#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:08:28 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/36/2003668.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_2003668 loop_ _publ_author_name 'Cox, P. J.' _publ_section_title ; Chloroxylenol, C~8~H~9~ClO ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1361 _journal_page_last 1364 _journal_paper_doi 10.1107/S0108270194012588 _journal_volume 51 _journal_year 1995 _chemical_compound_source Aldrich _chemical_formula_sum 'C8 H9 Cl O' _chemical_formula_weight 156.6 _chemical_name_common chloroxylenol _chemical_name_systematic ; 4-chloro-3,5-dimethylphenol ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _cell_angle_alpha 90.00 _cell_angle_beta 92.92(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 8.537(4) _cell_length_b 13.936(2) _cell_length_c 12.839(3) _cell_measurement_reflns_used 250 _cell_measurement_temperature 140(2) _cell_measurement_theta_max 25.03 _cell_measurement_theta_min 2.16 _cell_volume 1525.5(8) _computing_molecular_graphics 'SNOOPI (Davies, 1983)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 140(2) _diffrn_measurement_device 'Delft Instruments FAST' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5996 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 2.16 _exptl_absorpt_coefficient_mu 0.424 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.364 _exptl_crystal_description tablet _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.514 _refine_diff_density_min -0.304 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.990 _refine_ls_goodness_of_fit_obs 1.066 _refine_ls_matrix_type full _refine_ls_number_parameters 197 _refine_ls_number_reflns 2251 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.990 _refine_ls_restrained_S_obs 1.066 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_obs 0.0407 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(F~o~^2^) + (0.0621P)^2^] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1001 _refine_ls_wR_factor_obs 0.0979 _reflns_number_observed 1887 _reflns_number_total 2251 _reflns_observed_criterion >2sigma(I) _cod_data_source_file hu1115.cif _cod_data_source_block clp1 _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_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2003668 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 Cl 0.0335(4) 0.0103(2) 0.0020(3) 0.0273(4) -0.0046(3) 0.0439(4) O 0.0264(10) -0.0032(7) 0.0116(7) 0.0235(10) -0.0083(8) 0.0408(11) C1 0.0224(12) 0.0004(8) 0.0003(9) 0.0239(13) -0.0033(9) 0.0189(12) C2 0.0243(13) -0.0025(8) 0.0009(9) 0.0199(12) -0.0010(9) 0.0224(12) C3 0.0208(12) -0.0004(8) -0.0007(9) 0.0253(13) -0.0023(10) 0.0202(12) C4 0.0241(13) 0.0047(9) -0.0037(9) 0.0228(12) -0.0022(10) 0.0245(13) C5 0.0304(13) -0.0016(9) -0.0036(9) 0.0210(12) 0.0023(10) 0.0202(12) C6 0.0260(13) -0.0060(9) 0.0020(9) 0.0268(13) 0.0004(10) 0.0202(12) C7 0.040(2) -0.0031(10) 0.0007(11) 0.0240(13) 0.0037(11) 0.0348(15) C8 0.0267(14) 0.0000(10) 0.0080(10) 0.0304(14) -0.0066(11) 0.0360(15) Cl' 0.0430(4) -0.0049(2) 0.0129(3) 0.0316(4) -0.0013(3) 0.0300(4) O' 0.0230(11) 0.0005(7) 0.0045(7) 0.0322(10) 0.0063(7) 0.0273(10) C1' 0.0225(13) 0.0027(8) 0.0038(10) 0.0163(12) 0.0039(10) 0.0264(13) C2' 0.0193(13) 0.0000(8) 0.0059(10) 0.0181(12) 0.0005(10) 0.0351(15) C3' 0.0240(13) -0.0014(8) 0.0034(10) 0.0178(12) -0.0003(10) 0.0291(14) C4' 0.0311(14) -0.0009(8) 0.0089(10) 0.0154(12) 0.0006(9) 0.0272(14) C5' 0.0213(13) 0.0000(8) 0.0079(10) 0.0182(12) 0.0018(10) 0.038(2) C6' 0.0202(13) 0.0012(8) -0.0034(10) 0.0209(12) 0.0039(10) 0.0307(14) C7' 0.0260(14) -0.0015(10) 0.0125(11) 0.0319(14) 0.0031(12) 0.047(2) C8' 0.0341(15) -0.0060(11) 0.0017(11) 0.0373(15) -0.0029(12) 0.0319(15) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol Cl 1 0.22774(7) 1.12372(4) 0.44203(5) 0.0349(2) Uani d . Cl O 1 0.6301(2) 0.81811(13) 0.28752(14) 0.0299(4) Uani d . O H 1 0.5908(30) 0.7738(21) 0.2874(23) 0.043(10) Uiso d . H C1 1 0.5322(3) 0.88825(15) 0.3248(2) 0.0218(5) Uani d . C C2 1 0.3988(2) 0.8650(2) 0.3753(2) 0.0222(5) Uani d . C H2 1 0.3722(2) 0.7995(2) 0.3849(2) 0.021(4) Uiso calc R H C3 1 0.3026(2) 0.9368(2) 0.4127(2) 0.0222(5) Uani d . C C4 1 0.3480(2) 1.0320(2) 0.3977(2) 0.0239(5) Uani d . C C5 1 0.4839(2) 1.0575(2) 0.3489(2) 0.0240(5) Uani d . C C6 1 0.5755(2) 0.9835(2) 0.3121(2) 0.0243(5) Uani d . C H6 1 0.6686(2) 0.9982(2) 0.2778(2) 0.021(4) Uiso calc R H C7 1 0.5333(3) 1.1610(2) 0.3368(2) 0.0329(6) Uani d . C H7A 1 0.6319(9) 1.1635(2) 0.3009(10) 0.049(3) Uiso calc R H H7B 1 0.5483(16) 1.1907(3) 0.4058(2) 0.049(3) Uiso calc R H H7C 1 0.4518(8) 1.1958(3) 0.2957(10) 0.049(3) Uiso calc R H C8 1 0.1576(3) 0.9104(2) 0.4677(2) 0.0308(6) Uani d . C H8A 1 0.1498(10) 0.8404(2) 0.4725(11) 0.049(3) Uiso calc R H H8B 1 0.0650(3) 0.9356(10) 0.4285(7) 0.049(3) Uiso calc R H H8C 1 0.1633(9) 0.9380(9) 0.5380(5) 0.049(3) Uiso calc R H Cl' 1 1.07767(7) 0.89689(4) -0.19492(5) 0.0345(2) Uani d . Cl O' 1 0.9440(2) 0.84192(11) 0.24536(12) 0.0274(4) Uani d . O H' 1 0.8552(30) 0.8330(18) 0.2521(20) 0.034(8) Uiso d . H C1' 1 0.9697(2) 0.85655(15) 0.1414(2) 0.0216(5) Uani d . C C2' 1 0.8504(2) 0.85229(15) 0.0648(2) 0.0240(5) Uani d . C H2' 1 0.7460(2) 0.84042(15) 0.0836(2) 0.027(4) Uiso calc R H C3' 1 0.8817(2) 0.86523(15) -0.0401(2) 0.0235(5) Uani d . C C4' 1 1.0368(2) 0.88170(15) -0.0638(2) 0.0243(5) Uani d . C C5' 1 1.1596(2) 0.88608(15) 0.0126(2) 0.0256(6) Uani d . C C6' 1 1.1226(2) 0.87341(15) 0.1154(2) 0.0241(5) Uani d . C H6' 1 1.2034(2) 0.87635(15) 0.1689(2) 0.027(4) Uiso calc R H C7' 1 1.3268(3) 0.9033(2) -0.0145(2) 0.0346(6) Uani d . C H7A' 1 1.3949(3) 0.9019(11) 0.0493(2) 0.048(3) Uiso calc R H H7B' 1 1.3349(4) 0.9661(5) -0.0481(11) 0.048(3) Uiso calc R H H7C' 1 1.3593(6) 0.8530(6) -0.0622(10) 0.048(3) Uiso calc R H C8' 1 0.7521(3) 0.8602(2) -0.1233(2) 0.0344(6) Uani d . C H8A' 1 0.6540(4) 0.8424(11) -0.0918(3) 0.048(3) Uiso calc R H H8B' 1 0.7779(8) 0.8120(8) -0.1752(7) 0.048(3) Uiso calc R H H8C' 1 0.7397(12) 0.9230(3) -0.1571(8) 0.048(3) Uiso calc R H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001 H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 Cl Cl 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.1484 0.1 O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006 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 C2 C1 O 121.6(2) yes O C1 C6 117.6(2) yes C2 C1 C6 120.7(2) yes C1 C2 C3 120.6(2) yes C2 C3 C4 117.4(2) yes C2 C3 C8 120.0(2) yes C4 C3 C8 122.5(2) yes C5 C4 C3 123.1(2) yes C3 C4 Cl 118.4(2) yes C5 C4 Cl 118.4(2) yes C6 C5 C4 117.4(2) yes C6 C5 C7 120.5(2) yes C4 C5 C7 122.1(2) yes C1 C6 C5 120.7(2) yes O' C1' C2' 122.4(2) yes O' C1' C6' 117.2(2) yes C2' C1' C6' 120.3(2) yes C1' C2' C3' 120.8(2) yes C4' C3' C2' 117.5(2) yes C2' C3' C8' 120.7(2) yes C4' C3' C8' 121.8(2) yes C3' C4' C5' 122.7(2) yes C3' C4' Cl' 118.0(2) yes C5' C4' Cl' 119.3(2) yes C6' C5' C4' 117.6(2) yes C6' C5' C7' 120.4(2) yes C4' C5' C7' 122.0(2) yes C1' C6' C5' 121.1(2) yes C1 O H 109(2) no C1 C2 H2 119.69 no C3 C2 H2 119.69 no C1 C6 H6 119.66 no C5 C6 H6 119.66 no C5 C7 H7A 109.47 no C5 C7 H7B 109.47 no H7A C7 H7B 109.5 no C5 C7 H7C 109.47 no H7A C7 H7C 109.5 no H7B C7 H7C 109.5 no C3 C8 H8A 109.47 no C3 C8 H8B 109.47 no H8A C8 H8B 109.5 no C3 C8 H8C 109.47 no H8A C8 H8C 109.5 no H8B C8 H8C 109.5 no C1' O' H' 110(2) no C1' C2' H2' 119.62 no C3' C2' H2' 119.62 no C1' C6' H6' 119.46 no C5' C6' H6' 119.46 no C5' C7' H7A' 109.47 no C5' C7' H7B' 109.47 no H7A' C7' H7B' 109.5 no C5' C7' H7C' 109.47 no H7A' C7' H7C' 109.5 no H7B' C7' H7C' 109.5 no C3' C8' H8A' 109.47 no C3' C8' H8B' 109.47 no H8A' C8' H8B' 109.5 no C3' C8' H8C' 109.47 no H8A' C8' H8C' 109.5 no H8B' C8' H8C' 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl C4 1.752(2) yes O C1 1.387(3) yes C1 C2 1.377(3) yes C1 C6 1.390(3) yes C2 C3 1.395(3) yes C3 C4 1.399(3) yes C3 C8 1.502(3) yes C4 C5 1.392(3) yes C5 C6 1.391(3) yes C5 C7 1.514(3) yes Cl' C4' 1.749(2) yes O' C1' 1.378(3) yes C1' C2' 1.381(3) yes C1' C6' 1.384(3) yes C2' C3' 1.398(3) yes C3' C4' 1.393(3) yes C3' C8' 1.500(3) yes C4' C5' 1.400(3) yes C5' C6' 1.384(3) yes C5' C7' 1.505(3) yes O H 0.70(3) no C2 H2 0.95 no C6 H6 0.95 no C7 H7A 0.98 no C7 H7B 0.98 no C7 H7C 0.98 no C8 H8A 0.98 no C8 H8B 0.98 no C8 H8C 0.98 no O' H' 0.78(2) no C2' H2' 0.95 no C6' H6' 0.95 no C7' H7A' 0.98 no C7' H7B' 0.98 no C7' H7C' 0.98 no C8' H8A' 0.98 no C8' H8B' 0.98 no C8' H8C' 0.98 no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag O C1 C2 C3 179.6(2) no C6 C1 C2 C3 1.5(3) no C1 C2 C3 C4 -0.7(3) no C1 C2 C3 C8 180.0(2) no C2 C3 C4 C5 -0.7(3) no C8 C3 C4 C5 178.5(2) no C2 C3 C4 Cl 179.1(2) no C8 C3 C4 Cl -1.7(3) no C3 C4 C5 C6 1.3(3) no Cl C4 C5 C6 -178.4(2) no C3 C4 C5 C7 -177.9(2) no Cl C4 C5 C7 2.3(3) no C2 C1 C6 C5 -0.9(3) no O C1 C6 C5 -179.1(2) no C4 C5 C6 C1 -0.5(3) no C7 C5 C6 C1 178.8(2) no O' C1' C2' C3' -178.4(2) no C6' C1' C2' C3' -0.2(3) no C1' C2' C3' C4' 0.5(3) no C1' C2' C3' C8' 179.8(2) no C2' C3' C4' C5' -0.3(3) no C8' C3' C4' C5' -179.6(2) no C2' C3' C4' Cl' 179.4(2) no C8' C3' C4' Cl' 0.1(3) no C3' C4' C5' C6' -0.1(3) no Cl' C4' C5' C6' -179.8(2) no C3' C4' C5' C7' 179.6(2) no Cl' C4' C5' C7' -0.2(3) no O' C1' C6' C5' 178.1(2) no C2' C1' C6' C5' -0.2(3) no C4' C5' C6' C1' 0.3(3) no C7' C5' C6' C1' -179.3(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21106017