#------------------------------------------------------------------------------ #$Date: 2024-04-11 03:52:39 +0300 (Thu, 11 Apr 2024) $ #$Revision: 291171 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159891.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_7159891 loop_ _publ_author_name 'Nanda, Samik' 'Barik, Rasmita' _publ_section_title ; Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, F and 2,9-humuladien-6-ol-8-one ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB00393D _journal_year 2024 _chemical_formula_moiety 'C16 H26 O3' _chemical_formula_sum 'C16 H26 O3' _chemical_formula_weight 266.37 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-10-13 _audit_creation_method ; Olex2 1.3-ac4 (compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739) ; _audit_update_record ; 2023-11-05 deposited with the CCDC. 2024-04-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.436(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.7763(12) _cell_length_b 14.2275(14) _cell_length_c 12.0706(16) _cell_measurement_reflns_used 6201 _cell_measurement_temperature 297.6(6) _cell_measurement_theta_max 31.2050 _cell_measurement_theta_min 2.1710 _cell_volume 1601.8(4) _computing_cell_refinement 'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)' _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_environment air _diffrn_ambient_temperature 297.6(6) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.823 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \f -10.27 348.73 1.00 5.00 73.22 -17.64 31.50 -- 359 2 \w -67.13 -0.13 1.00 5.00 -- -17.64 94.56 145.16 67 3 \w -67.13 -0.13 1.00 5.00 -- -17.64 94.56 1.16 67 4 \w -67.13 -0.13 1.00 5.00 -- -17.64 94.56-142.84 67 5 \w -113.30 10.70 1.00 5.00 -- -17.64 -59.25 173.08 124 6 \w -113.30 10.70 1.00 5.00 -- -17.64 -59.25 -33.92 124 7 \w -67.13 -0.13 1.00 5.00 -- -17.64 94.56 73.16 67 8 \f -339.92 19.08 1.00 5.00 11.45 -17.64 -59.25 -- 359 9 \w -75.95 0.05 1.00 5.00 -- -26.47 94.56 -34.84 76 10 \w -113.30 10.70 1.00 5.00 -- -17.64 -59.25 71.08 124 11 \w -58.31 -0.31 1.00 5.00 -- -8.82 94.56 -34.84 58 12 \f -349.73 9.27 1.00 5.00 4.74 -17.64 -31.50 -- 359 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'Saxi-CrysAlisPro-abstract goniometer imported SAXI images' _diffrn_measurement_method '\w and \f scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0211410000 _diffrn_orient_matrix_UB_12 -0.0400541000 _diffrn_orient_matrix_UB_13 -0.0361062000 _diffrn_orient_matrix_UB_21 -0.0723464000 _diffrn_orient_matrix_UB_22 0.0151237000 _diffrn_orient_matrix_UB_23 -0.0151937000 _diffrn_orient_matrix_UB_31 0.0097171000 _diffrn_orient_matrix_UB_32 0.0255598000 _diffrn_orient_matrix_UB_33 -0.0475555000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.2346 _diffrn_reflns_av_unetI/netI 0.2864 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.823 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 110246 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.781 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 38.284 _diffrn_reflns_theta_min 1.768 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.34508 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.105 _exptl_crystal_F_000 584 _refine_diff_density_max 0.549 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.095 _refine_ls_abs_structure_details ; Flack x determined using 1023 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -1.7(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 353 _refine_ls_number_reflns 13876 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.994 _refine_ls_R_factor_all 0.4427 _refine_ls_R_factor_gt 0.1640 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3375 _refine_ls_wR_factor_ref 0.4664 _reflns_Friedel_coverage 0.843 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.737 _reflns_number_gt 3620 _reflns_number_total 13876 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00393d2.cif _cod_data_source_block sn_rb_r1673_pj_13oct _cod_original_cell_volume 1601.8(3) _cod_database_code 7159891 _shelx_shelxl_version_number 2018/3 _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. ; _reflns_odcompleteness_completeness 82.29 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 38.19 _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: C00C(H00V), C00E(H00E), C00G(H00G), C00J(H00J), C00K(H00Y), C00N(H00) 2.b Secondary CH2 refined with riding coordinates: C00D(H00W,H00X), C00O(H00A,H00B), C00P(H1,H), C00Q(H00C,H00D), C00R(H2,HA), C00Y(H00S,H00T) 2.c Aromatic/amide H refined with riding coordinates: C00A(H00U), C00F(H00F), C00I(H00I), C00L(H00Z) 2.d Idealised Me refined as rotating group: C00S(H00H,H00K,H00L), C00T(H3,HB,HC), C00U(H00M,H00N,H00O), C00V(H4,HD,HE), C00W(H5,HF,HG), C00X(H00P,H00Q,H00R), C00Z(H6,HH,HI), C010(H01A,H01B,H01C), C011(H01D,H01E,H01F), C012(H01G,H01H,H01I) ; _shelx_res_file ; TITL sn_rb_r1673_pj_13oct_a.res in P2(1) sn_rb_r1673_pj_13oct.res created by SHELXL-2018/3 at 20:26:37 on 13-Oct-2023 REM Old TITL sn_rb_r1673_pj_13oct in P2(1) REM SHELXT solution in P2(1): R1 0.259, Rweak 0.157, Alpha 0.026 REM 0.954 for 8 systematic absences, Orientation as input REM Flack x = -2.760 ( 1.578 ) from 1025 Parsons' quotients REM Formula found by SHELXT: C32 N2 O4 CELL 0.71073 9.7763 14.2275 12.0706 90 107.436 90 ZERR 4 0.0012 0.0014 0.0016 0 0.014 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O UNIT 64 104 12 L.S. 4 0 0 PLAN 11 TEMP 25 list 4 fmap 2 53 ACTA REM REM REM WGHT 0.200000 FVAR 0.66111 O001 3 0.598995 0.367110 1.088417 11.00000 0.14648 0.07633 = 0.06759 0.01196 0.03309 -0.01799 O002 3 0.585927 0.633713 0.207879 11.00000 0.10125 0.07002 = 0.08102 0.01978 0.04330 0.00005 O003 3 0.593675 0.404171 0.640221 11.00000 0.14811 0.11900 = 0.07242 0.03879 0.04421 0.02013 C004 1 0.594847 0.379830 0.545823 11.00000 0.08546 0.05302 = 0.05473 0.00766 0.00573 -0.00320 O005 3 0.916796 0.641088 1.039027 11.00000 0.09129 0.07953 = 0.12925 -0.01834 0.00621 -0.01120 C006 1 0.662952 0.389297 0.996485 11.00000 0.12130 0.06751 = 0.04564 0.01148 0.02379 0.00124 O007 3 0.888652 0.354990 0.404816 11.00000 0.10214 0.10945 = 0.11742 0.00124 0.03853 0.03033 O008 3 0.588984 0.631392 0.665556 11.00000 0.17233 0.12062 = 0.08521 0.01201 0.05998 -0.03544 C009 1 0.606155 0.638869 0.763458 11.00000 0.09649 0.05072 = 0.07191 0.00591 0.03521 -0.01019 C00A 1 0.405588 0.477314 0.428185 11.00000 0.09573 0.06339 = 0.06258 0.00880 0.03758 -0.00135 AFIX 43 H00U 2 0.425221 0.517657 0.491643 11.00000 -1.20000 AFIX 0 C00B 1 0.649959 0.612609 0.329170 11.00000 0.10129 0.07290 = 0.06231 0.00927 0.04541 0.00273 C00C 1 0.516995 0.570805 0.265872 11.00000 0.09193 0.07583 = 0.06585 0.01985 0.03689 0.00773 AFIX 13 H00V 2 0.527964 0.504955 0.246276 11.00000 -1.20000 AFIX 0 C00D 1 0.806717 0.495439 0.459973 11.00000 0.07563 0.05585 = 0.07388 -0.00125 0.01958 -0.00323 AFIX 23 H00W 2 0.748444 0.518974 0.506335 11.00000 -1.20000 H00X 2 0.906147 0.498344 0.507408 11.00000 -1.20000 AFIX 0 C00E 1 0.531339 0.436857 1.002390 11.00000 0.11020 0.06718 = 0.06598 0.01244 0.03361 -0.01265 AFIX 13 H00E 2 0.547079 0.501602 1.031105 11.00000 -1.20000 AFIX 0 C00F 1 0.418973 0.540860 0.792774 11.00000 0.10283 0.10380 = 0.04822 -0.00156 0.02716 -0.00992 AFIX 43 H00F 2 0.434851 0.504583 0.733719 11.00000 -1.20000 AFIX 0 C00G 1 0.751065 0.668747 0.847602 11.00000 0.10251 0.05605 = 0.10390 0.01163 0.04144 -0.00172 AFIX 13 H00G 2 0.739383 0.733359 0.871417 11.00000 -1.20000 AFIX 0 C00H 1 0.298119 0.511717 0.318614 11.00000 0.05423 0.07458 = 0.08195 0.00443 0.02276 -0.00020 C00I 1 0.494005 0.620387 0.817631 11.00000 0.08268 0.07536 = 0.07985 -0.00112 0.02066 -0.00528 AFIX 43 H00I 2 0.475078 0.663622 0.868943 11.00000 -1.20000 AFIX 0 C00J 1 0.791726 0.608974 0.958102 11.00000 0.06504 0.06575 = 0.09931 0.00630 0.02399 -0.00437 AFIX 13 H00J 2 0.713463 0.612425 0.993127 11.00000 -1.20000 AFIX 0 C00K 1 0.767202 0.393076 0.429230 11.00000 0.07073 0.07844 = 0.06829 -0.00102 0.02335 0.01330 AFIX 13 H00Y 2 0.686248 0.391479 0.357862 11.00000 -1.20000 AFIX 0 C00L 1 0.473912 0.398292 0.444602 11.00000 0.10817 0.05319 = 0.10621 0.02503 0.06273 0.00630 AFIX 43 H00Z 2 0.444096 0.351305 0.389013 11.00000 -1.20000 AFIX 0 C00M 1 0.313046 0.502775 0.847528 11.00000 0.07347 0.07709 = 0.10681 -0.00770 0.02894 -0.01109 C00N 1 0.725718 0.337060 0.523436 11.00000 0.09191 0.06160 = 0.08010 0.00032 0.03042 -0.00290 AFIX 13 H00 2 0.698393 0.273951 0.492054 11.00000 -1.20000 AFIX 0 C00O 1 0.819602 0.505384 0.937994 11.00000 0.09847 0.03750 = 0.06988 -0.00771 0.03149 0.00005 AFIX 23 H00A 2 0.752987 0.485557 0.864713 11.00000 -1.20000 H00B 2 0.915770 0.499269 0.931604 11.00000 -1.20000 AFIX 0 C00P 1 0.367354 0.592662 0.268623 11.00000 0.10153 0.07222 = 0.07150 0.00673 0.01699 0.00875 AFIX 23 H1 2 0.307736 0.606325 0.190309 11.00000 -1.20000 H 2 0.370090 0.648591 0.315195 11.00000 -1.20000 AFIX 0 C00Q 1 0.804558 0.440340 1.032985 11.00000 0.10335 0.05668 = 0.08596 -0.00064 0.01415 0.00536 AFIX 23 H00C 2 0.882085 0.394900 1.051161 11.00000 -1.20000 H00D 2 0.811829 0.476605 1.102565 11.00000 -1.20000 AFIX 0 C00R 1 0.787104 0.558601 0.356902 11.00000 0.09106 0.07778 = 0.08926 0.01524 0.04759 -0.00017 AFIX 23 H2 2 0.866774 0.602301 0.372394 11.00000 -1.20000 HA 2 0.787992 0.520998 0.290089 11.00000 -1.20000 AFIX 0 C00S 1 0.659381 0.310222 0.914189 11.00000 0.16879 0.05174 = 0.09154 -0.00186 0.05216 -0.00964 AFIX 137 H00H 2 0.735393 0.266856 0.948848 11.00000 -1.50000 H00K 2 0.671589 0.334624 0.843606 11.00000 -1.50000 H00L 2 0.568866 0.278383 0.897243 11.00000 -1.50000 AFIX 0 C00T 1 0.652530 0.695750 0.408093 11.00000 0.12540 0.08115 = 0.09349 0.00144 0.04322 -0.00451 AFIX 137 H3 2 0.733128 0.735107 0.410488 11.00000 -1.50000 HB 2 0.660525 0.673667 0.484931 11.00000 -1.50000 HC 2 0.565568 0.731185 0.378896 11.00000 -1.50000 AFIX 0 C00U 1 0.865437 0.671353 0.786312 11.00000 0.13404 0.10364 = 0.15457 0.03896 0.08885 -0.00240 AFIX 137 H00M 2 0.891408 0.608306 0.772607 11.00000 -1.50000 H00N 2 0.948338 0.703811 0.833965 11.00000 -1.50000 H00O 2 0.829048 0.703592 0.713522 11.00000 -1.50000 AFIX 0 C00V 1 0.171254 0.555077 0.349519 11.00000 0.10347 0.10843 = 0.19148 0.05750 0.06472 0.02291 AFIX 137 H4 2 0.115241 0.506098 0.369378 11.00000 -1.50000 HD 2 0.112747 0.589650 0.284126 11.00000 -1.50000 HE 2 0.206077 0.596721 0.414467 11.00000 -1.50000 AFIX 0 C00W 1 0.245456 0.436838 0.227820 11.00000 0.11962 0.10416 = 0.08517 0.00693 0.00253 -0.01008 AFIX 137 H5 2 0.320803 0.420170 0.195612 11.00000 -1.50000 HF 2 0.164684 0.460170 0.167309 11.00000 -1.50000 HG 2 0.217275 0.382387 0.262599 11.00000 -1.50000 AFIX 0 C00X 1 0.271173 0.577804 0.927043 11.00000 0.10535 0.10742 = 0.10544 0.00585 0.04872 -0.00126 AFIX 137 H00P 2 0.354261 0.593844 0.990171 11.00000 -1.50000 H00Q 2 0.198689 0.552343 0.957282 11.00000 -1.50000 H00R 2 0.234958 0.633114 0.882308 11.00000 -1.50000 AFIX 0 C00Y 1 0.389810 0.419876 0.928035 11.00000 0.10574 0.09577 = 0.11164 -0.00096 0.03561 -0.02838 AFIX 23 H00S 2 0.330520 0.401811 0.976140 11.00000 -1.20000 H00T 2 0.393601 0.366513 0.879023 11.00000 -1.20000 AFIX 0 C00Z 1 0.849194 0.324964 0.635648 11.00000 0.11401 0.07650 = 0.10853 0.02238 -0.00155 0.01188 AFIX 137 H6 2 0.882589 0.385643 0.667079 11.00000 -1.50000 HH 2 0.926174 0.291428 0.619335 11.00000 -1.50000 HI 2 0.816284 0.290231 0.690928 11.00000 -1.50000 AFIX 0 C010 1 0.891491 0.726669 1.094641 11.00000 0.14497 0.07881 = 0.15371 -0.05436 0.01307 -0.00424 AFIX 137 H01A 2 0.911614 0.779966 1.053296 11.00000 -1.50000 H01B 2 0.952902 0.728063 1.173348 11.00000 -1.50000 H01C 2 0.793171 0.728753 1.094174 11.00000 -1.50000 AFIX 0 C011 1 0.178825 0.471628 0.756878 11.00000 0.10802 0.17130 = 0.13623 -0.00396 0.00483 -0.06129 AFIX 137 H01D 2 0.128961 0.525594 0.716588 11.00000 -1.50000 H01E 2 0.118252 0.438740 0.793480 11.00000 -1.50000 H01F 2 0.203457 0.430639 0.702616 11.00000 -1.50000 AFIX 0 C012 1 0.855874 0.270039 0.336629 11.00000 0.17952 0.13075 = 0.15121 -0.03515 0.05405 0.06665 AFIX 137 H01G 2 0.878943 0.278577 0.265375 11.00000 -1.50000 H01H 2 0.755622 0.256075 0.319611 11.00000 -1.50000 H01I 2 0.911254 0.218956 0.379544 11.00000 -1.50000 AFIX 0 HKLF 4 REM sn_rb_r1673_pj_13oct_a.res in P2(1) REM wR2 = 0.4664, GooF = S = 0.994, Restrained GooF = 0.994 for all data REM R1 = 0.1640 for 3620 Fo > 4sig(Fo) and 0.4427 for all 13876 data REM 353 parameters refined using 1 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.549, deepest hole -0.238, 1-sigma level 0.095 Q1 1 0.9055 0.6447 0.5411 11.00000 0.05 0.55 Q2 1 0.6547 0.3936 0.4951 11.00000 0.05 0.50 Q3 1 0.6130 0.3691 0.5728 11.00000 0.05 0.49 Q4 1 0.9012 0.3557 0.9101 11.00000 0.05 0.44 Q5 1 0.5828 0.6265 0.7141 11.00000 0.05 0.43 Q6 1 0.5764 0.6293 0.1582 11.00000 0.05 0.43 Q7 1 0.4933 0.6135 0.2983 11.00000 0.05 0.41 Q8 1 0.7926 0.4452 0.5394 11.00000 0.05 0.38 Q9 1 0.4077 0.5454 0.2945 11.00000 0.05 0.36 Q10 1 0.8590 0.6808 0.2971 11.00000 0.05 0.36 Q11 1 0.6358 0.6274 0.8227 11.00000 0.05 0.36 ; _shelx_res_checksum 67327 _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 ; _oxdiff_exptl_absorpt_empirical_full_max 1.636 _oxdiff_exptl_absorpt_empirical_full_min 0.412 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 O001 O 0.5990(8) 0.3671(5) 1.0884(5) 0.097(2) Uani 1 1 d . . . . . O002 O 0.5859(7) 0.6337(4) 0.2079(5) 0.0806(17) Uani 1 1 d . . . . . O003 O 0.5937(9) 0.4042(6) 0.6402(6) 0.111(3) Uani 1 1 d . . . . . C004 C 0.5948(10) 0.3798(6) 0.5458(7) 0.068(2) Uani 1 1 d . . . . . O005 O 0.9168(7) 0.6411(6) 1.0390(7) 0.106(2) Uani 1 1 d . . . . . C006 C 0.6630(11) 0.3893(6) 0.9965(6) 0.078(3) Uani 1 1 d . . . . . O007 O 0.8887(8) 0.3550(6) 0.4048(7) 0.108(2) Uani 1 1 d . . . . . O008 O 0.5890(10) 0.6314(7) 0.6656(7) 0.121(3) Uani 1 1 d . . . . . C009 C 0.6062(10) 0.6389(6) 0.7635(8) 0.071(2) Uani 1 1 d . . . . . C00A C 0.4056(10) 0.4773(6) 0.4282(7) 0.071(2) Uani 1 1 d . . . . . H00U H 0.425221 0.517657 0.491643 0.085 Uiso 1 1 calc R . . . . C00B C 0.6500(10) 0.6126(6) 0.3292(7) 0.074(2) Uani 1 1 d . . . . . C00C C 0.5170(10) 0.5708(7) 0.2659(7) 0.075(2) Uani 1 1 d . . . . . H00V H 0.527964 0.504955 0.246276 0.090 Uiso 1 1 calc R . . . . C00D C 0.8067(9) 0.4954(6) 0.4600(7) 0.069(2) Uani 1 1 d . . . . . H00W H 0.748444 0.518974 0.506335 0.083 Uiso 1 1 calc R . . . . H00X H 0.906147 0.498344 0.507408 0.083 Uiso 1 1 calc R . . . . C00E C 0.5313(11) 0.4369(7) 1.0024(7) 0.080(3) Uani 1 1 d . . . . . H00E H 0.547079 0.501602 1.031105 0.095 Uiso 1 1 calc R . . . . C00F C 0.4190(11) 0.5409(8) 0.7928(7) 0.084(3) Uani 1 1 d . . . . . H00F H 0.434851 0.504583 0.733719 0.101 Uiso 1 1 calc R . . . . C00G C 0.7511(10) 0.6687(7) 0.8476(9) 0.085(3) Uani 1 1 d . . . . . H00G H 0.739383 0.733359 0.871417 0.102 Uiso 1 1 calc R . . . . C00H C 0.2981(8) 0.5117(7) 0.3186(7) 0.070(2) Uani 1 1 d . . . . . C00I C 0.4940(9) 0.6204(7) 0.8176(8) 0.080(2) Uani 1 1 d . . . . . H00I H 0.475078 0.663622 0.868943 0.096 Uiso 1 1 calc R . . . . C00J C 0.7917(9) 0.6090(6) 0.9581(8) 0.077(2) Uani 1 1 d . . . . . H00J H 0.713463 0.612425 0.993127 0.092 Uiso 1 1 calc R . . . . C00K C 0.7672(9) 0.3931(6) 0.4292(7) 0.072(2) Uani 1 1 d . . . . . H00Y H 0.686248 0.391479 0.357862 0.086 Uiso 1 1 calc R . . . . C00L C 0.4739(11) 0.3983(6) 0.4446(9) 0.082(3) Uani 1 1 d . . . . . H00Z H 0.444096 0.351305 0.389013 0.099 Uiso 1 1 calc R . . . . C00M C 0.3130(10) 0.5028(7) 0.8475(9) 0.085(3) Uani 1 1 d . . . . . C00N C 0.7257(10) 0.3371(6) 0.5234(8) 0.077(2) Uani 1 1 d . . . . . H00 H 0.698393 0.273951 0.492054 0.092 Uiso 1 1 calc R . . . . C00O C 0.8196(10) 0.5054(5) 0.9380(7) 0.067(2) Uani 1 1 d . . . . . H00A H 0.752987 0.485557 0.864713 0.081 Uiso 1 1 calc R . . . . H00B H 0.915770 0.499269 0.931604 0.081 Uiso 1 1 calc R . . . . C00P C 0.3674(11) 0.5927(7) 0.2686(8) 0.084(3) Uani 1 1 d . . . . . H1 H 0.307736 0.606325 0.190309 0.100 Uiso 1 1 calc R . . . . H H 0.370090 0.648591 0.315195 0.100 Uiso 1 1 calc R . . . . C00Q C 0.8046(11) 0.4403(7) 1.0330(8) 0.085(3) Uani 1 1 d . . . . . H00C H 0.882085 0.394900 1.051161 0.102 Uiso 1 1 calc R . . . . H00D H 0.811829 0.476605 1.102565 0.102 Uiso 1 1 calc R . . . . C00R C 0.7871(10) 0.5586(7) 0.3569(8) 0.082(3) Uani 1 1 d . . . . . H2 H 0.866774 0.602301 0.372394 0.098 Uiso 1 1 calc R . . . . HA H 0.787992 0.520998 0.290089 0.098 Uiso 1 1 calc R . . . . C00S C 0.6594(14) 0.3102(7) 0.9142(9) 0.101(3) Uani 1 1 d . . . . . H00H H 0.735393 0.266856 0.948848 0.152 Uiso 1 1 calc GR . . . . H00K H 0.671589 0.334624 0.843606 0.152 Uiso 1 1 calc GR . . . . H00L H 0.568866 0.278383 0.897243 0.152 Uiso 1 1 calc GR . . . . C00T C 0.6525(13) 0.6958(8) 0.4081(9) 0.098(3) Uani 1 1 d . . . . . H3 H 0.733128 0.735107 0.410488 0.147 Uiso 1 1 calc GR . . . . HB H 0.660525 0.673667 0.484931 0.147 Uiso 1 1 calc GR . . . . HC H 0.565568 0.731185 0.378896 0.147 Uiso 1 1 calc GR . . . . C00U C 0.8654(13) 0.6714(9) 0.7863(12) 0.121(4) Uani 1 1 d . . . . . H00M H 0.891408 0.608306 0.772607 0.181 Uiso 1 1 calc GR . . . . H00N H 0.948338 0.703811 0.833965 0.181 Uiso 1 1 calc GR . . . . H00O H 0.829048 0.703592 0.713522 0.181 Uiso 1 1 calc GR . . . . C00V C 0.1713(13) 0.5551(10) 0.3495(14) 0.130(5) Uani 1 1 d . . . . . H4 H 0.115241 0.506098 0.369378 0.195 Uiso 1 1 calc GR . . . . HD H 0.112747 0.589650 0.284126 0.195 Uiso 1 1 calc GR . . . . HE H 0.206077 0.596721 0.414467 0.195 Uiso 1 1 calc GR . . . . C00W C 0.2455(13) 0.4368(9) 0.2278(9) 0.109(4) Uani 1 1 d . . . . . H5 H 0.320803 0.420170 0.195612 0.164 Uiso 1 1 calc GR . . . . HF H 0.164684 0.460170 0.167309 0.164 Uiso 1 1 calc GR . . . . HG H 0.217275 0.382387 0.262599 0.164 Uiso 1 1 calc GR . . . . C00X C 0.2712(12) 0.5778(9) 0.9270(10) 0.102(3) Uani 1 1 d . . . . . H00P H 0.354261 0.593844 0.990171 0.153 Uiso 1 1 calc GR . . . . H00Q H 0.198689 0.552343 0.957282 0.153 Uiso 1 1 calc GR . . . . H00R H 0.234958 0.633114 0.882308 0.153 Uiso 1 1 calc GR . . . . C00Y C 0.3898(12) 0.4199(9) 0.9280(10) 0.104(3) Uani 1 1 d . . . . . H00S H 0.330520 0.401811 0.976140 0.124 Uiso 1 1 calc R . . . . H00T H 0.393601 0.366513 0.879023 0.124 Uiso 1 1 calc R . . . . C00Z C 0.8492(13) 0.3250(8) 0.6356(10) 0.107(3) Uani 1 1 d . . . . . H6 H 0.882589 0.385643 0.667079 0.161 Uiso 1 1 calc GR . . . . HH H 0.926174 0.291428 0.619335 0.161 Uiso 1 1 calc GR . . . . HI H 0.816284 0.290231 0.690928 0.161 Uiso 1 1 calc GR . . . . C010 C 0.8915(16) 0.7267(9) 1.0946(13) 0.133(5) Uani 1 1 d . . . . . H01A H 0.911614 0.779966 1.053296 0.199 Uiso 1 1 calc GR . . . . H01B H 0.952902 0.728063 1.173348 0.199 Uiso 1 1 calc GR . . . . H01C H 0.793171 0.728753 1.094174 0.199 Uiso 1 1 calc GR . . . . C011 C 0.1788(14) 0.4716(13) 0.7569(12) 0.145(6) Uani 1 1 d . . . . . H01D H 0.128961 0.525594 0.716588 0.218 Uiso 1 1 calc GR . . . . H01E H 0.118252 0.438740 0.793480 0.218 Uiso 1 1 calc GR . . . . H01F H 0.203457 0.430639 0.702616 0.218 Uiso 1 1 calc GR . . . . C012 C 0.8559(17) 0.2700(11) 0.3366(13) 0.153(6) Uani 1 1 d . . . . . H01G H 0.878943 0.278577 0.265375 0.229 Uiso 1 1 calc GR . . . . H01H H 0.755622 0.256075 0.319611 0.229 Uiso 1 1 calc GR . . . . H01I H 0.911254 0.218956 0.379544 0.229 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 O001 0.146(6) 0.076(4) 0.068(3) 0.012(3) 0.033(4) -0.018(4) O002 0.101(4) 0.070(4) 0.081(4) 0.020(3) 0.043(3) 0.000(3) O003 0.148(6) 0.119(6) 0.072(4) 0.039(4) 0.044(4) 0.020(5) C004 0.085(6) 0.053(5) 0.055(4) 0.008(4) 0.006(4) -0.003(4) O005 0.091(5) 0.080(4) 0.129(6) -0.018(4) 0.006(4) -0.011(4) C006 0.121(8) 0.068(6) 0.046(4) 0.011(4) 0.024(4) 0.001(5) O007 0.102(5) 0.109(6) 0.117(5) 0.001(5) 0.039(4) 0.030(4) O008 0.172(7) 0.121(6) 0.085(5) 0.012(5) 0.060(5) -0.035(6) C009 0.096(6) 0.051(4) 0.072(5) 0.006(4) 0.035(5) -0.010(4) C00A 0.096(6) 0.063(5) 0.063(5) 0.009(4) 0.038(4) -0.001(4) C00B 0.101(7) 0.073(6) 0.062(5) 0.009(4) 0.045(5) 0.003(5) C00C 0.092(7) 0.076(6) 0.066(5) 0.020(4) 0.037(5) 0.008(5) C00D 0.076(5) 0.056(5) 0.074(5) -0.001(4) 0.020(4) -0.003(4) C00E 0.110(8) 0.067(5) 0.066(5) 0.012(4) 0.034(5) -0.013(5) C00F 0.103(7) 0.104(8) 0.048(4) -0.002(5) 0.027(4) -0.010(6) C00G 0.103(7) 0.056(5) 0.104(7) 0.012(5) 0.041(6) -0.002(5) C00H 0.054(5) 0.075(6) 0.082(5) 0.004(5) 0.023(4) 0.000(4) C00I 0.083(6) 0.075(6) 0.080(6) -0.001(5) 0.021(5) -0.005(5) C00J 0.065(5) 0.066(5) 0.099(6) 0.006(5) 0.024(5) -0.004(4) C00K 0.071(5) 0.078(6) 0.068(5) -0.001(4) 0.023(4) 0.013(4) C00L 0.108(7) 0.053(5) 0.106(7) 0.025(5) 0.063(6) 0.006(5) C00M 0.073(6) 0.077(6) 0.107(7) -0.008(6) 0.029(5) -0.011(5) C00N 0.092(6) 0.062(5) 0.080(6) 0.000(4) 0.030(5) -0.003(5) C00O 0.098(6) 0.038(4) 0.070(5) -0.008(4) 0.031(4) 0.000(4) C00P 0.102(7) 0.072(6) 0.071(5) 0.007(4) 0.017(5) 0.009(5) C00Q 0.103(7) 0.057(5) 0.086(6) -0.001(5) 0.014(5) 0.005(5) C00R 0.091(6) 0.078(6) 0.089(6) 0.015(5) 0.048(5) 0.000(5) C00S 0.169(11) 0.052(5) 0.092(7) -0.002(5) 0.052(7) -0.010(6) C00T 0.125(8) 0.081(7) 0.093(7) 0.001(6) 0.043(6) -0.005(6) C00U 0.134(9) 0.104(9) 0.155(11) 0.039(8) 0.089(9) -0.002(7) C00V 0.103(8) 0.108(9) 0.191(13) 0.058(10) 0.065(8) 0.023(7) C00W 0.120(9) 0.104(8) 0.085(7) 0.007(6) 0.003(6) -0.010(7) C00X 0.105(7) 0.107(8) 0.105(7) 0.006(7) 0.049(6) -0.001(6) C00Y 0.106(8) 0.096(8) 0.112(8) -0.001(6) 0.036(7) -0.028(6) C00Z 0.114(8) 0.076(7) 0.109(7) 0.022(6) -0.002(6) 0.012(6) C010 0.145(11) 0.079(7) 0.154(11) -0.054(8) 0.013(8) -0.004(7) C011 0.108(10) 0.171(15) 0.136(10) -0.004(10) 0.005(8) -0.061(10) C012 0.180(14) 0.131(13) 0.151(12) -0.035(10) 0.054(10) 0.067(11) 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 C00E O001 C006 60.9(5) . . ? C00C O002 C00B 59.7(5) . . ? O003 C004 C00L 120.9(9) . . ? O003 C004 C00N 122.5(8) . . ? C00L C004 C00N 116.3(7) . . ? C00J O005 C010 111.4(8) . . ? O001 C006 C00E 59.0(6) . . ? O001 C006 C00Q 116.5(7) . . ? O001 C006 C00S 114.3(7) . . ? C00E C006 C00Q 120.2(8) . . ? C00E C006 C00S 122.1(9) . . ? C00S C006 C00Q 113.2(9) . . ? C00K O007 C012 112.5(10) . . ? O008 C009 C00G 121.9(8) . . ? O008 C009 C00I 123.2(9) . . ? C00I C009 C00G 114.9(8) . . ? C00L C00A C00H 127.7(9) . . ? O002 C00B C00R 115.0(6) . . ? O002 C00B C00T 113.4(7) . . ? C00C C00B O002 59.6(5) . . ? C00C C00B C00R 121.2(8) . . ? C00C C00B C00T 120.2(8) . . ? C00R C00B C00T 114.6(9) . . ? O002 C00C C00B 60.8(5) . . ? O002 C00C C00P 119.1(7) . . ? C00B C00C C00P 129.6(9) . . ? C00R C00D C00K 114.2(8) . . ? O001 C00E C006 60.1(6) . . ? C00Y C00E O001 119.0(8) . . ? C00Y C00E C006 126.0(9) . . ? C00I C00F C00M 128.2(9) . . ? C00J C00G C009 111.7(7) . . ? C00U C00G C009 110.7(9) . . ? C00U C00G C00J 113.7(9) . . ? C00A C00H C00P 108.3(7) . . ? C00A C00H C00V 108.7(9) . . ? C00A C00H C00W 114.0(8) . . ? C00V C00H C00P 106.1(8) . . ? C00W C00H C00P 109.7(7) . . ? C00W C00H C00V 109.8(9) . . ? C00F C00I C009 119.3(9) . . ? O005 C00J C00G 111.9(7) . . ? O005 C00J C00O 105.4(7) . . ? C00G C00J C00O 114.1(8) . . ? O007 C00K C00D 104.5(7) . . ? O007 C00K C00N 112.3(7) . . ? C00D C00K C00N 114.7(7) . . ? C00A C00L C004 122.8(10) . . ? C00F C00M C00X 111.6(9) . . ? C00F C00M C00Y 106.4(8) . . ? C00F C00M C011 110.9(9) . . ? C00Y C00M C00X 107.2(8) . . ? C011 C00M C00X 108.4(10) . . ? C011 C00M C00Y 112.4(10) . . ? C004 C00N C00K 110.4(7) . . ? C004 C00N C00Z 111.9(8) . . ? C00Z C00N C00K 113.6(8) . . ? C00Q C00O C00J 113.9(7) . . ? C00C C00P C00H 113.4(7) . . ? C006 C00Q C00O 111.2(7) . . ? C00B C00R C00D 112.2(7) . . ? C00E C00Y C00M 117.1(9) . . ? 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 O001 C006 1.462(11) . ? O001 C00E 1.445(12) . ? O002 C00B 1.441(10) . ? O002 C00C 1.424(10) . ? O003 C004 1.194(10) . ? C004 C00L 1.447(13) . ? C004 C00N 1.512(13) . ? O005 C00J 1.394(11) . ? O005 C010 1.447(14) . ? C006 C00E 1.474(14) . ? C006 C00Q 1.507(14) . ? C006 C00S 1.494(13) . ? O007 C00K 1.414(10) . ? O007 C012 1.443(17) . ? O008 C009 1.148(10) . ? C009 C00G 1.535(13) . ? C009 C00I 1.459(13) . ? C00A C00H 1.503(12) . ? C00A C00L 1.292(12) . ? C00B C00C 1.426(13) . ? C00B C00R 1.494(13) . ? C00B C00T 1.514(13) . ? C00C C00P 1.506(13) . ? C00D C00K 1.524(12) . ? C00D C00R 1.500(12) . ? C00E C00Y 1.426(15) . ? C00F C00I 1.333(14) . ? C00F C00M 1.488(13) . ? C00G C00J 1.531(13) . ? C00G C00U 1.515(13) . ? C00H C00P 1.547(13) . ? C00H C00V 1.528(15) . ? C00H C00W 1.504(15) . ? C00J C00O 1.531(11) . ? C00K C00N 1.539(12) . ? C00M C00X 1.570(15) . ? C00M C00Y 1.569(16) . ? C00M C011 1.502(15) . ? C00N C00Z 1.530(14) . ? C00O C00Q 1.515(12) . ?