#------------------------------------------------------------------------------ #$Date: 2021-10-30 03:28:48 +0300 (Sat, 30 Oct 2021) $ #$Revision: 270173 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061031.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_7061031 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 H14 Mn N8 O10' _chemical_formula_sum 'C16 H14 Mn N8 O10' _chemical_formula_weight 533.29 _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 difmap _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 105.20(2) _cell_angle_beta 97.89(2) _cell_angle_gamma 109.80(2) _cell_formula_units_Z 1 _cell_length_a 6.963(2) _cell_length_b 8.5910(10) _cell_length_c 10.532(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 17 _cell_measurement_theta_min 12 _cell_volume 554.0(2) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometr' _diffrn_measurement_method 'non-profiled omega scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_unetI/netI 0.0303 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2257 _diffrn_reflns_point_group_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.915 _diffrn_reflns_theta_min 4.492 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 5.50 _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.598 _exptl_crystal_description block _exptl_crystal_F_000 271 _exptl_crystal_size_max .27 _exptl_crystal_size_mid .23 _exptl_crystal_size_min .21 _refine_diff_density_max 0.324 _refine_diff_density_min -0.667 _refine_diff_density_rms 0.051 _refine_ls_extinction_coef 0.013(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 189 _refine_ls_number_reflns 2130 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0389 _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^)+(0.0486P)^2^+0.3199P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0985 _refine_ls_wR_factor_ref 0.1053 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1848 _reflns_number_total 2130 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01225h2.cif _cod_data_source_block mn1248 _cod_database_code 7061031 _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 mn1248 in P -1 P-1 CELL 1.54184 6.9630 8.5910 10.5320 105.200 97.890 109.800 ZERR 1 0.0020 0.0010 0.0020 0.020 0.020 0.020 LATT 1 SFAC C MN N O H UNIT 16 1 8 10 14 ACTA BOND $H L.S. 10 FMAP 2 PLAN 20 conf htab EQIV $1 -x+1, -y, -z+1 HTAB N1 O1_$1 EQIV $2 x+1, y, z HTAB O3 O5_$2 EQIV $3 -x+2, -y+1, -z+1 HTAB O3 O2_$3 HTAB O4 O5 HTAB O4 N3 EQIV $4 -x+2, -y+2, -z+1 HTAB O4 N4_$4 EQIV $5 x-1, y, z-1 HTAB O5 N4_$5 EQIV $6 x, y+1, z HTAB O5 O1_$6 WGHT 0.048600 0.319900 EXTI 0.013334 FVAR 3.20278 MN 2 0.500000 0.500000 0.000000 10.50000 0.04703 0.03494 = 0.02652 0.01493 -0.00604 0.01182 O1 4 0.439101 0.063214 0.349292 11.00000 0.05764 0.02946 = 0.03300 0.01371 -0.00234 0.00592 O2 4 0.924092 0.470263 0.733801 11.00000 0.05446 0.04626 = 0.03167 0.01840 -0.00911 0.01183 O3 4 0.839899 0.601006 0.063434 11.00000 0.04607 0.06872 = 0.05409 0.03742 -0.00434 0.01305 O4 4 0.504758 0.743156 0.122585 11.00000 0.06900 0.04526 = 0.05246 0.00024 -0.01933 0.02403 O5 4 0.205171 0.879631 0.065871 11.00000 0.08484 0.05550 = 0.04167 0.01654 0.00140 0.02562 N1 3 0.678181 0.233718 0.557139 11.00000 0.04733 0.03324 = 0.03009 0.02002 -0.00185 0.00860 N2 3 0.499766 0.405506 0.180369 11.00000 0.05973 0.04171 = 0.03192 0.01901 -0.00565 0.01048 N3 3 0.802527 0.831130 0.386580 11.00000 0.07231 0.03873 = 0.04689 0.02144 -0.01050 0.00986 N4 3 1.101631 0.886693 0.795562 11.00000 0.09742 0.04603 = 0.03939 0.01103 -0.01725 0.00366 C2 1 0.567407 0.205307 0.426780 11.00000 0.04038 0.03218 = 0.02571 0.01482 0.00182 0.01071 C3 1 0.633800 0.373515 0.405958 11.00000 0.03768 0.03032 = 0.02424 0.01424 -0.00038 0.01043 C4 1 0.773045 0.502641 0.524509 11.00000 0.03279 0.03217 = 0.02579 0.01467 0.00221 0.01220 C5 1 0.804568 0.405374 0.621739 11.00000 0.03785 0.03787 = 0.02670 0.01753 0.00218 0.01410 C6 1 0.559311 0.391843 0.281978 11.00000 0.04000 0.02811 = 0.02876 0.01321 -0.00142 0.00794 C7 1 0.870723 0.681774 0.559340 11.00000 0.03663 0.03218 = 0.02575 0.01143 -0.00057 0.00958 C8 1 0.836041 0.766711 0.464434 11.00000 0.04297 0.02754 = 0.03352 0.01050 -0.00466 0.00565 C9 1 0.999305 0.792419 0.691548 11.00000 0.05357 0.03596 = 0.03183 0.01333 -0.00329 0.00822 H1 5 0.650826 0.154643 0.586501 11.00000 0.05203 H3 5 0.924681 0.677658 0.045800 11.00000 0.06114 H31 5 0.911248 0.577240 0.119389 11.00000 0.11259 H4 5 0.417423 0.789085 0.108489 11.00000 0.07736 H41 5 0.599885 0.811498 0.183604 11.00000 0.11012 H5 5 0.197002 0.904716 -0.017357 11.00000 0.12499 H51 5 0.257592 0.981782 0.132349 11.00000 0.18267 HKLF 4 1 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 REM mn1248 in P -1 P-1 REM R1 = 0.0389 for 1848 Fo > 4sig(Fo) and 0.0506 for all 2130 data REM 189 parameters refined using 0 restraints END WGHT 0.0494 0.3386 REM Instructions for potential hydrogen bonds HTAB N1 O1_$1 HTAB O3 O5_$2 HTAB O3 O2_$3 HTAB O4 O5 HTAB O4 N3 HTAB O4 N4_$4 HTAB O5 N4_$5 HTAB O5 O1_$6 REM Highest difference peak 0.324, deepest hole -0.667, 1-sigma level 0.051 Q1 1 0.4614 0.4831 0.0894 11.00000 0.05 0.32 Q2 1 0.7082 0.5256 -0.0506 11.00000 0.05 0.23 Q3 1 0.5830 0.3069 0.4143 11.00000 0.05 0.22 Q4 1 0.3802 0.3915 -0.1260 11.00000 0.05 0.21 Q5 1 0.6944 0.4434 0.4558 11.00000 0.05 0.21 Q6 1 0.7566 0.4664 0.5783 11.00000 0.05 0.21 Q7 1 0.8167 0.5981 0.5439 11.00000 0.05 0.20 Q8 1 0.9471 0.7329 0.6224 11.00000 0.05 0.19 Q9 1 0.5881 0.6753 0.0436 11.00000 0.05 0.18 Q10 1 0.4667 0.3890 0.2414 11.00000 0.05 0.18 Q11 1 0.4644 0.0860 0.2626 11.00000 0.05 0.18 Q12 1 0.6787 0.2151 0.4795 11.00000 0.05 0.18 Q13 1 0.8308 0.4597 0.5506 11.00000 0.05 0.17 Q14 1 0.9755 0.8169 0.7748 11.00000 0.05 0.17 Q15 1 0.7869 0.8361 0.4642 11.00000 0.05 0.17 Q16 1 0.3817 0.9614 0.0710 11.00000 0.05 0.17 Q17 1 0.8362 0.7156 0.5236 11.00000 0.05 0.17 Q18 1 0.5604 0.3799 0.3672 11.00000 0.05 0.16 Q19 1 0.5753 0.2210 0.4985 11.00000 0.05 0.15 Q20 1 0.9003 0.8123 0.4091 11.00000 0.05 0.15 ; _shelx_res_checksum 42353 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 Mn Mn 0.5000 0.5000 0.0000 0.0380(2) Uani 1 2 d S . P . . O1 O 0.4391(3) 0.0632(2) 0.34929(18) 0.0439(5) Uani 1 1 d . . . . . O2 O 0.9241(3) 0.4703(2) 0.73380(18) 0.0473(5) Uani 1 1 d . . . . . O3 O 0.8399(4) 0.6010(3) 0.0634(2) 0.0571(6) Uani 1 1 d . . . . . O4 O 0.5048(4) 0.7432(3) 0.1226(2) 0.0622(7) Uani 1 1 d . . . . . O5 O 0.2052(4) 0.8796(3) 0.0659(3) 0.0626(6) Uani 1 1 d . . . . . N1 N 0.6782(4) 0.2337(3) 0.5571(2) 0.0381(5) Uani 1 1 d . . . . . N2 N 0.4998(4) 0.4055(3) 0.1804(2) 0.0475(6) Uani 1 1 d . . . . . N3 N 0.8025(4) 0.8311(3) 0.3866(3) 0.0572(7) Uani 1 1 d . . . . . N4 N 1.1016(5) 0.8867(4) 0.7956(3) 0.0721(9) Uani 1 1 d . . . . . C2 C 0.5674(4) 0.2053(3) 0.4268(2) 0.0333(5) Uani 1 1 d . . . . . C3 C 0.6338(4) 0.3735(3) 0.4060(2) 0.0313(5) Uani 1 1 d . . . . . C4 C 0.7730(4) 0.5026(3) 0.5245(2) 0.0299(5) Uani 1 1 d . . . . . C5 C 0.8046(4) 0.4054(3) 0.6217(2) 0.0335(5) Uani 1 1 d . . . . . C6 C 0.5593(4) 0.3918(3) 0.2820(2) 0.0341(5) Uani 1 1 d . . . . . C7 C 0.8707(4) 0.6818(3) 0.5593(2) 0.0331(5) Uani 1 1 d . . . . . C8 C 0.8360(4) 0.7667(3) 0.4644(2) 0.0384(6) Uani 1 1 d . . . . . C9 C 0.9993(5) 0.7924(3) 0.6915(3) 0.0441(6) Uani 1 1 d . . . . . H1 H 0.651(5) 0.155(4) 0.587(3) 0.052(9) Uiso 1 1 d . . . . . H3 H 0.925(6) 0.678(5) 0.046(4) 0.061(11) Uiso 1 1 d . . . . . H31 H 0.911(8) 0.577(7) 0.119(5) 0.113(18) Uiso 1 1 d . . . . . H4 H 0.417(7) 0.789(5) 0.108(4) 0.077(13) Uiso 1 1 d . . . . . H41 H 0.600(8) 0.811(7) 0.184(5) 0.110(18) Uiso 1 1 d . . . . . H5 H 0.197(8) 0.905(7) -0.017(6) 0.125(19) Uiso 1 1 d . . . . . H51 H 0.258(11) 0.982(9) 0.132(8) 0.18(3) 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 Mn 0.0470(4) 0.0349(3) 0.0265(3) 0.0149(2) -0.0060(2) 0.0118(2) O1 0.0576(12) 0.0295(9) 0.0330(9) 0.0137(7) -0.0023(8) 0.0059(8) O2 0.0545(11) 0.0463(10) 0.0317(9) 0.0184(8) -0.0091(8) 0.0118(9) O3 0.0461(12) 0.0687(15) 0.0541(13) 0.0374(12) -0.0043(10) 0.0131(11) O4 0.0690(15) 0.0453(12) 0.0525(13) 0.0002(10) -0.0193(11) 0.0240(12) O5 0.0848(17) 0.0555(14) 0.0417(12) 0.0165(11) 0.0014(11) 0.0256(12) N1 0.0473(12) 0.0332(10) 0.0301(10) 0.0200(9) -0.0018(9) 0.0086(9) N2 0.0597(14) 0.0417(12) 0.0319(11) 0.0190(9) -0.0057(10) 0.0105(11) N3 0.0723(17) 0.0387(13) 0.0469(14) 0.0214(11) -0.0105(12) 0.0099(12) N4 0.097(2) 0.0460(15) 0.0394(14) 0.0110(12) -0.0173(14) 0.0037(15) C2 0.0404(13) 0.0322(12) 0.0257(11) 0.0148(9) 0.0018(9) 0.0107(10) C3 0.0377(12) 0.0303(11) 0.0242(11) 0.0142(9) -0.0004(9) 0.0104(10) C4 0.0328(11) 0.0322(11) 0.0258(11) 0.0147(9) 0.0022(9) 0.0122(9) C5 0.0378(12) 0.0379(12) 0.0267(11) 0.0175(10) 0.0022(9) 0.0141(10) C6 0.0400(13) 0.0281(11) 0.0288(12) 0.0132(9) -0.0014(10) 0.0079(10) C7 0.0366(12) 0.0322(12) 0.0258(11) 0.0114(9) -0.0006(9) 0.0096(10) C8 0.0430(14) 0.0275(11) 0.0335(12) 0.0105(10) -0.0047(10) 0.0056(10) C9 0.0536(16) 0.0360(13) 0.0318(13) 0.0133(11) -0.0033(12) 0.0082(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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' 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 Mn O4 180.0 2_665 . ? O4 Mn O3 90.16(11) 2_665 2_665 ? O4 Mn O3 89.84(11) . 2_665 ? O4 Mn O3 89.84(11) 2_665 . ? O4 Mn O3 90.16(10) . . ? O3 Mn O3 180.0 2_665 . ? O4 Mn N2 90.09(10) 2_665 2_665 ? O4 Mn N2 89.92(10) . 2_665 ? O3 Mn N2 86.41(9) 2_665 2_665 ? O3 Mn N2 93.59(9) . 2_665 ? O4 Mn N2 89.92(10) 2_665 . ? O4 Mn N2 90.08(10) . . ? O3 Mn N2 93.59(9) 2_665 . ? O3 Mn N2 86.41(9) . . ? N2 Mn N2 180.0 2_665 . ? Mn O3 H3 128(3) . . ? Mn O3 H31 127(4) . . ? H3 O3 H31 105(4) . . ? Mn O4 H4 127(3) . . ? Mn O4 H41 124(4) . . ? H4 O4 H41 108(4) . . ? H5 O5 H51 107(5) . . ? C5 N1 C2 111.8(2) . . ? C5 N1 H1 129(2) . . ? C2 N1 H1 119(2) . . ? C6 N2 Mn 159.9(2) . . ? O1 C2 N1 124.6(2) . . ? O1 C2 C3 128.7(2) . . ? N1 C2 C3 106.64(19) . . ? C4 C3 C6 128.7(2) . . ? C4 C3 C2 109.41(19) . . ? C6 C3 C2 121.9(2) . . ? C7 C4 C3 132.2(2) . . ? C7 C4 C5 122.5(2) . . ? C3 C4 C5 105.29(19) . . ? O2 C5 N1 127.4(2) . . ? O2 C5 C4 125.8(2) . . ? N1 C5 C4 106.75(19) . . ? N2 C6 C3 179.2(3) . . ? C4 C7 C8 120.3(2) . . ? C4 C7 C9 123.0(2) . . ? C8 C7 C9 116.5(2) . . ? N3 C8 C7 178.0(3) . . ? N4 C9 C7 177.1(3) . . ? 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 Mn O4 2.135(2) 2_665 ? Mn O4 2.135(2) . ? Mn O3 2.161(2) 2_665 ? Mn O3 2.161(2) . ? Mn N2 2.253(2) 2_665 ? Mn N2 2.253(2) . ? O1 C2 1.222(3) . ? O2 C5 1.211(3) . ? O3 H3 0.80(4) . ? O3 H31 0.83(5) . ? O4 H4 0.85(4) . ? O4 H41 0.79(5) . ? O5 H5 0.95(6) . ? O5 H51 0.89(7) . ? N1 C5 1.357(3) . ? N1 C2 1.395(3) . ? N1 H1 0.80(3) . ? N2 C6 1.144(3) . ? N3 C8 1.143(3) . ? N4 C9 1.137(4) . ? C2 C3 1.446(3) . ? C3 C4 1.394(3) . ? C3 C6 1.406(3) . ? C4 C7 1.375(3) . ? C4 C5 1.519(3) . ? C7 C8 1.423(3) . ? C7 C9 1.425(3) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.80(3) 2.08(4) 2.876(3) 176(3) 2_656 O3 H3 O5 0.80(4) 2.07(4) 2.833(4) 159(4) 1_655 O3 H31 O2 0.83(5) 2.01(6) 2.835(3) 176(5) 2_766 O4 H4 O5 0.85(4) 1.94(5) 2.787(4) 176(4) . O4 H41 N3 0.79(5) 2.33(5) 2.976(3) 141(5) . O4 H41 N4 0.79(5) 2.65(5) 3.221(4) 131(5) 2_776 O5 H5 N4 0.95(6) 1.94(6) 2.861(4) 162(5) 1_454 O5 H51 O1 0.89(7) 2.25(8) 2.917(3) 132(6) 1_565 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 O1 -177.9(3) . . . . ? C5 N1 C2 C3 1.5(3) . . . . ? O1 C2 C3 C4 176.1(3) . . . . ? N1 C2 C3 C4 -3.3(3) . . . . ? O1 C2 C3 C6 -3.3(4) . . . . ? N1 C2 C3 C6 177.3(2) . . . . ? C6 C3 C4 C7 3.2(5) . . . . ? C2 C3 C4 C7 -176.1(3) . . . . ? C6 C3 C4 C5 -177.0(3) . . . . ? C2 C3 C4 C5 3.6(3) . . . . ? C2 N1 C5 O2 -177.7(3) . . . . ? C2 N1 C5 C4 0.7(3) . . . . ? C7 C4 C5 O2 -4.5(4) . . . . ? C3 C4 C5 O2 175.7(3) . . . . ? C7 C4 C5 N1 177.1(2) . . . . ? C3 C4 C5 N1 -2.7(3) . . . . ? C3 C4 C7 C8 -0.3(4) . . . . ? C5 C4 C7 C8 180.0(2) . . . . ? C3 C4 C7 C9 175.8(3) . . . . ? C5 C4 C7 C9 -3.9(4) . . . . ?