#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008131.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_2008131 loop_ _publ_author_name 'McCullough, Kevin J.' 'Perner, Iris' 'Rosair, Georgina M.' _publ_section_title ; 2-Benzyl-2-hydroxycyclohexanone ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 268 _journal_page_last 270 _journal_paper_doi 10.1107/S0108270198013869 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C13 H16 O2' _chemical_formula_weight 204.26 _chemical_melting_point 349 _chemical_name_systematic ; 2-benzyl-2-hydroxycyclohexanone ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 10.857(3) _cell_length_b 11.2892(9) _cell_length_c 18.5162(9) _cell_measurement_reflns_used 28 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.51 _cell_measurement_theta_min 4.90 _cell_volume 2269.5(7) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction 'SHELXTL/PC (Sheldrick, 1994)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXTL/PC _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution SHELXTL/PC _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_number 2575 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.83 _diffrn_standards_decay_% 10.75 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rectangular_block _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.4 _refine_diff_density_max 0.157 _refine_diff_density_min -0.177 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 1977 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.015 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0493 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w =1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.1676P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1350 _reflns_number_gt 1297 _reflns_number_total 1977 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bm1297.cif _cod_data_source_block ip1a _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 ; _cod_original_cell_volume 2269.5(6) _cod_database_code 2008131 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 -0.06902(19) 0.95354(14) 0.58297(10) 0.0611(5) Uani d . 1 . . O C1 -0.10699(19) 0.85320(18) 0.57253(12) 0.0429(5) Uani d . 1 . . C O2 0.05851(14) 0.82433(14) 0.48647(9) 0.0510(4) Uani d . 1 . . O H2 0.0479 0.8902 0.4688 0.061 Uiso calc R 1 . . H C2 -0.05606(18) 0.77834(18) 0.51061(12) 0.0405(5) Uani d . 1 . . C C3 -0.0283(2) 0.65386(19) 0.53805(13) 0.0468(5) Uani d . 1 . . C H3A -0.0061(5) 0.6038(9) 0.4972(8) 0.056 Uiso calc R 1 . . H H3B 0.0424(13) 0.6572(2) 0.5704(6) 0.056 Uiso calc R 1 . . H C4 -0.1359(2) 0.5977(2) 0.57785(14) 0.0539(6) Uani d . 1 . . C H4A -0.2057(14) 0.5884(3) 0.5444(7) 0.065 Uiso calc R 1 . . H H4B -0.1120(5) 0.5185(15) 0.5950(3) 0.065 Uiso calc R 1 . . H C5 -0.1751(3) 0.6726(2) 0.64130(14) 0.0584(6) Uani d . 1 . . C H5A -0.1093 0.6745 0.6767 0.070 Uiso calc R 1 . . H H5B -0.2468 0.6372 0.6639 0.070 Uiso calc R 1 . . H C6 -0.2059(2) 0.7993(2) 0.61810(14) 0.0518(6) Uani d . 1 . . C H6A -0.2811(15) 0.7988(2) 0.5916(5) 0.062 Uiso calc R 1 . . H H6B -0.2178(3) 0.8468(10) 0.6600(9) 0.062 Uiso calc R 1 . . H C7 -0.1528(2) 0.7823(2) 0.44893(13) 0.0479(5) Uani d . 1 . . C H7A -0.2322(15) 0.7617(4) 0.4686(4) 0.057 Uiso calc R 1 . . H H7B -0.1582(2) 0.8623(16) 0.4311(4) 0.057 Uiso calc R 1 . . H C8 -0.1257(2) 0.7012(2) 0.38657(13) 0.0515(6) Uani d . 1 . . C C9 -0.0302(3) 0.7243(3) 0.33847(15) 0.0662(8) Uani d . 1 . . C H9 0.0170 0.7926 0.3436 0.079 Uiso calc R 1 . . H C10 -0.0052(4) 0.6446(4) 0.28234(16) 0.0913(12) Uani d . 1 . . C H10 0.0591 0.6596 0.2505 0.110 Uiso calc R 1 . . H C11 -0.0761(5) 0.5435(4) 0.27431(18) 0.0974(13) Uani d . 1 . . C H11 -0.0587 0.4900 0.2375 0.117 Uiso calc R 1 . . H C12 -0.1711(5) 0.5227(4) 0.32024(19) 0.0961(12) Uani d . 1 . . C H12 -0.2195 0.4555 0.3142 0.115 Uiso calc R 1 . . H C13 -0.1966(3) 0.6000(3) 0.37563(16) 0.0727(8) Uani d . 1 . . C H13 -0.2623 0.5845 0.4064 0.087 Uiso calc R 1 . . 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 O1 0.0774(12) 0.0391(8) 0.0667(11) -0.0091(8) 0.0069(10) 0.0001(8) C1 0.0392(11) 0.0363(10) 0.0531(13) 0.0020(9) -0.0051(9) 0.0050(9) O2 0.0371(8) 0.0473(8) 0.0685(10) -0.0034(7) 0.0060(7) 0.0093(8) C2 0.0317(9) 0.0369(10) 0.0530(12) -0.0030(8) -0.0020(9) 0.0078(10) C3 0.0453(12) 0.0392(11) 0.0560(13) 0.0054(9) -0.0036(10) 0.0053(10) C4 0.0592(14) 0.0382(11) 0.0644(15) -0.0053(11) -0.0023(13) 0.0103(11) C5 0.0597(14) 0.0577(14) 0.0577(14) -0.0079(13) 0.0075(12) 0.0126(13) C6 0.0470(12) 0.0537(13) 0.0546(13) -0.0036(11) 0.0056(11) -0.0015(11) C7 0.0399(11) 0.0485(12) 0.0553(13) 0.0042(10) -0.0037(10) 0.0055(11) C8 0.0512(12) 0.0564(13) 0.0470(12) 0.0054(11) -0.0079(11) 0.0088(11) C9 0.0593(16) 0.088(2) 0.0517(14) 0.0046(15) -0.0035(12) 0.0091(15) C10 0.081(2) 0.146(4) 0.0474(16) 0.034(2) -0.0014(16) 0.002(2) C11 0.134(3) 0.101(3) 0.0568(17) 0.041(3) -0.026(2) -0.019(2) C12 0.147(4) 0.079(2) 0.0620(18) -0.005(3) -0.017(2) -0.0102(18) C13 0.092(2) 0.0700(18) 0.0560(16) -0.0149(17) -0.0082(16) -0.0018(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 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 O1 C1 C6 122.1(2) y O1 C1 C2 120.7(2) y C6 C1 C2 117.26(19) y O2 C2 C3 105.59(16) y O2 C2 C1 110.55(17) y C3 C2 C1 109.35(18) y O2 C2 C7 110.54(17) y C3 C2 C7 113.91(18) y C1 C2 C7 106.93(17) y C4 C3 C2 113.20(18) n C5 C4 C3 111.1(2) n C4 C5 C6 111.5(2) n C1 C6 C5 112.5(2) y C8 C7 C2 114.54(18) n C9 C8 C13 118.2(3) n C9 C8 C7 121.6(3) n C13 C8 C7 120.2(2) n C8 C9 C10 119.9(3) n C11 C10 C9 120.1(3) n C12 C11 C10 119.9(3) n C11 C12 C13 120.7(4) n C12 C13 C8 121.2(4) n 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 O1 C1 . 1.221(3) y C1 C6 . 1.496(3) y C1 C2 . 1.528(3) y O2 C2 . 1.420(2) y C2 C3 . 1.524(3) n C2 C7 . 1.553(3) n C3 C4 . 1.520(3) n C4 C5 . 1.509(4) n C5 C6 . 1.529(4) n C7 C8 . 1.502(3) n C8 C9 . 1.391(4) n C8 C13 . 1.392(4) n C9 C10 . 1.401(5) n C10 C11 . 1.385(6) n C11 C12 . 1.358(6) n C12 C13 . 1.375(5) n loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21105665 2 PubChem 100926390