# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2018 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_8 _database_code_depnum_ccdc_archive 'CCDC 1817386' _audit_update_record ; 2018-01-16 deposited with the CCDC. 2018-02-19 downloaded from the CCDC. ; _audit_creation_date 2018-01-08 _audit_creation_method 'by CrystalStructure 4.2' _chemical_formula_sum 'C12 H12 F4 O' _chemical_formula_moiety 'C12 H12 F4 O' _chemical_formula_weight 248.22 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _space_group_IT_number 19 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,-Y,1/2+Z 3 1/2+X,1/2-Y,-Z 4 -X,1/2+Y,1/2-Z #------------------------------------------------------------------------------ _cell_length_a 6.0422(12) _cell_length_b 11.778(3) _cell_length_c 15.448(3) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1099.4(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1219 _cell_measurement_theta_min 40.50 _cell_measurement_theta_max 68.00 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512.00 _exptl_absorpt_coefficient_mu 1.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.740 _exptl_absorpt_correction_T_max 0.976 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku XtaLAB P100' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.814 _diffrn_reflns_number 11746 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_theta_max 68.225 _diffrn_reflns_theta_min 4.721 _diffrn_reflns_theta_full 67.687 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? _reflns_number_total 1998 _reflns_number_gt 1911 _reflns_threshold_expression F^2^>2.0\s(F^2^) _reflns_Friedel_coverage 0.680 _reflns_Friedel_fraction_max 0.987 _reflns_Friedel_fraction_full 0.991 #============================================================================== # 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). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0833 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 1998 _refine_ls_number_parameters 158 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0548P)^2^+0.0186P] 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 0.000 _refine_diff_density_max 0.14 _refine_diff_density_min -0.13 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; Flack x determined using 746 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.06(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; F F 0.0727 0.0534 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F2 F 0.1835(2) 0.35526(9) 0.70271(7) 0.0435(3) Uani 1 1 d . . . . . F3 F 0.4378(3) 0.39588(12) 0.84392(8) 0.0603(4) Uani 1 1 d . . . . . F5 F -0.1757(3) 0.16099(13) 0.91137(9) 0.0629(4) Uani 1 1 d . . . . . F6 F -0.1692(2) 0.22179(12) 0.74306(8) 0.0496(3) Uani 1 1 d . . . . . O1 O 0.3458(3) 0.07006(12) 0.75558(9) 0.0444(4) Uani 1 1 d D . . . . C1 C 0.1983(3) 0.15263(15) 0.71971(11) 0.0308(4) Uani 1 1 d . . . . . C2 C 0.3121(3) 0.26799(16) 0.73672(12) 0.0337(4) Uani 1 1 d . . . . . H2 H 0.460046 0.268441 0.707739 0.040 Uiso 1 1 calc R U . . . C3 C 0.3434(4) 0.28774(18) 0.83282(12) 0.0400(5) Uani 1 1 d . . . . . H3 H 0.446149 0.228930 0.856567 0.048 Uiso 1 1 calc R U . . . C4 C 0.1270(4) 0.28358(19) 0.88183(12) 0.0411(5) Uani 1 1 d . . . . . H4A H 0.024930 0.342781 0.860046 0.049 Uiso 1 1 calc R U . . . H4B H 0.153002 0.296994 0.944271 0.049 Uiso 1 1 calc R U . . . C5 C 0.0284(4) 0.16693(18) 0.86791(13) 0.0425(5) Uani 1 1 d . . . . . H5 H 0.130933 0.108123 0.891826 0.051 Uiso 1 1 calc R U . . . C6 C -0.0145(3) 0.14263(17) 0.77308(12) 0.0393(4) Uani 1 1 d . . . . . H6 H -0.076463 0.064322 0.766775 0.047 Uiso 1 1 calc R U . . . C7 C 0.1634(4) 0.13085(15) 0.62307(11) 0.0328(4) Uani 1 1 d . . . . . C8 C -0.0332(4) 0.08568(18) 0.59158(15) 0.0466(5) Uani 1 1 d . . . . . H8 H -0.153694 0.072525 0.629813 0.056 Uiso 1 1 calc R U . . . C9 C -0.0538(5) 0.0597(2) 0.50409(16) 0.0598(7) Uani 1 1 d . . . . . H9 H -0.188347 0.028513 0.482951 0.072 Uiso 1 1 calc R U . . . C10 C 0.1180(5) 0.0787(2) 0.44824(14) 0.0601(8) Uani 1 1 d . . . . . H10 H 0.102255 0.060849 0.388578 0.072 Uiso 1 1 calc R U . . . C11 C 0.3133(6) 0.1236(2) 0.47844(14) 0.0578(7) Uani 1 1 d . . . . . H11 H 0.432011 0.137025 0.439447 0.069 Uiso 1 1 calc R U . . . C12 C 0.3382(4) 0.14958(18) 0.56634(13) 0.0431(5) Uani 1 1 d . . . . . H12 H 0.473921 0.179884 0.587102 0.052 Uiso 1 1 calc R U . . . H1 H 0.377(6) 0.009(2) 0.7146(16) 0.086(11) Uiso 1 1 d D . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.0597(8) 0.0336(6) 0.0373(5) 0.0046(4) 0.0009(5) 0.0013(5) F3 0.0686(10) 0.0613(8) 0.0511(7) -0.0169(6) 0.0037(7) -0.0281(7) F5 0.0653(9) 0.0744(9) 0.0491(7) 0.0006(6) 0.0278(7) -0.0135(8) F6 0.0321(6) 0.0675(8) 0.0491(7) -0.0039(6) 0.0000(5) 0.0029(6) O1 0.0580(9) 0.0419(7) 0.0335(7) 0.0027(6) -0.0037(6) 0.0153(7) C1 0.0343(9) 0.0319(8) 0.0262(8) 0.0020(7) 0.0012(7) -0.0005(8) C2 0.0335(9) 0.0359(9) 0.0317(9) 0.0003(7) 0.0011(7) -0.0039(8) C3 0.0423(11) 0.0433(11) 0.0345(9) -0.0054(8) -0.0022(9) -0.0086(9) C4 0.0478(12) 0.0473(11) 0.0283(8) -0.0046(8) 0.0031(8) -0.0026(9) C5 0.0487(12) 0.0464(11) 0.0324(9) 0.0046(8) 0.0137(9) -0.0025(10) C6 0.0386(10) 0.0400(10) 0.0393(10) 0.0015(8) 0.0054(9) -0.0072(9) C7 0.0426(10) 0.0272(8) 0.0285(8) 0.0012(7) -0.0025(8) 0.0011(8) C8 0.0542(13) 0.0402(10) 0.0455(10) -0.0087(9) -0.0079(10) -0.0039(10) C9 0.0788(18) 0.0497(13) 0.0510(12) -0.0160(11) -0.0257(13) 0.0078(12) C10 0.103(2) 0.0448(12) 0.0321(10) -0.0097(9) -0.0169(13) 0.0244(14) C11 0.093(2) 0.0466(12) 0.0337(10) 0.0009(9) 0.0123(12) 0.0140(13) C12 0.0555(12) 0.0418(10) 0.0322(9) 0.0004(8) 0.0072(9) 0.0010(10) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)' _computing_cell_refinement 'CrystalClear-SM Expert 2.1 b32' _computing_data_reduction 'CrystalClear-SM Expert 2.1 b32' _computing_structure_solution 'SIR2011 (Burla, et al., 2012)' _computing_structure_refinement 'SHELXL Version 2017/1 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.2 (Rigaku, 2015)' _computing_molecular_graphics 'CrystalStructure 4.2' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F2 C2 1.392(2) . ? F3 C3 1.406(2) . ? F5 C5 1.406(3) . ? F6 C6 1.399(2) . ? O1 C1 1.431(2) . ? O1 H1 0.975(7) . ? C1 C7 1.529(2) . ? C1 C6 1.532(3) . ? C1 C2 1.545(2) . ? C2 C3 1.514(3) . ? C2 H2 1.0000 . ? C3 C4 1.511(3) . ? C3 H3 1.0000 . ? C4 C5 1.513(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.515(3) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 C8 1.390(3) . ? C7 C12 1.390(3) . ? C8 C9 1.391(3) . ? C8 H8 0.9500 . ? C9 C10 1.368(4) . ? C9 H9 0.9500 . ? C10 C11 1.375(5) . ? C10 H10 0.9500 . ? C11 C12 1.400(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 112(2) . . ? O1 C1 C7 110.48(14) . . ? O1 C1 C6 105.20(14) . . ? C7 C1 C6 113.37(16) . . ? O1 C1 C2 104.75(15) . . ? C7 C1 C2 112.01(14) . . ? C6 C1 C2 110.46(14) . . ? F2 C2 C3 109.05(15) . . ? F2 C2 C1 109.69(15) . . ? C3 C2 C1 110.94(15) . . ? F2 C2 H2 109.0 . . ? C3 C2 H2 109.0 . . ? C1 C2 H2 109.0 . . ? F3 C3 C4 108.61(17) . . ? F3 C3 C2 108.02(16) . . ? C4 C3 C2 112.21(17) . . ? F3 C3 H3 109.3 . . ? C4 C3 H3 109.3 . . ? C2 C3 H3 109.3 . . ? C3 C4 C5 107.39(16) . . ? C3 C4 H4A 110.2 . . ? C5 C4 H4A 110.2 . . ? C3 C4 H4B 110.2 . . ? C5 C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? F5 C5 C4 108.83(17) . . ? F5 C5 C6 107.58(19) . . ? C4 C5 C6 112.12(16) . . ? F5 C5 H5 109.4 . . ? C4 C5 H5 109.4 . . ? C6 C5 H5 109.4 . . ? F6 C6 C5 108.00(16) . . ? F6 C6 C1 109.33(14) . . ? C5 C6 C1 111.22(17) . . ? F6 C6 H6 109.4 . . ? C5 C6 H6 109.4 . . ? C1 C6 H6 109.4 . . ? C8 C7 C12 119.32(18) . . ? C8 C7 C1 121.58(19) . . ? C12 C7 C1 118.96(19) . . ? C7 C8 C9 120.0(2) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.0(2) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 120.4(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C7 C12 C11 119.7(2) . . ? C7 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 F2 178.92(14) . . . . ? C7 C1 C2 F2 59.13(19) . . . . ? C6 C1 C2 F2 -68.27(18) . . . . ? O1 C1 C2 C3 -60.55(19) . . . . ? C7 C1 C2 C3 179.66(17) . . . . ? C6 C1 C2 C3 52.3(2) . . . . ? F2 C2 C3 F3 -56.4(2) . . . . ? C1 C2 C3 F3 -177.30(16) . . . . ? F2 C2 C3 C4 63.3(2) . . . . ? C1 C2 C3 C4 -57.6(2) . . . . ? F3 C3 C4 C5 179.40(16) . . . . ? C2 C3 C4 C5 60.1(2) . . . . ? C3 C4 C5 F5 -178.84(16) . . . . ? C3 C4 C5 C6 -60.0(2) . . . . ? F5 C5 C6 F6 57.5(2) . . . . ? C4 C5 C6 F6 -62.2(2) . . . . ? F5 C5 C6 C1 177.42(15) . . . . ? C4 C5 C6 C1 57.8(2) . . . . ? O1 C1 C6 F6 179.33(14) . . . . ? C7 C1 C6 F6 -59.8(2) . . . . ? C2 C1 C6 F6 66.80(19) . . . . ? O1 C1 C6 C5 60.15(19) . . . . ? C7 C1 C6 C5 -179.02(16) . . . . ? C2 C1 C6 C5 -52.4(2) . . . . ? O1 C1 C7 C8 106.4(2) . . . . ? C6 C1 C7 C8 -11.4(2) . . . . ? C2 C1 C7 C8 -137.27(18) . . . . ? O1 C1 C7 C12 -69.2(2) . . . . ? C6 C1 C7 C12 172.97(17) . . . . ? C2 C1 C7 C12 47.1(2) . . . . ? C12 C7 C8 C9 0.0(3) . . . . ? C1 C7 C8 C9 -175.6(2) . . . . ? C7 C8 C9 C10 -0.3(4) . . . . ? C8 C9 C10 C11 0.1(4) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C8 C7 C12 C11 0.5(3) . . . . ? C1 C7 C12 C11 176.17(18) . . . . ? C10 C11 C12 C7 -0.6(3) . . . . ? #============================================================================== 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 O1 H1 F3 . . 4_646 2.878(2) 0.98(2) 1.96(3) 155(3) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. _shelx_res_file ; TITL MADH6 shelxl.res created by SHELXL-2017/1 at 12:28:12 on 08-Jan-2018 CELL 1.54187 6.04220 11.77800 15.44800 90.00000 90.00000 90.00000 ZERR 4 0.00120 0.00300 0.00300 0.00000 0.00000 0.00000 LATT -1 SYMM .50-X, -Y, .50+Z SYMM .50+X, .50-Y, -Z SYMM -X, .50+Y, .50-Z SFAC C H F O UNIT 48 48 16 4 OMIT -1 2 1 L.S. 20 FMAP 2 PLAN 5 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -100.0 ACTA SIZE 0.240 0.060 0.020 DFIX 0.9800 0.0050 O1 H1 WGHT 0.054800 0.018600 FVAR 1.01260 F2 3 0.183450 0.355256 0.702714 11.00000 0.05972 0.03356 = 0.03729 0.00462 0.00092 0.00129 F3 3 0.437758 0.395880 0.843920 11.00000 0.06865 0.06127 = 0.05106 -0.01690 0.00369 -0.02811 F5 3 -0.175730 0.160994 0.911370 11.00000 0.06533 0.07435 = 0.04907 0.00058 0.02777 -0.01351 F6 3 -0.169184 0.221792 0.743056 11.00000 0.03210 0.06745 = 0.04914 -0.00388 -0.00004 0.00294 O1 4 0.345817 0.070062 0.755584 11.00000 0.05797 0.04186 = 0.03348 0.00274 -0.00366 0.01527 C1 1 0.198303 0.152627 0.719712 11.00000 0.03428 0.03192 = 0.02621 0.00196 0.00117 -0.00050 C2 1 0.312061 0.267985 0.736722 11.00000 0.03354 0.03589 = 0.03172 0.00027 0.00109 -0.00391 AFIX 13 H2 2 0.460046 0.268441 0.707739 11.00000 -1.20000 AFIX 0 C3 1 0.343374 0.287738 0.832816 11.00000 0.04231 0.04328 = 0.03446 -0.00541 -0.00220 -0.00860 AFIX 13 H3 2 0.446149 0.228930 0.856567 11.00000 -1.20000 AFIX 0 C4 1 0.127037 0.283576 0.881827 11.00000 0.04777 0.04725 = 0.02826 -0.00456 0.00312 -0.00261 AFIX 23 H4A 2 0.024930 0.342781 0.860046 11.00000 -1.20000 H4B 2 0.153002 0.296994 0.944271 11.00000 -1.20000 AFIX 0 C5 1 0.028415 0.166933 0.867908 11.00000 0.04867 0.04638 = 0.03239 0.00459 0.01373 -0.00248 AFIX 13 H5 2 0.130933 0.108123 0.891826 11.00000 -1.20000 AFIX 0 C6 1 -0.014549 0.142626 0.773079 11.00000 0.03862 0.03996 = 0.03929 0.00151 0.00536 -0.00716 AFIX 13 H6 2 -0.076463 0.064322 0.766775 11.00000 -1.20000 AFIX 0 C7 1 0.163423 0.130849 0.623073 11.00000 0.04264 0.02719 = 0.02854 0.00120 -0.00245 0.00112 C8 1 -0.033247 0.085675 0.591578 11.00000 0.05417 0.04024 = 0.04547 -0.00874 -0.00789 -0.00386 AFIX 43 H8 2 -0.153694 0.072525 0.629813 11.00000 -1.20000 AFIX 0 C9 1 -0.053809 0.059708 0.504095 11.00000 0.07881 0.04968 = 0.05100 -0.01601 -0.02569 0.00778 AFIX 43 H9 2 -0.188347 0.028513 0.482951 11.00000 -1.20000 AFIX 0 C10 1 0.117955 0.078688 0.448236 11.00000 0.10347 0.04478 = 0.03211 -0.00970 -0.01685 0.02441 AFIX 43 H10 2 0.102255 0.060849 0.388578 11.00000 -1.20000 AFIX 0 C11 1 0.313287 0.123577 0.478439 11.00000 0.09299 0.04665 = 0.03367 0.00091 0.01229 0.01405 AFIX 43 H11 2 0.432011 0.137025 0.439447 11.00000 -1.20000 AFIX 0 C12 1 0.338222 0.149585 0.566338 11.00000 0.05552 0.04175 = 0.03216 0.00039 0.00725 0.00098 AFIX 43 H12 2 0.473921 0.179884 0.587102 11.00000 -1.20000 AFIX 0 H1 2 0.376747 0.009121 0.714576 11.00000 0.08614 HKLF 4 REM MADH6 REM R1 = 0.0295 for 1911 Fo > 4sig(Fo) and 0.0303 for all 1998 data REM 158 parameters refined using 1 restraints END WGHT 0.0471 0.0338 REM Instructions for potential hydrogen bonds EQIV $1 x+1, y, z HTAB C2 F6_$1 HTAB C3 F5_$1 EQIV $2 x+1/2, -y+1/2, -z+2 HTAB C4 F5_$2 EQIV $3 -x, y-1/2, -z+3/2 HTAB C6 F2_$3 EQIV $4 -x+1, y-1/2, -z+3/2 HTAB O1 F3_$4 REM Highest difference peak 0.141, deepest hole -0.134, 1-sigma level 0.030 Q1 1 0.1770 0.1384 0.6684 11.00000 0.05 0.14 Q2 1 0.0147 0.1457 0.8202 11.00000 0.05 0.13 Q3 1 0.5660 0.3739 0.8349 11.00000 0.05 0.12 Q4 1 -0.0746 0.1259 0.9402 11.00000 0.05 0.12 Q5 1 0.2444 0.2753 0.8635 11.00000 0.05 0.11 ; _shelx_res_checksum 42889 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_12a _database_code_depnum_ccdc_archive 'CCDC 1817387' _audit_update_record ; 2018-01-16 deposited with the CCDC. 2018-02-19 downloaded from the CCDC. ; _audit_creation_date 2016-10-06 _audit_creation_method 'by CrystalStructure 4.2' _chemical_formula_sum 'C12 H14 F2 O' _chemical_formula_moiety 'C12 H14 F2 O' _chemical_formula_weight 212.24 _chemical_melting_point ? _chemical_absolute_configuration 'ad ' #============================================================================== # CRYSTAL DATA _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _space_group_IT_number 19 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,-Y,1/2+Z 3 1/2+X,1/2-Y,-Z 4 -X,1/2+Y,1/2-Z #------------------------------------------------------------------------------ _cell_length_a 5.25889(6) _cell_length_b 9.75241(11) _cell_length_c 20.4698(2) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1049.83(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10468 _cell_measurement_theta_min 4.25 _cell_measurement_theta_max 75.22 _cell_measurement_temperature 125 #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.020 _exptl_crystal_size_min 0.010 _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448.00 _exptl_absorpt_coefficient_mu 0.911 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.568 _exptl_absorpt_correction_T_max 0.991 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 125 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.811 _diffrn_reflns_number 12388 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_theta_max 75.399 _diffrn_reflns_theta_min 4.320 _diffrn_reflns_theta_full 67.687 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? _reflns_number_total 2150 _reflns_number_gt 2109 _reflns_threshold_expression F^2^>2.0\s(F^2^) _reflns_Friedel_coverage 0.663 _reflns_Friedel_fraction_max 0.973 _reflns_Friedel_fraction_full 1.000 #============================================================================== # 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). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0709 _refine_ls_wR_factor_gt 0.0705 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 2150 _refine_ls_number_parameters 140 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0403P)^2^+0.1640P] 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 0.14 _refine_diff_density_min -0.15 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; Flack x determined using 842 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.04(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; F F 0.0727 0.0534 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F2 F 0.19895(15) 0.59490(9) 0.61535(5) 0.0283(2) Uani 1 1 d . . . . . F3 F 0.4974(2) 0.76389(10) 0.54222(5) 0.0355(2) Uani 1 1 d . . . . . O5 O 0.7353(2) 0.28970(12) 0.51335(6) 0.0321(3) Uani 1 1 d D . . . . C1 C 0.5534(3) 0.48650(14) 0.66677(7) 0.0228(3) Uani 1 1 d . . . . . H1 H 0.7291 0.5066 0.6828 0.027 Uiso 1 1 calc R U . . . C2 C 0.4557(3) 0.61604(15) 0.63297(7) 0.0229(3) Uani 1 1 d . . . . . H2 H 0.4676 0.6954 0.6637 0.027 Uiso 1 1 calc R U . . . C3 C 0.6042(3) 0.64776(15) 0.57146(7) 0.0246(3) Uani 1 1 d . . . . . H3 H 0.7839 0.6691 0.5838 0.030 Uiso 1 1 calc R U . . . C4 C 0.6052(3) 0.52892(16) 0.52369(7) 0.0269(3) Uani 1 1 d . . . . . H4A H 0.7055 0.5534 0.4845 0.032 Uiso 1 1 calc R U . . . H4B H 0.4292 0.5079 0.5097 0.032 Uiso 1 1 calc R U . . . C5 C 0.7217(3) 0.40441(15) 0.55699(7) 0.0248(3) Uani 1 1 d . . . . . H5 H 0.8990 0.4287 0.5704 0.030 Uiso 1 1 calc R U . . . C6 C 0.5735(3) 0.36703(15) 0.61814(7) 0.0253(3) Uani 1 1 d . . . . . H6A H 0.6577 0.2885 0.6399 0.030 Uiso 1 1 calc R U . . . H6B H 0.4002 0.3376 0.6055 0.030 Uiso 1 1 calc R U . . . C7 C 0.3914(3) 0.45267(15) 0.72625(7) 0.0259(3) Uani 1 1 d . . . . . C8 C 0.1889(3) 0.36066(19) 0.72322(8) 0.0325(4) Uani 1 1 d . . . . . H8 H 0.1528 0.3153 0.6832 0.039 Uiso 1 1 calc R U . . . C9 C 0.0390(3) 0.3342(2) 0.77771(9) 0.0383(4) Uani 1 1 d . . . . . H9 H -0.0971 0.2704 0.7747 0.046 Uiso 1 1 calc R U . . . C10 C 0.0869(4) 0.40001(19) 0.83623(9) 0.0403(4) Uani 1 1 d . . . . . H10 H -0.0178 0.3833 0.8732 0.048 Uiso 1 1 calc R U . . . C11 C 0.2897(4) 0.49084(19) 0.84042(9) 0.0423(5) Uani 1 1 d . . . . . H11 H 0.3256 0.5354 0.8806 0.051 Uiso 1 1 calc R U . . . C12 C 0.4409(4) 0.51683(16) 0.78583(8) 0.0346(4) Uani 1 1 d . . . . . H12 H 0.5793 0.5790 0.7892 0.042 Uiso 1 1 calc R U . . . H5O H 0.563(2) 0.261(3) 0.5028(14) 0.074(8) Uiso 1 1 d D . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.0168(4) 0.0308(4) 0.0374(5) 0.0017(4) -0.0028(3) 0.0015(4) F3 0.0378(5) 0.0281(5) 0.0406(5) 0.0100(4) -0.0023(4) 0.0062(4) O5 0.0241(5) 0.0315(6) 0.0409(6) -0.0162(5) 0.0040(5) -0.0013(5) C1 0.0203(6) 0.0221(7) 0.0259(7) -0.0003(6) -0.0004(5) 0.0014(6) C2 0.0168(6) 0.0220(7) 0.0298(7) -0.0027(5) -0.0019(5) 0.0010(5) C3 0.0225(7) 0.0213(7) 0.0300(7) 0.0039(6) -0.0026(6) 0.0017(5) C4 0.0251(7) 0.0303(8) 0.0253(7) -0.0012(6) 0.0009(6) -0.0030(6) C5 0.0204(6) 0.0234(7) 0.0305(7) -0.0085(6) 0.0011(6) -0.0015(6) C6 0.0251(7) 0.0188(6) 0.0321(7) -0.0011(6) 0.0019(6) 0.0012(6) C7 0.0262(7) 0.0239(7) 0.0277(7) 0.0027(6) 0.0023(6) 0.0066(6) C8 0.0240(7) 0.0407(8) 0.0329(8) 0.0045(7) 0.0005(6) 0.0012(7) C9 0.0289(8) 0.0460(10) 0.0400(9) 0.0124(7) 0.0059(7) 0.0018(8) C10 0.0459(10) 0.0373(9) 0.0376(8) 0.0103(7) 0.0148(8) 0.0132(9) C11 0.0686(13) 0.0284(8) 0.0299(8) 0.0009(6) 0.0100(8) 0.0078(9) C12 0.0478(10) 0.0241(7) 0.0319(8) -0.0011(6) 0.0045(7) 0.0016(7) #============================================================================== _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_structure_solution 'SIR2011 (Burla, et al., 2012)' _computing_structure_refinement 'SHELXL Version 2014/7 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.2 (Rigaku, 2015)' _computing_molecular_graphics 'CrystalStructure 4.2' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F2 C2 1.4127(16) . ? F3 C3 1.3987(17) . ? O5 C5 1.4333(17) . ? O5 H5O 0.972(7) . ? C1 C7 1.522(2) . ? C1 C2 1.5292(19) . ? C1 C6 1.5362(19) . ? C1 H1 1.0000 . ? C2 C3 1.514(2) . ? C2 H2 1.0000 . ? C3 C4 1.516(2) . ? C3 H3 1.0000 . ? C4 C5 1.521(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.519(2) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.394(2) . ? C7 C12 1.395(2) . ? C8 C9 1.390(2) . ? C8 H8 0.9500 . ? C9 C10 1.382(3) . ? C9 H9 0.9500 . ? C10 C11 1.389(3) . ? C10 H10 0.9500 . ? C11 C12 1.395(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O5 H5O 108.6(19) . . ? C7 C1 C2 110.67(11) . . ? C7 C1 C6 113.11(12) . . ? C2 C1 C6 110.88(11) . . ? C7 C1 H1 107.3 . . ? C2 C1 H1 107.3 . . ? C6 C1 H1 107.3 . . ? F2 C2 C3 108.10(11) . . ? F2 C2 C1 108.42(12) . . ? C3 C2 C1 111.83(11) . . ? F2 C2 H2 109.5 . . ? C3 C2 H2 109.5 . . ? C1 C2 H2 109.5 . . ? F3 C3 C2 108.31(12) . . ? F3 C3 C4 110.14(12) . . ? C2 C3 C4 112.45(12) . . ? F3 C3 H3 108.6 . . ? C2 C3 H3 108.6 . . ? C4 C3 H3 108.6 . . ? C3 C4 C5 108.81(12) . . ? C3 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? C3 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? O5 C5 C6 110.60(12) . . ? O5 C5 C4 111.33(12) . . ? C6 C5 C4 110.73(12) . . ? O5 C5 H5 108.0 . . ? C6 C5 H5 108.0 . . ? C4 C5 H5 108.0 . . ? C5 C6 C1 112.79(12) . . ? C5 C6 H6A 109.0 . . ? C1 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C1 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C12 118.04(15) . . ? C8 C7 C1 122.10(14) . . ? C12 C7 C1 119.85(15) . . ? C9 C8 C7 121.15(17) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C10 C9 C8 120.36(18) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.32(16) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C10 C11 C12 120.26(17) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 120.85(17) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? 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 C7 C1 C2 F2 -57.74(15) . . . . ? C6 C1 C2 F2 68.62(14) . . . . ? C7 C1 C2 C3 -176.83(12) . . . . ? C6 C1 C2 C3 -50.47(16) . . . . ? F2 C2 C3 F3 58.42(15) . . . . ? C1 C2 C3 F3 177.71(12) . . . . ? F2 C2 C3 C4 -63.52(15) . . . . ? C1 C2 C3 C4 55.76(16) . . . . ? F3 C3 C4 C5 -179.87(12) . . . . ? C2 C3 C4 C5 -58.97(16) . . . . ? C3 C4 C5 O5 -178.12(12) . . . . ? C3 C4 C5 C6 58.41(16) . . . . ? O5 C5 C6 C1 179.92(12) . . . . ? C4 C5 C6 C1 -56.19(16) . . . . ? C7 C1 C6 C5 176.46(12) . . . . ? C2 C1 C6 C5 51.46(16) . . . . ? C2 C1 C7 C8 94.88(16) . . . . ? C6 C1 C7 C8 -30.2(2) . . . . ? C2 C1 C7 C12 -83.77(17) . . . . ? C6 C1 C7 C12 151.11(14) . . . . ? C12 C7 C8 C9 0.5(2) . . . . ? C1 C7 C8 C9 -178.18(14) . . . . ? C7 C8 C9 C10 0.6(3) . . . . ? C8 C9 C10 C11 -1.3(3) . . . . ? C9 C10 C11 C12 1.0(3) . . . . ? C10 C11 C12 C7 0.1(3) . . . . ? C8 C7 C12 C11 -0.8(2) . . . . ? C1 C7 C12 C11 177.87(15) . . . . ? #============================================================================== 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 O5 H5O O5 . . 3_456 2.7950(16) 0.972(17) 1.824(16) 177(3) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. _shelx_res_file ; shelxl.res created by SHELXL-2014/7 TITL AGDH1 CELL 1.54187 5.25889 9.75241 20.46980 90.00000 90.00000 90.00000 ZERR 4 0.00006 0.00011 0.00020 0.00000 0.00000 0.00000 LATT -1 SYMM .50-X, -Y, .50+Z SYMM .50+X, .50-Y, -Z SYMM -X, .50+Y, .50-Z SFAC C H F O UNIT 48 56 8 4 L.S. 20 FMAP 2 PLAN 5 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -148.0 ACTA SIZE 0.200 0.020 0.010 DFIX 0.9800 0.0050 O5 H5O WGHT 0.040300 0.164000 FVAR 2.50426 F2 3 0.198946 0.594896 0.615346 11.00000 0.01682 0.03076 = 0.03735 0.00167 -0.00276 0.00145 F3 3 0.497429 0.763892 0.542220 11.00000 0.03780 0.02806 = 0.04056 0.01003 -0.00229 0.00624 O5 4 0.735274 0.289701 0.513348 11.00000 0.02409 0.03146 = 0.04086 -0.01624 0.00396 -0.00134 C1 1 0.553379 0.486503 0.666774 11.00000 0.02030 0.02211 = 0.02594 -0.00035 -0.00043 0.00144 AFIX 13 H1 2 0.729128 0.506555 0.682794 11.00000 -1.20000 AFIX 0 C2 1 0.455703 0.616037 0.632968 11.00000 0.01683 0.02205 = 0.02982 -0.00270 -0.00187 0.00104 AFIX 13 H2 2 0.467577 0.695418 0.663741 11.00000 -1.20000 AFIX 0 C3 1 0.604245 0.647760 0.571458 11.00000 0.02254 0.02127 = 0.03002 0.00387 -0.00259 0.00169 AFIX 13 H3 2 0.783889 0.669097 0.583836 11.00000 -1.20000 AFIX 0 C4 1 0.605190 0.528918 0.523686 11.00000 0.02514 0.03030 = 0.02528 -0.00120 0.00094 -0.00304 AFIX 23 H4A 2 0.705539 0.553357 0.484458 11.00000 -1.20000 H4B 2 0.429178 0.507933 0.509746 11.00000 -1.20000 AFIX 0 C5 1 0.721736 0.404406 0.556985 11.00000 0.02039 0.02340 = 0.03051 -0.00850 0.00108 -0.00152 AFIX 13 H5 2 0.898977 0.428684 0.570378 11.00000 -1.20000 AFIX 0 C6 1 0.573463 0.367032 0.618138 11.00000 0.02509 0.01880 = 0.03214 -0.00113 0.00191 0.00123 AFIX 23 H6A 2 0.657691 0.288534 0.639867 11.00000 -1.20000 H6B 2 0.400155 0.337643 0.605466 11.00000 -1.20000 AFIX 0 C7 1 0.391412 0.452673 0.726252 11.00000 0.02620 0.02386 = 0.02768 0.00274 0.00226 0.00664 C8 1 0.188948 0.360661 0.723224 11.00000 0.02403 0.04073 = 0.03288 0.00447 0.00051 0.00125 AFIX 43 H8 2 0.152775 0.315271 0.683226 11.00000 -1.20000 AFIX 0 C9 1 0.039025 0.334150 0.777713 11.00000 0.02887 0.04598 = 0.04001 0.01241 0.00591 0.00178 AFIX 43 H9 2 -0.097093 0.270417 0.774717 11.00000 -1.20000 AFIX 0 C10 1 0.086917 0.400014 0.836230 11.00000 0.04591 0.03733 = 0.03759 0.01029 0.01476 0.01318 AFIX 43 H10 2 -0.017809 0.383334 0.873201 11.00000 -1.20000 AFIX 0 C11 1 0.289747 0.490844 0.840423 11.00000 0.06858 0.02845 = 0.02991 0.00087 0.00997 0.00778 AFIX 43 H11 2 0.325648 0.535434 0.880641 11.00000 -1.20000 AFIX 0 C12 1 0.440869 0.516826 0.785827 11.00000 0.04780 0.02410 = 0.03191 -0.00107 0.00450 0.00160 AFIX 43 H12 2 0.579277 0.579013 0.789248 11.00000 -1.20000 AFIX 0 H5O 2 0.563293 0.260838 0.502774 11.00000 0.07379 HKLF 4 REM AGDH1 REM R1 = 0.0260 for 2109 Fo > 4sig(Fo) and 0.0264 for all 2150 data REM 140 parameters refined using 1 restraints END WGHT 0.0354 0.1880 REM Instructions for potential hydrogen bonds EQIV $1 x+1, y, z HTAB C3 F2_$1 EQIV $2 x+1/2, -y+3/2, -z+1 HTAB C4 F3_$2 HTAB C5 F2_$1 EQIV $3 x-1/2, -y+1/2, -z+1 HTAB O5 O5_$3 REM Highest difference peak 0.145, deepest hole -0.146, 1-sigma level 0.032 Q1 1 0.6029 0.5838 0.5483 11.00000 0.05 0.14 Q2 1 0.2353 0.4307 0.8426 11.00000 0.05 0.12 Q3 1 0.5068 0.5492 0.6529 11.00000 0.05 0.12 Q4 1 0.4148 0.4789 0.7561 11.00000 0.05 0.12 Q5 1 0.6438 0.4654 0.5465 11.00000 0.05 0.11 ; _shelx_res_checksum 42851 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_11 _database_code_depnum_ccdc_archive 'CCDC 1817388' _audit_update_record ; 2018-01-16 deposited with the CCDC. 2018-02-19 downloaded from the CCDC. ; # start Validation Reply Form _vrf_PLAT084_11 ; PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.46 Report RESPONSE: Poor crystals- best result presented - good enough to show conformation. ; # end Validation Reply Form _audit_creation_date 2016-11-30 _audit_creation_method 'by CrystalStructure 4.2' _chemical_formula_sum 'C12 H14 F2 O' _chemical_formula_moiety 'C12 H14 F2 O' _chemical_formula_weight 212.24 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/a 1' _space_group_name_Hall '-P 2yab' _space_group_IT_number 14 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,-Z 3 -X,-Y,-Z 4 -1/2+X,-1/2-Y,+Z #------------------------------------------------------------------------------ _cell_length_a 13.5173(3) _cell_length_b 5.57303(15) _cell_length_c 27.4909(9) _cell_angle_alpha 90.0000 _cell_angle_beta 90.469(2) _cell_angle_gamma 90.0000 _cell_volume 2070.88(10) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9672 _cell_measurement_theta_min 3.66 _cell_measurement_theta_max 73.85 _cell_measurement_temperature 125 #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.010 _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896.00 _exptl_absorpt_coefficient_mu 0.924 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.577 _exptl_absorpt_correction_T_max 0.991 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 125 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.811 _diffrn_reflns_number 22453 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_theta_max 75.614 _diffrn_reflns_theta_min 3.215 _diffrn_reflns_theta_full 67.687 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? _reflns_number_total 4191 _reflns_number_gt 3710 _reflns_threshold_expression F^2^>2.0\s(F^2^) _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . #============================================================================== # 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). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.1345 _refine_ls_R_factor_gt 0.1282 _refine_ls_wR_factor_ref 0.4562 _refine_ls_wR_factor_gt 0.4485 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 4191 _refine_ls_number_parameters 279 _refine_ls_goodness_of_fit_ref 2.205 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^] 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 0.000 _refine_diff_density_max 1.65 _refine_diff_density_min -1.16 _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 0.0181 0.0091 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; F F 0.0727 0.0534 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F2 F 0.4612(2) 1.1946(5) 0.38074(13) 0.0709(10) Uani 1 1 d . . . . . F3 F 0.2670(2) 1.1568(7) 0.39943(12) 0.0792(11) Uani 1 1 d . . . . . F22 F 0.7593(4) 0.4943(7) 0.8999(2) 0.139(3) Uani 1 1 d . . . . . F23 F 0.8231(3) 0.5428(18) 0.9922(3) 0.197(4) Uani 1 1 d . . . . . O4 O 0.2753(2) 0.9040(6) 0.48702(13) 0.0611(10) Uani 1 1 d D . . . . O24 O 1.0037(3) 0.7600(9) 0.97730(15) 0.0779(13) Uani 1 1 d D . . . . C1 C 0.4835(3) 0.7726(6) 0.37514(14) 0.0384(9) Uani 1 1 d . . . . . H1 H 0.4440 0.6261 0.3670 0.046 Uiso 1 1 calc R U . . . C2 C 0.4133(3) 0.9844(8) 0.37032(15) 0.0459(9) Uani 1 1 d . . . . . H2 H 0.3878 0.9914 0.3361 0.055 Uiso 1 1 calc R U . . . C3 C 0.3265(3) 0.9620(10) 0.40447(15) 0.0535(11) Uani 1 1 d . . . . . H3 H 0.2878 0.8157 0.3953 0.064 Uiso 1 1 calc R U . . . C4 C 0.3593(3) 0.9382(7) 0.45621(14) 0.0431(9) Uani 1 1 d . . . . . H4A H 0.3947 1.0880 0.4663 0.052 Uiso 1 1 calc R U . . . C5 C 0.4287(3) 0.7261(8) 0.46204(17) 0.0548(11) Uani 1 1 d . . . . . H5A H 0.4519 0.7176 0.4962 0.066 Uiso 1 1 calc R U . . . H5B H 0.3921 0.5763 0.4547 0.066 Uiso 1 1 calc R U . . . C6 C 0.5175(3) 0.7443(8) 0.42877(16) 0.0511(11) Uani 1 1 d . . . . . H6A H 0.5586 0.5981 0.4321 0.061 Uiso 1 1 calc R U . . . H6B H 0.5584 0.8841 0.4384 0.061 Uiso 1 1 calc R U . . . C7 C 0.5698(2) 0.7760(6) 0.34053(12) 0.0350(8) Uani 1 1 d . . . . . C8 C 0.6401(2) 0.9608(7) 0.34042(13) 0.0376(8) Uani 1 1 d . . . . . H8 H 0.6338 1.0913 0.3624 0.045 Uiso 1 1 calc R U . . . C9 C 0.7190(3) 0.9544(7) 0.30837(15) 0.0432(9) Uani 1 1 d . . . . . H9 H 0.7658 1.0817 0.3084 0.052 Uiso 1 1 calc R U . . . C10 C 0.7302(3) 0.7651(7) 0.27645(15) 0.0449(9) Uani 1 1 d . . . . . H10 H 0.7844 0.7619 0.2547 0.054 Uiso 1 1 calc R U . . . C11 C 0.6618(3) 0.5796(7) 0.27641(14) 0.0441(9) Uani 1 1 d . . . . . H11 H 0.6690 0.4490 0.2545 0.053 Uiso 1 1 calc R U . . . C12 C 0.5830(3) 0.5848(6) 0.30838(13) 0.0392(8) Uani 1 1 d . . . . . H12 H 0.5370 0.4559 0.3084 0.047 Uiso 1 1 calc R U . . . C21 C 0.7567(3) 0.9068(6) 0.88563(14) 0.0423(9) Uani 1 1 d . . . . . H21 H 0.7502 1.0595 0.9044 0.051 Uiso 1 1 calc R U . . . C22 C 0.7504(3) 0.7043(14) 0.9212(2) 0.082(2) Uani 1 1 d . . . . . H22 H 0.6846 0.7113 0.9375 0.098 Uiso 1 1 calc R U . . . C23 C 0.8311(4) 0.7244(17) 0.9599(2) 0.091(3) Uani 1 1 d . . . . . H23 H 0.8199 0.8776 0.9780 0.109 Uiso 1 1 calc R U . . . C24 C 0.9313(3) 0.7354(8) 0.93929(17) 0.0521(11) Uani 1 1 d . . . . . H24A H 0.9437 0.5777 0.9231 0.062 Uiso 1 1 calc R U . . . C25 C 0.9418(4) 0.9242(11) 0.9014(2) 0.0720(16) Uani 1 1 d . . . . . H25A H 1.0073 0.9082 0.8859 0.086 Uiso 1 1 calc R U . . . H25B H 0.9388 1.0842 0.9170 0.086 Uiso 1 1 calc R U . . . C26 C 0.8606(3) 0.9064(12) 0.8624(2) 0.0713(17) Uani 1 1 d . . . . . H26A H 0.8695 0.7570 0.8434 0.086 Uiso 1 1 calc R U . . . H26B H 0.8662 1.0438 0.8397 0.086 Uiso 1 1 calc R U . . . C27 C 0.6757(2) 0.9058(6) 0.84692(13) 0.0373(8) Uani 1 1 d . . . . . C28 C 0.6685(3) 0.7247(7) 0.81181(15) 0.0454(9) Uani 1 1 d . . . . . H28 H 0.7146 0.5960 0.8120 0.054 Uiso 1 1 calc R U . . . C29 C 0.5943(3) 0.7328(8) 0.77673(16) 0.0503(10) Uani 1 1 d . . . . . H29 H 0.5899 0.6084 0.7532 0.060 Uiso 1 1 calc R U . . . C30 C 0.5265(3) 0.9188(7) 0.77545(14) 0.0430(9) Uani 1 1 d . . . . . H30 H 0.4754 0.9224 0.7515 0.052 Uiso 1 1 calc R U . . . C31 C 0.5346(3) 1.0995(8) 0.80985(16) 0.0490(10) Uani 1 1 d . . . . . H31 H 0.4892 1.2297 0.8091 0.059 Uiso 1 1 calc R U . . . C32 C 0.6077(3) 1.0930(7) 0.84521(16) 0.0459(9) Uani 1 1 d . . . . . H32 H 0.6117 1.2179 0.8687 0.055 Uiso 1 1 calc R U . . . H4O H 0.263(4) 1.037(7) 0.5095(17) 0.068(16) Uiso 1 1 d D . . . . H24O H 0.946(4) 0.722(15) 0.997(3) 0.11(3) Uiso 1 1 d D . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.0768(19) 0.0370(14) 0.099(2) 0.0027(13) 0.0320(16) 0.0027(12) F3 0.0672(18) 0.098(2) 0.0724(19) 0.0089(17) 0.0081(14) 0.0361(17) F22 0.162(4) 0.042(2) 0.210(5) 0.039(2) -0.118(4) -0.033(2) F23 0.073(3) 0.339(10) 0.179(5) 0.199(7) -0.024(3) -0.038(4) O4 0.0519(17) 0.065(2) 0.066(2) 0.0036(15) 0.0244(14) 0.0000(14) O24 0.0461(17) 0.115(4) 0.072(2) 0.020(2) -0.0164(15) 0.0043(19) C1 0.0374(16) 0.0303(18) 0.0475(19) -0.0023(13) 0.0041(14) -0.0072(12) C2 0.0411(18) 0.051(2) 0.0451(19) 0.0029(16) -0.0008(15) 0.0063(16) C3 0.0382(19) 0.075(3) 0.048(2) -0.0068(19) 0.0015(15) 0.0053(18) C4 0.0402(17) 0.043(2) 0.047(2) -0.0030(14) 0.0126(15) -0.0023(14) C5 0.058(2) 0.049(2) 0.057(2) 0.0175(18) 0.0190(19) 0.0123(19) C6 0.053(2) 0.050(2) 0.050(2) 0.0088(16) 0.0142(17) 0.0135(18) C7 0.0390(17) 0.0288(16) 0.0371(17) 0.0040(11) -0.0019(12) -0.0004(12) C8 0.0363(16) 0.0321(16) 0.0443(18) 0.0001(13) 0.0020(13) -0.0030(13) C9 0.0392(17) 0.0351(17) 0.055(2) 0.0065(15) 0.0035(15) -0.0053(14) C10 0.0470(19) 0.0400(19) 0.048(2) 0.0065(14) 0.0094(15) 0.0065(15) C11 0.054(2) 0.0337(18) 0.0444(19) 0.0009(13) 0.0052(15) 0.0053(15) C12 0.0449(18) 0.0284(17) 0.0441(18) -0.0015(12) -0.0022(14) 0.0004(13) C21 0.0441(19) 0.035(2) 0.0471(19) -0.0065(14) -0.0011(14) 0.0049(14) C22 0.041(2) 0.120(5) 0.085(4) 0.055(4) -0.009(2) -0.018(3) C23 0.045(2) 0.172(7) 0.056(3) 0.048(4) -0.0004(19) -0.001(3) C24 0.044(2) 0.058(3) 0.055(2) 0.0093(18) -0.0018(17) 0.0085(17) C25 0.046(2) 0.078(4) 0.092(4) 0.026(3) -0.012(2) -0.021(2) C26 0.043(2) 0.094(4) 0.077(3) 0.042(3) -0.014(2) -0.014(2) C27 0.0359(16) 0.0337(18) 0.0422(18) -0.0001(12) 0.0037(13) -0.0025(13) C28 0.0427(18) 0.042(2) 0.052(2) -0.0070(15) 0.0007(15) 0.0102(15) C29 0.047(2) 0.051(2) 0.053(2) -0.0122(16) -0.0050(16) 0.0042(16) C30 0.0367(17) 0.044(2) 0.0480(19) 0.0056(14) -0.0001(14) -0.0030(14) C31 0.0417(19) 0.043(2) 0.062(2) 0.0005(16) -0.0054(16) 0.0068(15) C32 0.0452(19) 0.0343(19) 0.058(2) -0.0084(15) -0.0013(16) 0.0047(14) #============================================================================== _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_structure_solution 'Superflip (Palatinus, et al., 2007)' _computing_structure_refinement 'SHELXL Version 2014/7 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.2 (Rigaku, 2015)' _computing_molecular_graphics 'CrystalStructure 4.2' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F2 C2 1.367(5) . ? F3 C3 1.358(6) . ? F22 C22 1.315(10) . ? F23 C23 1.352(8) . ? O4 C4 1.435(4) . ? O4 H4O 0.980(5) . ? O24 C24 1.433(6) . ? O24 H24O 0.980(5) . ? C1 C7 1.512(5) . ? C1 C2 1.519(5) . ? C1 C6 1.549(6) . ? C1 H1 1.0000 . ? C2 C3 1.514(5) . ? C2 H2 1.0000 . ? C3 C4 1.492(6) . ? C3 H3 1.0000 . ? C4 C5 1.516(6) . ? C4 H4A 1.0000 . ? C5 C6 1.519(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.397(5) . ? C7 C8 1.401(5) . ? C8 C9 1.389(5) . ? C8 H8 0.9500 . ? C9 C10 1.382(6) . ? C9 H9 0.9500 . ? C10 C11 1.387(6) . ? C10 H10 0.9500 . ? C11 C12 1.387(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C21 C22 1.496(7) . ? C21 C27 1.521(5) . ? C21 C26 1.548(6) . ? C21 H21 1.0000 . ? C22 C23 1.521(8) . ? C22 H22 1.0000 . ? C23 C24 1.473(6) . ? C23 H23 1.0000 . ? C24 C25 1.488(7) . ? C24 H24A 1.0000 . ? C25 C26 1.533(7) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C32 1.390(5) . ? C27 C28 1.399(5) . ? C28 C29 1.387(6) . ? C28 H28 0.9500 . ? C29 C30 1.384(6) . ? C29 H29 0.9500 . ? C30 C31 1.385(6) . ? C30 H30 0.9500 . ? C31 C32 1.381(6) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O4 H4O 114(4) . . ? C24 O24 H24O 81(5) . . ? C7 C1 C2 114.8(3) . . ? C7 C1 C6 112.1(3) . . ? C2 C1 C6 110.0(3) . . ? C7 C1 H1 106.4 . . ? C2 C1 H1 106.4 . . ? C6 C1 H1 106.4 . . ? F2 C2 C3 108.0(3) . . ? F2 C2 C1 110.7(3) . . ? C3 C2 C1 111.6(3) . . ? F2 C2 H2 108.8 . . ? C3 C2 H2 108.8 . . ? C1 C2 H2 108.8 . . ? F3 C3 C4 109.8(4) . . ? F3 C3 C2 109.4(4) . . ? C4 C3 C2 111.9(3) . . ? F3 C3 H3 108.6 . . ? C4 C3 H3 108.6 . . ? C2 C3 H3 108.6 . . ? O4 C4 C3 110.1(3) . . ? O4 C4 C5 109.0(3) . . ? C3 C4 C5 110.4(3) . . ? O4 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? C6 C5 C4 112.1(3) . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C1 110.5(4) . . ? C5 C6 H6A 109.6 . . ? C1 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? C1 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C12 C7 C8 118.0(3) . . ? C12 C7 C1 119.4(3) . . ? C8 C7 C1 122.5(3) . . ? C9 C8 C7 120.4(3) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.6(3) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C7 121.3(3) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? C22 C21 C27 114.2(3) . . ? C22 C21 C26 109.0(4) . . ? C27 C21 C26 111.2(3) . . ? C22 C21 H21 107.4 . . ? C27 C21 H21 107.4 . . ? C26 C21 H21 107.4 . . ? F22 C22 C21 112.0(5) . . ? F22 C22 C23 108.0(6) . . ? C21 C22 C23 110.9(5) . . ? F22 C22 H22 108.6 . . ? C21 C22 H22 108.6 . . ? C23 C22 H22 108.6 . . ? F23 C23 C24 111.3(5) . . ? F23 C23 C22 110.1(6) . . ? C24 C23 C22 113.0(5) . . ? F23 C23 H23 107.4 . . ? C24 C23 H23 107.4 . . ? C22 C23 H23 107.4 . . ? O24 C24 C23 110.4(4) . . ? O24 C24 C25 111.9(4) . . ? C23 C24 C25 113.1(4) . . ? O24 C24 H24A 107.0 . . ? C23 C24 H24A 107.0 . . ? C25 C24 H24A 107.0 . . ? C24 C25 C26 111.9(4) . . ? C24 C25 H25A 109.2 . . ? C26 C25 H25A 109.2 . . ? C24 C25 H25B 109.2 . . ? C26 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? C25 C26 C21 110.9(4) . . ? C25 C26 H26A 109.4 . . ? C21 C26 H26A 109.4 . . ? C25 C26 H26B 109.4 . . ? C21 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? C32 C27 C28 118.4(3) . . ? C32 C27 C21 119.5(3) . . ? C28 C27 C21 122.0(3) . . ? C29 C28 C27 120.1(3) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C30 C29 C28 121.1(4) . . ? C30 C29 H29 119.4 . . ? C28 C29 H29 119.4 . . ? C31 C30 C29 118.6(4) . . ? C31 C30 H30 120.7 . . ? C29 C30 H30 120.7 . . ? C32 C31 C30 120.9(4) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C27 120.8(4) . . ? C31 C32 H32 119.6 . . ? C27 C32 H32 119.6 . . ? 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 C7 C1 C2 F2 -62.4(4) . . . . ? C6 C1 C2 F2 65.2(4) . . . . ? C7 C1 C2 C3 177.3(3) . . . . ? C6 C1 C2 C3 -55.1(4) . . . . ? F2 C2 C3 F3 57.1(4) . . . . ? C1 C2 C3 F3 179.0(3) . . . . ? F2 C2 C3 C4 -64.9(5) . . . . ? C1 C2 C3 C4 57.0(5) . . . . ? F3 C3 C4 O4 61.5(5) . . . . ? C2 C3 C4 O4 -176.8(3) . . . . ? F3 C3 C4 C5 -178.1(3) . . . . ? C2 C3 C4 C5 -56.4(5) . . . . ? O4 C4 C5 C6 177.5(4) . . . . ? C3 C4 C5 C6 56.4(5) . . . . ? C4 C5 C6 C1 -55.6(5) . . . . ? C7 C1 C6 C5 -176.5(3) . . . . ? C2 C1 C6 C5 54.5(4) . . . . ? C2 C1 C7 C12 -121.5(4) . . . . ? C6 C1 C7 C12 111.9(4) . . . . ? C2 C1 C7 C8 60.8(4) . . . . ? C6 C1 C7 C8 -65.7(4) . . . . ? C12 C7 C8 C9 1.4(5) . . . . ? C1 C7 C8 C9 179.1(3) . . . . ? C7 C8 C9 C10 -0.7(6) . . . . ? C8 C9 C10 C11 0.0(6) . . . . ? C9 C10 C11 C12 -0.1(6) . . . . ? C10 C11 C12 C7 0.9(6) . . . . ? C8 C7 C12 C11 -1.5(5) . . . . ? C1 C7 C12 C11 -179.3(3) . . . . ? C27 C21 C22 F22 61.8(5) . . . . ? C26 C21 C22 F22 -63.3(5) . . . . ? C27 C21 C22 C23 -177.5(5) . . . . ? C26 C21 C22 C23 57.4(7) . . . . ? F22 C22 C23 F23 -58.1(8) . . . . ? C21 C22 C23 F23 178.8(7) . . . . ? F22 C22 C23 C24 67.0(8) . . . . ? C21 C22 C23 C24 -56.0(9) . . . . ? F23 C23 C24 O24 -56.9(9) . . . . ? C22 C23 C24 O24 178.6(6) . . . . ? F23 C23 C24 C25 176.8(7) . . . . ? C22 C23 C24 C25 52.3(9) . . . . ? O24 C24 C25 C26 -176.7(5) . . . . ? C23 C24 C25 C26 -51.2(8) . . . . ? C24 C25 C26 C21 53.6(7) . . . . ? C22 C21 C26 C25 -56.9(6) . . . . ? C27 C21 C26 C25 176.2(4) . . . . ? C22 C21 C27 C32 115.7(5) . . . . ? C26 C21 C27 C32 -120.4(4) . . . . ? C22 C21 C27 C28 -66.0(5) . . . . ? C26 C21 C27 C28 57.9(5) . . . . ? C32 C27 C28 C29 -0.7(6) . . . . ? C21 C27 C28 C29 -179.1(4) . . . . ? C27 C28 C29 C30 0.3(6) . . . . ? C28 C29 C30 C31 0.6(6) . . . . ? C29 C30 C31 C32 -1.0(6) . . . . ? C30 C31 C32 C27 0.6(6) . . . . ? C28 C27 C32 C31 0.3(6) . . . . ? C21 C27 C32 C31 178.7(4) . . . . ? #============================================================================== 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 O4 H4O O4 . . 2_556 2.958(5) 0.98(4) 2.11(4) 143(4) no O24 H24O F23 . . . 2.759(7) 0.98(6) 1.95(6) 139(6) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. _shelx_res_file ; shelxl.res created by SHELXL-2014/7 TITL AGDH2N CELL 1.54187 13.51730 5.57303 27.49090 90.00000 90.46900 90.00000 ZERR 8 0.00030 0.00015 0.00090 0.00000 0.00200 0.00000 LATT 1 SYMM .50-X, .50+Y, -Z SFAC C H F O UNIT 96 112 16 8 OMIT -2 5 3 OMIT -7 2 1 OMIT -2 0 2 OMIT 0 2 11 OMIT 2 1 0 OMIT 0 4 1 OMIT 4 3 6 OMIT -8 2 11 OMIT -3 1 13 OMIT -7 3 3 OMIT 7 2 9 OMIT 6 4 12 OMIT -2 4 4 OMIT 2 1 17 OMIT -1 2 7 OMIT 0 1 20 OMIT -1 4 7 OMIT 5 1 3 OMIT -4 2 4 OMIT -6 4 12 OMIT -8 4 11 OMIT -9 1 15 OMIT 4 3 18 OMIT -6 4 6 L.S. 20 FMAP 2 PLAN 5 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -148.0 ACTA SIZE 0.300 0.100 0.010 DFIX 0.9800 0.0050 O4 H4O O24 H24O WGHT 0.200000 FVAR 1.10508 F2 3 0.461160 1.194564 0.380741 11.00000 0.07676 0.03700 = 0.09934 0.00273 0.03203 0.00266 F3 3 0.267035 1.156839 0.399426 11.00000 0.06724 0.09813 = 0.07245 0.00891 0.00807 0.03609 F22 3 0.759283 0.494302 0.899934 11.00000 0.16197 0.04193 = 0.21041 0.03887 -0.11790 -0.03347 F23 3 0.823096 0.542815 0.992247 11.00000 0.07336 0.33941 = 0.17865 0.19881 -0.02383 -0.03796 O4 4 0.275300 0.903955 0.487018 11.00000 0.05194 0.06531 = 0.06638 0.00361 0.02445 0.00000 O24 4 1.003739 0.760042 0.977301 11.00000 0.04605 0.11515 = 0.07212 0.02002 -0.01642 0.00425 C1 1 0.483512 0.772623 0.375143 11.00000 0.03739 0.03033 = 0.04748 -0.00225 0.00414 -0.00724 AFIX 13 H1 2 0.444012 0.626078 0.367021 11.00000 -1.20000 AFIX 0 C2 1 0.413326 0.984417 0.370323 11.00000 0.04108 0.05140 = 0.04515 0.00288 -0.00077 0.00635 AFIX 13 H2 2 0.387772 0.991398 0.336113 11.00000 -1.20000 AFIX 0 C3 1 0.326514 0.961962 0.404472 11.00000 0.03815 0.07465 = 0.04775 -0.00678 0.00152 0.00530 AFIX 13 H3 2 0.287788 0.815650 0.395323 11.00000 -1.20000 AFIX 0 C4 1 0.359324 0.938193 0.456205 11.00000 0.04021 0.04271 = 0.04661 -0.00303 0.01261 -0.00225 AFIX 13 H4A 2 0.394741 1.087952 0.466260 11.00000 -1.20000 AFIX 0 C5 1 0.428664 0.726123 0.462037 11.00000 0.05791 0.04944 = 0.05733 0.01754 0.01899 0.01226 AFIX 23 H5A 2 0.451901 0.717606 0.496238 11.00000 -1.20000 H5B 2 0.392129 0.576320 0.454684 11.00000 -1.20000 AFIX 0 C6 1 0.517503 0.744313 0.428765 11.00000 0.05335 0.05032 = 0.04995 0.00882 0.01417 0.01350 AFIX 23 H6A 2 0.558599 0.598119 0.432128 11.00000 -1.20000 H6B 2 0.558428 0.884077 0.438374 11.00000 -1.20000 AFIX 0 C7 1 0.569825 0.776008 0.340533 11.00000 0.03897 0.02881 = 0.03707 0.00404 -0.00188 -0.00038 C8 1 0.640118 0.960786 0.340421 11.00000 0.03632 0.03210 = 0.04427 0.00010 0.00204 -0.00300 AFIX 43 H8 2 0.633784 1.091295 0.362407 11.00000 -1.20000 AFIX 0 C9 1 0.719017 0.954428 0.308375 11.00000 0.03920 0.03512 = 0.05521 0.00648 0.00345 -0.00527 AFIX 43 H9 2 0.765788 1.081663 0.308412 11.00000 -1.20000 AFIX 0 C10 1 0.730195 0.765051 0.276448 11.00000 0.04700 0.04003 = 0.04789 0.00650 0.00944 0.00648 AFIX 43 H10 2 0.784375 0.761944 0.254663 11.00000 -1.20000 AFIX 0 C11 1 0.661818 0.579558 0.276412 11.00000 0.05418 0.03367 = 0.04442 0.00091 0.00520 0.00529 AFIX 43 H11 2 0.668965 0.448965 0.254511 11.00000 -1.20000 AFIX 0 C12 1 0.582965 0.584821 0.308381 11.00000 0.04493 0.02841 = 0.04415 -0.00152 -0.00218 0.00039 AFIX 43 H12 2 0.537008 0.455854 0.308404 11.00000 -1.20000 AFIX 0 C21 1 0.756702 0.906756 0.885628 11.00000 0.04415 0.03548 = 0.04711 -0.00651 -0.00110 0.00490 AFIX 13 H21 2 0.750196 1.059527 0.904412 11.00000 -1.20000 AFIX 0 C22 1 0.750386 0.704327 0.921232 11.00000 0.04135 0.12008 = 0.08451 0.05488 -0.00940 -0.01788 AFIX 13 H22 2 0.684589 0.711349 0.937538 11.00000 -1.20000 AFIX 0 C23 1 0.831107 0.724359 0.959899 11.00000 0.04510 0.17235 = 0.05584 0.04774 -0.00037 -0.00050 AFIX 13 H23 2 0.819883 0.877562 0.977969 11.00000 -1.20000 AFIX 0 C24 1 0.931254 0.735437 0.939291 11.00000 0.04364 0.05763 = 0.05489 0.00933 -0.00185 0.00847 AFIX 13 H24A 2 0.943668 0.577735 0.923097 11.00000 -1.20000 AFIX 0 C25 1 0.941816 0.924214 0.901415 11.00000 0.04570 0.07845 = 0.09153 0.02647 -0.01229 -0.02061 AFIX 23 H25A 2 1.007291 0.908203 0.885870 11.00000 -1.20000 H25B 2 0.938818 1.084190 0.916989 11.00000 -1.20000 AFIX 0 C26 1 0.860586 0.906427 0.862356 11.00000 0.04313 0.09405 = 0.07651 0.04236 -0.01395 -0.01430 AFIX 23 H26A 2 0.869504 0.756960 0.843431 11.00000 -1.20000 H26B 2 0.866154 1.043767 0.839703 11.00000 -1.20000 AFIX 0 C27 1 0.675681 0.905833 0.846916 11.00000 0.03590 0.03371 = 0.04221 -0.00011 0.00365 -0.00246 C28 1 0.668504 0.724735 0.811811 11.00000 0.04266 0.04174 = 0.05168 -0.00699 0.00069 0.01025 AFIX 43 H28 2 0.714580 0.596013 0.812009 11.00000 -1.20000 AFIX 0 C29 1 0.594270 0.732764 0.776731 11.00000 0.04694 0.05102 = 0.05280 -0.01223 -0.00505 0.00422 AFIX 43 H29 2 0.589888 0.608437 0.753169 11.00000 -1.20000 AFIX 0 C30 1 0.526450 0.918784 0.775450 11.00000 0.03668 0.04448 = 0.04797 0.00557 -0.00010 -0.00300 AFIX 43 H30 2 0.475423 0.922448 0.751492 11.00000 -1.20000 AFIX 0 C31 1 0.534575 1.099521 0.809854 11.00000 0.04169 0.04333 = 0.06185 0.00046 -0.00536 0.00679 AFIX 43 H31 2 0.489222 1.229716 0.809119 11.00000 -1.20000 AFIX 0 C32 1 0.607728 1.092982 0.845212 11.00000 0.04521 0.03432 = 0.05813 -0.00844 -0.00129 0.00472 AFIX 43 H32 2 0.611655 1.217924 0.868657 11.00000 -1.20000 AFIX 0 H4O 2 0.263472 1.037162 0.509510 11.00000 0.06801 H24O 2 0.946281 0.722326 0.997426 11.00000 0.10605 HKLF 4 REM AGDH2N REM R1 = 0.1282 for 3710 Fo > 4sig(Fo) and 0.1345 for all 4191 data REM 279 parameters refined using 2 restraints END WGHT 0.2000 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 x, y-1, z HTAB C1 F2_$1 EQIV $2 x, y+1, z HTAB C21 F22_$2 EQIV $3 -x+3/2, y+1/2, -z+2 HTAB C23 F23_$3 EQIV $4 -x+1/2, y+1/2, -z+1 HTAB O4 O4_$4 HTAB O24 F23 REM Highest difference peak 1.653, deepest hole -1.161, 1-sigma level 0.110 Q1 1 0.4217 0.6649 0.4998 11.00000 0.05 1.36 Q2 1 0.9921 1.1356 0.9126 11.00000 0.05 0.84 Q3 1 0.9021 1.0212 0.9252 11.00000 0.05 0.72 Q4 1 0.8918 0.9039 0.8410 11.00000 0.05 0.55 Q5 1 0.8085 0.5235 0.8692 11.00000 0.05 0.47 ; _shelx_res_checksum 68199 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_12b _database_code_depnum_ccdc_archive 'CCDC 1817390' _audit_update_record ; 2018-01-16 deposited with the CCDC. 2018-02-19 downloaded from the CCDC. ; _audit_creation_date 2016-10-11 _audit_creation_method 'by CrystalStructure 4.2' _chemical_formula_sum 'C12 H14 F2 O' _chemical_formula_moiety 'C12 H14 F2 O' _chemical_formula_weight 212.24 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' _space_group_IT_number 14 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-1/2-Y,-1/2+Z #------------------------------------------------------------------------------ _cell_length_a 10.536(3) _cell_length_b 19.983(6) _cell_length_c 10.272(3) _cell_angle_alpha 90.0000 _cell_angle_beta 107.972(7) _cell_angle_gamma 90.0000 _cell_volume 2057.2(10) _cell_formula_units_Z 8 _cell_measurement_reflns_used 1824 _cell_measurement_theta_min 39.80 _cell_measurement_theta_max 67.80 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896.00 _exptl_absorpt_coefficient_mu 0.930 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.741 _exptl_absorpt_correction_T_max 0.955 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku XtaLAB P100' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.814 _diffrn_reflns_number 20733 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_theta_max 68.003 _diffrn_reflns_theta_min 4.412 _diffrn_reflns_theta_full 67.687 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? _reflns_number_total 3703 _reflns_number_gt 3343 _reflns_threshold_expression F^2^>2.0\s(F^2^) _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . #============================================================================== # 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). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.1055 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 3703 _refine_ls_number_parameters 279 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0637P)^2^+0.5449P] 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 0.000 _refine_diff_density_max 0.23 _refine_diff_density_min -0.19 _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 0.0181 0.0091 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; F F 0.0727 0.0534 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F2 F 0.77363(8) 0.12131(4) 0.11193(9) 0.0439(2) Uani 1 1 d . . . . . F3 F 0.51712(8) 0.07444(5) 0.04870(9) 0.0441(2) Uani 1 1 d . . . . . F22 F 0.40054(8) 0.27108(4) 0.78789(9) 0.0375(2) Uani 1 1 d . . . . . F23 F 0.66391(8) 0.23983(4) 0.90492(8) 0.0348(2) Uani 1 1 d . . . . . O5 O 0.68218(11) 0.02218(6) 0.46446(10) 0.0442(3) Uani 1 1 d D . . . . O25 O 0.51430(10) 0.07323(5) 0.65685(11) 0.0364(3) Uani 1 1 d D . . . . C1 C 0.85880(12) 0.04011(6) 0.28701(12) 0.0227(3) Uani 1 1 d . . . . . H1 H 0.8402 -0.0062 0.3134 0.027 Uiso 1 1 calc R U . . . C2 C 0.74985(13) 0.05706(7) 0.15321(13) 0.0273(3) Uani 1 1 d . . . . . H2 H 0.7525 0.0240 0.0811 0.033 Uiso 1 1 calc R U . . . C3 C 0.61369(13) 0.05592(7) 0.17270(13) 0.0272(3) Uani 1 1 d . . . . . H3 H 0.5943 0.0094 0.1969 0.033 Uiso 1 1 calc R U . . . C4 C 0.60433(15) 0.10277(7) 0.28420(17) 0.0376(3) Uani 1 1 d . . . . . H4A H 0.5150 0.0988 0.2964 0.045 Uiso 1 1 calc R U . . . H4B H 0.6156 0.1495 0.2575 0.045 Uiso 1 1 calc R U . . . C5 C 0.71125(15) 0.08654(7) 0.41872(15) 0.0352(3) Uani 1 1 d . . . . . H5A H 0.7080 0.1209 0.4884 0.042 Uiso 1 1 calc R U . . . C6 C 0.84962(14) 0.08697(7) 0.40167(14) 0.0293(3) Uani 1 1 d . . . . . H6A H 0.9160 0.0731 0.4888 0.035 Uiso 1 1 calc R U . . . H6B H 0.8719 0.1331 0.3810 0.035 Uiso 1 1 calc R U . . . C7 C 0.99444(12) 0.03829(6) 0.26428(12) 0.0236(3) Uani 1 1 d . . . . . C8 C 1.07728(14) 0.09392(7) 0.28217(14) 0.0298(3) Uani 1 1 d . . . . . H8 H 1.0512 0.1347 0.3142 0.036 Uiso 1 1 calc R U . . . C9 C 1.19799(14) 0.09056(7) 0.25367(15) 0.0347(3) Uani 1 1 d . . . . . H9 H 1.2538 0.1289 0.2669 0.042 Uiso 1 1 calc R U . . . C10 C 1.23731(14) 0.03199(8) 0.20631(15) 0.0344(3) Uani 1 1 d . . . . . H10 H 1.3192 0.0300 0.1859 0.041 Uiso 1 1 calc R U . . . C11 C 1.15636(15) -0.02375(7) 0.18890(16) 0.0364(3) Uani 1 1 d . . . . . H11 H 1.1827 -0.0644 0.1566 0.044 Uiso 1 1 calc R U . . . C12 C 1.03666(14) -0.02052(7) 0.21848(14) 0.0309(3) Uani 1 1 d . . . . . H12 H 0.9824 -0.0594 0.2072 0.037 Uiso 1 1 calc R U . . . C20 C 0.09032(13) 0.19758(7) 0.68254(14) 0.0309(3) Uani 1 1 d . . . . . H20 H 0.0979 0.2034 0.5934 0.037 Uiso 1 1 calc R U . . . C21 C 0.33217(12) 0.15726(6) 0.76631(12) 0.0214(3) Uani 1 1 d . . . . . H21 H 0.3607 0.1123 0.8078 0.026 Uiso 1 1 calc R U . . . C22 C 0.43699(13) 0.20749(6) 0.84465(13) 0.0246(3) Uani 1 1 d . . . . . H22 H 0.4406 0.2079 0.9431 0.030 Uiso 1 1 calc R U . . . C23 C 0.57280(12) 0.19055(6) 0.83396(13) 0.0244(3) Uani 1 1 d . . . . . H23 H 0.6012 0.1461 0.8781 0.029 Uiso 1 1 calc R U . . . C24 C 0.57371(13) 0.18756(7) 0.68716(13) 0.0279(3) Uani 1 1 d . . . . . H24A H 0.6631 0.1735 0.6848 0.033 Uiso 1 1 calc R U . . . H24B H 0.5549 0.2326 0.6454 0.033 Uiso 1 1 calc R U . . . C25 C 0.46916(13) 0.13827(7) 0.60526(13) 0.0281(3) Uani 1 1 d . . . . . H25A H 0.4651 0.1407 0.5068 0.034 Uiso 1 1 calc R U . . . C26 C 0.33112(12) 0.15373(6) 0.61702(12) 0.0257(3) Uani 1 1 d . . . . . H26A H 0.2677 0.1186 0.5688 0.031 Uiso 1 1 calc R U . . . H26B H 0.2996 0.1970 0.5716 0.031 Uiso 1 1 calc R U . . . C27 C 0.19822(12) 0.17265(6) 0.78665(13) 0.0230(3) Uani 1 1 d . . . . . C28 C 0.18288(13) 0.16295(7) 0.91531(14) 0.0292(3) Uani 1 1 d . . . . . H28 H 0.2550 0.1454 0.9875 0.035 Uiso 1 1 calc R U . . . C29 C 0.06376(14) 0.17851(7) 0.93947(15) 0.0349(3) Uani 1 1 d . . . . . H29 H 0.0545 0.1710 1.0274 0.042 Uiso 1 1 calc R U . . . C30 C -0.04167(14) 0.20502(7) 0.83574(16) 0.0366(3) Uani 1 1 d . . . . . H30 H -0.1223 0.2169 0.8529 0.044 Uiso 1 1 calc R U . . . C31 C -0.02860(14) 0.21407(7) 0.70713(16) 0.0372(3) Uani 1 1 d . . . . . H31 H -0.1010 0.2316 0.6352 0.045 Uiso 1 1 calc R U . . . H25O H 0.4495(16) 0.0390(8) 0.612(2) 0.064(6) Uiso 1 1 d D . . . . H5O H 0.682(4) 0.0250(18) 0.5594(13) 0.143(13) Uiso 1 1 d D . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.0389(5) 0.0433(5) 0.0457(5) 0.0242(4) 0.0075(4) -0.0029(4) F3 0.0311(4) 0.0530(6) 0.0394(5) 0.0154(4) -0.0019(4) 0.0026(4) F22 0.0340(4) 0.0161(4) 0.0619(6) -0.0018(3) 0.0142(4) 0.0016(3) F23 0.0278(4) 0.0341(5) 0.0406(5) -0.0086(3) 0.0075(3) -0.0090(3) O5 0.0495(6) 0.0561(7) 0.0286(5) -0.0016(5) 0.0144(5) -0.0195(5) O25 0.0340(5) 0.0250(5) 0.0479(6) -0.0055(4) 0.0090(4) 0.0051(4) C1 0.0273(6) 0.0173(6) 0.0227(6) 0.0003(5) 0.0067(5) -0.0008(5) C2 0.0309(7) 0.0266(7) 0.0238(6) 0.0020(5) 0.0077(5) -0.0008(5) C3 0.0266(7) 0.0257(7) 0.0261(6) 0.0043(5) 0.0032(5) 0.0023(5) C4 0.0324(7) 0.0303(7) 0.0520(9) -0.0075(6) 0.0158(7) 0.0040(6) C5 0.0396(8) 0.0350(8) 0.0353(7) -0.0159(6) 0.0180(6) -0.0082(6) C6 0.0327(7) 0.0282(7) 0.0269(6) -0.0070(5) 0.0090(5) -0.0055(5) C7 0.0262(6) 0.0213(6) 0.0217(6) 0.0027(5) 0.0048(5) 0.0003(5) C8 0.0334(7) 0.0221(7) 0.0334(7) -0.0001(5) 0.0094(6) -0.0020(5) C9 0.0313(7) 0.0339(8) 0.0375(8) 0.0030(6) 0.0085(6) -0.0098(6) C10 0.0271(7) 0.0423(8) 0.0349(7) 0.0057(6) 0.0110(6) 0.0006(6) C11 0.0364(8) 0.0319(8) 0.0444(8) -0.0023(6) 0.0177(6) 0.0032(6) C12 0.0322(7) 0.0229(7) 0.0389(7) -0.0026(5) 0.0128(6) -0.0032(5) C20 0.0284(7) 0.0310(7) 0.0327(7) 0.0030(5) 0.0084(6) 0.0019(5) C21 0.0245(6) 0.0156(6) 0.0229(6) 0.0007(4) 0.0055(5) 0.0016(4) C22 0.0276(6) 0.0196(6) 0.0263(6) -0.0028(5) 0.0080(5) -0.0009(5) C23 0.0241(6) 0.0191(6) 0.0281(6) -0.0011(5) 0.0052(5) -0.0029(5) C24 0.0280(6) 0.0273(7) 0.0302(7) 0.0033(5) 0.0116(5) 0.0014(5) C25 0.0305(7) 0.0295(7) 0.0248(6) -0.0020(5) 0.0093(5) 0.0032(5) C26 0.0269(6) 0.0253(7) 0.0232(6) -0.0012(5) 0.0054(5) 0.0026(5) C27 0.0261(6) 0.0150(6) 0.0276(6) -0.0033(5) 0.0077(5) -0.0035(5) C28 0.0303(7) 0.0290(7) 0.0281(7) -0.0038(5) 0.0087(5) -0.0028(5) C29 0.0385(8) 0.0354(8) 0.0353(7) -0.0100(6) 0.0178(6) -0.0063(6) C30 0.0299(7) 0.0308(8) 0.0530(9) -0.0127(6) 0.0185(7) -0.0036(6) C31 0.0272(7) 0.0361(8) 0.0455(8) 0.0005(6) 0.0073(6) 0.0033(6) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)' _computing_cell_refinement 'CrystalClear-SM Expert 2.1 b42' _computing_data_reduction 'CrystalClear-SM Expert 2.1 b42' _computing_structure_solution 'SIR2011 (Burla, et al., 2012)' _computing_structure_refinement 'SHELXL Version 2014/7 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.2 (Rigaku, 2015)' _computing_molecular_graphics 'CrystalStructure 4.2' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F2 C2 1.3987(16) . ? F3 C3 1.4124(15) . ? F22 C22 1.4014(15) . ? F23 C23 1.4110(14) . ? O5 C5 1.4344(19) . ? O5 H5O 0.976(5) . ? O25 C25 1.4285(17) . ? O25 H25O 0.975(5) . ? C1 C7 1.5179(17) . ? C1 C6 1.5308(17) . ? C1 C2 1.5322(17) . ? C1 H1 1.0000 . ? C2 C3 1.5085(19) . ? C2 H2 1.0000 . ? C3 C4 1.506(2) . ? C3 H3 1.0000 . ? C4 C5 1.524(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5211(19) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.3891(19) . ? C7 C8 1.3900(18) . ? C8 C9 1.392(2) . ? C8 H8 0.9500 . ? C9 C10 1.379(2) . ? C9 H9 0.9500 . ? C10 C11 1.381(2) . ? C10 H10 0.9500 . ? C11 C12 1.387(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C20 C27 1.3907(18) . ? C20 C31 1.392(2) . ? C20 H20 0.9500 . ? C21 C27 1.5204(17) . ? C21 C22 1.5253(17) . ? C21 C26 1.5318(17) . ? C21 H21 1.0000 . ? C22 C23 1.5070(18) . ? C22 H22 1.0000 . ? C23 C24 1.5121(18) . ? C23 H23 1.0000 . ? C24 C25 1.5230(19) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.5275(18) . ? C25 H25A 1.0000 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.3936(19) . ? C28 C29 1.388(2) . ? C28 H28 0.9500 . ? C29 C30 1.385(2) . ? C29 H29 0.9500 . ? C30 C31 1.382(2) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O5 H5O 110(2) . . ? C25 O25 H25O 111.0(13) . . ? C7 C1 C6 114.77(10) . . ? C7 C1 C2 110.34(10) . . ? C6 C1 C2 110.32(11) . . ? C7 C1 H1 107.0 . . ? C6 C1 H1 107.0 . . ? C2 C1 H1 107.0 . . ? F2 C2 C3 108.71(10) . . ? F2 C2 C1 108.67(10) . . ? C3 C2 C1 110.95(10) . . ? F2 C2 H2 109.5 . . ? C3 C2 H2 109.5 . . ? C1 C2 H2 109.5 . . ? F3 C3 C4 108.96(11) . . ? F3 C3 C2 109.05(10) . . ? C4 C3 C2 112.31(11) . . ? F3 C3 H3 108.8 . . ? C4 C3 H3 108.8 . . ? C2 C3 H3 108.8 . . ? C3 C4 C5 110.71(11) . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? O5 C5 C6 110.61(12) . . ? O5 C5 C4 108.36(11) . . ? C6 C5 C4 111.16(12) . . ? O5 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C5 C6 C1 112.05(11) . . ? C5 C6 H6A 109.2 . . ? C1 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? C1 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C12 C7 C8 117.88(12) . . ? C12 C7 C1 119.18(11) . . ? C8 C7 C1 122.89(11) . . ? C7 C8 C9 120.72(13) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 120.56(13) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.31(13) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C10 C11 C12 120.08(13) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C7 121.43(12) . . ? C11 C12 H12 119.3 . . ? C7 C12 H12 119.3 . . ? C27 C20 C31 120.89(13) . . ? C27 C20 H20 119.6 . . ? C31 C20 H20 119.6 . . ? C27 C21 C22 110.25(10) . . ? C27 C21 C26 115.25(10) . . ? C22 C21 C26 109.81(10) . . ? C27 C21 H21 107.0 . . ? C22 C21 H21 107.0 . . ? C26 C21 H21 107.0 . . ? F22 C22 C23 108.53(10) . . ? F22 C22 C21 108.44(10) . . ? C23 C22 C21 111.28(10) . . ? F22 C22 H22 109.5 . . ? C23 C22 H22 109.5 . . ? C21 C22 H22 109.5 . . ? F23 C23 C22 108.40(10) . . ? F23 C23 C24 109.27(10) . . ? C22 C23 C24 112.32(10) . . ? F23 C23 H23 108.9 . . ? C22 C23 H23 108.9 . . ? C24 C23 H23 108.9 . . ? C23 C24 C25 110.51(10) . . ? C23 C24 H24A 109.5 . . ? C25 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? O25 C25 C24 106.39(10) . . ? O25 C25 C26 111.76(11) . . ? C24 C25 C26 111.69(11) . . ? O25 C25 H25A 109.0 . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25A 109.0 . . ? C25 C26 C21 112.06(10) . . ? C25 C26 H26A 109.2 . . ? C21 C26 H26A 109.2 . . ? C25 C26 H26B 109.2 . . ? C21 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C20 C27 C28 118.20(12) . . ? C20 C27 C21 122.68(11) . . ? C28 C27 C21 119.10(11) . . ? C29 C28 C27 120.96(13) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C30 C29 C28 120.19(13) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C31 C30 C29 119.51(13) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C30 C31 C20 120.22(14) . . ? C30 C31 H31 119.9 . . ? C20 C31 H31 119.9 . . ? 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 C7 C1 C2 F2 -63.15(13) . . . . ? C6 C1 C2 F2 64.71(13) . . . . ? C7 C1 C2 C3 177.38(10) . . . . ? C6 C1 C2 C3 -54.76(14) . . . . ? F2 C2 C3 F3 58.18(13) . . . . ? C1 C2 C3 F3 177.63(10) . . . . ? F2 C2 C3 C4 -62.70(14) . . . . ? C1 C2 C3 C4 56.74(15) . . . . ? F3 C3 C4 C5 -177.41(11) . . . . ? C2 C3 C4 C5 -56.48(15) . . . . ? C3 C4 C5 O5 -66.85(15) . . . . ? C3 C4 C5 C6 54.89(16) . . . . ? O5 C5 C6 C1 65.63(14) . . . . ? C4 C5 C6 C1 -54.79(15) . . . . ? C7 C1 C6 C5 179.85(11) . . . . ? C2 C1 C6 C5 54.46(15) . . . . ? C6 C1 C7 C12 148.59(12) . . . . ? C2 C1 C7 C12 -86.03(14) . . . . ? C6 C1 C7 C8 -33.98(16) . . . . ? C2 C1 C7 C8 91.39(14) . . . . ? C12 C7 C8 C9 0.58(19) . . . . ? C1 C7 C8 C9 -176.87(12) . . . . ? C7 C8 C9 C10 0.4(2) . . . . ? C8 C9 C10 C11 -0.8(2) . . . . ? C9 C10 C11 C12 0.2(2) . . . . ? C10 C11 C12 C7 0.8(2) . . . . ? C8 C7 C12 C11 -1.2(2) . . . . ? C1 C7 C12 C11 176.39(12) . . . . ? C27 C21 C22 F22 -64.54(13) . . . . ? C26 C21 C22 F22 63.49(12) . . . . ? C27 C21 C22 C23 176.15(10) . . . . ? C26 C21 C22 C23 -55.81(13) . . . . ? F22 C22 C23 F23 59.04(12) . . . . ? C21 C22 C23 F23 178.30(10) . . . . ? F22 C22 C23 C24 -61.79(13) . . . . ? C21 C22 C23 C24 57.46(14) . . . . ? F23 C23 C24 C25 -175.99(10) . . . . ? C22 C23 C24 C25 -55.66(14) . . . . ? C23 C24 C25 O25 -68.52(13) . . . . ? C23 C24 C25 C26 53.69(14) . . . . ? O25 C25 C26 C21 64.73(14) . . . . ? C24 C25 C26 C21 -54.34(14) . . . . ? C27 C21 C26 C25 179.86(10) . . . . ? C22 C21 C26 C25 54.65(14) . . . . ? C31 C20 C27 C28 1.7(2) . . . . ? C31 C20 C27 C21 -176.86(12) . . . . ? C22 C21 C27 C20 110.00(13) . . . . ? C26 C21 C27 C20 -14.98(17) . . . . ? C22 C21 C27 C28 -68.52(14) . . . . ? C26 C21 C27 C28 166.50(11) . . . . ? C20 C27 C28 C29 -0.78(19) . . . . ? C21 C27 C28 C29 177.81(12) . . . . ? C27 C28 C29 C30 -1.0(2) . . . . ? C28 C29 C30 C31 1.8(2) . . . . ? C29 C30 C31 C20 -0.9(2) . . . . ? C27 C20 C31 C30 -0.8(2) . . . . ? #============================================================================== 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 O25 H25o O5 . . 3_656 2.8074(16) 0.974(16) 1.835(16) 175.1(18) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. _shelx_res_file ; shelxl.res created by SHELXL-2014/7 TITL AGDH4 CELL 1.54187 10.53600 19.98300 10.27200 90.00000 107.97200 90.00000 ZERR 8 0.00300 0.00600 0.00300 0.00000 0.00700 0.00000 LATT 1 SYMM -X, .50+Y, .50-Z SFAC C H F O UNIT 96 112 16 8 OMIT 0 4 1 OMIT 0 0 2 L.S. 20 FMAP 2 PLAN 5 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -100.0 ACTA SIZE 0.050 0.100 0.100 DFIX 0.9800 0.0050 O5 H5o O25 H25o WGHT 0.063700 0.544900 FVAR 0.89019 F2 3 0.773631 0.121306 0.111935 11.00000 0.03894 0.04325 = 0.04571 0.02417 0.00749 -0.00288 F3 3 0.517117 0.074442 0.048705 11.00000 0.03111 0.05301 = 0.03938 0.01545 -0.00188 0.00265 F22 3 0.400535 0.271077 0.787890 11.00000 0.03400 0.01614 = 0.06192 -0.00176 0.01418 0.00162 F23 3 0.663914 0.239831 0.904920 11.00000 0.02776 0.03407 = 0.04061 -0.00857 0.00753 -0.00896 O5 4 0.682182 0.022177 0.464464 11.00000 0.04945 0.05610 = 0.02860 -0.00161 0.01442 -0.01949 O25 4 0.514298 0.073234 0.656849 11.00000 0.03397 0.02504 = 0.04786 -0.00545 0.00904 0.00515 C1 1 0.858796 0.040114 0.287011 11.00000 0.02727 0.01734 = 0.02271 0.00032 0.00674 -0.00081 AFIX 13 H1 2 0.840177 -0.006157 0.313438 11.00000 -1.20000 AFIX 0 C2 1 0.749847 0.057062 0.153213 11.00000 0.03088 0.02659 = 0.02380 0.00199 0.00772 -0.00079 AFIX 13 H2 2 0.752532 0.023967 0.081087 11.00000 -1.20000 AFIX 0 C3 1 0.613692 0.055920 0.172701 11.00000 0.02664 0.02569 = 0.02605 0.00431 0.00322 0.00234 AFIX 13 H3 2 0.594317 0.009378 0.196934 11.00000 -1.20000 AFIX 0 C4 1 0.604335 0.102772 0.284202 11.00000 0.03237 0.03026 = 0.05198 -0.00748 0.01578 0.00396 AFIX 23 H4A 2 0.515018 0.098786 0.296369 11.00000 -1.20000 H4B 2 0.615552 0.149472 0.257494 11.00000 -1.20000 AFIX 0 C5 1 0.711252 0.086536 0.418723 11.00000 0.03963 0.03497 = 0.03534 -0.01589 0.01801 -0.00816 AFIX 13 H5A 2 0.708039 0.120913 0.488382 11.00000 -1.20000 AFIX 0 C6 1 0.849620 0.086970 0.401669 11.00000 0.03268 0.02817 = 0.02689 -0.00702 0.00901 -0.00549 AFIX 23 H6A 2 0.915958 0.073061 0.488752 11.00000 -1.20000 H6B 2 0.871872 0.133086 0.380984 11.00000 -1.20000 AFIX 0 C7 1 0.994436 0.038292 0.264279 11.00000 0.02620 0.02134 = 0.02168 0.00274 0.00485 0.00027 C8 1 1.077278 0.093917 0.282172 11.00000 0.03339 0.02207 = 0.03343 -0.00011 0.00937 -0.00202 AFIX 43 H8 2 1.051228 0.134669 0.314205 11.00000 -1.20000 AFIX 0 C9 1 1.197994 0.090559 0.253665 11.00000 0.03133 0.03389 = 0.03753 0.00304 0.00854 -0.00982 AFIX 43 H9 2 1.253770 0.128933 0.266937 11.00000 -1.20000 AFIX 0 C10 1 1.237311 0.031989 0.206314 11.00000 0.02708 0.04228 = 0.03486 0.00571 0.01098 0.00058 AFIX 43 H10 2 1.319245 0.030024 0.185894 11.00000 -1.20000 AFIX 0 C11 1 1.156356 -0.023752 0.188899 11.00000 0.03644 0.03194 = 0.04442 -0.00226 0.01775 0.00318 AFIX 43 H11 2 1.182674 -0.064372 0.156612 11.00000 -1.20000 AFIX 0 C12 1 1.036661 -0.020521 0.218482 11.00000 0.03222 0.02293 = 0.03890 -0.00261 0.01284 -0.00318 AFIX 43 H12 2 0.982367 -0.059373 0.207179 11.00000 -1.20000 AFIX 0 C20 1 0.090320 0.197577 0.682541 11.00000 0.02842 0.03095 = 0.03265 0.00304 0.00837 0.00189 AFIX 43 H20 2 0.097873 0.203428 0.593447 11.00000 -1.20000 AFIX 0 C21 1 0.332167 0.157255 0.766314 11.00000 0.02445 0.01561 = 0.02289 0.00071 0.00548 0.00156 AFIX 13 H21 2 0.360702 0.112290 0.807756 11.00000 -1.20000 AFIX 0 C22 1 0.436987 0.207489 0.844652 11.00000 0.02760 0.01960 = 0.02632 -0.00278 0.00798 -0.00094 AFIX 13 H22 2 0.440647 0.207861 0.943094 11.00000 -1.20000 AFIX 0 C23 1 0.572796 0.190550 0.833964 11.00000 0.02406 0.01910 = 0.02815 -0.00113 0.00524 -0.00287 AFIX 13 H23 2 0.601218 0.146122 0.878150 11.00000 -1.20000 AFIX 0 C24 1 0.573707 0.187565 0.687161 11.00000 0.02796 0.02725 = 0.03018 0.00326 0.01158 0.00135 AFIX 23 H24A 2 0.663082 0.173541 0.684775 11.00000 -1.20000 H24B 2 0.554948 0.232581 0.645381 11.00000 -1.20000 AFIX 0 C25 1 0.469156 0.138271 0.605263 11.00000 0.03050 0.02953 = 0.02476 -0.00197 0.00930 0.00321 AFIX 13 H25A 2 0.465070 0.140716 0.506816 11.00000 -1.20000 AFIX 0 C26 1 0.331125 0.153726 0.617021 11.00000 0.02691 0.02533 = 0.02321 -0.00124 0.00544 0.00260 AFIX 23 H26A 2 0.267736 0.118593 0.568804 11.00000 -1.20000 H26B 2 0.299584 0.197005 0.571640 11.00000 -1.20000 AFIX 0 C27 1 0.198223 0.172645 0.786653 11.00000 0.02610 0.01501 = 0.02763 -0.00332 0.00770 -0.00350 C28 1 0.182876 0.162951 0.915309 11.00000 0.03029 0.02905 = 0.02809 -0.00385 0.00867 -0.00282 AFIX 43 H28 2 0.255015 0.145438 0.987524 11.00000 -1.20000 AFIX 0 C29 1 0.063761 0.178506 0.939471 11.00000 0.03852 0.03538 = 0.03534 -0.01003 0.01783 -0.00626 AFIX 43 H29 2 0.054476 0.170953 1.027392 11.00000 -1.20000 AFIX 0 C30 1 -0.041668 0.205020 0.835744 11.00000 0.02990 0.03080 = 0.05300 -0.01267 0.01848 -0.00362 AFIX 43 H30 2 -0.122348 0.216889 0.852919 11.00000 -1.20000 AFIX 0 C31 1 -0.028604 0.214074 0.707130 11.00000 0.02725 0.03606 = 0.04551 0.00045 0.00726 0.00333 AFIX 43 H31 2 -0.101020 0.231614 0.635250 11.00000 -1.20000 AFIX 0 H25O 2 0.449524 0.039029 0.612294 11.00000 0.06412 H5O 2 0.682452 0.024989 0.559447 11.00000 0.14253 HKLF 4 REM AGDH4 REM R1 = 0.0359 for 3343 Fo > 4sig(Fo) and 0.0389 for all 3703 data REM 279 parameters refined using 2 restraints END WGHT 0.0477 0.6444 REM Instructions for potential hydrogen bonds EQIV $1 x, y, z+1 HTAB C21 F3_$1 HTAB C23 F2_$1 HTAB C23 F3_$1 EQIV $2 -x+1, -y, -z+1 HTAB O25 O5_$2 HTAB O5 O25 REM Highest difference peak 0.230, deepest hole -0.189, 1-sigma level 0.038 Q1 1 0.6204 0.0899 0.2225 11.00000 0.05 0.23 Q2 1 0.8094 0.0476 0.2180 11.00000 0.05 0.22 Q3 1 0.5039 0.1982 0.8358 11.00000 0.05 0.22 Q4 1 0.3360 0.1583 0.6946 11.00000 0.05 0.21 Q5 1 0.8562 0.0668 0.3404 11.00000 0.05 0.21 ; _shelx_res_checksum 14114 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_13 _database_code_depnum_ccdc_archive 'CCDC 1817389' _audit_update_record ; 2018-01-16 deposited with the CCDC. 2018-02-19 downloaded from the CCDC. ; _audit_creation_date 2016-12-01 _audit_creation_method 'by CrystalStructure 4.2' _chemical_formula_sum 'C12 H15 F O' _chemical_formula_moiety 'C12 H15 F O' _chemical_formula_weight 194.25 _chemical_melting_point ? _chemical_absolute_configuration ' ad ' #============================================================================== # CRYSTAL DATA _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _space_group_IT_number 19 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,-Y,1/2+Z 3 1/2+X,1/2-Y,-Z 4 -X,1/2+Y,1/2-Z #------------------------------------------------------------------------------ _cell_length_a 5.33024(13) _cell_length_b 9.6528(3) _cell_length_c 20.0332(7) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1030.74(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7965 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 75.27 _cell_measurement_temperature 125 #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.010 _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416.00 _exptl_absorpt_coefficient_mu 0.735 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.716 _exptl_absorpt_correction_T_max 0.993 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 125 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.811 _diffrn_reflns_number 11679 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_theta_max 75.375 _diffrn_reflns_theta_min 4.414 _diffrn_reflns_theta_full 67.687 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? _reflns_number_total 2104 _reflns_number_gt 2017 _reflns_threshold_expression F^2^>2.0\s(F^2^) _reflns_Friedel_coverage 0.667 _reflns_Friedel_fraction_max 0.976 _reflns_Friedel_fraction_full 0.999 #============================================================================== # 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). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1496 _refine_ls_wR_factor_gt 0.1485 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 2104 _refine_ls_number_parameters 135 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0961P)^2^+0.4402P] 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 0.000 _refine_diff_density_max 0.38 _refine_diff_density_min -0.22 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; F F 0.0727 0.0534 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F2 F 0.2818(3) 1.1143(2) 0.89389(9) 0.0450(5) Uani 1 1 d . . . A 1 O5 O -0.2673(5) 0.7943(3) 0.98741(12) 0.0342(6) Uani 0.8 1 d D . P A 1 C1 C -0.0554(6) 1.0022(3) 0.83665(14) 0.0346(6) Uani 1 1 d . . . A 1 H1 H -0.2263 1.0219 0.8184 0.041 Uiso 1 1 calc R U . A 1 C2 C 0.0290(5) 1.1324(3) 0.87342(15) 0.0356(6) Uani 1 1 d . . . A 1 H2 H 0.0189 1.2133 0.8423 0.043 Uiso 1 1 calc R U . A 1 C3 C -0.1267(6) 1.1626(3) 0.93491(15) 0.0386(7) Uani 1 1 d . . . A 1 H3A H -0.0516 1.2415 0.9593 0.046 Uiso 1 1 calc R U . A 1 H3B H -0.2980 1.1899 0.9210 0.046 Uiso 1 1 calc R U . A 1 C4 C -0.1435(6) 1.0380(3) 0.98158(15) 0.0418(7) Uani 1 1 d . . . A 1 H4A H 0.0251 1.0163 0.9995 0.050 Uiso 1 1 calc R U . A 1 H4B H -0.2548 1.0603 1.0197 0.050 Uiso 1 1 calc R U . A 1 C5 C -0.2455(6) 0.9135(3) 0.94460(15) 0.0376(6) Uani 1 1 d . . . A 1 H5A H -0.4171 0.9374 0.9280 0.045 Uiso 1 1 calc R U . A 1 C6 C -0.0834(6) 0.8799(3) 0.88468(15) 0.0374(6) Uani 1 1 d . . . A 1 H6A H -0.1582 0.8007 0.8604 0.045 Uiso 1 1 calc R U . A 1 H6B H 0.0850 0.8513 0.9003 0.045 Uiso 1 1 calc R U . A 1 C7 C 0.1124(6) 0.9693(3) 0.77720(14) 0.0366(6) Uani 1 1 d . . . A 1 C8 C 0.3126(6) 0.8759(4) 0.78173(15) 0.0422(7) Uani 1 1 d . . . A 1 H8 H 0.3435 0.8298 0.8228 0.051 Uiso 1 1 calc R U . A 1 C9 C 0.4675(7) 0.8491(4) 0.72708(17) 0.0490(8) Uani 1 1 d . . . A 1 H9 H 0.6016 0.7848 0.7310 0.059 Uiso 1 1 calc R U . A 1 C10 C 0.4254(7) 0.9162(4) 0.66735(17) 0.0495(8) Uani 1 1 d . . . A 1 H10 H 0.5323 0.8996 0.6303 0.059 Uiso 1 1 calc R U . A 1 C11 C 0.2260(9) 1.0081(3) 0.66162(17) 0.0539(9) Uani 1 1 d . . . A 1 H11 H 0.1956 1.0537 0.6204 0.065 Uiso 1 1 calc R U . A 1 C12 C 0.0710(8) 1.0337(3) 0.71596(15) 0.0465(8) Uani 1 1 d . . . A 1 H12 H -0.0656 1.0961 0.7113 0.056 Uiso 1 1 calc R U . A 1 H5O H -0.113(6) 0.748(6) 1.001(3) 0.057(14) Uiso 0.8 1 d D . P B 1 O5' O -0.052(3) 1.2779(18) 0.9613(8) 0.074(4) Uiso 0.2 1 d . . P C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.0313(9) 0.0442(10) 0.0595(11) -0.0042(8) -0.0051(8) -0.0015(7) O5 0.0327(12) 0.0324(12) 0.0376(12) 0.0176(9) 0.0054(10) 0.0006(10) C1 0.0348(14) 0.0305(14) 0.0383(14) 0.0019(11) 0.0008(11) -0.0016(11) C2 0.0277(13) 0.0323(13) 0.0466(15) 0.0027(12) -0.0033(11) -0.0010(11) C3 0.0374(15) 0.0323(14) 0.0461(16) -0.0050(12) -0.0017(13) -0.0014(12) C4 0.0435(16) 0.0442(16) 0.0378(14) 0.0004(13) -0.0009(12) 0.0034(14) C5 0.0378(14) 0.0331(14) 0.0419(14) 0.0111(11) 0.0009(13) 0.0009(12) C6 0.0397(15) 0.0275(13) 0.0450(15) 0.0040(11) 0.0021(12) -0.0006(11) C7 0.0372(15) 0.0324(13) 0.0403(15) -0.0013(12) 0.0014(11) -0.0060(11) C8 0.0353(15) 0.0497(17) 0.0417(15) -0.0010(13) -0.0012(12) -0.0003(13) C9 0.0393(16) 0.055(2) 0.0522(18) -0.0093(15) 0.0033(14) 0.0002(15) C10 0.057(2) 0.0462(17) 0.0453(17) -0.0090(14) 0.0143(15) -0.0109(16) C11 0.082(3) 0.0369(16) 0.0425(16) 0.0010(13) 0.0099(17) -0.0061(18) C12 0.062(2) 0.0333(14) 0.0438(16) 0.0042(13) 0.0058(14) 0.0006(14) #============================================================================== _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_structure_solution 'SIR2011 (Burla, et al., 2012)' _computing_structure_refinement 'SHELXL Version 2014/7 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.2 (Rigaku, 2015)' _computing_molecular_graphics 'CrystalStructure 4.2' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F2 C2 1.420(3) . ? O5 C5 1.439(3) . ? O5 H5O 0.975(7) . ? C1 C7 1.523(4) . ? C1 C2 1.525(4) . ? C1 C6 1.530(4) . ? C1 H1 1.0000 . ? C2 C3 1.514(4) . ? C2 H2 1.0000 . ? C3 C4 1.526(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.513(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.514(4) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.393(4) . ? C7 C8 1.400(4) . ? C8 C9 1.395(5) . ? C8 H8 0.9500 . ? C9 C10 1.379(5) . ? C9 H9 0.9500 . ? C10 C11 1.389(6) . ? C10 H10 0.9500 . ? C11 C12 1.389(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O5 H5O 118(4) . . ? C7 C1 C2 112.1(2) . . ? C7 C1 C6 112.8(2) . . ? C2 C1 C6 111.2(2) . . ? C7 C1 H1 106.8 . . ? C2 C1 H1 106.8 . . ? C6 C1 H1 106.8 . . ? F2 C2 C3 108.0(2) . . ? F2 C2 C1 108.5(2) . . ? C3 C2 C1 113.0(2) . . ? F2 C2 H2 109.1 . . ? C3 C2 H2 109.1 . . ? C1 C2 H2 109.1 . . ? C4 C3 C2 112.3(2) . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 110.3(2) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? O5 C5 C4 111.8(2) . . ? O5 C5 C6 110.3(2) . . ? C4 C5 C6 110.7(3) . . ? O5 C5 H5A 107.9 . . ? C4 C5 H5A 107.9 . . ? C6 C5 H5A 107.9 . . ? C5 C6 C1 112.9(2) . . ? C5 C6 H6A 109.0 . . ? C1 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C1 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C12 C7 C8 117.7(3) . . ? C12 C7 C1 120.2(3) . . ? C8 C7 C1 122.1(3) . . ? C9 C8 C7 121.3(3) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C10 C9 C8 119.8(3) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 119.7(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C7 C12 C11 121.1(3) . . ? C7 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C1 C2 F2 -57.1(3) . . . . ? C6 C1 C2 F2 70.2(3) . . . . ? C7 C1 C2 C3 -176.9(2) . . . . ? C6 C1 C2 C3 -49.5(3) . . . . ? F2 C2 C3 C4 -67.6(3) . . . . ? C1 C2 C3 C4 52.5(3) . . . . ? C2 C3 C4 C5 -55.9(3) . . . . ? C3 C4 C5 O5 -179.2(2) . . . . ? C3 C4 C5 C6 57.4(3) . . . . ? O5 C5 C6 C1 179.3(2) . . . . ? C4 C5 C6 C1 -56.4(3) . . . . ? C7 C1 C6 C5 178.7(2) . . . . ? C2 C1 C6 C5 51.8(3) . . . . ? C2 C1 C7 C12 -83.9(4) . . . . ? C6 C1 C7 C12 149.6(3) . . . . ? C2 C1 C7 C8 95.5(3) . . . . ? C6 C1 C7 C8 -30.9(4) . . . . ? C12 C7 C8 C9 0.8(5) . . . . ? C1 C7 C8 C9 -178.7(3) . . . . ? C7 C8 C9 C10 0.5(5) . . . . ? C8 C9 C10 C11 -1.2(5) . . . . ? C9 C10 C11 C12 0.7(5) . . . . ? C8 C7 C12 C11 -1.3(5) . . . . ? C1 C7 C12 C11 178.2(3) . . . . ? C10 C11 C12 C7 0.6(6) . . . . ? #============================================================================== 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 O5 H5O O5 . . 3_567 2.844(3) 0.97(4) 1.90(3) 162(4) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. _shelx_res_file ; shelxl.res created by SHELXL-2014/7 TITL AGDH6 CELL 1.54187 5.33024 9.65280 20.03320 90.00000 90.00000 90.00000 ZERR 4 0.00013 0.00030 0.00070 0.00000 0.00000 0.00000 LATT -1 SYMM .50-X, -Y, .50+Z SYMM .50+X, .50-Y, -Z SYMM -X, .50+Y, .50-Z SFAC C H F O UNIT 48 60 4 4 L.S. 20 FMAP 2 PLAN 5 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -148.0 ACTA SIZE 0.120 0.030 0.010 DFIX 0.9800 0.0050 O5 H5O WGHT 0.096100 0.440200 FVAR 2.44650 PART 1 F2 3 0.281787 1.114283 0.893886 11.00000 0.03132 0.04421 = 0.05951 -0.00417 -0.00510 -0.00153 O5 4 -0.267303 0.794343 0.987409 10.80000 0.03268 0.03236 = 0.03764 0.01761 0.00536 0.00057 C1 1 -0.055384 1.002186 0.836653 11.00000 0.03480 0.03051 = 0.03834 0.00193 0.00077 -0.00156 AFIX 13 H1 2 -0.226271 1.021920 0.818378 11.00000 -1.20000 AFIX 0 C2 1 0.028952 1.132448 0.873419 11.00000 0.02770 0.03235 = 0.04663 0.00273 -0.00326 -0.00104 AFIX 13 H2 2 0.018885 1.213328 0.842342 11.00000 -1.20000 AFIX 0 C3 1 -0.126745 1.162593 0.934914 11.00000 0.03736 0.03233 = 0.04607 -0.00504 -0.00168 -0.00137 AFIX 23 H3A 2 -0.051596 1.241539 0.959314 11.00000 -1.20000 H3B 2 -0.297994 1.189903 0.921027 11.00000 -1.20000 AFIX 0 C4 1 -0.143527 1.037963 0.981583 11.00000 0.04353 0.04416 = 0.03776 0.00042 -0.00091 0.00344 AFIX 23 H4A 2 0.025095 1.016251 0.999465 11.00000 -1.20000 H4B 2 -0.254775 1.060316 1.019662 11.00000 -1.20000 AFIX 0 C5 1 -0.245495 0.913498 0.944599 11.00000 0.03780 0.03306 = 0.04193 0.01114 0.00086 0.00094 AFIX 13 H5A 2 -0.417096 0.937383 0.928027 11.00000 -1.20000 AFIX 0 C6 1 -0.083392 0.879850 0.884675 11.00000 0.03972 0.02753 = 0.04500 0.00400 0.00210 -0.00062 AFIX 23 H6A 2 -0.158152 0.800666 0.860370 11.00000 -1.20000 H6B 2 0.084990 0.851267 0.900337 11.00000 -1.20000 AFIX 0 C7 1 0.112400 0.969344 0.777201 11.00000 0.03717 0.03241 = 0.04026 -0.00131 0.00137 -0.00601 C8 1 0.312580 0.875857 0.781731 11.00000 0.03532 0.04973 = 0.04165 -0.00101 -0.00124 -0.00031 AFIX 43 H8 2 0.343529 0.829766 0.822813 11.00000 -1.20000 AFIX 0 C9 1 0.467468 0.849082 0.727083 11.00000 0.03930 0.05543 = 0.05224 -0.00935 0.00330 0.00018 AFIX 43 H9 2 0.601584 0.784780 0.731015 11.00000 -1.20000 AFIX 0 C10 1 0.425394 0.916187 0.667350 11.00000 0.05708 0.04615 = 0.04534 -0.00896 0.01427 -0.01091 AFIX 43 H10 2 0.532323 0.899608 0.630262 11.00000 -1.20000 AFIX 0 C11 1 0.225994 1.008140 0.661624 11.00000 0.08221 0.03689 = 0.04254 0.00100 0.00989 -0.00608 AFIX 43 H11 2 0.195585 1.053716 0.620380 11.00000 -1.20000 AFIX 0 C12 1 0.071007 1.033667 0.715961 11.00000 0.06236 0.03331 = 0.04376 0.00425 0.00580 0.00065 AFIX 43 H12 2 -0.065643 1.096097 0.711277 11.00000 -1.20000 AFIX 0 H5O 2 -0.113110 0.747911 1.001008 10.80000 0.05741 PART 2 O5' 4 -0.052079 1.277852 0.961313 10.20000 0.07370 HKLF 4 REM AGDH6 REM R1 = 0.0496 for 2017 Fo > 4sig(Fo) and 0.0509 for all 2104 data REM 135 parameters refined using 1 restraints END WGHT 0.0841 0.3234 REM Instructions for potential hydrogen bonds EQIV $1 x-1, y, z HTAB C3 F2_$1 HTAB C5 F2_$1 EQIV $2 x+1/2, -y+3/2, -z+2 HTAB O5 O5_$2 REM Highest difference peak 0.382, deepest hole -0.223, 1-sigma level 0.057 Q1 1 0.0813 0.9853 0.8211 11.00000 0.05 0.16 Q2 1 0.2606 1.0996 0.9970 11.00000 0.05 0.14 Q3 1 0.2685 1.1017 0.9612 11.00000 0.05 0.13 Q4 1 0.1287 0.7843 0.9597 11.00000 0.05 0.13 Q5 1 0.3425 1.1151 0.8330 11.00000 0.05 0.13 ; _shelx_res_checksum 47513