# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_sc0921 _database_code_depnum_ccdc_archive 'CCDC 895081' #TrackingRef 'sc0921.cif.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C11 H14 F2 N2 O4' _chemical_formula_moiety 'C11 H14 F2 N2 O4' _chemical_formula_weight 276.24 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 19.14(3) _cell_length_b 6.288(9) _cell_length_c 19.81(3) _cell_angle_alpha 90.0000 _cell_angle_beta 91.934(15) _cell_angle_gamma 90.0000 _cell_volume 2383(7) _cell_formula_units_Z 8 _cell_measurement_reflns_used 1529 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.340 _exptl_crystal_size_mid 0.210 _exptl_crystal_size_min 0.130 _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152.00 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.879 _exptl_absorpt_correction_T_max 0.982 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku XtaLAB mini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.827 _diffrn_reflns_number 5048 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _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 2211 _reflns_number_gt 1843 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1596 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2210 _refine_ls_number_parameters 175 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0742P)^2^+5.7241P] 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 0.840 _refine_diff_density_min -0.500 _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 0.34874(8) 0.7538(3) 0.29725(9) 0.0272(5) Uani 1.0 8 d . . . F2 F 0.27588(8) 0.5059(3) 0.26379(7) 0.0242(4) Uani 1.0 8 d . . . O1 O 0.23711(10) 0.9016(3) 0.44016(10) 0.0221(5) Uani 1.0 8 d . . . O2 O 0.01259(9) 0.6688(4) 0.42459(10) 0.0276(5) Uani 1.0 8 d . . . O3 O 0.40876(9) 0.3862(3) 0.48207(9) 0.0206(5) Uani 1.0 8 d . . . O4 O 0.42935(15) 0.3215(4) 0.22743(13) 0.0519(8) Uani 1.0 8 d . . . N1 N 0.21703(10) 0.5718(4) 0.39328(10) 0.0164(5) Uani 1.0 8 d . . . N2 N 0.12592(11) 0.7730(4) 0.43557(11) 0.0180(5) Uani 1.0 8 d . . . C1 C 0.19637(13) 0.7597(4) 0.42385(12) 0.0170(6) Uani 1.0 8 d . . . C2 C 0.07456(13) 0.6318(5) 0.41424(12) 0.0179(6) Uani 1.0 8 d . . . C3 C 0.09873(13) 0.4428(5) 0.37986(12) 0.0174(6) Uani 1.0 8 d . . . C4 C 0.16799(13) 0.4225(4) 0.37134(12) 0.0159(6) Uani 1.0 8 d . . . C5 C 0.04595(14) 0.2812(5) 0.35571(14) 0.0237(6) Uani 1.0 8 d . . . C6 C 0.29149(12) 0.5398(4) 0.38455(13) 0.0157(6) Uani 1.0 8 d . . . C7 C 0.32266(13) 0.5605(4) 0.31480(13) 0.0172(6) Uani 1.0 8 d . . . C8 C 0.37480(13) 0.3831(4) 0.33220(13) 0.0173(6) Uani 1.0 8 d . . . C9 C 0.32447(13) 0.3141(4) 0.38923(13) 0.0166(6) Uani 1.0 8 d . . . C10 C 0.39103(14) 0.2233(5) 0.27829(14) 0.0234(6) Uani 1.0 8 d . . . C11 C 0.35572(14) 0.2442(5) 0.45709(13) 0.0194(6) Uani 1.0 8 d . . . H2 H 0.1123 0.8832 0.4591 0.0215 Uiso 1.0 8 calc R . . H3 H 0.4478 0.3459 0.4688 0.0247 Uiso 1.0 8 calc R . . H4A H 0.1841 0.2990 0.3491 0.0190 Uiso 1.0 8 calc R . . H4 H 0.4561 0.2319 0.2103 0.0623 Uiso 1.0 8 calc R . . H5A H 0.0701 0.1585 0.3369 0.0284 Uiso 1.0 8 calc R . . H5B H 0.0150 0.3447 0.3208 0.0284 Uiso 1.0 8 calc R . . H5C H 0.0182 0.2348 0.3937 0.0284 Uiso 1.0 8 calc R . . H6 H 0.3179 0.6358 0.4166 0.0189 Uiso 1.0 8 calc R . . H8 H 0.4190 0.4440 0.3524 0.0208 Uiso 1.0 8 calc R . . H9 H 0.2904 0.2053 0.3715 0.0199 Uiso 1.0 8 calc R . . H10A H 0.4185 0.1045 0.2984 0.0281 Uiso 1.0 8 calc R . . H10B H 0.3470 0.1646 0.2585 0.0281 Uiso 1.0 8 calc R . . H11A H 0.3181 0.2358 0.4901 0.0233 Uiso 1.0 8 calc R . . H11B H 0.3759 0.1002 0.4525 0.0233 Uiso 1.0 8 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.0272(9) 0.0184(9) 0.0366(10) -0.0031(7) 0.0089(8) 0.0088(7) F2 0.0216(8) 0.0329(10) 0.0180(8) 0.0011(7) -0.0014(7) 0.0022(7) O1 0.0217(10) 0.0190(10) 0.0259(10) -0.0020(8) 0.0036(8) -0.0044(8) O2 0.0136(10) 0.0355(12) 0.0337(11) 0.0003(9) 0.0021(8) -0.0094(10) O3 0.0141(9) 0.0244(11) 0.0231(10) 0.0020(8) 0.0005(8) -0.0066(8) O4 0.0730(19) 0.0386(14) 0.0468(15) -0.0135(14) 0.0413(14) -0.0139(12) N1 0.0122(10) 0.0173(11) 0.0196(11) 0.0006(9) 0.0017(9) -0.0006(9) N2 0.0148(11) 0.0185(12) 0.0206(11) 0.0014(9) 0.0017(9) -0.0039(9) C1 0.0176(13) 0.0190(13) 0.0145(12) -0.0007(11) 0.0023(10) 0.0004(10) C2 0.0163(13) 0.0252(15) 0.0123(12) 0.0012(11) 0.0006(10) 0.0010(10) C3 0.0161(12) 0.0200(14) 0.0161(13) -0.0002(10) -0.0003(10) 0.0021(10) C4 0.0184(13) 0.0160(13) 0.0131(12) 0.0008(10) -0.0008(10) -0.0005(10) C5 0.0167(13) 0.0271(16) 0.0270(14) -0.0026(11) -0.0031(11) -0.0021(12) C6 0.0113(12) 0.0159(13) 0.0200(13) -0.0009(10) 0.0012(10) -0.0003(10) C7 0.0168(12) 0.0161(13) 0.0189(13) 0.0025(10) 0.0020(10) 0.0031(10) C8 0.0163(12) 0.0158(13) 0.0201(13) -0.0012(10) 0.0023(10) 0.0005(10) C9 0.0143(12) 0.0176(13) 0.0180(13) -0.0003(10) 0.0017(10) -0.0010(11) C10 0.0211(14) 0.0219(14) 0.0275(15) -0.0037(11) 0.0052(12) -0.0053(12) C11 0.0179(13) 0.0230(14) 0.0175(12) -0.0001(11) 0.0022(10) 0.0010(11) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _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 C7 1.363(4) yes . . F2 C7 1.371(4) yes . . O1 C1 1.222(4) yes . . O2 C2 1.233(4) yes . . O3 C11 1.428(4) yes . . O4 C10 1.409(5) yes . . N1 C1 1.391(4) yes . . N1 C4 1.387(4) yes . . N1 C6 1.455(4) yes . . N2 C1 1.379(4) yes . . N2 C2 1.380(4) yes . . C2 C3 1.453(4) yes . . C3 C4 1.348(4) yes . . C3 C5 1.500(4) yes . . C6 C7 1.529(5) yes . . C6 C9 1.555(4) yes . . C7 C8 1.528(4) yes . . C8 C9 1.570(4) yes . . C8 C10 1.506(4) yes . . C9 C11 1.518(4) yes . . O3 H3 0.840 no . . O4 H4 0.840 no . . N2 H2 0.880 no . . C4 H4A 0.950 no . . C5 H5A 0.980 no . . C5 H5B 0.980 no . . C5 H5C 0.980 no . . C6 H6 1.000 no . . C8 H8 1.000 no . . C9 H9 1.000 no . . C10 H10A 0.990 no . . C10 H10B 0.990 no . . C11 H11A 0.990 no . . C11 H11B 0.990 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 C1 N1 C4 120.8(3) yes . . . C1 N1 C6 117.6(2) yes . . . C4 N1 C6 121.6(3) yes . . . C1 N2 C2 126.9(3) yes . . . O1 C1 N1 123.2(3) yes . . . O1 C1 N2 122.0(3) yes . . . N1 C1 N2 114.8(3) yes . . . O2 C2 N2 120.4(3) yes . . . O2 C2 C3 123.8(3) yes . . . N2 C2 C3 115.8(3) yes . . . C2 C3 C4 117.8(3) yes . . . C2 C3 C5 118.8(3) yes . . . C4 C3 C5 123.4(3) yes . . . N1 C4 C3 123.7(3) yes . . . N1 C6 C7 120.6(2) yes . . . N1 C6 C9 121.1(2) yes . . . C7 C6 C9 87.80(19) yes . . . F1 C7 F2 105.7(2) yes . . . F1 C7 C6 117.6(3) yes . . . F1 C7 C8 117.8(3) yes . . . F2 C7 C6 112.3(3) yes . . . F2 C7 C8 112.9(3) yes . . . C6 C7 C8 90.3(2) yes . . . C7 C8 C9 87.3(2) yes . . . C7 C8 C10 118.4(3) yes . . . C9 C8 C10 118.2(3) yes . . . C6 C9 C8 87.9(2) yes . . . C6 C9 C11 117.7(3) yes . . . C8 C9 C11 119.0(3) yes . . . O4 C10 C8 109.9(3) yes . . . O3 C11 C9 112.3(3) yes . . . C11 O3 H3 109.470 no . . . C10 O4 H4 109.475 no . . . C1 N2 H2 116.564 no . . . C2 N2 H2 116.575 no . . . N1 C4 H4A 118.153 no . . . C3 C4 H4A 118.157 no . . . C3 C5 H5A 109.482 no . . . C3 C5 H5B 109.470 no . . . C3 C5 H5C 109.480 no . . . H5A C5 H5B 109.460 no . . . H5A C5 H5C 109.468 no . . . H5B C5 H5C 109.467 no . . . N1 C6 H6 108.497 no . . . C7 C6 H6 108.503 no . . . C9 C6 H6 108.504 no . . . C7 C8 H8 110.368 no . . . C9 C8 H8 110.380 no . . . C10 C8 H8 110.357 no . . . C6 C9 H9 110.188 no . . . C8 C9 H9 110.182 no . . . C11 C9 H9 110.188 no . . . O4 C10 H10A 109.691 no . . . O4 C10 H10B 109.694 no . . . C8 C10 H10A 109.699 no . . . C8 C10 H10B 109.692 no . . . H10A C10 H10B 108.186 no . . . O3 C11 H11A 109.141 no . . . O3 C11 H11B 109.140 no . . . C9 C11 H11A 109.125 no . . . C9 C11 H11B 109.123 no . . . H11A C11 H11B 107.860 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 C1 N1 C4 C3 -2.5(4) no . . . . C4 N1 C1 O1 -175.3(2) no . . . . C4 N1 C1 N2 5.7(3) no . . . . C1 N1 C6 C7 -106.0(3) no . . . . C1 N1 C6 C9 146.2(2) no . . . . C6 N1 C1 O1 4.0(4) no . . . . C6 N1 C1 N2 -175.03(19) no . . . . C4 N1 C6 C7 73.2(3) no . . . . C4 N1 C6 C9 -34.5(4) no . . . . C6 N1 C4 C3 178.3(2) no . . . . C1 N2 C2 O2 -175.5(3) no . . . . C1 N2 C2 C3 4.5(4) no . . . . C2 N2 C1 O1 174.0(3) no . . . . C2 N2 C1 N1 -7.0(4) no . . . . O2 C2 C3 C4 179.5(3) no . . . . O2 C2 C3 C5 -0.5(4) no . . . . N2 C2 C3 C4 -0.5(4) no . . . . N2 C2 C3 C5 179.52(19) no . . . . C2 C3 C4 N1 -0.2(4) no . . . . C5 C3 C4 N1 179.7(2) no . . . . N1 C6 C7 F1 93.0(3) no . . . . N1 C6 C7 F2 -30.1(4) no . . . . N1 C6 C7 C8 -145.1(2) no . . . . N1 C6 C9 C8 144.1(2) no . . . . N1 C6 C9 C11 -94.0(3) no . . . . C7 C6 C9 C8 19.26(15) no . . . . C7 C6 C9 C11 141.1(2) no . . . . C9 C6 C7 F1 -141.8(3) no . . . . C9 C6 C7 F2 95.2(3) no . . . . C9 C6 C7 C8 -19.80(16) no . . . . F1 C7 C8 C9 141.4(2) no . . . . F1 C7 C8 C10 -97.8(3) no . . . . F2 C7 C8 C9 -94.9(3) no . . . . F2 C7 C8 C10 25.9(3) no . . . . C6 C7 C8 C9 19.60(16) no . . . . C6 C7 C8 C10 140.3(2) no . . . . C7 C8 C9 C6 -19.28(16) no . . . . C7 C8 C9 C11 -140.0(2) no . . . . C7 C8 C10 O4 69.4(3) no . . . . C9 C8 C10 O4 172.58(19) no . . . . C10 C8 C9 C6 -140.2(3) no . . . . C10 C8 C9 C11 99.1(3) no . . . . C6 C9 C11 O3 -57.2(3) no . . . . C8 C9 C11 O3 46.8(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 O4 3.439(5) no . . F1 N1 3.407(5) no . . F1 C9 3.352(5) no . . F1 C10 3.456(6) no . . F2 O4 3.261(6) no . . F2 N1 2.866(5) no . . F2 C4 3.062(5) no . . F2 C9 2.888(5) no . . F2 C10 2.838(5) no . . O1 C2 3.566(6) no . . O1 C4 3.544(5) no . . O1 C6 2.748(5) no . . O2 C1 3.564(7) no . . O2 C4 3.545(6) no . . O2 C5 2.876(5) no . . O3 C6 3.068(5) no . . O3 C8 3.018(6) no . . O4 C7 3.109(5) no . . N1 C2 2.798(6) no . . N1 C8 3.498(6) no . . N1 C11 3.558(5) no . . N2 C4 2.682(5) no . . C1 C3 2.848(5) no . . C1 C7 3.526(5) no . . C4 C7 3.316(6) no . . C4 C9 3.080(6) no . . C6 C10 3.506(5) no . . C7 C11 3.490(6) no . . F1 F2 3.078(4) no . 6_555 F1 C4 3.509(6) no . 6_555 F1 C10 3.088(6) no . 1_565 F2 F1 3.078(4) no . 6_545 F2 F2 3.336(5) no . 6_545 F2 F2 3.336(5) no . 6_555 F2 C10 3.548(6) no . 6_555 O1 O1 3.070(5) no . 7_566 O1 O3 3.498(5) no . 7_566 O1 N1 3.390(6) no . 7_566 O1 C1 3.111(5) no . 7_566 O1 C6 3.553(7) no . 7_566 O1 C9 3.264(5) no . 1_565 O1 C11 3.139(5) no . 1_565 O1 C11 3.536(5) no . 7_566 O2 O3 2.696(4) no . 5_455 O2 O4 3.384(6) no . 6_555 O2 C8 3.434(5) no . 5_455 O2 C11 3.128(6) no . 5_455 O3 O1 3.498(5) no . 7_566 O3 O2 2.696(4) no . 5_545 O3 N2 2.787(4) no . 7_566 O3 C1 3.569(5) no . 7_566 O3 C3 3.436(5) no . 7_556 O3 C5 3.464(6) no . 7_556 O4 O2 3.384(6) no . 6_545 O4 O4 2.820(6) no . 2_655 O4 N2 3.378(6) no . 6_545 O4 C2 3.048(6) no . 6_545 O4 C3 3.225(5) no . 6_545 O4 C5 3.368(6) no . 6_555 O4 C10 3.499(7) no . 2_655 N1 O1 3.390(6) no . 7_566 N2 O3 2.787(4) no . 7_566 N2 O4 3.378(6) no . 6_555 C1 O1 3.111(5) no . 7_566 C1 O3 3.569(5) no . 7_566 C1 C1 3.594(6) no . 7_566 C2 O4 3.048(6) no . 6_555 C3 O3 3.436(5) no . 7_556 C3 O4 3.225(5) no . 6_555 C3 C11 3.519(6) no . 7_556 C4 F1 3.509(6) no . 6_545 C5 O3 3.464(6) no . 7_556 C5 O4 3.368(6) no . 6_545 C6 O1 3.553(7) no . 7_566 C8 O2 3.434(5) no . 5_545 C9 O1 3.264(5) no . 1_545 C10 F1 3.088(6) no . 1_545 C10 F2 3.548(6) no . 6_545 C10 O4 3.499(7) no . 2_655 C11 O1 3.139(5) no . 1_545 C11 O1 3.536(5) no . 7_566 C11 O2 3.128(6) no . 5_545 C11 C3 3.519(6) no . 7_556 F1 H6 2.5650 no . . F1 H8 2.5882 no . . F2 H4A 2.7982 no . . F2 H6 3.2106 no . . F2 H8 3.2272 no . . F2 H9 2.8576 no . . F2 H10B 2.5456 no . . O1 H2 2.4345 no . . O1 H6 2.3353 no . . O2 H2 2.4156 no . . O2 H5B 2.8970 no . . O2 H5C 2.7998 no . . O3 H6 2.6494 no . . O3 H8 2.6073 no . . O3 H9 3.2990 no . . O4 H8 2.6076 no . . N1 H2 3.1197 no . . N1 H9 2.7408 no . . N1 H11A 3.4118 no . . C1 H4A 3.2584 no . . C1 H6 2.4620 no . . C2 H4A 3.2596 no . . C2 H5A 3.3474 no . . C2 H5B 2.8005 no . . C2 H5C 2.7442 no . . C3 H2 3.1894 no . . C4 H2 3.5605 no . . C4 H5A 2.5780 no . . C4 H5B 3.1010 no . . C4 H5C 3.1456 no . . C4 H6 3.2649 no . . C4 H9 2.7124 no . . C5 H4A 2.6547 no . . C6 H3 3.5904 no . . C6 H4A 2.6292 no . . C6 H8 2.6130 no . . C6 H11A 2.8664 no . . C6 H11B 3.4526 no . . C7 H4A 3.2120 no . . C7 H9 2.5845 no . . C7 H10A 3.4255 no . . C7 H10B 2.7744 no . . C8 H3 3.0130 no . . C8 H4 3.0670 no . . C8 H6 2.5740 no . . C8 H11A 3.4713 no . . C8 H11B 2.9738 no . . C9 H3 2.8017 no . . C9 H4A 2.7775 no . . C9 H10A 2.9034 no . . C9 H10B 2.8028 no . . C10 H9 2.7152 no . . C10 H11B 3.5587 no . . C11 H6 2.6817 no . . C11 H8 2.7406 no . . C11 H10A 3.5140 no . . H3 H6 3.2256 no . . H3 H8 2.4318 no . . H3 H11A 2.6246 no . . H3 H11B 2.0867 no . . H4A H5A 2.3590 no . . H4A H5B 3.2784 no . . H4A H5C 3.3496 no . . H4A H6 3.5492 no . . H4A H9 2.1505 no . . H4 H8 3.2162 no . . H4 H10A 2.0713 no . . H4 H10B 2.3632 no . . H6 H8 2.6414 no . . H6 H9 2.8924 no . . H6 H11A 2.9064 no . . H8 H9 2.9176 no . . H8 H10A 2.3878 no . . H8 H10B 2.8778 no . . H8 H11B 3.0647 no . . H9 H10A 2.9575 no . . H9 H10B 2.5332 no . . H9 H11A 2.3988 no . . H9 H11B 2.3480 no . . H10A H11B 3.1859 no . . F1 H4A 2.9586 no . 6_555 F1 H5A 3.1792 no . 6_555 F1 H5B 3.2518 no . 5_555 F1 H9 3.4035 no . 1_565 F1 H10A 2.5777 no . 1_565 F1 H10B 2.6948 no . 1_565 F2 H4A 3.0158 no . 6_555 F2 H9 3.1842 no . 6_555 F2 H10B 2.5782 no . 6_555 O1 H4A 3.2260 no . 1_565 O1 H6 3.0695 no . 7_566 O1 H9 2.5749 no . 1_565 O1 H11A 2.7746 no . 1_565 O1 H11A 2.8845 no . 7_566 O1 H11B 2.9387 no . 1_565 O2 H3 1.9019 no . 5_455 O2 H4 2.7872 no . 6_555 O2 H8 2.8412 no . 5_455 O2 H10A 3.0575 no . 5_455 O2 H11B 2.7260 no . 5_455 O3 H2 1.9115 no . 7_566 O3 H3 3.3375 no . 3_666 O3 H5C 3.5364 no . 5_555 O3 H5C 2.8910 no . 7_556 O4 H4 2.5424 no . 2_655 O4 H5A 2.4725 no . 6_555 O4 H5B 3.3322 no . 6_545 O4 H5B 3.5967 no . 6_555 O4 H8 3.4400 no . 2_655 O4 H10A 3.2720 no . 2_655 N1 H10B 3.2599 no . 6_555 N1 H11A 3.1042 no . 7_556 N2 H3 3.5234 no . 5_455 N2 H3 3.3915 no . 7_566 N2 H4 3.2523 no . 6_555 N2 H5A 3.2708 no . 1_565 N2 H6 3.1390 no . 7_566 N2 H11A 3.5699 no . 7_566 N2 H11B 3.2292 no . 7_556 C1 H6 3.2496 no . 7_566 C1 H9 3.5062 no . 1_565 C1 H11A 3.5668 no . 7_556 C2 H3 3.0071 no . 5_455 C2 H4 2.5946 no . 6_555 C2 H11A 3.5898 no . 7_556 C2 H11B 3.1341 no . 7_556 C3 H4 2.7331 no . 6_555 C3 H10B 3.2749 no . 6_555 C3 H11A 3.1859 no . 7_556 C3 H11B 3.3503 no . 7_556 C4 H4 3.4323 no . 6_555 C4 H10B 2.9933 no . 6_555 C4 H11A 2.9230 no . 7_556 C5 H2 3.4490 no . 1_545 C5 H3 3.5648 no . 7_556 C5 H4 3.1210 no . 6_555 C5 H8 3.2240 no . 5_445 C5 H10A 3.3442 no . 5_455 C6 H2 3.5824 no . 7_566 C7 H4A 3.5740 no . 6_555 C7 H10B 3.5715 no . 6_555 C8 H4 3.5037 no . 2_655 C10 H4 2.9279 no . 2_655 C10 H5B 3.4461 no . 5_545 C11 H2 2.9243 no . 7_566 C11 H11A 3.5240 no . 7_556 H2 O3 1.9115 no . 7_566 H2 C5 3.4490 no . 1_565 H2 C6 3.5824 no . 7_566 H2 C11 2.9243 no . 7_566 H2 H3 3.1680 no . 5_455 H2 H3 2.5244 no . 7_566 H2 H5A 3.0630 no . 1_565 H2 H5C 3.1068 no . 1_565 H2 H6 2.7647 no . 7_566 H2 H11A 2.9041 no . 7_566 H2 H11B 3.5108 no . 7_556 H3 O2 1.9019 no . 5_545 H3 O3 3.3375 no . 3_666 H3 N2 3.5234 no . 5_545 H3 N2 3.3915 no . 7_566 H3 C2 3.0071 no . 5_545 H3 C5 3.5648 no . 7_556 H3 H2 3.1680 no . 5_545 H3 H2 2.5244 no . 7_566 H3 H3 3.0172 no . 3_666 H3 H5C 3.1850 no . 5_555 H3 H5C 2.8247 no . 7_556 H4A F1 2.9586 no . 6_545 H4A F2 3.0158 no . 6_545 H4A O1 3.2260 no . 1_545 H4A C7 3.5740 no . 6_545 H4A H10B 3.1759 no . 6_555 H4A H11A 3.1951 no . 7_556 H4 O2 2.7872 no . 6_545 H4 O4 2.5424 no . 2_655 H4 N2 3.2523 no . 6_545 H4 C2 2.5946 no . 6_545 H4 C3 2.7331 no . 6_545 H4 C4 3.4323 no . 6_545 H4 C5 3.1210 no . 6_545 H4 C8 3.5037 no . 2_655 H4 C10 2.9279 no . 2_655 H4 H4 2.2624 no . 2_655 H4 H5A 2.8792 no . 6_555 H4 H5B 3.4383 no . 5_545 H4 H5B 2.5762 no . 6_545 H4 H8 3.0404 no . 2_655 H4 H10A 2.5422 no . 2_655 H5A F1 3.1792 no . 6_545 H5A O4 2.4725 no . 6_545 H5A N2 3.2708 no . 1_545 H5A H2 3.0630 no . 1_545 H5A H4 2.8792 no . 6_545 H5A H8 3.2159 no . 5_445 H5B F1 3.2518 no . 5_445 H5B O4 3.5967 no . 6_545 H5B O4 3.3322 no . 6_555 H5B C10 3.4461 no . 5_455 H5B H4 3.4383 no . 5_455 H5B H4 2.5762 no . 6_555 H5B H5B 2.8436 no . 2_555 H5B H8 3.1935 no . 5_445 H5B H10A 2.4946 no . 5_455 H5B H10A 3.1730 no . 6_555 H5C O3 3.5364 no . 5_445 H5C O3 2.8910 no . 7_556 H5C H2 3.1068 no . 1_545 H5C H3 3.1850 no . 5_445 H5C H3 2.8247 no . 7_556 H5C H8 2.7409 no . 5_445 H5C H10A 3.5160 no . 5_455 H6 O1 3.0695 no . 7_566 H6 N2 3.1390 no . 7_566 H6 C1 3.2496 no . 7_566 H6 H2 2.7647 no . 7_566 H6 H11B 3.1965 no . 1_565 H8 O2 2.8412 no . 5_545 H8 O4 3.4400 no . 2_655 H8 C5 3.2240 no . 5_555 H8 H4 3.0404 no . 2_655 H8 H5A 3.2159 no . 5_555 H8 H5B 3.1935 no . 5_555 H8 H5C 2.7409 no . 5_555 H9 F1 3.4035 no . 1_545 H9 F2 3.1842 no . 6_545 H9 O1 2.5749 no . 1_545 H9 C1 3.5062 no . 1_545 H9 H11A 3.5144 no . 7_556 H10A F1 2.5777 no . 1_545 H10A O2 3.0575 no . 5_545 H10A O4 3.2720 no . 2_655 H10A C5 3.3442 no . 5_545 H10A H4 2.5422 no . 2_655 H10A H5B 2.4946 no . 5_545 H10A H5B 3.1730 no . 6_545 H10A H5C 3.5160 no . 5_545 H10B F1 2.6948 no . 1_545 H10B F2 2.5782 no . 6_545 H10B N1 3.2599 no . 6_545 H10B C3 3.2749 no . 6_545 H10B C4 2.9933 no . 6_545 H10B C7 3.5715 no . 6_545 H10B H4A 3.1759 no . 6_545 H11A O1 2.7746 no . 1_545 H11A O1 2.8845 no . 7_566 H11A N1 3.1042 no . 7_556 H11A N2 3.5699 no . 7_566 H11A C1 3.5668 no . 7_556 H11A C2 3.5898 no . 7_556 H11A C3 3.1859 no . 7_556 H11A C4 2.9230 no . 7_556 H11A C11 3.5240 no . 7_556 H11A H2 2.9041 no . 7_566 H11A H4A 3.1951 no . 7_556 H11A H9 3.5144 no . 7_556 H11A H11A 2.6569 no . 7_556 H11B O1 2.9387 no . 1_545 H11B O2 2.7260 no . 5_545 H11B N2 3.2292 no . 7_556 H11B C2 3.1341 no . 7_556 H11B C3 3.3503 no . 7_556 H11B H2 3.5108 no . 7_556 H11B H6 3.1965 no . 1_545 #============================================================================== 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 O3 H3 O2 . . 5_545 2.696(4) 0.840 1.902 157.1 no O4 H4 O4 . . 2_655 2.820(6) 0.840 2.542 100.5 no N2 H2 O3 . . 7_566 2.787(4) 0.880 1.911 173.2 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 #==============================================================================