#------------------------------------------------------------------------------ #$Date: 2016-01-05 06:35:08 +0200 (Tue, 05 Jan 2016) $ #$Revision: 173490 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/37/7223723.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_7223723 loop_ _publ_author_name 'Saritemur, Gizem' 'Nomen Miralles, Laura' 'Husson, Debby' 'Pitak, Mateusz' 'Coles, Simon' 'WALLIS, JOHN D' _publ_section_title ; Two Modes of Peri-Interaction Between an Aldehyde Group and a Carboxylate Anion in Naphthalaldehydate Salts. ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C5CE02282G _journal_year 2016 _chemical_formula_sum 'C31 H26 N2 O6' _chemical_formula_weight 522.54 _chemical_melting_point 416.5(5) _chemical_name_systematic '4-dimethylaminopyridium naphthalaldehydate.naphthalaldehydic acidDMAP.14.15' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2013 _audit_update_record ; 2015-11-05 deposited with the CCDC. 2016-01-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 105.966(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.3271(4) _cell_length_b 8.3575(3) _cell_length_c 20.6960(6) _cell_measurement_reflns_used 4839 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 28.8000 _cell_measurement_theta_min 3.5960 _cell_volume 2548.81(14) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 150(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9832 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.848 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _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 0.0347 _diffrn_reflns_av_unetI/netI 0.0461 _diffrn_reflns_laue_measured_fraction_full 0.971 _diffrn_reflns_laue_measured_fraction_max 0.848 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 14522 _diffrn_reflns_point_group_measured_fraction_full 0.971 _diffrn_reflns_point_group_measured_fraction_max 0.848 _diffrn_reflns_theta_full 27.500 _diffrn_reflns_theta_max 29.524 _diffrn_reflns_theta_min 2.953 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.367 _exptl_crystal_description block _exptl_crystal_F_000 1104 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: acetonitrile' _exptl_crystal_size_max 0.3790 _exptl_crystal_size_mid 0.3061 _exptl_crystal_size_min 0.1894 _refine_diff_density_max 0.379 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 366 _refine_ls_number_reflns 6036 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.098 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0626 _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^)+(0.0541P)^2^+1.2137P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1327 _refine_ls_wR_factor_ref 0.1414 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4920 _reflns_number_total 6036 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5ce02282g2.cif _cod_data_source_block DMABSB _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '416-417' was changed to '416.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas ; _cod_database_code 7223723 _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. ; _shelxl_version_number 2013-4 _shelx_res_file ; REM P2(1)/n (#14 in standard setting) REM DMAPNAP2015B in P2(1)/n REM R1 = 0.0627 for 4920 Fo > 4sig(Fo) and 0.0808 for all 6036 data REM 357 parameters refined using 0 restraints REM Highest difference peak 0.382, deepest hole -0.362, 1-sigma level 0.054 TITL DMAPNAP2015B in P2(1)/n CELL 0.71073 15.3271 8.3575 20.6960 90.000 105.966 90.000 ZERR 4.0000 0.0004 0.0003 0.0006 0.000 0.003 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 124 112 8 24 MERG 2 FMAP 2 GRID PLAN 20 TEMP -123 L.S. 6 EQIV $1 -x+1/2, y+1/2, -z+1/2 HTAB O6 O1_$1 HTAB N1 O2 EQIV $2 -x, -y, -z HTAB C41 O2_$2 ACTA 55 WGHT 0.054100 1.213700 FVAR 3.84029 O1 4 0.004259 -0.099339 0.198534 11.00000 0.06567 0.02491 = 0.02115 -0.00030 0.01009 -0.01394 O2 4 0.011815 -0.002148 0.100637 11.00000 0.04536 0.02535 = 0.01686 -0.00449 0.00714 -0.00900 O3 4 -0.215335 0.072390 0.197845 11.00000 0.04829 0.07497 = 0.10418 -0.04058 0.04564 -0.03792 O4 4 0.286497 0.136539 0.096238 11.00000 0.03900 0.03092 = 0.03367 0.00684 0.00946 -0.00916 O5 4 0.336243 0.371926 0.137593 11.00000 0.03402 0.03758 = 0.02088 -0.00337 0.01079 -0.01045 O6 4 0.488235 0.439268 0.171866 11.00000 0.03136 0.03311 = 0.02134 -0.00144 0.00392 -0.00121 H61 2 0.490758 0.427590 0.216201 11.00000 0.05952 N1 3 -0.064146 -0.273754 0.048801 11.00000 0.02817 0.02032 = 0.02306 -0.00506 0.00249 -0.00337 H1 2 -0.038845 -0.180783 0.068518 11.00000 0.03615 N2 3 -0.168408 -0.696027 -0.042297 11.00000 0.03517 0.01951 = 0.02850 -0.00027 -0.00450 -0.00420 C1 1 0.054935 0.168683 0.194457 11.00000 0.02286 0.01948 = 0.01193 0.00213 0.00343 0.00053 C2 1 0.143518 0.205405 0.197616 11.00000 0.02296 0.02747 = 0.01555 0.00023 0.00609 0.00264 AFIX 43 H2 2 0.177565 0.133704 0.178455 11.00000 -1.20000 AFIX 0 C3 1 0.184911 0.346465 0.228509 11.00000 0.01961 0.03530 = 0.01782 0.00043 0.00338 -0.00578 AFIX 43 H3 2 0.246507 0.368480 0.230835 11.00000 -1.20000 AFIX 0 C4 1 0.136323 0.450912 0.254971 11.00000 0.02674 0.02177 = 0.01910 -0.00089 0.00219 -0.00768 AFIX 43 H4 2 0.164303 0.546176 0.275844 11.00000 -1.20000 AFIX 0 C5 1 0.044281 0.419712 0.251876 11.00000 0.02578 0.01797 = 0.01631 0.00296 0.00397 -0.00016 C6 1 -0.004889 0.532221 0.279196 11.00000 0.03735 0.01977 = 0.02900 -0.00496 0.00843 0.00115 AFIX 43 H6 2 0.024209 0.627448 0.299233 11.00000 -1.20000 AFIX 0 C7 1 -0.092879 0.505933 0.277157 11.00000 0.03742 0.03192 = 0.03890 -0.00621 0.01648 0.01020 AFIX 43 H7 2 -0.124951 0.581803 0.296058 11.00000 -1.20000 AFIX 0 C8 1 -0.136251 0.366670 0.247115 11.00000 0.02255 0.04011 = 0.03196 0.00018 0.01165 0.00281 AFIX 43 H8 2 -0.198032 0.349760 0.245727 11.00000 -1.20000 AFIX 0 C9 1 -0.092181 0.253650 0.219565 11.00000 0.02265 0.02500 = 0.01773 0.00207 0.00615 -0.00119 C10 1 0.001568 0.276898 0.221204 11.00000 0.02052 0.01754 = 0.01208 0.00286 0.00308 -0.00016 C11 1 0.020756 0.009338 0.162813 11.00000 0.02294 0.02038 = 0.01835 -0.00222 0.00429 -0.00013 C12 1 -0.148846 0.118083 0.185120 11.00000 0.02483 0.03654 = 0.03440 -0.00410 0.00911 -0.00626 H12 2 -0.138239 0.072504 0.144199 11.00000 0.04411 C21 1 0.333516 0.313858 0.022386 11.00000 0.02378 0.02400 = 0.02041 -0.00139 0.00615 -0.00208 C22 1 0.306313 0.215868 -0.032596 11.00000 0.03387 0.02949 = 0.03245 -0.00693 0.01231 -0.00886 AFIX 43 H22 2 0.283354 0.112176 -0.027975 11.00000 -1.20000 AFIX 0 C23 1 0.312255 0.268232 -0.095850 11.00000 0.04202 0.05147 = 0.02545 -0.01366 0.01211 -0.01349 AFIX 43 H23 2 0.294125 0.199260 -0.133670 11.00000 -1.20000 AFIX 0 C24 1 0.344077 0.418224 -0.103027 11.00000 0.03730 0.05345 = 0.02005 0.00138 0.00978 -0.00612 AFIX 43 H24 2 0.346920 0.452860 -0.146120 11.00000 -1.20000 AFIX 0 C25 1 0.372838 0.522731 -0.047417 11.00000 0.02817 0.03602 = 0.02378 0.00471 0.00780 -0.00356 C26 1 0.406435 0.678456 -0.052076 11.00000 0.03942 0.04052 = 0.03406 0.01269 0.01149 -0.00529 AFIX 43 H26 2 0.410017 0.717605 -0.094365 11.00000 -1.20000 AFIX 0 C27 1 0.433682 0.772839 0.003287 11.00000 0.04562 0.02710 = 0.05226 0.00934 0.01455 -0.00972 AFIX 43 H27 2 0.455290 0.877799 -0.000905 11.00000 -1.20000 AFIX 0 C28 1 0.430328 0.717109 0.066941 11.00000 0.03850 0.02625 = 0.03680 -0.00337 0.00735 -0.00655 AFIX 43 H28 2 0.449600 0.784510 0.105188 11.00000 -1.20000 AFIX 0 C29 1 0.399466 0.566668 0.073624 11.00000 0.02579 0.02410 = 0.02480 -0.00264 0.00649 -0.00132 C30 1 0.368519 0.468063 0.016623 11.00000 0.02198 0.02435 = 0.02135 0.00131 0.00598 -0.00017 C31 1 0.318649 0.263459 0.087170 11.00000 0.02203 0.02737 = 0.02492 0.00327 0.00565 -0.00160 C32 1 0.402409 0.498868 0.141297 11.00000 0.02876 0.02622 = 0.02105 -0.00622 0.00535 -0.00317 AFIX 13 H32 2 0.389171 0.586957 0.169912 11.00000 -1.20000 AFIX 0 C41 1 -0.077327 -0.292789 -0.017937 11.00000 0.02640 0.02143 = 0.02027 0.00342 0.00446 -0.00007 AFIX 43 H41 2 -0.062008 -0.207925 -0.043341 11.00000 -1.20000 AFIX 0 C42 1 -0.111880 -0.430029 -0.049552 11.00000 0.02497 0.02382 = 0.01582 0.00054 0.00120 0.00012 AFIX 43 H42 2 -0.120448 -0.440330 -0.096602 11.00000 -1.20000 AFIX 0 C43 1 -0.135265 -0.558043 -0.012902 11.00000 0.02099 0.01961 = 0.02228 0.00108 -0.00299 -0.00029 C44 1 -0.121270 -0.532356 0.057166 11.00000 0.03006 0.02561 = 0.02240 0.00553 0.00289 -0.00451 AFIX 43 H44 2 -0.136496 -0.613793 0.084198 11.00000 -1.20000 AFIX 0 C45 1 -0.086155 -0.391484 0.085451 11.00000 0.03041 0.03292 = 0.01662 0.00059 0.00255 -0.00130 AFIX 43 H45 2 -0.076968 -0.376000 0.132324 11.00000 -1.20000 AFIX 0 C46 1 -0.184661 -0.719942 -0.114668 11.00000 0.04302 0.02899 = 0.03298 -0.01276 -0.00591 0.00127 AFIX 137 H46C 2 -0.219605 -0.629593 -0.138875 11.00000 -1.50000 H46A 2 -0.218829 -0.819259 -0.128099 11.00000 -1.50000 H46B 2 -0.126437 -0.726995 -0.125511 11.00000 -1.50000 AFIX 0 C47 1 -0.186613 -0.829817 -0.002600 11.00000 0.05319 0.02470 = 0.05033 0.00598 -0.00317 -0.01460 AFIX 137 H47A 2 -0.130341 -0.861218 0.030684 11.00000 -1.50000 H47B 2 -0.210021 -0.920546 -0.032310 11.00000 -1.50000 H47C 2 -0.231704 -0.797541 0.020489 11.00000 -1.50000 AFIX 0 HKLF 4 REM DMAPNAP2015B in P2(1)/n REM R1 = 0.0626 for 4920 Fo > 4sig(Fo) and 0.0806 for all 6036 data REM 366 parameters refined using 0 restraints END WGHT 0.0541 1.2147 REM Highest difference peak 0.379, deepest hole -0.362, 1-sigma level 0.054 Q1 1 -0.0400 0.2368 0.2265 11.00000 0.05 0.38 Q2 1 -0.2362 0.1285 0.1534 11.00000 0.05 0.33 Q3 1 0.0205 0.2247 0.2029 11.00000 0.05 0.33 Q4 1 0.0221 0.3455 0.2435 11.00000 0.05 0.30 Q5 1 0.0328 0.0965 0.1798 11.00000 0.05 0.28 Q6 1 0.0143 0.4838 0.2644 11.00000 0.05 0.28 Q7 1 -0.1002 0.3124 0.2399 11.00000 0.05 0.28 Q8 1 -0.0954 -0.4996 -0.0235 11.00000 0.05 0.26 Q9 1 -0.0318 0.0193 0.1170 11.00000 0.05 0.25 Q10 1 0.0785 0.4587 0.2398 11.00000 0.05 0.25 Q11 1 0.1001 0.1850 0.2089 11.00000 0.05 0.25 Q12 1 -0.1435 -0.4824 -0.0331 11.00000 0.05 0.24 Q13 1 -0.1032 0.1688 0.2114 11.00000 0.05 0.24 Q14 1 0.4140 0.5087 0.0514 11.00000 0.05 0.24 Q15 1 0.0646 -0.0922 0.1893 11.00000 0.05 0.24 Q16 1 -0.1226 -0.3638 -0.0303 11.00000 0.05 0.23 Q17 1 0.3772 0.6607 0.0668 11.00000 0.05 0.22 Q18 1 0.3532 0.2701 0.0603 11.00000 0.05 0.22 Q19 1 0.2977 0.3676 -0.1071 11.00000 0.05 0.22 Q20 1 0.3611 0.6231 -0.0486 11.00000 0.05 0.22 ; _shelx_res_checksum 94888 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 0.00426(11) -0.09934(17) 0.19853(7) 0.0376(4) Uani 1 1 d . . O2 O 0.01182(9) -0.00215(16) 0.10064(6) 0.0295(3) Uani 1 1 d . . O3 O -0.21533(12) 0.0724(3) 0.19785(11) 0.0709(6) Uani 1 1 d . . O4 O 0.28650(9) 0.13654(18) 0.09624(7) 0.0346(3) Uani 1 1 d . . O5 O 0.33624(9) 0.37193(17) 0.13759(6) 0.0302(3) Uani 1 1 d . . O6 O 0.48823(9) 0.43927(17) 0.17187(7) 0.0293(3) Uani 1 1 d . . H61 H 0.4908(17) 0.428(3) 0.2162(15) 0.060(8) Uiso 1 1 d . . N1 N -0.06415(10) -0.2738(2) 0.04880(8) 0.0248(3) Uani 1 1 d . . H1 H -0.0388(15) -0.181(3) 0.0685(11) 0.036(6) Uiso 1 1 d . . N2 N -0.16841(11) -0.69603(19) -0.04230(8) 0.0304(4) Uani 1 1 d . . C1 C 0.05493(11) 0.1687(2) 0.19446(8) 0.0184(3) Uani 1 1 d . . C2 C 0.14352(11) 0.2054(2) 0.19762(8) 0.0218(4) Uani 1 1 d . . H2 H 0.1776 0.1337 0.1785 0.026 Uiso 1 1 calc R U C3 C 0.18491(11) 0.3465(2) 0.22851(9) 0.0246(4) Uani 1 1 d . . H3 H 0.2465 0.3685 0.2308 0.030 Uiso 1 1 calc R U C4 C 0.13632(12) 0.4509(2) 0.25497(9) 0.0234(4) Uani 1 1 d . . H4 H 0.1643 0.5462 0.2758 0.028 Uiso 1 1 calc R U C5 C 0.04428(11) 0.4197(2) 0.25188(8) 0.0204(4) Uani 1 1 d . . C6 C -0.00489(13) 0.5322(2) 0.27920(10) 0.0288(4) Uani 1 1 d . . H6 H 0.0242 0.6274 0.2992 0.035 Uiso 1 1 calc R U C7 C -0.09288(14) 0.5059(3) 0.27716(11) 0.0349(5) Uani 1 1 d . . H7 H -0.1250 0.5818 0.2961 0.042 Uiso 1 1 calc R U C8 C -0.13625(12) 0.3667(3) 0.24711(10) 0.0307(4) Uani 1 1 d . . H8 H -0.1980 0.3498 0.2457 0.037 Uiso 1 1 calc R U C9 C -0.09218(11) 0.2536(2) 0.21956(8) 0.0217(4) Uani 1 1 d . . C10 C 0.00157(10) 0.2769(2) 0.22120(8) 0.0170(3) Uani 1 1 d . . C11 C 0.02076(11) 0.0093(2) 0.16281(9) 0.0208(4) Uani 1 1 d . . C12 C -0.14885(12) 0.1181(3) 0.18512(11) 0.0317(5) Uani 1 1 d . . H12 H -0.1382(15) 0.073(3) 0.1442(12) 0.044(7) Uiso 1 1 d . . C21 C 0.33352(11) 0.3139(2) 0.02239(9) 0.0227(4) Uani 1 1 d . . C22 C 0.30631(13) 0.2159(3) -0.03260(10) 0.0313(4) Uani 1 1 d . . H22 H 0.2834 0.1122 -0.0280 0.038 Uiso 1 1 calc R U C23 C 0.31226(15) 0.2682(3) -0.09585(10) 0.0391(5) Uani 1 1 d . . H23 H 0.2941 0.1993 -0.1337 0.047 Uiso 1 1 calc R U C24 C 0.34408(14) 0.4182(3) -0.10303(10) 0.0366(5) Uani 1 1 d . . H24 H 0.3469 0.4529 -0.1461 0.044 Uiso 1 1 calc R U C25 C 0.37284(12) 0.5227(3) -0.04742(10) 0.0292(4) Uani 1 1 d . . C26 C 0.40644(14) 0.6785(3) -0.05208(11) 0.0377(5) Uani 1 1 d . . H26 H 0.4100 0.7176 -0.0944 0.045 Uiso 1 1 calc R U C27 C 0.43368(15) 0.7728(3) 0.00329(12) 0.0414(5) Uani 1 1 d . . H27 H 0.4553 0.8778 -0.0009 0.050 Uiso 1 1 calc R U C28 C 0.43033(14) 0.7171(3) 0.06694(11) 0.0344(5) Uani 1 1 d . . H28 H 0.4496 0.7845 0.1052 0.041 Uiso 1 1 calc R U C29 C 0.39947(12) 0.5667(2) 0.07362(9) 0.0250(4) Uani 1 1 d . . C30 C 0.36852(11) 0.4681(2) 0.01662(9) 0.0226(4) Uani 1 1 d . . C31 C 0.31865(11) 0.2635(2) 0.08717(9) 0.0249(4) Uani 1 1 d . . C32 C 0.40241(12) 0.4989(2) 0.14130(9) 0.0256(4) Uani 1 1 d . . H32 H 0.3892 0.5870 0.1699 0.031 Uiso 1 1 calc R U C41 C -0.07733(11) -0.2928(2) -0.01794(9) 0.0231(4) Uani 1 1 d . . H41 H -0.0620 -0.2079 -0.0433 0.028 Uiso 1 1 calc R U C42 C -0.11188(11) -0.4300(2) -0.04955(9) 0.0224(4) Uani 1 1 d . . H42 H -0.1204 -0.4403 -0.0966 0.027 Uiso 1 1 calc R U C43 C -0.13526(11) -0.5580(2) -0.01290(9) 0.0227(4) Uani 1 1 d . . C44 C -0.12127(12) -0.5324(2) 0.05717(9) 0.0269(4) Uani 1 1 d . . H44 H -0.1365 -0.6138 0.0842 0.032 Uiso 1 1 calc R U C45 C -0.08615(12) -0.3915(2) 0.08545(9) 0.0274(4) Uani 1 1 d . . H45 H -0.0770 -0.3760 0.1323 0.033 Uiso 1 1 calc R U C46 C -0.18466(15) -0.7199(3) -0.11467(11) 0.0382(5) Uani 1 1 d . . H46C H -0.2196 -0.6296 -0.1389 0.057 Uiso 1 1 calc R U H46A H -0.2188 -0.8193 -0.1281 0.057 Uiso 1 1 calc R U H46B H -0.1264 -0.7270 -0.1255 0.057 Uiso 1 1 calc R U C47 C -0.18661(17) -0.8298(3) -0.00260(13) 0.0462(6) Uani 1 1 d . . H47A H -0.1303 -0.8612 0.0307 0.069 Uiso 1 1 calc R U H47B H -0.2100 -0.9205 -0.0323 0.069 Uiso 1 1 calc R U H47C H -0.2317 -0.7975 0.0205 0.069 Uiso 1 1 calc R U loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0657(10) 0.0249(8) 0.0211(7) -0.0003(6) 0.0101(7) -0.0139(7) O2 0.0454(8) 0.0253(7) 0.0169(6) -0.0045(6) 0.0071(6) -0.0090(6) O3 0.0483(10) 0.0750(14) 0.1042(16) -0.0406(12) 0.0456(10) -0.0379(10) O4 0.0390(7) 0.0309(8) 0.0337(8) 0.0068(7) 0.0095(6) -0.0092(6) O5 0.0340(7) 0.0376(8) 0.0209(7) -0.0034(6) 0.0108(5) -0.0105(6) O6 0.0314(7) 0.0331(8) 0.0213(7) -0.0014(6) 0.0039(6) -0.0012(6) N1 0.0282(7) 0.0203(8) 0.0231(8) -0.0051(7) 0.0025(6) -0.0034(7) N2 0.0352(8) 0.0195(8) 0.0285(9) -0.0003(7) -0.0045(7) -0.0042(7) C1 0.0229(8) 0.0195(9) 0.0119(8) 0.0021(7) 0.0034(6) 0.0005(7) C2 0.0230(8) 0.0275(10) 0.0156(8) 0.0002(7) 0.0061(7) 0.0026(7) C3 0.0196(8) 0.0353(11) 0.0178(9) 0.0004(8) 0.0034(7) -0.0058(8) C4 0.0267(8) 0.0218(9) 0.0191(8) -0.0009(7) 0.0022(7) -0.0077(7) C5 0.0258(8) 0.0180(8) 0.0163(8) 0.0030(7) 0.0040(7) -0.0002(7) C6 0.0374(10) 0.0198(9) 0.0290(10) -0.0050(8) 0.0084(8) 0.0012(8) C7 0.0374(10) 0.0319(11) 0.0389(12) -0.0062(10) 0.0165(9) 0.0102(9) C8 0.0226(8) 0.0401(12) 0.0320(10) 0.0002(9) 0.0117(8) 0.0028(8) C9 0.0226(8) 0.0250(9) 0.0177(8) 0.0021(7) 0.0062(7) -0.0012(7) C10 0.0205(7) 0.0175(8) 0.0121(7) 0.0029(7) 0.0031(6) -0.0002(7) C11 0.0229(8) 0.0204(9) 0.0184(8) -0.0022(7) 0.0043(7) -0.0001(7) C12 0.0248(9) 0.0365(12) 0.0344(11) -0.0041(10) 0.0091(8) -0.0063(8) C21 0.0238(8) 0.0240(9) 0.0204(9) -0.0014(8) 0.0061(7) -0.0021(7) C22 0.0339(10) 0.0295(11) 0.0325(11) -0.0069(9) 0.0123(8) -0.0089(9) C23 0.0420(11) 0.0515(15) 0.0255(10) -0.0137(10) 0.0121(9) -0.0135(11) C24 0.0373(10) 0.0535(14) 0.0201(9) 0.0014(10) 0.0098(8) -0.0061(10) C25 0.0282(9) 0.0360(11) 0.0238(9) 0.0047(9) 0.0078(8) -0.0036(8) C26 0.0394(11) 0.0405(13) 0.0341(11) 0.0127(10) 0.0115(9) -0.0053(10) C27 0.0456(12) 0.0271(11) 0.0523(14) 0.0093(11) 0.0145(11) -0.0097(10) C28 0.0385(10) 0.0262(10) 0.0368(11) -0.0034(9) 0.0074(9) -0.0066(9) C29 0.0258(8) 0.0241(9) 0.0248(9) -0.0026(8) 0.0065(7) -0.0013(7) C30 0.0220(8) 0.0244(9) 0.0214(9) 0.0013(8) 0.0060(7) -0.0002(7) C31 0.0220(8) 0.0274(10) 0.0249(9) 0.0033(8) 0.0057(7) -0.0016(8) C32 0.0288(9) 0.0262(10) 0.0211(9) -0.0062(8) 0.0053(7) -0.0032(8) C41 0.0264(8) 0.0214(9) 0.0203(9) 0.0034(8) 0.0045(7) -0.0001(7) C42 0.0250(8) 0.0238(9) 0.0158(8) 0.0005(7) 0.0012(7) 0.0001(7) C43 0.0210(8) 0.0196(9) 0.0223(9) 0.0011(7) -0.0030(7) -0.0003(7) C44 0.0301(9) 0.0256(10) 0.0224(9) 0.0055(8) 0.0029(7) -0.0045(8) C45 0.0304(9) 0.0329(11) 0.0166(9) 0.0006(8) 0.0026(7) -0.0013(8) C46 0.0430(11) 0.0290(11) 0.0330(11) -0.0128(10) -0.0059(9) 0.0013(9) C47 0.0532(13) 0.0247(11) 0.0503(14) 0.0060(11) -0.0032(11) -0.0146(10) 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' N N 0.0061 0.0033 '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 C31 O5 C32 121.17(14) C45 N1 C41 120.16(17) C43 N2 C47 120.81(17) C43 N2 C46 121.33(17) C47 N2 C46 117.82(17) C2 C1 C10 120.19(16) C2 C1 C11 115.89(15) C10 C1 C11 123.91(14) C1 C2 C3 121.63(16) C4 C3 C2 119.59(16) C3 C4 C5 120.86(17) C6 C5 C4 119.45(17) C6 C5 C10 120.30(16) C4 C5 C10 120.25(16) C7 C6 C5 120.93(18) C6 C7 C8 119.73(18) C9 C8 C7 121.95(17) C8 C9 C10 119.91(17) C8 C9 C12 115.76(16) C10 C9 C12 124.18(16) C5 C10 C1 117.46(14) C5 C10 C9 117.17(15) C1 C10 C9 125.36(16) O1 C11 O2 124.78(17) O1 C11 C1 119.33(15) O2 C11 C1 115.90(15) O3 C12 C9 124.4(2) C22 C21 C30 120.70(17) C22 C21 C31 119.61(17) C30 C21 C31 119.47(16) C21 C22 C23 120.26(19) C24 C23 C22 120.2(2) C23 C24 C25 121.19(19) C26 C25 C24 123.43(19) C26 C25 C30 118.13(18) C24 C25 C30 118.44(19) C27 C26 C25 120.70(19) C26 C27 C28 120.9(2) C29 C28 C27 120.1(2) C28 C29 C30 120.02(18) C28 C29 C32 121.39(18) C30 C29 C32 118.51(17) C29 C30 C21 120.69(17) C29 C30 C25 120.09(17) C21 C30 C25 119.22(17) O4 C31 O5 118.22(17) O4 C31 C21 124.20(18) O5 C31 C21 117.39(16) O6 C32 O5 108.80(15) O6 C32 C29 110.06(15) O5 C32 C29 112.63(14) N1 C41 C42 121.54(17) C41 C42 C43 120.33(16) N2 C43 C42 121.96(17) N2 C43 C44 121.72(17) C42 C43 C44 116.32(16) C45 C44 C43 120.06(17) N1 C45 C44 121.58(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C11 1.240(2) O2 C11 1.260(2) O3 C12 1.184(2) O4 C31 1.206(2) O5 C31 1.352(2) O5 C32 1.455(2) O6 C32 1.386(2) N1 C45 1.341(2) N1 C41 1.349(2) N2 C43 1.337(2) N2 C47 1.459(3) N2 C46 1.463(3) C1 C2 1.376(2) C1 C10 1.429(2) C1 C11 1.513(2) C2 C3 1.406(3) C3 C4 1.357(3) C4 C5 1.419(2) C5 C6 1.416(3) C5 C10 1.424(2) C6 C7 1.356(3) C7 C8 1.398(3) C8 C9 1.373(3) C9 C10 1.441(2) C9 C12 1.485(3) C21 C22 1.371(3) C21 C30 1.414(3) C21 C31 1.482(2) C22 C23 1.407(3) C23 C24 1.368(3) C24 C25 1.415(3) C25 C26 1.413(3) C25 C30 1.421(3) C26 C27 1.359(3) C27 C28 1.411(3) C28 C29 1.364(3) C29 C30 1.410(3) C29 C32 1.500(3) C41 C42 1.354(3) C42 C43 1.414(3) C43 C44 1.423(3) C44 C45 1.358(3) 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 H61 O1 0.91(3) 1.76(3) 2.6724(19) 179(3) 2 N1 H1 O2 0.91(2) 1.73(3) 2.640(2) 176(2) . C41 H41 O2 0.95 2.36 3.310(2) 175.3 3