#------------------------------------------------------------------------------ #$Date: 2019-12-18 04:12:26 +0200 (Wed, 18 Dec 2019) $ #$Revision: 245289 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125662.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_7125662 loop_ _publ_author_name 'Yi, Xiangyan' 'Feng, Jiangjun' 'Huang, Fei' 'Baell, Jonathan Bayldon' _publ_section_title ; Metal-free C-C, C-O, C-S and C-N Bond Formation Enabled by SBA-15 Supported TFMSA ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC08389H _journal_year 2020 _chemical_formula_sum 'C17 H20 O4' _chemical_formula_weight 288.33 _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 _audit_creation_method SHELXL-2013 _audit_update_record ; 2019-05-22 deposited with the CCDC. 2019-12-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.4030(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.2804(4) _cell_length_b 8.1597(3) _cell_length_c 23.4123(9) _cell_measurement_reflns_used 9505 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 54.225 _cell_measurement_theta_min 4.919 _cell_volume 1581.83(11) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 193(2) _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0748 _diffrn_reflns_av_unetI/netI 0.0381 _diffrn_reflns_Laue_measured_fraction_full 0.969 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 23273 _diffrn_reflns_point_group_measured_fraction_full 0.969 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 24.996 _diffrn_reflns_theta_min 2.643 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.4933 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.211 _exptl_crystal_description prismatic _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.394 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.035 _refine_ls_extinction_coef 0.034(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 231 _refine_ls_number_reflns 2765 _refine_ls_number_restraints 82 _refine_ls_restrained_S_all 1.082 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0580 _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^)+(0.0683P)^2^+0.7576P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1491 _refine_ls_wR_factor_ref 0.1606 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2302 _reflns_number_total 2765 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc08389h2.cif _cod_data_source_block mo_dd19034_0m _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7125662 _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 0.983 _shelx_estimated_absorpt_t_max 0.988 _shelxl_version_number 2013-4 _shelx_res_file ; TITL mo_dd19034_0m_a.res in P2(1)/c CELL 0.71073 8.2804 8.1597 23.4123 90 90.403 90 ZERR 4 0.0004 0.0003 0.0009 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 68 80 16 OMIT 0 1 2 OMIT 0 0 2 OMIT 0 3 5 OMIT 3 3 3 OMIT 1 0 0 OMIT -3.00 50.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 conf htab mpla c9 > c14 mpla 5 c1 c2 c3 c5 c6 c4 c4' wpdb -1 size 0.20 0.16 0.14 dfix 1.55 0.02 c16 c17 c16' c17' dfix 1.45 0.02 o4 c16' o4 c16 simu 0.004 c4 c4' c7 c7' c16 c17 c16' c17' dfix 1.55 0.02 c3 c4 c4 c5 c4 c7 c3 c4' c4' c5 c4' c7' EQIV $1 -x+1, y-1/2, -z+3/2 HTAB C1 O1_$1 HTAB C8 O1_$1 TEMP -80.15 WGHT 0.068300 0.757600 EXTI 0.034439 FVAR 1.15387 O1 3 0.402905 0.903248 0.761774 11.00000 0.10109 0.07131 = 0.04799 -0.00824 0.01151 0.00876 O2 3 0.634503 0.700520 0.592341 11.00000 0.06224 0.05847 = 0.03770 0.00367 -0.00256 0.01501 O3 3 0.931224 0.795501 0.629254 11.00000 0.07889 0.05192 = 0.07306 0.00253 0.00412 -0.01488 O4 3 0.950536 0.575716 0.684252 11.00000 0.07566 0.06780 = 0.08234 0.02128 -0.03923 -0.01709 C1 1 0.524143 0.796078 0.680601 11.00000 0.05412 0.04975 = 0.04192 0.00034 -0.00554 0.00139 AFIX 43 H1 2 0.571097 0.707859 0.701343 11.00000 -1.20000 AFIX 0 C2 1 0.427634 0.915387 0.710233 11.00000 0.06242 0.05177 = 0.04913 -0.00683 -0.00070 -0.00324 C3 1 0.360828 1.055424 0.676237 11.00000 0.08796 0.06176 = 0.06675 -0.00384 0.00115 0.01844 PART 1 AFIX 3 H3A 2 0.359710 1.150211 0.700487 10.50000 -1.20000 H3B 2 0.251010 1.029409 0.666387 10.50000 -1.20000 PART 2 H3C 2 0.431410 1.147609 0.681187 10.50000 -1.20000 H3D 2 0.257510 1.083511 0.691787 10.50000 -1.20000 PART 1 AFIX 0 C4 1 0.443571 1.098601 0.624486 10.50000 0.05635 0.05214 = 0.06363 0.00391 -0.00640 0.00338 AFIX 13 H4 2 0.550007 1.144979 0.636837 10.50000 -1.20000 AFIX 0 C7 1 0.363035 1.231217 0.588460 10.50000 0.06845 0.05846 = 0.07876 0.01302 -0.01143 0.00955 AFIX 137 H7A 2 0.262236 1.188611 0.572061 10.50000 -1.50000 H7B 2 0.435644 1.263971 0.557618 10.50000 -1.50000 H7C 2 0.339399 1.326410 0.612516 10.50000 -1.50000 PART 2 AFIX 0 C4' 1 0.339260 1.027310 0.615234 10.50000 0.04877 0.04529 = 0.05914 -0.00003 -0.00923 0.00113 AFIX 13 H4' 2 0.245403 0.951158 0.610746 10.50000 -1.20000 AFIX 0 C7' 1 0.298023 1.183007 0.581534 10.50000 0.06106 0.05401 = 0.07736 0.00466 -0.01591 0.00484 AFIX 137 H7'1 2 0.204936 1.237245 0.598936 10.50000 -1.50000 H7'2 2 0.271839 1.153918 0.541926 10.50000 -1.50000 H7'3 2 0.390927 1.257405 0.582192 10.50000 -1.50000 PART 0 AFIX 0 C5 1 0.483844 0.943657 0.588133 11.00000 0.05361 0.05641 = 0.04756 0.00656 -0.00700 0.00205 PART 1 AFIX 3 H5A 2 0.562541 0.972152 0.559874 10.50000 -1.20000 H5B 2 0.387242 0.906853 0.569074 10.50000 -1.20000 PART 2 H5C 2 0.567543 1.023253 0.582474 10.50000 -1.20000 H5D 2 0.451642 0.900153 0.557674 10.50000 -1.20000 PART 0 AFIX 0 C6 1 0.548754 0.807643 0.624113 11.00000 0.04483 0.04850 = 0.04217 -0.00076 -0.00601 -0.00017 C8 1 0.730588 0.580445 0.621485 11.00000 0.05058 0.04742 = 0.03809 0.00549 -0.00538 0.00190 AFIX 13 H8 2 0.667754 0.531126 0.653501 11.00000 -1.20000 AFIX 0 C9 1 0.778062 0.448807 0.579339 11.00000 0.04278 0.04591 = 0.04515 0.00149 -0.00484 -0.00474 C10 1 0.779231 0.477766 0.521224 11.00000 0.09124 0.05354 = 0.04690 -0.00028 -0.00497 0.00968 AFIX 43 H10 2 0.747538 0.581798 0.506784 11.00000 -1.20000 AFIX 0 C11 1 0.826672 0.354998 0.483909 11.00000 0.09881 0.07145 = 0.05008 -0.01025 -0.00293 0.00913 AFIX 43 H11 2 0.826709 0.375494 0.443965 11.00000 -1.20000 AFIX 0 C12 1 0.873118 0.205639 0.503916 11.00000 0.06238 0.05772 = 0.07485 -0.01878 -0.00398 0.00475 AFIX 43 H12 2 0.906514 0.122586 0.478131 11.00000 -1.20000 AFIX 0 C13 1 0.871418 0.175550 0.561851 11.00000 0.06361 0.04812 = 0.08673 0.00058 -0.00035 0.00649 AFIX 43 H13 2 0.902990 0.071231 0.576069 11.00000 -1.20000 AFIX 0 C14 1 0.823903 0.296822 0.599194 11.00000 0.05836 0.05314 = 0.05946 0.00835 0.00094 0.00140 AFIX 43 H14 2 0.822800 0.275219 0.639061 11.00000 -1.20000 AFIX 0 C15 1 0.880616 0.666424 0.644917 11.00000 0.05758 0.04911 = 0.04638 0.00227 -0.00255 0.00106 PART 1 C16 1 1.105239 0.643331 0.704791 10.80000 0.05931 0.07268 = 0.06983 0.01387 -0.02349 -0.01384 AFIX 23 H16A 2 1.185245 0.644837 0.673571 10.80000 -1.20000 H16B 2 1.090358 0.756725 0.718843 10.80000 -1.20000 AFIX 0 C17 1 1.160587 0.536130 0.751379 10.80000 0.07745 0.08869 = 0.08416 0.01843 -0.04149 -0.00881 AFIX 137 H17A 2 1.076975 0.529837 0.780715 10.80000 -1.50000 H17B 2 1.259959 0.580820 0.768191 10.80000 -1.50000 H17C 2 1.181751 0.426215 0.736312 10.80000 -1.50000 PART 2 AFIX 0 C16' 1 1.061472 0.619419 0.734142 10.20000 0.07257 0.07733 = 0.08336 0.01139 -0.01859 -0.00918 AFIX 23 H16C 2 1.086523 0.737710 0.737353 10.20000 -1.20000 H16D 2 1.027664 0.573156 0.771275 10.20000 -1.20000 AFIX 0 C17' 1 1.185915 0.522513 0.704489 10.20000 0.07697 0.08045 = 0.08666 0.00647 -0.01639 -0.01498 AFIX 137 H17D 2 1.159726 0.405689 0.707352 10.20000 -1.50000 H17E 2 1.291537 0.542899 0.722252 10.20000 -1.50000 H17F 2 1.189099 0.554616 0.664177 10.20000 -1.50000 PART 0 AFIX 0 HKLF 4 REM mo_dd19034_0m_a.res in P2(1)/c REM R1 = 0.0580 for 2302 Fo > 4sig(Fo) and 0.0696 for all 2765 data REM 231 parameters refined using 82 restraints END WGHT 0.0685 0.7558 REM Instructions for potential hydrogen bonds HTAB C1 O1_$1 HTAB C8 O1_$1 REM Highest difference peak 0.394, deepest hole -0.204, 1-sigma level 0.035 Q1 1 1.1285 0.6402 0.7602 11.00000 0.05 0.39 Q2 1 1.0001 0.4807 0.6702 11.00000 0.05 0.30 Q3 1 0.2836 1.1373 0.7000 11.00000 0.05 0.29 Q4 1 0.8790 0.5522 0.7119 11.00000 0.05 0.25 Q5 1 1.0092 0.7412 0.6528 11.00000 0.05 0.17 Q6 1 0.4989 0.9602 0.7609 11.00000 0.05 0.16 Q7 1 0.5097 1.1458 0.6718 11.00000 0.05 0.15 Q8 1 1.1281 0.5467 0.6942 11.00000 0.05 0.14 Q9 1 0.7782 0.5120 0.6007 11.00000 0.05 0.13 Q10 1 0.2217 0.9575 0.6344 11.00000 0.05 0.13 Q11 1 0.8155 0.1686 0.5289 11.00000 0.05 0.13 Q12 1 0.9282 0.5983 0.6747 11.00000 0.05 0.13 Q13 1 0.4713 0.7879 0.6510 11.00000 0.05 0.13 Q14 1 0.4931 0.8586 0.6022 11.00000 0.05 0.12 Q15 1 0.6915 0.5203 0.6391 11.00000 0.05 0.12 Q16 1 1.0945 0.4705 0.7744 11.00000 0.05 0.12 Q17 1 0.4227 0.8783 0.5452 11.00000 0.05 0.11 Q18 1 1.1969 0.5255 0.7312 11.00000 0.05 0.11 Q19 1 0.8196 0.4839 0.5581 11.00000 0.05 0.11 Q20 1 1.1598 0.7460 0.6820 11.00000 0.05 0.11 ; _shelx_res_checksum 56298 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 0.4029(2) 0.9032(2) 0.76177(7) 0.0734(6) Uani 1 1 d . . . . . O2 O 0.63450(18) 0.70052(18) 0.59234(6) 0.0528(4) Uani 1 1 d . . . . . O3 O 0.9312(2) 0.7955(2) 0.62925(7) 0.0679(5) Uani 1 1 d . . . . . O4 O 0.9505(2) 0.5757(2) 0.68425(8) 0.0755(6) Uani 1 1 d D . . . . C1 C 0.5241(3) 0.7961(3) 0.68060(8) 0.0486(5) Uani 1 1 d . . . . . H1 H 0.5711 0.7079 0.7013 0.058 Uiso 1 1 calc R U . . . C2 C 0.4276(3) 0.9154(3) 0.71023(9) 0.0544(6) Uani 1 1 d . . . . . C3 C 0.3608(4) 1.0554(3) 0.67624(11) 0.0722(7) Uani 1 1 d D . . . . H3A H 0.3597 1.1502 0.7005 0.087 Uiso 0.5 1 d R U P A 1 H3B H 0.2510 1.0294 0.6664 0.087 Uiso 0.5 1 d R U P A 1 H3C H 0.4314 1.1476 0.6812 0.087 Uiso 0.5 1 d R U P B 2 H3D H 0.2575 1.0835 0.6918 0.087 Uiso 0.5 1 d R U P B 2 C4 C 0.4436(6) 1.0986(6) 0.62449(19) 0.0574(10) Uani 0.5 1 d D U P C 1 H4 H 0.5500 1.1450 0.6368 0.069 Uiso 0.5 1 calc R U P C 1 C7 C 0.3630(8) 1.2312(8) 0.5885(3) 0.0686(15) Uani 0.5 1 d D U P C 1 H7A H 0.2622 1.1886 0.5721 0.103 Uiso 0.5 1 calc R U P C 1 H7B H 0.4356 1.2640 0.5576 0.103 Uiso 0.5 1 calc R U P C 1 H7C H 0.3394 1.3264 0.6125 0.103 Uiso 0.5 1 calc R U P C 1 C4' C 0.3393(5) 1.0273(5) 0.61523(18) 0.0511(9) Uani 0.5 1 d D U P C 2 H4' H 0.2454 0.9512 0.6107 0.061 Uiso 0.5 1 calc R U P C 2 C7' C 0.2980(8) 1.1830(7) 0.5815(3) 0.0642(14) Uani 0.5 1 d D U P C 2 H7'1 H 0.2049 1.2372 0.5989 0.096 Uiso 0.5 1 calc R U P C 2 H7'2 H 0.2718 1.1539 0.5419 0.096 Uiso 0.5 1 calc R U P C 2 H7'3 H 0.3909 1.2574 0.5822 0.096 Uiso 0.5 1 calc R U P C 2 C5 C 0.4838(3) 0.9437(3) 0.58813(9) 0.0526(6) Uani 1 1 d D . . . . H5A H 0.5625 0.9722 0.5599 0.063 Uiso 0.5 1 d R U P C 1 H5B H 0.3872 0.9069 0.5691 0.063 Uiso 0.5 1 d R U P C 1 H5C H 0.5675 1.0233 0.5825 0.063 Uiso 0.5 1 d R U P C 2 H5D H 0.4516 0.9002 0.5577 0.063 Uiso 0.5 1 d R U P C 2 C6 C 0.5488(2) 0.8076(2) 0.62411(8) 0.0452(5) Uani 1 1 d . . . . . C8 C 0.7306(2) 0.5804(2) 0.62148(8) 0.0454(5) Uani 1 1 d . . . . . H8 H 0.6678 0.5311 0.6535 0.054 Uiso 1 1 calc R U . . . C9 C 0.7781(2) 0.4488(2) 0.57934(8) 0.0446(5) Uani 1 1 d . . . . . C10 C 0.7792(3) 0.4778(3) 0.52122(9) 0.0639(7) Uani 1 1 d . . . . . H10 H 0.7475 0.5818 0.5068 0.077 Uiso 1 1 calc R U . . . C11 C 0.8267(4) 0.3550(3) 0.48391(11) 0.0735(8) Uani 1 1 d . . . . . H11 H 0.8267 0.3755 0.4440 0.088 Uiso 1 1 calc R U . . . C12 C 0.8731(3) 0.2056(3) 0.50392(12) 0.0650(7) Uani 1 1 d . . . . . H12 H 0.9065 0.1226 0.4781 0.078 Uiso 1 1 calc R U . . . C13 C 0.8714(3) 0.1756(3) 0.56185(12) 0.0662(7) Uani 1 1 d . . . . . H13 H 0.9030 0.0712 0.5761 0.079 Uiso 1 1 calc R U . . . C14 C 0.8239(3) 0.2968(3) 0.59919(10) 0.0570(6) Uani 1 1 d . . . . . H14 H 0.8228 0.2752 0.6391 0.068 Uiso 1 1 calc R U . . . C15 C 0.8806(3) 0.6664(3) 0.64492(9) 0.0510(5) Uani 1 1 d . . . . . C16 C 1.1052(4) 0.6433(5) 0.70479(16) 0.0674(9) Uani 0.8 1 d D U P D 1 H16A H 1.1852 0.6448 0.6736 0.081 Uiso 0.8 1 calc R U P D 1 H16B H 1.0904 0.7567 0.7188 0.081 Uiso 0.8 1 calc R U P D 1 C17 C 1.1606(5) 0.5361(5) 0.75138(16) 0.0836(10) Uani 0.8 1 d D U P D 1 H17A H 1.0770 0.5298 0.7807 0.125 Uiso 0.8 1 calc R U P D 1 H17B H 1.2600 0.5808 0.7682 0.125 Uiso 0.8 1 calc R U P D 1 H17C H 1.1818 0.4262 0.7363 0.125 Uiso 0.8 1 calc R U P D 1 C16' C 1.0615(17) 0.619(2) 0.7341(7) 0.0778(19) Uani 0.2 1 d D U P D 2 H16C H 1.0865 0.7377 0.7374 0.093 Uiso 0.2 1 calc R U P D 2 H16D H 1.0277 0.5732 0.7713 0.093 Uiso 0.2 1 calc R U P D 2 C17' C 1.1859(17) 0.5225(19) 0.7045(7) 0.081(2) Uani 0.2 1 d D U P D 2 H17D H 1.1597 0.4057 0.7074 0.122 Uiso 0.2 1 calc R U P D 2 H17E H 1.2915 0.5429 0.7223 0.122 Uiso 0.2 1 calc R U P D 2 H17F H 1.1891 0.5546 0.6642 0.122 Uiso 0.2 1 calc R U P D 2 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 0.1011(14) 0.0713(12) 0.0480(9) -0.0082(8) 0.0115(9) 0.0088(10) O2 0.0622(9) 0.0585(9) 0.0377(7) 0.0037(6) -0.0026(6) 0.0150(7) O3 0.0789(12) 0.0519(10) 0.0731(11) 0.0025(8) 0.0041(9) -0.0149(8) O4 0.0757(12) 0.0678(11) 0.0823(12) 0.0213(9) -0.0392(9) -0.0171(9) C1 0.0541(12) 0.0498(12) 0.0419(11) 0.0003(9) -0.0055(9) 0.0014(9) C2 0.0624(13) 0.0518(12) 0.0491(12) -0.0068(10) -0.0007(10) -0.0032(10) C3 0.0880(19) 0.0618(15) 0.0668(16) -0.0038(12) 0.0012(13) 0.0184(13) C4 0.056(2) 0.052(2) 0.064(2) 0.0039(19) -0.0064(19) 0.0034(18) C7 0.068(3) 0.058(3) 0.079(3) 0.013(3) -0.011(3) 0.010(3) C4' 0.049(2) 0.045(2) 0.059(2) 0.0000(17) -0.0092(17) 0.0011(17) C7' 0.061(3) 0.054(3) 0.077(3) 0.005(2) -0.016(3) 0.005(2) C5 0.0536(12) 0.0564(13) 0.0476(12) 0.0066(10) -0.0070(9) 0.0021(10) C6 0.0448(11) 0.0485(11) 0.0422(10) -0.0008(9) -0.0060(8) -0.0002(9) C8 0.0506(11) 0.0474(11) 0.0381(10) 0.0055(8) -0.0054(8) 0.0019(9) C9 0.0428(10) 0.0459(11) 0.0452(11) 0.0015(9) -0.0048(8) -0.0047(9) C10 0.0912(18) 0.0535(13) 0.0469(12) -0.0003(10) -0.0050(12) 0.0097(12) C11 0.099(2) 0.0715(17) 0.0501(13) -0.0103(12) -0.0029(13) 0.0091(15) C12 0.0624(14) 0.0577(14) 0.0748(16) -0.0188(12) -0.0040(12) 0.0048(11) C13 0.0636(15) 0.0481(13) 0.0867(18) 0.0006(12) -0.0003(13) 0.0065(11) C14 0.0584(13) 0.0531(13) 0.0595(13) 0.0084(10) 0.0009(10) 0.0014(10) C15 0.0576(13) 0.0491(12) 0.0464(11) 0.0023(9) -0.0025(9) 0.0011(10) C16 0.0593(18) 0.0727(19) 0.070(2) 0.0139(17) -0.0235(16) -0.0138(15) C17 0.077(2) 0.089(2) 0.084(2) 0.018(2) -0.0415(19) -0.0088(18) C16' 0.073(4) 0.077(4) 0.083(4) 0.011(4) -0.019(3) -0.009(3) C17' 0.077(4) 0.080(4) 0.087(5) 0.006(5) -0.016(4) -0.015(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 C6 O2 C8 118.18(14) C15 O4 C16 113.3(2) C15 O4 C16' 131.8(7) C6 C1 C2 121.0(2) C6 C1 H1 119.5 C2 C1 H1 119.5 O1 C2 C1 121.0(2) O1 C2 C3 121.3(2) C1 C2 C3 117.65(19) C4 C3 C2 117.3(3) C4' C3 C2 116.3(2) C4 C3 H3A 107.9 C2 C3 H3A 107.8 C4 C3 H3B 107.9 C2 C3 H3B 107.7 H3A C3 H3B 107.9 C4' C3 H3C 108.2 C2 C3 H3C 108.2 C4' C3 H3D 107.8 C2 C3 H3D 107.9 H3C C3 H3D 108.1 C3 C4 C7 115.5(4) C3 C4 C5 111.4(3) C7 C4 C5 111.6(4) C3 C4 H4 105.8 C7 C4 H4 105.8 C5 C4 H4 105.8 C4 C7 H7A 109.5 C4 C7 H7B 109.5 H7A C7 H7B 109.5 C4 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 C3 C4' C5 112.9(3) C3 C4' C7' 113.6(4) C5 C4' C7' 109.3(4) C3 C4' H4' 106.9 C5 C4' H4' 106.9 C7' C4' H4' 106.9 C4' C7' H7'1 109.5 C4' C7' H7'2 109.5 H7'1 C7' H7'2 109.5 C4' C7' H7'3 109.5 H7'1 C7' H7'3 109.5 H7'2 C7' H7'3 109.5 C6 C5 C4' 112.3(2) C6 C5 C4 111.9(2) C6 C5 H5A 109.0 C4 C5 H5A 109.1 C6 C5 H5B 109.0 C4 C5 H5B 109.0 H5A C5 H5B 108.8 C6 C5 H5C 108.9 C4' C5 H5C 109.0 C6 C5 H5D 106.1 C4' C5 H5D 107.4 H5C C5 H5D 113.3 C1 C6 O2 125.46(18) C1 C6 C5 123.51(19) O2 C6 C5 111.03(16) O2 C8 C9 108.73(15) O2 C8 C15 107.76(16) C9 C8 C15 110.27(17) O2 C8 H8 110.0 C9 C8 H8 110.0 C15 C8 H8 110.0 C14 C9 C10 118.9(2) C14 C9 C8 119.45(18) C10 C9 C8 121.66(19) C9 C10 C11 120.0(2) C9 C10 H10 120.0 C11 C10 H10 120.0 C12 C11 C10 120.7(2) C12 C11 H11 119.6 C10 C11 H11 119.6 C11 C12 C13 119.6(2) C11 C12 H12 120.2 C13 C12 H12 120.2 C12 C13 C14 120.0(2) C12 C13 H13 120.0 C14 C13 H13 120.0 C9 C14 C13 120.7(2) C9 C14 H14 119.6 C13 C14 H14 119.6 O3 C15 O4 124.0(2) O3 C15 C8 125.65(19) O4 C15 C8 110.30(18) C17 C16 O4 106.6(3) C17 C16 H16A 110.4 O4 C16 H16A 110.4 C17 C16 H16B 110.4 O4 C16 H16B 110.4 H16A C16 H16B 108.6 C16 C17 H17A 109.5 C16 C17 H17B 109.5 H17A C17 H17B 109.5 C16 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 C17' C16' O4 86.2(10) C17' C16' H16C 114.3 O4 C16' H16C 114.3 C17' C16' H16D 114.3 O4 C16' H16D 114.3 H16C C16' H16D 111.4 C16' C17' H17D 109.5 C16' C17' H17E 109.5 H17D C17' H17E 109.5 C16' C17' H17F 109.5 H17D C17' H17F 109.5 H17E C17' H17F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.229(3) O2 C6 1.352(2) O2 C8 1.432(2) O3 C15 1.192(3) O4 C15 1.313(3) O4 C16 1.472(3) O4 C16' 1.523(13) C1 C6 1.343(3) C1 C2 1.441(3) C1 H1 0.9500 C2 C3 1.496(3) C3 C4 1.440(5) C3 C4' 1.456(5) C3 H3A 0.9595 C3 H3B 0.9603 C3 H3C 0.9591 C3 H3D 0.9599 C4 C7 1.523(7) C4 C5 1.561(5) C4 H4 1.0000 C7 H7A 0.9800 C7 H7B 0.9800 C7 H7C 0.9800 C4' C5 1.521(5) C4' C7' 1.533(7) C4' H4' 1.0000 C7' H7'1 0.9800 C7' H7'2 0.9800 C7' H7'3 0.9800 C5 C6 1.491(3) C5 H5A 0.9605 C5 H5B 0.9613 C5 H5C 0.9597 C5 H5D 0.8384 C8 C9 1.512(3) C8 C15 1.525(3) C8 H8 1.0000 C9 C14 1.377(3) C9 C10 1.381(3) C10 C11 1.388(3) C10 H10 0.9500 C11 C12 1.360(4) C11 H11 0.9500 C12 C13 1.379(4) C12 H12 0.9500 C13 C14 1.380(3) C13 H13 0.9500 C14 H14 0.9500 C16 C17 1.469(4) C16 H16A 0.9900 C16 H16B 0.9900 C17 H17A 0.9800 C17 H17B 0.9800 C17 H17C 0.9800 C16' C17' 1.476(16) C16' H16C 0.9900 C16' H16D 0.9900 C17' H17D 0.9800 C17' H17E 0.9800 C17' H17F 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 C1 H1 O1 0.95 2.64 3.528(3) 155.9 2_646 C8 H8 O1 1.00 2.32 3.290(2) 163.3 2_646 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 C6 C1 C2 O1 178.8(2) C6 C1 C2 C3 -2.1(3) O1 C2 C3 C4 155.5(3) C1 C2 C3 C4 -23.6(4) O1 C2 C3 C4' -156.0(3) C1 C2 C3 C4' 24.9(4) C4' C3 C4 C7 74.3(5) C2 C3 C4 C7 174.6(4) C4' C3 C4 C5 -54.4(3) C2 C3 C4 C5 46.0(4) C4 C3 C4' C5 57.5(4) C2 C3 C4' C5 -45.2(4) C4 C3 C4' C7' -67.6(5) C2 C3 C4' C7' -170.3(4) C3 C4' C5 C6 42.8(4) C7' C4' C5 C6 170.2(3) C3 C4' C5 C4 -55.1(4) C7' C4' C5 C4 72.2(4) C3 C4 C5 C6 -44.0(4) C7 C4 C5 C6 -174.7(4) C3 C4 C5 C4' 55.2(4) C7 C4 C5 C4' -75.5(5) C2 C1 C6 O2 -178.64(19) C2 C1 C6 C5 1.6(3) C8 O2 C6 C1 -11.5(3) C8 O2 C6 C5 168.30(17) C4' C5 C6 C1 -22.1(3) C4 C5 C6 C1 21.5(3) C4' C5 C6 O2 158.1(2) C4 C5 C6 O2 -158.2(2) C6 O2 C8 C9 164.94(17) C6 O2 C8 C15 -75.5(2) O2 C8 C9 C14 -159.05(18) C15 C8 C9 C14 83.0(2) O2 C8 C9 C10 22.0(3) C15 C8 C9 C10 -95.9(2) C14 C9 C10 C11 -0.3(4) C8 C9 C10 C11 178.7(2) C9 C10 C11 C12 -0.3(4) C10 C11 C12 C13 0.7(4) C11 C12 C13 C14 -0.4(4) C10 C9 C14 C13 0.5(3) C8 C9 C14 C13 -178.5(2) C12 C13 C14 C9 -0.1(4) C16 O4 C15 O3 -4.0(4) C16' O4 C15 O3 26.0(9) C16 O4 C15 C8 174.3(2) C16' O4 C15 C8 -155.7(8) O2 C8 C15 O3 -18.6(3) C9 C8 C15 O3 99.9(3) O2 C8 C15 O4 163.16(17) C9 C8 C15 O4 -78.3(2) C15 O4 C16 C17 175.5(3) C16' O4 C16 C17 41.8(12) C15 O4 C16' C17' -115.7(9) C16 O4 C16' C17' -52.7(10)