#------------------------------------------------------------------------------ #$Date: 2018-04-21 15:07:10 +0300 (Sat, 21 Apr 2018) $ #$Revision: 207426 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/05/7230514.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_7230514 loop_ _publ_author_name 'Chakraborty, Shaunak' 'Desiraju, Gautam R.' _publ_section_title ; Exploring the structural landscape with ‘partial’ fluoro-substitution as a probe ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C8CE00336J _journal_year 2018 _chemical_formula_moiety 'C9 H7 F O2' _chemical_formula_sum 'C9 H7 F O2' _chemical_formula_weight 166.15 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014 _audit_update_record ; 2018-04-14 deposited with the CCDC. 2018-04-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.01(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.416(14) _cell_length_b 3.922(9) _cell_length_c 31.56(6) _cell_measurement_reflns_used 1086 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.2 _cell_volume 794(3) _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type CCD _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1094 _diffrn_reflns_av_unetI/netI 0.0963 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_number 5741 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.479 _diffrn_reflns_theta_min 3.175 _exptl_absorpt_coefficient_mu 0.113 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.390 _exptl_crystal_description plate _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.204 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 1805 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.1572 _refine_ls_R_factor_gt 0.1008 _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^)+(0.1458P)^2^+0.5344P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2796 _refine_ls_wR_factor_ref 0.3288 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1024 _reflns_number_total 1805 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8ce00336j2.cif _cod_data_source_block 1 _cod_database_code 7230514 _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. ; _shelxl_version_number 2014-3 _shelx_res_file ; TITL datam in P2/c New: P21/c CELL 0.71073 6.4160 3.9220 31.5600 90.000 90.010 90.000 ZERR 4.00 0.0140 0.0090 0.0600 0.000 0.030 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H F O UNIT 36 28 4 8 MERG 2 OMIT -2.00 55.00 EQIV $1 -x, -y+1, -z+1 HTAB C2 O2_$1 EQIV $2 -x, y-1/2, -z+1/2 HTAB C6 F1_$2 EQIV $3 -x+1, -y+2, -z+1 HTAB O2 O1_$3 OMIT 0 0 2 OMIT 0 0 4 FMAP 2 PLAN 20 ACTA HTAB 2.00000 BOND BOND $H L.S. 50 TEMP 23.00 WGHT 0.145800 0.534400 FVAR 0.51726 0.38967 MOLE 1 C1 1 0.276286 0.840628 0.464759 11.00000 0.06357 0.07611 = 0.05113 0.00333 -0.00084 -0.01549 C2 1 0.104084 0.716206 0.438018 11.00000 0.06290 0.07611 = 0.05864 -0.00129 0.00450 -0.01759 AFIX 43 H2 2 -0.006744 0.603370 0.450824 11.00000 -1.20000 AFIX 0 C3 1 0.101471 0.758813 0.396843 11.00000 0.05913 0.06457 = 0.05358 0.00356 0.00186 -0.01238 AFIX 43 H3 2 0.216144 0.869080 0.385138 11.00000 -1.20000 AFIX 0 C4 1 -0.061973 0.652214 0.367082 11.00000 0.05638 0.05333 = 0.05921 -0.00352 0.00009 -0.00071 C5 1 -0.033503 0.695145 0.323728 11.00000 0.06167 0.07669 = 0.05787 0.00236 0.00556 -0.00455 PART 1 AFIX 43 H5 2 0.091273 0.788836 0.314281 21.00000 -1.20000 AFIX 0 PART 2 F1 3 0.141035 0.845800 0.309694 -21.00000 0.06799 0.15785 = 0.05980 0.01811 0.00874 -0.00422 PART 0 C6 1 -0.182474 0.604788 0.293912 11.00000 0.08281 0.10147 = 0.05246 -0.00676 -0.00967 0.01129 AFIX 43 H6 2 -0.160973 0.642646 0.265153 11.00000 -1.20000 AFIX 0 C7 1 -0.363335 0.456965 0.308504 11.00000 0.07863 0.07792 = 0.08503 -0.01301 -0.02204 0.00145 PART 1 AFIX 43 H7 2 -0.464398 0.389673 0.289102 -21.00000 -1.20000 AFIX 0 PART 2 F2 3 -0.505241 0.367638 0.281500 21.00000 0.11280 0.13528 = 0.12346 -0.01986 -0.05476 -0.01421 PART 0 C8 1 -0.398191 0.406611 0.350671 11.00000 0.06422 0.07948 = 0.09517 -0.00141 -0.00406 -0.01432 AFIX 43 H8 2 -0.522176 0.307719 0.359722 11.00000 -1.20000 AFIX 0 C9 1 -0.249093 0.502681 0.379936 11.00000 0.06183 0.07371 = 0.06634 -0.00285 0.00244 -0.00739 AFIX 43 H9 2 -0.273758 0.467195 0.408636 11.00000 -1.20000 AFIX 0 O1 4 0.427080 0.995338 0.448306 11.00000 0.07566 0.11150 = 0.05925 0.01047 -0.00299 -0.02939 O2 4 0.264456 0.780445 0.504330 11.00000 0.08276 0.13705 = 0.04796 0.00730 -0.00475 -0.03862 AFIX 147 H2A 2 0.371345 0.845947 0.516023 11.00000 -1.50000 AFIX 0 HKLF 4 REM datam in P2/c New: P21/c REM R1 = 0.1008 for 1024 Fo > 4sig(Fo) and 0.1572 for all 1805 data REM 120 parameters refined using 0 restraints END WGHT 0.0684 0.3988 REM Instructions for potential hydrogen bonds HTAB C2 O2_$1 HTAB C6 F1_$2 HTAB O2 O1_$3 REM Highest difference peak 0.204, deepest hole -0.254, 1-sigma level 0.061 Q1 1 0.4448 0.7509 0.4484 11.00000 0.05 0.20 Q2 1 -0.1044 1.1031 0.3268 11.00000 0.05 0.19 Q3 1 0.2480 0.4273 0.5057 11.00000 0.05 0.19 Q4 1 0.4658 1.3654 0.4487 11.00000 0.05 0.18 Q5 1 0.5784 0.8257 0.4125 11.00000 0.05 0.17 Q6 1 -0.7152 0.5010 0.3349 11.00000 0.05 0.16 Q7 1 -0.0810 0.6428 0.4970 11.00000 0.05 0.16 Q8 1 -0.5397 0.0396 0.3457 11.00000 0.05 0.15 Q9 1 -0.1541 0.2263 0.3499 11.00000 0.05 0.15 Q10 1 -0.3580 0.9596 0.3991 11.00000 0.05 0.15 Q11 1 0.0608 1.1337 0.4365 11.00000 0.05 0.15 Q12 1 -0.1969 1.0078 0.2979 11.00000 0.05 0.15 Q13 1 0.1313 0.3214 0.4826 11.00000 0.05 0.14 Q14 1 0.2497 1.2713 0.3179 11.00000 0.05 0.13 Q15 1 -0.7480 0.3529 0.3171 11.00000 0.05 0.13 Q16 1 0.0283 0.2228 0.4503 11.00000 0.05 0.13 Q17 1 0.0849 1.0648 0.3966 11.00000 0.05 0.13 Q18 1 0.0362 1.2326 0.3144 11.00000 0.05 0.13 Q19 1 0.3940 0.7646 0.4025 11.00000 0.05 0.12 Q20 1 0.3070 0.4915 0.4667 11.00000 0.05 0.12 ; _shelx_res_checksum 39919 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 C1 C 0.2763(7) 0.8406(12) 0.46476(13) 0.0636(12) Uani 1 1 d . . . . . C2 C 0.1041(7) 0.7162(12) 0.43802(13) 0.0659(12) Uani 1 1 d . . . . . H2 H -0.0067 0.6034 0.4508 0.079 Uiso 1 1 calc R U . . . C3 C 0.1015(6) 0.7588(11) 0.39684(12) 0.0591(11) Uani 1 1 d . . . . . H3 H 0.2161 0.8691 0.3851 0.071 Uiso 1 1 calc R U . . . C4 C -0.0620(6) 0.6522(10) 0.36708(12) 0.0563(10) Uani 1 1 d . . . . . C5 C -0.0335(7) 0.6951(12) 0.32373(13) 0.0654(12) Uani 1 1 d . . . . . H5 H 0.0913 0.7888 0.3143 0.078 Uiso 0.390(6) 1 calc R U P A 1 F1 F 0.1410(7) 0.8458(15) 0.30969(13) 0.095(2) Uani 0.610(6) 1 d . . P A 2 C6 C -0.1825(8) 0.6048(15) 0.29391(14) 0.0789(14) Uani 1 1 d . . . . . H6 H -0.1610 0.6426 0.2652 0.095 Uiso 1 1 calc R U . . . C7 C -0.3633(8) 0.4570(14) 0.30850(17) 0.0805(14) Uani 1 1 d . . . . . H7 H -0.4644 0.3897 0.2891 0.097 Uiso 0.610(6) 1 calc R U P A 1 F2 F -0.5052(15) 0.368(3) 0.2815(3) 0.124(4) Uani 0.390(6) 1 d . . P A 2 C8 C -0.3982(8) 0.4066(14) 0.35067(17) 0.0796(14) Uani 1 1 d . . . . . H8 H -0.5222 0.3077 0.3597 0.096 Uiso 1 1 calc R U . . . C9 C -0.2491(6) 0.5027(12) 0.37994(14) 0.0673(12) Uani 1 1 d . . . . . H9 H -0.2738 0.4672 0.4086 0.081 Uiso 1 1 calc R U . . . O1 O 0.4271(5) 0.9953(9) 0.44831(10) 0.0821(11) Uani 1 1 d . . . . . O2 O 0.2645(5) 0.7804(11) 0.50433(9) 0.0893(13) Uani 1 1 d . . . . . H2A H 0.3713 0.8459 0.5160 0.134 Uiso 1 1 calc R U . . . 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 C1 0.064(3) 0.076(3) 0.051(2) 0.0033(19) -0.0008(18) -0.015(2) C2 0.063(3) 0.076(3) 0.059(2) -0.001(2) 0.0045(18) -0.018(2) C3 0.059(2) 0.065(3) 0.054(2) 0.0036(17) 0.0019(17) -0.012(2) C4 0.056(2) 0.053(2) 0.059(2) -0.0035(17) 0.0001(17) -0.0007(18) C5 0.062(2) 0.077(3) 0.058(2) 0.002(2) 0.0056(18) -0.005(2) F1 0.068(3) 0.158(5) 0.060(3) 0.018(3) 0.009(2) -0.004(3) C6 0.083(3) 0.101(4) 0.052(2) -0.007(2) -0.010(2) 0.011(3) C7 0.079(3) 0.078(3) 0.085(3) -0.013(3) -0.022(3) 0.001(3) F2 0.113(7) 0.135(8) 0.123(7) -0.020(6) -0.055(5) -0.014(6) C8 0.064(3) 0.079(3) 0.095(4) -0.001(3) -0.004(2) -0.014(2) C9 0.062(3) 0.074(3) 0.066(3) -0.003(2) 0.0024(19) -0.007(2) O1 0.076(2) 0.112(3) 0.0592(19) 0.0105(17) -0.0030(14) -0.029(2) O2 0.083(2) 0.137(3) 0.0480(18) 0.0073(18) -0.0048(14) -0.039(2) 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' F F 0.0171 0.0103 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C1 O2 122.8(4) O1 C1 C2 120.1(4) O2 C1 C2 117.1(4) C3 C2 C1 122.4(4) C3 C2 H2 118.8 C1 C2 H2 118.8 C2 C3 C4 127.4(4) C2 C3 H3 116.3 C4 C3 H3 116.3 C5 C4 C9 116.7(4) C5 C4 C3 120.1(4) C9 C4 C3 123.2(4) F1 C5 C6 117.6(4) F1 C5 C4 119.2(4) C6 C5 C4 123.1(4) C6 C5 H5 118.5 C4 C5 H5 118.5 C7 C6 C5 117.5(4) C7 C6 H6 121.3 C5 C6 H6 121.3 F2 C7 C8 119.2(7) F2 C7 C6 119.1(7) C8 C7 C6 121.7(4) C8 C7 H7 119.1 C6 C7 H7 119.1 C7 C8 C9 119.9(5) C7 C8 H8 120.0 C9 C8 H8 120.0 C8 C9 C4 121.0(4) C8 C9 H9 119.5 C4 C9 H9 119.5 C1 O2 H2A 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.255(5) C1 O2 1.273(5) C1 C2 1.473(6) C2 C3 1.310(6) C2 H2 0.9300 C3 C4 1.468(6) C3 H3 0.9300 C4 C5 1.391(6) C4 C9 1.396(6) C5 F1 1.341(7) C5 C6 1.387(7) C5 H5 0.9300 C6 C7 1.377(7) C6 H6 0.9300 C7 F2 1.295(9) C7 C8 1.364(8) C7 H7 0.9300 C8 C9 1.382(6) C8 H8 0.9300 C9 H9 0.9300 O2 H2A 0.8200 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 C2 H2 O2 0.93 2.65 3.563(7) 168.8 3_566 C6 H6 F1 0.93 2.64 3.434(8) 144.2 2_545 O2 H2A O1 0.82 1.82 2.631(6) 167.8 3_676