#------------------------------------------------------------------------------ #$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $ #$Revision: 176809 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/05/2240559.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_2240559 loop_ _publ_author_name 'Benosmane, Ali' 'Benaouida, Mohamed Amine' 'Mili, Assia' 'Bouchoul, Abdelkader' 'Merazig, Hocine' _publ_section_title ; Crystal structure of 1-[(Z)-2-phenylhydrazin-1-ylidene]naphthalen-2(1H)-one ; _journal_coeditor_code XU5845 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o303 _journal_paper_doi 10.1107/S2056989015006775 _journal_volume 71 _journal_year 2015 _chemical_formula_iupac 'C16 H12 N2 O' _chemical_formula_moiety 'C16 H12 N2 O' _chemical_formula_sum 'C16 H12 N2 O' _chemical_formula_weight 248.28 _chemical_name_common ; 1-[(Z)-2-Phenylhydrazin-1-ylidene]naphthalen-2(1H)-one ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90.000(5) _cell_angle_beta 103.243(5) _cell_angle_gamma 90.000(5) _cell_formula_units_Z 8 _cell_length_a 28.109(5) _cell_length_b 6.039(5) _cell_length_c 15.181(5) _cell_measurement_temperature 293(2) _cell_volume 2508(2) _computing_cell_refinement ; SAINT (Bruker, 2006) ; _computing_data_collection ; APEX2 (Bruker, 2006) ; _computing_data_reduction ; SAINT (Bruker, 2006) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009) ; _computing_publication_material ; PLATON (Spek, 2009) ; _computing_structure_refinement ; SHELXL97 (Sheldrick, 2008) ; _computing_structure_solution ; SHELXS97 (Sheldrick, 2008) ; _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 4481 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.032 _diffrn_reflns_theta_min 2.757 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1040 _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.199 _refine_diff_density_min -0.203 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 176 _refine_ls_number_reflns 2450 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0571 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0920P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1404 _refine_ls_wR_factor_ref 0.1692 _reflns_number_gt 1469 _reflns_number_total 2450 _reflns_threshold_expression I>2sigma(I) _cod_data_source_file xu5845sup1.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2240559 _cod_database_fobs_code 2240559 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,1/2-z 3 -x,-y,-z 4 x,-y,1/2+z 5 1/2+x,1/2+y,z 6 1/2-x,1/2+y,1/2-z 7 1/2-x,1/2-y,-z 8 1/2+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 O1 0.0554(9) 0.0765(10) 0.0933(12) -0.0043(7) 0.0103(8) 0.0133(8) N1 0.0601(11) 0.0475(9) 0.0584(11) 0.0026(8) 0.0153(9) 0.0031(7) N2 0.0601(10) 0.0441(8) 0.0455(9) 0.0048(7) 0.0139(8) -0.0013(7) C1 0.0666(13) 0.0414(9) 0.0457(11) 0.0035(9) 0.0160(9) -0.0021(8) C2 0.0695(14) 0.0496(11) 0.0568(13) 0.0017(9) 0.0180(11) 0.0021(9) C3 0.0791(15) 0.0538(11) 0.0594(13) 0.0129(11) 0.0119(12) 0.0008(10) C4 0.0995(19) 0.0508(11) 0.0515(13) 0.0121(12) 0.0201(12) 0.0054(9) C5 0.1042(19) 0.0529(11) 0.0638(14) -0.0047(12) 0.0371(13) 0.0041(10) C6 0.0723(14) 0.0594(12) 0.0607(13) -0.0004(10) 0.0244(11) 0.0013(10) C7 0.0555(11) 0.0441(9) 0.0411(10) 0.0051(8) 0.0080(9) -0.0020(8) C8 0.0557(13) 0.0568(11) 0.0553(12) 0.0009(10) 0.0057(10) -0.0013(9) C9 0.0566(13) 0.0693(13) 0.0664(14) 0.0093(11) 0.0003(11) 0.0102(11) C10 0.0722(15) 0.0562(12) 0.0566(12) 0.0164(10) 0.0069(11) 0.0111(10) C12 0.0806(16) 0.0512(11) 0.0556(12) 0.0085(10) 0.0198(11) 0.0076(9) C13 0.0737(15) 0.0608(12) 0.0719(15) -0.0033(11) 0.0297(12) 0.0048(11) C14 0.0583(13) 0.0662(13) 0.0704(14) 0.0050(10) 0.0195(11) 0.0013(11) C15 0.0603(13) 0.0524(10) 0.0565(12) 0.0098(9) 0.0161(10) 0.0056(9) C16 0.0568(12) 0.0436(9) 0.0394(9) 0.0064(8) 0.0117(8) -0.0039(8) C17 0.0627(13) 0.0468(10) 0.0438(10) 0.0060(9) 0.0123(9) -0.0011(8) loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy O O1 0.73024(5) 0.6381(3) 0.09280(11) 0.0762(6) Uani . . 1.000 N N1 0.65766(7) 0.8669(3) 0.00890(12) 0.0551(6) Uani . . 1.000 N N2 0.62773(6) 0.7373(2) 0.03831(10) 0.0496(5) Uani . . 1.000 C C1 0.63841(7) 1.0493(3) -0.04642(12) 0.0507(6) Uani . . 1.000 C C2 0.58893(8) 1.0917(3) -0.07177(13) 0.0581(7) Uani . . 1.000 C C3 0.57264(9) 1.2751(3) -0.12414(14) 0.0647(8) Uani . . 1.000 C C4 0.60525(10) 1.4165(3) -0.15058(14) 0.0668(9) Uani . . 1.000 C C5 0.65432(10) 1.3745(3) -0.12602(15) 0.0708(9) Uani . . 1.000 C C6 0.67128(8) 1.1886(3) -0.07340(14) 0.0627(8) Uani . . 1.000 C C7 0.64663(7) 0.5645(3) 0.09114(12) 0.0474(6) Uani . . 1.000 C C8 0.69840(7) 0.5157(3) 0.11735(13) 0.0571(7) Uani . . 1.000 C C9 0.71329(8) 0.3216(3) 0.17167(14) 0.0663(8) Uani . . 1.000 C C10 0.68014(8) 0.1878(3) 0.19510(14) 0.0629(8) Uani . . 1.000 C C12 0.59514(8) 0.0806(3) 0.19309(14) 0.0618(8) Uani . . 1.000 C C13 0.54622(8) 0.1209(3) 0.16897(15) 0.0667(8) Uani . . 1.000 C C14 0.52907(8) 0.3124(3) 0.12094(14) 0.0642(8) Uani . . 1.000 C C15 0.56100(7) 0.4592(3) 0.09687(13) 0.0560(7) Uani . . 1.000 C C16 0.61175(7) 0.4199(3) 0.11928(12) 0.0465(6) Uani . . 1.000 C C17 0.62863(7) 0.2274(3) 0.16940(12) 0.0511(6) Uani . . 1.000 H H1 0.6900(5) 0.835(4) 0.022(2) 0.127(11) Uiso . . 1.000 H H2 0.56680 0.99750 -0.05370 0.0700 Uiso calc R 1.000 H H3 0.53930 1.30370 -0.14180 0.0780 Uiso calc R 1.000 H H4 0.59390 1.54080 -0.18520 0.0800 Uiso calc R 1.000 H H5 0.67630 1.46940 -0.14430 0.0850 Uiso calc R 1.000 H H6 0.70460 1.15890 -0.05660 0.0750 Uiso calc R 1.000 H H9 0.74640 0.28840 0.19080 0.0800 Uiso calc R 1.000 H H10 0.69120 0.06310 0.22980 0.0750 Uiso calc R 1.000 H H12 0.60650 -0.04640 0.22580 0.0740 Uiso calc R 1.000 H H13 0.52430 0.02100 0.18450 0.0800 Uiso calc R 1.000 H H14 0.49570 0.34080 0.10510 0.0770 Uiso calc R 1.000 H H15 0.54900 0.58690 0.06520 0.0670 Uiso calc R 1.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 '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 N2 N1 C1 118.85(18) . N1 N2 C7 118.17(17) . N2 N1 H1 119.5(16) no C1 N1 H1 121.6(16) no N1 C1 C2 122.28(18) . N1 C1 C6 117.38(18) . C2 C1 C6 120.34(18) no C1 C2 C3 119.4(2) no C2 C3 C4 120.7(2) no C3 C4 C5 120.15(19) no C4 C5 C6 119.7(2) no C1 C6 C5 119.7(2) no C8 C7 C16 120.11(16) no N2 C7 C8 123.70(17) . N2 C7 C16 116.15(17) . C7 C8 C9 117.72(18) no O1 C8 C9 120.41(19) . O1 C8 C7 121.87(17) . C8 C9 C10 120.9(2) no C9 C10 C17 123.23(18) no C13 C12 C17 121.02(18) no C12 C13 C14 119.8(2) no C13 C14 C15 120.5(2) no C14 C15 C16 121.05(18) no C7 C16 C17 119.28(18) no C15 C16 C17 117.77(17) no C7 C16 C15 122.93(17) no C12 C17 C16 119.86(18) no C10 C17 C12 121.51(17) no C10 C17 C16 118.63(17) no C1 C2 H2 120.00 no C3 C2 H2 120.00 no C2 C3 H3 120.00 no C4 C3 H3 120.00 no C3 C4 H4 120.00 no C5 C4 H4 120.00 no C4 C5 H5 120.00 no C6 C5 H5 120.00 no C1 C6 H6 120.00 no C5 C6 H6 120.00 no C8 C9 H9 120.00 no C10 C9 H9 120.00 no C9 C10 H10 118.00 no C17 C10 H10 118.00 no C13 C12 H12 120.00 no C17 C12 H12 119.00 no C12 C13 H13 120.00 no C14 C13 H13 120.00 no C13 C14 H14 120.00 no C15 C14 H14 120.00 no C14 C15 H15 119.00 no C16 C15 H15 119.00 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C8 1.280(3) . N1 N2 1.301(3) . N1 C1 1.415(3) . N2 C7 1.349(3) . N1 H1 0.906(17) no C1 C2 1.379(3) no C1 C6 1.379(3) no C2 C3 1.379(3) no C3 C4 1.378(4) no C4 C5 1.368(4) no C5 C6 1.397(3) no C7 C8 1.448(3) no C7 C16 1.449(3) no C8 C9 1.439(3) no C9 C10 1.342(3) no C10 C17 1.431(3) no C12 C17 1.399(3) no C12 C13 1.361(3) no C13 C14 1.393(3) no C14 C15 1.369(3) no C15 C16 1.409(3) no C16 C17 1.411(3) no C2 H2 0.9300 no C3 H3 0.9300 no C4 H4 0.9300 no C5 H5 0.9300 no C6 H6 0.9300 no C9 H9 0.9300 no C10 H10 0.9300 no C12 H12 0.9300 no C13 H13 0.9300 no C14 H14 0.9300 no C15 H15 0.9300 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 N1 2.550(3) . no O1 N2 2.873(3) . no O1 H1 1.81(2) . no O1 H6 2.7100 7_665 no N1 O1 2.550(3) . no N1 C10 3.366(4) 1_565 no N2 O1 2.873(3) . no N2 C4 3.398(4) 1_545 no N2 C12 3.412(4) 1_565 no N2 H2 2.5000 . no N2 H15 2.5100 . no C1 C16 3.572(4) 1_565 no C1 C17 3.519(4) 1_565 no C2 C16 3.450(4) 1_565 no C4 N2 3.398(4) 1_565 no C5 C7 3.544(4) 1_565 no C6 C8 3.443(4) 1_565 no C6 C7 3.559(4) 1_565 no C7 C5 3.544(4) 1_545 no C7 C6 3.559(4) 1_545 no C8 C6 3.443(4) 1_545 no C10 N1 3.366(4) 1_545 no C12 N2 3.412(4) 1_545 no C16 C1 3.572(4) 1_545 no C16 C2 3.450(4) 1_545 no C17 C1 3.519(4) 1_545 no C3 H12 3.0000 4_564 no C3 H14 3.0700 3_675 no C4 H12 2.9200 4_564 no C5 H12 3.0700 4_564 no C8 H1 2.39(3) . no C12 H4 2.9400 4_575 no C13 H4 3.0800 4_575 no C14 H3 3.0700 3_675 no C17 H4 2.9600 4_575 no H1 O1 1.81(2) . no H1 C8 2.39(3) . no H1 H6 2.3800 . no H2 N2 2.5000 . no H3 C14 3.0700 3_675 no H3 H14 2.4800 3_675 no H4 C12 2.9400 4_574 no H4 C13 3.0800 4_574 no H4 C17 2.9600 4_574 no H6 H1 2.3800 . no H6 O1 2.7100 7_665 no H9 H10 2.5100 6_655 no H10 H12 2.4600 . no H10 H9 2.5100 6_645 no H12 H10 2.4600 . no H12 C3 3.0000 4_565 no H12 C4 2.9200 4_565 no H12 C5 3.0700 4_565 no H14 C3 3.0700 3_675 no H14 H3 2.4800 3_675 no H15 N2 2.5100 . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1 O1 . 0.906(17) 1.81(2) 2.550(3) 137(2) C4 H4 Cg3 4_574 0.93 2.76 3.568(4) 145 C12 H12 Cg1 4_565 0.93 2.83 3.612(4) 142 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 C1 N1 N2 C7 -179.84(16) no N2 N1 C1 C2 -1.4(3) no N2 N1 C1 C6 177.41(17) no N1 N2 C7 C8 0.3(3) no N1 N2 C7 C16 -177.64(16) no N1 C1 C2 C3 178.57(18) no C6 C1 C2 C3 -0.2(3) no N1 C1 C6 C5 -178.28(18) no C2 C1 C6 C5 0.5(3) no C1 C2 C3 C4 -0.5(3) no C2 C3 C4 C5 0.9(3) no C3 C4 C5 C6 -0.5(3) no C4 C5 C6 C1 -0.2(3) no N2 C7 C8 O1 1.2(3) no N2 C7 C8 C9 -178.06(17) no C16 C7 C8 O1 179.10(18) no C16 C7 C8 C9 -0.2(3) no N2 C7 C16 C15 -2.6(3) no N2 C7 C16 C17 175.67(16) no C8 C7 C16 C15 179.34(17) no C8 C7 C16 C17 -2.4(3) no O1 C8 C9 C10 -177.61(19) no C7 C8 C9 C10 1.7(3) no C8 C9 C10 C17 -0.6(3) no C9 C10 C17 C12 178.22(19) no C9 C10 C17 C16 -2.0(3) no C17 C12 C13 C14 -0.8(3) no C13 C12 C17 C10 179.41(19) no C13 C12 C17 C16 -0.4(3) no C12 C13 C14 C15 0.8(3) no C13 C14 C15 C16 0.5(3) no C14 C15 C16 C7 176.67(18) no C14 C15 C16 C17 -1.7(3) no C7 C16 C17 C10 3.4(3) no C7 C16 C17 C12 -176.80(17) no C15 C16 C17 C10 -178.21(17) no C15 C16 C17 C12 1.6(3) no