#------------------------------------------------------------------------------ #$Date: 2021-10-30 03:28:48 +0300 (Sat, 30 Oct 2021) $ #$Revision: 270173 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061032.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_7061032 loop_ _publ_author_name 'Gurskiy, Stanislav Igorevich' 'Maklakov, Sergey' 'Dmitrieva, Natalia Evgenievna' 'Tafeenko, Viktor' _publ_section_title ; Effects of transition metal cations and temperature on luminescence of 3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrole-2-olate anion ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ01225H _journal_year 2021 _chemical_formula_moiety 'C16 H10 N8 O8 Zn' _chemical_formula_sum 'C16 H10 N8 O8 Zn' _chemical_formula_weight 507.69 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2020-02-25 deposited with the CCDC. 2021-10-29 downloaded from the CCDC. ; _cell_angle_alpha 90.829(6) _cell_angle_beta 110.004(6) _cell_angle_gamma 93.622(6) _cell_formula_units_Z 1 _cell_length_a 7.0540(6) _cell_length_b 7.9485(6) _cell_length_c 9.4149(7) _cell_measurement_reflns_used 4207 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 34.12 _cell_measurement_theta_min 2.11 _cell_volume 494.68(7) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 295 _diffrn_detector Pilatus100K _diffrn_detector_area_resol_mean 5.81 _diffrn_detector_type STOE _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.901 _diffrn_measurement_device_type STOE _diffrn_measurement_method 'rotation method' _diffrn_radiation_collimation '0.5 mm diameter, monocapillary' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0975 _diffrn_reflns_av_unetI/netI 0.1142 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.901 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8519 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.901 _diffrn_reflns_theta_full 25.234 _diffrn_reflns_theta_max 36.782 _diffrn_reflns_theta_min 2.569 _diffrn_source 'Mo LFF Sealed Tube' _diffrn_source_current 40 _diffrn_source_power 2.000 _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 1.307 _exptl_absorpt_correction_T_max 0.8925 _exptl_absorpt_correction_T_min 0.7173 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'STOE X-AREA' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.704 _exptl_crystal_description block _exptl_crystal_F_000 256 _exptl_crystal_size_max .24 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .10 _refine_diff_density_max 1.143 _refine_diff_density_min -1.011 _refine_diff_density_rms 0.125 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 4473 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.963 _refine_ls_R_factor_all 0.1720 _refine_ls_R_factor_gt 0.0764 _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^)+(0.1236P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1875 _refine_ls_wR_factor_ref 0.2706 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1766 _reflns_number_total 4473 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01225h2.cif _cod_data_source_block znan _cod_database_code 7061032 _shelx_shelxl_version_number 2014/7 _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 shelxt_a.res in P1 CELL 0.71054 7.0540 7.9485 9.4149 90.829 110.004 93.622 ZERR 1.00 0.0006 0.0006 0.0007 0.006 0.006 0.006 LATT 1 SFAC C H N O ZN UNIT 16 10 8 8 1 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H LIST 4 L.S. 10 WGHT 0.123600 FVAR 0.69897 ZN1 5 0.500000 0.000000 0.000000 10.50000 0.04342 0.04319 = 0.03862 0.00147 0.00570 -0.00075 O1 4 1.210244 0.916443 0.306956 11.00000 0.06192 0.04402 = 0.06332 -0.00012 0.01984 -0.00261 O2 4 0.789322 0.474590 0.046416 11.00000 0.06012 0.05125 = 0.04851 0.00058 -0.00359 -0.00428 O3 4 0.673907 -0.124549 -0.115774 11.00000 0.05545 0.04570 = 0.04361 0.00144 0.01243 -0.00063 O4 4 0.506951 0.213589 -0.116326 11.00000 0.06564 0.04848 = 0.04161 0.00591 -0.00277 -0.00708 N1 3 0.976994 0.720114 0.145709 11.00000 0.05412 0.04737 = 0.04756 0.00641 0.01026 0.00536 AFIX 43 H1 2 0.923161 0.785007 0.072659 11.00000 -1.20000 AFIX 0 N2 3 1.447080 0.647710 0.636753 11.00000 0.05092 0.07051 = 0.05043 -0.01058 0.00673 0.00218 N3 3 1.257300 0.223228 0.589875 11.00000 0.06349 0.07390 = 0.04661 0.00496 0.00180 0.00030 N4 3 0.776568 0.101990 0.160408 11.00000 0.04634 0.05313 = 0.04687 -0.00045 -0.00213 -0.00121 C2 1 1.134219 0.773810 0.279974 11.00000 0.04539 0.04361 = 0.04812 -0.00186 0.01744 0.00083 C3 1 1.182674 0.624712 0.370701 11.00000 0.04060 0.04773 = 0.04353 -0.00064 0.01177 0.00168 C4 1 1.058311 0.486649 0.294151 11.00000 0.03735 0.04605 = 0.04012 0.00242 0.00827 0.00831 C5 1 0.920237 0.553625 0.145073 11.00000 0.04843 0.04342 = 0.04240 0.00177 0.01236 0.00241 C6 1 1.329262 0.634838 0.517748 11.00000 0.03763 0.04907 = 0.04659 -0.00416 0.00991 -0.00255 C7 1 1.039982 0.319898 0.330174 11.00000 0.03665 0.04833 = 0.04249 0.00109 0.00752 -0.00086 C8 1 1.160239 0.263119 0.472245 11.00000 0.04259 0.05034 = 0.04236 0.00436 0.00663 -0.00030 C9 1 0.892039 0.199930 0.234555 11.00000 0.04253 0.04668 = 0.03891 0.00494 0.00799 0.00225 H3 2 0.701364 -0.069504 -0.160582 11.00000 0.07073 H31 2 0.596893 -0.214465 -0.167437 11.00000 0.11117 H4 2 0.431543 0.220558 -0.195743 11.00000 0.08508 H41 2 0.556159 0.312222 -0.077812 11.00000 0.06462 HKLF 4 REM shelxt_a.res in P1 REM R1 = 0.0764 for 1766 Fo > 4sig(Fo) and 0.1720 for all 4473 data REM 167 parameters refined using 0 restraints END WGHT 0.1237 0.0000 REM Highest difference peak 1.143, deepest hole -1.011, 1-sigma level 0.125 Q1 1 0.6345 0.0442 0.0924 11.00000 0.05 1.14 Q2 1 0.4122 -0.1016 -0.0844 11.00000 0.05 1.03 Q3 1 0.3564 0.0316 -0.0581 11.00000 0.05 0.97 Q4 1 1.0717 0.8829 0.2019 11.00000 0.05 0.45 Q5 1 1.3819 0.5232 0.5888 11.00000 0.05 0.43 Q6 1 1.2564 0.2045 0.5203 11.00000 0.05 0.39 Q7 1 0.8148 -0.0819 -0.0350 11.00000 0.05 0.38 Q8 1 0.9261 0.0657 0.2206 11.00000 0.05 0.37 Q9 1 0.8851 0.8418 0.1786 11.00000 0.05 0.36 Q10 1 0.5101 -0.1417 -0.2042 11.00000 0.05 0.36 Q11 1 0.7750 0.2505 0.1646 11.00000 0.05 0.35 Q12 1 1.1654 0.2570 0.3516 11.00000 0.05 0.32 Q13 1 1.2637 0.4714 0.3550 11.00000 0.05 0.32 Q14 1 1.3383 0.8649 0.3587 11.00000 0.05 0.32 Q15 1 0.6618 0.2237 -0.0416 11.00000 0.05 0.32 Q16 1 1.1854 0.4759 0.3576 11.00000 0.05 0.32 Q17 1 0.5222 -0.0438 -0.1424 11.00000 0.05 0.31 Q18 1 1.6154 0.6047 0.7197 11.00000 0.05 0.31 Q19 1 1.2736 0.0629 0.5653 11.00000 0.05 0.31 Q20 1 1.0414 0.6210 0.2496 11.00000 0.05 0.31 ; _shelx_res_checksum 91973 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.0000 0.0000 0.0441(3) Uani 1 2 d S . P . . O1 O 1.2102(7) 0.9164(5) 0.3070(5) 0.0572(9) Uani 1 1 d . . . . . O2 O 0.7893(6) 0.4746(5) 0.0464(4) 0.0595(10) Uani 1 1 d . . . . . O3 O 0.6739(6) -0.1245(5) -0.1158(4) 0.0496(8) Uani 1 1 d . . . . . O4 O 0.5070(7) 0.2136(5) -0.1163(5) 0.0579(10) Uani 1 1 d . . . . . N1 N 0.9770(7) 0.7201(6) 0.1457(5) 0.0514(10) Uani 1 1 d . . . . . H1 H 0.9232 0.7850 0.0727 0.062 Uiso 1 1 calc R U . . . N2 N 1.4471(8) 0.6477(7) 0.6368(6) 0.0603(12) Uani 1 1 d . . . . . N3 N 1.2573(9) 0.2232(7) 0.5899(6) 0.0660(14) Uani 1 1 d . . . . . N4 N 0.7766(7) 0.1020(6) 0.1604(5) 0.0537(10) Uani 1 1 d . . . . . C2 C 1.1342(8) 0.7738(6) 0.2800(6) 0.0455(10) Uani 1 1 d . . . . . C3 C 1.1827(7) 0.6247(6) 0.3707(6) 0.0447(9) Uani 1 1 d . . . . . C4 C 1.0583(7) 0.4866(6) 0.2942(5) 0.0422(9) Uani 1 1 d . . . . . C5 C 0.9202(8) 0.5536(6) 0.1451(6) 0.0456(10) Uani 1 1 d . . . . . C6 C 1.3293(7) 0.6348(6) 0.5177(6) 0.0459(10) Uani 1 1 d . . . . . C7 C 1.0400(7) 0.3199(6) 0.3302(5) 0.0442(9) Uani 1 1 d . . . . . C8 C 1.1602(8) 0.2631(7) 0.4722(6) 0.0473(10) Uani 1 1 d . . . . . C9 C 0.8920(7) 0.1999(6) 0.2346(5) 0.0443(9) Uani 1 1 d . . . . . H3 H 0.701(13) -0.070(10) -0.161(9) 0.07(3) Uiso 1 1 d . . . . . H31 H 0.597(16) -0.214(13) -0.167(12) 0.11(3) Uiso 1 1 d . . . . . H4 H 0.432(14) 0.221(11) -0.196(11) 0.09(3) Uiso 1 1 d . . . . . H41 H 0.556(11) 0.312(10) -0.078(8) 0.06(2) Uiso 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 Zn1 0.0434(4) 0.0432(5) 0.0386(4) 0.0015(3) 0.0057(3) -0.0008(3) O1 0.062(2) 0.044(2) 0.063(2) -0.0001(16) 0.0198(19) -0.0026(16) O2 0.060(2) 0.051(2) 0.0485(19) 0.0006(15) -0.0036(17) -0.0043(17) O3 0.055(2) 0.046(2) 0.0436(18) 0.0014(15) 0.0124(16) -0.0006(16) O4 0.066(2) 0.048(2) 0.0416(18) 0.0059(15) -0.0028(17) -0.0071(17) N1 0.054(2) 0.047(2) 0.048(2) 0.0064(17) 0.0103(18) 0.0054(18) N2 0.051(2) 0.071(3) 0.050(2) -0.011(2) 0.007(2) 0.002(2) N3 0.063(3) 0.074(3) 0.047(2) 0.005(2) 0.002(2) 0.000(2) N4 0.046(2) 0.053(2) 0.047(2) -0.0004(17) -0.0021(17) -0.0012(18) C2 0.045(2) 0.044(2) 0.048(2) -0.0019(18) 0.0174(19) 0.0008(18) C3 0.041(2) 0.048(2) 0.044(2) -0.0006(17) 0.0118(17) 0.0017(17) C4 0.037(2) 0.046(2) 0.040(2) 0.0024(16) 0.0083(16) 0.0083(16) C5 0.048(2) 0.043(2) 0.042(2) 0.0018(17) 0.0124(18) 0.0024(18) C6 0.038(2) 0.049(3) 0.047(2) -0.0042(18) 0.0099(18) -0.0025(17) C7 0.0366(19) 0.048(2) 0.042(2) 0.0011(17) 0.0075(16) -0.0009(17) C8 0.043(2) 0.050(3) 0.042(2) 0.0044(18) 0.0066(18) -0.0003(18) C9 0.043(2) 0.047(2) 0.039(2) 0.0049(16) 0.0080(17) 0.0022(17) 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' Zn Zn 0.2839 1.4301 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 O4 180.0 2_655 . ? O4 Zn1 N4 86.19(18) 2_655 2_655 ? O4 Zn1 N4 93.81(18) . 2_655 ? O4 Zn1 N4 93.81(18) 2_655 . ? O4 Zn1 N4 86.19(18) . . ? N4 Zn1 N4 180.0 2_655 . ? O4 Zn1 O3 89.14(19) 2_655 . ? O4 Zn1 O3 90.86(19) . . ? N4 Zn1 O3 91.64(18) 2_655 . ? N4 Zn1 O3 88.36(18) . . ? O4 Zn1 O3 90.86(19) 2_655 2_655 ? O4 Zn1 O3 89.14(19) . 2_655 ? N4 Zn1 O3 88.36(18) 2_655 2_655 ? N4 Zn1 O3 91.64(18) . 2_655 ? O3 Zn1 O3 180.0 . 2_655 ? Zn1 O3 H3 110(7) . . ? Zn1 O3 H31 107(6) . . ? H3 O3 H31 113(9) . . ? Zn1 O4 H4 120(7) . . ? Zn1 O4 H41 126(5) . . ? H4 O4 H41 110(8) . . ? C5 N1 C2 112.0(4) . . ? C5 N1 H1 124.0 . . ? C2 N1 H1 124.0 . . ? C9 N4 Zn1 158.5(4) . . ? O1 C2 N1 124.2(5) . . ? O1 C2 C3 129.6(5) . . ? N1 C2 C3 106.2(4) . . ? C4 C3 C6 128.7(5) . . ? C4 C3 C2 109.8(4) . . ? C6 C3 C2 121.4(4) . . ? C7 C4 C3 132.9(5) . . ? C7 C4 C5 121.6(4) . . ? C3 C4 C5 105.4(4) . . ? O2 C5 N1 126.5(5) . . ? O2 C5 C4 126.9(5) . . ? N1 C5 C4 106.6(4) . . ? N2 C6 C3 178.1(6) . . ? C4 C7 C8 120.7(4) . . ? C4 C7 C9 122.9(4) . . ? C8 C7 C9 116.2(4) . . ? N3 C8 C7 177.3(6) . . ? N4 C9 C7 178.5(6) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 2.041(4) 2_655 ? Zn1 O4 2.041(4) . ? Zn1 N4 2.120(4) 2_655 ? Zn1 N4 2.120(4) . ? Zn1 O3 2.170(4) . ? Zn1 O3 2.170(4) 2_655 ? O1 C2 1.208(6) . ? O2 C5 1.197(6) . ? O3 H3 0.68(8) . ? O3 H31 0.90(11) . ? O4 H4 0.76(9) . ? O4 H41 0.86(8) . ? N1 C5 1.357(7) . ? N1 C2 1.406(7) . ? N1 H1 0.8600 . ? N2 C6 1.143(7) . ? N3 C8 1.147(7) . ? N4 C9 1.128(6) . ? C2 C3 1.460(7) . ? C3 C4 1.384(7) . ? C3 C6 1.414(7) . ? C4 C7 1.382(7) . ? C4 C5 1.534(7) . ? C7 C8 1.415(7) . ? C7 C9 1.420(6) . ?