#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:01:59 +0200 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/01/2100150.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_2100150 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 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/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 93.954(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 8.7086(11) _cell_length_b 15.4523(19) _cell_length_c 8.7414(11) _cell_measurement_reflns_used 3307 _cell_measurement_temperature 150 _cell_measurement_theta_max 29 _cell_measurement_theta_min 2 _cell_volume 1173.5(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 'SIR92 (Altomare et al, 1994)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.925 _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 0.024 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7471 _diffrn_reflns_theta_full 27.114 _diffrn_reflns_theta_max 28.844 _diffrn_reflns_theta_min 2.344 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.534 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.455 _exptl_crystal_description block _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.33 _refine_diff_density_min -0.31 _refine_ls_extinction_coef 45(11) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _refine_ls_goodness_of_fit_ref 0.7348 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 152 _refine_ls_number_reflns 2839 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0387 _refine_ls_shift/su_max 0.001444 _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: 0.684E-01 0.725 0.00 0.00 0.00 0.333 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1006 _refine_ls_wR_factor_gt 0.0966 _refine_ls_wR_factor_ref 0.1006 _reflns_number_gt 2442 _reflns_number_total 2839 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bs5012.cif _cod_data_source_block 4CL1 _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_enum 1527 2010-12-29 10:47:43Z saulius 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_original_sg_symbol_H-M 'P 21/c' _cod_original_formula_sum 'C6 H5 Cl1 O1' _cod_database_code 2100150 _cod_database_fobs_code 2100150 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C11 1.06333(17) 0.86425(11) 0.17530(18) 0.0249 Uani 1.0000 . . C C21 1.16611(19) 0.85202(11) 0.0632(2) 0.0291 Uani 1.0000 . . C C31 1.2470(2) 0.92194(12) 0.01072(19) 0.0308 Uani 1.0000 . . C C41 1.22279(18) 1.00316(11) 0.07053(19) 0.0271 Uani 1.0000 . . C C51 1.11976(19) 1.01599(11) 0.18165(19) 0.0284 Uani 1.0000 . . C C61 1.03955(18) 0.94587(11) 0.23426(19) 0.0272 Uani 1.0000 . . C O71 0.98528(14) 0.79260(8) 0.22328(14) 0.0304 Uani 1.0000 . . O Cl81 1.32180(5) 1.09146(3) 0.00165(5) 0.0380 Uani 1.0000 . . Cl C12 0.69379(17) 0.67154(10) 0.01969(18) 0.0238 Uani 1.0000 . . C C22 0.62387(19) 0.70668(11) 0.14329(18) 0.0278 Uani 1.0000 . . C C32 0.47123(19) 0.68836(11) 0.16344(19) 0.0282 Uani 1.0000 . . C C42 0.39015(18) 0.63485(10) 0.06042(19) 0.0256 Uani 1.0000 . . C C52 0.4581(2) 0.60033(11) -0.06413(19) 0.0281 Uani 1.0000 . . C C62 0.61153(19) 0.61851(10) -0.08394(19) 0.0277 Uani 1.0000 . . C O72 0.84562(14) 0.68764(8) -0.00399(14) 0.0315 Uani 1.0000 . . O Cl82 0.19921(5) 0.61016(3) 0.08950(5) 0.0353 Uani 1.0000 . . Cl H71 0.942(3) 0.8050(16) 0.300(2) 0.0500 Uiso 1.0000 . . H H72 0.885(3) 0.7164(15) 0.066(3) 0.0500 Uiso 1.0000 . . H H21 1.1811 0.7959 0.0224 0.0351 Uiso 1.0000 . . H H31 1.3183 0.9141 -0.0656 0.0373 Uiso 1.0000 . . H H51 1.1041 1.0723 0.2215 0.0339 Uiso 1.0000 . . H H61 0.9684 0.9538 0.3107 0.0328 Uiso 1.0000 . . H H22 0.6807 0.7432 0.2139 0.0335 Uiso 1.0000 . . H H32 0.4225 0.7124 0.2476 0.0342 Uiso 1.0000 . . H H52 0.4004 0.5646 -0.1354 0.0336 Uiso 1.0000 . . H H62 0.6600 0.5946 -0.1684 0.0335 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 0.0220(7) 0.0286(8) 0.0240(7) -0.0004(6) 0.0013(6) 0.0016(6) C21 0.0295(8) 0.0290(8) 0.0293(8) 0.0030(7) 0.0066(6) -0.0022(6) C31 0.0292(8) 0.0384(9) 0.0256(8) 0.0000(7) 0.0071(6) 0.0009(7) C41 0.0243(7) 0.0320(8) 0.0246(8) -0.0051(6) -0.0023(6) 0.0045(6) C51 0.0291(8) 0.0272(8) 0.0285(8) 0.0002(6) -0.0006(6) -0.0030(6) C61 0.0230(7) 0.0332(9) 0.0258(8) 0.0017(6) 0.0037(6) -0.0024(6) O71 0.0319(6) 0.0299(6) 0.0308(7) -0.0036(5) 0.0107(5) -0.0008(5) Cl81 0.0403(3) 0.0389(3) 0.0346(2) -0.01376(18) 0.00157(18) 0.00619(18) C12 0.0238(7) 0.0240(7) 0.0241(7) 0.0004(6) 0.0048(6) 0.0038(6) C22 0.0293(8) 0.0295(8) 0.0249(8) -0.0048(6) 0.0049(6) -0.0044(6) C32 0.0288(8) 0.0317(8) 0.0250(8) -0.0013(6) 0.0084(6) -0.0018(6) C42 0.0234(7) 0.0258(8) 0.0278(8) -0.0020(6) 0.0043(6) 0.0048(6) C52 0.0313(8) 0.0270(8) 0.0257(8) -0.0030(6) -0.0009(6) -0.0006(6) C62 0.0325(8) 0.0274(8) 0.0239(8) 0.0007(6) 0.0076(6) -0.0018(6) O72 0.0261(6) 0.0380(7) 0.0314(6) -0.0047(5) 0.0089(5) -0.0057(5) Cl82 0.0253(2) 0.0422(3) 0.0387(3) -0.00696(17) 0.00520(17) 0.00136(18) 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 120.58(15) yes C21 C11 O71 117.49(15) yes C61 C11 O71 121.93(14) yes C11 C21 C31 119.74(16) yes C11 C21 H21 120.132 no C31 C21 H21 120.133 no C21 C31 C41 119.28(15) yes C21 C31 H31 120.358 no C41 C31 H31 120.358 no C31 C41 C51 121.33(15) yes C31 C41 Cl81 119.24(13) yes C51 C41 Cl81 119.42(13) yes C41 C51 C61 119.22(15) yes C41 C51 H51 120.391 no C61 C51 H51 120.391 no C51 C61 C11 119.85(15) yes C51 C61 H61 120.077 no C11 C61 H61 120.077 no C11 O71 H71 109.2(18) no C22 C12 C62 120.43(14) yes C22 C12 O72 121.66(14) yes C62 C12 O72 117.92(14) yes C12 C22 C32 119.79(15) yes C12 C22 H22 120.105 no C32 C22 H22 120.106 no C22 C32 C42 119.52(15) yes C22 C32 H32 120.242 no C42 C32 H32 120.241 no C32 C42 C52 121.19(15) yes C32 C42 Cl82 119.11(13) yes C52 C42 Cl82 119.69(13) yes C42 C52 C62 119.23(15) yes C42 C52 H52 120.386 no C62 C52 H52 120.386 no C52 C62 C12 119.83(14) yes C52 C62 H62 120.084 no C12 C62 H62 120.083 no C12 O72 H72 110.4(17) 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 . . 1.385(2) yes C11 C61 . . 1.383(2) yes C11 O71 . . 1.3795(19) yes C21 C31 . . 1.385(2) yes C21 H21 . . 0.950 no C31 C41 . . 1.381(2) yes C31 H31 . . 0.950 no C41 C51 . . 1.381(2) yes C41 Cl81 . . 1.7433(17) yes C51 C61 . . 1.385(2) yes C51 H51 . . 0.950 no C61 H61 . . 0.950 no O71 H71 . . 0.815(19) no C12 C22 . . 1.387(2) yes C12 C62 . . 1.384(2) yes C12 O72 . . 1.3750(18) yes C22 C32 . . 1.382(2) yes C22 H22 . . 0.950 no C32 C42 . . 1.380(2) yes C32 H32 . . 0.950 no C42 C52 . . 1.381(2) yes C42 Cl82 . . 1.7416(16) yes C52 C62 . . 1.388(2) yes C52 H52 . . 0.950 no C62 H62 . . 0.950 no O72 H72 . . 0.816(19) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 13875219 2 PubChem 69671381