# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2018 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_lzd-14-1-51a _database_code_depnum_ccdc_archive 'CCDC 1813311' _audit_update_record ; 2017-12-24 deposited with the CCDC. 2018-09-03 downloaded from the CCDC. ; _audit_creation_date 2017-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _shelx_SHELXL_version_number 2018/1 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C23 H19 N5 O4' _chemical_formula_sum 'C23 H19 N5 O4' _chemical_formula_weight 429.43 _chemical_absolute_configuration ? _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 0.0181 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' O O 0.0492 0.0322 '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 orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.44940(7) _cell_length_b 13.81570(14) _cell_length_c 18.11204(16) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1864.07(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 14667 _cell_measurement_temperature 100 _cell_measurement_theta_max 68.7580 _cell_measurement_theta_min 2.4150 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 0.893 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.76887 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'light colourless' _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_unetI/netI 0.0129 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 15719 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 68.627 _diffrn_reflns_theta_min 4.024 _diffrn_ambient_temperature 100 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -65.00 89.00 1.00 1.00 -- 0.00 45.00 0.00 154 2 \w -135.00 15.00 1.00 1.00 -- -45.00 60.00 270.00 150 3 \w -135.00 -3.00 1.00 1.00 -- -45.00 30.00 0.00 132 4 \w -135.00 31.00 1.00 1.00 -- -45.00 45.00 90.00 166 5 \w -180.00 -1.00 1.00 2.00 -- -90.00 60.00 270.00 179 6 \w -180.00 -1.00 1.00 2.00 -- -90.00 45.00 0.00 179 7 \w -155.00 -45.00 1.00 2.00 -- -90.00 30.00 0.00 110 8 \w -144.00 -2.00 1.00 2.00 -- -90.00 60.00 90.00 142 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0688550000 _diffrn_orient_matrix_UB_12 -0.1006105000 _diffrn_orient_matrix_UB_13 -0.0232439000 _diffrn_orient_matrix_UB_21 -0.0640074000 _diffrn_orient_matrix_UB_22 0.0188369000 _diffrn_orient_matrix_UB_23 -0.0795740000 _diffrn_orient_matrix_UB_31 0.1842490000 _diffrn_orient_matrix_UB_32 0.0441646000 _diffrn_orient_matrix_UB_33 -0.0190536000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _reflns_Friedel_coverage 0.717 _reflns_Friedel_fraction_full 0.973 _reflns_Friedel_fraction_max 0.963 _reflns_number_gt 3308 _reflns_number_total 3344 _reflns_odcompleteness_completeness 98.45 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.51 _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 'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _refine_diff_density_max 0.184 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.031 _refine_ls_abs_structure_details ; Flack x determined using 1363 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.07(5) _refine_ls_extinction_coef 0.0024(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/1 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 292 _refine_ls_number_reflns 3344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0252 _refine_ls_R_factor_gt 0.0245 _refine_ls_restrained_S_all 1.047 _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^)+(0.0320P)^2^+0.5420P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.0626 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C17(H17), C14(H14), C26(H26), C3(H3A) 2.b Secondary CH2 refined with riding coordinates: C15(H15A,H15B) 2.c Aromatic/amide H refined with riding coordinates: N2(H2), C21(H21), C20(H20), C10(H10), C23(H23), C22(H22), C9(H9), C7(H7), C8(H8) 2.d Idealised Me refined as rotating group: C28(H28A,H28B,H28C) 2.e Idealised tetrahedral OH refined as rotating group: O3(H3) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _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 O3 O 0.89384(16) 0.40489(9) 0.51854(7) 0.0174(3) Uani 1 1 d . . . . . H3 H 0.824332 0.357378 0.523055 0.026 Uiso 1 1 calc GR . . . . O2 O 1.14087(17) 0.58159(10) 0.63455(7) 0.0208(3) Uani 1 1 d . . . . . O1 O 0.67410(19) 0.75092(9) 0.50681(8) 0.0239(3) Uani 1 1 d . . . . . O4 O 0.34931(18) 0.27837(9) 0.41164(8) 0.0247(3) Uani 1 1 d . . . . . N13 N 0.8423(2) 0.55631(10) 0.61613(8) 0.0160(3) Uani 1 1 d . . . . . N2 N 0.5218(2) 0.62733(11) 0.56102(9) 0.0199(3) Uani 1 1 d . . . . . H2 H 0.419606 0.659312 0.560550 0.024 Uiso 1 1 calc R . . . . N25 N 0.5246(2) 0.45350(11) 0.52973(8) 0.0184(3) Uani 1 1 d . . . . . N18 N 0.5583(2) 0.40198(11) 0.41167(8) 0.0181(3) Uani 1 1 d . . . . . N5 N 0.6684(2) 0.44896(11) 0.68876(8) 0.0201(3) Uani 1 1 d . . . . . C12 C 1.0028(2) 0.54031(13) 0.65348(10) 0.0171(4) Uani 1 1 d . . . . . C1 C 0.6726(2) 0.67199(13) 0.53748(9) 0.0174(4) Uani 1 1 d . . . . . C24 C 0.8559(3) 0.42510(12) 0.38700(9) 0.0173(4) Uani 1 1 d . . . . . C17 C 0.6186(2) 0.47672(12) 0.46258(10) 0.0163(4) Uani 1 1 d . . . . . H17 H 0.581314 0.542013 0.444332 0.020 Uiso 1 1 calc R . . . . C27 C 0.4165(2) 0.35040(13) 0.43872(10) 0.0188(4) Uani 1 1 d . . . . . C16 C 0.8259(2) 0.46873(12) 0.46370(9) 0.0158(4) Uani 1 1 d . . . . . C14 C 0.8491(2) 0.61881(12) 0.54991(9) 0.0159(4) Uani 1 1 d . . . . . H14 H 0.940683 0.669843 0.560632 0.019 Uiso 1 1 calc R . . . . C11 C 0.9878(3) 0.47173(13) 0.71472(10) 0.0194(4) Uani 1 1 d . . . . . C19 C 0.6986(3) 0.38106(13) 0.36204(10) 0.0183(4) Uani 1 1 d . . . . . C21 C 0.8533(3) 0.31459(14) 0.25996(10) 0.0244(4) Uani 1 1 d . . . . . H21 H 0.854927 0.276288 0.216408 0.029 Uiso 1 1 calc R . . . . C15 C 0.9140(2) 0.56636(13) 0.47877(9) 0.0155(4) Uani 1 1 d . . . . . H15A H 0.891407 0.609275 0.435995 0.019 Uiso 1 1 calc R . . . . H15B H 1.045344 0.556592 0.482336 0.019 Uiso 1 1 calc R . . . . C20 C 0.6929(3) 0.32526(14) 0.29843(10) 0.0217(4) Uani 1 1 d . . . . . H20 H 0.584844 0.295792 0.281957 0.026 Uiso 1 1 calc R . . . . C10 C 1.1378(3) 0.44939(14) 0.75834(10) 0.0230(4) Uani 1 1 d . . . . . H10 H 1.250574 0.478669 0.748292 0.028 Uiso 1 1 calc R . . . . C23 C 1.0135(3) 0.41374(13) 0.34766(10) 0.0201(4) Uani 1 1 d . . . . . H23 H 1.121558 0.443188 0.364141 0.024 Uiso 1 1 calc R . . . . C22 C 1.0110(3) 0.35832(14) 0.28341(10) 0.0238(4) Uani 1 1 d . . . . . H22 H 1.117954 0.350424 0.255471 0.029 Uiso 1 1 calc R . . . . C9 C 1.1205(3) 0.38447(15) 0.81604(10) 0.0273(5) Uani 1 1 d . . . . . H9 H 1.220804 0.370740 0.846715 0.033 Uiso 1 1 calc R . . . . C4 C 0.6867(2) 0.50954(13) 0.63537(9) 0.0172(4) Uani 1 1 d . . . . . C26 C 0.3590(2) 0.40135(13) 0.51030(10) 0.0195(4) Uani 1 1 d . . . . . H26 H 0.260278 0.448445 0.499832 0.023 Uiso 1 1 calc R . . . . C3 C 0.5238(2) 0.52710(13) 0.58733(10) 0.0188(4) Uani 1 1 d . . . . . H3A H 0.414391 0.516910 0.618370 0.023 Uiso 1 1 calc R . . . . C28 C 0.3010(3) 0.33102(14) 0.56923(11) 0.0251(4) Uani 1 1 d . . . . . H28A H 0.400396 0.286994 0.580642 0.038 Uiso 1 1 calc GR . . . . H28B H 0.197925 0.293582 0.551539 0.038 Uiso 1 1 calc GR . . . . H28C H 0.267134 0.366737 0.613852 0.038 Uiso 1 1 calc GR . . . . C6 C 0.8215(3) 0.42795(13) 0.72901(10) 0.0200(4) Uani 1 1 d . . . . . C7 C 0.8077(3) 0.35991(14) 0.78674(10) 0.0252(4) Uani 1 1 d . . . . . H7 H 0.696619 0.328549 0.796242 0.030 Uiso 1 1 calc R . . . . C8 C 0.9562(3) 0.33904(14) 0.82936(11) 0.0285(5) Uani 1 1 d . . . . . H8 H 0.946547 0.293200 0.868255 0.034 Uiso 1 1 calc R . . . . 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 O3 0.0180(7) 0.0158(6) 0.0184(6) 0.0037(5) -0.0012(5) -0.0005(5) O2 0.0150(6) 0.0247(7) 0.0227(6) 0.0011(5) -0.0016(5) 0.0008(5) O1 0.0247(7) 0.0162(6) 0.0309(7) 0.0020(5) -0.0052(6) 0.0033(5) O4 0.0226(7) 0.0172(6) 0.0343(7) -0.0020(6) -0.0052(6) -0.0031(6) N13 0.0161(7) 0.0162(7) 0.0156(7) -0.0001(6) 0.0009(6) 0.0018(6) N2 0.0143(8) 0.0195(8) 0.0259(8) -0.0035(7) -0.0013(6) 0.0036(6) N25 0.0152(8) 0.0198(8) 0.0201(7) -0.0008(6) 0.0009(6) -0.0027(6) N18 0.0180(7) 0.0164(8) 0.0198(7) -0.0012(6) -0.0042(6) -0.0007(6) N5 0.0211(8) 0.0208(8) 0.0185(7) -0.0017(6) 0.0030(6) -0.0013(7) C12 0.0175(9) 0.0176(8) 0.0163(8) -0.0046(7) 0.0003(7) 0.0036(7) C1 0.0186(9) 0.0165(9) 0.0172(8) -0.0038(7) -0.0030(7) 0.0021(7) C24 0.0223(9) 0.0128(8) 0.0169(8) 0.0017(7) -0.0018(7) 0.0015(7) C17 0.0188(9) 0.0131(8) 0.0172(8) 0.0000(7) -0.0019(7) 0.0000(7) C27 0.0162(9) 0.0154(9) 0.0250(9) 0.0027(7) -0.0065(7) 0.0015(7) C16 0.0171(9) 0.0144(8) 0.0158(8) 0.0019(7) -0.0003(7) 0.0008(7) C14 0.0160(9) 0.0148(8) 0.0168(8) 0.0002(7) -0.0004(7) 0.0004(7) C11 0.0239(9) 0.0183(9) 0.0160(8) -0.0032(7) 0.0002(7) 0.0043(8) C19 0.0228(9) 0.0151(8) 0.0169(8) 0.0037(7) -0.0018(7) 0.0006(7) C21 0.0378(11) 0.0183(9) 0.0169(9) 0.0000(7) 0.0000(8) 0.0036(9) C15 0.0157(9) 0.0157(9) 0.0151(8) 0.0011(7) -0.0004(6) -0.0002(7) C20 0.0284(10) 0.0171(9) 0.0196(9) 0.0009(7) -0.0063(8) -0.0003(8) C10 0.0289(10) 0.0217(9) 0.0185(9) -0.0038(7) -0.0023(8) 0.0062(8) C23 0.0234(9) 0.0184(9) 0.0186(8) 0.0025(7) -0.0001(7) 0.0005(8) C22 0.0294(10) 0.0224(10) 0.0197(9) 0.0018(8) 0.0040(8) 0.0035(8) C9 0.0387(12) 0.0251(10) 0.0180(9) -0.0037(8) -0.0047(9) 0.0126(9) C4 0.0165(9) 0.0169(8) 0.0182(9) -0.0041(7) 0.0030(7) -0.0001(7) C26 0.0145(9) 0.0173(9) 0.0267(9) 0.0010(7) -0.0032(7) -0.0005(7) C3 0.0147(9) 0.0201(9) 0.0215(9) -0.0012(7) 0.0021(7) -0.0005(7) C28 0.0229(10) 0.0217(9) 0.0307(10) 0.0017(8) 0.0024(8) -0.0031(8) C6 0.0268(10) 0.0178(9) 0.0155(8) -0.0044(7) 0.0021(7) 0.0019(8) C7 0.0366(11) 0.0197(9) 0.0195(9) -0.0020(7) 0.0059(8) 0.0002(8) C8 0.0503(13) 0.0185(10) 0.0166(9) 0.0011(8) 0.0024(9) 0.0089(9) _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 O3 H3 0.8400 . ? O3 C16 1.422(2) . ? O2 C12 1.225(2) . ? O1 C1 1.224(2) . ? O4 C27 1.217(2) . ? N13 C12 1.391(2) . ? N13 C14 1.479(2) . ? N13 C4 1.372(2) . ? N2 H2 0.8800 . ? N2 C1 1.351(2) . ? N2 C3 1.465(3) . ? N25 C17 1.440(2) . ? N25 C26 1.471(2) . ? N25 C3 1.457(2) . ? N18 C17 1.455(2) . ? N18 C27 1.365(2) . ? N18 C19 1.408(2) . ? N5 C4 1.286(2) . ? N5 C6 1.384(3) . ? C12 C11 1.463(3) . ? C1 C14 1.523(2) . ? C24 C16 1.531(2) . ? C24 C19 1.396(3) . ? C24 C23 1.382(3) . ? C17 H17 1.0000 . ? C17 C16 1.548(2) . ? C27 C26 1.536(3) . ? C16 C15 1.525(2) . ? C14 H14 1.0000 . ? C14 C15 1.555(2) . ? C11 C10 1.403(3) . ? C11 C6 1.402(3) . ? C19 C20 1.387(3) . ? C21 H21 0.9500 . ? C21 C20 1.391(3) . ? C21 C22 1.388(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C20 H20 0.9500 . ? C10 H10 0.9500 . ? C10 C9 1.383(3) . ? C23 H23 0.9500 . ? C23 C22 1.393(3) . ? C22 H22 0.9500 . ? C9 H9 0.9500 . ? C9 C8 1.397(3) . ? C4 C3 1.513(2) . ? C26 H26 1.0000 . ? C26 C28 1.507(3) . ? C3 H3A 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C6 C7 1.410(3) . ? C7 H7 0.9500 . ? C7 C8 1.379(3) . ? C8 H8 0.9500 . ? 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 C16 O3 H3 109.5 . . ? C12 N13 C14 117.24(15) . . ? C4 N13 C12 121.85(14) . . ? C4 N13 C14 120.65(14) . . ? C1 N2 H2 119.1 . . ? C1 N2 C3 121.74(15) . . ? C3 N2 H2 119.1 . . ? C17 N25 C26 108.35(14) . . ? C17 N25 C3 116.84(14) . . ? C3 N25 C26 120.65(14) . . ? C27 N18 C17 112.43(15) . . ? C27 N18 C19 134.11(15) . . ? C19 N18 C17 108.74(14) . . ? C4 N5 C6 116.44(16) . . ? O2 C12 N13 120.76(16) . . ? O2 C12 C11 125.29(17) . . ? N13 C12 C11 113.94(16) . . ? O1 C1 N2 123.92(17) . . ? O1 C1 C14 119.26(16) . . ? N2 C1 C14 116.81(15) . . ? C19 C24 C16 110.05(16) . . ? C23 C24 C16 129.55(17) . . ? C23 C24 C19 119.78(16) . . ? N25 C17 N18 103.14(14) . . ? N25 C17 H17 110.2 . . ? N25 C17 C16 117.26(15) . . ? N18 C17 H17 110.2 . . ? N18 C17 C16 105.39(14) . . ? C16 C17 H17 110.2 . . ? O4 C27 N18 126.90(18) . . ? O4 C27 C26 126.86(18) . . ? N18 C27 C26 106.23(15) . . ? O3 C16 C24 109.73(13) . . ? O3 C16 C17 114.12(14) . . ? O3 C16 C15 105.70(14) . . ? C24 C16 C17 99.32(14) . . ? C15 C16 C24 116.61(15) . . ? C15 C16 C17 111.64(14) . . ? N13 C14 C1 111.84(14) . . ? N13 C14 H14 106.1 . . ? N13 C14 C15 114.24(13) . . ? C1 C14 H14 106.1 . . ? C1 C14 C15 111.75(14) . . ? C15 C14 H14 106.1 . . ? C10 C11 C12 120.56(18) . . ? C6 C11 C12 119.12(17) . . ? C6 C11 C10 120.32(17) . . ? C24 C19 N18 109.08(15) . . ? C20 C19 N18 128.43(17) . . ? C20 C19 C24 122.49(18) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C22 C21 C20 121.87(17) . . ? C16 C15 C14 115.27(14) . . ? C16 C15 H15A 108.5 . . ? C16 C15 H15B 108.5 . . ? C14 C15 H15A 108.5 . . ? C14 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C19 C20 C21 116.65(18) . . ? C19 C20 H20 121.7 . . ? C21 C20 H20 121.7 . . ? C11 C10 H10 120.2 . . ? C9 C10 C11 119.6(2) . . ? C9 C10 H10 120.2 . . ? C24 C23 H23 120.6 . . ? C24 C23 C22 118.80(18) . . ? C22 C23 H23 120.6 . . ? C21 C22 C23 120.41(18) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C10 C9 H9 119.9 . . ? C10 C9 C8 120.22(19) . . ? C8 C9 H9 119.9 . . ? N13 C4 C3 117.14(15) . . ? N5 C4 N13 125.92(17) . . ? N5 C4 C3 116.87(17) . . ? N25 C26 C27 101.09(14) . . ? N25 C26 H26 110.1 . . ? N25 C26 C28 112.74(15) . . ? C27 C26 H26 110.1 . . ? C28 C26 C27 112.47(15) . . ? C28 C26 H26 110.1 . . ? N2 C3 C4 110.30(15) . . ? N2 C3 H3A 107.9 . . ? N25 C3 N2 115.29(15) . . ? N25 C3 C4 107.26(14) . . ? N25 C3 H3A 107.9 . . ? C4 C3 H3A 107.9 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28B 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N5 C6 C11 122.69(16) . . ? N5 C6 C7 118.07(18) . . ? C11 C6 C7 119.25(18) . . ? C6 C7 H7 120.1 . . ? C8 C7 C6 119.75(19) . . ? C8 C7 H7 120.1 . . ? C9 C8 H8 119.6 . . ? C7 C8 C9 120.81(18) . . ? C7 C8 H8 119.6 . . ? _shelx_res_file ; TITL lzd-14-1-51a_a.res in P2(1)2(1)2(1) lzd-14-1-51a.res created by SHELXL-2018/1 at 18:02:35 on 24-Dec-2017 REM Old TITL LZD-14-1-51A in P212121 #19 REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.082, Rweak 0.027, Alpha 0.001, Orientation as input REM Flack x = 0.116 ( 0.241 ) from Parsons' quotients REM Formula found by SHELXT: C23 N5 O4 CELL 1.54184 7.449401 13.815704 18.112042 90 90 90 ZERR 4 0.000072 0.000138 0.000159 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 92 76 20 16 L.S. 27 PLAN 20 TEMP -173.15 BOND $H LIST 6 fmap 2 acta OMIT 4 10 11 OMIT 8 5 2 OMIT 7 8 5 OMIT 8 2 1 OMIT 8 1 1 OMIT 3 2 6 OMIT 0 7 12 REM REM REM WGHT 0.032000 0.542000 EXTI 0.002413 FVAR 1.09390 O3 4 0.893837 0.404887 0.518541 11.00000 0.01801 0.01575 = 0.01841 0.00373 -0.00120 -0.00045 AFIX 147 H3 2 0.824332 0.357378 0.523055 11.00000 -1.50000 AFIX 0 O2 4 1.140869 0.581588 0.634554 11.00000 0.01497 0.02466 = 0.02274 0.00106 -0.00160 0.00075 O1 4 0.674096 0.750918 0.506808 11.00000 0.02469 0.01620 = 0.03091 0.00200 -0.00517 0.00332 O4 4 0.349306 0.278368 0.411637 11.00000 0.02256 0.01719 = 0.03427 -0.00196 -0.00518 -0.00306 N13 3 0.842320 0.556311 0.616127 11.00000 0.01609 0.01617 = 0.01562 -0.00006 0.00088 0.00176 N2 3 0.521762 0.627332 0.561025 11.00000 0.01426 0.01949 = 0.02593 -0.00348 -0.00133 0.00360 AFIX 43 H2 2 0.419606 0.659312 0.560550 11.00000 -1.20000 AFIX 0 N25 3 0.524559 0.453503 0.529733 11.00000 0.01519 0.01980 = 0.02010 -0.00078 0.00088 -0.00273 N18 3 0.558317 0.401975 0.411674 11.00000 0.01804 0.01638 = 0.01982 -0.00125 -0.00417 -0.00069 N5 3 0.668403 0.448956 0.688758 11.00000 0.02112 0.02075 = 0.01845 -0.00175 0.00301 -0.00131 C12 1 1.002784 0.540312 0.653477 11.00000 0.01747 0.01757 = 0.01625 -0.00463 0.00032 0.00359 C1 1 0.672565 0.671991 0.537476 11.00000 0.01863 0.01646 = 0.01716 -0.00377 -0.00299 0.00215 C24 1 0.855917 0.425097 0.387000 11.00000 0.02229 0.01281 = 0.01685 0.00167 -0.00183 0.00150 C17 1 0.618551 0.476715 0.462577 11.00000 0.01876 0.01312 = 0.01717 0.00000 -0.00190 -0.00002 AFIX 13 H17 2 0.581314 0.542013 0.444332 11.00000 -1.20000 AFIX 0 C27 1 0.416539 0.350398 0.438724 11.00000 0.01620 0.01536 = 0.02499 0.00266 -0.00651 0.00148 C16 1 0.825871 0.468735 0.463703 11.00000 0.01706 0.01438 = 0.01582 0.00195 -0.00030 0.00083 C14 1 0.849125 0.618811 0.549909 11.00000 0.01602 0.01477 = 0.01680 0.00023 -0.00037 0.00038 AFIX 13 H14 2 0.940683 0.669843 0.560632 11.00000 -1.20000 AFIX 0 C11 1 0.987765 0.471726 0.714724 11.00000 0.02388 0.01826 = 0.01603 -0.00318 0.00020 0.00433 C19 1 0.698589 0.381062 0.362038 11.00000 0.02281 0.01505 = 0.01691 0.00373 -0.00180 0.00063 C21 1 0.853302 0.314593 0.259962 11.00000 0.03780 0.01835 = 0.01693 -0.00002 -0.00002 0.00362 AFIX 43 H21 2 0.854927 0.276288 0.216408 11.00000 -1.20000 AFIX 0 C15 1 0.913974 0.566361 0.478773 11.00000 0.01570 0.01569 = 0.01510 0.00106 -0.00042 -0.00018 AFIX 23 H15A 2 0.891407 0.609275 0.435995 11.00000 -1.20000 H15B 2 1.045344 0.556592 0.482336 11.00000 -1.20000 AFIX 0 C20 1 0.692884 0.325258 0.298431 11.00000 0.02843 0.01715 = 0.01959 0.00087 -0.00627 -0.00028 AFIX 43 H20 2 0.584844 0.295792 0.281957 11.00000 -1.20000 AFIX 0 C10 1 1.137802 0.449386 0.758335 11.00000 0.02891 0.02170 = 0.01849 -0.00384 -0.00233 0.00621 AFIX 43 H10 2 1.250574 0.478669 0.748292 11.00000 -1.20000 AFIX 0 C23 1 1.013506 0.413740 0.347662 11.00000 0.02338 0.01844 = 0.01857 0.00247 -0.00012 0.00048 AFIX 43 H23 2 1.121558 0.443188 0.364141 11.00000 -1.20000 AFIX 0 C22 1 1.011020 0.358324 0.283408 11.00000 0.02935 0.02240 = 0.01966 0.00179 0.00398 0.00351 AFIX 43 H22 2 1.117954 0.350424 0.255471 11.00000 -1.20000 AFIX 0 C9 1 1.120546 0.384472 0.816039 11.00000 0.03866 0.02513 = 0.01803 -0.00368 -0.00469 0.01259 AFIX 43 H9 2 1.220804 0.370740 0.846715 11.00000 -1.20000 AFIX 0 C4 1 0.686666 0.509540 0.635366 11.00000 0.01653 0.01690 = 0.01817 -0.00413 0.00297 -0.00009 C26 1 0.358993 0.401355 0.510303 11.00000 0.01452 0.01734 = 0.02667 0.00104 -0.00323 -0.00046 AFIX 13 H26 2 0.260278 0.448445 0.499832 11.00000 -1.20000 AFIX 0 C3 1 0.523779 0.527099 0.587325 11.00000 0.01466 0.02013 = 0.02148 -0.00119 0.00209 -0.00053 AFIX 13 H3A 2 0.414391 0.516910 0.618370 11.00000 -1.20000 AFIX 0 C28 1 0.301049 0.331021 0.569233 11.00000 0.02286 0.02172 = 0.03069 0.00174 0.00237 -0.00315 AFIX 137 H28A 2 0.400396 0.286994 0.580642 11.00000 -1.50000 H28B 2 0.197925 0.293582 0.551539 11.00000 -1.50000 H28C 2 0.267134 0.366737 0.613852 11.00000 -1.50000 AFIX 0 C6 1 0.821491 0.427949 0.729008 11.00000 0.02679 0.01783 = 0.01546 -0.00438 0.00210 0.00190 C7 1 0.807734 0.359908 0.786736 11.00000 0.03659 0.01966 = 0.01947 -0.00197 0.00590 0.00023 AFIX 43 H7 2 0.696619 0.328549 0.796242 11.00000 -1.20000 AFIX 0 C8 1 0.956186 0.339037 0.829359 11.00000 0.05027 0.01852 = 0.01662 0.00105 0.00235 0.00895 AFIX 43 H8 2 0.946547 0.293200 0.868255 11.00000 -1.20000 AFIX 0 HKLF 4 REM lzd-14-1-51a_a.res in P2(1)2(1)2(1) REM R1 = 0.0245 for 3308 Fo > 4sig(Fo) and 0.0252 for all 3344 data REM 292 parameters refined using 0 restraints END WGHT 0.0317 0.5381 REM Highest difference peak 0.184, deepest hole -0.130, 1-sigma level 0.031 Q1 1 0.8497 0.4525 0.4198 11.00000 0.05 0.18 Q2 1 0.7169 0.4741 0.4701 11.00000 0.05 0.15 Q3 1 0.4053 0.6484 0.5321 11.00000 0.05 0.15 Q4 1 0.8418 0.5805 0.5808 11.00000 0.05 0.14 Q5 1 0.2185 0.2919 0.5070 11.00000 0.05 0.14 Q6 1 0.9369 0.4001 0.3788 11.00000 0.05 0.13 Q7 1 0.8703 0.5909 0.5143 11.00000 0.05 0.13 Q8 1 0.8611 0.5150 0.4682 11.00000 0.05 0.13 Q9 1 0.7865 0.3880 0.3827 11.00000 0.05 0.13 Q10 1 0.3832 0.3712 0.4770 11.00000 0.05 0.13 Q11 1 0.8204 0.3631 0.7413 11.00000 0.05 0.13 Q12 1 0.6037 0.5194 0.6140 11.00000 0.05 0.13 Q13 1 0.7148 0.3257 0.3457 11.00000 0.05 0.12 Q14 1 1.0631 0.4501 0.7257 11.00000 0.05 0.12 Q15 1 0.7567 0.6338 0.5422 11.00000 0.05 0.12 Q16 1 0.9063 0.3294 0.7847 11.00000 0.05 0.11 Q17 1 1.0100 0.3688 0.3224 11.00000 0.05 0.11 Q18 1 1.0015 0.4893 0.6806 11.00000 0.05 0.11 Q19 1 0.7794 0.5221 0.6140 11.00000 0.05 0.11 Q20 1 0.9402 0.3231 0.2837 11.00000 0.05 0.11 ; _shelx_res_checksum 86426 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.438 _oxdiff_exptl_absorpt_empirical_full_min 0.575