#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:16:58 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257988 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240369.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_7240369 loop_ _publ_author_name 'Carnero, Alejandro' 'Mart\'in-Nieves, Virginia' 'Sanghvi, Yogesh S.' 'Russel, Olivia O.' 'Bassit, Leda' 'Schinazi, Raymond F.' 'Fern\'andez, Susana' 'Ferrero, Miguel' _publ_section_title ; Novel 1′-homo-N-2′-deoxy-\a-nucleosides: synthesis, characterization and biological activity ; _journal_issue 27 _journal_name_full 'RSC Advances' _journal_page_first 15815 _journal_page_last 15824 _journal_paper_doi 10.1039/D0RA03254A _journal_volume 10 _journal_year 2020 _chemical_absolute_configuration syn _chemical_formula_moiety 'C11 H15 N5 O3' _chemical_formula_sum 'C11 H15 N5 O3' _chemical_formula_weight 265.28 _chemical_name_systematic 1'-Homo-N-2'-deoxy-alfa-adenosine _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' _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2018-07-10 _audit_creation_method 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _audit_update_record ; 2020-01-28 deposited with the CCDC. 2020-04-15 downloaded from the CCDC. ; _cell_angle_alpha 90.0 _cell_angle_beta 117.058(4) _cell_angle_gamma 90.0 _cell_formula_units_Z 6 _cell_length_a 15.8711(6) _cell_length_b 8.04111(18) _cell_length_c 16.4342(5) _cell_measurement_reflns_used 5358 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 68.9410 _cell_measurement_theta_min 3.0090 _cell_volume 1867.79(12) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SIR2004 (Burla, 2005)' _diffrn_ambient_temperature 150(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.2640 _diffrn_detector_type Onyx _diffrn_measured_fraction_theta_full 0.9954 _diffrn_measured_fraction_theta_max 0.6925 _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 -68.00 18.90 1.10 8.00 -- -43.48 37.00 90.00 79 2 \w -112.00 -80.10 1.10 8.00 -- -43.48 -99.00 30.00 29 3 \w -125.00 -82.10 1.10 8.00 -- -43.48 -99.00 150.00 39 4 \w 54.00 125.50 1.10 37.50 -- 94.50 -77.00 -30.00 65 5 \w 70.00 97.50 1.10 37.50 -- 94.50-125.00 0.00 25 6 \w 62.00 87.30 1.10 37.50 -- 94.50 -45.00 -30.00 23 7 \w 69.00 164.70 1.10 37.50 -- 94.50 30.00 -60.00 87 8 \w 120.00 158.50 1.10 37.50 -- 94.50 45.00-180.00 35 9 \w 127.00 153.40 1.10 37.50 -- 94.50 125.00-150.00 24 10 \w 95.00 120.30 1.10 37.50 -- 94.50 125.00-180.00 23 11 \w 72.00 96.20 1.10 37.50 -- 94.50 45.00-180.00 22 12 \w 49.00 111.70 1.10 37.50 -- 94.50 -45.00-180.00 57 13 \w 26.00 60.10 1.10 37.50 -- 94.50 -45.00 -30.00 31 14 \w 78.00 109.90 1.10 37.50 -- 94.50 -30.00 120.00 29 15 \w 99.00 124.30 1.10 37.50 -- 94.50 -77.00 120.00 23 16 \w 27.00 71.00 1.10 37.50 -- 94.50 -77.00 120.00 40 17 \w 24.00 58.10 1.10 37.50 -- 94.50 -30.00 120.00 31 18 \w -107.00 -80.60 1.10 8.00 -- -43.48 -99.00-180.00 24 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Onyx, Nova' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0978495000 _diffrn_orient_matrix_UB_12 0.0388436000 _diffrn_orient_matrix_UB_13 -0.0063636000 _diffrn_orient_matrix_UB_21 0.0448463000 _diffrn_orient_matrix_UB_22 0.0135189000 _diffrn_orient_matrix_UB_23 0.1049244000 _diffrn_orient_matrix_UB_31 0.0171318000 _diffrn_orient_matrix_UB_32 0.1870617000 _diffrn_orient_matrix_UB_33 -0.0062373000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_av_unetI/netI 0.0367 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 9891 _diffrn_reflns_point_group_measured_fraction_full 0.704 _diffrn_reflns_point_group_measured_fraction_max 0.693 _diffrn_reflns_theta_full 68.1328 _diffrn_reflns_theta_max 69.5376 _diffrn_reflns_theta_min 3.0195 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Nova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.892 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.88784 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear intense white' _exptl_crystal_density_diffrn 1.415 _exptl_crystal_description plate _exptl_crystal_F_000 840 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.255 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.043 _refine_ls_abs_structure_details ; Flack x determined using 898 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). The absolute configuration was assigned by prior knowledge of chiral centers. ; _refine_ls_abs_structure_Flack 0.2(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 520 _refine_ls_number_reflns 4865 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0424 _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^)+(0.0756P)^2^+0.0248P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1102 _refine_ls_wR_factor_ref 0.1183 _reflns_Friedel_coverage 0.304 _reflns_Friedel_fraction_full 0.362 _reflns_Friedel_fraction_max 0.349 _reflns_number_gt 4279 _reflns_number_total 4865 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03254a2.cif _cod_data_source_block 18030_vm1_c _cod_depositor_comments 'Adding full bibliography for 7240369.cif.' _cod_original_cell_volume 1867.77(12) _cod_database_code 7240369 _cell_oxdiff_length_a 15.8723(8) _cell_oxdiff_length_b 8.0435(2) _cell_oxdiff_length_c 16.4284(8) _cell_oxdiff_angle_alpha 90.000(3) _cell_oxdiff_angle_beta 117.061(5) _cell_oxdiff_angle_gamma 90.025(3) _cell_oxdiff_volume 1867.77(15) _cell_oxdiff_measurement_reflns_used 5358 _oxdiff_exptl_absorpt_empirical_full_min 0.719 _oxdiff_exptl_absorpt_empirical_full_max 1.704 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _reflns_odcompleteness_completeness 99.54 _reflns_odcompleteness_theta 68.13 _reflns_odcompleteness_iscentric 1 _chemical_oxdiff_formula C11H15N5O3 _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 0.776 _shelx_estimated_absorpt_t_max 0.974 _shelx_res_file ; TITL 18038_vm1_c in P2(1) 18038_vm1_c.res created by SHELXL-2018/3 at 17:21:35 on 21-Aug-2018 CELL 1.54184 15.871063 8.041107 16.434160 90.0000 117.0584 90.0000 ZERR 6.00 0.000579 0.000179 0.000518 0.0000 0.0043 0.0000 LATT -1 SYMM -X,1/2+Y,-Z SFAC C H N O UNIT 66 90 30 18 TEMP -123.13 SIZE 0.03 0.16 0.30 ACTA BOND $H LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 10 FMAP 2 PLAN 25 REM Instructions for potential hydrogen bonds EQIV $1 x-1, y+1, z-1 EQIV $2 x-1, y, z-1 EQIV $3 x, y+1, z EQIV $4 x, y-1, z EQIV $5 -x+2, y-1/2, -z+2 EQIV $6 -x+2, y+1/2, -z+2 EQIV $7 x+1, y, z+1 EQIV $8 x+1, y-1, z+1 HTAB N10 N47_$1 HTAB N10 N41_$2 HTAB O17 O59_$3 HTAB O19 N3_$4 HTAB N30 N27_$5 HTAB N30 N21_$6 HTAB O37 O17 HTAB O39 N23_$3 HTAB N50 N7_$7 HTAB N50 N1_$8 HTAB O57 O19 HTAB O59 N43_$4 WGHT 0.075600 0.024800 FVAR 5.83374 MOLE 1 N1 3 0.091660 1.338005 -0.271057 11.00000 0.05388 0.04386 = 0.04258 0.00475 0.00690 -0.00030 N3 3 0.188849 1.289915 -0.110255 11.00000 0.05676 0.04406 = 0.04132 -0.00131 0.00587 -0.00213 N5 3 0.176048 1.006766 -0.067116 11.00000 0.04918 0.04265 = 0.03305 0.00144 0.00889 0.00434 N7 3 0.075481 0.903084 -0.204358 11.00000 0.04559 0.03891 = 0.04158 -0.00014 0.01125 0.00356 N10 3 0.001197 1.137514 -0.372591 11.00000 0.05349 0.04240 = 0.03581 0.00192 0.00733 -0.00012 AFIX 93 H101 2 -0.016668 1.212812 -0.416130 11.00000 -1.50000 H102 2 -0.020370 1.035111 -0.385635 11.00000 -1.50000 AFIX 0 C2 1 0.152814 1.382136 -0.185957 11.00000 0.06243 0.04085 = 0.04921 0.00031 0.00876 -0.00519 AFIX 43 H2 2 0.173386 1.494567 -0.178426 11.00000 -1.50000 AFIX 0 C4 1 0.155778 1.133540 -0.128634 11.00000 0.04432 0.03771 = 0.03784 0.00132 0.01210 0.00369 C6 1 0.125887 0.871941 -0.116230 11.00000 0.05226 0.03994 = 0.04115 0.00158 0.01373 0.00227 AFIX 43 H6 2 0.127204 0.766516 -0.089587 11.00000 -1.50000 AFIX 0 C8 1 0.093311 1.068906 -0.212611 11.00000 0.03927 0.04193 = 0.03696 -0.00070 0.01105 0.00568 C9 1 0.060689 1.178407 -0.287223 11.00000 0.04039 0.03997 = 0.03847 0.00175 0.01272 0.00441 C11 1 0.242068 1.022445 0.030313 11.00000 0.06180 0.04915 = 0.03463 -0.00124 0.00802 0.00517 AFIX 23 H111 2 0.222134 1.117528 0.055769 11.00000 -1.50000 H112 2 0.305784 1.048015 0.036635 11.00000 -1.50000 AFIX 0 C12 1 0.248507 0.871173 0.085320 11.00000 0.05503 0.05631 = 0.03992 0.00514 0.01466 0.00636 AFIX 13 H12 2 0.184685 0.843631 0.079824 11.00000 -1.50000 AFIX 0 C13 1 0.319107 0.894366 0.185910 11.00000 0.06341 0.06111 = 0.03682 0.00505 0.01393 0.01546 AFIX 23 H131 2 0.369581 0.974024 0.193071 11.00000 -1.50000 H132 2 0.287188 0.933746 0.221928 11.00000 -1.50000 AFIX 0 C14 1 0.358281 0.720937 0.214111 11.00000 0.04842 0.05065 = 0.03728 0.00770 0.01001 -0.00105 AFIX 13 H14 2 0.312659 0.655599 0.227849 11.00000 -1.50000 AFIX 0 C15 1 0.357067 0.650584 0.126853 11.00000 0.04742 0.04095 = 0.04085 0.00418 0.01155 -0.00176 AFIX 13 H15 2 0.418514 0.676925 0.126576 11.00000 -1.50000 AFIX 0 C18 1 0.340124 0.466522 0.115576 11.00000 0.06552 0.04433 = 0.05442 0.00383 0.01778 -0.00577 AFIX 23 H181 2 0.385089 0.409548 0.172157 11.00000 -1.50000 H182 2 0.275245 0.442305 0.106443 11.00000 -1.50000 AFIX 0 O16 4 0.282992 0.734970 0.053563 11.00000 0.10672 0.06209 = 0.03694 0.00252 0.00794 0.03203 O17 4 0.447955 0.715248 0.291624 11.00000 0.05204 0.05900 = 0.04055 0.01049 0.00805 0.00339 AFIX 147 H17 2 0.488677 0.757786 0.278647 11.00000 -1.50000 AFIX 0 O19 4 0.351094 0.403047 0.040832 11.00000 0.05409 0.05370 = 0.05858 -0.01331 0.00921 -0.00144 AFIX 147 H19 2 0.298335 0.371480 -0.000098 11.00000 -1.50000 AFIX 0 MOLE 2 N21 3 0.903375 -0.176382 0.899688 11.00000 0.06367 0.04348 = 0.04494 0.00129 0.01555 -0.00403 N23 3 0.819235 -0.122160 0.738308 11.00000 0.05904 0.04364 = 0.04407 -0.00216 0.01096 -0.00020 N25 3 0.837121 0.164772 0.702693 11.00000 0.05155 0.03899 = 0.03669 0.00165 0.01289 0.00742 N27 3 0.928782 0.260576 0.843908 11.00000 0.05567 0.04180 = 0.04123 -0.00139 0.01765 0.00151 N30 3 0.988166 0.021676 1.007758 11.00000 0.07525 0.04354 = 0.03731 0.00249 0.00956 -0.00281 AFIX 93 H301 2 1.002872 -0.054254 1.050647 11.00000 -1.50000 H302 2 1.008979 0.124185 1.022485 11.00000 -1.50000 AFIX 0 C22 1 0.849576 -0.216429 0.812267 11.00000 0.06764 0.04098 = 0.04722 0.00025 0.01594 -0.00642 AFIX 43 H22 2 0.830164 -0.329448 0.801524 11.00000 -1.50000 AFIX 0 C24 1 0.851740 0.033545 0.760412 11.00000 0.04473 0.04273 = 0.04064 -0.00037 0.01460 0.00355 C26 1 0.884736 0.295260 0.756487 11.00000 0.05775 0.03719 = 0.04668 0.00326 0.01959 0.00617 AFIX 43 H26 2 0.885989 0.402451 0.732755 11.00000 -1.50000 AFIX 0 C28 1 0.908065 0.094812 0.847642 11.00000 0.04262 0.03892 = 0.03950 0.00055 0.01441 0.00515 C29 1 0.934532 -0.018459 0.920756 11.00000 0.04905 0.03983 = 0.04320 0.00195 0.01634 0.00296 C31 1 0.780679 0.162911 0.602736 11.00000 0.05453 0.05180 = 0.03661 0.00255 0.01528 0.00844 AFIX 23 H311 2 0.772241 0.046349 0.581042 11.00000 -1.50000 H312 2 0.815738 0.222648 0.574946 11.00000 -1.50000 AFIX 0 C32 1 0.685964 0.241217 0.571357 11.00000 0.05521 0.05302 = 0.04442 0.00576 0.01512 0.01175 AFIX 13 H32 2 0.652529 0.188963 0.603806 11.00000 -1.50000 AFIX 0 C33 1 0.625307 0.223950 0.468095 11.00000 0.06346 0.04758 = 0.04447 0.00044 0.00942 0.01002 AFIX 23 H331 2 0.665128 0.207116 0.436719 11.00000 -1.50000 H332 2 0.580318 0.130130 0.453279 11.00000 -1.50000 AFIX 0 C34 1 0.573965 0.388213 0.441951 11.00000 0.04911 0.04991 = 0.04166 0.00305 0.01154 0.00468 AFIX 13 H34 2 0.517905 0.385856 0.454427 11.00000 -1.50000 AFIX 0 C35 1 0.647611 0.507692 0.506918 11.00000 0.04772 0.05100 = 0.05613 0.00034 0.02073 0.00155 AFIX 13 H35 2 0.693029 0.536288 0.482362 11.00000 -1.50000 AFIX 0 C38 1 0.608888 0.664522 0.525610 11.00000 0.06982 0.04786 = 0.06295 -0.00283 0.00858 0.00430 AFIX 23 H381 2 0.552142 0.697452 0.469255 11.00000 -1.50000 H382 2 0.588304 0.641461 0.573032 11.00000 -1.50000 AFIX 0 O36 4 0.696371 0.415757 0.590109 11.00000 0.07864 0.06011 = 0.04978 -0.00976 -0.00038 0.02306 O37 4 0.544515 0.421809 0.348618 11.00000 0.09162 0.06965 = 0.04506 0.00717 0.01743 0.02294 AFIX 147 H37 2 0.507171 0.503074 0.332261 11.00000 -1.50000 AFIX 0 O39 4 0.671982 0.798772 0.554602 11.00000 0.12542 0.05611 = 0.06940 -0.00182 -0.00248 -0.02011 AFIX 147 H39 2 0.708038 0.789988 0.610846 11.00000 -1.50000 AFIX 0 MOLE 3 N41 3 0.886927 0.835628 0.538219 11.00000 0.06018 0.04021 = 0.04539 -0.00156 0.01096 0.00344 N43 3 0.770096 0.767091 0.386321 11.00000 0.05058 0.03897 = 0.04068 0.00394 0.01356 0.00522 N45 3 0.778043 0.477644 0.350028 11.00000 0.05149 0.03509 = 0.03771 0.00003 0.01314 0.00225 N47 3 0.896541 0.391867 0.482701 11.00000 0.05287 0.03760 = 0.04303 0.00291 0.01064 0.00245 N50 3 0.989195 0.643673 0.640570 11.00000 0.06940 0.04454 = 0.04390 -0.00213 -0.00001 0.00416 AFIX 93 H501 2 1.012957 0.722858 0.681807 11.00000 -1.50000 H502 2 1.011172 0.541568 0.653983 11.00000 -1.50000 AFIX 0 C42 1 0.815891 0.868439 0.456380 11.00000 0.06222 0.03718 = 0.04982 0.00001 0.01652 0.00463 AFIX 43 H42 2 0.794973 0.980712 0.446772 11.00000 -1.50000 AFIX 0 C44 1 0.805829 0.612884 0.405893 11.00000 0.04328 0.03652 = 0.03711 0.00250 0.01425 0.00102 C46 1 0.834525 0.348927 0.399667 11.00000 0.05644 0.03700 = 0.04509 0.00142 0.01432 0.00174 AFIX 43 H46 2 0.829393 0.239263 0.376367 11.00000 -1.50000 AFIX 0 C48 1 0.879113 0.559016 0.487782 11.00000 0.04405 0.03986 = 0.04029 0.00569 0.01463 -0.00094 C49 1 0.919211 0.678743 0.556950 11.00000 0.04784 0.04056 = 0.04114 0.00013 0.01376 -0.00213 C51 1 0.697689 0.475731 0.257652 11.00000 0.05145 0.04493 = 0.04037 -0.00058 0.01030 0.00259 AFIX 23 H511 2 0.699961 0.577980 0.225152 11.00000 -1.50000 H512 2 0.638134 0.478320 0.263172 11.00000 -1.50000 AFIX 0 C52 1 0.695617 0.328064 0.201235 11.00000 0.05253 0.05024 = 0.04056 -0.00026 0.01644 -0.00665 AFIX 13 H52 2 0.757195 0.320301 0.198564 11.00000 -1.50000 AFIX 0 C53 1 0.614680 0.343280 0.103819 11.00000 0.07424 0.05374 = 0.03811 0.00240 0.01284 -0.00986 AFIX 23 H531 2 0.569845 0.431890 0.100317 11.00000 -1.50000 H532 2 0.639509 0.368597 0.059776 11.00000 -1.50000 AFIX 0 C54 1 0.567267 0.175104 0.084469 11.00000 0.05236 0.04650 = 0.04074 -0.00322 0.00924 0.00229 AFIX 13 H54 2 0.601775 0.100139 0.061205 11.00000 -1.50000 AFIX 0 C55 1 0.586499 0.116021 0.179169 11.00000 0.04518 0.04184 = 0.04577 -0.00206 0.01037 -0.00008 AFIX 13 H55 2 0.539629 0.166696 0.196827 11.00000 -1.50000 AFIX 0 C58 1 0.584815 -0.069935 0.186409 11.00000 0.05899 0.04303 = 0.06520 0.00071 0.01310 -0.00592 AFIX 23 H581 2 0.527021 -0.112921 0.134261 11.00000 -1.50000 H582 2 0.640062 -0.116518 0.181494 11.00000 -1.50000 AFIX 0 O56 4 0.679509 0.175907 0.238161 11.00000 0.05549 0.04713 = 0.04448 0.00688 0.00308 -0.00912 O57 4 0.470619 0.174236 0.020785 11.00000 0.06240 0.05732 = 0.05438 -0.01111 -0.00378 0.00492 AFIX 147 H57 2 0.443303 0.254990 0.031132 11.00000 -1.50000 AFIX 0 O59 4 0.586590 -0.126689 0.268452 11.00000 0.05026 0.06460 = 0.06974 0.02137 0.00938 -0.00514 AFIX 147 H59 2 0.642826 -0.143962 0.307369 11.00000 -1.50000 AFIX 0 HKLF 4 REM 18038_vm1_c in P2(1) REM wR2 = 0.1183, GooF = S = 1.037, Restrained GooF = 1.037 for all data REM R1 = 0.0424 for 4279 Fo > 4sig(Fo) and 0.0485 for all 4865 data REM 520 parameters refined using 1 restraints END WGHT 0.0756 0.0248 REM Highest difference peak 0.255, deepest hole -0.224, 1-sigma level 0.043 Q1 1 0.8512 -0.4752 0.7722 11.00000 0.05 0.25 Q2 1 0.8938 -0.3406 0.8469 11.00000 0.05 0.20 Q3 1 0.8661 0.4112 0.7820 11.00000 0.05 0.20 Q4 1 0.5593 0.1200 0.4724 11.00000 0.05 0.20 Q5 1 0.7674 0.5005 0.6565 11.00000 0.05 0.19 Q6 1 0.4787 0.9372 0.3624 11.00000 0.05 0.19 Q7 1 1.0523 -0.1160 1.0953 11.00000 0.05 0.19 Q8 1 0.5570 0.6978 0.6816 11.00000 0.05 0.18 Q9 1 0.6006 0.4288 0.0750 11.00000 0.05 0.18 Q10 1 0.6497 0.1657 0.5281 11.00000 0.05 0.17 Q11 1 0.5699 0.2005 0.3988 11.00000 0.05 0.17 Q12 1 0.7710 -0.3988 0.6889 11.00000 0.05 0.16 Q13 1 0.4387 0.3811 0.4332 11.00000 0.05 0.16 Q14 1 1.0686 0.0680 1.0984 11.00000 0.05 0.16 Q15 1 0.6844 0.9188 0.6732 11.00000 0.05 0.16 Q16 1 0.1896 0.6537 0.0131 11.00000 0.05 0.15 Q17 1 -0.0808 1.0799 -0.4574 11.00000 0.05 0.14 Q18 1 0.3528 0.8196 0.2015 11.00000 0.05 0.14 Q19 1 0.9741 0.7227 0.6857 11.00000 0.05 0.14 Q20 1 0.3369 0.9154 0.1112 11.00000 0.05 0.14 Q21 1 0.7828 0.3897 0.6093 11.00000 0.05 0.13 Q22 1 0.0680 1.4046 -0.3119 11.00000 0.05 0.13 Q23 1 0.5346 0.2010 0.0091 11.00000 0.05 0.13 Q24 1 0.5412 0.6208 0.5503 11.00000 0.05 0.13 Q25 1 0.4908 0.6534 0.2728 11.00000 0.05 0.13 ; _shelx_res_checksum 75871 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 N1 N 0.0917(2) 1.3380(4) -0.27106(18) 0.0525(7) Uani 1 1 d . . . . . N3 N 0.1888(2) 1.2899(4) -0.11025(18) 0.0537(7) Uani 1 1 d . . . . . N5 N 0.17605(18) 1.0068(4) -0.06712(16) 0.0454(6) Uani 1 1 d . . . . . N7 N 0.07548(18) 0.9031(4) -0.20436(17) 0.0453(6) Uani 1 1 d . . . . . N10 N 0.00120(19) 1.1375(4) -0.37259(16) 0.0489(6) Uani 1 1 d . . . . . H101 H -0.016668 1.212812 -0.416130 0.073 Uiso 1 1 calc R U . . . H102 H -0.020370 1.035111 -0.385635 0.073 Uiso 1 1 calc R U . . . C2 C 0.1528(3) 1.3821(5) -0.1860(2) 0.0572(9) Uani 1 1 d . . . . . H2 H 0.173386 1.494567 -0.178426 0.086 Uiso 1 1 calc R U . . . C4 C 0.1558(2) 1.1335(4) -0.12863(19) 0.0425(7) Uani 1 1 d . . . . . C6 C 0.1259(2) 0.8719(5) -0.1162(2) 0.0473(7) Uani 1 1 d . . . . . H6 H 0.127204 0.766516 -0.089587 0.071 Uiso 1 1 calc R U . . . C8 C 0.0933(2) 1.0689(4) -0.21261(19) 0.0418(7) Uani 1 1 d . . . . . C9 C 0.0607(2) 1.1784(4) -0.28722(19) 0.0416(7) Uani 1 1 d . . . . . C11 C 0.2421(3) 1.0224(5) 0.0303(2) 0.0538(9) Uani 1 1 d . . . . . H111 H 0.222134 1.117528 0.055769 0.081 Uiso 1 1 calc R U . . . H112 H 0.305784 1.048015 0.036635 0.081 Uiso 1 1 calc R U . . . C12 C 0.2485(3) 0.8712(5) 0.0853(2) 0.0531(8) Uani 1 1 d . . . . . H12 H 0.184685 0.843631 0.079824 0.080 Uiso 1 1 calc R U . . . C13 C 0.3191(3) 0.8944(6) 0.1859(2) 0.0572(9) Uani 1 1 d . . . . . H131 H 0.369581 0.974024 0.193071 0.086 Uiso 1 1 calc R U . . . H132 H 0.287188 0.933746 0.221928 0.086 Uiso 1 1 calc R U . . . C14 C 0.3583(2) 0.7209(5) 0.2141(2) 0.0491(8) Uani 1 1 d . . . . . H14 H 0.312659 0.655599 0.227849 0.074 Uiso 1 1 calc R U . . . C15 C 0.3571(2) 0.6506(5) 0.1269(2) 0.0463(7) Uani 1 1 d . . . . . H15 H 0.418514 0.676925 0.126576 0.069 Uiso 1 1 calc R U . . . C18 C 0.3401(3) 0.4665(5) 0.1156(2) 0.0584(9) Uani 1 1 d . . . . . H181 H 0.385089 0.409548 0.172157 0.088 Uiso 1 1 calc R U . . . H182 H 0.275245 0.442305 0.106443 0.088 Uiso 1 1 calc R U . . . O16 O 0.2830(2) 0.7350(4) 0.05356(16) 0.0780(9) Uani 1 1 d . . . . . O17 O 0.44795(16) 0.7152(4) 0.29162(14) 0.0555(6) Uani 1 1 d . . . . . H17 H 0.488677 0.757786 0.278647 0.083 Uiso 1 1 calc R U . . . O19 O 0.35109(17) 0.4030(4) 0.04083(16) 0.0617(7) Uani 1 1 d . . . . . H19 H 0.298335 0.371480 -0.000098 0.093 Uiso 1 1 calc R U . . . N21 N 0.9034(2) -0.1764(4) 0.89969(19) 0.0542(7) Uani 1 1 d . . . . . N23 N 0.8192(2) -0.1222(4) 0.73831(18) 0.0537(7) Uani 1 1 d . . . . . N25 N 0.83712(18) 0.1648(4) 0.70269(15) 0.0452(6) Uani 1 1 d . . . . . N27 N 0.9288(2) 0.2606(4) 0.84391(17) 0.0479(6) Uani 1 1 d . . . . . N30 N 0.9882(2) 0.0217(4) 1.00776(18) 0.0582(8) Uani 1 1 d . . . . . H301 H 1.002872 -0.054254 1.050647 0.087 Uiso 1 1 calc R U . . . H302 H 1.008979 0.124185 1.022485 0.087 Uiso 1 1 calc R U . . . C22 C 0.8496(3) -0.2164(5) 0.8123(2) 0.0558(9) Uani 1 1 d . . . . . H22 H 0.830164 -0.329448 0.801524 0.084 Uiso 1 1 calc R U . . . C24 C 0.8517(2) 0.0335(4) 0.7604(2) 0.0445(7) Uani 1 1 d . . . . . C26 C 0.8847(2) 0.2953(5) 0.7565(2) 0.0488(8) Uani 1 1 d . . . . . H26 H 0.885989 0.402451 0.732755 0.073 Uiso 1 1 calc R U . . . C28 C 0.9081(2) 0.0948(4) 0.84764(19) 0.0420(7) Uani 1 1 d . . . . . C29 C 0.9345(2) -0.0185(5) 0.9208(2) 0.0458(7) Uani 1 1 d . . . . . C31 C 0.7807(2) 0.1629(5) 0.60274(19) 0.0497(8) Uani 1 1 d . . . . . H311 H 0.772241 0.046349 0.581042 0.075 Uiso 1 1 calc R U . . . H312 H 0.815738 0.222648 0.574946 0.075 Uiso 1 1 calc R U . . . C32 C 0.6860(3) 0.2412(5) 0.5714(2) 0.0538(8) Uani 1 1 d . . . . . H32 H 0.652529 0.188963 0.603806 0.081 Uiso 1 1 calc R U . . . C33 C 0.6253(3) 0.2240(5) 0.4681(2) 0.0576(9) Uani 1 1 d . . . . . H331 H 0.665128 0.207116 0.436719 0.086 Uiso 1 1 calc R U . . . H332 H 0.580318 0.130130 0.453279 0.086 Uiso 1 1 calc R U . . . C34 C 0.5740(2) 0.3882(5) 0.4420(2) 0.0504(8) Uani 1 1 d . . . . . H34 H 0.517905 0.385856 0.454427 0.076 Uiso 1 1 calc R U . . . C35 C 0.6476(2) 0.5077(5) 0.5069(2) 0.0527(8) Uani 1 1 d . . . . . H35 H 0.693029 0.536288 0.482362 0.079 Uiso 1 1 calc R U . . . C38 C 0.6089(3) 0.6645(6) 0.5256(3) 0.0685(10) Uani 1 1 d . . . . . H381 H 0.552142 0.697452 0.469255 0.103 Uiso 1 1 calc R U . . . H382 H 0.588304 0.641461 0.573032 0.103 Uiso 1 1 calc R U . . . O36 O 0.6964(2) 0.4158(4) 0.59011(17) 0.0742(9) Uani 1 1 d . . . . . O37 O 0.5445(2) 0.4218(4) 0.34862(16) 0.0740(8) Uani 1 1 d . . . . . H37 H 0.507171 0.503074 0.332261 0.111 Uiso 1 1 calc R U . . . O39 O 0.6720(3) 0.7988(5) 0.5546(2) 0.1015(13) Uani 1 1 d . . . . . H39 H 0.708038 0.789988 0.610846 0.152 Uiso 1 1 calc R U . . . N41 N 0.8869(2) 0.8356(4) 0.53822(18) 0.0536(7) Uani 1 1 d . . . . . N43 N 0.77010(19) 0.7671(4) 0.38632(17) 0.0462(6) Uani 1 1 d . . . . . N45 N 0.77804(19) 0.4776(4) 0.35003(16) 0.0442(6) Uani 1 1 d . . . . . N47 N 0.8965(2) 0.3919(4) 0.48270(17) 0.0488(6) Uani 1 1 d . . . . . N50 N 0.9892(2) 0.6437(4) 0.64057(18) 0.0625(8) Uani 1 1 d . . . . . H501 H 1.012957 0.722858 0.681807 0.094 Uiso 1 1 calc R U . . . H502 H 1.011172 0.541568 0.653983 0.094 Uiso 1 1 calc R U . . . C42 C 0.8159(3) 0.8684(5) 0.4564(2) 0.0532(8) Uani 1 1 d . . . . . H42 H 0.794973 0.980712 0.446772 0.080 Uiso 1 1 calc R U . . . C44 C 0.8058(2) 0.6129(4) 0.40589(19) 0.0405(7) Uani 1 1 d . . . . . C46 C 0.8345(2) 0.3489(5) 0.3997(2) 0.0495(8) Uani 1 1 d . . . . . H46 H 0.829393 0.239263 0.376367 0.074 Uiso 1 1 calc R U . . . C48 C 0.8791(2) 0.5590(4) 0.4878(2) 0.0431(7) Uani 1 1 d . . . . . C49 C 0.9192(2) 0.6787(5) 0.5570(2) 0.0457(7) Uani 1 1 d . . . . . C51 C 0.6977(2) 0.4757(5) 0.2577(2) 0.0496(8) Uani 1 1 d . . . . . H511 H 0.699961 0.577980 0.225152 0.074 Uiso 1 1 calc R U . . . H512 H 0.638134 0.478320 0.263172 0.074 Uiso 1 1 calc R U . . . C52 C 0.6956(2) 0.3281(5) 0.2012(2) 0.0496(8) Uani 1 1 d . . . . . H52 H 0.757195 0.320301 0.198564 0.074 Uiso 1 1 calc R U . . . C53 C 0.6147(3) 0.3433(5) 0.1038(2) 0.0602(10) Uani 1 1 d . . . . . H531 H 0.569845 0.431890 0.100317 0.090 Uiso 1 1 calc R U . . . H532 H 0.639509 0.368597 0.059776 0.090 Uiso 1 1 calc R U . . . C54 C 0.5673(2) 0.1751(5) 0.0845(2) 0.0511(8) Uani 1 1 d . . . . . H54 H 0.601775 0.100139 0.061205 0.077 Uiso 1 1 calc R U . . . C55 C 0.5865(2) 0.1160(5) 0.1792(2) 0.0482(7) Uani 1 1 d . . . . . H55 H 0.539629 0.166696 0.196827 0.072 Uiso 1 1 calc R U . . . C58 C 0.5848(3) -0.0699(5) 0.1864(3) 0.0615(10) Uani 1 1 d . . . . . H581 H 0.527021 -0.112921 0.134261 0.092 Uiso 1 1 calc R U . . . H582 H 0.640062 -0.116518 0.181494 0.092 Uiso 1 1 calc R U . . . O56 O 0.67951(17) 0.1759(4) 0.23816(15) 0.0566(6) Uani 1 1 d . . . . . O57 O 0.47062(18) 0.1742(4) 0.02078(17) 0.0696(8) Uani 1 1 d . . . . . H57 H 0.443303 0.254990 0.031132 0.104 Uiso 1 1 calc R U . . . O59 O 0.58659(18) -0.1267(4) 0.26845(18) 0.0684(7) Uani 1 1 d . . . . . H59 H 0.642826 -0.143962 0.307369 0.103 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 N1 0.0539(15) 0.0439(17) 0.0426(13) 0.0048(12) 0.0069(12) -0.0003(14) N3 0.0568(16) 0.0441(17) 0.0413(14) -0.0013(12) 0.0059(12) -0.0021(14) N5 0.0492(14) 0.0426(16) 0.0331(11) 0.0014(11) 0.0089(10) 0.0043(13) N7 0.0456(13) 0.0389(15) 0.0416(12) -0.0001(11) 0.0112(10) 0.0036(12) N10 0.0535(14) 0.0424(16) 0.0358(12) 0.0019(11) 0.0073(11) -0.0001(14) C2 0.062(2) 0.041(2) 0.0492(17) 0.0003(16) 0.0088(15) -0.0052(18) C4 0.0443(14) 0.0377(18) 0.0378(13) 0.0013(13) 0.0121(12) 0.0037(14) C6 0.0523(17) 0.0399(19) 0.0412(14) 0.0016(14) 0.0137(13) 0.0023(16) C8 0.0393(14) 0.0419(18) 0.0370(13) -0.0007(13) 0.0111(12) 0.0057(14) C9 0.0404(14) 0.0400(18) 0.0385(14) 0.0018(13) 0.0127(12) 0.0044(14) C11 0.0618(19) 0.049(2) 0.0346(14) -0.0012(14) 0.0080(13) 0.0052(18) C12 0.0550(18) 0.056(2) 0.0399(15) 0.0051(15) 0.0147(13) 0.0064(17) C13 0.063(2) 0.061(2) 0.0368(15) 0.0051(16) 0.0139(14) 0.0155(19) C14 0.0484(16) 0.051(2) 0.0373(14) 0.0077(14) 0.0100(13) -0.0010(15) C15 0.0474(16) 0.0409(18) 0.0408(14) 0.0042(14) 0.0116(12) -0.0018(15) C18 0.066(2) 0.044(2) 0.0544(18) 0.0038(16) 0.0178(16) -0.0058(18) O16 0.107(2) 0.0621(19) 0.0369(11) 0.0025(12) 0.0079(13) 0.0320(17) O17 0.0520(12) 0.0590(17) 0.0406(11) 0.0105(11) 0.0081(9) 0.0034(12) O19 0.0541(13) 0.0537(16) 0.0586(13) -0.0133(12) 0.0092(11) -0.0014(13) N21 0.0637(17) 0.0435(17) 0.0449(14) 0.0013(13) 0.0155(13) -0.0040(15) N23 0.0590(16) 0.0436(17) 0.0441(13) -0.0022(13) 0.0110(12) -0.0002(15) N25 0.0516(13) 0.0390(15) 0.0367(12) 0.0017(11) 0.0129(10) 0.0074(13) N27 0.0557(15) 0.0418(16) 0.0412(13) -0.0014(12) 0.0177(11) 0.0015(14) N30 0.0753(19) 0.0435(17) 0.0373(12) 0.0025(13) 0.0096(12) -0.0028(16) C22 0.068(2) 0.041(2) 0.0472(17) 0.0003(15) 0.0159(15) -0.0064(18) C24 0.0447(15) 0.0427(19) 0.0406(14) -0.0004(13) 0.0146(12) 0.0036(15) C26 0.0577(18) 0.0372(18) 0.0467(16) 0.0033(14) 0.0196(14) 0.0062(15) C28 0.0426(15) 0.0389(18) 0.0395(14) 0.0006(13) 0.0144(12) 0.0051(14) C29 0.0491(16) 0.0398(18) 0.0432(15) 0.0019(14) 0.0163(13) 0.0030(15) C31 0.0545(17) 0.052(2) 0.0366(14) 0.0026(14) 0.0153(13) 0.0084(17) C32 0.0552(18) 0.053(2) 0.0444(16) 0.0058(16) 0.0151(14) 0.0117(17) C33 0.063(2) 0.048(2) 0.0445(16) 0.0004(15) 0.0094(15) 0.0100(17) C34 0.0491(16) 0.050(2) 0.0417(14) 0.0030(15) 0.0115(13) 0.0047(16) C35 0.0477(17) 0.051(2) 0.0561(18) 0.0003(16) 0.0207(14) 0.0016(17) C38 0.070(2) 0.048(2) 0.063(2) -0.0028(19) 0.0086(18) 0.004(2) O36 0.0786(17) 0.0601(19) 0.0498(13) -0.0098(13) -0.0004(12) 0.0231(16) O37 0.092(2) 0.070(2) 0.0451(12) 0.0072(13) 0.0174(12) 0.0229(17) O39 0.125(3) 0.056(2) 0.0694(19) -0.0018(15) -0.0025(19) -0.020(2) N41 0.0602(17) 0.0402(16) 0.0454(14) -0.0016(12) 0.0110(12) 0.0034(14) N43 0.0506(14) 0.0390(15) 0.0407(13) 0.0039(12) 0.0136(11) 0.0052(13) N45 0.0515(14) 0.0351(14) 0.0377(12) 0.0000(11) 0.0131(10) 0.0022(13) N47 0.0529(14) 0.0376(15) 0.0430(13) 0.0029(12) 0.0106(11) 0.0025(13) N50 0.0694(18) 0.0445(18) 0.0439(14) -0.0021(13) 0.0000(13) 0.0042(16) C42 0.0622(19) 0.0372(19) 0.0498(17) 0.0000(15) 0.0165(15) 0.0046(17) C44 0.0433(15) 0.0365(17) 0.0371(13) 0.0025(12) 0.0142(12) 0.0010(14) C46 0.0564(18) 0.0370(18) 0.0451(16) 0.0014(14) 0.0143(14) 0.0017(16) C48 0.0440(15) 0.0399(18) 0.0403(14) 0.0057(13) 0.0146(12) -0.0009(14) C49 0.0478(16) 0.0406(19) 0.0411(14) 0.0001(14) 0.0138(13) -0.0021(15) C51 0.0515(17) 0.045(2) 0.0404(15) -0.0006(14) 0.0103(13) 0.0026(16) C52 0.0525(17) 0.050(2) 0.0406(15) -0.0003(14) 0.0164(13) -0.0067(16) C53 0.074(2) 0.054(2) 0.0381(15) 0.0024(16) 0.0128(15) -0.010(2) C54 0.0524(17) 0.047(2) 0.0407(15) -0.0032(14) 0.0092(13) 0.0023(16) C55 0.0452(15) 0.0418(19) 0.0458(15) -0.0021(13) 0.0104(13) -0.0001(15) C58 0.0590(19) 0.043(2) 0.065(2) 0.0007(17) 0.0131(17) -0.0059(17) O56 0.0555(12) 0.0471(14) 0.0445(11) 0.0069(10) 0.0031(10) -0.0091(12) O57 0.0624(14) 0.0573(17) 0.0544(13) -0.0111(13) -0.0038(11) 0.0049(14) O59 0.0503(13) 0.0646(19) 0.0697(15) 0.0214(14) 0.0094(11) -0.0051(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' N N 0.0311 0.0180 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C9 118.8(3) . . ? C2 N3 C4 110.7(3) . . ? C4 N5 C6 106.0(2) . . ? C4 N5 C11 123.7(3) . . ? C6 N5 C11 130.3(3) . . ? C6 N7 C8 104.0(3) . . ? C9 N10 H101 120.0 . . ? C9 N10 H102 120.0 . . ? H101 N10 H102 120.0 . . ? N3 C2 N1 128.9(4) . . ? N3 C2 H2 115.6 . . ? N1 C2 H2 115.6 . . ? N3 C4 N5 126.5(3) . . ? N3 C4 C8 127.3(3) . . ? N5 C4 C8 106.2(3) . . ? N7 C6 N5 113.3(3) . . ? N7 C6 H6 123.3 . . ? N5 C6 H6 123.3 . . ? N7 C8 C4 110.5(3) . . ? N7 C8 C9 132.9(3) . . ? C4 C8 C9 116.6(3) . . ? N10 C9 N1 117.5(3) . . ? N10 C9 C8 124.8(3) . . ? N1 C9 C8 117.8(3) . . ? N5 C11 C12 114.2(3) . . ? N5 C11 H111 108.7 . . ? C12 C11 H111 108.7 . . ? N5 C11 H112 108.7 . . ? C12 C11 H112 108.7 . . ? H111 C11 H112 107.6 . . ? O16 C12 C11 109.7(3) . . ? O16 C12 C13 106.0(3) . . ? C11 C12 C13 111.7(3) . . ? O16 C12 H12 109.8 . . ? C11 C12 H12 109.8 . . ? C13 C12 H12 109.8 . . ? C14 C13 C12 102.5(3) . . ? C14 C13 H131 111.3 . . ? C12 C13 H131 111.3 . . ? C14 C13 H132 111.3 . . ? C12 C13 H132 111.3 . . ? H131 C13 H132 109.2 . . ? O17 C14 C13 114.3(3) . . ? O17 C14 C15 114.2(3) . . ? C13 C14 C15 103.0(2) . . ? O17 C14 H14 108.4 . . ? C13 C14 H14 108.4 . . ? C15 C14 H14 108.4 . . ? O16 C15 C18 109.6(3) . . ? O16 C15 C14 105.7(3) . . ? C18 C15 C14 113.9(3) . . ? O16 C15 H15 109.2 . . ? C18 C15 H15 109.2 . . ? C14 C15 H15 109.2 . . ? O19 C18 C15 112.2(3) . . ? O19 C18 H181 109.2 . . ? C15 C18 H181 109.2 . . ? O19 C18 H182 109.2 . . ? C15 C18 H182 109.2 . . ? H181 C18 H182 107.9 . . ? C15 O16 C12 111.4(3) . . ? C14 O17 H17 109.5 . . ? C18 O19 H19 109.5 . . ? C22 N21 C29 118.9(3) . . ? C22 N23 C24 110.6(3) . . ? C26 N25 C24 106.0(2) . . ? C26 N25 C31 127.6(3) . . ? C24 N25 C31 126.3(3) . . ? C26 N27 C28 103.6(3) . . ? C29 N30 H301 120.0 . . ? C29 N30 H302 120.0 . . ? H301 N30 H302 120.0 . . ? N23 C22 N21 129.6(4) . . ? N23 C22 H22 115.2 . . ? N21 C22 H22 115.2 . . ? N23 C24 N25 127.6(3) . . ? N23 C24 C28 126.8(3) . . ? N25 C24 C28 105.6(3) . . ? N27 C26 N25 114.2(3) . . ? N27 C26 H26 122.9 . . ? N25 C26 H26 122.9 . . ? N27 C28 C24 110.5(3) . . ? N27 C28 C29 132.6(3) . . ? C24 C28 C29 116.9(3) . . ? N30 C29 N21 119.0(3) . . ? N30 C29 C28 123.8(3) . . ? N21 C29 C28 117.2(3) . . ? N25 C31 C32 112.9(3) . . ? N25 C31 H311 109.0 . . ? C32 C31 H311 109.0 . . ? N25 C31 H312 109.0 . . ? C32 C31 H312 109.0 . . ? H311 C31 H312 107.8 . . ? O36 C32 C31 109.9(3) . . ? O36 C32 C33 106.3(3) . . ? C31 C32 C33 111.9(3) . . ? O36 C32 H32 109.6 . . ? C31 C32 H32 109.6 . . ? C33 C32 H32 109.6 . . ? C34 C33 C32 102.8(3) . . ? C34 C33 H331 111.2 . . ? C32 C33 H331 111.2 . . ? C34 C33 H332 111.2 . . ? C32 C33 H332 111.2 . . ? H331 C33 H332 109.1 . . ? O37 C34 C33 110.3(3) . . ? O37 C34 C35 114.4(3) . . ? C33 C34 C35 102.2(3) . . ? O37 C34 H34 109.9 . . ? C33 C34 H34 109.9 . . ? C35 C34 H34 109.9 . . ? O36 C35 C38 109.5(3) . . ? O36 C35 C34 104.7(3) . . ? C38 C35 C34 115.0(3) . . ? O36 C35 H35 109.2 . . ? C38 C35 H35 109.2 . . ? C34 C35 H35 109.2 . . ? O39 C38 C35 115.0(4) . . ? O39 C38 H381 108.5 . . ? C35 C38 H381 108.5 . . ? O39 C38 H382 108.5 . . ? C35 C38 H382 108.5 . . ? H381 C38 H382 107.5 . . ? C32 O36 C35 110.0(3) . . ? C34 O37 H37 109.5 . . ? C38 O39 H39 109.5 . . ? C42 N41 C49 118.5(3) . . ? C42 N43 C44 110.8(3) . . ? C44 N45 C46 106.2(2) . . ? C44 N45 C51 124.5(3) . . ? C46 N45 C51 129.1(3) . . ? C46 N47 C48 104.0(3) . . ? C49 N50 H501 120.0 . . ? C49 N50 H502 120.0 . . ? H501 N50 H502 120.0 . . ? N43 C42 N41 129.3(3) . . ? N43 C42 H42 115.3 . . ? N41 C42 H42 115.3 . . ? N43 C44 N45 127.3(3) . . ? N43 C44 C48 126.7(3) . . ? N45 C44 C48 106.0(3) . . ? N47 C46 N45 113.5(3) . . ? N47 C46 H46 123.3 . . ? N45 C46 H46 123.3 . . ? N47 C48 C44 110.3(3) . . ? N47 C48 C49 133.4(3) . . ? C44 C48 C49 116.3(3) . . ? N41 C49 N50 118.8(3) . . ? N41 C49 C48 118.3(3) . . ? N50 C49 C48 122.9(3) . . ? N45 C51 C52 114.3(3) . . ? N45 C51 H511 108.7 . . ? C52 C51 H511 108.7 . . ? N45 C51 H512 108.7 . . ? C52 C51 H512 108.7 . . ? H511 C51 H512 107.6 . . ? O56 C52 C51 111.8(3) . . ? O56 C52 C53 106.4(3) . . ? C51 C52 C53 110.8(3) . . ? O56 C52 H52 109.3 . . ? C51 C52 H52 109.3 . . ? C53 C52 H52 109.3 . . ? C54 C53 C52 104.4(3) . . ? C54 C53 H531 110.9 . . ? C52 C53 H531 110.9 . . ? C54 C53 H532 110.9 . . ? C52 C53 H532 110.9 . . ? H531 C53 H532 108.9 . . ? O57 C54 C53 115.5(3) . . ? O57 C54 C55 113.7(3) . . ? C53 C54 C55 102.5(3) . . ? O57 C54 H54 108.3 . . ? C53 C54 H54 108.3 . . ? C55 C54 H54 108.3 . . ? O56 C55 C58 109.4(3) . . ? O56 C55 C54 104.7(3) . . ? C58 C55 C54 113.0(3) . . ? O56 C55 H55 109.9 . . ? C58 C55 H55 109.9 . . ? C54 C55 H55 109.9 . . ? O59 C58 C55 113.9(3) . . ? O59 C58 H581 108.8 . . ? C55 C58 H581 108.8 . . ? O59 C58 H582 108.8 . . ? C55 C58 H582 108.8 . . ? H581 C58 H582 107.7 . . ? C55 O56 C52 109.1(2) . . ? C54 O57 H57 109.5 . . ? C58 O59 H59 109.5 . . ? 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 N1 C2 1.338(4) . ? N1 C9 1.357(5) . ? N3 C2 1.333(5) . ? N3 C4 1.343(5) . ? N5 C4 1.367(4) . ? N5 C6 1.370(5) . ? N5 C11 1.467(4) . ? N7 C6 1.321(4) . ? N7 C8 1.383(5) . ? N10 C9 1.328(4) . ? N10 H101 0.8800 . ? N10 H102 0.8800 . ? C2 H2 0.9500 . ? C4 C8 1.383(4) . ? C6 H6 0.9500 . ? C8 C9 1.403(4) . ? C11 C12 1.491(5) . ? C11 H111 0.9900 . ? C11 H112 0.9900 . ? C12 O16 1.425(5) . ? C12 C13 1.529(4) . ? C12 H12 1.0000 . ? C13 C14 1.511(6) . ? C13 H131 0.9900 . ? C13 H132 0.9900 . ? C14 O17 1.415(4) . ? C14 C15 1.534(5) . ? C14 H14 1.0000 . ? C15 O16 1.416(4) . ? C15 C18 1.501(6) . ? C15 H15 1.0000 . ? C18 O19 1.412(5) . ? C18 H181 0.9900 . ? C18 H182 0.9900 . ? O17 H17 0.8400 . ? O19 H19 0.8400 . ? N21 C22 1.334(4) . ? N21 C29 1.350(5) . ? N23 C22 1.323(5) . ? N23 C24 1.340(5) . ? N25 C26 1.359(5) . ? N25 C24 1.366(5) . ? N25 C31 1.471(4) . ? N27 C26 1.310(4) . ? N27 C28 1.381(5) . ? N30 C29 1.329(4) . ? N30 H301 0.8800 . ? N30 H302 0.8800 . ? C22 H22 0.9500 . ? C24 C28 1.390(4) . ? C26 H26 0.9500 . ? C28 C29 1.411(5) . ? C31 C32 1.489(5) . ? C31 H311 0.9900 . ? C31 H312 0.9900 . ? C32 O36 1.430(5) . ? C32 C33 1.530(5) . ? C32 H32 1.0000 . ? C33 C34 1.508(6) . ? C33 H331 0.9900 . ? C33 H332 0.9900 . ? C34 O37 1.411(4) . ? C34 C35 1.515(5) . ? C34 H34 1.0000 . ? C35 O36 1.432(5) . ? C35 C38 1.495(6) . ? C35 H35 1.0000 . ? C38 O39 1.400(6) . ? C38 H381 0.9900 . ? C38 H382 0.9900 . ? O37 H37 0.8400 . ? O39 H39 0.8400 . ? N41 C42 1.330(4) . ? N41 C49 1.344(5) . ? N43 C42 1.325(5) . ? N43 C44 1.340(4) . ? N45 C44 1.361(4) . ? N45 C46 1.369(4) . ? N45 C51 1.473(4) . ? N47 C46 1.315(4) . ? N47 C48 1.382(5) . ? N50 C49 1.346(4) . ? N50 H501 0.8800 . ? N50 H502 0.8800 . ? C42 H42 0.9500 . ? C44 C48 1.388(4) . ? C46 H46 0.9500 . ? C48 C49 1.402(5) . ? C51 C52 1.498(5) . ? C51 H511 0.9900 . ? C51 H512 0.9900 . ? C52 O56 1.439(4) . ? C52 C53 1.535(5) . ? C52 H52 1.0000 . ? C53 C54 1.509(6) . ? C53 H531 0.9900 . ? C53 H532 0.9900 . ? C54 O57 1.410(4) . ? C54 C55 1.519(5) . ? C54 H54 1.0000 . ? C55 O56 1.431(4) . ? C55 C58 1.501(5) . ? C55 H55 1.0000 . ? C58 O59 1.412(5) . ? C58 H581 0.9900 . ? C58 H582 0.9900 . ? O57 H57 0.8400 . ? O59 H59 0.8400 . ? 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 N10 H101 N47 0.88 2.16 3.001(4) 160.5 1_464 yes N10 H102 N41 0.88 2.15 2.985(4) 157.9 1_454 yes O17 H17 O59 0.84 1.88 2.714(4) 170.2 1_565 yes O19 H19 N3 0.84 1.97 2.794(4) 168.4 1_545 yes N30 H301 N27 0.88 2.16 3.027(4) 166.4 2_747 yes N30 H302 N21 0.88 2.13 2.965(5) 158.8 2_757 yes O37 H37 O17 0.84 1.92 2.736(4) 165.3 . yes O39 H39 N23 0.84 2.15 2.926(4) 152.8 1_565 yes N50 H501 N7 0.88 2.21 3.090(4) 174.4 1_656 yes N50 H502 N1 0.88 2.10 2.940(5) 160.3 1_646 yes O57 H57 O19 0.84 1.95 2.768(4) 164.8 . yes O59 H59 N43 0.84 1.97 2.798(4) 167.5 1_545 yes