#------------------------------------------------------------------------------ #$Date: 2026-05-04 23:24:13 +0100 (Mon, 04 May 2026) $ #$Revision: 305712 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064399.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_7064399 loop_ _publ_author_name 'Almin, Arzu' 'Basumatary, Devi' 'Konwar, Dipika' 'Dutta, Prajjalita' 'Borah, Jagat C.' 'Bora, Utpal' _publ_section_title ; Regioselective N2-arylation of tetrazoles under CuO nanocatalysis: a route to potent anti-MRSA agents ; _journal_issue 14 _journal_name_full 'New Journal of Chemistry' _journal_page_first 6040 _journal_page_last 6047 _journal_paper_doi 10.1039/D5NJ04286K _journal_volume 50 _journal_year 2026 _chemical_formula_sum 'C13 H10 N4' _chemical_formula_weight 222.25 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2026-03-04 deposited with the CCDC. 2026-03-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.01(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.08(2) _cell_length_b 16.32(7) _cell_length_c 13.82(6) _cell_measurement_reflns_used 926 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 12.67 _cell_measurement_theta_min 2.91 _cell_volume 1146(8) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _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 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.2199 _diffrn_reflns_av_unetI/netI 0.1359 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 39529 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.993 _diffrn_reflns_theta_min 1.473 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.288 _exptl_crystal_description block _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.270 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.130 _refine_diff_density_max 0.160 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.053 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack -5(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 308 _refine_ls_number_reflns 4455 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.1715 _refine_ls_R_factor_gt 0.0688 _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^)] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1277 _refine_ls_wR_factor_ref 0.1576 _reflns_Friedel_coverage 0.929 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 2055 _reflns_number_total 4455 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj04286k2.cif _cod_data_source_block BS_AA207 _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7064399 _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 0.978 _shelx_estimated_absorpt_t_max 0.989 _exptl_absorpt_special_details SADABS _shelx_res_file ; BS_AA207.res created by SHELXL-2014/7 TITL AAA_a.res in P1 New: P21 CELL 0.71073 5.0800 16.3200 13.8200 90.000 90.010 90.000 ZERR 4 0.0200 0.0700 0.0600 0.000 0.040 0.000 LATT -1 SYMM - X , 0.50000 + Y , - Z SFAC C N H UNIT 52 16 40 OMIT 0 -11 9 OMIT -2 7 10 OMIT -1 -6 8 OMIT -3 4 10 OMIT 0 -10 3 OMIT 3 -11 3 OMIT 4 -3 0 OMIT 1 0 2 OMIT 4 -11 6 OMIT 2 -14 2 OMIT 3 -3 6 OMIT 1 13 6 OMIT 5 -6 0 OMIT -1 2 1 OMIT 5 3 1 OMIT -2 -12 7 OMIT 0 6 8 OMIT 0 -18 6 OMIT 0 -7 9 OMIT 1 -12 8 OMIT -3 7 7 OMIT 0 -12 6 OMIT 2 -11 2 OMIT 1 -6 12 OMIT -2 -1 3 OMIT 0 -5 10 OMIT -4 0 4 OMIT -1 -9 11 OMIT 2 5 10 OMIT -1 -2 1 OMIT -3 9 8 OMIT -1 11 5 OMIT 2 1 0 OMIT -1 4 10 OMIT -1 13 6 OMIT 1 -10 2 OMIT -3 12 6 OMIT 4 -8 3 OMIT 1 1 11 OMIT 4 8 6 OMIT 4 8 2 OMIT 2 8 8 OMIT 0 -15 1 OMIT -1 1 2 OMIT -4 8 2 OMIT -4 6 2 OMIT -1 -1 1 OMIT -3 0 6 OMIT 0 -10 4 OMIT -1 -5 6 OMIT -1 52 L.S. 20 ACTA BOND $H FMAP 2 PLAN 5 SIZE 0.27 0.19 0.13 WGHT 0.000000 BASF -4.98649 FVAR 1.12667 RESI 0 TWIN CONF TEMP -173.00 N3 2 0.841980 0.394508 0.000011 11.00000 0.07841 0.05306 = 0.06723 -0.00273 -0.01009 0.00169 N4 2 0.687596 0.414476 0.076860 11.00000 0.06828 0.05486 = 0.05314 -0.00768 -0.00227 0.00862 N1 2 0.601115 0.288772 0.022325 11.00000 0.08145 0.05151 = 0.08560 -0.00669 -0.00284 -0.00310 N2 2 0.790051 0.318514 -0.034062 11.00000 0.08717 0.04798 = 0.08446 -0.01993 -0.00060 0.00407 C1 1 0.538648 0.346292 0.087393 11.00000 0.05516 0.03316 = 0.05248 -0.00351 -0.00346 -0.00259 C2 1 0.344074 0.336419 0.160383 11.00000 0.07200 0.03883 = 0.05935 0.00127 -0.01660 0.00185 C8 1 1.038822 0.447375 -0.041966 11.00000 0.05790 0.05019 = 0.06116 -0.00085 -0.00739 -0.00051 C3 1 0.300912 0.395006 0.231092 11.00000 0.07364 0.06545 = 0.06182 -0.00144 -0.00298 -0.00735 AFIX 43 H3 3 0.404583 0.443446 0.232042 11.00000 -1.20000 AFIX 0 C9 1 1.196668 0.418044 -0.116410 11.00000 0.08841 0.05467 = 0.06240 -0.00479 -0.00477 0.00846 AFIX 43 H9 3 1.177325 0.363270 -0.138565 11.00000 -1.20000 AFIX 0 C7 1 0.186012 0.266276 0.159093 11.00000 0.07661 0.05303 = 0.06962 0.00447 -0.00222 0.00328 AFIX 43 H7 3 0.208150 0.226169 0.109942 11.00000 -1.20000 AFIX 0 C4 1 0.108036 0.383500 0.300306 11.00000 0.09087 0.06744 = 0.06490 -0.00014 -0.00574 -0.00590 AFIX 43 H4 3 0.081788 0.424139 0.348567 11.00000 -1.20000 AFIX 0 C10 1 1.381547 0.468935 -0.157924 11.00000 0.07848 0.08111 = 0.07394 0.00363 0.00443 -0.00058 AFIX 43 H10 3 1.490194 0.449050 -0.208700 11.00000 -1.20000 AFIX 0 C6 1 -0.003807 0.255835 0.230450 11.00000 0.08867 0.05317 = 0.08525 0.01387 -0.00995 -0.00664 AFIX 43 H6 3 -0.106714 0.207233 0.230952 11.00000 -1.20000 AFIX 0 C5 1 -0.045981 0.314599 0.300619 11.00000 0.08822 0.07081 = 0.06529 0.02213 0.00138 -0.00185 AFIX 43 H5 3 -0.179078 0.307401 0.348144 11.00000 -1.20000 AFIX 0 C13 1 1.066391 0.526920 -0.008493 11.00000 0.07995 0.05333 = 0.07767 -0.00792 0.00092 -0.00159 AFIX 43 H13 3 0.959133 0.547071 0.042535 11.00000 -1.20000 AFIX 0 C11 1 1.409392 0.548112 -0.126289 11.00000 0.07390 0.07581 = 0.07073 0.00837 0.00151 -0.00638 AFIX 43 H11 3 1.534997 0.583065 -0.156112 11.00000 -1.20000 AFIX 0 C12 1 1.257847 0.577021 -0.052249 11.00000 0.09004 0.06094 = 0.07676 -0.00096 -0.00996 -0.01239 AFIX 43 H12 3 1.281878 0.631587 -0.029995 11.00000 -1.20000 AFIX 0 N6 2 0.959969 0.151903 0.587611 11.00000 0.08542 0.04864 = 0.07023 0.00424 0.01148 0.00254 N7 2 0.899580 0.210653 0.521032 11.00000 0.08652 0.05150 = 0.07679 0.01106 0.00593 0.00348 N8 2 0.707769 0.180847 0.466347 11.00000 0.08090 0.06181 = 0.07418 0.00794 0.00072 0.00147 N5 2 0.812145 0.084927 0.576263 11.00000 0.06745 0.04070 = 0.06586 0.00167 0.00803 -0.00548 C14 1 0.659261 0.104404 0.501130 11.00000 0.06192 0.03500 = 0.05010 0.00635 0.00782 0.00165 C21 1 1.161875 0.162376 0.660071 11.00000 0.06177 0.05181 = 0.05618 -0.00241 0.01245 -0.00181 C15 1 0.463954 0.051375 0.458323 11.00000 0.07554 0.04748 = 0.05325 -0.00341 0.01407 0.00839 C17 1 0.121228 0.030553 0.342097 11.00000 0.08731 0.07334 = 0.06783 0.00382 0.00240 0.00255 AFIX 43 H17 3 0.016737 0.050222 0.290027 11.00000 -1.20000 AFIX 0 C22 1 1.197732 0.104268 0.731861 11.00000 0.07159 0.05909 = 0.06382 -0.00083 0.00629 -0.01489 AFIX 43 H22 3 1.088209 0.057124 0.734112 11.00000 -1.20000 AFIX 0 C24 1 1.547185 0.185185 0.801156 11.00000 0.07472 0.07217 = 0.07547 -0.01754 0.00481 -0.00081 AFIX 43 H24 3 1.677666 0.192972 0.849542 11.00000 -1.20000 AFIX 0 C26 1 1.311843 0.233917 0.659798 11.00000 0.07924 0.05301 = 0.07313 0.00239 0.00937 0.00149 AFIX 43 H26 3 1.281884 0.275251 0.612662 11.00000 -1.20000 AFIX 0 C23 1 1.392779 0.114991 0.800074 11.00000 0.08755 0.06226 = 0.06345 0.00122 0.01585 -0.00913 AFIX 43 H23 3 1.422065 0.073598 0.847194 11.00000 -1.20000 AFIX 0 C20 1 0.433094 -0.027539 0.491561 11.00000 0.07597 0.05908 = 0.06987 0.00794 0.00074 -0.00388 AFIX 43 H20 3 0.537972 -0.047423 0.543411 11.00000 -1.20000 AFIX 0 C16 1 0.305843 0.081319 0.383845 11.00000 0.07770 0.05770 = 0.06510 0.00715 0.01090 0.00547 AFIX 43 H16 3 0.325185 0.136204 0.362078 11.00000 -1.20000 AFIX 0 C18 1 0.086564 -0.048047 0.374840 11.00000 0.07946 0.07916 = 0.08013 -0.01505 0.00405 -0.00545 AFIX 43 H18 3 -0.045852 -0.082040 0.347542 11.00000 -1.20000 AFIX 0 C19 1 0.247502 -0.077355 0.448436 11.00000 0.09864 0.05933 = 0.08114 0.00048 0.00405 -0.01085 AFIX 43 H19 3 0.229495 -0.132514 0.469378 11.00000 -1.20000 AFIX 0 C25 1 1.506312 0.243692 0.729854 11.00000 0.08193 0.05627 = 0.09320 -0.01530 0.00947 -0.00841 AFIX 43 H25 3 1.613296 0.291428 0.728822 11.00000 -1.20000 AFIX 0 HKLF 4 1 -1.0000 0.0000 0.0000 0.0000 0.0000 1.0000 0.0000 1.0000 0.0000 REM AAA_a.res in P1 New: P21 REM R1 = 0.0688 for 2055 Fo > 4sig(Fo) and 0.1715 for all 4455 data REM 308 parameters refined using 1 restraints END WGHT 0.0717 0.0000 REM Highest difference peak 0.160, deepest hole -0.276, 1-sigma level 0.053 Q1 1 1.4418 0.6645 -0.2164 11.00000 0.05 0.16 Q2 1 0.0593 0.1612 0.3948 11.00000 0.05 0.16 Q3 1 0.5927 0.2640 0.5443 11.00000 0.05 0.15 Q4 1 0.2935 0.5187 0.2803 11.00000 0.05 0.15 Q5 1 -0.3328 0.2216 0.2014 11.00000 0.05 0.15 ; _shelx_res_checksum 25495 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N3 N 0.8420(12) 0.3945(4) 0.0000(4) 0.0662(17) Uani 1 1 d . . . . . N4 N 0.6876(11) 0.4145(3) 0.0769(4) 0.0588(15) Uani 1 1 d . . . . . N1 N 0.6011(13) 0.2888(4) 0.0223(5) 0.0729(18) Uani 1 1 d . . . . . N2 N 0.7901(13) 0.3185(4) -0.0341(5) 0.0732(18) Uani 1 1 d . . . . . C1 C 0.5386(13) 0.3463(4) 0.0874(5) 0.0469(17) Uani 1 1 d . . . . . C2 C 0.3441(14) 0.3364(4) 0.1604(5) 0.0567(19) Uani 1 1 d . . . . . C8 C 1.0388(13) 0.4474(4) -0.0420(5) 0.0564(18) Uani 1 1 d . . . . . C3 C 0.3009(14) 0.3950(5) 0.2311(5) 0.067(2) Uani 1 1 d . . . . . H3 H 0.4046 0.4434 0.2320 0.080 Uiso 1 1 calc R U . . . C9 C 1.1967(15) 0.4180(5) -0.1164(5) 0.068(2) Uani 1 1 d . . . . . H9 H 1.1773 0.3633 -0.1386 0.082 Uiso 1 1 calc R U . . . C7 C 0.1860(14) 0.2663(5) 0.1591(6) 0.066(2) Uani 1 1 d . . . . . H7 H 0.2081 0.2262 0.1099 0.080 Uiso 1 1 calc R U . . . C4 C 0.1080(16) 0.3835(5) 0.3003(6) 0.074(2) Uani 1 1 d . . . . . H4 H 0.0818 0.4241 0.3486 0.089 Uiso 1 1 calc R U . . . C10 C 1.3815(16) 0.4689(6) -0.1579(6) 0.078(2) Uani 1 1 d . . . . . H10 H 1.4902 0.4490 -0.2087 0.093 Uiso 1 1 calc R U . . . C6 C -0.0038(16) 0.2558(5) 0.2305(6) 0.076(2) Uani 1 1 d . . . . . H6 H -0.1067 0.2072 0.2310 0.091 Uiso 1 1 calc R U . . . C5 C -0.0460(16) 0.3146(5) 0.3006(6) 0.075(2) Uani 1 1 d . . . . . H5 H -0.1791 0.3074 0.3481 0.090 Uiso 1 1 calc R U . . . C13 C 1.0664(15) 0.5269(5) -0.0085(6) 0.070(2) Uani 1 1 d . . . . . H13 H 0.9591 0.5471 0.0425 0.084 Uiso 1 1 calc R U . . . C11 C 1.4094(16) 0.5481(5) -0.1263(6) 0.073(2) Uani 1 1 d . . . . . H11 H 1.5350 0.5831 -0.1561 0.088 Uiso 1 1 calc R U . . . C12 C 1.2578(16) 0.5770(5) -0.0522(6) 0.076(2) Uani 1 1 d . . . . . H12 H 1.2819 0.6316 -0.0300 0.091 Uiso 1 1 calc R U . . . N6 N 0.9600(13) 0.1519(3) 0.5876(5) 0.0681(18) Uani 1 1 d . . . . . N7 N 0.8996(13) 0.2107(4) 0.5210(5) 0.0716(18) Uani 1 1 d . . . . . N8 N 0.7078(13) 0.1808(4) 0.4663(5) 0.0723(18) Uani 1 1 d . . . . . N5 N 0.8121(11) 0.0849(3) 0.5763(4) 0.0580(15) Uani 1 1 d . . . . . C14 C 0.6593(13) 0.1044(4) 0.5011(5) 0.0490(17) Uani 1 1 d . . . . . C21 C 1.1619(14) 0.1624(4) 0.6601(5) 0.0566(19) Uani 1 1 d . . . . . C15 C 0.4640(14) 0.0514(4) 0.4583(5) 0.0588(19) Uani 1 1 d . . . . . C17 C 0.1212(17) 0.0306(5) 0.3421(6) 0.076(2) Uani 1 1 d . . . . . H17 H 0.0167 0.0502 0.2900 0.091 Uiso 1 1 calc R U . . . C22 C 1.1977(14) 0.1043(4) 0.7319(5) 0.0648(19) Uani 1 1 d . . . . . H22 H 1.0882 0.0571 0.7341 0.078 Uiso 1 1 calc R U . . . C24 C 1.5472(15) 0.1852(5) 0.8012(6) 0.074(2) Uani 1 1 d . . . . . H24 H 1.6777 0.1930 0.8495 0.089 Uiso 1 1 calc R U . . . C26 C 1.3118(15) 0.2339(5) 0.6598(6) 0.068(2) Uani 1 1 d . . . . . H26 H 1.2819 0.2753 0.6127 0.082 Uiso 1 1 calc R U . . . C23 C 1.3928(15) 0.1150(5) 0.8001(5) 0.071(2) Uani 1 1 d . . . . . H23 H 1.4221 0.0736 0.8472 0.085 Uiso 1 1 calc R U . . . C20 C 0.4331(15) -0.0275(5) 0.4916(6) 0.068(2) Uani 1 1 d . . . . . H20 H 0.5380 -0.0474 0.5434 0.082 Uiso 1 1 calc R U . . . C16 C 0.3058(14) 0.0813(5) 0.3838(5) 0.067(2) Uani 1 1 d . . . . . H16 H 0.3252 0.1362 0.3621 0.080 Uiso 1 1 calc R U . . . C18 C 0.0866(17) -0.0480(5) 0.3748(6) 0.080(2) Uani 1 1 d . . . . . H18 H -0.0459 -0.0820 0.3475 0.095 Uiso 1 1 calc R U . . . C19 C 0.2475(17) -0.0774(5) 0.4484(6) 0.080(2) Uani 1 1 d . . . . . H19 H 0.2295 -0.1325 0.4694 0.096 Uiso 1 1 calc R U . . . C25 C 1.5063(16) 0.2437(5) 0.7299(7) 0.077(2) Uani 1 1 d . . . . . H25 H 1.6133 0.2914 0.7288 0.093 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N3 0.078(4) 0.053(4) 0.067(4) -0.003(3) -0.010(4) 0.002(3) N4 0.068(4) 0.055(4) 0.053(4) -0.008(3) -0.002(3) 0.009(3) N1 0.081(5) 0.052(4) 0.086(5) -0.007(4) -0.003(4) -0.003(3) N2 0.087(5) 0.048(4) 0.084(5) -0.020(4) -0.001(4) 0.004(4) C1 0.055(4) 0.033(4) 0.052(4) -0.004(3) -0.003(4) -0.003(3) C2 0.072(5) 0.039(4) 0.059(5) 0.001(4) -0.017(4) 0.002(4) C8 0.058(4) 0.050(5) 0.061(5) -0.001(4) -0.007(4) -0.001(4) C3 0.074(5) 0.065(5) 0.062(5) -0.001(4) -0.003(4) -0.007(4) C9 0.088(6) 0.055(5) 0.062(5) -0.005(4) -0.005(4) 0.008(4) C7 0.077(5) 0.053(5) 0.070(5) 0.004(4) -0.002(4) 0.003(4) C4 0.091(6) 0.067(6) 0.065(5) 0.000(4) -0.006(5) -0.006(5) C10 0.078(6) 0.081(6) 0.074(6) 0.004(5) 0.004(5) -0.001(5) C6 0.089(6) 0.053(5) 0.085(6) 0.014(5) -0.010(5) -0.007(4) C5 0.088(6) 0.071(6) 0.065(5) 0.022(5) 0.001(4) -0.002(5) C13 0.080(5) 0.053(5) 0.078(5) -0.008(4) 0.001(4) -0.002(4) C11 0.074(6) 0.076(6) 0.071(6) 0.008(5) 0.002(4) -0.006(5) C12 0.090(6) 0.061(5) 0.077(6) -0.001(5) -0.010(5) -0.012(5) N6 0.085(5) 0.049(4) 0.070(5) 0.004(3) 0.011(4) 0.003(3) N7 0.087(5) 0.051(4) 0.077(5) 0.011(4) 0.006(4) 0.003(3) N8 0.081(5) 0.062(4) 0.074(5) 0.008(4) 0.001(4) 0.001(4) N5 0.067(4) 0.041(3) 0.066(4) 0.002(3) 0.008(3) -0.005(3) C14 0.062(4) 0.035(4) 0.050(4) 0.006(3) 0.008(4) 0.002(3) C21 0.062(5) 0.052(5) 0.056(5) -0.002(4) 0.012(4) -0.002(4) C15 0.076(5) 0.047(5) 0.053(5) -0.003(4) 0.014(4) 0.008(4) C17 0.087(6) 0.073(6) 0.068(5) 0.004(5) 0.002(5) 0.003(5) C22 0.072(5) 0.059(5) 0.064(5) -0.001(4) 0.006(4) -0.015(4) C24 0.075(5) 0.072(6) 0.075(6) -0.018(5) 0.005(4) -0.001(5) C26 0.079(6) 0.053(5) 0.073(6) 0.002(4) 0.009(5) 0.001(4) C23 0.088(6) 0.062(6) 0.063(5) 0.001(4) 0.016(5) -0.009(5) C20 0.076(5) 0.059(5) 0.070(5) 0.008(4) 0.001(4) -0.004(4) C16 0.078(5) 0.058(5) 0.065(5) 0.007(4) 0.011(4) 0.005(4) C18 0.079(6) 0.079(7) 0.080(6) -0.015(5) 0.004(5) -0.005(5) C19 0.099(6) 0.059(5) 0.081(6) 0.000(5) 0.004(5) -0.011(5) C25 0.082(6) 0.056(5) 0.093(7) -0.015(5) 0.009(5) -0.008(4) 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' N N 0.0061 0.0033 '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' 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 N2 N3 N4 112.3(6) . . ? N2 N3 C8 122.9(6) . . ? N4 N3 C8 124.8(6) . . ? C1 N4 N3 102.1(6) . . ? N2 N1 C1 108.0(6) . . ? N1 N2 N3 105.8(6) . . ? N1 C1 N4 111.8(7) . . ? N1 C1 C2 124.2(6) . . ? N4 C1 C2 123.9(6) . . ? C3 C2 C7 118.9(7) . . ? C3 C2 C1 122.2(7) . . ? C7 C2 C1 118.9(7) . . ? C13 C8 C9 120.8(7) . . ? C13 C8 N3 119.8(7) . . ? C9 C8 N3 119.5(7) . . ? C4 C3 C2 120.5(8) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C10 C9 C8 119.6(8) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C6 C7 C2 119.3(8) . . ? C6 C7 H7 120.3 . . ? C2 C7 H7 120.3 . . ? C5 C4 C3 121.2(8) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C9 C10 C11 120.3(8) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C5 C6 C7 121.4(8) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C4 C5 C6 118.6(8) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C8 C13 C12 118.1(8) . . ? C8 C13 H13 121.0 . . ? C12 C13 H13 121.0 . . ? C12 C11 C10 120.4(8) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 120.8(8) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? N5 N6 N7 111.7(7) . . ? N5 N6 C21 125.3(6) . . ? N7 N6 C21 123.0(6) . . ? N8 N7 N6 107.0(6) . . ? N7 N8 C14 105.6(6) . . ? C14 N5 N6 102.9(6) . . ? N5 C14 N8 112.8(6) . . ? N5 C14 C15 125.2(6) . . ? N8 C14 C15 122.0(7) . . ? C22 C21 C26 120.2(7) . . ? C22 C21 N6 120.6(7) . . ? C26 C21 N6 119.0(7) . . ? C20 C15 C16 120.6(7) . . ? C20 C15 C14 120.2(7) . . ? C16 C15 C14 119.2(7) . . ? C18 C17 C16 120.8(8) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C23 C22 C21 119.8(7) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C25 C24 C23 118.4(8) . . ? C25 C24 H24 120.8 . . ? C23 C24 H24 120.8 . . ? C25 C26 C21 118.8(8) . . ? C25 C26 H26 120.6 . . ? C21 C26 H26 120.6 . . ? C22 C23 C24 121.2(8) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? C15 C20 C19 119.0(8) . . ? C15 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C17 C16 C15 119.4(8) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C17 C18 C19 119.2(8) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C20 C19 C18 121.0(8) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C24 C25 C26 121.4(8) . . ? C24 C25 H25 119.3 . . ? C26 C25 H25 119.3 . . ? 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 N3 N2 1.353(9) . ? N3 N4 1.360(8) . ? N3 C8 1.443(9) . ? N4 C1 1.354(9) . ? N1 N2 1.328(8) . ? N1 C1 1.338(9) . ? C1 C2 1.422(10) . ? C2 C3 1.385(10) . ? C2 C7 1.398(10) . ? C8 C13 1.385(11) . ? C8 C9 1.390(10) . ? C3 C4 1.382(11) . ? C3 H3 0.9500 . ? C9 C10 1.379(10) . ? C9 H9 0.9500 . ? C7 C6 1.390(11) . ? C7 H7 0.9500 . ? C4 C5 1.370(11) . ? C4 H4 0.9500 . ? C10 C11 1.371(12) . ? C10 H10 0.9500 . ? C6 C5 1.381(12) . ? C6 H6 0.9500 . ? C5 H5 0.9500 . ? C13 C12 1.407(11) . ? C13 H13 0.9500 . ? C11 C12 1.365(11) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? N6 N5 1.335(9) . ? N6 N7 1.364(9) . ? N6 C21 1.443(10) . ? N7 N8 1.326(8) . ? N8 C14 1.359(9) . ? N5 C14 1.335(9) . ? C14 C15 1.443(10) . ? C21 C22 1.384(10) . ? C21 C26 1.394(10) . ? C15 C20 1.376(11) . ? C15 C16 1.394(10) . ? C17 C18 1.372(12) . ? C17 C16 1.378(10) . ? C17 H17 0.9500 . ? C22 C23 1.379(10) . ? C22 H22 0.9500 . ? C24 C25 1.388(12) . ? C24 C23 1.388(11) . ? C24 H24 0.9500 . ? C26 C25 1.392(11) . ? C26 H26 0.9500 . ? C23 H23 0.9500 . ? C20 C19 1.380(11) . ? C20 H20 0.9500 . ? C16 H16 0.9500 . ? C18 C19 1.390(12) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C25 H25 0.9500 . ? 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 N2 N3 N4 C1 -0.1(7) . . . . ? C8 N3 N4 C1 179.6(6) . . . . ? C1 N1 N2 N3 1.1(7) . . . . ? N4 N3 N2 N1 -0.6(8) . . . . ? C8 N3 N2 N1 179.7(6) . . . . ? N2 N1 C1 N4 -1.2(8) . . . . ? N2 N1 C1 C2 -179.7(6) . . . . ? N3 N4 C1 N1 0.8(7) . . . . ? N3 N4 C1 C2 179.3(6) . . . . ? N1 C1 C2 C3 174.6(6) . . . . ? N4 C1 C2 C3 -3.8(10) . . . . ? N1 C1 C2 C7 -7.3(10) . . . . ? N4 C1 C2 C7 174.4(6) . . . . ? N2 N3 C8 C13 174.6(7) . . . . ? N4 N3 C8 C13 -5.0(10) . . . . ? N2 N3 C8 C9 -4.6(10) . . . . ? N4 N3 C8 C9 175.7(6) . . . . ? C7 C2 C3 C4 1.2(10) . . . . ? C1 C2 C3 C4 179.4(6) . . . . ? C13 C8 C9 C10 -0.5(11) . . . . ? N3 C8 C9 C10 178.8(6) . . . . ? C3 C2 C7 C6 -2.1(10) . . . . ? C1 C2 C7 C6 179.6(6) . . . . ? C2 C3 C4 C5 -0.4(11) . . . . ? C8 C9 C10 C11 -0.2(12) . . . . ? C2 C7 C6 C5 2.3(10) . . . . ? C3 C4 C5 C6 0.5(11) . . . . ? C7 C6 C5 C4 -1.5(11) . . . . ? C9 C8 C13 C12 0.2(11) . . . . ? N3 C8 C13 C12 -179.0(6) . . . . ? C9 C10 C11 C12 1.2(13) . . . . ? C10 C11 C12 C13 -1.5(12) . . . . ? C8 C13 C12 C11 0.8(11) . . . . ? N5 N6 N7 N8 0.4(7) . . . . ? C21 N6 N7 N8 179.9(6) . . . . ? N6 N7 N8 C14 -0.5(7) . . . . ? N7 N6 N5 C14 -0.2(7) . . . . ? C21 N6 N5 C14 -179.6(6) . . . . ? N6 N5 C14 N8 -0.2(7) . . . . ? N6 N5 C14 C15 179.0(6) . . . . ? N7 N8 C14 N5 0.4(8) . . . . ? N7 N8 C14 C15 -178.7(6) . . . . ? N5 N6 C21 C22 -7.0(10) . . . . ? N7 N6 C21 C22 173.6(6) . . . . ? N5 N6 C21 C26 176.2(6) . . . . ? N7 N6 C21 C26 -3.2(9) . . . . ? N5 C14 C15 C20 -3.4(10) . . . . ? N8 C14 C15 C20 175.6(7) . . . . ? N5 C14 C15 C16 176.0(6) . . . . ? N8 C14 C15 C16 -5.0(9) . . . . ? C26 C21 C22 C23 -3.7(10) . . . . ? N6 C21 C22 C23 179.5(6) . . . . ? C22 C21 C26 C25 3.2(10) . . . . ? N6 C21 C26 C25 180.0(6) . . . . ? C21 C22 C23 C24 3.1(11) . . . . ? C25 C24 C23 C22 -1.9(11) . . . . ? C16 C15 C20 C19 1.6(11) . . . . ? C14 C15 C20 C19 -179.1(6) . . . . ? C18 C17 C16 C15 1.9(11) . . . . ? C20 C15 C16 C17 -1.4(10) . . . . ? C14 C15 C16 C17 179.3(6) . . . . ? C16 C17 C18 C19 -2.6(12) . . . . ? C15 C20 C19 C18 -2.3(12) . . . . ? C17 C18 C19 C20 2.8(12) . . . . ? C23 C24 C25 C26 1.5(11) . . . . ? C21 C26 C25 C24 -2.1(10) . . . . ?