#------------------------------------------------------------------------------ #$Date: 2024-12-11 01:37:27 +0200 (Wed, 11 Dec 2024) $ #$Revision: 296833 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249686.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_7249686 loop_ _publ_author_name 'wang, jiapeng' 'Wang, Jian-Hua' 'Liu, Yucun' 'Yuan, Junming' 'Yu, Yan-Wu' 'zhang, Yankang' 'Yan, Xuejian' _publ_section_title ; A novel bis(triazole)furoxan energetic compound---graphene-like crystal structure for balancing energy and sensitivity ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D4CE01116C _journal_year 2025 _chemical_formula_sum 'C18 H28 N12 O3' _chemical_formula_weight 460.52 _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 geom _audit_block_doi 10.5517/ccdc.csd.cc2k4wk5 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2024-05-25 deposited with the CCDC. 2024-12-05 downloaded from the CCDC. ; _cell_angle_alpha 90.850(4) _cell_angle_beta 94.688(4) _cell_angle_gamma 96.027(4) _cell_formula_units_Z 2 _cell_length_a 10.205(2) _cell_length_b 10.512(2) _cell_length_c 11.184(3) _cell_measurement_reflns_used 2171 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 24.50 _cell_measurement_theta_min 2.64 _cell_volume 1188.8(5) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_unetI/netI 0.0380 _diffrn_reflns_Laue_measured_fraction_full 0.986 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6023 _diffrn_reflns_point_group_measured_fraction_full 0.986 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 2.948 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_colour COLORLESS _exptl_crystal_density_diffrn 1.287 _exptl_crystal_description BLOCK _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.220 _refine_diff_density_max 0.753 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 332 _refine_ls_number_reflns 4139 _refine_ls_number_restraints 10 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0917 _refine_ls_R_factor_gt 0.0595 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1076P)^2^+0.0551P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1679 _refine_ls_wR_factor_ref 0.1821 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2760 _reflns_number_total 4139 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ce01116c2.cif _cod_data_source_block 1 _cod_database_code 7249686 _shelx_shelxl_version_number 2014/7 _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 0.976 _shelx_estimated_absorpt_t_max 0.980 _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1_a.res in P-1 CELL 0.71073 10.205 10.5119 11.1843 90.85 94.688 96.027 ZERR 2 0.0022 0.0023 0.0027 0.004 0.004 0.004 LATT 1 SFAC C H N O UNIT 36 56 24 6 OMIT 4 1 0 OMIT 1 0 1 OMIT -1 1 0 OMIT -1 2 0 OMIT 1 1 1 OMIT 0 1 1 OMIT -1 -2 1 OMIT 0 0 2 OMIT 0 -1 2 OMIT 1 -1 1 OMIT -1 -3 1 OMIT 0 -1 3 OMIT -1 1 2 OMIT -2 1 3 OMIT -3 0 1 OMIT 3 0 1 OMIT 1 0 2 OMIT -1 -2 3 OMIT -1 2 3 OMIT -2 0 1 OMIT 1 1 3 OMIT 2 2 1 OMIT 0.00 50.00 L.S. 23 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 SADI O3 C15 O3a C15a SADI O3 C18 O3a C18a SADI C15 C16 C15a C16a SADI C16 C17 C16a C17a SADI C17 C18 C17a C18a SADI 0.04 O3 C16 O3a C16a SADI 0.04 O3 C17 O3a C17a SADI 0.04 C15 C17 C15a C17a SADI 0.04 C15 C18 C15a C18a SADI 0.04 C16 C18 C16a C18a SIZE 0.26 0.24 0.22 HTAB C14 O3 CONF HTAB HTAB C12 O3A EQIV $1 x+1, y, z HTAB C5 O1_$1 HTAB C14 O3 HTAB C14 O3A TEMP 23 WGHT 0.107600 0.055100 FVAR 0.52637 0.65641 O1 4 0.198604 0.430182 0.152355 11.00000 0.04115 0.05508 = 0.10317 0.00455 0.00384 0.01786 N10 3 0.477407 0.134685 0.274214 11.00000 0.04883 0.03432 = 0.05907 -0.00141 0.00248 0.00475 N0AA 3 0.596888 0.579555 0.157869 11.00000 0.04032 0.03123 = 0.06048 -0.00177 0.00353 0.00251 N5 3 0.747290 0.450953 0.130307 11.00000 0.03342 0.03815 = 0.07542 -0.00191 0.00468 0.00502 N4 3 0.633426 0.372373 0.132346 11.00000 0.03752 0.03376 = 0.06848 -0.00237 0.00386 0.00389 N9 3 0.411410 -0.032547 0.155151 11.00000 0.04784 0.03425 = 0.06843 -0.00622 0.00130 0.00464 N8 3 0.349337 0.065780 0.105712 11.00000 0.04626 0.03793 = 0.06632 -0.00464 -0.00205 0.00663 N1 3 0.885560 0.886683 0.157574 11.00000 0.05008 0.04223 = 0.07298 -0.00324 0.00464 -0.00967 N2 3 0.827133 0.669885 0.146501 11.00000 0.04126 0.03856 = 0.07034 -0.00276 0.00213 -0.00117 N7 3 0.216758 0.297539 0.163356 11.00000 0.03309 0.04653 = 0.08319 0.00349 0.00298 0.00011 N6 3 0.320831 0.497618 0.146917 11.00000 0.03742 0.05074 = 0.07651 0.00118 0.00256 0.00612 N11 3 0.555761 -0.073937 0.320925 11.00000 0.07142 0.04108 = 0.06780 0.00550 0.00188 0.01760 O2 4 0.117535 0.225926 0.170168 11.00000 0.04822 0.06116 = 0.15565 0.01378 0.00986 -0.00300 C6 1 0.547900 0.454838 0.148843 11.00000 0.03741 0.03282 = 0.04827 -0.00118 0.00062 0.00455 C4 1 0.725226 0.574964 0.145267 11.00000 0.03775 0.03411 = 0.05278 0.00052 -0.00053 0.00280 C9 1 0.393405 0.161625 0.180233 11.00000 0.03184 0.03255 = 0.05631 0.00010 0.00223 0.00009 C7 1 0.407411 0.412464 0.154430 11.00000 0.03752 0.03636 = 0.05094 -0.00361 0.00155 0.00681 C10 1 0.486266 0.009708 0.255518 11.00000 0.04942 0.03468 = 0.05682 0.00240 0.00905 0.00665 C8 1 0.344927 0.287205 0.164437 11.00000 0.03345 0.03739 = 0.05141 0.00005 0.00295 0.00284 N12 3 0.713050 -0.096708 0.475069 11.00000 0.08363 0.08011 = 0.07086 0.02321 -0.00001 0.02437 C0AA 1 0.796259 0.786010 0.152803 11.00000 0.04303 0.04122 = 0.06364 -0.00035 0.00470 -0.00511 AFIX 43 H0AA 2 0.707619 0.798987 0.154016 11.00000 -1.20000 AFIX 0 C12 1 0.639187 -0.026051 0.406159 11.00000 0.05945 0.05290 = 0.07161 0.01630 0.00908 0.01286 AFIX 43 H12 2 0.648091 0.062000 0.420063 11.00000 -1.20000 AFIX 0 C5 1 0.871806 0.400725 0.111146 11.00000 0.04175 0.05332 = 0.12720 0.00013 0.01929 0.01505 AFIX 137 H5A 2 0.880511 0.326583 0.159056 11.00000 -1.50000 H5B 2 0.943933 0.464921 0.133827 11.00000 -1.50000 H5C 2 0.873046 0.377567 0.027925 11.00000 -1.50000 AFIX 0 C11 1 0.392051 -0.160361 0.100635 11.00000 0.06818 0.03962 = 0.10102 -0.01911 0.00154 0.00704 AFIX 137 H11A 2 0.301908 -0.195581 0.104846 11.00000 -1.50000 H11B 2 0.449882 -0.213985 0.142894 11.00000 -1.50000 H11C 2 0.411587 -0.155863 0.018190 11.00000 -1.50000 AFIX 0 C1 1 0.848483 1.016589 0.164045 11.00000 0.08102 0.04079 = 0.10807 -0.00771 0.01862 -0.01335 AFIX 137 H1A 2 0.753859 1.014126 0.156601 11.00000 -1.50000 H1B 2 0.884282 1.065263 0.100068 11.00000 -1.50000 H1C 2 0.882879 1.055963 0.239731 11.00000 -1.50000 AFIX 0 C2 1 1.023622 0.870412 0.152797 11.00000 0.05237 0.07803 = 0.14905 -0.00968 0.01372 -0.01672 AFIX 137 H2A 2 1.058176 0.841173 0.228730 11.00000 -1.50000 H2B 2 1.071405 0.950711 0.135488 11.00000 -1.50000 H2C 2 1.033188 0.808521 0.090995 11.00000 -1.50000 AFIX 0 C14 1 0.808519 -0.039673 0.569705 11.00000 0.08328 0.13860 = 0.10689 0.04673 -0.01961 -0.00024 AFIX 137 H14A 2 0.806032 0.051364 0.572094 11.00000 -1.50000 H14B 2 0.895571 -0.058602 0.553932 11.00000 -1.50000 H14C 2 0.786918 -0.074165 0.645502 11.00000 -1.50000 AFIX 0 C13 1 0.697659 -0.236026 0.461716 11.00000 0.17302 0.07596 = 0.11032 0.02016 -0.00799 0.05809 AFIX 137 H13A 2 0.667226 -0.273043 0.533741 11.00000 -1.50000 H13B 2 0.781235 -0.265072 0.447448 11.00000 -1.50000 H13C 2 0.634400 -0.261536 0.395182 11.00000 -1.50000 PART 1 AFIX 56 O3 4 0.862235 0.291817 0.525212 21.00000 0.51926 0.16935 = 0.17574 0.02170 0.10761 0.14828 C15 1 0.802232 0.335028 0.416359 21.00000 0.33791 0.14193 = 0.06545 -0.00095 0.02532 -0.05908 AFIX 23 H15A 2 0.867098 0.387257 0.374488 21.00000 -1.20000 H15B 2 0.766629 0.262554 0.364687 21.00000 -1.20000 AFIX 55 C16 1 0.699170 0.408032 0.445160 21.00000 0.36879 0.16057 = 0.09410 -0.02427 -0.02891 0.09062 AFIX 23 H16A 2 0.615171 0.369838 0.407011 21.00000 -1.20000 H16B 2 0.715640 0.494541 0.416812 21.00000 -1.20000 AFIX 55 C17 1 0.695476 0.409940 0.571813 21.00000 0.46050 0.40746 = 0.11456 -0.01400 -0.04346 0.11496 AFIX 23 H17A 2 0.609743 0.372641 0.593136 21.00000 -1.20000 H17B 2 0.710212 0.497344 0.602937 21.00000 -1.20000 AFIX 55 C18 1 0.796256 0.338115 0.621288 21.00000 0.49927 0.20086 = 0.07266 -0.01246 -0.03002 0.20198 AFIX 23 H18A 2 0.858315 0.391793 0.675644 21.00000 -1.20000 H18B 2 0.757846 0.267090 0.665843 21.00000 -1.20000 PART 2 AFIX 56 O3A 4 0.804414 0.248878 0.532114 -21.00000 0.20522 0.07028 = 0.24815 0.05124 -0.09748 -0.00937 C18A 1 0.890753 0.347422 0.485811 -21.00000 0.25193 0.37459 = 0.77957 0.37159 -0.11979 0.01614 AFIX 23 H18C 2 0.906654 0.326116 0.403935 -21.00000 -1.20000 H18D 2 0.974882 0.357353 0.533863 -21.00000 -1.20000 AFIX 55 C17A 1 0.829896 0.462706 0.489284 -21.00000 0.19144 0.11330 = 0.62160 0.18136 0.18017 0.09229 AFIX 23 H17C 2 0.817220 0.495533 0.409038 -21.00000 -1.20000 H17D 2 0.885448 0.526771 0.538966 -21.00000 -1.20000 AFIX 55 C16A 1 0.705945 0.435412 0.537732 -21.00000 0.25401 0.07939 = 0.17123 0.00580 0.06916 0.05168 AFIX 23 H16C 2 0.703294 0.486659 0.610164 -21.00000 -1.20000 H16D 2 0.635065 0.455422 0.480236 -21.00000 -1.20000 AFIX 55 C15A 1 0.690196 0.303258 0.564202 -21.00000 0.29805 0.18772 = 0.16014 -0.03917 0.10284 -0.02627 AFIX 23 H15C 2 0.680149 0.292451 0.649064 -21.00000 -1.20000 H15D 2 0.611921 0.261214 0.519135 -21.00000 -1.20000 PART 0 AFIX 0 HKLF 4 REM 1_a.res in P-1 REM R1 = 0.0595 for 2760 Fo > 4sig(Fo) and 0.0917 for all 4139 data REM 332 parameters refined using 10 restraints END WGHT 0.1068 0.0336 REM Instructions for potential hydrogen bonds HTAB C12 O3A HTAB C5 O1_$1 HTAB C14 O3 HTAB C14 O3A REM Highest difference peak 0.753, deepest hole -0.189, 1-sigma level 0.042 Q1 1 0.2859 0.5848 0.1419 11.00000 0.05 0.75 Q2 1 0.7059 0.3209 0.4742 11.00000 0.05 0.19 Q3 1 0.8542 0.2958 0.0960 11.00000 0.05 0.16 Q4 1 0.4827 0.4265 0.1757 11.00000 0.05 0.16 Q5 1 0.7792 0.4561 0.4392 11.00000 0.05 0.15 Q6 1 0.1487 0.3598 0.1819 11.00000 0.05 0.15 Q7 1 0.7989 0.4812 0.5707 11.00000 0.05 0.15 Q8 1 0.3822 0.3553 0.2093 11.00000 0.05 0.15 Q9 1 0.8791 0.0299 0.5122 11.00000 0.05 0.14 Q10 1 0.3209 0.2654 0.2218 11.00000 0.05 0.14 Q11 1 0.8744 0.4241 0.5987 11.00000 0.05 0.14 Q12 1 0.8515 0.4310 0.4383 11.00000 0.05 0.14 Q13 1 0.6186 0.6034 0.1049 11.00000 0.05 0.14 Q14 1 0.3704 -0.2235 0.1798 11.00000 0.05 0.14 Q15 1 0.4101 0.4441 0.1823 11.00000 0.05 0.14 Q16 1 0.5389 0.5083 0.1678 11.00000 0.05 0.13 Q17 1 0.7541 0.3546 0.4052 11.00000 0.05 0.13 Q18 1 0.4755 -0.1722 0.0611 11.00000 0.05 0.12 Q19 1 0.7648 -0.1684 0.4500 11.00000 0.05 0.12 Q20 1 0.8947 0.3733 0.2066 11.00000 0.05 0.12 ; _shelx_res_checksum 41129 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 0.19860(16) 0.43018(17) 0.15235(19) 0.0657(6) Uani 1 1 d . . . . . N10 N 0.47741(19) 0.13468(17) 0.2742(2) 0.0475(5) Uani 1 1 d . . . . . N0AA N 0.59689(18) 0.57955(16) 0.15787(19) 0.0442(5) Uani 1 1 d . . . . . N5 N 0.74729(18) 0.45095(18) 0.1303(2) 0.0489(6) Uani 1 1 d . . . . . N4 N 0.63343(18) 0.37237(17) 0.1323(2) 0.0466(5) Uani 1 1 d . . . . . N9 N 0.41141(19) -0.03255(18) 0.1552(2) 0.0504(6) Uani 1 1 d . . . . . N8 N 0.34934(19) 0.06578(18) 0.1057(2) 0.0504(6) Uani 1 1 d . . . . . N1 N 0.8856(2) 0.88668(19) 0.1576(2) 0.0562(6) Uani 1 1 d . . . . . N2 N 0.82713(19) 0.66989(18) 0.1465(2) 0.0506(6) Uani 1 1 d . . . . . N7 N 0.21676(19) 0.29754(19) 0.1634(2) 0.0546(6) Uani 1 1 d . . . . . N6 N 0.32083(19) 0.4976(2) 0.1469(2) 0.0549(6) Uani 1 1 d . . . . . N11 N 0.5558(2) -0.0739(2) 0.3209(2) 0.0595(6) Uani 1 1 d . . . . . O2 O 0.11753(19) 0.22593(19) 0.1702(2) 0.0888(8) Uani 1 1 d . . . . . C6 C 0.5479(2) 0.4548(2) 0.1488(2) 0.0396(6) Uani 1 1 d . . . . . C4 C 0.7252(2) 0.5750(2) 0.1453(2) 0.0419(6) Uani 1 1 d . . . . . C9 C 0.3934(2) 0.1616(2) 0.1802(2) 0.0406(6) Uani 1 1 d . . . . . C7 C 0.4074(2) 0.4125(2) 0.1544(2) 0.0416(6) Uani 1 1 d . . . . . C10 C 0.4863(2) 0.0097(2) 0.2555(2) 0.0466(6) Uani 1 1 d . . . . . C8 C 0.3449(2) 0.2872(2) 0.1644(2) 0.0409(6) Uani 1 1 d . . . . . N12 N 0.7131(3) -0.0967(3) 0.4751(3) 0.0772(8) Uani 1 1 d . . . . . C0AA C 0.7963(2) 0.7860(2) 0.1528(2) 0.0500(6) Uani 1 1 d . . . . . H0AA H 0.7076 0.7990 0.1540 0.060 Uiso 1 1 calc R U . . . C12 C 0.6392(3) -0.0261(3) 0.4062(3) 0.0605(8) Uani 1 1 d . . . . . H12 H 0.6481 0.0620 0.4201 0.073 Uiso 1 1 calc R U . . . C5 C 0.8718(3) 0.4007(3) 0.1111(4) 0.0727(9) Uani 1 1 d . . . . . H5A H 0.8805 0.3266 0.1591 0.109 Uiso 1 1 calc R U . . . H5B H 0.9439 0.4649 0.1338 0.109 Uiso 1 1 calc R U . . . H5C H 0.8730 0.3776 0.0279 0.109 Uiso 1 1 calc R U . . . C11 C 0.3921(3) -0.1604(2) 0.1006(3) 0.0700(9) Uani 1 1 d . . . . . H11A H 0.3019 -0.1956 0.1048 0.105 Uiso 1 1 calc R U . . . H11B H 0.4499 -0.2140 0.1429 0.105 Uiso 1 1 calc R U . . . H11C H 0.4116 -0.1559 0.0182 0.105 Uiso 1 1 calc R U . . . C1 C 0.8485(3) 1.0166(3) 0.1640(3) 0.0775(10) Uani 1 1 d . . . . . H1A H 0.7539 1.0141 0.1566 0.116 Uiso 1 1 calc R U . . . H1B H 0.8843 1.0653 0.1001 0.116 Uiso 1 1 calc R U . . . H1C H 0.8829 1.0560 0.2397 0.116 Uiso 1 1 calc R U . . . C2 C 1.0236(3) 0.8704(3) 0.1528(4) 0.0947(12) Uani 1 1 d . . . . . H2A H 1.0582 0.8412 0.2287 0.142 Uiso 1 1 calc R U . . . H2B H 1.0714 0.9507 0.1355 0.142 Uiso 1 1 calc R U . . . H2C H 1.0332 0.8085 0.0910 0.142 Uiso 1 1 calc R U . . . C14 C 0.8085(4) -0.0397(5) 0.5697(4) 0.1115(15) Uani 1 1 d . . . . . H14A H 0.8060 0.0514 0.5721 0.167 Uiso 1 1 calc R U . . . H14B H 0.8956 -0.0586 0.5539 0.167 Uiso 1 1 calc R U . . . H14C H 0.7869 -0.0742 0.6455 0.167 Uiso 1 1 calc R U . . . C13 C 0.6977(5) -0.2360(4) 0.4617(4) 0.1175(15) Uani 1 1 d . . . . . H13A H 0.6672 -0.2730 0.5337 0.176 Uiso 1 1 calc R U . . . H13B H 0.7812 -0.2651 0.4474 0.176 Uiso 1 1 calc R U . . . H13C H 0.6344 -0.2615 0.3952 0.176 Uiso 1 1 calc R U . . . O3 O 0.8622(15) 0.2918(13) 0.5252(10) 0.276(9) Uani 0.656(13) 1 d DG . P A 1 C15 C 0.8022(14) 0.3350(11) 0.4164(6) 0.187(7) Uani 0.656(13) 1 d DG . P A 1 H15A H 0.8671 0.3873 0.3745 0.225 Uiso 0.656(13) 1 calc R U P A 1 H15B H 0.7666 0.2626 0.3647 0.225 Uiso 0.656(13) 1 calc R U P A 1 C16 C 0.6992(14) 0.4080(12) 0.4452(10) 0.206(8) Uani 0.656(13) 1 d DG . P A 1 H16A H 0.6152 0.3698 0.4070 0.248 Uiso 0.656(13) 1 calc R U P A 1 H16B H 0.7156 0.4945 0.4168 0.248 Uiso 0.656(13) 1 calc R U P A 1 C17 C 0.6955(14) 0.4099(14) 0.5718(11) 0.327(19) Uani 0.656(13) 1 d DG . P A 1 H17A H 0.6097 0.3726 0.5931 0.392 Uiso 0.656(13) 1 calc R U P A 1 H17B H 0.7102 0.4973 0.6029 0.392 Uiso 0.656(13) 1 calc R U P A 1 C18 C 0.7963(18) 0.3381(13) 0.6213(6) 0.249(11) Uani 0.656(13) 1 d DG . P A 1 H18A H 0.8583 0.3918 0.6756 0.299 Uiso 0.656(13) 1 calc R U P A 1 H18B H 0.7578 0.2671 0.6658 0.299 Uiso 0.656(13) 1 calc R U P A 1 O3A O 0.8044(18) 0.2489(9) 0.5321(18) 0.182(10) Uani 0.344(13) 1 d DG . P A 2 C18A C 0.8908(18) 0.3474(16) 0.486(3) 0.48(6) Uani 0.344(13) 1 d DG . P A 2 H18C H 0.9067 0.3261 0.4039 0.570 Uiso 0.344(13) 1 calc R U P A 2 H18D H 0.9749 0.3574 0.5339 0.570 Uiso 0.344(13) 1 calc R U P A 2 C17A C 0.830(2) 0.4627(13) 0.489(3) 0.29(2) Uani 0.344(13) 1 d DG . P A 2 H17C H 0.8172 0.4955 0.4090 0.352 Uiso 0.344(13) 1 calc R U P A 2 H17D H 0.8854 0.5268 0.5390 0.352 Uiso 0.344(13) 1 calc R U P A 2 C16A C 0.706(2) 0.4354(15) 0.538(2) 0.163(13) Uani 0.344(13) 1 d DG . P A 2 H16C H 0.7033 0.4867 0.6102 0.196 Uiso 0.344(13) 1 calc R U P A 2 H16D H 0.6351 0.4554 0.4802 0.196 Uiso 0.344(13) 1 calc R U P A 2 C15A C 0.690(2) 0.3033(17) 0.564(2) 0.215(17) Uani 0.344(13) 1 d DG . P A 2 H15C H 0.6801 0.2925 0.6491 0.258 Uiso 0.344(13) 1 calc R U P A 2 H15D H 0.6119 0.2612 0.5191 0.258 Uiso 0.344(13) 1 calc R U P A 2 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 0.0411(10) 0.0551(11) 0.1032(17) 0.0045(10) 0.0038(10) 0.0179(8) N10 0.0488(12) 0.0343(11) 0.0591(14) -0.0014(9) 0.0025(10) 0.0047(8) N0AA 0.0403(11) 0.0312(10) 0.0605(14) -0.0018(9) 0.0035(9) 0.0025(8) N5 0.0334(10) 0.0381(11) 0.0754(16) -0.0019(10) 0.0047(9) 0.0050(8) N4 0.0375(10) 0.0338(10) 0.0685(15) -0.0024(9) 0.0039(9) 0.0039(8) N9 0.0478(12) 0.0342(11) 0.0684(16) -0.0062(10) 0.0013(10) 0.0046(9) N8 0.0463(11) 0.0379(11) 0.0663(15) -0.0046(10) -0.0021(10) 0.0066(9) N1 0.0501(12) 0.0422(12) 0.0730(17) -0.0032(11) 0.0046(11) -0.0097(9) N2 0.0413(11) 0.0386(11) 0.0703(16) -0.0028(10) 0.0021(10) -0.0012(9) N7 0.0331(11) 0.0465(12) 0.0832(17) 0.0035(11) 0.0030(10) 0.0001(9) N6 0.0374(11) 0.0507(13) 0.0765(17) 0.0012(11) 0.0026(10) 0.0061(9) N11 0.0714(15) 0.0411(12) 0.0678(17) 0.0055(11) 0.0019(12) 0.0176(11) O2 0.0482(12) 0.0612(13) 0.156(2) 0.0138(14) 0.0099(12) -0.0030(10) C6 0.0374(12) 0.0328(12) 0.0483(15) -0.0012(10) 0.0006(10) 0.0046(9) C4 0.0377(12) 0.0341(12) 0.0528(16) 0.0005(10) -0.0005(10) 0.0028(9) C9 0.0318(11) 0.0325(12) 0.0563(16) 0.0001(11) 0.0022(11) 0.0001(9) C7 0.0375(12) 0.0364(12) 0.0509(16) -0.0036(11) 0.0016(10) 0.0068(9) C10 0.0494(14) 0.0347(13) 0.0568(17) 0.0024(11) 0.0090(12) 0.0067(10) C8 0.0335(12) 0.0374(12) 0.0514(15) 0.0001(10) 0.0030(10) 0.0028(9) N12 0.0836(18) 0.0801(18) 0.0709(18) 0.0232(14) 0.0000(14) 0.0244(14) C0AA 0.0430(13) 0.0412(14) 0.0636(18) -0.0004(12) 0.0047(12) -0.0051(10) C12 0.0595(17) 0.0529(16) 0.072(2) 0.0163(15) 0.0091(15) 0.0129(13) C5 0.0417(14) 0.0533(16) 0.127(3) 0.0001(17) 0.0193(15) 0.0151(12) C11 0.0682(18) 0.0396(15) 0.101(3) -0.0191(15) 0.0015(16) 0.0070(13) C1 0.081(2) 0.0408(16) 0.108(3) -0.0077(16) 0.0186(18) -0.0134(14) C2 0.0524(19) 0.078(2) 0.149(4) -0.010(2) 0.014(2) -0.0167(16) C14 0.083(3) 0.139(4) 0.107(3) 0.047(3) -0.020(2) 0.000(2) C13 0.173(4) 0.076(2) 0.110(3) 0.020(2) -0.008(3) 0.058(3) O3 0.52(3) 0.169(10) 0.176(11) 0.022(8) 0.108(14) 0.148(13) C15 0.34(2) 0.142(10) 0.065(6) -0.001(6) 0.025(8) -0.059(12) C16 0.37(2) 0.161(11) 0.094(9) -0.024(7) -0.029(11) 0.091(13) C17 0.46(5) 0.41(4) 0.115(14) -0.014(19) -0.043(16) 0.11(3) C18 0.50(3) 0.201(15) 0.073(6) -0.012(7) -0.030(11) 0.202(18) O3A 0.205(14) 0.070(7) 0.25(2) 0.051(9) -0.097(15) -0.009(8) C18A 0.25(4) 0.37(7) 0.78(14) 0.37(9) -0.12(6) 0.02(4) C17A 0.19(2) 0.113(16) 0.62(7) 0.18(3) 0.18(3) 0.092(15) C16A 0.25(3) 0.079(12) 0.17(3) 0.006(14) 0.07(2) 0.052(15) C15A 0.30(4) 0.19(3) 0.16(3) -0.04(2) 0.10(3) -0.03(3) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 O1 N7 108.06(15) . . ? C10 N10 C9 102.0(2) . . ? C4 N0AA C6 102.72(18) . . ? N4 N5 C4 110.84(17) . . ? N4 N5 C5 121.27(19) . . ? C4 N5 C5 127.9(2) . . ? C6 N4 N5 101.45(18) . . ? C10 N9 N8 109.65(19) . . ? C10 N9 C11 129.0(2) . . ? N8 N9 C11 121.4(2) . . ? C9 N8 N9 101.95(19) . . ? C0AA N1 C2 120.3(2) . . ? C0AA N1 C1 121.7(2) . . ? C2 N1 C1 118.0(2) . . ? C0AA N2 C4 116.4(2) . . ? O2 N7 C8 136.5(2) . . ? O2 N7 O1 115.76(19) . . ? C8 N7 O1 107.71(18) . . ? C7 N6 O1 106.24(19) . . ? C12 N11 C10 117.1(2) . . ? N4 C6 N0AA 116.3(2) . . ? N4 C6 C7 121.1(2) . . ? N0AA C6 C7 122.57(19) . . ? N0AA C4 N5 108.67(19) . . ? N0AA C4 N2 131.0(2) . . ? N5 C4 N2 120.3(2) . . ? N8 C9 N10 116.32(19) . . ? N8 C9 C8 120.4(2) . . ? N10 C9 C8 123.1(2) . . ? N6 C7 C8 111.6(2) . . ? N6 C7 C6 119.4(2) . . ? C8 C7 C6 129.0(2) . . ? N10 C10 N9 110.1(2) . . ? N10 C10 N11 130.4(2) . . ? N9 C10 N11 119.5(2) . . ? N7 C8 C7 106.39(19) . . ? N7 C8 C9 119.7(2) . . ? C7 C8 C9 133.83(19) . . ? C12 N12 C14 121.7(3) . . ? C12 N12 C13 120.9(3) . . ? C14 N12 C13 117.4(3) . . ? N2 C0AA N1 122.6(2) . . ? N2 C0AA H0AA 118.7 . . ? N1 C0AA H0AA 118.7 . . ? N11 C12 N12 122.8(3) . . ? N11 C12 H12 118.6 . . ? N12 C12 H12 118.6 . . ? N5 C5 H5A 109.5 . . ? N5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N9 C11 H11A 109.5 . . ? N9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N12 C14 H14A 109.5 . . ? N12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N12 C13 H13A 109.5 . . ? N12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C18 O3 C15 108.0 . . ? C16 C15 O3 108.0 . . ? C16 C15 H15A 110.1 . . ? O3 C15 H15A 110.1 . . ? C16 C15 H15B 110.1 . . ? O3 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? C15 C16 C17 108.0 . . ? C15 C16 H16A 110.1 . . ? C17 C16 H16A 110.1 . . ? C15 C16 H16B 110.1 . . ? C17 C16 H16B 110.1 . . ? H16A C16 H16B 108.4 . . ? C16 C17 C18 108.0 . . ? C16 C17 H17A 110.1 . . ? C18 C17 H17A 110.1 . . ? C16 C17 H17B 110.1 . . ? C18 C17 H17B 110.1 . . ? H17A C17 H17B 108.4 . . ? O3 C18 C17 108.0 . . ? O3 C18 H18A 110.1 . . ? C17 C18 H18A 110.1 . . ? O3 C18 H18B 110.1 . . ? C17 C18 H18B 110.1 . . ? H18A C18 H18B 108.4 . . ? C18A O3A C15A 108.0 . . ? O3A C18A C17A 108.0 . . ? O3A C18A H18C 110.1 . . ? C17A C18A H18C 110.1 . . ? O3A C18A H18D 110.1 . . ? C17A C18A H18D 110.1 . . ? H18C C18A H18D 108.4 . . ? C18A C17A C16A 108.0 . . ? C18A C17A H17C 110.1 . . ? C16A C17A H17C 110.1 . . ? C18A C17A H17D 110.1 . . ? C16A C17A H17D 110.1 . . ? H17C C17A H17D 108.4 . . ? C15A C16A C17A 108.0 . . ? C15A C16A H16C 110.1 . . ? C17A C16A H16C 110.1 . . ? C15A C16A H16D 110.1 . . ? C17A C16A H16D 110.1 . . ? H16C C16A H16D 108.4 . . ? O3A C15A C16A 108.0 . . ? O3A C15A H15C 110.1 . . ? C16A C15A H15C 110.1 . . ? O3A C15A H15D 110.1 . . ? C16A C15A H15D 110.1 . . ? H15C C15A H15D 108.4 . . ? 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 N6 1.375(3) . ? O1 N7 1.432(3) . ? N10 C10 1.341(3) . ? N10 C9 1.354(3) . ? N0AA C4 1.334(3) . ? N0AA C6 1.352(3) . ? N5 N4 1.355(3) . ? N5 C4 1.356(3) . ? N5 C5 1.456(3) . ? N4 C6 1.314(3) . ? N9 C10 1.347(3) . ? N9 N8 1.368(3) . ? N9 C11 1.455(3) . ? N8 C9 1.316(3) . ? N1 C0AA 1.320(3) . ? N1 C2 1.442(4) . ? N1 C1 1.457(3) . ? N2 C0AA 1.295(3) . ? N2 C4 1.363(3) . ? N7 O2 1.205(2) . ? N7 C8 1.323(3) . ? N6 C7 1.321(3) . ? N11 C12 1.285(4) . ? N11 C10 1.370(3) . ? C6 C7 1.463(3) . ? C9 C8 1.466(3) . ? C7 C8 1.412(3) . ? N12 C12 1.324(4) . ? N12 C14 1.456(5) . ? N12 C13 1.461(5) . ? C0AA H0AA 0.9300 . ? C12 H12 0.9300 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? O3 C18 1.4200 . ? O3 C15 1.4200 . ? C15 C16 1.4200 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.4200 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.4200 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? O3A C18A 1.4200 . ? O3A C15A 1.4200 . ? C18A C17A 1.4200 . ? C18A H18C 0.9700 . ? C18A H18D 0.9700 . ? C17A C16A 1.4200 . ? C17A H17C 0.9700 . ? C17A H17D 0.9700 . ? C16A C15A 1.4200 . ? C16A H16C 0.9700 . ? C16A H16D 0.9700 . ? C15A H15C 0.9700 . ? C15A H15D 0.9700 . ? 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 C14 H14A O3 0.96 2.60 3.519(15) 159.7 . C12 H12 O3A 0.93 2.63 3.413(12) 142.2 . C5 H5B O1 0.96 2.65 3.310(3) 126.0 1_655 C14 H14A O3 0.96 2.60 3.519(15) 159.7 . C14 H14A O3A 0.96 2.13 3.073(10) 166.2 . 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 C4 N5 N4 C6 -0.1(3) . . . . ? C5 N5 N4 C6 -178.7(3) . . . . ? C10 N9 N8 C9 0.8(3) . . . . ? C11 N9 N8 C9 -179.6(2) . . . . ? N6 O1 N7 O2 179.4(2) . . . . ? N6 O1 N7 C8 0.0(3) . . . . ? N7 O1 N6 C7 -0.2(3) . . . . ? N5 N4 C6 N0AA -0.1(3) . . . . ? N5 N4 C6 C7 178.6(2) . . . . ? C4 N0AA C6 N4 0.3(3) . . . . ? C4 N0AA C6 C7 -178.5(2) . . . . ? C6 N0AA C4 N5 -0.3(3) . . . . ? C6 N0AA C4 N2 -179.7(3) . . . . ? N4 N5 C4 N0AA 0.3(3) . . . . ? C5 N5 C4 N0AA 178.8(3) . . . . ? N4 N5 C4 N2 179.7(2) . . . . ? C5 N5 C4 N2 -1.7(4) . . . . ? C0AA N2 C4 N0AA -5.3(4) . . . . ? C0AA N2 C4 N5 175.3(2) . . . . ? N9 N8 C9 N10 -0.6(3) . . . . ? N9 N8 C9 C8 -176.5(2) . . . . ? C10 N10 C9 N8 0.2(3) . . . . ? C10 N10 C9 C8 175.9(2) . . . . ? O1 N6 C7 C8 0.3(3) . . . . ? O1 N6 C7 C6 178.8(2) . . . . ? N4 C6 C7 N6 -166.5(2) . . . . ? N0AA C6 C7 N6 12.2(4) . . . . ? N4 C6 C7 C8 11.8(4) . . . . ? N0AA C6 C7 C8 -169.5(2) . . . . ? C9 N10 C10 N9 0.3(3) . . . . ? C9 N10 C10 N11 -179.2(3) . . . . ? N8 N9 C10 N10 -0.7(3) . . . . ? C11 N9 C10 N10 179.6(2) . . . . ? N8 N9 C10 N11 178.9(2) . . . . ? C11 N9 C10 N11 -0.7(4) . . . . ? C12 N11 C10 N10 -9.6(4) . . . . ? C12 N11 C10 N9 170.8(3) . . . . ? O2 N7 C8 C7 -179.1(3) . . . . ? O1 N7 C8 C7 0.1(3) . . . . ? O2 N7 C8 C9 -1.8(5) . . . . ? O1 N7 C8 C9 177.3(2) . . . . ? N6 C7 C8 N7 -0.2(3) . . . . ? C6 C7 C8 N7 -178.6(2) . . . . ? N6 C7 C8 C9 -176.9(3) . . . . ? C6 C7 C8 C9 4.7(5) . . . . ? N8 C9 C8 N7 57.3(3) . . . . ? N10 C9 C8 N7 -118.3(3) . . . . ? N8 C9 C8 C7 -126.4(3) . . . . ? N10 C9 C8 C7 58.0(4) . . . . ? C4 N2 C0AA N1 178.3(2) . . . . ? C2 N1 C0AA N2 1.6(4) . . . . ? C1 N1 C0AA N2 179.7(3) . . . . ? C10 N11 C12 N12 -179.4(3) . . . . ? C14 N12 C12 N11 178.9(3) . . . . ? C13 N12 C12 N11 -3.6(5) . . . . ? C18 O3 C15 C16 0.0 . . . . ? O3 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C15 O3 C18 C17 0.0 . . . . ? C16 C17 C18 O3 0.0 . . . . ? C15A O3A C18A C17A 0.0 . . . . ? O3A C18A C17A C16A 0.0 . . . . ? C18A C17A C16A C15A 0.0 . . . . ? C18A O3A C15A C16A 0.0 . . . . ? C17A C16A C15A O3A 0.0 . . . . ?