#------------------------------------------------------------------------------ #$Date: 2019-11-24 15:22:33 +0200 (Sun, 24 Nov 2019) $ #$Revision: 238325 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/51/1555109.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_1555109 loop_ _publ_author_name 'Rashid, Showkat' 'Bhat, Bilal A.' 'Mehta, Goverdhan' _publ_section_title ; Regenerative \g-Lactone Annulations: A Modular, Iterative Approach to Oligo-tetrahydrofuran Molecular Stairs and Related Frameworks. ; _journal_issue 14 _journal_name_full 'Organic letters' _journal_page_first 3604 _journal_page_last 3607 _journal_paper_doi 10.1021/acs.orglett.5b01707 _journal_volume 17 _journal_year 2015 _chemical_absolute_configuration unk _chemical_compound_source 'see text' _chemical_formula_iupac 'C8 H10 O4' _chemical_formula_moiety 'C8 H10 O4' _chemical_formula_structural 'C8 H10 O4' _chemical_formula_sum 'C8 H10 O4' _chemical_formula_weight 170.16 _chemical_name_systematic ; (1S,2R,6R,8R)-5,7,9-trioxatricyclo[6.3.0.0^2,6^]undecan-4-one ; _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 114.32(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.3883(11) _cell_length_b 12.812(2) _cell_length_c 6.0438(13) _cell_measurement_reflns_used 741 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 29.1500 _cell_measurement_theta_min 4.0480 _cell_volume 380.21(16) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'PLATON (Spek, 2003) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 291(2) _diffrn_detector_area_resol_mean 16.3291 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -28.00 37.00 1.0000 35.0000 omega____ theta____ kappa____ phi______ frames - 18.9347 -77.0000 -180.0000 65 #__ type_ start__ end____ width___ exp.time_ 2 omega -11.00 92.00 1.0000 35.0000 omega____ theta____ kappa____ phi______ frames - 18.9347 19.0000 -30.0000 103 #__ type_ start__ end____ width___ exp.time_ 3 omega -23.00 17.00 1.0000 35.0000 omega____ theta____ kappa____ phi______ frames - -19.1691 -99.0000 -90.0000 40 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0521603000 _diffrn_orient_matrix_UB_12 -0.0413011000 _diffrn_orient_matrix_UB_13 -0.0465146000 _diffrn_orient_matrix_UB_21 -0.0391901000 _diffrn_orient_matrix_UB_22 -0.0364980000 _diffrn_orient_matrix_UB_23 0.0680605000 _diffrn_orient_matrix_UB_31 -0.1290045000 _diffrn_orient_matrix_UB_32 -0.0054787000 _diffrn_orient_matrix_UB_33 -0.0989238000 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_number 1397 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.48 _diffrn_reflns_theta_min 3.18 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.51649 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_meas_temp 291(2) _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description block _exptl_crystal_F_000 180 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.212 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.047 _refine_ls_abs_structure_details 'see text' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 746 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0430 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0838P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1133 _refine_ls_wR_factor_ref 0.1164 _reflns_number_gt 702 _reflns_number_total 746 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ol5b01707_si_002.cif _cod_data_source_block compound_41 _cod_depositor_comments ; The following automatic conversions were performed: data item '_symmetry_cell_setting' value 'Monoclinic' was changed to 'monoclinic' in accordance with the /home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas ; _cod_original_cell_volume 380.19(16) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1555109 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O4 O 1.0489(4) 0.42114(17) -0.0928(4) 0.0515(6) Uani 1 1 d . O2 O 1.1366(4) 0.6931(2) -0.0109(4) 0.0574(7) Uani 1 1 d . O3 O 1.1659(4) 0.5428(2) 0.2139(4) 0.0622(7) Uani 1 1 d . O1 O 0.8064(7) 0.3674(2) -0.4687(5) 0.0796(9) Uani 1 1 d . C2 C 0.5838(6) 0.4292(3) -0.2217(5) 0.0516(8) Uani 1 1 d . H2A H 0.5026 0.3668 -0.1890 0.062 Uiso 1 1 calc R H2B H 0.4450 0.4675 -0.3530 0.062 Uiso 1 1 calc R C8 C 1.0008(7) 0.4597(3) 0.1098(5) 0.0491(8) Uani 1 1 d . H8 H 1.0282 0.4043 0.2294 0.059 Uiso 1 1 calc R C1 C 0.8126(7) 0.4025(2) -0.2832(5) 0.0491(8) Uani 1 1 d . C3 C 0.7084(6) 0.4958(3) 0.0021(5) 0.0475(7) Uani 1 1 d . H3 H 0.6222 0.4820 0.1138 0.057 Uiso 1 1 calc R C7 C 1.0296(7) 0.6389(3) 0.1273(5) 0.0476(7) Uani 1 1 d . H7 H 1.0412 0.6821 0.2651 0.057 Uiso 1 1 calc R C4 C 0.7335(6) 0.6139(3) -0.0299(6) 0.0519(8) Uani 1 1 d . H4 H 0.6139 0.6525 0.0269 0.062 Uiso 1 1 calc R C6 C 0.9845(9) 0.6661(3) -0.2576(7) 0.0667(10) Uani 1 1 d . H6A H 1.0496 0.6012 -0.2974 0.080 Uiso 1 1 calc R H6B H 0.9950 0.7207 -0.3647 0.080 Uiso 1 1 calc R C5 C 0.7025(8) 0.6546(3) -0.2767(7) 0.0737(12) Uani 1 1 d . H5A H 0.6004 0.6056 -0.4041 0.088 Uiso 1 1 calc R H5B H 0.6088 0.7213 -0.3118 0.088 Uiso 1 1 calc R 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 O4 0.0467(12) 0.0475(12) 0.0660(13) 0.0025(11) 0.0290(10) 0.0040(10) O2 0.0584(12) 0.0589(15) 0.0594(12) -0.0026(13) 0.0288(11) -0.0082(12) O3 0.0541(13) 0.0581(14) 0.0527(12) 0.0015(11) 0.0002(10) -0.0071(12) O1 0.134(2) 0.0606(19) 0.0654(13) -0.0125(13) 0.0620(16) -0.0017(17) C2 0.0429(14) 0.0548(17) 0.0536(15) -0.0041(17) 0.0163(12) -0.0063(16) C8 0.0540(17) 0.0510(19) 0.0386(13) 0.0070(13) 0.0154(13) -0.0002(13) C1 0.072(2) 0.0362(15) 0.0462(14) 0.0038(13) 0.0319(15) 0.0003(14) C3 0.0455(14) 0.0595(19) 0.0460(14) -0.0046(15) 0.0273(13) -0.0062(15) C7 0.0570(17) 0.0494(16) 0.0404(13) -0.0088(13) 0.0240(13) -0.0054(14) C4 0.0445(15) 0.0514(18) 0.0648(18) -0.0044(16) 0.0275(15) 0.0055(14) C6 0.113(3) 0.0446(18) 0.0581(17) 0.0023(15) 0.0510(19) -0.0025(19) C5 0.074(2) 0.055(2) 0.0608(19) 0.0152(18) -0.0042(17) 0.0024(19) 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 C1 O4 C8 110.6(2) C7 O2 C6 108.0(2) C8 O3 C7 111.6(2) C1 C2 C3 104.5(2) C1 C2 H2A 110.9 C3 C2 H2A 110.9 C1 C2 H2B 110.9 C3 C2 H2B 110.9 H2A C2 H2B 108.9 O3 C8 O4 110.4(3) O3 C8 C3 109.0(3) O4 C8 C3 105.1(2) O3 C8 H8 110.7 O4 C8 H8 110.7 C3 C8 H8 110.7 O1 C1 O4 121.5(3) O1 C1 C2 128.6(3) O4 C1 C2 110.0(2) C2 C3 C8 102.4(3) C2 C3 C4 118.4(3) C8 C3 C4 103.0(3) C2 C3 H3 110.8 C8 C3 H3 110.8 C4 C3 H3 110.8 O2 C7 O3 112.2(3) O2 C7 C4 108.7(2) O3 C7 C4 107.4(3) O2 C7 H7 109.5 O3 C7 H7 109.5 C4 C7 H7 109.5 C7 C4 C5 101.7(3) C7 C4 C3 104.7(3) C5 C4 C3 118.7(3) C7 C4 H4 110.4 C5 C4 H4 110.4 C3 C4 H4 110.4 O2 C6 C5 103.6(3) O2 C6 H6A 111.0 C5 C6 H6A 111.0 O2 C6 H6B 111.0 C5 C6 H6B 111.0 H6A C6 H6B 109.0 C6 C5 C4 105.2(3) C6 C5 H5A 110.7 C4 C5 H5A 110.7 C6 C5 H5B 110.7 C4 C5 H5B 110.7 H5A C5 H5B 108.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O4 C1 1.340(4) O4 C8 1.440(3) O2 C7 1.381(4) O2 C6 1.417(4) O3 C8 1.364(4) O3 C7 1.419(4) O1 C1 1.195(4) C2 C1 1.467(5) C2 C3 1.504(4) C2 H2A 0.9700 C2 H2B 0.9700 C8 C3 1.508(5) C8 H8 0.9800 C3 C4 1.538(5) C3 H3 0.9800 C7 C4 1.518(5) C7 H7 0.9800 C4 C5 1.523(5) C4 H4 0.9800 C6 C5 1.484(5) C6 H6A 0.9700 C6 H6B 0.9700 C5 H5A 0.9700 C5 H5B 0.9700 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 C7 O3 C8 O4 96.8(3) C7 O3 C8 C3 -18.2(3) C1 O4 C8 O3 -135.1(3) C1 O4 C8 C3 -17.6(3) C8 O4 C1 O1 -178.1(3) C8 O4 C1 C2 0.8(3) C3 C2 C1 O1 -164.9(3) C3 C2 C1 O4 16.3(4) C1 C2 C3 C8 -25.6(3) C1 C2 C3 C4 86.8(3) O3 C8 C3 C2 144.7(3) O4 C8 C3 C2 26.3(3) O3 C8 C3 C4 21.3(3) O4 C8 C3 C4 -97.1(3) C6 O2 C7 O3 93.0(3) C6 O2 C7 C4 -25.6(4) C8 O3 C7 O2 -112.5(3) C8 O3 C7 C4 6.9(3) O2 C7 C4 C5 4.2(4) O3 C7 C4 C5 -117.4(3) O2 C7 C4 C3 128.4(3) O3 C7 C4 C3 6.8(3) C2 C3 C4 C7 -128.3(3) C8 C3 C4 C7 -16.3(3) C2 C3 C4 C5 -15.8(4) C8 C3 C4 C5 96.3(3) C7 O2 C6 C5 36.3(4) O2 C6 C5 C4 -32.5(4) C7 C4 C5 C6 17.2(4) C3 C4 C5 C6 -96.9(4)