data_CRYSTALS_cif _audit_creation_date 09-12-28 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title '?' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.8713(2) _cell_length_b 9.1449(3) _cell_length_c 9.5056(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 597.31(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' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 '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 H8 F1 N1 O2 # Dc = 1.61 Fooo = 304.00 Mu = 1.41 M = 145.13 # Found Formula = C6 H8 F1 N1 O2 # Dc = 1.61 FOOO = 304.00 Mu = 1.41 M = 145.13 _chemical_formula_sum 'C6 H8 F1 N1 O2' _chemical_formula_moiety 'C6 H8 F1 N1 O2' _chemical_compound_source ? _chemical_formula_weight 145.13 _cell_measurement_reflns_used 831 _cell_measurement_theta_min 1 _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 0.35 _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.141 # Sheldrick geometric approximatio 0.96 0.97 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; Gaussian Integration (Busing and Levy, 1957) ; _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 'SIR92 (Altomare et al., 1994)' _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 1369 _reflns_number_total 818 _diffrn_reflns_av_R_equivalents 0.005 # Number of reflections with Friedels Law is 818 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 683 _diffrn_reflns_theta_min 3.091 _diffrn_reflns_theta_max 27.462 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.462 _diffrn_measured_fraction_theta_full 1.000 _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 -12 _diffrn_reflns_limit_l_max 12 _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 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 -0.18 _refine_diff_density_max 0.12 _refine_ls_number_reflns 749 _refine_ls_number_restraints 0 _refine_ls_number_parameters 123 #_refine_ls_R_factor_ref 0.0256 _refine_ls_wR_factor_ref 0.0263 _refine_ls_goodness_of_fit_ref 1.0715 #_reflns_number_all 815 _refine_ls_R_factor_all 0.0280 _refine_ls_wR_factor_all 0.0282 # 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 0.0256 _refine_ls_wR_factor_gt 0.0263 _refine_ls_shift/su_max 0.000088 # 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: 0.327 0.122 0.117 ; # 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_contact_author_name 'Anthony Other' _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_phone '+44 1865 000000' _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_email 'a.n.other@chem.no.ac.uk' _publ_requested_journal 'Section C' _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 ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Other, Anthony N.' # Author 1 ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Else, S. O.' # Author 2 ; ? # Address 2 ; ; ? # Footnote 2 ; _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 ; ? ; # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Busing, W.R. & Levy, H.A., (1975). Acta Cryst 10, 180 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. 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 -0.13490(15) -0.18808(11) -0.45890(9) 0.0302 1.0000 Uani . . . . . . O1 O -0.28288(17) -0.19261(12) -0.17271(11) 0.0234 1.0000 Uani . . . . . . O2 O -0.43316(17) -0.39841(13) -0.10110(12) 0.0266 1.0000 Uani . . . . . . N1 N -0.1485(2) -0.53438(15) -0.25786(16) 0.0271 1.0000 Uani . . . . . . C1 C -0.2519(2) -0.32515(18) -0.09677(16) 0.0230 1.0000 Uani . . . . . . C2 C -0.0888(2) -0.41048(17) -0.16761(17) 0.0233 1.0000 Uani . . . . . . C3 C -0.0764(2) -0.39875(17) -0.32375(16) 0.0234 1.0000 Uani . . . . . . C4 C -0.2302(2) -0.30962(18) -0.39714(15) 0.0205 1.0000 Uani . . . . . . C5 C -0.3808(2) -0.24741(17) -0.29666(15) 0.0201 1.0000 Uani . . . . . . C6 C -0.5178(2) -0.36228(17) -0.23552(17) 0.0231 1.0000 Uani . . . . . . H11 H -0.216(3) -0.3005(18) 0.004(2) 0.025(4) 1.0000 Uiso . . . . . . H21 H 0.031(3) -0.418(2) -0.118(2) 0.025(5) 1.0000 Uiso . . . . . . H31 H 0.051(3) -0.398(2) -0.372(2) 0.032(5) 1.0000 Uiso . . . . . . H41 H -0.292(3) -0.362(2) -0.4752(19) 0.025(5) 1.0000 Uiso . . . . . . H51 H -0.447(3) -0.167(2) -0.3425(18) 0.024(4) 1.0000 Uiso . . . . . . H61 H -0.526(3) -0.452(2) -0.2998(19) 0.029(5) 1.0000 Uiso . . . . . . H62 H -0.649(3) -0.321(2) -0.2209(19) 0.026(5) 1.0000 Uiso . . . . . . H1 H -0.051(3) -0.599(2) -0.259(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 F1 0.0307(5) 0.0322(5) 0.0278(4) 0.0068(4) 0.0046(4) -0.0090(5) O1 0.0288(5) 0.0195(5) 0.0220(5) -0.0025(4) -0.0048(4) 0.0000(5) O2 0.0245(5) 0.0331(6) 0.0223(5) 0.0056(5) 0.0013(5) -0.0029(5) N1 0.0291(7) 0.0202(6) 0.0319(7) -0.0021(6) -0.0042(7) 0.0040(6) C1 0.0255(7) 0.0237(7) 0.0198(6) 0.0018(6) -0.0021(6) -0.0016(7) C2 0.0210(7) 0.0256(7) 0.0234(7) 0.0012(6) -0.0050(7) 0.0007(7) C3 0.0191(7) 0.0258(7) 0.0252(7) -0.0022(6) -0.0006(6) 0.0012(7) C4 0.0213(7) 0.0206(6) 0.0196(6) 0.0011(6) 0.0013(6) -0.0032(7) C5 0.0219(7) 0.0186(6) 0.0198(6) -0.0013(5) -0.0021(6) 0.0002(6) C6 0.0200(7) 0.0266(7) 0.0229(7) 0.0020(6) -0.0007(6) -0.0006(6) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 0.962(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 . 1.4172(17) yes O1 . C1 . 1.4267(19) yes O1 . C5 . 1.4463(17) yes O2 . C1 . 1.4150(19) yes O2 . C6 . 1.4423(19) yes N1 . C2 . 1.479(2) yes N1 . C3 . 1.475(2) yes N1 . H1 . 0.89(2) no C1 . C2 . 1.523(2) yes C1 . H11 . 1.012(19) no C2 . C3 . 1.490(2) yes C2 . H21 . 0.95(2) no C3 . C4 . 1.506(2) yes C3 . H31 . 0.99(2) no C4 . C5 . 1.519(2) yes C4 . H41 . 0.980(18) no C5 . C6 . 1.526(2) yes C5 . H51 . 0.969(19) no C6 . H61 . 1.022(19) no C6 . H62 . 0.989(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 . 100.79(11) yes C1 . O2 . C6 . 105.81(12) yes C2 . N1 . C3 . 60.59(9) yes C2 . N1 . H1 . 107.7(14) no C3 . N1 . H1 . 107.4(14) no O1 . C1 . O2 . 104.84(12) yes O1 . C1 . C2 . 108.76(12) yes O2 . C1 . C2 . 113.11(13) yes O1 . C1 . H11 . 108.9(10) no O2 . C1 . H11 . 110.4(10) no C2 . C1 . H11 . 110.5(10) no C1 . C2 . N1 . 116.39(14) yes C1 . C2 . C3 . 116.44(14) yes N1 . C2 . C3 . 59.57(10) yes C1 . C2 . H21 . 116.9(12) no N1 . C2 . H21 . 118.1(12) no C3 . C2 . H21 . 117.1(12) no C2 . C3 . N1 . 59.85(11) yes C2 . C3 . C4 . 117.42(14) yes N1 . C3 . C4 . 114.60(14) yes C2 . C3 . H31 . 121.1(12) no N1 . C3 . H31 . 120.3(12) no C4 . C3 . H31 . 113.4(12) no C3 . C4 . F1 . 107.01(12) yes C3 . C4 . C5 . 112.92(12) yes F1 . C4 . C5 . 106.35(12) yes C3 . C4 . H41 . 112.7(11) no F1 . C4 . H41 . 105.7(10) no C5 . C4 . H41 . 111.5(11) no C4 . C5 . O1 . 108.97(12) yes C4 . C5 . C6 . 113.71(13) yes O1 . C5 . C6 . 102.44(12) yes C4 . C5 . H51 . 108.8(11) no O1 . C5 . H51 . 108.9(10) no C6 . C5 . H51 . 113.7(11) no C5 . C6 . O2 . 104.25(12) yes C5 . C6 . H61 . 110.9(11) no O2 . C6 . H61 . 111.6(11) no C5 . C6 . H62 . 110.6(12) no O2 . C6 . H62 . 109.3(11) no H61 . C6 . H62 . 110.0(16) no