#------------------------------------------------------------------------------ #$Date: 2016-02-14 15:26:36 +0100 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/01/2100149.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_2100149 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 4.0949(4) _cell_length_b 13.875(3) _cell_length_c 20.716(3) _cell_measurement_reflns_used 983 _cell_measurement_temperature 293 _cell_measurement_theta_max 23 _cell_measurement_theta_min 3 _cell_volume 1177.0(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 293 _diffrn_measured_fraction_theta_full 0.827 _diffrn_measured_fraction_theta_max 0.754 _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 0.147 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 6533 _diffrn_reflns_theta_full 17.448 _diffrn_reflns_theta_max 23.265 _diffrn_reflns_theta_min 2.454 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.532 _exptl_absorpt_correction_T_max 0.91 _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour block _exptl_crystal_density_diffrn 1.451 _exptl_crystal_description colourless _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.59 _refine_diff_density_min -0.56 _refine_ls_abs_structure_details 'Flack, 0 Friedel-pairs' _refine_ls_abs_structure_Flack 1.1(5) _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9863 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 62 _refine_ls_number_reflns 780 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.1462 _refine_ls_R_factor_gt 0.0978 _refine_ls_shift/su_max 0.003791 _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: 0.106 5.04 0.00 0.00 0.00 0.333 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.2444 _refine_ls_wR_factor_gt 0.2171 _refine_ls_wR_factor_ref 0.2444 _reflns_number_gt 476 _reflns_number_total 780 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bs5012.cif _cod_data_source_block 3CLP _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 2100149 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 0.1433 -0.4528 -1.0157 0.043(4) Uiso 1.0000 . . C C21 0.2743 -0.5021 -0.9634 0.047(4) Uiso 1.0000 . . C C31 0.4446 -0.5875 -0.9732 0.054(4) Uiso 1.0000 . . C C41 0.4839 -0.6236 -1.0353 0.064(4) Uiso 1.0000 . . C C51 0.3529 -0.5743 -1.0876 0.058(4) Uiso 1.0000 . . C C61 0.1826 -0.4888 -1.0778 0.050(4) Uiso 1.0000 . . C O71 -0.026(2) -0.3696(2) -1.00767(10) 0.0683 Uani 1.0000 . . O Cl81 0.5969(11) -0.6480(2) -0.90755(14) 0.0800 Uani 1.0000 . . Cl C12 -0.0220 -0.2536 -0.8523 0.049(4) Uiso 1.0000 . . C C22 -0.1816 -0.3392 -0.8375 0.053(4) Uiso 1.0000 . . C C32 -0.2985 -0.3550 -0.7754 0.054(4) Uiso 1.0000 . . C C42 -0.2557 -0.2852 -0.7281 0.061(4) Uiso 1.0000 . . C C52 -0.0960 -0.1995 -0.7428 0.066(5) Uiso 1.0000 . . C C62 0.0208 -0.1838 -0.8049 0.061(4) Uiso 1.0000 . . C O72 0.1012(16) -0.2366(3) -0.9123(2) 0.0641 Uani 1.0000 . . O Cl82 -0.4850(11) -0.4630(3) -0.75811(10) 0.0773 Uani 1.0000 . . Cl H71 -0.1478 -0.3540 -1.0393 0.0500 Uiso 1.0000 . . H H72 0.0260 -0.2718 -0.9414 0.0500 Uiso 1.0000 . . H H21 0.2475 -0.4775 -0.9209 0.0562 Uiso 1.0000 . . H H41 0.6003 -0.6820 -1.0420 0.0762 Uiso 1.0000 . . H H51 0.3797 -0.5989 -1.1301 0.0703 Uiso 1.0000 . . H H61 0.0930 -0.4551 -1.1136 0.0610 Uiso 1.0000 . . H H22 -0.2109 -0.3870 -0.8699 0.0630 Uiso 1.0000 . . H H42 -0.3356 -0.2959 -0.6856 0.0724 Uiso 1.0000 . . H H52 -0.0668 -0.1518 -0.7105 0.0798 Uiso 1.0000 . . H H62 0.1299 -0.1252 -0.8150 0.0731 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 O71 0.087(7) 0.060(10) 0.059(7) 0.020(7) -0.015(6) -0.006(4) Cl81 0.104(3) 0.061(4) 0.074(3) 0.013(3) 0.003(3) 0.024(2) O72 0.108(8) 0.038(9) 0.047(6) -0.018(6) 0.016(6) -0.005(4) Cl82 0.099(3) 0.060(4) 0.073(3) 0.003(3) 0.018(3) 0.0178(19) 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 120.00 yes C21 C11 O71 121.37(7) yes C61 C11 O71 118.63(7) yes C11 C21 C31 120.00 yes C11 C21 H21 120.000 no C31 C21 H21 120.000 no C21 C31 C41 120.00 yes C21 C31 Cl81 118.95(6) yes C41 C31 Cl81 121.04(6) yes C31 C41 C51 120.00 yes C31 C41 H41 120.000 no C51 C41 H41 120.000 no C41 C51 C61 120.00 yes C41 C51 H51 120.000 no C61 C51 H51 120.000 no C11 C61 C51 120.00 yes C11 C61 H61 120.000 no C51 C61 H61 120.000 no C11 O71 H71 114.868 no C22 C12 C62 120.00 yes C22 C12 O72 121.51(7) yes C62 C12 O72 118.48(6) yes C12 C22 C32 120.00 yes C12 C22 H22 120.000 no C32 C22 H22 120.000 no C22 C32 C42 120.00 yes C22 C32 Cl82 118.91(6) yes C42 C32 Cl82 121.06(6) yes C32 C42 C52 120.00 yes C32 C42 H42 120.000 no C52 C42 H42 120.000 no C42 C52 C62 120.00 yes C42 C52 H52 120.000 no C62 C52 H52 120.000 no C12 C62 C52 120.00 yes C12 C62 H62 120.000 no C52 C62 H62 120.000 no C12 O72 H72 114.913 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 . . 1.39 yes C11 C61 . . 1.39 yes C11 O71 . . 1.356(4) yes C21 C31 . . 1.39 yes C21 H21 . . 0.950 no C31 C41 . . 1.39 yes C31 Cl81 . . 1.715(4) yes C41 C51 . . 1.39 yes C41 H41 . . 0.950 no C51 C61 . . 1.39 yes C51 H51 . . 0.950 no C61 H61 . . 0.950 no O71 H71 . . 0.852 no C12 C22 . . 1.39 yes C12 C62 . . 1.39 yes C12 O72 . . 1.361(3) yes C22 C32 . . 1.39 yes C22 H22 . . 0.950 no C32 C42 . . 1.39 yes C32 Cl82 . . 1.719(4) yes C42 C52 . . 1.39 yes C42 H42 . . 0.950 no C52 C62 . . 1.39 yes C52 H52 . . 0.950 no C62 H62 . . 0.950 no O72 H72 . . 0.834 no