#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/69/2206900.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_2206900 loop_ _publ_author_name 'You, Zhong-Lu' _publ_section_title ; {1-[2-(Dimethylamino)ethyliminomethyl]-2-naphtholato}thiocyanatonickel(II) ; _journal_coeditor_code CF6451 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m1963 _journal_page_last m1964 _journal_paper_doi 10.1107/S1600536805028175 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac '[Ni (C15 H17 N2 O) (N C S)]' _chemical_formula_moiety 'C16 H17 N3 Ni O S' _chemical_formula_sum 'C16 H17 N3 Ni O S' _chemical_formula_weight 358.10 _chemical_name_systematic ; {1-[2-(Dimethylamino)ethyliminomethyl]-2-naphthalato}thiocyanatonickel(II) ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 93.04(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.413(2) _cell_length_b 6.167(2) _cell_length_c 30.683(6) _cell_measurement_reflns_used 1147 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 21.32 _cell_measurement_theta_min 2.48 _cell_volume 1589.7(7) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _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 0.0858 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_number 12963 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 1.33 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.356 _exptl_absorpt_correction_T_max 0.8023 _exptl_absorpt_correction_T_min 0.6786 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.491 _refine_diff_density_min -0.411 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 3617 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.998 _refine_ls_R_factor_all 0.1219 _refine_ls_R_factor_gt 0.0619 _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^)+(0.0615P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1271 _refine_ls_wR_factor_ref 0.1514 _reflns_number_gt 2051 _reflns_number_total 3617 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf6451.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2206900 _cod_database_fobs_code 2206900 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_type_symbol Ni1 0.73977(7) 0.30340(10) 0.106195(18) 0.0417(2) Uani d . 1 Ni S1 0.23326(18) 0.0588(3) 0.06465(6) 0.0832(5) Uani d . 1 S O1 0.7474(4) 0.0726(5) 0.14312(10) 0.0495(8) Uani d . 1 O N1 0.9231(4) 0.4202(6) 0.13116(12) 0.0409(9) Uani d . 1 N N2 0.7465(5) 0.5259(6) 0.06227(12) 0.0467(10) Uani d . 1 N N3 0.5415(5) 0.2030(7) 0.08382(14) 0.0587(11) Uani d . 1 N C1 0.9453(5) 0.2008(7) 0.19585(14) 0.0381(10) Uani d . 1 C C2 0.8339(5) 0.0494(7) 0.17941(16) 0.0428(11) Uani d . 1 C C3 0.8105(6) -0.1459(7) 0.20316(17) 0.0488(12) Uani d . 1 C H3 0.7445 -0.2537 0.1911 0.059 Uiso calc R 1 H C4 0.8831(6) -0.1753(8) 0.24283(18) 0.0522(13) Uani d . 1 C H4 0.8683 -0.3056 0.2573 0.063 Uiso calc R 1 H C5 0.9820(5) -0.0140(8) 0.26339(15) 0.0438(12) Uani d . 1 C C6 1.0359(6) -0.0344(9) 0.30716(18) 0.0585(15) Uani d . 1 C H6 1.0131 -0.1599 0.3224 0.070 Uiso calc R 1 H C7 1.1211(6) 0.1263(10) 0.32766(18) 0.0630(16) Uani d . 1 C H7 1.1530 0.1129 0.3570 0.076 Uiso calc R 1 H C8 1.1605(6) 0.3114(9) 0.30449(17) 0.0600(14) Uani d . 1 C H8 1.2205 0.4204 0.3184 0.072 Uiso calc R 1 H C9 1.1115(6) 0.3339(8) 0.26136(16) 0.0503(13) Uani d . 1 C H9 1.1412 0.4564 0.2461 0.060 Uiso calc R 1 H C10 1.0175(5) 0.1756(7) 0.23998(15) 0.0405(11) Uani d . 1 C C11 0.9900(5) 0.3736(7) 0.16859(15) 0.0414(11) Uani d . 1 C H11 1.0747 0.4603 0.1786 0.050 Uiso calc R 1 H C12 0.9947(6) 0.5860(9) 0.10361(17) 0.0614(15) Uani d . 1 C H12A 1.0510 0.6926 0.1218 0.074 Uiso calc R 1 H H12B 1.0701 0.5188 0.0850 0.074 Uiso calc R 1 H C13 0.8685(8) 0.6906(9) 0.07712(19) 0.0787(19) Uani d . 1 C H13A 0.9127 0.7588 0.0520 0.094 Uiso calc R 1 H H13B 0.8189 0.8023 0.0941 0.094 Uiso calc R 1 H C14 0.5971(7) 0.6478(9) 0.0534(2) 0.0801(19) Uani d . 1 C H14A 0.6148 0.7623 0.0331 0.120 Uiso calc R 1 H H14B 0.5628 0.7085 0.0802 0.120 Uiso calc R 1 H H14C 0.5165 0.5517 0.0413 0.120 Uiso calc R 1 H C15 0.7928(7) 0.4197(10) 0.02182(17) 0.0729(17) Uani d . 1 C H15A 0.7152 0.3117 0.0132 0.109 Uiso calc R 1 H H15B 0.8950 0.3523 0.0268 0.109 Uiso calc R 1 H H15C 0.7983 0.5260 -0.0009 0.109 Uiso calc R 1 H C16 0.4138(6) 0.1419(7) 0.07604(16) 0.0497(13) Uani d . 1 C 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 Ni1 0.0423(4) 0.0390(4) 0.0433(4) -0.0058(3) -0.0021(3) -0.0037(3) S1 0.0503(9) 0.0790(11) 0.1182(14) -0.0186(8) -0.0154(9) 0.0132(10) O1 0.054(2) 0.0419(19) 0.052(2) -0.0156(16) -0.0072(17) 0.0007(16) N1 0.040(2) 0.040(2) 0.042(2) -0.0093(18) -0.0027(18) 0.0052(18) N2 0.054(3) 0.048(2) 0.037(2) -0.007(2) -0.0035(19) 0.0002(19) N3 0.050(3) 0.062(3) 0.064(3) -0.011(2) -0.003(2) 0.001(2) C1 0.037(2) 0.034(2) 0.044(3) 0.001(2) 0.008(2) 0.005(2) C2 0.042(3) 0.036(3) 0.051(3) -0.003(2) 0.011(2) -0.004(2) C3 0.052(3) 0.035(3) 0.060(3) -0.006(2) 0.007(3) 0.001(2) C4 0.047(3) 0.040(3) 0.071(4) 0.004(2) 0.015(3) 0.020(3) C5 0.035(3) 0.049(3) 0.049(3) 0.021(2) 0.013(2) 0.010(2) C6 0.044(3) 0.067(4) 0.066(4) 0.015(3) 0.011(3) 0.024(3) C7 0.040(3) 0.099(5) 0.049(3) 0.018(3) -0.001(2) 0.021(3) C8 0.043(3) 0.077(4) 0.058(3) 0.004(3) -0.008(2) -0.001(3) C9 0.049(3) 0.052(3) 0.049(3) 0.005(2) -0.003(2) 0.006(3) C10 0.031(2) 0.042(3) 0.049(3) 0.007(2) 0.012(2) 0.004(2) C11 0.035(3) 0.037(3) 0.052(3) -0.008(2) 0.000(2) 0.000(2) C12 0.064(4) 0.066(4) 0.053(3) -0.031(3) -0.012(3) 0.023(3) C13 0.103(5) 0.062(4) 0.067(4) -0.036(4) -0.028(3) 0.021(3) C14 0.085(5) 0.069(4) 0.087(4) 0.026(3) 0.004(4) 0.015(3) C15 0.088(5) 0.075(4) 0.056(4) 0.007(3) 0.011(3) 0.000(3) C16 0.053(3) 0.043(3) 0.053(3) -0.005(2) -0.002(3) 0.004(2) 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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 O1 Ni1 N1 92.64(15) y O1 Ni1 N3 88.33(17) y N1 Ni1 N3 174.52(18) y O1 Ni1 N2 172.86(16) y N1 Ni1 N2 87.54(16) y N3 Ni1 N2 92.16(17) y C2 O1 Ni1 128.1(3) ? C11 N1 C12 119.6(4) ? C11 N1 Ni1 127.2(3) ? C12 N1 Ni1 113.1(3) ? C15 N2 C14 109.4(4) ? C15 N2 C13 110.5(5) ? C14 N2 C13 105.9(4) ? C15 N2 Ni1 106.9(3) ? C14 N2 Ni1 115.7(3) ? C13 N2 Ni1 108.4(3) ? C16 N3 Ni1 170.4(4) y C2 C1 C11 118.9(4) ? C2 C1 C10 120.1(4) ? C11 C1 C10 121.0(4) ? O1 C2 C1 124.6(4) ? O1 C2 C3 116.3(4) ? C1 C2 C3 119.2(5) ? C4 C3 C2 120.5(5) ? C4 C3 H3 119.7 ? C2 C3 H3 119.7 ? C3 C4 C5 122.3(5) ? C3 C4 H4 118.9 ? C5 C4 H4 118.9 ? C6 C5 C10 119.7(5) ? C6 C5 C4 121.0(5) ? C10 C5 C4 119.2(4) ? C7 C6 C5 121.0(5) ? C7 C6 H6 119.5 ? C5 C6 H6 119.5 ? C6 C7 C8 119.7(5) ? C6 C7 H7 120.1 ? C8 C7 H7 120.1 ? C9 C8 C7 120.5(5) ? C9 C8 H8 119.8 ? C7 C8 H8 119.8 ? C8 C9 C10 121.1(5) ? C8 C9 H9 119.5 ? C10 C9 H9 119.5 ? C9 C10 C5 118.0(4) ? C9 C10 C1 123.9(4) ? C5 C10 C1 118.0(4) ? N1 C11 C1 125.3(4) ? N1 C11 H11 117.3 ? C1 C11 H11 117.3 ? C13 C12 N1 108.6(4) ? C13 C12 H12A 110.0 ? N1 C12 H12A 110.0 ? C13 C12 H12B 110.0 ? N1 C12 H12B 110.0 ? H12A C12 H12B 108.3 ? C12 C13 N2 109.7(4) ? C12 C13 H13A 109.7 ? N2 C13 H13A 109.7 ? C12 C13 H13B 109.7 ? N2 C13 H13B 109.7 ? H13A C13 H13B 108.2 ? N2 C14 H14A 109.5 ? N2 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? N2 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? N2 C15 H15A 109.5 ? N2 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? N2 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? N3 C16 S1 179.2(5) y loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Ni1 O1 1.818(3) y Ni1 N1 1.833(4) y Ni1 N3 1.875(4) y Ni1 N2 1.926(4) y S1 C16 1.623(5) ? O1 C2 1.305(5) ? N1 C11 1.285(5) ? N1 C12 1.476(5) ? N2 C15 1.474(6) ? N2 C14 1.477(6) ? N2 C13 1.497(6) ? N3 C16 1.152(6) ? C1 C2 1.398(6) ? C1 C11 1.418(6) ? C1 C10 1.462(6) ? C2 C3 1.427(6) ? C3 C4 1.345(7) ? C3 H3 0.930 ? C4 C5 1.422(7) ? C4 H4 0.930 ? C5 C6 1.400(7) ? C5 C10 1.413(6) ? C6 C7 1.358(7) ? C6 H6 0.930 ? C7 C8 1.394(7) ? C7 H7 0.930 ? C8 C9 1.372(7) ? C8 H8 0.930 ? C9 C10 1.398(6) ? C9 H9 0.930 ? C11 H11 0.930 ? C12 C13 1.453(7) ? C12 H12A 0.970 ? C12 H12B 0.970 ? C13 H13A 0.970 ? C13 H13B 0.970 ? C14 H14A 0.960 ? C14 H14B 0.960 ? C14 H14C 0.960 ? C15 H15A 0.960 ? C15 H15B 0.960 ? C15 H15C 0.960 ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 168308885