#------------------------------------------------------------------------------ #$Date: 2026-05-04 14:11:28 +0100 (Mon, 04 May 2026) $ #$Revision: 305706 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/09/7720978.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_7720978 loop_ _publ_author_name 'Balayan, Kajal' 'Biswas, Arindam' 'Sharma, Himanshu' 'Tiwari, Prabhakar' 'Vanka, Kumar' 'Gonnade, Rajesh G.' 'Rath, Arup K.' 'Sen, Sakya S.' _publ_section_title ; Unveiling the reactivity of N-heterocyclic methylene hydrazines. ; _journal_issue 14 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 5432 _journal_page_last 5436 _journal_paper_doi 10.1039/d6dt00611f _journal_volume 55 _journal_year 2026 _chemical_formula_moiety 'C17 H21 N7' _chemical_formula_sum 'C17 H21 N7' _chemical_formula_weight 323.41 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2026-02-08 deposited with the CCDC. 2026-03-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.1540(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.6450(6) _cell_length_b 11.6884(4) _cell_length_c 10.8720(4) _cell_measurement_reflns_used 9890 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.84 _cell_measurement_theta_min 2.29 _cell_volume 1735.62(11) _computing_cell_refinement 'SAINT (Bruker, 2016)' _computing_data_collection 'APEX3 (Bruker, 2016)' _computing_data_reduction 'SAINT (Bruker, 2016)' _computing_molecular_graphics 'Bruker SHELXTL, Mercury 2020.20' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'Photon II CPAD Area Detector' _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'multilayer mirrors' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0950 _diffrn_reflns_av_unetI/netI 0.0331 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 94288 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.104 _diffrn_reflns_theta_min 2.659 _diffrn_source 'micro-focus sealed tube' _diffrn_source_type 'Incoatech I\mS HB' _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_correction_T_min 0.6041 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour Red _exptl_crystal_density_diffrn 1.238 _exptl_crystal_description block _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.320 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 223 _refine_ls_number_reflns 5101 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0456 _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^)+(0.0332P)^2^+0.9057P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0999 _refine_ls_wR_factor_ref 0.1057 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4251 _reflns_number_total 5101 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt00611f2.cif _cod_data_source_block mo_Kb_ItBuCH2_TCNE_0m_a _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7720978 _shelx_shelxl_version_number 2018/3 _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 0.971 _shelx_estimated_absorpt_t_max 0.991 _shelx_res_file ; TITL mo_Kb_ItBuCH2_TCNE_0m_a.res in P2(1)/c mo_Kb_ItBuCH2_TCNE_0m_a.res created by SHELXL-2018/3 at 11:18:57 on 08-Oct-2024 REM Old TITL Integration of Kb_ItBuCH2_TCNE REM SHELXT solution in P2(1)/c: R1 0.106, Rweak 0.008, Alpha 0.030 REM 0.731 for 192 systematic absences, Orientation a'=c, b'=-b, c'=a REM Formula found by SHELXT: C17 N7 CELL 0.71073 14.6450 11.6884 10.8720 90.000 111.154 90.000 ZERR 4.000 0.0006 0.0004 0.0004 0.000 0.001 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N UNIT 68 84 28 ACTA TEMP -173.150 L.S. 10 BOND $H CONF SIZE 0.37 0.23 0.11 HTAB OMIT 1 1 0 LIST 4 FMAP 2 PLAN 20 WGHT 0.033200 0.905700 FVAR 0.72606 N1 3 0.668057 0.769667 0.710098 11.00000 0.01518 0.01243 = 0.01396 0.00043 0.00556 0.00123 N2 3 0.808555 0.767488 0.678035 11.00000 0.01375 0.01296 = 0.01165 0.00070 0.00394 -0.00013 N3 3 0.714463 0.585627 0.674680 11.00000 0.01471 0.01284 = 0.01491 -0.00028 0.00566 0.00041 N4 3 0.754605 0.523508 0.608522 11.00000 0.01296 0.01448 = 0.01373 -0.00101 0.00381 0.00096 N5 3 0.830903 0.067009 0.437414 11.00000 0.03209 0.02386 = 0.02731 -0.00604 0.01010 0.00371 N6 3 0.643839 0.142720 0.669546 11.00000 0.02791 0.01774 = 0.04271 0.00692 0.01851 0.00444 N7 3 0.874960 0.401085 0.412510 11.00000 0.02663 0.02527 = 0.02786 0.00314 0.01532 0.00419 C1 1 0.733589 0.700312 0.683606 11.00000 0.01356 0.01293 = 0.01042 0.00074 0.00358 0.00099 C2 1 0.786668 0.879399 0.698434 11.00000 0.02003 0.01213 = 0.01589 0.00048 0.00592 -0.00009 AFIX 43 H2 2 0.825613 0.944473 0.698732 11.00000 -1.20000 AFIX 0 C3 1 0.700743 0.880594 0.717829 11.00000 0.02083 0.01238 = 0.01733 0.00004 0.00711 0.00204 AFIX 43 H3 2 0.668590 0.946340 0.733944 11.00000 -1.20000 AFIX 0 C4 1 0.577074 0.731568 0.733428 11.00000 0.01415 0.01807 = 0.01632 0.00054 0.00692 0.00100 C5 1 0.509580 0.665237 0.614092 11.00000 0.01438 0.02823 = 0.01714 -0.00044 0.00316 -0.00058 AFIX 137 H5A 2 0.448322 0.647081 0.626996 11.00000 -1.50000 H5B 2 0.541780 0.594153 0.604275 11.00000 -1.50000 H5C 2 0.495362 0.711943 0.534484 11.00000 -1.50000 AFIX 0 C6 1 0.608411 0.659305 0.858942 11.00000 0.01894 0.02323 = 0.01510 0.00181 0.00765 -0.00015 AFIX 137 H6A 2 0.550329 0.635625 0.877107 11.00000 -1.50000 H6B 2 0.651413 0.704566 0.933128 11.00000 -1.50000 H6C 2 0.643591 0.591370 0.847101 11.00000 -1.50000 AFIX 0 C7 1 0.523071 0.838538 0.752018 11.00000 0.02401 0.02181 = 0.03586 0.00164 0.01741 0.00586 AFIX 137 H7A 2 0.463174 0.815811 0.766100 11.00000 -1.50000 H7B 2 0.506063 0.886666 0.673100 11.00000 -1.50000 H7C 2 0.565417 0.881594 0.828750 11.00000 -1.50000 AFIX 0 C8 1 0.903264 0.733270 0.660922 11.00000 0.01229 0.01751 = 0.01397 0.00023 0.00498 -0.00042 C9 1 0.971587 0.837036 0.691450 11.00000 0.01658 0.02092 = 0.02350 -0.00089 0.00654 -0.00450 AFIX 137 H9A 2 1.034685 0.814780 0.686496 11.00000 -1.50000 H9B 2 0.981688 0.865105 0.780345 11.00000 -1.50000 H9C 2 0.942135 0.897663 0.627055 11.00000 -1.50000 AFIX 0 C10 1 0.879398 0.699106 0.517119 11.00000 0.01771 0.02258 = 0.01406 0.00088 0.00741 -0.00073 AFIX 137 H10A 2 0.939782 0.677093 0.503922 11.00000 -1.50000 H10B 2 0.849232 0.763987 0.459750 11.00000 -1.50000 H10C 2 0.833861 0.634312 0.495389 11.00000 -1.50000 AFIX 0 C11 1 0.953161 0.637918 0.758202 11.00000 0.01500 0.02047 = 0.01558 0.00245 0.00458 0.00325 AFIX 137 H11A 2 1.013311 0.614568 0.745193 11.00000 -1.50000 H11B 2 0.908857 0.572245 0.743180 11.00000 -1.50000 H11C 2 0.969301 0.665815 0.848599 11.00000 -1.50000 AFIX 0 C12 1 0.733640 0.412147 0.611783 11.00000 0.01490 0.01471 = 0.01697 -0.00014 0.00644 -0.00054 AFIX 43 H12 2 0.693544 0.387526 0.658605 11.00000 -1.20000 AFIX 0 C13 1 0.770655 0.332537 0.546508 11.00000 0.01285 0.01547 = 0.01415 -0.00093 0.00302 0.00049 C14 1 0.754132 0.214277 0.547071 11.00000 0.01562 0.01451 = 0.01782 -0.00120 0.00466 0.00076 C15 1 0.796265 0.133622 0.485298 11.00000 0.01927 0.01629 = 0.01859 -0.00180 0.00327 -0.00034 C16 1 0.693790 0.172319 0.614580 11.00000 0.01908 0.01231 = 0.02568 0.00147 0.00682 0.00262 C17 1 0.829018 0.372678 0.473179 11.00000 0.01691 0.01535 = 0.01779 -0.00099 0.00492 0.00268 HKLF 4 REM mo_Kb_ItBuCH2_TCNE_0m_a.res in P2(1)/c REM wR2 = 0.105744, GooF = S = 1.06047, Restrained GooF = 1.06047 for all data REM R1 = 0.045571 for 4251 Fo > 4sig(Fo) and 0.058536 for all 5101 data REM 223 parameters refined using 0 restraints END WGHT 0.0332 0.9057 REM Instructions for potential hydrogen bonds EQIV $1 x, y+1, z HTAB C3 N6_$1 HTAB C5 N3 HTAB C6 N3 EQIV $2 -x+2, -y+1, -z+1 HTAB C10 N7_$2 HTAB C10 N4 HTAB C11 N3 HTAB C11 N4 REM Highest difference peak 0.320, deepest hole -0.239, 1-sigma level 0.045 Q1 1 0.8840 0.7176 0.5837 11.00000 0.05 0.32 Q2 1 0.5919 0.7011 0.7977 11.00000 0.05 0.32 Q3 1 0.7610 0.2716 0.5398 11.00000 0.05 0.31 Q4 1 0.9417 0.7797 0.6782 11.00000 0.05 0.29 Q5 1 0.5502 0.7829 0.7450 11.00000 0.05 0.28 Q6 1 0.7517 0.3683 0.5783 11.00000 0.05 0.26 Q7 1 0.9245 0.6792 0.7050 11.00000 0.05 0.26 Q8 1 0.5469 0.7001 0.6751 11.00000 0.05 0.25 Q9 1 0.7961 0.8245 0.6889 11.00000 0.05 0.25 Q10 1 0.7469 0.8889 0.7213 11.00000 0.05 0.24 Q11 1 0.7610 0.1793 0.4991 11.00000 0.05 0.23 Q12 1 0.6855 0.8243 0.7187 11.00000 0.05 0.22 Q13 1 0.7307 0.6411 0.6761 11.00000 0.05 0.22 Q14 1 0.6981 0.7290 0.6997 11.00000 0.05 0.20 Q15 1 0.7117 0.5663 0.7422 11.00000 0.05 0.19 Q16 1 0.7153 0.8940 0.6475 11.00000 0.05 0.19 Q17 1 0.7517 0.4634 0.6145 11.00000 0.05 0.19 Q18 1 0.6639 0.2064 0.6369 11.00000 0.05 0.18 Q19 1 0.6989 0.1487 0.6854 11.00000 0.05 0.18 Q20 1 0.7833 0.7275 0.6976 11.00000 0.05 0.17 ; _shelx_res_checksum 88147 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.66806(7) 0.76967(8) 0.71010(9) 0.01377(18) Uani 1 1 d . . . . . N2 N 0.80856(7) 0.76749(8) 0.67803(9) 0.01297(18) Uani 1 1 d . . . . . N3 N 0.71446(7) 0.58563(8) 0.67468(9) 0.01407(18) Uani 1 1 d . . . . . N4 N 0.75461(7) 0.52351(8) 0.60852(9) 0.01400(18) Uani 1 1 d . . . . . N5 N 0.83090(9) 0.06701(10) 0.43741(12) 0.0279(2) Uani 1 1 d . . . . . N6 N 0.64384(9) 0.14272(9) 0.66955(13) 0.0279(3) Uani 1 1 d . . . . . N7 N 0.87496(8) 0.40109(10) 0.41251(11) 0.0251(2) Uani 1 1 d . . . . . C1 C 0.73359(8) 0.70031(9) 0.68361(10) 0.01251(19) Uani 1 1 d . . . . . C2 C 0.78667(8) 0.87940(9) 0.69843(11) 0.0162(2) Uani 1 1 d . . . . . H2 H 0.825613 0.944473 0.698732 0.019 Uiso 1 1 calc R U . . . C3 C 0.70074(9) 0.88059(10) 0.71783(11) 0.0168(2) Uani 1 1 d . . . . . H3 H 0.668590 0.946340 0.733944 0.020 Uiso 1 1 calc R U . . . C4 C 0.57707(8) 0.73157(10) 0.73343(11) 0.0158(2) Uani 1 1 d . . . . . C5 C 0.50958(8) 0.66524(11) 0.61409(12) 0.0206(2) Uani 1 1 d . . . . . H5A H 0.448322 0.647081 0.626996 0.031 Uiso 1 1 calc R U . . . H5B H 0.541780 0.594153 0.604275 0.031 Uiso 1 1 calc R U . . . H5C H 0.495362 0.711943 0.534484 0.031 Uiso 1 1 calc R U . . . C6 C 0.60841(9) 0.65930(11) 0.85894(11) 0.0187(2) Uani 1 1 d . . . . . H6A H 0.550329 0.635625 0.877107 0.028 Uiso 1 1 calc R U . . . H6B H 0.651413 0.704566 0.933128 0.028 Uiso 1 1 calc R U . . . H6C H 0.643591 0.591370 0.847101 0.028 Uiso 1 1 calc R U . . . C7 C 0.52307(10) 0.83854(11) 0.75202(14) 0.0254(3) Uani 1 1 d . . . . . H7A H 0.463174 0.815811 0.766100 0.038 Uiso 1 1 calc R U . . . H7B H 0.506063 0.886666 0.673100 0.038 Uiso 1 1 calc R U . . . H7C H 0.565417 0.881594 0.828750 0.038 Uiso 1 1 calc R U . . . C8 C 0.90326(8) 0.73327(10) 0.66092(11) 0.0145(2) Uani 1 1 d . . . . . C9 C 0.97159(9) 0.83704(10) 0.69145(12) 0.0205(2) Uani 1 1 d . . . . . H9A H 1.034685 0.814780 0.686496 0.031 Uiso 1 1 calc R U . . . H9B H 0.981688 0.865105 0.780345 0.031 Uiso 1 1 calc R U . . . H9C H 0.942135 0.897663 0.627055 0.031 Uiso 1 1 calc R U . . . C10 C 0.87940(8) 0.69911(10) 0.51712(11) 0.0177(2) Uani 1 1 d . . . . . H10A H 0.939782 0.677093 0.503922 0.026 Uiso 1 1 calc R U . . . H10B H 0.849232 0.763987 0.459750 0.026 Uiso 1 1 calc R U . . . H10C H 0.833861 0.634312 0.495389 0.026 Uiso 1 1 calc R U . . . C11 C 0.95316(8) 0.63792(10) 0.75820(11) 0.0173(2) Uani 1 1 d . . . . . H11A H 1.013311 0.614568 0.745193 0.026 Uiso 1 1 calc R U . . . H11B H 0.908857 0.572245 0.743180 0.026 Uiso 1 1 calc R U . . . H11C H 0.969301 0.665815 0.848599 0.026 Uiso 1 1 calc R U . . . C12 C 0.73364(8) 0.41215(10) 0.61178(11) 0.0153(2) Uani 1 1 d . . . . . H12 H 0.693544 0.387526 0.658605 0.018 Uiso 1 1 calc R U . . . C13 C 0.77065(8) 0.33254(10) 0.54651(11) 0.0147(2) Uani 1 1 d . . . . . C14 C 0.75413(8) 0.21428(10) 0.54707(11) 0.0164(2) Uani 1 1 d . . . . . C15 C 0.79627(9) 0.13362(10) 0.48530(12) 0.0190(2) Uani 1 1 d . . . . . C16 C 0.69379(9) 0.17232(10) 0.61458(12) 0.0194(2) Uani 1 1 d . . . . . C17 C 0.82902(8) 0.37268(10) 0.47318(11) 0.0171(2) Uani 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 N1 0.0152(4) 0.0124(4) 0.0140(4) 0.0004(3) 0.0056(3) 0.0012(3) N2 0.0138(4) 0.0130(4) 0.0117(4) 0.0007(3) 0.0039(3) -0.0001(3) N3 0.0147(4) 0.0128(4) 0.0149(4) -0.0003(3) 0.0057(3) 0.0004(3) N4 0.0130(4) 0.0145(4) 0.0137(4) -0.0010(3) 0.0038(3) 0.0010(3) N5 0.0321(6) 0.0239(6) 0.0273(6) -0.0060(4) 0.0101(5) 0.0037(5) N6 0.0279(6) 0.0177(5) 0.0427(7) 0.0069(5) 0.0185(5) 0.0044(4) N7 0.0266(5) 0.0253(5) 0.0279(6) 0.0031(4) 0.0153(5) 0.0042(4) C1 0.0136(5) 0.0129(5) 0.0104(4) 0.0007(4) 0.0036(4) 0.0010(4) C2 0.0200(5) 0.0121(5) 0.0159(5) 0.0005(4) 0.0059(4) -0.0001(4) C3 0.0208(5) 0.0124(5) 0.0173(5) 0.0000(4) 0.0071(4) 0.0020(4) C4 0.0141(5) 0.0181(5) 0.0163(5) 0.0005(4) 0.0069(4) 0.0010(4) C5 0.0144(5) 0.0282(6) 0.0171(5) -0.0004(5) 0.0032(4) -0.0006(4) C6 0.0189(5) 0.0232(6) 0.0151(5) 0.0018(4) 0.0076(4) -0.0001(4) C7 0.0240(6) 0.0218(6) 0.0359(7) 0.0016(5) 0.0174(5) 0.0059(5) C8 0.0123(5) 0.0175(5) 0.0140(5) 0.0002(4) 0.0050(4) -0.0004(4) C9 0.0166(5) 0.0209(6) 0.0235(6) -0.0009(5) 0.0065(4) -0.0045(4) C10 0.0177(5) 0.0226(6) 0.0141(5) 0.0009(4) 0.0074(4) -0.0007(4) C11 0.0150(5) 0.0205(5) 0.0156(5) 0.0025(4) 0.0046(4) 0.0032(4) C12 0.0149(5) 0.0147(5) 0.0170(5) -0.0001(4) 0.0064(4) -0.0005(4) C13 0.0128(5) 0.0155(5) 0.0141(5) -0.0009(4) 0.0030(4) 0.0005(4) C14 0.0156(5) 0.0145(5) 0.0178(5) -0.0012(4) 0.0047(4) 0.0008(4) C15 0.0193(5) 0.0163(5) 0.0186(5) -0.0018(4) 0.0033(4) -0.0003(4) C16 0.0191(5) 0.0123(5) 0.0257(6) 0.0015(4) 0.0068(4) 0.0026(4) C17 0.0169(5) 0.0154(5) 0.0178(5) -0.0010(4) 0.0049(4) 0.0027(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' 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' 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 C1 N1 C3 108.51(9) . . ? C1 N1 C4 126.21(9) . . ? C3 N1 C4 125.22(9) . . ? C1 N2 C2 107.42(9) . . ? C1 N2 C8 129.58(9) . . ? C2 N2 C8 122.92(9) . . ? N4 N3 C1 117.69(9) . . ? N3 N4 C12 111.93(9) . . ? N1 C1 N3 117.16(9) . . ? N1 C1 N2 107.77(9) . . ? N3 C1 N2 135.00(10) . . ? C3 C2 N2 108.54(10) . . ? C3 C2 H2 125.7 . . ? N2 C2 H2 125.7 . . ? C2 C3 N1 107.74(10) . . ? C2 C3 H3 126.1 . . ? N1 C3 H3 126.1 . . ? N1 C4 C6 108.31(9) . . ? N1 C4 C5 110.27(9) . . ? C6 C4 C5 111.81(10) . . ? N1 C4 C7 108.08(9) . . ? C6 C4 C7 109.66(10) . . ? C5 C4 C7 108.64(10) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C10 108.22(8) . . ? N2 C8 C11 109.70(9) . . ? C10 C8 C11 113.16(9) . . ? N2 C8 C9 108.62(9) . . ? C10 C8 C9 108.63(9) . . ? C11 C8 C9 108.41(9) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 C13 120.00(10) . . ? N4 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 123.79(11) . . ? C12 C13 C17 118.80(10) . . ? C14 C13 C17 117.42(10) . . ? C13 C14 C15 123.11(11) . . ? C13 C14 C16 118.77(10) . . ? C15 C14 C16 118.11(10) . . ? N5 C15 C14 178.68(13) . . ? N6 C16 C14 177.31(12) . . ? N7 C17 C13 177.63(13) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3641(14) . ? N1 C3 1.3741(14) . ? N1 C4 1.5106(14) . ? N2 C1 1.3688(14) . ? N2 C2 1.3836(14) . ? N2 C8 1.5181(14) . ? N3 N4 1.3020(12) . ? N3 C1 1.3657(14) . ? N4 C12 1.3408(14) . ? N5 C15 1.1512(16) . ? N6 C16 1.1522(16) . ? N7 C17 1.1482(16) . ? C2 C3 1.3490(16) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C6 1.5278(16) . ? C4 C5 1.5283(16) . ? C4 C7 1.5313(16) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C10 1.5269(15) . ? C8 C11 1.5287(15) . ? C8 C9 1.5306(16) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.3932(15) . ? C12 H12 0.9500 . ? C13 C14 1.4037(16) . ? C13 C17 1.4415(16) . ? C14 C15 1.4211(16) . ? C14 C16 1.4242(16) . ? 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 C1 N3 N4 C12 177.35(10) . . . . ? C3 N1 C1 N3 178.79(9) . . . . ? C4 N1 C1 N3 1.37(15) . . . . ? C3 N1 C1 N2 1.49(12) . . . . ? C4 N1 C1 N2 -175.93(9) . . . . ? N4 N3 C1 N1 157.57(9) . . . . ? N4 N3 C1 N2 -26.07(18) . . . . ? C2 N2 C1 N1 -1.40(11) . . . . ? C8 N2 C1 N1 175.39(9) . . . . ? C2 N2 C1 N3 -177.99(12) . . . . ? C8 N2 C1 N3 -1.2(2) . . . . ? C1 N2 C2 C3 0.78(12) . . . . ? C8 N2 C2 C3 -176.27(9) . . . . ? N2 C2 C3 N1 0.13(13) . . . . ? C1 N1 C3 C2 -1.01(13) . . . . ? C4 N1 C3 C2 176.44(10) . . . . ? C1 N1 C4 C6 64.24(13) . . . . ? C3 N1 C4 C6 -112.77(12) . . . . ? C1 N1 C4 C5 -58.40(14) . . . . ? C3 N1 C4 C5 124.59(11) . . . . ? C1 N1 C4 C7 -177.02(10) . . . . ? C3 N1 C4 C7 5.97(15) . . . . ? C1 N2 C8 C10 74.56(13) . . . . ? C2 N2 C8 C10 -109.09(11) . . . . ? C1 N2 C8 C11 -49.34(14) . . . . ? C2 N2 C8 C11 127.01(11) . . . . ? C1 N2 C8 C9 -167.67(10) . . . . ? C2 N2 C8 C9 8.68(14) . . . . ? N3 N4 C12 C13 -179.83(10) . . . . ? N4 C12 C13 C14 178.61(11) . . . . ? N4 C12 C13 C17 -1.72(16) . . . . ? C12 C13 C14 C15 -176.87(11) . . . . ? C17 C13 C14 C15 3.45(17) . . . . ? C12 C13 C14 C16 1.95(17) . . . . ? C17 C13 C14 C16 -177.73(10) . . . . ?