# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_date 2013-09-09T14:26:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H16 N4 O6' _chemical_formula_sum 'C16 H16 N4 O6' _chemical_formula_weight 360.33 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.0171(2) _cell_length_b 16.1781(6) _cell_length_c 10.3154(4) _cell_angle_alpha 90 _cell_angle_beta 102.463(2) _cell_angle_gamma 90 _cell_volume 817.54(5) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4178 _cell_measurement_theta_min 5.17 _cell_measurement_theta_max 67.6 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prisms _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.97 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_av_unetI/netI 0.028 _diffrn_reflns_number 2471 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.17 _diffrn_reflns_theta_max 67.88 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.932 _reflns_number_total 2471 _reflns_number_gt 2342 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1291P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2471 _refine_ls_number_parameters 236 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1503 _refine_ls_wR_factor_gt 0.148 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 1042 Friedel pairs' _refine_ls_abs_structure_Flack 0.0(3) _refine_diff_density_max 0.396 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.067 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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 C1 C 0.2415(5) 0.28663(19) -0.1862(3) 0.0312(6) Uani 1 1 d . . . C2 C 0.4412(5) 0.34480(17) -0.1328(3) 0.0283(6) Uani 1 1 d . . . C3 C 0.5956(6) 0.3792(2) -0.2171(3) 0.0361(7) Uani 1 1 d . . . H3 H 0.7331 0.4168 -0.1834 0.043 Uiso 1 1 calc R . . C4 C 0.5466(7) 0.3580(2) -0.3495(3) 0.0439(8) Uani 1 1 d . . . H4 H 0.6524 0.3809 -0.404 0.053 Uiso 1 1 calc R . . C5 C 0.3423(7) 0.3031(2) -0.4014(3) 0.0407(7) Uani 1 1 d . . . H5 H 0.3076 0.2899 -0.4912 0.049 Uiso 1 1 calc R . . C6 C 0.1877(6) 0.2674(2) -0.3198(3) 0.0390(7) Uani 1 1 d . . . H6 H 0.0484 0.2306 -0.355 0.047 Uiso 1 1 calc R . . O7 O 0.1067(4) 0.25172(14) -0.0975(2) 0.0395(5) Uani 1 1 d . . . C8 C -0.0676(7) 0.1836(2) -0.1432(3) 0.0421(8) Uani 1 1 d . . . H81 H -0.1266 0.1589 -0.0696 0.063 Uiso 1 1 calc R . . H82 H 0.03 0.1435 -0.1835 0.063 Uiso 1 1 calc R . . H83 H -0.2236 0.2025 -0.2074 0.063 Uiso 1 1 calc R . . C9 C 0.4880(5) 0.36665(18) 0.0135(3) 0.0300(6) Uani 1 1 d . . . H9 H 0.3113 0.3745 0.0378 0.036 Uiso 1 1 calc R . . C10 C 0.6424(6) 0.2969(2) 0.0967(3) 0.0371(7) Uani 1 1 d . . . H101 H 0.5834 0.2447 0.0537 0.045 Uiso 1 1 calc R . . H102 H 0.8355 0.303 0.0983 0.045 Uiso 1 1 calc R . . N11 N 0.6050(6) 0.29342(18) 0.2372(2) 0.0441(7) Uani 1 1 d . . . O12 O 0.7840(7) 0.2617(3) 0.3191(3) 0.0830(11) Uani 1 1 d . . . O13 O 0.3925(6) 0.3185(2) 0.2615(3) 0.0645(8) Uani 1 1 d . . . N14 N 0.6449(5) 0.44399(17) 0.0366(2) 0.0364(6) Uani 1 1 d . . . H14 H 0.679 0.4738 -0.027 0.044 Uiso 1 1 calc R . . N15 N 0.7348(5) 0.46525(16) 0.1713(2) 0.0340(6) Uani 1 1 d . . . H15 H 0.9031 0.4574 0.2092 0.041 Uiso 1 1 calc R . . C16 C 0.5641(5) 0.49758(18) 0.2427(3) 0.0307(6) Uani 1 1 d . . . O17 O 0.3201(4) 0.50643(14) 0.1961(2) 0.0430(6) Uani 1 1 d . . . C18 C 0.6887(5) 0.52225(18) 0.3823(3) 0.0310(6) Uani 1 1 d . . . C19 C 0.9304(6) 0.4882(2) 0.4560(3) 0.0406(7) Uani 1 1 d . . . H19 H 1.0263 0.4496 0.4173 0.049 Uiso 1 1 calc R . . C20 C 1.0266(6) 0.5118(2) 0.5859(3) 0.0452(8) Uani 1 1 d . . . H20 H 1.186 0.4888 0.6356 0.054 Uiso 1 1 calc R . . C21 C 0.8851(7) 0.5697(2) 0.6412(3) 0.0412(7) Uani 1 1 d . . . C22 C 0.6480(7) 0.6049(2) 0.5712(3) 0.0447(8) Uani 1 1 d . . . H22 H 0.5553 0.6443 0.6101 0.054 Uiso 1 1 calc R . . C23 C 0.5516(6) 0.5800(2) 0.4419(3) 0.0393(7) Uani 1 1 d . . . H23 H 0.3901 0.6026 0.3935 0.047 Uiso 1 1 calc R . . N24 N 0.9851(7) 0.5937(2) 0.7797(3) 0.0591(9) Uani 1 1 d . . . O25 O 1.2114(7) 0.5725(3) 0.8367(3) 0.0936(12) Uani 1 1 d . . . O26 O 0.8346(8) 0.6359(3) 0.8322(3) 0.0938(12) Uani 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 C1 0.0328(13) 0.0391(16) 0.0214(13) 0.0008(12) 0.0053(10) 0.0027(12) C2 0.0309(13) 0.0341(16) 0.0197(13) 0.0022(11) 0.0051(10) 0.0040(10) C3 0.0387(15) 0.0384(17) 0.0329(16) 0.0030(12) 0.0115(12) -0.0003(13) C4 0.0528(18) 0.053(2) 0.0300(17) 0.0080(15) 0.0185(14) 0.0074(16) C5 0.0539(17) 0.050(2) 0.0178(13) -0.0007(12) 0.0063(12) 0.0112(15) C6 0.0417(14) 0.0472(19) 0.0254(15) -0.0069(13) 0.0015(11) -0.0001(13) O7 0.0456(11) 0.0482(13) 0.0254(10) -0.0064(9) 0.0090(8) -0.0152(10) C8 0.0485(17) 0.0434(19) 0.0331(16) -0.0081(14) 0.0064(13) -0.0087(14) C9 0.0302(12) 0.0362(15) 0.0234(14) -0.0013(12) 0.0054(10) -0.0013(12) C10 0.0448(15) 0.0443(18) 0.0226(14) 0.0031(12) 0.0080(12) -0.0008(13) N11 0.0552(16) 0.0500(18) 0.0264(13) 0.0026(12) 0.0072(12) -0.0115(13) O12 0.0848(19) 0.121(3) 0.0350(14) 0.0279(17) -0.0048(14) 0.005(2) O13 0.0773(18) 0.080(2) 0.0443(14) 0.0070(14) 0.0310(13) -0.0023(16) N14 0.0441(13) 0.0440(15) 0.0224(12) -0.0011(11) 0.0100(10) -0.0102(11) N15 0.0292(11) 0.0439(15) 0.0273(13) -0.0081(11) 0.0028(9) -0.0042(10) C16 0.0290(12) 0.0292(15) 0.0334(14) -0.0022(12) 0.0058(11) -0.0041(11) O17 0.0302(10) 0.0567(15) 0.0392(11) -0.0058(10) 0.0009(8) 0.0053(9) C18 0.0352(13) 0.0299(15) 0.0283(14) 0.0000(12) 0.0075(11) -0.0031(12) C19 0.0376(14) 0.0491(18) 0.0345(17) -0.0050(14) 0.0060(12) 0.0057(13) C20 0.0393(15) 0.055(2) 0.0361(17) 0.0013(16) -0.0026(13) 0.0004(15) C21 0.0525(17) 0.0426(18) 0.0278(16) -0.0027(13) 0.0069(13) -0.0118(14) C22 0.0593(19) 0.039(2) 0.0362(17) -0.0070(13) 0.0119(15) 0.0060(15) C23 0.0435(14) 0.0399(18) 0.0329(16) 0.0016(14) 0.0048(12) 0.0075(14) N24 0.077(2) 0.062(2) 0.0324(16) -0.0065(15) -0.0017(15) -0.0085(18) O25 0.099(2) 0.120(3) 0.0445(17) -0.0201(19) -0.0231(17) 0.020(2) O26 0.112(3) 0.118(3) 0.0481(18) -0.0362(19) 0.0101(18) 0.015(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O7 1.372(3) . ? C1 C6 1.382(4) . ? C1 C2 1.398(4) . ? C2 C3 1.399(4) . ? C2 C9 1.519(4) . ? C3 C4 1.377(4) . ? C3 H3 0.93 . ? C4 C5 1.375(5) . ? C4 H4 0.93 . ? C5 C6 1.387(5) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? O7 C8 1.422(4) . ? C8 H81 0.96 . ? C8 H82 0.96 . ? C8 H83 0.96 . ? C9 N14 1.470(4) . ? C9 C10 1.524(4) . ? C9 H9 0.98 . ? C10 N11 1.503(4) . ? C10 H101 0.97 . ? C10 H102 0.97 . ? N11 O12 1.206(4) . ? N11 O13 1.216(4) . ? N14 N15 1.408(3) . ? N14 H14 0.86 . ? N15 C16 1.349(4) . ? N15 H15 0.86 . ? C16 O17 1.223(3) . ? C16 C18 1.495(4) . ? C18 C23 1.380(4) . ? C18 C19 1.398(4) . ? C19 C20 1.376(5) . ? C19 H19 0.93 . ? C20 C21 1.372(5) . ? C20 H20 0.93 . ? C21 C22 1.374(5) . ? C21 N24 1.462(4) . ? C22 C23 1.377(5) . ? C22 H22 0.93 . ? C23 H23 0.93 . ? N24 O25 1.210(5) . ? N24 O26 1.226(5) . ? 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 O7 C1 C6 123.7(3) . . ? O7 C1 C2 115.4(2) . . ? C6 C1 C2 120.9(2) . . ? C1 C2 C3 117.9(2) . . ? C1 C2 C9 119.5(2) . . ? C3 C2 C9 122.5(3) . . ? C4 C3 C2 120.9(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120 . . ? C6 C5 H5 120 . . ? C1 C6 C5 119.8(3) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C1 O7 C8 117.0(2) . . ? O7 C8 H81 109.5 . . ? O7 C8 H82 109.5 . . ? H81 C8 H82 109.5 . . ? O7 C8 H83 109.5 . . ? H81 C8 H83 109.5 . . ? H82 C8 H83 109.5 . . ? N14 C9 C2 108.7(2) . . ? N14 C9 C10 110.5(2) . . ? C2 C9 C10 109.8(2) . . ? N14 C9 H9 109.3 . . ? C2 C9 H9 109.3 . . ? C10 C9 H9 109.3 . . ? N11 C10 C9 114.6(3) . . ? N11 C10 H101 108.6 . . ? C9 C10 H101 108.6 . . ? N11 C10 H102 108.6 . . ? C9 C10 H102 108.6 . . ? H101 C10 H102 107.6 . . ? O12 N11 O13 123.4(3) . . ? O12 N11 C10 117.5(3) . . ? O13 N11 C10 118.9(3) . . ? N15 N14 C9 114.4(2) . . ? N15 N14 H14 122.8 . . ? C9 N14 H14 122.8 . . ? C16 N15 N14 121.8(2) . . ? C16 N15 H15 119.1 . . ? N14 N15 H15 119.1 . . ? O17 C16 N15 122.0(3) . . ? O17 C16 C18 121.5(3) . . ? N15 C16 C18 116.5(2) . . ? C23 C18 C19 118.7(3) . . ? C23 C18 C16 117.7(2) . . ? C19 C18 C16 123.5(3) . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 119.3(3) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 122.1(3) . . ? C20 C21 N24 119.3(3) . . ? C22 C21 N24 118.6(3) . . ? C21 C22 C23 118.1(3) . . ? C21 C22 H22 121 . . ? C23 C22 H22 121 . . ? C22 C23 C18 121.6(3) . . ? C22 C23 H23 119.2 . . ? C18 C23 H23 119.2 . . ? O25 N24 O26 123.1(3) . . ? O25 N24 C21 119.2(4) . . ? O26 N24 C21 117.7(3) . . ? 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 O7 C1 C2 C3 176.6(2) . . . . ? C6 C1 C2 C3 -3.7(4) . . . . ? O7 C1 C2 C9 -1.8(4) . . . . ? C6 C1 C2 C9 177.9(3) . . . . ? C1 C2 C3 C4 1.8(4) . . . . ? C9 C2 C3 C4 -179.8(3) . . . . ? C2 C3 C4 C5 0.7(5) . . . . ? C3 C4 C5 C6 -1.4(5) . . . . ? O7 C1 C6 C5 -177.2(3) . . . . ? C2 C1 C6 C5 3.1(5) . . . . ? C4 C5 C6 C1 -0.5(5) . . . . ? C6 C1 O7 C8 9.6(4) . . . . ? C2 C1 O7 C8 -170.7(3) . . . . ? C1 C2 C9 N14 -163.8(2) . . . . ? C3 C2 C9 N14 17.8(4) . . . . ? C1 C2 C9 C10 75.2(3) . . . . ? C3 C2 C9 C10 -103.1(3) . . . . ? N14 C9 C10 N11 83.6(3) . . . . ? C2 C9 C10 N11 -156.5(2) . . . . ? C9 C10 N11 O12 -154.5(3) . . . . ? C9 C10 N11 O13 29.2(4) . . . . ? C2 C9 N14 N15 -171.7(2) . . . . ? C10 C9 N14 N15 -51.2(3) . . . . ? C9 N14 N15 C16 -76.5(4) . . . . ? N14 N15 C16 O17 3.6(4) . . . . ? N14 N15 C16 C18 -176.4(3) . . . . ? O17 C16 C18 C23 -22.2(4) . . . . ? N15 C16 C18 C23 157.8(3) . . . . ? O17 C16 C18 C19 155.8(3) . . . . ? N15 C16 C18 C19 -24.2(4) . . . . ? C23 C18 C19 C20 0.5(5) . . . . ? C16 C18 C19 C20 -177.4(3) . . . . ? C18 C19 C20 C21 -0.9(5) . . . . ? C19 C20 C21 C22 0.4(5) . . . . ? C19 C20 C21 N24 179.0(3) . . . . ? C20 C21 C22 C23 0.5(5) . . . . ? N24 C21 C22 C23 -178.2(3) . . . . ? C21 C22 C23 C18 -0.8(5) . . . . ? C19 C18 C23 C22 0.4(5) . . . . ? C16 C18 C23 C22 178.5(3) . . . . ? C20 C21 N24 O25 11.6(6) . . . . ? C22 C21 N24 O25 -169.7(4) . . . . ? C20 C21 N24 O26 -169.3(4) . . . . ? C22 C21 N24 O26 9.4(6) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 959956'