#------------------------------------------------------------------------------ #$Date: 2020-06-05 13:19:57 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252736 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/80/1558023.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1558023 loop_ _publ_author_name 'Vil', Vera A.' 'Barsegyan, Yana A.' 'Kuhn, Leah' 'Ekimova, Maria V.' 'Semenov, Egor A.' 'Korlyukov, Alexander A.' 'Terent'ev, Alexander O.' 'Alabugin, Igor V.' _publ_section_title ; Synthesis of unstrained Criegee intermediates: inverse \a-effect and other protective stereoelectronic forces can stop Baeyer--Villiger rearrangement of \g-hydroperoxy-\g-peroxylactones ; _journal_issue 20 _journal_name_full 'Chemical Science' _journal_page_first 5313 _journal_paper_doi 10.1039/D0SC01025A _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C5 H8 O5' _chemical_formula_sum 'C5 H8 O5' _chemical_formula_weight 148.11 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-05-20 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-01-29 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.850(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.8512(13) _cell_length_b 5.7699(8) _cell_length_c 11.7734(16) _cell_measurement_reflns_used 3032 _cell_measurement_temperature 120 _cell_measurement_theta_max 31.94 _cell_measurement_theta_min 3.55 _cell_volume 652.45(15) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_unetI/netI 0.0302 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 9425 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 32.054 _diffrn_reflns_theta_min 2.120 _diffrn_source 'sealed tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_T_max 0.7463 _exptl_absorpt_correction_T_min 0.6102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1525 before and 0.0472 after correction. The Ratio of minimum to maximum transmission is 0.8176. The \l/2 correction factor is 0.00150.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.508 _exptl_crystal_description plate _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.414 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 94 _refine_ls_number_reflns 2274 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0366 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.1645P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0910 _refine_ls_wR_factor_ref 0.0970 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1852 _reflns_number_total 2274 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc01025a3.cif _cod_data_source_block me129 _cod_depositor_comments 'Adding full bibliography for 1558023.cif.' _cod_database_code 1558023 _shelxl_version_number 2014/6 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.993 _shelx_estimated_absorpt_t_min 0.947 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Rotating group: O4(H4) 2.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B) 2.c Idealised Me refined as rotating group: C5(H5A,H5B,H5C) ; _shelx_res_file ; TITL me129_a.res in P2(1)/c REM Old TITL me129 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.096, Rweak 0.002, Alpha 0.017, Orientation as input REM Formula found by SHELXT: C5 O5 CELL 0.71073 9.8512 5.7699 11.7734 90 102.85 90 ZERR 4 0.0013 0.0008 0.0016 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 20 32 20 EQIV $1 1-X,-0.5+Y,1.5-Z L.S. 4 0 0 PLAN 20 SIZE 0.05 0.2 0.4 TEMP -153.15 HTAB O4 O5_$1 BOND $H list 4 fmap 2 53 ACTA REM REM REM WGHT 0.044800 0.164500 FVAR 1.19185 O1 3 0.684517 0.655193 0.811469 11.00000 0.01437 0.02058 = 0.01313 -0.00116 0.00220 0.00230 O2 3 0.554659 0.590744 0.728850 11.00000 0.01353 0.02076 = 0.01972 0.00228 0.00201 -0.00055 O3 3 0.806170 0.323825 0.773296 11.00000 0.02256 0.01411 = 0.02058 -0.00016 0.00525 0.00146 O4 3 0.831603 0.242552 0.893992 11.00000 0.02152 0.02282 = 0.02628 0.01097 0.00220 0.00202 AFIX 7 0.8500 H4 2 0.747066 0.220316 0.896711 11.00000 0.03851 AFIX 0 O5 3 0.430018 0.706774 0.560310 11.00000 0.01961 0.03006 = 0.02113 -0.00480 -0.00116 0.00690 C1 1 0.803419 0.568997 0.772053 11.00000 0.01460 0.01367 = 0.01491 -0.00005 0.00419 0.00105 C2 1 0.791956 0.632479 0.643780 11.00000 0.01820 0.02389 = 0.01471 0.00102 0.00562 0.00144 AFIX 23 H2A 2 0.771426 0.491871 0.594773 11.00000 -1.20000 H2B 2 0.881338 0.697936 0.633487 11.00000 -1.20000 AFIX 0 C3 1 0.675134 0.810990 0.606162 11.00000 0.02268 0.02169 = 0.01660 0.00534 0.00453 0.00110 AFIX 23 H3A 2 0.697793 0.955200 0.652022 11.00000 -1.20000 H3B 2 0.664479 0.849178 0.522662 11.00000 -1.20000 AFIX 0 C4 1 0.543222 0.708754 0.626498 11.00000 0.01921 0.01653 = 0.01627 -0.00186 0.00254 0.00465 C5 1 0.924228 0.681110 0.856341 11.00000 0.01819 0.01956 = 0.02036 -0.00139 0.00109 -0.00224 AFIX 137 H5A 2 0.919167 0.642873 0.936396 11.00000 -1.50000 H5B 2 0.919560 0.849645 0.845874 11.00000 -1.50000 H5C 2 1.012119 0.623350 0.841289 11.00000 -1.50000 AFIX 0 HKLF 4 REM me129_a.res in P2(1)/c REM R1 = 0.0366 for 1852 Fo > 4sig(Fo) and 0.0478 for all 2274 data REM 94 parameters refined using 0 restraints END WGHT 0.0454 0.1624 REM Highest difference peak 0.414, deepest hole -0.253, 1-sigma level 0.050 Q1 1 0.6135 0.7561 0.6190 11.00000 0.05 0.41 Q2 1 0.8052 0.4573 0.7761 11.00000 0.05 0.40 Q3 1 0.7914 0.5996 0.7100 11.00000 0.05 0.36 Q4 1 0.7374 0.7220 0.6260 11.00000 0.05 0.34 Q5 1 0.8586 0.6191 0.8159 11.00000 0.05 0.32 Q6 1 0.7450 0.5891 0.7832 11.00000 0.05 0.27 Q7 1 0.5518 0.6764 0.6783 11.00000 0.05 0.22 Q8 1 0.6793 0.7875 0.7951 11.00000 0.05 0.22 Q9 1 0.8456 0.0926 0.8893 11.00000 0.05 0.21 Q10 1 0.6863 0.5215 0.8400 11.00000 0.05 0.20 Q11 1 0.8328 0.3785 0.8855 11.00000 0.05 0.19 Q12 1 0.4612 0.7240 0.6161 11.00000 0.05 0.19 Q13 1 0.4086 0.5994 0.5767 11.00000 0.05 0.18 Q14 1 0.8194 0.2014 0.7490 11.00000 0.05 0.17 Q15 1 0.4390 0.8465 0.5558 11.00000 0.05 0.17 Q16 1 0.5597 0.4449 0.7248 11.00000 0.05 0.17 Q17 1 0.6823 0.9378 0.6011 11.00000 0.05 0.16 Q18 1 0.6355 0.8480 0.5442 11.00000 0.05 0.16 Q19 1 0.3785 0.7222 0.5785 11.00000 0.05 0.15 Q20 1 0.6330 0.7553 0.4850 11.00000 0.05 0.15 ; _shelx_res_checksum 64292 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.68452(7) 0.65519(12) 0.81147(6) 0.01616(15) Uani 1 1 d . . . . . O2 O 0.55466(7) 0.59074(13) 0.72885(6) 0.01827(15) Uani 1 1 d . . . . . O3 O 0.80617(8) 0.32383(12) 0.77330(6) 0.01901(16) Uani 1 1 d . . . . . O4 O 0.83160(8) 0.24255(14) 0.89399(7) 0.02402(17) Uani 1 1 d . . . . . H4 H 0.7471 0.2203 0.8967 0.039(4) Uiso 1 1 d GR . . . . O5 O 0.43002(8) 0.70677(15) 0.56031(7) 0.02449(18) Uani 1 1 d . . . . . C1 C 0.80342(9) 0.56900(16) 0.77205(8) 0.01425(17) Uani 1 1 d . . . . . C2 C 0.79196(10) 0.63248(18) 0.64378(8) 0.01863(19) Uani 1 1 d . . . . . H2A H 0.7714 0.4919 0.5948 0.022 Uiso 1 1 calc R . . . . H2B H 0.8813 0.6979 0.6335 0.022 Uiso 1 1 calc R . . . . C3 C 0.67513(11) 0.81099(18) 0.60616(9) 0.0203(2) Uani 1 1 d . . . . . H3A H 0.6978 0.9552 0.6520 0.024 Uiso 1 1 calc R . . . . H3B H 0.6645 0.8492 0.5227 0.024 Uiso 1 1 calc R . . . . C4 C 0.54322(10) 0.70875(17) 0.62650(8) 0.01756(19) Uani 1 1 d . . . . . C5 C 0.92423(10) 0.68111(18) 0.85634(9) 0.01987(19) Uani 1 1 d . . . . . H5A H 0.9192 0.6429 0.9364 0.030 Uiso 1 1 calc GR . . . . H5B H 0.9196 0.8496 0.8459 0.030 Uiso 1 1 calc GR . . . . H5C H 1.0121 0.6234 0.8413 0.030 Uiso 1 1 calc GR . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0144(3) 0.0206(3) 0.0131(3) -0.0012(2) 0.0022(2) 0.0023(2) O2 0.0135(3) 0.0208(3) 0.0197(3) 0.0023(3) 0.0020(2) -0.0005(2) O3 0.0226(3) 0.0141(3) 0.0206(3) -0.0002(2) 0.0053(3) 0.0015(3) O4 0.0215(4) 0.0228(4) 0.0263(4) 0.0110(3) 0.0022(3) 0.0020(3) O5 0.0196(3) 0.0301(4) 0.0211(4) -0.0048(3) -0.0012(3) 0.0069(3) C1 0.0146(4) 0.0137(4) 0.0149(4) -0.0001(3) 0.0042(3) 0.0010(3) C2 0.0182(4) 0.0239(5) 0.0147(4) 0.0010(3) 0.0056(3) 0.0014(4) C3 0.0227(5) 0.0217(5) 0.0166(4) 0.0053(3) 0.0045(3) 0.0011(4) C4 0.0192(4) 0.0165(4) 0.0163(4) -0.0019(3) 0.0025(3) 0.0046(3) C5 0.0182(4) 0.0196(4) 0.0204(4) -0.0014(3) 0.0011(3) -0.0022(3) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 O2 110.44(6) . . ? C4 O2 O1 110.23(7) . . ? C1 O3 O4 109.21(7) . . ? O3 O4 H4 97.3 . . ? O1 C1 C2 110.34(7) . . ? O1 C1 C5 102.60(7) . . ? O3 C1 O1 110.90(7) . . ? O3 C1 C2 104.24(7) . . ? O3 C1 C5 114.19(8) . . ? C5 C1 C2 114.72(8) . . ? C1 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? C1 C2 C3 109.32(8) . . ? H2A C2 H2B 108.3 . . ? C3 C2 H2A 109.8 . . ? C3 C2 H2B 109.8 . . ? C2 C3 H3A 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? C4 C3 C2 108.18(8) . . ? C4 C3 H3A 110.1 . . ? C4 C3 H3B 110.1 . . ? O2 C4 C3 115.71(8) . . ? O5 C4 O2 116.52(9) . . ? O5 C4 C3 127.61(9) . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 O2 1.4722(10) . ? O1 C1 1.4410(11) . ? O2 C4 1.3668(12) . ? O3 O4 1.4641(11) . ? O3 C1 1.4149(12) . ? O4 H4 0.8502 . ? O5 C4 1.2102(12) . ? C1 C2 1.5336(13) . ? C1 C5 1.5147(13) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.5345(14) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.4941(14) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O5 0.85 1.92 2.7552(12) 165.8 2_646