#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:21 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306586 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577401.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_1577401 loop_ _publ_author_name 'Hogan, David Thomas' 'Krappe, Alexander R.' 'Feyerherm, R.' 'Weber, Manuela' 'Resch-Genger, Ute' 'Eigler, Siegfried' _publ_section_title ; Large Stokes shift fluorophores from meta-substituted zwitterions ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC03405E _journal_year 2026 _chemical_absolute_configuration rm _chemical_formula_sum 'C14 H12 N4' _chemical_formula_weight 236.28 _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2025-10-08 deposited with the CCDC. 2026-06-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.90861(9) _cell_length_b 8.59323(6) _cell_length_c 10.50182(7) _cell_measurement_reflns_used 8489 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 68.11 _cell_measurement_theta_min 6.05 _cell_volume 1255.176(15) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX4' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker Photon CMOS Detector, D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_unetI/netI 0.0328 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 9057 _diffrn_reflns_point_group_measured_fraction_full 0.960 _diffrn_reflns_point_group_measured_fraction_max 0.959 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.105 _diffrn_reflns_theta_min 6.053 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 0.624 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.250 _exptl_crystal_description chunk _exptl_crystal_F_000 496 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.420 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.100 _exptl_transmission_factor_max 0.9022 _exptl_transmission_factor_min 0.6873 _refine_diff_density_max 0.148 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; Flack x determined using 971 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(14) _refine_ls_extinction_coef 0.0062(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 2219 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0300 _refine_ls_R_factor_gt 0.0291 _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^)+(0.0379P)^2^+0.3232P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.0761 _reflns_Friedel_coverage 0.814 _reflns_Friedel_fraction_full 0.919 _reflns_Friedel_fraction_max 0.915 _reflns_number_gt 2176 _reflns_number_total 2219 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc03405e2.cif _cod_data_source_block 0501DH _cod_database_code 1577401 _shelx_shelxl_version_number 2019/3 _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_estimated_absorpt_t_min 0.780 _shelx_estimated_absorpt_t_max 0.940 _shelx_res_file ; TITL uf_a.res in Pna2(1) 0501DH.res created by SHELXL-2019/3 at 14:05:06 on 11-Jun-2025 REM Old TITL uf in Pna2(1) REM SHELXT solution in Pna2(1): R1 0.081, Rweak 0.008, Alpha 0.001 REM 0.436 for 136 systematic absences, Orientation as input REM Flack x = 0.346 ( 0.216 ) from 780 Parsons' quotients REM Formula found by SHELXT: C14 N4 CELL 1.54178 13.90861 8.59323 10.50182 90 90 90 ZERR 4 0.00009 0.00006 0.00007 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SYMM 0.5-X,0.5+Y,0.5+Z SFAC C H N UNIT 56 48 16 OMIT 14 0 4 L.S. 30 PLAN 5 SIZE 0.1 0.14 0.42 TEMP -173.15 CONF BOND $H LIST 4 MORE -1 fmap 2 acta REM REM REM WGHT 0.037900 0.323200 EXTI 0.006154 FVAR 0.92467 N1 3 0.112128 0.572687 0.364015 11.00000 0.01897 0.01708 = 0.01926 0.00115 -0.00117 0.00014 N2 3 0.157714 0.797360 0.294795 11.00000 0.01749 0.01768 = 0.01659 0.00207 -0.00032 -0.00032 N3 3 0.662462 0.375620 0.577457 11.00000 0.02222 0.02163 = 0.02991 -0.00434 -0.00128 0.00163 N4 3 0.611064 0.838078 0.748523 11.00000 0.02137 0.02045 = 0.04082 -0.00413 -0.00847 0.00195 C1 1 0.314688 0.776028 0.504432 11.00000 0.01787 0.01698 = 0.01993 0.00050 0.00188 0.00122 AFIX 43 H1 2 0.277824 0.867717 0.517489 11.00000 -1.20000 AFIX 0 C6 1 0.278606 0.656767 0.427401 11.00000 0.01759 0.01937 = 0.01404 0.00313 -0.00030 0.00042 C7 1 0.185311 0.674440 0.363866 11.00000 0.01987 0.01670 = 0.01604 -0.00090 0.00241 -0.00026 C8 1 0.037099 0.633061 0.293439 11.00000 0.01789 0.02247 = 0.02215 -0.00144 -0.00210 -0.00100 AFIX 43 H8 2 -0.023070 0.584478 0.277546 11.00000 -1.20000 AFIX 0 C9 1 0.065378 0.773721 0.251463 11.00000 0.01787 0.02337 = 0.01872 0.00067 -0.00159 0.00260 AFIX 43 H9 2 0.028522 0.843726 0.201272 11.00000 -1.20000 AFIX 0 C10 1 0.554170 0.615876 0.603590 11.00000 0.01808 0.01599 = 0.01925 0.00130 -0.00026 0.00030 C11 1 0.613797 0.484014 0.589202 11.00000 0.01504 0.02032 = 0.01913 -0.00072 -0.00023 -0.00359 C12 1 0.587378 0.735975 0.683353 11.00000 0.01537 0.01813 = 0.02523 0.00325 -0.00168 0.00192 C13 1 0.108252 0.424645 0.434002 11.00000 0.02922 0.01902 = 0.03049 0.00644 -0.00557 -0.00583 AFIX 137 H13A 2 0.041349 0.400612 0.455688 11.00000 -1.50000 H13B 2 0.146253 0.433361 0.512260 11.00000 -1.50000 H13C 2 0.134571 0.341280 0.380711 11.00000 -1.50000 AFIX 0 C14 1 0.217341 0.933152 0.263370 11.00000 0.02532 0.01969 = 0.02351 0.00710 -0.00220 -0.00444 AFIX 137 H14A 2 0.196008 0.977486 0.182168 11.00000 -1.50000 H14B 2 0.284740 0.901043 0.256321 11.00000 -1.50000 H14C 2 0.211049 1.011507 0.330660 11.00000 -1.50000 AFIX 0 C2 1 0.403690 0.761145 0.561636 11.00000 0.01926 0.01683 = 0.01724 -0.00070 -0.00080 -0.00104 AFIX 43 H2 2 0.426707 0.842720 0.614535 11.00000 -1.20000 AFIX 0 C3 1 0.461134 0.627928 0.543417 11.00000 0.01740 0.01900 = 0.01422 0.00329 0.00252 -0.00097 C4 1 0.423599 0.508672 0.465491 11.00000 0.02011 0.01704 = 0.01608 0.00049 0.00156 0.00244 AFIX 43 H4 2 0.460546 0.417376 0.451070 11.00000 -1.20000 AFIX 0 C5 1 0.334090 0.522559 0.409910 11.00000 0.02007 0.01821 = 0.01434 -0.00109 0.00050 -0.00096 AFIX 43 H5 2 0.309817 0.439948 0.359115 11.00000 -1.20000 REM REM 0501DH.hkl REM AFIX 0 HKLF 4 REM uf_a.res in Pna2(1) REM wR2 = 0.0761, GooF = S = 1.043, Restrained GooF = 1.043 for all data REM R1 = 0.0291 for 2176 Fo > 4sig(Fo) and 0.0300 for all 2219 data REM 166 parameters refined using 1 restraints END WGHT 0.0337 0.3194 REM Highest difference peak 0.148, deepest hole -0.146, 1-sigma level 0.035 Q1 1 0.1220 0.7775 0.2376 11.00000 0.05 0.15 Q2 1 0.4186 0.6694 0.5945 11.00000 0.05 0.14 Q3 1 0.1775 0.8584 0.2780 11.00000 0.05 0.13 Q4 1 0.2780 0.6937 0.4932 11.00000 0.05 0.13 Q5 1 0.3191 0.7473 0.4240 11.00000 0.05 0.13 ; _shelx_res_checksum 11395 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' 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 N1 N 0.11213(12) 0.57269(18) 0.36402(17) 0.0184(4) Uani 1 1 d . . . . . N2 N 0.15771(11) 0.79736(18) 0.29480(16) 0.0173(4) Uani 1 1 d . . . . . N3 N 0.66246(12) 0.3756(2) 0.57746(19) 0.0246(4) Uani 1 1 d . . . . . N4 N 0.61106(13) 0.8381(2) 0.7485(2) 0.0275(4) Uani 1 1 d . . . . . C1 C 0.31469(14) 0.7760(2) 0.50443(19) 0.0183(4) Uani 1 1 d . . . . . H1 H 0.277824 0.867717 0.517489 0.022 Uiso 1 1 calc R U . . . C6 C 0.27861(14) 0.6568(2) 0.42740(17) 0.0170(4) Uani 1 1 d . . . . . C7 C 0.18531(15) 0.6744(2) 0.36387(19) 0.0175(4) Uani 1 1 d . . . . . C8 C 0.03710(14) 0.6331(2) 0.2934(2) 0.0208(4) Uani 1 1 d . . . . . H8 H -0.023070 0.584478 0.277546 0.025 Uiso 1 1 calc R U . . . C9 C 0.06538(15) 0.7737(2) 0.2515(2) 0.0200(4) Uani 1 1 d . . . . . H9 H 0.028522 0.843726 0.201272 0.024 Uiso 1 1 calc R U . . . C10 C 0.55417(14) 0.6159(2) 0.60359(19) 0.0178(4) Uani 1 1 d . . . . . C11 C 0.61380(13) 0.4840(2) 0.58920(19) 0.0182(4) Uani 1 1 d . . . . . C12 C 0.58738(14) 0.7360(2) 0.6834(2) 0.0196(4) Uani 1 1 d . . . . . C13 C 0.10825(16) 0.4246(2) 0.4340(2) 0.0262(5) Uani 1 1 d . . . . . H13A H 0.041349 0.400612 0.455688 0.039 Uiso 1 1 calc R U . . . H13B H 0.146253 0.433361 0.512260 0.039 Uiso 1 1 calc R U . . . H13C H 0.134571 0.341280 0.380711 0.039 Uiso 1 1 calc R U . . . C14 C 0.21734(15) 0.9332(2) 0.2634(2) 0.0228(4) Uani 1 1 d . . . . . H14A H 0.196008 0.977486 0.182168 0.034 Uiso 1 1 calc R U . . . H14B H 0.284740 0.901043 0.256321 0.034 Uiso 1 1 calc R U . . . H14C H 0.211049 1.011507 0.330660 0.034 Uiso 1 1 calc R U . . . C2 C 0.40369(14) 0.7611(2) 0.56164(19) 0.0178(4) Uani 1 1 d . . . . . H2 H 0.426707 0.842720 0.614535 0.021 Uiso 1 1 calc R U . . . C3 C 0.46113(14) 0.6279(2) 0.54342(18) 0.0169(4) Uani 1 1 d . . . . . C4 C 0.42360(14) 0.5087(2) 0.46549(19) 0.0177(4) Uani 1 1 d . . . . . H4 H 0.460546 0.417376 0.451070 0.021 Uiso 1 1 calc R U . . . C5 C 0.33409(14) 0.5226(2) 0.40991(19) 0.0175(4) Uani 1 1 d . . . . . H5 H 0.309817 0.439948 0.359115 0.021 Uiso 1 1 calc R U . . . 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 N1 0.0190(9) 0.0171(8) 0.0193(8) 0.0012(6) -0.0012(6) 0.0001(6) N2 0.0175(8) 0.0177(7) 0.0166(8) 0.0021(6) -0.0003(7) -0.0003(6) N3 0.0222(9) 0.0216(8) 0.0299(10) -0.0043(7) -0.0013(8) 0.0016(7) N4 0.0214(9) 0.0205(8) 0.0408(11) -0.0041(8) -0.0085(8) 0.0019(7) C1 0.0179(9) 0.0170(9) 0.0199(10) 0.0005(7) 0.0019(8) 0.0012(7) C6 0.0176(9) 0.0194(9) 0.0140(9) 0.0031(7) -0.0003(8) 0.0004(7) C7 0.0199(10) 0.0167(9) 0.0160(9) -0.0009(7) 0.0024(8) -0.0003(7) C8 0.0179(10) 0.0225(10) 0.0221(10) -0.0014(8) -0.0021(8) -0.0010(8) C9 0.0179(10) 0.0234(10) 0.0187(10) 0.0007(8) -0.0016(8) 0.0026(8) C10 0.0181(10) 0.0160(9) 0.0192(10) 0.0013(8) -0.0003(8) 0.0003(7) C11 0.0150(10) 0.0203(10) 0.0191(9) -0.0007(8) -0.0002(8) -0.0036(7) C12 0.0154(9) 0.0181(9) 0.0252(10) 0.0032(9) -0.0017(8) 0.0019(7) C13 0.0292(12) 0.0190(10) 0.0305(12) 0.0064(9) -0.0056(10) -0.0058(8) C14 0.0253(10) 0.0197(9) 0.0235(10) 0.0071(8) -0.0022(8) -0.0044(8) C2 0.0193(9) 0.0168(9) 0.0172(9) -0.0007(7) -0.0008(8) -0.0010(7) C3 0.0174(9) 0.0190(9) 0.0142(10) 0.0033(7) 0.0025(7) -0.0010(7) C4 0.0201(10) 0.0170(9) 0.0161(10) 0.0005(8) 0.0016(8) 0.0024(7) C5 0.0201(10) 0.0182(9) 0.0143(9) -0.0011(8) 0.0005(7) -0.0010(7) 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' H H 0.0000 0.0000 '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' 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 C7 N1 C8 109.13(16) . . ? C7 N1 C13 126.32(16) . . ? C8 N1 C13 124.45(17) . . ? C7 N2 C9 109.28(16) . . ? C7 N2 C14 125.95(16) . . ? C9 N2 C14 124.69(17) . . ? C2 C1 C6 120.33(17) . . ? C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C1 C6 C5 118.80(17) . . ? C1 C6 C7 120.30(16) . . ? C5 C6 C7 120.88(17) . . ? N2 C7 N1 107.31(17) . . ? N2 C7 C6 125.61(17) . . ? N1 C7 C6 127.08(17) . . ? C9 C8 N1 107.00(17) . . ? C9 C8 H8 126.5 . . ? N1 C8 H8 126.5 . . ? C8 C9 N2 107.27(17) . . ? C8 C9 H9 126.4 . . ? N2 C9 H9 126.4 . . ? C12 C10 C11 117.35(17) . . ? C12 C10 C3 120.14(17) . . ? C11 C10 C3 122.48(17) . . ? N3 C11 C10 179.8(2) . . ? N4 C12 C10 177.1(2) . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 . . ? C1 C2 C3 121.61(18) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C3 C4 117.31(17) . . ? C2 C3 C10 120.47(17) . . ? C4 C3 C10 122.22(17) . . ? C5 C4 C3 121.07(17) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.87(17) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? 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 N1 C7 1.342(3) . ? N1 C8 1.381(3) . ? N1 C13 1.470(2) . ? N2 C7 1.338(3) . ? N2 C9 1.378(3) . ? N2 C14 1.469(2) . ? N3 C11 1.158(3) . ? N4 C12 1.160(3) . ? C1 C2 1.382(3) . ? C1 C6 1.399(3) . ? C1 H1 0.9500 . ? C6 C5 1.400(3) . ? C6 C7 1.467(3) . ? C8 C9 1.345(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C12 1.407(3) . ? C10 C11 1.412(3) . ? C10 C3 1.444(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C2 C3 1.409(3) . ? C2 H2 0.9500 . ? C3 C4 1.412(3) . ? C4 C5 1.380(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? 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 C2 C1 C6 C5 0.2(3) . . . . ? C2 C1 C6 C7 -178.31(18) . . . . ? C9 N2 C7 N1 0.5(2) . . . . ? C14 N2 C7 N1 -176.40(18) . . . . ? C9 N2 C7 C6 -179.25(19) . . . . ? C14 N2 C7 C6 3.8(3) . . . . ? C8 N1 C7 N2 0.1(2) . . . . ? C13 N1 C7 N2 -176.30(18) . . . . ? C8 N1 C7 C6 179.82(19) . . . . ? C13 N1 C7 C6 3.5(3) . . . . ? C1 C6 C7 N2 49.5(3) . . . . ? C5 C6 C7 N2 -129.0(2) . . . . ? C1 C6 C7 N1 -130.2(2) . . . . ? C5 C6 C7 N1 51.3(3) . . . . ? C7 N1 C8 C9 -0.6(2) . . . . ? C13 N1 C8 C9 175.82(18) . . . . ? N1 C8 C9 N2 0.9(2) . . . . ? C7 N2 C9 C8 -0.9(2) . . . . ? C14 N2 C9 C8 176.06(18) . . . . ? C6 C1 C2 C3 0.8(3) . . . . ? C1 C2 C3 C4 -0.8(3) . . . . ? C1 C2 C3 C10 179.54(18) . . . . ? C12 C10 C3 C2 1.4(3) . . . . ? C11 C10 C3 C2 179.32(19) . . . . ? C12 C10 C3 C4 -178.21(19) . . . . ? C11 C10 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C10 C3 C4 C5 179.46(18) . . . . ? C3 C4 C5 C6 1.2(3) . . . . ? C1 C6 C5 C4 -1.2(3) . . . . ? C7 C6 C5 C4 177.32(18) . . . . ?