3.27(3) no . . C8 H4 3.34(2) no . . C8 H8 3.31(3) no . . C9 H5 3.28(3) no . . C10 H4 3.35(3) no . . C10 H6 3.23(3) no . . C11 H13 2.65(2) no . . C11 H17 2.73(3) no . . C12 H1A 2.6325 no . . C12 H1B 3.2462 no . . C12 H1C 2.6073 no . . C12 H17 2.99(3) no . . C13 H1A 3.2800 no . . C13 H1B 2.6364 no . . C13 H1C 2.7125 no . . C13 H9 3.41(3) no . . C13 H10 2.72(3) no . . C13 H11 2.68(2) no . . C13 H14 3.31(3) no . . C13 H16 3.31(3) no . . C14 H1B 3.4957 no . . C14 H11 3.39(2) no . . C14 H12 2.54(3) no . . C14 H15 3.28(3) no . . C14 H17 3.29(2) no . . C15 H16 3.30(2) no . . C16 H13 3.36(3) no . . C16 H17 3.28(3) no . . C17 H14 3.292(19) no . . C18 H1B 3.3127 no . . C18 H1C 2.9079 no . . C18 H10 2.83(3) no . . C18 H11 3.32(2) no . . C18 H12 3.36(2) no . . C18 H13 3.33(2) no . . C18 H15 3.28(3) no . . H1A H9 2.5032 no . . H1A H10 2.9949 no . . H1A H11 3.5291 no . . H1A H12 2.2854 no . . H1B H9 3.5360 no . . H1B H10 3.5369 no . . H1B H12 2.3462 no . . H1B H13 3.5714 no . . H1B H17 3.3357 no . . H1C H9 2.9080 no . . H1C H10 2.5306 no . . H1C H11 3.5407 no . . H1C H12 2.8015 no . . H1C H17 2.5201 no . . H4 H5 2.38(3) no . . H5 H6 2.35(4) no . . H6 H7 2.32(4) no . . H7 H8 2.38(3) no . . H9 H12 2.41(3) no . . H10 H12 2.87(4) no . . H10 H17 2.48(4) no . . H11 H12 2.32(4) no . . H11 H13 3.57(3) no . . H11 H17 3.43(3) no . . H12 H13 2.26(3) no . . H13 H14 2.45(4) no . . H14 H15 2.37(3) no . . H15 H16 2.37(3) no . . H16 H17 2.35(4) no . . F1 H1 3.35(3) no . 1_545 F1 H1 3.56(3) no . 2_547 F1 H2 2.61(3) no . 2_547 F1 H16 3.59(2) no . 2_546 F1 H17 3.42(2) no . 2_546 F2 H1 3.36(2) no . 1_545 F2 H2 3.21(3) no . 2_547 F2 H6 2.76(3) no . 2_647 F2 H7 2.858(19) no . 2_647 F2 H8 3.42(3) no . 1_545 F3 H1 3.47(3) no . 2_547 F3 H2 3.18(3) no . 2_547 F3 H5 3.55(2) no . 2_657 F3 H7 3.29(2) no . 2_647 F3 H16 2.70(3) no . 1_556 O1 H1A 3.4082 no . 1_545 O1 H1A 3.2474 no . . O1 H1A 3.1006 no . 2_546 O1 H1B 1.8702 no . . O1 H1B 3.2821 no . 2_546 O1 H1C 3.1231 no . . O1 H1C 1.8910 no . 2_546 O1 H9 2.67(3) no . 1_545 O1 H10 3.02(3) no . 2_546 O1 H17 2.72(3) no . 2_546 O2 H1 2.47(3) no . 1_545 O2 H1A 1.9388 no . 1_545 O2 H1B 3.3149 no . 1_545 O2 H1C 3.3049 no . 1_545 O2 H1C 3.1695 no . 2_546 O2 H9 2.68(3) no . 1_545 O2 H12 3.22(3) no . 1_545 O2 H17 2.73(2) no . 2_546 O3 H1A 2.9477 no . . O3 H1B 2.6432 no . . O3 H12 3.29(3) no . . N1 H1 3.28(3) no . . N1 H3 3.44(3) no . . C1 H1 3.59(3) no . 1_545 C1 H1A 2.9379 no . 1_545 C1 H1B 2.8592 no . . C1 H1C 2.8213 no . 2_546 C1 H9 2.69(3) no . 1_545 C1 H17 2.75(3) no . 2_546 C2 H1B 3.1684 no . . C3 H2 3.24(3) no . 2_547 C3 H7 3.545(19) no . 2_647 C4 H1A 3.0963 no . . C4 H1B 3.0482 no . . C4 H10 3.59(3) no . 2_546 C4 H16 3.41(3) no . 2_556 C5 H7 3.35(2) no . 2_647 C5 H9 3.58(2) no . 1_545 C5 H12 3.47(2) no . . C5 H13 3.05(3) no . . C6 H7 3.24(2) no . 2_647 C6 H9 3.006(19) no . 1_545 C6 H11 3.58(3) no . 1_545 C6 H12 3.37(2) no . 1_545 C6 H13 3.08(3) no . . C7 H7 3.40(3) no . 2_647 C7 H8 3.48(2) no . 2_647 C7 H13 2.98(3) no . . C8 H8 3.23(3) no . 2_647 C8 H13 2.85(2) no . . C9 H12 3.543(18) no . . C9 H13 2.83(3) no . . C9 H15 3.58(3) no . 2_656 C10 H7 3.56(3) no . 2_647 C10 H12 3.02(2) no . . C10 H13 2.93(3) no . . C11 H4 3.16(2) no . 1_565 C12 H4 3.11(2) no . 1_565 C12 H14 3.46(3) no . 1_565 C12 H14 3.54(3) no . 2_656 C13 H14 3.04(3) no . 2_656 C14 H9 3.22(3) no . 1_545 C14 H11 3.30(2) no . 1_545 C14 H14 2.87(3) no . 2_656 C14 H15 2.98(3) no . 2_656 C15 H9 3.30(3) no . 1_545 C15 H10 3.46(3) no . 1_545 C15 H11 2.71(3) no . 1_545 C15 H11 3.02(3) no . 2_646 C15 H14 2.97(3) no . 2_656 C15 H15 3.49(3) no . 2_656 C16 H5 3.25(3) no . 2_656 C16 H10 3.30(3) no . 1_545 C16 H11 3.08(3) no . 1_545 C16 H11 3.34(3) no . 2_646 C16 H13 3.46(3) no . 2_646 C16 H14 3.25(2) no . 2_656 C17 H1 3.25(2) no . 2_546 C17 H5 3.31(3) no . 2_656 C17 H10 3.60(3) no . 1_545 C17 H14 3.43(2) no . 2_656 C18 H1 3.60(2) no . 2_546 C18 H14 3.32(3) no . 2_656 H1 F1 3.35(3) no . 1_565 H1 F1 3.56(3) no . 2_557 H1 F2 3.36(2) no . 1_565 H1 F3 3.47(3) no . 2_557 H1 O2 2.47(3) no . 1_565 H1 N1 3.28(3) no . . H1 C1 3.59(3) no . 1_565 H1 C17 3.25(2) no . 2_556 H1 C18 3.60(2) no . 2_556 H1 H1A 2.6355 no . . H1 H1B 3.0933 no . . H1 H16 2.74(3) no . 2_556 H1 H17 3.41(4) no . 2_556 H1A O1 3.2474 no . . H1A O1 3.4082 no . 1_565 H1A O1 3.1006 no . 2_556 H1A O2 1.9388 no . 1_565 H1A O3 2.9477 no . . H1A C1 2.9379 no . 1_565 H1A C4 3.0963 no . . H1A H1 2.6355 no . . H1A H1B 3.4606 no . 2_556 H1A H1C 3.3677 no . 2_556 H1A H3 3.2148 no . . H1A H4 3.2274 no . 1_565 H1A H17 3.5030 no . 2_556 H1B O1 1.8702 no . . H1B O1 3.2821 no . 2_556 H1B O2 3.3149 no . 1_565 H1B O3 2.6432 no . . H1B C1 2.8592 no . . H1B C2 3.1684 no . . H1B C4 3.0482 no . . H1B H1 3.0933 no . . H1B H1A 3.4606 no . 2_546 H1B H1C 2.9567 no . 2_546 H1B H3 2.8441 no . . H1B H9 3.5963 no . 2_546 H1B H10 3.2696 no . 2_546 H1C O1 3.1231 no . . H1C O1 1.8910 no . 2_556 H1C O2 3.3049 no . 1_565 H1C O2 3.1695 no . 2_556 H1C C1 2.8213 no . 2_556 H1C H1A 3.3677 no . 2_546 H1C H1B 2.9567 no . 2_556 H1C H1C 3.4960 no . 2_546 H1C H1C 3.4960 no . 2_556 H1C H9 3.1365 no . 2_546 H1C H10 3.4759 no . 2_546 H2 F1 2.61(3) no . 2_557 H2 F2 3.21(3) no . 2_557 H2 F3 3.18(3) no . 2_557 H2 C3 3.24(3) no . 2_557 H2 H16 3.52(3) no . 2_556 H3 N1 3.44(3) no . . H3 H1A 3.2148 no . . H3 H1B 2.8441 no . . H3 H10 2.67(4) no . 2_546 H3 H16 3.47(4) no . 2_556 H3 H17 2.78(4) no . 2_546 H4 C11 3.16(2) no . 1_545 H4 C12 3.11(2) no . 1_545 H4 H1A 3.2274 no . 1_545 H4 H8 2.90(4) no . 1_545 H4 H9 2.56(3) no . 1_545 H4 H11 3.21(4) no . 1_545 H4 H12 2.47(3) no . 1_545 H5 F3 3.55(2) no . 2_647 H5 C16 3.25(3) no . 2_646 H5 C17 3.31(3) no . 2_646 H5 H7 2.98(4) no . 1_545 H5 H11 3.47(3) no . 1_545 H5 H12 3.49(3) no . 1_545 H5 H13 3.56(3) no . . H5 H14 3.55(3) no . . H5 H15 2.99(4) no . 2_646 H5 H16 3.11(4) no . 2_646 H6 F2 2.76(3) no . 2_657 H6 H8 3.20(4) no . 2_647 H6 H13 3.32(3) no . . H6 H15 3.57(4) no . 2_656 H7 F2 2.858(19) no . 2_657 H7 F3 3.29(2) no . 2_657 H7 C3 3.545(19) no . 2_657 H7 C5 3.35(2) no . 2_657 H7 C6 3.24(2) no . 2_657 H7 C7 3.40(3) no . 2_657 H7 C10 3.56(3) no . 2_657 H7 H5 2.98(4) no . 1_565 H7 H13 3.31(3) no . . H7 H15 3.33(4) no . 2_656 H8 F2 3.42(3) no . 1_565 H8 C7 3.48(2) no . 2_657 H8 C8 3.23(3) no . 2_657 H8 H4 2.90(4) no . 1_565 H8 H6 3.20(4) no . 2_657 H8 H12 2.88(3) no . . H8 H13 3.49(4) no . . H9 O1 2.67(3) no . 1_565 H9 O2 2.68(3) no . 1_565 H9 C1 2.69(3) no . 1_565 H9 C5 3.58(2) no . 1_565 H9 C6 3.006(19) no . 1_565 H9 C14 3.22(3) no . 1_565 H9 C15 3.30(3) no . 1_565 H9 H1B 3.5963 no . 2_556 H9 H1C 3.1365 no . 2_556 H9 H4 2.56(3) no . 1_565 H9 H13 3.44(3) no . 1_565 H9 H14 3.55(4) no . 1_565 H10 O1 3.02(3) no . 2_556 H10 C4 3.59(3) no . 2_556 H10 C15 3.46(3) no . 1_565 H10 C16 3.30(3) no . 1_565 H10 C17 3.60(3) no . 1_565 H10 H1B 3.2696 no . 2_556 H10 H1C 3.4759 no . 2_556 H10 H3 2.67(4) no . 2_556 H10 H15 3.52(4) no . 1_565 H11 C6 3.58(3) no . 1_565 H11 C14 3.30(2) no . 1_565 H11 C15 2.71(3) no . 1_565 H11 C15 3.02(3) no . 2_656 H11 C16 3.08(3) no . 1_565 H11 C16 3.34(3) no . 2_656 H11 H4 3.21(4) no . 1_565 H11 H5 3.47(3) no . 1_565 H11 H14 2.60(4) no . 1_565 H11 H14 2.77(4) no . 2_656 H11 H15 3.26(4) no . 1_565 H11 H15 3.31(3) no . 2_656 H12 O2 3.22(3) no . 1_565 H12 O3 3.29(3) no . . H12 C5 3.47(2) no . . H12 C6 3.37(2) no . 1_565 H12 C9 3.543(18) no . . H12 C10 3.02(2) no . . H12 H4 2.47(3) no . 1_565 H12 H5 3.49(3) no . 1_565 H12 H8 2.88(3) no . . H12 H15 3.49(4) no . 2_656 H13 C5 3.05(3) no . . H13 C6 3.08(3) no . . H13 C7 2.98(3) no . . H13 C8 2.85(2) no . . H13 C9 2.83(3) no . . H13 C10 2.93(3) no . . H13 C16 3.46(3) no . 2_656 H13 H5 3.56(3) no . . H13 H6 3.32(3) no . . H13 H7 3.31(3) no . . H13 H8 3.49(4) no . . H13 H9 3.44(3) no . 1_545 H13 H14 3.34(4) no . 2_656 H13 H15 2.63(4) no . 2_656 H14 C12 3.46(3) no . 1_545 H14 C12 3.54(3) no . 2_646 H14 C13 3.04(3) no . 2_646 H14 C14 2.87(3) no . 2_646 H14 C15 2.97(3) no . 2_646 H14 C16 3.25(2) no . 2_646 H14 C17 3.43(2) no . 2_646 H14 C18 3.32(3) no . 2_646 H14 H5 3.55(3) no . . H14 H9 3.55(4) no . 1_545 H14 H11 2.60(4) no . 1_545 H14 H11 2.77(4) no . 2_646 H14 H13 3.34(4) no . 2_646 H14 H14 3.45(3) no . 2_646 H14 H14 3.45(3) no . 2_656 H14 H15 3.53(4) no . 2_656 H15 C9 3.58(3) no . 2_646 H15 C14 2.98(3) no . 2_646 H15 C15 3.49(3) no . 2_646 H15 H5 2.99(4) no . 2_656 H15 H6 3.57(4) no . 2_646 H15 H7 3.33(4) no . 2_646 H15 H10 3.52(4) no . 1_545 H15 H11 3.26(4) no . 1_545 H15 H11 3.31(3) no . 2_646 H15 H12 3.49(4) no . 2_646 H15 H13 2.63(4) no . 2_646 H15 H14 3.53(4) no . 2_646 H16 F1 3.59(2) no . 2_556 H16 F3 2.70(3) no . 1_554 H16 C4 3.41(3) no . 2_546 H16 H1 2.74(3) no . 2_546 H16 H2 3.52(3) no . 2_546 H16 H3 3.47(4) no . 2_546 H16 H5 3.11(4) no . 2_656 H17 F1 3.42(2) no . 2_556 H17 O1 2.72(3) no . 2_556 H17 O2 2.73(2) no . 2_556 H17 C1 2.75(3) no . 2_556 H17 H1 3.41(4) no . 2_546 H17 H1A 3.5030 no . 2_546 H17 H3 2.78(4) no . 2_556 #============================================================================== 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_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1A O2 . . 1_565 2.819(2) 0.910 1.939 162.1 no N1 H1B O1 . . . 2.774(2) 0.910 1.870 171.6 no N1 H1C O1 . . 2_556 2.7871(18) 0.910 1.891 167.8 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 934003'