# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_compound_1 _database_code_depnum_ccdc_archive 'CCDC 734294' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 N4' _chemical_formula_weight 198.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.0582(13) _cell_length_b 17.577(3) _cell_length_c 8.5676(16) _cell_angle_alpha 90.00 _cell_angle_beta 101.257(2) _cell_angle_gamma 90.00 _cell_volume 1042.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4010 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 26.84 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9761 _exptl_absorpt_correction_T_max 0.9840 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8798 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.61 _reflns_number_total 2408 _reflns_number_gt 1848 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0276P)^2^+0.4539P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2408 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1209 _refine_ls_goodness_of_fit_ref 1.198 _refine_ls_restrained_S_all 1.198 _refine_ls_shift/su_max 0.000 _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 C1 C 0.2748(3) -0.03236(12) 0.0261(2) 0.0518(5) Uani 1 1 d . . . C2 C 0.2020(3) 0.08808(12) 0.0018(2) 0.0532(5) Uani 1 1 d . . . H2 H 0.159(3) 0.1378(14) 0.031(3) 0.070(7) Uiso 1 1 d . . . C3 C 0.2263(3) 0.05935(13) -0.1389(2) 0.0558(5) Uani 1 1 d . . . H3 H 0.213(3) 0.0851(13) -0.238(3) 0.070(7) Uiso 1 1 d . . . C4 C 0.2179(4) 0.02926(15) 0.2750(2) 0.0584(6) Uani 1 1 d . . . H4A H 0.082(4) 0.0467(13) 0.286(3) 0.073(7) Uiso 1 1 d . . . H4B H 0.227(4) -0.0258(15) 0.315(3) 0.080(8) Uiso 1 1 d . . . C5 C 0.3648(3) 0.07983(11) 0.3757(2) 0.0464(4) Uani 1 1 d . . . C6 C 0.5005(3) 0.15279(10) 0.5622(2) 0.0494(5) Uani 1 1 d . . . C7 C 0.5500(5) 0.19944(13) 0.6965(3) 0.0679(7) Uani 1 1 d . . . H7 H 0.455(3) 0.2109(13) 0.754(3) 0.065(7) Uiso 1 1 d . . . C8 C 0.7347(5) 0.22585(14) 0.7361(3) 0.0816(9) Uani 1 1 d . . . H8 H 0.780(4) 0.2578(16) 0.824(3) 0.091(8) Uiso 1 1 d . . . C9 C 0.8716(5) 0.20804(15) 0.6453(4) 0.0814(8) Uani 1 1 d . . . H9 H 1.005(4) 0.2269(16) 0.675(3) 0.099(9) Uiso 1 1 d . . . C10 C 0.8280(4) 0.16313(14) 0.5114(3) 0.0672(6) Uani 1 1 d . . . H10 H 0.922(3) 0.1499(13) 0.448(3) 0.066(7) Uiso 1 1 d . . . C11 C 0.6393(3) 0.13583(11) 0.4725(2) 0.0502(5) Uani 1 1 d . . . H1 H 0.302(3) -0.0832(13) 0.076(3) 0.067(6) Uiso 1 1 d . . . N1 N 0.2725(3) -0.01626(11) -0.12391(19) 0.0575(5) Uani 1 1 d . . . N2 N 0.2334(2) 0.02850(9) 0.10722(17) 0.0461(4) Uani 1 1 d . . . N3 N 0.3265(3) 0.11726(10) 0.49850(17) 0.0513(4) Uani 1 1 d . . . N4 N 0.5474(3) 0.08857(10) 0.35226(19) 0.0520(4) Uani 1 1 d . . . H4 H 0.605(4) 0.0666(14) 0.277(3) 0.077(8) 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 C1 0.0506(12) 0.0527(11) 0.0498(11) -0.0066(9) 0.0040(9) -0.0021(9) C2 0.0626(13) 0.0519(11) 0.0439(10) 0.0007(9) 0.0073(9) -0.0005(10) C3 0.0570(13) 0.0713(14) 0.0374(10) 0.0023(10) 0.0051(9) -0.0081(10) C4 0.0656(15) 0.0752(15) 0.0340(10) -0.0039(10) 0.0093(9) -0.0143(12) C5 0.0548(12) 0.0535(10) 0.0299(8) 0.0028(8) 0.0058(8) 0.0008(9) C6 0.0675(13) 0.0449(10) 0.0325(9) 0.0017(7) 0.0015(8) 0.0067(9) C7 0.105(2) 0.0537(12) 0.0418(11) -0.0072(9) 0.0066(12) 0.0051(13) C8 0.123(3) 0.0522(13) 0.0561(14) -0.0097(11) -0.0164(15) -0.0096(15) C9 0.085(2) 0.0625(15) 0.0814(19) -0.0018(13) -0.0220(16) -0.0141(14) C10 0.0623(15) 0.0637(14) 0.0710(15) -0.0016(12) 0.0022(12) -0.0057(12) C11 0.0595(12) 0.0457(10) 0.0409(10) 0.0004(8) -0.0012(9) 0.0024(9) N1 0.0545(11) 0.0737(12) 0.0434(9) -0.0158(8) 0.0075(8) -0.0054(9) N2 0.0502(9) 0.0540(9) 0.0327(7) -0.0032(7) 0.0049(6) -0.0043(7) N3 0.0611(11) 0.0602(10) 0.0324(8) 0.0009(7) 0.0090(7) 0.0042(8) N4 0.0571(11) 0.0592(10) 0.0397(8) -0.0100(7) 0.0090(7) -0.0001(8) _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 N1 1.313(3) . ? C1 N2 1.339(2) . ? C1 H1 0.99(2) . ? C2 C3 1.348(3) . ? C2 N2 1.373(2) . ? C2 H2 0.98(2) . ? C3 N1 1.369(3) . ? C3 H3 0.95(2) . ? C4 N2 1.463(2) . ? C4 C5 1.503(3) . ? C4 H4A 1.03(3) . ? C4 H4B 1.03(2) . ? C5 N3 1.313(2) . ? C5 N4 1.351(3) . ? C6 C11 1.390(3) . ? C6 N3 1.391(3) . ? C6 C7 1.400(3) . ? C7 C8 1.363(4) . ? C7 H7 0.93(2) . ? C8 C9 1.389(4) . ? C8 H8 0.95(3) . ? C9 C10 1.377(4) . ? C9 H9 0.98(3) . ? C10 C11 1.394(3) . ? C10 H10 0.96(2) . ? C11 N4 1.383(2) . ? N4 H4 0.91(3) . ? 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 N1 C1 N2 111.95(19) . . ? N1 C1 H1 125.3(13) . . ? N2 C1 H1 122.7(13) . . ? C3 C2 N2 105.68(19) . . ? C3 C2 H2 132.0(13) . . ? N2 C2 H2 122.0(13) . . ? C2 C3 N1 110.46(19) . . ? C2 C3 H3 127.7(14) . . ? N1 C3 H3 121.8(14) . . ? N2 C4 C5 113.16(17) . . ? N2 C4 H4A 109.9(13) . . ? C5 C4 H4A 109.0(13) . . ? N2 C4 H4B 108.1(14) . . ? C5 C4 H4B 111.9(14) . . ? H4A C4 H4B 104.6(19) . . ? N3 C5 N4 114.43(17) . . ? N3 C5 C4 121.93(19) . . ? N4 C5 C4 123.59(18) . . ? C11 C6 N3 110.51(16) . . ? C11 C6 C7 119.3(2) . . ? N3 C6 C7 130.2(2) . . ? C8 C7 C6 118.5(3) . . ? C8 C7 H7 123.3(15) . . ? C6 C7 H7 118.2(15) . . ? C7 C8 C9 121.3(2) . . ? C7 C8 H8 123.8(17) . . ? C9 C8 H8 114.8(17) . . ? C10 C9 C8 121.9(3) . . ? C10 C9 H9 117.2(17) . . ? C8 C9 H9 120.9(17) . . ? C9 C10 C11 116.3(3) . . ? C9 C10 H10 122.9(14) . . ? C11 C10 H10 120.7(14) . . ? N4 C11 C6 105.19(18) . . ? N4 C11 C10 132.2(2) . . ? C6 C11 C10 122.6(2) . . ? C1 N1 C3 104.97(17) . . ? C1 N2 C2 106.93(17) . . ? C1 N2 C4 125.69(18) . . ? C2 N2 C4 127.34(18) . . ? C5 N3 C6 103.61(17) . . ? C5 N4 C11 106.25(17) . . ? C5 N4 H4 128.8(16) . . ? C11 N4 H4 124.8(16) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.144 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.035 ####################################################################### # # 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_compound_2 _database_code_depnum_ccdc_archive 'CCDC 734295' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 N4 O2' _chemical_formula_weight 234.26 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 14.032(8) _cell_length_b 19.114(10) _cell_length_c 4.625(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1240.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1917 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 20.24 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9823 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10276 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.77 _reflns_number_total 2857 _reflns_number_gt 1669 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0546P)^2^+0.0434P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3(2) _refine_ls_number_reflns 2857 _refine_ls_number_parameters 198 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.000 _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 0.11398(14) 0.88175(11) -0.3813(5) 0.0789(6) Uani 1 1 d . . . H1A H 0.1214 0.9256 -0.3612 0.155(19) Uiso 1 1 d R . . H1B H 0.1336 0.8700 -0.2143 0.129(17) Uiso 1 1 d R . . O2 O 0.17674(14) 0.81672(10) 0.1363(5) 0.0785(6) Uani 1 1 d . . . H2B H 0.2362 0.8126 0.1061 0.129(15) Uiso 1 1 d R . . H2A H 0.1639 0.8391 0.2903 0.101(13) Uiso 1 1 d R . . C1 C -0.0830(3) 0.92786(16) 0.2054(8) 0.0819(9) Uani 1 1 d . . . C2 C -0.2042(2) 0.87160(18) 0.0345(9) 0.0844(10) Uani 1 1 d . . . H2 H -0.250(2) 0.8318(17) 0.000(8) 0.100(11) Uiso 1 1 d . . . C3 C -0.2090(3) 0.93898(19) -0.0417(10) 0.0982(11) Uani 1 1 d . . . H3 H -0.251(2) 0.9633(18) -0.188(9) 0.113(12) Uiso 1 1 d . . . C4 C -0.0880(2) 0.80032(14) 0.3280(6) 0.0651(7) Uani 1 1 d . . . H4B H -0.135(2) 0.7869(14) 0.487(8) 0.091(9) Uiso 1 1 d . . . C5 C -0.06837(18) 0.74539(12) 0.1101(6) 0.0549(6) Uani 1 1 d . . . C6 C 0.01095(18) 0.68174(13) -0.2031(5) 0.0548(6) Uani 1 1 d . . . C7 C 0.0752(2) 0.64926(16) -0.3880(7) 0.0687(7) Uani 1 1 d . . . H7 H 0.1325(18) 0.6672(12) -0.404(7) 0.062(8) Uiso 1 1 d . . . C8 C 0.0435(3) 0.59271(16) -0.5437(7) 0.0761(9) Uani 1 1 d . . . H8 H 0.092(2) 0.5675(17) -0.692(9) 0.107(11) Uiso 1 1 d . . . C9 C -0.0499(2) 0.56848(16) -0.5172(7) 0.0769(8) Uani 1 1 d . . . H9 H -0.069(2) 0.5275(16) -0.636(9) 0.104(11) Uiso 1 1 d . . . C10 C -0.1140(2) 0.60049(14) -0.3381(7) 0.0697(8) Uani 1 1 d . . . H10 H -0.184(2) 0.5816(16) -0.313(8) 0.098(10) Uiso 1 1 d . . . C11 C -0.08331(18) 0.65782(12) -0.1791(5) 0.0559(6) Uani 1 1 d . . . N1 N -0.1330(2) 0.97542(12) 0.0661(7) 0.0951(9) Uani 1 1 d . . . N2 N -0.12341(15) 0.86484(11) 0.1947(5) 0.0612(6) Uani 1 1 d . . . N3 N 0.01748(16) 0.73728(11) -0.0179(4) 0.0573(5) Uani 1 1 d . . . H3A H 0.068(2) 0.7630(14) 0.031(7) 0.077(9) Uiso 1 1 d . . . N4 N -0.13171(14) 0.69930(10) 0.0204(5) 0.0588(5) Uani 1 1 d . . . H4A H -0.030(2) 0.8154(13) 0.448(8) 0.078(8) Uiso 1 1 d . . . H1 H -0.024(2) 0.9364(16) 0.300(8) 0.095(11) 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 0.0862(14) 0.0696(13) 0.0811(15) -0.0097(12) -0.0040(13) 0.0023(9) O2 0.0604(13) 0.0948(14) 0.0804(13) -0.0206(13) -0.0014(11) -0.0060(10) C1 0.082(2) 0.0604(18) 0.103(2) 0.0000(17) -0.027(2) 0.0001(16) C2 0.0738(19) 0.073(2) 0.106(3) -0.0100(19) -0.028(2) 0.0113(16) C3 0.103(3) 0.078(2) 0.114(3) -0.004(2) -0.029(3) 0.030(2) C4 0.0775(19) 0.0598(16) 0.0581(16) 0.0037(14) -0.0088(16) 0.0030(15) C5 0.0640(16) 0.0488(13) 0.0519(13) 0.0068(12) -0.0045(14) 0.0054(11) C6 0.0602(16) 0.0536(14) 0.0505(13) 0.0062(12) -0.0055(13) 0.0053(12) C7 0.0641(18) 0.0764(19) 0.0655(17) 0.0104(18) -0.0018(16) 0.0067(15) C8 0.097(2) 0.0692(19) 0.0626(18) 0.0048(16) 0.0036(18) 0.0219(17) C9 0.100(2) 0.0599(18) 0.0706(18) 0.0002(17) -0.007(2) 0.0076(16) C10 0.077(2) 0.0588(16) 0.0738(18) -0.0039(15) -0.0035(17) 0.0005(14) C11 0.0591(15) 0.0518(14) 0.0569(15) 0.0065(13) -0.0015(13) 0.0021(12) N1 0.1034(19) 0.0607(14) 0.121(2) 0.0033(17) -0.0237(19) 0.0083(14) N2 0.0641(13) 0.0539(12) 0.0656(14) -0.0045(10) -0.0085(11) 0.0085(10) N3 0.0554(13) 0.0584(12) 0.0581(12) 0.0038(12) -0.0014(12) -0.0011(11) N4 0.0596(13) 0.0520(11) 0.0649(13) 0.0027(11) -0.0025(11) -0.0005(10) _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 H1A 0.8501 . ? O1 H1B 0.8500 . ? O2 H2B 0.8500 . ? O2 H2A 0.8499 . ? C1 N1 1.317(4) . ? C1 N2 1.333(4) . ? C1 H1 0.95(3) . ? C2 C3 1.337(5) . ? C2 N2 1.360(4) . ? C2 H2 1.01(3) . ? C3 N1 1.367(5) . ? C3 H3 1.01(4) . ? C4 N2 1.466(3) . ? C4 C5 1.481(4) . ? C4 H4B 1.02(3) . ? C4 H4A 1.02(3) . ? C5 N4 1.318(3) . ? C5 N3 1.351(3) . ? C6 N3 1.367(3) . ? C6 C7 1.389(4) . ? C6 C11 1.404(4) . ? C7 C8 1.373(4) . ? C7 H7 0.88(2) . ? C8 C9 1.395(4) . ? C8 H8 1.08(4) . ? C9 C10 1.367(4) . ? C9 H9 0.99(4) . ? C10 C11 1.388(4) . ? C10 H10 1.05(3) . ? C11 N4 1.393(3) . ? N3 H3A 0.89(3) . ? 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 H1A O1 H1B 97.0 . . ? H2B O2 H2A 113.1 . . ? N1 C1 N2 112.3(3) . . ? N1 C1 H1 125(2) . . ? N2 C1 H1 123(2) . . ? C3 C2 N2 106.1(3) . . ? C3 C2 H2 130.6(19) . . ? N2 C2 H2 123.2(19) . . ? C2 C3 N1 110.8(3) . . ? C2 C3 H3 131(2) . . ? N1 C3 H3 118(2) . . ? N2 C4 C5 111.9(2) . . ? N2 C4 H4B 107.2(16) . . ? C5 C4 H4B 115.6(17) . . ? N2 C4 H4A 105.1(15) . . ? C5 C4 H4A 115.0(15) . . ? H4B C4 H4A 101(2) . . ? N4 C5 N3 112.7(2) . . ? N4 C5 C4 124.3(2) . . ? N3 C5 C4 123.0(2) . . ? N3 C6 C7 133.6(3) . . ? N3 C6 C11 105.5(2) . . ? C7 C6 C11 121.0(3) . . ? C8 C7 C6 117.7(3) . . ? C8 C7 H7 124.2(18) . . ? C6 C7 H7 118.1(18) . . ? C7 C8 C9 121.3(3) . . ? C7 C8 H8 118.5(18) . . ? C9 C8 H8 120.1(18) . . ? C10 C9 C8 121.5(3) . . ? C10 C9 H9 121(2) . . ? C8 C9 H9 117(2) . . ? C9 C10 C11 118.0(3) . . ? C9 C10 H10 121.7(18) . . ? C11 C10 H10 120.2(19) . . ? C10 C11 N4 130.5(3) . . ? C10 C11 C6 120.5(3) . . ? N4 C11 C6 109.0(2) . . ? C1 N1 C3 104.0(3) . . ? C1 N2 C2 106.8(3) . . ? C1 N2 C4 126.9(3) . . ? C2 N2 C4 126.3(3) . . ? C5 N3 C6 107.7(2) . . ? C5 N3 H3A 122(2) . . ? C6 N3 H3A 130(2) . . ? C5 N4 C11 105.1(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.77 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.117 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.031 ####################################################################### # # 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_ibi _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 N4 O3' _chemical_formula_weight 252.28 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 13.554(2) _cell_length_b 21.511(3) _cell_length_c 4.5170(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1317.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2315 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 22.83 _exptl_crystal_description needle _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9630 _exptl_absorpt_correction_T_max 0.9813 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10153 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.37 _reflns_number_total 2667 _reflns_number_gt 2147 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0931P)^2^+0.1205P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.9(16) _refine_ls_number_reflns 2667 _refine_ls_number_parameters 173 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 0.829 _refine_ls_restrained_S_all 0.829 _refine_ls_shift/su_max 0.000 _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 O1W O 1.10869(12) 0.36815(7) 0.1685(4) 0.0385(4) Uani 1 1 d . . . H1WA H 1.0885 0.3503 0.0119 0.063(10) Uiso 1 1 d R . . H1WB H 1.0942 0.4064 0.1502 0.059(8) Uiso 1 1 d R . . O2W O 1.05740(12) 0.49000(7) 0.1369(4) 0.0405(4) Uani 1 1 d . . . H2WB H 1.0239 0.4981 0.2912 0.072(11) Uiso 1 1 d R . . H2WA H 1.1042 0.5161 0.1226 0.071(10) Uiso 1 1 d R . . O3W O 1.06654(12) 0.30076(8) 0.6789(4) 0.0426(4) Uani 1 1 d . . . H3WA H 1.0792 0.3207 0.5210 0.082(12) Uiso 1 1 d R . . H3WB H 1.0126 0.2814 0.6512 0.068(10) Uiso 1 1 d R . . C1 C 0.84313(17) 0.36834(10) 0.3633(6) 0.0403(6) Uani 1 1 d . . . H1A H 0.9006 0.3700 0.2509 0.048 Uiso 1 1 calc R . . C2 C 0.70670(15) 0.33453(10) 0.5582(6) 0.0353(5) Uani 1 1 d . . . H2A H 0.6527 0.3100 0.6076 0.042 Uiso 1 1 calc R . . C3 C 0.72729(17) 0.39144(10) 0.6615(7) 0.0412(6) Uani 1 1 d . . . H3A H 0.6888 0.4131 0.7973 0.049 Uiso 1 1 calc R . . C4 C 0.79470(18) 0.26056(10) 0.2165(5) 0.0397(6) Uani 1 1 d . . . H4A H 0.8411 0.2659 0.0549 0.048 Uiso 1 1 calc R . . H4B H 0.7324 0.2470 0.1332 0.048 Uiso 1 1 calc R . . C5 C 0.83264(16) 0.21171(9) 0.4232(5) 0.0303(5) Uani 1 1 d . . . C6 C 0.84254(15) 0.12226(9) 0.6542(6) 0.0322(5) Uani 1 1 d . . . C7 C 0.8330(2) 0.06240(10) 0.7723(6) 0.0464(7) Uani 1 1 d . . . H7A H 0.7827 0.0357 0.7133 0.056 Uiso 1 1 calc R . . C8 C 0.9018(2) 0.04510(12) 0.9800(6) 0.0525(8) Uani 1 1 d . . . H8A H 0.8980 0.0055 1.0618 0.063 Uiso 1 1 calc R . . C9 C 0.9771(2) 0.08481(13) 1.0728(6) 0.0492(7) Uani 1 1 d . . . H9A H 1.0221 0.0712 1.2142 0.059 Uiso 1 1 calc R . . C10 C 0.98580(17) 0.14313(12) 0.9596(6) 0.0400(6) Uani 1 1 d . . . H10A H 1.0356 0.1697 1.0234 0.048 Uiso 1 1 calc R . . C11 C 0.91810(15) 0.16209(9) 0.7453(5) 0.0306(5) Uani 1 1 d . . . N1 N 0.81274(14) 0.41324(9) 0.5392(5) 0.0432(5) Uani 1 1 d . . . N2 N 0.78073(13) 0.31974(8) 0.3664(4) 0.0312(4) Uani 1 1 d . . . N3 N 0.78984(14) 0.15545(9) 0.4490(5) 0.0340(5) Uani 1 1 d . . . N4 N 0.90980(12) 0.21835(7) 0.5963(4) 0.0317(4) Uani 1 1 d . . . H3 H 0.7408(19) 0.1468(12) 0.363(7) 0.037(7) 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 O1W 0.0432(9) 0.0330(8) 0.0393(9) 0.0063(8) -0.0032(8) 0.0020(7) O2W 0.0456(9) 0.0322(7) 0.0437(10) -0.0006(8) 0.0033(9) -0.0057(7) O3W 0.0421(9) 0.0430(8) 0.0428(10) 0.0082(9) -0.0030(9) -0.0108(7) C1 0.0333(12) 0.0367(12) 0.0509(16) 0.0083(12) 0.0035(12) 0.0005(9) C2 0.0303(11) 0.0332(11) 0.0425(14) 0.0038(10) 0.0038(10) 0.0019(9) C3 0.0420(13) 0.0319(11) 0.0497(14) -0.0038(12) 0.0022(12) 0.0095(9) C4 0.0513(14) 0.0338(12) 0.0341(13) -0.0025(10) -0.0041(12) 0.0086(10) C5 0.0336(11) 0.0272(10) 0.0301(12) -0.0040(9) 0.0034(10) 0.0055(8) C6 0.0362(11) 0.0259(10) 0.0347(12) -0.0021(9) 0.0137(11) 0.0046(8) C7 0.0637(16) 0.0275(11) 0.0480(16) -0.0064(11) 0.0234(13) -0.0039(11) C8 0.0831(19) 0.0306(12) 0.0438(16) 0.0108(11) 0.0258(15) 0.0215(13) C9 0.0584(16) 0.0493(14) 0.0400(15) 0.0120(12) 0.0166(13) 0.0254(12) C10 0.0331(12) 0.0489(14) 0.0380(14) 0.0072(12) 0.0089(11) 0.0102(10) C11 0.0295(11) 0.0283(10) 0.0340(13) 0.0012(9) 0.0098(9) 0.0044(8) N1 0.0397(11) 0.0320(9) 0.0580(14) 0.0015(9) -0.0010(11) -0.0025(8) N2 0.0346(9) 0.0275(9) 0.0314(10) 0.0022(8) -0.0007(9) 0.0046(7) N3 0.0300(10) 0.0320(10) 0.0400(12) -0.0098(9) 0.0033(9) -0.0022(8) N4 0.0362(9) 0.0269(9) 0.0319(11) 0.0020(8) 0.0024(9) -0.0020(7) _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 O1W H1WA 0.8500 . ? O1W H1WB 0.8499 . ? O2W H2WB 0.8500 . ? O2W H2WA 0.8500 . ? O3W H3WA 0.8499 . ? O3W H3WB 0.8500 . ? C1 N1 1.317(3) . ? C1 N2 1.345(3) . ? C1 H1A 0.9300 . ? C2 C3 1.339(3) . ? C2 N2 1.363(3) . ? C2 H2A 0.9300 . ? C3 N1 1.366(3) . ? C3 H3A 0.9300 . ? C4 N2 1.454(3) . ? C4 C5 1.497(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N4 1.314(3) . ? C5 N3 1.347(3) . ? C6 N3 1.371(3) . ? C6 C11 1.397(3) . ? C6 C7 1.400(3) . ? C7 C8 1.374(4) . ? C7 H7A 0.9300 . ? C8 C9 1.396(4) . ? C8 H8A 0.9300 . ? C9 C10 1.360(4) . ? C9 H9A 0.9300 . ? C10 C11 1.395(3) . ? C10 H10A 0.9300 . ? C11 N4 1.389(3) . ? N3 H3 0.79(3) . ? 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 H1WA O1W H1WB 106.3 . . ? H2WB O2W H2WA 108.9 . . ? H3WA O3W H3WB 107.3 . . ? N1 C1 N2 111.5(2) . . ? N1 C1 H1A 124.2 . . ? N2 C1 H1A 124.2 . . ? C3 C2 N2 106.33(19) . . ? C3 C2 H2A 126.8 . . ? N2 C2 H2A 126.8 . . ? C2 C3 N1 110.5(2) . . ? C2 C3 H3A 124.8 . . ? N1 C3 H3A 124.8 . . ? N2 C4 C5 111.66(19) . . ? N2 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N2 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? N4 C5 N3 112.89(19) . . ? N4 C5 C4 124.6(2) . . ? N3 C5 C4 122.5(2) . . ? N3 C6 C11 105.17(18) . . ? N3 C6 C7 133.5(2) . . ? C11 C6 C7 121.3(2) . . ? C8 C7 C6 116.5(2) . . ? C8 C7 H7A 121.7 . . ? C6 C7 H7A 121.7 . . ? C7 C8 C9 122.4(2) . . ? C7 C8 H8A 118.8 . . ? C9 C8 H8A 118.8 . . ? C10 C9 C8 121.0(3) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C9 C10 C11 118.3(2) . . ? C9 C10 H10A 120.9 . . ? C11 C10 H10A 120.9 . . ? N4 C11 C10 130.1(2) . . ? N4 C11 C6 109.40(19) . . ? C10 C11 C6 120.5(2) . . ? C1 N1 C3 104.92(19) . . ? C1 N2 C2 106.74(19) . . ? C1 N2 C4 126.4(2) . . ? C2 N2 C4 126.58(19) . . ? C5 N3 C6 107.6(2) . . ? C5 N3 H3 122.0(19) . . ? C6 N3 H3 130.3(19) . . ? C5 N4 C11 104.96(17) . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 27.37 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.138 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.031 #==END of File _database_code_depnum_ccdc_archive 'CCDC 734296'