# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address 'Rafel Prohens' ; Plataforma de Polimorfisme i Calorimetria, Centres Cient fics i Tecnol gics Universitat de Barcelona, 08028 Barcelona, Spain ; 'Anna Portell' ; Plataforma de Polimorfisme i Calorimetria, Centres Cient fics i Tecnol gics Universitat de Barcelona, 08028 Barcelona, Spain ; 'Cristina Puigjaner' ; Plataforma de Polimorfisme i Calorimetria, Centres Cient fics i Tecnol gics Universitat de Barcelona, 08028 Barcelona, Spain ; 'Rafael Barbas' ; Plataforma de Polimorfisme i Calorimetria, Centres Cient fics i Tecnol gics Universitat de Barcelona, 08028 Barcelona, Spain ; 'Xavier Alcob ' ; Unitat de Difracci\'o de Raigs X, Centres Cient fics i Tecnol gics Universitat de Barcelona, 08028 Barcelona, Spain ; ; M.Font-Bardia ; ; Unitat de Difracci\'o de Raigs X, Centres Cient fics i Tecnol gics Universitat de Barcelona, 08028 Barcelona, Spain ; 'Salvador Tomas' ; Department of Biological Sciences School of Science, Birkbeck University of London Malet Street, London WC1E 7HX United Kingdom ; _publ_contact_author_name 'Dr Rafel Prohens' _publ_contact_author_email rafel@sct.ub.es _publ_section_title ; Cooperative Induction in Double H-Bonding Donor/Acceptor compounds: Chains vs. Ribbons ; data_anom131a2 _database_code_depnum_ccdc_archive 'CCDC 865057' #TrackingRef '- 865057.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N2 O2' _chemical_formula_sum 'C6 H8 N2 O2' _chemical_formula_weight 140.14 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.087(4) _cell_length_b 7.307(3) _cell_length_c 16.041(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.98(3) _cell_angle_gamma 90.00 _cell_volume 670.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 179 _cell_measurement_theta_min 3 _cell_measurement_theta_max 31 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.106 _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 293(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 'MAR345 with image plate detector' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4842 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 30.47 _reflns_number_total 1619 _reflns_number_gt 1500 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MARXDS (Claudio Klein, 2005)' _computing_cell_refinement 'AUTOMAR (Claudio Klein, 2007)' _computing_data_reduction 'MARSCALE (Claudio Klein, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Brueggermann and Smith, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0438P)^2^+0.0599P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1619 _refine_ls_number_parameters 92 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.112 _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 0.60824(13) 0.69254(11) -0.04518(5) 0.0515(2) Uani 1 1 d . . . O2 O 0.79267(12) 0.90462(11) 0.14419(5) 0.0532(2) Uani 1 1 d U . . N1 N 0.07539(13) 0.69767(11) -0.04161(5) 0.0445(2) Uani 1 1 d U . . H1N H -0.0422 0.7201 -0.0291 0.053 Uiso 1 1 d R . . N2 N 0.25993(14) 0.91428(12) 0.14851(5) 0.0454(2) Uani 1 1 d U . . H2N H 0.1131 0.8999 0.1358 0.054 Uiso 1 1 d R . . C1 C 0.0471(2) 0.60292(17) -0.12412(7) 0.0564(3) Uani 1 1 d U . . H1A H -0.1124 0.5645 -0.1509 0.085 Uiso 1 1 calc R . . H1B H 0.1476 0.4977 -0.1123 0.085 Uiso 1 1 calc R . . H1C H 0.0876 0.6838 -0.1638 0.085 Uiso 1 1 calc R . . C2 C 0.27994(15) 0.75600(12) 0.01107(6) 0.0383(2) Uani 1 1 d U . . C3 C 0.51770(16) 0.75102(12) 0.00744(6) 0.0402(2) Uani 1 1 d . . . C4 C 0.60096(15) 0.84880(13) 0.09401(6) 0.0411(2) Uani 1 1 d U . . C5 C 0.36091(15) 0.85056(12) 0.09391(6) 0.0372(2) Uani 1 1 d U . . C6 C 0.3884(2) 1.01863(16) 0.22804(7) 0.0545(3) Uani 1 1 d U . . H6A H 0.2797 1.0781 0.2506 0.082 Uiso 1 1 calc R . . H6B H 0.4838 1.1090 0.2134 0.082 Uiso 1 1 calc R . . H6C H 0.4859 0.9373 0.2723 0.082 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 O1 0.0421(4) 0.0627(5) 0.0534(4) -0.0022(3) 0.0210(3) 0.0014(3) O2 0.0378(4) 0.0657(5) 0.0554(4) -0.0027(3) 0.0151(3) -0.0026(3) N1 0.0338(4) 0.0529(5) 0.0476(4) -0.0003(3) 0.0149(3) 0.0004(3) N2 0.0360(4) 0.0535(5) 0.0490(4) -0.0014(3) 0.0174(3) 0.0000(3) C1 0.0477(6) 0.0670(7) 0.0527(6) -0.0047(5) 0.0149(4) 0.0010(5) C2 0.0317(4) 0.0424(5) 0.0426(4) 0.0029(3) 0.0149(3) 0.0017(3) C3 0.0324(5) 0.0453(5) 0.0441(5) 0.0031(3) 0.0145(3) 0.0014(3) C4 0.0329(5) 0.0468(5) 0.0454(5) 0.0034(4) 0.0156(3) 0.0015(3) C5 0.0311(4) 0.0405(4) 0.0409(4) 0.0027(3) 0.0135(3) 0.0004(3) C6 0.0498(6) 0.0596(6) 0.0546(6) -0.0050(4) 0.0184(4) 0.0004(4) _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 C3 1.2315(13) . ? O2 C4 1.2386(13) . ? N1 C2 1.3141(13) . ? N1 C1 1.4510(15) . ? N1 H1N 0.8228 . ? N2 C5 1.3151(13) . ? N2 C6 1.4625(14) . ? N2 H2N 0.8525 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C5 1.4278(14) . ? C2 C3 1.4687(16) . ? C3 C4 1.4882(14) . ? C4 C5 1.4607(16) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C1 122.16(9) . . ? C2 N1 H1N 119.4 . . ? C1 N1 H1N 118.4 . . ? C5 N2 C6 122.24(9) . . ? C5 N2 H2N 119.1 . . ? C6 N2 H2N 118.5 . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C5 134.86(9) . . ? N1 C2 C3 134.14(9) . . ? C5 C2 C3 91.00(8) . . ? O1 C3 C2 135.53(9) . . ? O1 C3 C4 135.78(9) . . ? C2 C3 C4 88.69(8) . . ? O2 C4 C5 135.87(10) . . ? O2 C4 C3 135.18(9) . . ? C5 C4 C3 88.95(8) . . ? N2 C5 C2 134.42(9) . . ? N2 C5 C4 134.22(9) . . ? C2 C5 C4 91.37(8) . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.791 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.135 _refine_diff_density_min -0.110 _refine_diff_density_rms 0.027 # Attachment '- 865058.cif' data_anpm149a _database_code_depnum_ccdc_archive 'CCDC 865058' #TrackingRef '- 865058.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N2 O2' _chemical_formula_sum 'C8 H10 N2 O2' _chemical_formula_weight 166.18 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.995(4) _cell_length_b 11.203(7) _cell_length_c 14.389(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.44(4) _cell_angle_gamma 90.00 _cell_volume 802.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 80 _cell_measurement_theta_min 3 _cell_measurement_theta_max 31 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 105(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 'MAR345 with image plate detector' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6377 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 32.45 _reflns_number_total 2422 _reflns_number_gt 1692 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MARXDS (Claudio Klein, 2005)' _computing_cell_refinement 'AUTOMAR (Claudio Klein, 2007)' _computing_data_reduction 'MARSCALE (Claudio Klein, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Brueggermann and Smith, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0261P)^2^+0.0898P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2422 _refine_ls_number_parameters 109 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.102 _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 0.80121(19) 0.41526(8) 0.57530(7) 0.0560(3) Uani 1 1 d U . . O2 O 1.08434(19) 0.15055(8) 0.56354(7) 0.0547(3) Uani 1 1 d . . . N1 N 0.6358(2) 0.06892(9) 0.40622(7) 0.0452(3) Uani 1 1 d . . . H1N H 0.7576 0.0145 0.4092 0.054 Uiso 1 1 calc R . . N2 N 0.3790(2) 0.34684(10) 0.40344(8) 0.0484(3) Uani 1 1 d . . . H2N H 0.3348 0.4150 0.4250 0.058 Uiso 1 1 calc R . . C1 C 0.8904(2) 0.20253(11) 0.52408(8) 0.0422(3) Uani 1 1 d . . . C2 C 0.7659(2) 0.32417(11) 0.52837(8) 0.0428(3) Uani 1 1 d U . . C3 C 0.5710(2) 0.28683(11) 0.45177(8) 0.0423(3) Uani 1 1 d . . . C4 C 0.6851(2) 0.17041(11) 0.45186(8) 0.0405(3) Uani 1 1 d . . . C5 C 0.3830(3) 0.04574(12) 0.35100(9) 0.0480(3) Uani 1 1 d . . . H5A H 0.2364 0.0763 0.3845 0.058 Uiso 1 1 calc R . . H5B H 0.3592 -0.0399 0.3448 0.058 Uiso 1 1 calc R . . C6 C 0.3657(3) 0.10047(13) 0.25506(10) 0.0563(4) Uani 1 1 d . . . H6A H 0.1906 0.0824 0.2244 0.068 Uiso 1 1 calc R . . H6B H 0.4993 0.0629 0.2192 0.068 Uiso 1 1 calc R . . C7 C 0.4075(3) 0.23542(13) 0.25278(10) 0.0530(3) Uani 1 1 d . . . H7A H 0.3691 0.2630 0.1892 0.064 Uiso 1 1 calc R . . H7B H 0.5950 0.2523 0.2704 0.064 Uiso 1 1 calc R . . C8 C 0.2354(3) 0.30695(13) 0.31630(9) 0.0520(3) Uani 1 1 d . . . H8A H 0.1645 0.3764 0.2825 0.062 Uiso 1 1 calc R . . H8B H 0.0841 0.2581 0.3312 0.062 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 O1 0.0623(6) 0.0477(5) 0.0569(6) -0.0062(4) -0.0027(4) 0.0052(5) O2 0.0559(6) 0.0478(6) 0.0586(6) -0.0019(4) -0.0076(4) 0.0072(4) N1 0.0465(6) 0.0409(6) 0.0476(6) -0.0014(5) -0.0013(4) 0.0047(5) N2 0.0487(6) 0.0424(6) 0.0532(6) -0.0015(5) -0.0022(5) 0.0064(5) C1 0.0434(6) 0.0407(6) 0.0422(6) -0.0003(5) 0.0017(5) 0.0031(5) C2 0.0447(6) 0.0410(6) 0.0425(6) 0.0002(5) 0.0022(5) 0.0040(5) C3 0.0428(6) 0.0394(6) 0.0443(6) 0.0004(5) 0.0013(5) 0.0033(5) C4 0.0418(6) 0.0383(6) 0.0411(6) 0.0010(5) 0.0006(5) 0.0031(5) C5 0.0486(7) 0.0420(7) 0.0525(7) -0.0022(6) -0.0008(6) -0.0001(6) C6 0.0598(8) 0.0558(9) 0.0522(8) -0.0021(6) -0.0029(6) 0.0035(7) C7 0.0538(7) 0.0556(8) 0.0487(7) 0.0032(6) -0.0020(6) 0.0021(7) C8 0.0506(7) 0.0484(8) 0.0554(8) 0.0025(6) -0.0060(6) 0.0037(6) _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 C2 1.2288(15) . ? O2 C1 1.2308(16) . ? N1 C4 1.3265(17) . ? N1 C5 1.4623(18) . ? N1 H1N 0.8600 . ? N2 C3 1.3237(17) . ? N2 C8 1.4654(18) . ? N2 H2N 0.8600 . ? C1 C4 1.4478(19) . ? C1 C2 1.5012(19) . ? C2 C3 1.4734(19) . ? C3 C4 1.4231(18) . ? C5 C6 1.507(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.527(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.529(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 C4 N1 C5 122.72(11) . . ? C4 N1 H1N 118.6 . . ? C5 N1 H1N 118.6 . . ? C3 N2 C8 125.55(12) . . ? C3 N2 H2N 117.2 . . ? C8 N2 H2N 117.2 . . ? O2 C1 C4 134.59(13) . . ? O2 C1 C2 136.42(12) . . ? C4 C1 C2 88.99(10) . . ? O1 C2 C3 134.85(12) . . ? O1 C2 C1 137.23(12) . . ? C3 C2 C1 87.90(10) . . ? N2 C3 C4 137.70(12) . . ? N2 C3 C2 131.19(12) . . ? C4 C3 C2 91.05(10) . . ? N1 C4 C3 136.57(12) . . ? N1 C4 C1 131.47(11) . . ? C3 C4 C1 91.96(10) . . ? N1 C5 C6 114.29(12) . . ? N1 C5 H5A 108.7 . . ? C6 C5 H5A 108.7 . . ? N1 C5 H5B 108.7 . . ? C6 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C5 C6 C7 115.11(12) . . ? C5 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? C5 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C6 C7 C8 114.96(13) . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7A 108.5 . . ? C6 C7 H7B 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? N2 C8 C7 114.25(12) . . ? N2 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? N2 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? _diffrn_measured_fraction_theta_max 0.833 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.112 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.030 # Attachment '- 865059.cif' data_anom122a _database_code_depnum_ccdc_archive 'CCDC 865059' #TrackingRef '- 865059.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O2' _chemical_formula_sum 'C12 H10 N2 O2' _chemical_formula_weight 214.22 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 Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 18.938(19) _cell_length_b 11.841(11) _cell_length_c 4.309(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 966.3(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 240 _cell_measurement_theta_min 3 _cell_measurement_theta_max 31 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'MAR345 with image plate detector' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8451 _diffrn_reflns_av_R_equivalents 0.1013 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 32.38 _reflns_number_total 1664 _reflns_number_gt 1038 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MARXDS (Claudio Klein, 2005)' _computing_cell_refinement 'AUTOMAR (Claudio Klein, 2007)' _computing_data_reduction 'MARSCALE (Claudio Klein, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Brueggermann and Smith, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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. Regarding the crystal refinement parameter, for the structural resolution, it has been considered only reflections that have a value max of theta = 25\% (ACTA 50). Reflections between 25\% and 32\% have not been taken into account due to the poor quality of the reflections over this value. The poor quality of reflections could be due to the fact that the crystal does not diffract very well and to the kind of detector (image plate with spindle axis only) that was used. Other attempts of crystallization were done, but no single crystals of better quality were obtained ; _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^)+(0.0869P)^2^+0.0042P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1664 _refine_ls_number_parameters 73 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1362 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.2100 _refine_ls_wR_factor_gt 0.1836 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.183 _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 0.57545(10) 0.11111(14) -0.1009(4) 0.0591(5) Uani 1 1 d . . . N1 N 0.44276(10) 0.10751(15) 0.3502(4) 0.0421(5) Uani 1 1 d U . . H1N H 0.4563 0.0393 0.3164 0.050 Uiso 1 1 calc R . . C1 C 0.54249(12) 0.18726(17) 0.0272(5) 0.0423(5) Uani 1 1 d . . . C2 C 0.48130(11) 0.18996(17) 0.2328(5) 0.0391(5) Uani 1 1 d U . . C3 C 0.37876(12) 0.12415(19) 0.5334(5) 0.0425(5) Uani 1 1 d . . . H3A H 0.3911 0.1626 0.7246 0.051 Uiso 1 1 calc R . . H3B H 0.3595 0.0509 0.5881 0.051 Uiso 1 1 calc R . . C4 C 0.32288(11) 0.19122(19) 0.3690(5) 0.0391(5) Uani 1 1 d U . . C5 C 0.26946(13) 0.1341(2) 0.2074(5) 0.0450(5) Uani 1 1 d U . . H5 H 0.2690 0.0555 0.2061 0.054 Uiso 1 1 calc R . . C6 C 0.21797(13) 0.1921(2) 0.0514(5) 0.0524(6) Uani 1 1 d U . . H6 H 0.1829 0.1529 -0.0547 0.063 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 O1 0.0516(11) 0.0435(10) 0.0821(12) -0.0094(9) 0.0163(9) 0.0007(8) N1 0.0406(10) 0.0331(9) 0.0525(11) 0.0053(7) -0.0026(8) 0.0008(7) C1 0.0400(12) 0.0330(11) 0.0538(12) -0.0011(9) -0.0005(9) -0.0037(9) C2 0.0391(11) 0.0331(11) 0.0450(11) 0.0004(8) -0.0067(8) -0.0011(8) C3 0.0459(13) 0.0399(12) 0.0419(11) 0.0064(8) -0.0009(9) 0.0014(10) C4 0.0386(10) 0.0435(12) 0.0353(10) 0.0021(8) 0.0047(7) -0.0004(8) C5 0.0471(12) 0.0399(13) 0.0481(12) -0.0014(8) 0.0025(8) -0.0092(8) C6 0.0382(12) 0.0628(16) 0.0563(14) -0.0037(10) -0.0023(9) -0.0103(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 C1 1.228(3) . ? N1 C2 1.320(3) . ? N1 C3 1.460(3) . ? N1 H1N 0.8600 . ? C1 C2 1.459(3) . ? C1 C1 1.486(4) 8_565 ? C2 C2 1.422(4) 8_565 ? C3 C4 1.501(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C4 1.392(5) 8_565 ? C4 C5 1.402(3) . ? C5 C6 1.369(4) . ? C5 H5 0.9300 . ? C6 C6 1.371(5) 8_565 ? C6 H6 0.9300 . ? 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 C2 N1 C3 124.51(19) . . ? C2 N1 H1N 117.7 . . ? C3 N1 H1N 117.7 . . ? O1 C1 C2 133.9(2) . . ? O1 C1 C1 137.25(14) . 8_565 ? C2 C1 C1 88.74(11) . 8_565 ? N1 C2 C2 137.71(13) . 8_565 ? N1 C2 C1 131.0(2) . . ? C2 C2 C1 91.26(11) 8_565 . ? N1 C3 C4 113.67(19) . . ? N1 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? N1 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C4 C4 C5 118.86(14) 8_565 . ? C4 C4 C3 121.94(13) 8_565 . ? C5 C4 C3 119.2(2) . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C6 120.13(15) . 8_565 ? C5 C6 H6 119.9 . . ? C6 C6 H6 119.9 8_565 . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.184 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.052 # Attachment '- 865060.cif' data_anpm48a1 _database_code_depnum_ccdc_archive 'CCDC 865060' #TrackingRef '- 865060.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 N O3' _chemical_formula_sum 'C7 H9 N O3' _chemical_formula_weight 155.15 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.619(14) _cell_length_b 7.888(11) _cell_length_c 8.147(9) _cell_angle_alpha 65.33(9) _cell_angle_beta 66.81(8) _cell_angle_gamma 72.58(10) _cell_volume 403.6(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 256 _cell_measurement_theta_min 3 _cell_measurement_theta_max 31 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 164 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'MAR345 with image plate detector' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3151 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 32.29 _reflns_number_total 1938 _reflns_number_gt 1005 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MARXDS (Claudio Klein, 2005)' _computing_cell_refinement 'AUTOMAR (Claudio Klein, 2007)' _computing_data_reduction 'MARSCALE (Claudio Klein, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Brueggermann and Smith, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0530P)^2^+0.0808P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1938 _refine_ls_number_parameters 109 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1378 _refine_ls_R_factor_gt 0.0746 _refine_ls_wR_factor_ref 0.1910 _refine_ls_wR_factor_gt 0.1674 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.136 _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 0.1158(3) 0.2706(3) 0.6578(3) 0.0980(7) Uani 1 1 d . . . O2 O 0.5491(3) 0.0328(3) 0.6649(3) 0.0939(7) Uani 1 1 d . . . O3 O 0.7274(3) 0.3680(3) 0.2586(3) 0.0906(7) Uani 1 1 d U B . N N 0.2952(3) 0.5922(3) 0.2639(3) 0.0740(7) Uani 1 1 d . . . H1N H 0.1712 0.6214 0.2979 0.089 Uiso 1 1 calc R . . C1 C 0.4064(4) 0.7196(4) 0.0869(4) 0.0811(8) Uani 1 1 d . . . H1A H 0.3193 0.8228 0.0300 0.122 Uiso 1 1 calc R . . H1B H 0.4830 0.6517 0.0010 0.122 Uiso 1 1 calc R . . H1C H 0.4899 0.7679 0.1138 0.122 Uiso 1 1 calc R . . C2 C 0.3732(4) 0.4343(4) 0.3754(4) 0.0634(6) Uani 1 1 d U . . C3 C 0.2851(4) 0.2922(4) 0.5551(4) 0.0719(7) Uani 1 1 d U . . C4 C 0.4822(4) 0.1843(4) 0.5577(4) 0.0730(8) Uani 1 1 d . . . C5 C 0.5558(4) 0.3340(4) 0.3824(4) 0.0673(7) Uani 1 1 d U . . C6 C 0.8967(6) 0.2247(6) 0.3095(6) 0.1245(14) Uani 1 1 d U . . H6A H 0.9553 0.2726 0.3643 0.149 Uiso 0.50 1 calc PR A 1 H6B H 0.8512 0.1089 0.4043 0.149 Uiso 0.50 1 calc PR A 1 H6A' H 0.8998 0.2213 0.4287 0.149 Uiso 0.50 1 calc PR A 2 H6B' H 0.8794 0.1005 0.3274 0.149 Uiso 0.50 1 calc PR A 2 C7 C 1.0290(17) 0.1871(14) 0.1581(16) 0.120(3) Uani 0.50 1 d P B 1 H7A H 1.1345 0.0955 0.1953 0.180 Uiso 0.50 1 calc PR B 1 H7B H 1.0761 0.3011 0.0650 0.180 Uiso 0.50 1 calc PR B 1 H7C H 0.9718 0.1377 0.1048 0.180 Uiso 0.50 1 calc PR B 1 C7' C 1.0670(15) 0.2642(12) 0.1745(15) 0.098(3) Uani 0.50 1 d PU B 2 H7D H 1.1705 0.1705 0.2134 0.147 Uiso 0.50 1 calc PR B 2 H7E H 1.0853 0.3866 0.1569 0.147 Uiso 0.50 1 calc PR B 2 H7F H 1.0663 0.2636 0.0571 0.147 Uiso 0.50 1 calc PR B 2 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 0.0870(16) 0.0960(16) 0.0941(15) -0.0176(13) -0.0241(13) -0.0190(12) O2 0.1037(17) 0.0845(15) 0.0911(15) -0.0206(12) -0.0417(13) -0.0099(12) O3 0.0732(11) 0.0904(14) 0.0918(14) -0.0237(11) -0.0218(9) -0.0072(10) N 0.0679(14) 0.0719(14) 0.0743(15) -0.0196(12) -0.0205(12) -0.0105(11) C1 0.082(2) 0.0779(18) 0.0779(19) -0.0223(15) -0.0230(16) -0.0150(15) C2 0.0661(15) 0.0578(14) 0.0676(13) -0.0206(10) -0.0236(12) -0.0090(11) C3 0.0747(19) 0.0661(16) 0.0723(15) -0.0185(11) -0.0235(14) -0.0144(13) C4 0.0788(19) 0.0681(18) 0.0736(18) -0.0211(15) -0.0286(15) -0.0115(14) C5 0.0687(14) 0.0620(15) 0.0746(17) -0.0243(14) -0.0282(10) -0.0058(12) C6 0.096(3) 0.124(3) 0.121(3) -0.031(3) -0.030(2) 0.004(2) C7 0.118(9) 0.104(8) 0.119(7) -0.047(6) -0.029(6) 0.009(6) C7' 0.096(4) 0.078(6) 0.118(6) -0.017(5) -0.045(3) -0.020(5) _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 C3 1.247(4) . ? O2 C4 1.251(4) . ? O3 C5 1.321(4) . ? O3 C6 1.507(5) . ? N C2 1.330(4) . ? N C1 1.465(4) . ? N H1N 0.8600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C5 1.389(4) . ? C2 C3 1.469(4) . ? C3 C4 1.492(5) . ? C3 C5 2.019(5) . ? C4 C5 1.451(4) . ? C6 C7 1.331(11) . ? C6 C7' 1.350(11) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H6A' 0.9700 . ? C6 H6B' 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C7' H7D 0.9600 . ? C7' H7E 0.9600 . ? C7' H7F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O3 C6 115.3(3) . . ? C2 N C1 124.4(3) . . ? C2 N H1N 117.8 . . ? C1 N H1N 117.8 . . ? N C1 H1A 109.5 . . ? N C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N C2 C5 138.6(3) . . ? N C2 C3 131.5(3) . . ? C5 C2 C3 89.8(3) . . ? O1 C3 C2 134.7(3) . . ? O1 C3 C4 136.0(3) . . ? C2 C3 C4 89.3(3) . . ? O1 C3 C5 178.1(2) . . ? C2 C3 C5 43.48(17) . . ? C4 C3 C5 45.87(19) . . ? O2 C4 C5 137.8(3) . . ? O2 C4 C3 135.6(3) . . ? C5 C4 C3 86.6(3) . . ? O3 C5 C2 129.5(3) . . ? O3 C5 C4 136.1(3) . . ? C2 C5 C4 94.2(3) . . ? O3 C5 C3 175.7(2) . . ? C2 C5 C3 46.67(19) . . ? C4 C5 C3 47.53(18) . . ? C7 C6 C7' 35.7(5) . . ? C7 C6 O3 111.6(6) . . ? C7' C6 O3 112.3(5) . . ? C7 C6 H6A 109.3 . . ? C7' C6 H6A 76.1 . . ? O3 C6 H6A 109.3 . . ? C7 C6 H6B 109.3 . . ? C7' C6 H6B 133.8 . . ? O3 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C7 C6 H6A' 134.7 . . ? C7' C6 H6A' 109.1 . . ? O3 C6 H6A' 109.1 . . ? H6A C6 H6A' 36.5 . . ? H6B C6 H6A' 74.1 . . ? C7 C6 H6B' 76.5 . . ? C7' C6 H6B' 109.1 . . ? O3 C6 H6B' 109.1 . . ? H6A C6 H6B' 135.1 . . ? H6B C6 H6B' 36.2 . . ? H6A' C6 H6B' 107.9 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C7' H7D 109.5 . . ? C6 C7' H7E 109.5 . . ? H7D C7' H7E 109.5 . . ? C6 C7' H7F 109.5 . . ? H7D C7' H7F 109.5 . . ? H7E C7' H7F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.673 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.123 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.028