#------------------------------------------------------------------------------ #$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/58/2005898.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2005898 loop_ _publ_author_name 'Swenson, D. C.' 'Lu, H.' 'Burton, D. J.' _publ_section_title ; (Z)-3-Phenyl-2-(trifluoromethyl)prop-2-enoic Acid: a Hydrogen-Bonded Dimer ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 111 _journal_page_last 113 _journal_paper_doi 10.1107/S0108270196010803 _journal_volume 53 _journal_year 1997 _chemical_formula_sum 'C10 H7 F3 O2' _chemical_formula_weight 216.16 _chemical_name_systematic ' ?' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_type_scat_source International_Tables_for_Xray_Crystallography _cell_angle_alpha 90.00 _cell_angle_beta 90.693(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 9.4512(7) _cell_length_b 9.8717(6) _cell_length_c 21.145(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 291 _cell_measurement_theta_max 41 _cell_measurement_theta_min 28 _cell_volume 1972.7(3) _computing_cell_refinement CAD-4 _computing_data_collection 'CAD-4 (Enraf-Nonius, 1977)' _computing_data_reduction 'PROCESS MolEN (Fair, 1990)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'CIF VAX MolEN' _computing_structure_refinement 'LSFM MolEN' _computing_structure_solution 'MULTAN (Main et al., 1980) (direct methods)' _diffrn_ambient_temperature 291 _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 2 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 4825 _diffrn_reflns_theta_max 70.0 _diffrn_reflns_theta_min 4.0 _diffrn_standards_decay_% '1.68 linear correction (MOLEN; Fair, 1990)' _diffrn_standards_interval_time 240 _diffrn_standards_number 4 _exptl_absorpt_coefficient_mu 1.193 _exptl_absorpt_correction_type none _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.46 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.21 _refine_diff_density_min -0.11 _refine_ls_abs_structure_details ; ? ; _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.175 _refine_ls_hydrogen_treatment ; H3, H13, HO2, HO4 refined isotropically; all other H atoms riding, U = 1.3 x U(bonding atom) ; _refine_ls_number_parameters 287 _refine_ls_number_reflns 2920 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.000 _refine_ls_R_factor_obs 0.056 _refine_ls_shift/esd_max 0.030 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'sigma (Killean & Lawrence, 1969)' _refine_ls_wR_factor_obs 0.082 _reflns_number_observed 2920 _reflns_number_total 3730 _reflns_observed_criterion >2.0\s(I) _cod_data_source_file sx1008.cif _cod_data_source_block BUR14 _cod_original_cell_volume 1972.7(4) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2005898 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.0966(8) 0.0654(6) 0.0843(7) 0.0129(6) -0.0092(7) 0.0067(6) F2 0.1066(9) 0.0819(7) 0.0686(7) -0.0287(6) -0.0142(6) -0.0034(6) F3 0.0863(7) 0.1074(9) 0.0621(6) -0.0194(7) 0.0082(6) 0.0159(6) F4 0.0735(7) 0.0756(7) 0.1580(10) 0.0093(6) 0.0227(8) 0.0017(9) F5 0.0618(6) 0.0979(9) 0.1600(10) -0.0073(6) 0.0277(7) 0.0252(9) F6 0.0900(9) 0.160(2) 0.1190(10) 0.0080(10) -0.0315(8) -0.0140(10) O1 0.0607(7) 0.0599(7) 0.0939(9) -0.0034(6) 0.0055(7) 0.0117(7) O2 0.0697(8) 0.0752(8) 0.0805(8) -0.0100(6) 0.0021(7) 0.0240(7) O3 0.0590(7) 0.0710(7) 0.0888(9) -0.0082(6) 0.0077(7) 0.0165(7) O4 0.0662(8) 0.0882(9) 0.1060(10) -0.0011(7) 0.0082(7) 0.0366(8) C1 0.0603(9) 0.0479(8) 0.0595(9) -0.0018(7) 0.0048(7) -0.0008(7) C2 0.0601(9) 0.0479(8) 0.0571(9) -0.0004(7) 0.0070(8) -0.0013(7) C3 0.0620(10) 0.0528(8) 0.0625(9) 0.0027(7) 0.0042(8) 0.0054(8) C4 0.0680(10) 0.0560(9) 0.0598(9) -0.0094(8) 0.0012(8) 0.0012(8) C5 0.0540(8) 0.0560(8) 0.0609(9) 0.0004(7) 0.0000(8) 0.0027(8) C6 0.0600(10) 0.0710(10) 0.0800(10) 0.0086(9) -0.0036(9) 0.0020(10) C7 0.0520(10) 0.107(2) 0.0940(10) 0.0000(10) 0.0000(10) 0.0000(10) C8 0.0690(10) 0.0930(10) 0.0870(10) -0.0230(10) 0.0020(10) 0.0090(10) C9 0.0760(10) 0.0650(10) 0.0860(10) -0.0144(9) -0.0050(10) 0.0110(10) C10 0.0559(9) 0.0590(9) 0.0810(10) 0.0012(8) -0.0001(9) 0.0046(9) C11 0.0603(9) 0.0546(9) 0.0690(10) 0.0000(8) 0.0095(8) 0.0035(8) C12 0.0586(9) 0.0613(9) 0.0660(10) -0.0064(8) 0.0089(8) -0.0005(8) C13 0.0585(9) 0.0610(9) 0.0630(10) -0.0062(8) 0.0090(8) -0.0016(8) C14 0.0630(10) 0.0730(10) 0.099(2) -0.0030(10) 0.0070(10) 0.0060(10) C15 0.0612(9) 0.0575(9) 0.0583(9) -0.0027(8) 0.0125(8) -0.0015(8) C16 0.0860(10) 0.0750(10) 0.0760(10) -0.0200(10) -0.0030(10) 0.0100(10) C17 0.0860(10) 0.0780(10) 0.101(2) -0.0240(10) 0.0050(10) 0.0070(10) C18 0.0880(10) 0.0680(10) 0.0970(10) -0.0030(10) 0.0280(10) 0.0140(10) C19 0.1020(10) 0.0770(10) 0.0670(10) 0.0130(10) 0.0130(10) 0.0140(10) C20 0.0770(10) 0.0650(10) 0.0680(10) 0.0042(9) 0.0030(10) -0.0031(9) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag F1 0.2947(1) -0.4260(1) 0.73639(6) 0.0822(4) Uani ? F2 0.3019(1) -0.2332(1) 0.78237(6) 0.0858(4) Uani ? F3 0.1131(1) -0.3485(1) 0.78419(5) 0.0852(4) Uani ? F4 0.8349(1) -0.0086(1) 0.54347(8) 0.1022(5) Uani ? F5 0.8964(1) 0.1893(2) 0.51766(9) 0.1062(5) Uani ? F6 0.8620(2) 0.1404(2) 0.61480(9) 0.1232(6) Uani ? O1 0.4038(1) -0.1699(1) 0.66865(7) 0.0715(4) Uani ? O2 0.2261(1) -0.0685(1) 0.61675(7) 0.0751(4) Uani ? O3 0.4271(1) 0.0738(1) 0.56229(8) 0.0729(4) Uani ? O4 0.6023(2) -0.0210(2) 0.61750(8) 0.0868(4) Uani ? C1 0.2762(2) -0.1557(2) 0.65649(8) 0.0559(4) Uani ? C2 0.1698(2) -0.2452(2) 0.68709(8) 0.0550(4) Uani ? C3 0.0427(2) -0.2612(2) 0.66046(9) 0.0590(5) Uani ? C4 0.2198(2) -0.3135(2) 0.74670(9) 0.0612(5) Uani ? C5 -0.0719(2) -0.3561(2) 0.67585(9) 0.0570(4) Uani ? C6 -0.2112(2) -0.3099(2) 0.6742(1) 0.0701(5) Uani ? C7 -0.3212(2) -0.3964(3) 0.6902(1) 0.0844(7) Uani ? C8 -0.2937(2) -0.5282(3) 0.7052(1) 0.0828(6) Uani ? C9 -0.1575(2) -0.5773(2) 0.7043(1) 0.0756(6) Uani ? C10 -0.0467(2) -0.4909(2) 0.6900(1) 0.0652(5) Uani ? C11 0.5531(2) 0.0645(2) 0.5768(1) 0.0612(5) Uani ? C12 0.6596(2) 0.1583(2) 0.54878(9) 0.0618(5) Uani ? C13 0.6088(2) 0.2675(2) 0.51857(9) 0.0607(5) Uani ? C14 0.8122(2) 0.1205(2) 0.5565(1) 0.0780(6) Uani ? C15 0.6759(2) 0.3885(2) 0.49210(9) 0.0589(4) Uani ? C16 0.7826(2) 0.4605(2) 0.5230(1) 0.0790(6) Uani ? C17 0.8334(3) 0.5795(2) 0.4974(1) 0.0883(7) Uani ? C18 0.7802(2) 0.6284(2) 0.4411(1) 0.0838(6) Uani ? C19 0.6752(3) 0.5597(2) 0.4107(1) 0.0821(7) Uani ? C20 0.6205(2) 0.4412(2) 0.4362(1) 0.0701(6) Uani ? H3 0.020(2) -0.208(2) 0.6269(9) 0.072(6) Uiso ? H13 0.507(2) 0.266(2) 0.512(1) 0.067(5) Uiso ? H_O4 0.533(3) -0.065(3) 0.631(1) 0.12(1) Uiso ? H_O2 0.288(3) -0.029(3) 0.602(1) 0.13(1) Uiso ? H6 -0.2310 -0.2191 0.6621 0.0840 Uiso calc H7 -0.4157 -0.3636 0.6908 0.1012 Uiso calc H8 -0.3693 -0.5867 0.7164 0.0992 Uiso calc H9 -0.1394 -0.6700 0.7135 0.0906 Uiso calc H10 0.0475 -0.5246 0.6898 0.0782 Uiso calc H16 0.8208 0.4276 0.5619 0.0946 Uiso calc H17 0.9061 0.6281 0.5190 0.1058 Uiso calc H18 0.8166 0.7098 0.4236 0.1004 Uiso calc H19 0.6387 0.5929 0.3716 0.0984 Uiso calc H20 0.5446 0.3959 0.4152 0.0840 Uiso calc loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 O2 H_O2 110(3) yes C11 O4 H_O4 106(3) yes O1 C1 O2 124.1(2) yes O1 C1 C2 120.2(2) yes O2 C1 C2 115.7(2) yes C1 C2 C3 119.8(2) yes C1 C2 C4 115.0(2) yes C3 C2 C4 125.1(2) yes C2 C3 C5 130.2(2) yes C2 C3 H3 118(2) yes C5 C3 H3 112(2) yes F1 C4 F2 106.3(2) yes F1 C4 F3 106.7(2) yes F1 C4 C2 113.5(2) yes F2 C4 F3 104.8(2) yes F2 C4 C2 112.5(2) yes F3 C4 C2 112.5(2) yes C3 C5 C6 119.0(2) yes C3 C5 C10 122.3(2) yes C6 C5 C10 118.7(2) yes C5 C6 C7 120.2(2) yes C5 C6 H6 119.9 ? C7 C6 H6 119.9 ? C6 C7 C8 120.1(2) yes C6 C7 H7 120.0 ? C8 C7 H7 120.0 ? C7 C8 C9 120.6(2) yes C7 C8 H8 119.7 ? C9 C8 H8 119.7 ? C8 C9 C10 119.7(2) yes C8 C9 H9 120.2 ? C10 C9 H9 120.2 ? C5 C10 C9 120.7(2) yes C5 C10 H10 119.7 ? C9 C10 H10 119.7 ? O3 C11 O4 123.8(2) yes O3 C11 C12 120.7(2) yes O4 C11 C12 115.5(2) yes C11 C12 C13 116.6(2) yes C11 C12 C14 117.1(2) yes C13 C12 C14 126.3(2) yes C12 C13 C15 133.1(2) yes C12 C13 H13 114.0(10) yes C15 C13 H13 113.0(10) yes F4 C14 F5 105.2(2) yes F4 C14 F6 106.2(2) yes F4 C14 C12 112.1(2) yes F5 C14 F6 106.8(2) yes F5 C14 C12 112.8(2) yes F6 C14 C12 113.2(2) yes C13 C15 C16 123.5(2) yes C13 C15 C20 118.0(2) yes C16 C15 C20 118.2(2) yes C15 C16 C17 120.3(2) yes C15 C16 H16 119.9 ? C17 C16 H16 119.8 ? C16 C17 C18 120.8(3) yes C16 C17 H17 119.6 ? C18 C17 H17 119.6 ? C17 C18 C19 119.5(2) yes C17 C18 H18 120.3 ? C19 C18 H18 120.3 ? C18 C19 C20 120.6(2) yes C18 C19 H19 119.7 ? C20 C19 H19 119.7 ? C15 C20 C19 120.5(2) yes C15 C20 H20 119.8 ? C19 C20 H20 119.7 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag F1 C4 1.336(2) yes F2 C4 1.336(2) yes F3 C4 1.335(2) yes F4 C14 1.323(3) yes F5 C14 1.335(3) yes F6 C14 1.329(3) yes O1 C1 1.239(3) yes O2 C1 1.289(3) yes O2 H_O2 0.77(5) no O3 C11 1.230(3) yes O4 C11 1.288(3) yes O4 H_O4 0.84(4) no C1 C2 1.492(3) yes C2 C3 1.330(3) yes C2 C4 1.501(3) yes C3 C5 1.471(3) yes C3 H3 0.91(3) yes C5 C6 1.393(3) yes C5 C10 1.384(3) yes C6 C7 1.391(4) yes C6 H6 0.95 ? C7 C8 1.363(4) yes C7 H7 0.95 ? C8 C9 1.375(4) yes C8 H8 0.95 ? C9 C10 1.387(3) yes C9 H9 0.95 ? C10 H10 0.95 ? C11 C12 1.495(3) yes C12 C13 1.339(3) yes C12 C14 1.497(3) yes C13 C15 1.467(3) yes C13 H13 0.97(3) yes C15 C16 1.390(3) yes C15 C20 1.388(3) yes C16 C17 1.382(3) yes C16 H16 0.95 ? C17 C18 1.374(4) yes C17 H17 0.95 ? C18 C19 1.357(4) yes C18 H18 0.95 ? C19 C20 1.391(4) yes C19 H19 0.95 ? C20 H20 0.95 ? 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 O1 C1 C2 C3 -158.35(0.18) O1 C1 C2 C4 20.34(0.24) O2 C1 C2 C3 19.98(0.25) O2 C1 C2 C4 -161.34(0.16) C1 C2 C3 C5 170.60(0.18) C4 C2 C3 C5 -7.94(0.32) C1 C2 C4 F1 -82.47(0.19) C1 C2 C4 F2 38.21(0.22) C1 C2 C4 F3 156.25(0.15) C3 C2 C4 F1 96.14(0.22) C3 C2 C4 F2 -143.19(0.18) C3 C2 C4 F3 -25.14(0.26) C2 C3 C5 C6 139.43(0.22) C2 C3 C5 C10 -42.69(0.31) C3 C5 C6 C7 -178.21(0.20) C10 C5 C6 C7 3.84(0.32) C3 C5 C10 C9 179.93(0.21) C6 C5 C10 C9 -2.19(0.31) C5 C6 C7 C8 -2.62(0.37) C6 C7 C8 C9 -0.35(0.39) C7 C8 C9 C10 2.00(0.38) C8 C9 C10 C5 -0.71(0.34) O3 C11 C12 C13 13.48(0.28) O3 C11 C12 C14 -165.86(0.19) O4 C11 C12 C13 -164.51(0.18) O4 C11 C12 C14 16.16(0.27) C11 C12 C14 F4 45.93(0.27) C11 C12 C14 F5 164.45(0.18) C11 C12 C14 F6 -74.15(0.26) C13 C12 C14 F4 -133.33(0.22) C13 C12 C14 F5 -14.81(0.32) C13 C12 C14 F6 106.59(0.26)