#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/06/2010633.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2010633 loop_ _publ_author_name 'Bats, Jan W.' 'Parsch, J\"org' 'Engels, Joachim W.' _publ_section_title ; 1-Deoxy-1-(4-fluorophenyl)-\b-D-ribofuranose, its hemihydrate, and 1-deoxy-1-(2,4-difluorophenyl)-\b-D-ribofuranose: structural evidence for intermolecular C---H···F---C interactions ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 201 _journal_page_last 205 _journal_paper_doi 10.1107/S010827019901361X _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C11 H13 F O4' _chemical_formula_weight 228.21 _chemical_name_systematic ; 1'-deoxy-1'-(4-fluorophenyl)-\b-D-ribofuranose ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.7109(14) _cell_length_b 6.7653(7) _cell_length_c 22.846(3) _cell_measurement_reflns_used 161 _cell_measurement_temperature 135(2) _cell_measurement_theta_max 23 _cell_measurement_theta_min 3 _cell_volume 1037.2(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_molecular_graphics 'XP in SHELXTL' _computing_publication_material 'CIF in SHELXL97' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL (Sheldrick, 1996)' _diffrn_ambient_temperature 135(2) _diffrn_measured_fraction_theta_full .944 _diffrn_measured_fraction_theta_max .944 _diffrn_measurement_device_type 'Siemens SMART' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .058 _diffrn_reflns_av_sigmaI/netI .041 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 19895 _diffrn_reflns_theta_full 32.70 _diffrn_reflns_theta_max 31.9 _diffrn_reflns_theta_min 1.78 _diffrn_standards_decay_% .0 _diffrn_standards_interval_time 540 _diffrn_standards_number 275 _exptl_absorpt_coefficient_mu .122 _exptl_absorpt_correction_T_max .968 _exptl_absorpt_correction_T_min .932 _exptl_absorpt_correction_type 'numerical (SHELXTL; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 480 _exptl_crystal_size_max .66 _exptl_crystal_size_mid .45 _exptl_crystal_size_min .28 _refine_diff_density_max .302 _refine_diff_density_min -.203 _refine_ls_extinction_coef .010(3) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 198 _refine_ls_number_reflns 3512 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.114 _refine_ls_R_factor_all .053 _refine_ls_R_factor_gt .039 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.05P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .090 _reflns_number_gt 2944 _reflns_number_total 3512 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ka1343.cif _cod_data_source_block Ib _cod_database_code 2010633 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O3 .13084(14) .41021(13) .76631(4) .02036(19) Uani d . 1 . . O O5 .73253(12) .22777(12) .66755(4) .02106(19) Uani d . 1 . . O F .33765(16) 1.11352(13) .46221(4) .0454(3) Uani d . 1 . . F O4 .46441(12) .56444(12) .68270(4) .02004(19) Uani d . 1 . . O O2 -.06632(12) .57415(13) .67107(4) .01943(18) Uani d . 1 . . O C7 .4733(2) .77456(18) .57821(6) .0244(3) Uani d . 1 . . C C4 .42437(16) .36681(17) .70464(5) .0159(2) Uani d . 1 . . C C11 .14812(19) .91003(18) .59712(5) .0215(3) Uani d . 1 . . C C1 .28136(16) .66180(15) .66811(5) .0154(2) Uani d . 1 . . C C6 .30337(19) .78431(16) .61310(5) .0178(2) Uani d . 1 . . C C5 .52017(17) .21584(17) .66459(6) .0189(2) Uani d . 1 . . C C2 .12640(16) .49594(16) .66321(5) .0153(2) Uani d . 1 . . C C3 .19792(17) .34891(17) .70967(5) .0159(2) Uani d . 1 . . C C10 .1592(2) 1.0222(2) .54614(6) .0281(3) Uani d . 1 . . C C9 .3288(2) 1.00628(19) .51258(5) .0303(3) Uani d . 1 . . C C8 .4866(2) .8878(2) .52740(6) .0311(3) Uani d . 1 . . C H2 .142(2) .437(2) .6228(6) .022(4) Uiso d . 1 . . H H4 .485(2) .3559(18) .7426(5) .007(3) Uiso d . 1 . . H H1 .239(2) .751(2) .7013(6) .016(3) Uiso d . 1 . . H H3 .148(2) .217(2) .7025(5) .014(3) Uiso d . 1 . . H H11 .022(2) .9189(19) .6210(6) .012(3) Uiso d . 1 . . H HO5 .775(3) .133(3) .6905(7) .028(4) Uiso d . 1 . . H H5B .483(2) .242(2) .6230(7) .030(4) Uiso d . 1 . . H H5A .472(2) .084(2) .6770(6) .020(4) Uiso d . 1 . . H H7 .582(2) .693(3) .5899(6) .028(4) Uiso d . 1 . . H HO3 .122(3) .317(4) .7873(9) .057(6) Uiso d . 1 . . H H8 .599(2) .885(2) .5036(7) .029(4) Uiso d . 1 . . H H10 .054(3) 1.100(3) .5344(8) .038(5) Uiso d . 1 . . H HO2 -.152(2) .485(3) .6690(7) .036(4) Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O3 .0240(5) .0182(4) .0189(4) -.0025(4) .0051(3) .0011(3) O5 .0134(4) .0181(4) .0316(5) .0007(3) .0001(3) .0017(4) F .0740(7) .0364(5) .0260(4) -.0143(5) .0018(5) .0117(3) O4 .0134(4) .0128(4) .0340(5) -.0007(3) -.0020(3) .0033(3) O2 .0121(4) .0173(4) .0289(5) -.0002(3) -.0001(3) -.0014(4) C7 .0259(7) .0180(5) .0292(6) -.0007(5) .0079(5) -.0025(5) C4 .0147(5) .0147(5) .0182(5) -.0008(4) -.0010(4) .0005(4) C11 .0237(6) .0187(5) .0221(6) -.0009(5) -.0018(5) .0010(4) C1 .0139(5) .0138(4) .0185(5) -.0012(4) -.0001(4) -.0017(4) C6 .0212(6) .0132(5) .0188(5) -.0034(4) .0011(4) -.0023(4) C5 .0144(5) .0166(5) .0258(6) -.0003(4) .0002(5) -.0039(5) C2 .0131(5) .0147(5) .0182(5) -.0006(4) -.0004(4) -.0018(4) C3 .0150(5) .0144(5) .0183(5) -.0017(4) .0021(4) -.0010(4) C10 .0357(8) .0203(6) .0284(7) -.0022(5) -.0070(6) .0048(5) C9 .0515(10) .0206(6) .0186(5) -.0115(6) .0005(6) .0027(5) C8 .0402(9) .0255(7) .0275(7) -.0058(6) .0149(6) -.0015(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O4 C4 110.16(8) C6 C7 C8 120.18(13) O4 C4 C5 109.48(9) O4 C4 C3 106.42(9) C5 C4 C3 114.45(10) C10 C11 C6 120.78(12) O4 C1 C6 111.18(9) O4 C1 C2 105.18(9) C6 C1 C2 113.98(9) C7 C6 C11 119.41(11) C7 C6 C1 121.96(11) C11 C6 C1 118.62(11) O5 C5 C4 110.89(10) O2 C2 C3 116.31(9) O2 C2 C1 109.77(9) C3 C2 C1 102.24(9) O3 C3 C4 110.95(9) O3 C3 C2 109.86(9) C4 C3 C2 102.00(9) C9 C10 C11 117.89(13) F C9 C8 119.12(13) F C9 C10 117.73(13) C8 C9 C10 123.15(12) C9 C8 C7 118.55(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O3 C3 . 1.4314(14) ? O5 C5 . 1.4290(14) ? F C9 . 1.3616(14) ? O4 C1 . 1.4332(14) ? O4 C4 . 1.4530(14) ? O2 C2 . 1.4089(13) ? C7 C6 . 1.3932(17) ? C7 C8 . 1.3938(19) ? C4 C5 . 1.5146(16) ? C4 C3 . 1.5288(16) ? C11 C10 . 1.3920(17) ? C11 C6 . 1.3937(17) ? C1 C6 . 1.5126(15) ? C1 C2 . 1.5340(15) ? C2 C3 . 1.5318(16) ? C10 C9 . 1.3762(19) ? C9 C8 . 1.371(2) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O2 HO2 O5 1_455 .83(2) 1.91(2) 2.7060(10) 160.0(10) yes O3 HO3 O2 3_546 .79(2) 1.94(2) 2.7210(10) 170.0(10) yes O5 HO5 O3 3_646 .88(2) 1.91(2) 2.7820(10) 174.0(10) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C1 O4 C4 C5 118.21(10) C1 O4 C4 C3 -5.98(12) C4 O4 C1 C6 -141.43(9) C4 O4 C1 C2 -17.61(11) C8 C7 C6 C11 -.79(18) C8 C7 C6 C1 179.09(11) C10 C11 C6 C7 1.45(17) C10 C11 C6 C1 -178.44(11) O4 C1 C6 C7 8.79(14) C2 C1 C6 C7 -109.87(12) O4 C1 C6 C11 -171.33(10) C2 C1 C6 C11 70.01(13) O4 C4 C5 O5 67.36(13) C3 C4 C5 O5 -173.29(10) O4 C1 C2 O2 157.86(9) C6 C1 C2 O2 -80.11(11) O4 C1 C2 C3 33.81(11) C6 C1 C2 C3 155.85(9) O4 C4 C3 O3 -90.15(11) C5 C4 C3 O3 148.78(10) O4 C4 C3 C2 26.81(11) C5 C4 C3 C2 -94.26(11) O2 C2 C3 O3 -38.12(13) C1 C2 C3 O3 81.44(10) O2 C2 C3 C4 -155.86(9) C1 C2 C3 C4 -36.30(10) C6 C11 C10 C9 -.66(18) C11 C10 C9 F 178.85(11) C11 C10 C9 C8 -.8(2) F C9 C8 C7 -178.21(12) C10 C9 C8 C7 1.5(2) C6 C7 C8 C9 -.63(19)