# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Roberto Centore' _publ_contact_author_email ROBERTO.CENTORE@UNINA.IT _publ_section_title ; Competitive H bonding synthons in organic hydrazides ; loop_ _publ_author_name 'Roberto Centore' 'Amedeo Capobianco' 'Andrea Peluso' 'Angela Tuzi' # Attachment 'hydr1.cif' data_hoidrlt _database_code_depnum_ccdc_archive 'CCDC 731632' #TrackingRef 'hydr1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-hydroxybenzohydrazide ; _chemical_formula_moiety 'C7 H8 N2 O2' _chemical_formula_sum 'C7 H8 N2 O2' _chemical_formula_weight 152.15 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 monoclinic _space_group_name_H-M_alt 'P 21/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 5.035(3) _cell_length_b 17.205(9) _cell_length_c 7.734(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.23(5) _cell_angle_gamma 90.00 _cell_volume 668.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 62 _cell_measurement_theta_min 5.708 _cell_measurement_theta_max 21.320 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9434 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details ; SADABS (Bruker-Nonius, 2002) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_detector 'CCD plate' _diffrn_detector_type ; Bruker-Nonius 95mm CCD camera on \k-goniostat ; _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method ; CCD rotation images, thick slices ; loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _diffrn_reflns_number 4425 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 26.99 _reflns_number_total 1426 _reflns_number_gt 1003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1999)' _computing_cell_refinement ; CELLFITW (Centore, 2004) ; _computing_data_reduction ; EvalCCD (Duisenberg et al., 2003) ; _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997), Mercury 2.2 (CCDC 2001-2008)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0541P)^2^+0.0680P] 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_number_reflns 1426 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.4068(3) 0.36311(9) 0.3756(2) 0.0187(4) Uani 1 1 d . . . C2 C 0.3517(3) 0.27885(10) 0.3718(2) 0.0183(4) Uani 1 1 d . . . C3 C 0.5315(3) 0.22826(10) 0.4551(2) 0.0210(4) Uani 1 1 d . . . C4 C 0.4923(3) 0.14906(10) 0.4499(2) 0.0249(4) Uani 1 1 d . . . C5 C 0.2708(3) 0.11860(9) 0.3587(2) 0.0214(4) Uani 1 1 d . . . C6 C 0.0907(3) 0.16845(10) 0.2727(2) 0.0234(4) Uani 1 1 d . . . C7 C 0.1311(3) 0.24733(10) 0.2806(2) 0.0223(4) Uani 1 1 d . . . N1 N 0.2229(3) 0.49102(8) 0.3220(2) 0.0265(4) Uani 1 1 d . . . N2 N 0.1962(3) 0.41001(8) 0.34746(18) 0.0228(4) Uani 1 1 d . . . O1 O 0.6344(2) 0.39001(7) 0.39844(15) 0.0253(3) Uani 1 1 d . . . O2 O 0.2430(2) 0.04011(7) 0.35446(18) 0.0326(4) Uani 1 1 d . . . H3 H 0.682(4) 0.2492(11) 0.521(3) 0.039 Uiso 1 1 d . . . H4 H 0.614(4) 0.1125(11) 0.512(2) 0.039 Uiso 1 1 d . . . H6 H -0.054(4) 0.1462(11) 0.203(3) 0.039 Uiso 1 1 d . . . H7 H 0.005(4) 0.2851(11) 0.218(3) 0.039 Uiso 1 1 d . . . H1A H 0.359(4) 0.4967(11) 0.252(2) 0.039 Uiso 1 1 d . . . H1B H 0.263(4) 0.5120(12) 0.428(3) 0.039 Uiso 1 1 d . . . H2 H 0.033(4) 0.3911(11) 0.350(2) 0.039 Uiso 1 1 d . . . H1 H 0.102(4) 0.0295(12) 0.295(3) 0.039 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 0.0168(8) 0.0199(9) 0.0192(9) -0.0003(7) 0.0005(6) -0.0011(7) C2 0.0167(8) 0.0184(9) 0.0202(9) -0.0008(7) 0.0040(6) 0.0004(7) C3 0.0176(8) 0.0215(10) 0.0236(10) -0.0021(7) -0.0020(7) -0.0005(7) C4 0.0235(8) 0.0235(10) 0.0276(10) 0.0016(8) -0.0003(7) 0.0039(7) C5 0.0216(8) 0.0168(9) 0.0263(9) -0.0022(7) 0.0056(7) -0.0004(7) C6 0.0183(8) 0.0213(10) 0.0303(10) -0.0036(7) -0.0015(7) -0.0023(7) C7 0.0183(8) 0.0207(10) 0.0272(10) 0.0003(7) -0.0026(7) 0.0003(7) N1 0.0221(7) 0.0170(8) 0.0399(10) -0.0007(7) -0.0022(7) 0.0013(6) N2 0.0154(7) 0.0147(8) 0.0381(9) 0.0000(6) -0.0007(6) -0.0009(6) O1 0.0166(6) 0.0211(7) 0.0379(7) -0.0023(5) -0.0023(5) -0.0015(5) O2 0.0273(7) 0.0179(7) 0.0514(9) -0.0009(6) -0.0088(6) -0.0013(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 C1 O1 1.2394(18) . ? C1 N2 1.340(2) . ? C1 C2 1.476(2) . ? C2 C3 1.388(2) . ? C2 C7 1.392(2) . ? C3 C4 1.377(3) . ? C3 H3 0.96(2) . ? C4 C5 1.388(2) . ? C4 H4 0.985(19) . ? C5 O2 1.358(2) . ? C5 C6 1.390(2) . ? C6 C7 1.373(2) . ? C6 H6 0.960(19) . ? C7 H7 1.01(2) . ? N1 N2 1.415(2) . ? N1 H1A 0.90(2) . ? N1 H1B 0.91(2) . ? N2 H2 0.885(19) . ? O2 H1 0.84(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 O1 C1 N2 121.00(16) . . ? O1 C1 C2 122.73(14) . . ? N2 C1 C2 116.25(13) . . ? C3 C2 C7 118.15(16) . . ? C3 C2 C1 119.35(14) . . ? C7 C2 C1 122.43(14) . . ? C4 C3 C2 121.25(16) . . ? C4 C3 H3 119.6(11) . . ? C2 C3 H3 119.1(11) . . ? C3 C4 C5 119.85(15) . . ? C3 C4 H4 122.2(11) . . ? C5 C4 H4 117.9(11) . . ? O2 C5 C4 117.80(14) . . ? O2 C5 C6 122.58(15) . . ? C4 C5 C6 119.60(16) . . ? C7 C6 C5 119.82(16) . . ? C7 C6 H6 121.6(12) . . ? C5 C6 H6 118.4(12) . . ? C6 C7 C2 121.32(16) . . ? C6 C7 H7 121.7(11) . . ? C2 C7 H7 116.9(11) . . ? N2 N1 H1A 105.7(12) . . ? N2 N1 H1B 106.4(13) . . ? H1A N1 H1B 111.1(18) . . ? C1 N2 N1 122.36(13) . . ? C1 N2 H2 120.1(13) . . ? N1 N2 H2 117.5(13) . . ? C5 O2 H1 108.1(14) . . ? 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 O1 C1 C2 C3 23.8(2) . . . . ? N2 C1 C2 C3 -158.10(15) . . . . ? O1 C1 C2 C7 -153.09(16) . . . . ? N2 C1 C2 C7 25.0(2) . . . . ? C7 C2 C3 C4 -0.8(2) . . . . ? C1 C2 C3 C4 -177.82(15) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C3 C4 C5 O2 178.78(14) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? O2 C5 C6 C7 -179.42(15) . . . . ? C4 C5 C6 C7 -0.9(3) . . . . ? C5 C6 C7 C2 0.8(3) . . . . ? C3 C2 C7 C6 0.0(3) . . . . ? C1 C2 C7 C6 176.99(15) . . . . ? O1 C1 N2 N1 7.6(2) . . . . ? C2 C1 N2 N1 -170.48(14) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.194 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.048 _chemical_name_common 4-hydroxybenzohydrazide # Attachment 'hydr2.cif' data_o2nidrzlt _database_code_depnum_ccdc_archive 'CCDC 731633' #TrackingRef 'hydr2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-nitrobenzohydrazide ; _chemical_formula_moiety 'C7 H7 N3 O3' _chemical_formula_sum 'C7 H7 N3 O3' _chemical_formula_weight 181.16 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 _space_group_name_H-M_alt 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 21.648(7) _cell_length_b 3.594(3) _cell_length_c 9.704(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 755.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 4.608 _cell_measurement_theta_max 19.341 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9389 _exptl_absorpt_correction_T_max 0.9968 _exptl_absorpt_process_details ; SADABS (Bruker-Nonius, 2002) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_detector 'CCD plate' _diffrn_detector_type ; Bruker-Nonius 95mm CCD camera on \k-goniostat ; _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method ; CCD rotation images, thick slices ; loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _diffrn_reflns_number 2844 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 27.48 _reflns_number_total 880 _reflns_number_gt 682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'CELLFITW (Centore, 2004)' _computing_data_reduction ; EvalCCD (Duisenberg & Schreurs 1990-2000) ; _computing_structure_solution 'SIR97 (Altomare at al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and Mercury 2.2 (CCDC 2001-2008) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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. Friedel pairs were merged because the lack of heavy atoms did not allow reliable estimation of absolute structure. ; _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^)+(0.0513P)^2^+0.0000P] 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_number_reflns 880 _refine_ls_number_parameters 139 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.75935(12) -0.0640(9) 0.1553(3) 0.0203(7) Uani 1 1 d . . . C2 C 0.82686(12) 0.0116(9) 0.1320(3) 0.0192(7) Uani 1 1 d . . . C3 C 0.86592(14) -0.0318(8) 0.2441(3) 0.0196(7) Uani 1 1 d . . . H3 H 0.8489(13) -0.102(9) 0.333(4) 0.024 Uiso 1 1 d . . . C4 C 0.92826(14) 0.0494(9) 0.2326(3) 0.0209(7) Uani 1 1 d . . . H4 H 0.9569(14) 0.034(9) 0.313(4) 0.025 Uiso 1 1 d . . . C5 C 0.94949(12) 0.1829(9) 0.1076(3) 0.0183(7) Uani 1 1 d . . . C6 C 0.91219(14) 0.2241(8) -0.0069(3) 0.0200(7) Uani 1 1 d . . . H6 H 0.9274(14) 0.313(10) -0.092(4) 0.024 Uiso 1 1 d . . . C7 C 0.85017(14) 0.1331(8) 0.0065(3) 0.0206(7) Uani 1 1 d . . . H7 H 0.8248(15) 0.179(10) -0.070(4) 0.025 Uiso 1 1 d . . . N1 N 0.66605(12) -0.3324(10) 0.0671(3) 0.0303(7) Uani 1 1 d . . . H1A H 0.6642(16) -0.452(11) 0.146(5) 0.036 Uiso 1 1 d . . . H1B H 0.6457(17) -0.142(11) 0.061(4) 0.036 Uiso 1 1 d . . . N2 N 0.72845(11) -0.2176(7) 0.0513(3) 0.0233(6) Uani 1 1 d . . . H2 H 0.7459(15) -0.302(10) -0.029(4) 0.028 Uiso 1 1 d . . . N3 N 1.01450(11) 0.2924(8) 0.0990(3) 0.0240(6) Uani 1 1 d . . . O1 O 0.73512(9) 0.0075(6) 0.2678(2) 0.0265(6) Uani 1 1 d . . . O2 O 1.03214(9) 0.4603(7) -0.0041(3) 0.0330(6) Uani 1 1 d . . . O3 O 1.04911(11) 0.2164(7) 0.1960(3) 0.0386(7) 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 0.0219(14) 0.0184(15) 0.0204(18) 0.0005(14) 0.0036(14) 0.0023(12) C2 0.0215(13) 0.0152(17) 0.0210(17) -0.0034(13) 0.0006(13) 0.0016(13) C3 0.0266(14) 0.0192(15) 0.0129(17) -0.0014(14) 0.0036(12) 0.0020(13) C4 0.0247(14) 0.0204(16) 0.0176(17) -0.0016(14) -0.0034(13) 0.0016(13) C5 0.0205(14) 0.0157(14) 0.0187(17) -0.0021(13) 0.0040(13) -0.0009(13) C6 0.0250(15) 0.0210(16) 0.0140(17) 0.0004(15) 0.0055(13) 0.0015(12) C7 0.0238(14) 0.0223(16) 0.0157(17) 0.0002(14) 0.0004(13) 0.0047(13) N1 0.0206(13) 0.0417(17) 0.0285(17) -0.0078(17) 0.0004(13) -0.0023(13) N2 0.0182(12) 0.0328(16) 0.0188(15) -0.0073(14) 0.0031(11) -0.0029(11) N3 0.0245(13) 0.0229(15) 0.0247(15) -0.0064(13) 0.0038(13) 0.0009(11) O1 0.0257(10) 0.0345(14) 0.0193(12) -0.0036(11) 0.0053(10) -0.0026(9) O2 0.0302(11) 0.0370(13) 0.0318(13) 0.0056(13) 0.0092(10) -0.0084(10) O3 0.0255(11) 0.0562(17) 0.0341(16) 0.0014(13) -0.0078(11) -0.0033(12) _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 O1 1.238(4) . ? C1 N2 1.331(4) . ? C1 C2 1.504(4) . ? C2 C3 1.386(4) . ? C2 C7 1.389(4) . ? C3 C4 1.385(4) . ? C3 H3 0.97(3) . ? C4 C5 1.383(4) . ? C4 H4 1.00(3) . ? C5 C6 1.382(4) . ? C5 N3 1.464(3) . ? C6 C7 1.388(4) . ? C6 H6 0.95(3) . ? C7 H7 0.94(4) . ? N1 N2 1.421(4) . ? N1 H1A 0.88(5) . ? N1 H1B 0.82(4) . ? N2 H2 0.92(4) . ? N3 O2 1.229(4) . ? N3 O3 1.234(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 O1 C1 N2 122.8(3) . . ? O1 C1 C2 120.4(3) . . ? N2 C1 C2 116.7(3) . . ? C3 C2 C7 120.1(3) . . ? C3 C2 C1 117.1(3) . . ? C7 C2 C1 122.8(3) . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.6(18) . . ? C2 C3 H3 119.7(18) . . ? C5 C4 C3 117.9(3) . . ? C5 C4 H4 119.7(18) . . ? C3 C4 H4 122.2(18) . . ? C6 C5 C4 123.3(2) . . ? C6 C5 N3 119.1(3) . . ? C4 C5 N3 117.6(3) . . ? C5 C6 C7 117.7(3) . . ? C5 C6 H6 122.4(19) . . ? C7 C6 H6 119.9(19) . . ? C6 C7 C2 120.5(3) . . ? C6 C7 H7 117(2) . . ? C2 C7 H7 123(2) . . ? N2 N1 H1A 106(2) . . ? N2 N1 H1B 105(3) . . ? H1A N1 H1B 116(4) . . ? C1 N2 N1 121.1(3) . . ? C1 N2 H2 125(2) . . ? N1 N2 H2 113(2) . . ? O2 N3 O3 122.8(2) . . ? O2 N3 C5 118.5(3) . . ? O3 N3 C5 118.7(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 O1 C1 C2 C3 33.5(4) . . . . ? N2 C1 C2 C3 -144.8(3) . . . . ? O1 C1 C2 C7 -144.2(3) . . . . ? N2 C1 C2 C7 37.5(5) . . . . ? C7 C2 C3 C4 0.8(5) . . . . ? C1 C2 C3 C4 -176.9(3) . . . . ? C2 C3 C4 C5 1.6(4) . . . . ? C3 C4 C5 C6 -2.7(5) . . . . ? C3 C4 C5 N3 175.9(3) . . . . ? C4 C5 C6 C7 1.3(4) . . . . ? N3 C5 C6 C7 -177.2(3) . . . . ? C5 C6 C7 C2 1.2(4) . . . . ? C3 C2 C7 C6 -2.2(5) . . . . ? C1 C2 C7 C6 175.4(3) . . . . ? O1 C1 N2 N1 -4.3(5) . . . . ? C2 C1 N2 N1 174.0(3) . . . . ? C6 C5 N3 O2 8.9(4) . . . . ? C4 C5 N3 O2 -169.7(3) . . . . ? C6 C5 N3 O3 -171.9(3) . . . . ? C4 C5 N3 O3 9.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.268 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.050 _chemical_name_common 4-nitrobenzohydrazide # Attachment 'hydr3.cif' data_cnidrzlt _database_code_depnum_ccdc_archive 'CCDC 731634' #TrackingRef 'hydr3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-cyanobenzohydrazide ; _chemical_formula_moiety 'C8 H7 N3 O' _chemical_formula_sum 'C8 H7 N3 O' _chemical_formula_weight 161.17 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 _space_group_name_H-M_alt 'P 21/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 15.930(10) _cell_length_b 3.816(3) _cell_length_c 12.689(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.11(7) _cell_angle_gamma 90.00 _cell_volume 765.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 37 _cell_measurement_theta_min 3.297 _cell_measurement_theta_max 19.965 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9435 _exptl_absorpt_correction_T_max 0.9976 _exptl_absorpt_process_details ; SADABS (Bruker-Nonius, 2002) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_detector 'CCD plate' _diffrn_detector_type ; Bruker-Nonius 95mm CCD camera on \k-goniostat ; _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method ; CCD rotation images, thick slices ; loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _diffrn_reflns_number 6482 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0684 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1712 _reflns_number_gt 1085 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'CELLFITW (Centore, 2004)' _computing_data_reduction ; EvalCCD (Duisenberg & Schreurs 1990-2000) ; _computing_structure_solution 'SIR97 (Altomare at al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and Mercury 2.2 (CCDC 2001-2008) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0524P)^2^+0.0000P] 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_number_reflns 1712 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 0.11820(10) -0.1557(4) 0.42556(13) 0.0203(4) Uani 1 1 d . . . C2 C 0.20431(10) -0.0435(4) 0.40393(13) 0.0201(4) Uani 1 1 d . . . C3 C 0.25978(11) 0.0748(5) 0.49022(14) 0.0262(4) Uani 1 1 d . . . H3 H 0.2389(11) 0.089(5) 0.5596(15) 0.031 Uiso 1 1 d . . . C4 C 0.34133(11) 0.1723(5) 0.47738(14) 0.0283(4) Uani 1 1 d . . . H4 H 0.3812(11) 0.257(5) 0.5377(15) 0.034 Uiso 1 1 d . . . C5 C 0.36862(10) 0.1453(5) 0.37750(14) 0.0246(4) Uani 1 1 d . . . C6 C 0.31399(11) 0.0256(5) 0.29089(15) 0.0273(5) Uani 1 1 d . . . H6 H 0.3368(11) 0.002(5) 0.2251(15) 0.033 Uiso 1 1 d . . . C7 C 0.23178(11) -0.0651(5) 0.30438(14) 0.0251(4) Uani 1 1 d . . . H7 H 0.1945(12) -0.144(5) 0.2423(14) 0.030 Uiso 1 1 d . . . C8 C 0.45513(12) 0.2401(5) 0.36680(15) 0.0296(5) Uani 1 1 d . . . N1 N -0.02747(9) -0.2398(5) 0.35351(12) 0.0233(4) Uani 1 1 d . . . H1A H -0.0231(11) -0.401(5) 0.4035(15) 0.028 Uiso 1 1 d . . . H1B H -0.0573(12) -0.064(5) 0.3833(14) 0.028 Uiso 1 1 d . . . N2 N 0.05537(8) -0.1098(4) 0.34678(11) 0.0226(4) Uani 1 1 d . . . H2 H 0.0622(11) 0.018(5) 0.2842(15) 0.027 Uiso 1 1 d . . . N3 N 0.52378(10) 0.3163(5) 0.36050(13) 0.0392(5) Uani 1 1 d . . . O1 O 0.10691(7) -0.2905(3) 0.51155(9) 0.0260(3) 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 0.0230(9) 0.0182(9) 0.0200(9) -0.0020(8) 0.0040(7) 0.0001(7) C2 0.0200(9) 0.0166(9) 0.0232(9) 0.0016(7) 0.0012(7) 0.0015(7) C3 0.0227(10) 0.0311(10) 0.0244(9) -0.0018(8) 0.0015(8) 0.0004(8) C4 0.0241(11) 0.0300(11) 0.0294(10) -0.0024(9) -0.0020(8) -0.0040(8) C5 0.0188(9) 0.0220(10) 0.0328(10) 0.0040(8) 0.0025(8) 0.0004(8) C6 0.0248(10) 0.0328(11) 0.0258(10) 0.0023(8) 0.0083(8) -0.0001(8) C7 0.0229(10) 0.0283(10) 0.0238(9) -0.0026(8) 0.0015(8) -0.0015(8) C8 0.0256(11) 0.0310(11) 0.0317(10) 0.0005(9) 0.0013(8) -0.0035(9) N1 0.0182(8) 0.0309(9) 0.0216(8) 0.0008(7) 0.0055(6) -0.0026(7) N2 0.0175(8) 0.0307(9) 0.0197(7) 0.0042(7) 0.0025(6) -0.0033(7) N3 0.0265(10) 0.0517(12) 0.0394(10) -0.0011(9) 0.0041(8) -0.0087(8) O1 0.0242(7) 0.0321(7) 0.0216(6) 0.0064(6) 0.0032(5) -0.0008(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 C1 O1 1.239(2) . ? C1 N2 1.336(2) . ? C1 C2 1.495(2) . ? C2 C7 1.390(2) . ? C2 C3 1.394(3) . ? C3 C4 1.380(3) . ? C3 H3 0.981(19) . ? C4 C5 1.394(3) . ? C4 H4 0.986(19) . ? C5 C6 1.392(3) . ? C5 C8 1.447(3) . ? C6 C7 1.385(3) . ? C6 H6 0.955(19) . ? C7 H7 0.973(19) . ? C8 N3 1.144(2) . ? N1 N2 1.422(2) . ? N1 H1A 0.88(2) . ? N1 H1B 0.93(2) . ? N2 H2 0.950(18) . ? 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 O1 C1 N2 122.45(16) . . ? O1 C1 C2 121.14(16) . . ? N2 C1 C2 116.40(15) . . ? C7 C2 C3 119.51(16) . . ? C7 C2 C1 123.34(16) . . ? C3 C2 C1 117.10(15) . . ? C4 C3 C2 120.59(17) . . ? C4 C3 H3 121.3(11) . . ? C2 C3 H3 118.1(11) . . ? C3 C4 C5 119.44(18) . . ? C3 C4 H4 121.4(10) . . ? C5 C4 H4 119.1(10) . . ? C6 C5 C4 120.49(16) . . ? C6 C5 C8 121.16(17) . . ? C4 C5 C8 118.34(17) . . ? C7 C6 C5 119.51(17) . . ? C7 C6 H6 123.5(11) . . ? C5 C6 H6 116.9(11) . . ? C6 C7 C2 120.43(18) . . ? C6 C7 H7 117.9(10) . . ? C2 C7 H7 121.6(10) . . ? N3 C8 C5 178.6(2) . . ? N2 N1 H1A 107.2(12) . . ? N2 N1 H1B 107.4(11) . . ? H1A N1 H1B 102.0(15) . . ? C1 N2 N1 121.61(15) . . ? C1 N2 H2 122.7(11) . . ? N1 N2 H2 115.6(11) . . ? 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 O1 C1 C2 C7 145.32(18) . . . . ? N2 C1 C2 C7 -33.3(2) . . . . ? O1 C1 C2 C3 -32.1(2) . . . . ? N2 C1 C2 C3 149.35(16) . . . . ? C7 C2 C3 C4 0.4(3) . . . . ? C1 C2 C3 C4 177.88(17) . . . . ? C2 C3 C4 C5 -1.2(3) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C3 C4 C5 C8 -178.33(17) . . . . ? C4 C5 C6 C7 0.4(3) . . . . ? C8 C5 C6 C7 179.53(18) . . . . ? C5 C6 C7 C2 -1.2(3) . . . . ? C3 C2 C7 C6 0.9(3) . . . . ? C1 C2 C7 C6 -176.48(17) . . . . ? C6 C5 C8 N3 -177(100) . . . . ? C4 C5 C8 N3 2(9) . . . . ? O1 C1 N2 N1 -5.3(3) . . . . ? C2 C1 N2 N1 173.21(15) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.179 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.053 _chemical_name_common 4-cyanobenzohydrazide # Attachment 'hydr4.cif' data_gehlenlt _database_code_depnum_ccdc_archive 'CCDC 731635' #TrackingRef 'hydr4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminobenzohydrazide ; _chemical_formula_moiety 'C7 H9 N3 O' _chemical_formula_sum 'C7 H9 N3 O' _chemical_formula_weight 151.17 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 _space_group_name_H-M_alt 'P 21/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 5.416(2) _cell_length_b 13.971(4) _cell_length_c 9.958(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.63(2) _cell_angle_gamma 90.00 _cell_volume 732.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 51 _cell_measurement_theta_min 4.931 _cell_measurement_theta_max 20.229 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9309 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details ; SADABS (Bruker-Nonius, 2002) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_detector 'CCD plate' _diffrn_detector_type ; Bruker-Nonius 95mm CCD camera on \k-goniostat ; _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method ; CCD rotation images, thick slices ; loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _diffrn_reflns_number 6525 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 28.39 _reflns_number_total 1661 _reflns_number_gt 1136 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'CELLFITW (Centore, 2004)' _computing_data_reduction ; EvalCCD (Duisenberg & Schreurs 1990-2000) ; _computing_structure_solution 'SIR97 (Altomare at al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and Mercury 2.2 (CCDC 2001-2008) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0464P)^2^+0.1621P] 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_number_reflns 1661 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.0095(3) 0.04540(11) 0.18493(15) 0.0217(3) Uani 1 1 d . . . C2 C 0.1082(3) 0.13652(10) 0.14385(15) 0.0211(3) Uani 1 1 d . . . C3 C 0.3624(3) 0.16373(11) 0.21262(15) 0.0239(4) Uani 1 1 d . . . H3 H 0.470(3) 0.1224(12) 0.2848(17) 0.029 Uiso 1 1 d . . . C4 C 0.4627(3) 0.24845(11) 0.18170(16) 0.0250(4) Uani 1 1 d . . . H4 H 0.637(3) 0.2648(11) 0.2306(17) 0.030 Uiso 1 1 d . . . C5 C 0.3123(3) 0.30995(10) 0.08028(15) 0.0236(4) Uani 1 1 d . . . C6 C 0.0594(3) 0.28197(11) 0.00923(16) 0.0264(4) Uani 1 1 d . . . H6 H -0.048(3) 0.3248(12) -0.0594(17) 0.032 Uiso 1 1 d . . . C7 C -0.0410(3) 0.19699(11) 0.04048(16) 0.0247(4) Uani 1 1 d . . . H7 H -0.219(3) 0.1793(11) -0.0115(16) 0.030 Uiso 1 1 d . . . N1 N -0.3376(3) -0.06984(10) 0.13378(15) 0.0271(3) Uani 1 1 d . . . H1A H -0.242(3) -0.1232(13) 0.1245(17) 0.032 Uiso 1 1 d . . . H1B H -0.326(3) -0.0660(12) 0.221(2) 0.032 Uiso 1 1 d . . . N2 N -0.2145(2) 0.01260(9) 0.10116(14) 0.0256(3) Uani 1 1 d . . . H2 H -0.314(3) 0.0424(12) 0.0258(18) 0.031 Uiso 1 1 d . . . N3 N 0.4050(3) 0.39675(10) 0.05479(15) 0.0328(4) Uani 1 1 d . . . H3A H 0.565(4) 0.4122(13) 0.100(2) 0.039 Uiso 1 1 d . . . H3B H 0.316(3) 0.4289(13) -0.017(2) 0.039 Uiso 1 1 d . . . O1 O 0.1257(2) 0.00165(8) 0.29170(11) 0.0328(3) 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 0.0216(8) 0.0222(7) 0.0216(8) -0.0014(6) 0.0055(6) 0.0025(6) C2 0.0217(8) 0.0221(8) 0.0201(8) -0.0024(6) 0.0063(6) -0.0005(6) C3 0.0218(8) 0.0283(8) 0.0213(8) -0.0007(7) 0.0043(6) 0.0019(7) C4 0.0198(8) 0.0312(8) 0.0236(8) -0.0047(7) 0.0041(6) -0.0043(7) C5 0.0265(8) 0.0245(8) 0.0214(8) -0.0050(6) 0.0087(6) -0.0055(7) C6 0.0267(9) 0.0260(8) 0.0245(9) 0.0040(7) 0.0021(7) -0.0004(6) C7 0.0208(8) 0.0261(8) 0.0253(8) 0.0002(6) 0.0017(6) -0.0033(6) N1 0.0308(8) 0.0249(7) 0.0262(8) 0.0042(6) 0.0079(6) -0.0060(6) N2 0.0259(7) 0.0254(7) 0.0239(7) 0.0061(6) 0.0029(6) -0.0064(6) N3 0.0333(8) 0.0319(8) 0.0294(8) 0.0053(6) -0.0005(6) -0.0118(7) O1 0.0322(6) 0.0297(6) 0.0312(7) 0.0086(5) -0.0029(5) -0.0021(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 C1 O1 1.2588(18) . ? C1 N2 1.379(2) . ? C1 C2 1.476(2) . ? C2 C7 1.426(2) . ? C2 C3 1.437(2) . ? C3 C4 1.367(2) . ? C3 H3 0.995(17) . ? C4 C5 1.426(2) . ? C4 H4 0.982(17) . ? C5 N3 1.359(2) . ? C5 C6 1.440(2) . ? C6 C7 1.372(2) . ? C6 H6 0.989(17) . ? C7 H7 1.012(17) . ? N1 N2 1.4067(17) . ? N1 H1A 0.925(18) . ? N1 H1B 0.858(19) . ? N2 H2 0.915(18) . ? N3 H3A 0.90(2) . ? N3 H3B 0.88(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 O1 C1 N2 122.91(14) . . ? O1 C1 C2 120.75(13) . . ? N2 C1 C2 116.34(13) . . ? C7 C2 C3 120.24(13) . . ? C7 C2 C1 122.03(13) . . ? C3 C2 C1 117.72(13) . . ? C4 C3 C2 120.58(14) . . ? C4 C3 H3 118.0(9) . . ? C2 C3 H3 121.4(9) . . ? C3 C4 C5 119.33(14) . . ? C3 C4 H4 118.4(10) . . ? C5 C4 H4 122.2(10) . . ? N3 C5 C4 119.69(14) . . ? N3 C5 C6 120.06(15) . . ? C4 C5 C6 120.19(14) . . ? C7 C6 C5 120.38(15) . . ? C7 C6 H6 118.7(10) . . ? C5 C6 H6 120.9(10) . . ? C6 C7 C2 119.25(14) . . ? C6 C7 H7 118.5(9) . . ? C2 C7 H7 122.3(9) . . ? N2 N1 H1A 109.2(10) . . ? N2 N1 H1B 104.8(12) . . ? H1A N1 H1B 104.0(15) . . ? C1 N2 N1 121.99(13) . . ? C1 N2 H2 127.5(11) . . ? N1 N2 H2 110.1(10) . . ? C5 N3 H3A 118.3(12) . . ? C5 N3 H3B 116.7(12) . . ? H3A N3 H3B 123.7(17) . . ? 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 O1 C1 C2 C7 -167.55(13) . . . . ? N2 C1 C2 C7 11.92(19) . . . . ? O1 C1 C2 C3 12.0(2) . . . . ? N2 C1 C2 C3 -168.58(12) . . . . ? C7 C2 C3 C4 1.1(2) . . . . ? C1 C2 C3 C4 -178.37(13) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C3 C4 C5 N3 176.13(14) . . . . ? C3 C4 C5 C6 -1.3(2) . . . . ? N3 C5 C6 C7 -176.05(14) . . . . ? C4 C5 C6 C7 1.4(2) . . . . ? C5 C6 C7 C2 -0.2(2) . . . . ? C3 C2 C7 C6 -1.1(2) . . . . ? C1 C2 C7 C6 178.43(13) . . . . ? O1 C1 N2 N1 3.8(2) . . . . ? C2 C1 N2 N1 -175.64(12) . . . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.904 _refine_diff_density_max 0.233 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.044 _chemical_name_common 4-aminobenzohydrazide