#------------------------------------------------------------------------------ #$Date: 2017-07-17 12:27:47 +0300 (Mon, 17 Jul 2017) $ #$Revision: 198755 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242104.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2242104 loop_ _publ_author_name 'Chidan Kumar, C. S.' 'Sim, Ai Jia' 'Ng, Weng Zhun' 'Chia, Tze Shyang' 'Loh, Wan-Sin' 'Kwong, Huey Chong' 'Quah, Ching Kheng' 'Naveen, S.' 'Lokanath, N. K.' 'Warad, Ismail' _publ_section_title ; The crystal structure of zwitterionic 2-{[(4-iminiumyl-3-methyl-1,4-dihydropyridin-1-yl)methyl]carbamoyl}benzoate hemihydrate ; _journal_coeditor_code SJ5531 _journal_issue 7 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first 927 _journal_page_last 931 _journal_paper_doi 10.1107/S2056989017007836 _journal_volume 73 _journal_year 2017 _chemical_formula_iupac 'C15 H15 N3 O3, 0.5H2 O' _chemical_formula_moiety 'C15 H15 N3 O3, 0.5(H2 O)' _chemical_formula_sum 'C15 H16 N3 O3.5' _chemical_formula_weight 294.31 _chemical_name_systematic ; 2-{[(4-Iminiumyl-3-methyl-1,4-dihydropyridin-1-yl)methyl]carbamoyl}benzoate hemihydrate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _cell_angle_alpha 90 _cell_angle_beta 103.729(2) _cell_angle_gamma 90 _cell_formula_units_Z 16 _cell_length_a 21.3157(18) _cell_length_b 11.9883(8) _cell_length_c 22.8642(15) _cell_measurement_reflns_used 8600 _cell_measurement_temperature 294 _cell_measurement_theta_max 21.24 _cell_measurement_theta_min 2.35 _cell_volume 5675.8(7) _computing_cell_refinement ; SAINT (Bruker, 2012) ; _computing_data_collection ; APEX2 (Bruker, 2012) ; _computing_data_reduction ; SAINT (Bruker, 2012) ; _computing_molecular_graphics ; SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al., 2006) ; _computing_publication_material ; SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009) ; _computing_structure_refinement ; SHELXL2013 (Sheldrick, 2015) ; _computing_structure_solution ; SHELXS97 (Sheldrick, 2008) ; _diffrn_ambient_temperature 294 _diffrn_detector_area_resol_mean 18.4 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEXII DUO CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 65196 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.24 _diffrn_reflns_theta_max 25.81 _diffrn_reflns_theta_min 1.83 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2014/5' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description block _exptl_crystal_F_000 2480 _exptl_crystal_size_max 0.282 _exptl_crystal_size_mid 0.262 _exptl_crystal_size_min 0.131 _refine_diff_density_max 0.483 _refine_diff_density_min -0.286 _refine_ls_abs_structure_Flack . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 414 _refine_ls_number_reflns 5430 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0465 _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^)+(0.0647P)^2^+3.8981P] where P=(FO^2^+2FC^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1191 _refine_ls_wR_factor_ref 0.1362 _reflns_number_gt 3849 _reflns_number_total 5430 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL a in C2/c CELL 0.71073 21.31567 11.98830 22.86420 90.0000 103.7289 90.0000 ZERR 8.00 0.00179 0.00080 0.00150 0.0000 0.0024 0.0000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O UNIT 240 256 48 56 TEMP 21.000 SIZE 0.131 0.262 0.282 L.S. 10 BOND $H FMAP 2 2 60 PLAN 20 ACTA CONF rem DFIX 0.85 0.01 O1W H1W1 O1W H2W1 rem DANG 1.34 0.01 H1W1 H2W1 WGHT 0.064700 3.898100 FVAR 0.20288 O1A 4 0.225834 0.401059 0.400318 11.00000 0.06009 0.03819 = 0.06497 -0.00169 0.01286 0.01084 O2A 4 0.343332 0.408487 0.335647 11.00000 0.09763 0.06412 = 0.04869 0.00788 0.00961 -0.01386 O3A 4 0.385356 0.533159 0.407103 11.00000 0.09424 0.04960 = 0.07577 -0.00401 0.04767 -0.01607 N1A 3 0.110352 0.258574 0.314409 11.00000 0.03412 0.04015 = 0.03900 0.00260 0.01054 -0.00230 N2A 3 0.226525 0.238447 0.351553 11.00000 0.03429 0.03736 = 0.05166 -0.00160 0.01035 0.00187 H2N2 2 0.248478 0.178055 0.348067 11.00000 0.03593 N3A 3 -0.069185 0.215687 0.347587 11.00000 0.03981 0.04915 = 0.05801 0.00386 0.02031 0.00022 H2N3 2 -0.089270 0.279525 0.357956 11.00000 0.07501 H1N3 2 -0.082137 0.147356 0.357492 11.00000 0.07209 C1A 1 0.073528 0.347657 0.319381 11.00000 0.04385 0.03752 = 0.04179 0.00252 0.00988 -0.00186 AFIX 43 H1AA 2 0.089420 0.419035 0.316067 11.00000 -1.20000 AFIX 0 C2A 1 0.014053 0.335052 0.329078 11.00000 0.04343 0.03816 = 0.04235 0.00207 0.01274 0.00598 AFIX 43 H2AA 2 -0.010826 0.397888 0.331406 11.00000 -1.20000 AFIX 0 C3A 1 -0.011202 0.228509 0.335763 11.00000 0.03664 0.04444 = 0.03232 0.00201 0.00742 -0.00007 C4A 1 0.027538 0.135300 0.329047 11.00000 0.04100 0.04004 = 0.04533 -0.00102 0.01434 -0.00263 C5A 1 0.086700 0.154684 0.318522 11.00000 0.04121 0.03894 = 0.04805 -0.00022 0.01335 0.00398 AFIX 43 H5AA 2 0.112151 0.093816 0.313927 11.00000 -1.20000 AFIX 0 C6A 1 0.004237 0.018504 0.333758 11.00000 0.06182 0.04278 = 0.10057 0.00226 0.03817 -0.00438 AFIX 137 H6AA 2 -0.037103 0.008918 0.306282 11.00000 -1.50000 H6AB 2 0.000335 0.004937 0.374123 11.00000 -1.50000 H6AC 2 0.034547 -0.033189 0.323888 11.00000 -1.50000 AFIX 0 C7A 1 0.175137 0.271998 0.302302 11.00000 0.03664 0.04971 = 0.04526 0.00447 0.01296 -0.00240 AFIX 23 H7AA 2 0.177191 0.228222 0.267126 11.00000 -1.20000 H7AB 2 0.181232 0.349654 0.293093 11.00000 -1.20000 AFIX 0 C8A 1 0.252604 0.313083 0.394861 11.00000 0.04250 0.03387 = 0.04552 0.00517 0.01713 -0.00150 C9A 1 0.315668 0.282112 0.436076 11.00000 0.04130 0.03909 = 0.03649 -0.00080 0.01265 0.00139 C10A 1 0.320822 0.195642 0.476930 11.00000 0.05646 0.04423 = 0.04900 0.00441 0.01920 0.00024 AFIX 43 H10A 2 0.284877 0.151976 0.477376 11.00000 -1.20000 AFIX 0 C11A 1 0.378953 0.173561 0.517115 11.00000 0.07246 0.05827 = 0.04189 0.01074 0.01268 0.00773 AFIX 43 H11A 2 0.382072 0.115176 0.544438 11.00000 -1.20000 AFIX 0 C12A 1 0.431747 0.237511 0.516650 11.00000 0.06109 0.07702 = 0.03661 -0.00116 0.00223 0.01356 AFIX 43 H12A 2 0.471001 0.221886 0.543323 11.00000 -1.20000 AFIX 0 C13A 1 0.427243 0.325149 0.476872 11.00000 0.04436 0.06232 = 0.04913 -0.00718 0.00994 -0.00555 AFIX 43 H13A 2 0.463270 0.369335 0.477552 11.00000 -1.20000 AFIX 0 C14A 1 0.369556 0.348048 0.435884 11.00000 0.04320 0.04593 = 0.03705 -0.00221 0.01346 0.00009 C15A 1 0.365047 0.438519 0.389314 11.00000 0.05191 0.04454 = 0.05744 -0.00008 0.02428 -0.00819 O1B 4 0.339466 0.043303 0.230608 11.00000 0.07940 0.04553 = 0.04846 -0.00841 -0.00146 0.01021 O3B 4 0.358519 -0.109859 0.386746 11.00000 0.06579 0.04231 = 0.07750 0.02037 0.02767 0.00708 O2B 4 0.293294 0.029044 0.347757 11.00000 0.03938 0.04269 = 0.07650 0.00349 0.01026 0.00059 N1B 3 0.293463 0.241855 0.133437 11.00000 0.04317 0.03911 = 0.04446 0.00692 0.01154 0.00523 N2B 3 0.322198 0.226084 0.242850 11.00000 0.05380 0.03705 = 0.04377 0.00666 0.01319 0.00609 H1N2 2 0.331122 0.284626 0.268239 11.00000 0.08697 N3B 3 0.352852 0.277766 -0.024106 11.00000 0.05845 0.04758 = 0.04614 -0.00748 0.01754 0.00494 H4N3 2 0.353744 0.218863 -0.047121 11.00000 0.06017 H3N3 2 0.362937 0.348602 -0.038203 11.00000 0.07710 C1B 1 0.298523 0.152024 0.099854 11.00000 0.04183 0.03778 = 0.05220 0.00543 0.00454 -0.00001 AFIX 43 H1BA 2 0.288610 0.081933 0.112601 11.00000 -1.20000 AFIX 0 C2B 1 0.317836 0.161548 0.047637 11.00000 0.04178 0.03763 = 0.04915 -0.00550 0.00254 0.00565 AFIX 43 H2BA 2 0.320878 0.097942 0.025188 11.00000 -1.20000 AFIX 0 C3B 1 0.333335 0.266138 0.026916 11.00000 0.03143 0.04331 = 0.04059 -0.00044 0.00439 0.00676 C4B 1 0.326689 0.360499 0.062723 11.00000 0.04318 0.03583 = 0.04129 0.00102 0.01003 0.00275 C5B 1 0.306836 0.343837 0.114342 11.00000 0.04838 0.03618 = 0.04325 0.00297 0.01195 0.00450 AFIX 43 H5BA 2 0.302245 0.405566 0.137608 11.00000 -1.20000 AFIX 0 C6B 1 0.338684 0.475647 0.042773 11.00000 0.08617 0.04339 = 0.05164 -0.00041 0.02456 -0.00425 AFIX 137 H6BA 2 0.310808 0.489855 0.003893 11.00000 -1.50000 H6BB 2 0.382898 0.482125 0.040391 11.00000 -1.50000 H6BC 2 0.330048 0.528914 0.071222 11.00000 -1.50000 AFIX 0 C7B 1 0.270552 0.230891 0.189632 11.00000 0.04847 0.05290 = 0.04956 0.01516 0.01891 0.00615 AFIX 23 H7BA 2 0.242990 0.293896 0.192777 11.00000 -1.20000 H7BB 2 0.244723 0.163697 0.187286 11.00000 -1.20000 AFIX 0 C8B 1 0.352139 0.128398 0.260475 11.00000 0.04945 0.03612 = 0.04006 0.00248 0.01613 0.00224 C9B 1 0.405178 0.131265 0.316469 11.00000 0.03904 0.03825 = 0.04431 -0.00349 0.01401 0.00023 C10B 1 0.458388 0.198770 0.318293 11.00000 0.05747 0.06065 = 0.06523 0.00541 0.02343 -0.01329 AFIX 43 H10B 2 0.458143 0.248453 0.287001 11.00000 -1.20000 AFIX 0 C11B 1 0.511782 0.192894 0.366189 11.00000 0.04709 0.08044 = 0.09071 -0.00562 0.01115 -0.02255 AFIX 43 H11B 2 0.547357 0.238245 0.366920 11.00000 -1.20000 AFIX 0 C12B 1 0.512399 0.120421 0.412569 11.00000 0.04235 0.08189 = 0.06738 -0.00846 0.00079 -0.00556 AFIX 43 H12B 2 0.548457 0.116104 0.444692 11.00000 -1.20000 AFIX 0 C13B 1 0.459614 0.054085 0.411537 11.00000 0.04738 0.05833 = 0.04633 -0.00125 0.00619 0.00308 AFIX 43 H13B 2 0.460272 0.005332 0.443316 11.00000 -1.20000 AFIX 0 C14B 1 0.405385 0.058357 0.364075 11.00000 0.03780 0.03622 = 0.03797 -0.00401 0.01052 0.00349 C15B 1 0.347647 -0.013488 0.366019 11.00000 0.04352 0.03430 = 0.03961 0.00086 0.01311 0.00319 O1W 4 0.182244 0.022348 0.262987 11.00000 0.06486 0.13159 = 0.07521 -0.03855 0.00743 0.02132 AFIX 3 H1W1 2 0.222184 0.014128 0.282037 11.00000 -1.50000 H2W1 2 0.175974 -0.036372 0.240427 11.00000 -1.50000 HKLF 4 1 1 2 0 -1 0 0 0 0 1 REM a in C2/c REM R1 = 0.0465 for 3847 Fo > 4sig(Fo) and 0.0714 for all 5430 data REM 414 parameters refined using 0 restraints END WGHT 0.0647 3.9097 REM Highest difference peak 0.482, deepest hole -0.285, 1-sigma level 0.041 Q1 1 0.3242 0.4746 0.3566 11.00000 0.05 0.48 Q2 1 0.1769 -0.0622 0.2611 11.00000 0.05 0.40 Q3 1 0.4146 0.5568 0.4441 11.00000 0.05 0.28 Q4 1 0.1786 -0.0080 0.2133 11.00000 0.05 0.23 Q5 1 0.3196 0.0739 0.0081 11.00000 0.05 0.19 Q6 1 0.3227 0.3219 0.0425 11.00000 0.05 0.17 Q7 1 0.3419 0.3305 0.4428 11.00000 0.05 0.15 Q8 1 0.3633 -0.0817 0.3640 11.00000 0.05 0.14 Q9 1 0.3032 0.1405 0.4015 11.00000 0.05 0.14 Q10 1 0.0018 0.1781 0.3293 11.00000 0.05 0.14 Q11 1 0.3612 0.5711 0.3800 11.00000 0.05 0.14 Q12 1 0.0244 0.1623 0.3442 11.00000 0.05 0.14 Q13 1 0.2732 0.1697 0.1629 11.00000 0.05 0.13 Q14 1 0.4018 -0.1200 0.4234 11.00000 0.05 0.13 Q15 1 0.1020 0.1115 0.3012 11.00000 0.05 0.13 Q16 1 0.2400 -0.1183 0.2220 11.00000 0.05 0.13 Q17 1 0.0844 0.2998 0.3011 11.00000 0.05 0.13 Q18 1 0.1795 0.4609 0.4399 11.00000 0.05 0.12 Q19 1 0.0216 0.0898 0.3382 11.00000 0.05 0.12 Q20 1 0.1644 0.1873 0.2574 11.00000 0.05 0.12 ; _cod_data_source_file sj5531.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2242104 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,1/2-z 3 -x,-y,-z 4 x,-y,1/2+z 5 1/2+x,1/2+y,z 6 1/2-x,1/2+y,1/2-z 7 1/2-x,1/2-y,-z 8 1/2+x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1A 0.0601(10) 0.0382(8) 0.0649(10) 0.0109(7) 0.0128(8) -0.0017(7) O2A 0.0976(14) 0.0641(11) 0.0488(10) -0.0138(10) 0.0096(9) 0.0080(8) O3A 0.0942(14) 0.0495(10) 0.0758(12) -0.0161(9) 0.0477(10) -0.0041(9) N1A 0.0341(9) 0.0401(9) 0.0390(9) -0.0023(7) 0.0105(7) 0.0026(7) N2A 0.0343(9) 0.0373(10) 0.0516(11) 0.0018(8) 0.0104(8) -0.0016(8) N3A 0.0398(11) 0.0490(12) 0.0581(12) 0.0002(9) 0.0204(9) 0.0038(10) C1A 0.0438(12) 0.0375(11) 0.0418(11) -0.0019(9) 0.0099(9) 0.0025(9) C2A 0.0434(12) 0.0381(11) 0.0424(11) 0.0060(9) 0.0127(9) 0.0021(9) C3A 0.0367(11) 0.0444(11) 0.0323(10) -0.0001(9) 0.0074(8) 0.0020(8) C4A 0.0411(12) 0.0400(11) 0.0452(12) -0.0026(9) 0.0143(9) -0.0010(9) C5A 0.0411(12) 0.0389(11) 0.0480(12) 0.0040(9) 0.0133(9) -0.0003(9) C6A 0.0618(16) 0.0428(13) 0.100(2) -0.0044(12) 0.0381(15) 0.0023(13) C7A 0.0366(11) 0.0497(12) 0.0452(12) -0.0024(9) 0.0129(9) 0.0045(9) C8A 0.0425(12) 0.0339(11) 0.0455(11) -0.0015(9) 0.0171(9) 0.0052(9) C9A 0.0413(11) 0.0391(11) 0.0365(10) 0.0014(9) 0.0127(9) -0.0008(8) C10A 0.0564(14) 0.0443(12) 0.0490(13) 0.0002(10) 0.0192(11) 0.0044(10) C11A 0.0724(17) 0.0582(15) 0.0419(12) 0.0077(13) 0.0126(12) 0.0107(11) C12A 0.0611(16) 0.0770(17) 0.0366(12) 0.0135(14) 0.0022(11) -0.0013(12) C13A 0.0444(13) 0.0623(15) 0.0491(13) -0.0056(11) 0.0099(10) -0.0072(11) C14A 0.0432(12) 0.0459(12) 0.0370(11) 0.0001(9) 0.0134(9) -0.0022(9) C15A 0.0519(14) 0.0446(13) 0.0573(14) -0.0082(10) 0.0242(11) -0.0001(11) O1B 0.0794(12) 0.0455(9) 0.0485(9) 0.0102(8) -0.0015(8) -0.0085(7) O2B 0.0394(9) 0.0426(9) 0.0765(11) 0.0006(7) 0.0102(8) 0.0035(8) O3B 0.0658(11) 0.0423(9) 0.0775(11) 0.0070(8) 0.0277(9) 0.0203(8) N1B 0.0431(10) 0.0390(10) 0.0444(10) 0.0052(8) 0.0116(8) 0.0069(8) N2B 0.0538(11) 0.0369(10) 0.0439(10) 0.0061(8) 0.0133(9) 0.0066(8) N3B 0.0584(12) 0.0475(12) 0.0461(11) 0.0049(10) 0.0176(9) -0.0073(10) C1B 0.0418(12) 0.0378(12) 0.0522(13) 0.0000(9) 0.0046(10) 0.0054(10) C2B 0.0418(12) 0.0376(11) 0.0492(12) 0.0057(9) 0.0025(10) -0.0055(9) C3B 0.0315(10) 0.0432(11) 0.0405(11) 0.0067(9) 0.0044(9) -0.0004(9) C4B 0.0432(12) 0.0358(11) 0.0412(11) 0.0028(9) 0.0100(9) 0.0011(9) C5B 0.0483(12) 0.0362(11) 0.0433(11) 0.0045(9) 0.0120(9) 0.0030(9) C6B 0.0861(18) 0.0434(13) 0.0516(14) -0.0042(12) 0.0246(13) -0.0004(10) C7B 0.0484(13) 0.0529(13) 0.0495(13) 0.0062(10) 0.0189(11) 0.0153(10) C8B 0.0494(12) 0.0362(11) 0.0401(11) 0.0022(9) 0.0161(9) 0.0025(9) C9B 0.0391(11) 0.0382(11) 0.0443(11) 0.0002(9) 0.0140(9) -0.0035(9) C10B 0.0575(15) 0.0606(15) 0.0652(16) -0.0133(12) 0.0235(13) 0.0054(12) C11B 0.0470(15) 0.080(2) 0.091(2) -0.0225(14) 0.0111(14) -0.0056(16) C12B 0.0423(14) 0.0819(19) 0.0674(17) -0.0056(13) 0.0008(12) -0.0084(15) C13B 0.0473(13) 0.0583(14) 0.0463(12) 0.0031(11) 0.0062(10) -0.0013(11) C14B 0.0378(11) 0.0362(10) 0.0379(11) 0.0035(9) 0.0105(9) -0.0040(8) C15B 0.0435(12) 0.0343(11) 0.0396(11) 0.0032(9) 0.0131(9) 0.0008(9) O1W 0.0648(12) 0.1316(19) 0.0752(13) 0.0212(12) 0.0074(10) -0.0386(12) loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1A 0.22583(8) 0.40107(12) 0.40032(7) 0.0547(5) Uani d . 1.000 . . O O2A 0.34333(10) 0.40853(15) 0.33565(7) 0.0715(7) Uani d . 1.000 . . O O3A 0.38535(9) 0.53318(14) 0.40709(8) 0.0686(7) Uani d . 1.000 . . N N1A 0.11034(8) 0.25855(14) 0.31440(7) 0.0374(5) Uani d . 1.000 . . N N2A 0.22652(8) 0.23844(15) 0.35155(8) 0.0410(6) Uani d . 1.000 . . N N3A -0.06918(9) 0.2157(2) 0.34758(9) 0.0475(7) Uani d . 1.000 . . C C1A 0.07352(10) 0.34764(17) 0.31936(9) 0.0411(7) Uani d . 1.000 . . C C2A 0.01405(10) 0.33503(17) 0.32906(9) 0.0409(7) Uani d . 1.000 . . C C3A -0.01122(10) 0.22851(17) 0.33576(8) 0.0379(6) Uani d . 1.000 . . C C4A 0.02754(10) 0.13531(17) 0.32905(9) 0.0414(7) Uani d . 1.000 . . C C5A 0.08670(10) 0.15470(17) 0.31853(9) 0.0422(7) Uani d . 1.000 . . C C6A 0.00423(13) 0.01857(19) 0.33375(14) 0.0650(10) Uani d . 1.000 . . C C7A 0.17511(10) 0.27198(19) 0.30229(9) 0.0433(7) Uani d . 1.000 . . C C8A 0.25260(10) 0.31309(17) 0.39486(9) 0.0395(7) Uani d . 1.000 . . C C9A 0.31568(10) 0.28213(16) 0.43608(9) 0.0384(6) Uani d . 1.000 . . C C10A 0.32083(12) 0.19564(18) 0.47694(10) 0.0488(8) Uani d . 1.000 . . C C11A 0.37896(13) 0.1736(2) 0.51714(10) 0.0577(9) Uani d . 1.000 . . C C12A 0.43176(13) 0.2375(2) 0.51666(10) 0.0598(9) Uani d . 1.000 . . C C13A 0.42725(11) 0.3252(2) 0.47687(10) 0.0521(8) Uani d . 1.000 . . C C14A 0.36955(10) 0.34807(18) 0.43589(9) 0.0414(7) Uani d . 1.000 . . C C15A 0.36504(11) 0.43856(19) 0.38932(11) 0.0494(8) Uani d . 1.000 . . O O1B 0.33946(9) 0.04329(13) 0.23061(7) 0.0606(6) Uani d . 1.000 . . O O2B 0.29329(7) 0.02903(12) 0.34775(7) 0.0534(6) Uani d . 1.000 . . O O3B 0.35853(8) -0.10987(13) 0.38676(8) 0.0601(6) Uani d . 1.000 . . N N1B 0.29345(8) 0.24185(14) 0.13343(8) 0.0420(6) Uani d . 1.000 . . N N2B 0.32218(9) 0.22607(16) 0.24284(8) 0.0446(6) Uani d . 1.000 . . N N3B 0.35284(10) 0.27772(19) -0.02411(9) 0.0498(7) Uani d . 1.000 . . C C1B 0.29850(10) 0.15205(18) 0.09987(10) 0.0450(7) Uani d . 1.000 . . C C2B 0.31782(10) 0.16157(17) 0.04763(10) 0.0443(7) Uani d . 1.000 . . C C3B 0.33333(9) 0.26616(17) 0.02691(9) 0.0391(6) Uani d . 1.000 . . C C4B 0.32668(10) 0.36049(16) 0.06271(9) 0.0401(7) Uani d . 1.000 . . C C5B 0.30681(10) 0.34382(17) 0.11433(9) 0.0424(7) Uani d . 1.000 . . C C6B 0.33867(14) 0.47561(19) 0.04276(11) 0.0590(9) Uani d . 1.000 . . C C7B 0.27054(11) 0.2309(2) 0.18961(10) 0.0491(8) Uani d . 1.000 . . C C8B 0.35212(10) 0.12839(17) 0.26047(9) 0.0410(7) Uani d . 1.000 . . C C9B 0.40518(10) 0.13125(17) 0.31648(9) 0.0399(6) Uani d . 1.000 . . C C10B 0.45840(12) 0.1987(2) 0.31831(12) 0.0596(9) Uani d . 1.000 . . C C11B 0.51180(13) 0.1928(3) 0.36621(14) 0.0736(11) Uani d . 1.000 . . C C12B 0.51240(12) 0.1204(2) 0.41257(13) 0.0659(10) Uani d . 1.000 . . C C13B 0.45962(11) 0.0541(2) 0.41153(10) 0.0515(8) Uani d . 1.000 . . C C14B 0.40539(9) 0.05834(16) 0.36407(9) 0.0371(6) Uani d . 1.000 . . C C15B 0.34765(10) -0.01351(16) 0.36602(9) 0.0386(7) Uani d . 1.000 . . O O1W 0.18224(9) 0.0223(2) 0.26300(9) 0.0921(9) Uani d . 1.000 . . H H2N2 0.2484(10) 0.1778(19) 0.3480(9) 0.036(6) Uiso d . 1.000 . . H H2N3 -0.0890(14) 0.279(2) 0.3580(12) 0.074(9) Uiso d . 1.000 . . H H1N3 -0.0822(13) 0.148(2) 0.3573(12) 0.071(8) Uiso d . 1.000 . . H H1AA 0.08940 0.41900 0.31600 0.0490 Uiso c RU 1.000 . . H H2AA -0.01080 0.39790 0.33140 0.0490 Uiso c RU 1.000 . . H H5AA 0.11220 0.09380 0.31390 0.0510 Uiso c RU 1.000 . . H H6AA -0.03720 0.00910 0.30630 0.0980 Uiso c RU 1.000 . . H H6AB 0.00040 0.00490 0.37410 0.0980 Uiso c RU 1.000 . . H H6AC 0.03450 -0.03310 0.32380 0.0980 Uiso c RU 1.000 . . H H7AA 0.17720 0.22820 0.26710 0.0520 Uiso c RU 1.000 . . H H10A 0.28490 0.15200 0.47740 0.0590 Uiso c RU 1.000 . . H H7AB 0.18120 0.34960 0.29310 0.0520 Uiso c RU 1.000 . . H H11A 0.38210 0.11520 0.54450 0.0690 Uiso c RU 1.000 . . H H12A 0.47100 0.22190 0.54330 0.0720 Uiso c RU 1.000 . . H H13A 0.46330 0.36940 0.47750 0.0630 Uiso c RU 1.000 . . H H10B 0.45820 0.24840 0.28700 0.0720 Uiso c RU 1.000 . . H H11B 0.54740 0.23820 0.36690 0.0880 Uiso c RU 1.000 . . H H1N2 0.3306(14) 0.285(3) 0.2678(14) 0.086(10) Uiso d . 1.000 . . H H12B 0.54850 0.11610 0.44470 0.0790 Uiso c RU 1.000 . . H H4N3 0.3539(12) 0.218(2) -0.0473(12) 0.061(7) Uiso d . 1.000 . . H H13B 0.46030 0.00530 0.44330 0.0620 Uiso c RU 1.000 . . H H3N3 0.3629(13) 0.348(3) -0.0382(12) 0.077(9) Uiso d . 1.000 . . H H1BA 0.28860 0.08200 0.11260 0.0540 Uiso c RU 1.000 . . H H2BA 0.32090 0.09800 0.02520 0.0530 Uiso c RU 1.000 . . H H5BA 0.30220 0.40550 0.13760 0.0510 Uiso c RU 1.000 . . H H6BA 0.31080 0.48980 0.00390 0.0890 Uiso c RU 1.000 . . H H6BB 0.38290 0.48200 0.04030 0.0890 Uiso c RU 1.000 . . H H6BC 0.33010 0.52890 0.07120 0.0890 Uiso c RU 1.000 . . H H7BA 0.24300 0.29390 0.19280 0.0590 Uiso c RU 1.000 . . H H7BB 0.24470 0.16370 0.18730 0.0590 Uiso c RU 1.000 . . H H1W1 0.22220 0.01410 0.28200 0.1380 Uiso d RU 1.000 . . H H2W1 0.17600 -0.03640 0.24040 0.1380 Uiso d RU 1.000 . . 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_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H1W1 O1W H2W1 . . . 102.00 no C1A N1A C5A . . . 119.30(18) yes C5A N1A C7A . . . 119.47(17) yes C1A N1A C7A . . . 121.19(17) yes C7A N2A C8A . . . 119.71(18) yes C7A N2A H2N2 . . . 119.0(13) no C8A N2A H2N2 . . . 118.7(14) no C3A N3A H2N3 . . . 117.3(18) no H2N3 N3A H1N3 . . . 119(2) no C3A N3A H1N3 . . . 120.5(18) no C8B N2B H1N2 . . . 119(2) no C7B N2B H1N2 . . . 120(2) no C3B N3B H3N3 . . . 122.2(18) no C3B N3B H4N3 . . . 119.5(17) no H4N3 N3B H3N3 . . . 118(2) no N1A C1A C2A . . . 121.03(19) yes C1A C2A C3A . . . 121.3(2) no C2A C3A C4A . . . 117.04(19) no N3A C3A C2A . . . 121.5(2) yes N3A C3A C4A . . . 121.5(2) yes C3A C4A C6A . . . 121.1(2) no C3A C4A C5A . . . 118.23(19) no C5A C4A C6A . . . 120.7(2) no N1A C5A C4A . . . 123.08(19) yes N1A C7A N2A . . . 113.36(16) yes O1A C8A N2A . . . 121.8(2) yes N2A C8A C9A . . . 116.71(18) yes O1A C8A C9A . . . 121.54(18) yes C8A C9A C14A . . . 118.39(18) no C10A C9A C14A . . . 119.6(2) no C8A C9A C10A . . . 121.9(2) no C9A C10A C11A . . . 120.5(2) no C10A C11A C12A . . . 119.9(2) no C11A C12A C13A . . . 120.4(2) no C12A C13A C14A . . . 120.6(2) no C9A C14A C15A . . . 119.71(19) no C13A C14A C15A . . . 121.2(2) no C9A C14A C13A . . . 119.0(2) no O3A C15A C14A . . . 117.7(2) yes O2A C15A O3A . . . 126.7(2) yes O2A C15A C14A . . . 115.5(2) yes C2A C1A H1AA . . . 119.00 no N1A C1A H1AA . . . 119.00 no C3A C2A H2AA . . . 119.00 no C1A C2A H2AA . . . 119.00 no N1A C5A H5AA . . . 118.00 no C4A C5A H5AA . . . 119.00 no C4A C6A H6AC . . . 109.00 no H6AA C6A H6AB . . . 109.00 no C4A C6A H6AB . . . 110.00 no C4A C6A H6AA . . . 109.00 no H6AA C6A H6AC . . . 110.00 no H6AB C6A H6AC . . . 109.00 no H7AA C7A H7AB . . . 108.00 no N2A C7A H7AB . . . 109.00 no N2A C7A H7AA . . . 109.00 no N1A C7A H7AA . . . 109.00 no N1A C7A H7AB . . . 109.00 no C11A C10A H10A . . . 120.00 no C9A C10A H10A . . . 120.00 no C10A C11A H11A . . . 120.00 no C12A C11A H11A . . . 120.00 no C13A C12A H12A . . . 120.00 no C11A C12A H12A . . . 120.00 no C14A C13A H13A . . . 120.00 no C12A C13A H13A . . . 120.00 no C1B N1B C5B . . . 119.32(18) yes C1B N1B C7B . . . 120.78(18) yes C5B N1B C7B . . . 119.84(17) yes C7B N2B C8B . . . 120.11(19) yes N1B C1B C2B . . . 121.2(2) yes C1B C2B C3B . . . 121.04(19) no N3B C3B C2B . . . 122.2(2) yes N3B C3B C4B . . . 120.95(19) yes C2B C3B C4B . . . 116.82(18) no C3B C4B C5B . . . 118.46(18) no C3B C4B C6B . . . 120.72(19) no C5B C4B C6B . . . 120.77(19) no N1B C5B C4B . . . 123.12(19) yes N1B C7B N2B . . . 113.19(19) yes O1B C8B C9B . . . 121.33(19) yes N2B C8B C9B . . . 116.39(18) yes O1B C8B N2B . . . 122.1(2) yes C10B C9B C14B . . . 119.4(2) no C8B C9B C10B . . . 119.14(19) no C8B C9B C14B . . . 121.05(19) no C9B C10B C11B . . . 120.6(2) no C10B C11B C12B . . . 120.1(3) no C11B C12B C13B . . . 119.8(3) no C12B C13B C14B . . . 121.3(2) no C9B C14B C13B . . . 118.78(19) no C9B C14B C15B . . . 121.88(18) no C13B C14B C15B . . . 119.32(18) no O2B C15B C14B . . . 117.17(17) yes O2B C15B O3B . . . 125.5(2) yes O3B C15B C14B . . . 117.32(19) yes C2B C1B H1BA . . . 119.00 no N1B C1B H1BA . . . 119.00 no C1B C2B H2BA . . . 119.00 no C3B C2B H2BA . . . 119.00 no C4B C5B H5BA . . . 118.00 no N1B C5B H5BA . . . 118.00 no C4B C6B H6BA . . . 109.00 no C4B C6B H6BC . . . 110.00 no H6BA C6B H6BB . . . 109.00 no C4B C6B H6BB . . . 109.00 no H6BB C6B H6BC . . . 110.00 no H6BA C6B H6BC . . . 110.00 no N1B C7B H7BB . . . 109.00 no N2B C7B H7BA . . . 109.00 no N1B C7B H7BA . . . 109.00 no H7BA C7B H7BB . . . 108.00 no N2B C7B H7BB . . . 109.00 no C9B C10B H10B . . . 120.00 no C11B C10B H10B . . . 120.00 no C12B C11B H11B . . . 120.00 no C10B C11B H11B . . . 120.00 no C11B C12B H12B . . . 120.00 no C13B C12B H12B . . . 120.00 no C12B C13B H13B . . . 119.00 no C14B C13B H13B . . . 119.00 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1A C8A . . 1.220(3) yes O2A C15A . . 1.257(3) yes O3A C15A . . 1.247(3) yes O1W H1W1 . . 0.8700 no O1W H2W1 . . 0.8600 no N1A C1A . . 1.346(3) yes N1A C7A . . 1.480(3) yes N1A C5A . . 1.355(3) yes N2A C8A . . 1.353(3) yes N2A C7A . . 1.430(3) yes N3A C3A . . 1.335(3) yes N2A H2N2 . . 0.88(2) no N3A H1N3 . . 0.90(2) no N3A H2N3 . . 0.93(3) no O1B C8B . . 1.222(3) yes O2B C15B . . 1.244(3) yes O3B C15B . . 1.249(3) yes N1B C7B . . 1.484(3) yes N1B C1B . . 1.341(3) yes N1B C5B . . 1.351(3) yes N2B C7B . . 1.435(3) yes N2B C8B . . 1.349(3) yes N3B C3B . . 1.335(3) yes N2B H1N2 . . 0.90(3) no N3B H3N3 . . 0.95(3) no N3B H4N3 . . 0.89(2) no C1A C2A . . 1.346(3) no C2A C3A . . 1.408(3) no C3A C4A . . 1.419(3) no C4A C6A . . 1.498(3) no C4A C5A . . 1.359(3) no C8A C9A . . 1.494(3) no C9A C10A . . 1.383(3) no C9A C14A . . 1.395(3) no C10A C11A . . 1.382(4) no C11A C12A . . 1.364(4) no C12A C13A . . 1.379(3) no C13A C14A . . 1.385(3) no C14A C15A . . 1.507(3) no C1A H1AA . . 0.9300 no C2A H2AA . . 0.9300 no C5A H5AA . . 0.9300 no C6A H6AB . . 0.9600 no C6A H6AA . . 0.9600 no C6A H6AC . . 0.9600 no C7A H7AB . . 0.9700 no C7A H7AA . . 0.9700 no C10A H10A . . 0.9300 no C11A H11A . . 0.9300 no C12A H12A . . 0.9300 no C13A H13A . . 0.9300 no C1B C2B . . 1.358(3) no C2B C3B . . 1.407(3) no C3B C4B . . 1.423(3) no C4B C6B . . 1.494(3) no C4B C5B . . 1.360(3) no C8B C9B . . 1.494(3) no C9B C10B . . 1.386(3) no C9B C14B . . 1.395(3) no C10B C11B . . 1.381(4) no C11B C12B . . 1.368(4) no C12B C13B . . 1.373(4) no C13B C14B . . 1.386(3) no C14B C15B . . 1.512(3) no C1B H1BA . . 0.9300 no C2B H2BA . . 0.9300 no C5B H5BA . . 0.9300 no C6B H6BB . . 0.9600 no C6B H6BA . . 0.9600 no C6B H6BC . . 0.9600 no C7B H7BB . . 0.9700 no C7B H7BA . . 0.9700 no C10B H10B . . 0.9300 no C11B H11B . . 0.9300 no C12B H12B . . 0.9300 no C13B H13B . . 0.9300 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2A H2N2 O2B . 0.88(2) 2.03(2) 2.897(2) 173(2) yes N3A H2N3 O3B 5_455 0.93(3) 1.95(3) 2.864(3) 168(2) yes N3A H1N3 O3A 5_445 0.90(2) 2.01(3) 2.864(3) 157(2) yes N2B H1N2 O2A . 0.90(3) 2.12(3) 3.006(3) 171(3) yes N3B H4N3 O3B 4_554 0.89(2) 2.01(3) 2.887(3) 167(2) yes N3B H3N3 O3A 4_564 0.95(3) 2.03(3) 2.935(3) 161(3) yes O1W H1W1 O2B . 0.8700 1.8700 2.681(3) 155 yes O1W H2W1 O2A 6_545 0.8600 1.8100 2.581(3) 147 yes C1A H1AA O1B 6_555 0.9300 2.5300 3.355(3) 147 yes C5A H5AA O1W . 0.9300 2.2700 3.083(3) 146 yes C7A H7AA O1W . 0.9700 2.4700 3.139(3) 126 yes C7A H7AB O1B 6_555 0.9700 2.4000 3.336(3) 162 yes C1B H1BA O1A 6_545 0.9300 2.2000 3.053(3) 152 yes C2A H2AA Cg1 5_455 0.93 2.95 3.831(2) 158 y C11B H11B Cg2 2_655 0.93 2.94 3.721(3) 142 y 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5A N1A C1A C2A . . . . 0.8(3) no C7A N1A C1A C2A . . . . 178.52(18) no C1A N1A C5A C4A . . . . -1.7(3) no C7A N1A C5A C4A . . . . -179.45(18) no C1A N1A C7A N2A . . . . 112.8(2) no C5A N1A C7A N2A . . . . -69.5(2) no C8A N2A C7A N1A . . . . -88.4(2) no C7A N2A C8A O1A . . . . 15.1(3) no C7A N2A C8A C9A . . . . -165.31(18) no C7B N1B C5B C4B . . . . -178.6(2) no C1B N1B C7B N2B . . . . 97.4(2) no C5B N1B C7B N2B . . . . -85.4(2) no C5B N1B C1B C2B . . . . 1.1(3) no C7B N1B C1B C2B . . . . 178.3(2) no C1B N1B C5B C4B . . . . -1.4(3) no C8B N2B C7B N1B . . . . -83.4(2) no C7B N2B C8B O1B . . . . 4.4(3) no C7B N2B C8B C9B . . . . -179.84(19) no N1A C1A C2A C3A . . . . 1.5(3) no C1A C2A C3A N3A . . . . 177.5(2) no C1A C2A C3A C4A . . . . -2.8(3) no N3A C3A C4A C5A . . . . -178.40(19) no C2A C3A C4A C6A . . . . -178.4(2) no C2A C3A C4A C5A . . . . 2.0(3) no N3A C3A C4A C6A . . . . 1.3(3) no C6A C4A C5A N1A . . . . -179.4(2) no C3A C4A C5A N1A . . . . 0.3(3) no O1A C8A C9A C10A . . . . 111.7(2) no N2A C8A C9A C14A . . . . 116.8(2) no O1A C8A C9A C14A . . . . -63.6(3) no N2A C8A C9A C10A . . . . -67.9(3) no C14A C9A C10A C11A . . . . -0.5(3) no C8A C9A C14A C13A . . . . 175.42(19) no C8A C9A C14A C15A . . . . -7.8(3) no C10A C9A C14A C13A . . . . 0.0(3) no C10A C9A C14A C15A . . . . 176.8(2) no C8A C9A C10A C11A . . . . -175.8(2) no C9A C10A C11A C12A . . . . 0.0(4) no C10A C11A C12A C13A . . . . 1.0(4) no C11A C12A C13A C14A . . . . -1.6(4) no C12A C13A C14A C15A . . . . -175.7(2) no C12A C13A C14A C9A . . . . 1.0(3) no C9A C14A C15A O2A . . . . -51.8(3) no C13A C14A C15A O3A . . . . -52.1(3) no C9A C14A C15A O3A . . . . 131.2(2) no C13A C14A C15A O2A . . . . 125.0(2) no N1B C1B C2B C3B . . . . 0.1(3) no C1B C2B C3B N3B . . . . 179.6(2) no C1B C2B C3B C4B . . . . -1.0(3) no N3B C3B C4B C5B . . . . -179.8(2) no N3B C3B C4B C6B . . . . 2.6(3) no C2B C3B C4B C5B . . . . 0.8(3) no C2B C3B C4B C6B . . . . -176.8(2) no C3B C4B C5B N1B . . . . 0.4(3) no C6B C4B C5B N1B . . . . 178.0(2) no O1B C8B C9B C10B . . . . 115.5(3) no O1B C8B C9B C14B . . . . -57.2(3) no N2B C8B C9B C10B . . . . -60.3(3) no N2B C8B C9B C14B . . . . 127.0(2) no C8B C9B C10B C11B . . . . -171.8(2) no C14B C9B C10B C11B . . . . 1.1(4) no C8B C9B C14B C13B . . . . 171.6(2) no C8B C9B C14B C15B . . . . -10.1(3) no C10B C9B C14B C13B . . . . -1.2(3) no C10B C9B C14B C15B . . . . 177.2(2) no C9B C10B C11B C12B . . . . -0.4(4) no C10B C11B C12B C13B . . . . -0.4(4) no C11B C12B C13B C14B . . . . 0.4(4) no C12B C13B C14B C9B . . . . 0.4(3) no C12B C13B C14B C15B . . . . -178.0(2) no C9B C14B C15B O2B . . . . -38.6(3) no C9B C14B C15B O3B . . . . 142.6(2) no C13B C14B C15B O2B . . . . 139.7(2) no C13B C14B C15B O3B . . . . -39.1(3) no