data_za37 loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 8 _journal_issue 1 _journal_year 2017 _journal_page_first 46 _journal_page_last 51 # start Validation Reply Form _vrf_PLAT353_za37 ; PROBLEM: Long N-H Bond (0.87A) N5 - H2 ... 1.23 Ang. RESPONSE: The H atom is midway between N and O. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H22 N2 O2, 0.5(H2 O)' _chemical_formula_sum 'C19 H23 N2 O2.50' _chemical_formula_weight 319.39 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_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' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.8783(14) _cell_length_b 7.3112(4) _cell_length_c 22.1486(14) _cell_angle_alpha 90.00 _cell_angle_beta 103.612(5) _cell_angle_gamma 90.00 _cell_volume 3443.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16493 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 26.7 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _exptl_special_details ; ; ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 19557 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 26.41 _reflns_number_total 3513 _reflns_number_gt 2864 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.4766P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0046(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3513 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.68797(5) 0.52434(14) 0.44210(4) 0.0368(2) Uani 1 1 d . . . H1 H 0.6542(10) 0.427(3) 0.4243(9) 0.069(6) Uiso 1 1 d . . . O2 O 0.48695(4) 0.64436(12) 0.35161(4) 0.0343(2) Uani 1 1 d . . . H2 H 0.5030(11) 0.488(3) 0.3790(10) 0.084(7) Uiso 1 1 d . . . C1 C 0.62448(6) 0.37500(16) 0.32296(5) 0.0277(3) Uani 1 1 d . . . N2 N 0.61054(5) 0.31332(13) 0.37267(5) 0.0269(2) Uani 1 1 d . . . C3 C 0.56864(6) 0.15663(16) 0.37255(6) 0.0278(3) Uani 1 1 d . . . H3 H 0.5381 0.1475 0.3312 0.033 Uiso 1 1 calc R . . C4 C 0.53307(6) 0.18638(16) 0.42303(6) 0.0281(3) Uani 1 1 d . . . H4A H 0.5049 0.0811 0.4242 0.034 Uiso 1 1 calc R . . H4B H 0.5632 0.1952 0.4640 0.034 Uiso 1 1 calc R . . N5 N 0.49605(5) 0.35426(13) 0.41073(4) 0.0264(2) Uani 1 1 d . . . C6 C 0.44958(5) 0.39457(16) 0.43547(5) 0.0256(3) Uani 1 1 d . . . C7 C 0.59918(8) 0.2979(2) 0.25865(6) 0.0440(4) Uani 1 1 d . . . H7A H 0.5759 0.1849 0.2616 0.066 Uiso 1 1 calc R . . H7B H 0.6342 0.2714 0.2394 0.066 Uiso 1 1 calc R . . H7C H 0.5710 0.3873 0.2333 0.066 Uiso 1 1 calc R . . C8 C 0.60775(7) -0.01776(18) 0.38505(7) 0.0386(3) Uani 1 1 d . . . H8A H 0.6294 -0.0371 0.3515 0.058 Uiso 1 1 calc R . . H8B H 0.5801 -0.1221 0.3870 0.058 Uiso 1 1 calc R . . H8C H 0.6389 -0.0063 0.4247 0.058 Uiso 1 1 calc R . . C9 C 0.43002(6) 0.27127(18) 0.48163(6) 0.0332(3) Uani 1 1 d . . . H9A H 0.3957 0.1918 0.4601 0.050 Uiso 1 1 calc R . . H9B H 0.4157 0.3453 0.5125 0.050 Uiso 1 1 calc R . . H9C H 0.4659 0.1961 0.5025 0.050 Uiso 1 1 calc R . . C11 C 0.66911(6) 0.53043(16) 0.33024(5) 0.0269(3) Uani 1 1 d . . . C12 C 0.69928(5) 0.59794(16) 0.38979(5) 0.0270(3) Uani 1 1 d . . . C13 C 0.74162(6) 0.74253(18) 0.39575(6) 0.0316(3) Uani 1 1 d . . . H13 H 0.7622 0.7854 0.4359 0.038 Uiso 1 1 calc R . . C14 C 0.75386(6) 0.82408(18) 0.34355(6) 0.0344(3) Uani 1 1 d . . . H14 H 0.7827 0.9231 0.3480 0.041 Uiso 1 1 calc R . . C15 C 0.72428(6) 0.76211(19) 0.28453(6) 0.0376(3) Uani 1 1 d . . . H15 H 0.7326 0.8190 0.2487 0.045 Uiso 1 1 calc R . . C16 C 0.68273(6) 0.61720(18) 0.27833(6) 0.0342(3) Uani 1 1 d . . . H16 H 0.6628 0.5751 0.2379 0.041 Uiso 1 1 calc R . . C21 C 0.41670(5) 0.56676(16) 0.41640(5) 0.0255(3) Uani 1 1 d . . . C22 C 0.43759(6) 0.68493(16) 0.37399(5) 0.0281(3) Uani 1 1 d . . . C23 C 0.40408(7) 0.84841(18) 0.35557(6) 0.0358(3) Uani 1 1 d . . . H23 H 0.4175 0.9288 0.3276 0.043 Uiso 1 1 calc R . . C24 C 0.35225(7) 0.89300(19) 0.37759(6) 0.0396(3) Uani 1 1 d . . . H24 H 0.3302 1.0032 0.3642 0.047 Uiso 1 1 calc R . . C25 C 0.33155(6) 0.7790(2) 0.41922(6) 0.0387(3) Uani 1 1 d . . . H25 H 0.2958 0.8112 0.4343 0.046 Uiso 1 1 calc R . . C26 C 0.36364(6) 0.61912(18) 0.43822(6) 0.0320(3) Uani 1 1 d . . . H26 H 0.3497 0.5420 0.4668 0.038 Uiso 1 1 calc R . . O1W O 0.5000 0.8752(2) 0.2500 0.0463(4) Uani 1 2 d S . . H1W H 0.4993(9) 0.799(3) 0.2841(9) 0.069(6) 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 O1 0.0421(5) 0.0431(5) 0.0272(4) -0.0021(4) 0.0120(4) -0.0091(4) O2 0.0391(5) 0.0305(5) 0.0383(5) 0.0083(4) 0.0194(4) 0.0047(4) C1 0.0275(6) 0.0261(6) 0.0301(6) -0.0009(5) 0.0078(5) 0.0039(4) N2 0.0260(5) 0.0246(5) 0.0310(5) 0.0012(4) 0.0083(4) 0.0026(4) C3 0.0283(6) 0.0239(6) 0.0315(6) 0.0009(5) 0.0072(5) 0.0006(5) C4 0.0292(6) 0.0234(6) 0.0318(6) 0.0044(4) 0.0076(5) 0.0009(5) N5 0.0273(5) 0.0238(5) 0.0287(5) 0.0025(4) 0.0078(4) 0.0013(4) C6 0.0270(6) 0.0274(6) 0.0222(5) -0.0011(4) 0.0051(4) -0.0044(4) C7 0.0543(9) 0.0467(8) 0.0323(7) -0.0068(6) 0.0130(6) -0.0171(7) C8 0.0413(8) 0.0275(6) 0.0494(8) 0.0025(6) 0.0158(6) 0.0074(5) C9 0.0373(7) 0.0325(6) 0.0327(6) 0.0048(5) 0.0140(5) -0.0016(5) C11 0.0266(6) 0.0255(6) 0.0295(6) 0.0005(4) 0.0085(5) 0.0044(4) C12 0.0252(6) 0.0283(6) 0.0293(6) 0.0002(5) 0.0104(5) 0.0057(4) C13 0.0276(6) 0.0335(7) 0.0341(6) -0.0038(5) 0.0082(5) 0.0009(5) C14 0.0302(6) 0.0308(6) 0.0431(7) 0.0012(5) 0.0105(5) -0.0025(5) C15 0.0398(7) 0.0385(7) 0.0358(7) 0.0073(6) 0.0117(6) -0.0042(6) C16 0.0377(7) 0.0356(7) 0.0292(6) 0.0021(5) 0.0079(5) -0.0016(5) C21 0.0265(6) 0.0273(6) 0.0221(5) -0.0030(4) 0.0044(4) -0.0008(5) C22 0.0313(6) 0.0267(6) 0.0260(6) -0.0018(5) 0.0061(5) -0.0002(5) C23 0.0445(8) 0.0284(6) 0.0337(6) 0.0026(5) 0.0074(5) 0.0045(5) C24 0.0444(8) 0.0339(7) 0.0371(7) -0.0047(5) 0.0029(6) 0.0122(6) C25 0.0332(7) 0.0448(8) 0.0378(7) -0.0087(6) 0.0079(5) 0.0086(6) C26 0.0310(6) 0.0374(7) 0.0283(6) -0.0056(5) 0.0083(5) -0.0010(5) O1W 0.0768(11) 0.0316(7) 0.0357(7) 0.000 0.0238(7) 0.000 _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 C12 1.3520(15) . ? O1 H1 1.04(2) . ? O2 C22 1.3235(15) . ? O2 H2 1.30(2) . ? C1 N2 1.2908(16) . ? C1 C11 1.4822(17) . ? C1 C7 1.5107(17) . ? N2 C3 1.4669(15) . ? C3 C4 1.5206(17) . ? C3 C8 1.5242(17) . ? C3 H3 1.0000 . ? C4 N5 1.4604(15) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N5 C6 1.2973(15) . ? N5 H2 1.24(2) . ? C6 C21 1.4621(17) . ? C6 C9 1.4989(16) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C11 C16 1.4052(17) . ? C11 C12 1.4174(17) . ? C12 C13 1.3912(18) . ? C13 C14 1.3820(18) . ? C13 H13 0.9500 . ? C14 C15 1.3909(19) . ? C14 H14 0.9500 . ? C15 C16 1.3816(19) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.4113(17) . ? C21 C22 1.4282(17) . ? C22 C23 1.4113(17) . ? C23 C24 1.375(2) . ? C23 H23 0.9500 . ? C24 C25 1.395(2) . ? C24 H24 0.9500 . ? C25 C26 1.3773(19) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? O1W H1W 0.94(2) . ? 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 C12 O1 H1 101.9(11) . . ? C22 O2 H2 100.2(10) . . ? N2 C1 C11 117.19(11) . . ? N2 C1 C7 124.48(12) . . ? C11 C1 C7 118.33(11) . . ? C1 N2 C3 122.98(10) . . ? N2 C3 C4 108.35(9) . . ? N2 C3 C8 109.21(10) . . ? C4 C3 C8 110.41(10) . . ? N2 C3 H3 109.6 . . ? C4 C3 H3 109.6 . . ? C8 C3 H3 109.6 . . ? N5 C4 C3 109.90(9) . . ? N5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? N5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C6 N5 C4 124.58(10) . . ? C6 N5 H2 105.9(11) . . ? C4 N5 H2 129.4(11) . . ? N5 C6 C21 117.05(10) . . ? N5 C6 C9 121.96(11) . . ? C21 C6 C9 120.99(11) . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C16 C11 C12 117.53(11) . . ? C16 C11 C1 121.22(11) . . ? C12 C11 C1 121.25(11) . . ? O1 C12 C13 118.24(11) . . ? O1 C12 C11 121.31(11) . . ? C13 C12 C11 120.44(11) . . ? C14 C13 C12 120.28(12) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.46(12) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 119.52(12) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C11 121.75(12) . . ? C15 C16 H16 119.1 . . ? C11 C16 H16 119.1 . . ? C26 C21 C22 118.52(11) . . ? C26 C21 C6 121.54(11) . . ? C22 C21 C6 119.94(10) . . ? O2 C22 C23 119.71(11) . . ? O2 C22 C21 121.76(11) . . ? C23 C22 C21 118.53(11) . . ? C24 C23 C22 120.93(12) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C25 121.05(12) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C26 C25 C24 119.18(12) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? C25 C26 C21 121.79(12) . . ? C25 C26 H26 119.1 . . ? C21 C26 H26 119.1 . . ? 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 C11 C1 N2 C3 -178.02(10) . . . . ? C7 C1 N2 C3 1.07(19) . . . . ? C1 N2 C3 C4 -147.32(11) . . . . ? C1 N2 C3 C8 92.38(13) . . . . ? N2 C3 C4 N5 60.15(12) . . . . ? C8 C3 C4 N5 179.70(10) . . . . ? C3 C4 N5 C6 162.26(11) . . . . ? C4 N5 C6 C21 -178.34(10) . . . . ? C4 N5 C6 C9 1.68(18) . . . . ? N2 C1 C11 C16 -174.25(11) . . . . ? C7 C1 C11 C16 6.61(18) . . . . ? N2 C1 C11 C12 5.27(17) . . . . ? C7 C1 C11 C12 -173.87(12) . . . . ? C16 C11 C12 O1 178.85(11) . . . . ? C1 C11 C12 O1 -0.69(18) . . . . ? C16 C11 C12 C13 -1.24(17) . . . . ? C1 C11 C12 C13 179.22(11) . . . . ? O1 C12 C13 C14 -178.92(11) . . . . ? C11 C12 C13 C14 1.17(18) . . . . ? C12 C13 C14 C15 -0.31(19) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C14 C15 C16 C11 0.3(2) . . . . ? C12 C11 C16 C15 0.50(19) . . . . ? C1 C11 C16 C15 -179.96(12) . . . . ? N5 C6 C21 C26 176.88(11) . . . . ? C9 C6 C21 C26 -3.14(17) . . . . ? N5 C6 C21 C22 -2.15(16) . . . . ? C9 C6 C21 C22 177.83(11) . . . . ? C26 C21 C22 O2 -179.93(11) . . . . ? C6 C21 C22 O2 -0.87(17) . . . . ? C26 C21 C22 C23 -0.28(17) . . . . ? C6 C21 C22 C23 178.78(11) . . . . ? O2 C22 C23 C24 179.31(12) . . . . ? C21 C22 C23 C24 -0.34(19) . . . . ? C22 C23 C24 C25 0.6(2) . . . . ? C23 C24 C25 C26 -0.2(2) . . . . ? C24 C25 C26 C21 -0.4(2) . . . . ? C22 C21 C26 C25 0.67(18) . . . . ? C6 C21 C26 C25 -178.37(11) . . . . ? 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 O1 H1 N2 1.04(2) 1.55(2) 2.5276(14) 155.6(18) . N5 H2 O2 1.24(2) 1.30(2) 2.4759(13) 155(2) . O1W H1W O2 0.94(2) 1.94(2) 2.8806(12) 173.1(18) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.275 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.043