#------------------------------------------------------------------------------ #$Date: 2019-11-17 09:06:29 +0200 (Sun, 17 Nov 2019) $ #$Revision: 229011 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229965.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7229965 loop_ _publ_author_name 'Dankhoff, Katja' 'Weber, Birgit' _publ_section_title ; Novel Cu(ii) complexes with NNO-Schiff base-like ligands -- structures and magnetic properties ; _journal_issue 6 _journal_name_full CrystEngComm _journal_page_first 818 _journal_paper_doi 10.1039/C7CE02007D _journal_volume 20 _journal_year 2018 _chemical_formula_moiety 'C12 H13 N3 O2' _chemical_formula_sum 'C12 H13 N3 O2' _chemical_formula_weight 231.25 _chemical_name_common HL30d _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2017-07-27 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-01-11 deposited with the CCDC. 2018-01-15 downloaded from the CCDC. ; _cell_angle_alpha 74.653(5) _cell_angle_beta 75.243(5) _cell_angle_gamma 87.728(5) _cell_formula_units_Z 2 _cell_length_a 6.0280(4) _cell_length_b 9.2207(6) _cell_length_c 11.3737(7) _cell_measurement_reflns_used 5045 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 28.42 _cell_measurement_theta_min 1.92 _cell_volume 589.26(7) _computing_cell_refinement X-AREA-STOE _computing_data_collection X-AREA-STOE _computing_data_reduction X-AREA-STOE _computing_molecular_graphics ORTEP-III _computing_publication_material PLATON _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution SIR97 _diffrn_ambient_temperature 133(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measurement_device_type STOE-STADIVARI _diffrn_measurement_method omega-scan _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_unetI/netI 0.0353 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.937 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6744 _diffrn_reflns_point_group_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.937 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.395 _diffrn_reflns_theta_min 1.919 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 244 _exptl_crystal_size_max 0.266 _exptl_crystal_size_mid 0.182 _exptl_crystal_size_min 0.137 _refine_diff_density_max 0.280 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2762 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0421 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0156P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1119 _refine_ls_wR_factor_ref 0.1172 _reflns_number_gt 2075 _reflns_number_total 2762 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02007d2.cif _cod_data_source_block cl107 _cod_depositor_comments 'Adding full bibliography for 7229962--7229987.cif.' _cod_database_code 7229965 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL SIR97 run in space group P -1 CELL 0.71073 6.0280 9.2207 11.3737 74.653 75.243 87.728 ZERR 2.00 0.0004 0.0006 0.0007 0.005 0.005 0.005 LATT 1 SFAC C H N O UNIT 24 26 6 4 MERG 2 FMAP 2 PLAN 10 ACTA BOND $H CONF LIST 4 L.S. 20 TEMP -140.00 WGHT 0.068000 0.015600 FVAR 0.95016 C1 1 0.062315 -0.073998 0.325947 11.00000 0.03469 0.03186 = 0.05140 -0.01193 -0.00729 -0.00718 AFIX 43 H1 2 -0.049840 -0.135000 0.314662 11.00000 -1.20000 AFIX 0 C2 1 0.259895 -0.140379 0.349865 11.00000 0.04261 0.02929 = 0.03598 -0.00929 -0.00239 0.00404 AFIX 43 H2 2 0.282387 -0.244510 0.356505 11.00000 -1.20000 AFIX 0 C3 1 0.423927 -0.051706 0.363888 11.00000 0.03605 0.04162 = 0.04688 -0.01365 -0.01497 0.01277 AFIX 43 H3 2 0.562666 -0.093676 0.380716 11.00000 -1.20000 AFIX 0 C4 1 0.384659 0.099532 0.353206 11.00000 0.02844 0.03785 = 0.04014 -0.01339 -0.01443 0.00271 AFIX 43 H4 2 0.497294 0.163293 0.360800 11.00000 -1.20000 AFIX 0 C5 1 0.179148 0.156367 0.331331 11.00000 0.02317 0.02828 = 0.01811 -0.00499 -0.00328 -0.00227 C6 1 0.114754 0.318495 0.320600 11.00000 0.02363 0.02751 = 0.02652 -0.00529 -0.00678 -0.00201 AFIX 23 H6A 2 0.065991 0.358358 0.241596 11.00000 -1.20000 H6B 2 -0.018182 0.322314 0.391705 11.00000 -1.20000 AFIX 0 C7 1 0.452827 0.482099 0.216929 11.00000 0.03054 0.02502 = 0.02253 -0.00846 -0.00895 0.00078 AFIX 43 H7 2 0.428968 0.471854 0.140075 11.00000 -1.20000 AFIX 0 C8 1 0.644564 0.565042 0.208533 11.00000 0.02881 0.02502 = 0.02347 -0.00893 -0.00878 -0.00083 C12 1 0.696819 0.584062 0.318677 11.00000 0.02497 0.02054 = 0.02428 -0.00564 -0.00441 -0.00144 C9 1 0.796286 0.629703 0.084491 11.00000 0.03073 0.02600 = 0.02591 -0.00817 -0.00991 -0.00191 C10 1 1.141015 0.770625 -0.027088 11.00000 0.04054 0.03711 = 0.02373 -0.00818 -0.00048 -0.01118 AFIX 23 H10A 2 1.063126 0.826052 -0.091729 11.00000 -1.20000 H10B 2 1.229583 0.689385 -0.057813 11.00000 -1.20000 AFIX 0 C11 1 1.297620 0.875237 -0.002563 11.00000 0.03639 0.04038 = 0.03664 -0.00884 -0.00506 -0.01208 AFIX 133 H11A 2 1.209665 0.958615 0.022536 11.00000 -1.50000 H11B 2 1.419205 0.915015 -0.079372 11.00000 -1.50000 H11C 2 1.366347 0.820456 0.065177 11.00000 -1.50000 AFIX 0 N1 3 0.017935 0.071058 0.317552 11.00000 0.02773 0.02946 = 0.04327 -0.00779 -0.01118 -0.00358 N2 3 0.300010 0.415896 0.320979 11.00000 0.03183 0.02904 = 0.02098 -0.00764 -0.00753 -0.00403 AFIX 43 H2A 2 0.309499 0.430631 0.392913 11.00000 -1.20000 AFIX 0 N3 3 0.731586 0.595514 0.410195 11.00000 0.03665 0.03307 = 0.02372 -0.00776 -0.00690 -0.00564 O1 4 0.767774 0.615235 -0.013857 11.00000 0.04303 0.04579 = 0.02304 -0.01060 -0.01008 -0.01181 O2 4 0.972922 0.707580 0.091608 11.00000 0.03260 0.03427 = 0.02147 -0.00842 -0.00569 -0.00924 HKLF 4 REM SIR97 run in space group P -1 REM R1 = 0.0421 for 2075 Fo > 4sig(Fo) and 0.0560 for all 2762 data REM 154 parameters refined using 0 restraints END WGHT 0.0684 0.0102 REM Highest difference peak 0.280, deepest hole -0.196, 1-sigma level 0.046 Q1 1 0.6626 0.5657 0.0434 11.00000 0.05 0.28 Q2 1 1.2071 0.8268 -0.0055 11.00000 0.05 0.27 Q3 1 0.0898 0.1093 0.3314 11.00000 0.05 0.26 Q4 1 0.8227 0.6189 0.4304 11.00000 0.05 0.24 Q5 1 0.3288 0.4071 0.2224 11.00000 0.05 0.24 Q6 1 0.3278 -0.0839 0.3511 11.00000 0.05 0.23 Q7 1 0.2692 0.1087 0.3658 11.00000 0.05 0.22 Q8 1 0.5345 0.5422 0.2152 11.00000 0.05 0.22 Q9 1 0.7918 0.6253 0.3344 11.00000 0.05 0.20 Q10 1 0.6666 0.5595 0.2629 11.00000 0.05 0.20 ; _shelx_res_checksum 44141 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp C1 C 0.0623(3) -0.07400(17) 0.32595(16) 0.0396(4) Uani 1 1 d . . H1 H -0.0498 -0.1350 0.3147 0.047 Uiso 1 1 calc R U C2 C 0.2599(3) -0.14038(17) 0.34986(15) 0.0373(3) Uani 1 1 d . . H2 H 0.2824 -0.2445 0.3565 0.045 Uiso 1 1 calc R U C3 C 0.4239(3) -0.05171(19) 0.36389(16) 0.0406(4) Uani 1 1 d . . H3 H 0.5627 -0.0937 0.3807 0.049 Uiso 1 1 calc R U C4 C 0.3847(2) 0.09953(17) 0.35321(14) 0.0338(3) Uani 1 1 d . . H4 H 0.4973 0.1633 0.3608 0.041 Uiso 1 1 calc R U C5 C 0.1791(2) 0.15637(15) 0.33133(11) 0.0237(3) Uani 1 1 d . . C6 C 0.1148(2) 0.31850(15) 0.32060(12) 0.0261(3) Uani 1 1 d . . H6A H 0.0660 0.3584 0.2416 0.031 Uiso 1 1 calc R U H6B H -0.0182 0.3223 0.3917 0.031 Uiso 1 1 calc R U C7 C 0.4528(2) 0.48210(14) 0.21693(12) 0.0252(3) Uani 1 1 d . . H7 H 0.4290 0.4719 0.1401 0.030 Uiso 1 1 calc R U C8 C 0.6446(2) 0.56504(14) 0.20853(12) 0.0248(3) Uani 1 1 d . . C12 C 0.6968(2) 0.58406(14) 0.31868(12) 0.0236(3) Uani 1 1 d . . C9 C 0.7963(2) 0.62970(15) 0.08449(12) 0.0267(3) Uani 1 1 d . . C10 C 1.1410(3) 0.77063(17) -0.02709(13) 0.0349(3) Uani 1 1 d . . H10A H 1.0631 0.8261 -0.0917 0.042 Uiso 1 1 calc R U H10B H 1.2296 0.6894 -0.0578 0.042 Uiso 1 1 calc R U C11 C 1.2976(3) 0.87524(18) -0.00256(15) 0.0385(3) Uani 1 1 d . . H11A H 1.2097 0.9586 0.0225 0.058 Uiso 1 1 calc R U H11B H 1.4192 0.9150 -0.0794 0.058 Uiso 1 1 calc R U H11C H 1.3663 0.8205 0.0652 0.058 Uiso 1 1 calc R U N1 N 0.01793(19) 0.07106(14) 0.31755(12) 0.0333(3) Uani 1 1 d . . N2 N 0.30001(18) 0.41590(12) 0.32098(10) 0.0268(2) Uani 1 1 d . . H2A H 0.3095 0.4306 0.3929 0.032 Uiso 1 1 calc R U N3 N 0.7316(2) 0.59551(14) 0.41019(11) 0.0310(3) Uani 1 1 d . . O1 O 0.76777(17) 0.61523(12) -0.01386(9) 0.0363(3) Uani 1 1 d . . O2 O 0.97292(16) 0.70758(11) 0.09161(8) 0.0292(2) Uani 1 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0347(7) 0.0319(8) 0.0514(9) -0.0119(7) -0.0073(6) -0.0072(6) C2 0.0426(8) 0.0293(7) 0.0360(8) -0.0093(6) -0.0024(6) 0.0040(6) C3 0.0360(8) 0.0416(9) 0.0469(9) -0.0136(7) -0.0150(6) 0.0128(6) C4 0.0284(7) 0.0379(8) 0.0401(8) -0.0134(6) -0.0144(6) 0.0027(5) C5 0.0232(6) 0.0283(6) 0.0181(5) -0.0050(5) -0.0033(4) -0.0023(5) C6 0.0236(6) 0.0275(6) 0.0265(6) -0.0053(5) -0.0068(5) -0.0020(5) C7 0.0305(6) 0.0250(6) 0.0225(6) -0.0085(5) -0.0089(5) 0.0008(5) C8 0.0288(6) 0.0250(6) 0.0235(6) -0.0089(5) -0.0088(5) -0.0008(5) C12 0.0250(6) 0.0205(6) 0.0243(6) -0.0056(5) -0.0044(4) -0.0014(4) C9 0.0307(6) 0.0260(6) 0.0259(6) -0.0082(5) -0.0099(5) -0.0019(5) C10 0.0405(8) 0.0371(8) 0.0237(7) -0.0082(6) -0.0005(5) -0.0112(6) C11 0.0364(7) 0.0404(8) 0.0366(8) -0.0088(7) -0.0051(6) -0.0121(6) N1 0.0277(6) 0.0295(6) 0.0433(7) -0.0078(5) -0.0112(5) -0.0036(4) N2 0.0318(6) 0.0290(6) 0.0210(5) -0.0076(4) -0.0075(4) -0.0040(4) N3 0.0367(6) 0.0331(6) 0.0237(6) -0.0078(5) -0.0069(4) -0.0056(5) O1 0.0430(6) 0.0458(6) 0.0230(5) -0.0106(4) -0.0101(4) -0.0118(5) O2 0.0326(5) 0.0343(5) 0.0215(5) -0.0084(4) -0.0057(4) -0.0092(4) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 C2 124.11(14) N1 C1 H1 117.9 C2 C1 H1 117.9 C3 C2 C1 117.99(14) C3 C2 H2 121.0 C1 C2 H2 121.0 C2 C3 C4 119.18(13) C2 C3 H3 120.4 C4 C3 H3 120.4 C5 C4 C3 118.97(13) C5 C4 H4 120.5 C3 C4 H4 120.5 N1 C5 C4 122.39(13) N1 C5 C6 113.80(11) C4 C5 C6 123.81(12) N2 C6 C5 114.01(10) N2 C6 H6A 108.8 C5 C6 H6A 108.8 N2 C6 H6B 108.8 C5 C6 H6B 108.8 H6A C6 H6B 107.6 N2 C7 C8 126.31(11) N2 C7 H7 116.8 C8 C7 H7 116.8 C7 C8 C12 120.86(11) C7 C8 C9 118.66(11) C12 C8 C9 120.46(11) N3 C12 C8 177.24(13) O1 C9 O2 123.69(12) O1 C9 C8 124.65(11) O2 C9 C8 111.66(10) O2 C10 C11 107.23(11) O2 C10 H10A 110.3 C11 C10 H10A 110.3 O2 C10 H10B 110.3 C11 C10 H10B 110.3 H10A C10 H10B 108.5 C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C1 N1 C5 117.34(12) C7 N2 C6 121.89(11) C7 N2 H2A 119.1 C6 N2 H2A 119.1 C9 O2 C10 115.88(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.337(2) C1 C2 1.373(2) C1 H1 0.9500 C2 C3 1.373(2) C2 H2 0.9500 C3 C4 1.384(2) C3 H3 0.9500 C4 C5 1.3812(18) C4 H4 0.9500 C5 N1 1.3383(16) C5 C6 1.5106(19) C6 N2 1.4621(15) C6 H6A 0.9900 C6 H6B 0.9900 C7 N2 1.3147(17) C7 C8 1.3802(17) C7 H7 0.9500 C8 C12 1.4216(16) C8 C9 1.4571(18) C12 N3 1.1444(17) C9 O1 1.2154(15) C9 O2 1.3384(15) C10 O2 1.4566(16) C10 C11 1.4994(19) C10 H10A 0.9900 C10 H10B 0.9900 C11 H11A 0.9800 C11 H11B 0.9800 C11 H11C 0.9800 N2 H2A 0.8800 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 C2 C3 -1.2(2) C1 C2 C3 C4 -0.2(2) C2 C3 C4 C5 1.3(2) C3 C4 C5 N1 -1.4(2) C3 C4 C5 C6 178.70(14) N1 C5 C6 N2 -173.30(11) C4 C5 C6 N2 6.65(18) N2 C7 C8 C12 1.2(2) N2 C7 C8 C9 179.63(12) C7 C8 C9 O1 -0.6(2) C12 C8 C9 O1 177.85(13) C7 C8 C9 O2 179.53(12) C12 C8 C9 O2 -2.05(17) C2 C1 N1 C5 1.2(2) C4 C5 N1 C1 0.1(2) C6 C5 N1 C1 -179.95(13) C8 C7 N2 C6 -173.99(12) C5 C6 N2 C7 86.96(15) O1 C9 O2 C10 -2.8(2) C8 C9 O2 C10 177.09(11) C11 C10 O2 C9 169.83(12)