#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2100153.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_2100153 loop_ _publ_author_name 'Oswald, Iain D. H.' 'Allan, David R.' 'Motherwell, W. D. Samuel' 'Parsons, Simon' _publ_section_title ; Structures of the monofluoro- and monochlorophenols at low temperature and high pressure ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 69 _journal_page_last 79 _journal_volume 61 _journal_year 2005 _chemical_formula_moiety 'C6 H5 F1 O1' _chemical_formula_sum 'C6 H5 F O' _chemical_formula_weight 112.10 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_method CRYSTALS_ver_12.39 _cell_angle_alpha 90 _cell_angle_beta 100.234(2) _cell_angle_gamma 90 _cell_formula_units_Z 12 _cell_length_a 17.1336(10) _cell_length_b 8.2766(5) _cell_length_c 11.4975(7) _cell_measurement_reflns_used 2044 _cell_measurement_temperature 150 _cell_measurement_theta_max 26 _cell_measurement_theta_min 2 _cell_volume 1604.50(17) _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.944 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 7505 _diffrn_reflns_theta_full 27.264 _diffrn_reflns_theta_max 28.699 _diffrn_reflns_theta_min 2.416 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.575 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.392 _exptl_crystal_description cylinder _exptl_crystal_F_000 696 _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.38 _refine_diff_density_max 0.32 _refine_diff_density_min -0.40 _refine_ls_extinction_coef 29(9) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _refine_ls_goodness_of_fit_ref 1.0751 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 125 _refine_ls_number_reflns 1956 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0562 _refine_ls_shift/su_max 0.000179 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F^2^)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.172E-01 1.34 0.00 0.00 0.00 0.333 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1107 _refine_ls_wR_factor_gt 0.1032 _refine_ls_wR_factor_ref 0.1107 _reflns_number_gt 1302 _reflns_number_total 1957 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bs5012.cif _[local]_cod_data_source_block 2F1 _[local]_cod_cif_authors_sg_H-M 'C 2/c ' _[local]_cod_chemical_formula_sum_orig 'C6 H5 F1 O1' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2100153 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 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_occupancy _atom_site_type_symbol C11 0.63513(11) 0.0773(3) 0.59162(18) 0.0371 Uani 1.0000 C C21 0.66814(13) -0.0140(3) 0.5134(2) 0.0457 Uani 1.0000 C C31 0.74867(14) -0.0170(3) 0.5146(2) 0.0545 Uani 1.0000 C C41 0.79752(13) 0.0740(4) 0.5970(2) 0.0560 Uani 1.0000 C C51 0.76568(13) 0.1655(4) 0.6765(2) 0.0542 Uani 1.0000 C C61 0.68456(13) 0.1672(3) 0.67446(19) 0.0446 Uani 1.0000 C O71 0.55429(9) 0.0768(2) 0.58623(14) 0.0443 Uani 1.0000 O F81 0.61874(8) -0.1033(2) 0.43296(13) 0.0707 Uani 1.0000 F C12 0.5000 0.4249(4) 0.7500 0.0319 Uani 1.0000 C C22 0.53050(11) 0.5110(3) 0.66635(18) 0.0377 Uani 1.0000 C C32 0.53071(13) 0.6767(3) 0.6650(2) 0.0484 Uani 1.0000 C C42 0.5000 0.7589(4) 0.7500 0.0560 Uani 1.0000 C O72 0.5000 0.2598(3) 0.7500 0.0454 Uani 1.0000 O F82 0.56421(14) 0.4402(3) 0.5881(2) 0.0438 Uani 0.5000 F H72 0.511(3) 0.214(6) 0.694(4) 0.0500 Uiso 0.5000 H H71 0.541(3) 0.145(5) 0.632(4) 0.0527 Uiso 0.5000 H H712 0.527(2) 0.032(6) 0.527(3) 0.0527 Uiso 0.5000 H H31 0.7701 -0.0811 0.4593 0.0665 Uiso 1.0000 H H41 0.8532 0.0737 0.5990 0.0666 Uiso 1.0000 H H51 0.7996 0.2284 0.7335 0.0635 Uiso 1.0000 H H61 0.6631 0.2304 0.7302 0.0531 Uiso 1.0000 H H32 0.5519 0.7337 0.6059 0.0566 Uiso 1.0000 H H42 0.5000 0.8737 0.7500 0.0645 Uiso 1.0000 H H62 0.5521 0.4541 0.6077 0.0449 Uiso 0.5000 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 C11 0.0317(10) 0.0416(13) 0.0380(12) -0.0015(10) 0.0063(9) 0.0065(10) C21 0.0365(12) 0.0536(15) 0.0462(13) -0.0059(11) 0.0048(10) -0.0052(12) C31 0.0407(12) 0.0704(18) 0.0553(15) 0.0058(13) 0.0160(11) -0.0029(14) C41 0.0303(11) 0.083(2) 0.0535(15) 0.0011(13) 0.0037(11) 0.0092(15) C51 0.0368(12) 0.0772(19) 0.0447(14) -0.0074(12) -0.0035(11) 0.0023(13) C61 0.0389(12) 0.0545(15) 0.0393(13) -0.0008(11) 0.0044(10) -0.0013(11) O71 0.0310(8) 0.0479(11) 0.0544(11) -0.0031(7) 0.0084(7) -0.0049(8) F81 0.0471(8) 0.0907(12) 0.0761(10) -0.0108(8) 0.0159(7) -0.0408(10) C12 0.0267(13) 0.0319(16) 0.0356(15) 0.0000 0.0012(11) 0.0000 C22 0.0297(10) 0.0443(13) 0.0383(12) 0.0039(10) 0.0043(9) 0.0079(11) C32 0.0439(13) 0.0409(14) 0.0567(15) -0.0054(11) -0.0009(11) 0.0184(12) C42 0.059(2) 0.0324(19) 0.070(3) 0.0000 -0.0073(19) 0.0000 O72 0.0623(15) 0.0312(13) 0.0416(14) 0.0000 0.0065(12) 0.0000 F82 0.0513(14) 0.0443(16) 0.0399(14) 0.0068(12) 0.0194(11) 0.0049(12) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 'International Tables Vol C 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C21 C11 C61 . . 118.51(19) yes C21 C11 O71 . . 119.87(19) yes C61 C11 O71 . . 121.6(2) yes C11 C21 C31 . . 122.2(2) yes C11 C21 F81 . . 117.86(18) yes C31 C21 F81 . . 120.0(2) yes C21 C31 C41 . . 118.9(2) yes C21 C31 H31 . . 120.534 no C41 C31 H31 . . 120.529 no C31 C41 C51 . . 119.8(2) yes C31 C41 H41 . . 120.110 no C51 C41 H41 . . 120.108 no C41 C51 C61 . . 120.7(2) yes C41 C51 H51 . . 119.663 no C61 C51 H51 . . 119.655 no C51 C61 C11 . . 119.9(2) yes C51 C61 H61 . . 120.048 no C11 C61 H61 . . 120.048 no C11 O71 H71 . . 111(3) no C11 O71 H712 . . 117(3) no H71 O71 H712 . . 129(5) no C22 C12 C22 5_656 . 117.5(3) yes C22 C12 O72 5_656 . 121.27(14) yes C22 C12 O72 . . 121.27(14) yes C12 C22 C32 . . 122.0(2) yes C12 C22 F82 . . 121.7(2) yes C32 C22 F82 . . 116.3(2) yes C12 C22 H62 . . 119.020 no C32 C22 H62 . . 119.018 no F82 C22 H62 . . 4.045 no C22 C32 C42 . . 119.1(2) yes C22 C32 H32 . . 120.461 no C42 C32 H32 . . 120.458 no C32 C42 C32 . 5_656 120.5(3) yes C32 C42 H42 . . 119.769 no C32 C42 H42 5_656 . 119.769 no C12 O72 H72 . 5_656 118(4) no C12 O72 H72 . . 118(4) no H72 O72 H72 5_656 . 123(7) no 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 C11 C21 . 1.371(3) yes C11 C61 . 1.375(3) yes C11 O71 . 1.375(2) yes C21 C31 . 1.378(3) yes C21 F81 . 1.357(2) yes C31 C41 . 1.372(3) yes C31 H31 . 0.950 no C41 C51 . 1.373(4) yes C41 H41 . 0.950 no C51 C61 . 1.386(3) yes C51 H51 . 0.950 no C61 H61 . 0.950 no O71 H71 . 0.830(19) no O71 H712 . 0.836(19) no C12 C22 5_656 1.373(2) yes C12 C22 . 1.373(2) yes C12 O72 . 1.366(4) yes C22 C32 . 1.372(3) yes C22 F82 . 1.293(3) yes C22 H62 . 0.950 no C32 C42 . 1.371(3) yes C32 H32 . 0.950 no C42 H42 . 0.950 no O72 H72 5_656 0.80(3) no O72 H72 . 0.80(3) no