# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? loop_ _publ_author_name _publ_author_address _publ_author_footnote A.N.Other ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; S.O.ElseJ.Karban ; ? # Address 2 ; ; ? # Footnote 2 ; I.Cisarova '' '' T.Strasak '' '' L.C.Stastna '' '' J.Sykora '' '' _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_email karban@icpf.cas.cz _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' _publ_contact_author_name 'Jindrich Karban' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' _publ_section_title # Title of paper ; ? ; data_CRYSTALS_cif1 _database_code_depnum_ccdc_archive 'CCDC 832048' #TrackingRef '- comp_3.cif' _audit_creation_date 11-06-27 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e372_sykora_0m in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.2773(3) _cell_length_b 9.4898(6) _cell_length_c 10.1036(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 601.87(6) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H8 O4 # Dc = 1.59 Fooo = 304.00 Mu = 1.36 M = 144.13 # Found Formula = C6 H8 O4 # Dc = 1.59 FOOO = 304.00 Mu = 1.36 M = 144.13 _chemical_formula_sum 'C6 H8 O4' _chemical_formula_moiety 'C6 H8 O4' _chemical_compound_source ? _chemical_formula_weight 144.13 _cell_measurement_reflns_used 5095 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.28 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_max 0.59 _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.136 # Sheldrick geometric approximatio 0.95 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 5152 _reflns_number_total 829 _diffrn_reflns_av_R_equivalents 0.026 # Number of reflections with Friedels Law is 829 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 693 _diffrn_reflns_theta_min 2.945 _diffrn_reflns_theta_max 27.528 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.528 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.18 _refine_diff_density_max 0.17 _refine_ls_number_reflns 743 _refine_ls_number_restraints 0 _refine_ls_number_parameters 123 #_refine_ls_R_factor_ref 0.0264 _refine_ls_wR_factor_ref 0.0301 _refine_ls_goodness_of_fit_ref 1.0409 #_reflns_number_all 825 _refine_ls_R_factor_all 0.0292 _refine_ls_wR_factor_all 0.0332 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 743 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_gt 0.0301 _refine_ls_shift/su_max 0.000271 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.266 0.250 0.119 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.06061(17) 0.94540(12) 0.21629(9) 0.0209 1.0000 Uani . . . . . . O2 O -0.10759(16) 0.78967(11) 0.34686(11) 0.0216 1.0000 Uani . . . . . . O3 O -0.0664(2) 0.99372(13) 0.53107(11) 0.0308 1.0000 Uani . . . . . . O4 O 0.37791(18) 1.13465(12) 0.32885(11) 0.0261 1.0000 Uani . . . . . . C1 C -0.1260(2) 0.92699(16) 0.29253(15) 0.0192 1.0000 Uani . . . . . . C2 C -0.1365(2) 1.03849(16) 0.40164(16) 0.0239 1.0000 Uani . . . . . . C3 C 0.0665(3) 1.08803(15) 0.45630(14) 0.0234 1.0000 Uani . . . . . . C4 C 0.2694(2) 1.02694(16) 0.40080(14) 0.0192 1.0000 Uani . . . . . . C5 C 0.2216(2) 0.90175(17) 0.30926(15) 0.0205 1.0000 Uani . . . . . . C6 C 0.1175(3) 0.77377(17) 0.37582(17) 0.0257 1.0000 Uani . . . . . . H11 H -0.243(3) 0.932(2) 0.2342(19) 0.024(5) 1.0000 Uiso . . . . . . H21 H -0.252(4) 1.100(3) 0.400(2) 0.038(6) 1.0000 Uiso . . . . . . H31 H 0.079(4) 1.187(2) 0.492(2) 0.036(6) 1.0000 Uiso . . . . . . H41 H 0.362(3) 0.9961(19) 0.4725(18) 0.021(4) 1.0000 Uiso . . . . . . H51 H 0.346(4) 0.876(2) 0.256(2) 0.030(5) 1.0000 Uiso . . . . . . H61 H 0.142(4) 0.771(2) 0.470(2) 0.038(6) 1.0000 Uiso . . . . . . H62 H 0.166(4) 0.690(2) 0.343(2) 0.029(5) 1.0000 Uiso . . . . . . H1 H 0.301(4) 1.159(3) 0.267(3) 0.042(7) 1.0000 Uiso . . . . . . 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 O1 0.0202(5) 0.0299(5) 0.0125(4) 0.0005(4) -0.0019(4) -0.0030(4) O2 0.0233(5) 0.0198(5) 0.0217(5) 0.0031(4) -0.0045(4) -0.0036(4) O3 0.0357(6) 0.0373(6) 0.0193(5) -0.0054(5) 0.0105(5) -0.0063(6) O4 0.0190(5) 0.0313(6) 0.0280(6) 0.0060(4) -0.0060(5) -0.0076(5) C1 0.0154(6) 0.0223(6) 0.0200(6) 0.0031(6) -0.0039(5) -0.0017(5) C2 0.0181(6) 0.0236(7) 0.0300(7) -0.0007(6) 0.0059(6) 0.0037(6) C3 0.0265(7) 0.0219(6) 0.0219(6) -0.0058(5) 0.0030(6) -0.0021(6) C4 0.0169(6) 0.0223(7) 0.0185(6) 0.0005(6) -0.0043(5) -0.0009(6) C5 0.0159(6) 0.0253(7) 0.0203(6) -0.0054(6) -0.0016(6) 0.0042(6) C6 0.0291(8) 0.0177(6) 0.0303(8) -0.0009(6) -0.0108(7) 0.0027(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4906(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.4126(18) yes O1 . C5 . 1.4407(18) yes O2 . C1 . 1.4187(17) yes O2 . C6 . 1.4510(19) yes O3 . C2 . 1.444(2) yes O3 . C3 . 1.4380(19) yes O4 . C4 . 1.4272(18) yes O4 . H1 . 0.83(3) no C1 . C2 . 1.529(2) yes C1 . H11 . 0.94(2) no C2 . C3 . 1.466(2) yes C2 . H21 . 0.93(2) no C3 . C4 . 1.508(2) yes C3 . H31 . 1.01(2) no C4 . C5 . 1.535(2) yes C4 . H41 . 0.975(19) no C5 . C6 . 1.534(2) yes C5 . H51 . 0.98(2) no C6 . H61 . 0.97(3) no C6 . H62 . 0.91(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 100.99(10) yes C1 . O2 . C6 . 104.64(11) yes C2 . O3 . C3 . 61.17(10) yes C4 . O4 . H1 . 108.1(18) no O2 . C1 . O1 . 104.90(12) yes O2 . C1 . C2 . 111.11(12) yes O1 . C1 . C2 . 110.08(12) yes O2 . C1 . H11 . 110.8(13) no O1 . C1 . H11 . 107.3(12) no C2 . C1 . H11 . 112.3(13) no C1 . C2 . O3 . 115.86(13) yes C1 . C2 . C3 . 117.11(13) yes O3 . C2 . C3 . 59.22(10) yes C1 . C2 . H21 . 117.1(14) no O3 . C2 . H21 . 115.9(14) no C3 . C2 . H21 . 118.9(14) no C2 . C3 . O3 . 59.61(10) yes C2 . C3 . C4 . 118.09(11) yes O3 . C3 . C4 . 116.51(12) yes C2 . C3 . H31 . 120.1(14) no O3 . C3 . H31 . 115.8(12) no C4 . C3 . H31 . 115.1(14) no C3 . C4 . O4 . 108.49(12) yes C3 . C4 . C5 . 110.88(11) yes O4 . C4 . C5 . 109.92(12) yes C3 . C4 . H41 . 110.2(11) no O4 . C4 . H41 . 108.0(11) no C5 . C4 . H41 . 109.4(11) no C4 . C5 . O1 . 107.91(12) yes C4 . C5 . C6 . 115.58(12) yes O1 . C5 . C6 . 102.39(12) yes C4 . C5 . H51 . 111.4(13) no O1 . C5 . H51 . 105.8(13) no C6 . C5 . H51 . 112.8(13) no C5 . C6 . O2 . 104.13(12) yes C5 . C6 . H61 . 113.0(14) no O2 . C6 . H61 . 110.8(14) no C5 . C6 . H62 . 112.7(14) no O2 . C6 . H62 . 110.0(14) no H61 . C6 . H62 . 106(2) no # Attachment '- comp_4.cif' data_CRYSTALS_cif2 _database_code_depnum_ccdc_archive 'CCDC 832049' #TrackingRef '- comp_4.cif' _audit_creation_date 11-06-27 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e338_1f_sykora_0m in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.7114(3) _cell_length_b 10.2593(4) _cell_length_c 17.4506(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1201.55(9) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C6 H8 O4 # Dc = 1.59 Fooo = 608.00 Mu = 1.36 M = 288.25 # Found Formula = C6 H8 O4 # Dc = 1.59 FOOO = 608.00 Mu = 1.36 M = 288.25 _chemical_formula_sum 'C6 H8 O4' _chemical_formula_moiety 'C6 H8 O4' _chemical_compound_source ? _chemical_formula_weight 144.13 _cell_measurement_reflns_used 8981 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.28 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_max 0.60 _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.136 # Sheldrick geometric approximatio 0.94 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 9035 _reflns_number_total 1608 _diffrn_reflns_av_R_equivalents 0.020 # Number of reflections with Friedels Law is 1608 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1379 _diffrn_reflns_theta_min 2.303 _diffrn_reflns_theta_max 27.494 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.494 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.26 _refine_ls_number_reflns 1383 _refine_ls_number_restraints 0 _refine_ls_number_parameters 245 #_refine_ls_R_factor_ref 0.0253 _refine_ls_wR_factor_ref 0.0305 _refine_ls_goodness_of_fit_ref 1.0396 #_reflns_number_all 1599 _refine_ls_R_factor_all 0.0287 _refine_ls_wR_factor_all 0.0355 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 1383 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_gt 0.0305 _refine_ls_shift/su_max 0.000383 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.246 0.246 0.938E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.84702(18) 0.77023(11) 0.30715(6) 0.0190 1.0000 Uani . . . . . . O2 O 0.79730(19) 0.72735(12) 0.43269(7) 0.0232 1.0000 Uani . . . . . . O3 O 1.24401(18) 0.71567(12) 0.31573(7) 0.0243 1.0000 Uani . . . . . . O4 O 0.9241(2) 0.42017(11) 0.30650(8) 0.0219 1.0000 Uani . . . . . . O11 O 1.15907(17) 0.38379(12) 0.56136(6) 0.0191 1.0000 Uani . . . . . . O12 O 1.11285(18) 0.44494(11) 0.68437(7) 0.0206 1.0000 Uani . . . . . . O13 O 0.95833(18) 0.15107(11) 0.58360(7) 0.0195 1.0000 Uani . . . . . . O14 O 0.62484(18) 0.43580(13) 0.55795(8) 0.0231 1.0000 Uani . . . . . . C1 C 0.9316(3) 0.78694(16) 0.38082(9) 0.0190 1.0000 Uani . . . . . . C2 C 1.1284(3) 0.71540(17) 0.38538(9) 0.0194 1.0000 Uani . . . . . . C3 C 1.1464(2) 0.59628(15) 0.33887(9) 0.0187 1.0000 Uani . . . . . . C4 C 0.9707(2) 0.55271(15) 0.28994(8) 0.0161 1.0000 Uani . . . . . . C5 C 0.7877(2) 0.63439(15) 0.30865(9) 0.0153 1.0000 Uani . . . . . . C6 C 0.7135(3) 0.61792(17) 0.39133(9) 0.0185 1.0000 Uani . . . . . . C11 C 1.1593(2) 0.33619(16) 0.63740(9) 0.0178 1.0000 Uani . . . . . . C12 C 0.9969(3) 0.23548(15) 0.64820(9) 0.0171 1.0000 Uani . . . . . . C13 C 0.8171(2) 0.25298(15) 0.60159(9) 0.0165 1.0000 Uani . . . . . . C14 C 0.8062(2) 0.36698(15) 0.54575(9) 0.0160 1.0000 Uani . . . . . . C15 C 0.9794(2) 0.46051(16) 0.55950(9) 0.0161 1.0000 Uani . . . . . . C16 C 0.9768(2) 0.52324(15) 0.63944(9) 0.0174 1.0000 Uani . . . . . . H11 H 0.946(3) 0.880(2) 0.3911(12) 0.023(5) 1.0000 Uiso . . . . . . H21 H 1.201(4) 0.728(2) 0.4293(14) 0.032(6) 1.0000 Uiso . . . . . . H31 H 1.235(4) 0.525(2) 0.3549(12) 0.027(6) 1.0000 Uiso . . . . . . H41 H 1.003(3) 0.565(2) 0.2354(12) 0.019(5) 1.0000 Uiso . . . . . . H51 H 0.686(3) 0.622(2) 0.2709(11) 0.019(5) 1.0000 Uiso . . . . . . H61 H 0.760(3) 0.536(2) 0.4133(12) 0.025(5) 1.0000 Uiso . . . . . . H62 H 0.572(4) 0.625(2) 0.3923(13) 0.025(5) 1.0000 Uiso . . . . . . H111 H 1.289(3) 0.2998(19) 0.6488(11) 0.016(5) 1.0000 Uiso . . . . . . H121 H 0.990(3) 0.194(2) 0.6974(12) 0.020(5) 1.0000 Uiso . . . . . . H131 H 0.687(3) 0.221(2) 0.6231(12) 0.022(5) 1.0000 Uiso . . . . . . H141 H 0.809(3) 0.3338(19) 0.4933(10) 0.011(4) 1.0000 Uiso . . . . . . H151 H 0.990(3) 0.524(2) 0.5184(12) 0.018(5) 1.0000 Uiso . . . . . . H161 H 1.027(3) 0.609(2) 0.6379(11) 0.014(5) 1.0000 Uiso . . . . . . H162 H 0.848(4) 0.519(2) 0.6617(12) 0.020(5) 1.0000 Uiso . . . . . . H1 H 0.974(5) 0.374(3) 0.2739(18) 0.060(10) 1.0000 Uiso . . . . . . H2 H 0.547(6) 0.404(4) 0.529(2) 0.085(13) 1.0000 Uiso . . . . . . 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 O1 0.0256(6) 0.0121(5) 0.0194(5) 0.0022(4) -0.0025(5) 0.0005(5) O2 0.0255(6) 0.0252(6) 0.0189(5) -0.0070(4) 0.0076(5) -0.0059(5) O3 0.0212(6) 0.0233(6) 0.0282(6) -0.0052(5) 0.0072(5) -0.0082(5) O4 0.0271(6) 0.0108(5) 0.0276(6) -0.0028(4) 0.0034(5) -0.0023(5) O11 0.0148(5) 0.0218(5) 0.0208(5) -0.0001(5) 0.0031(4) 0.0010(5) O12 0.0242(6) 0.0165(5) 0.0212(6) -0.0038(4) -0.0092(5) 0.0042(5) O13 0.0224(6) 0.0132(5) 0.0229(5) -0.0042(4) 0.0013(5) 0.0023(5) O14 0.0161(5) 0.0233(6) 0.0299(6) -0.0058(5) -0.0083(5) 0.0051(5) C1 0.0241(8) 0.0140(7) 0.0189(7) -0.0045(5) 0.0031(6) -0.0034(7) C2 0.0189(7) 0.0217(8) 0.0176(7) -0.0029(6) -0.0011(6) -0.0064(7) C3 0.0153(7) 0.0164(7) 0.0244(8) -0.0010(6) -0.0005(6) -0.0018(6) C4 0.0207(7) 0.0121(6) 0.0156(7) -0.0013(5) 0.0009(6) -0.0019(6) C5 0.0179(7) 0.0126(7) 0.0155(6) 0.0016(5) -0.0038(6) -0.0015(6) C6 0.0172(7) 0.0191(7) 0.0191(7) -0.0002(6) 0.0012(6) -0.0017(6) C11 0.0159(7) 0.0172(7) 0.0201(7) -0.0009(5) -0.0035(6) 0.0031(6) C12 0.0227(7) 0.0123(7) 0.0164(7) 0.0002(5) 0.0013(6) 0.0025(6) C13 0.0160(7) 0.0129(7) 0.0204(7) -0.0021(6) 0.0023(6) -0.0013(6) C14 0.0159(7) 0.0150(7) 0.0171(7) -0.0017(5) -0.0024(5) 0.0003(6) C15 0.0155(6) 0.0160(6) 0.0168(7) 0.0029(6) -0.0009(6) -0.0007(6) C16 0.0166(7) 0.0128(7) 0.0228(8) -0.0013(6) -0.0034(6) 0.0006(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2641(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.4157(19) yes O1 . C5 . 1.4497(18) yes O2 . C1 . 1.416(2) yes O2 . C6 . 1.448(2) yes O3 . C2 . 1.4419(19) yes O3 . C3 . 1.4465(19) yes O4 . C4 . 1.4249(19) yes O4 . H1 . 0.81(3) no O11 . C11 . 1.4139(18) yes O11 . C15 . 1.4404(19) yes O12 . C11 . 1.4190(19) yes O12 . C16 . 1.4468(19) yes O13 . C12 . 1.4449(18) yes O13 . C13 . 1.4458(19) yes O14 . C14 . 1.4234(19) yes O14 . H2 . 0.80(4) no C1 . C2 . 1.513(2) yes C1 . H11 . 0.98(2) no C2 . C3 . 1.472(2) yes C2 . H21 . 0.92(2) no C3 . C4 . 1.523(2) yes C3 . H31 . 0.99(2) no C4 . C5 . 1.523(2) yes C4 . H41 . 0.98(2) no C5 . C6 . 1.536(2) yes C5 . H51 . 0.96(2) no C6 . H61 . 0.98(2) no C6 . H62 . 0.95(2) no C11 . C12 . 1.513(2) yes C11 . H111 . 0.97(2) no C12 . C13 . 1.466(2) yes C12 . H121 . 0.96(2) no C13 . C14 . 1.524(2) yes C13 . H131 . 1.00(2) no C14 . C15 . 1.526(2) yes C14 . H141 . 0.977(18) no C15 . C16 . 1.536(2) yes C15 . H151 . 0.97(2) no C16 . H161 . 0.95(2) no C16 . H162 . 0.95(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 102.13(11) yes C1 . O2 . C6 . 105.27(11) yes C2 . O3 . C3 . 61.27(10) yes C4 . O4 . H1 . 109(2) no C11 . O11 . C15 . 102.16(11) yes C11 . O12 . C16 . 105.19(11) yes C12 . O13 . C13 . 60.97(10) yes C14 . O14 . H2 . 105(3) no O2 . C1 . O1 . 105.84(13) yes O2 . C1 . C2 . 108.21(14) yes O1 . C1 . C2 . 109.82(12) yes O2 . C1 . H11 . 111.5(13) no O1 . C1 . H11 . 108.9(13) no C2 . C1 . H11 . 112.3(13) no C1 . C2 . O3 . 115.11(13) yes C1 . C2 . C3 . 116.44(14) yes O3 . C2 . C3 . 59.52(10) yes C1 . C2 . H21 . 116.0(15) no O3 . C2 . H21 . 114.6(16) no C3 . C2 . H21 . 122.4(15) no C2 . C3 . O3 . 59.21(10) yes C2 . C3 . C4 . 119.30(14) yes O3 . C3 . C4 . 116.27(14) yes C2 . C3 . H31 . 120.8(13) no O3 . C3 . H31 . 116.0(14) no C4 . C3 . H31 . 114.0(13) no C3 . C4 . O4 . 109.65(13) yes C3 . C4 . C5 . 110.05(13) yes O4 . C4 . C5 . 107.73(12) yes C3 . C4 . H41 . 109.4(13) no O4 . C4 . H41 . 111.5(13) no C5 . C4 . H41 . 108.5(13) no C4 . C5 . O1 . 107.66(12) yes C4 . C5 . C6 . 113.74(13) yes O1 . C5 . C6 . 102.23(12) yes C4 . C5 . H51 . 110.6(12) no O1 . C5 . H51 . 108.4(13) no C6 . C5 . H51 . 113.6(12) no C5 . C6 . O2 . 104.89(13) yes C5 . C6 . H61 . 111.0(13) no O2 . C6 . H61 . 110.5(13) no C5 . C6 . H62 . 109.3(14) no O2 . C6 . H62 . 108.7(14) no H61 . C6 . H62 . 112(2) no O12 . C11 . O11 . 105.68(12) yes O12 . C11 . C12 . 107.86(13) yes O11 . C11 . C12 . 110.60(12) yes O12 . C11 . H111 . 112.5(12) no O11 . C11 . H111 . 109.1(12) no C12 . C11 . H111 . 111.0(12) no C11 . C12 . O13 . 116.17(13) yes C11 . C12 . C13 . 116.10(13) yes O13 . C12 . C13 . 59.55(10) yes C11 . C12 . H121 . 116.7(13) no O13 . C12 . H121 . 115.1(13) no C13 . C12 . H121 . 120.6(13) no C12 . C13 . O13 . 59.49(10) yes C12 . C13 . C14 . 119.20(14) yes O13 . C13 . C14 . 116.57(13) yes C12 . C13 . H131 . 117.9(12) no O13 . C13 . H131 . 114.5(13) no C14 . C13 . H131 . 116.6(13) no C13 . C14 . O14 . 109.02(13) yes C13 . C14 . C15 . 110.21(12) yes O14 . C14 . C15 . 108.42(12) yes C13 . C14 . H141 . 109.3(11) no O14 . C14 . H141 . 109.3(12) no C15 . C14 . H141 . 110.6(12) no C14 . C15 . O11 . 107.31(12) yes C14 . C15 . C16 . 113.44(13) yes O11 . C15 . C16 . 102.58(12) yes C14 . C15 . H151 . 111.2(13) no O11 . C15 . H151 . 108.7(13) no C16 . C15 . H151 . 113.0(12) no C15 . C16 . O12 . 104.62(12) yes C15 . C16 . H161 . 111.2(12) no O12 . C16 . H161 . 108.0(12) no C15 . C16 . H162 . 111.2(12) no O12 . C16 . H162 . 109.1(12) no H161 . C16 . H162 . 112.4(17) no # Attachment '- comp_6.cif' data_CRYSTALS_cif3 _database_code_depnum_ccdc_archive 'CCDC 832050' #TrackingRef '- comp_6.cif' _audit_creation_date 11-06-27 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e338_f2_sykora_0ma in P2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.0789(2) _cell_length_b 11.0036(5) _cell_length_c 10.9164(5) _cell_angle_alpha 90 _cell_angle_beta 90.128(2) _cell_angle_gamma 90 _cell_volume 610.07(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H8 O4 # Dc = 1.57 Fooo = 304.00 Mu = 1.34 M = 288.25 # Found Formula = C6 H8 O4 # Dc = 1.57 FOOO = 304.00 Mu = 1.34 M = 288.25 _chemical_formula_sum 'C6 H8 O4' _chemical_formula_moiety 'C6 H8 O4' _chemical_compound_source ? _chemical_formula_weight 144.13 _cell_measurement_reflns_used 8256 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.27 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.134 # Sheldrick geometric approximatio 0.95 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 8294 _reflns_number_total 1484 _diffrn_reflns_av_R_equivalents 0.014 # Number of reflections with Friedels Law is 1484 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1410 _diffrn_reflns_theta_min 1.866 _diffrn_reflns_theta_max 27.557 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.557 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.13 _refine_diff_density_max 0.18 _refine_ls_number_reflns 1346 _refine_ls_number_restraints 1 _refine_ls_number_parameters 245 #_refine_ls_R_factor_ref 0.0214 _refine_ls_wR_factor_ref 0.0252 _refine_ls_goodness_of_fit_ref 1.1423 #_reflns_number_all 1479 _refine_ls_R_factor_all 0.0235 _refine_ls_wR_factor_all 0.0283 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 1346 _refine_ls_R_factor_gt 0.0214 _refine_ls_wR_factor_gt 0.0252 _refine_ls_shift/su_max 0.000293 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.158 0.123 0.493E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.0217(2) 0.97620(12) -0.01307(10) 0.0190 1.0000 Uani . . . . . . O2 O 0.4101(2) 1.01605(12) 0.08164(10) 0.0240 1.0000 Uani . . . . . . O3 O 0.3234(2) 0.84328(13) -0.20083(9) 0.0218 1.0000 Uani . . . . . . O4 O 0.3525(3) 0.75253(14) 0.12451(11) 0.0298 1.0000 Uani . . . . . . O11 O 0.4974(2) 0.45112(12) 0.50492(10) 0.0190 1.0000 Uani . . . . . . O12 O 0.1146(2) 0.50440(14) 0.59663(10) 0.0257 1.0000 Uani . . . . . . O13 O 0.1767(2) 0.33807(12) 0.31023(10) 0.0186 1.0000 Uani . . . . . . O14 O 0.1217(3) 0.66783(12) 0.37798(12) 0.0275 1.0000 Uani . . . . . . C1 C 0.2961(3) 0.98256(15) -0.03263(14) 0.0181 1.0000 Uani . . . . . . C2 C 0.3995(3) 0.85906(15) -0.07582(13) 0.0169 1.0000 Uani . . . . . . C3 C 0.2792(3) 0.75641(15) -0.00341(15) 0.0226 1.0000 Uani . . . . . . C4 C 0.0851(3) 0.78599(16) 0.09199(15) 0.0231 1.0000 Uani . . . . . . C5 C 0.0117(3) 0.91851(16) 0.10669(13) 0.0188 1.0000 Uani . . . . . . C6 C 0.2173(3) 0.99130(18) 0.17569(14) 0.0229 1.0000 Uani . . . . . . C11 C 0.2268(3) 0.42290(16) 0.51031(13) 0.0182 1.0000 Uani . . . . . . C12 C 0.0994(3) 0.43989(16) 0.38432(13) 0.0170 1.0000 Uani . . . . . . C13 C 0.1935(3) 0.55459(16) 0.32213(15) 0.0208 1.0000 Uani . . . . . . C14 C 0.3947(3) 0.62876(15) 0.38365(15) 0.0222 1.0000 Uani . . . . . . C15 C 0.4917(3) 0.58299(16) 0.50707(16) 0.0207 1.0000 Uani . . . . . . C16 C 0.2933(3) 0.60523(17) 0.60916(15) 0.0230 1.0000 Uani . . . . . . H11 H 0.333(4) 1.046(2) -0.0917(19) 0.020(5) 1.0000 Uiso . . . . . . H21 H 0.585(4) 0.861(2) -0.0702(18) 0.019(5) 1.0000 Uiso . . . . . . H31 H 0.279(4) 0.679(2) -0.041(2) 0.025(5) 1.0000 Uiso . . . . . . H41 H -0.041(5) 0.726(2) 0.115(2) 0.034(6) 1.0000 Uiso . . . . . . H51 H -0.169(4) 0.927(2) 0.138(2) 0.027(5) 1.0000 Uiso . . . . . . H61 H 0.153(4) 1.067(2) 0.205(2) 0.024(5) 1.0000 Uiso . . . . . . H62 H 0.307(4) 0.944(2) 0.242(2) 0.027(5) 1.0000 Uiso . . . . . . H111 H 0.204(4) 0.338(2) 0.536(2) 0.026(5) 1.0000 Uiso . . . . . . H121 H -0.085(4) 0.441(2) 0.3937(19) 0.023(5) 1.0000 Uiso . . . . . . H131 H 0.193(4) 0.552(2) 0.235(2) 0.024(5) 1.0000 Uiso . . . . . . H141 H 0.513(4) 0.676(2) 0.336(2) 0.028(5) 1.0000 Uiso . . . . . . H151 H 0.666(4) 0.612(2) 0.528(2) 0.026(5) 1.0000 Uiso . . . . . . H161 H 0.372(4) 0.601(2) 0.690(2) 0.022(5) 1.0000 Uiso . . . . . . H162 H 0.199(4) 0.683(2) 0.599(2) 0.024(5) 1.0000 Uiso . . . . . . H1 H 0.461(5) 0.841(2) -0.243(2) 0.029(5) 1.0000 Uiso . . . . . . H2 H 0.054(5) 0.325(2) 0.265(2) 0.037(6) 1.0000 Uiso . . . . . . 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 O1 0.0171(5) 0.0211(5) 0.0187(5) 0.0030(4) 0.0006(4) 0.0052(4) O2 0.0205(5) 0.0307(6) 0.0209(5) -0.0090(5) 0.0052(4) -0.0096(5) O3 0.0166(5) 0.0360(6) 0.0129(5) -0.0044(5) 0.0003(4) 0.0009(5) O4 0.0341(6) 0.0333(7) 0.0220(6) 0.0104(5) -0.0020(5) 0.0111(5) O11 0.0156(4) 0.0197(5) 0.0216(5) -0.0003(4) -0.0014(4) 0.0029(4) O12 0.0220(5) 0.0375(7) 0.0178(5) -0.0087(5) 0.0056(4) -0.0015(5) O13 0.0171(5) 0.0206(5) 0.0182(5) -0.0054(4) 0.0009(4) -0.0011(4) O14 0.0330(7) 0.0212(6) 0.0281(6) -0.0029(5) -0.0087(5) 0.0092(5) C1 0.0195(6) 0.0177(7) 0.0171(6) 0.0010(6) 0.0022(5) -0.0027(5) C2 0.0134(6) 0.0236(8) 0.0137(6) -0.0024(5) -0.0005(5) 0.0023(5) C3 0.0296(8) 0.0167(7) 0.0213(7) 0.0016(6) -0.0019(6) 0.0048(6) C4 0.0246(7) 0.0220(8) 0.0226(8) 0.0051(6) 0.0012(6) -0.0054(6) C5 0.0153(6) 0.0250(8) 0.0162(7) 0.0004(6) 0.0028(5) -0.0004(5) C6 0.0210(7) 0.0288(8) 0.0191(6) -0.0069(6) 0.0051(6) -0.0033(6) C11 0.0191(6) 0.0209(7) 0.0145(6) -0.0002(5) 0.0033(5) -0.0013(6) C12 0.0132(6) 0.0210(7) 0.0169(6) -0.0040(6) 0.0013(5) 0.0009(5) C13 0.0244(7) 0.0207(7) 0.0171(7) -0.0002(6) -0.0017(6) 0.0042(6) C14 0.0254(7) 0.0184(7) 0.0227(8) 0.0019(6) 0.0012(6) -0.0009(6) C15 0.0175(6) 0.0208(7) 0.0239(7) -0.0027(6) -0.0027(5) 0.0008(6) C16 0.0235(7) 0.0267(8) 0.0186(7) -0.0067(6) -0.0037(6) 0.0046(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4493(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.4119(17) yes O1 . C5 . 1.4543(17) yes O2 . C1 . 1.4226(18) yes O2 . C6 . 1.4463(18) yes O3 . C2 . 1.4280(16) yes O3 . H1 . 0.84(2) no O4 . C3 . 1.445(2) yes O4 . C4 . 1.451(2) yes O11 . C11 . 1.4108(18) yes O11 . C15 . 1.4515(19) yes O12 . C11 . 1.4208(19) yes O12 . C16 . 1.440(2) yes O13 . C12 . 1.4370(18) yes O13 . H2 . 0.81(3) no O14 . C13 . 1.4347(19) yes O14 . C14 . 1.453(2) yes C1 . C2 . 1.532(2) yes C1 . H11 . 0.97(2) no C2 . C3 . 1.509(2) yes C2 . H21 . 0.95(2) no C3 . C4 . 1.472(2) yes C3 . H31 . 0.95(2) no C4 . C5 . 1.514(2) yes C4 . H41 . 0.95(3) no C5 . C6 . 1.515(2) yes C5 . H51 . 0.98(2) no C6 . H61 . 0.95(2) no C6 . H62 . 1.00(2) no C11 . C12 . 1.530(2) yes C11 . H111 . 0.99(3) no C12 . C13 . 1.511(2) yes C12 . H121 . 0.94(2) no C13 . C14 . 1.469(2) yes C13 . H131 . 0.95(2) no C14 . C15 . 1.519(2) yes C14 . H141 . 0.95(2) no C15 . C16 . 1.524(2) yes C15 . H151 . 0.97(2) no C16 . H161 . 0.97(2) no C16 . H162 . 0.99(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 101.19(11) yes C1 . O2 . C6 . 107.38(11) yes C2 . O3 . H1 . 107.4(16) no C3 . O4 . C4 . 61.12(10) yes C11 . O11 . C15 . 101.52(11) yes C11 . O12 . C16 . 107.21(12) yes C12 . O13 . H2 . 105.5(19) no C13 . O14 . C14 . 61.15(10) yes O2 . C1 . O1 . 106.27(12) yes O2 . C1 . C2 . 111.14(12) yes O1 . C1 . C2 . 109.98(12) yes O2 . C1 . H11 . 108.5(12) no O1 . C1 . H11 . 109.2(12) no C2 . C1 . H11 . 111.6(13) no C1 . C2 . O3 . 108.05(12) yes C1 . C2 . C3 . 111.32(12) yes O3 . C2 . C3 . 107.51(13) yes C1 . C2 . H21 . 107.6(13) no O3 . C2 . H21 . 109.4(12) no C3 . C2 . H21 . 112.9(13) no C2 . C3 . O4 . 115.14(14) yes C2 . C3 . C4 . 118.54(14) yes O4 . C3 . C4 . 59.63(11) yes C2 . C3 . H31 . 116.7(13) no O4 . C3 . H31 . 112.9(13) no C4 . C3 . H31 . 120.3(13) no C3 . C4 . O4 . 59.25(10) yes C3 . C4 . C5 . 116.96(13) yes O4 . C4 . C5 . 116.69(14) yes C3 . C4 . H41 . 119.1(15) no O4 . C4 . H41 . 113.0(15) no C5 . C4 . H41 . 118.1(15) no C4 . C5 . O1 . 108.43(12) yes C4 . C5 . C6 . 113.10(14) yes O1 . C5 . C6 . 100.99(12) yes C4 . C5 . H51 . 111.3(14) no O1 . C5 . H51 . 107.4(13) no C6 . C5 . H51 . 114.8(13) no C5 . C6 . O2 . 102.33(12) yes C5 . C6 . H61 . 113.2(13) no O2 . C6 . H61 . 108.0(14) no C5 . C6 . H62 . 113.6(13) no O2 . C6 . H62 . 107.6(12) no H61 . C6 . H62 . 111.4(19) no O12 . C11 . O11 . 106.31(12) yes O12 . C11 . C12 . 110.47(13) yes O11 . C11 . C12 . 110.22(12) yes O12 . C11 . H111 . 111.3(13) no O11 . C11 . H111 . 109.7(12) no C12 . C11 . H111 . 108.9(13) no C11 . C12 . O13 . 107.17(12) yes C11 . C12 . C13 . 111.86(12) yes O13 . C12 . C13 . 108.13(11) yes C11 . C12 . H121 . 108.8(13) no O13 . C12 . H121 . 109.9(14) no C13 . C12 . H121 . 111.0(14) no C12 . C13 . O14 . 116.97(13) yes C12 . C13 . C14 . 118.62(14) yes O14 . C13 . C14 . 60.04(10) yes C12 . C13 . H131 . 114.9(14) no O14 . C13 . H131 . 116.8(14) no C14 . C13 . H131 . 118.5(13) no C13 . C14 . O14 . 58.81(10) yes C13 . C14 . C15 . 116.42(14) yes O14 . C14 . C15 . 116.32(13) yes C13 . C14 . H141 . 119.8(14) no O14 . C14 . H141 . 114.9(14) no C15 . C14 . H141 . 117.3(14) no C14 . C15 . O11 . 108.88(13) yes C14 . C15 . C16 . 112.44(13) yes O11 . C15 . C16 . 100.71(13) yes C14 . C15 . H151 . 113.3(13) no O11 . C15 . H151 . 108.2(14) no C16 . C15 . H151 . 112.3(13) no C15 . C16 . O12 . 102.97(13) yes C15 . C16 . H161 . 112.7(12) no O12 . C16 . H161 . 107.9(13) no C15 . C16 . H162 . 112.0(13) no O12 . C16 . H162 . 110.6(13) no H161 . C16 . H162 . 110.3(18) no # Attachment '- comp_8.cif' data_CRYSTALS_cif4 _database_code_depnum_ccdc_archive 'CCDC 832051' #TrackingRef '- comp_8.cif' _audit_creation_date 11-06-27 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e999_sykora_0m in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.6736(2) _cell_length_b 9.5781(4) _cell_length_c 10.7239(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 582.76(4) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H8 O4 # Dc = 1.64 Fooo = 304.00 Mu = 1.40 M = 144.13 # Found Formula = C6 H8 O4 # Dc = 1.64 FOOO = 304.00 Mu = 1.40 M = 144.13 _chemical_formula_sum 'C6 H8 O4' _chemical_formula_moiety 'C6 H8 O4' _chemical_compound_source ? _chemical_formula_weight 144.13 _cell_measurement_reflns_used 4835 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.37 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_max 0.52 _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.140 # Sheldrick geometric approximatio 0.95 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.95 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 4869 _reflns_number_total 805 _diffrn_reflns_av_R_equivalents 0.014 # Number of reflections with Friedels Law is 805 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 670 _diffrn_reflns_theta_min 2.851 _diffrn_reflns_theta_max 27.513 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.513 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.17 _refine_diff_density_max 0.23 _refine_ls_number_reflns 719 _refine_ls_number_restraints 0 _refine_ls_number_parameters 123 #_refine_ls_R_factor_ref 0.0245 _refine_ls_wR_factor_ref 0.0291 _refine_ls_goodness_of_fit_ref 1.1434 #_reflns_number_all 802 _refine_ls_R_factor_all 0.0276 _refine_ls_wR_factor_all 0.0348 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 719 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_gt 0.0291 _refine_ls_shift/su_max 0.000242 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.182 0.138 0.532E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.9998(2) 0.91615(13) 0.21790(10) 0.0196 1.0000 Uani . . . . . . O2 O 0.7246(2) 0.79150(12) 0.32055(10) 0.0207 1.0000 Uani . . . . . . O3 O 0.6348(2) 1.03302(13) 0.43662(10) 0.0184 1.0000 Uani . . . . . . O4 O 1.1332(2) 1.03740(15) 0.53412(11) 0.0236 1.0000 Uani . . . . . . C1 C 0.7532(3) 0.90796(17) 0.24101(14) 0.0189 1.0000 Uani . . . . . . C2 C 0.6707(3) 1.04283(18) 0.30348(14) 0.0186 1.0000 Uani . . . . . . C3 C 0.8354(3) 1.11051(17) 0.39014(14) 0.0183 1.0000 Uani . . . . . . C4 C 1.0763(3) 1.04609(17) 0.40532(14) 0.0166 1.0000 Uani . . . . . . C5 C 1.0918(3) 0.90221(16) 0.34245(14) 0.0160 1.0000 Uani . . . . . . C6 C 0.9327(3) 0.78928(17) 0.39860(15) 0.0193 1.0000 Uani . . . . . . H11 H 0.676(3) 0.8911(19) 0.1621(17) 0.014(4) 1.0000 Uiso . . . . . . H21 H 0.546(4) 1.096(2) 0.258(2) 0.030(6) 1.0000 Uiso . . . . . . H31 H 0.824(4) 1.207(2) 0.4052(17) 0.017(5) 1.0000 Uiso . . . . . . H41 H 1.182(4) 1.107(2) 0.3605(17) 0.018(5) 1.0000 Uiso . . . . . . H51 H 1.248(4) 0.870(2) 0.3394(17) 0.017(4) 1.0000 Uiso . . . . . . H61 H 0.893(4) 0.808(2) 0.4860(19) 0.023(5) 1.0000 Uiso . . . . . . H62 H 1.002(4) 0.696(2) 0.3900(17) 0.019(5) 1.0000 Uiso . . . . . . H1 H 1.270(6) 1.042(3) 0.541(2) 0.044(7) 1.0000 Uiso . . . . . . 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 O1 0.0156(6) 0.0291(6) 0.0143(5) 0.0005(4) 0.0026(4) 0.0033(5) O2 0.0168(5) 0.0211(6) 0.0243(5) 0.0005(4) -0.0033(5) -0.0037(5) O3 0.0126(5) 0.0257(6) 0.0169(5) -0.0005(4) 0.0032(4) -0.0005(5) O4 0.0155(6) 0.0339(7) 0.0213(6) -0.0058(5) -0.0030(4) 0.0000(6) C1 0.0155(7) 0.0255(8) 0.0156(6) 0.0005(6) -0.0009(6) 0.0008(7) C2 0.0134(7) 0.0246(7) 0.0177(7) 0.0042(6) 0.0017(6) 0.0036(6) C3 0.0160(7) 0.0170(6) 0.0217(7) 0.0018(6) 0.0043(6) 0.0003(6) C4 0.0120(6) 0.0177(7) 0.0199(6) 0.0004(6) 0.0024(5) -0.0019(6) C5 0.0133(7) 0.0186(7) 0.0160(6) 0.0001(5) 0.0005(5) 0.0017(6) C6 0.0191(7) 0.0174(7) 0.0213(7) 0.0015(6) -0.0026(6) -0.0018(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4567(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.4230(19) yes O1 . C5 . 1.4402(17) yes O2 . C1 . 1.4136(19) yes O2 . C6 . 1.4476(19) yes O3 . C2 . 1.4454(17) yes O3 . C3 . 1.4473(19) yes O4 . C4 . 1.4209(18) yes O4 . H1 . 0.78(3) no C1 . C2 . 1.528(2) yes C1 . H11 . 0.966(19) no C2 . C3 . 1.469(2) yes C2 . H21 . 0.99(2) no C3 . C4 . 1.509(2) yes C3 . H31 . 0.941(19) no C4 . C5 . 1.537(2) yes C4 . H41 . 0.97(2) no C5 . C6 . 1.532(2) yes C5 . H51 . 0.94(2) no C6 . H61 . 0.98(2) no C6 . H62 . 0.981(19) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 100.94(11) yes C1 . O2 . C6 . 105.48(12) yes C2 . O3 . C3 . 61.02(10) yes C4 . O4 . H1 . 108.7(20) no O1 . C1 . O2 . 105.15(13) yes O1 . C1 . C2 . 109.31(13) yes O2 . C1 . C2 . 111.56(12) yes O1 . C1 . H11 . 107.5(11) no O2 . C1 . H11 . 110.2(11) no C2 . C1 . H11 . 112.8(11) no C1 . C2 . O3 . 114.91(13) yes C1 . C2 . C3 . 117.11(13) yes O3 . C2 . C3 . 59.56(10) yes C1 . C2 . H21 . 115.8(12) no O3 . C2 . H21 . 114.4(13) no C3 . C2 . H21 . 122.3(13) no C2 . C3 . O3 . 59.43(9) yes C2 . C3 . C4 . 117.66(14) yes O3 . C3 . C4 . 117.75(13) yes C2 . C3 . H31 . 120.0(12) no O3 . C3 . H31 . 113.1(12) no C4 . C3 . H31 . 116.4(12) no C3 . C4 . O4 . 109.56(13) yes C3 . C4 . C5 . 111.79(13) yes O4 . C4 . C5 . 111.16(13) yes C3 . C4 . H41 . 105.2(12) no O4 . C4 . H41 . 112.2(11) no C5 . C4 . H41 . 106.8(11) no C4 . C5 . O1 . 107.64(12) yes C4 . C5 . C6 . 115.28(13) yes O1 . C5 . C6 . 102.50(12) yes C4 . C5 . H51 . 111.5(12) no O1 . C5 . H51 . 109.9(12) no C6 . C5 . H51 . 109.6(12) no C5 . C6 . O2 . 104.06(12) yes C5 . C6 . H61 . 112.4(13) no O2 . C6 . H61 . 111.4(14) no C5 . C6 . H62 . 111.6(12) no O2 . C6 . H62 . 106.7(12) no H61 . C6 . H62 . 110.4(16) no # Attachment '- comp_9.cif' data_CRYSTALS_cif5 _database_code_depnum_ccdc_archive 'CCDC 832052' #TrackingRef '- comp_9.cif' _audit_creation_date 11-06-27 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e12_sykora_0m in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.4573(3) _cell_length_b 9.4912(5) _cell_length_c 10.0281(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 614.60(5) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H8 O4 # Dc = 1.56 Fooo = 304.00 Mu = 1.33 M = 144.13 # Found Formula = C6 H8 O4 # Dc = 1.56 FOOO = 304.00 Mu = 1.33 M = 144.13 _chemical_formula_sum 'C6 H8 O4' _chemical_formula_moiety 'C6 H8 O4' _chemical_compound_source ? _chemical_formula_weight 144.13 _cell_measurement_reflns_used 5355 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_max 0.47 _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.133 # Sheldrick geometric approximatio 0.94 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 5399 _reflns_number_total 840 _diffrn_reflns_av_R_equivalents 0.018 # Number of reflections with Friedels Law is 840 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 710 _diffrn_reflns_theta_min 2.955 _diffrn_reflns_theta_max 27.550 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.999 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.21 _refine_ls_number_reflns 746 _refine_ls_number_restraints 0 _refine_ls_number_parameters 123 #_refine_ls_R_factor_ref 0.0242 _refine_ls_wR_factor_ref 0.0283 _refine_ls_goodness_of_fit_ref 1.0708 #_reflns_number_all 836 _refine_ls_R_factor_all 0.0268 _refine_ls_wR_factor_all 0.0314 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 746 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_gt 0.0283 _refine_ls_shift/su_max 0.000060 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.231 0.212 0.946E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.14957(16) 0.07977(11) -0.04394(10) 0.0185 1.0000 Uani . . . . . . O2 O 0.06934(16) -0.12460(10) 0.06167(11) 0.0207 1.0000 Uani . . . . . . O3 O -0.27237(17) 0.00034(13) 0.18634(12) 0.0225 1.0000 Uani . . . . . . O4 O 0.14100(18) 0.27146(11) 0.16050(11) 0.0203 1.0000 Uani . . . . . . C1 C -0.0187(2) 0.00081(17) 0.00726(13) 0.0183 1.0000 Uani . . . . . . C2 C -0.1278(2) 0.08549(15) 0.11633(14) 0.0164 1.0000 Uani . . . . . . C3 C 0.0288(2) 0.14948(15) 0.21119(14) 0.0172 1.0000 Uani . . . . . . C4 C 0.2502(2) 0.13968(15) 0.18066(14) 0.0176 1.0000 Uani . . . . . . C5 C 0.3064(2) 0.05932(15) 0.05612(14) 0.0171 1.0000 Uani . . . . . . C6 C 0.2869(2) -0.09786(16) 0.08666(16) 0.0203 1.0000 Uani . . . . . . H11 H -0.116(3) -0.024(2) -0.065(2) 0.025(5) 1.0000 Uiso . . . . . . H21 H -0.203(3) 0.159(2) 0.073(2) 0.025(5) 1.0000 Uiso . . . . . . H31 H -0.016(3) 0.1594(19) 0.3050(18) 0.018(4) 1.0000 Uiso . . . . . . H41 H 0.355(3) 0.138(2) 0.2482(19) 0.023(5) 1.0000 Uiso . . . . . . H51 H 0.441(3) 0.088(2) 0.0184(19) 0.022(5) 1.0000 Uiso . . . . . . H61 H 0.318(3) -0.120(2) 0.177(2) 0.023(5) 1.0000 Uiso . . . . . . H62 H 0.366(4) -0.159(2) 0.028(2) 0.029(5) 1.0000 Uiso . . . . . . H1 H -0.215(4) -0.067(2) 0.221(2) 0.028(5) 1.0000 Uiso . . . . . . 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 O1 0.0214(5) 0.0207(5) 0.0135(5) 0.0026(4) 0.0012(4) -0.0038(4) O2 0.0235(5) 0.0132(5) 0.0254(5) -0.0005(4) 0.0023(4) -0.0022(4) O3 0.0157(5) 0.0219(5) 0.0300(5) 0.0109(5) 0.0041(4) 0.0020(5) O4 0.0247(5) 0.0124(4) 0.0240(5) -0.0005(4) -0.0013(4) -0.0012(4) C1 0.0210(6) 0.0185(6) 0.0153(6) 0.0010(5) -0.0030(5) -0.0043(6) C2 0.0141(5) 0.0164(6) 0.0186(6) 0.0052(5) -0.0003(5) -0.0004(5) C3 0.0217(7) 0.0143(6) 0.0155(6) -0.0002(5) 0.0005(5) 0.0016(6) C4 0.0196(7) 0.0151(6) 0.0180(6) 0.0012(6) -0.0047(5) -0.0011(5) C5 0.0156(6) 0.0170(6) 0.0186(6) 0.0031(6) 0.0018(5) -0.0001(5) C6 0.0214(7) 0.0159(6) 0.0235(7) 0.0012(5) 0.0052(6) 0.0031(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4422(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.4163(17) yes O1 . C5 . 1.4388(17) yes O2 . C1 . 1.4275(19) yes O2 . C6 . 1.4492(19) yes O3 . C2 . 1.4203(17) yes O3 . H1 . 0.82(2) no O4 . C3 . 1.4572(18) yes O4 . C4 . 1.4500(17) yes C1 . C2 . 1.5293(19) yes C1 . H11 . 0.98(2) no C2 . C3 . 1.516(2) yes C2 . H21 . 0.96(2) no C3 . C4 . 1.465(2) yes C3 . H31 . 0.989(18) no C4 . C5 . 1.508(2) yes C4 . H41 . 0.96(2) no C5 . C6 . 1.528(2) yes C5 . H51 . 0.98(2) no C6 . H61 . 0.95(2) no C6 . H62 . 0.97(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 102.46(10) yes C1 . O2 . C6 . 107.82(11) yes C2 . O3 . H1 . 111.0(16) no C3 . O4 . C4 . 60.52(9) yes O2 . C1 . O1 . 105.92(11) yes O2 . C1 . C2 . 110.39(11) yes O1 . C1 . C2 . 109.55(12) yes O2 . C1 . H11 . 109.3(11) no O1 . C1 . H11 . 110.6(12) no C2 . C1 . H11 . 110.9(12) no C1 . C2 . O3 . 110.93(12) yes C1 . C2 . C3 . 110.61(12) yes O3 . C2 . C3 . 110.88(11) yes C1 . C2 . H21 . 106.8(12) no O3 . C2 . H21 . 108.0(12) no C3 . C2 . H21 . 109.5(12) no C2 . C3 . O4 . 115.54(11) yes C2 . C3 . C4 . 119.65(12) yes O4 . C3 . C4 . 59.50(9) yes C2 . C3 . H31 . 116.1(11) no O4 . C3 . H31 . 113.7(11) no C4 . C3 . H31 . 119.4(11) no C3 . C4 . O4 . 59.98(9) yes C3 . C4 . C5 . 116.11(12) yes O4 . C4 . C5 . 115.97(12) yes C3 . C4 . H41 . 122.9(12) no O4 . C4 . H41 . 117.4(12) no C5 . C4 . H41 . 113.9(12) no C4 . C5 . O1 . 109.88(11) yes C4 . C5 . C6 . 107.93(12) yes O1 . C5 . C6 . 102.32(12) yes C4 . C5 . H51 . 113.1(12) no O1 . C5 . H51 . 108.4(11) no C6 . C5 . H51 . 114.7(12) no C5 . C6 . O2 . 102.50(12) yes C5 . C6 . H61 . 113.0(12) no O2 . C6 . H61 . 109.4(13) no C5 . C6 . H62 . 114.7(12) no O2 . C6 . H62 . 107.7(13) no H61 . C6 . H62 . 109.1(17) no # Attachment '- comp_11.cif' data_CRYSTALS_cif6 _database_code_depnum_ccdc_archive 'CCDC 832053' #TrackingRef '- comp_11.cif' _audit_creation_date 11-06-27 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e290b_sykora_0m in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.1219(3) _cell_length_b 8.5353(6) _cell_length_c 11.8539(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 619.39(7) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H8 O4 # Dc = 1.55 Fooo = 304.00 Mu = 1.32 M = 144.13 # Found Formula = C6 H8 O4 # Dc = 1.55 FOOO = 304.00 Mu = 1.32 M = 144.13 _chemical_formula_sum 'C6 H8 O4' _chemical_formula_moiety 'C6 H8 O4' _chemical_compound_source ? _chemical_formula_weight 144.13 _cell_measurement_reflns_used 5397 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description bar _exptl_crystal_colour colourless _exptl_crystal_size_min 0.21 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_max 0.60 _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.132 # Sheldrick geometric approximatio 0.96 0.97 # No experimental values of Tmin/max available _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 5459 _reflns_number_total 852 _diffrn_reflns_av_R_equivalents 0.024 # Number of reflections with Friedels Law is 852 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 712 _diffrn_reflns_theta_min 2.941 _diffrn_reflns_theta_max 27.514 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.514 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.19 _refine_diff_density_max 0.18 _refine_ls_number_reflns 696 _refine_ls_number_restraints 0 _refine_ls_number_parameters 123 #_refine_ls_R_factor_ref 0.0255 _refine_ls_wR_factor_ref 0.0295 _refine_ls_goodness_of_fit_ref 0.9937 #_reflns_number_all 849 _refine_ls_R_factor_all 0.0309 _refine_ls_wR_factor_all 0.0388 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 696 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_gt 0.0295 _refine_ls_shift/su_max 0.000198 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.222 0.207 0.764E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 1.06737(19) 0.33796(13) 0.60473(9) 0.0209 1.0000 Uani . . . . . . O2 O 1.15724(19) 0.59572(14) 0.60010(10) 0.0225 1.0000 Uani . . . . . . O3 O 0.9805(2) 0.40112(17) 0.85875(9) 0.0252 1.0000 Uani . . . . . . O4 O 0.65291(19) 0.34596(17) 0.68700(10) 0.0267 1.0000 Uani . . . . . . C1 C 1.1333(3) 0.4637(2) 0.67422(14) 0.0196 1.0000 Uani . . . . . . C2 C 0.9634(3) 0.5023(2) 0.76397(12) 0.0197 1.0000 Uani . . . . . . C3 C 0.7362(3) 0.5009(2) 0.71408(15) 0.0227 1.0000 Uani . . . . . . C4 C 0.7080(3) 0.4524(2) 0.59629(14) 0.0232 1.0000 Uani . . . . . . C5 C 0.9121(3) 0.4118(2) 0.53085(13) 0.0205 1.0000 Uani . . . . . . C6 C 1.0331(3) 0.5614(2) 0.49860(13) 0.0223 1.0000 Uani . . . . . . H11 H 1.275(3) 0.440(2) 0.7112(18) 0.020(5) 1.0000 Uiso . . . . . . H21 H 0.992(4) 0.615(2) 0.7901(17) 0.022(5) 1.0000 Uiso . . . . . . H31 H 0.635(4) 0.568(3) 0.7500(19) 0.035(6) 1.0000 Uiso . . . . . . H41 H 0.588(4) 0.496(3) 0.5531(18) 0.026(5) 1.0000 Uiso . . . . . . H51 H 0.878(3) 0.342(3) 0.4718(18) 0.030(6) 1.0000 Uiso . . . . . . H61 H 1.128(3) 0.545(3) 0.434(2) 0.028(6) 1.0000 Uiso . . . . . . H62 H 0.938(4) 0.655(2) 0.4807(18) 0.023(5) 1.0000 Uiso . . . . . . H1 H 0.930(4) 0.316(3) 0.8444(19) 0.031(6) 1.0000 Uiso . . . . . . 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 O1 0.0228(5) 0.0207(5) 0.0193(5) -0.0023(5) 0.0025(5) 0.0039(5) O2 0.0217(5) 0.0267(5) 0.0190(5) 0.0007(5) 0.0002(5) -0.0079(5) O3 0.0326(6) 0.0291(6) 0.0141(5) 0.0012(5) -0.0039(5) -0.0038(6) O4 0.0193(5) 0.0367(7) 0.0241(6) 0.0082(6) -0.0016(5) -0.0071(6) C1 0.0138(6) 0.0256(9) 0.0195(7) 0.0003(6) 0.0003(6) -0.0003(6) C2 0.0232(8) 0.0209(6) 0.0149(6) -0.0019(6) 0.0012(6) -0.0017(7) C3 0.0185(7) 0.0286(8) 0.0209(7) 0.0044(7) 0.0062(6) 0.0056(7) C4 0.0159(7) 0.0318(8) 0.0218(7) 0.0080(8) -0.0036(7) -0.0033(7) C5 0.0235(7) 0.0235(8) 0.0145(6) -0.0013(6) -0.0011(6) -0.0044(7) C6 0.0228(8) 0.0287(8) 0.0154(6) 0.0000(6) 0.0008(6) -0.0051(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3722(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.412(2) yes O1 . C5 . 1.438(2) yes O2 . C1 . 1.437(2) yes O2 . C6 . 1.4528(19) yes O3 . C2 . 1.4207(19) yes O3 . H1 . 0.80(3) no O4 . C3 . 1.453(2) yes O4 . C4 . 1.447(2) yes C1 . C2 . 1.524(2) yes C1 . H11 . 0.99(2) no C2 . C3 . 1.511(2) yes C2 . H21 . 1.03(2) no C3 . C4 . 1.467(2) yes C3 . H31 . 0.94(3) no C4 . C5 . 1.511(2) yes C4 . H41 . 0.97(2) no C5 . C6 . 1.525(2) yes C5 . H51 . 0.94(2) no C6 . H61 . 0.97(2) no C6 . H62 . 1.01(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 102.21(12) yes C1 . O2 . C6 . 107.16(12) yes C2 . O3 . H1 . 110.5(17) no C3 . O4 . C4 . 60.74(11) yes O2 . C1 . O1 . 105.58(12) yes O2 . C1 . C2 . 109.09(14) yes O1 . C1 . C2 . 112.12(13) yes O2 . C1 . H11 . 110.1(12) no O1 . C1 . H11 . 110.5(12) no C2 . C1 . H11 . 109.4(12) no C1 . C2 . O3 . 111.74(14) yes C1 . C2 . C3 . 110.69(13) yes O3 . C2 . C3 . 111.87(13) yes C1 . C2 . H21 . 107.3(12) no O3 . C2 . H21 . 108.5(11) no C3 . C2 . H21 . 106.4(12) no C2 . C3 . O4 . 114.61(14) yes C2 . C3 . C4 . 118.88(14) yes O4 . C3 . C4 . 59.43(11) yes C2 . C3 . H31 . 114.9(15) no O4 . C3 . H31 . 115.0(16) no C4 . C3 . H31 . 121.6(15) no C3 . C4 . O4 . 59.82(12) yes C3 . C4 . C5 . 117.16(14) yes O4 . C4 . C5 . 115.48(14) yes C3 . C4 . H41 . 119.1(13) no O4 . C4 . H41 . 117.1(13) no C5 . C4 . H41 . 116.2(13) no C4 . C5 . O1 . 109.54(12) yes C4 . C5 . C6 . 109.76(14) yes O1 . C5 . C6 . 101.44(12) yes C4 . C5 . H51 . 110.2(13) no O1 . C5 . H51 . 108.6(13) no C6 . C5 . H51 . 116.8(14) no C5 . C6 . O2 . 102.43(13) yes C5 . C6 . H61 . 111.4(14) no O2 . C6 . H61 . 111.9(13) no C5 . C6 . H62 . 115.7(12) no O2 . C6 . H62 . 108.4(12) no H61 . C6 . H62 . 107.0(17) no # Attachment '- comp_12.cif' data_CRYSTALS_cif7 _database_code_depnum_ccdc_archive 'CCDC 832054' #TrackingRef '- comp_12.cif' _audit_creation_date 11-06-27 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e998_sykora_0m in P2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.6936(5) _cell_length_b 7.0452(5) _cell_length_c 6.7070(5) _cell_angle_alpha 90 _cell_angle_beta 99.357(2) _cell_angle_gamma 90 _cell_volume 312.08(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C6 H8 O4 # Dc = 1.53 Fooo = 152.00 Mu = 1.31 M = 144.13 # Found Formula = C6 H8 O4 # Dc = 1.53 FOOO = 152.00 Mu = 1.31 M = 144.13 _chemical_formula_sum 'C6 H8 O4' _chemical_formula_moiety 'C6 H8 O4' _chemical_compound_source ? _chemical_formula_weight 144.13 _cell_measurement_reflns_used 2700 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.27 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_max 0.68 _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 152 _exptl_absorpt_coefficient_mu 0.131 # Sheldrick geometric approximatio 0.96 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 2713 _reflns_number_total 779 _diffrn_reflns_av_R_equivalents 0.016 # Number of reflections with Friedels Law is 779 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 716 _diffrn_reflns_theta_min 3.078 _diffrn_reflns_theta_max 27.488 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.488 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 8 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.19 _refine_diff_density_max 0.19 _refine_ls_number_reflns 692 _refine_ls_number_restraints 1 _refine_ls_number_parameters 123 #_refine_ls_R_factor_ref 0.0235 _refine_ls_wR_factor_ref 0.0268 _refine_ls_goodness_of_fit_ref 1.1023 #_reflns_number_all 776 _refine_ls_R_factor_all 0.0263 _refine_ls_wR_factor_all 0.0294 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 692 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_gt 0.0268 _refine_ls_shift/su_max 0.000156 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.207 0.178 0.885E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.01600(15) 0.2181(2) 0.63400(16) 0.0168 1.0000 Uani . . . . . . O2 O 0.15335(18) 0.0279(2) 0.89137(18) 0.0201 1.0000 Uani . . . . . . O3 O 0.2015(2) 0.5348(2) 0.81683(19) 0.0236 1.0000 Uani . . . . . . O4 O 0.30962(18) 0.4480(2) 0.43383(18) 0.0192 1.0000 Uani . . . . . . C1 C 0.0634(2) 0.2088(3) 0.8478(2) 0.0166 1.0000 Uani . . . . . . C2 C 0.2181(3) 0.3584(3) 0.9263(2) 0.0191 1.0000 Uani . . . . . . C3 C 0.3686(3) 0.4081(3) 0.7979(2) 0.0192 1.0000 Uani . . . . . . C4 C 0.3546(2) 0.3135(3) 0.5919(2) 0.0160 1.0000 Uani . . . . . . C5 C 0.2022(2) 0.1511(3) 0.5741(2) 0.0159 1.0000 Uani . . . . . . C6 C 0.2664(3) -0.0086(3) 0.7279(3) 0.0211 1.0000 Uani . . . . . . H11 H -0.053(3) 0.216(3) 0.907(3) 0.012(4) 1.0000 Uiso . . . . . . H21 H 0.252(3) 0.369(3) 1.064(3) 0.020(5) 1.0000 Uiso . . . . . . H31 H 0.499(3) 0.456(4) 0.854(3) 0.022(5) 1.0000 Uiso . . . . . . H41 H 0.483(3) 0.257(3) 0.576(3) 0.015(5) 1.0000 Uiso . . . . . . H51 H 0.170(3) 0.110(3) 0.435(3) 0.015(5) 1.0000 Uiso . . . . . . H61 H 0.411(3) -0.006(3) 0.781(3) 0.018(5) 1.0000 Uiso . . . . . . H62 H 0.230(4) -0.130(4) 0.673(4) 0.026(6) 1.0000 Uiso . . . . . . H4 H 0.204(4) 0.495(5) 0.447(4) 0.039(7) 1.0000 Uiso . . . . . . 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 O1 0.0150(5) 0.0191(6) 0.0163(5) 0.0003(4) 0.0023(4) -0.0005(5) O2 0.0262(6) 0.0166(6) 0.0198(5) 0.0050(5) 0.0108(4) 0.0028(5) O3 0.0358(6) 0.0141(6) 0.0238(6) -0.0012(5) 0.0133(5) -0.0008(5) O4 0.0210(6) 0.0208(6) 0.0174(5) 0.0057(5) 0.0083(4) 0.0022(5) C1 0.0189(7) 0.0157(7) 0.0163(7) 0.0014(6) 0.0066(5) -0.0007(6) C2 0.0259(8) 0.0194(9) 0.0127(7) -0.0017(6) 0.0053(6) -0.0018(7) C3 0.0199(7) 0.0211(8) 0.0164(7) -0.0011(6) 0.0026(6) -0.0063(6) C4 0.0154(7) 0.0171(8) 0.0165(7) 0.0016(6) 0.0054(5) 0.0010(6) C5 0.0193(8) 0.0155(7) 0.0134(6) -0.0003(6) 0.0040(5) 0.0011(6) C6 0.0281(8) 0.0169(9) 0.0206(8) 0.0028(7) 0.0105(6) 0.0049(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5795(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.4190(17) yes O1 . C5 . 1.4493(18) yes O2 . C1 . 1.420(2) yes O2 . C6 . 1.4530(19) yes O3 . C2 . 1.438(2) yes O3 . C3 . 1.453(2) yes O4 . C4 . 1.4171(19) yes O4 . H4 . 0.80(3) no C1 . C2 . 1.511(2) yes C1 . H11 . 0.931(18) no C2 . C3 . 1.471(2) yes C2 . H21 . 0.92(2) no C3 . C4 . 1.523(2) yes C3 . H31 . 0.95(2) no C4 . C5 . 1.525(2) yes C4 . H41 . 0.97(2) no C5 . C6 . 1.540(2) yes C5 . H51 . 0.97(2) no C6 . H61 . 0.98(2) no C6 . H62 . 0.95(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 101.78(11) yes C1 . O2 . C6 . 105.00(11) yes C2 . O3 . C3 . 61.16(10) yes C4 . O4 . H4 . 106(2) no O2 . C1 . O1 . 105.49(13) yes O2 . C1 . C2 . 108.12(13) yes O1 . C1 . C2 . 110.37(13) yes O2 . C1 . H11 . 108.5(14) no O1 . C1 . H11 . 111.3(11) no C2 . C1 . H11 . 112.7(13) no C1 . C2 . O3 . 115.66(14) yes C1 . C2 . C3 . 117.25(13) yes O3 . C2 . C3 . 59.89(10) yes C1 . C2 . H21 . 117.0(15) no O3 . C2 . H21 . 115.2(16) no C3 . C2 . H21 . 119.2(13) no C2 . C3 . O3 . 58.95(10) yes C2 . C3 . C4 . 118.69(14) yes O3 . C3 . C4 . 114.42(14) yes C2 . C3 . H31 . 121.6(13) no O3 . C3 . H31 . 114.7(16) no C4 . C3 . H31 . 115.4(13) no C3 . C4 . O4 . 111.11(13) yes C3 . C4 . C5 . 109.97(12) yes O4 . C4 . C5 . 112.66(13) yes C3 . C4 . H41 . 110.6(12) no O4 . C4 . H41 . 106.1(12) no C5 . C4 . H41 . 106.2(14) no C4 . C5 . O1 . 109.16(13) yes C4 . C5 . C6 . 112.67(13) yes O1 . C5 . C6 . 102.19(12) yes C4 . C5 . H51 . 110.2(13) no O1 . C5 . H51 . 107.2(12) no C6 . C5 . H51 . 114.8(14) no C5 . C6 . O2 . 104.69(12) yes C5 . C6 . H61 . 112.6(14) no O2 . C6 . H61 . 109.2(12) no C5 . C6 . H62 . 112.0(14) no O2 . C6 . H62 . 108.6(14) no H61 . C6 . H62 . 109.5(20) no # Attachment '- comp_14.cif' data_CRYSTALS_cif8 _database_code_depnum_ccdc_archive 'CCDC 832055' #TrackingRef '- comp_14.cif' _audit_creation_date 11-06-27 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e298c_sykora_0m in P2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.1357(4) _cell_length_b 5.1847(3) _cell_length_c 9.4064(6) _cell_angle_alpha 90 _cell_angle_beta 93.064(2) _cell_angle_gamma 90 _cell_volume 298.81(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C6 H8 O4 # Dc = 1.60 Fooo = 152.00 Mu = 1.37 M = 144.13 # Found Formula = C6 H8 O4 # Dc = 1.60 FOOO = 152.00 Mu = 1.37 M = 144.13 _chemical_formula_sum 'C6 H8 O4' _chemical_formula_moiety 'C6 H8 O4' _chemical_compound_source ? _chemical_formula_weight 144.13 _cell_measurement_reflns_used 3483 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.19 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 152 _exptl_absorpt_coefficient_mu 0.137 # Sheldrick geometric approximatio 0.97 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 3601 _reflns_number_total 804 _diffrn_reflns_av_R_equivalents 0.018 # Number of reflections with Friedels Law is 804 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 726 _diffrn_reflns_theta_min 2.168 _diffrn_reflns_theta_max 28.070 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.070 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.14 _refine_diff_density_max 0.25 _refine_ls_number_reflns 739 _refine_ls_number_restraints 1 _refine_ls_number_parameters 123 #_refine_ls_R_factor_ref 0.0242 _refine_ls_wR_factor_ref 0.0275 _refine_ls_goodness_of_fit_ref 1.1586 #_reflns_number_all 800 _refine_ls_R_factor_all 0.0264 _refine_ls_wR_factor_all 0.0313 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 739 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_gt 0.0275 _refine_ls_shift/su_max 0.000139 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.172 0.934E-01 0.426E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.68458(19) -0.0091(3) 0.32739(13) 0.0239 1.0000 Uani . . . . . . O2 O 0.74001(17) 0.3942(3) 0.41549(12) 0.0207 1.0000 Uani . . . . . . O3 O 0.38899(19) 0.5879(3) 0.24317(13) 0.0217 1.0000 Uani . . . . . . O4 O 0.8036(2) 0.4686(3) 0.10508(13) 0.0277 1.0000 Uani . . . . . . C1 C 0.5765(3) 0.2233(4) 0.35910(16) 0.0191 1.0000 Uani . . . . . . C2 C 0.4645(2) 0.3333(4) 0.22164(16) 0.0186 1.0000 Uani . . . . . . C3 C 0.6079(3) 0.3130(4) 0.09674(15) 0.0237 1.0000 Uani . . . . . . C4 C 0.8220(3) 0.1899(4) 0.1177(2) 0.0276 1.0000 Uani . . . . . . C5 C 0.8805(3) 0.0869(4) 0.26557(19) 0.0249 1.0000 Uani . . . . . . C6 C 0.9473(2) 0.2997(4) 0.37117(19) 0.0246 1.0000 Uani . . . . . . H11 H 0.471(3) 0.197(4) 0.4325(19) 0.018(5) 1.0000 Uiso . . . . . . H21 H 0.331(3) 0.231(5) 0.195(2) 0.025(5) 1.0000 Uiso . . . . . . H31 H 0.542(3) 0.305(5) 0.004(2) 0.024(5) 1.0000 Uiso . . . . . . H41 H 0.880(3) 0.117(5) 0.037(2) 0.026(5) 1.0000 Uiso . . . . . . H51 H 0.977(3) -0.054(5) 0.268(2) 0.025(5) 1.0000 Uiso . . . . . . H61 H 1.034(3) 0.234(4) 0.454(2) 0.021(5) 1.0000 Uiso . . . . . . H62 H 1.023(3) 0.443(5) 0.327(2) 0.025(5) 1.0000 Uiso . . . . . . H1 H 0.496(4) 0.674(5) 0.273(2) 0.033(6) 1.0000 Uiso . . . . . . 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 O1 0.0246(5) 0.0129(5) 0.0348(6) 0.0012(5) 0.0064(4) -0.0013(5) O2 0.0209(5) 0.0184(6) 0.0229(5) -0.0036(4) 0.0002(4) -0.0010(4) O3 0.0196(5) 0.0180(5) 0.0273(6) -0.0028(5) 0.0000(4) 0.0012(5) O4 0.0317(6) 0.0235(6) 0.0291(6) 0.0023(5) 0.0126(5) -0.0028(6) C1 0.0208(6) 0.0153(7) 0.0217(7) -0.0003(6) 0.0048(5) -0.0022(6) C2 0.0174(6) 0.0161(8) 0.0224(6) -0.0024(6) 0.0023(5) -0.0022(6) C3 0.0324(8) 0.0207(7) 0.0182(6) -0.0031(7) 0.0039(5) -0.0020(8) C4 0.0297(9) 0.0238(8) 0.0308(9) -0.0064(7) 0.0149(7) -0.0005(8) C5 0.0191(7) 0.0160(7) 0.0401(10) -0.0009(7) 0.0062(6) 0.0025(7) C6 0.0180(6) 0.0199(8) 0.0354(8) 0.0016(7) -0.0016(6) 0.0010(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.8239(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.415(2) yes O1 . C5 . 1.4513(19) yes O2 . C1 . 1.4197(19) yes O2 . C6 . 1.4452(19) yes O3 . C2 . 1.4167(19) yes O3 . H1 . 0.83(3) no O4 . C3 . 1.446(2) yes O4 . C4 . 1.454(2) yes C1 . C2 . 1.541(2) yes C1 . H11 . 0.980(18) no C2 . C3 . 1.508(2) yes C2 . H21 . 1.00(2) no C3 . C4 . 1.464(3) yes C3 . H31 . 0.94(2) no C4 . C5 . 1.515(3) yes C4 . H41 . 0.93(2) no C5 . C6 . 1.526(2) yes C5 . H51 . 0.94(3) no C6 . H61 . 0.98(2) no C6 . H62 . 0.98(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 101.53(12) yes C1 . O2 . C6 . 107.22(12) yes C2 . O3 . H1 . 107.1(18) no C3 . O4 . C4 . 60.67(12) yes O2 . C1 . O1 . 106.28(12) yes O2 . C1 . C2 . 110.91(13) yes O1 . C1 . C2 . 109.35(12) yes O2 . C1 . H11 . 107.7(12) no O1 . C1 . H11 . 111.2(13) no C2 . C1 . H11 . 111.3(11) no C1 . C2 . O3 . 111.07(13) yes C1 . C2 . C3 . 112.04(12) yes O3 . C2 . C3 . 112.67(14) yes C1 . C2 . H21 . 109.5(13) no O3 . C2 . H21 . 105.2(13) no C3 . C2 . H21 . 106.0(12) no C2 . C3 . O4 . 115.84(13) yes C2 . C3 . C4 . 118.83(14) yes O4 . C3 . C4 . 59.96(11) yes C2 . C3 . H31 . 118.9(12) no O4 . C3 . H31 . 113.0(13) no C4 . C3 . H31 . 116.2(13) no C3 . C4 . O4 . 59.38(13) yes C3 . C4 . C5 . 116.34(13) yes O4 . C4 . C5 . 116.01(16) yes C3 . C4 . H41 . 116.3(13) no O4 . C4 . H41 . 111.6(16) no C5 . C4 . H41 . 121.4(14) no C4 . C5 . O1 . 109.14(13) yes C4 . C5 . C6 . 112.65(16) yes O1 . C5 . C6 . 100.76(13) yes C4 . C5 . H51 . 114.6(12) no O1 . C5 . H51 . 105.0(14) no C6 . C5 . H51 . 113.4(13) no C5 . C6 . O2 . 102.88(12) yes C5 . C6 . H61 . 112.4(13) no O2 . C6 . H61 . 109.6(11) no C5 . C6 . H62 . 112.9(12) no O2 . C6 . H62 . 108.1(13) no H61 . C6 . H62 . 110.5(16) no # Attachment '- comp_15.cif' data_CRYSTALS_cif9 _database_code_depnum_ccdc_archive 'CCDC 832056' #TrackingRef '- comp_15.cif' _audit_creation_date 11-06-29 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title ? _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.6980(2) _cell_length_b 8.7730(2) _cell_length_c 8.8850(3) _cell_angle_alpha 90 _cell_angle_beta 94.9760(16) _cell_angle_gamma 90 _cell_volume 597.78(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H7 F1 O3 # Dc = 1.62 Fooo = 304.00 Mu = 1.49 M = 292.24 # Found Formula = C6 H7 F1 O3 # Dc = 1.62 FOOO = 304.00 Mu = 1.49 M = 292.24 _chemical_formula_sum 'C6 H7 F1 O3' _chemical_formula_moiety 'C6 H7 F1 O3' _chemical_compound_source ? _chemical_formula_weight 146.12 _cell_measurement_reflns_used 1434 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.149 # Sheldrick geometric approximatio 0.96 0.96 # No experimental values of Tmin/max available _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 2731 _reflns_number_total 1455 _diffrn_reflns_av_R_equivalents 0.006 # Number of reflections with Friedels Law is 1455 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1369 _diffrn_reflns_theta_min 2.301 _diffrn_reflns_theta_max 27.470 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.470 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.14 _refine_ls_number_reflns 1284 _refine_ls_number_restraints 1 _refine_ls_number_parameters 237 #_refine_ls_R_factor_ref 0.0273 _refine_ls_wR_factor_ref 0.0308 _refine_ls_goodness_of_fit_ref 1.0295 #_reflns_number_all 1449 _refine_ls_R_factor_all 0.0325 _refine_ls_wR_factor_all 0.0366 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 1284 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_gt 0.0308 _refine_ls_shift/su_max 0.000255 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.422 0.234 0.165 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 0.96211(19) -0.33362(18) -0.05732(13) 0.0363 1.0000 Uani . . . . . . F11 F 0.39624(19) 0.1582(2) 0.51636(14) 0.0401 1.0000 Uani . . . . . . O1 O 1.18693(18) -0.25776(19) 0.19526(16) 0.0259 1.0000 Uani . . . . . . O2 O 0.90666(18) -0.4605(2) 0.15597(17) 0.0268 1.0000 Uani . . . . . . O3 O 1.0944(2) -0.1474(2) 0.44267(18) 0.0344 1.0000 Uani . . . . . . O11 O 0.65990(18) 0.0707(2) 0.34027(17) 0.0284 1.0000 Uani . . . . . . O12 O 0.3917(2) 0.2812(2) 0.29080(18) 0.0307 1.0000 Uani . . . . . . O13 O 0.6173(2) -0.0459(2) 0.07629(19) 0.0331 1.0000 Uani . . . . . . C1 C 0.9008(3) -0.3188(3) 0.0868(2) 0.0263 1.0000 Uani . . . . . . C2 C 1.0117(3) -0.2006(3) 0.1739(2) 0.0247 1.0000 Uani . . . . . . C3 C 0.9543(3) -0.1927(3) 0.3324(2) 0.0275 1.0000 Uani . . . . . . C4 C 1.0584(3) -0.3076(3) 0.4165(2) 0.0268 1.0000 Uani . . . . . . C5 C 1.1718(3) -0.3777(3) 0.3045(2) 0.0237 1.0000 Uani . . . . . . C6 C 1.0777(3) -0.5089(2) 0.2226(2) 0.0258 1.0000 Uani . . . . . . C11 C 0.3649(3) 0.1429(3) 0.3587(2) 0.0282 1.0000 Uani . . . . . . C12 C 0.4841(3) 0.0174(3) 0.3098(2) 0.0257 1.0000 Uani . . . . . . C13 C 0.4613(3) 0.0070(3) 0.1388(2) 0.0257 1.0000 Uani . . . . . . C14 C 0.5849(3) 0.1159(3) 0.0859(3) 0.0272 1.0000 Uani . . . . . . C15 C 0.6739(3) 0.1874(3) 0.2272(2) 0.0276 1.0000 Uani . . . . . . C16 C 0.5718(3) 0.3236(3) 0.2751(3) 0.0298 1.0000 Uani . . . . . . H11 H 0.774(3) -0.286(3) 0.072(3) 0.029(6) 1.0000 Uiso . . . . . . H21 H 1.011(3) -0.103(3) 0.121(3) 0.030(7) 1.0000 Uiso . . . . . . H31 H 0.837(4) -0.166(4) 0.353(3) 0.036(7) 1.0000 Uiso . . . . . . H41 H 1.018(4) -0.371(4) 0.500(3) 0.032(6) 1.0000 Uiso . . . . . . H51 H 1.287(3) -0.409(3) 0.347(3) 0.028(6) 1.0000 Uiso . . . . . . H61 H 1.146(3) -0.544(3) 0.141(3) 0.030(7) 1.0000 Uiso . . . . . . H62 H 1.053(3) -0.591(3) 0.294(3) 0.032(7) 1.0000 Uiso . . . . . . H111 H 0.241(3) 0.114(3) 0.337(3) 0.026(6) 1.0000 Uiso . . . . . . H121 H 0.467(3) -0.081(4) 0.362(3) 0.034(7) 1.0000 Uiso . . . . . . H131 H 0.349(4) -0.022(3) 0.088(3) 0.036(7) 1.0000 Uiso . . . . . . H141 H 0.569(3) 0.174(4) -0.009(3) 0.035(7) 1.0000 Uiso . . . . . . H151 H 0.798(3) 0.216(3) 0.222(3) 0.033(7) 1.0000 Uiso . . . . . . H161 H 0.627(4) 0.362(4) 0.373(3) 0.037(7) 1.0000 Uiso . . . . . . H162 H 0.566(4) 0.409(4) 0.198(3) 0.044(8) 1.0000 Uiso . . . . . . 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 0.0528(8) 0.0308(7) 0.0246(6) -0.0005(6) -0.0011(5) 0.0057(6) F11 0.0513(8) 0.0422(9) 0.0286(6) -0.0020(7) 0.0138(6) 0.0026(7) O1 0.0233(7) 0.0248(8) 0.0300(7) 0.0039(6) 0.0049(5) -0.0029(6) O2 0.0236(7) 0.0209(7) 0.0350(7) 0.0012(6) -0.0029(5) -0.0019(6) O3 0.0393(9) 0.0289(9) 0.0334(8) -0.0090(7) -0.0056(6) 0.0033(7) O11 0.0254(7) 0.0282(8) 0.0307(8) 0.0015(6) -0.0030(6) 0.0052(6) O12 0.0282(7) 0.0249(8) 0.0400(8) 0.0036(7) 0.0081(6) 0.0085(6) O13 0.0347(8) 0.0273(8) 0.0386(9) -0.0070(7) 0.0098(7) 0.0053(7) C1 0.0278(10) 0.0227(10) 0.0277(9) 0.0001(9) -0.0019(7) 0.0051(8) C2 0.0278(10) 0.0168(10) 0.0291(10) 0.0024(8) -0.0007(8) 0.0009(8) C3 0.0253(9) 0.0258(11) 0.0311(10) -0.0063(9) 0.0009(8) 0.0031(8) C4 0.0294(9) 0.0253(11) 0.0258(9) -0.0016(8) 0.0028(8) 0.0009(9) C5 0.0238(9) 0.0215(9) 0.0259(9) 0.0013(8) 0.0024(7) 0.0022(8) C6 0.0271(10) 0.0200(10) 0.0297(10) 0.0011(9) -0.0015(8) 0.0031(8) C11 0.0266(10) 0.0294(11) 0.0296(10) 0.0003(9) 0.0083(8) 0.0014(9) C12 0.0277(10) 0.0221(10) 0.0274(9) 0.0025(9) 0.0029(7) 0.0001(8) C13 0.0249(9) 0.0258(10) 0.0264(9) -0.0004(9) 0.0012(7) 0.0026(8) C14 0.0290(10) 0.0260(11) 0.0271(10) -0.0016(8) 0.0056(8) 0.0015(9) C15 0.0235(9) 0.0283(11) 0.0311(10) -0.0016(9) 0.0038(8) -0.0013(8) C16 0.0318(11) 0.0226(10) 0.0352(11) -0.0012(10) 0.0046(9) -0.0024(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.9842(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C1 . 1.409(2) yes F11 . C11 . 1.407(3) yes O1 . C2 . 1.436(2) yes O1 . C5 . 1.443(2) yes O2 . C1 . 1.386(3) yes O2 . C6 . 1.459(2) yes O3 . C3 . 1.448(3) yes O3 . C4 . 1.447(3) yes O11 . C12 . 1.435(3) yes O11 . C15 . 1.445(3) yes O12 . C11 . 1.379(3) yes O12 . C16 . 1.454(3) yes O13 . C13 . 1.443(3) yes O13 . C14 . 1.445(3) yes C1 . C2 . 1.513(3) yes C1 . H11 . 1.01(2) no C2 . C3 . 1.514(3) yes C2 . H21 . 0.98(3) no C3 . C4 . 1.453(3) yes C3 . H31 . 0.96(3) no C4 . C5 . 1.510(3) yes C4 . H41 . 1.00(3) no C5 . C6 . 1.512(3) yes C5 . H51 . 0.97(3) no C6 . H61 . 0.98(3) no C6 . H62 . 0.99(3) no C11 . C12 . 1.521(3) yes C11 . H111 . 0.99(2) no C12 . C13 . 1.516(3) yes C12 . H121 . 0.99(3) no C13 . C14 . 1.454(3) yes C13 . H131 . 0.97(3) no C14 . C15 . 1.514(3) yes C14 . H141 . 0.98(3) no C15 . C16 . 1.512(3) yes C15 . H151 . 0.99(3) no C16 . H161 . 1.00(3) no C16 . H162 . 1.02(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C5 . 102.32(15) yes C1 . O2 . C6 . 115.75(16) yes C3 . O3 . C4 . 60.25(14) yes C12 . O11 . C15 . 103.04(15) yes C11 . O12 . C16 . 116.57(17) yes C13 . O13 . C14 . 60.48(14) yes F1 . C1 . O2 . 108.64(17) yes F1 . C1 . C2 . 108.04(17) yes O2 . C1 . C2 . 113.11(16) yes F1 . C1 . H11 . 107.7(13) no O2 . C1 . H11 . 107.7(16) no C2 . C1 . H11 . 111.5(16) no C1 . C2 . O1 . 108.07(17) yes C1 . C2 . C3 . 108.09(17) yes O1 . C2 . C3 . 103.88(16) yes C1 . C2 . H21 . 112.0(16) no O1 . C2 . H21 . 109.5(16) no C3 . C2 . H21 . 114.9(15) no C2 . C3 . O3 . 112.44(18) yes C2 . C3 . C4 . 104.69(18) yes O3 . C3 . C4 . 59.85(13) yes C2 . C3 . H31 . 122.8(15) no O3 . C3 . H31 . 117.3(16) no C4 . C3 . H31 . 123.5(17) no C3 . C4 . O3 . 59.90(14) yes C3 . C4 . C5 . 105.58(18) yes O3 . C4 . C5 . 112.86(19) yes C3 . C4 . H41 . 125.1(17) no O3 . C4 . H41 . 119.5(17) no C5 . C4 . H41 . 119.7(17) no C4 . C5 . O1 . 103.34(17) yes C4 . C5 . C6 . 110.32(17) yes O1 . C5 . C6 . 107.15(16) yes C4 . C5 . H51 . 114.6(15) no O1 . C5 . H51 . 110.3(15) no C6 . C5 . H51 . 110.7(16) no C5 . C6 . O2 . 110.59(16) yes C5 . C6 . H61 . 109.1(17) no O2 . C6 . H61 . 108.3(15) no C5 . C6 . H62 . 110.7(16) no O2 . C6 . H62 . 104.9(15) no H61 . C6 . H62 . 113(2) no F11 . C11 . O12 . 109.40(19) yes F11 . C11 . C12 . 107.35(17) yes O12 . C11 . C12 . 113.26(17) yes F11 . C11 . H111 . 107.3(14) no O12 . C11 . H111 . 108.4(16) no C12 . C11 . H111 . 111.0(16) no C11 . C12 . O11 . 107.02(18) yes C11 . C12 . C13 . 108.03(18) yes O11 . C12 . C13 . 103.54(16) yes C11 . C12 . H121 . 112.8(15) no O11 . C12 . H121 . 110.6(15) no C13 . C12 . H121 . 114.2(16) no C12 . C13 . O13 . 112.15(17) yes C12 . C13 . C14 . 105.22(18) yes O13 . C13 . C14 . 59.83(14) yes C12 . C13 . H131 . 120.3(16) no O13 . C13 . H131 . 118.1(16) no C14 . C13 . H131 . 126.7(17) no C13 . C14 . O13 . 59.69(14) yes C13 . C14 . C15 . 105.40(18) yes O13 . C14 . C15 . 112.82(19) yes C13 . C14 . H141 . 125.4(16) no O13 . C14 . H141 . 117.9(18) no C15 . C14 . H141 . 120.7(18) no C14 . C15 . O11 . 103.15(17) yes C14 . C15 . C16 . 110.62(18) yes O11 . C15 . C16 . 106.97(16) yes C14 . C15 . H151 . 115.6(15) no O11 . C15 . H151 . 110.2(15) no C16 . C15 . H151 . 109.9(16) no C15 . C16 . O12 . 110.40(18) yes C15 . C16 . H161 . 108.6(17) no O12 . C16 . H161 . 109.9(16) no C15 . C16 . H162 . 112.7(17) no O12 . C16 . H162 . 105.5(17) no H161 . C16 . H162 . 110(2) no # Attachment '- comp_16.cif' data_CRYSTALS_cif10 _database_code_depnum_ccdc_archive 'CCDC 832057' #TrackingRef '- comp_16.cif' _audit_creation_date 11-06-29 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title ? _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.1930(3) _cell_length_b 7.1640(3) _cell_length_c 10.9410(5) _cell_angle_alpha 90 _cell_angle_beta 109.287(2) _cell_angle_gamma 90 _cell_volume 606.14(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H7 F1 O3 # Dc = 1.60 Fooo = 304.00 Mu = 1.47 M = 292.24 # Found Formula = C6 H7 F1 O3 # Dc = 1.60 FOOO = 304.00 Mu = 1.47 M = 292.24 _chemical_formula_sum 'C6 H7 F1 O3' _chemical_formula_moiety 'C6 H7 F1 O3' _chemical_compound_source ? _chemical_formula_weight 146.12 _cell_measurement_reflns_used 1432 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.147 # Sheldrick geometric approximatio 0.97 0.97 # No experimental values of Tmin/max available _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 2763 _reflns_number_total 1493 _diffrn_reflns_av_R_equivalents 0.014 # Number of reflections with Friedels Law is 1493 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1375 _diffrn_reflns_theta_min 1.972 _diffrn_reflns_theta_max 27.398 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.398 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.19 _refine_diff_density_max 0.19 _refine_ls_number_reflns 1098 _refine_ls_number_restraints 1 _refine_ls_number_parameters 237 #_refine_ls_R_factor_ref 0.0304 _refine_ls_wR_factor_ref 0.0345 _refine_ls_goodness_of_fit_ref 1.0842 #_reflns_number_all 1484 _refine_ls_R_factor_all 0.0470 _refine_ls_wR_factor_all 0.0581 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 1098 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_gt 0.0345 _refine_ls_shift/su_max 0.000100 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.378 0.255 0.160 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 1.0114(2) 0.1728(3) -0.1190(2) 0.0483 1.0000 Uani . . . . . . F11 F 0.3055(2) -0.1872(3) -0.44272(19) 0.0403 1.0000 Uani . . . . . . O1 O 0.5956(3) 0.1123(4) -0.08385(19) 0.0324 1.0000 Uani . . . . . . O2 O 0.8141(3) 0.3832(3) -0.1250(2) 0.0322 1.0000 Uani . . . . . . O3 O 0.7461(3) 0.1075(4) 0.1622(2) 0.0370 1.0000 Uani . . . . . . O11 O 0.4003(2) 0.3026(4) -0.42234(18) 0.0279 1.0000 Uani . . . . . . O12 O 0.1704(3) 0.0431(3) -0.3848(2) 0.0312 1.0000 Uani . . . . . . O13 O 0.2577(3) 0.3109(4) -0.6693(2) 0.0386 1.0000 Uani . . . . . . C1 C 0.8349(4) 0.1930(5) -0.1444(4) 0.0329 1.0000 Uani . . . . . . C2 C 0.7764(4) 0.0733(5) -0.0519(3) 0.0306 1.0000 Uani . . . . . . C3 C 0.8551(4) 0.1443(5) 0.0843(3) 0.0318 1.0000 Uani . . . . . . C4 C 0.7363(4) 0.2872(5) 0.0987(3) 0.0307 1.0000 Uani . . . . . . C5 C 0.5945(4) 0.2961(5) -0.0307(3) 0.0296 1.0000 Uani . . . . . . C6 C 0.6467(4) 0.4330(5) -0.1171(3) 0.0328 1.0000 Uani . . . . . . C11 C 0.3336(4) -0.0089(4) -0.3892(3) 0.0290 1.0000 Uani . . . . . . C12 C 0.3952(3) 0.1190(5) -0.4757(3) 0.0247 1.0000 Uani . . . . . . C13 C 0.2567(4) 0.1337(5) -0.6071(3) 0.0289 1.0000 Uani . . . . . . C14 C 0.1446(4) 0.2833(5) -0.5937(3) 0.0318 1.0000 Uani . . . . . . C15 C 0.2191(4) 0.3520(5) -0.4562(3) 0.0304 1.0000 Uani . . . . . . C16 C 0.1476(5) 0.2408(5) -0.3684(3) 0.0330 1.0000 Uani . . . . . . H11 H 0.775(4) 0.159(5) -0.234(3) 0.031(8) 1.0000 Uiso . . . . . . H21 H 0.794(4) -0.055(6) -0.064(3) 0.031(9) 1.0000 Uiso . . . . . . H31 H 0.978(4) 0.147(6) 0.128(3) 0.036(9) 1.0000 Uiso . . . . . . H41 H 0.773(4) 0.398(5) 0.153(3) 0.031(9) 1.0000 Uiso . . . . . . H51 H 0.480(4) 0.321(6) -0.028(3) 0.026(8) 1.0000 Uiso . . . . . . H61 H 0.664(4) 0.562(6) -0.079(3) 0.033(9) 1.0000 Uiso . . . . . . H62 H 0.558(5) 0.433(6) -0.204(4) 0.043(9) 1.0000 Uiso . . . . . . H111 H 0.424(4) -0.013(5) -0.302(3) 0.032(8) 1.0000 Uiso . . . . . . H121 H 0.513(4) 0.080(6) -0.475(3) 0.029(8) 1.0000 Uiso . . . . . . H131 H 0.220(4) 0.020(5) -0.660(3) 0.032(9) 1.0000 Uiso . . . . . . H141 H 0.029(5) 0.287(5) -0.633(3) 0.037(9) 1.0000 Uiso . . . . . . H151 H 0.207(4) 0.495(6) -0.449(3) 0.036(9) 1.0000 Uiso . . . . . . H161 H 0.020(4) 0.259(5) -0.388(3) 0.037(9) 1.0000 Uiso . . . . . . H162 H 0.212(4) 0.275(6) -0.277(3) 0.042(9) 1.0000 Uiso . . . . . . 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 0.0466(10) 0.0516(13) 0.0565(11) 0.0068(10) 0.0300(9) 0.0069(10) F11 0.0452(10) 0.0191(8) 0.0611(11) -0.0010(9) 0.0236(8) -0.0027(8) O1 0.0323(11) 0.0286(12) 0.0352(11) -0.0040(11) 0.0097(9) -0.0055(10) O2 0.0363(11) 0.0267(12) 0.0355(12) 0.0016(10) 0.0144(9) -0.0026(9) O3 0.0439(12) 0.0387(13) 0.0333(11) 0.0098(12) 0.0192(9) 0.0041(12) O11 0.0312(11) 0.0211(10) 0.0319(10) -0.0053(10) 0.0113(8) -0.0058(9) O12 0.0331(10) 0.0267(12) 0.0390(12) 0.0009(10) 0.0189(9) -0.0028(9) O13 0.0496(13) 0.0365(12) 0.0341(11) 0.0095(13) 0.0197(10) 0.0068(12) C1 0.0374(15) 0.0330(18) 0.0315(16) 0.0000(13) 0.0155(13) -0.0016(14) C2 0.0363(16) 0.0224(19) 0.0353(15) -0.0021(13) 0.0148(13) 0.0006(14) C3 0.0332(16) 0.035(2) 0.0282(13) 0.0051(14) 0.0112(12) 0.0014(14) C4 0.0383(16) 0.0302(19) 0.0248(13) 0.0006(14) 0.0123(11) -0.0009(14) C5 0.0321(15) 0.0256(17) 0.0319(14) 0.0000(15) 0.0115(11) 0.0009(14) C6 0.0352(17) 0.0290(19) 0.0316(17) 0.0034(13) 0.0076(14) 0.0039(14) C11 0.0329(15) 0.0185(16) 0.0357(17) -0.0001(12) 0.0114(13) -0.0036(12) C12 0.0234(13) 0.0213(15) 0.0304(13) -0.0029(13) 0.0104(10) -0.0008(13) C13 0.0331(14) 0.0274(18) 0.0260(13) -0.0001(14) 0.0095(11) 0.0022(14) C14 0.0315(16) 0.033(2) 0.0313(14) 0.0048(14) 0.0105(12) 0.0067(14) C15 0.0339(16) 0.025(2) 0.0356(16) 0.0011(13) 0.0156(12) 0.0032(14) C16 0.0356(16) 0.0289(16) 0.0394(19) -0.0058(14) 0.0190(14) 0.0010(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.7166(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C1 . 1.387(4) yes F11 . C11 . 1.392(4) yes O1 . C2 . 1.432(4) yes O1 . C5 . 1.441(4) yes O2 . C1 . 1.398(4) yes O2 . C6 . 1.447(4) yes O3 . C3 . 1.448(4) yes O3 . C4 . 1.453(4) yes O11 . C12 . 1.434(4) yes O11 . C15 . 1.450(4) yes O12 . C11 . 1.404(4) yes O12 . C16 . 1.447(4) yes O13 . C13 . 1.441(4) yes O13 . C14 . 1.445(4) yes C1 . C2 . 1.520(5) yes C1 . H11 . 0.97(3) no C2 . C3 . 1.504(4) yes C2 . H21 . 0.95(4) no C3 . C4 . 1.457(5) yes C3 . H31 . 0.96(3) no C4 . C5 . 1.507(4) yes C4 . H41 . 0.98(4) no C5 . C6 . 1.518(5) yes C5 . H51 . 0.97(3) no C6 . H61 . 1.01(4) no C6 . H62 . 0.98(4) no C11 . C12 . 1.519(4) yes C11 . H111 . 1.00(3) no C12 . C13 . 1.512(4) yes C12 . H121 . 1.00(3) no C13 . C14 . 1.450(4) yes C13 . H131 . 0.99(4) no C14 . C15 . 1.507(4) yes C14 . H141 . 0.90(4) no C15 . C16 . 1.507(5) yes C15 . H151 . 1.04(4) no C16 . H161 . 1.00(3) no C16 . H162 . 0.99(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C5 . 102.9(2) yes C1 . O2 . C6 . 114.5(2) yes C3 . O3 . C4 . 60.3(2) yes C12 . O11 . C15 . 103.3(2) yes C11 . O12 . C16 . 115.3(2) yes C13 . O13 . C14 . 60.31(19) yes F1 . C1 . O2 . 104.0(3) yes F1 . C1 . C2 . 110.2(3) yes O2 . C1 . C2 . 111.5(3) yes F1 . C1 . H11 . 108.9(17) no O2 . C1 . H11 . 111(2) no C2 . C1 . H11 . 111.4(20) no C1 . C2 . O1 . 104.8(3) yes C1 . C2 . C3 . 110.0(3) yes O1 . C2 . C3 . 104.3(2) yes C1 . C2 . H21 . 111(2) no O1 . C2 . H21 . 110(2) no C3 . C2 . H21 . 116(2) no C2 . C3 . O3 . 112.1(3) yes C2 . C3 . C4 . 105.2(3) yes O3 . C3 . C4 . 60.01(19) yes C2 . C3 . H31 . 122(2) no O3 . C3 . H31 . 117.2(19) no C4 . C3 . H31 . 124(2) no C3 . C4 . O3 . 59.7(2) yes C3 . C4 . C5 . 105.3(3) yes O3 . C4 . C5 . 113.0(3) yes C3 . C4 . H41 . 123.4(18) no O3 . C4 . H41 . 118(2) no C5 . C4 . H41 . 121.7(19) no C4 . C5 . O1 . 103.6(3) yes C4 . C5 . C6 . 108.9(3) yes O1 . C5 . C6 . 107.4(2) yes C4 . C5 . H51 . 116.0(16) no O1 . C5 . H51 . 108(2) no C6 . C5 . H51 . 112(2) no C5 . C6 . O2 . 110.2(3) yes C5 . C6 . H61 . 111.5(19) no O2 . C6 . H61 . 104.0(19) no C5 . C6 . H62 . 109(2) no O2 . C6 . H62 . 110.9(19) no H61 . C6 . H62 . 111(3) no F11 . C11 . O12 . 103.4(2) yes F11 . C11 . C12 . 109.5(2) yes O12 . C11 . C12 . 112.2(3) yes F11 . C11 . H111 . 110(2) no O12 . C11 . H111 . 113.0(17) no C12 . C11 . H111 . 108.5(19) no C11 . C12 . O11 . 105.7(2) yes C11 . C12 . C13 . 109.5(2) yes O11 . C12 . C13 . 103.6(2) yes C11 . C12 . H121 . 110(2) no O11 . C12 . H121 . 111(2) no C13 . C12 . H121 . 116.2(17) no C12 . C13 . O13 . 113.0(3) yes C12 . C13 . C14 . 104.9(2) yes O13 . C13 . C14 . 60.0(2) yes C12 . C13 . H131 . 119.1(19) no O13 . C13 . H131 . 119.9(20) no C14 . C13 . H131 . 126.0(19) no C13 . C14 . O13 . 59.72(19) yes C13 . C14 . C15 . 106.3(2) yes O13 . C14 . C15 . 113.7(3) yes C13 . C14 . H141 . 125(2) no O13 . C14 . H141 . 119(2) no C15 . C14 . H141 . 119(2) no C14 . C15 . O11 . 102.6(2) yes C14 . C15 . C16 . 110.4(3) yes O11 . C15 . C16 . 106.8(3) yes C14 . C15 . H151 . 112.6(19) no O11 . C15 . H151 . 109.9(20) no C16 . C15 . H151 . 113.9(20) no C15 . C16 . O12 . 110.2(3) yes C15 . C16 . H161 . 113.2(20) no O12 . C16 . H161 . 106(2) no C15 . C16 . H162 . 109(2) no O12 . C16 . H162 . 108(2) no H161 . C16 . H162 . 110(3) no # Attachment '- comp_17.cif' data_CRYSTALS_cif11 _database_code_depnum_ccdc_archive 'CCDC 832058' #TrackingRef '- comp_17.cif' _audit_creation_date 11-06-29 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title ? _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.3628(2) _cell_length_b 9.2072(3) _cell_length_c 10.1628(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 595.37(3) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H7 F1 O3 # Dc = 1.63 Fooo = 304.00 Mu = 1.49 M = 146.12 # Found Formula = C6 H7 F1 O3 # Dc = 1.63 FOOO = 304.00 Mu = 1.49 M = 146.12 _chemical_formula_sum 'C6 H7 F1 O3' _chemical_formula_moiety 'C6 H7 F1 O3' _chemical_compound_source ? _chemical_formula_weight 146.12 _cell_measurement_reflns_used 839 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.149 # Sheldrick geometric approximatio 0.96 0.96 # No experimental values of Tmin/max available _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 1374 _reflns_number_total 824 _diffrn_reflns_av_R_equivalents 0.006 # Number of reflections with Friedels Law is 824 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 683 _diffrn_reflns_theta_min 2.985 _diffrn_reflns_theta_max 27.507 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.507 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.21 _refine_diff_density_max 0.14 _refine_ls_number_reflns 722 _refine_ls_number_restraints 0 _refine_ls_number_parameters 119 #_refine_ls_R_factor_ref 0.0295 _refine_ls_wR_factor_ref 0.0341 _refine_ls_goodness_of_fit_ref 1.1757 #_reflns_number_all 820 _refine_ls_R_factor_all 0.0347 _refine_ls_wR_factor_all 0.0384 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 722 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_gt 0.0341 _refine_ls_shift/su_max 0.000085 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.447 0.418 0.224 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 0.04768(18) -0.27825(15) -0.15222(11) 0.0403 1.0000 Uani . . . . . . O1 O -0.2614(2) -0.16863(13) -0.19630(13) 0.0285 1.0000 Uani . . . . . . O2 O -0.2596(2) -0.47527(12) -0.20130(12) 0.0258 1.0000 Uani . . . . . . O3 O -0.3869(2) -0.21423(14) -0.44019(12) 0.0315 1.0000 Uani . . . . . . C1 C -0.0964(3) -0.2465(2) -0.25246(18) 0.0281 1.0000 Uani . . . . . . C2 C -0.1722(3) -0.39100(19) -0.30727(16) 0.0240 1.0000 Uani . . . . . . C3 C -0.3475(3) -0.36508(18) -0.40473(17) 0.0258 1.0000 Uani . . . . . . C4 C -0.5144(3) -0.2819(2) -0.34098(17) 0.0274 1.0000 Uani . . . . . . C5 C -0.4547(3) -0.24848(17) -0.19831(18) 0.0243 1.0000 Uani . . . . . . C6 C -0.4220(3) -0.3947(2) -0.13200(17) 0.0272 1.0000 Uani . . . . . . H11 H -0.018(4) -0.186(2) -0.318(2) 0.030(5) 1.0000 Uiso . . . . . . H21 H -0.057(3) -0.443(3) -0.338(2) 0.030(6) 1.0000 Uiso . . . . . . H31 H -0.373(3) -0.435(2) -0.472(2) 0.027(5) 1.0000 Uiso . . . . . . H41 H -0.665(4) -0.297(3) -0.356(2) 0.036(6) 1.0000 Uiso . . . . . . H51 H -0.565(3) -0.189(2) -0.152(2) 0.028(5) 1.0000 Uiso . . . . . . H61 H -0.547(3) -0.452(3) -0.136(2) 0.028(5) 1.0000 Uiso . . . . . . H62 H -0.377(4) -0.382(3) -0.039(3) 0.038(6) 1.0000 Uiso . . . . . . 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 0.0279(6) 0.0573(8) 0.0356(6) -0.0088(6) -0.0079(5) -0.0029(6) O1 0.0289(6) 0.0235(5) 0.0329(6) -0.0072(5) 0.0054(6) -0.0032(5) O2 0.0300(6) 0.0221(5) 0.0252(5) 0.0022(5) 0.0019(6) 0.0040(5) O3 0.0385(7) 0.0301(6) 0.0260(6) 0.0068(5) 0.0046(6) 0.0078(6) C1 0.0239(8) 0.0323(9) 0.0280(7) -0.0041(7) 0.0007(7) -0.0026(7) C2 0.0246(8) 0.0247(7) 0.0228(7) -0.0018(7) 0.0020(7) 0.0024(6) C3 0.0304(8) 0.0261(8) 0.0210(7) -0.0009(6) -0.0016(7) 0.0019(7) C4 0.0259(8) 0.0310(9) 0.0253(8) 0.0024(7) 0.0003(6) 0.0037(7) C5 0.0240(7) 0.0226(8) 0.0263(7) -0.0008(7) 0.0037(7) 0.0023(6) C6 0.0315(9) 0.0244(8) 0.0259(7) 0.0022(7) 0.0045(8) 0.0025(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.800(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C1 . 1.401(2) yes O1 . C1 . 1.394(2) yes O1 . C5 . 1.433(2) yes O2 . C2 . 1.439(2) yes O2 . C6 . 1.454(2) yes O3 . C3 . 1.457(2) yes O3 . C4 . 1.436(2) yes C1 . C2 . 1.521(2) yes C1 . H11 . 1.00(2) no C2 . C3 . 1.510(2) yes C2 . H21 . 0.93(2) no C3 . C4 . 1.461(2) yes C3 . H31 . 0.95(2) no C4 . C5 . 1.530(3) yes C4 . H41 . 0.98(2) no C5 . C6 . 1.520(2) yes C5 . H51 . 1.00(2) no C6 . H61 . 0.95(2) no C6 . H62 . 0.99(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 112.15(12) yes C2 . O2 . C6 . 111.22(12) yes C3 . O3 . C4 . 60.64(12) yes F1 . C1 . O1 . 107.61(14) yes F1 . C1 . C2 . 106.92(15) yes O1 . C1 . C2 . 111.13(14) yes F1 . C1 . H11 . 105.8(13) no O1 . C1 . H11 . 111.2(13) no C2 . C1 . H11 . 113.8(13) no C1 . C2 . O2 . 108.68(14) yes C1 . C2 . C3 . 109.65(14) yes O2 . C2 . C3 . 106.91(13) yes C1 . C2 . H21 . 108.8(14) no O2 . C2 . H21 . 106.4(14) no C3 . C2 . H21 . 116.1(14) no C2 . C3 . O3 . 116.10(14) yes C2 . C3 . C4 . 109.18(15) yes O3 . C3 . C4 . 58.99(11) yes C2 . C3 . H31 . 119.4(13) no O3 . C3 . H31 . 115.7(13) no C4 . C3 . H31 . 123.3(14) no C3 . C4 . O3 . 60.37(11) yes C3 . C4 . C5 . 110.21(15) yes O3 . C4 . C5 . 115.96(16) yes C3 . C4 . H41 . 124.5(15) no O3 . C4 . H41 . 120.0(15) no C5 . C4 . H41 . 115.0(15) no C4 . C5 . O1 . 109.25(14) yes C4 . C5 . C6 . 106.01(14) yes O1 . C5 . C6 . 109.32(14) yes C4 . C5 . H51 . 112.2(12) no O1 . C5 . H51 . 108.2(12) no C6 . C5 . H51 . 111.8(13) no C5 . C6 . O2 . 109.54(14) yes C5 . C6 . H61 . 111.1(14) no O2 . C6 . H61 . 106.7(13) no C5 . C6 . H62 . 110.7(14) no O2 . C6 . H62 . 108.4(14) no H61 . C6 . H62 . 110(2) no # Attachment '- comp_19.cif' data_CRYSTALS_cif12 _database_code_depnum_ccdc_archive 'CCDC 832059' #TrackingRef '- comp_19.cif' _audit_creation_date 11-06-29 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e343_2f_sykora_0m in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.7591(3) _cell_length_b 6.2197(3) _cell_length_c 16.2984(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 583.81(5) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H7 F1 O3 # Dc = 1.66 Fooo = 304.00 Mu = 1.52 M = 146.12 # Found Formula = C6 H7 F1 O3 # Dc = 1.66 FOOO = 304.00 Mu = 1.52 M = 146.12 _chemical_formula_sum 'C6 H7 F1 O3' _chemical_formula_moiety 'C6 H7 F1 O3' _chemical_compound_source ? _chemical_formula_weight 146.12 _cell_measurement_reflns_used 2931 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.152 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 6767 _reflns_number_total 947 _diffrn_reflns_av_R_equivalents 0.022 # Number of reflections with Friedels Law is 947 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 875 _diffrn_reflns_theta_min 2.499 _diffrn_reflns_theta_max 30.302 _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 27.575 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.27 _refine_ls_number_reflns 771 _refine_ls_number_restraints 0 _refine_ls_number_parameters 119 #_refine_ls_R_factor_ref 0.0271 _refine_ls_wR_factor_ref 0.0308 _refine_ls_goodness_of_fit_ref 1.1361 #_reflns_number_all 944 _refine_ls_R_factor_all 0.0373 _refine_ls_wR_factor_all 0.0413 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 771 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_gt 0.0308 _refine_ls_shift/su_max 0.000363 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.219 0.170 0.101 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 0.0507(2) 1.26172(18) 0.81512(7) 0.0262 1.0000 Uani . . . . . . O1 O 0.1031(2) 1.0600(2) 0.92871(7) 0.0170 1.0000 Uani . . . . . . O2 O 0.4921(2) 1.1115(2) 0.82442(7) 0.0170 1.0000 Uani . . . . . . O3 O 0.5757(2) 0.7263(2) 0.88514(8) 0.0205 1.0000 Uani . . . . . . C1 C 0.0853(3) 1.0509(3) 0.84320(11) 0.0166 1.0000 Uani . . . . . . C2 C 0.3103(3) 0.9665(3) 0.80529(10) 0.0140 1.0000 Uani . . . . . . C3 C 0.3529(3) 0.7481(3) 0.84550(10) 0.0170 1.0000 Uani . . . . . . C4 C 0.3731(3) 0.7742(3) 0.93440(10) 0.0171 1.0000 Uani . . . . . . C5 C 0.3375(3) 1.0092(3) 0.95646(10) 0.0147 1.0000 Uani . . . . . . C6 C 0.5074(3) 1.1513(3) 0.91152(10) 0.0161 1.0000 Uani . . . . . . H11 H -0.055(4) 0.974(3) 0.8277(13) 0.015(5) 1.0000 Uiso . . . . . . H21 H 0.303(4) 0.956(3) 0.7475(13) 0.009(5) 1.0000 Uiso . . . . . . H31 H 0.294(4) 0.622(4) 0.8218(15) 0.022(6) 1.0000 Uiso . . . . . . H41 H 0.338(4) 0.663(4) 0.9720(15) 0.022(6) 1.0000 Uiso . . . . . . H51 H 0.340(4) 1.038(3) 1.0137(13) 0.016(5) 1.0000 Uiso . . . . . . H61 H 0.468(4) 1.302(3) 0.9224(13) 0.011(5) 1.0000 Uiso . . . . . . H62 H 0.661(4) 1.119(4) 0.9286(13) 0.013(5) 1.0000 Uiso . . . . . . 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 0.0283(6) 0.0217(5) 0.0288(5) 0.0073(5) -0.0060(5) 0.0070(5) O1 0.0132(6) 0.0234(6) 0.0144(6) -0.0018(5) 0.0007(4) 0.0045(5) O2 0.0166(6) 0.0198(6) 0.0145(5) 0.0013(5) 0.0005(5) -0.0055(5) O3 0.0186(6) 0.0203(6) 0.0228(6) -0.0012(5) 0.0018(5) 0.0066(5) C1 0.0153(8) 0.0163(7) 0.0183(8) 0.0009(6) -0.0020(6) 0.0006(7) C2 0.0149(8) 0.0173(8) 0.0096(7) -0.0002(6) 0.0000(6) -0.0032(6) C3 0.0179(8) 0.0139(7) 0.0192(7) -0.0024(6) 0.0014(6) -0.0011(7) C4 0.0171(8) 0.0168(7) 0.0173(7) 0.0031(6) 0.0016(6) 0.0021(7) C5 0.0138(7) 0.0175(8) 0.0128(7) -0.0022(6) -0.0014(6) 0.0034(6) C6 0.0158(7) 0.0165(7) 0.0160(8) -0.0030(6) -0.0032(7) 0.0002(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3703(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C1 . 1.403(2) yes O1 . C1 . 1.399(2) yes O1 . C5 . 1.458(2) yes O2 . C2 . 1.417(2) yes O2 . C6 . 1.444(2) yes O3 . C3 . 1.443(2) yes O3 . C4 . 1.447(2) yes C1 . C2 . 1.528(2) yes C1 . H11 . 0.97(2) no C2 . C3 . 1.528(3) yes C2 . H21 . 0.94(2) no C3 . C4 . 1.463(2) yes C3 . H31 . 0.94(2) no C4 . C5 . 1.520(2) yes C4 . H41 . 0.95(2) no C5 . C6 . 1.509(3) yes C5 . H51 . 0.95(2) no C6 . H61 . 0.98(2) no C6 . H62 . 0.95(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 111.58(13) yes C2 . O2 . C6 . 111.75(13) yes C3 . O3 . C4 . 60.82(11) yes F1 . C1 . O1 . 107.29(13) yes F1 . C1 . C2 . 108.04(14) yes O1 . C1 . C2 . 110.80(14) yes F1 . C1 . H11 . 104.9(12) no O1 . C1 . H11 . 109.9(13) no C2 . C1 . H11 . 115.5(13) no C1 . C2 . O2 . 108.61(13) yes C1 . C2 . C3 . 105.55(14) yes O2 . C2 . C3 . 110.65(14) yes C1 . C2 . H21 . 112.8(13) no O2 . C2 . H21 . 107.2(12) no C3 . C2 . H21 . 112.0(12) no C2 . C3 . O3 . 114.73(15) yes C2 . C3 . C4 . 109.81(14) yes O3 . C3 . C4 . 59.74(11) yes C2 . C3 . H31 . 120.7(14) no O3 . C3 . H31 . 115.2(14) no C4 . C3 . H31 . 122.0(15) no C3 . C4 . O3 . 59.45(11) yes C3 . C4 . C5 . 109.30(15) yes O3 . C4 . C5 . 115.99(14) yes C3 . C4 . H41 . 122.9(14) no O3 . C4 . H41 . 112.4(15) no C5 . C4 . H41 . 121.4(14) no C4 . C5 . O1 . 105.08(14) yes C4 . C5 . C6 . 111.17(14) yes O1 . C5 . C6 . 108.84(13) yes C4 . C5 . H51 . 114.5(13) no O1 . C5 . H51 . 106.1(14) no C6 . C5 . H51 . 110.8(14) no C5 . C6 . O2 . 109.72(14) yes C5 . C6 . H61 . 108.7(13) no O2 . C6 . H61 . 109.1(12) no C5 . C6 . H62 . 109.7(13) no O2 . C6 . H62 . 107.9(13) no H61 . C6 . H62 . 111.6(19) no # Attachment '- comp_20.cif' data_CRYSTALS_cif13 _database_code_depnum_ccdc_archive 'CCDC 832060' #TrackingRef '- comp_20.cif' _audit_creation_date 11-06-29 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e343_1f_sykora_0m in P2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.1181(3) _cell_length_b 7.1297(3) _cell_length_c 6.9272(4) _cell_angle_alpha 90 _cell_angle_beta 94.628(2) _cell_angle_gamma 90 _cell_volume 301.18(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C6 H7 F1 O3 # Dc = 1.61 Fooo = 152.00 Mu = 1.48 M = 146.12 # Found Formula = C6 H7 F1 O3 # Dc = 1.61 FOOO = 152.00 Mu = 1.48 M = 146.12 _chemical_formula_sum 'C6 H7 F1 O3' _chemical_formula_moiety 'C6 H7 F1 O3' _chemical_compound_source ? _chemical_formula_weight 146.12 _cell_measurement_reflns_used 3722 _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.36 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_max 0.66 _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 152 _exptl_absorpt_coefficient_mu 0.148 # Sheldrick geometric approximatio 0.95 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.95 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 4728 _reflns_number_total 846 _diffrn_reflns_av_R_equivalents 0.022 # Number of reflections with Friedels Law is 846 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 857 _diffrn_reflns_theta_min 2.950 _diffrn_reflns_theta_max 29.727 _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 27.051 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 9 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.14 _refine_diff_density_max 0.24 _refine_ls_number_reflns 749 _refine_ls_number_restraints 1 _refine_ls_number_parameters 119 #_refine_ls_R_factor_ref 0.0235 _refine_ls_wR_factor_ref 0.0277 _refine_ls_goodness_of_fit_ref 1.1481 #_reflns_number_all 844 _refine_ls_R_factor_all 0.0266 _refine_ls_wR_factor_all 0.0318 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 749 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_gt 0.0277 _refine_ls_shift/su_max 0.000181 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.171 0.115 0.530E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 0.19528(18) 0.42450(17) 0.69543(16) 0.0320 1.0000 Uani . . . . . . O1 O 0.39970(19) 0.2025(2) 0.85677(17) 0.0244 1.0000 Uani . . . . . . O2 O 0.28123(18) -0.0589(2) 0.57660(16) 0.0233 1.0000 Uani . . . . . . O3 O -0.06368(18) -0.0866(2) 0.78653(17) 0.0262 1.0000 Uani . . . . . . C1 C 0.3157(3) 0.2598(2) 0.6741(2) 0.0216 1.0000 Uani . . . . . . C2 C 0.1613(2) 0.1118(2) 0.5811(2) 0.0188 1.0000 Uani . . . . . . C3 C -0.0262(2) 0.0972(2) 0.7107(2) 0.0219 1.0000 Uani . . . . . . C4 C 0.0588(3) 0.0484(3) 0.9077(2) 0.0237 1.0000 Uani . . . . . . C5 C 0.3051(3) 0.0255(2) 0.9140(2) 0.0212 1.0000 Uani . . . . . . C6 C 0.3655(2) -0.1188(2) 0.7683(2) 0.0231 1.0000 Uani . . . . . . H11 H 0.439(4) 0.294(4) 0.595(3) 0.028(5) 1.0000 Uiso . . . . . . H21 H 0.117(4) 0.143(4) 0.454(3) 0.029(6) 1.0000 Uiso . . . . . . H31 H -0.151(4) 0.168(4) 0.684(4) 0.033(6) 1.0000 Uiso . . . . . . H41 H -0.012(4) 0.090(4) 1.014(4) 0.031(6) 1.0000 Uiso . . . . . . H51 H 0.369(4) 0.005(4) 1.037(3) 0.029(6) 1.0000 Uiso . . . . . . H61 H 0.532(4) -0.123(4) 0.767(3) 0.030(6) 1.0000 Uiso . . . . . . H62 H 0.303(4) -0.239(3) 0.804(3) 0.027(5) 1.0000 Uiso . . . . . . 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 0.0435(5) 0.0144(5) 0.0366(5) 0.0007(4) -0.0053(4) 0.0008(4) O1 0.0265(5) 0.0192(6) 0.0259(6) 0.0008(4) -0.0078(4) -0.0069(4) O2 0.0275(5) 0.0209(6) 0.0220(5) -0.0049(5) 0.0048(4) 0.0031(4) O3 0.0218(5) 0.0223(6) 0.0350(6) 0.0022(5) 0.0048(4) -0.0065(5) C1 0.0243(7) 0.0173(7) 0.0232(7) 0.0018(6) 0.0017(6) -0.0042(6) C2 0.0219(7) 0.0172(7) 0.0169(6) 0.0002(5) -0.0010(5) -0.0012(5) C3 0.0163(7) 0.0182(7) 0.0308(8) 0.0005(6) 0.0002(5) 0.0009(6) C4 0.0282(8) 0.0206(7) 0.0237(8) -0.0010(6) 0.0100(6) -0.0008(6) C5 0.0264(7) 0.0176(7) 0.0184(7) 0.0028(5) -0.0054(5) -0.0025(5) C6 0.0188(7) 0.0186(8) 0.0313(8) 0.0009(6) -0.0010(6) 0.0029(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.7237(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C1 . 1.4003(19) yes O1 . C1 . 1.3886(19) yes O1 . C5 . 1.4566(19) yes O2 . C2 . 1.4225(19) yes O2 . C6 . 1.449(2) yes O3 . C3 . 1.437(2) yes O3 . C4 . 1.446(2) yes C1 . C2 . 1.524(2) yes C1 . H11 . 1.00(2) no C2 . C3 . 1.516(2) yes C2 . H21 . 0.93(2) no C3 . C4 . 1.463(2) yes C3 . H31 . 0.92(3) no C4 . C5 . 1.513(2) yes C4 . H41 . 0.93(3) no C5 . C6 . 1.508(2) yes C5 . H51 . 0.92(2) no C6 . H61 . 1.02(2) no C6 . H62 . 0.98(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 112.15(11) yes C2 . O2 . C6 . 112.22(11) yes C3 . O3 . C4 . 60.98(11) yes F1 . C1 . O1 . 108.04(13) yes F1 . C1 . C2 . 108.18(12) yes O1 . C1 . C2 . 110.64(13) yes F1 . C1 . H11 . 106.4(15) no O1 . C1 . H11 . 109.5(13) no C2 . C1 . H11 . 113.9(14) no C1 . C2 . O2 . 107.35(12) yes C1 . C2 . C3 . 105.66(12) yes O2 . C2 . C3 . 111.77(12) yes C1 . C2 . H21 . 111.1(15) no O2 . C2 . H21 . 107.1(15) no C3 . C2 . H21 . 113.8(13) no C2 . C3 . O3 . 115.42(12) yes C2 . C3 . C4 . 109.86(13) yes O3 . C3 . C4 . 59.80(11) yes C2 . C3 . H31 . 119.8(15) no O3 . C3 . H31 . 114.9(15) no C4 . C3 . H31 . 123.0(15) no C3 . C4 . O3 . 59.22(10) yes C3 . C4 . C5 . 109.33(13) yes O3 . C4 . C5 . 114.42(13) yes C3 . C4 . H41 . 120.4(15) no O3 . C4 . H41 . 114.8(16) no C5 . C4 . H41 . 122.5(15) no C4 . C5 . O1 . 108.41(13) yes C4 . C5 . C6 . 110.57(13) yes O1 . C5 . C6 . 106.53(13) yes C4 . C5 . H51 . 112.9(13) no O1 . C5 . H51 . 104.1(15) no C6 . C5 . H51 . 113.8(15) no C5 . C6 . O2 . 108.89(12) yes C5 . C6 . H61 . 108.8(14) no O2 . C6 . H61 . 106.5(13) no C5 . C6 . H62 . 108.0(14) no O2 . C6 . H62 . 111.7(14) no H61 . C6 . H62 . 113(2) no # Attachment '- comp_21.cif' data_CRYSTALS_cif14 _database_code_depnum_ccdc_archive 'CCDC 832061' #TrackingRef '- comp_21.cif' _audit_creation_date 11-06-29 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'Compound X' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.2710(2) _cell_length_b 7.6812(2) _cell_length_c 12.1999(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 587.65(3) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H7 F1 O3 # Dc = 1.65 Fooo = 304.00 Mu = 1.51 M = 146.12 # Found Formula = C6 H7 F1 O3 # Dc = 1.65 FOOO = 304.00 Mu = 1.51 M = 146.12 _chemical_formula_sum 'C6 H7 F1 O3' _chemical_formula_moiety 'C6 H7 F1 O3' _chemical_compound_source ? _chemical_formula_weight 146.12 _cell_measurement_reflns_used 815 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description oktahedron _exptl_crystal_colour colourless _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.151 # Sheldrick geometric approximatio 0.96 0.96 # No experimental values of Tmin/max available _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 1339 _reflns_number_total 803 _diffrn_reflns_av_R_equivalents 0.004 # Number of reflections with Friedels Law is 803 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 673 _diffrn_reflns_theta_min 3.134 _diffrn_reflns_theta_max 27.472 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.472 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.21 _refine_diff_density_max 0.14 _refine_ls_number_reflns 759 _refine_ls_number_restraints 0 _refine_ls_number_parameters 119 #_refine_ls_R_factor_ref 0.0267 _refine_ls_wR_factor_ref 0.0298 _refine_ls_goodness_of_fit_ref 1.1424 #_reflns_number_all 800 _refine_ls_R_factor_all 0.0281 _refine_ls_wR_factor_all 0.0303 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 759 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_gt 0.0298 _refine_ls_shift/su_max 0.000199 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.977 0.918 0.715 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 0.96786(13) 0.40838(11) 0.27925(6) 0.0305 1.0000 Uani . . . . . . O1 O 0.62465(14) 0.30705(11) 0.41237(7) 0.0226 1.0000 Uani . . . . . . O2 O 0.67272(14) 0.57666(11) 0.26511(7) 0.0217 1.0000 Uani . . . . . . O3 O 0.52420(15) 0.70099(11) 0.46104(7) 0.0255 1.0000 Uani . . . . . . C1 C 0.83712(19) 0.53126(16) 0.33363(9) 0.0209 1.0000 Uani . . . . . . C2 C 0.77051(19) 0.44515(15) 0.44045(9) 0.0204 1.0000 Uani . . . . . . C3 C 0.6400(2) 0.56233(16) 0.51569(9) 0.0236 1.0000 Uani . . . . . . C4 C 0.41938(19) 0.53543(17) 0.48099(9) 0.0236 1.0000 Uani . . . . . . C5 C 0.4341(2) 0.40626(15) 0.38615(9) 0.0208 1.0000 Uani . . . . . . C6 C 0.4705(2) 0.48646(15) 0.27396(9) 0.0218 1.0000 Uani . . . . . . H11 H 0.923(3) 0.634(2) 0.3425(14) 0.024(4) 1.0000 Uiso . . . . . . H21 H 0.895(3) 0.398(3) 0.4751(15) 0.031(5) 1.0000 Uiso . . . . . . H31 H 0.684(3) 0.575(2) 0.5901(16) 0.034(5) 1.0000 Uiso . . . . . . H41 H 0.297(3) 0.535(2) 0.5229(15) 0.028(4) 1.0000 Uiso . . . . . . H51 H 0.314(3) 0.326(2) 0.3849(14) 0.027(4) 1.0000 Uiso . . . . . . H61 H 0.359(4) 0.565(2) 0.2586(16) 0.035(5) 1.0000 Uiso . . . . . . H62 H 0.463(4) 0.396(3) 0.2182(16) 0.039(5) 1.0000 Uiso . . . . . . 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 0.0245(4) 0.0402(4) 0.0268(4) -0.0039(3) 0.0034(3) 0.0094(3) O1 0.0222(4) 0.0182(4) 0.0273(4) 0.0033(3) -0.0030(3) 0.0005(3) O2 0.0217(4) 0.0242(4) 0.0192(4) 0.0047(3) -0.0004(3) -0.0004(3) O3 0.0273(4) 0.0208(4) 0.0283(4) -0.0020(3) 0.0014(4) 0.0008(4) C1 0.0200(5) 0.0228(5) 0.0198(5) -0.0002(4) 0.0006(4) 0.0009(4) C2 0.0204(5) 0.0219(5) 0.0190(5) 0.0023(4) -0.0020(4) -0.0002(4) C3 0.0282(6) 0.0255(6) 0.0172(5) -0.0006(4) 0.0007(4) -0.0015(5) C4 0.0229(6) 0.0251(6) 0.0228(5) 0.0000(4) 0.0046(4) -0.0001(4) C5 0.0196(5) 0.0194(5) 0.0234(5) 0.0020(4) -0.0022(4) -0.0002(4) C6 0.0226(5) 0.0206(5) 0.0223(5) 0.0009(4) -0.0045(4) -0.0010(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.397(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C1 . 1.4154(13) yes O1 . C2 . 1.4420(13) yes O1 . C5 . 1.4529(14) yes O2 . C1 . 1.3723(14) yes O2 . C6 . 1.4489(16) yes O3 . C3 . 1.4512(14) yes O3 . C4 . 1.4521(15) yes C1 . C2 . 1.5199(15) yes C1 . H11 . 0.959(18) no C2 . C3 . 1.5240(16) yes C2 . H21 . 0.957(19) no C3 . C4 . 1.4614(17) yes C3 . H31 . 0.95(2) no C4 . C5 . 1.5270(17) yes C4 . H41 . 0.92(2) no C5 . C6 . 1.5182(15) yes C5 . H51 . 0.97(2) no C6 . H61 . 0.94(2) no C6 . H62 . 0.97(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C5 . 100.85(8) yes C1 . O2 . C6 . 119.38(8) yes C3 . O3 . C4 . 60.44(8) yes F1 . C1 . O2 . 108.61(9) yes F1 . C1 . C2 . 105.72(9) yes O2 . C1 . C2 . 115.24(10) yes F1 . C1 . H11 . 105.9(10) no O2 . C1 . H11 . 106.4(11) no C2 . C1 . H11 . 114.5(10) no C1 . C2 . O1 . 106.91(9) yes C1 . C2 . C3 . 114.02(9) yes O1 . C2 . C3 . 103.70(9) yes C1 . C2 . H21 . 108.6(12) no O1 . C2 . H21 . 110.0(12) no C3 . C2 . H21 . 113.2(11) no C2 . C3 . O3 . 115.18(9) yes C2 . C3 . C4 . 104.50(9) yes O3 . C3 . C4 . 59.81(8) yes C2 . C3 . H31 . 118.5(13) no O3 . C3 . H31 . 120.6(12) no C4 . C3 . H31 . 124.2(13) no C3 . C4 . O3 . 59.75(8) yes C3 . C4 . C5 . 104.72(9) yes O3 . C4 . C5 . 114.50(9) yes C3 . C4 . H41 . 128.9(12) no O3 . C4 . H41 . 118.3(10) no C5 . C4 . H41 . 117.9(11) no C4 . C5 . O1 . 102.92(9) yes C4 . C5 . C6 . 115.38(10) yes O1 . C5 . C6 . 106.71(10) yes C4 . C5 . H51 . 112.2(10) no O1 . C5 . H51 . 107.7(11) no C6 . C5 . H51 . 111.1(11) no C5 . C6 . O2 . 113.14(9) yes C5 . C6 . H61 . 109.2(12) no O2 . C6 . H61 . 109.0(12) no C5 . C6 . H62 . 109.6(12) no O2 . C6 . H62 . 109.5(14) no H61 . C6 . H62 . 106.3(17) no # Attachment '- comp_22.cif' data_CRYSTALS_cif15 _database_code_depnum_ccdc_archive 'CCDC 832062' #TrackingRef '- comp_22.cif' _audit_creation_date 11-06-29 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title ? _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.3457(2) _cell_length_b 7.8536(4) _cell_length_c 12.1288(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 604.46(4) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H7 F1 O3 # Dc = 1.61 Fooo = 304.00 Mu = 1.47 M = 146.12 # Found Formula = C6 H7 F1 O3 # Dc = 1.61 FOOO = 304.00 Mu = 1.47 M = 146.12 _chemical_formula_sum 'C6 H7 F1 O3' _chemical_formula_moiety 'C6 H7 F1 O3' _chemical_compound_source ? _chemical_formula_weight 146.12 _cell_measurement_reflns_used 828 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 293 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.27 _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.147 # Sheldrick geometric approximatio 0.96 0.96 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 1379 _reflns_number_total 828 _diffrn_reflns_av_R_equivalents 0.007 # Number of reflections with Friedels Law is 828 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 691 _diffrn_reflns_theta_min 3.090 _diffrn_reflns_theta_max 27.456 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.456 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.17 _refine_diff_density_max 0.13 _refine_ls_number_reflns 745 _refine_ls_number_restraints 0 _refine_ls_number_parameters 119 #_refine_ls_R_factor_ref 0.0281 _refine_ls_wR_factor_ref 0.0295 _refine_ls_goodness_of_fit_ref 1.1513 #_reflns_number_all 825 _refine_ls_R_factor_all 0.0317 _refine_ls_wR_factor_all 0.0351 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 745 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_gt 0.0295 _refine_ls_shift/su_max 0.000140 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.285 0.114 0.446E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 1.0274(2) -0.11470(18) 0.05543(11) 0.0396 1.0000 Uani . . . . . . O1 O 0.7151(2) 0.25926(16) 0.10827(10) 0.0262 1.0000 Uani . . . . . . O2 O 0.47723(19) 0.05938(18) 0.15603(11) 0.0285 1.0000 Uani . . . . . . O3 O 0.8010(2) -0.07725(16) 0.26786(10) 0.0261 1.0000 Uani . . . . . . C1 C 0.6124(3) 0.1849(3) 0.20093(14) 0.0258 1.0000 Uani . . . . . . C2 C 0.7773(3) 0.1051(2) 0.27656(14) 0.0243 1.0000 Uani . . . . . . C3 C 0.9649(3) 0.0312(2) 0.22475(16) 0.0259 1.0000 Uani . . . . . . C4 C 0.9797(3) 0.0450(2) 0.10186(16) 0.0265 1.0000 Uani . . . . . . C5 C 0.7776(3) 0.1100(2) 0.04819(15) 0.0241 1.0000 Uani . . . . . . C6 C 0.5848(3) -0.0052(3) 0.05984(16) 0.0277 1.0000 Uani . . . . . . H11 H 0.522(4) 0.272(3) 0.2423(19) 0.038(6) 1.0000 Uiso . . . . . . H21 H 0.775(3) 0.148(2) 0.3521(15) 0.019(5) 1.0000 Uiso . . . . . . H31 H 1.095(3) 0.030(3) 0.2639(18) 0.029(6) 1.0000 Uiso . . . . . . H41 H 1.103(4) 0.121(3) 0.0841(17) 0.029(6) 1.0000 Uiso . . . . . . H51 H 0.810(3) 0.144(3) -0.0300(16) 0.023(5) 1.0000 Uiso . . . . . . H61 H 0.629(4) -0.129(3) 0.0712(19) 0.038(7) 1.0000 Uiso . . . . . . H62 H 0.488(4) 0.012(3) -0.0032(19) 0.043(7) 1.0000 Uiso . . . . . . 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 0.0431(7) 0.0359(6) 0.0399(6) -0.0010(5) 0.0072(6) 0.0175(6) O1 0.0312(7) 0.0215(6) 0.0260(6) 0.0027(5) 0.0001(6) 0.0052(6) O2 0.0190(6) 0.0383(8) 0.0282(6) -0.0046(6) 0.0010(5) -0.0021(6) O3 0.0263(6) 0.0241(6) 0.0279(6) 0.0054(6) 0.0008(6) -0.0032(6) C1 0.0244(8) 0.0286(9) 0.0242(8) -0.0038(7) 0.0002(7) 0.0000(9) C2 0.0268(8) 0.0245(9) 0.0215(7) 0.0003(7) -0.0004(8) -0.0017(8) C3 0.0198(8) 0.0291(9) 0.0287(9) 0.0075(8) -0.0032(7) -0.0033(8) C4 0.0236(8) 0.0251(9) 0.0307(9) 0.0046(8) 0.0042(8) 0.0021(8) C5 0.0270(8) 0.0234(9) 0.0218(8) 0.0019(7) 0.0007(7) 0.0034(8) C6 0.0247(8) 0.0340(11) 0.0243(8) -0.0059(8) -0.0033(7) 0.0006(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.935(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C4 . 1.408(2) yes O1 . C1 . 1.424(2) yes O1 . C5 . 1.436(2) yes O2 . C1 . 1.416(2) yes O2 . C6 . 1.443(2) yes O3 . C2 . 1.444(2) yes O3 . C3 . 1.443(2) yes C1 . C2 . 1.526(3) yes C1 . H11 . 1.02(2) no C2 . C3 . 1.466(3) yes C2 . H21 . 0.978(19) no C3 . C4 . 1.497(3) yes C3 . H31 . 0.96(2) no C4 . C5 . 1.526(3) yes C4 . H41 . 1.01(2) no C5 . C6 . 1.528(3) yes C5 . H51 . 1.01(2) no C6 . H61 . 1.02(3) no C6 . H62 . 0.99(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 101.07(13) yes C1 . O2 . C6 . 105.60(13) yes C2 . O3 . C3 . 61.05(12) yes O1 . C1 . O2 . 105.02(14) yes O1 . C1 . C2 . 109.22(15) yes O2 . C1 . C2 . 111.13(16) yes O1 . C1 . H11 . 111.7(13) no O2 . C1 . H11 . 108.3(14) no C2 . C1 . H11 . 111.3(13) no C1 . C2 . O3 . 115.80(16) yes C1 . C2 . C3 . 117.49(15) yes O3 . C2 . C3 . 59.43(12) yes C1 . C2 . H21 . 114.4(12) no O3 . C2 . H21 . 114.5(11) no C3 . C2 . H21 . 123.3(12) no C2 . C3 . O3 . 59.52(11) yes C2 . C3 . C4 . 116.67(16) yes O3 . C3 . C4 . 116.65(16) yes C2 . C3 . H31 . 119.8(13) no O3 . C3 . H31 . 115.9(13) no C4 . C3 . H31 . 116.2(13) no C3 . C4 . F1 . 110.31(16) yes C3 . C4 . C5 . 113.35(16) yes F1 . C4 . C5 . 107.95(17) yes C3 . C4 . H41 . 107.7(12) no F1 . C4 . H41 . 106.0(13) no C5 . C4 . H41 . 111.3(12) no C4 . C5 . O1 . 106.76(15) yes C4 . C5 . C6 . 115.83(16) yes O1 . C5 . C6 . 102.42(15) yes C4 . C5 . H51 . 108.5(12) no O1 . C5 . H51 . 108.7(11) no C6 . C5 . H51 . 114.0(12) no C5 . C6 . O2 . 104.21(15) yes C5 . C6 . H61 . 110.9(14) no O2 . C6 . H61 . 110.8(14) no C5 . C6 . H62 . 110.2(14) no O2 . C6 . H62 . 106.6(14) no H61 . C6 . H62 . 114(2) no # Attachment '- comp_23.cif' data_CRYSTALS_cif16 _database_code_depnum_ccdc_archive 'CCDC 832063' #TrackingRef '- comp_23.cif' _audit_creation_date 11-06-29 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e340_f1_sykora_0m in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.2178(10) _cell_length_b 8.7675(13) _cell_length_c 9.500(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 601.20(19) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H7 F1 O3 # Dc = 1.61 Fooo = 304.00 Mu = 1.48 M = 146.12 # Found Formula = C6 H7 F1 O3 # Dc = 1.61 FOOO = 304.00 Mu = 1.48 M = 146.12 _chemical_formula_sum 'C6 H7 F1 O3' _chemical_formula_moiety 'C6 H7 F1 O3' _chemical_compound_source ? _chemical_formula_weight 146.12 _cell_measurement_reflns_used 243 _cell_measurement_theta_min 3 _cell_measurement_theta_max 29 _cell_measurement_temperature 150 _exptl_crystal_description bar _exptl_crystal_colour colourless _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_max 0.61 _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.148 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 5468 _reflns_number_total 939 _diffrn_reflns_av_R_equivalents 0.019 # Number of reflections with Friedels Law is 939 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 865 _diffrn_reflns_theta_min 3.162 _diffrn_reflns_theta_max 30.082 _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 26.473 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min 0 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.20 _refine_ls_number_reflns 767 _refine_ls_number_restraints 0 _refine_ls_number_parameters 119 #_refine_ls_R_factor_ref 0.0295 _refine_ls_wR_factor_ref 0.0334 _refine_ls_goodness_of_fit_ref 1.0651 #_reflns_number_all 936 _refine_ls_R_factor_all 0.0377 _refine_ls_wR_factor_all 0.0475 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 767 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_gt 0.0334 _refine_ls_shift/su_max 0.000218 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.250 0.214 0.103 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 0.59453(15) 0.55200(16) 0.37879(17) 0.0341 1.0000 Uani . . . . . . O1 O 0.14896(18) 0.56444(16) 0.54855(14) 0.0201 1.0000 Uani . . . . . . O2 O 0.05271(18) 0.60494(15) 0.32584(15) 0.0203 1.0000 Uani . . . . . . O3 O 0.2537(2) 0.26811(14) 0.48915(15) 0.0215 1.0000 Uani . . . . . . C1 C 0.0543(3) 0.4945(2) 0.43570(19) 0.0170 1.0000 Uani . . . . . . C2 C 0.1600(3) 0.3570(2) 0.3821(2) 0.0171 1.0000 Uani . . . . . . C3 C 0.3618(3) 0.3631(2) 0.3956(2) 0.0195 1.0000 Uani . . . . . . C4 C 0.4489(3) 0.5006(2) 0.4649(2) 0.0215 1.0000 Uani . . . . . . C5 C 0.3080(3) 0.6290(2) 0.4792(2) 0.0191 1.0000 Uani . . . . . . C6 C 0.2304(3) 0.68076(19) 0.3363(2) 0.0192 1.0000 Uani . . . . . . H11 H -0.070(4) 0.471(3) 0.461(3) 0.028(6) 1.0000 Uiso . . . . . . H21 H 0.105(3) 0.305(3) 0.310(3) 0.021(6) 1.0000 Uiso . . . . . . H31 H 0.439(4) 0.309(3) 0.330(3) 0.029(6) 1.0000 Uiso . . . . . . H41 H 0.497(4) 0.473(3) 0.557(3) 0.040(8) 1.0000 Uiso . . . . . . H51 H 0.349(3) 0.707(3) 0.532(3) 0.024(6) 1.0000 Uiso . . . . . . H61 H 0.205(3) 0.790(3) 0.334(3) 0.026(6) 1.0000 Uiso . . . . . . H62 H 0.307(3) 0.651(3) 0.261(3) 0.017(5) 1.0000 Uiso . . . . . . 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 0.0138(5) 0.0343(6) 0.0541(8) 0.0100(7) 0.0057(5) -0.0028(5) O1 0.0241(6) 0.0191(6) 0.0170(6) -0.0016(5) 0.0039(5) -0.0020(5) O2 0.0164(5) 0.0196(6) 0.0250(6) 0.0073(5) -0.0030(6) 0.0004(5) O3 0.0218(6) 0.0163(5) 0.0265(7) 0.0067(5) -0.0022(6) 0.0007(5) C1 0.0146(7) 0.0172(7) 0.0193(8) 0.0042(7) -0.0005(7) -0.0003(6) C2 0.0207(8) 0.0139(7) 0.0168(7) 0.0002(7) -0.0031(7) -0.0015(7) C3 0.0185(7) 0.0171(8) 0.0230(8) 0.0027(8) 0.0012(7) 0.0038(7) C4 0.0142(7) 0.0223(8) 0.0279(9) 0.0046(8) -0.0026(8) -0.0022(7) C5 0.0196(8) 0.0165(7) 0.0213(8) -0.0018(7) -0.0025(7) -0.0026(6) C6 0.0183(7) 0.0162(7) 0.0232(8) 0.0048(6) -0.0001(8) -0.0011(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3889(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C4 . 1.406(2) yes O1 . C1 . 1.411(2) yes O1 . C5 . 1.439(2) yes O2 . C1 . 1.424(2) yes O2 . C6 . 1.448(2) yes O3 . C2 . 1.449(2) yes O3 . C3 . 1.447(2) yes C1 . C2 . 1.514(3) yes C1 . H11 . 0.95(3) no C2 . C3 . 1.463(2) yes C2 . H21 . 0.92(3) no C3 . C4 . 1.510(3) yes C3 . H31 . 0.96(3) no C4 . C5 . 1.523(3) yes C4 . H41 . 0.97(3) no C5 . C6 . 1.538(3) yes C5 . H51 . 0.90(3) no C6 . H61 . 0.98(3) no C6 . H62 . 0.94(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 102.08(13) yes C1 . O2 . C6 . 104.76(14) yes C2 . O3 . C3 . 60.70(11) yes O2 . C1 . O1 . 105.37(14) yes O2 . C1 . C2 . 107.39(15) yes O1 . C1 . C2 . 110.96(15) yes O2 . C1 . H11 . 108.9(16) no O1 . C1 . H11 . 110.9(16) no C2 . C1 . H11 . 113.0(16) no C1 . C2 . O3 . 115.28(16) yes C1 . C2 . C3 . 116.28(17) yes O3 . C2 . C3 . 59.57(12) yes C1 . C2 . H21 . 115.7(15) no O3 . C2 . H21 . 117.4(16) no C3 . C2 . H21 . 120.8(15) no C2 . C3 . O3 . 59.74(12) yes C2 . C3 . C4 . 118.82(17) yes O3 . C3 . C4 . 114.62(17) yes C2 . C3 . H31 . 120.4(17) no O3 . C3 . H31 . 115.4(15) no C4 . C3 . H31 . 115.6(16) no C3 . C4 . F1 . 108.28(17) yes C3 . C4 . C5 . 110.52(16) yes F1 . C4 . C5 . 108.33(15) yes C3 . C4 . H41 . 109.9(18) no F1 . C4 . H41 . 109.7(18) no C5 . C4 . H41 . 110.1(18) no C4 . C5 . O1 . 106.45(14) yes C4 . C5 . C6 . 112.48(16) yes O1 . C5 . C6 . 103.29(14) yes C4 . C5 . H51 . 113.0(16) no O1 . C5 . H51 . 107.8(17) no C6 . C5 . H51 . 113.0(16) no C5 . C6 . O2 . 104.33(14) yes C5 . C6 . H61 . 112.0(16) no O2 . C6 . H61 . 106.6(14) no C5 . C6 . H62 . 112.4(14) no O2 . C6 . H62 . 109.8(14) no H61 . C6 . H62 . 111(2) no # Attachment '- comp_26.cif' data_CRYSTALS_cif17 _database_code_depnum_ccdc_archive 'CCDC 832064' #TrackingRef '- comp_26.cif' _audit_creation_date 11-06-29 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title ? _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.1716(2) _cell_length_b 5.2806(2) _cell_length_c 6.0820(3) _cell_angle_alpha 68.403(2) _cell_angle_beta 67.501(2) _cell_angle_gamma 80.743(3) _cell_volume 142.640(11) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C6 H7 F1 O3 # Dc = 1.70 Fooo = 76.00 Mu = 1.56 M = 146.12 # Found Formula = C6 H7 F1 O3 # Dc = 1.70 FOOO = 76.00 Mu = 1.56 M = 146.12 _chemical_formula_sum 'C6 H7 F1 O3' _chemical_formula_moiety 'C6 H7 F1 O3' _chemical_compound_source ? _chemical_formula_weight 146.12 _cell_measurement_reflns_used 639 _cell_measurement_theta_min 4 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description desk _exptl_crystal_colour colourless _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.65 _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 76 _exptl_absorpt_coefficient_mu 0.156 # Sheldrick geometric approximatio 0.95 0.96 # No experimental values of Tmin/max available _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 1283 _reflns_number_total 647 _diffrn_reflns_av_R_equivalents 0.009 # Number of reflections with Friedels Law is 647 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 652 _diffrn_reflns_theta_min 3.850 _diffrn_reflns_theta_max 27.445 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.445 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min -5 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 7 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.21 _refine_diff_density_max 0.17 _refine_ls_number_reflns 629 _refine_ls_number_restraints 3 _refine_ls_number_parameters 118 #_refine_ls_R_factor_ref 0.0261 _refine_ls_wR_factor_ref 0.0274 _refine_ls_goodness_of_fit_ref 1.1790 #_reflns_number_all 646 _refine_ls_R_factor_all 0.0270 _refine_ls_wR_factor_all 0.0281 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 629 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_gt 0.0274 _refine_ls_shift/su_max 0.000048 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.542 0.212 0.270 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F -0.0173(3) -0.1577(3) 0.5326(3) 0.0245 1.0000 Uani . . . . . . O1 O 0.2150(3) 0.0240(3) 0.0409(3) 0.0207 1.0000 Uani . . . . . . O2 O 0.6254(3) 0.2391(3) -0.1671(3) 0.0235 1.0000 Uani . . . . . . O3 O 0.4293(3) 0.3569(3) 0.2432(3) 0.0216 1.0000 Uani . . . . . . C1 C 0.4879(4) 0.0156(4) 0.0466(4) 0.0201 1.0000 Uani . . . . . . C2 C 0.4603(4) 0.0618(4) 0.2930(4) 0.0201 1.0000 Uani . . . . . . C3 C 0.1534(4) 0.0537(4) 0.4699(3) 0.0204 1.0000 Uani . . . . . . C4 C 0.1366(4) 0.3336(4) 0.2704(3) 0.0203 1.0000 Uani . . . . . . C5 C 0.1453(4) 0.3063(4) 0.0239(4) 0.0192 1.0000 Uani . . . . . . C6 C 0.4047(4) 0.4432(4) -0.1985(3) 0.0218 1.0000 Uani . . . . . . H11 H 0.578(5) -0.156(6) 0.031(5) 0.026(6) 1.0000 Uiso . . . . . . H21 H 0.616(5) -0.024(5) 0.359(4) 0.022(6) 1.0000 Uiso . . . . . . H31 H 0.142(4) 0.078(4) 0.624(4) 0.010(4) 1.0000 Uiso . . . . . . H41 H 0.013(5) 0.487(5) 0.317(4) 0.020(5) 1.0000 Uiso . . . . . . H51 H -0.029(6) 0.343(5) -0.001(5) 0.030(7) 1.0000 Uiso . . . . . . H61 H 0.451(5) 0.611(5) -0.197(5) 0.027(6) 1.0000 Uiso . . . . . . H62 H 0.383(6) 0.474(6) -0.361(5) 0.032(6) 1.0000 Uiso . . . . . . 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 0.0211(5) 0.0227(5) 0.0249(5) -0.0021(4) -0.0060(4) -0.0073(4) O1 0.0251(6) 0.0187(6) 0.0222(6) -0.0082(5) -0.0100(5) -0.0033(5) O2 0.0225(6) 0.0235(6) 0.0178(6) -0.0045(5) -0.0023(5) -0.0006(5) O3 0.0233(6) 0.0211(6) 0.0227(6) -0.0074(5) -0.0087(5) -0.0050(5) C1 0.0204(8) 0.0175(7) 0.0194(7) -0.0052(6) -0.0046(6) -0.0008(6) C2 0.0195(8) 0.0206(8) 0.0189(7) -0.0026(6) -0.0079(6) -0.0037(6) C3 0.0192(8) 0.0221(8) 0.0190(8) -0.0058(6) -0.0052(6) -0.0049(6) C4 0.0177(7) 0.0215(8) 0.0208(7) -0.0084(6) -0.0042(6) -0.0011(6) C5 0.0192(8) 0.0175(7) 0.0213(8) -0.0050(6) -0.0090(6) -0.0002(6) C6 0.0255(8) 0.0212(8) 0.0182(8) -0.0052(6) -0.0080(7) -0.0021(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.298 loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C3 . 1.385(2) yes O1 . C1 . 1.418(2) yes O1 . C5 . 1.451(2) yes O2 . C1 . 1.422(2) yes O2 . C6 . 1.456(2) yes O3 . C2 . 1.468(2) yes O3 . C4 . 1.479(2) yes C1 . C2 . 1.555(3) yes C1 . H11 . 0.97(3) no C2 . C3 . 1.536(2) yes C2 . H21 . 1.00(2) no C3 . C4 . 1.544(3) yes C3 . H31 . 0.97(2) no C4 . C5 . 1.541(2) yes C4 . H41 . 1.00(2) no C5 . C6 . 1.535(2) yes C5 . H51 . 0.95(3) no C6 . H61 . 0.96(3) no C6 . H62 . 0.99(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 97.75(12) yes C1 . O2 . C6 . 104.89(13) yes C2 . O3 . C4 . 87.33(12) yes O2 . C1 . O1 . 104.73(14) yes O2 . C1 . C2 . 109.77(15) yes O1 . C1 . C2 . 108.04(13) yes O2 . C1 . H11 . 111.1(15) no O1 . C1 . H11 . 108.3(15) no C2 . C1 . H11 . 114.4(15) no C1 . C2 . O3 . 106.91(13) yes C1 . C2 . C3 . 111.38(14) yes O3 . C2 . C3 . 84.77(12) yes C1 . C2 . H21 . 114.5(14) no O3 . C2 . H21 . 113.0(14) no C3 . C2 . H21 . 121.8(14) no C2 . C3 . F1 . 121.37(15) yes C2 . C3 . C4 . 82.68(12) yes F1 . C3 . C4 . 121.81(15) yes C2 . C3 . H31 . 109.8(12) no F1 . C3 . H31 . 108.8(12) no C4 . C3 . H31 . 110.0(12) no C3 . C4 . O3 . 84.13(12) yes C3 . C4 . C5 . 112.03(14) yes O3 . C4 . C5 . 107.01(13) yes C3 . C4 . H41 . 122.3(13) no O3 . C4 . H41 . 112.1(14) no C5 . C4 . H41 . 114.4(13) no C4 . C5 . O1 . 107.43(13) yes C4 . C5 . C6 . 110.73(14) yes O1 . C5 . C6 . 99.75(13) yes C4 . C5 . H51 . 113.9(17) no O1 . C5 . H51 . 105.6(16) no C6 . C5 . H51 . 117.8(16) no C5 . C6 . O2 . 102.62(13) yes C5 . C6 . H61 . 114.5(16) no O2 . C6 . H61 . 110.0(16) no C5 . C6 . H62 . 110.5(17) no O2 . C6 . H62 . 109.5(16) no H61 . C6 . H62 . 110(2) no # Attachment '- comp_27.cif' data_CRYSTALS_cif18 _database_code_depnum_ccdc_archive 'CCDC 832065' #TrackingRef '- comp_27.cif' _audit_creation_date 11-06-27 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'e350_f2_sykora_0m in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.7058(5) _cell_length_b 8.1556(5) _cell_length_c 10.7504(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 587.94(7) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C6 H7 F1 O3 # Dc = 1.65 Fooo = 304.00 Mu = 1.51 M = 146.12 # Found Formula = C6 H7 F1 O3 # Dc = 1.65 FOOO = 304.00 Mu = 1.51 M = 146.12 _chemical_formula_sum 'C6 H7 F1 O3' _chemical_formula_moiety 'C6 H7 F1 O3' _chemical_compound_source ? _chemical_formula_weight 146.12 _cell_measurement_reflns_used 5042 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_max 0.62 _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.151 # Sheldrick geometric approximatio 0.96 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 5178 _reflns_number_total 844 _diffrn_reflns_av_R_equivalents 0.016 # Number of reflections with Friedels Law is 844 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 708 _diffrn_reflns_theta_min 3.135 _diffrn_reflns_theta_max 27.971 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.971 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.15 _refine_diff_density_max 0.19 _refine_ls_number_reflns 691 _refine_ls_number_restraints 0 _refine_ls_number_parameters 119 #_refine_ls_R_factor_ref 0.0261 _refine_ls_wR_factor_ref 0.0308 _refine_ls_goodness_of_fit_ref 1.0307 #_reflns_number_all 840 _refine_ls_R_factor_all 0.0327 _refine_ls_wR_factor_all 0.0399 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 691 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_gt 0.0308 _refine_ls_shift/su_max 0.000094 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.197 0.133 0.623E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 0.3588(2) -0.08610(16) -0.07259(12) 0.0380 1.0000 Uani . . . . . . O1 O 0.6070(2) 0.09542(17) -0.05138(11) 0.0262 1.0000 Uani . . . . . . O2 O 0.4865(2) 0.17672(16) 0.14191(13) 0.0286 1.0000 Uani . . . . . . O3 O 0.9200(2) -0.03656(19) 0.05970(15) 0.0342 1.0000 Uani . . . . . . C1 C 0.6518(3) 0.1791(2) 0.06076(17) 0.0231 1.0000 Uani . . . . . . C2 C 0.8245(3) 0.0954(3) 0.12650(17) 0.0265 1.0000 Uani . . . . . . C3 C 0.7718(3) -0.0751(2) 0.15300(16) 0.0240 1.0000 Uani . . . . . . C4 C 0.5636(3) -0.1103(2) 0.10598(15) 0.0195 1.0000 Uani . . . . . . C5 C 0.5556(3) -0.0688(2) -0.03092(16) 0.0227 1.0000 Uani . . . . . . C6 C 0.4292(3) 0.0102(2) 0.1749(2) 0.0275 1.0000 Uani . . . . . . H11 H 0.676(3) 0.293(3) 0.0411(19) 0.026(6) 1.0000 Uiso . . . . . . H21 H 0.908(4) 0.165(3) 0.179(2) 0.036(6) 1.0000 Uiso . . . . . . H31 H 0.819(4) -0.133(3) 0.226(2) 0.037(6) 1.0000 Uiso . . . . . . H41 H 0.520(3) -0.227(3) 0.118(2) 0.026(6) 1.0000 Uiso . . . . . . H51 H 0.637(4) -0.139(3) -0.085(2) 0.024(5) 1.0000 Uiso . . . . . . H61 H 0.289(4) -0.001(3) 0.155(2) 0.030(6) 1.0000 Uiso . . . . . . H62 H 0.446(3) -0.004(3) 0.265(3) 0.033(6) 1.0000 Uiso . . . . . . 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 0.0363(6) 0.0306(6) 0.0470(7) -0.0036(6) -0.0238(6) -0.0020(5) O1 0.0391(8) 0.0231(6) 0.0165(5) 0.0024(5) -0.0036(5) -0.0042(6) O2 0.0337(7) 0.0187(6) 0.0333(7) -0.0025(5) 0.0080(6) 0.0035(5) O3 0.0205(6) 0.0395(8) 0.0426(8) -0.0049(7) 0.0033(6) 0.0011(6) C1 0.0309(9) 0.0183(7) 0.0200(7) 0.0001(7) 0.0006(7) -0.0046(7) C2 0.0257(8) 0.0282(9) 0.0255(8) -0.0035(8) -0.0040(7) -0.0050(7) C3 0.0254(8) 0.0257(8) 0.0211(7) -0.0008(7) -0.0045(7) 0.0017(8) C4 0.0230(8) 0.0158(7) 0.0197(7) 0.0009(6) 0.0010(6) 0.0004(7) C5 0.0264(9) 0.0208(8) 0.0211(8) -0.0025(7) -0.0065(7) 0.0025(7) C6 0.0291(10) 0.0229(8) 0.0307(9) -0.0001(7) 0.0109(9) 0.0001(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4577(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C5 . 1.401(2) yes O1 . C1 . 1.417(2) yes O1 . C5 . 1.400(2) yes O2 . C1 . 1.411(2) yes O2 . C6 . 1.455(2) yes O3 . C2 . 1.444(2) yes O3 . C3 . 1.447(2) yes C1 . C2 . 1.519(3) yes C1 . H11 . 0.97(2) no C2 . C3 . 1.463(3) yes C2 . H21 . 0.97(3) no C3 . C4 . 1.512(2) yes C3 . H31 . 0.97(3) no C4 . C5 . 1.511(2) yes C4 . C6 . 1.526(2) yes C4 . H41 . 1.00(2) no C5 . H51 . 0.98(2) no C6 . H61 . 0.97(2) no C6 . H62 . 0.98(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 112.26(12) yes C1 . O2 . C6 . 111.77(14) yes C2 . O3 . C3 . 60.80(12) yes O1 . C1 . O2 . 110.68(15) yes O1 . C1 . C2 . 109.95(15) yes O2 . C1 . C2 . 107.78(14) yes O1 . C1 . H11 . 108.2(12) no O2 . C1 . H11 . 106.3(13) no C2 . C1 . H11 . 114.0(13) no C1 . C2 . O3 . 116.21(14) yes C1 . C2 . C3 . 109.46(15) yes O3 . C2 . C3 . 59.70(13) yes C1 . C2 . H21 . 116.2(15) no O3 . C2 . H21 . 118.0(15) no C3 . C2 . H21 . 125.6(15) no C2 . C3 . O3 . 59.50(12) yes C2 . C3 . C4 . 109.81(15) yes O3 . C3 . C4 . 116.34(14) yes C2 . C3 . H31 . 122.8(15) no O3 . C3 . H31 . 116.3(15) no C4 . C3 . H31 . 118.6(15) no C3 . C4 . C5 . 108.40(14) yes C3 . C4 . C6 . 105.11(15) yes C5 . C4 . C6 . 107.88(15) yes C3 . C4 . H41 . 114.1(13) no C5 . C4 . H41 . 109.4(12) no C6 . C4 . H41 . 111.8(13) no C4 . C5 . F1 . 108.79(15) yes C4 . C5 . O1 . 111.04(14) yes F1 . C5 . O1 . 106.15(14) yes C4 . C5 . H51 . 115.2(13) no F1 . C5 . H51 . 106.0(14) no O1 . C5 . H51 . 109.2(13) no C4 . C6 . O2 . 109.09(15) yes C4 . C6 . H61 . 113.9(15) no O2 . C6 . H61 . 107.0(16) no C4 . C6 . H62 . 109.6(14) no O2 . C6 . H62 . 108.6(14) no H61 . C6 . H62 . 108.4(19) no # Attachment '- comp_29.cif' data_CRYSTALS_cif19 _database_code_depnum_ccdc_archive 'CCDC 832066' #TrackingRef '- comp_29.cif' _audit_creation_date 11-06-29 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title ? _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.2240(4) _cell_length_b 10.6879(6) _cell_length_c 8.8554(4) _cell_angle_alpha 90 _cell_angle_beta 106.700(4) _cell_angle_gamma 90 _cell_volume 564.23(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C13 H13 F1 O4 # Dc = 1.48 Fooo = 264.00 Mu = 1.20 M = 252.24 # Found Formula = C13 H13 F1 O4 # Dc = 1.48 FOOO = 264.00 Mu = 1.20 M = 252.24 _chemical_formula_sum 'C13 H13 F1 O4' _chemical_formula_moiety 'C13 H13 F1 O4' _chemical_compound_source ? _chemical_formula_weight 252.24 _cell_measurement_reflns_used 1299 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.120 # Sheldrick geometric approximatio 0.96 0.98 # No experimental values of Tmin/max available _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 2465 _reflns_number_total 1303 _diffrn_reflns_av_R_equivalents 0.010 # Number of reflections with Friedels Law is 1303 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1242 _diffrn_reflns_theta_min 2.401 _diffrn_reflns_theta_max 27.077 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.077 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.16 _refine_diff_density_max 0.14 _refine_ls_number_reflns 1057 _refine_ls_number_restraints 1 _refine_ls_number_parameters 215 #_refine_ls_R_factor_ref 0.0310 _refine_ls_wR_factor_ref 0.0309 _refine_ls_goodness_of_fit_ref 1.1805 #_reflns_number_all 1296 _refine_ls_R_factor_all 0.0413 _refine_ls_wR_factor_all 0.0445 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 1057 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_gt 0.0309 _refine_ls_shift/su_max 0.000138 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.246 0.568E-01 0.433E-01 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F -0.1281(3) 0.58523(19) -0.25879(19) 0.0421 1.0000 Uani . . . . . . O1 O 0.3184(3) 0.3594(2) -0.1348(2) 0.0347 1.0000 Uani . . . . . . O2 O 0.4577(3) 0.5057(2) 0.0525(2) 0.0349 1.0000 Uani . . . . . . O3 O 0.1742(3) 0.42192(19) 0.2287(2) 0.0297 1.0000 Uani . . . . . . O4 O -0.0073(3) 0.57114(18) 0.0559(2) 0.0253 1.0000 Uani . . . . . . C1 C 0.3645(5) 0.3837(3) 0.0287(3) 0.0322 1.0000 Uani . . . . . . C2 C 0.1449(5) 0.3731(3) 0.0729(3) 0.0280 1.0000 Uani . . . . . . C3 C -0.0391(5) 0.4560(3) -0.0307(3) 0.0266 1.0000 Uani . . . . . . C4 C -0.0178(5) 0.4742(3) -0.1957(3) 0.0317 1.0000 Uani . . . . . . C5 C 0.2219(5) 0.4764(3) -0.2020(3) 0.0338 1.0000 Uani . . . . . . C6 C 0.3716(5) 0.5723(3) -0.0950(4) 0.0373 1.0000 Uani . . . . . . C7 C 0.0321(4) 0.5297(3) 0.2144(3) 0.0249 1.0000 Uani . . . . . . C8 C 0.1405(4) 0.6291(3) 0.3305(3) 0.0272 1.0000 Uani . . . . . . C9 C 0.3501(5) 0.6776(3) 0.3374(4) 0.0341 1.0000 Uani . . . . . . C10 C 0.4451(5) 0.7695(3) 0.4466(4) 0.0370 1.0000 Uani . . . . . . C11 C 0.3310(5) 0.8139(3) 0.5497(3) 0.0351 1.0000 Uani . . . . . . C12 C 0.1226(5) 0.7660(3) 0.5436(3) 0.0340 1.0000 Uani . . . . . . C13 C 0.0276(5) 0.6730(3) 0.4348(3) 0.0304 1.0000 Uani . . . . . . H11 H 0.474(5) 0.322(3) 0.089(4) 0.037(8) 1.0000 Uiso . . . . . . H21 H 0.102(5) 0.287(3) 0.065(3) 0.039(9) 1.0000 Uiso . . . . . . H31 H -0.193(5) 0.431(3) -0.039(3) 0.027(7) 1.0000 Uiso . . . . . . H41 H -0.097(6) 0.402(4) -0.266(4) 0.055(11) 1.0000 Uiso . . . . . . H51 H 0.229(5) 0.485(3) -0.317(3) 0.033(8) 1.0000 Uiso . . . . . . H61 H 0.495(5) 0.596(3) -0.141(3) 0.041(9) 1.0000 Uiso . . . . . . H62 H 0.283(5) 0.656(3) -0.083(4) 0.040(9) 1.0000 Uiso . . . . . . H71 H -0.120(5) 0.506(3) 0.224(3) 0.029(7) 1.0000 Uiso . . . . . . H91 H 0.436(6) 0.644(3) 0.269(4) 0.049(10) 1.0000 Uiso . . . . . . H101 H 0.607(5) 0.804(3) 0.458(4) 0.038(9) 1.0000 Uiso . . . . . . H111 H 0.394(5) 0.879(3) 0.628(4) 0.042(9) 1.0000 Uiso . . . . . . H121 H 0.037(5) 0.793(3) 0.612(4) 0.036(9) 1.0000 Uiso . . . . . . H131 H -0.125(5) 0.639(3) 0.430(3) 0.032(8) 1.0000 Uiso . . . . . . 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 0.0483(10) 0.0441(10) 0.0340(9) 0.0083(8) 0.0122(7) 0.0136(9) O1 0.0450(11) 0.0281(10) 0.0355(11) -0.0041(8) 0.0186(9) 0.0052(9) O2 0.0300(10) 0.0348(11) 0.0420(12) -0.0048(9) 0.0138(8) -0.0043(9) O3 0.0371(11) 0.0258(10) 0.0269(10) 0.0021(8) 0.0101(8) 0.0055(8) O4 0.0292(8) 0.0223(8) 0.0245(8) -0.0011(7) 0.0080(7) 0.0003(8) C1 0.0348(14) 0.0274(14) 0.0348(15) -0.0026(12) 0.0105(11) 0.0050(11) C2 0.0356(14) 0.0216(13) 0.0292(14) 0.0005(11) 0.0129(11) 0.0004(11) C3 0.0294(14) 0.0225(13) 0.0284(14) -0.0057(11) 0.0090(11) -0.0038(11) C4 0.0393(15) 0.0287(14) 0.0267(13) -0.0015(12) 0.0090(12) 0.0042(12) C5 0.0428(15) 0.0290(14) 0.0339(14) -0.0003(13) 0.0179(12) 0.0025(12) C6 0.0388(15) 0.0281(14) 0.0514(18) 0.0010(14) 0.0234(13) -0.0012(13) C7 0.0266(13) 0.0240(12) 0.0251(12) 0.0028(10) 0.0091(10) 0.0030(10) C8 0.0291(13) 0.0254(12) 0.0267(12) 0.0018(11) 0.0071(10) 0.0047(11) C9 0.0279(14) 0.0364(16) 0.0388(16) -0.0046(13) 0.0106(12) 0.0017(12) C10 0.0290(14) 0.0379(16) 0.0411(16) -0.0077(14) 0.0053(11) -0.0026(13) C11 0.0410(16) 0.0316(15) 0.0286(14) -0.0035(13) 0.0035(12) 0.0019(13) C12 0.0448(16) 0.0318(15) 0.0286(14) -0.0033(12) 0.0156(12) 0.0008(14) C13 0.0348(15) 0.0295(14) 0.0287(14) 0.0002(12) 0.0118(11) 0.0006(12) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.8163(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C4 . 1.404(3) yes O1 . C1 . 1.417(3) yes O1 . C5 . 1.440(3) yes O2 . C1 . 1.418(3) yes O2 . C6 . 1.448(4) yes O3 . C2 . 1.437(3) yes O3 . C7 . 1.435(3) yes O4 . C3 . 1.433(3) yes O4 . C7 . 1.424(3) yes C1 . C2 . 1.530(4) yes C1 . H11 . 0.99(3) no C2 . C3 . 1.528(4) yes C2 . H21 . 0.96(3) no C3 . C4 . 1.517(4) yes C3 . H31 . 0.98(3) no C4 . C5 . 1.509(4) yes C4 . H41 . 1.02(4) no C5 . C6 . 1.520(4) yes C5 . H51 . 1.03(3) no C6 . H61 . 1.00(3) no C6 . H62 . 1.07(3) no C7 . C8 . 1.497(4) yes C7 . H71 . 1.01(3) no C8 . C9 . 1.389(4) yes C8 . C13 . 1.393(4) yes C9 . C10 . 1.385(4) yes C9 . H91 . 0.99(3) no C10 . C11 . 1.392(4) yes C10 . H101 . 1.05(3) no C11 . C12 . 1.381(4) yes C11 . H111 . 0.98(4) no C12 . C13 . 1.392(4) yes C12 . H121 . 0.96(3) no C13 . H131 . 1.01(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 101.6(2) yes C1 . O2 . C6 . 106.8(2) yes C2 . O3 . C7 . 107.6(2) yes C3 . O4 . C7 . 102.62(19) yes O2 . C1 . O1 . 105.9(2) yes O2 . C1 . C2 . 112.8(2) yes O1 . C1 . C2 . 108.3(2) yes O2 . C1 . H11 . 110.4(19) no O1 . C1 . H11 . 109.6(18) no C2 . C1 . H11 . 109.8(19) no C1 . C2 . O3 . 110.0(2) yes C1 . C2 . C3 . 112.0(2) yes O3 . C2 . C3 . 103.4(2) yes C1 . C2 . H21 . 107.6(20) no O3 . C2 . H21 . 112.0(19) no C3 . C2 . H21 . 111.8(18) no C2 . C3 . O4 . 102.24(19) yes C2 . C3 . C4 . 113.2(2) yes O4 . C3 . C4 . 111.6(2) yes C2 . C3 . H31 . 115.9(17) no O4 . C3 . H31 . 105.1(18) no C4 . C3 . H31 . 108.4(16) no C3 . C4 . F1 . 108.8(2) yes C3 . C4 . C5 . 113.5(2) yes F1 . C4 . C5 . 110.4(2) yes C3 . C4 . H41 . 108.9(20) no F1 . C4 . H41 . 107.6(20) no C5 . C4 . H41 . 107.5(19) no C4 . C5 . O1 . 105.7(2) yes C4 . C5 . C6 . 115.0(2) yes O1 . C5 . C6 . 102.7(2) yes C4 . C5 . H51 . 111.2(16) no O1 . C5 . H51 . 110.5(18) no C6 . C5 . H51 . 111.2(17) no C5 . C6 . O2 . 103.5(2) yes C5 . C6 . H61 . 108.8(18) no O2 . C6 . H61 . 111.3(18) no C5 . C6 . H62 . 112.7(17) no O2 . C6 . H62 . 112.8(17) no H61 . C6 . H62 . 108(3) no O3 . C7 . O4 . 105.29(19) yes O3 . C7 . C8 . 111.4(2) yes O4 . C7 . C8 . 111.8(2) yes O3 . C7 . H71 . 111.4(18) no O4 . C7 . H71 . 105.3(16) no C8 . C7 . H71 . 111.4(16) no C7 . C8 . C9 . 121.8(2) yes C7 . C8 . C13 . 118.8(2) yes C9 . C8 . C13 . 119.4(3) yes C8 . C9 . C10 . 120.2(3) yes C8 . C9 . H91 . 120.5(20) no C10 . C9 . H91 . 119.3(19) no C9 . C10 . C11 . 120.2(3) yes C9 . C10 . H101 . 121.5(18) no C11 . C10 . H101 . 118.2(18) no C10 . C11 . C12 . 119.9(3) yes C10 . C11 . H111 . 121.8(19) no C12 . C11 . H111 . 118.3(19) no C11 . C12 . C13 . 120.0(3) yes C11 . C12 . H121 . 123.3(19) no C13 . C12 . H121 . 116.7(19) no C8 . C13 . C12 . 120.3(3) yes C8 . C13 . H131 . 120.0(18) no C12 . C13 . H131 . 119.7(18) no