#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/06/2200609.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_2200609 loop_ _publ_author_name 'Yatsenko, A. V.' 'Paseshnichenko, K. A.' _publ_section_title ; \p--\p Stacks and C--H···O bonded sheets in 4-[(2-nitrophenyl)hydrazono]-4H-naphthalen-1-one ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1025 _journal_page_last o1026 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C16 H11 N3 O3' _chemical_formula_moiety 'C16 H11 N3 O3' _chemical_formula_sum 'C16 H11 N3 O3' _chemical_formula_weight 293.28 _chemical_melting_point 517 _chemical_name_systematic ; 4-[(2-nitrophenyl)hydrazono]-4H-naphthalen-1-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 99.33(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.328(2) _cell_length_b 16.366(4) _cell_length_c 11.131(3) _cell_measurement_reflns_used 22 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16.3 _cell_measurement_theta_min 14.7 _cell_volume 1317.3(6) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'PROFIT (Streltsov & Zavodnik, 1989)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2001)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0175 _diffrn_reflns_av_sigmaI/netI .0225 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3173 _diffrn_reflns_theta_full 27.46 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_min 2.23 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .105 _exptl_absorpt_correction_type none _exptl_crystal_colour 'dark red' _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 608 _exptl_crystal_size_max .55 _exptl_crystal_size_mid .16 _exptl_crystal_size_min .09 _refine_diff_density_max .201 _refine_diff_density_min -.156 _refine_ls_extinction_coef .0027(8) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.309 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 244 _refine_ls_number_reflns 3025 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.309 _refine_ls_R_factor_all .0748 _refine_ls_R_factor_gt .0450 _refine_ls_shift/su_max .006 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.04P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1077 _reflns_number_gt 2041 _reflns_number_total 3025 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf6106.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2200609 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .60667(17) .57864(7) .93712(9) .0572(4) Uani d . 1 . . O O2 .23492(18) .27875(7) .44880(11) .0656(4) Uani d . 1 . . O O3 .1408(2) .20724(7) .28875(13) .0759(4) Uani d . 1 . . O N1 .21431(17) .43700(7) .44329(10) .0401(3) Uani d . 1 . . N N2 .23925(16) .51405(7) .48507(10) .0380(3) Uani d . 1 . . N N3 .15886(19) .27320(8) .34107(13) .0498(4) Uani d . 1 . . N C1 .5250(2) .56377(9) .83466(13) .0386(4) Uani d . 1 . . C C2 .5072(2) .48104(9) .78856(14) .0425(4) Uani d . 1 . . C C3 .4199(2) .46339(9) .67641(14) .0426(4) Uani d . 1 . . C C4 .33440(19) .52586(8) .59335(12) .0336(3) Uani d . 1 . . C C5 .2814(2) .67590(9) .55850(14) .0445(4) Uani d . 1 . . C C6 .2949(2) .75520(10) .59902(16) .0517(4) Uani d . 1 . . C C7 .3810(2) .77243(9) .71679(16) .0523(4) Uani d . 1 . . C C8 .4546(2) .71045(10) .79169(15) .0469(4) Uani d . 1 . . C C9 .4430(2) .62964(9) .75147(13) .0366(3) Uani d . 1 . . C C10 .35333(19) .61141(8) .63376(12) .0352(3) Uani d . 1 . . C C11 .11540(19) .42454(8) .32735(12) .0356(3) Uani d . 1 . . C C12 .0890(2) .34606(9) .27546(13) .0390(4) Uani d . 1 . . C C13 -.0090(2) .33540(11) .15852(15) .0478(4) Uani d . 1 . . C C14 -.0833(2) .40066(11) .09289(15) .0523(5) Uani d . 1 . . C C15 -.0601(2) .47837(11) .14233(15) .0491(4) Uani d . 1 . . C C16 .0393(2) .49030(9) .25649(14) .0416(4) Uani d . 1 . . C H2 .555(2) .4411(10) .8370(14) .053(5) Uiso d . 1 . . H H3 .419(2) .4083(11) .6500(16) .069(5) Uiso d . 1 . . H H5 .226(2) .6630(10) .4827(15) .051(5) Uiso d . 1 . . H H6 .241(2) .7953(11) .5459(14) .061(5) Uiso d . 1 . . H H7 .383(2) .8270(10) .7417(13) .055(5) Uiso d . 1 . . H H8 .508(2) .7184(11) .8724(16) .062(5) Uiso d . 1 . . H H13 -.022(3) .2800(12) .1302(16) .072(6) Uiso d . 1 . . H H14 -.153(2) .3925(10) .0167(15) .060(5) Uiso d . 1 . . H H15 -.114(2) .5221(10) .0985(14) .055(5) Uiso d . 1 . . H H16 .054(2) .5419(10) .2910(13) .052(5) Uiso d . 1 . . H H1 .257(2) .3828(10) .4895(13) .047(4) Uiso d . 1 . . H 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 .0728(8) .0503(7) .0403(6) -.0017(6) -.0153(6) -.0015(5) O2 .0868(10) .0455(7) .0558(8) .0033(6) -.0150(7) .0075(6) O3 .0982(11) .0346(6) .0878(10) -.0061(7) -.0059(8) -.0118(6) N1 .0484(8) .0330(6) .0355(7) .0011(6) -.0037(6) -.0011(5) N2 .0417(7) .0341(6) .0367(7) .0005(5) .0020(6) -.0021(5) N3 .0534(8) .0344(7) .0595(9) -.0051(6) .0027(7) .0012(6) C1 .0382(8) .0396(8) .0358(8) -.0017(7) -.0007(6) .0008(6) C2 .0485(10) .0361(8) .0392(9) .0059(7) -.0042(7) .0071(7) C3 .0488(10) .0332(7) .0436(9) .0025(7) .0004(7) -.0009(7) C4 .0345(8) .0338(7) .0314(7) .0002(6) .0017(6) .0000(6) C5 .0506(10) .0373(8) .0409(9) -.0003(7) -.0064(8) .0043(7) C6 .0576(11) .0356(8) .0572(10) .0016(8) -.0048(8) .0092(8) C7 .0586(11) .0305(8) .0637(11) -.0027(8) -.0019(9) -.0037(8) C8 .0507(10) .0406(8) .0454(9) -.0040(7) -.0042(8) -.0055(7) C9 .0349(8) .0368(7) .0365(7) -.0022(6) .0006(6) -.0005(6) C10 .0337(8) .0351(7) .0361(8) -.0004(6) .0030(6) .0028(6) C11 .0334(8) .0387(8) .0333(8) -.0018(6) .0015(6) -.0004(6) C12 .0365(8) .0387(8) .0409(8) -.0037(6) .0036(6) -.0011(6) C13 .0471(10) .0511(10) .0445(9) -.0116(8) .0049(7) -.0095(8) C14 .0491(10) .0681(12) .0359(9) -.0104(9) -.0045(7) -.0030(8) C15 .0465(10) .0566(10) .0417(9) .0030(8) -.0002(8) .0102(8) C16 .0449(9) .0376(8) .0405(9) .0026(7) .0014(7) -.0002(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.2235(17) yes O2 N3 . 1.2410(16) no O3 N3 . 1.2235(16) no N1 N2 . 1.3462(17) yes N1 C11 . 1.3889(17) no N1 H1 . 1.047(15) no N2 C4 . 1.3053(17) yes N3 C12 . 1.4479(19) no C1 C2 . 1.446(2) yes C1 C9 . 1.483(2) yes C2 C3 . 1.339(2) yes C2 H2 . .884(16) no C3 C4 . 1.451(2) yes C3 H3 . .949(18) no C4 C10 . 1.4703(19) yes C5 C6 . 1.372(2) no C5 C10 . 1.397(2) no C5 H5 . .900(16) no C6 C7 . 1.389(2) no C6 H6 . .929(17) no C7 C8 . 1.367(2) no C7 H7 . .935(16) no C8 C9 . 1.394(2) no C8 H8 . .929(17) no C9 C10 . 1.3995(19) no C11 C16 . 1.396(2) no C11 C12 . 1.409(2) no C12 C13 . 1.392(2) no C13 C14 . 1.357(2) no C13 H13 . .960(19) no C14 C15 . 1.385(2) no C14 H14 . .926(17) no C15 C16 . 1.372(2) no C15 H15 . .918(16) no C16 H16 . .927(16) no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 '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 C11 118.67(12) yes N2 N1 H1 127.6(8) no C11 N1 H1 113.7(8) no C4 N2 N1 118.69(12) yes O3 N3 O2 121.44(14) no O3 N3 C12 118.97(14) no O2 N3 C12 119.59(13) no O1 C1 C2 121.28(14) no O1 C1 C9 121.65(14) no C2 C1 C9 117.06(13) no C3 C2 C1 122.32(14) no C3 C2 H2 119.5(10) no C1 C2 H2 118.2(10) no C2 C3 C4 122.28(14) no C2 C3 H3 118.1(11) no C4 C3 H3 119.5(11) no N2 C4 C3 126.51(13) yes N2 C4 C10 115.68(12) yes C3 C4 C10 117.81(12) no C6 C5 C10 121.16(15) no C6 C5 H5 121.9(11) no C10 C5 H5 117.0(11) no C5 C6 C7 119.99(15) no C5 C6 H6 117.3(11) no C7 C6 H6 122.7(11) no C8 C7 C6 119.93(15) no C8 C7 H7 122.9(10) no C6 C7 H7 117.1(10) no C7 C8 C9 120.70(15) no C7 C8 H8 123.3(11) no C9 C8 H8 115.9(11) no C8 C9 C10 119.84(14) no C8 C9 C1 119.45(13) no C10 C9 C1 120.71(13) no C5 C10 C9 118.35(13) no C5 C10 C4 121.90(13) no C9 C10 C4 119.75(12) no N1 C11 C16 120.81(13) no N1 C11 C12 122.09(13) no C16 C11 C12 117.10(13) no C13 C12 C11 120.90(14) no C13 C12 N3 117.07(14) no C11 C12 N3 122.02(13) no C14 C13 C12 120.39(16) no C14 C13 H13 123.9(11) no C12 C13 H13 115.7(11) no C13 C14 C15 119.73(15) no C13 C14 H14 119.6(11) no C15 C14 H14 120.6(11) no C16 C15 C14 120.73(16) no C16 C15 H15 119.9(10) no C14 C15 H15 119.3(10) no C15 C16 C11 121.12(15) no C15 C16 H16 121.5(10) no C11 C16 H16 117.3(10) 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 _geom_hbond_publ_flag N1 H1 O2 . 1.05(2) 1.76(2) 2.594(2) 133.0(10) yes C2 H2 O3 2_555 .88(2) 2.58(2) 3.233(2) 131.0(10) yes C6 H6 O1 2_464 .93(2) 2.51(2) 3.426(2) 169.0(10) yes C13 H13 O2 2_454 .96(2) 2.65(2) 3.323(2) 128.0(10) yes C15 H15 O1 1_454 .92(2) 2.66(2) 3.474(2) 148.0(10) yes