#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/47/2004762.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2004762 loop_ _publ_author_name 'Breu, J.' 'Range, K.-J.' 'Biedermann, N.' 'Schmid, K.' 'Sauer, J.' _publ_section_title ; Arene--Arene Stacking in 6,6'-Diphenyl-3,3'-bi-1,2,4,5-tetrazine and 6-Phenyl-1,2,4,5-tetrazine-3-carbaldehyde Benzoylhydrazone Monohydrate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 936 _journal_page_last 940 _journal_paper_doi 10.1107/S0108270195015216 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C16 H12 N6 O, H2 O' _chemical_formula_sum 'C16 H14 N6 O2' _chemical_formula_weight 322.33 _chemical_name_systematic ; 6-Phenyl-1,2,4,5-tetrazine-3-carbaldehyde-benzoylhydrazone monohydrate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 96.052(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.5300(3) _cell_length_b 8.6338(6) _cell_length_c 27.7016(9) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.22 _cell_measurement_theta_min 9.38 _cell_volume 1553.08(14) _computing_cell_refinement 'SET4 (Boer & Duisenberg, 1984)' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1993)' _computing_molecular_graphics 'PLATON (Spek, 1990) and PLUTON (Spek, 1991)' _computing_publication_material PLATON _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2460 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_max 64.98 _diffrn_reflns_theta_min 3.21 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.80 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.378 _exptl_crystal_description lath _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.165 _refine_diff_density_min -0.155 _refine_ls_extinction_coef 0.0016(3) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 0.808 _refine_ls_goodness_of_fit_obs 1.005 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 263 _refine_ls_number_reflns 2404 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.808 _refine_ls_restrained_S_obs 1.005 _refine_ls_R_factor_all 0.1345 _refine_ls_R_factor_obs 0.0428 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(F~o~^2^) + (0.0653P)^2^] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1186 _refine_ls_wR_factor_obs 0.0994 _reflns_number_observed 1230 _reflns_number_total 2404 _reflns_observed_criterion >2\s(I) _cod_data_source_file jz1094.cif _cod_data_source_block IV _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2004762 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O6 0.0429(13) 0.089(2) 0.0737(14) -0.0018(12) 0.0030(11) -0.0183(12) N3 0.0476(15) 0.054(2) 0.0493(14) -0.0014(12) 0.0079(12) -0.0001(12) N4 0.0403(14) 0.062(2) 0.0529(14) -0.0017(13) 0.0066(13) -0.0086(12) N22 0.055(2) 0.081(2) 0.0547(14) -0.0045(14) 0.0001(13) -0.0120(14) N23 0.056(2) 0.076(2) 0.057(2) -0.0043(14) 0.0028(13) -0.0123(14) N25 0.053(2) 0.065(2) 0.0528(14) -0.0047(13) 0.0030(13) -0.0059(13) N26 0.050(2) 0.060(2) 0.0522(14) -0.0064(13) 0.0057(12) -0.0051(13) C2 0.048(2) 0.060(2) 0.053(2) -0.004(2) 0.005(2) 0.001(2) C5 0.047(2) 0.055(2) 0.049(2) -0.005(2) 0.0005(14) 0.0040(14) C11 0.045(2) 0.050(2) 0.0456(15) -0.0007(14) 0.0049(13) 0.0019(14) C12 0.054(2) 0.101(3) 0.058(2) 0.009(2) -0.001(2) -0.013(2) C13 0.085(3) 0.124(3) 0.058(2) 0.007(3) -0.002(2) -0.029(2) C14 0.087(3) 0.088(3) 0.066(2) 0.015(2) 0.017(2) -0.019(2) C15 0.060(2) 0.073(2) 0.077(2) 0.016(2) 0.013(2) -0.006(2) C16 0.052(2) 0.062(2) 0.057(2) 0.002(2) 0.003(2) -0.004(2) C21 0.047(2) 0.051(2) 0.045(2) -0.0075(14) 0.0049(14) 0.0051(14) C24 0.049(2) 0.052(2) 0.043(2) -0.0081(15) 0.0046(13) 0.0014(14) C31 0.059(2) 0.049(2) 0.042(2) -0.008(2) 0.0064(14) 0.0041(14) C32 0.071(2) 0.068(2) 0.054(2) 0.001(2) 0.001(2) -0.004(2) C33 0.103(3) 0.076(3) 0.062(2) -0.011(2) 0.003(2) -0.018(2) C34 0.098(3) 0.060(2) 0.073(2) 0.001(2) 0.030(2) -0.008(2) C35 0.072(2) 0.064(2) 0.081(2) 0.000(2) 0.015(2) -0.002(2) C36 0.063(2) 0.058(2) 0.066(2) -0.009(2) 0.006(2) -0.005(2) O1 0.0462(13) 0.089(2) 0.084(2) 0.0007(12) 0.0091(11) -0.0205(15) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type O6 1.000 1.0234(3) 1.1390(3) .15423(7) .0688(9) Uani N3 1.000 .8324(3) .9912(3) .07980(8) .0501(10) Uani N4 1.000 .7245(4) 1.0696(3) .11113(8) .0516(9) Uani N22 1.000 .7262(4) .7628(3) -.02503(8) .0640(11) Uani N23 1.000 .8202(4) .6728(3) -.05451(8) .0632(12) Uani N25 1.000 1.1377(4) .7154(3) -.00664(8) .0571(11) Uani N26 1.000 1.0436(4) .8063(3) .02250(8) .0540(11) Uani C2 1.000 .7291(5) .9169(3) .04545(11) .0537(12) Uani C5 1.000 .8342(4) 1.1430(3) .14923(10) .0507(12) Uani C11 1.000 .7170(4) 1.2298(3) .18333(9) .0469(11) Uani C12 1.000 .8222(5) 1.2749(4) .22693(11) .0715(14) Uani C13 1.000 .7230(6) 1.3584(5) .25979(13) .0897(16) Uani C14 1.000 .5214(7) 1.3986(5) .24988(14) .0797(16) Uani C15 1.000 .4154(5) 1.3553(4) .20695(13) .0696(12) Uani C16 1.000 .5129(5) 1.2710(4) .17334(11) .0572(12) Uani C21 1.000 .8404(4) .8256(3) .01267(10) .0477(12) Uani C24 1.000 1.0220(4) .6478(3) -.04408(9) .0480(12) Uani C31 1.000 1.1275(5) .5427(3) -.07528(9) .0499(12) Uani C32 1.000 1.0195(5) .4739(4) -0.11527(11) .0647(12) Uani C33 1.000 1.1208(7) .3764(4) -0.14439(13) .0807(16) Uani C34 1.000 1.3257(7) .3456(4) -0.13421(14) .0755(14) Uani C35 1.000 1.4322(6) .4114(4) -.09409(14) .0718(12) Uani C36 1.000 1.3352(5) .5103(4) -.06505(12) .0624(12) Uani O1 1.000 .3048(3) .9593(3) .10778(8) .0729(10) Uani H2 1.000 .579(4) .915(3) .0397(9) .055(6) Uiso H4 1.000 .589(4) 1.063(3) .1105(9) .055(6) Uiso H12 1.000 .965(5) 1.248(4) .2322(10) .079(3) Uiso H13 1.000 .800(5) 1.388(4) .2890(11) .079(3) Uiso H14 1.000 .453(5) 1.456(4) .2736(11) .079(3) Uiso H15 1.000 .267(5) 1.389(3) .2004(11) .079(3) Uiso H16 1.000 .448(5) 1.238(4) .1430(10) .079(3) Uiso H32 1.000 .879(5) .499(4) -0.1218(10) .079(3) Uiso H33 1.000 1.047(5) .338(4) -0.1690(11) .079(3) Uiso H34 1.000 1.395(5) .278(4) -0.1568(10) .079(3) Uiso H35 1.000 1.577(5) .383(4) -.0873(11) .079(3) Uiso H36 1.000 1.421(5) .564(3) -.0371(10) .079(3) Uiso H1A 1.000 .200(6) 1.018(5) .1227(12) .119(10) Uiso H1B 1.000 .234(6) .911(5) .0838(15) .119(10) Uiso loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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_publ_flag N4 N3 C2 117.2(2) yes N3 N4 C5 117.4(2) yes N23 N22 C21 117.7(2) yes N22 N23 C24 118.2(2) yes N26 N25 C24 117.8(2) yes N25 N26 C21 117.7(2) yes N3 C2 C21 118.5(3) yes O6 C5 N4 120.8(3) yes O6 C5 C11 121.6(2) yes N4 C5 C11 117.6(2) yes C5 C11 C12 117.2(2) no C5 C11 C16 123.8(2) no C12 C11 C16 118.9(3) no C11 C12 C13 120.1(3) no C12 C13 C14 120.9(3) no C13 C14 C15 119.8(4) no C14 C15 C16 120.1(3) no C11 C16 C15 120.2(3) no N22 C21 N26 124.8(3) yes N22 C21 C2 115.8(2) yes N26 C21 C2 119.4(3) yes N23 C24 N25 123.7(2) yes N23 C24 C31 118.9(2) yes N25 C24 C31 117.3(2) yes C24 C31 C32 120.3(3) no C24 C31 C36 120.9(3) no C32 C31 C36 118.9(3) no C31 C32 C33 119.6(3) no C32 C33 C34 121.2(3) no C33 C34 C35 119.3(4) no C34 C35 C36 120.5(4) no C31 C36 C35 120.5(3) no N3 N4 H4 122.8(17) no C5 N4 H4 119.1(16) no N3 C2 H2 124.8(15) no C21 C2 H2 116.6(15) no C11 C12 H12 116.9(18) no C13 C12 H12 123.1(18) no C12 C13 H13 118(2) no C14 C13 H13 121(2) no C13 C14 H14 119.9(19) no C15 C14 H14 120.2(19) no C14 C15 H15 117.8(17) no C16 C15 H15 122.0(17) no C11 C16 H16 116(2) no C15 C16 H16 124(2) no C31 C32 H32 117.3(19) no C33 C32 H32 123.0(19) no C32 C33 H33 116(2) no C34 C33 H33 123(2) no C33 C34 H34 118.9(18) no C35 C34 H34 121.7(18) no C34 C35 H35 116.8(19) no C36 C35 H35 122.7(19) no C31 C36 H36 120.8(18) no C35 C36 H36 118.5(18) no H1A O1 H1B 103(3) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O6 C5 1.229(3) yes N3 N4 1.355(3) yes N3 C2 1.279(4) yes N4 C5 1.367(4) yes N22 N23 1.324(3) yes N22 C21 1.333(4) yes N23 C24 1.337(4) yes N25 N26 1.323(3) yes N25 C24 1.350(3) yes N26 C21 1.337(4) yes C2 C21 1.454(4) no C5 C11 1.481(4) no C11 C12 1.381(4) no C11 C16 1.379(4) no C12 C13 1.376(5) no C13 C14 1.361(6) no C14 C15 1.364(5) no C15 C16 1.388(5) no C24 C31 1.473(4) no C31 C32 1.383(4) no C31 C36 1.385(5) no C32 C33 1.382(5) no C33 C34 1.364(6) no C34 C35 1.371(5) no C35 C36 1.373(5) no N4 H4 0.88(3) no C2 H2 0.98(3) no C12 H12 0.96(3) no C13 H13 0.94(3) no C14 H14 0.97(3) no C15 H15 1.01(3) no C16 H16 0.94(3) no C32 H32 0.94(3) no C33 H33 0.86(3) no C34 H34 1.00(3) no C35 H35 0.98(3) no C36 H36 1.02(3) no O1 H1A 0.98(4) no O1 H1B 0.87(4) no 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_publ_flag C2 N3 N4 C5 176.9(3) no N4 N3 C2 C21 -177.1(2) no N3 N4 C5 C11 179.5(3) no N3 N4 C5 O6 0.9(4) no N23 N22 C21 N26 1.1(4) no C21 N22 N23 C24 1.5(4) no N23 N22 C21 C2 -176.9(2) no N22 N23 C24 C31 177.4(2) no N22 N23 C24 N25 -3.6(4) no C24 N25 N26 C21 -0.4(4) no N26 N25 C24 N23 3.0(4) no N26 N25 C24 C31 -178.0(2) no N25 N26 C21 C2 176.3(2) no N25 N26 C21 N22 -1.6(4) no N3 C2 C21 N26 8.0(4) no N3 C2 C21 N22 -173.9(3) no O6 C5 C11 C12 -15.0(4) no O6 C5 C11 C16 163.1(3) no N4 C5 C11 C12 166.3(3) no N4 C5 C11 C16 -15.6(4) no C16 C11 C12 C13 0.6(5) no C5 C11 C16 C15 -178.7(3) no C12 C11 C16 C15 -0.6(4) no C5 C11 C12 C13 178.8(3) no C11 C12 C13 C14 -0.4(5) no C12 C13 C14 C15 0.3(6) no C13 C14 C15 C16 -0.3(6) no C14 C15 C16 C11 0.4(5) no N23 C24 C31 C32 1.3(4) no N23 C24 C31 C36 -178.3(3) no N25 C24 C31 C32 -177.7(3) no N25 C24 C31 C36 2.7(4) no C24 C31 C32 C33 179.6(3) no C36 C31 C32 C33 -0.8(5) no C24 C31 C36 C35 179.5(3) no C32 C31 C36 C35 -0.1(5) no C31 C32 C33 C34 0.5(5) no C32 C33 C34 C35 0.7(6) no C33 C34 C35 C36 -1.6(5) no C34 C35 C36 C31 1.3(5) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21186935 2 PubChem 139054856