#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/12/2101203.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_2101203 loop_ _publ_author_name 'Bertolasi, V.' 'Gilli, P.' 'Ferretti, V.' 'Gilli, G.' _publ_section_title ; Intramolecular N--H^{···^}O hydrogen bonding assisted by resonance. III. Structural studies of 1-ketone-2-arylhydrazone derivatives ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 617 _journal_page_last 625 _journal_paper_doi 10.1107/S0108768194003034 _journal_volume 50 _journal_year 1994 _chemical_formula_sum 'C10 H8 Cl N3 O2' _chemical_formula_weight 237.6 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 18.324(2) _cell_length_b 5.7710(10) _cell_length_c 20.016(2) _cell_volume 2116.6(5) _diffrn_radiation_type Mo _diffrn_radiation_wavelength 0.71069 _exptl_absorpt_coefficient_mu 0.345 _exptl_crystal_density_diffrn 1.49 _exptl_crystal_F_000 976 _cod_data_source_file na0053.cif _cod_data_source_block na0053c _cod_original_cell_volume 2116.6(6) _cod_database_code 2101203 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z Cl(1A) .26280(10) -.4807(3) .0 O(1A) .1978(2) .3520(7) .3126(2) O(2A) .2839(2) .6274(6) .3000(2) N(1A) .2113(2) .0480(7) .2009(2) N(2A) .2696(2) .1701(7) .1840(2) N(3A) .3450(3) .6710(7) .2550(2) C(1A) .2860(3) .3490(8) .2224(2) C(2A) .2501(3) .4241(8) .2815(3) C(3A) .3449(2) .5084(8) .2101(2) C(4A) .4020(3) .4983(10) .1550(3) C(5A) .1939(3) -.1451(8) .1612(2) C(6A) .1346(3) -.2794(9) .1811(3) C(7A) .1177(3) -.4725(10) .1450(3) C(8A) .1559(3) -.5385(9) .0874(3) C(9A) .2117(3) -.4021(9) .0692(3) C(10A) .2327(3) -.2041(8) .1037(3) H(1A) .178(3) .091(9) .236(2) Cl(1B) -.00920(10) .9857(3) .57990(10) O(1B) .0493(2) .1596(7) .2649(2) O(2B) -.0366(2) -.1153(7) .2764(2) N(1B) .0351(2) .4642(7) .3786(2) N(2B) -.0204(2) .3347(7) .3936(2) N(3B) -.0953(2) -.1650(7) .3252(2) C(1B) -.0367(3) .1597(8) .3563(2) C(2B) -.0009(3) .0750(9) .2954(3) C(3B) -.0924(3) -.0026(9) .3671(3) C(4B) -.1437(4) .0065(13) .4210(3) C(5B) .0563(3) .6571(8) .4157(2) C(6B) .1133(3) .7963(9) .3940(2) C(7B) .1337(3) .9882(9) .4305(3) C(8B) .0974(3) 1.0412(8) .4863(2) C(9B) .0386(3) .9050(11) .5084(2) C(10B) .0186(3) .7106(8) .4740(2) H(1B) .054(2) .432(6) .346(2) H6A .110(2) -.231(8) .224(2) H7A .078(2) -.569(7) .159(2) H8A .142(2) -.650(6) .059(2) H10A .270(2) -.124(7) .083(2) H101A .423(3) .316(9) .157(3) H102A .431(3) .610(9) .158(2) H103A .38(3) .510(10) .111(3) H6B .145(2) .723(8) .353(2) H7B .167(2) 1.059(7) .419(2) H8B .106(2) 1.183(7) .510(2) H10B -.021(2) .613(8) .487(2) H101B -.132(3) .030(8) .464(2) H102B -.175(3) -.096(9) .421(2) H103B -.186(4) .100(10) .407(3) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N(3A) O(2A) C(2A) 109.0(4) N(2A) N(1A) C(5A) 117.4(4) N(1A) N(2A) C(1A) 116.8(4) O(2A) N(3A) C(3A) 107.5(4) N(2A) C(1A) C(3A) 124.8(4) N(2A) C(1A) C(2A) 128.1(5) C(2A) C(1A) C(3A) 107.1(4) O(2A) C(2A) C(1A) 106.0(4) O(1A) C(2A) C(1A) 133.4(5) O(1A) C(2A) O(2A) 120.5(5) N(3A) C(3A) C(1A) 110.1(4) C(1A) C(3A) C(4A) 128.0(4) N(3A) C(3A) C(4A) 121.9(4) N(1A) C(5A) C(10A) 123.0(4) N(1A) C(5A) C(6A) 117.2(4) C(6A) C(5A) C(10A) 119.8(5) C(5A) C(6A) C(7A) 118.7(5) C(6A) C(7A) C(8A) 123.0(5) C(7A) C(8A) C(9A) 116.4(5) Cl(1A) C(9A) C(8A) 118.4(4) C(8A) C(9A) C(10A) 124.0(5) Cl(1A) C(9A) C(10A) 117.6(4) C(5A) C(10A) C((9A) 118.0(5) N(3B O(2B) C(2B) 109.1(4) N(2B) N(1B) C(5B) 123.7(4) N(1B) N(2B) C(1B) 119.9(4) O(2B) N(3B) C(3B) 105.3(4) N(2B) C(1B) C(3B) 127.0(4) N(2B) C(1B) C(2B) 129.6(5) C(2B) C(1B) C(3B) 103.4(4) O(2B) C(2B) C(1B) 107.0(4) O(1B) C(2B) C(1B) 128.7(5) O(1B) C(2B) O(2B) 124.2(5) N(3B) C(3B) C(1B) 115.2(5) C(1B) C(3B) C(4B) 124.7(5) N(3B) C(3B) C(4B) 120.1(5) N(1B) C(5B) C(10B) 119.1(4) N(1B) C(5B) C(6B) 120.4(4) C(6B) C(5B) C(10B) 120.5(4) C(5B) C(6B) C(7B) 120.2(4) C(6B) C(7B) C(8B) 119.5(5) C(7B) C(8B) C(9B) 121.1(4) Cl(1B) C(9B) C(8B) 119.6(4) C(8B) C(9B) C(10B) 120.4(4) Cl(1B) C(9B) C(10B) 119.9(4) C(5B) C(10B) C(9B) 118.2(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl(1A) C(9A) 1.733(6) O(1A) C(2A) 1.216(7) O(2A) N(3A) 1.459(6) O(2A) C(2A) 1.377(6) N(1A) N(2A) 1.324(5) N(1A) C(5A) 1.405(6) N(2A) C(1A) 1.322(6) N(3A) C(3A) 1.299(6) C(1A) C(2A) 1.421(7) C(1A) C(3A) 1.439(7) C(3A) C(4A) 1.521(7) C(5A) C(6A) 1.393(7) C(5A) C(10A) 1.395(7) C(6A) C(7A) 1.364(8) C(7A) C(8A) 1.401(8) C(8A) C(9A) 1.341(8) C(9A) C(10A) 1.390(7) Cl(1B) C(9B) 1.742(5) O(1B) C(2B) 1.207(7) O(2B) N(3B) 1.481(5) O(2B) C(2B) 1.334(7) N(1B) N(2B) 1.297(5) N(1B) C(5B) 1.393(6) N(2B) C(1B) 1.291(6) N(3B) C(3B) 1.259(7) C(1B) C(2B) 1.468(7) C(1B) C(3B) 1.402(7) C(3B) C(4B) 1.432(9) C(5B) C(6B) 1.387(7) C(5B) C(10B) 1.391(6) C(6B) C(7B) 1.378(7) C(7B) C(8B) 1.336(7) C(8B) C(9B) 1.405(8) C(9B) C(10B) 1.367(7) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139063207