#------------------------------------------------------------------------------ #$Date: 2020-04-05 13:26:12 +0300 (Sun, 05 Apr 2020) $ #$Revision: 250217 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557263.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_1557263 loop_ _publ_author_name 'Groves, Alistair' 'Sun, Jinwei' 'Parke, Hal R. I.' 'Callingham, Michael' 'Argent, Stephen P.' 'Taylor, Laurence J.' 'Lam, Hon Wai' _publ_section_title ; Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration ; _journal_issue 10 _journal_name_full 'Chemical Science' _journal_page_first 2759 _journal_paper_doi 10.1039/C9SC06309A _journal_volume 11 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C22 H22 O2' _chemical_formula_sum 'C22 H22 O2' _chemical_formula_weight 318.39 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2019-07-17 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-10-17 deposited with the CCDC. 2020-02-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.5439(2) _cell_length_b 10.5734(2) _cell_length_c 17.3218(3) _cell_measurement_reflns_used 14650 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 77.2300 _cell_measurement_theta_min 4.6370 _cell_volume 1747.97(6) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _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 'N2 gas' _diffrn_ambient_temperature 120(2) _diffrn_crystal_treatment 'flash frozen in gaseous N2' _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_type 'PILATUS3 R 200K Hybrid Pixel Array Detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.985 _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 -33.00 33.00 0.50 1.00 -- 0.00 -82.00 120.00 132 2 \w -33.00 33.00 0.50 1.00 -- 0.00 -82.00 60.00 132 3 \w -33.00 33.00 0.50 1.00 -- 0.00 -82.00 0.00 132 4 \w 13.00 129.00 0.50 4.00 -- 102.40 -61.00-180.00 232 5 \w 13.00 69.00 0.50 4.00 -- 102.40 -30.00 30.00 112 6 \w 13.00 69.00 0.50 4.00 -- 102.40 -30.00 0.00 112 7 \w 13.00 69.00 0.50 4.00 -- 102.40 -30.00 60.00 112 8 \w 13.00 77.00 0.50 4.00 -- 102.40 -45.00 -60.00 128 9 \w 13.00 136.00 0.50 4.00 -- 102.40 -82.00-150.00 246 10 \w 80.00 192.00 0.50 4.00 -- 102.40 77.00 30.00 224 11 \w 13.00 77.00 0.50 4.00 -- 102.40 -45.00 150.00 128 12 \w 65.00 192.00 0.50 4.00 -- 102.40 15.00 -90.00 254 13 \w 13.00 192.00 0.50 4.00 -- 102.40 0.00-120.00 358 14 \w -33.00 33.00 0.50 1.00 -- 0.00 -82.00-120.00 132 15 \w -33.00 33.00 0.50 1.00 -- 0.00 -82.00 -60.00 132 16 \w 78.00 192.00 0.50 4.00 -- 102.40 30.00 0.00 228 17 \w 13.00 81.00 0.50 4.00 -- 102.40 -82.00 30.00 136 ; _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'XtalLAB PRO MM007, PILATUS3 R 200K' _diffrn_measurement_method '\w scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0628039000 _diffrn_orient_matrix_UB_12 -0.0388046000 _diffrn_orient_matrix_UB_13 -0.0783831000 _diffrn_orient_matrix_UB_21 -0.1232541000 _diffrn_orient_matrix_UB_22 -0.0645001000 _diffrn_orient_matrix_UB_23 0.0418290000 _diffrn_orient_matrix_UB_31 -0.0829352000 _diffrn_orient_matrix_UB_32 0.1249774000 _diffrn_orient_matrix_UB_33 -0.0027808000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0971 _diffrn_reflns_av_unetI/netI 0.0411 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 15494 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.788 _diffrn_reflns_theta_min 4.900 _diffrn_source 'rotating anode' _diffrn_source_type 'MicroMax 007 HF' _exptl_absorpt_coefficient_mu 0.595 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.644 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 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 colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.210 _exptl_crystal_description block _exptl_crystal_F_000 680 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: pentane/dichloromethane' _exptl_crystal_size_max 0.243 _exptl_crystal_size_mid 0.191 _exptl_crystal_size_min 0.143 _refine_diff_density_max 0.255 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.067 _refine_ls_abs_structure_details ; Flack x determined using 1443 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.04(14) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 3631 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.132 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0499 _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^)+(0.0780P)^2^+0.4869P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1346 _refine_ls_wR_factor_ref 0.1384 _reflns_Friedel_coverage 0.728 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.960 _reflns_number_gt 3520 _reflns_number_total 3631 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06309a2.cif _cod_data_source_block aghwlb _cod_depositor_comments 'Adding full bibliography for 1557262--1557263.cif.' _cod_database_code 1557263 _nottingham_internal_coll_name AGHWLB _nottingham_internal_coll_number 17920 _nottingham_internal_coll_client AG/HWL _nottingham_internal_coll_type custom _nottingham_internal_coll_frame_method '\w scans' _nottingham_internal_coll_frame_time '1.00, 4.00' _nottingham_internal_coll_frame_width 0.50 _nottingham_internal_coll_user pczlt _nottingham_internal_coll_date 11/09/2018 _nottingham_internal_coll_location NOTTS _nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876' _nottingham_internal_process_date 12/09/2018 _nottingham_internal_process_user pczlt _nottingham_internal_solution_date 17/07/2019 _nottingham_internal_solution_user pczspa _nottingham_internal_refinement_date 17/07/2019 _nottingham_internal_refinement_user pczspa _nottingham_internal_validation_date 17/07/2019 _nottingham_internal_validation_user pczspa _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C22 H22 O2' _chemical_oxdiff_usercomment 'AGHWLB #17920 Crystal mounted on Micromount in fomblin for AG/HWL' _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_max 0.920 _shelx_estimated_absorpt_t_min 0.869 _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 67.13 _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, All O(H) groups 2. Restrained distances O2-H2 0.82 with sigma of 0.02 3.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B) 3.b Aromatic/amide H refined with riding coordinates: C13(H13), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24) 3.c Idealised Me refined as rotating group: C4(H4A,H4B,H4C), C15(H15A,H15B,H15C) ; _shelx_res_file ; TITL aghwlb_a.res in P2(1)2(1)2(1) aghwlb.res created by SHELXL-2018/3 at 12:34:53 on 17-Jul-2019 REM Old TITL AGHWLB in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.117, Rweak 0.031, Alpha 0.001, Orientation as input REM Flack x = 0.085 ( 0.204 ) from Parsons' quotients REM Formula found by SHELXT: C22 O2 CELL 1.54184 9.5439 10.5734 17.3218 90 90 90 ZERR 4 0.0002 0.0002 0.0003 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H O UNIT 88 88 8 EQIV $1 1-X,0.5+Y,1.5-Z DFIX 0.82 O2 H2 L.S. 8 PLAN 5 SIZE 0.143 0.191 0.243 TEMP -153(2) HTAB O2 O6_$1 BOND $H list 4 fmap 2 acta OMIT 11 0 9 OMIT 5 4 19 OMIT 2 0 0 OMIT 0 13 1 OMIT 5 7 16 OMIT -1 11 11 OMIT -11 2 7 OMIT -9 4 13 OMIT 2 3 21 OMIT -11 2 8 OMIT -3 12 8 REM REM REM WGHT 0.078000 0.486900 FVAR 0.59857 C1 1 0.497853 0.708486 0.631910 11.00000 0.02632 0.03070 = 0.02446 -0.00588 -0.00290 0.00323 O2 3 0.594711 0.733518 0.692878 11.00000 0.03456 0.04068 = 0.02868 -0.01089 -0.00908 0.00748 H2 2 0.562886 0.785352 0.725537 11.00000 -1.50000 C3 1 0.529503 0.573193 0.605199 11.00000 0.02558 0.02750 = 0.02321 -0.00025 -0.00093 0.00187 C4 1 0.684066 0.544488 0.593411 11.00000 0.02929 0.03216 = 0.03022 0.00233 -0.00038 0.00794 AFIX 137 H4A 2 0.694813 0.457566 0.574686 11.00000 -1.50000 H4B 2 0.733852 0.554039 0.642547 11.00000 -1.50000 H4C 2 0.723197 0.603351 0.555398 11.00000 -1.50000 AFIX 0 C5 1 0.464230 0.496784 0.669644 11.00000 0.03407 0.03377 = 0.02279 0.00175 -0.00108 0.00151 O6 3 0.506412 0.393657 0.691433 11.00000 0.05578 0.03316 = 0.02943 0.00696 0.00590 0.00501 C7 1 0.342428 0.568670 0.704110 11.00000 0.03518 0.04899 = 0.03124 0.00354 0.00862 0.00558 AFIX 23 H7A 2 0.352769 0.576052 0.760800 11.00000 -1.20000 H7B 2 0.252682 0.525707 0.692548 11.00000 -1.20000 AFIX 0 C8 1 0.347765 0.699165 0.665869 11.00000 0.02999 0.03757 = 0.03019 -0.00520 0.00179 0.00829 AFIX 23 H8A 2 0.331269 0.766881 0.704279 11.00000 -1.20000 H8B 2 0.276490 0.706005 0.624555 11.00000 -1.20000 AFIX 0 C9 1 0.445998 0.546357 0.530125 11.00000 0.02561 0.02788 = 0.02361 -0.00165 0.00134 -0.00209 AFIX 23 H9A 2 0.459864 0.457317 0.514184 11.00000 -1.20000 H9B 2 0.344746 0.559908 0.539392 11.00000 -1.20000 AFIX 0 C10 1 0.496465 0.634154 0.466955 11.00000 0.02075 0.02464 = 0.02494 0.00146 -0.00198 -0.00038 C11 1 0.510573 0.768278 0.489410 11.00000 0.02012 0.02412 = 0.03069 0.00112 -0.00341 0.00051 C12 1 0.508913 0.805391 0.567472 11.00000 0.02305 0.02185 = 0.03336 -0.00452 -0.00740 0.00259 C13 1 0.513287 0.933560 0.586774 11.00000 0.03536 0.02711 = 0.04216 -0.00709 -0.01099 0.00399 AFIX 43 H13 2 0.510242 0.956844 0.639718 11.00000 -1.20000 AFIX 0 C14 1 0.521912 1.028088 0.531489 11.00000 0.03571 0.02516 = 0.05551 -0.00242 -0.01673 0.00312 C15 1 0.519666 1.165688 0.552868 11.00000 0.07010 0.02788 = 0.07619 -0.00310 -0.02817 0.00316 AFIX 137 H15A 2 0.592722 1.210559 0.524051 11.00000 -1.50000 H15B 2 0.536913 1.174657 0.608371 11.00000 -1.50000 H15C 2 0.427896 1.201659 0.540136 11.00000 -1.50000 AFIX 0 C16 1 0.529212 0.990282 0.454125 11.00000 0.03022 0.02603 = 0.04896 0.00982 -0.00817 -0.00083 AFIX 43 H16 2 0.539575 1.052539 0.414996 11.00000 -1.20000 AFIX 0 C17 1 0.521678 0.864814 0.433676 11.00000 0.02547 0.02867 = 0.03529 0.00389 -0.00213 -0.00069 AFIX 43 H17 2 0.524022 0.842624 0.380547 11.00000 -1.20000 AFIX 0 C18 1 0.532283 0.591703 0.396642 11.00000 0.02876 0.02630 = 0.02604 0.00223 0.00122 -0.00380 AFIX 43 H18 2 0.574932 0.651855 0.363363 11.00000 -1.20000 AFIX 0 C19 1 0.513995 0.464164 0.364550 11.00000 0.03229 0.02777 = 0.02026 0.00197 0.00051 -0.00103 C20 1 0.617978 0.410906 0.317974 11.00000 0.03664 0.03440 = 0.03237 -0.00179 0.00690 -0.00198 AFIX 43 H20 2 0.701533 0.457109 0.308324 11.00000 -1.20000 AFIX 0 C21 1 0.601463 0.291478 0.285459 11.00000 0.04827 0.03857 = 0.03227 -0.00409 0.00774 0.00778 AFIX 43 H21 2 0.673693 0.256499 0.254343 11.00000 -1.20000 AFIX 0 C22 1 0.480037 0.223943 0.298476 11.00000 0.05379 0.02706 = 0.02547 -0.00293 -0.00111 0.00191 AFIX 43 H22 2 0.469291 0.141846 0.276994 11.00000 -1.20000 AFIX 0 C23 1 0.373808 0.275732 0.342832 11.00000 0.03942 0.03055 = 0.02882 -0.00045 -0.00390 -0.00403 AFIX 43 H23 2 0.289910 0.229413 0.351296 11.00000 -1.20000 AFIX 0 C24 1 0.389724 0.395875 0.375146 11.00000 0.02884 0.03143 = 0.02506 -0.00206 -0.00118 -0.00099 AFIX 43 H24 2 0.315626 0.431595 0.404568 11.00000 -1.20000 AFIX 0 HKLF 4 REM aghwlb_a.res in P2(1)2(1)2(1) REM wR2 = 0.1384, GooF = S = 1.132, Restrained GooF = 1.132 for all data REM R1 = 0.0499 for 3520 Fo > 4sig(Fo) and 0.0511 for all 3631 data REM 222 parameters refined using 1 restraints END WGHT 0.0780 0.4865 REM Highest difference peak 0.255, deepest hole -0.336, 1-sigma level 0.067 Q1 1 0.4794 0.9812 0.6621 11.00000 0.05 0.25 Q2 1 0.5101 0.9271 0.2985 11.00000 0.05 0.24 Q3 1 0.4775 0.5972 0.4872 11.00000 0.05 0.24 Q4 1 0.5027 1.1729 0.6927 11.00000 0.05 0.23 Q5 1 0.4844 0.5902 0.5784 11.00000 0.05 0.23 ; _shelx_res_checksum 47915 _olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount' _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 3.477 _oxdiff_exptl_absorpt_empirical_full_min 0.563 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -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 C1 C 0.4979(3) 0.7085(2) 0.63191(13) 0.0272(5) Uani 1 1 d . O2 O 0.5947(2) 0.73352(19) 0.69288(10) 0.0346(4) Uani 1 1 d D H2 H 0.563(4) 0.785(3) 0.726(2) 0.052 Uiso 1 1 d DR C3 C 0.5295(3) 0.5732(2) 0.60520(13) 0.0254(5) Uani 1 1 d . C4 C 0.6841(3) 0.5445(2) 0.59341(15) 0.0306(5) Uani 1 1 d . H4A H 0.694813 0.457566 0.574686 0.046 Uiso 1 1 calc GR H4B H 0.733852 0.554039 0.642547 0.046 Uiso 1 1 calc GR H4C H 0.723197 0.603351 0.555398 0.046 Uiso 1 1 calc GR C5 C 0.4642(3) 0.4968(3) 0.66964(13) 0.0302(5) Uani 1 1 d . O6 O 0.5064(2) 0.39366(18) 0.69143(10) 0.0395(5) Uani 1 1 d . C7 C 0.3424(3) 0.5687(3) 0.70411(16) 0.0385(6) Uani 1 1 d . H7A H 0.352769 0.576052 0.760800 0.046 Uiso 1 1 calc R H7B H 0.252682 0.525707 0.692548 0.046 Uiso 1 1 calc R C8 C 0.3478(3) 0.6992(3) 0.66587(15) 0.0326(6) Uani 1 1 d . H8A H 0.331269 0.766881 0.704279 0.039 Uiso 1 1 calc R H8B H 0.276490 0.706005 0.624555 0.039 Uiso 1 1 calc R C9 C 0.4460(2) 0.5464(2) 0.53013(13) 0.0257(5) Uani 1 1 d . H9A H 0.459864 0.457317 0.514184 0.031 Uiso 1 1 calc R H9B H 0.344746 0.559908 0.539392 0.031 Uiso 1 1 calc R C10 C 0.4965(2) 0.6342(2) 0.46695(13) 0.0234(5) Uani 1 1 d . C11 C 0.5106(2) 0.7683(2) 0.48941(13) 0.0250(5) Uani 1 1 d . C12 C 0.5089(3) 0.8054(2) 0.56747(14) 0.0261(5) Uani 1 1 d . C13 C 0.5133(3) 0.9336(2) 0.58677(16) 0.0349(6) Uani 1 1 d . H13 H 0.510242 0.956844 0.639718 0.042 Uiso 1 1 calc R C14 C 0.5219(3) 1.0281(2) 0.53149(18) 0.0388(6) Uani 1 1 d . C15 C 0.5197(5) 1.1657(3) 0.5529(2) 0.0581(10) Uani 1 1 d . H15A H 0.592722 1.210559 0.524051 0.087 Uiso 1 1 calc GR H15B H 0.536913 1.174657 0.608371 0.087 Uiso 1 1 calc GR H15C H 0.427896 1.201659 0.540136 0.087 Uiso 1 1 calc GR C16 C 0.5292(3) 0.9903(2) 0.45413(17) 0.0351(6) Uani 1 1 d . H16 H 0.539575 1.052539 0.414996 0.042 Uiso 1 1 calc R C17 C 0.5217(3) 0.8648(2) 0.43368(15) 0.0298(5) Uani 1 1 d . H17 H 0.524022 0.842624 0.380547 0.036 Uiso 1 1 calc R C18 C 0.5323(2) 0.5917(2) 0.39664(14) 0.0270(5) Uani 1 1 d . H18 H 0.574932 0.651855 0.363363 0.032 Uiso 1 1 calc R C19 C 0.5140(3) 0.4642(2) 0.36455(12) 0.0268(5) Uani 1 1 d . C20 C 0.6180(3) 0.4109(3) 0.31797(15) 0.0345(6) Uani 1 1 d . H20 H 0.701533 0.457109 0.308324 0.041 Uiso 1 1 calc R C21 C 0.6015(3) 0.2915(3) 0.28546(16) 0.0397(6) Uani 1 1 d . H21 H 0.673693 0.256499 0.254343 0.048 Uiso 1 1 calc R C22 C 0.4800(3) 0.2239(2) 0.29848(14) 0.0354(6) Uani 1 1 d . H22 H 0.469291 0.141846 0.276994 0.043 Uiso 1 1 calc R C23 C 0.3738(3) 0.2757(3) 0.34283(14) 0.0329(5) Uani 1 1 d . H23 H 0.289910 0.229413 0.351296 0.040 Uiso 1 1 calc R C24 C 0.3897(3) 0.3959(2) 0.37515(13) 0.0284(5) Uani 1 1 d . H24 H 0.315626 0.431595 0.404568 0.034 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0263(11) 0.0307(11) 0.0245(10) -0.0059(9) -0.0029(9) 0.0032(9) O2 0.0346(10) 0.0407(10) 0.0287(9) -0.0109(8) -0.0091(7) 0.0075(8) C3 0.0256(11) 0.0275(11) 0.0232(10) -0.0002(9) -0.0009(9) 0.0019(9) C4 0.0293(12) 0.0322(13) 0.0302(12) 0.0023(10) -0.0004(9) 0.0079(10) C5 0.0341(13) 0.0338(12) 0.0228(10) 0.0017(10) -0.0011(9) 0.0015(10) O6 0.0558(12) 0.0332(10) 0.0294(8) 0.0070(7) 0.0059(9) 0.0050(9) C7 0.0352(13) 0.0490(16) 0.0312(12) 0.0035(11) 0.0086(10) 0.0056(12) C8 0.0300(12) 0.0376(14) 0.0302(12) -0.0052(10) 0.0018(10) 0.0083(10) C9 0.0256(11) 0.0279(11) 0.0236(10) -0.0017(9) 0.0013(8) -0.0021(9) C10 0.0207(10) 0.0246(10) 0.0249(10) 0.0015(8) -0.0020(9) -0.0004(9) C11 0.0201(10) 0.0241(11) 0.0307(11) 0.0011(9) -0.0034(9) 0.0005(9) C12 0.0231(11) 0.0219(11) 0.0334(11) -0.0045(9) -0.0074(9) 0.0026(9) C13 0.0354(13) 0.0271(12) 0.0422(13) -0.0071(10) -0.0110(11) 0.0040(10) C14 0.0357(14) 0.0252(12) 0.0555(16) -0.0024(11) -0.0167(13) 0.0031(11) C15 0.070(2) 0.0279(14) 0.076(2) -0.0031(16) -0.028(2) 0.0032(15) C16 0.0302(13) 0.0260(12) 0.0490(15) 0.0098(11) -0.0082(11) -0.0008(10) C17 0.0255(11) 0.0287(12) 0.0353(12) 0.0039(10) -0.0021(10) -0.0007(10) C18 0.0288(12) 0.0263(11) 0.0260(10) 0.0022(9) 0.0012(9) -0.0038(10) C19 0.0323(12) 0.0278(11) 0.0203(9) 0.0020(8) 0.0005(9) -0.0010(10) C20 0.0366(14) 0.0344(13) 0.0324(12) -0.0018(10) 0.0069(10) -0.0020(11) C21 0.0483(16) 0.0386(14) 0.0323(13) -0.0041(11) 0.0077(12) 0.0078(12) C22 0.0538(16) 0.0271(12) 0.0255(10) -0.0029(9) -0.0011(11) 0.0019(12) C23 0.0394(14) 0.0306(12) 0.0288(11) -0.0005(10) -0.0039(10) -0.0040(11) C24 0.0288(11) 0.0314(12) 0.0251(11) -0.0021(10) -0.0012(9) -0.0010(9) 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' O O 0.0492 0.0322 '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 0 -11 0.0684 3 -6 0 0.1440 1 -1 11 0.1157 -6 2 1 0.0815 6 0 -1 0.0469 2 6 -1 0.0655 -5 -4 1 0.0994 -3 -6 1 0.1179 4 -1 8 0.0806 4 3 7 0.0724 0 7 3 0.0785 -4 -4 6 0.0985 -3 1 9 0.1147 -2 5 6 0.0796 -5 -4 4 0.0849 -6 1 4 0.0749 6 0 2 0.0460 2 6 2 0.0594 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O2 C1 C3 105.57(19) O2 C1 C8 109.21(19) O2 C1 C12 111.9(2) C3 C1 C8 103.7(2) C12 C1 C3 113.20(18) C12 C1 C8 112.7(2) C1 O2 H2 113(3) C1 C3 C9 108.80(19) C4 C3 C1 114.7(2) C4 C3 C9 110.45(19) C5 C3 C1 101.22(19) C5 C3 C4 113.1(2) C5 C3 C9 108.03(19) C3 C4 H4A 109.5 C3 C4 H4B 109.5 C3 C4 H4C 109.5 H4A C4 H4B 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 O6 C5 C3 124.7(2) O6 C5 C7 125.4(2) C7 C5 C3 109.9(2) C5 C7 H7A 110.8 C5 C7 H7B 110.8 C5 C7 C8 104.9(2) H7A C7 H7B 108.8 C8 C7 H7A 110.8 C8 C7 H7B 110.8 C1 C8 H8A 110.8 C1 C8 H8B 110.8 C7 C8 C1 104.6(2) C7 C8 H8A 110.8 C7 C8 H8B 110.8 H8A C8 H8B 108.9 C3 C9 H9A 109.8 C3 C9 H9B 109.8 H9A C9 H9B 108.3 C10 C9 C3 109.29(19) C10 C9 H9A 109.8 C10 C9 H9B 109.8 C11 C10 C9 115.3(2) C18 C10 C9 122.1(2) C18 C10 C11 122.5(2) C12 C11 C10 121.3(2) C12 C11 C17 117.2(2) C17 C11 C10 121.5(2) C11 C12 C1 121.23(19) C13 C12 C1 118.7(2) C13 C12 C11 120.0(2) C12 C13 H13 118.8 C14 C13 C12 122.4(3) C14 C13 H13 118.8 C13 C14 C15 121.8(3) C13 C14 C16 117.3(2) C16 C14 C15 120.9(3) C14 C15 H15A 109.5 C14 C15 H15B 109.5 C14 C15 H15C 109.5 H15A C15 H15B 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C14 C16 H16 119.4 C17 C16 C14 121.3(3) C17 C16 H16 119.4 C11 C17 H17 119.1 C16 C17 C11 121.8(3) C16 C17 H17 119.1 C10 C18 H18 115.8 C10 C18 C19 128.3(2) C19 C18 H18 115.8 C20 C19 C18 120.3(2) C20 C19 C24 118.0(2) C24 C19 C18 121.6(2) C19 C20 H20 119.4 C21 C20 C19 121.3(3) C21 C20 H20 119.4 C20 C21 H21 120.0 C22 C21 C20 119.9(3) C22 C21 H21 120.0 C21 C22 H22 120.0 C21 C22 C23 120.1(2) C23 C22 H22 120.0 C22 C23 H23 119.9 C22 C23 C24 120.2(2) C24 C23 H23 119.9 C19 C24 H24 119.7 C23 C24 C19 120.6(2) C23 C24 H24 119.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O2 1.428(3) C1 C3 1.534(3) C1 C8 1.552(4) C1 C12 1.519(3) O2 H2 0.84(2) C3 C4 1.520(3) C3 C5 1.512(3) C3 C9 1.551(3) C4 H4A 0.9800 C4 H4B 0.9800 C4 H4C 0.9800 C5 O6 1.222(3) C5 C7 1.512(4) C7 H7A 0.9900 C7 H7B 0.9900 C7 C8 1.531(4) C8 H8A 0.9900 C8 H8B 0.9900 C9 H9A 0.9900 C9 H9B 0.9900 C9 C10 1.514(3) C10 C11 1.477(3) C10 C18 1.342(3) C11 C12 1.408(3) C11 C17 1.409(3) C12 C13 1.396(3) C13 H13 0.9500 C13 C14 1.387(4) C14 C15 1.501(4) C14 C16 1.400(4) C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 C16 H16 0.9500 C16 C17 1.375(4) C17 H17 0.9500 C18 H18 0.9500 C18 C19 1.469(3) C19 C20 1.397(4) C19 C24 1.401(4) C20 H20 0.9500 C20 C21 1.392(4) C21 H21 0.9500 C21 C22 1.380(4) C22 H22 0.9500 C22 C23 1.385(4) C23 H23 0.9500 C23 C24 1.396(4) C24 H24 0.9500 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 O6 0.84(2) 1.95(2) 2.795(3) 175(4) 3_656 yes 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 0.0031 -0.0270 -11.0046 0.8634 -0.4590 0.0270 3.0085 -5.9970 0.0091 0.0431 0.0164 -0.9990 0.9984 -0.9722 11.0053 -0.8876 0.4000 -0.2349 -6.0043 1.9976 1.0058 0.2207 0.6533 0.7448 6.0017 0.0021 -1.0105 -0.2978 -0.7821 -0.4947 1.9930 5.9983 -1.0179 -0.2781 -0.6751 0.5872 -4.9962 -4.0008 1.0182 0.3892 0.9165 -0.0885 -2.9932 -5.9991 1.0196 0.3409 0.7985 -0.5043 4.0000 -0.9772 7.9990 -0.8403 -0.0954 -0.4761 3.9951 3.0198 6.9892 -0.9159 -0.3948 0.0266 -0.0099 7.0065 2.9848 -0.5052 -0.3258 0.8682 -3.9974 -3.9878 6.0187 -0.0660 1.0017 -0.1836 -3.0045 1.0197 9.0065 -0.5568 0.6813 0.3516 -2.0123 5.1424 6.4863 -0.5816 0.1877 0.7915 -5.0054 -3.9901 4.0031 0.1554 1.0417 -0.0947 -5.9986 1.0133 4.0035 0.0236 0.8415 0.6130 6.0022 -0.0101 1.9932 -0.5328 -0.6558 -0.5046 2.0097 5.9991 1.9964 -0.5155 -0.5511 0.5775