#------------------------------------------------------------------------------ #$Date: 2015-05-20 07:35:20 +0300 (Wed, 20 May 2015) $ #$Revision: 137020 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/04/7220499.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_7220499 loop_ _publ_author_name 'Kavuru, Padmini' 'Grebinoski, Stephanie' 'Patel, Mitulkumar A.' 'Wojtas, Lukasz' 'Chadwick, Keith' _publ_section_title ; Polymorphism of Vanillin Revisited: The Discovery and Selective Crystallization of a Rare Crystal Structure ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C5CE00568J _journal_year 2015 _chemical_formula_moiety 'C8 H8 O3' _chemical_formula_sum 'C8 H8 O3' _chemical_formula_weight 152.14 _chemical_name_systematic Vanillin _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014 _audit_update_record ; 2015-03-20 deposited with the CCDC. 2015-05-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 16 _cell_length_a 16.3977(7) _cell_length_b 3.80990(10) _cell_length_c 45.645(2) _cell_measurement_temperature 100(2) _cell_volume 2851.61(19) _computing_cell_refinement 'APEX2 (Bruker, 2013); SAINT (Bruker, 2013)' _computing_data_collection 'APEX2 (Bruker, 2013)' _computing_data_reduction 'SAINT (Bruker, 2013);XPREP(Sheldrick,2008)' _computing_publication_material 'APEX2 (Bruker, 2010)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type ' BRUKER ApexII X8 CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'ImuS microsource' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_unetI/netI 0.0485 _diffrn_reflns_laue_measured_fraction_full 0.997 _diffrn_reflns_laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 54 _diffrn_reflns_limit_l_min -56 _diffrn_reflns_number 14594 _diffrn_reflns_point_group_measured_fraction_full 0.951 _diffrn_reflns_point_group_measured_fraction_max 0.943 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 72.340 _diffrn_reflns_theta_min 3.874 _exptl_absorpt_coefficient_mu 0.918 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_correction_T_min 0.5946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.418 _exptl_crystal_description plate _exptl_crystal_F_000 1280 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Isopropanol' _exptl_crystal_size_max 0.110 _exptl_crystal_size_mid 0.040 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.181 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 1966 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.12(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 432 _refine_ls_number_reflns 5340 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0387 _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^)+(0.0480P)^2^+0.1276P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0887 _refine_ls_wR_factor_ref 0.0925 _reflns_Friedel_coverage 0.870 _reflns_friedel_fraction_full 0.903 _reflns_friedel_fraction_max 0.889 _reflns_number_gt 4737 _reflns_number_total 5340 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5ce00568j2.cif _cod_data_source_block shelx _cod_database_code 7220499 _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 0.906 _shelx_estimated_absorpt_t_max 0.982 _shelxl_version_number 2014-1 _shelx_res_file ; TITL VAN_IPA in Pna2(1) CELL 1.54178 16.3977 3.8099 45.645 90 90 90 ZERR 16 0.0007 0.0001 0.002 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SYMM 0.5-X,0.5+Y,0.5+Z SFAC C H O UNIT 128 128 48 EQIV $1 0.5+X,1.5-Y,+Z EQIV $2 0.5-X,0.5+Y,0.5+Z EQIV $3 -0.5+X,0.5-Y,+Z EQIV $4 +X,-1+Y,+Z L.S. 10 PLAN 20 SIZE 0.11 0.04 0.02 TEMP -173.15 HTAB O6 O3_$1 HTAB O8 O9_$2 HTAB O9 O7_$3 HTAB O10 O6_$4 BOND BOND $H LIST 4 MORE -1 CONF fmap 2 acta REM D:/structures/external/Padmini/PK_VAN_IPA/work/refine/VAN_IPA.hkl WGHT 0.048000 0.127600 FVAR 0.13573 O1 3 0.181315 0.231931 0.383664 11.00000 0.01811 0.03120 = 0.01702 -0.00458 0.00293 0.00131 O2 3 0.596844 0.281421 0.577096 11.00000 0.02246 0.03154 = 0.01549 -0.00119 0.00108 0.00350 O3 3 0.224013 0.722961 0.468679 11.00000 0.01906 0.03453 = 0.02028 -0.00229 -0.00024 -0.00198 O4 3 0.349947 0.664633 0.760117 11.00000 0.01707 0.03757 = 0.01907 0.00543 0.00083 0.00280 O5 3 0.539019 0.770719 0.449199 11.00000 0.02082 0.03137 = 0.01584 -0.00491 0.00126 0.00128 O6 3 0.595751 1.048714 0.498556 11.00000 0.01583 0.03400 = 0.01967 -0.00387 -0.00287 -0.00023 O7 3 0.496094 0.313423 0.363820 11.00000 0.01924 0.03481 = 0.02093 -0.00110 -0.00006 -0.00294 O8 3 0.480022 0.390547 0.786359 11.00000 0.02428 0.03824 = 0.01400 0.00549 0.00043 0.00324 O9 3 0.125840 -0.057573 0.334473 11.00000 0.01869 0.03255 = 0.02284 -0.00294 0.00058 -0.00103 H9 2 0.088236 0.052847 0.351339 11.00000 -1.50000 O10 3 0.708260 -0.041512 0.543897 11.00000 0.02264 0.03653 = 0.01545 -0.00206 -0.00060 0.00182 O11 3 0.462265 0.978789 0.655109 11.00000 0.03736 0.03624 = 0.01946 0.00515 -0.00067 -0.00181 O12 3 0.738897 0.309496 0.680404 11.00000 0.03607 0.04841 = 0.02015 -0.00783 -0.00088 0.00488 C1 1 0.346683 0.958672 0.488464 11.00000 0.02096 0.01658 = 0.01602 0.00172 0.00235 -0.00050 C2 1 0.797878 -0.103760 0.583826 11.00000 0.02150 0.02410 = 0.01889 -0.00214 0.00200 -0.00153 AFIX 43 H2 2 0.836138 -0.215538 0.571288 11.00000 -1.20000 AFIX 0 C3 1 0.397831 0.839310 0.466172 11.00000 0.02045 0.01939 = 0.01473 0.00079 -0.00332 0.00019 AFIX 43 H3 2 0.375403 0.735999 0.449028 11.00000 -1.20000 AFIX 0 C4 1 0.462905 1.149706 0.516423 11.00000 0.02406 0.02733 = 0.01209 -0.00214 -0.00096 -0.00013 AFIX 43 H4 2 0.485109 1.255623 0.533493 11.00000 -1.20000 AFIX 0 C5 1 0.667096 0.178066 0.591033 11.00000 0.01893 0.02259 = 0.01969 0.00305 -0.00018 -0.00193 C6 1 0.258483 0.904090 0.487289 11.00000 0.02072 0.02272 = 0.01560 0.00333 -0.00129 0.00191 C7 1 0.723784 0.012494 0.572693 11.00000 0.02526 0.02189 = 0.01152 0.00223 0.00052 -0.00413 C8 1 0.513650 1.024749 0.494771 11.00000 0.01849 0.01891 = 0.01973 0.00339 -0.00219 -0.00190 C9 1 0.207557 -0.020350 0.338232 11.00000 0.01848 0.02088 = 0.01734 0.00358 -0.00104 -0.00209 C10 1 0.322148 0.183136 0.366495 11.00000 0.02141 0.01897 = 0.01735 -0.00053 0.00065 -0.00053 AFIX 43 H10 2 0.344011 0.290928 0.383541 11.00000 -1.20000 AFIX 0 C11 1 0.239294 0.137528 0.363722 11.00000 0.02224 0.01900 = 0.01481 0.00126 0.00387 0.00303 C12 1 0.461856 0.139406 0.344875 11.00000 0.02289 0.02380 = 0.01842 0.00161 0.00160 0.00439 C13 1 0.487104 0.507130 0.758460 11.00000 0.02434 0.02312 = 0.01631 0.00060 0.00226 -0.00030 C14 1 0.481079 0.872192 0.469173 11.00000 0.01890 0.01963 = 0.01409 0.00206 0.00160 0.00213 C15 1 0.815940 -0.056702 0.613185 11.00000 0.01909 0.02405 = 0.01957 0.00156 0.00061 -0.00108 AFIX 43 H15 2 0.866597 -0.135647 0.620838 11.00000 -1.20000 AFIX 0 C16 1 0.342977 -0.094994 0.319289 11.00000 0.02419 0.02143 = 0.01584 0.00029 0.00157 0.00139 AFIX 43 H16 2 0.378700 -0.176459 0.304381 11.00000 -1.20000 AFIX 0 C17 1 0.503450 0.739035 0.701155 11.00000 0.02704 0.02100 = 0.01753 -0.00193 0.00076 -0.00267 C18 1 0.420057 0.655385 0.743587 11.00000 0.02299 0.01813 = 0.01913 0.00086 0.00123 -0.00315 C19 1 0.427898 0.773099 0.715382 11.00000 0.02564 0.01865 = 0.01849 0.00082 -0.00319 -0.00081 AFIX 43 H19 2 0.382820 0.876484 0.705561 11.00000 -1.20000 AFIX 0 C20 1 0.259162 -0.140194 0.316427 11.00000 0.02193 0.02454 = 0.01482 -0.00131 -0.00137 0.00053 AFIX 43 H20 2 0.237450 -0.252840 0.299577 11.00000 -1.20000 AFIX 0 C21 1 0.374255 0.069464 0.343988 11.00000 0.01946 0.02036 = 0.01708 0.00129 0.00063 0.00235 C22 1 0.510037 0.625685 0.422206 11.00000 0.02562 0.02474 = 0.01492 -0.00529 0.00169 -0.00101 AFIX 137 H22A 2 0.478116 0.413692 0.426250 11.00000 -1.50000 H22B 2 0.556555 0.565699 0.409691 11.00000 -1.50000 H22C 2 0.475601 0.798374 0.412199 11.00000 -1.50000 AFIX 0 C23 1 0.569839 0.589757 0.715709 11.00000 0.02322 0.02795 = 0.02226 -0.00326 0.00238 -0.00202 AFIX 43 H23 2 0.620726 0.565999 0.705960 11.00000 -1.20000 AFIX 0 C24 1 0.379301 1.119785 0.513122 11.00000 0.02423 0.01930 = 0.01574 -0.00083 0.00369 0.00221 AFIX 43 H24 2 0.344001 1.209976 0.527808 11.00000 -1.20000 AFIX 0 C25 1 0.759528 0.106893 0.631461 11.00000 0.02485 0.02375 = 0.01909 0.00115 0.00036 -0.00265 C26 1 0.684434 0.225419 0.620365 11.00000 0.02558 0.02008 = 0.01668 -0.00003 0.00269 -0.00054 AFIX 43 H26 2 0.646092 0.336737 0.632899 11.00000 -1.20000 AFIX 0 C27 1 0.514932 0.855505 0.671012 11.00000 0.03341 0.02552 = 0.02114 0.00024 0.00325 -0.00443 C28 1 0.209992 0.381353 0.410624 11.00000 0.02557 0.02617 = 0.01772 -0.00163 0.00441 -0.00094 AFIX 137 H28A 2 0.163322 0.440427 0.423096 11.00000 -1.50000 H28B 2 0.241385 0.594400 0.406434 11.00000 -1.50000 H28C 2 0.244853 0.211267 0.420752 11.00000 -1.50000 AFIX 0 C29 1 0.535304 0.442736 0.594892 11.00000 0.02039 0.03174 = 0.02132 -0.00101 0.00297 0.00432 AFIX 137 H29A 2 0.516335 0.274847 0.609662 11.00000 -1.50000 H29B 2 0.489357 0.514009 0.582518 11.00000 -1.50000 H29C 2 0.558157 0.649609 0.604659 11.00000 -1.50000 AFIX 0 C30 1 0.781214 0.158698 0.662199 11.00000 0.02776 0.03086 = 0.02029 -0.00116 -0.00413 -0.00032 C31 1 0.561415 0.476673 0.744305 11.00000 0.01959 0.02563 = 0.02134 -0.00109 -0.00143 0.00043 AFIX 43 H31 2 0.606760 0.377710 0.754284 11.00000 -1.20000 AFIX 0 C32 1 0.277392 0.784049 0.745536 11.00000 0.01954 0.03191 = 0.02505 0.00338 -0.00254 0.00670 AFIX 137 H32A 2 0.230872 0.766069 0.758931 11.00000 -1.50000 H32B 2 0.267367 0.638402 0.728210 11.00000 -1.50000 H32C 2 0.284461 1.029105 0.739525 11.00000 -1.50000 AFIX 0 H12 2 0.495276 0.041593 0.327905 11.00000 0.01879 H6A 2 0.225368 1.018757 0.503613 11.00000 0.02597 H30 2 0.834305 0.065376 0.668668 11.00000 0.02408 H27 2 0.572177 0.817809 0.663876 11.00000 0.02599 H6 2 0.624913 0.902231 0.482867 11.00000 0.04665 H8 2 0.430032 0.451773 0.796486 11.00000 0.07781 H10A 2 0.662790 0.037119 0.537665 11.00000 0.04028 HKLF 4 REM VAN_IPA in Pna2(1) REM R1 = 0.0387 for 4737 Fo > 4sig(Fo) and 0.0465 for all 5340 data REM 432 parameters refined using 1 restraints END WGHT 0.0480 0.1276 REM Highest difference peak 0.181, deepest hole -0.231, 1-sigma level 0.045 Q1 1 0.3923 0.3246 0.4042 11.00000 0.05 0.18 Q2 1 0.5089 0.5482 0.6576 11.00000 0.05 0.18 Q3 1 0.5028 0.2004 0.5710 11.00000 0.05 0.18 Q4 1 0.1191 0.2095 0.3302 11.00000 0.05 0.17 Q5 1 0.1205 -0.2770 0.3350 11.00000 0.05 0.16 Q6 1 0.5249 0.6520 0.6346 11.00000 0.05 0.16 Q7 1 0.5072 1.2006 0.6573 11.00000 0.05 0.15 Q8 1 0.5758 0.5275 0.4992 11.00000 0.05 0.15 Q9 1 0.3716 -0.0964 0.3374 11.00000 0.05 0.15 Q10 1 0.4422 0.7218 0.8157 11.00000 0.05 0.15 Q11 1 0.7057 0.3596 0.5459 11.00000 0.05 0.15 Q12 1 0.3418 -0.3835 0.3379 11.00000 0.05 0.15 Q13 1 0.2912 0.5656 0.4435 11.00000 0.05 0.14 Q14 1 0.3033 0.6044 0.4056 11.00000 0.05 0.14 Q15 1 0.7416 0.2214 0.6188 11.00000 0.05 0.14 Q16 1 0.2521 1.2447 0.5103 11.00000 0.05 0.14 Q17 1 0.3215 0.9375 0.4885 11.00000 0.05 0.14 Q18 1 0.6899 0.3955 0.5491 11.00000 0.05 0.14 Q19 1 0.6821 0.0058 0.5796 11.00000 0.05 0.14 Q20 1 0.4921 0.3843 0.8229 11.00000 0.05 0.14 ; _shelx_res_checksum 84255 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, 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 O1 O 0.18131(14) 0.2319(6) 0.38366(5) 0.0221(5) Uani 1 1 d . . O2 O 0.59684(14) 0.2814(6) 0.57710(5) 0.0232(5) Uani 1 1 d . . O3 O 0.22401(13) 0.7230(7) 0.46868(5) 0.0246(5) Uani 1 1 d . . O4 O 0.34995(14) 0.6646(6) 0.76012(5) 0.0246(5) Uani 1 1 d . . O5 O 0.53902(14) 0.7707(6) 0.44920(5) 0.0227(5) Uani 1 1 d . . O6 O 0.59575(14) 1.0487(7) 0.49856(5) 0.0232(5) Uani 1 1 d . . O7 O 0.49609(14) 0.3134(7) 0.36382(5) 0.0250(5) Uani 1 1 d . . O8 O 0.48002(15) 0.3905(7) 0.78636(5) 0.0255(5) Uani 1 1 d . . O9 O 0.12584(14) -0.0576(6) 0.33447(5) 0.0247(5) Uani 1 1 d . . H9 H 0.088(3) 0.053(11) 0.3513(9) 0.037 Uiso 1 1 d . U O10 O 0.70826(16) -0.0415(7) 0.54390(5) 0.0249(5) Uani 1 1 d . . O11 O 0.46226(17) 0.9788(7) 0.65511(6) 0.0310(6) Uani 1 1 d . . O12 O 0.73890(17) 0.3095(7) 0.68040(5) 0.0349(7) Uani 1 1 d . . C1 C 0.3467(2) 0.9587(8) 0.48846(7) 0.0179(7) Uani 1 1 d . . C2 C 0.7979(2) -0.1038(9) 0.58383(7) 0.0215(7) Uani 1 1 d . . H2 H 0.8361 -0.2155 0.5713 0.026 Uiso 1 1 calc R U C3 C 0.3978(2) 0.8393(8) 0.46617(8) 0.0182(6) Uani 1 1 d . . H3 H 0.3754 0.7360 0.4490 0.022 Uiso 1 1 calc R U C4 C 0.4629(2) 1.1497(9) 0.51642(7) 0.0212(7) Uani 1 1 d . . H4 H 0.4851 1.2556 0.5335 0.025 Uiso 1 1 calc R U C5 C 0.6671(2) 0.1781(9) 0.59103(7) 0.0204(7) Uani 1 1 d . . C6 C 0.2585(2) 0.9041(9) 0.48729(7) 0.0197(7) Uani 1 1 d . . C7 C 0.7238(2) 0.0125(8) 0.57269(7) 0.0196(7) Uani 1 1 d . . C8 C 0.51365(19) 1.0247(9) 0.49477(8) 0.0190(7) Uani 1 1 d . . C9 C 0.2076(2) -0.0203(8) 0.33823(7) 0.0189(7) Uani 1 1 d . . C10 C 0.3221(2) 0.1831(9) 0.36650(8) 0.0192(7) Uani 1 1 d . . H10 H 0.3440 0.2909 0.3835 0.023 Uiso 1 1 calc R U C11 C 0.2393(2) 0.1375(8) 0.36372(7) 0.0187(7) Uani 1 1 d . . C12 C 0.4619(2) 0.1394(9) 0.34487(8) 0.0217(7) Uani 1 1 d . . C13 C 0.4871(2) 0.5071(9) 0.75846(8) 0.0213(7) Uani 1 1 d . . C14 C 0.4811(2) 0.8722(8) 0.46917(7) 0.0175(6) Uani 1 1 d . . C15 C 0.8159(2) -0.0567(9) 0.61319(7) 0.0209(7) Uani 1 1 d . . H15 H 0.8666 -0.1356 0.6208 0.025 Uiso 1 1 calc R U C16 C 0.3430(2) -0.0950(8) 0.31929(7) 0.0205(7) Uani 1 1 d . . H16 H 0.3787 -0.1765 0.3044 0.025 Uiso 1 1 calc R U C17 C 0.5034(2) 0.7390(9) 0.70115(7) 0.0219(7) Uani 1 1 d . . C18 C 0.4201(2) 0.6554(8) 0.74359(7) 0.0201(7) Uani 1 1 d . . C19 C 0.4279(2) 0.7731(8) 0.71538(8) 0.0209(7) Uani 1 1 d . . H19 H 0.3828 0.8765 0.7056 0.025 Uiso 1 1 calc R U C20 C 0.2592(2) -0.1402(9) 0.31643(7) 0.0204(7) Uani 1 1 d . . H20 H 0.2374 -0.2528 0.2996 0.025 Uiso 1 1 calc R U C21 C 0.3743(2) 0.0695(9) 0.34399(7) 0.0190(7) Uani 1 1 d . . C22 C 0.5100(2) 0.6257(9) 0.42221(7) 0.0218(7) Uani 1 1 d . . H22A H 0.4781 0.4137 0.4263 0.033 Uiso 1 1 calc R U H22B H 0.5566 0.5657 0.4097 0.033 Uiso 1 1 calc R U H22C H 0.4756 0.7984 0.4122 0.033 Uiso 1 1 calc R U C23 C 0.5698(2) 0.5898(9) 0.71571(8) 0.0245(7) Uani 1 1 d . . H23 H 0.6207 0.5660 0.7060 0.029 Uiso 1 1 calc R U C24 C 0.3793(2) 1.1198(8) 0.51312(7) 0.0198(7) Uani 1 1 d . . H24 H 0.3440 1.2100 0.5278 0.024 Uiso 1 1 calc R U C25 C 0.7595(2) 0.1069(9) 0.63146(7) 0.0226(7) Uani 1 1 d . . C26 C 0.6844(2) 0.2254(9) 0.62036(7) 0.0208(7) Uani 1 1 d . . H26 H 0.6461 0.3367 0.6329 0.025 Uiso 1 1 calc R U C27 C 0.5149(2) 0.8555(10) 0.67101(8) 0.0267(8) Uani 1 1 d . . C28 C 0.2100(2) 0.3814(9) 0.41062(8) 0.0231(7) Uani 1 1 d . . H28A H 0.1633 0.4404 0.4231 0.035 Uiso 1 1 calc R U H28B H 0.2414 0.5944 0.4064 0.035 Uiso 1 1 calc R U H28C H 0.2449 0.2113 0.4208 0.035 Uiso 1 1 calc R U C29 C 0.5353(2) 0.4427(10) 0.59489(8) 0.0245(7) Uani 1 1 d . . H29A H 0.5163 0.2748 0.6097 0.037 Uiso 1 1 calc R U H29B H 0.4894 0.5140 0.5825 0.037 Uiso 1 1 calc R U H29C H 0.5582 0.6496 0.6047 0.037 Uiso 1 1 calc R U C30 C 0.7812(2) 0.1587(10) 0.66220(8) 0.0263(8) Uani 1 1 d . . C31 C 0.5614(2) 0.4767(9) 0.74430(8) 0.0222(7) Uani 1 1 d . . H31 H 0.6068 0.3777 0.7543 0.027 Uiso 1 1 calc R U C32 C 0.2774(2) 0.7840(10) 0.74554(8) 0.0255(8) Uani 1 1 d . . H32A H 0.2309 0.7661 0.7589 0.038 Uiso 1 1 calc R U H32B H 0.2674 0.6384 0.7282 0.038 Uiso 1 1 calc R U H32C H 0.2845 1.0291 0.7395 0.038 Uiso 1 1 calc R U H12 H 0.495(2) 0.042(9) 0.3279(8) 0.019(9) Uiso 1 1 d . . H6A H 0.225(2) 1.019(10) 0.5036(9) 0.026(10) Uiso 1 1 d . . H30 H 0.834(2) 0.065(10) 0.6687(8) 0.024(10) Uiso 1 1 d . . H27 H 0.572(2) 0.818(10) 0.6639(9) 0.026(10) Uiso 1 1 d . . H6 H 0.625(3) 0.902(12) 0.4829(10) 0.047(13) Uiso 1 1 d . . H8 H 0.430(4) 0.452(16) 0.7965(13) 0.078(19) Uiso 1 1 d . . H10A H 0.663(3) 0.037(12) 0.5377(11) 0.040(13) Uiso 1 1 d . . 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 0.0181(12) 0.0312(13) 0.0170(12) -0.0046(10) 0.0029(9) 0.0013(10) O2 0.0225(12) 0.0315(13) 0.0155(12) -0.0012(10) 0.0011(9) 0.0035(10) O3 0.0191(12) 0.0345(13) 0.0203(13) -0.0023(11) -0.0002(10) -0.0020(10) O4 0.0171(12) 0.0376(14) 0.0191(13) 0.0054(10) 0.0008(9) 0.0028(10) O5 0.0208(12) 0.0314(13) 0.0158(12) -0.0049(10) 0.0013(10) 0.0013(10) O6 0.0158(11) 0.0340(14) 0.0197(13) -0.0039(11) -0.0029(10) -0.0002(10) O7 0.0192(12) 0.0348(14) 0.0209(13) -0.0011(11) -0.0001(10) -0.0029(10) O8 0.0243(13) 0.0382(15) 0.0140(12) 0.0055(11) 0.0004(10) 0.0032(10) O9 0.0187(12) 0.0326(14) 0.0228(14) -0.0029(10) 0.0006(10) -0.0010(10) O10 0.0226(12) 0.0365(14) 0.0154(12) -0.0021(10) -0.0006(10) 0.0018(11) O11 0.0374(15) 0.0362(15) 0.0195(13) 0.0051(11) -0.0007(11) -0.0018(11) O12 0.0361(15) 0.0484(17) 0.0201(14) -0.0078(12) -0.0009(11) 0.0049(12) C1 0.0210(16) 0.0166(16) 0.0160(17) 0.0017(13) 0.0023(13) -0.0005(12) C2 0.0215(16) 0.0241(17) 0.0189(17) -0.0021(14) 0.0020(13) -0.0015(13) C3 0.0204(16) 0.0194(16) 0.0147(16) 0.0008(13) -0.0033(12) 0.0002(12) C4 0.0241(17) 0.0273(18) 0.0121(16) -0.0021(13) -0.0010(13) -0.0001(14) C5 0.0189(16) 0.0226(17) 0.0197(18) 0.0030(13) -0.0002(13) -0.0019(12) C6 0.0207(17) 0.0227(17) 0.0156(17) 0.0033(14) -0.0013(14) 0.0019(13) C7 0.0253(17) 0.0219(17) 0.0115(17) 0.0022(13) 0.0005(13) -0.0041(13) C8 0.0185(16) 0.0189(17) 0.0197(18) 0.0034(13) -0.0022(13) -0.0019(13) C9 0.0185(15) 0.0209(17) 0.0173(17) 0.0036(13) -0.0010(13) -0.0021(12) C10 0.0214(16) 0.0190(16) 0.0174(17) -0.0005(12) 0.0006(13) -0.0005(13) C11 0.0222(16) 0.0190(16) 0.0148(17) 0.0013(12) 0.0039(13) 0.0030(13) C12 0.0229(17) 0.0238(17) 0.0184(18) 0.0016(13) 0.0016(14) 0.0044(14) C13 0.0243(17) 0.0231(18) 0.0163(18) 0.0006(13) 0.0023(13) -0.0003(13) C14 0.0189(16) 0.0196(16) 0.0141(16) 0.0021(13) 0.0016(13) 0.0021(12) C15 0.0191(16) 0.0240(17) 0.0196(18) 0.0016(14) 0.0006(13) -0.0011(13) C16 0.0242(17) 0.0214(16) 0.0158(17) 0.0003(13) 0.0016(13) 0.0014(13) C17 0.0270(18) 0.0210(16) 0.0175(18) -0.0019(13) 0.0008(14) -0.0027(13) C18 0.0230(17) 0.0181(16) 0.0191(17) 0.0009(13) 0.0012(13) -0.0032(12) C19 0.0256(17) 0.0186(16) 0.0185(17) 0.0008(13) -0.0032(13) -0.0008(12) C20 0.0219(17) 0.0245(17) 0.0148(17) -0.0013(13) -0.0014(13) 0.0005(13) C21 0.0195(16) 0.0204(16) 0.0171(17) 0.0013(13) 0.0006(13) 0.0024(12) C22 0.0256(17) 0.0247(17) 0.0149(17) -0.0053(14) 0.0017(13) -0.0010(13) C23 0.0232(17) 0.0279(18) 0.0223(19) -0.0033(14) 0.0024(14) -0.0020(13) C24 0.0242(17) 0.0193(16) 0.0157(17) -0.0008(13) 0.0037(13) 0.0022(13) C25 0.0249(17) 0.0237(17) 0.0191(18) 0.0011(14) 0.0004(14) -0.0027(14) C26 0.0256(17) 0.0201(17) 0.0167(17) 0.0000(13) 0.0027(13) -0.0005(13) C27 0.0334(19) 0.0255(19) 0.0211(19) 0.0002(15) 0.0033(15) -0.0044(15) C28 0.0256(17) 0.0262(17) 0.0177(17) -0.0016(14) 0.0044(14) -0.0009(14) C29 0.0204(16) 0.032(2) 0.0213(18) -0.0010(15) 0.0030(14) 0.0043(14) C30 0.0278(19) 0.031(2) 0.0203(19) -0.0012(15) -0.0041(15) -0.0003(15) C31 0.0196(16) 0.0256(18) 0.0213(18) -0.0011(14) -0.0014(14) 0.0004(13) C32 0.0195(17) 0.032(2) 0.0251(19) 0.0034(15) -0.0025(14) 0.0067(14) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C11 O1 C28 116.6(3) C5 O2 C29 116.8(3) C18 O4 C32 116.5(3) C14 O5 C22 116.8(3) C8 O6 H6 110(3) C13 O8 H8 116(3) C9 O9 H9 116(2) C7 O10 H10A 116(3) C24 C1 C3 120.2(3) C24 C1 C6 118.3(3) C3 C1 C6 121.4(3) C15 C2 C7 120.0(3) C15 C2 H2 120.0 C7 C2 H2 120.0 C14 C3 C1 119.6(3) C14 C3 H3 120.2 C1 C3 H3 120.2 C8 C4 C24 119.5(3) C8 C4 H4 120.3 C24 C4 H4 120.3 O2 C5 C26 125.8(3) O2 C5 C7 114.1(3) C26 C5 C7 120.1(3) O3 C6 C1 124.0(3) O3 C6 H6A 120(2) C1 C6 H6A 116(2) O10 C7 C2 118.1(3) O10 C7 C5 121.6(3) C2 C7 C5 120.3(3) O6 C8 C4 118.9(3) O6 C8 C14 120.5(3) C4 C8 C14 120.6(3) O9 C9 C20 118.5(3) O9 C9 C11 120.9(3) C20 C9 C11 120.6(3) C11 C10 C21 119.6(3) C11 C10 H10 120.2 C21 C10 H10 120.2 O1 C11 C10 126.4(3) O1 C11 C9 114.0(3) C10 C11 C9 119.6(3) O7 C12 C21 124.6(3) O7 C12 H12 119(2) C21 C12 H12 116(2) O8 C13 C31 119.2(3) O8 C13 C18 121.2(3) C31 C13 C18 119.7(3) O5 C14 C3 126.5(3) O5 C14 C8 113.9(3) C3 C14 C8 119.7(3) C2 C15 C25 119.7(3) C2 C15 H15 120.1 C25 C15 H15 120.1 C21 C16 C20 119.8(3) C21 C16 H16 120.1 C20 C16 H16 120.1 C23 C17 C19 120.3(3) C23 C17 C27 118.2(3) C19 C17 C27 121.5(3) C19 C18 O4 125.9(3) C19 C18 C13 120.7(3) O4 C18 C13 113.4(3) C18 C19 C17 119.2(3) C18 C19 H19 120.4 C17 C19 H19 120.4 C9 C20 C16 119.7(3) C9 C20 H20 120.1 C16 C20 H20 120.1 C16 C21 C10 120.6(3) C16 C21 C12 117.9(3) C10 C21 C12 121.4(3) O5 C22 H22A 109.5 O5 C22 H22B 109.5 H22A C22 H22B 109.5 O5 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 C31 C23 C17 119.9(3) C31 C23 H23 120.0 C17 C23 H23 120.0 C4 C24 C1 120.4(3) C4 C24 H24 119.8 C1 C24 H24 119.8 C15 C25 C26 120.6(3) C15 C25 C30 118.3(3) C26 C25 C30 121.1(3) C5 C26 C25 119.2(3) C5 C26 H26 120.4 C25 C26 H26 120.4 O11 C27 C17 125.9(4) O11 C27 H27 122(2) C17 C27 H27 113(2) O1 C28 H28A 109.5 O1 C28 H28B 109.5 H28A C28 H28B 109.5 O1 C28 H28C 109.5 H28A C28 H28C 109.5 H28B C28 H28C 109.5 O2 C29 H29A 109.5 O2 C29 H29B 109.5 H29A C29 H29B 109.5 O2 C29 H29C 109.5 H29A C29 H29C 109.5 H29B C29 H29C 109.5 O12 C30 C25 125.2(3) O12 C30 H30 118(2) C25 C30 H30 117(2) C23 C31 C13 120.2(3) C23 C31 H31 119.9 C13 C31 H31 119.9 O4 C32 H32A 109.5 O4 C32 H32B 109.5 H32A C32 H32B 109.5 O4 C32 H32C 109.5 H32A C32 H32C 109.5 H32B C32 H32C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C11 1.364(4) O1 C28 1.435(4) O2 C5 1.374(4) O2 C29 1.434(4) O3 C6 1.232(4) O4 C18 1.376(4) O4 C32 1.437(4) O5 C14 1.372(4) O5 C22 1.431(4) O6 C8 1.360(4) O6 H6 1.03(5) O7 C12 1.226(4) O8 C13 1.354(4) O8 H8 0.97(6) O9 C9 1.358(4) O9 H9 1.07(4) O10 C7 1.355(4) O10 H10A 0.85(5) O11 C27 1.222(5) O12 C30 1.226(4) C1 C24 1.389(5) C1 C3 1.395(4) C1 C6 1.462(4) C2 C15 1.384(5) C2 C7 1.389(5) C2 H2 0.9500 C3 C14 1.378(4) C3 H3 0.9500 C4 C8 1.377(5) C4 C24 1.384(5) C4 H4 0.9500 C5 C26 1.381(5) C5 C7 1.401(5) C6 H6A 1.02(4) C8 C14 1.410(5) C9 C20 1.384(5) C9 C11 1.409(5) C10 C11 1.376(4) C10 C21 1.405(4) C10 H10 0.9500 C12 C21 1.462(4) C12 H12 1.02(4) C13 C31 1.384(5) C13 C18 1.410(5) C15 C25 1.393(5) C15 H15 0.9500 C16 C21 1.388(5) C16 C20 1.391(5) C16 H16 0.9500 C17 C23 1.396(5) C17 C19 1.405(5) C17 C27 1.458(5) C18 C19 1.369(5) C19 H19 0.9500 C20 H20 0.9500 C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 C23 C31 1.381(5) C23 H23 0.9500 C24 H24 0.9500 C25 C26 1.406(5) C25 C30 1.461(5) C26 H26 0.9500 C27 H27 1.00(4) C28 H28A 0.9800 C28 H28B 0.9800 C28 H28C 0.9800 C29 H29A 0.9800 C29 H29B 0.9800 C29 H29C 0.9800 C30 H30 0.99(4) C31 H31 0.9500 C32 H32A 0.9800 C32 H32B 0.9800 C32 H32C 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 O6 H6 O3 1.03(5) 1.81(5) 2.712(3) 144(4) 3_565 O8 H8 O9 0.97(6) 1.96(6) 2.806(3) 144(5) 4 O9 H9 O7 1.07(4) 1.69(4) 2.681(3) 151(3) 3_455 O10 H10A O6 0.85(5) 2.10(5) 2.794(3) 139(4) 1_545 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 C24 C1 C3 C14 2.0(5) C6 C1 C3 C14 -175.1(3) C29 O2 C5 C26 -2.1(5) C29 O2 C5 C7 178.1(3) C24 C1 C6 O3 -169.6(3) C3 C1 C6 O3 7.6(5) C15 C2 C7 O10 -179.4(3) C15 C2 C7 C5 0.1(5) O2 C5 C7 O10 -0.9(5) C26 C5 C7 O10 179.2(3) O2 C5 C7 C2 179.6(3) C26 C5 C7 C2 -0.3(5) C24 C4 C8 O6 -178.6(3) C24 C4 C8 C14 1.0(5) C28 O1 C11 C10 -2.5(5) C28 O1 C11 C9 177.6(3) C21 C10 C11 O1 179.6(3) C21 C10 C11 C9 -0.5(5) O9 C9 C11 O1 2.2(4) C20 C9 C11 O1 -177.9(3) O9 C9 C11 C10 -177.7(3) C20 C9 C11 C10 2.1(5) C22 O5 C14 C3 2.0(5) C22 O5 C14 C8 -177.7(3) C1 C3 C14 O5 -179.4(3) C1 C3 C14 C8 0.2(5) O6 C8 C14 O5 -2.5(4) C4 C8 C14 O5 177.9(3) O6 C8 C14 C3 177.8(3) C4 C8 C14 C3 -1.8(5) C7 C2 C15 C25 0.1(5) C32 O4 C18 C19 5.1(5) C32 O4 C18 C13 -174.8(3) O8 C13 C18 C19 179.9(3) C31 C13 C18 C19 -0.7(5) O8 C13 C18 O4 -0.3(5) C31 C13 C18 O4 179.1(3) O4 C18 C19 C17 -178.7(3) C13 C18 C19 C17 1.1(5) C23 C17 C19 C18 -0.6(5) C27 C17 C19 C18 179.2(3) O9 C9 C20 C16 177.9(3) C11 C9 C20 C16 -1.9(5) C21 C16 C20 C9 0.1(5) C20 C16 C21 C10 1.6(5) C20 C16 C21 C12 -174.6(3) C11 C10 C21 C16 -1.4(5) C11 C10 C21 C12 174.7(3) O7 C12 C21 C16 172.2(3) O7 C12 C21 C10 -4.0(5) C19 C17 C23 C31 -0.4(5) C27 C17 C23 C31 179.9(3) C8 C4 C24 C1 1.3(5) C3 C1 C24 C4 -2.8(5) C6 C1 C24 C4 174.3(3) C2 C15 C25 C26 -0.1(5) C2 C15 C25 C30 -178.8(3) O2 C5 C26 C25 -179.6(3) C7 C5 C26 C25 0.2(5) C15 C25 C26 C5 0.0(5) C30 C25 C26 C5 178.6(3) C23 C17 C27 O11 177.2(4) C19 C17 C27 O11 -2.5(6) C15 C25 C30 O12 177.2(4) C26 C25 C30 O12 -1.5(6) C17 C23 C31 C13 0.8(5) O8 C13 C31 C23 179.2(3) C18 C13 C31 C23 -0.2(5)