#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:21 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306586 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577399.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_1577399 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_formula_sum 'C14 H12 N4' _chemical_formula_weight 236.28 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _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 96.704(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.0059(3) _cell_length_b 7.6326(3) _cell_length_c 19.6494(8) _cell_measurement_reflns_used 7671 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 66.94 _cell_measurement_theta_min 4.53 _cell_volume 1192.48(8) _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 0.976 _diffrn_measured_fraction_theta_max 0.976 _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 0.0524 _diffrn_reflns_av_unetI/netI 0.0422 _diffrn_reflns_Laue_measured_fraction_full 0.976 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 9833 _diffrn_reflns_point_group_measured_fraction_full 0.976 _diffrn_reflns_point_group_measured_fraction_max 0.976 _diffrn_reflns_theta_full 66.979 _diffrn_reflns_theta_max 66.978 _diffrn_reflns_theta_min 4.531 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 0.657 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.316 _exptl_crystal_description platelet _exptl_crystal_F_000 496 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.530 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.070 _exptl_transmission_factor_max 0.8892 _exptl_transmission_factor_min 0.4106 _refine_diff_density_max 0.272 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.065 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2076 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.079 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0593 _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^)+(0.0438P)^2^+1.8105P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1355 _refine_ls_wR_factor_ref 0.1425 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1809 _reflns_number_total 2076 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc03405e2.cif _cod_data_source_block 0392DH _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1577399 _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 0.722 _shelx_estimated_absorpt_t_max 0.955 _shelx_res_file ; TITL test_a.res in P2(1)/c 0392DH.res created by SHELXL-2019/3 at 09:16:06 on 10-Apr-2025 REM Old TITL test in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.154, Rweak 0.001, Alpha 0.021 REM 0.418 for 101 systematic absences, Orientation as input REM Formula found by SHELXT: C14 N4 REM test_a.res in P2(1)/c REM wR2 = 0.1413, GooF = S = 1.090, Restrained GooF = 1.090 for all data REM 165 parameters refined using 0 restraints CELL 1.54178 8.0059 7.6326 19.6494 90 96.704 90 ZERR 4 0.0003 0.0003 0.0008 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N UNIT 56 48 16 OMIT -8 1 5 OMIT -8 2 5 OMIT -9 1 1 OMIT -8 3 4 OMIT -8 4 4 OMIT -7 1 3 L.S. 30 PLAN 5 SIZE 0.07 0.16 0.53 TEMP -173.15 CONF BOND $H LIST 4 MORE -1 fmap 2 acta WGHT 0.043800 1.810500 FVAR 0.77472 N1 3 0.485416 0.646448 0.131007 11.00000 0.02108 0.01617 = 0.02070 0.00069 0.00147 -0.00024 N2 3 0.244759 0.762878 0.145014 11.00000 0.01704 0.01616 = 0.02324 0.00214 0.00013 0.00058 N3 3 0.993008 0.900280 0.332604 11.00000 0.02339 0.02650 = 0.02824 0.00186 0.00011 -0.00140 N4 3 0.833587 0.691015 0.524882 11.00000 0.02805 0.03925 = 0.02541 0.00283 0.00037 -0.00653 C1 1 0.295541 0.596006 0.288742 11.00000 0.01871 0.01333 = 0.02536 -0.00064 0.00032 -0.00005 AFIX 43 H1 2 0.188960 0.565303 0.265363 11.00000 -1.20000 AFIX 0 C2 1 0.330942 0.569202 0.358934 11.00000 0.02286 0.01405 = 0.02427 0.00063 0.00556 -0.00032 AFIX 43 H2 2 0.247538 0.519484 0.383699 11.00000 -1.20000 AFIX 0 C3 1 0.485964 0.613917 0.393250 11.00000 0.02330 0.01403 = 0.02109 0.00072 0.00325 0.00140 AFIX 43 H3 2 0.507748 0.591807 0.441041 11.00000 -1.20000 AFIX 0 C4 1 0.612100 0.691405 0.358970 11.00000 0.02056 0.01212 = 0.02340 -0.00169 0.00156 0.00325 C5 1 0.577012 0.714414 0.287657 11.00000 0.02065 0.01185 = 0.02238 0.00158 0.00391 -0.00063 AFIX 43 H5 2 0.661159 0.761370 0.262584 11.00000 -1.20000 AFIX 0 C6 1 0.420592 0.669344 0.253218 11.00000 0.02073 0.01186 = 0.02066 -0.00009 0.00186 0.00158 C7 1 0.385992 0.693260 0.178717 11.00000 0.01824 0.01135 = 0.02349 -0.00062 0.00196 -0.00115 C8 1 0.404257 0.686444 0.066719 11.00000 0.03004 0.01870 = 0.01913 0.00047 0.00054 -0.00405 AFIX 43 H8 2 0.446482 0.666750 0.024152 11.00000 -1.20000 AFIX 0 C9 1 0.254920 0.758176 0.075501 11.00000 0.02485 0.01957 = 0.01961 0.00167 -0.00272 -0.00129 AFIX 43 H9 2 0.171995 0.798111 0.040399 11.00000 -1.20000 AFIX 0 C10 1 0.772298 0.743433 0.395367 11.00000 0.02237 0.01759 = 0.01915 0.00041 0.00197 0.00030 C11 1 0.894438 0.829635 0.361744 11.00000 0.01953 0.01695 = 0.02245 -0.00185 -0.00361 0.00196 C12 1 0.807387 0.716330 0.466544 11.00000 0.02131 0.01863 = 0.02557 0.00079 0.00016 -0.00042 C13 1 0.651489 0.563386 0.142233 11.00000 0.02254 0.01921 = 0.02552 0.00011 0.00351 0.00272 AFIX 137 H13A 2 0.662143 0.477724 0.105839 11.00000 -1.50000 H13B 2 0.664338 0.503938 0.186744 11.00000 -1.50000 H13C 2 0.738984 0.652978 0.141620 11.00000 -1.50000 AFIX 0 C14 1 0.102776 0.838499 0.175518 11.00000 0.01786 0.02142 = 0.02817 -0.00004 0.00173 0.00215 AFIX 137 H14A 2 0.058324 0.939031 0.148126 11.00000 -1.50000 H14B 2 0.140600 0.877049 0.222361 11.00000 -1.50000 H14C 2 0.014366 0.750034 0.176485 11.00000 -1.50000 REM REM 0392DH.hkl REM AFIX 0 HKLF 4 REM test_a.res in P2(1)/c REM wR2 = 0.1425, GooF = S = 1.079, Restrained GooF = 1.079 for all data REM R1 = 0.0593 for 1809 Fo > 4sig(Fo) and 0.0670 for all 2076 data REM 165 parameters refined using 0 restraints END WGHT 0.0444 1.8079 REM Highest difference peak 0.272, deepest hole -0.339, 1-sigma level 0.065 Q1 1 0.5821 0.6000 0.3731 11.00000 0.05 0.27 Q2 1 0.5236 0.6702 0.0260 11.00000 0.05 0.24 Q3 1 0.5058 0.7364 0.3825 11.00000 0.05 0.23 Q4 1 0.7221 0.6422 0.1026 11.00000 0.05 0.22 Q5 1 0.6038 0.6548 0.1369 11.00000 0.05 0.22 ; _shelx_res_checksum 57541 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.4854(2) 0.6464(2) 0.13101(9) 0.0194(4) Uani 1 1 d . . . . . N2 N 0.2448(2) 0.7629(2) 0.14501(9) 0.0190(4) Uani 1 1 d . . . . . N3 N 0.9930(2) 0.9003(3) 0.33260(10) 0.0263(5) Uani 1 1 d . . . . . N4 N 0.8336(3) 0.6910(3) 0.52488(10) 0.0311(5) Uani 1 1 d . . . . . C1 C 0.2955(3) 0.5960(3) 0.28874(11) 0.0193(5) Uani 1 1 d . . . . . H1 H 0.188960 0.565303 0.265363 0.023 Uiso 1 1 calc R U . . . C2 C 0.3309(3) 0.5692(3) 0.35893(11) 0.0202(5) Uani 1 1 d . . . . . H2 H 0.247538 0.519484 0.383699 0.024 Uiso 1 1 calc R U . . . C3 C 0.4860(3) 0.6139(3) 0.39325(11) 0.0194(5) Uani 1 1 d . . . . . H3 H 0.507748 0.591807 0.441041 0.023 Uiso 1 1 calc R U . . . C4 C 0.6121(3) 0.6914(3) 0.35897(11) 0.0188(5) Uani 1 1 d . . . . . C5 C 0.5770(3) 0.7144(3) 0.28766(10) 0.0182(5) Uani 1 1 d . . . . . H5 H 0.661159 0.761370 0.262584 0.022 Uiso 1 1 calc R U . . . C6 C 0.4206(3) 0.6693(3) 0.25322(10) 0.0178(5) Uani 1 1 d . . . . . C7 C 0.3860(3) 0.6933(3) 0.17872(11) 0.0177(5) Uani 1 1 d . . . . . C8 C 0.4043(3) 0.6864(3) 0.06672(11) 0.0228(5) Uani 1 1 d . . . . . H8 H 0.446482 0.666750 0.024152 0.027 Uiso 1 1 calc R U . . . C9 C 0.2549(3) 0.7582(3) 0.07550(11) 0.0218(5) Uani 1 1 d . . . . . H9 H 0.171995 0.798111 0.040399 0.026 Uiso 1 1 calc R U . . . C10 C 0.7723(3) 0.7434(3) 0.39537(11) 0.0197(5) Uani 1 1 d . . . . . C11 C 0.8944(3) 0.8296(3) 0.36174(11) 0.0201(5) Uani 1 1 d . . . . . C12 C 0.8074(3) 0.7163(3) 0.46654(11) 0.0220(5) Uani 1 1 d . . . . . C13 C 0.6515(3) 0.5634(3) 0.14223(11) 0.0224(5) Uani 1 1 d . . . . . H13A H 0.662143 0.477724 0.105839 0.034 Uiso 1 1 calc R U . . . H13B H 0.664338 0.503938 0.186744 0.034 Uiso 1 1 calc R U . . . H13C H 0.738984 0.652978 0.141620 0.034 Uiso 1 1 calc R U . . . C14 C 0.1028(3) 0.8385(3) 0.17552(11) 0.0226(5) Uani 1 1 d . . . . . H14A H 0.058324 0.939031 0.148126 0.034 Uiso 1 1 calc R U . . . H14B H 0.140600 0.877049 0.222361 0.034 Uiso 1 1 calc R U . . . H14C H 0.014366 0.750034 0.176485 0.034 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 0.0211(9) 0.0162(10) 0.0207(9) 0.0007(7) 0.0015(7) -0.0002(7) N2 0.0170(9) 0.0162(10) 0.0232(9) 0.0021(7) 0.0001(7) 0.0006(7) N3 0.0234(10) 0.0265(11) 0.0282(10) 0.0019(8) 0.0001(8) -0.0014(8) N4 0.0280(11) 0.0393(13) 0.0254(11) 0.0028(9) 0.0004(8) -0.0065(9) C1 0.0187(11) 0.0133(11) 0.0254(11) -0.0006(8) 0.0003(8) 0.0000(8) C2 0.0229(11) 0.0141(11) 0.0243(11) 0.0006(8) 0.0056(8) -0.0003(8) C3 0.0233(11) 0.0140(11) 0.0211(10) 0.0007(8) 0.0033(8) 0.0014(8) C4 0.0206(11) 0.0121(11) 0.0234(11) -0.0017(8) 0.0016(8) 0.0033(8) C5 0.0206(11) 0.0118(11) 0.0224(11) 0.0016(8) 0.0039(8) -0.0006(8) C6 0.0207(11) 0.0119(11) 0.0207(10) -0.0001(8) 0.0019(8) 0.0016(8) C7 0.0182(10) 0.0114(11) 0.0235(11) -0.0006(8) 0.0020(8) -0.0011(8) C8 0.0300(12) 0.0187(12) 0.0191(10) 0.0005(9) 0.0005(9) -0.0041(9) C9 0.0248(12) 0.0196(12) 0.0196(10) 0.0017(8) -0.0027(8) -0.0013(9) C10 0.0224(11) 0.0176(12) 0.0191(10) 0.0004(8) 0.0020(8) 0.0003(9) C11 0.0195(11) 0.0169(12) 0.0225(11) -0.0019(9) -0.0036(9) 0.0020(9) C12 0.0213(11) 0.0186(12) 0.0256(12) 0.0008(9) 0.0002(9) -0.0004(9) C13 0.0225(11) 0.0192(12) 0.0255(11) 0.0001(9) 0.0035(9) 0.0027(9) C14 0.0179(11) 0.0214(12) 0.0282(11) 0.0000(9) 0.0017(8) 0.0021(9) 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 108.89(18) . . ? C7 N1 C13 127.53(18) . . ? C8 N1 C13 123.57(18) . . ? C7 N2 C9 109.44(18) . . ? C7 N2 C14 126.86(18) . . ? C9 N2 C14 123.67(18) . . ? C2 C1 C6 118.55(19) . . ? C2 C1 H1 120.7 . . ? C6 C1 H1 120.7 . . ? C3 C2 C1 120.9(2) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 121.53(19) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C3 117.24(19) . . ? C5 C4 C10 121.29(19) . . ? C3 C4 C10 121.46(19) . . ? C6 C5 C4 121.04(19) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.63(19) . . ? C5 C6 C7 120.45(19) . . ? C1 C6 C7 118.89(18) . . ? N1 C7 N2 106.98(18) . . ? N1 C7 C6 127.05(19) . . ? N2 C7 C6 125.95(19) . . ? C9 C8 N1 107.59(19) . . ? C9 C8 H8 126.2 . . ? N1 C8 H8 126.2 . . ? C8 C9 N2 107.10(18) . . ? C8 C9 H9 126.4 . . ? N2 C9 H9 126.4 . . ? C11 C10 C12 117.78(19) . . ? C11 C10 C4 121.36(19) . . ? C12 C10 C4 120.80(19) . . ? N3 C11 C10 178.5(2) . . ? N4 C12 C10 178.5(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 . . ? 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 1.347(3) . ? N1 C8 1.385(3) . ? N1 C13 1.466(3) . ? N2 C7 1.351(3) . ? N2 C9 1.378(3) . ? N2 C14 1.464(3) . ? N3 C11 1.161(3) . ? N4 C12 1.157(3) . ? C1 C2 1.390(3) . ? C1 C6 1.402(3) . ? C1 H1 0.9500 . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? C3 C4 1.408(3) . ? C3 H3 0.9500 . ? C4 C5 1.408(3) . ? C4 C10 1.449(3) . ? C5 C6 1.395(3) . ? C5 H5 0.9500 . ? C6 C7 1.469(3) . ? C8 C9 1.344(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.406(3) . ? C10 C12 1.409(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 . ? 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 C6 C1 C2 C3 0.1(3) . . . . ? C1 C2 C3 C4 1.4(3) . . . . ? C2 C3 C4 C5 -2.8(3) . . . . ? C2 C3 C4 C10 177.9(2) . . . . ? C3 C4 C5 C6 2.8(3) . . . . ? C10 C4 C5 C6 -177.9(2) . . . . ? C4 C5 C6 C1 -1.5(3) . . . . ? C4 C5 C6 C7 -179.70(19) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? C2 C1 C6 C7 178.20(19) . . . . ? C8 N1 C7 N2 -0.4(2) . . . . ? C13 N1 C7 N2 -179.29(19) . . . . ? C8 N1 C7 C6 177.9(2) . . . . ? C13 N1 C7 C6 -0.9(3) . . . . ? C9 N2 C7 N1 0.6(2) . . . . ? C14 N2 C7 N1 -177.42(19) . . . . ? C9 N2 C7 C6 -177.8(2) . . . . ? C14 N2 C7 C6 4.2(3) . . . . ? C5 C6 C7 N1 46.7(3) . . . . ? C1 C6 C7 N1 -131.6(2) . . . . ? C5 C6 C7 N2 -135.3(2) . . . . ? C1 C6 C7 N2 46.5(3) . . . . ? C7 N1 C8 C9 0.1(2) . . . . ? C13 N1 C8 C9 179.0(2) . . . . ? N1 C8 C9 N2 0.3(2) . . . . ? C7 N2 C9 C8 -0.5(2) . . . . ? C14 N2 C9 C8 177.56(19) . . . . ? C5 C4 C10 C11 4.4(3) . . . . ? C3 C4 C10 C11 -176.4(2) . . . . ? C5 C4 C10 C12 -178.6(2) . . . . ? C3 C4 C10 C12 0.6(3) . . . . ?