data_15srv036 _audit_creation_date 2015-02-06 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998) ; _publ_contact_author_address ; Science site South Rd Durham ; _publ_contact_author_email d.s.yufit@durham.ac.uk _publ_contact_author_name 'Yufit, D.S.' _publ_contact_author_phone '' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H17 F O4' _chemical_formula_sum 'C18 H17 F O4' _chemical_formula_weight 316.32 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 8.6393(2) _cell_length_b 20.2165(4) _cell_length_c 8.7948(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.495(4) _cell_angle_gamma 90.00 _cell_volume 1535.55(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9972 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 31.16 _cell_measurement_theta_min 2.36 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn F1 F 0.04024(11) 0.51971(5) 0.34763(11) 0.0214(2) Uani 1 d . . . O1 O -0.11628(14) 0.53811(6) 0.09801(14) 0.0240(3) Uani 1 d . . . O2 O 0.04498(13) 0.61766(6) 0.01835(12) 0.0192(2) Uani 1 d . . . O3 O 0.31295(14) 0.49476(6) 0.23821(15) 0.0277(3) Uani 1 d . . . O4 O 0.34859(13) 0.60099(6) 0.17469(14) 0.0214(3) Uani 1 d . . . C1 C 0.09934(18) 0.57015(8) 0.26018(17) 0.0162(3) Uani 1 d . . . C2 C 0.08847(17) 0.63657(8) 0.34441(17) 0.0157(3) Uani 1 d . . . H2 H 0.1301 0.6710 0.2748 0.020(5) Uiso 1 calc . . R C3 C -0.07998(17) 0.65491(7) 0.37116(17) 0.0153(3) Uani 1 d . . . C4 C -0.14840(18) 0.70527(8) 0.28570(18) 0.0183(3) Uani 1 d . . . C5 C -0.2997(2) 0.72478(9) 0.3117(2) 0.0238(4) Uani 1 d . . . C6 C -0.38407(19) 0.69331(10) 0.4219(2) 0.0259(4) Uani 1 d . . . C7 C -0.3173(2) 0.64219(9) 0.5063(2) 0.0243(4) Uani 1 d . . . C8 C -0.16583(19) 0.62338(8) 0.48188(18) 0.0194(3) Uani 1 d . . . C9 C 0.18369(17) 0.64130(8) 0.49255(17) 0.0163(3) Uani 1 d . . . C10 C 0.23767(19) 0.58774(9) 0.57763(19) 0.0214(3) Uani 1 d . . . C11 C 0.3207(2) 0.59813(9) 0.7143(2) 0.0252(4) Uani 1 d . . . C12 C 0.35131(19) 0.66150(9) 0.7650(2) 0.0236(4) Uani 1 d . . . C13 C 0.29878(18) 0.71519(9) 0.68034(19) 0.0200(3) Uani 1 d . . . C14 C 0.21423(18) 0.70519(8) 0.54654(18) 0.0179(3) Uani 1 d . . . C15 C -0.00446(17) 0.57235(8) 0.11503(17) 0.0162(3) Uani 1 d . . . C16 C -0.0478(2) 0.62396(9) -0.1209(2) 0.0238(4) Uani 1 d . . . C17 C 0.26680(18) 0.55015(8) 0.22379(17) 0.0175(3) Uani 1 d . . . C18 C 0.5064(2) 0.58580(10) 0.1343(2) 0.0274(4) Uani 1 d . . . H4 H -0.092(2) 0.7277(11) 0.209(2) 0.027(5) Uiso 1 d . . . H5 H -0.342(2) 0.7606(11) 0.251(2) 0.026(5) Uiso 1 d . . . H6 H -0.485(3) 0.7075(11) 0.442(2) 0.029(5) Uiso 1 d . . . H7 H -0.371(3) 0.6207(13) 0.580(3) 0.043(7) Uiso 1 d . . . H8 H -0.119(2) 0.5879(10) 0.543(2) 0.025(5) Uiso 1 d . . . H10 H 0.215(2) 0.5432(10) 0.547(2) 0.019(5) Uiso 1 d . . . H11 H 0.356(3) 0.5597(11) 0.773(3) 0.034(6) Uiso 1 d . . . H12 H 0.409(2) 0.6688(11) 0.860(3) 0.031(6) Uiso 1 d . . . H13 H 0.321(2) 0.7590(11) 0.714(2) 0.030(6) Uiso 1 d . . . H14 H 0.173(2) 0.7432(10) 0.488(2) 0.022(5) Uiso 1 d . . . H16A H 0.009(3) 0.6560(12) -0.183(3) 0.037(6) Uiso 1 d . . . H16B H -0.152(3) 0.6380(12) -0.092(3) 0.046(7) Uiso 1 d . . . H16C H -0.054(3) 0.5819(13) -0.172(3) 0.044(7) Uiso 1 d . . . H18A H 0.559(2) 0.5635(11) 0.217(3) 0.028(5) Uiso 1 d . . . H18B H 0.555(3) 0.6275(11) 0.106(3) 0.031(5) Uiso 1 d . . . H18C H 0.507(3) 0.5574(12) 0.043(3) 0.034(6) Uiso 1 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 F1 0.0267(5) 0.0167(5) 0.0209(5) 0.0031(4) 0.0027(4) -0.0036(4) O1 0.0240(6) 0.0246(6) 0.0234(6) 0.0003(5) -0.0009(5) -0.0062(5) O2 0.0208(6) 0.0201(6) 0.0167(5) -0.0002(4) -0.0005(4) -0.0032(4) O3 0.0269(6) 0.0210(6) 0.0352(7) 0.0000(5) -0.0026(5) 0.0041(5) O4 0.0180(5) 0.0203(6) 0.0262(6) -0.0008(5) 0.0054(5) 0.0013(4) C1 0.0174(7) 0.0162(7) 0.0149(7) 0.0004(5) 0.0012(6) -0.0009(6) C2 0.0152(7) 0.0154(7) 0.0164(7) -0.0020(5) 0.0017(5) 0.0001(6) C3 0.0147(7) 0.0166(7) 0.0144(7) -0.0056(5) -0.0001(5) 0.0000(5) C4 0.0180(7) 0.0185(7) 0.0184(7) -0.0014(6) 0.0023(6) -0.0010(6) C5 0.0210(8) 0.0264(8) 0.0239(8) 0.0005(7) -0.0006(6) 0.0072(7) C6 0.0135(7) 0.0397(10) 0.0247(9) -0.0050(7) 0.0012(6) 0.0032(7) C7 0.0223(8) 0.0331(9) 0.0176(8) -0.0025(7) 0.0049(6) -0.0064(7) C8 0.0217(8) 0.0212(8) 0.0153(7) -0.0011(6) -0.0002(6) 0.0001(6) C9 0.0117(6) 0.0214(8) 0.0159(7) -0.0037(6) 0.0021(5) 0.0003(6) C10 0.0203(8) 0.0211(8) 0.0226(8) -0.0014(6) -0.0017(6) -0.0006(6) C11 0.0233(8) 0.0274(9) 0.0247(9) 0.0033(7) -0.0052(7) 0.0013(7) C12 0.0182(7) 0.0336(9) 0.0188(8) -0.0043(7) -0.0024(6) -0.0014(7) C13 0.0155(7) 0.0241(8) 0.0206(8) -0.0078(6) 0.0043(6) -0.0026(6) C14 0.0161(7) 0.0207(8) 0.0172(7) -0.0031(6) 0.0034(6) 0.0008(6) C15 0.0169(7) 0.0177(7) 0.0140(7) -0.0040(5) 0.0021(5) 0.0038(6) C16 0.0281(9) 0.0250(9) 0.0180(8) 0.0040(7) -0.0038(7) -0.0004(7) C17 0.0174(7) 0.0204(7) 0.0148(7) -0.0030(6) -0.0011(6) 0.0020(6) C18 0.0168(8) 0.0333(10) 0.0323(10) -0.0067(8) 0.0060(7) 0.0009(7) _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 F1 C1 1.3830(18) . ? O1 C15 1.1947(19) . ? O2 C15 1.3279(19) . ? O2 C16 1.452(2) . ? O3 C17 1.194(2) . ? O4 C17 1.326(2) . ? O4 C18 1.450(2) . ? C1 C2 1.537(2) . ? C1 C15 1.541(2) . ? C1 C17 1.544(2) . ? C2 H2 1.0000 . ? C2 C3 1.526(2) . ? C2 C9 1.526(2) . ? C3 C4 1.389(2) . ? C3 C8 1.394(2) . ? C4 C5 1.390(2) . ? C4 H4 0.96(2) . ? C5 C6 1.383(3) . ? C5 H5 0.96(2) . ? C6 C7 1.389(3) . ? C6 H6 0.94(2) . ? C7 C8 1.385(2) . ? C7 H7 0.91(3) . ? C8 H8 0.98(2) . ? C9 C10 1.390(2) . ? C9 C14 1.399(2) . ? C10 C11 1.399(2) . ? C10 H10 0.96(2) . ? C11 C12 1.380(3) . ? C11 H11 0.98(2) . ? C12 C13 1.386(3) . ? C12 H12 0.97(2) . ? C13 C14 1.384(2) . ? C13 H13 0.95(2) . ? C14 H14 0.98(2) . ? C16 H16A 0.99(2) . ? C16 H16B 0.98(3) . ? C16 H16C 0.96(3) . ? C18 H18A 0.96(2) . ? C18 H18B 0.98(2) . ? C18 H18C 0.99(2) . ? 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 C15 O2 C16 114.90(13) . . ? C17 O4 C18 115.33(13) . . ? F1 C1 C2 110.36(12) . . ? F1 C1 C15 105.46(12) . . ? F1 C1 C17 106.48(12) . . ? C2 C1 C15 109.41(12) . . ? C2 C1 C17 113.45(12) . . ? C15 C1 C17 111.34(12) . . ? C1 C2 H2 106.6 . . ? C3 C2 C1 110.91(12) . . ? C3 C2 H2 106.6 . . ? C9 C2 C1 115.34(13) . . ? C9 C2 H2 106.6 . . ? C9 C2 C3 110.38(12) . . ? C4 C3 C2 119.27(14) . . ? C4 C3 C8 119.13(14) . . ? C8 C3 C2 121.58(14) . . ? C3 C4 C5 120.52(15) . . ? C3 C4 H4 120.6(13) . . ? C5 C4 H4 118.8(13) . . ? C4 C5 H5 117.9(13) . . ? C6 C5 C4 120.00(16) . . ? C6 C5 H5 122.1(13) . . ? C5 C6 C7 119.86(16) . . ? C5 C6 H6 120.1(13) . . ? C7 C6 H6 120.0(13) . . ? C6 C7 H7 121.4(16) . . ? C8 C7 C6 120.14(16) . . ? C8 C7 H7 118.4(16) . . ? C3 C8 H8 120.2(12) . . ? C7 C8 C3 120.34(16) . . ? C7 C8 H8 119.5(12) . . ? C10 C9 C2 125.22(14) . . ? C10 C9 C14 118.62(14) . . ? C14 C9 C2 116.14(14) . . ? C9 C10 C11 120.18(16) . . ? C9 C10 H10 121.1(12) . . ? C11 C10 H10 118.7(12) . . ? C10 C11 H11 118.7(13) . . ? C12 C11 C10 120.46(16) . . ? C12 C11 H11 120.8(13) . . ? C11 C12 C13 119.72(16) . . ? C11 C12 H12 120.5(13) . . ? C13 C12 H12 119.7(13) . . ? C12 C13 H13 120.3(13) . . ? C14 C13 C12 120.05(15) . . ? C14 C13 H13 119.7(13) . . ? C9 C14 H14 118.8(12) . . ? C13 C14 C9 120.96(15) . . ? C13 C14 H14 120.3(12) . . ? O1 C15 O2 126.30(14) . . ? O1 C15 C1 122.56(14) . . ? O2 C15 C1 111.12(13) . . ? O2 C16 H16A 104.5(14) . . ? O2 C16 H16B 107.5(15) . . ? O2 C16 H16C 110.0(15) . . ? H16A C16 H16B 115(2) . . ? H16A C16 H16C 110(2) . . ? H16B C16 H16C 110(2) . . ? O3 C17 O4 125.60(15) . . ? O3 C17 C1 122.39(15) . . ? O4 C17 C1 112.01(13) . . ? O4 C18 H18A 110.4(13) . . ? O4 C18 H18B 107.3(13) . . ? O4 C18 H18C 110.1(13) . . ? H18A C18 H18B 113.4(19) . . ? H18A C18 H18C 109.3(19) . . ? H18B C18 H18C 106.2(19) . . ? 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 C15 C1 F1 4.3(2) . . . . ? O2 C15 C1 F1 -177.53(12) . . . . ? O3 C17 C1 F1 16.8(2) . . . . ? O4 C17 C1 F1 -163.86(12) . . . . ? C1 C2 C3 C4 -106.80(16) . . . . ? C1 C2 C3 C8 74.75(18) . . . . ? C1 C2 C9 C10 -20.5(2) . . . . ? C1 C2 C9 C14 161.18(13) . . . . ? C2 C1 C15 O1 -114.38(16) . . . . ? C2 C1 C15 O2 63.77(16) . . . . ? C2 C1 C17 O3 138.35(16) . . . . ? C2 C1 C17 O4 -42.27(17) . . . . ? C3 C2 C1 F1 -62.96(16) . . . . ? C3 C2 C1 C15 52.65(16) . . . . ? C3 C2 C1 C17 177.64(12) . . . . ? C3 C2 C9 C10 106.18(17) . . . . ? C3 C2 C9 C14 -72.15(17) . . . . ? C4 C3 C2 C9 124.10(15) . . . . ? C8 C3 C2 C9 -54.35(19) . . . . ? C9 C2 C1 F1 63.44(16) . . . . ? C9 C2 C1 C15 179.05(12) . . . . ? C9 C2 C1 C17 -55.96(17) . . . . ? C15 C1 C17 O3 -97.70(18) . . . . ? C15 C1 C17 O4 81.68(16) . . . . ? C17 C1 C15 O1 119.41(16) . . . . ? C17 C1 C15 O2 -62.44(16) . . . . ? _olex2_submission_special_instructions 'No special instructions were received'