#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:28:26 +0200 (Fri, 13 Oct 2017) $ #$Revision: 201972 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/01/2100148.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_2100148 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_paper_doi 10.1107/S0108768104030617 _journal_volume 61 _journal_year 2005 _chemical_formula_moiety 'C6 H5 Cl1 O1' _chemical_formula_sum 'C6 H5 Cl O' _chemical_formula_weight 128.56 _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_method CRYSTALS_ver_12.39 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 3.9846(5) _cell_length_b 13.9272(19) _cell_length_c 20.699(3) _cell_measurement_reflns_used 1504 _cell_measurement_temperature 150 _cell_measurement_theta_max 25 _cell_measurement_theta_min 5 _cell_volume 1148.7(3) _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 0.983 _diffrn_measured_fraction_theta_max 0.983 _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 0.052 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 4548 _diffrn_reflns_theta_full 25.025 _diffrn_reflns_theta_max 25.025 _diffrn_reflns_theta_min 1.762 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.545 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_correction_T_min 0.22 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.487 _exptl_crystal_description rod _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.56 _refine_diff_density_min -0.58 _refine_ls_abs_structure_details 'Flack, 10 Friedel-pairs' _refine_ls_abs_structure_Flack 0.1(2) _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9424 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 152 _refine_ls_number_reflns 1977 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0685 _refine_ls_shift/su_max 0.000204 _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: 0.00 0.00 0.00 0.00 0.00 0.333 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1425 _refine_ls_wR_factor_gt 0.1314 _refine_ls_wR_factor_ref 0.1425 _reflns_number_gt 1376 _reflns_number_total 1987 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bs5012.cif _cod_data_source_block 3CL _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_original_sg_symbol_H-M 'P 21 21 21 ' _cod_original_formula_sum 'C6 H5 Cl1 O1' _cod_database_code 2100148 _cod_database_fobs_code 2100148 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_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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C11 0.1389(17) -0.4542(5) -1.0155(3) 0.0307 Uani 1.0000 . . C C21 0.2721(18) -0.5022(5) -0.9628(3) 0.0298 Uani 1.0000 . . C C31 0.4339(17) -0.5888(4) -0.9724(3) 0.0285 Uani 1.0000 . . C C41 0.4796(19) -0.6256(5) -1.0352(3) 0.0354 Uani 1.0000 . . C C51 0.3484(18) -0.5759(5) -1.0870(4) 0.0390 Uani 1.0000 . . C C61 0.1842(17) -0.4893(5) -1.0775(3) 0.0292 Uani 1.0000 . . C O71 -0.0253(14) -0.3688(3) -1.0033(2) 0.0380 Uani 1.0000 . . O Cl81 0.5944(5) -0.64964(14) -0.90659(9) 0.0436 Uani 1.0000 . . Cl C12 -0.0342(18) -0.2531(5) -0.8518(3) 0.0299 Uani 1.0000 . . C C22 -0.1901(16) -0.3385(5) -0.8375(3) 0.0264 Uani 1.0000 . . C C32 -0.3016(15) -0.3544(5) -0.7756(3) 0.0339 Uani 1.0000 . . C C42 -0.2603(17) -0.2870(5) -0.7263(3) 0.0348 Uani 1.0000 . . C C52 -0.1052(17) -0.2016(5) -0.7422(3) 0.0351 Uani 1.0000 . . C C62 0.0089(19) -0.1837(4) -0.8041(3) 0.0344 Uani 1.0000 . . C O72 0.0864(14) -0.2336(3) -0.9123(2) 0.0385 Uani 1.0000 . . O Cl82 -0.4871(5) -0.46531(12) -0.75731(8) 0.0423 Uani 1.0000 . . Cl H72 0.02(2) -0.277(4) -0.935(3) 0.0500 Uiso 1.0000 . . H H71 -0.08(2) -0.351(5) -1.043(2) 0.0500 Uiso 1.0000 . . H H21 0.2523 -0.4760 -0.9206 0.0358 Uiso 1.0000 . . H H41 0.5991 -0.6838 -1.0417 0.0425 Uiso 1.0000 . . H H51 0.3707 -0.6011 -1.1294 0.0468 Uiso 1.0000 . . H H61 0.1026 -0.4541 -1.1135 0.0351 Uiso 1.0000 . . H H22 -0.2204 -0.3859 -0.8699 0.0316 Uiso 1.0000 . . H H42 -0.3358 -0.2995 -0.6836 0.0418 Uiso 1.0000 . . H H52 -0.0762 -0.1539 -0.7098 0.0421 Uiso 1.0000 . . H H62 0.1159 -0.1246 -0.8140 0.0413 Uiso 1.0000 . . 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 0.030(4) 0.026(4) 0.036(4) -0.009(3) 0.003(3) 0.002(3) C21 0.026(4) 0.037(4) 0.026(4) -0.006(3) -0.001(3) -0.002(3) C31 0.021(4) 0.019(3) 0.045(4) -0.008(3) -0.001(3) 0.002(3) C41 0.025(4) 0.032(4) 0.049(4) 0.000(3) 0.001(4) -0.006(3) C51 0.035(4) 0.041(4) 0.042(4) 0.000(3) 0.003(4) -0.014(4) C61 0.037(4) 0.024(4) 0.026(4) -0.006(3) 0.000(3) 0.005(3) O71 0.046(3) 0.029(3) 0.039(3) 0.003(3) -0.010(3) -0.001(2) Cl81 0.0423(11) 0.0392(10) 0.0493(10) 0.0064(9) 0.0005(10) 0.0103(9) C12 0.027(4) 0.033(4) 0.030(3) 0.004(3) -0.002(3) 0.004(3) C22 0.033(4) 0.015(3) 0.031(3) 0.004(3) -0.001(3) 0.001(3) C32 0.020(3) 0.035(4) 0.046(4) 0.009(3) 0.002(3) 0.014(4) C42 0.032(4) 0.042(4) 0.030(4) 0.007(4) 0.000(3) 0.002(3) C52 0.034(4) 0.036(4) 0.036(4) 0.005(3) -0.005(4) -0.005(3) C62 0.035(4) 0.026(3) 0.042(4) -0.005(3) -0.003(4) 0.002(3) O72 0.052(3) 0.032(3) 0.032(3) -0.010(3) 0.004(3) 0.001(2) Cl82 0.0432(10) 0.0337(9) 0.0500(10) -0.0004(9) 0.0075(10) 0.0070(8) 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' Cl 0.1484 0.1585 '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 _geom_angle_publ_flag C21 C11 C61 120.6(7) yes C21 C11 O71 116.9(6) yes C61 C11 O71 122.4(6) yes C11 C21 C31 119.0(6) yes C11 C21 H21 120.476 no C31 C21 H21 120.475 no C21 C31 C41 120.8(6) yes C21 C31 Cl81 119.1(5) yes C41 C31 Cl81 120.1(5) yes C31 C41 C51 119.0(7) yes C31 C41 H41 120.481 no C51 C41 H41 120.486 no C41 C51 C61 120.3(7) yes C41 C51 H51 119.827 no C61 C51 H51 119.827 no C51 C61 C11 120.0(6) yes C51 C61 H61 119.981 no C11 C61 H61 119.981 no C11 O71 H71 101(5) no C22 C12 C62 120.2(6) yes C22 C12 O72 121.9(6) yes C62 C12 O72 117.9(6) yes C12 C22 C32 119.1(6) yes C12 C22 H22 120.427 no C32 C22 H22 120.427 no C22 C32 C42 122.4(6) yes C22 C32 Cl82 118.6(6) yes C42 C32 Cl82 118.9(5) yes C32 C42 C52 117.3(6) yes C32 C42 H42 121.369 no C52 C42 H42 121.368 no C42 C52 C62 121.5(6) yes C42 C52 H52 119.250 no C62 C52 H52 119.249 no C12 C62 C52 119.5(6) yes C12 C62 H62 120.240 no C52 C62 H62 120.235 no C12 O72 H72 105(5) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C11 C21 . . 1.387(9) yes C11 C61 . . 1.384(8) yes C11 O71 . . 1.381(8) yes C21 C31 . . 1.382(9) yes C21 H21 . . 0.950 no C31 C41 . . 1.409(8) yes C31 Cl81 . . 1.727(7) yes C41 C51 . . 1.380(10) yes C41 H41 . . 0.950 no C51 C61 . . 1.385(9) yes C51 H51 . . 0.950 no C61 H61 . . 0.950 no O71 H71 . . 0.89(4) no C12 C22 . . 1.374(9) yes C12 C62 . . 1.393(8) yes C12 O72 . . 1.368(7) yes C22 C32 . . 1.373(8) yes C22 H22 . . 0.950 no C32 C42 . . 1.396(9) yes C32 Cl82 . . 1.754(7) yes C42 C52 . . 1.381(9) yes C42 H42 . . 0.950 no C52 C62 . . 1.382(9) yes C52 H52 . . 0.950 no C62 H62 . . 0.950 no O72 H72 . . 0.81(4) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 13875432