#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:16:59 +0300 (Thu, 07 May 2020) $ #$Revision: 251828 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240465.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_7240465 loop_ _publ_author_name 'Wallis, John D.' 'Garner, Alun Christopher' 'Yang, Songjie' _publ_section_title ; N-H···O Hydrogen Bonding to the Alkoxy Oxygen of a Carboxylic Ester Group: Crystal Structures of Methyl 2,6-Diaminobenzoate and Its Derivatives. ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00495B _journal_year 2020 _chemical_formula_sum 'C48 H46 B2 N4 O2' _chemical_formula_weight 732.51 _chemical_name_systematic 'Methyl 2,6-diaminobenzoate bis BPh3 complex bis acetontrile solvate' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014 _audit_update_record ; 2020-04-01 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 67.212(6) _cell_angle_beta 77.440(5) _cell_angle_gamma 77.991(6) _cell_formula_units_Z 2 _cell_length_a 11.5169(8) _cell_length_b 12.9904(10) _cell_length_c 15.2893(9) _cell_measurement_reflns_used 2166 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 29.0500 _cell_measurement_theta_min 3.6150 _cell_volume 2038.8(3) _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-2014 (Sheldrick, 2014)' _computing_structure_solution SHELXS _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 15.9832 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_unetI/netI 0.1154 _diffrn_reflns_Laue_measured_fraction_full 0.980 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 13681 _diffrn_reflns_point_group_measured_fraction_full 0.980 _diffrn_reflns_point_group_measured_fraction_max 0.979 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 26.368 _diffrn_reflns_theta_min 2.883 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.862 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.193 _exptl_crystal_description block _exptl_crystal_F_000 776 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: acetonitrile' _exptl_crystal_size_max 0.414 _exptl_crystal_size_mid 0.316 _exptl_crystal_size_min 0.213 _refine_diff_density_max 0.274 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 524 _refine_ls_number_reflns 8170 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.1469 _refine_ls_R_factor_gt 0.0721 _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^)+(0.0635P)^2^+0.0734P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1450 _refine_ls_wR_factor_ref 0.1797 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4549 _reflns_number_total 8170 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00495b2.cif _cod_data_source_block BPh3COMPLEX _cod_database_code 7240465 _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 2014-3 _shelx_res_file ; REM Old TITL saltDJBABSfilt2 in P-1 REM SHELXT solution in P-1 REM R1 0.218, Rweak 0.018, Alpha 0.060, Orientation as input REM Formula found by SHELXT: C48 B2 N4 O2 REM REM REM REM saltdjbabsfilt2_a.res in P-1 REM R1 = 0.0723 for 4549 Fo > 4sig(Fo) and 0.1473 for all 8170 data REM 508 parameters refined using 0 restraints REM Highest difference peak 0.282, deepest hole -0.258, 1-sigma level 0.052 REM saltdjbabsfilt2_a.res in P-1 REM R1 = 0.0721 for 4549 Fo > 4sig(Fo) and 0.1469 for all 8170 data REM 524 parameters refined using 0 restraints REM Highest difference peak 0.274, deepest hole -0.258, 1-sigma level 0.051 TITL saltdjbabsfilt2_a.res in P-1 CELL 0.71073 11.5169 12.9904 15.2893 67.212 77.440 77.991 ZERR 2.0000 0.0008 0.0010 0.0009 0.006 0.005 0.006 LATT 1 SFAC C H B N O UNIT 96 92 4 8 4 MERG 2 SHEL 100.00 0.80 FMAP 2 GRID PLAN 20 TEMP -123 BOND $H CONF HTAB N2 N81 HTAB N1 O1 HTAB N2 O2 HTAB N1 N71 MPLA 4 O1 O2 C7 C8 MPLA 6 C1 C2 C3 C4 C5 C6 N1 N2 C7 L.S. 4 ACTA 52 WGHT 0.063500 0.073400 FVAR 0.60311 O1 5 0.447802 0.561366 0.113166 11.00000 0.03156 0.04686 = 0.02434 -0.01149 -0.00186 -0.00231 O2 5 0.264146 0.519462 0.125988 11.00000 0.03486 0.04406 = 0.02348 -0.01883 -0.00924 0.00104 N1 4 0.530735 0.457233 0.284491 11.00000 0.02716 0.03041 = 0.02084 -0.01084 -0.00447 -0.00197 N2 4 0.099202 0.595104 0.251111 11.00000 0.02640 0.03116 = 0.02019 -0.01157 -0.00293 -0.00303 N71 4 0.631518 0.624417 0.327240 11.00000 0.04981 0.05458 = 0.04298 -0.01918 -0.01054 -0.01505 N81 4 -0.052660 0.416881 0.375230 11.00000 0.04614 0.04607 = 0.03965 -0.01703 -0.00283 -0.01201 C1 1 0.316832 0.527333 0.263577 11.00000 0.02837 0.02550 = 0.02169 -0.00860 -0.00674 -0.00452 C2 1 0.407268 0.489086 0.322023 11.00000 0.02689 0.02582 = 0.02526 -0.01087 -0.00443 -0.00243 C3 1 0.380480 0.476524 0.418009 11.00000 0.03143 0.02994 = 0.02433 -0.01225 -0.00917 -0.00124 AFIX 43 H3 2 0.442457 0.450388 0.456731 11.00000 -1.20000 AFIX 0 C4 1 0.263904 0.501979 0.457169 11.00000 0.03538 0.03244 = 0.02204 -0.01195 -0.00386 -0.00469 AFIX 43 H4 2 0.245688 0.493161 0.523123 11.00000 -1.20000 AFIX 0 C5 1 0.173172 0.540156 0.401775 11.00000 0.02352 0.03324 = 0.02476 -0.01311 -0.00100 -0.00329 AFIX 43 H5 2 0.092945 0.558120 0.429299 11.00000 -1.20000 AFIX 0 C6 1 0.199452 0.552203 0.305891 11.00000 0.02667 0.02067 = 0.02446 -0.00758 -0.00921 0.00007 C7 1 0.351502 0.539214 0.160382 11.00000 0.02787 0.02853 = 0.02406 -0.00981 -0.00639 0.00250 C8 1 0.289597 0.528454 0.025970 11.00000 0.04721 0.05641 = 0.02150 -0.01954 -0.01270 0.00564 AFIX 137 H8C 2 0.285116 0.608116 -0.015647 11.00000 -1.50000 H8B 2 0.230469 0.493691 0.013166 11.00000 -1.50000 H8A 2 0.370339 0.489610 0.013056 11.00000 -1.50000 AFIX 0 C11 1 0.706633 0.313787 0.236685 11.00000 0.03011 0.03426 = 0.02249 -0.00961 -0.01312 -0.00143 C12 1 0.782429 0.396237 0.202558 11.00000 0.03180 0.03447 = 0.02684 -0.01393 -0.00587 0.00086 AFIX 43 H12 2 0.755430 0.464148 0.215088 11.00000 -1.20000 AFIX 0 C13 1 0.896214 0.382799 0.150800 11.00000 0.03288 0.04466 = 0.03549 -0.01613 -0.00724 -0.00824 AFIX 43 H13 2 0.945474 0.440816 0.129180 11.00000 -1.20000 AFIX 0 C14 1 0.937791 0.285698 0.130753 11.00000 0.02775 0.05287 = 0.03540 -0.01919 -0.00660 0.00252 AFIX 43 H14 2 1.014566 0.277120 0.093913 11.00000 -1.20000 AFIX 0 C15 1 0.866188 0.201026 0.165012 11.00000 0.03939 0.03816 = 0.02808 -0.01605 -0.01131 0.00430 AFIX 43 H15 2 0.894543 0.132891 0.153061 11.00000 -1.20000 AFIX 0 C16 1 0.753660 0.215071 0.216515 11.00000 0.03395 0.03271 = 0.02891 -0.01199 -0.00920 -0.00153 AFIX 43 H16 2 0.706011 0.155686 0.239275 11.00000 -1.20000 AFIX 0 C21 1 0.595495 0.252774 0.413804 11.00000 0.02420 0.03092 = 0.02674 -0.01376 -0.00365 -0.00387 C22 1 0.637069 0.299625 0.467847 11.00000 0.03811 0.03203 = 0.02993 -0.01148 -0.01131 -0.00151 AFIX 43 H22 2 0.646319 0.377285 0.440840 11.00000 -1.20000 AFIX 0 C23 1 0.665234 0.237087 0.559188 11.00000 0.04769 0.04054 = 0.03100 -0.01456 -0.01671 -0.00117 AFIX 43 H23 2 0.691308 0.272523 0.594013 11.00000 -1.20000 AFIX 0 C24 1 0.655500 0.124017 0.599391 11.00000 0.04894 0.04074 = 0.02614 -0.00568 -0.01389 -0.00136 AFIX 43 H24 2 0.675326 0.080767 0.661722 11.00000 -1.20000 AFIX 0 C25 1 0.616598 0.073997 0.548194 11.00000 0.04818 0.02819 = 0.03720 -0.00636 -0.01169 -0.00448 AFIX 43 H25 2 0.609815 -0.004198 0.574994 11.00000 -1.20000 AFIX 0 C26 1 0.587339 0.138497 0.457171 11.00000 0.03673 0.03725 = 0.03559 -0.01719 -0.00929 -0.00646 AFIX 43 H26 2 0.560515 0.102525 0.423155 11.00000 -1.20000 AFIX 0 C31 1 0.472605 0.279685 0.270625 11.00000 0.02634 0.02853 = 0.02627 -0.01119 -0.00860 0.00183 C32 1 0.367979 0.247020 0.332909 11.00000 0.03424 0.03523 = 0.02701 -0.01208 -0.00759 -0.00233 AFIX 43 H32 2 0.359443 0.243903 0.397068 11.00000 -1.20000 AFIX 0 C33 1 0.275832 0.218886 0.305040 11.00000 0.03129 0.04780 = 0.03859 -0.01295 -0.00465 -0.00979 AFIX 43 H33 2 0.204859 0.199051 0.349140 11.00000 -1.20000 AFIX 0 C34 1 0.287545 0.219784 0.212904 11.00000 0.03580 0.04636 = 0.04864 -0.01999 -0.01610 -0.00945 AFIX 43 H34 2 0.225544 0.199032 0.193633 11.00000 -1.20000 AFIX 0 C35 1 0.388972 0.250748 0.149831 11.00000 0.03895 0.04776 = 0.03500 -0.02212 -0.01091 -0.00241 AFIX 43 H35 2 0.397564 0.251592 0.086345 11.00000 -1.20000 AFIX 0 C36 1 0.480067 0.281151 0.178008 11.00000 0.02893 0.04084 = 0.03044 -0.01661 -0.00587 -0.00448 AFIX 43 H36 2 0.549375 0.303563 0.132640 11.00000 -1.20000 AFIX 0 C41 1 0.184515 0.785475 0.146251 11.00000 0.02830 0.02351 = 0.02927 -0.00689 -0.00885 0.00062 C42 1 0.223081 0.800087 0.049334 11.00000 0.03084 0.03173 = 0.03396 -0.01558 -0.00535 -0.00416 AFIX 43 H42 2 0.174055 0.781218 0.016709 11.00000 -1.20000 AFIX 0 C43 1 0.328790 0.840545 -0.000841 11.00000 0.03528 0.04088 = 0.03389 -0.01552 0.00150 -0.00408 AFIX 43 H43 2 0.350423 0.850610 -0.066952 11.00000 -1.20000 AFIX 0 C44 1 0.403107 0.866401 0.044782 11.00000 0.03366 0.04090 = 0.05447 -0.01512 -0.00115 -0.01018 AFIX 43 H44 2 0.476538 0.893789 0.010824 11.00000 -1.20000 AFIX 0 C45 1 0.369462 0.851992 0.140174 11.00000 0.03834 0.05504 = 0.05590 -0.01906 -0.01690 -0.01177 AFIX 43 H45 2 0.420081 0.869630 0.172373 11.00000 -1.20000 AFIX 0 C46 1 0.262893 0.812160 0.189779 11.00000 0.03880 0.04249 = 0.02963 -0.00739 -0.01268 -0.00781 AFIX 43 H46 2 0.242169 0.802574 0.255832 11.00000 -1.20000 AFIX 0 C51 1 -0.006596 0.781326 0.289642 11.00000 0.03132 0.02901 = 0.02266 -0.00810 -0.01136 0.00020 C52 1 -0.084760 0.721344 0.367996 11.00000 0.03366 0.03910 = 0.03239 -0.01523 -0.00783 0.00141 AFIX 43 H52 2 -0.091832 0.646673 0.375598 11.00000 -1.20000 AFIX 0 C53 1 -0.152210 0.765789 0.434898 11.00000 0.04354 0.04544 = 0.02823 -0.01084 -0.00212 0.00103 AFIX 43 H53 2 -0.202411 0.721145 0.488147 11.00000 -1.20000 AFIX 0 C54 1 -0.146517 0.875185 0.424219 11.00000 0.06254 0.04165 = 0.02930 -0.01805 -0.01029 0.01183 AFIX 43 H54 2 -0.193266 0.906806 0.469430 11.00000 -1.20000 AFIX 0 C55 1 -0.072239 0.937650 0.347236 11.00000 0.07724 0.03229 = 0.03325 -0.01543 -0.01140 0.00046 AFIX 43 H55 2 -0.068819 1.013530 0.338448 11.00000 -1.20000 AFIX 0 C56 1 -0.002177 0.890840 0.282215 11.00000 0.05191 0.03250 = 0.03020 -0.01173 -0.00661 -0.00381 AFIX 43 H56 2 0.050598 0.934931 0.230892 11.00000 -1.20000 AFIX 0 C61 1 -0.037636 0.755995 0.135591 11.00000 0.02494 0.03113 = 0.02364 -0.01256 -0.00056 -0.00203 C62 1 -0.105322 0.677046 0.139375 11.00000 0.03584 0.02850 = 0.02948 -0.00731 -0.01009 -0.00339 AFIX 43 H62 2 -0.091114 0.601988 0.183286 11.00000 -1.20000 AFIX 0 C63 1 -0.193123 0.703633 0.081350 11.00000 0.03336 0.03685 = 0.03720 -0.01435 -0.00899 -0.00851 AFIX 43 H63 2 -0.236622 0.646850 0.085530 11.00000 -1.20000 AFIX 0 C64 1 -0.217088 0.811716 0.018051 11.00000 0.02989 0.04411 = 0.03352 -0.01826 -0.01216 -0.00087 AFIX 43 H64 2 -0.277261 0.830158 -0.021412 11.00000 -1.20000 AFIX 0 C65 1 -0.152899 0.893116 0.012410 11.00000 0.03487 0.03387 = 0.03148 -0.01227 -0.00904 0.00050 AFIX 43 H65 2 -0.168378 0.968135 -0.031238 11.00000 -1.20000 AFIX 0 C66 1 -0.065914 0.865191 0.070500 11.00000 0.03279 0.02937 = 0.03126 -0.01133 -0.00724 -0.00578 AFIX 43 H66 2 -0.023313 0.922697 0.066098 11.00000 -1.20000 AFIX 0 C71 1 0.641273 0.717409 0.298201 11.00000 0.03107 0.04842 = 0.03367 -0.01894 -0.00901 -0.00536 C72 1 0.654239 0.837175 0.260481 11.00000 0.03972 0.04797 = 0.05564 -0.02029 -0.01132 -0.00536 AFIX 137 H72C 2 0.646378 0.869368 0.192189 11.00000 -1.50000 H72A 2 0.733416 0.845856 0.268409 11.00000 -1.50000 H72B 2 0.591607 0.876540 0.295573 11.00000 -1.50000 AFIX 0 C81 1 -0.058853 0.325590 0.387353 11.00000 0.02717 0.04593 = 0.03437 -0.01493 -0.00595 -0.00526 C82 1 -0.065537 0.211217 0.400926 11.00000 0.04157 0.04052 = 0.05873 -0.01770 -0.01676 -0.00283 AFIX 137 H82A 2 -0.012606 0.191223 0.348671 11.00000 -1.50000 H82C 2 -0.148385 0.203443 0.400968 11.00000 -1.50000 H82B 2 -0.040184 0.160859 0.462410 11.00000 -1.50000 AFIX 0 B1 3 0.576247 0.320130 0.302252 11.00000 0.02655 0.02850 = 0.02237 -0.01059 -0.00701 -0.00208 B2 3 0.061070 0.735516 0.204331 11.00000 0.03413 0.02508 = 0.02103 -0.00527 -0.00799 -0.00251 H21B 2 0.033600 0.557997 0.291697 11.00000 0.02663 H11A 2 0.546004 0.496125 0.216279 11.00000 0.04518 H21A 2 0.125890 0.575897 0.196862 11.00000 0.02712 H11B 2 0.580801 0.488958 0.308359 11.00000 0.05048 HKLF 4 REM saltdjbabsfilt2_a.res in P-1 REM R1 = 0.0721 for 4549 Fo > 4sig(Fo) and 0.1469 for all 8170 data REM 524 parameters refined using 0 restraints END WGHT 0.0635 0.0734 REM Highest difference peak 0.274, deepest hole -0.258, 1-sigma level 0.051 Q1 1 0.0231 0.7589 0.2386 11.00000 0.05 0.27 Q2 1 0.5305 0.2729 0.2999 11.00000 0.05 0.25 Q3 1 0.6291 0.3346 0.2395 11.00000 0.05 0.25 Q4 1 0.6639 0.3052 0.2942 11.00000 0.05 0.24 Q5 1 0.4318 0.7059 0.0809 11.00000 0.05 0.23 Q6 1 0.4372 0.4826 0.1409 11.00000 0.05 0.22 Q7 1 0.4151 0.2986 0.3059 11.00000 0.05 0.22 Q8 1 0.1198 0.1249 0.4183 11.00000 0.05 0.22 Q9 1 -0.0403 0.4925 0.3420 11.00000 0.05 0.21 Q10 1 0.0987 0.6816 0.2335 11.00000 0.05 0.21 Q11 1 0.7147 0.2350 0.4957 11.00000 0.05 0.20 Q12 1 -0.1500 0.9036 0.0759 11.00000 0.05 0.20 Q13 1 0.4668 0.5582 0.0540 11.00000 0.05 0.20 Q14 1 0.0102 0.1620 0.4075 11.00000 0.05 0.20 Q15 1 0.5356 0.3172 0.3751 11.00000 0.05 0.19 Q16 1 0.3385 0.1805 0.3479 11.00000 0.05 0.19 Q17 1 0.5891 0.9000 0.2489 11.00000 0.05 0.19 Q18 1 0.7207 0.2595 0.2452 11.00000 0.05 0.19 Q19 1 0.5838 0.2836 0.3568 11.00000 0.05 0.19 Q20 1 0.4551 0.2078 0.3045 11.00000 0.05 0.19 ; _shelx_res_checksum 36647 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 O1 O 0.44780(19) 0.56137(19) 0.11317(14) 0.0355(5) Uani 1 1 d . . . . . O2 O 0.26415(18) 0.51946(18) 0.12599(13) 0.0323(5) Uani 1 1 d . . . . . N1 N 0.5307(2) 0.4572(2) 0.28449(19) 0.0258(6) Uani 1 1 d . . . . . N2 N 0.0992(2) 0.5951(2) 0.25111(19) 0.0254(6) Uani 1 1 d . . . . . N71 N 0.6315(3) 0.6244(3) 0.3272(2) 0.0468(8) Uani 1 1 d . . . . . N81 N -0.0527(3) 0.4169(3) 0.37523(19) 0.0431(7) Uani 1 1 d . . . . . C1 C 0.3168(3) 0.5273(2) 0.2636(2) 0.0245(7) Uani 1 1 d . . . . . C2 C 0.4073(3) 0.4891(2) 0.3220(2) 0.0256(7) Uani 1 1 d . . . . . C3 C 0.3805(3) 0.4765(3) 0.4180(2) 0.0274(7) Uani 1 1 d . . . . . H3 H 0.4425 0.4504 0.4567 0.033 Uiso 1 1 calc R U . . . C4 C 0.2639(3) 0.5020(3) 0.4572(2) 0.0293(7) Uani 1 1 d . . . . . H4 H 0.2457 0.4932 0.5231 0.035 Uiso 1 1 calc R U . . . C5 C 0.1732(3) 0.5402(3) 0.4018(2) 0.0269(7) Uani 1 1 d . . . . . H5 H 0.0929 0.5581 0.4293 0.032 Uiso 1 1 calc R U . . . C6 C 0.1995(2) 0.5522(2) 0.3059(2) 0.0237(7) Uani 1 1 d . . . . . C7 C 0.3515(3) 0.5392(3) 0.1604(2) 0.0273(7) Uani 1 1 d . . . . . C8 C 0.2896(3) 0.5285(3) 0.0260(2) 0.0407(9) Uani 1 1 d . . . . . H8C H 0.2851 0.6081 -0.0156 0.061 Uiso 1 1 calc R U . . . H8B H 0.2305 0.4937 0.0132 0.061 Uiso 1 1 calc R U . . . H8A H 0.3703 0.4896 0.0131 0.061 Uiso 1 1 calc R U . . . C11 C 0.7066(3) 0.3138(3) 0.2367(2) 0.0281(7) Uani 1 1 d . . . . . C12 C 0.7824(3) 0.3962(3) 0.2026(2) 0.0307(7) Uani 1 1 d . . . . . H12 H 0.7554 0.4641 0.2151 0.037 Uiso 1 1 calc R U . . . C13 C 0.8962(3) 0.3828(3) 0.1508(2) 0.0363(8) Uani 1 1 d . . . . . H13 H 0.9455 0.4408 0.1292 0.044 Uiso 1 1 calc R U . . . C14 C 0.9378(3) 0.2857(3) 0.1308(2) 0.0386(9) Uani 1 1 d . . . . . H14 H 1.0146 0.2771 0.0939 0.046 Uiso 1 1 calc R U . . . C15 C 0.8662(3) 0.2010(3) 0.1650(2) 0.0344(8) Uani 1 1 d . . . . . H15 H 0.8945 0.1329 0.1531 0.041 Uiso 1 1 calc R U . . . C16 C 0.7537(3) 0.2151(3) 0.2165(2) 0.0313(8) Uani 1 1 d . . . . . H16 H 0.7060 0.1557 0.2393 0.038 Uiso 1 1 calc R U . . . C21 C 0.5955(3) 0.2528(3) 0.4138(2) 0.0262(7) Uani 1 1 d . . . . . C22 C 0.6371(3) 0.2996(3) 0.4678(2) 0.0327(8) Uani 1 1 d . . . . . H22 H 0.6463 0.3773 0.4408 0.039 Uiso 1 1 calc R U . . . C23 C 0.6652(3) 0.2371(3) 0.5592(2) 0.0382(8) Uani 1 1 d . . . . . H23 H 0.6913 0.2725 0.5940 0.046 Uiso 1 1 calc R U . . . C24 C 0.6555(3) 0.1240(3) 0.5994(2) 0.0400(9) Uani 1 1 d . . . . . H24 H 0.6753 0.0808 0.6617 0.048 Uiso 1 1 calc R U . . . C25 C 0.6166(3) 0.0740(3) 0.5482(2) 0.0388(8) Uani 1 1 d . . . . . H25 H 0.6098 -0.0042 0.5750 0.047 Uiso 1 1 calc R U . . . C26 C 0.5873(3) 0.1385(3) 0.4572(2) 0.0344(8) Uani 1 1 d . . . . . H26 H 0.5605 0.1025 0.4232 0.041 Uiso 1 1 calc R U . . . C31 C 0.4726(3) 0.2797(3) 0.2706(2) 0.0267(7) Uani 1 1 d . . . . . C32 C 0.3680(3) 0.2470(3) 0.3329(2) 0.0318(8) Uani 1 1 d . . . . . H32 H 0.3594 0.2439 0.3971 0.038 Uiso 1 1 calc R U . . . C33 C 0.2758(3) 0.2189(3) 0.3050(2) 0.0394(9) Uani 1 1 d . . . . . H33 H 0.2049 0.1991 0.3491 0.047 Uiso 1 1 calc R U . . . C34 C 0.2875(3) 0.2198(3) 0.2129(2) 0.0405(9) Uani 1 1 d . . . . . H34 H 0.2255 0.1990 0.1936 0.049 Uiso 1 1 calc R U . . . C35 C 0.3890(3) 0.2507(3) 0.1498(2) 0.0380(8) Uani 1 1 d . . . . . H35 H 0.3976 0.2516 0.0863 0.046 Uiso 1 1 calc R U . . . C36 C 0.4801(3) 0.2812(3) 0.1780(2) 0.0320(8) Uani 1 1 d . . . . . H36 H 0.5494 0.3036 0.1326 0.038 Uiso 1 1 calc R U . . . C41 C 0.1845(3) 0.7855(2) 0.1463(2) 0.0277(7) Uani 1 1 d . . . . . C42 C 0.2231(3) 0.8001(3) 0.0493(2) 0.0309(7) Uani 1 1 d . . . . . H42 H 0.1741 0.7812 0.0167 0.037 Uiso 1 1 calc R U . . . C43 C 0.3288(3) 0.8405(3) -0.0008(2) 0.0373(8) Uani 1 1 d . . . . . H43 H 0.3504 0.8506 -0.0670 0.045 Uiso 1 1 calc R U . . . C44 C 0.4031(3) 0.8664(3) 0.0448(3) 0.0437(9) Uani 1 1 d . . . . . H44 H 0.4765 0.8938 0.0108 0.052 Uiso 1 1 calc R U . . . C45 C 0.3695(3) 0.8520(3) 0.1402(3) 0.0476(10) Uani 1 1 d . . . . . H45 H 0.4201 0.8696 0.1724 0.057 Uiso 1 1 calc R U . . . C46 C 0.2629(3) 0.8122(3) 0.1898(2) 0.0371(8) Uani 1 1 d . . . . . H46 H 0.2422 0.8026 0.2558 0.045 Uiso 1 1 calc R U . . . C51 C -0.0066(3) 0.7813(3) 0.2896(2) 0.0275(7) Uani 1 1 d . . . . . C52 C -0.0848(3) 0.7213(3) 0.3680(2) 0.0348(8) Uani 1 1 d . . . . . H52 H -0.0918 0.6467 0.3756 0.042 Uiso 1 1 calc R U . . . C53 C -0.1522(3) 0.7658(3) 0.4349(2) 0.0415(9) Uani 1 1 d . . . . . H53 H -0.2024 0.7211 0.4881 0.050 Uiso 1 1 calc R U . . . C54 C -0.1465(3) 0.8752(3) 0.4242(2) 0.0453(9) Uani 1 1 d . . . . . H54 H -0.1933 0.9068 0.4694 0.054 Uiso 1 1 calc R U . . . C55 C -0.0722(3) 0.9376(3) 0.3472(2) 0.0472(10) Uani 1 1 d . . . . . H55 H -0.0688 1.0135 0.3384 0.057 Uiso 1 1 calc R U . . . C56 C -0.0022(3) 0.8908(3) 0.2822(2) 0.0383(8) Uani 1 1 d . . . . . H56 H 0.0506 0.9349 0.2309 0.046 Uiso 1 1 calc R U . . . C61 C -0.0376(3) 0.7560(3) 0.1356(2) 0.0265(7) Uani 1 1 d . . . . . C62 C -0.1053(3) 0.6770(3) 0.1394(2) 0.0315(8) Uani 1 1 d . . . . . H62 H -0.0911 0.6020 0.1833 0.038 Uiso 1 1 calc R U . . . C63 C -0.1931(3) 0.7036(3) 0.0813(2) 0.0343(8) Uani 1 1 d . . . . . H63 H -0.2366 0.6468 0.0855 0.041 Uiso 1 1 calc R U . . . C64 C -0.2171(3) 0.8117(3) 0.0181(2) 0.0339(8) Uani 1 1 d . . . . . H64 H -0.2773 0.8302 -0.0214 0.041 Uiso 1 1 calc R U . . . C65 C -0.1529(3) 0.8931(3) 0.0124(2) 0.0334(8) Uani 1 1 d . . . . . H65 H -0.1684 0.9681 -0.0312 0.040 Uiso 1 1 calc R U . . . C66 C -0.0659(3) 0.8652(3) 0.0705(2) 0.0304(7) Uani 1 1 d . . . . . H66 H -0.0233 0.9227 0.0661 0.036 Uiso 1 1 calc R U . . . C71 C 0.6413(3) 0.7174(3) 0.2982(2) 0.0357(8) Uani 1 1 d . . . . . C72 C 0.6542(3) 0.8372(3) 0.2605(3) 0.0467(9) Uani 1 1 d . . . . . H72C H 0.6464 0.8694 0.1922 0.070 Uiso 1 1 calc R U . . . H72A H 0.7334 0.8459 0.2684 0.070 Uiso 1 1 calc R U . . . H72B H 0.5916 0.8765 0.2956 0.070 Uiso 1 1 calc R U . . . C81 C -0.0589(3) 0.3256(3) 0.3874(2) 0.0354(8) Uani 1 1 d . . . . . C82 C -0.0655(3) 0.2112(3) 0.4009(3) 0.0459(9) Uani 1 1 d . . . . . H82A H -0.0126 0.1912 0.3487 0.069 Uiso 1 1 calc R U . . . H82C H -0.1484 0.2034 0.4010 0.069 Uiso 1 1 calc R U . . . H82B H -0.0402 0.1609 0.4624 0.069 Uiso 1 1 calc R U . . . B1 B 0.5762(3) 0.3201(3) 0.3023(2) 0.0251(8) Uani 1 1 d . . . . . B2 B 0.0611(3) 0.7355(3) 0.2043(2) 0.0273(8) Uani 1 1 d . . . . . H21B H 0.034(3) 0.558(2) 0.292(2) 0.027(8) Uiso 1 1 d . . . . . H11A H 0.546(3) 0.496(3) 0.216(2) 0.045(10) Uiso 1 1 d . . . . . H21A H 0.126(2) 0.576(2) 0.197(2) 0.027(8) Uiso 1 1 d . . . . . H11B H 0.581(3) 0.489(3) 0.308(2) 0.050(10) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0316(13) 0.0469(15) 0.0243(11) -0.0115(10) -0.0019(10) -0.0023(11) O2 0.0349(12) 0.0441(14) 0.0235(11) -0.0188(10) -0.0092(9) 0.0010(10) N1 0.0272(14) 0.0304(16) 0.0208(14) -0.0108(12) -0.0045(12) -0.0020(12) N2 0.0264(15) 0.0312(16) 0.0202(14) -0.0116(12) -0.0029(12) -0.0030(12) N71 0.0498(19) 0.055(2) 0.0430(18) -0.0192(16) -0.0105(15) -0.0151(17) N81 0.0461(18) 0.046(2) 0.0396(17) -0.0170(15) -0.0028(14) -0.0120(16) C1 0.0284(17) 0.0255(18) 0.0217(15) -0.0086(13) -0.0067(13) -0.0045(13) C2 0.0269(17) 0.0258(18) 0.0253(16) -0.0109(13) -0.0044(13) -0.0024(13) C3 0.0314(18) 0.0299(19) 0.0243(16) -0.0122(14) -0.0092(14) -0.0012(14) C4 0.0354(19) 0.0324(19) 0.0220(16) -0.0120(14) -0.0039(14) -0.0047(15) C5 0.0235(16) 0.0332(19) 0.0248(16) -0.0131(14) -0.0010(13) -0.0033(14) C6 0.0267(17) 0.0207(17) 0.0245(16) -0.0076(13) -0.0092(13) 0.0001(13) C7 0.0279(18) 0.0285(19) 0.0241(16) -0.0098(14) -0.0064(14) 0.0025(14) C8 0.047(2) 0.056(2) 0.0215(17) -0.0195(16) -0.0127(15) 0.0056(17) C11 0.0301(17) 0.0343(19) 0.0225(16) -0.0096(14) -0.0131(13) -0.0014(15) C12 0.0318(18) 0.034(2) 0.0268(17) -0.0139(14) -0.0059(14) 0.0009(15) C13 0.0329(19) 0.045(2) 0.0355(19) -0.0161(16) -0.0072(15) -0.0082(16) C14 0.0277(18) 0.053(2) 0.0354(19) -0.0192(17) -0.0066(15) 0.0025(17) C15 0.039(2) 0.038(2) 0.0281(17) -0.0160(15) -0.0113(15) 0.0043(16) C16 0.0339(19) 0.033(2) 0.0289(17) -0.0120(15) -0.0092(15) -0.0015(15) C21 0.0242(16) 0.0309(19) 0.0267(16) -0.0138(14) -0.0037(13) -0.0039(14) C22 0.0381(19) 0.032(2) 0.0299(18) -0.0115(15) -0.0113(15) -0.0015(15) C23 0.048(2) 0.041(2) 0.0310(19) -0.0146(16) -0.0167(16) -0.0012(17) C24 0.049(2) 0.041(2) 0.0261(18) -0.0057(16) -0.0139(16) -0.0014(17) C25 0.048(2) 0.028(2) 0.037(2) -0.0064(16) -0.0117(16) -0.0045(16) C26 0.0367(19) 0.037(2) 0.0356(19) -0.0172(16) -0.0093(15) -0.0065(16) C31 0.0263(17) 0.0285(18) 0.0263(17) -0.0112(14) -0.0086(14) 0.0018(14) C32 0.0342(19) 0.035(2) 0.0270(17) -0.0121(15) -0.0076(14) -0.0023(15) C33 0.0313(19) 0.048(2) 0.039(2) -0.0130(17) -0.0047(16) -0.0098(16) C34 0.036(2) 0.046(2) 0.049(2) -0.0200(18) -0.0161(17) -0.0094(17) C35 0.039(2) 0.048(2) 0.0350(19) -0.0221(17) -0.0109(16) -0.0024(17) C36 0.0289(17) 0.041(2) 0.0304(18) -0.0166(15) -0.0059(14) -0.0045(15) C41 0.0283(17) 0.0235(18) 0.0293(17) -0.0069(14) -0.0088(14) 0.0006(13) C42 0.0308(18) 0.0317(19) 0.0340(18) -0.0156(15) -0.0054(15) -0.0042(15) C43 0.0353(19) 0.041(2) 0.0339(19) -0.0155(16) 0.0015(16) -0.0041(16) C44 0.0337(19) 0.041(2) 0.054(2) -0.0151(18) -0.0012(18) -0.0102(17) C45 0.038(2) 0.055(3) 0.056(2) -0.019(2) -0.0169(19) -0.0118(18) C46 0.039(2) 0.042(2) 0.0296(18) -0.0074(16) -0.0127(15) -0.0078(16) C51 0.0313(17) 0.0290(19) 0.0227(16) -0.0081(14) -0.0114(14) 0.0002(14) C52 0.0337(18) 0.039(2) 0.0324(18) -0.0152(16) -0.0078(15) 0.0014(16) C53 0.044(2) 0.045(2) 0.0282(18) -0.0108(16) -0.0021(16) 0.0010(17) C54 0.063(2) 0.042(2) 0.0293(19) -0.0181(17) -0.0103(18) 0.0118(19) C55 0.077(3) 0.032(2) 0.033(2) -0.0154(17) -0.0114(19) 0.0005(19) C56 0.052(2) 0.032(2) 0.0302(18) -0.0117(15) -0.0066(16) -0.0038(17) C61 0.0249(16) 0.0311(19) 0.0236(16) -0.0126(14) -0.0006(13) -0.0020(14) C62 0.0358(18) 0.0285(19) 0.0295(17) -0.0073(14) -0.0101(14) -0.0034(15) C63 0.0334(18) 0.037(2) 0.0372(19) -0.0143(16) -0.0090(15) -0.0085(16) C64 0.0299(18) 0.044(2) 0.0335(18) -0.0183(16) -0.0122(14) -0.0009(16) C65 0.0349(18) 0.034(2) 0.0315(18) -0.0123(15) -0.0090(15) 0.0005(15) C66 0.0328(18) 0.0294(19) 0.0313(18) -0.0113(15) -0.0072(14) -0.0058(14) C71 0.0311(19) 0.048(2) 0.0337(19) -0.0189(18) -0.0090(15) -0.0054(18) C72 0.040(2) 0.048(3) 0.056(2) -0.0203(19) -0.0113(18) -0.0054(18) C81 0.0272(18) 0.046(2) 0.0344(19) -0.0149(17) -0.0059(14) -0.0053(17) C82 0.042(2) 0.041(2) 0.059(2) -0.0177(18) -0.0168(18) -0.0028(17) B1 0.0265(19) 0.028(2) 0.0224(18) -0.0106(15) -0.0070(15) -0.0021(16) B2 0.034(2) 0.025(2) 0.0210(18) -0.0053(15) -0.0080(15) -0.0025(16) 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' B B 0.0013 0.0007 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O2 C8 116.4(2) . . ? C2 N1 B1 117.5(2) . . ? C2 N1 H11A 110(2) . . ? B1 N1 H11A 105.7(19) . . ? C2 N1 H11B 107(2) . . ? B1 N1 H11B 113(2) . . ? H11A N1 H11B 103(3) . . ? C6 N2 B2 117.8(2) . . ? C6 N2 H21B 106.0(17) . . ? B2 N2 H21B 112.2(17) . . ? C6 N2 H21A 105.0(17) . . ? B2 N2 H21A 102.7(17) . . ? H21B N2 H21A 113(2) . . ? C6 C1 C2 117.6(2) . . ? C6 C1 C7 123.9(2) . . ? C2 C1 C7 118.5(3) . . ? C3 C2 C1 121.0(3) . . ? C3 C2 N1 118.0(3) . . ? C1 C2 N1 121.0(3) . . ? C4 C3 C2 119.8(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 121.2(3) . . ? C5 C6 N2 116.7(2) . . ? C1 C6 N2 122.1(2) . . ? O1 C7 O2 123.2(3) . . ? O1 C7 C1 124.5(3) . . ? O2 C7 C1 112.3(3) . . ? O2 C8 H8C 109.5 . . ? O2 C8 H8B 109.5 . . ? H8C C8 H8B 109.5 . . ? O2 C8 H8A 109.5 . . ? H8C C8 H8A 109.5 . . ? H8B C8 H8A 109.5 . . ? C12 C11 C16 115.4(3) . . ? C12 C11 B1 125.4(3) . . ? C16 C11 B1 119.1(3) . . ? C13 C12 C11 122.4(3) . . ? C13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 119.0(3) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 122.6(3) . . ? C15 C16 H16 118.7 . . ? C11 C16 H16 118.7 . . ? C26 C21 C22 115.2(3) . . ? C26 C21 B1 120.6(3) . . ? C22 C21 B1 123.6(3) . . ? C23 C22 C21 122.6(3) . . ? C23 C22 H22 118.7 . . ? C21 C22 H22 118.7 . . ? C24 C23 C22 120.1(3) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.2(3) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C24 C25 C26 119.8(3) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C21 C26 C25 123.1(3) . . ? C21 C26 H26 118.5 . . ? C25 C26 H26 118.5 . . ? C32 C31 C36 115.8(3) . . ? C32 C31 B1 122.1(3) . . ? C36 C31 B1 122.0(3) . . ? C33 C32 C31 122.6(3) . . ? C33 C32 H32 118.7 . . ? C31 C32 H32 118.7 . . ? C34 C33 C32 119.8(3) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C35 C34 C33 119.4(3) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? C34 C35 C36 120.4(3) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 122.0(3) . . ? C31 C36 H36 119.0 . . ? C35 C36 H36 119.0 . . ? C46 C41 C42 115.1(3) . . ? C46 C41 B2 122.7(3) . . ? C42 C41 B2 122.1(3) . . ? C43 C42 C41 123.0(3) . . ? C43 C42 H42 118.5 . . ? C41 C42 H42 118.5 . . ? C44 C43 C42 120.0(3) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C45 C44 C43 118.9(3) . . ? C45 C44 H44 120.5 . . ? C43 C44 H44 120.5 . . ? C44 C45 C46 120.7(3) . . ? C44 C45 H45 119.6 . . ? C46 C45 H45 119.6 . . ? C45 C46 C41 122.3(3) . . ? C45 C46 H46 118.9 . . ? C41 C46 H46 118.9 . . ? C56 C51 C52 115.4(3) . . ? C56 C51 B2 120.9(3) . . ? C52 C51 B2 123.2(3) . . ? C53 C52 C51 122.9(3) . . ? C53 C52 H52 118.5 . . ? C51 C52 H52 118.5 . . ? C54 C53 C52 119.9(3) . . ? C54 C53 H53 120.1 . . ? C52 C53 H53 120.1 . . ? C55 C54 C53 119.0(3) . . ? C55 C54 H54 120.5 . . ? C53 C54 H54 120.5 . . ? C54 C55 C56 120.5(3) . . ? C54 C55 H55 119.7 . . ? C56 C55 H55 119.7 . . ? C55 C56 C51 122.2(3) . . ? C55 C56 H56 118.9 . . ? C51 C56 H56 118.9 . . ? C62 C61 C66 115.1(3) . . ? C62 C61 B2 126.4(3) . . ? C66 C61 B2 118.3(3) . . ? C61 C62 C63 122.6(3) . . ? C61 C62 H62 118.7 . . ? C63 C62 H62 118.7 . . ? C64 C63 C62 120.2(3) . . ? C64 C63 H63 119.9 . . ? C62 C63 H63 119.9 . . ? C63 C64 C65 119.3(3) . . ? C63 C64 H64 120.4 . . ? C65 C64 H64 120.4 . . ? C64 C65 C66 119.7(3) . . ? C64 C65 H65 120.1 . . ? C66 C65 H65 120.1 . . ? C65 C66 C61 123.1(3) . . ? C65 C66 H66 118.5 . . ? C61 C66 H66 118.5 . . ? N71 C71 C72 179.8(5) . . ? C71 C72 H72C 109.5 . . ? C71 C72 H72A 109.5 . . ? H72C C72 H72A 109.5 . . ? C71 C72 H72B 109.5 . . ? H72C C72 H72B 109.5 . . ? H72A C72 H72B 109.5 . . ? N81 C81 C82 179.0(4) . . ? C81 C82 H82A 109.5 . . ? C81 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? C81 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? H82C C82 H82B 109.5 . . ? C11 B1 C31 114.4(2) . . ? C11 B1 C21 107.4(2) . . ? C31 B1 C21 114.2(3) . . ? C11 B1 N1 106.1(2) . . ? C31 B1 N1 105.2(2) . . ? C21 B1 N1 109.2(2) . . ? C41 B2 C51 115.6(3) . . ? C41 B2 C61 113.4(2) . . ? C51 B2 C61 106.8(2) . . ? C41 B2 N2 105.6(2) . . ? C51 B2 N2 109.2(2) . . ? C61 B2 N2 105.7(2) . . ? 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 O1 C7 1.207(3) . ? O2 C7 1.340(3) . ? O2 C8 1.456(3) . ? N1 C2 1.451(4) . ? N1 B1 1.679(4) . ? N1 H11A 0.96(3) . ? N1 H11B 0.97(4) . ? N2 C6 1.462(3) . ? N2 B2 1.681(4) . ? N2 H21B 0.95(3) . ? N2 H21A 0.93(3) . ? N71 C71 1.135(4) . ? N81 C81 1.142(4) . ? C1 C6 1.397(4) . ? C1 C2 1.406(4) . ? C1 C7 1.495(4) . ? C2 C3 1.384(4) . ? C3 C4 1.375(4) . ? C3 H3 0.9500 . ? C4 C5 1.378(4) . ? C4 H4 0.9500 . ? C5 C6 1.384(4) . ? C5 H5 0.9500 . ? C8 H8C 0.9800 . ? C8 H8B 0.9800 . ? C8 H8A 0.9800 . ? C11 C12 1.393(4) . ? C11 C16 1.406(4) . ? C11 B1 1.620(5) . ? C12 C13 1.391(4) . ? C12 H12 0.9500 . ? C13 C14 1.378(4) . ? C13 H13 0.9500 . ? C14 C15 1.381(4) . ? C14 H14 0.9500 . ? C15 C16 1.379(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.386(4) . ? C21 C22 1.402(4) . ? C21 B1 1.628(4) . ? C22 C23 1.387(4) . ? C22 H22 0.9500 . ? C23 C24 1.374(4) . ? C23 H23 0.9500 . ? C24 C25 1.380(5) . ? C24 H24 0.9500 . ? C25 C26 1.391(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C32 1.393(4) . ? C31 C36 1.393(4) . ? C31 B1 1.626(4) . ? C32 C33 1.386(4) . ? C32 H32 0.9500 . ? C33 C34 1.381(4) . ? C33 H33 0.9500 . ? C34 C35 1.364(4) . ? C34 H34 0.9500 . ? C35 C36 1.394(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C46 1.396(4) . ? C41 C42 1.400(4) . ? C41 B2 1.618(5) . ? C42 C43 1.376(4) . ? C42 H42 0.9500 . ? C43 C44 1.376(5) . ? C43 H43 0.9500 . ? C44 C45 1.373(5) . ? C44 H44 0.9500 . ? C45 C46 1.380(4) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C51 C56 1.393(4) . ? C51 C52 1.397(4) . ? C51 B2 1.621(4) . ? C52 C53 1.381(4) . ? C52 H52 0.9500 . ? C53 C54 1.380(5) . ? C53 H53 0.9500 . ? C54 C55 1.374(5) . ? C54 H54 0.9500 . ? C55 C56 1.387(5) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? C61 C62 1.389(4) . ? C61 C66 1.401(4) . ? C61 B2 1.626(4) . ? C62 C63 1.392(4) . ? C62 H62 0.9500 . ? C63 C64 1.373(4) . ? C63 H63 0.9500 . ? C64 C65 1.378(4) . ? C64 H64 0.9500 . ? C65 C66 1.382(4) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? C71 C72 1.463(5) . ? C72 H72C 0.9800 . ? C72 H72A 0.9800 . ? C72 H72B 0.9800 . ? C81 C82 1.435(5) . ? C82 H82A 0.9800 . ? C82 H82C 0.9800 . ? C82 H82B 0.9800 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H21B N81 0.95(3) 2.09(3) 2.976(4) 154(2) . N1 H11A O1 0.96(3) 1.96(3) 2.722(3) 135(3) . N2 H21A O2 0.93(3) 1.90(3) 2.708(3) 144(2) . N1 H11B N71 0.97(4) 2.10(4) 2.995(4) 152(3) . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.1(4) . . . . ? C7 C1 C2 C3 180.0(3) . . . . ? C6 C1 C2 N1 177.6(3) . . . . ? C7 C1 C2 N1 -2.6(4) . . . . ? B1 N1 C2 C3 82.2(3) . . . . ? B1 N1 C2 C1 -95.3(3) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? N1 C2 C3 C4 -177.7(3) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C3 C4 C5 C6 0.5(4) . . . . ? C4 C5 C6 C1 -0.6(4) . . . . ? C4 C5 C6 N2 -178.9(3) . . . . ? C2 C1 C6 C5 0.3(4) . . . . ? C7 C1 C6 C5 -179.6(3) . . . . ? C2 C1 C6 N2 178.5(3) . . . . ? C7 C1 C6 N2 -1.4(4) . . . . ? B2 N2 C6 C5 84.6(3) . . . . ? B2 N2 C6 C1 -93.7(3) . . . . ? C8 O2 C7 O1 -1.4(4) . . . . ? C8 O2 C7 C1 -179.7(2) . . . . ? C6 C1 C7 O1 149.8(3) . . . . ? C2 C1 C7 O1 -30.1(4) . . . . ? C6 C1 C7 O2 -31.8(4) . . . . ? C2 C1 C7 O2 148.3(3) . . . . ? C16 C11 C12 C13 0.9(4) . . . . ? B1 C11 C12 C13 176.5(3) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? C12 C13 C14 C15 -1.7(5) . . . . ? C13 C14 C15 C16 1.5(4) . . . . ? C14 C15 C16 C11 -0.1(4) . . . . ? C12 C11 C16 C15 -1.1(4) . . . . ? B1 C11 C16 C15 -177.0(3) . . . . ? C26 C21 C22 C23 -1.6(4) . . . . ? B1 C21 C22 C23 -172.8(3) . . . . ? C21 C22 C23 C24 1.5(5) . . . . ? C22 C23 C24 C25 -0.5(5) . . . . ? C23 C24 C25 C26 -0.3(5) . . . . ? C22 C21 C26 C25 0.7(4) . . . . ? B1 C21 C26 C25 172.2(3) . . . . ? C24 C25 C26 C21 0.2(5) . . . . ? C36 C31 C32 C33 -0.8(4) . . . . ? B1 C31 C32 C33 176.0(3) . . . . ? C31 C32 C33 C34 1.8(5) . . . . ? C32 C33 C34 C35 -1.4(5) . . . . ? C33 C34 C35 C36 0.0(5) . . . . ? C32 C31 C36 C35 -0.6(4) . . . . ? B1 C31 C36 C35 -177.4(3) . . . . ? C34 C35 C36 C31 1.0(5) . . . . ? C46 C41 C42 C43 -1.6(4) . . . . ? B2 C41 C42 C43 -178.8(3) . . . . ? C41 C42 C43 C44 1.4(5) . . . . ? C42 C43 C44 C45 -0.5(5) . . . . ? C43 C44 C45 C46 0.0(5) . . . . ? C44 C45 C46 C41 -0.4(5) . . . . ? C42 C41 C46 C45 1.1(5) . . . . ? B2 C41 C46 C45 178.3(3) . . . . ? C56 C51 C52 C53 -1.0(4) . . . . ? B2 C51 C52 C53 -172.7(3) . . . . ? C51 C52 C53 C54 1.9(5) . . . . ? C52 C53 C54 C55 -0.7(5) . . . . ? C53 C54 C55 C56 -1.3(5) . . . . ? C54 C55 C56 C51 2.3(5) . . . . ? C52 C51 C56 C55 -1.1(5) . . . . ? B2 C51 C56 C55 170.8(3) . . . . ? C66 C61 C62 C63 1.3(4) . . . . ? B2 C61 C62 C63 176.1(3) . . . . ? C61 C62 C63 C64 -0.9(5) . . . . ? C62 C63 C64 C65 0.3(5) . . . . ? C63 C64 C65 C66 -0.2(5) . . . . ? C64 C65 C66 C61 0.7(5) . . . . ? C62 C61 C66 C65 -1.3(4) . . . . ? B2 C61 C66 C65 -176.5(3) . . . . ? C12 C11 B1 C31 136.7(3) . . . . ? C16 C11 B1 C31 -47.9(4) . . . . ? C12 C11 B1 C21 -95.5(3) . . . . ? C16 C11 B1 C21 79.9(3) . . . . ? C12 C11 B1 N1 21.2(4) . . . . ? C16 C11 B1 N1 -163.4(2) . . . . ? C32 C31 B1 C11 160.2(3) . . . . ? C36 C31 B1 C11 -23.2(4) . . . . ? C32 C31 B1 C21 36.0(4) . . . . ? C36 C31 B1 C21 -147.5(3) . . . . ? C32 C31 B1 N1 -83.8(3) . . . . ? C36 C31 B1 N1 92.8(3) . . . . ? C26 C21 B1 C11 -90.4(3) . . . . ? C22 C21 B1 C11 80.4(4) . . . . ? C26 C21 B1 C31 37.6(4) . . . . ? C22 C21 B1 C31 -151.7(3) . . . . ? C26 C21 B1 N1 155.0(3) . . . . ? C22 C21 B1 N1 -34.2(4) . . . . ? C2 N1 B1 C11 169.7(2) . . . . ? C2 N1 B1 C31 48.2(3) . . . . ? C2 N1 B1 C21 -74.9(3) . . . . ? C46 C41 B2 C51 33.9(4) . . . . ? C42 C41 B2 C51 -149.2(3) . . . . ? C46 C41 B2 C61 157.7(3) . . . . ? C42 C41 B2 C61 -25.4(4) . . . . ? C46 C41 B2 N2 -87.0(3) . . . . ? C42 C41 B2 N2 90.0(3) . . . . ? C56 C51 B2 C41 33.2(4) . . . . ? C52 C51 B2 C41 -155.5(3) . . . . ? C56 C51 B2 C61 -94.0(3) . . . . ? C52 C51 B2 C61 77.3(3) . . . . ? C56 C51 B2 N2 152.0(3) . . . . ? C52 C51 B2 N2 -36.7(4) . . . . ? C62 C61 B2 C41 134.7(3) . . . . ? C66 C61 B2 C41 -50.7(4) . . . . ? C62 C61 B2 C51 -96.8(3) . . . . ? C66 C61 B2 C51 77.8(3) . . . . ? C62 C61 B2 N2 19.4(4) . . . . ? C66 C61 B2 N2 -165.9(2) . . . . ? C6 N2 B2 C41 51.2(3) . . . . ? C6 N2 B2 C51 -73.7(3) . . . . ? C6 N2 B2 C61 171.7(2) . . . . ?