#============================================================================= data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 13 _journal_issue 4 _journal_year 2022 _journal_page_first 468 _journal_page_last 477 #============================================================================= data_shelx _audit_creation_date 2022-09-25 _audit_creation_method ; Olex2 1.3-beta (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_contact_author_address ? _audit_contact_author_email ? _audit_contact_author_name '' _audit_contact_author_phone ? _publ_contact_author_id_orcid ? _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C6 H2 N3 O7, C8 H12 N' _chemical_formula_sum 'C14 H14 N4 O7' _chemical_formula_weight 350.29 _chemical_melting_point ? 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' _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. ; _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' 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' _cell_length_a 4.0174(4) _cell_length_b 27.863(3) _cell_length_c 13.9247(17) _cell_angle_alpha 90 _cell_angle_beta 95.741(4) _cell_angle_gamma 90 _cell_volume 1550.9(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9535 _cell_measurement_temperature 296 _cell_measurement_theta_max 28.07 _cell_measurement_theta_min 3.03 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6894 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ? _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.500 _exptl_crystal_description prism _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_unetI/netI 0.0226 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 62749 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.529 _diffrn_reflns_theta_min 2.940 _diffrn_ambient_temperature 296 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source ? _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2846 _reflns_number_total 3911 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _refine_diff_density_max 0.330 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef 0.067(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 3911 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0569 _refine_ls_restrained_S_all 1.063 _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^)+(0.0753P)^2^+0.9076P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1513 _refine_ls_wR_factor_ref 0.1710 _olex2_refinement_description ; 1. Others Fixed Uiso: H44(0.042) H4(0.043) H8(0.048) H2(0.044) H10(0.05) H12A(0.071) H12B(0.071) H12C(0.071) H14A(0.08) H14B(0.08) H14C(0.08) H13A(0.095) H13B(0.095) H13C(0.095) Fixed X: H44(0.792057) H4(0.289551) H8(0.957989) H2(0.681223) H10(0.499097) H12A(1.127659) H12B(0.886064) H12C(1.235889) H14A(0.391692) H14B(0.672453) H14C(0.327118) H13A(0.599167) H13B(0.582256) H13C(0.929536) Fixed Y: H44(0.624345) H4(0.528441) H8(0.605472) H2(0.645073) H10(0.723895) H12A(0.544338) H12B(0.53997) H12C(0.564686) H14A(0.733448) H14B(0.710485) H14C(0.684457) H13A(0.718056) H13B(0.665581) H13C(0.690812) Fixed Z: H44(0.444136) H4(0.112225) H8(0.721768) H2(-0.003113) H10(0.612448) H12A(0.61616) H12B(0.520935) H12C(0.519026) H14A(0.440027) H14B(0.384351) H14C(0.386002) H13A(0.779583) H13B(0.819409) H13C(0.815741) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary ? _atom_sites_solution_secondary ? 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 O1 O 0.8935(4) 0.62525(6) 0.30965(10) 0.0497(4) Uani 1 1 d . . . . . N4 N 0.7741(4) 0.63465(6) 0.50160(11) 0.0349(4) Uani 1 1 d . . . . . H44 H 0.792057 0.624345 0.444136 0.042 Uiso 1 1 calc R U . . . O7 O 0.5521(6) 0.55156(7) 0.37182(12) 0.0730(6) Uani 1 1 d . . . . . N1 N 0.9706(5) 0.68578(6) 0.14343(13) 0.0432(4) Uani 1 1 d . . . . . O3 O 1.0519(5) 0.70235(7) 0.06785(13) 0.0675(6) Uani 1 1 d . . . . . N3 N 0.4759(5) 0.53981(7) 0.28941(13) 0.0461(4) Uani 1 1 d . . . . . O5 O 0.1627(6) 0.53324(8) -0.06332(13) 0.0766(6) Uani 1 1 d . . . . . N2 N 0.3183(5) 0.57039(7) -0.05461(13) 0.0513(5) Uani 1 1 d . . . . . O2 O 1.0371(7) 0.70650(7) 0.21965(14) 0.0866(8) Uani 1 1 d . . . . . C7 C 0.8986(5) 0.60712(7) 0.57698(13) 0.0348(4) Uani 1 1 d . . . . . C4 C 0.4138(5) 0.55659(7) 0.11978(14) 0.0361(4) Uani 1 1 d . . . . . H4 H 0.289551 0.528441 0.112225 0.043 Uiso 1 1 calc R U . . . C11 C 0.6230(5) 0.67754(7) 0.51186(14) 0.0371(4) Uani 1 1 d . . . . . C1 C 0.7845(5) 0.64083(6) 0.14038(13) 0.0333(4) Uani 1 1 d . . . . . C5 C 0.5483(5) 0.57089(7) 0.20933(13) 0.0346(4) Uani 1 1 d . . . . . C6 C 0.7530(5) 0.61383(7) 0.22860(13) 0.0334(4) Uani 1 1 d . . . . . C3 C 0.4655(5) 0.58473(7) 0.04027(13) 0.0367(4) Uani 1 1 d . . . . . C8 C 0.8749(5) 0.62391(7) 0.66907(14) 0.0401(5) Uani 1 1 d . . . . . H8 H 0.957989 0.605472 0.721768 0.048 Uiso 1 1 calc R U . . . C2 C 0.6492(5) 0.62655(7) 0.05075(13) 0.0364(4) Uani 1 1 d . . . . . H2 H 0.681223 0.645073 -0.003113 0.044 Uiso 1 1 calc R U . . . C9 C 0.7284(5) 0.66801(8) 0.68415(15) 0.0420(5) Uani 1 1 d . . . . . C10 C 0.6007(5) 0.69444(7) 0.60379(16) 0.0417(5) Uani 1 1 d . . . . . H10 H 0.499097 0.723895 0.612448 0.050 Uiso 1 1 calc R U . . . O4 O 0.3565(8) 0.59661(9) -0.12274(13) 0.1011(9) Uani 1 1 d . . . . . O6 O 0.3336(9) 0.50257(10) 0.27085(16) 0.1231(12) Uani 1 1 d . . . . . C12 C 1.0506(6) 0.55981(8) 0.55644(16) 0.0470(5) Uani 1 1 d . . . . . H12A H 1.127659 0.544338 0.616160 0.071 Uiso 1 1 calc R U . . . H12B H 0.886064 0.539970 0.520935 0.071 Uiso 1 1 calc R U . . . H12C H 1.235889 0.564686 0.519026 0.071 Uiso 1 1 calc R U . . . C14 C 0.4919(6) 0.70383(9) 0.42260(17) 0.0534(6) Uani 1 1 d . . . . . H14A H 0.391692 0.733448 0.440027 0.080 Uiso 1 1 calc R U . . . H14B H 0.672453 0.710485 0.384351 0.080 Uiso 1 1 calc R U . . . H14C H 0.327118 0.684457 0.386002 0.080 Uiso 1 1 calc R U . . . C13 C 0.7080(8) 0.68735(10) 0.78363(17) 0.0636(7) Uani 1 1 d . . . . . H13A H 0.599167 0.718056 0.779583 0.095 Uiso 1 1 calc R U . . . H13B H 0.582256 0.665581 0.819409 0.095 Uiso 1 1 calc R U . . . H13C H 0.929536 0.690812 0.815741 0.095 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 O1 0.0619(10) 0.0590(10) 0.0271(7) -0.0005(6) -0.0012(6) -0.0110(8) N4 0.0443(9) 0.0348(8) 0.0254(7) 0.0012(6) 0.0030(6) -0.0021(7) O7 0.1107(16) 0.0762(13) 0.0320(9) 0.0093(8) 0.0074(9) -0.0195(11) N1 0.0504(10) 0.0349(9) 0.0429(10) 0.0020(7) -0.0021(8) 0.0013(7) O3 0.0937(14) 0.0552(11) 0.0557(11) 0.0050(8) 0.0176(10) -0.0249(10) N3 0.0513(10) 0.0525(11) 0.0343(9) 0.0105(8) 0.0024(7) -0.0064(8) O5 0.0987(15) 0.0802(14) 0.0478(10) -0.0084(9) -0.0089(10) -0.0422(12) N2 0.0648(12) 0.0551(12) 0.0317(9) -0.0004(8) -0.0053(8) -0.0097(9) O2 0.149(2) 0.0559(11) 0.0501(11) -0.0023(9) -0.0163(12) -0.0379(13) C7 0.0376(9) 0.0339(9) 0.0326(9) 0.0040(7) 0.0017(7) -0.0046(7) C4 0.0379(10) 0.0374(10) 0.0329(9) 0.0004(8) 0.0033(7) -0.0012(8) C11 0.0406(10) 0.0327(10) 0.0374(10) 0.0040(8) 0.0012(8) -0.0048(8) C1 0.0368(9) 0.0314(9) 0.0317(9) -0.0006(7) 0.0024(7) 0.0027(7) C5 0.0374(10) 0.0390(10) 0.0276(9) 0.0046(7) 0.0041(7) 0.0037(8) C6 0.0353(9) 0.0390(10) 0.0259(8) -0.0007(7) 0.0028(7) 0.0056(7) C3 0.0417(10) 0.0414(10) 0.0261(9) -0.0013(8) -0.0016(7) 0.0016(8) C8 0.0503(11) 0.0411(11) 0.0283(9) 0.0050(8) 0.0010(8) -0.0065(9) C2 0.0443(10) 0.0368(10) 0.0277(9) 0.0048(7) 0.0023(7) 0.0028(8) C9 0.0503(12) 0.0431(11) 0.0337(10) -0.0039(8) 0.0097(8) -0.0131(9) C10 0.0477(11) 0.0334(10) 0.0449(11) -0.0022(8) 0.0091(9) -0.0038(8) O4 0.167(2) 0.0954(16) 0.0337(9) 0.0179(10) -0.0271(12) -0.0545(16) O6 0.199(3) 0.1128(19) 0.0520(13) 0.0269(13) -0.0157(15) -0.103(2) C12 0.0550(13) 0.0404(11) 0.0458(12) 0.0030(9) 0.0058(10) 0.0064(9) C14 0.0610(14) 0.0508(13) 0.0468(13) 0.0131(10) -0.0023(10) 0.0088(11) C13 0.094(2) 0.0597(15) 0.0395(13) -0.0112(11) 0.0183(13) -0.0116(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 C6 1.251(2) . ? N4 H44 0.8600 . ? N4 C7 1.355(2) . ? N4 C11 1.354(3) . ? O7 N3 1.203(2) . ? N1 O3 1.223(2) . ? N1 O2 1.214(2) . ? N1 C1 1.457(3) . ? N3 C5 1.464(2) . ? N3 O6 1.200(3) . ? O5 N2 1.209(3) . ? N2 C3 1.449(3) . ? N2 O4 1.219(3) . ? C7 C8 1.377(3) . ? C7 C12 1.492(3) . ? C4 H4 0.9300 . ? C4 C5 1.368(3) . ? C4 C3 1.389(3) . ? C11 C10 1.375(3) . ? C11 C14 1.493(3) . ? C1 C6 1.457(3) . ? C1 C2 1.370(3) . ? C5 C6 1.462(3) . ? C3 C2 1.379(3) . ? C8 H8 0.9300 . ? C8 C9 1.387(3) . ? C2 H2 0.9300 . ? C9 C10 1.394(3) . ? C9 C13 1.496(3) . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 N4 H44 118.2 . . ? C11 N4 H44 118.2 . . ? C11 N4 C7 123.54(17) . . ? O3 N1 C1 118.66(18) . . ? O2 N1 O3 121.2(2) . . ? O2 N1 C1 120.11(18) . . ? O7 N3 C5 120.96(19) . . ? O6 N3 O7 120.7(2) . . ? O6 N3 C5 118.29(19) . . ? O5 N2 C3 119.18(19) . . ? O5 N2 O4 122.6(2) . . ? O4 N2 C3 118.20(19) . . ? N4 C7 C8 118.32(18) . . ? N4 C7 C12 118.57(17) . . ? C8 C7 C12 123.11(18) . . ? C5 C4 H4 120.5 . . ? C5 C4 C3 119.03(18) . . ? C3 C4 H4 120.5 . . ? N4 C11 C10 118.15(18) . . ? N4 C11 C14 118.02(18) . . ? C10 C11 C14 123.83(19) . . ? C6 C1 N1 120.45(17) . . ? C2 C1 N1 115.60(17) . . ? C2 C1 C6 123.94(18) . . ? C4 C5 N3 115.58(18) . . ? C4 C5 C6 124.72(17) . . ? C6 C5 N3 119.70(16) . . ? O1 C6 C1 124.05(18) . . ? O1 C6 C5 124.64(17) . . ? C1 C6 C5 111.26(16) . . ? C4 C3 N2 119.41(18) . . ? C2 C3 N2 119.67(17) . . ? C2 C3 C4 120.91(17) . . ? C7 C8 H8 119.6 . . ? C7 C8 C9 120.78(18) . . ? C9 C8 H8 119.6 . . ? C1 C2 C3 120.09(18) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C8 C9 C10 118.29(18) . . ? C8 C9 C13 121.5(2) . . ? C10 C9 C13 120.2(2) . . ? C11 C10 C9 120.90(19) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 N4 C7 C8 C9 -0.3(3) . . . . ? N4 C11 C10 C9 -0.4(3) . . . . ? O7 N3 C5 C4 -172.2(2) . . . . ? O7 N3 C5 C6 7.9(3) . . . . ? N1 C1 C6 O1 -4.1(3) . . . . ? N1 C1 C6 C5 178.24(16) . . . . ? N1 C1 C2 C3 -179.36(17) . . . . ? O3 N1 C1 C6 164.98(19) . . . . ? O3 N1 C1 C2 -14.5(3) . . . . ? N3 C5 C6 O1 4.7(3) . . . . ? N3 C5 C6 C1 -177.65(16) . . . . ? O5 N2 C3 C4 -2.6(3) . . . . ? O5 N2 C3 C2 178.7(2) . . . . ? N2 C3 C2 C1 178.86(19) . . . . ? O2 N1 C1 C6 -16.3(3) . . . . ? O2 N1 C1 C2 164.2(2) . . . . ? C7 N4 C11 C10 1.3(3) . . . . ? C7 N4 C11 C14 -178.98(19) . . . . ? C7 C8 C9 C10 1.1(3) . . . . ? C7 C8 C9 C13 -178.5(2) . . . . ? C4 C5 C6 O1 -175.2(2) . . . . ? C4 C5 C6 C1 2.4(3) . . . . ? C4 C3 C2 C1 0.2(3) . . . . ? C11 N4 C7 C8 -1.0(3) . . . . ? C11 N4 C7 C12 178.20(18) . . . . ? C5 C4 C3 N2 -178.74(19) . . . . ? C5 C4 C3 C2 -0.1(3) . . . . ? C6 C1 C2 C3 1.1(3) . . . . ? C3 C4 C5 N3 178.68(18) . . . . ? C3 C4 C5 C6 -1.4(3) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C2 C1 C6 O1 175.4(2) . . . . ? C2 C1 C6 C5 -2.3(3) . . . . ? O4 N2 C3 C4 177.2(2) . . . . ? O4 N2 C3 C2 -1.4(4) . . . . ? O6 N3 C5 C4 6.6(3) . . . . ? O6 N3 C5 C6 -173.3(3) . . . . ? C12 C7 C8 C9 -179.4(2) . . . . ? C14 C11 C10 C9 179.9(2) . . . . ? C13 C9 C10 C11 178.8(2) . . . . ? _olex2_submission_special_instructions 'No special instructions were received'