#------------------------------------------------------------------------------ #$Date: 2024-05-23 01:15:19 +0300 (Thu, 23 May 2024) $ #$Revision: 291993 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/16/1571698.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_1571698 loop_ _publ_author_name 'Kilgallon, Landon J.' 'McFadden, Timothy P.' 'Sigman, Matthew S.' 'Johnson, Jeremiah A.' _publ_section_title ; Tricyclononenes and tricyclononadienes as efficient monomers for controlled ROMP: understanding structure--propagation rate relationships and enabling facile post-polymerization modification ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC01986E _journal_year 2024 _chemical_formula_sum 'C11 H10 O5' _chemical_formula_weight 222.19 _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 direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2019/1 _audit_update_record ; 2024-04-27 deposited with the CCDC. 2024-05-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.886(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.9853(11) _cell_length_b 11.7489(17) _cell_length_c 10.3831(15) _cell_measurement_reflns_used 9791 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 31.55 _cell_measurement_theta_min 2.63 _cell_volume 945.7(2) _computing_cell_refinement 'SAINT 8.38A (Bruker-AXS, 2017)' _computing_data_collection 'APEX3 v2017.3.0 (Bruker-AXS, 2017)' _computing_data_reduction 'SAINT 8.38A (Bruker-AXS, 2017)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2019/1 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT-2015 (Sheldrick, 2015)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.4 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker Photon3 CPAD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0654 _diffrn_reflns_av_unetI/netI 0.0291 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 39227 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.552 _diffrn_reflns_theta_min 2.627 _diffrn_source 'I\mS micro-focus sealed tube, multilayer optics' _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_T_max 0.6748 _exptl_absorpt_correction_T_min 0.5743 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Herbst-Irmer et al., 2015)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_description blade _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.290 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.055 _refine_diff_density_max 0.478 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 151 _refine_ls_number_reflns 3157 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0469 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+0.6425P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1192 _refine_ls_wR_factor_ref 0.1269 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2725 _reflns_number_total 3157 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc01986e2.cif _cod_data_source_block P23127 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1571698 _shelx_shelxl_version_number 2019/1 _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_min 0.965 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; TITL P23127 in P2(1)/c P23127.res created by SHELXL-2019/1 at 12:44:12 on 08-Jun-2023 CELL 0.71073 7.98530 11.74890 10.38310 90.0000 103.8857 90.0000 ZERR 4.00 0.00110 0.00170 0.00150 0.0000 0.0060 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H O UNIT 44 40 20 TEMP -173 SIZE 0.055 0.12 0.29 wpdb -2 acta OMIT 3 1 0 ! outlier, Fo > Fc DFIX 0.84 o2 h2 o4 h4 L.S. 10 BOND $H FMAP 2 PLAN 20 EQIV $1 x-1, -y+1/2, z-1/2 EQIV $2 -x+1, -y+1, -z+2 EQIV $3 x+1, -y+1/2, z+1/2 HTAB O2 O3 HTAB O4 O5_$1 HTAB C5 O1_$2 HTAB C6 O3_$3 htab WGHT 0.061700 0.642500 FVAR 0.28231 O1 3 0.110771 0.625450 0.806743 11.00000 0.02128 0.02001 = 0.02403 -0.00464 0.00240 0.00133 O2 3 -0.107429 0.548019 0.657983 11.00000 0.01292 0.01865 = 0.02485 0.00017 0.00077 0.00142 H2 2 -0.122289 0.486299 0.613828 11.00000 -1.50000 REM Q2 1 -0.1174 0.4854 0.6123 11.00000 0.05 0.73 O3 3 -0.142458 0.359516 0.515939 11.00000 0.01219 0.02104 = 0.02106 -0.00082 -0.00018 0.00117 O4 3 0.037239 0.221916 0.480881 11.00000 0.01255 0.01941 = 0.02136 -0.00404 0.00021 -0.00073 H4 2 -0.050780 0.201703 0.418249 11.00000 -1.20000 REM Q1 1 -0.0526 0.2013 0.4198 11.00000 0.05 0.83 O5 3 0.759028 0.352958 0.807112 11.00000 0.01160 0.02437 = 0.02255 0.00197 0.00103 0.00000 C1 1 0.049860 0.544340 0.739170 11.00000 0.01361 0.01861 = 0.01788 0.00034 0.00358 0.00052 C2 1 0.148812 0.437141 0.740746 11.00000 0.01126 0.01727 = 0.01618 0.00111 0.00175 0.00014 C3 1 0.320236 0.401248 0.828958 11.00000 0.01257 0.01671 = 0.01519 0.00042 -0.00011 -0.00029 AFIX 13 H3 2 0.318440 0.384580 0.923063 11.00000 -1.20000 AFIX 0 C4 1 0.486046 0.460327 0.810359 11.00000 0.01249 0.01599 = 0.01829 0.00082 -0.00063 -0.00093 AFIX 13 H4A 2 0.502235 0.541498 0.839679 11.00000 -1.20000 AFIX 0 C5 1 0.625468 0.377187 0.879282 11.00000 0.01210 0.02005 = 0.01746 0.00120 -0.00077 0.00043 AFIX 13 H5 2 0.650043 0.366016 0.977515 11.00000 -1.20000 AFIX 0 C6 1 0.609345 0.278424 0.789950 11.00000 0.01167 0.01921 = 0.02159 -0.00004 -0.00031 0.00141 AFIX 13 H6 2 0.622526 0.199518 0.827126 11.00000 -1.20000 AFIX 0 C7 1 0.460259 0.306879 0.671863 11.00000 0.01272 0.02195 = 0.01744 -0.00278 -0.00011 0.00206 AFIX 13 H7 2 0.455581 0.263190 0.588419 11.00000 -1.20000 AFIX 0 C8 1 0.303507 0.292596 0.734940 11.00000 0.01208 0.01496 = 0.01859 0.00019 -0.00005 -0.00063 AFIX 13 H8 2 0.295848 0.217689 0.778899 11.00000 -1.20000 AFIX 0 C9 1 0.133162 0.343837 0.662597 11.00000 0.01021 0.01681 = 0.01750 0.00090 -0.00024 -0.00111 C10 1 -0.003696 0.308816 0.546559 11.00000 0.01140 0.01719 = 0.01787 0.00041 0.00115 -0.00168 C11 1 0.476708 0.437386 0.662811 11.00000 0.01254 0.02301 = 0.01742 0.00441 0.00083 0.00068 AFIX 23 H11A 2 0.582898 0.460878 0.636594 11.00000 -1.20000 H11B 2 0.374394 0.472685 0.603175 11.00000 -1.20000 AFIX 0 HKLF 4 REM P23127 in P2(1)/c REM wR2 = 0.1269, GooF = S = 1.028, Restrained GooF = 1.028 for all data REM R1 = 0.0469 for 2725 Fo > 4sig(Fo) and 0.0553 for all 3157 data REM 151 parameters refined using 2 restraints END WGHT 0.0617 0.6425 REM Instructions for potential hydrogen bonds HTAB O2 O3 HTAB O4 O5_$1 HTAB C5 O1_$2 HTAB C6 O3_$3 REM Highest difference peak 0.478, deepest hole -0.269, 1-sigma level 0.064 Q1 1 0.1217 0.3944 0.6955 11.00000 0.05 0.48 Q2 1 0.4851 0.4545 0.7371 11.00000 0.05 0.42 Q3 1 0.0759 0.3280 0.5981 11.00000 0.05 0.40 Q4 1 0.5898 0.3182 0.8446 11.00000 0.05 0.40 Q5 1 0.6990 0.3833 0.9853 11.00000 0.05 0.39 Q6 1 0.3874 0.2954 0.7016 11.00000 0.05 0.37 Q7 1 0.5294 0.2852 0.7226 11.00000 0.05 0.37 Q8 1 0.5546 0.4219 0.8415 11.00000 0.05 0.37 Q9 1 0.2441 0.4334 0.7825 11.00000 0.05 0.34 Q10 1 0.2220 0.3184 0.6812 11.00000 0.05 0.33 Q11 1 0.6666 0.2050 0.7951 11.00000 0.05 0.33 Q12 1 0.4682 0.3700 0.6555 11.00000 0.05 0.32 Q13 1 0.4076 0.4311 0.8141 11.00000 0.05 0.32 Q14 1 0.3228 0.3445 0.8004 11.00000 0.05 0.31 Q15 1 0.0969 0.4846 0.7415 11.00000 0.05 0.28 Q16 1 0.7618 0.2977 0.7272 11.00000 0.05 0.25 Q17 1 -0.0826 0.3285 0.5242 11.00000 0.05 0.20 Q18 1 0.0476 0.5808 0.8236 11.00000 0.05 0.19 Q19 1 0.0873 0.3587 0.7572 11.00000 0.05 0.19 Q20 1 0.0313 0.2754 0.4964 11.00000 0.05 0.19 ; _shelx_res_checksum 25530 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 0.11077(13) 0.62545(8) 0.80674(10) 0.0223(2) Uani 1 1 d . . . . . O2 O -0.10743(11) 0.54802(8) 0.65798(10) 0.01944(19) Uani 1 1 d D . . . . H2 H -0.122(3) 0.4863(14) 0.6138(18) 0.029 Uiso 1 1 d D U . . . O3 O -0.14246(11) 0.35952(8) 0.51594(9) 0.01880(19) Uani 1 1 d . . . . . O4 O 0.03724(11) 0.22192(8) 0.48088(9) 0.01843(19) Uani 1 1 d D . . . . H4 H -0.051(2) 0.2017(15) 0.4182(16) 0.022 Uiso 1 1 d D U . . . O5 O 0.75903(11) 0.35296(8) 0.80711(9) 0.0200(2) Uani 1 1 d . . . . . C1 C 0.04986(15) 0.54434(10) 0.73917(12) 0.0167(2) Uani 1 1 d . . . . . C2 C 0.14881(14) 0.43714(10) 0.74075(11) 0.0152(2) Uani 1 1 d . . . . . C3 C 0.32024(14) 0.40125(10) 0.82896(11) 0.0154(2) Uani 1 1 d . . . . . H3 H 0.318440 0.384580 0.923063 0.018 Uiso 1 1 calc R U . . . C4 C 0.48605(14) 0.46033(10) 0.81036(12) 0.0163(2) Uani 1 1 d . . . . . H4A H 0.502235 0.541498 0.839679 0.020 Uiso 1 1 calc R U . . . C5 C 0.62547(15) 0.37719(10) 0.87928(12) 0.0173(2) Uani 1 1 d . . . . . H5 H 0.650043 0.366016 0.977515 0.021 Uiso 1 1 calc R U . . . C6 C 0.60935(15) 0.27842(11) 0.78995(12) 0.0182(2) Uani 1 1 d . . . . . H6 H 0.622526 0.199518 0.827126 0.022 Uiso 1 1 calc R U . . . C7 C 0.46026(15) 0.30688(11) 0.67186(12) 0.0180(2) Uani 1 1 d . . . . . H7 H 0.455581 0.263190 0.588419 0.022 Uiso 1 1 calc R U . . . C8 C 0.30351(14) 0.29260(10) 0.73494(12) 0.0158(2) Uani 1 1 d . . . . . H8 H 0.295848 0.217689 0.778899 0.019 Uiso 1 1 calc R U . . . C9 C 0.13316(14) 0.34384(10) 0.66260(12) 0.0154(2) Uani 1 1 d . . . . . C10 C -0.00370(14) 0.30882(10) 0.54656(12) 0.0159(2) Uani 1 1 d . . . . . C11 C 0.47671(15) 0.43739(11) 0.66281(12) 0.0181(2) Uani 1 1 d . . . . . H11A H 0.582898 0.460878 0.636594 0.022 Uiso 1 1 calc R U . . . H11B H 0.374394 0.472685 0.603175 0.022 Uiso 1 1 calc R U . . . 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 0.0213(4) 0.0200(4) 0.0240(4) -0.0046(3) 0.0024(3) 0.0013(3) O2 0.0129(4) 0.0186(4) 0.0248(4) 0.0002(3) 0.0008(3) 0.0014(3) O3 0.0122(4) 0.0210(4) 0.0211(4) -0.0008(3) -0.0002(3) 0.0012(3) O4 0.0126(4) 0.0194(4) 0.0214(4) -0.0040(3) 0.0002(3) -0.0007(3) O5 0.0116(4) 0.0244(4) 0.0225(4) 0.0020(3) 0.0010(3) 0.0000(3) C1 0.0136(5) 0.0186(5) 0.0179(5) 0.0003(4) 0.0036(4) 0.0005(4) C2 0.0113(4) 0.0173(5) 0.0162(5) 0.0011(4) 0.0018(4) 0.0001(4) C3 0.0126(5) 0.0167(5) 0.0152(5) 0.0004(4) -0.0001(4) -0.0003(4) C4 0.0125(5) 0.0160(5) 0.0183(5) 0.0008(4) -0.0006(4) -0.0009(4) C5 0.0121(5) 0.0201(5) 0.0175(5) 0.0012(4) -0.0008(4) 0.0004(4) C6 0.0117(5) 0.0192(5) 0.0216(5) 0.0000(4) -0.0003(4) 0.0014(4) C7 0.0127(5) 0.0219(6) 0.0174(5) -0.0028(4) -0.0001(4) 0.0021(4) C8 0.0121(4) 0.0150(5) 0.0186(5) 0.0002(4) -0.0001(4) -0.0006(4) C9 0.0102(4) 0.0168(5) 0.0175(5) 0.0009(4) -0.0002(4) -0.0011(4) C10 0.0114(4) 0.0172(5) 0.0179(5) 0.0004(4) 0.0011(4) -0.0017(4) C11 0.0125(5) 0.0230(6) 0.0174(5) 0.0044(4) 0.0008(4) 0.0007(4) 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 O2 H2 107.5(14) . . ? C10 O4 H4 110.1(12) . . ? C6 O5 C5 60.33(8) . . ? O1 C1 O2 121.70(11) . . ? O1 C1 C2 121.42(11) . . ? O2 C1 C2 116.87(10) . . ? C9 C2 C1 135.15(11) . . ? C9 C2 C3 94.43(9) . . ? C1 C2 C3 130.16(10) . . ? C2 C3 C4 118.45(10) . . ? C2 C3 C8 85.51(8) . . ? C4 C3 C8 103.38(9) . . ? C2 C3 H3 115.0 . . ? C4 C3 H3 115.0 . . ? C8 C3 H3 115.0 . . ? C5 C4 C11 102.15(10) . . ? C5 C4 C3 101.79(9) . . ? C11 C4 C3 101.95(9) . . ? C5 C4 H4A 116.2 . . ? C11 C4 H4A 116.2 . . ? C3 C4 H4A 116.2 . . ? O5 C5 C6 59.39(8) . . ? O5 C5 C4 114.96(10) . . ? C6 C5 C4 105.41(9) . . ? O5 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? O5 C6 C5 60.28(8) . . ? O5 C6 C7 115.15(10) . . ? C5 C6 C7 105.48(10) . . ? O5 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C11 101.83(9) . . ? C6 C7 C8 100.92(10) . . ? C11 C7 C8 102.81(9) . . ? C6 C7 H7 116.3 . . ? C11 C7 H7 116.3 . . ? C8 C7 H7 116.3 . . ? C9 C8 C7 117.84(10) . . ? C9 C8 C3 85.33(8) . . ? C7 C8 C3 102.36(9) . . ? C9 C8 H8 115.5 . . ? C7 C8 H8 115.5 . . ? C3 C8 H8 115.5 . . ? C2 C9 C10 131.23(11) . . ? C2 C9 C8 94.71(9) . . ? C10 C9 C8 134.05(11) . . ? O3 C10 O4 124.30(11) . . ? O3 C10 C9 121.31(11) . . ? O4 C10 C9 114.38(10) . . ? C4 C11 C7 95.61(9) . . ? C4 C11 H11A 112.6 . . ? C7 C11 H11A 112.6 . . ? C4 C11 H11B 112.6 . . ? C7 C11 H11B 112.6 . . ? H11A C11 H11B 110.1 . . ? 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 C1 1.2137(15) . ? O2 C1 1.3349(14) . ? O2 H2 0.851(15) . ? O3 C10 1.2307(14) . ? O4 C10 1.3120(15) . ? O4 H4 0.868(14) . ? O5 C6 1.4577(15) . ? O5 C5 1.4709(16) . ? C1 C2 1.4848(16) . ? C2 C9 1.3517(16) . ? C2 C3 1.5129(15) . ? C3 C4 1.5475(16) . ? C3 C8 1.5930(17) . ? C3 H3 1.0000 . ? C4 C5 1.5243(16) . ? C4 C11 1.5396(17) . ? C4 H4A 1.0000 . ? C5 C6 1.4717(17) . ? C5 H5 1.0000 . ? C6 C7 1.5270(16) . ? C6 H6 1.0000 . ? C7 C11 1.5437(18) . ? C7 C8 1.5548(17) . ? C7 H7 1.0000 . ? C8 C9 1.5121(16) . ? C8 H8 1.0000 . ? C9 C10 1.4776(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 _geom_hbond_publ_flag O2 H2 O3 0.851(15) 1.789(15) 2.6382(14) 176(2) . yes O4 H4 O5 0.868(14) 1.791(15) 2.6535(13) 171.6(18) 4_465 yes C5 H5 O1 1.00 2.57 3.4306(16) 143.7 3_667 yes C6 H6 O3 1.00 2.47 3.1350(15) 123.9 4_666 yes