#------------------------------------------------------------------------------ #$Date: 2024-08-05 21:07:46 +0300 (Mon, 05 Aug 2024) $ #$Revision: 293767 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572014.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_1572014 loop_ _publ_author_name 'Bao, Ming' 'Bohórquez, Arnold R Romero' 'Arman, Hadi' 'Doyle, Michael P.' _publ_section_title ; Photoinduced [4 + 2]-cycloaddition reactions of vinyldiazo compounds for the construction of heterocyclic and bicyclic rings. ; _journal_issue 30 _journal_name_full 'Chemical science' _journal_page_first 12042 _journal_page_last 12046 _journal_paper_doi 10.1039/d4sc03558e _journal_volume 15 _journal_year 2024 _chemical_formula_moiety 'C26 H35 N O3 Si' _chemical_formula_sum 'C26 H35 N O3 Si' _chemical_formula_weight 437.64 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-02-14 _audit_creation_method ; Olex2 1.5-ac5-024 (compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498) ; _audit_update_record ; 2024-04-05 deposited with the CCDC. 2024-06-27 downloaded from the CCDC. ; _cell_angle_alpha 84.659(2) _cell_angle_beta 88.405(2) _cell_angle_gamma 83.737(2) _cell_formula_units_Z 2 _cell_length_a 6.03320(10) _cell_length_b 11.3990(3) _cell_length_c 17.7451(3) _cell_measurement_reflns_used 13988 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 76.5250 _cell_measurement_theta_min 2.4880 _cell_volume 1207.63(4) _computing_cell_refinement 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.939 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -51.00 -19.00 0.50 0.23 -- -91.75 45.00 -60.00 64 2 \w -71.00 -19.00 0.50 0.23 -- -91.75 61.00 -60.00 104 3 \w -71.00 -19.00 0.50 0.23 -- -91.75 61.00-150.00 104 4 \w -71.00 -19.00 0.50 0.23 -- -91.75 61.00-180.00 104 5 \w -51.00 -19.00 0.50 0.23 -- -91.75 45.00-180.00 64 6 \w -51.00 -19.00 0.50 0.23 -- -91.75 45.00 -30.00 64 7 \w -51.00 -19.00 0.50 0.23 -- -91.75 45.00 0.00 64 8 \w -51.00 -19.00 0.50 0.23 -- -91.75 45.00 30.00 64 9 \w -85.00 -22.00 0.50 0.23 -- -91.75 125.00 -30.00 126 10 \w -119.00 -83.00 0.50 0.06 -- -46.90 -57.00-150.00 72 11 \w -119.00 -83.00 0.50 0.06 -- -46.90 -57.00-180.00 72 12 \w -80.00 -19.00 0.50 0.23 -- -91.75 95.00-129.00 122 13 \w -79.00 26.00 0.50 0.06 -- -46.90 95.00-129.00 210 14 \w -119.00 -83.00 0.50 0.06 -- -46.90 -57.00 90.00 72 15 \w -164.00-101.00 0.50 0.23 -- -91.75 -77.00 150.00 126 16 \w -164.00-101.00 0.50 0.23 -- -91.75 -77.00 90.00 126 17 \w -164.00-101.00 0.50 0.23 -- -91.75 -77.00-180.00 126 18 \w -164.00 -86.00 0.50 0.23 -- -91.75 -58.00-155.85 156 19 \w -164.00-100.00 0.50 0.23 -- -91.75 -94.00 -90.00 128 20 \w -164.00-100.00 0.50 0.23 -- -91.75 -94.00-120.00 128 21 \w -164.00 -83.00 0.50 0.23 -- -91.75 -95.00 120.00 162 22 \w 32.00 119.00 0.50 0.06 -- 46.90 54.00-171.48 174 23 \w 83.00 119.00 0.50 0.06 -- 46.90 57.00 -90.00 72 24 \w 32.00 119.00 0.50 0.06 -- 46.90 52.00-122.86 174 25 \w 32.00 109.00 0.50 0.06 -- 46.90 49.00 -66.17 154 26 \w 31.00 119.00 0.50 0.06 -- 46.90 55.00 96.75 176 27 \w 32.00 119.00 0.50 0.06 -- 46.90 53.00 0.59 174 28 \w -28.00 30.00 0.50 0.06 -- 46.90 -19.00 120.00 116 29 \w 34.00 101.00 0.50 0.23 -- 106.91 -77.00 60.00 134 30 \w 93.00 178.00 0.50 0.23 -- 106.91 45.00 150.00 170 31 \w 105.00 178.00 0.50 0.23 -- 106.91 95.00-129.00 146 32 \w -28.00 30.00 0.50 0.06 -- 46.90 -19.00-150.00 116 33 \w -27.00 43.00 0.50 0.06 -- 46.90 -37.00-150.00 140 34 \w 34.00 94.00 0.50 0.06 -- 46.90-125.00-180.00 120 35 \w 37.00 112.00 0.50 0.23 -- 106.91-125.00-180.00 150 36 \w 37.00 112.00 0.50 0.23 -- 106.91-125.00 -90.00 150 37 \w 34.00 106.00 0.50 0.23 -- 106.91 -94.00-180.00 144 38 \w 36.00 107.00 0.50 0.23 -- 106.91-105.00 -38.48 142 39 \w 34.00 106.00 0.50 0.23 -- 106.91 -94.00 -30.00 144 40 \w 37.00 112.00 0.50 0.23 -- 106.91-125.00 90.00 150 41 \w 34.00 105.00 0.50 0.23 -- 106.91 -95.00 120.00 142 42 \w -9.00 79.00 0.50 0.06 -- 46.90 -95.00 120.00 176 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0718354000 _diffrn_orient_matrix_UB_12 -0.0263460000 _diffrn_orient_matrix_UB_13 -0.0812330000 _diffrn_orient_matrix_UB_21 -0.1381141000 _diffrn_orient_matrix_UB_22 -0.1065897000 _diffrn_orient_matrix_UB_23 0.0065764000 _diffrn_orient_matrix_UB_31 -0.2043851000 _diffrn_orient_matrix_UB_32 0.0811339000 _diffrn_orient_matrix_UB_33 -0.0310365000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_unetI/netI 0.0262 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.939 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 22726 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.939 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.687 _diffrn_reflns_theta_min 2.501 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.062 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.796 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.204 _exptl_crystal_description plate _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.121 _exptl_crystal_size_mid 0.071 _exptl_crystal_size_min 0.061 _refine_diff_density_max 0.291 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 286 _refine_ls_number_reflns 4794 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.992 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0341 _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^)+(0.0481P)^2^+0.5289P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0900 _refine_ls_wR_factor_ref 0.0924 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4388 _reflns_number_total 4794 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc03558e2.cif _cod_data_source_block hpd842_auto _cod_depositor_comments 'Adding full bibliography for 1572014--1572015.cif.' _cod_database_code 1572014 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C H N O Si' _chemical_oxdiff_usercomment 784 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C7(H7), C5(H5), C2(H2) 2.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C17(H17A,H17B) 2.c Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C18(H18), C3(H3), C4(H4), C25(H25), C21(H21), C24(H24), C23(H23), C22(H22) 2.d Idealised Me refined as rotating group: C26(H26A,H26B,H26C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C13(H13A,H13B, H13C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C) ; _shelx_res_file ; TITL hpd842_auto_a.res in P-1 hpd842_auto.res created by SHELXL-2018/3 at 15:04:44 on 14-Feb-2024 REM Old TITL hpd842_auto in P-1 REM SHELXT solution in P-1: R1 0.105, Rweak 0.005, Alpha 0.039 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C13 N O1 Si CELL 1.54184 6.0332 11.399 17.7451 84.659 88.405 83.737 ZERR 2 0.0001 0.0003 0.0003 0.002 0.002 0.002 LATT 1 SFAC C H N O Si UNIT 52 70 2 6 2 L.S. 4 PLAN 7 TEMP -173 fmap 2 ACTA OMIT 6 10 3 REM REM REM WGHT 0.048100 0.528900 FVAR 9.47825 SI1 5 0.623578 0.693074 0.110389 11.00000 0.01670 0.01445 = 0.01591 0.00085 -0.00031 -0.00206 O3 4 0.453661 0.170050 0.355581 11.00000 0.02313 0.01545 = 0.02058 -0.00099 -0.00873 0.00252 O2 4 0.355361 0.356398 0.384899 11.00000 0.02666 0.01769 = 0.02170 -0.00347 -0.00690 0.00073 O1 4 0.512328 0.626691 0.189092 11.00000 0.02561 0.01725 = 0.01781 -0.00062 -0.00053 -0.00994 N1 3 0.406030 0.526754 0.171653 11.00000 0.02278 0.01535 = 0.02049 -0.00067 -0.00168 -0.00691 C9 1 0.293586 0.488291 0.228716 11.00000 0.01850 0.01457 = 0.01523 0.00080 -0.00262 -0.00047 AFIX 43 H9 2 0.294752 0.523732 0.275064 11.00000 -1.20000 AFIX 0 C16 1 0.330094 0.276607 0.346794 11.00000 0.01652 0.01444 = 0.01552 0.00179 0.00092 -0.00095 C1 1 0.161320 0.388110 0.222247 11.00000 0.01748 0.01340 = 0.01478 0.00178 -0.00265 -0.00094 C7 1 -0.033648 0.372074 0.276047 11.00000 0.01635 0.01465 = 0.01838 0.00151 -0.00134 -0.00179 AFIX 13 H7 2 -0.161221 0.342061 0.251676 11.00000 -1.20000 AFIX 0 C19 1 0.938661 -0.003395 0.403882 11.00000 0.02522 0.01728 = 0.01553 0.00168 -0.00105 -0.00323 AFIX 43 H19 2 1.030126 0.055572 0.384440 11.00000 -1.20000 AFIX 0 C6 1 0.170651 0.280381 0.284116 11.00000 0.01695 0.01271 = 0.01511 0.00127 -0.00048 -0.00252 C20 1 1.046719 -0.125929 0.414492 11.00000 0.02298 0.01857 = 0.01559 -0.00206 -0.00387 -0.00022 C5 1 0.191588 0.171717 0.234771 11.00000 0.02008 0.01269 = 0.01697 -0.00074 -0.00126 -0.00096 AFIX 13 H5 2 0.245348 0.093567 0.262151 11.00000 -1.20000 AFIX 0 C18 1 0.726975 0.033146 0.418652 11.00000 0.02248 0.01689 = 0.01897 0.00287 -0.00502 -0.00237 AFIX 43 H18 2 0.629876 -0.024374 0.435810 11.00000 -1.20000 AFIX 0 C3 1 -0.023143 0.264577 0.137112 11.00000 0.02390 0.01883 = 0.01955 -0.00333 -0.00717 -0.00260 AFIX 43 H3 2 -0.135125 0.286801 0.100354 11.00000 -1.20000 AFIX 0 C4 1 -0.018374 0.173229 0.189922 11.00000 0.02197 0.01714 = 0.02196 -0.00404 -0.00186 -0.00507 AFIX 43 H4 2 -0.127224 0.118879 0.197942 11.00000 -1.20000 AFIX 0 C8 1 0.349558 0.218018 0.171522 11.00000 0.02107 0.01731 = 0.01694 -0.00108 0.00012 -0.00142 AFIX 23 H8A 2 0.490041 0.239993 0.191055 11.00000 -1.20000 H8B 2 0.381650 0.162983 0.131652 11.00000 -1.20000 AFIX 0 C17 1 0.634365 0.160042 0.409609 11.00000 0.02055 0.01949 = 0.01920 0.00046 -0.00681 0.00046 AFIX 23 H17A 2 0.577143 0.186127 0.458844 11.00000 -1.20000 H17B 2 0.751459 0.210204 0.390458 11.00000 -1.20000 AFIX 0 C26 1 -0.108679 0.459522 0.333092 11.00000 0.01920 0.01797 = 0.02251 -0.00072 0.00165 0.00078 AFIX 137 H26A 2 0.022190 0.484507 0.356133 11.00000 -1.50000 H26B 2 -0.201263 0.421889 0.372528 11.00000 -1.50000 H26C 2 -0.195585 0.528838 0.307579 11.00000 -1.50000 AFIX 0 C2 1 0.183055 0.326474 0.146511 11.00000 0.02234 0.01652 = 0.01447 0.00046 -0.00180 -0.00309 AFIX 13 H2 2 0.229859 0.376901 0.100949 11.00000 -1.20000 AFIX 0 C25 1 0.947932 -0.216828 0.456596 11.00000 0.02703 0.02054 = 0.02047 -0.00071 -0.00261 -0.00264 AFIX 43 H25 2 0.805045 -0.200365 0.479468 11.00000 -1.20000 AFIX 0 C21 1 1.257442 -0.152976 0.381892 11.00000 0.02524 0.02370 = 0.01825 -0.00184 -0.00114 -0.00098 AFIX 43 H21 2 1.327941 -0.092220 0.353452 11.00000 -1.20000 AFIX 0 C12 1 0.722949 0.829324 0.144902 11.00000 0.01989 0.01570 = 0.02340 -0.00089 0.00266 -0.00281 C24 1 1.056180 -0.330623 0.465313 11.00000 0.03753 0.01747 = 0.02588 -0.00024 -0.00768 -0.00296 AFIX 43 H24 2 0.986831 -0.391474 0.494094 11.00000 -1.20000 AFIX 0 C10 1 0.852935 0.591996 0.072700 11.00000 0.02496 0.02107 = 0.02344 -0.00478 -0.00192 0.00118 AFIX 137 H10A 2 0.964609 0.568660 0.111871 11.00000 -1.50000 H10B 2 0.922494 0.632615 0.028567 11.00000 -1.50000 H10C 2 0.793001 0.521255 0.057729 11.00000 -1.50000 AFIX 0 C23 1 1.265420 -0.356728 0.432356 11.00000 0.03907 0.01816 = 0.02846 -0.00709 -0.01272 0.00642 AFIX 43 H23 2 1.338994 -0.434964 0.438513 11.00000 -1.20000 AFIX 0 C22 1 1.365630 -0.267519 0.390436 11.00000 0.02719 0.03074 = 0.02419 -0.00910 -0.00431 0.00617 AFIX 43 H22 2 1.508270 -0.284584 0.367521 11.00000 -1.20000 AFIX 0 C15 1 0.800367 0.909221 0.076601 11.00000 0.02693 0.01932 = 0.03211 0.00308 0.00351 -0.00609 AFIX 137 H15A 2 0.915381 0.864041 0.047738 11.00000 -1.50000 H15B 2 0.861826 0.977496 0.094556 11.00000 -1.50000 H15C 2 0.673153 0.936961 0.044051 11.00000 -1.50000 AFIX 0 C13 1 0.916173 0.794960 0.200124 11.00000 0.02930 0.02447 = 0.02853 -0.00376 -0.00414 -0.00733 AFIX 137 H13A 2 0.864712 0.746166 0.244191 11.00000 -1.50000 H13B 2 0.967649 0.866864 0.216709 11.00000 -1.50000 H13C 2 1.039285 0.749951 0.174662 11.00000 -1.50000 AFIX 0 C11 1 0.408205 0.731561 0.036627 11.00000 0.02127 0.03399 = 0.02241 0.00483 -0.00304 -0.00332 AFIX 137 H11A 2 0.341755 0.660023 0.026522 11.00000 -1.50000 H11B 2 0.477431 0.764989 -0.009977 11.00000 -1.50000 H11C 2 0.291918 0.789954 0.054462 11.00000 -1.50000 AFIX 0 C14 1 0.530501 0.897916 0.186287 11.00000 0.03130 0.01860 = 0.03948 -0.00791 0.01075 -0.00393 AFIX 137 H14A 2 0.409313 0.924141 0.150936 11.00000 -1.50000 H14B 2 0.583824 0.967098 0.205979 11.00000 -1.50000 H14C 2 0.475601 0.846264 0.228347 11.00000 -1.50000 AFIX 0 HKLF 4 REM hpd842_auto_a.res in P-1 REM wR2 = 0.0924, GooF = S = 0.992, Restrained GooF = 0.992 for all data REM R1 = 0.0341 for 4388 Fo > 4sig(Fo) and 0.0371 for all 4794 data REM 286 parameters refined using 0 restraints END WGHT 0.0427 0.4653 REM Highest difference peak 0.291, deepest hole -0.300, 1-sigma level 0.041 Q1 1 0.5068 0.7182 0.0701 11.00000 0.05 0.29 Q2 1 0.6657 0.7713 0.1314 11.00000 0.05 0.28 Q3 1 0.0448 0.3988 0.2424 11.00000 0.05 0.25 Q4 1 1.1540 -0.1395 0.4059 11.00000 0.05 0.25 Q5 1 0.0757 0.3015 0.1405 11.00000 0.05 0.24 Q6 1 0.1668 0.3629 0.1852 11.00000 0.05 0.24 Q7 1 0.2767 0.1870 0.2062 11.00000 0.05 0.23 ; _shelx_res_checksum 8526 _olex2_exptl_crystal_mounting_method 'nylon loop' _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling - B-factor correction ; _oxdiff_exptl_absorpt_empirical_full_max 1.250 _oxdiff_exptl_absorpt_empirical_full_min 0.824 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -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_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 Si1 Si 0.62358(5) 0.69307(3) 0.11039(2) 0.01580(10) Uani 1 1 d . . . . . O3 O 0.45366(14) 0.17005(7) 0.35558(5) 0.01994(19) Uani 1 1 d . . . . . O2 O 0.35536(15) 0.35640(8) 0.38490(5) 0.0220(2) Uani 1 1 d . . . . . O1 O 0.51233(15) 0.62669(8) 0.18909(5) 0.01972(19) Uani 1 1 d . . . . . N1 N 0.40603(17) 0.52675(9) 0.17165(6) 0.0192(2) Uani 1 1 d . . . . . C9 C 0.29359(19) 0.48829(10) 0.22872(7) 0.0163(2) Uani 1 1 d . . . . . H9 H 0.294752 0.523732 0.275064 0.020 Uiso 1 1 calc R U . . . C16 C 0.33009(19) 0.27661(10) 0.34679(7) 0.0158(2) Uani 1 1 d . . . . . C1 C 0.16132(19) 0.38811(10) 0.22225(7) 0.0154(2) Uani 1 1 d . . . . . C7 C -0.03365(19) 0.37207(10) 0.27605(7) 0.0166(2) Uani 1 1 d . . . . . H7 H -0.161221 0.342061 0.251676 0.020 Uiso 1 1 calc R U . . . C19 C 0.9387(2) -0.00340(11) 0.40388(7) 0.0195(3) Uani 1 1 d . . . . . H19 H 1.030126 0.055572 0.384440 0.023 Uiso 1 1 calc R U . . . C6 C 0.17065(19) 0.28038(10) 0.28412(7) 0.0150(2) Uani 1 1 d . . . . . C20 C 1.0467(2) -0.12593(11) 0.41449(7) 0.0191(3) Uani 1 1 d . . . . . C5 C 0.1916(2) 0.17172(10) 0.23477(7) 0.0167(2) Uani 1 1 d . . . . . H5 H 0.245348 0.093567 0.262151 0.020 Uiso 1 1 calc R U . . . C18 C 0.7270(2) 0.03315(11) 0.41865(7) 0.0196(3) Uani 1 1 d . . . . . H18 H 0.629876 -0.024374 0.435810 0.024 Uiso 1 1 calc R U . . . C3 C -0.0231(2) 0.26458(11) 0.13711(7) 0.0205(3) Uani 1 1 d . . . . . H3 H -0.135125 0.286801 0.100354 0.025 Uiso 1 1 calc R U . . . C4 C -0.0184(2) 0.17323(11) 0.18992(7) 0.0200(3) Uani 1 1 d . . . . . H4 H -0.127224 0.118879 0.197942 0.024 Uiso 1 1 calc R U . . . C8 C 0.3496(2) 0.21802(11) 0.17152(7) 0.0185(3) Uani 1 1 d . . . . . H8A H 0.490041 0.239993 0.191055 0.022 Uiso 1 1 calc R U . . . H8B H 0.381650 0.162983 0.131652 0.022 Uiso 1 1 calc R U . . . C17 C 0.6344(2) 0.16004(11) 0.40961(7) 0.0200(3) Uani 1 1 d . . . . . H17A H 0.577143 0.186127 0.458844 0.024 Uiso 1 1 calc R U . . . H17B H 0.751459 0.210204 0.390458 0.024 Uiso 1 1 calc R U . . . C26 C -0.1087(2) 0.45952(11) 0.33309(7) 0.0202(3) Uani 1 1 d . . . . . H26A H 0.022190 0.484507 0.356133 0.030 Uiso 1 1 calc R U . . . H26B H -0.201263 0.421889 0.372528 0.030 Uiso 1 1 calc R U . . . H26C H -0.195585 0.528838 0.307579 0.030 Uiso 1 1 calc R U . . . C2 C 0.1831(2) 0.32647(11) 0.14651(7) 0.0178(2) Uani 1 1 d . . . . . H2 H 0.229859 0.376901 0.100949 0.021 Uiso 1 1 calc R U . . . C25 C 0.9479(2) -0.21683(11) 0.45660(7) 0.0227(3) Uani 1 1 d . . . . . H25 H 0.805045 -0.200365 0.479468 0.027 Uiso 1 1 calc R U . . . C21 C 1.2574(2) -0.15298(12) 0.38189(7) 0.0225(3) Uani 1 1 d . . . . . H21 H 1.327941 -0.092220 0.353452 0.027 Uiso 1 1 calc R U . . . C12 C 0.7229(2) 0.82932(11) 0.14490(7) 0.0197(3) Uani 1 1 d . . . . . C24 C 1.0562(2) -0.33062(12) 0.46531(8) 0.0269(3) Uani 1 1 d . . . . . H24 H 0.986831 -0.391474 0.494094 0.032 Uiso 1 1 calc R U . . . C10 C 0.8529(2) 0.59200(12) 0.07270(8) 0.0232(3) Uani 1 1 d . . . . . H10A H 0.964609 0.568660 0.111871 0.035 Uiso 1 1 calc R U . . . H10B H 0.922494 0.632615 0.028567 0.035 Uiso 1 1 calc R U . . . H10C H 0.793001 0.521255 0.057729 0.035 Uiso 1 1 calc R U . . . C23 C 1.2654(3) -0.35673(12) 0.43236(8) 0.0287(3) Uani 1 1 d . . . . . H23 H 1.338994 -0.434964 0.438513 0.034 Uiso 1 1 calc R U . . . C22 C 1.3656(2) -0.26752(13) 0.39044(8) 0.0276(3) Uani 1 1 d . . . . . H22 H 1.508270 -0.284584 0.367521 0.033 Uiso 1 1 calc R U . . . C15 C 0.8004(2) 0.90922(12) 0.07660(8) 0.0263(3) Uani 1 1 d . . . . . H15A H 0.915381 0.864041 0.047738 0.039 Uiso 1 1 calc R U . . . H15B H 0.861826 0.977496 0.094556 0.039 Uiso 1 1 calc R U . . . H15C H 0.673153 0.936961 0.044051 0.039 Uiso 1 1 calc R U . . . C13 C 0.9162(2) 0.79496(12) 0.20012(8) 0.0270(3) Uani 1 1 d . . . . . H13A H 0.864712 0.746166 0.244191 0.040 Uiso 1 1 calc R U . . . H13B H 0.967649 0.866864 0.216709 0.040 Uiso 1 1 calc R U . . . H13C H 1.039285 0.749951 0.174662 0.040 Uiso 1 1 calc R U . . . C11 C 0.4082(2) 0.73156(13) 0.03663(8) 0.0263(3) Uani 1 1 d . . . . . H11A H 0.341755 0.660023 0.026522 0.039 Uiso 1 1 calc R U . . . H11B H 0.477431 0.764989 -0.009977 0.039 Uiso 1 1 calc R U . . . H11C H 0.291918 0.789954 0.054462 0.039 Uiso 1 1 calc R U . . . C14 C 0.5305(2) 0.89792(12) 0.18629(9) 0.0296(3) Uani 1 1 d . . . . . H14A H 0.409313 0.924141 0.150936 0.044 Uiso 1 1 calc R U . . . H14B H 0.583824 0.967098 0.205979 0.044 Uiso 1 1 calc R U . . . H14C H 0.475601 0.846264 0.228347 0.044 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 Si1 0.01670(16) 0.01445(17) 0.01591(17) 0.00085(12) -0.00031(12) -0.00206(12) O3 0.0231(4) 0.0154(4) 0.0206(4) -0.0010(3) -0.0087(4) 0.0025(3) O2 0.0267(5) 0.0177(4) 0.0217(5) -0.0035(4) -0.0069(4) 0.0007(4) O1 0.0256(4) 0.0172(4) 0.0178(4) -0.0006(3) -0.0005(3) -0.0099(4) N1 0.0228(5) 0.0153(5) 0.0205(5) -0.0007(4) -0.0017(4) -0.0069(4) C9 0.0185(5) 0.0146(5) 0.0152(6) 0.0008(4) -0.0026(4) -0.0005(4) C16 0.0165(5) 0.0144(6) 0.0155(6) 0.0018(4) 0.0009(4) -0.0009(4) C1 0.0175(5) 0.0134(5) 0.0148(6) 0.0018(4) -0.0027(4) -0.0009(4) C7 0.0163(5) 0.0146(6) 0.0184(6) 0.0015(5) -0.0013(4) -0.0018(4) C19 0.0252(6) 0.0173(6) 0.0155(6) 0.0017(5) -0.0011(5) -0.0032(5) C6 0.0169(5) 0.0127(5) 0.0151(6) 0.0013(4) -0.0005(4) -0.0025(4) C20 0.0230(6) 0.0186(6) 0.0156(6) -0.0021(5) -0.0039(5) -0.0002(5) C5 0.0201(6) 0.0127(5) 0.0170(6) -0.0007(4) -0.0013(5) -0.0010(4) C18 0.0225(6) 0.0169(6) 0.0190(6) 0.0029(5) -0.0050(5) -0.0024(5) C3 0.0239(6) 0.0188(6) 0.0195(6) -0.0033(5) -0.0072(5) -0.0026(5) C4 0.0220(6) 0.0171(6) 0.0220(6) -0.0040(5) -0.0019(5) -0.0051(5) C8 0.0211(6) 0.0173(6) 0.0169(6) -0.0011(5) 0.0001(5) -0.0014(5) C17 0.0205(6) 0.0195(6) 0.0192(6) 0.0005(5) -0.0068(5) 0.0005(5) C26 0.0192(6) 0.0180(6) 0.0225(6) -0.0007(5) 0.0017(5) 0.0008(5) C2 0.0223(6) 0.0165(6) 0.0145(6) 0.0005(5) -0.0018(5) -0.0031(5) C25 0.0270(6) 0.0205(6) 0.0205(6) -0.0007(5) -0.0026(5) -0.0026(5) C21 0.0252(6) 0.0237(6) 0.0183(6) -0.0018(5) -0.0011(5) -0.0010(5) C12 0.0199(6) 0.0157(6) 0.0234(6) -0.0009(5) 0.0027(5) -0.0028(5) C24 0.0375(8) 0.0175(6) 0.0259(7) -0.0002(5) -0.0077(6) -0.0030(5) C10 0.0250(6) 0.0211(6) 0.0234(6) -0.0048(5) -0.0019(5) 0.0012(5) C23 0.0391(8) 0.0182(6) 0.0285(7) -0.0071(5) -0.0127(6) 0.0064(6) C22 0.0272(7) 0.0307(7) 0.0242(7) -0.0091(6) -0.0043(5) 0.0062(6) C15 0.0269(7) 0.0193(6) 0.0321(7) 0.0031(5) 0.0035(6) -0.0061(5) C13 0.0293(7) 0.0245(7) 0.0285(7) -0.0038(6) -0.0041(6) -0.0073(6) C11 0.0213(6) 0.0340(7) 0.0224(7) 0.0048(6) -0.0030(5) -0.0033(5) C14 0.0313(7) 0.0186(6) 0.0395(8) -0.0079(6) 0.0108(6) -0.0039(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 6 8 0.0114 -4 -1 3 0.0613 -1 -5 7 0.0244 4 1 -2 0.0412 0 5 -7 0.0441 -3 1 -7 0.0761 0 -6 -8 0.0408 3 0 8 0.0260 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 O1 Si1 C12 103.03(5) . . ? O1 Si1 C10 109.80(5) . . ? O1 Si1 C11 110.36(5) . . ? C10 Si1 C12 112.94(6) . . ? C10 Si1 C11 108.82(6) . . ? C11 Si1 C12 111.77(6) . . ? C16 O3 C17 115.87(9) . . ? N1 O1 Si1 110.72(7) . . ? C9 N1 O1 110.23(10) . . ? N1 C9 C1 119.46(11) . . ? O3 C16 C6 110.78(10) . . ? O2 C16 O3 122.62(11) . . ? O2 C16 C6 126.57(11) . . ? C9 C1 C7 119.05(10) . . ? C9 C1 C6 121.33(10) . . ? C9 C1 C2 117.67(10) . . ? C7 C1 C6 59.50(7) . . ? C7 C1 C2 120.80(10) . . ? C6 C1 C2 102.77(9) . . ? C1 C7 C6 62.09(7) . . ? C1 C7 C26 122.41(10) . . ? C26 C7 C6 124.90(10) . . ? C18 C19 C20 126.77(12) . . ? C16 C6 C1 118.18(10) . . ? C16 C6 C7 122.16(10) . . ? C16 C6 C5 117.34(10) . . ? C1 C6 C5 102.13(9) . . ? C7 C6 C1 58.41(7) . . ? C7 C6 C5 119.47(10) . . ? C25 C20 C19 122.68(11) . . ? C21 C20 C19 119.09(11) . . ? C21 C20 C25 118.23(12) . . ? C4 C5 C6 109.77(9) . . ? C4 C5 C8 99.82(10) . . ? C8 C5 C6 99.16(9) . . ? C19 C18 C17 123.09(12) . . ? C4 C3 C2 107.38(11) . . ? C3 C4 C5 107.65(11) . . ? C2 C8 C5 93.18(9) . . ? O3 C17 C18 107.07(10) . . ? C3 C2 C1 109.32(10) . . ? C3 C2 C8 99.61(10) . . ? C8 C2 C1 99.47(9) . . ? C24 C25 C20 120.67(13) . . ? C22 C21 C20 121.03(13) . . ? C15 C12 Si1 109.23(9) . . ? C13 C12 Si1 110.58(9) . . ? C13 C12 C15 109.83(11) . . ? C14 C12 Si1 109.50(9) . . ? C14 C12 C15 109.07(11) . . ? C14 C12 C13 108.62(11) . . ? C25 C24 C23 120.65(13) . . ? C22 C23 C24 119.37(12) . . ? C23 C22 C21 120.05(13) . . ? 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 Si1 O1 1.6839(9) . ? Si1 C12 1.8834(13) . ? Si1 C10 1.8530(13) . ? Si1 C11 1.8594(13) . ? O3 C16 1.3524(14) . ? O3 C17 1.4600(14) . ? O2 C16 1.2076(15) . ? O1 N1 1.4286(13) . ? N1 C9 1.2735(16) . ? C9 C1 1.4773(16) . ? C16 C6 1.4852(16) . ? C1 C7 1.5101(16) . ? C1 C6 1.5665(15) . ? C1 C2 1.5694(16) . ? C7 C6 1.5274(16) . ? C7 C26 1.5123(17) . ? C19 C20 1.4733(17) . ? C19 C18 1.3262(18) . ? C6 C5 1.5744(16) . ? C20 C25 1.3975(18) . ? C20 C21 1.3974(18) . ? C5 C4 1.5123(17) . ? C5 C8 1.5448(16) . ? C18 C17 1.4885(17) . ? C3 C4 1.3329(18) . ? C3 C2 1.5160(17) . ? C8 C2 1.5447(16) . ? C25 C24 1.3844(19) . ? C21 C22 1.3916(19) . ? C12 C15 1.5403(17) . ? C12 C13 1.5379(18) . ? C12 C14 1.5363(18) . ? C24 C23 1.391(2) . ? C23 C22 1.386(2) . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.1673 5.5431 8.3775 -0.8146 -0.5588 0.1555 -3.7824 -1.1199 2.5658 -0.4506 0.6587 0.6026 -0.5383 -5.3448 7.1142 -0.4758 0.6908 -0.5444 3.8070 0.9439 -2.3439 0.4390 -0.6418 -0.6288 0.2758 5.3835 -7.0876 0.4537 -0.6585 0.6004 -2.9026 1.0693 -7.2464 0.3520 0.2393 0.9049 0.2210 -5.8550 -7.6340 0.7903 0.5433 -0.2833 2.8238 -0.4723 7.8548 -0.4228 -0.2880 -0.8592