Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Dipankar Datta' _publ_contact_author_address ; Dept. of Inorg. Chemistry IACS Jadavpur Calcutta West Bengal 700 032 INDIA ; _publ_contact_author_email ICDD@MAHENDRA.IACS.RES.IN _publ_section_title ; Molecular and supramolecular structures of benzil dihydrazone, an organic helical molecule. Comparison with diacetyl dihydrazone ; loop_ _publ_author_name 'Dipankar Datta' Shubhamoy 'Senjuti De' 'D. Tocher' data_str0229 _database_code_depnum_ccdc_archive 'CCDC 607989' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 N4' _chemical_formula_weight 238.29 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.0695(16) _cell_length_b 6.1051(4) _cell_length_c 32.4245(19) _cell_angle_alpha 90.00 _cell_angle_beta 111.4430(10) _cell_angle_gamma 90.00 _cell_volume 4987.6(5) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9651 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21247 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5959 _reflns_number_gt 5227 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+5.4326P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5959 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.30060(5) 0.9384(2) 0.03292(5) 0.0297(3) Uani 1 1 d . . . N2 N 0.34780(5) 0.9686(2) 0.06717(4) 0.0248(3) Uani 1 1 d . . . N3 N 0.33577(6) 0.4644(3) 0.06097(5) 0.0314(3) Uani 1 1 d . . . N4 N 0.36229(5) 0.4976(2) 0.03259(4) 0.0253(3) Uani 1 1 d . . . N5 N 0.20235(6) 0.7239(3) 0.07681(5) 0.0325(3) Uani 1 1 d . . . N6 N 0.25173(5) 0.6910(2) 0.10748(4) 0.0287(3) Uani 1 1 d . . . N7 N 0.21761(6) 0.2511(2) 0.05100(4) 0.0268(3) Uani 1 1 d . . . N8 N 0.20023(5) 0.2202(2) 0.08539(4) 0.0241(3) Uani 1 1 d . . . C1 C 0.38834(6) 0.8559(2) 0.06783(5) 0.0227(3) Uani 1 1 d . . . C2 C 0.43986(6) 0.8954(3) 0.10377(5) 0.0286(3) Uani 1 1 d . . . C3 C 0.45001(7) 1.0874(3) 0.12875(6) 0.0379(4) Uani 1 1 d . . . H3A H 0.4239 1.1947 0.1227 0.045 Uiso 1 1 calc R . . C4 C 0.49854(8) 1.1195(4) 0.16245(6) 0.0501(5) Uani 1 1 d . . . H4A H 0.5050 1.2486 0.1788 0.060 Uiso 1 1 calc R . . C5 C 0.53746(8) 0.9611(5) 0.17200(6) 0.0556(6) Uani 1 1 d . . . H5A H 0.5700 0.9831 0.1948 0.067 Uiso 1 1 calc R . . C6 C 0.52793(8) 0.7704(4) 0.14769(7) 0.0531(6) Uani 1 1 d . . . H6A H 0.5541 0.6632 0.1541 0.064 Uiso 1 1 calc R . . C7 C 0.47959(7) 0.7376(3) 0.11369(6) 0.0388(4) Uani 1 1 d . . . H7A H 0.4736 0.6088 0.0973 0.047 Uiso 1 1 calc R . . C8 C 0.38559(6) 0.6826(2) 0.03428(5) 0.0222(3) Uani 1 1 d . . . C9 C 0.41022(6) 0.7279(3) 0.00133(5) 0.0238(3) Uani 1 1 d . . . C10 C 0.41917(10) 0.9382(3) -0.00852(8) 0.0553(6) Uani 1 1 d . . . H10A H 0.4119 1.0539 0.0070 0.066 Uiso 1 1 calc R . . C11 C 0.43909(13) 0.9807(4) -0.04153(10) 0.0787(10) Uani 1 1 d . . . H11A H 0.4448 1.1249 -0.0479 0.094 Uiso 1 1 calc R . . C12 C 0.45038(8) 0.8149(3) -0.06464(6) 0.0450(5) Uani 1 1 d . . . H12A H 0.4642 0.8444 -0.0864 0.054 Uiso 1 1 calc R . . C13 C 0.44122(10) 0.6073(4) -0.05538(7) 0.0526(6) Uani 1 1 d . . . H13A H 0.4481 0.4928 -0.0714 0.063 Uiso 1 1 calc R . . C14 C 0.42177(9) 0.5615(3) -0.02244(7) 0.0487(5) Uani 1 1 d . . . H14A H 0.4164 0.4167 -0.0162 0.058 Uiso 1 1 calc R . . C15 C 0.26259(6) 0.5050(3) 0.12738(5) 0.0243(3) Uani 1 1 d . . . C16 C 0.31752(6) 0.4678(3) 0.15834(5) 0.0305(4) Uani 1 1 d . . . C17 C 0.35573(7) 0.6338(4) 0.16672(5) 0.0402(4) Uani 1 1 d . . . H17A H 0.3467 0.7683 0.1525 0.048 Uiso 1 1 calc R . . C18 C 0.40682(7) 0.5973(5) 0.19616(6) 0.0573(7) Uani 1 1 d . . . H18A H 0.4322 0.7070 0.2014 0.069 Uiso 1 1 calc R . . C19 C 0.42035(8) 0.3996(6) 0.21779(7) 0.0675(8) Uani 1 1 d . . . H19A H 0.4545 0.3778 0.2383 0.081 Uiso 1 1 calc R . . C20 C 0.38350(8) 0.2341(5) 0.20919(7) 0.0591(7) Uani 1 1 d . . . H20A H 0.3930 0.1001 0.2236 0.071 Uiso 1 1 calc R . . C21 C 0.33225(7) 0.2663(4) 0.17915(6) 0.0409(4) Uani 1 1 d . . . H21A H 0.3077 0.1528 0.1729 0.049 Uiso 1 1 calc R . . C22 C 0.22186(6) 0.3298(2) 0.12139(5) 0.0225(3) Uani 1 1 d . . . C23 C 0.20449(6) 0.2824(3) 0.15888(5) 0.0263(3) Uani 1 1 d . . . C24 C 0.17997(7) 0.0854(3) 0.16145(6) 0.0362(4) Uani 1 1 d . . . H24A H 0.1742 -0.0195 0.1394 0.043 Uiso 1 1 calc R . . C25 C 0.16415(8) 0.0451(4) 0.19675(6) 0.0443(5) Uani 1 1 d . . . H25A H 0.1478 -0.0870 0.1983 0.053 Uiso 1 1 calc R . . C26 C 0.17242(7) 0.1992(4) 0.22957(6) 0.0479(5) Uani 1 1 d . . . H26A H 0.1616 0.1711 0.2532 0.057 Uiso 1 1 calc R . . C27 C 0.19670(7) 0.3953(4) 0.22751(6) 0.0457(5) Uani 1 1 d . . . H27A H 0.2023 0.4992 0.2497 0.055 Uiso 1 1 calc R . . C28 C 0.21276(7) 0.4374(3) 0.19217(5) 0.0345(4) Uani 1 1 d . . . H28A H 0.2291 0.5698 0.1908 0.041 Uiso 1 1 calc R . . H1NA H 0.2736(8) 0.989(3) 0.0414(6) 0.039(5) Uiso 1 1 d . . . H1NB H 0.2952(9) 0.805(4) 0.0189(7) 0.053(6) Uiso 1 1 d . . . H3NA H 0.3468(8) 0.545(3) 0.0860(7) 0.041(5) Uiso 1 1 d . . . H3NB H 0.3357(8) 0.323(4) 0.0675(7) 0.044(6) Uiso 1 1 d . . . H5NA H 0.1938(8) 0.866(4) 0.0749(7) 0.042(6) Uiso 1 1 d . . . H5NB H 0.1767(8) 0.638(4) 0.0790(7) 0.041(6) Uiso 1 1 d . . . H7NA H 0.2326(7) 0.381(3) 0.0504(6) 0.032(5) Uiso 1 1 d . . . H7NB H 0.1918(8) 0.215(3) 0.0258(7) 0.035(5) 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 N1 0.0247(7) 0.0321(8) 0.0314(7) -0.0043(6) 0.0093(6) 0.0039(6) N2 0.0269(6) 0.0257(7) 0.0242(6) 0.0005(5) 0.0123(5) -0.0002(5) N3 0.0452(8) 0.0256(7) 0.0328(7) -0.0030(6) 0.0256(7) -0.0047(6) N4 0.0273(6) 0.0272(7) 0.0243(6) -0.0003(5) 0.0128(5) 0.0019(5) N5 0.0343(8) 0.0250(8) 0.0320(7) 0.0031(6) 0.0049(6) -0.0003(6) N6 0.0323(7) 0.0311(7) 0.0225(6) -0.0018(5) 0.0097(5) -0.0038(6) N7 0.0343(7) 0.0276(7) 0.0199(6) -0.0014(5) 0.0116(6) 0.0003(6) N8 0.0268(6) 0.0246(6) 0.0215(6) 0.0029(5) 0.0096(5) 0.0045(5) C1 0.0262(7) 0.0241(7) 0.0204(7) 0.0010(5) 0.0117(6) 0.0005(6) C2 0.0265(8) 0.0414(9) 0.0204(7) -0.0036(6) 0.0117(6) 0.0001(7) C3 0.0342(9) 0.0497(11) 0.0296(8) -0.0120(8) 0.0115(7) -0.0007(8) C4 0.0400(10) 0.0735(15) 0.0345(10) -0.0232(10) 0.0110(8) -0.0082(10) C5 0.0310(9) 0.0991(19) 0.0300(9) -0.0158(11) 0.0032(8) -0.0020(11) C6 0.0322(10) 0.0835(17) 0.0378(10) -0.0058(10) 0.0058(8) 0.0163(10) C7 0.0315(9) 0.0538(11) 0.0285(8) -0.0054(8) 0.0079(7) 0.0079(8) C8 0.0216(7) 0.0251(7) 0.0205(7) 0.0004(6) 0.0083(6) 0.0035(6) C9 0.0198(7) 0.0314(8) 0.0204(7) -0.0017(6) 0.0077(5) 0.0004(6) C10 0.0947(17) 0.0338(10) 0.0678(14) -0.0141(9) 0.0659(14) -0.0162(11) C11 0.149(3) 0.0366(12) 0.102(2) -0.0087(12) 0.106(2) -0.0204(14) C12 0.0582(12) 0.0506(12) 0.0420(10) -0.0025(9) 0.0370(10) -0.0083(9) C13 0.0806(16) 0.0433(11) 0.0578(13) -0.0054(10) 0.0536(12) 0.0052(11) C14 0.0794(15) 0.0302(10) 0.0593(12) 0.0028(9) 0.0526(12) 0.0076(9) C15 0.0254(7) 0.0327(8) 0.0161(6) -0.0016(6) 0.0089(6) -0.0011(6) C16 0.0255(7) 0.0523(10) 0.0165(7) -0.0021(7) 0.0111(6) 0.0014(7) C17 0.0299(8) 0.0711(13) 0.0227(8) -0.0097(8) 0.0134(7) -0.0102(9) C18 0.0269(9) 0.118(2) 0.0287(9) -0.0165(12) 0.0119(8) -0.0132(11) C19 0.0221(9) 0.147(3) 0.0294(10) 0.0016(13) 0.0050(8) 0.0153(13) C20 0.0355(10) 0.105(2) 0.0369(10) 0.0202(12) 0.0137(9) 0.0268(12) C21 0.0297(9) 0.0650(13) 0.0291(8) 0.0098(8) 0.0121(7) 0.0124(8) C22 0.0229(7) 0.0246(7) 0.0199(7) 0.0034(5) 0.0077(6) 0.0042(6) C23 0.0224(7) 0.0362(9) 0.0213(7) 0.0062(6) 0.0092(6) 0.0066(6) C24 0.0363(9) 0.0407(10) 0.0348(9) 0.0083(7) 0.0170(7) 0.0038(8) C25 0.0394(10) 0.0555(12) 0.0446(10) 0.0210(9) 0.0232(9) 0.0066(9) C26 0.0373(10) 0.0842(16) 0.0297(9) 0.0210(10) 0.0213(8) 0.0147(10) C27 0.0363(10) 0.0778(15) 0.0259(8) -0.0017(9) 0.0149(8) 0.0080(10) C28 0.0295(8) 0.0513(11) 0.0243(8) -0.0014(7) 0.0115(7) 0.0013(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N2 1.3648(18) . ? N1 H1NA 0.92(2) . ? N1 H1NB 0.92(2) . ? N2 C1 1.2892(19) . ? N3 N4 1.3734(18) . ? N3 H3NA 0.90(2) . ? N3 H3NB 0.89(2) . ? N4 C8 1.285(2) . ? N5 N6 1.3579(19) . ? N5 H5NA 0.89(2) . ? N5 H5NB 0.89(2) . ? N6 C15 1.286(2) . ? N7 N8 1.3726(17) . ? N7 H7NA 0.89(2) . ? N7 H7NB 0.89(2) . ? N8 C22 1.2858(19) . ? C1 C2 1.474(2) . ? C1 C8 1.500(2) . ? C2 C7 1.391(2) . ? C2 C3 1.394(2) . ? C3 C4 1.382(3) . ? C3 H3A 0.9300 . ? C4 C5 1.379(3) . ? C4 H4A 0.9300 . ? C5 C6 1.376(3) . ? C5 H5A 0.9300 . ? C6 C7 1.383(3) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.4777(19) . ? C9 C10 1.366(2) . ? C9 C14 1.379(2) . ? C10 C11 1.388(3) . ? C10 H10A 0.9300 . ? C11 C12 1.359(3) . ? C11 H11A 0.9300 . ? C12 C13 1.346(3) . ? C12 H12A 0.9300 . ? C13 C14 1.381(2) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.476(2) . ? C15 C22 1.497(2) . ? C16 C21 1.390(3) . ? C16 C17 1.402(3) . ? C17 C18 1.382(3) . ? C17 H17A 0.9300 . ? C18 C19 1.377(4) . ? C18 H18A 0.9300 . ? C19 C20 1.375(4) . ? C19 H19A 0.9300 . ? C20 C21 1.387(3) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 C23 1.4834(19) . ? C23 C24 1.391(2) . ? C23 C28 1.391(2) . ? C24 C25 1.383(2) . ? C24 H24A 0.9300 . ? C25 C26 1.376(3) . ? C25 H25A 0.9300 . ? C26 C27 1.379(3) . ? C26 H26A 0.9300 . ? C27 C28 1.390(2) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? 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 N1 H1NA 108.6(12) . . ? N2 N1 H1NB 117.0(14) . . ? H1NA N1 H1NB 116.3(19) . . ? C1 N2 N1 118.62(13) . . ? N4 N3 H3NA 116.0(13) . . ? N4 N3 H3NB 110.6(13) . . ? H3NA N3 H3NB 110.1(19) . . ? C8 N4 N3 118.03(13) . . ? N6 N5 H5NA 110.7(13) . . ? N6 N5 H5NB 116.3(13) . . ? H5NA N5 H5NB 112.6(19) . . ? C15 N6 N5 118.76(14) . . ? N8 N7 H7NA 115.6(12) . . ? N8 N7 H7NB 109.0(12) . . ? H7NA N7 H7NB 114.4(17) . . ? C22 N8 N7 119.23(13) . . ? N2 C1 C2 118.63(13) . . ? N2 C1 C8 123.27(13) . . ? C2 C1 C8 118.08(13) . . ? C7 C2 C3 118.45(16) . . ? C7 C2 C1 119.84(15) . . ? C3 C2 C1 121.71(15) . . ? C4 C3 C2 120.48(18) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C5 C4 C3 120.4(2) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C6 C5 C4 119.77(18) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C5 C6 C7 120.23(19) . . ? C5 C6 H6A 119.9 . . ? C7 C6 H6A 119.9 . . ? C6 C7 C2 120.69(18) . . ? C6 C7 H7A 119.7 . . ? C2 C7 H7A 119.7 . . ? N4 C8 C9 118.56(13) . . ? N4 C8 C1 123.00(13) . . ? C9 C8 C1 118.44(13) . . ? C10 C9 C14 117.78(15) . . ? C10 C9 C8 120.72(14) . . ? C14 C9 C8 121.38(15) . . ? C9 C10 C11 120.55(18) . . ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 . . ? C12 C11 C10 121.0(2) . . ? C12 C11 H11A 119.5 . . ? C10 C11 H11A 119.5 . . ? C13 C12 C11 118.78(17) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C12 C13 C14 121.08(18) . . ? C12 C13 H13A 119.5 . . ? C14 C13 H13A 119.5 . . ? C9 C14 C13 120.79(18) . . ? C9 C14 H14A 119.6 . . ? C13 C14 H14A 119.6 . . ? N6 C15 C16 117.76(14) . . ? N6 C15 C22 122.91(13) . . ? C16 C15 C22 119.31(14) . . ? C21 C16 C17 119.04(16) . . ? C21 C16 C15 120.35(16) . . ? C17 C16 C15 120.60(16) . . ? C18 C17 C16 119.9(2) . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C19 C18 C17 120.4(2) . . ? C19 C18 H18A 119.8 . . ? C17 C18 H18A 119.8 . . ? C20 C19 C18 120.18(19) . . ? C20 C19 H19A 119.9 . . ? C18 C19 H19A 119.9 . . ? C19 C20 C21 120.2(2) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C20 C21 C16 120.2(2) . . ? C20 C21 H21A 119.9 . . ? C16 C21 H21A 119.9 . . ? N8 C22 C23 117.81(14) . . ? N8 C22 C15 124.00(13) . . ? C23 C22 C15 118.18(13) . . ? C24 C23 C28 119.13(15) . . ? C24 C23 C22 121.29(15) . . ? C28 C23 C22 119.58(15) . . ? C25 C24 C23 120.16(18) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? C26 C25 C24 120.43(19) . . ? C26 C25 H25A 119.8 . . ? C24 C25 H25A 119.8 . . ? C25 C26 C27 120.11(16) . . ? C25 C26 H26A 119.9 . . ? C27 C26 H26A 119.9 . . ? C26 C27 C28 119.93(19) . . ? C26 C27 H27A 120.0 . . ? C28 C27 H27A 120.0 . . ? C27 C28 C23 120.24(18) . . ? C27 C28 H28A 119.9 . . ? C23 C28 H28A 119.9 . . ? 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 N1 N2 C1 C2 177.38(13) . . . . ? N1 N2 C1 C8 -3.9(2) . . . . ? N2 C1 C2 C7 160.30(15) . . . . ? C8 C1 C2 C7 -18.5(2) . . . . ? N2 C1 C2 C3 -19.1(2) . . . . ? C8 C1 C2 C3 162.12(15) . . . . ? C7 C2 C3 C4 0.2(3) . . . . ? C1 C2 C3 C4 179.56(16) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C5 C6 C7 0.2(3) . . . . ? C5 C6 C7 C2 -0.5(3) . . . . ? C3 C2 C7 C6 0.3(3) . . . . ? C1 C2 C7 C6 -179.11(17) . . . . ? N3 N4 C8 C9 -174.71(13) . . . . ? N3 N4 C8 C1 4.5(2) . . . . ? N2 C1 C8 N4 -70.7(2) . . . . ? C2 C1 C8 N4 108.04(17) . . . . ? N2 C1 C8 C9 108.49(16) . . . . ? C2 C1 C8 C9 -72.78(18) . . . . ? N4 C8 C9 C10 157.62(18) . . . . ? C1 C8 C9 C10 -21.6(2) . . . . ? N4 C8 C9 C14 -18.2(2) . . . . ? C1 C8 C9 C14 162.58(17) . . . . ? C14 C9 C10 C11 0.2(4) . . . . ? C8 C9 C10 C11 -175.8(2) . . . . ? C9 C10 C11 C12 -0.3(5) . . . . ? C10 C11 C12 C13 0.9(4) . . . . ? C11 C12 C13 C14 -1.3(4) . . . . ? C10 C9 C14 C13 -0.7(3) . . . . ? C8 C9 C14 C13 175.28(19) . . . . ? C12 C13 C14 C9 1.3(4) . . . . ? N5 N6 C15 C16 175.96(13) . . . . ? N5 N6 C15 C22 -5.8(2) . . . . ? N6 C15 C16 C21 -176.85(14) . . . . ? C22 C15 C16 C21 4.9(2) . . . . ? N6 C15 C16 C17 2.3(2) . . . . ? C22 C15 C16 C17 -176.03(13) . . . . ? C21 C16 C17 C18 -1.6(2) . . . . ? C15 C16 C17 C18 179.28(15) . . . . ? C16 C17 C18 C19 -0.8(3) . . . . ? C17 C18 C19 C20 2.1(3) . . . . ? C18 C19 C20 C21 -0.9(3) . . . . ? C19 C20 C21 C16 -1.5(3) . . . . ? C17 C16 C21 C20 2.7(2) . . . . ? C15 C16 C21 C20 -178.15(16) . . . . ? N7 N8 C22 C23 -176.24(13) . . . . ? N7 N8 C22 C15 5.0(2) . . . . ? N6 C15 C22 N8 69.5(2) . . . . ? C16 C15 C22 N8 -112.32(16) . . . . ? N6 C15 C22 C23 -109.28(16) . . . . ? C16 C15 C22 C23 68.93(18) . . . . ? N8 C22 C23 C24 20.7(2) . . . . ? C15 C22 C23 C24 -160.43(14) . . . . ? N8 C22 C23 C28 -159.21(15) . . . . ? C15 C22 C23 C28 19.6(2) . . . . ? C28 C23 C24 C25 0.0(2) . . . . ? C22 C23 C24 C25 180.00(15) . . . . ? C23 C24 C25 C26 0.1(3) . . . . ? C24 C25 C26 C27 -0.1(3) . . . . ? C25 C26 C27 C28 0.1(3) . . . . ? C26 C27 C28 C23 -0.1(3) . . . . ? C24 C23 C28 C27 0.0(2) . . . . ? C22 C23 C28 C27 179.99(15) . . . . ? 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 N1 H1NA N7 0.92(2) 2.30(2) 3.162(2) 154.6(17) 1_565 N1 H1NB N3 0.92(2) 2.51(2) 3.078(2) 120.6(17) . N1 H1NB N4 0.92(2) 2.53(2) 3.169(2) 126.7(18) . N3 H3NA N2 0.90(2) 2.66(2) 3.095(2) 110.7(15) . N3 H3NB N2 0.89(2) 2.19(2) 3.043(2) 160.8(19) 1_545 N3 H3NB N1 0.89(2) 2.63(2) 3.378(2) 142.9(17) 1_545 N5 H5NA N8 0.89(2) 2.19(2) 3.045(2) 161.0(18) 1_565 N5 H5NA N7 0.89(2) 2.63(2) 3.389(2) 143.4(17) 1_565 N5 H5NB N8 0.89(2) 2.62(2) 3.090(2) 113.8(15) . N7 H7NA N5 0.89(2) 2.51(2) 3.075(2) 121.7(14) . N7 H7NA N6 0.89(2) 2.56(2) 3.191(2) 127.8(14) . N7 H7NB N4 0.89(2) 2.32(2) 3.1691(19) 160.1(17) 7 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.299 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.043