#------------------------------------------------------------------------------ #$Date: 2020-04-30 01:08:32 +0300 (Thu, 30 Apr 2020) $ #$Revision: 251294 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126458.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7126458 loop_ _publ_author_name 'Valverde, Pablo' 'Vendeville, Jean-Baptiste' 'Hollingsworth, Kristian' 'Mattey, Ashley Philip' 'Keenan, Tessa' 'Chidwick, Harriet S.' 'Ledru, Helene' 'Huonnic, Kler' 'Huang, Kun' 'Light, Mark E.' 'Turner, Nicholas J.' 'Jimenez-Barbero, Jesus' 'Galan, M. Carmen' 'Fascione, Martin A.' 'Flitsch, Sabine L.' 'Turnbull, W. Bruce' 'Linclau, Bruno' _publ_section_title ; Chemoenzymatic synthesis of 3-deoxy-3-fluoro-L-fucose and its enzymatic incorporation into glycoconjugates ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D0CC02209H _journal_year 2020 _chemical_absolute_configuration unk _chemical_formula_moiety 'C6 H11 F O4' _chemical_formula_sum 'C6 H11 F O4' _chemical_formula_weight 166.15 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-06-13 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-06-13 deposited with the CCDC. 2020-04-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.908(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.1522(3) _cell_length_b 4.7390(2) _cell_length_c 9.7711(4) _cell_measurement_reflns_used 4101 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.6840 _cell_measurement_theta_min 4.5240 _cell_volume 371.86(3) _computing_cell_refinement 'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 28.5714 _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -55.00 70.00 1.00 2.00 -- -19.30 60.00 120.00 125 2 \w -55.00 70.00 1.00 2.00 -- -19.30 57.00 60.00 125 3 \w -109.00 13.00 1.00 2.00 -- -19.30 -38.00-150.00 122 4 \w -52.00 70.00 1.00 2.00 -- -19.30 38.00-180.00 122 5 \w -109.00 7.00 1.00 2.00 -- -19.30 -60.00 0.00 116 ; _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 FRE-HF' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0581441000 _diffrn_orient_matrix_UB_12 0.0041564000 _diffrn_orient_matrix_UB_13 -0.0462298000 _diffrn_orient_matrix_UB_21 -0.0663775000 _diffrn_orient_matrix_UB_22 0.0136276000 _diffrn_orient_matrix_UB_23 -0.0569703000 _diffrn_orient_matrix_UB_31 0.0042962000 _diffrn_orient_matrix_UB_32 0.1490264000 _diffrn_orient_matrix_UB_33 0.0065583000 _diffrn_radiation_collimation 0.3 _diffrn_radiation_monochromator 'Confocal mirrors, HF Varimax' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_unetI/netI 0.0252 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5611 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.493 _diffrn_reflns_theta_min 3.011 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_current 55.0 _diffrn_source_power 2.475 _diffrn_source_target Mo _diffrn_source_type 'Rigaku FR-E+ SuperBright' _diffrn_source_voltage 45.0 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.18b (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.484 _exptl_crystal_description prism _exptl_crystal_F_000 176 _exptl_crystal_recrystallization_method 'The material was recrystallised from methanol by slow evaporation' _exptl_crystal_size_max 0.288 _exptl_crystal_size_mid 0.112 _exptl_crystal_size_min 0.062 _refine_diff_density_max 0.422 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 785 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.0(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 113 _refine_ls_number_reflns 1895 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0296 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.0652P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.0791 _reflns_Friedel_coverage 0.791 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 1854 _reflns_number_total 1895 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc02209h2.cif _cod_data_source_block 2019sot0012_k1_100k _cod_database_code 7126458 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_formula C6H11F1O4 _chemical_oxdiff_usercomment 3F-fucose _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _diffrn_measurement_device_type2 'Rigaku AFC12 (Right)' _reflns_odcompleteness_completeness 99.79 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 27.42 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C1(H1), C2(H2A), C3(H3A), C4(H4A), C5(H5) 2.b Idealised Me refined as rotating group: C6(H6A,H6B,H6C) ; _shelx_res_file ; TITL 2019sot0012_k1_100k_a.res in P2(1) 2019sot0012_k1_100k.res created by SHELXL-2016/6 at 10:40:36 on 13-Jun-2019 REM Old TITL 2019sot0012_K1_100K in P2(1) REM SHELXT solution in P2(1) REM R1 0.105, Rweak 0.026, Alpha 0.002, Orientation as input REM Flack x = 0.371 ( 0.315 ) from Parsons' quotients REM Formula found by SHELXT: C6 O2 F3 CELL 0.71073 8.1522 4.739 9.7711 90 99.908 90 ZERR 2 0.0003 0.0002 0.0004 0 0.004 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O F UNIT 12 22 8 2 EQIV $1 1-X,0.5+Y,1-Z EQIV $2 -X,-0.5+Y,-Z L.S. 4 0 0 PLAN 20 TEMP -173(2) HTAB O2 O1_$1 HTAB O4 F1_$2 BOND $H list 4 fmap 2 53 ACTA OMIT -3 57 REM REM REM WGHT 0.043400 0.065200 FVAR 1.46887 F1 4 -0.037503 0.464732 0.120616 11.00000 0.00971 0.02078 = 0.01332 0.00028 -0.00241 -0.00196 O1 3 0.422125 0.433545 0.367256 11.00000 0.01047 0.01771 = 0.00927 0.00151 0.00143 0.00317 O2 3 0.286157 0.799950 0.463173 11.00000 0.01300 0.01488 = 0.01771 -0.00425 -0.00070 -0.00008 H2 2 0.377047 0.854532 0.524004 11.00000 0.02835 O3 3 -0.011888 0.532702 0.412679 11.00000 0.01162 0.01717 = 0.01542 0.00018 0.00663 -0.00074 H3 2 -0.040579 0.407047 0.457290 11.00000 0.03503 O4 3 0.258718 0.197454 0.109160 11.00000 0.01445 0.01563 = 0.01302 -0.00348 -0.00056 0.00196 H4 2 0.184990 0.171837 0.044016 11.00000 0.02844 C1 1 0.288740 0.510747 0.437076 11.00000 0.01057 0.01496 = 0.00956 -0.00010 0.00158 0.00260 AFIX 13 H1 2 0.301602 0.407151 0.527453 11.00000 -1.20000 AFIX 0 C2 1 0.120858 0.431490 0.348958 11.00000 0.01060 0.01236 = 0.00993 0.00031 0.00244 -0.00055 AFIX 13 H2A 2 0.112762 0.221732 0.338844 11.00000 -1.20000 AFIX 0 C3 1 0.108660 0.566698 0.206780 11.00000 0.00795 0.01287 = 0.00969 -0.00037 -0.00115 -0.00121 AFIX 13 H3A 2 0.101391 0.776322 0.215834 11.00000 -1.20000 AFIX 0 C4 1 0.256488 0.491930 0.137360 11.00000 0.01139 0.01393 = 0.00958 0.00193 0.00200 0.00083 AFIX 13 H4A 2 0.248498 0.599201 0.048326 11.00000 -1.20000 AFIX 0 C5 1 0.416897 0.572427 0.233738 11.00000 0.01109 0.01676 = 0.01041 0.00187 0.00113 -0.00024 AFIX 13 H5 2 0.419533 0.781515 0.247744 11.00000 -1.20000 AFIX 0 C6 1 0.572610 0.481639 0.180026 11.00000 0.01121 0.03308 = 0.01670 0.00178 0.00433 0.00040 AFIX 137 H6A 2 0.575397 0.275327 0.173967 11.00000 -1.50000 H6B 2 0.671243 0.547965 0.243714 11.00000 -1.50000 H6C 2 0.571785 0.562972 0.087697 11.00000 -1.50000 AFIX 0 HKLF 4 REM 2019sot0012_k1_100k_a.res in P2(1) REM R1 = 0.0296 for 1854 Fo > 4sig(Fo) and 0.0304 for all 1895 data REM 113 parameters refined using 1 restraints END WGHT 0.0434 0.0652 REM Highest difference peak 0.422, deepest hole -0.165, 1-sigma level 0.045 Q1 1 0.2034 0.4872 0.3871 11.00000 0.05 0.42 Q2 1 0.3401 0.5358 0.1808 11.00000 0.05 0.38 Q3 1 0.1150 0.4947 0.2787 11.00000 0.05 0.31 Q4 1 0.1876 0.5158 0.1703 11.00000 0.05 0.30 Q5 1 0.3551 0.4681 0.3995 11.00000 0.05 0.27 Q6 1 0.3504 0.4882 0.5588 11.00000 0.05 0.25 Q7 1 0.4918 0.5091 0.2065 11.00000 0.05 0.23 Q8 1 0.0544 0.4769 0.3807 11.00000 0.05 0.23 Q9 1 0.0459 0.5306 0.1633 11.00000 0.05 0.18 Q10 1 0.4368 0.5181 0.3171 11.00000 0.05 0.18 Q11 1 0.5023 0.3862 0.4056 11.00000 0.05 0.17 Q12 1 0.1347 0.2938 0.3446 11.00000 0.05 0.16 Q13 1 0.3816 0.8695 0.4155 11.00000 0.05 0.15 Q14 1 0.2136 0.2171 0.1783 11.00000 0.05 0.15 Q15 1 0.2378 0.8996 0.3997 11.00000 0.05 0.14 Q16 1 0.2565 0.3643 0.1224 11.00000 0.05 0.14 Q17 1 0.2953 0.0122 0.1364 11.00000 0.05 0.14 Q18 1 0.4043 0.7158 0.2415 11.00000 0.05 0.13 Q19 1 0.4592 0.2670 0.3731 11.00000 0.05 0.13 Q20 1 0.3189 0.1984 0.0453 11.00000 0.05 0.13 ; _shelx_res_checksum 2042 _olex2_date_sample_submission 2019-05-21 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems' _olex2_exptl_crystal_mounting_method 'The crystal was mounted on a MITIGEN holder with silicon oil' _olex2_submission_original_sample_id 3F-fucose _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.539 _oxdiff_exptl_absorpt_empirical_full_min 0.424 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F -0.03750(11) 0.4647(2) 0.12062(10) 0.0151(2) Uani 1 1 d . . . . . O1 O 0.42213(14) 0.4335(3) 0.36726(12) 0.0125(3) Uani 1 1 d . . . . . O2 O 0.28616(16) 0.7999(3) 0.46317(13) 0.0156(3) Uani 1 1 d . . . . . H2 H 0.377(3) 0.855(6) 0.524(3) 0.028(7) Uiso 1 1 d . . . . . O3 O -0.01189(15) 0.5327(3) 0.41268(12) 0.0142(3) Uani 1 1 d . . . . . H3 H -0.041(4) 0.407(7) 0.457(3) 0.035(8) Uiso 1 1 d . . . . . O4 O 0.25872(16) 0.1975(3) 0.10916(13) 0.0147(3) Uani 1 1 d . . . . . H4 H 0.185(4) 0.172(6) 0.044(3) 0.028(7) Uiso 1 1 d . . . . . C1 C 0.28874(19) 0.5107(4) 0.43708(16) 0.0117(3) Uani 1 1 d . . . . . H1 H 0.301602 0.407151 0.527453 0.014 Uiso 1 1 calc R . . . . C2 C 0.12086(19) 0.4315(4) 0.34896(16) 0.0109(3) Uani 1 1 d . . . . . H2A H 0.112762 0.221732 0.338844 0.013 Uiso 1 1 calc R . . . . C3 C 0.1087(2) 0.5667(4) 0.20678(16) 0.0105(3) Uani 1 1 d . . . . . H3A H 0.101391 0.776322 0.215834 0.013 Uiso 1 1 calc R . . . . C4 C 0.25649(19) 0.4919(4) 0.13736(16) 0.0116(3) Uani 1 1 d . . . . . H4A H 0.248498 0.599201 0.048326 0.014 Uiso 1 1 calc R . . . . C5 C 0.4169(2) 0.5724(4) 0.23374(17) 0.0128(3) Uani 1 1 d . . . . . H5 H 0.419533 0.781515 0.247744 0.015 Uiso 1 1 calc R . . . . C6 C 0.5726(2) 0.4816(5) 0.18003(18) 0.0201(4) Uani 1 1 d . . . . . H6A H 0.575397 0.275327 0.173967 0.030 Uiso 1 1 calc GR . . . . H6B H 0.671243 0.547965 0.243714 0.030 Uiso 1 1 calc GR . . . . H6C H 0.571785 0.562972 0.087697 0.030 Uiso 1 1 calc GR . . . . 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 0.0097(4) 0.0208(6) 0.0133(4) 0.0003(4) -0.0024(3) -0.0020(4) O1 0.0105(5) 0.0177(6) 0.0093(5) 0.0015(5) 0.0014(4) 0.0032(5) O2 0.0130(6) 0.0149(7) 0.0177(6) -0.0043(5) -0.0007(4) -0.0001(5) O3 0.0116(5) 0.0172(6) 0.0154(5) 0.0002(5) 0.0066(4) -0.0007(5) O4 0.0145(6) 0.0156(7) 0.0130(6) -0.0035(5) -0.0006(5) 0.0020(5) C1 0.0106(7) 0.0150(8) 0.0096(6) -0.0001(6) 0.0016(5) 0.0026(6) C2 0.0106(7) 0.0124(8) 0.0099(7) 0.0003(6) 0.0024(5) -0.0005(6) C3 0.0080(7) 0.0129(8) 0.0097(6) -0.0004(6) -0.0012(5) -0.0012(6) C4 0.0114(7) 0.0139(9) 0.0096(6) 0.0019(6) 0.0020(5) 0.0008(6) C5 0.0111(7) 0.0168(9) 0.0104(7) 0.0019(6) 0.0011(6) -0.0002(6) C6 0.0112(7) 0.0331(11) 0.0167(8) 0.0018(8) 0.0043(6) 0.0004(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 2 0 5 0.0562 -2 0 -5 0.0562 -5 0 4 0.0308 5 0 -4 0.0308 0 -5 -1 0.1372 0 5 1 0.1372 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C5 113.91(12) . . ? C1 O2 H2 111.4(19) . . ? C2 O3 H3 108(2) . . ? C4 O4 H4 106(2) . . ? O1 C1 H1 108.9 . . ? O1 C1 C2 110.41(12) . . ? O2 C1 O1 112.08(14) . . ? O2 C1 H1 108.9 . . ? O2 C1 C2 107.66(13) . . ? C2 C1 H1 108.9 . . ? O3 C2 C1 110.16(12) . . ? O3 C2 H2A 109.7 . . ? O3 C2 C3 108.88(13) . . ? C1 C2 H2A 109.7 . . ? C3 C2 C1 108.80(13) . . ? C3 C2 H2A 109.7 . . ? F1 C3 C2 108.37(13) . . ? F1 C3 H3A 109.5 . . ? F1 C3 C4 107.72(12) . . ? C2 C3 H3A 109.5 . . ? C2 C3 C4 112.17(13) . . ? C4 C3 H3A 109.5 . . ? O4 C4 C3 110.60(13) . . ? O4 C4 H4A 109.3 . . ? O4 C4 C5 109.10(14) . . ? C3 C4 H4A 109.3 . . ? C5 C4 C3 109.11(13) . . ? C5 C4 H4A 109.3 . . ? O1 C5 C4 109.31(13) . . ? O1 C5 H5 109.2 . . ? O1 C5 C6 106.54(13) . . ? C4 C5 H5 109.2 . . ? C6 C5 C4 113.31(14) . . ? C6 C5 H5 109.2 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C3 1.4202(18) . ? O1 C1 1.4272(18) . ? O1 C5 1.4553(19) . ? O2 H2 0.90(3) . ? O2 C1 1.395(2) . ? O3 H3 0.80(3) . ? O3 C2 1.4215(18) . ? O4 H4 0.81(3) . ? O4 C4 1.423(2) . ? C1 H1 1.0000 . ? C1 C2 1.533(2) . ? C2 H2A 1.0000 . ? C2 C3 1.518(2) . ? C3 H3A 1.0000 . ? C3 C4 1.523(2) . ? C4 H4A 1.0000 . ? C4 C5 1.523(2) . ? C5 H5 1.0000 . ? C5 C6 1.517(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1 0.90(3) 1.83(3) 2.7287(17) 172(3) 2_656 O4 H4 F1 0.81(3) 2.08(3) 2.8489(16) 159(3) 2_545 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 1.9967 0.0000 4.9928 -0.1147 -0.4170 0.0413 -1.9967 -0.0000 -4.9928 0.1147 0.4170 -0.0413 -4.9922 -0.0006 3.9954 -0.4750 0.1037 0.0047 4.9922 0.0006 -3.9954 0.4750 -0.1037 -0.0047 0.0023 -4.9944 -1.0015 0.0257 -0.0112 -0.7509 -0.0023 4.9944 1.0015 -0.0257 0.0112 0.7509