#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/74/2007455.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_2007455 loop_ _publ_author_name 'Bruno, Giuseppe' 'Maccari, Rosanna' 'Nicol\'o, Francesco' 'Ottan\'a, Rosaria' 'Panzalorto, Manuela' 'Scopelliti, Rosario' 'Vigorita, Maria Gabriella' _publ_section_title ; 2'-[1-(4-Fluorophenyl)ethyl]isonicotino-\kN-hydrazide--Cyanoborane ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1038 _journal_page_last 1040 _journal_paper_doi 10.1107/S0108270198001681 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C15 H16 B F N4 O' _chemical_formula_sum 'C15 H16 B F N4 O' _chemical_formula_weight 298.13 _chemical_name_systematic ; 2'-[1-(4-Fluorophenyl)ethyl]isonicotino-\kN-hydrazide--Cyanoborane ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 91.57(4) _cell_angle_beta 92.83(3) _cell_angle_gamma 99.74(3) _cell_formula_units_Z 2 _cell_length_a 7.049(2) _cell_length_b 7.492(4) _cell_length_c 15.077(6) _cell_measurement_reflns_used 46 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 13 _cell_measurement_theta_min 5 _cell_volume 783.3(6) _computing_cell_refinement P3/V _computing_data_collection 'P3/V (Siemens,1989)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_molecular_graphics 'XPW (Siemens, 1996)' _computing_publication_material 'PARST97 (Nardelli, 1995) and SHELXL97' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens R3m/V diffractometer' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_av_sigmaI/netI 0.075 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3011 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 2.71 _diffrn_standards_decay_% 1.31 _diffrn_standards_interval_count 197 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description prismatic _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.169 _refine_diff_density_min -0.199 _refine_ls_extinction_coef 0.029(7) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_all 0.820 _refine_ls_goodness_of_fit_obs 1.193 _refine_ls_hydrogen_treatment 'H atoms: see text' _refine_ls_matrix_type full _refine_ls_number_parameters 257 _refine_ls_number_reflns 2768 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.820 _refine_ls_restrained_S_obs 1.193 _refine_ls_R_factor_all 0.152 _refine_ls_R_factor_obs .063 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1043P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.187 _refine_ls_wR_factor_obs .152 _reflns_number_observed 1066 _reflns_number_total 2768 _reflns_observed_criterion I>2\s(I) _cod_data_source_file na1320.cif _cod_data_source_block vigor _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.1043P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.1043P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 783.3(5) _cod_database_code 2007455 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 N1 1.2062(5) .0789(5) 1.2087(2) .1002(12) Uani d . 1 . . N C1 1.1309(5) .1995(6) 1.2001(2) .0731(11) Uani d . 1 . . C B1 1.0282(7) .3665(6) 1.1852(3) .0850(14) Uani d . 1 . . B H1A 1.1217 .4703 1.1703 .080 Uiso calc R 1 . . H H1B .9700 .3971 1.2393 .080 Uiso calc R 1 . . H N2 .8660(4) .3183(3) 1.10637(18) .0644(8) Uani d . 1 . . N C2 .9130(5) .2669(5) 1.0268(3) .0753(11) Uani d . 1 . . C H2 1.0413 .2602 1.0181 .080 Uiso calc R 1 . . H C3 .7803(5) .2232(5) .9565(2) .0707(10) Uani d . 1 . . C H3 .8174 .1855 .9017 .080 Uiso calc R 1 . . H C4 .5896(4) .2366(4) .9691(2) .0562(8) Uani d . 1 . . C C5 .5431(5) .2905(5) 1.0504(2) .0734(11) Uani d . 1 . . C H5 .4159 .2994 1.0606 .080 Uiso calc R 1 . . H C6 .6833(6) .3322(5) 1.1181(2) .0798(11) Uani d . 1 . . C H6 .6494 .3710 1.1733 .080 Uiso calc R 1 . . H C7 .4270(5) .1906(5) .8976(2) .0636(9) Uani d . 1 . . C O1 .2659(4) .2242(4) .91061(17) .1012(10) Uani d . 1 . . O N3 .4693(4) .1134(4) .82332(18) .0689(8) Uani d . 1 . . N H7 .5868 .1036 .8145 .080 Uiso calc R 1 . . H N4 .3216(4) .0467(4) .7581(2) .0839(10) Uani d . 1 . . N H8 .2082 -.0021 .7722 .080 Uiso calc R 1 A 1 H C8A .3683(9) .0639(9) .6715(4) .0665(15) Uani d P .60 B 1 C H8A .4633 -.0147 .6606 .080 Uiso calc PR .60 B 1 H C9A .4579(14) .2525(8) .6512(7) .075(5) Uani d PG .60 B 1 C C10A .3539(10) .3935(12) .6593(5) .091(3) Uani d PG .60 B 1 C H10A .2301 .3714 .6798 .080 Uiso calc PR .60 B 1 H C11A .4351(15) .5676(10) .6370(7) .117(5) Uani d PG .60 B 1 C H11A .3655 .6619 .6424 .080 Uiso calc PR .60 B 1 H C12A .6201(17) .6006(10) .6064(8) .118(9) Uani d PG .60 B 1 C C13A .7241(11) .4595(14) .5982(6) .100(4) Uani d PG .60 B 1 C H13A .8479 .4816 .5778 .080 Uiso calc PR .60 B 1 H C14A .6429(13) .2855(11) .6206(6) .086(3) Uani d PG .60 B 1 C H14A .7125 .1911 .6151 .080 Uiso calc PR .60 B 1 H F1A .6910(9) .7698(7) .5836(3) .162(2) Uani d P .60 B 1 F C15A .1896(18) -.0077(13) .6130(7) .101(3) Uani d P .60 B 1 C H15A .1414 -.1305 .6273 .080 Uiso calc PR .60 B 1 H H15B .2212 -.0037 .5518 .080 Uiso calc PR .60 B 1 H H15C .0929 .0657 .6227 .080 Uiso calc PR .60 B 1 H C8B .2837(13) .1973(15) .6928(6) .076(3) Uani d P .40 B 2 C H8B .2259 .2859 .7266 .080 Uiso calc PR .40 B 2 H C9B .4516(17) .297(2) .6524(9) .053(5) Uani d PG .40 B 2 C C10B .4658(19) .483(2) .6438(9) .098(5) Uani d PG .40 B 2 C H10B .3710 .5425 .6653 .080 Uiso calc PR .40 B 2 H C11B .622(3) .5799(13) .6031(12) .117(17) Uani d PG .40 B 2 C H11B .6312 .7043 .5974 .080 Uiso calc PR .40 B 2 H C12B .763(2) .491(2) .5710(10) .130(10) Uani d PG .40 B 2 C C13B .7491(19) .305(2) .5796(8) .120(6) Uani d PG .40 B 2 C H13B .8439 .2452 .5582 .080 Uiso calc PR .40 B 2 H C14B .593(2) .2079(13) .6203(10) .125(7) Uani d PG .40 B 2 C H14B .5838 .0835 .6261 .080 Uiso calc PR .40 B 2 H F1B .9174(12) .5962(13) .5365(6) .180(4) Uani d P .40 B 2 F C15B .134(3) .109(3) .6240(12) .164(10) Uani d P .40 B 2 C H15D .0278 .0418 .6526 .080 Uiso calc PR .40 B 2 H H15E .1895 .0289 .5861 .080 Uiso calc PR .40 B 2 H H15F .0899 .2007 .5890 .080 Uiso calc PR .40 B 2 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 N1 .092(3) .128(3) .087(2) .052(2) -.0217(19) -.017(2) C1 .057(2) .099(3) .062(2) .016(2) -.0141(17) -.007(2) B1 .088(3) .083(3) .078(3) .010(3) -.029(3) -.004(2) N2 .0665(19) .0679(19) .0598(18) .0172(15) -.0083(14) .0061(15) C2 .053(2) .099(3) .073(3) .015(2) -.0054(19) -.004(2) C3 .059(2) .089(3) .063(2) .0136(19) -.0026(18) -.0027(19) C4 .055(2) .061(2) .054(2) .0139(17) -.0018(16) .0174(16) C5 .058(2) .104(3) .062(2) .026(2) -.0049(18) .011(2) C6 .089(3) .097(3) .061(2) .035(2) .001(2) .004(2) C7 .063(2) .070(2) .058(2) .0126(19) -.0041(19) .0146(18) O1 .0548(16) .169(3) .0839(19) .0349(17) -.0062(13) -.0014(17) N3 .0510(16) .090(2) .0644(19) .0136(15) -.0133(14) .0029(16) N4 .0632(19) .095(2) .083(2) -.0073(17) -.0269(17) .0143(18) C8A .068(4) .070(4) .061(4) .013(4) -.008(3) .003(3) C9A .078(10) .093(8) .057(7) .026(7) -.005(6) -.004(6) C10A .103(7) .078(6) .093(6) .018(6) .000(5) .002(5) C11A .169(13) .091(8) .090(7) .016(8) .004(8) .016(6) C12A .16(2) .134(17) .046(8) -.006(13) .003(10) .015(8) C13A .083(7) .140(11) .062(7) -.024(8) -.008(5) .011(7) C14A .087(7) .112(7) .060(6) .024(6) -.001(5) -.005(5) F1A .248(7) .112(4) .095(3) -.052(4) -.012(4) .029(3) C15A .115(8) .107(7) .065(5) -.018(6) -.026(5) .005(5) C8B .065(6) .094(8) .073(6) .022(6) -.001(5) .028(6) C9B .059(11) .070(8) .033(8) .021(8) -.012(7) .007(6) C10B .109(14) .135(16) .051(8) .031(14) -.023(9) -.009(9) C11B .15(3) .058(13) .11(2) -.040(17) -.06(2) .010(12) C12B .097(12) .20(2) .077(12) -.015(13) -.004(8) .082(14) C13B .148(14) .145(15) .088(10) .072(12) .041(9) .044(11) C14B .092(12) .165(16) .115(14) .000(14) .010(11) .060(14) F1B .133(7) .232(10) .154(7) -.033(6) -.016(6) .079(6) C15B .097(12) .24(2) .125(14) -.050(16) -.058(10) .090(16) 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' B B 0.0013 0.0007 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 0 -4 1 0 4 -1 -2 2 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 N1 C1 B1 178.3(4) y C1 B1 N2 109.2(3) y C2 N2 C6 118.5(3) y C2 N2 B1 120.0(3) y C6 N2 B1 121.4(3) y N2 C2 C3 122.8(3) ? C2 C3 C4 118.5(3) ? C5 C4 C3 118.3(3) ? C5 C4 C7 117.4(3) ? C3 C4 C7 124.3(3) ? C4 C5 C6 120.2(3) ? N2 C6 C5 121.6(3) ? O1 C7 N3 123.1(3) y O1 C7 C4 120.5(3) y N3 C7 C4 116.5(3) y C7 N3 N4 119.9(3) y C8A N4 N3 116.5(4) y C8A N4 C8B 51.6(4) ? N3 N4 C8B 111.5(4) ? N4 C8A C9A 112.9(6) ? N4 C8A C15A 108.1(7) ? C9A C8A C15A 113.1(7) ? C10A C9A C14A 120.0 ? C10A C9A C8A 120.2(7) ? C14A C9A C8A 119.7(7) ? C9A C10A C11A 120.0 ? C12A C11A C10A 120.0 ? F1A C12A C11A 118.0(9) ? F1A C12A C13A 122.0(9) ? C11A C12A C13A 120.0 ? C14A C13A C12A 120.0 ? C13A C14A C9A 120.0 ? C9B C8B C15B 111.6(12) ? C9B C8B N4 116.6(9) ? C15B C8B N4 106.9(10) ? C10B C9B C14B 120.0 ? C10B C9B C8B 119.0(13) ? C14B C9B C8B 121.0(13) ? C11B C10B C9B 120.0 ? C10B C11B C12B 120.0 ? F1B C12B C11B 116.7(13) ? F1B C12B C13B 123.2(13) ? C11B C12B C13B 120.0 ? C14B C13B C12B 120.0 ? C13B C14B C9B 120.0 ? 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 N1 C1 . 1.130(4) y C1 B1 . 1.563(6) y B1 N2 . 1.598(4) y N2 C2 . 1.325(4) y N2 C6 . 1.330(4) y C2 C3 . 1.373(4) ? C3 C4 . 1.386(4) ? C4 C5 . 1.354(4) ? C4 C7 . 1.522(4) y C5 C6 . 1.376(5) ? C7 O1 . 1.228(4) y C7 N3 . 1.317(4) y N3 N4 . 1.413(3) y N4 C8A . 1.367(6) ? N4 C8B . 1.566(10) ? C8A C9A . 1.493(8) ? C8A C15A . 1.512(12) ? C9A C10A . 1.3900 ? C9A C14A . 1.3900 ? C10A C11A . 1.3900 ? C11A C12A . 1.3900 ? C12A F1A . 1.342(7) ? C12A C13A . 1.3900 ? C13A C14A . 1.3900 ? C8B C9B . 1.458(14) ? C8B C15B . 1.497(18) ? C9B C10B . 1.3900 ? C9B C14B . 1.3900 ? C10B C11B . 1.3900 ? C11B C12B . 1.3900 ? C12B F1B . 1.365(12) ? C12B C13B . 1.3900 ? C13B C14B . 1.3900 ? 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 N3 H7 N1 2_757 0.86 2.20 2.954(5) 147 C3 H3 N1 2_757 0.93 2.53 3.335(5) 145 C2 H2 O1 1_655 0.93 2.36 3.166(5) 145 C5 H5 O1 . 0.93 2.46 2.778(4) 100 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 N1 C1 B1 N2 57(14) C1 B1 N2 C2 -57.4(5) C1 B1 N2 C6 124.0(4) C6 N2 C2 C3 -1.6(5) B1 N2 C2 C3 179.8(4) N2 C2 C3 C4 1.2(6) C2 C3 C4 C5 -0.6(5) C2 C3 C4 C7 -179.3(3) C3 C4 C5 C6 0.6(5) C7 C4 C5 C6 179.3(3) C2 N2 C6 C5 1.6(5) B1 N2 C6 C5 -179.9(3) C4 C5 C6 N2 -1.1(6) C5 C4 C7 O1 9.2(5) C3 C4 C7 O1 -172.1(4) C5 C4 C7 N3 -170.3(3) C3 C4 C7 N3 8.3(5) O1 C7 N3 N4 -7.2(5) C4 C7 N3 N4 172.4(3) C7 N3 N4 C8A 144.2(4) C7 N3 N4 C8B 87.6(6) N3 N4 C8A C9A -51.7(7) C8B N4 C8A C9A 45.7(7) N3 N4 C8A C15A -177.6(5) C8B N4 C8A C15A -80.2(7) N4 C8A C9A C10A -62.7(8) C15A C8A C9A C10A 60.5(9) N4 C8A C9A C14A 119.9(6) C15A C8A C9A C14A -117.0(8) C14A C9A C10A C11A 0.0 C8A C9A C10A C11A -177.4(10) C9A C10A C11A C12A 0.0 C10A C11A C12A F1A 178.5(11) C10A C11A C12A C13A 0.0 F1A C12A C13A C14A -178.4(11) C11A C12A C13A C14A 0.0 C12A C13A C14A C9A 0.0 C10A C9A C14A C13A 0.0 C8A C9A C14A C13A 177.4(9) C8A N4 C8B C9B -56.3(9) N3 N4 C8B C9B 51.1(11) C8A N4 C8B C15B 69.2(11) N3 N4 C8B C15B 176.6(10) C15B C8B C9B C10B 97.6(14) N4 C8B C9B C10B -139.2(10) C15B C8B C9B C14B -80.4(13) N4 C8B C9B C14B 42.7(11) C14B C9B C10B C11B 0.0 C8B C9B C10B C11B -178.1(12) C9B C10B C11B C12B 0.0 C10B C11B C12B F1B -176.4(14) C10B C11B C12B C13B 0.0 F1B C12B C13B C14B 176.2(15) C11B C12B C13B C14B 0.0 C12B C13B C14B C9B 0.0 C10B C9B C14B C13B 0.0 C8B C9B C14B C13B 178.0(12) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139056105